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WO2017099695A1 - N-[(aminosulfonyl)phenyl]-2-(1,2-dihydro-2-oxo-3h-indol-3-ylidene)-hydrazinecarbothioamide derivatives for treating cancer and immunological disorders - Google Patents

N-[(aminosulfonyl)phenyl]-2-(1,2-dihydro-2-oxo-3h-indol-3-ylidene)-hydrazinecarbothioamide derivatives for treating cancer and immunological disorders Download PDF

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Publication number
WO2017099695A1
WO2017099695A1 PCT/TR2016/050491 TR2016050491W WO2017099695A1 WO 2017099695 A1 WO2017099695 A1 WO 2017099695A1 TR 2016050491 W TR2016050491 W TR 2016050491W WO 2017099695 A1 WO2017099695 A1 WO 2017099695A1
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WIPO (PCT)
Prior art keywords
indole
dihydro
dione
oxo
sulphamoilphenyl
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PCT/TR2016/050491
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French (fr)
Inventor
Nilgun KARALI
Fusun GOKTAS
Gokce Cihan USTUNDAG
Pinar ERASLAN
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Istanbul Universitesi Rektorlugu
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Istanbul Universitesi Rektorlugu
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Priority claimed from TR2015/15912A external-priority patent/TR201515912A2/en
Priority claimed from TR2015/16135A external-priority patent/TR201516135A2/en
Application filed by Istanbul Universitesi Rektorlugu filed Critical Istanbul Universitesi Rektorlugu
Publication of WO2017099695A1 publication Critical patent/WO2017099695A1/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
    • C07D209/40—Nitrogen atoms, not forming part of a nitro radical, e.g. isatin semicarbazone
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
    • C07D209/32—Oxygen atoms
    • C07D209/38—Oxygen atoms in positions 2 and 3, e.g. isatin

Definitions

  • the present invention relates to 1 -substituted 1 H-indole-2,3-dione derivatives shown by Formula II and 1 H-indole-2,3-dione 3-thiosemi carbazone derivative compounds having sulphamoil residue shown by Formula II I for being use as medicine, and the synthesis methods of these compounds.
  • 1 H-indole-2,3-dione is a versatile molecule having a wide spectrum.
  • the anti-cancer, anti-viral and anti-inflammatory activity attracts attention.
  • the halogenated isatin derivatives show anticancer activity.
  • Mannich bases of the 5-Bromo-3-o-nitrophenyl isatin hydrazone and 5- bromo-(2-oxo-3-indolinil) tiyazolidin-2,4-dione series are found to be effective against Walker carcinoma-256 and P388 lymphatic leukemia in mice.
  • 5,7-dibromoisatin has shown cyto-toxic effect against U937 cells (human monocyte-like histiocytic lymphoma) and the N-benzyl derivatives of this molecule have shown cyto-toxic effect against metastatic breast adenocarcinoma cells (MDA-MB-231 ) and against various cancer cells.
  • 5-Fluoro-3- substituted-2-indolinon derivative SU1 1248 (Sunitinib) has been approved by FDA in year 2006 for the treatment of gastro-intestinal-stromal tumors and advanced renal cell
  • Angiogenesis is a substantially attractive target in cancer treatment.
  • SU5416 (Semaxanib), which is tyrosine kinase inhibitor, is a potential inhibitor of VEGF (vascular endothelial growth factor) which plays an important role in angiogenesis.
  • VEGF vascular endothelial growth factor
  • Pre-clinical studies have shown that the tumor growth after SU5416 treatment is inhibited and that the vascular concentration is reduced (O'Donnell et al, 2005).
  • 3-substituted-2-indolinon compound SU9516 which is another tyrosine kinase inhibitor, selectively inhibits cdk2 (cyclin dependent kinase) and it pr Lane et al, 2001 ).
  • Liang et al, (201 1 ) have synthesized various isatin derivative hydrazides starting from this point of view. It has been observed that since there are halogen in 5-position and hydrophobic substituents in position N1 , the inhibitor activity is increased. D25 molecule is
  • the isatin derivative anti-viral compound (I) rhino-virus effectively inhibits 3C protease.
  • the proteases of SARS corona-virus (SARS CoV 3CL pro ) leading to rhino-virus and Severe Acute Respiratory Syndrome (SARS) are in sistein protease class and their active parts show structural similarity.
  • SARS CoV 3CL pro SARS corona-virus
  • SARS Severe Acute Respiratory Syndrome
  • N-phenethyl, N-pheneacyl, N-(1 - naphtyl)methyl and N-(2-naphtyl)methyl derivatives of 5,7-dibromoisatin show cyto-toxic effect in U937, Jurkat and MDA-MB-231 cells. It has been detected that the most efficient derivative in the test results is N-(1 -naphtyl)methyl derivative. These derivatives act by deteriorating the micro-tubule dynamics of the cells, for instance like vinblastine which is a chemotherapeutic agent (Matesic et al, 2008).
  • 1 -Methyl-1 H-indole-2,3-dione 3-(N,N-diethylthio- semicarbazone) and 1 -allyl-1 7-indole-2,3-dione 3-(N,N-diallylthiosemicarbazone) compounds are effective against HIV as reverse-transcriptase inhibitors (Teitz et al, 1994).
  • n-alkyl (C1 -4), allyl, cyclo-hexyl, phenyl, 4- tuted phenyl, benzyl
  • P-glycoprotein plays an important role in formation of MDR - Multi-drug Resistance in cancer treatment.
  • P-gp whose synthesis substantially increases in cancer cells, substantially decreases the positive response to chemotherapy.
  • Hall et al 2009 and 201 1 ) have tested the cyto-toxic effect of the 1 H-lndol-2,3-dione 3-thiosemicarbazone derivative compounds on these cancer cells producing excessive P-gp.
  • N 4 -phenyl substituted thiosemi carbazone derivatives is much more effective than the N 4 -alkyl, N 4 -cycloalkyl and N 4 -non-substituted derivatives.
  • R 1 H, 5-CH 3 , 5-OCF 3 , 5-F, 5-CI, 5-Br, 5-N0 2 , 5,7-diBr
  • the basic object of the present invention is to synthesize Formula II and Formula III molecules which selectively target receptor or enzyme systems and which will provide overcoming of the disadvantages led by the agents which are present in the known state of the art.
  • Another object of the present invention is to determine the methods to be used in obtaining the molecules, shown by Formula II and Formula III, with high efficiency and in a pure manner.
  • One of the basic targets of searches for developing medicine against pluralities of diseases including cancer and diseases in the immunity system is to suppress the related enzyme or receptor mechanisms which are specific to the disease.
  • the success of the treatments and the minimization of the side effects of medicines will become possible by means of developing medicines which selectively target disease cells and/or pathogens without damaging healthy cells.
  • the present invention relates to 2-indolinon derivative molecules whose general chemical structure is shown by Formula I I.
  • F>1 is selected from a group comprising hydrogen, alkyl, metoxy, trifluorometoxy, halogen, nitro, carbonitryl, carboxamide, sodium sulphonate, sulphonamide.
  • F>2 is selected from a group comprising hydrogen, halogens.
  • F>3 is selected from a group comprising hydrogen, methyl, trifluoromethyl, metoxy, halogen.
  • F>4 is independently selected from a group comprising alkyl, alkenil, alkanoic acid, alkanoic acid alkyl ester, benzyl, substituted benzyl, 1 -naphtylmethyl, 2-naphtylmethyl.
  • said alkyl is selected from groups comprising methyl, isopropyl and tersiyer butyl.
  • the halogen in F ⁇ is selected from fluor, chlor, bromine and iodine groups.
  • the halogen in R 2 is selected from fluor, chlor and bromine groups.
  • the halogen in R 3 is selected from fluor, chlor and bromine groups.
  • R 1 fluor groups can be selected, and in R 2 , chlor groups can be selected; in R 1 : chlor groups can be selected, and in R 3 , methyl groups can be selected; in and R 3 , dichlor groups can be selected; in and R 3 , dibromine groups can be selected.
  • R 4 is selected from a group comprising saturated or unsaturated, branched or unbranched Ci-3 alkyl, branched or unbranched C 2 . 4 alkanoic acid, branched or unbranched C 2 . 4 alkyl ester of C 2 . 4 branched or unbranched alkanoic acid.
  • R 4 is selected from a group comprising saturated or unsaturated, branched or unbranched Ci-3 alkyl; methyl, ethyl, n-propyl, isopropyl, allyl.
  • R 4 is selected from a group comprising branched or unbranched C 2 . 4 alkanoic acid, acetic acid, 2-methyl acetic acid, propaneonic acid, butanoic acid.
  • R 4 is selected from a group comprising branched or unbranched C 2 .
  • substituted benzyl carries Ci_ 4 straight or branched alkyl, trifluoromethyl, metoxy, trifluorometoxy, fluor, chlor, bromine, iodine, nitro, carbonitryl, carboxy, hydroxy groups in positions 2, 3 or 4 of the phenyl ring.
  • Ci_ 4 straight or branched alkyl it is selected from a group comprising methyl, ethyl, isopropyl and tersiyer butyl groups.
  • Substituted benzyl moreover may carry a group selected from 2,4-dimethyl, 2,5-dimethyl, 2,6-dimethyl, 3,4-dimethyl, 3,5-dimethyl, 2,3-difluor, 2,4-difluor, 2,5-difluor, 2,6-difluor, 3,4- difluor, 3,5-difluor, 2,4-dichlor, 2,6-dichlor, 3,4-dichlor, 3,5-dichlor, 2-chlor-4-fluor, 2-chlor-6- fluor, 3,4,5-trifluor, 2,3,4,5,6-pentafluor in phenyl ring.
  • the general chemical name of the compounds shown by Formula II is 1 -Substituted 1 7- indole-2,3-dione derivatives.
  • the terms of "Formula II" and/or ⁇ -substituted 1 H-indole-2,3-dione" can be interchangeably used.
  • 1 -methyl-2,3- dioxo-2,3-dihydro-1 H-indole-5-sulphonamide compound (Formula 11-1 ) is used.
  • the terms of "11-1 ", “Formula 11-1 " and/or "1 -methyl-2,3-dioxo-2,3-dihydro-1 H-indole-5-sulphonamide” are interchangeably used.
  • 1 -Methyl-5- fluoro-6-chloro-1 7-indole-2,3-dione compound (Formula II-2) is used.
  • the terms of "II-2", “Formula II-2” and/or "1 -Methyl-5-fluoro-6-chloro-1 - -indole-2,3-dione” are interchangeably used.
  • the particular examples described in the present invention and belonging to the molecules shown by Formula II are given below. These examples have been given for describing the present invention in a better manner, and the invention is not limited to these examples in any manner.
  • the compounds shown by Formula II are selected nyl)-1 H-indole-2,3-dione
  • the compounds shown by Formula II are selected -Dioxo-2,3-dihydro-1 H-indole-1 -acetic acid
  • the compounds shown by Formula II are selected ihydro-1 7-indole-1 -yl)propaneoic acid
  • the compounds shown by Formula II are selected dihydro-1 H-indole-1 -acetate
  • the compounds shown by Formula II are selected ydro-1 H-indole-1 -yl)propanoate
  • the compounds shown by Formula II are selected from ethyl 2-(2,3-dioxo-2,3-dihydro-1 H-indole-1 -yl)propanoate
  • the compounds shown by Formula II are selected o-1 H-indole-1 -yl)butanoat
  • the compounds shown by Formula II are selected ylbenzyl)-1 H-indole-2,3-dione
  • the compounds shown by Formula II are selected oromethylbenzyl)-1 H-indole-2,3-dione
  • the compounds shown by Formula II are selected enzyl)-1 H-indole-2,3-dione
  • the compounds shown by Formula II are selected from 1 - 4-Trif luorometoxybenzyl)-1 H-indole-2,3-dione
  • the compounds shown by Formula II are selected from 1 -(4-Fluorobenzyl)-1 H-indole-2,3-dione
  • the compounds shown by Formula II are selected from 1 -(4-Chlorobenzyl)-1 H-indole-2,3-dione
  • the compounds shown by Formula II are selected from 1 -(4-Bromobenzyl)-1 H-indole-2,3-dione
  • the compounds shown by Formula II are selected from 1 -(4-iyodobenzyl)-1 H-indole-2,3-dione
  • the compounds shown by Formula II are selected from 1 -(4-Cyanobenzyl)-1 H-indole-2,3-dione
  • Cyanobenzyl)-2,3-dioxo-2,3-dihydro-1 H-indole-5-sulphonamide 1 -(4-Cyanobenzyl)-7- trifluoromethyl-1H-indole-2,3-dione,1-(4-Cyanobenzyl)-7-metoxy-1 H-indole-2,3-dione,1-(4- Cyanobenzyl)-5-fluoro-6-chloro-1 --indole-2,3-dione,1-(4-Cyanobenzyl)-5-chloro-7-methyl- 1H-indole-2,3-dione,1-(4-Cyanobenzyl)-5,7-dichloro-1 7-indole-2,3-dione,1-(4-Cyanobenzyl)- 5,7-dibromo-1 H-indole-2,3-dione.
  • the compounds shown by Formula II are selected e-2-yl)benzyl]-1 H-indole-2,3-dione
  • the compounds shown by Formula II are selected nzyl)-1H-indole-2,3-dione
  • the compounds shown by Formula II are selected benzyl)-1 H-indole-2,3-dione
  • the compounds shown by Formula II are selected lbenzyl)-1 H-indole-2,3-dione
  • the compounds shown by Formula II are selected from 1 -(3-Trif luoromethylbenzyl)-1 H-indole-2,3-dione
  • Trif luoromethylbenzyl)-2,3-dioxo-2,3-dihydro-1 H-indole-5-sulphonamide 1 -(3- Trifluoromethylbenzyl)-6-fluoro-1 --indole-2,3-dione,1-(3-Trifluoromethylbenzyl)-6-chloro-1 -- indole-2,3-dione,1-(3-Trifluoromethylbenzyl)-6-bromo-1 --indole-2,3-dione,1-(3- Trifluoromethylbenzyl)-7-trifluoromethyl-1H-indole-2,3-dione,1-(3-Trifluoromethylbenzyl)-7- metoxy-1 --indole-2,3-dione,1-(3-Trifluoromethylbenzyl)-7-bromo-1 --indole-2,3-dione.1-(3- Trifluoromethylbenz
  • the compounds shown by Formula II are selected enzyl)-1 H-indole-2,3-dione
  • the compounds shown by Formula II are selected ometoxybenzyl)-1 H-indole-2,3-dione
  • the compounds shown by Formula II are selected enzyl)-1 H-indole-2,3-dione
  • the compounds shown by Formula II are selected mobenzyl)-1H-indole-2,3-dione
  • the compounds shown by Formula II are selected from 1 -(3-iyodobenzyl)-1 H-indole-2,3-dione
  • the compounds shown by Formula II are selected from 1 -(3-Nitrobenzyl)-1 H-indole-2,3-dione
  • the compounds shown by Formula II are selected from 1-(3-Ethylbenzyl)-1H-indole-2,3-dione
  • the compounds shown by Formula II are selected from 1 -[3-(Propane-2-yl)benzyl]-1 H-indole-2,3-dione
  • the compounds shown by Formula II are selected benzyl)-1H-indole-2,3-dione
  • the compounds shown by Formula II are selected hylbenzyl)-1 H-indole-2,3-dione
  • the compounds shown by Formula II are selected from 1 -(2-Trif luoromethylbenzyl)-1 H-indole-2,3-dione
  • the compounds shown by Formula II are selected from 1-(2-Metoxybenzyl)-1H-indole-2,3-dione
  • the compounds shown by Formula II are selected from 1 -(2-Trif luorometoxybenzyl)-1 H-indole-2, 3-dione
  • the compounds shown by Formula II are selected from 1 -(2-Fluorobenzyl)-1 H-indole-2, 3-dione
  • the compounds shown by Formula II are selected Anlagenzyl)-1 H-indole-2,3-dione
  • the compounds shown by Formula II are selected from 1 -(2-Bromobenzyl)-1 H-indole-2,3-dione
  • the compounds shown by Formula II are selected from 1 -(2-iodobenzyl)-1 H-indole-2,3-dione
  • the compounds shown by Formula II are selected from 1 -(2-Nitrobenzyl)-1 H-indole-2,3-dione
  • the compounds shown by Formula II are selected Anlagenzyl)-1 H-indole-2,3-dione
  • the compounds shown by Formula II are selected from 1-(2-Ethylbenzyl)-1H-indole-2,3-dione
  • the compounds shown by Formula II are selected from 1 -(2-t-butylbenzyl)-1 H-indole-2,3-dione
  • the compounds shown by Formula II are selected xo-2,3-dihydro-1 H-indole-1 -yl)methyl]benzoic acid
  • the compounds shown by Formula II are selected oxybenzyl)-1 H-indole-2,3-dione
  • the compounds shown by Formula II are selected from 1 -(2,5-Dimethylbenzyl)-1 H-indole-2,3-dione
  • the compounds shown by Formula II are selected ethylbenzyl)-1 H-indole-2,3-dione
  • the compounds shown by Formula II are selected f imethylbenzyl)-1 H-indole-2,3-dione
  • the compounds shown by Formula II are selected thylbenzyl)-1 H-indole-2,3-dione
  • the compounds shown by Formula II are selected from 1 -(2,3-Difluorobenzyl)-1 H-indole-2,3-dione
  • the compounds shown by Formula II are selected fluorobenzyl)-1 H-indole-2,3-dione
  • the compounds shown by Formula II are selected robenzyl)-1 H-indole-2,3-dione
  • the compounds shown by Formula II are selected orobenzyl)-1 H-indole-2,3-dione
  • the compounds shown by Formula II are selected from 1 -(3,4-Difluorobenzyl)-1 H-indole-2,3-dione
  • the compounds shown by Formula II are selected from 1 -(3,5-Difluorobenzyl)-1 H-indole-2,3-dione
  • the compounds shown by Formula II are selected from 1 -(2,3-Dichlorobenzyl)-1 H-indole-2,3-dione
  • the compounds shown by Formula II are selected from 1 -(2-Chloro-4-fluorobenzyl)-1 H-indole-2,3-dione
  • the compounds shown by Formula II are selected oro-6-fluorobenzyl)-1 H-indole-2,3-dione
  • the compounds shown by Formula II are selected from 1 -(3,4,5-Trif luorobenzyl)-1 H-indole-2,3-dione
  • Trifluorobenzyl)-2,3-dioxo-2,3-dihydro-1 H-indole-5-sulphonamide 1 -(3,4,5-Trifluorobenzyl)-6- fluoro-1 H-indole-2,3-dione,1 -(3,4,5-Trifluorobenzyl)-6-chloro-1 H-indole-2,3-dione,1 -(3,4,5- Trifluorobenzyl)-6-bromo-1 /7-indole-2,3-dione,1 -(3,4, 5-Trifluorobenzyl)-7-methyl-1 /-/-indole- 2,3-dione,1 -(3,4,5-Trifluorobenzyl)-7-trifluoromethyl-1 H-indole-2,3-dione,1 -(3,4,5- Trifluorobenzyl)-7-metoxy-1 H-indole-2,3-dione,1 -
  • the compounds shown by Formula II are selected from 1 -Naphtylmethyl-1 H-indole-2,3-dione
  • the present invention relates to 2-indolinon derivative molecules whose general chemical structure is shown by Formula III:
  • F>2 represents hydrogen, halogen.
  • R 3 represents hydrogen, alkyl, trifluoromethyl, metoxy, halogen.
  • R 4 represents hydrogen, alkyl, alkenil, aralkyl, alkanoic acid, alkanoic acid alkyl ester.
  • R 5 , R 6 and R 7 represent sulphonamide in an independent manner.
  • the alkyl substituent in R ⁇ defines methyl, isopropyl and tersiyer butyl groups.
  • the halogen in R ⁇ is fluor, chlor, bromine and iodine.
  • the halogen in R 2 is fluor, chlor and bromine.
  • the halogen in R 3 represents fluor, chlor and bromine.
  • R 1 fluor groups are defined and in R 2 , chlor groups are defined, in R 1 : chlor groups are defined and in R 3 , methyl groups are defined, in R ⁇ and R 3 , dichlor groups are defined, in R ⁇ and R 3 , dibromine groups are defined.
  • R 4 represents saturated or unsaturated, branched or unbranched Ci_ 3 alkyl, branched or unbranched C 2 . 4 alkanoic acid, C 2 . 4 branched or unbranched alkanoic acid, branched or unbranched C 2 . 4 alkyl ester.
  • R 4 as saturated or unsaturated, branched or unbranched Ci_ 3 alkyl, methyl, ethyl, n- propyl, isopropyl and allyl are defined.
  • branched or unbranched C 2 . 4 alkanoic acid is represented by acetic acid, 2- methylacetic acid, propanonic acid, butanoic acid.
  • branched or unbranched C 2 . 4 alkyl ester of the C 2 . 4 branched or unbranched alkanoic acid is represented by ethyl acetate, isopropyl acetate, tersiyer butyl acetate, ethyl propanoate, ethyl 2-methylacetate, ethyl butanoate.
  • substituted benzyl carries Ci_ 4 straight or branched alkyl, trifluoromethyl, metoxy, trifluorometoxy, fluor, chlor, bromine, iodine, nitro, carbonitryl, carboxy, hydroxy groups in positions 2, 3 or 4 of the phenyl ring.
  • Ci_ 4 straight or branched alkyl defines methyl, ethyl, isopropyl and tersiyer butyl groups.
  • Substituted benzyl moreover carries 2,4-dimethyl, 2,5-dimethyl, 2,6-dimethyl, 3,4-dimethyl, 3,5-dimethyl, 2,3-difluor, 2,4-difluor, 2,5-difluor, 2,6- difluor, 3,4-difluor, 3,5-difluor, 2,4-dichlor, 2,6-dichlor, 3,4-dichlor, 3,5-dichlor, 2-chlor-4-fluor, 2-chlor-6-fluor, 3,4,5-trifluor, 2,3,4,5,6-pentafluor in the phenyl ring.
  • the general chemical name of the compounds shown by Formula III is 2-(2-oxo-1 ,2-dihydro- 3 - -indole-3-yliden)-/V-(2/3/4-sulphamoilphenyl)hydrazine carbothioamide derivatives.
  • the compounds shown by Formula III are selected from 2-(2-oxo-1 ,2-dihydro-3W-indole-3-yliden)-A -(2-sulphamoilphenyl) hydrazine- carbothioamide
  • hydrazinecarbothioamide 2-(5-chloro-7-methyl-2-oxo-1 ,2-dihydro-3 - -indole-3-yliden)-/V-(2- sulphamoilphenyl)hydrazinecarbothioamide, 2-(5,7-dichloro-2-oxo-1 ,2-dihydro-3 7-indole-3- yliden)-/V-(2-sulphamoilphenyl)hydrazinecarbothioamide.
  • the compounds shown by Formula III are selected from 2-(1-Methyl-2-oxo-1 ,2-dihydro-3W-indole-3-yliden)-A -(2-sulphamoilphenyl) hydrazinecarbothioamide and from its derivatives, for instance 2-(1 -methyl-2-oxo-1 ,2-dihydro-3H-indole-3-yliden)-/V-(2- sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 ,5-dimethyl-2-oxo-1 ,2-dihydro-3 7-indole-3- yliden)-/V-(2-sulphamoilphenyl)hydrazinecarbothioamide, 2-[1 -methyl-5-(propane-2-yl)-2-oxo- 1 ,2-dihydro-3 - -indole-3-yliden]-/V-(
  • the compounds shown by Formula III are selected from 2-(1-Ethyl-2-oxo-1 ,2-dihydro-3W-indole-3-yliden)-A -(2-sulphamoilphenyl) hydrazinecarbothioamide
  • the compounds shown by Formula III are selected from 2-(1 -Allyl-2-oxo-1 ,2-dihydro-3W-indole-3-yliden)-A -(2-sulphamoilphenyl) e
  • the compounds shown by Formula III are selected from 2-oxo-3-[2-[(2-sulphamoilphenyl)karbamotioil]hydrazineiliden]-2,3-dihydro-1 H- indole-1-aceticacid
  • the compounds shown by Formula III are selected from ethyl 2-oxo-3-[2-[(2-sulphamoilphenyl)karbamotioil]hydrazineiliden]-2,3-dihydro- 1 H-indole-1 -acetate
  • the compounds shown by Formula III are selected from 2-(1 -Benzyl-2-oxo-1 ,2-dihydro-3H-indole-3-yliden)-A/-(2- sulphamoilphenyl)hydrazinecarbothioamide s
  • the compounds shown by Formula III are selected from 2-[1-(4-trifluoromethylbenzyl)-2-oxo-1 ,2-dihydro-3W-indole-3-yliden]-A -(2- sulphamoilphenyl)hydrazinecarbothioamide and from its derivatives, for instance2-[1 -(4-trifluoromethylbenzyl)-2-oxo-1 ,2-dihydro-3 7- indole-3-yliden]-/V-(2-sulphamoilphenyl)hydrazinecarbothioamide,2-[1 -(4- trifluoromethylbenzyl)-5-methyl-2-oxo-1 ,2-dihydro-3H-indole-3-yliden]-/V-(2- sulphamoilphenyl)hydrazinecarbothioamide,2-[1 -(4-trifluoromethylbenzyl)-5-(propane
  • the compounds shown by Formula III are selected from 2-[1-(3-trifluoromethylbenzyl)-2-oxo-1 ,2-dihydro-3W-indole-3-yliden]-A -(2- sulphamoilphenyl)hydrazinecarbothioamide
  • the compounds shown by Formula III are selected from 2-[1-(2-trifluoromethylbenzyl)-2-oxo-1 ,2-dihydro-3W-indole-3-yliden]-A -(2- sulphamoilphenyl)hydrazinecarbothioamide
  • the compounds shown by Formula III are selected from 2-(1-Naphtylmethyl-2-oxo-1 ,2-dihydro-3W-indole-3-yliden)-A -(2-sulphamoilphenyl) mide
  • the compounds shown by Formula III are selected from 2-(2-Naphtylmethyl-2-oxo-1 ,2-dihydro-3W-indole-3-yliden)-A -(2- sulphamoilphenyl)hydrazinecarbothioamide
  • the compounds shown by Formula III are selected from 2-(2-oxo-1 ,2-dihydro-3W-indole-3-yliden)-A -(3-sulphamoilphenyl) hydrazinecarbothioamide
  • the compounds shown by Formula III are selected from 2-(1-Methyl-2-oxo-1 ,2-dihydro-3H-indole-3-yliden)-A/-(3- sulphamoilphenyl)hydrazinecarbothioamide
  • the compounds shown by Formula III are selected from 2-(1-Ethyl-2-oxo-1 ,2-dihydro-3W-indole-3-yliden)-A -(3-sulphamoilphenyl) hydrazinecarbothioamide
  • the compounds shown by Formula III are selected from 2-oxo-3-[2-[(3-sulphamoilphenyl)karbamotioil]hydrazineiliden]-2,3-dihydro-1 H-
  • the compounds shown by Formula III are selected from 2-(1 -Benzyl-2-oxo-1 ,2-dihydro-3H-indole-3-yliden)-N-(3- sulphamoilphenyl)hydrazinecarbothioamide and from its derivatives, for instance2-(1 -benzyl-2-oxo-1 ,2-dihydro-3H-indole-3-yliden)-N-(3- sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 -benzyl-5-methyl-2-oxo-1 ,2-dihydro-3H- indole-3-yliden)-N-(3-sulphamoilphenyl)hydrazinecarbothioamide, 2-[1 -benzyl-5-(propane-2- yl)-2-oxo-1 ,2-dihydro-3H-indole-3-yliden]-N-
  • the compounds shown by Formula III are selected from 2-[1-(1-naphtylmethyl)-2-oxo-1 ,2-dihydro-3W-indole-3-yliden]-A -(3- sulphamoilphenyl) hydrazinecarbothioamide
  • the compounds shown by Formula III are selected from 2-[1-(2-naphtylmethyl)-2-oxo-1 ,2-dihydro-3W-indole-3-yliden]-A -(3- sulphamoilphenyl) hydrazinecarbothioamide
  • the compounds shown by Formula III are selected from 2-(2-oxo-1 ,2-dihydro-3W-indole-3-yliden)-A -(4-sulphamoilphenyl) hydrazinecarbothioamide
  • the compounds shown by Formula III are selected from 2-(1-Methyl-2-oxo-1 ,2-dihydro-3H-indole-3-yliden)-A/-(4- sulphamoilphenyl)hydrazinecarbothioamide
  • the compounds shown by Formula III are selected from 2-(1 -Ethyl-2-oxo-1 ,2-d i hyd ro-3 W-i ndole-3-yl iden)-A -(4- razinecarbothioamide
  • the compounds shown by Formula III are selected from 2-oxo-3-[2-[(4-sulphamoilphenyl)karbamotioil]hydrazineiliden]-2,3-dihydro-1 H- indole-1-aceticacid
  • the compounds shown by Formula III are selected from 2-(1 -Benzyl-2-oxo-1 ,2-dihydro-3H-indole-3-yliden)-A/-(4- sulphamoilphenyl)hydrazinecarbothioamide and from its derivatives, for instance2-(1 -benzyl-2-oxo-1 ,2-dihydro-3H-indole-3-yliden)-/V-(4- sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 -benzyl-5-methyl-2-oxo-1 ,2-dihydro-3H- indole-3-yliden)-/V-(4-sulphamoilphenyl)hydrazinecarbothioamide, 2-[1 -benzyl-5-(propane-2- yl)-2-oxo-1 ,2-dihydro-3H-indole-3-yliden]
  • the compounds shown by Formula III are selected from 2-(1 -Naphtylmethyl-2-oxo-1 ,2-dihydro-3H-indole-3-yliden)-A/-(4- sulphamoilphenyl)hydrazinecarbothioamide
  • the compounds shown by Formula III are selected from 2-(2-Naphtylmethyl-2-oxo-1 ,2-dihydro-3W-indole-3-yliden)-A -(4- sulphamoilphenyl)hydrazinecarbothioamide
  • the present invention relates to molecules shown by Formula II and Formula III whose general structures and specific examples are given above.
  • the present invention relates to a method to be used in preparation of the molecules shown by Formula II.
  • the substances shown by Formula II described in the present invention can be prepared by means of different methods by taking into consideration the beginning substances shown by Formula I.
  • R 1 H, CH 3 , CH(CH 3 ) 2 , C(CH 3 ) 3 , OCH 3 , OCF 3 , F, CI, Br, I, N0 2 , CN, CONH 2 , S0 3 Na, S0 2 NH 2 ,
  • R 2 H, F, CI, Br
  • R 3 H, CH 3 , CF 3 , OCH 3 , F, CI, Br
  • the present invention relates to a method to be used in preparation of the molecules shown by Formula III.
  • the Formula III compounds are obtained by means of (i) obtaining substance B from compound A shown below, (ii) afterwards, obtaining compound C from compound B and (iii) reacting this compound C with the compound shown by Formula I or II.
  • compound A is mentioned as “A”
  • compound B is mentioned as “B”
  • compound C is mentioned as "C”.
  • compound A is transformed into compound B (i):
  • this compound C is reacted with the compound shown by Formula I or II,
  • R 3 H, CH 3 , CF 3 , OCH 3 , F, CI, Br
  • Example 1 1st method which can be used in preparation of the Formula II substances
  • 1 H-indole-2,3-dione (isatin) derivatives are heated and mixed for 1 hour at 40-60°C inside approximately 10 mL dimethyl formamide (DMF) where I (10 mmole) and potassium carbonate (K 2 C0 3 ) (14.5 mmole) are solvents.
  • R 4 halogenure (1 1 .0 mmole) and potassium iodure (Kl) (2.0 mmole) as catalyst are added to the formed dark colored suspension.
  • the mixture is continued to be heated and mixed at 40-60°C by being controlled by means of thin layer chromatography such that no I residue remains.
  • the mixture is neutralized with hydrochloric acid (HCI), and it is extracted by means of 20 mL ethyl acetate four times and it is dried with the help of anhydrous sodium sulphate (Na 2 S0 4 ).
  • HCI hydrochloric acid
  • Na 2 S0 4 anhydrous sodium sulphate
  • the solvent is removed from the medium under vacuum. The remaining solid part is purified with the help of column chromatography.
  • Example 2 2nd method which can be used in preparation of the Formula II substances
  • Example 4 4th method which can be used in preparation of the Formula II substances I (1 g) is dissolved by mixing in icy medium inside anhydrous DMF. After solid K 2 C0 3 (7.2 mmole) is added, the temperature is brought to room temperature, and it is continued to be mixed for 1 hour. At the end of the duration, R 4 halogenure (1 g) is added, and the reaction is heated and mixed for 5-24 hours at 80°C under the Kl (6 mmole) catalyst. The end of the reaction is controlled with TLC, and the mixture is poured into 50 ml_ HCI, and it is extracted with 50 ml ethyl acetate. The ethyl acetate layer is washed with salty water, and it is dried with the help of MgS0 4 , and it is removed from the medium under solvent vacuum.
  • Example 5 5th method which can be used in preparation of the Formula II substances I (1 mmole) is dissolved in approximately 20 ml_ DMF. Anhydrous K 2 C0 3 (3 mmole) is added to the reaction medium. The mixture is mixed at room temperature such that there remains no I residue. The solvent is removed from the medium under vacuum. The remaining solid part is purified and cleaned with the help of column chromatography.
  • Example 6 6th method which can be used in preparation of the Formula II substances
  • Example 7 7th method which can be used in preparation of the Formula II substances I (1 equiv.), ⁇ in 0.1 mmole corresponding to 1 ml_ is dissolved in anhydrous DMF. It is cooled and stirred in ice. Solid K 2 C0 3 or cesium carbonate (Cs 2 C0 3 ) (1 .2 equiv.) is added to the medium. The dark colored suspension formed is stirred for 1 hour at room temperature. R 4 halogenure (1 .1 equiv.) and Kl (0.2 equiv.) are added thereon, and the reaction is heated and mixed for 5-24 hours at 80°C until there remains no I residue in the medium.
  • the part with ethyl acetate is separated, and it is washed with 25 ml_ salty water, and it is dried and filtered with the help of anhydrous Na 2 S0 4 .
  • the solvent is removed from the medium and solid part is purified and cleaned with the help of column chromatography.
  • Example 9 9th method which can be used in preparation of the Formula II substances I (0.10 mmole) and CaH 2 (0.10 mole) are stirred in 50 ml_ DMF.
  • the reaction mixture is heated in oil bath for 1 hour at 100°C. At the end of the duration, the mixture is cooled down to approximately 40°C. Afterwards, R 4 halogenure (1 10-150 mmole) is slowly added to medium. After the adding process is completed, the mixture is heated for 2-4 hours by being controlled chromatographically with ITK until there remains no isatin residue in the oil bath at 100°C.
  • the part precipitating in the medium is separated, and it is poured in watery HCI (200 ml_, 0.5 M). The watery solution is filtered and the remaining residue is washed with water. It is recommended to extract the watery part with ethyl acetate for increasing efficiency.
  • the formed solid product is crystallized and cleaned from the hexane/ CHCI 2 mixture.
  • Example 10 10th method which can be used in preparation of the Formula II substances
  • Example 11 11th method which can be used in preparation of the Formula II substances
  • Example 12 12th method which can be used in preparation of the Formula II substances
  • the solution of sodium (0.8 g) in 16 ml_ absolute ethanol is added to I provided in suspension form in 24 ml_ absolute alcohol.
  • the sodium salt of the formed purple-black colored I is removed from the medium. It is substantially washed with alcohol and benzene and dried.
  • the sodium salt (1 mmole) of the obtained I and R 4 halogenure (1 .1 mmole) are heated by being subject to microwave rays under 200-500 watt energy in durations changing between 3-5 minutes. The reaction is cooled down to room temperature.
  • the compound formed when substantially mixed with icy water is filtered and removed from the medium.
  • Example 13 13th method which can be used in preparation of the Formula II substances
  • Neutral aluminum 400 mg is added to the solution of sodium salt (Na ) (1 mmole) of I in very small amount of water.
  • the excessive portion of the solvent is vaporized in rato vapor, and the solid portion is dried at 1 10°C for one hour and the R 4 halogenure (1 .1 mmole) is absorbed to the aluminum in I.
  • the reaction is subjected to microwave rays under 400-800 watt energy in durations changing between 4-10 minutes.
  • the mixture is extracted with CH 2 CI 2 after it is cooled down to room temperature.
  • the solid part is purified after the solvent is vaporized.
  • Example 14 14th method which can be used in preparation of the Formula II substances
  • Example 17 1st method which can be used in preparation of the Formula III substances
  • Example 20 4th method which can be used in preparation of the Formula III substances C is added to the solution of I or II having equal molar amount into the solution of approximately 30 ml_ ethanol. The mixture is heated for approximately 30 minutes - 2 hours. At the end of the duration, it is cooled down to room temperature and it is waited for a night. The precipitated solid substance is filtered and removed from the medium and it is washed by alcohol and dried.
  • Example 21 5th method which can be used in preparation of the Formula III substances
  • Example 23 7th method which can be used in preparation of the Formula III substances

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Abstract

N-[(aminosulfonyl)phenyl]-2-(1,2-dihydro-2-oxo-3H-indol-3-ylidene)-hydrazinecarbothioamide derivatives of the following formula (III) for treating cancer and immunological disorders. R5, R6 and R7 are each independently selected from hydrogen and a sulfonamide group, provided that at least one of R5, R6 or R7 is a sulfonamide group. The substituents R1 to R4 are each independently either hydrogen or one of the substituents defined in the claims.

Description

N-[(AMINOSULFONYL)PHENYL]-2-(1 ,2-DIHYDRO-2-OXO-3H-INDOL-3-YLIDENE)- HYDRAZINECARBOTHIOAMIDE DERIVATIVES FOR TREATING CANCER AND IMMUNOLOGICAL DISORDERS
SPECIFICATION
TECHNICAL FIELD
The present invention relates to 1 -substituted 1 H-indole-2,3-dione derivatives shown by Formula II and 1 H-indole-2,3-dione 3-thiosemi carbazone derivative compounds having sulphamoil residue shown by Formula II I for being use as medicine, and the synthesis methods of these compounds.
PRIOR ART One of the most basic objects of medicine development studies is to develop and synthesize the compounds to selectively act on the enzyme and receptor systems seen as an important target in treatment of diseases like atherosclerotic vascular disease, diabetes, gout, Alzheimer since said systems play a critical role in pathogenesis of pluralities of inflammatory diseases and cancer, viral and bacterial infections. The success of their treatments and minimization of the side effects of the medicines will become possible by developing medicines which selectively target the target cell, enzyme or receptors without damaging healthy cells.
In general, chemotherapy medicines lead to death by creating DNA damage and cell stress. Therefore, it is difficult to find medicines having nano-molar binding affinity and which are specific to the target. The success of the cancer treatment and minimization the side effects of the chemotherapy are possible for developing selective medicines to the enzyme or receptor mechanisms. This approach will increase the susceptibility of the tumor cells to the chemotherapeutic medicines, and thus, at lower doses, this will provide obtaining anti-tumor effect. By means of this, the side effects of the chemotherapeutic medicines will also become possible.
1 H-indole-2,3-dione (isatin) is a versatile molecule having a wide spectrum. When the literature is observed, the anti-cancer, anti-viral and anti-inflammatory activity attracts attention. Particularly, it has been detected that the halogenated isatin derivatives show anticancer activity. Mannich bases of the 5-Bromo-3-o-nitrophenyl isatin hydrazone and 5- bromo-(2-oxo-3-indolinil) tiyazolidin-2,4-dione series are found to be effective against Walker carcinoma-256 and P388 lymphatic leukemia in mice. 5,7-dibromoisatin has shown cyto-toxic effect against U937 cells (human monocyte-like histiocytic lymphoma) and the N-benzyl derivatives of this molecule have shown cyto-toxic effect against metastatic breast adenocarcinoma cells (MDA-MB-231 ) and against various cancer cells. 5-Fluoro-3- substituted-2-indolinon derivative SU1 1248 (Sunitinib) has been approved by FDA in year 2006 for the treatment of gastro-intestinal-stromal tumors and advanced renal cell
Figure imgf000003_0001
SU 1 1248
(Sunitinib)
Angiogenesis is a substantially attractive target in cancer treatment. SU5416 (Semaxanib), which is tyrosine kinase inhibitor, is a potential inhibitor of VEGF (vascular endothelial growth factor) which plays an important role in angiogenesis. Pre-clinical studies have shown that the tumor growth after SU5416 treatment is inhibited and that the vascular concentration is reduced (O'Donnell et al, 2005). 3-substituted-2-indolinon compound SU9516, which is another tyrosine kinase inhibitor, selectively inhibits cdk2 (cyclin dependent kinase) and it pr Lane et al, 2001 ).
Figure imgf000003_0002
SU5416 SU9516
(Semaxanib)
One of the tyrosine kinases which play role in tumor formation is the c-Met kinase. In order to inhibit c-Met kinase signal path until now, various therapeutic strategies have been tried. Liang et al, (201 1 ) have synthesized various isatin derivative hydrazides starting from this point of view. It has been observed that since there are halogen in 5-position and hydrophobic substituents in position N1 , the inhibitor activity is increased. D25 molecule is
.
Figure imgf000004_0001
The isatin derivative anti-viral compound (I) rhino-virus effectively inhibits 3C protease. The proteases of SARS corona-virus (SARS CoV 3CLpro) leading to rhino-virus and Severe Acute Respiratory Syndrome (SARS) are in sistein protease class and their active parts show structural similarity. Starting from this point of view, isatin derivative protease inhibitors (II
Figure imgf000004_0002
The structure-activity relation studies in isatin derivatives have shown that the substituents, attracting electron in position 5 of the indole ring, and the N-benzyl derivatives and the electron attracting groups which are substituted to the orthogonal para positions of the N- benzyl derivatives have increased activity against tumor cells. It has been found that 5,7- dibromo-N-(p-methyl-benzyl)isatin, which is the most effective derivative among a series compound synthesized within this scope, inhibits the metabolic activity of U937 and Jurkat cancer cells (Vine et al, 2007).
In another study, it has been detected that the N-phenethyl, N-pheneacyl, N-(1 - naphtyl)methyl and N-(2-naphtyl)methyl derivatives of 5,7-dibromoisatin show cyto-toxic effect in U937, Jurkat and MDA-MB-231 cells. It has been detected that the most efficient derivative in the test results is N-(1 -naphtyl)methyl derivative. These derivatives act by deteriorating the micro-tubule dynamics of the cells, for instance like vinblastine which is a chemotherapeutic agent (Matesic et al, 2008). The study made by Matheus et al (2007) has shown that isatin and its derivatives inhibit cyclooxygenase-2 (COX-2) related to inflammatory response in macrophage cells and the nitric oxide-synthase which can be induced, and depending on this, the study has shown that the PGE2 and NO levels in these cells are reduced. Since COX-2 and iNOS enzyme levels in inflamed and cancer cells substantially increase, this has shown that the isatin derivatives which inhibit these enzymes can be used both as anti-carcinogenase and as anti- inflammatory.
Figure imgf000005_0001
On the other hand, the anti-viral activities of 1 -Alkyl-1 H-indole-2,3-dione3-thiosemi- carbazone derivatives have been known for a long time. 1 -Methyl-1 H-indole-2,3-dione 3- thiosemicarbazone (methisazone) has been the first anti-viral agent used as prophylactic in pox disease (Heiner et al, 1971 ). 1 -Methyl-1 H-indole-2,3-dione 3-(N,N-diethylthio- semicarbazone) and 1 -allyl-1 7-indole-2,3-dione 3-(N,N-diallylthiosemicarbazone) compounds are effective against HIV as reverse-transcriptase inhibitors (Teitz et al, 1994).
It has been recorded that 1 -Alkyl-7-alkyl/halo-substituted 1 H-indole-2,3-dione 3-(N-aralkylthio semicarbazone) derivatives are New Delhi metallo-lactamase (NDM-1 ) inhibitors (Zhengming et al, CN 102626408a, 2012). It has been detected that 7-Substituted 1 H-indole-2,3-dione 3- [N-(substituted-phenyl) thiosemicarbazone] derivatives are very effective in inhibition of methicillin-resistant Staphylococcusaurei (MRSA) and vancomycin-resistant enterococcus (VRE) (Wang et al, CN 103483239 A, 2014). The studies of Karali et al related to 1 H-indole-2,3-dione N-alkyl/ cyclo-alkyl/ phenyl-3- thiosemicarbazone and its derivatives have shown that these derivatives are substantially anti-cancer and anti-tuberculosis effective (Karali 2002, Karali et al, 2002, Karali et al, 2007, Guzel et al, 2008). In the patent of Hall et al with title as methods for usage and definitions of compounds which are suitable for cancer cells which are resistant to medicine, said articles of Karali et al have been shown as reference, and within the scope of this study, the compounds recorded in the literature under the name of Karali et al have been tested, and it has been recorded that these compounds have substantial selective effect (2013/ EP 2240175 B1 ). , CH3, OCF3, F, Br, N02
, CH3, morpholinomethyl, piperidinomethyl
n-alkyl (C1 -4), allyl, cyclo-hexyl, phenyl, 4- tuted phenyl, benzyl
Figure imgf000006_0001
P-glycoprotein (P-gp) plays an important role in formation of MDR - Multi-drug Resistance in cancer treatment. P-gp, whose synthesis substantially increases in cancer cells, substantially decreases the positive response to chemotherapy. Hall et al (2009 and 201 1 ) have tested the cyto-toxic effect of the 1 H-lndol-2,3-dione 3-thiosemicarbazone derivative compounds on these cancer cells producing excessive P-gp. This study has shown the importance of aromatic/hydrophobic residue in position N4 of the isatin ring and thiosemi carbazone and this study has proven that N4-phenyl substituted thiosemi carbazone derivatives is much more effective than the N4-alkyl, N4-cycloalkyl and N4-non-substituted derivatives.
In another study where the anti-proliferative effect of 1 H-indole-2,3-dione thiosemi carbazone is searched, it has been determined that L3 compound has strong anti-proliferative effect on
) (Ali et al, 2014).
Figure imgf000006_0002
The structure-activity relation studies in 2-indolinon derivatives have shown that the electron attracting substituents in position 5 of the indole ring, N-alkylation and thiosemi carbazone formation increase efficiency against different virus and tumor cells (Vine et al, 2007) and moreover the studies have shown that by means of N-methylation, a small change has been detected in the activity, and by means of greater hydrophobic groups (allyl, tersiyer butyl- acetate, benzyl etc.), the N-alkylation results in effective derivatives at low nano-molar level. (Lee et al, 2001 ). Matesic et al (2008) have examined N-phenethyl, N-pheneacyl and N-(1 and 2-naphtylmethyl) isatin derivatives against different cancer cells, and they have recorded that the most efficient derivative in the test results is N-(l -naphtylmethyl). While the QSAR analyses (Sabet et al, 2010) of the isatin analogs with anti-cancer effect express the importance of the presence of the halogens attracting electron at positions 5 and 7 of the indole ring, and they have shown that an aromatic ring, bonded to the position-1 by means of 1 or 3 carbon chains, substantially affects the activity. It has been determined that 1 -Benzyl- 1 H-indole-2,3-dione 3-thiosemicarbazone is a non-toxic anti-oxidant and a promising anti- atherogenic agent (Barcelos et al, 2012). Moreover, the studies related to isatin 1 H-indole- 2,3-dione 3-thiosemicarbazone derivatives have proven that N4-phenyl substituted thiosemi carbazone derivatives are much more effective than the N4-alkyl, N4-cycloalkyl and N4-non- substituted derivatives.
The synthesis of seven new thiosemi carbazone derivatives obtained by the condensation of thiosemi carbazide derivatives having 4-Sulphamoilphenyl residue with substituted 1 H- indole-2,3-dione derivatives, the anti-cancer and anti-viral results thereof have been presented in Tetrahedron congress (Karali et al, 2013). In this congress, the activity findings of 1 H-indole-2,3-dione3-(4-sulphamoilphenyl)thiosemi-carbazone synthesized by Abdel- Rahman et al (2010) and whose biological activity scan has not been made have also been provided. These eight derivatives have been kept outside the scope of the patent.
Figure imgf000007_0001
R1 = H, 5-CH3, 5-OCF3, 5-F, 5-CI, 5-Br, 5-N02, 5,7-diBr
In the known state of the art, various 1 H-indole-2,3-dione derivatives and the anti-cancer, anti-viral and anti-inflammatory effects of the derivatives thereof having this structure have been recorded. In the related art, new therapeutic agents, which selectively target pathogen virus and bacteria and tumor cells without damaging healthy cells, are strongly required. These small molecules, which will act on enzyme systems which are seen as an important target in treatment of diseases like atherosclerotic vascular disease, diabetes, gout, Alzheimer, are strictly going to attract attention at the global level since they will play a critical role in pathogenesis of pluralities of inflammatory diseases. These molecules which are not recorded in literature and which are synthesized within the scope of the patent are compounds which will selectively target the treatment of said diseases.
OBJECT OF THE INVENTION
By means of the developed compounds, it is aimed to suppress specifically related enzyme or receptor mechanisms against various diseases including cancer and diseases in the immunity system, and thus, it will become possible to develop medicines which selectively target disease cells without damaging healthy cells and to become successful in the treatments and to minimize the side effects of the medicines. Accordingly, the basic object of the present invention is to synthesize Formula II and Formula III molecules which selectively target receptor or enzyme systems and which will provide overcoming of the disadvantages led by the agents which are present in the known state of the art.
Another object of the present invention is to determine the methods to be used in obtaining the molecules, shown by Formula II and Formula III, with high efficiency and in a pure manner. BRIEF DESCRIPTION OF THE INVENTION
One of the basic targets of searches for developing medicine against pluralities of diseases including cancer and diseases in the immunity system is to suppress the related enzyme or receptor mechanisms which are specific to the disease. However, the success of the treatments and the minimization of the side effects of medicines will become possible by means of developing medicines which selectively target disease cells and/or pathogens without damaging healthy cells.
Within the scope of the present invention, the molecules shown by Formula II and which are suitable for use in the treatment of various diseases and the -(non) substituted 1 H-indole-2,3- dione 3-thiosemi carbazone derivatives shown by Formula III are described.
Since 1 H-indole-2,3-dione derivatives and sulphonamide residue substantially increase the anti-cancer, anti-viral and anti-inflammatory effects, in this study, 2, 3 or 4-sulphamoil- phenylthio-semi-carbazides D have been used, and by means of interaction of these derivatives with derivatives II having 1 -alkyl, alkenyl, aralkyl, alkanoic acid, alkanoic acid alkyl ester of 1 H-indole-2,3-dione and 1 H-indole-2,3-dione, 1 -(non) substituted 1 H-indole-2,3- dione 3-thiosemi carbazone derivatives I II, which have sulphamoil residue in positions 2, 3 or 4 of the phenyl ring, have been synthesized. These derivatives have sulphonamide residue in position 4 of the phenyl ring. Within the scope of this study, substituted III derivatives have been synthesized which are at positions 1 , 5, 6 and/or 7 of the indole ring first having sulphonamide residue at positions 2 and 3 of the phenyl ring besides the III derivatives having 4-sulphonamideophenyl residue which are not recorded in the literature, and various synthesis methods of the III derivatives have been recorded. DETAILED DESCRIPTION OF THE INVENTION
From one perspective, the present invention relates to 2-indolinon derivative molecules whose general chemical structure is shown by Formula I I.
Figure imgf000009_0001
Here, F>1 is selected from a group comprising hydrogen, alkyl, metoxy, trifluorometoxy, halogen, nitro, carbonitryl, carboxamide, sodium sulphonate, sulphonamide.
F>2 is selected from a group comprising hydrogen, halogens.
F>3 is selected from a group comprising hydrogen, methyl, trifluoromethyl, metoxy, halogen. F>4 is independently selected from a group comprising alkyl, alkenil, alkanoic acid, alkanoic acid alkyl ester, benzyl, substituted benzyl, 1 -naphtylmethyl, 2-naphtylmethyl.
In Formula II,
In R said alkyl is selected from groups comprising methyl, isopropyl and tersiyer butyl. The halogen in F^ is selected from fluor, chlor, bromine and iodine groups.
The halogen in R2 is selected from fluor, chlor and bromine groups.
The halogen in R3 is selected from fluor, chlor and bromine groups.
In a preferred application of the present invention, in R1 : fluor groups can be selected, and in R2, chlor groups can be selected; in R1 : chlor groups can be selected, and in R3, methyl groups can be selected; in and R3, dichlor groups can be selected; in and R3, dibromine groups can be selected.
R4 is selected from a group comprising saturated or unsaturated, branched or unbranched Ci-3 alkyl, branched or unbranched C2.4 alkanoic acid, branched or unbranched C2.4 alkyl ester of C2.4 branched or unbranched alkanoic acid.
R4 is selected from a group comprising saturated or unsaturated, branched or unbranched Ci-3 alkyl; methyl, ethyl, n-propyl, isopropyl, allyl. R4 is selected from a group comprising branched or unbranched C2.4 alkanoic acid, acetic acid, 2-methyl acetic acid, propaneonic acid, butanoic acid. R4 is selected from a group comprising branched or unbranched C2.4 alkyl ester of branched or unbranched alkanoic acid, ethyl acetate, isopropyl acetate, tersiyer butyl acetate, ethyl propanoate, ethyl 2-methylacetate, ethyl butanoate. In R4, substituted benzyl carries Ci_4 straight or branched alkyl, trifluoromethyl, metoxy, trifluorometoxy, fluor, chlor, bromine, iodine, nitro, carbonitryl, carboxy, hydroxy groups in positions 2, 3 or 4 of the phenyl ring. Here, as the Ci_4 straight or branched alkyl, it is selected from a group comprising methyl, ethyl, isopropyl and tersiyer butyl groups. Substituted benzyl moreover may carry a group selected from 2,4-dimethyl, 2,5-dimethyl, 2,6-dimethyl, 3,4-dimethyl, 3,5-dimethyl, 2,3-difluor, 2,4-difluor, 2,5-difluor, 2,6-difluor, 3,4- difluor, 3,5-difluor, 2,4-dichlor, 2,6-dichlor, 3,4-dichlor, 3,5-dichlor, 2-chlor-4-fluor, 2-chlor-6- fluor, 3,4,5-trifluor, 2,3,4,5,6-pentafluor in phenyl ring.
The general chemical name of the compounds shown by Formula II is 1 -Substituted 1 7- indole-2,3-dione derivatives. In order to describe these molecules within the scope of the present invention, the terms of "Formula II" and/or Ί -substituted 1 H-indole-2,3-dione" can be interchangeably used.
In a preferred application of the present invention, as the Formula II compound, 1 -methyl-2,3- dioxo-2,3-dihydro-1 H-indole-5-sulphonamide compound (Formula 11-1 ) is used. In order to describe this molecule within the scope of the present invention, the terms of "11-1 ", "Formula 11-1 " and/or "1 -methyl-2,3-dioxo-2,3-dihydro-1 H-indole-5-sulphonamide" are interchangeably used. In a preferred application of the present invention, as the Formula II compound, 1 -Methyl-5- fluoro-6-chloro-1 7-indole-2,3-dione compound (Formula II-2) is used. In order to describe this molecule within the scope of the present invention, the terms of "II-2", "Formula II-2" and/or "1 -Methyl-5-fluoro-6-chloro-1 - -indole-2,3-dione" are interchangeably used. The particular examples described in the present invention and belonging to the molecules shown by Formula II are given below. These examples have been given for describing the present invention in a better manner, and the invention is not limited to these examples in any manner. The chemical structures given in the examples show the R4 group, and the R2 and R3 groups to be used are selected from the R1 : R2, R3 groups described above, and naming is realized accordingly. In an application of the present invention, the compounds shown by Formula II are selected l-1 H-indole-2,3-dione
Figure imgf000011_0001
and from the derivatives thereof, for instance 1 -Methyl-2,3-dioxo-2,3-dihydro-1 7-indole-5- sulphonamide, 1 -Methyl-5-fluoro-6-chloro-1 H-indole-2,3-dione.
In an application of the present invention, the compounds shown by Formula II are selected
H-indole-2,3-dione
Figure imgf000011_0002
and from the derivatives thereof, for instance 1 -Ethyl-5-trifluorometoxy-1 7-indole-2,3-dione, 1 -Ethyl-2,3-dioxo-2,3-dihydro-1 H-indole-5-carbonitryl, Sodium 1 -ethyl-2,3-dioxo, 2,3-dihydro- 1 H-indole-5-sulphonate, 1 -Ethyl-2,3-dioxo-2,3-dihydro-1 H-indole-5-sulphonamide, 1 -Ethyl-7- trifluoromethyl-1 H-indole-2,3-dione, 1 -Ethyl-5-fluoro-6-chloro-1 H-indole-2,3-dione. In an application of the present invention, the compounds shown by Formula II are selected l-1 H-indole-2,3-dione
Figure imgf000011_0003
and from the derivatives thereof, for instance 1 -Propyl-5-(propane-2-yl)-1 H-indole-2,3-dione, 1 - Propyl-5-t-butyl-1 7-indole-2,3-dione, 1 -Propyl-5-trifluorometoxy-1 7-indole-2,3-dione, 1 - Propyl-2,3-dioxo-2,3-dihydro-1 H-indole-5-carbonitryl, 1 - Propyl-2,3-dioxo-2,3-dihydro-1 H- indole-5-sulphonamide, 1 - Propyl-7-trifluoromethyl-1 H-indole-2,3-dione, 1 - Propyl-7-metoxy- 1 H-indole-2,3-dione, 1 - Propyl-5-fluoro-6-chloro-1 7-indole-2,3-dione, 1 - Propyl-5-chloro-7- methyl-1 H-indole-2,3-dione. In an application of the present invention, the compounds shown by Formula II are selected from 1 -(Propane-2-yl)-1 H-indole-2,3-dione
Figure imgf000012_0001
and from its derivatives, for instance 1 -(Propane-2-yl)-5-trifluorometoxy-1 Hindole-2,3-dione, 1 -(Propane-2-yl)-2,3-dioxo-2,3-dihydro-1 H-indole-5-carbonitryl, 1 -(Propane-2-yl)-2,3-dioxo- 2,3-dihydro-1 Hindole-5-carboxamide, Sodium 1 -(propane-2-yl)-2,3-dioxo-2,3-dihydro-1 H- indole-5-sulphonate, 1 -(Propane-2-yl)-2,3-dioxo-2,3-dihydro-1 H-indole-5-sulphonamide, 1 - (Propane-2-yl)-7-trif luoromethyl-1 H-indole-2,3-dione, 1 -(Propane-2-yl)-5-fluoro-6-chloro-1 H- indole-2,3-dione, 1 -(Propane-2-yl)-5-chloro-7-methyl-1 H-indole-2,3-dione.
In an application of the present invention, the compounds shown by Formula II are selected nyl)-1 H-indole-2,3-dione
Figure imgf000012_0002
and from its derivatives, for instance 1 -(2-Propenyl)-5-(propane-2-yl)-1 H-indole-2,3-dione, 1 - (2-Propenyl)-5-t-butyl-1 H-indole-2,3-dione, 1 -(2-Propenyl)-5-trifluorometoxy-1 H-indole-2,3- dione, 1 -(2-Propenyl)-2,3-dioxo-2,3-dihydro-1 H-indole-5-carbonitryl, 1 -(2-Propenyl)-2,3- dioxo-2,3-dihydro-1 7-indole-5-carboxamide, 1 -(2-Propenyl)-2,3-dioxo-2,3-dihydro-1 H-indole- 5-sulphonamide, 1 -(2-Propenyl)-7-trif luoromethyl-1 H-indole-2,3-dione, 1 -(2-Propenyl)-7- metoxy-1 7-indole-2,3-dione, 1 -(2-Propenyl)-5-fluoro-6-chloro-1 H-indole-2,3-dione.
In an application of the present invention, the compounds shown by Formula II are selected -Dioxo-2,3-dihydro-1 H-indole-1 -acetic acid
Figure imgf000012_0003
and from its derivatives, for instance 5- t-Butyl-2,3-dioxo-2,3-dihydro-1 7-indole-1 -aceticacid, 5-Trifluorometoxy-2,3-dioxo-2,3-dihydro-1 H-indole-1 -aceticacid, 5-Cyano-2,3-dioxo-2,3- dihydro-1 H-indole-1 -aceticacid, 5-Karbamoil-2,3-dioxo-2,3-dihydro-1 H-indole-1 -aceticacid, sodium 1 -(carboxymethyl)-2,3-dioxo-2,3-dihydro-1 H-indole-5-sulphonate, 5-Sulphamoil-2,3- dioxo-2,3-dihydro-1 H-indole-1 -aceticacid, 7-Metoxy-2,3-dioxo-2,3-dihydro-1 H-indole-1 - aceticacid, 5-Fluoro-6-chloro-2,3-dioxo-2,3-dihydro-1 H-indole-1 -aceticacid, 5-Chloro-7- methyl-2,3-dioxo-2,3-dihydro-1 H-indole-1 -aceticacid, 5,7-Dibromo-2,3-dioxo-2,3-dihydro-1 H- indole-1 -acetic acid.
In an application of the present invention, the compounds shown by Formula II are selected ihydro-1 7-indole-1 -yl)propaneoic acid
Figure imgf000013_0001
and from its derivatives, for instance 3-[5-(propane-2-yl)-2,3-dioxo-2,3-dihydro-1 H-indole-1 - yl]propaneoic acid,3-[5-t-butyl-2,3-dioxo-2,3-dihydro-1 H-indole-1 -yl]propaneoic acid, 3- [5- trifluorometoxy-2,3-dioxo-2,3-dihydro-1 H-indole-1 -yl]propaneoic acid,3-[5-iyodo-2,3-dioxo- 2,3-dihydro-1 H-indole-1 -yl]propaneoic acid,3-[5-cyano-2,3-dioxo-2,3-dihydro-1 H-indole-1 - yl]propaneoic acid,3-[5-karbamoil-2,3-dioxo-2,3-dihydro-1 H-indole-1 -yl]propaneoic acid, Sodium 1 -(2-carboxyethyl)-2,3-dioxo-2,3-dihydro-1 H-indole-5-sulphonate, 3-[5-sulphamoil- 2,3-dioxo-2,3-dihydro-1 H-indole-1 -yl]propaneoic acid,3-[7-trifluoromethyl-2,3-dioxo-2,3- dihydro-1 H-indole-1 -yl]propaneoic acid,3-[7-metoxy-2,3-dioxo-2,3-dihydro-1 H-indole-1 - yl]propaneoic acid,3-[5-f luoro-6-chloro-2,3-dioxo-2,3-dihydro-1 H-indole-1 -yl]propaneoic acid,3-[5-chloro-7-methyl-2,3-dioxo-2,3-dihydro-1 H-indole-1 -yl]propaneoic acid,3-[5,7- dichloro-2,3-dioxo-2,3-dihydro-1 H-indole-1 -yl]propaneoic acid,3-[5,7-dibromo-2,3-dioxo-2,3- dihydro-1 H-indole-1 -yl]propaneoic acid. In an application of the present invention, the compounds shown by Formula II are selected
-2,3-dihydro-1 H-indole-1 -yl)propaneoic acid
Figure imgf000013_0002
and from its derivatives, for instance2-[5-(Propane-2-yl)-2,3-dioxo-2,3-dihydro-1 H-indole-1 - yl]propaneoic acid, 2-(5-t-Butyl-2,3-dioxo-2,3-dihydro-1 H-indole-1 -yl)propaneoic acid, 2-(5- Trifluorometoxy-2,3-dioxo-2,3-dihydro-1 H-indole-1 -yl)propaneoic acid, 2-(5-Karbamoil-2,3- dioxo-2,3-dihydro-1 H-indole-1 -yl)propaneoic acid, Sodium 1 -(1 -carboxyethyl)-2,3-dioxo-2,3- dihydro-1 H-indole-5-sulphonate, 2-(5-Sulphamoil-2,3-dioxo-2,3-dihydro-1 H-indole-1 - yl)propaneoic acid, 2-(7-Trifluoromethyl-2,3-dioxo-2,3-dihydro-1 H-indole-1 -yl)propaneoic acid, 2-(7-Metoxy-2,3-dioxo-2,3-dihydro-1 H-indole-1 -yl)propaneoic acid, 2-(5-Chloro-7- methyl-2,3-dioxo-2,3-dihydro-1 H-indole-1 -yl)propaneoic acid, 2-(5-Fluoro-6-chloro-2,3-dioxo- 2,3-dihydro-1 H-indole-1 -yl)propaneoic acid, 2-(5,7-Dibromo-2,3-dioxo-2,3-dihydro-1 H-indole- 1 -yl)propaneoic acid.
In an application of the present invention, the compounds shown by Formula II are selected
-2,3-dihydro-1 7-indole-1 -yl)butanoic acid
Figure imgf000014_0001
and from its derivatives, for instance 4-(5-(propane-2-yl)-2,3-dioxo-2,3-dihydro-1 7-indole-1 - yl)butanoicacid,4-(5-t-butyl-2,3-dioxo-2,3-dihydro-1 H-indole-1 -yl)butanoicacid, 4-(5- trifluorometoxy-2,3-dioxo-2,3-dihydro-1 - -indole-1 -yl)butanoicacid,4-(5-iyodo-2,3-dioxo-2,3- dihydro-1 H-indole-1 -yl)butanoicacid,4-(5-nitro-2,3-dioxo-2,3-dihydro-1 H-indole-1 - yl)butanoicacid,4-(5-cyano-2,3-dioxo-2,3-dihydro-1 H-indole-1 -yl)butanoicacid, 4-(5-karbamoil- 2, 3-dioxo-2,3-dihydro-1 H-indole-1 -yl)butanoic acid, Sodium 1 -(3-carboxypropyl)-2,3-dioxo- 2,3-dihydro-1 H-indole-5-sulphonate, 4-(5-sulphamoil-2,3-dioxo-2,3-dihydro-1 H-indole-1 - yl)butanoicacid,4-(7-trifluoromethyl-2,3-dioxo-2,3-dihydro-1 H-indole-1 -yl)butanoicacid,4-(7- metoxy-2,3-dioxo-2,3-dihydro-1 H-indole-1 -yl)butanoicacid,4-(5-fluoro-6-chloro-2,3-dioxo-2, 3- dihydro-1 H-indole-1 -yl)butanoicacid,4-(5-chloro-7-methyl-2,3-dioxo-2,3-dihydro-1 H-indole-1 - yl)butanoicacid,4-(5,7-dichloro-2,3-dioxo-2,3-dihydro-1 H-indole-1 -yl)butanoicacid,4-(5, 7- dibromo-2,3-dioxo-2,3-dihydro-1 H-indole-1 -yl)butanoic acid. In an application of the present invention, the compounds shown by Formula II are selected dihydro-1 H-indole-1 -acetate
Figure imgf000014_0002
and from its derivatives, for instance ethyl 5-(propane-2-yl)-2,3-dioxo-2,3-dihydro-1 H-indole- 1 -acetate, ethyl 5- t-butyl-2,3-dioxo-2,3-dihydro-1 H-indole-1 -acetate, ethyl 5-trifluorometoxy- 2,3-dioxo-2,3-dihydro-1 H-indole-1 -acetate, ethyl 5-iyodo-2,3-dioxo-2,3-dihydro-1 H-indole-1 - acetate, ethyl 5-cyano-2,3-dioxo-2,3-dihydro-1 H-indole-1 -acetate, ethyl 5-karbamoil-2,3- dioxo-2,3-dihydro-1 H-indole-1 -acetate, Sodium 1 -(2-etoxy-2-oxoethyl)-2,3-dioxo-2,3-dihydro- 1 H-indole-5-sulphonate, ethyl 5-sulphamoil-2,3-dioxo-2,3-dihydro-1 H-indole-1 -acetate, ethyl 7-trif luoromethyl-2,3-dioxo-2,3-dihydro-1 H-indole-1 acetate, ethyl 7-metoxy-2,3-dioxo-2,3- dihydro-1 H-indole-1 acetate, ethyl 5-f luoro-6-chloro-2,3-dioxo-2,3-dihydro-1 H-indole-1 acetate, ethyl 5-chloro-7-methyl-2,3-dioxo-2,3-dihydro-1 H-indole-1 acetate. In an application of the present invention, the compounds shown by Formula II are selected oxo-2,3-dihydro-1 H-indole-1 -acetate
Figure imgf000015_0001
and from its derivatives, for instancePropane-2-yl 5-(propane-2-yl)-2,3-dioxo-2,3-dihydro-1 H- indole-1 -acetate, Propane-2-yl 5-t-butyl-2,3-dioxo-2,3-dihydro-1 H-indole-1 -acetate, Propane- 2-yl 5-trifluorometoxy-2,3-dioxo-2,3-dihydro-1 H-indole-1 -acetate, Propane-2-yl 5-iyodo-2,3- dioxo-2,3-dihydro-1 H-indole-1 -acetate, Propane-2-yl 5-cyano-2,3-dioxo-2,3-dihydro-1 H- indole-1 -acetate, Propane-2-yl 5-karbamoil-2,3-dioxo-2,3-dihydro-1 H-indole-1 -acetate, Sodium 1 -[2-oxo-2-(propane-2-yloxy)ethyl]-2,3-dioxo-2,3-dihydro-1 H-indole-5-sulphonate, Propane-2-yl 5-sulphamoil-2,3-dioxo-2,3-dihydro-1 H-indole-1 -acetate, Propane-2-yl 7- trifluoromethyl-2,3-dioxo-2,3-dihydro-1 H-indole-1 -acetate, Propane-2-yl 7-metoxy-2,3-dioxo- 2,3-dihydro-1 H-indole-1 -acetate, Propane-2-yl 7-chloro-2,3-dioxo-2,3-dihydro-1 H-indole-1 - acetate, Propane-2-yl 5-fluoro-6-chloro-2,3-dioxo-2,3-dihydro-1 H-indole-1 -acetate, Propane- 2-yl 5-chloro-7-methyl-2,3-dioxo-2,3-dihydro-1 H-indole-1 -acetate, Propane-2-yl 5,7-dichloro- 2,3-dioxo-2,3-dihydro-1 H-indole-1 -acetate, Propane-2-yl 5,7-dibromo-2,3-dioxo-2,3-dihydro- 1 H-indole-1 -acetate.
In an application of the present invention, the compounds shown by Formula II are selected dihydro-1 H-indole-1 -acetate
Figure imgf000015_0002
and from its derivatives, for instance t-Butyl 5-methyl-2,3-dioxo-2,3-dihydro-1 H-indole-1 - acetate, t-Butyl 5-(propane-2-yl)-2,3-dioxo-2,3-dihydro-1 H-indole-1 -acetate, t-Butyl 5-t-butyl- 2,3-dioxo-2,3-dihydro-1 H-indole-1 -acetate, t-Butyl 5-trif luorometoxy-2,3-dioxo-2,3-dihydro- 1 H-indole-1 -acetate, t-Butyl 5-fluoro-2,3-dioxo-2,3-dihydro-1 H-indole-1 -acetate, t-Butyl 5- iyodo-2,3-dioxo-2,3-dihydro-1 H-indole-1 -acetate, t-Butyl 5-cyano-2,3-dioxo-2,3-dihydro-1 H- indole-1 -acetate, t-Butyl 5-karbamoil-2,3-dioxo-2,3-dihydro-1 H-indole-1 -acetate, Sodium 1 - (2-t-butoxy-2-oxoethyl)-2,3-dioxo-2,3-dihydro-1 H-indole-5-sulphonate, t-Butyl 5-sulphamoil- 2,3-dioxo-2,3-dihydro-1 H-indole-1 -acetate, t-Butyl 6-chloro-2,3-dioxo-2,3-dihydro-1 H-indole- 1 -acetate, t-Butyl 6-bromo-2,3-dioxo-2,3-dihydro-1 H-indole-1 -acetate, t-Butyl 7-methyl-2,3- dioxo-2,3-dihydro-1 H-indole-1 -acetate, t-Butyl 7-trifluoromethyl-2,3-dioxo-2,3-dihydro-1 H- indole-1 -acetate, t-Butyl 7-metoxy-2,3-dioxo-2,3-dihydro-1 H-indole-1 -acetate, t-Butyl 7- fluoro-2,3-dioxo-2,3-dihydro-1 H-indole-1 -acetate, t-Butyl 7-chloro-2,3-dioxo-2,3-dihydro-1 H- indole-1 -acetate, t-Butyl 7-bromo-2,3-dioxo-2,3-dihydro-1 H-indole-1 -acetate, t-Butyl 5-fluoro- 6-chloro-2,3-dioxo-2,3-dihydro-1 H-indole-1 -acetate, t-Butyl 5-chloro-7-methyl-2,3-dioxo-2,3- dihydro-1 H-indole-1 -acetate, t-Butyl 5,7-dichloro-2,3-dioxo-2,3-dihydro-1 H-indole-1 -acetate, t-Butyl 5,7-dibromo-2,3-dioxo-2,3-dihydro-1 H-indole-1 -acetate.
In an application of the present invention, the compounds shown by Formula II are selected ydro-1 H-indole-1 -yl)propanoate
Figure imgf000016_0001
and from its derivatives, for instance ethyl 3-[5-(propane-2-yl)-2,3-dioxo-2,3-dihydro-1 H- indole-1 -yl]propanoate, ethyl 3-[5-t-butyl-2,3-dioxo-2,3-dihydro-1 H-indole-1 -yl]propanoate, ethyl 3-[5-trifluorometoxy-2,3-dioxo-2,3-dihydro-1 H-indole-1 -yl]propanoate, ethyl 3-[5-iyodo- 2,3-dioxo-2,3-dihydro-1 H-indole-1 -yl]propanoate, ethyl 3-[5-cyano-2,3-dioxo-2,3-dihydro-1 H- indole-1 -yl]propanoate, ethyl 3-[5-karbamoil-2,3-dioxo-2,3-dihydro-1 H-indole-1 - yl]propanoate, Sodium 1 -(3-etoxy-3-oxopropyl)-2,3-dioxo-2,3-dihydro-1 H-indole-5- sulphonate, ethyl 3-[5-sulphamoil-2,3-dioxo-2,3-dihydro-1 H-indole-1 -yl]propanoate, ethyl 3- [7-trifluoromethyl-2,3-dioxo-2,3-dihydro-1 H-indole-1 -yl]propanoate, ethyl 3-[7-metoxy-2,3- dioxo-2,3-dihydro-1 H-indole-1 -yl]propanoate, ethyl 3-[5-fluoro-6-chloro-2,3-dioxo-2,3-dihydro- 1 H-indole-1 -yl]propanoate, ethyl 3-[5-chloro-7-methyl-2,3-dioxo-2,3-dihydro-1 H-indole-1 - yl]propanoate, ethyl 3-[5,7-dichloro-2,3-dioxo-2,3-dihydro-1 H-indole-1 -yl]propanoate, ethyl 3- [5,7-dibromo-2,3-dioxo-2,3-dihydro-1 H-indole-1 -yl]propanoate.
In an application of the present invention, the compounds shown by Formula II are selected from ethyl 2-(2,3-dioxo-2,3-dihydro-1 H-indole-1 -yl)propanoate
Figure imgf000017_0001
and from its derivatives, for instance ethyl 2-[5-(propane-2-yl)-2,3-dioxo-2,3-dihydro-1 H- indole-1 -yl]propanoate, ethyl 2-[5-t-butyl-2,3-dioxo-2,3-dihydro-1 H-indole-1 -yl]propanoate, ethyl 2-[5-metoxy-2,3-dioxo-2,3-dihydro-1 H-indole-1 -yl]propanoate, ethyl 2-[5- trifluorometoxy-2,3-dioxo-2,3-dihydro-1 H-indole-1 -yl]propanoate, ethyl 2-[5-f luoro-2,3-dioxo- 2,3-dihydro-1 H-indole-1 -yl]propanoate, ethyl 2-[5-iyodo-2,3-dioxo-2,3-dihydro-1 H-indole-1 - yl]propanoate, ethyl 2-[5-nitro-2,3-dioxo-2,3-dihydro-1 H-indole-1 -yl]propanoate, ethyl 2-[5- cyano-2,3-dioxo-2,3-dihydro-1 H-indole-1 -yl]propanoate, ethyl 2-[5-karbamoil-2,3-dioxo-2,3- dihydro-1 H-indole-1 -yl]propanoate, Sodium 1 -(1 -etoxy-1 -oxopropane-2-yl)-2,3-dioxo-2,3- dihydro-1 H-indole-5-sulphonate, ethyl 2-[5-sulphamoil-2,3-dioxo-2,3-dihydro-1 H-indole-1 - yl]propanoate, ethyl 2-[6-fluoro-2,3-dioxo-2,3-dihydro-1 H-indole-1 -yl]propanoate, ethyl 2-[6- chloro-2,3-dioxo-2,3-dihydro-1 H-indole-1 -yl]propanoate, ethyl 2-[6-bromo-2,3-dioxo-2,3- dihydro-1 H-indole-1 -yl]propanoate, ethyl 2-[7-methyl-2,3-dioxo-2,3-dihydro-1 H-indole-1 - yl]propanoate, ethyl 2-[7-metoxy-2,3-dioxo-2,3-dihydro-1 H-indole-1 -yl]propanoate, ethyl 2-[7- trifluoromethyl-2,3-dioxo-2,3-dihydro-1 H-indole-1 -yl]propanoate, ethyl 2-[7-chloro-2,3-dioxo- 2,3-dihydro-1 H-indole-1 -yl]propanoate, ethyl 2-[7-bromo-2,3-dioxo-2,3-dihydro-1 H-indole-1 - yl]propanoate, ethyl 2-[5-fluoro-6-chloro-2,3-dioxo-2,3-dihydro-1 H-indole-1 -yl]propanoate, ethyl 2-[5-chloro-7-methyl-2,3-dioxo-2,3-dihydro-1 H-indole-1 -yl]propanoate, ethyl 2-[5,7- dichloro-2,3-dioxo-2,3-dihydro-1 H-indole-1 -yl]propanoate, ethyl 2-[5,7-dibromo-2,3-dioxo-2,3- dihydro-1 H-indole-1 -yl]propanoate.
In an application of the present invention, the compounds shown by Formula II are selected o-1 H-indole-1 -yl)butanoat
Figure imgf000017_0002
and from its derivatives, for instance ethyl 4-(5-methyl-2,3-dioxo-2,3-dihydro-1 H-indole-1 - yl)butanoat, ethyl 4-(5-(propane-2-yl)-2,3-dioxo-2,3-dihydro-1 H-indole-1 -yl)butanoat, ethyl 4- (5-t-butyl-2,3-dioxo-2,3-dihydro-1 H-indole-1 -yl)butanoat, ethyl 4-(5-metoxy-2,3-dioxo-2,3- dihydro-1 H-indole-1 -yl)butanoat, ethyl 4-(5-trifluorometoxy-2,3-dioxo-2,3-dihydro-1 H-indole- 1 -yl)butanoat, ethyl 4-(5-fluoro-2,3-dioxo-2,3-dihydro-1 H-indole-1 -yl)butanoat, ethyl 4-(5- chloro-2,3-dioxo-2,3-dihydro-1 H-indole-1 -yl)butanoat, ethyl 4-(5-bromo-2,3-dioxo-2,3- dihydro-1 H-indole-1 -yl)butanoat, ethyl 4-(5-iyodo-2,3-dioxo-2,3-dihydro-1 H-indole-1 - yl)butanoat, ethyl 4-(5-nitro-2,3-dioxo-2,3-dihydro-1 H-indole-1 -yl)butanoat, ethyl 4-(5-cyano- 2,3-dioxo-2,3-dihydro-1 H-indole-1 -yl)butanoat, ethyl 4-(5-karbamoil-2,3-dioxo-2,3-dihydro- 1 H-indole-1 -yl)butanoat, Sodium 1 -(4-etoxy-4-oxobutyl)-2,3-dioxo-2,3-dihydro-1 H-indole-5- sulphonate, ethyl 4-(5-sulphamoil-2,3-dioxo-2,3-dihydro-1 H-indole-1 -yl)butanoat, ethyl 4-(6- fluoro-2,3-dioxo-2,3-dihydro-1 H-indole-1 -yl)butanoat, ethyl 4-(6-chloro-2,3-dioxo-2,3-dihydro- 1 H-indole-1 -yl)butanoat, ethyl 4-(6-bromo-2,3-dioxo-2,3-dihydro-1 H-indole-1 -yl)butanoat, ethyl 4-(7-trifluoromethyl-2,3-dioxo-2,3-dihydro-1 H-indole-1 -yl)butanoat, ethyl 4-(7-metoxy- 2,3-dioxo-2,3-dihydro-1 H-indole-1 -yl)butanoat, ethyl 4-(7-fluoro-2,3-dioxo-2,3-dihydro-1 H- indole-1 -yl)butanoat, ethyl 4-(7-chloro-2,3-dioxo-2,3-dihydro-1 H-indole-1 -yl)butanoat, ethyl 4- (7-bromo-2,3-dioxo-2,3-dihydro-1 H-indole-1 -yl)butanoat, ethyl 4-(5-fluoro-6-chloro-2,3-dioxo- 2,3-dihydro-1 H-indole-1 -yl)butanoat, ethyl 4-(5-chloro-7-methyl-2,3-dioxo-2,3-dihydro-1 H- indole-1 -yl)butanoat, ethyl 4-(5,7-dichloro-2,3-dioxo-2,3-dihydro-1 H-indole-1 -yl)butanoat, ethyl 4-(5,7-dibromo-2,3-dioxo-2,3-dihydro-1 H-indole-1 -yl)butanoat.
In an application of the present invention, the compounds shown by Formula II are selected
1 H-indole-2,3-dione
Figure imgf000018_0001
and from its derivatives, for instance 1 -Benzyl-7-metoxy-1 H-indole-2,3-dione,1 -Benzyl-5- fluoro-6-chloro-1 H-indole-2,3-dione,1 -Benzyl-5,7-dichloro-1 Hindole-2,3-dione.
In an application of the present invention, the compounds shown by Formula II are selected ylbenzyl)-1 H-indole-2,3-dione
Figure imgf000018_0002
and from its derivatives, for instance 1 -(4-Methylbenzyl)-5-(propane-2-yl)-1 H-indole-2,3- dione,1 -(4-Methylbenzyl)-5-t-butyl-1 H-indole-2,3-dione, 1 -(4-Methylbenzyl)-5-trifluorometoxy- 1 H-indole-2,3-dione,1 -(4-Methylbenzyl)-5-iyodo-1 H-indole-2,3-dione ϋ 1 -(4-Methylbenzyl)- 2,3-dioxo-2,3-dihydro-1 - -indole-5-carbonitryl, Sodium 1 -(4-methylbenzyl)-2,3-dioxo-2,3- dihydro-1 7-indole-5-sulphonate, 1 -(4-Methylbenzyl)-2,3-dioxo-2,3-dihydro-1 H-indole-5- sulphonamide, 1 -(4-Methylbenzyl)-7-metoxy-1 H-indole-2,3-dione,1 -(4-Methylbenzyl)-5- fluoro-6-chloro-1 Hindole-2,3-dione,1 -(4-Methylbenzyl)-5-chloro-7-methyl-1 H-indole-2,3- dione,1 -(4-Methylbenzyl)-5,7-dichloro-1 H-indole-2,3-dione.
In an application of the present invention, the compounds shown by Formula II are selected oromethylbenzyl)-1 H-indole-2,3-dione
Figure imgf000019_0001
and from its derivatives, for instance 1 -(4-Trif luoromethylbenzyl)-5-(propane-2-yl)-1 H-indole- 2,3-dione,1 -(4-Trifluoromethylbenzyl)-5-t-butyl-1 H-indole-2,3-dione,1 -(4- Trifluoromethylbenzyl)-5-metoxy-1 - -indole-2,3-dione,1 -(4-Trif luoromethylbenzyl)-5-bromo- 1 H-indole-2,3-dione,1 -(4-Trifluoromethylbenzyl)-2,3-dioxo-2,3-dihydro-1 - -indole-5- carbonitryl, 1 -(4-Trifluoromethylbenzyl)-2,3-dioxo-2,3-dihydro-1 7-indole-5-carboxamide, Sodium 1 -(4-trifluoromethylbenzyl)-2,3-dioxo-2,3-dihydro-1 - -indole-5-sulphonate, 1 -(4- Trif luoromethylbenzyl)-2,3-dioxo-2,3-dihydro-1 H-indole-5-sulphonamide, 1 -(4-
Trifluoromethylbenzyl)-6-fluoro-1 - -indole-2,3-dione,1 -(4-Trif luoromethylbenzyl)-6-chloro-1 7- indole-2,3-dione,1 -(4-Trifluoromethylbenzyl)-7-methyl-1 H-indole-2,3-dione,1 -(4- Trifluoromethylbenzyl)-7-metoxy-1 - -indole-2,3-dione,1 -(4-Trif luoromethylbenzyl)-5-fluoro-6- chloro-1 H-indole-2,3-dione,1 -(4-Trifluoromethylbenzyl)-5-chloro-7-methyl-1 H-indole-2,3- dione,1 -(4-Trif luoromethylbenzyl)-5,7-dichloro-1 - -indole-2,3-dione.
In an application of the present invention, the compounds shown by Formula II are selected enzyl)-1 H-indole-2,3-dione
Figure imgf000019_0002
and from its derivatives, for instance 1 -(4-Metoxybenzyl)-5-(propane-2-yl)-1 H-indole-2,3- dione,1 -(4-Metoxybenzyl)-5-t-butyl-1 H-indole-2,3-dione,1 -(4-Metoxybenzyl)-2,3-dioxo-2,3- dihydro-1 - -indole-5-carbonitryl, 1 -(4-Metoxybenzyl)-2,3-dioxo-2,3-dihydro-1 - -indole-5- carboxamide, Sodium 1 -(4-metoxybenzyl)-2,3-dioxo-2,3-dihydro-1 Hindole-5-sulphonate, 1 - (4-Metoxybenzyl)-2,3-dioxo-2,3-dihydro-1 H-indole-5-sulphonamide, 1 -(4-Metoxybenzyl)-7- metoxy-1 H-indole-2,3-dione,1 -(4-Metoxybenzyl)-5-fluoro-6-chloro-1 H-indole-2,3-dione,1 -(4- Metoxybenzyl)-5-chloro-7-methyl-1 H-indole-2,3-dione, 1 -(4-Metoxybenzyl)-57-dichloro-1 H- indole-2,3-dione.
In an application of the present invention, the compounds shown by Formula II are selected from 1 - 4-Trif luorometoxybenzyl)-1 H-indole-2,3-dione
Figure imgf000020_0001
and from its derivatives, for instance 1 -(4-Trifluorometoxybenzyl)-5-(propane-2-yl)-1 H-indole- 2,3-dione,1 -(4-Trifluorometoxybenzyl)-5-t-butyl-1 H-indole-2,3-dione,1 -(4- Trifluorometoxybenzyl)-5-metoxy-1 - -indole-2,3-dione,1 -(4-Trif luorometoxybenzyl)-5-bromo- 1 H-indole-2,3-dione,1 -(4-Trifluorometoxybenzyl)-5-iyodo-1 - -indole-2,3-dione,1 -(4- Trifluorometoxybenzyl)-5-nitro-1 - -indole-2,3-dione, 1 -(4-Trifluorometoxybenzyl)-2,3-dioxo- 2,3-dihydro-1 7-indole-5-carbonitryl, 1 -(4-Trifluorometoxybenzyl)-2,3-dioxo-2,3-dihydro-1 H- indole-5-carboxamide, Sodium 1 -(4-trif luorometoxybenzyl)-2,3-dioxo-2,3-dihydro-1 H-indole- 5-sulphonate, 1 -(4-Trif luorometoxybenzyl)-2,3-dioxo-2,3-dihydro-1 H-indole-5-sulphonamide, 1 -(4-Trifluorometoxybenzyl)-6-fluoro-1 - -indole-2,3-dione,1 -(4-Trifluorometoxybenzyl)-6- chloro-1 H-indole-2,3-dione,1 -(4-Trifluorometoxybenzyl)-6-bromo-1 - -indole-2,3-dione,1 -(4- Trifluorometoxybenzyl)-7-methyl-1 H-indole-2,3-dione,1 -(4-Trif luorometoxybenzyl)-7- trifluoromethyl-1 H-indole-2,3-dione,1 -(4-Trifluorometoxybenzyl)-7-metoxy-1 H-indole-2,3- dione,1 -(4-Trifluorometoxybenzyl)-5-fluoro-6-chloro-1 - -indole-2,3-dione,1 -(4- Trifluorometoxybenzyl)-5-chloro-7-methyl-1 H-indole-2,3-dione,1 -(4-Trif luorometoxybenzyl)- 5,7-dichloro-1 H-indole-2,3-dione,1 -(4-Trifluorometoxybenzyl)-5,7-dibromo-1 - -indole-2,3- dione.
In an application of the present invention, the compounds shown by Formula II are selected from 1 -(4-Fluorobenzyl)-1 H-indole-2,3-dione
Figure imgf000021_0001
and from its derivatives, for instance 1 -(4-Fluorobenzyl)-5-(propane-2-yl)-1 H-indole-2,3- dione,1 -(4-Fluorobenzyl)-5-t-butyl-1 H-indole-2,3-dione,1 -(4-Fluorobenzyl)-5-iyodo-1 A7-indole- 2,3-dione,1 -(4-Fluorobenzyl)-2,3-dioxo-2,3-dihydro-1 - -indole-5-carbonitryl, 1 -(4- Fluorobenzyl)-2,3-dioxo-2,3-dihydro-1 Hindole-5-carboxamide, Sodium 1 -(4-forobenzyl)-2,3- dioxo-2,3-dihydro-1 7-indole-5-sulphonate, 1 -(4-Fluorobenzyl)-7-metoxy-1 H-indole-2,3- dione,1 -(4-Fluorobenzyl)-5-fluoro-6-chloro-1 H-indole-2,3-dione,1 -(4-Fluorobenzyl)-5-chloro- 7-methyl-1 H-indole-2,3-dione,1 -(4-Fluorobenzyl)-5,7-dichloro-1 H-indole-2,3-dione,1 -(4- Fluorobenzyl)-5,7-dibromo-1 - -indole-2,3-dione.
In an application of the present invention, the compounds shown by Formula II are selected from 1 -(4-Chlorobenzyl)-1 H-indole-2,3-dione
Figure imgf000021_0002
and from its derivatives, for instance 1 -(4-Chlorobenzyl)-5-(propane-2-yl)-1 H-indole-2,3- dione,1 -(4-Chlorobenzyl)-2,3-dioxo-2,3-dihydro-1 7-indole-5-carbonitryl, 1 -(4-Chlorobenzyl)- 2,3-dioxo-2,3-dihydro-1 7-indole-5-carboxamide, Sodium 1 -(4-chlorobenzyl)-2,3-dioxo-2,3- dihydro-1 7-indole-5-sulphonate, 1 -(4-Chlorobenzyl)-2,3-dioxo-2,3-dihydro-1 H-indole-5- sulphonamide, 1 -(4-Chlorobenzyl)-7-metoxy-1 H-indole-2,3-dione,1 -(4-Chlorobenzyl)-5- fluoro-6-chloro-1 - -indole-2,3-dione,1 -(4-Chlorobenzyl)-5-chloro-7-methyl-1 H-indole-2,3- dione.
In an application of the present invention, the compounds shown by Formula II are selected from 1 -(4-Bromobenzyl)-1 H-indole-2,3-dione
Figure imgf000022_0001
and from its derivatives, for instance 1 -(4-Bromobenzyl)-5-(propane-2-yl)-1 H-indole-2,3- dione,1 -(4-Bromobenzyl)-5-t-butyl-1 H-indole-2,3-dione,1 -(4-Bromobenzyl)-5-iyodo-1 - -indole- 2,3-dione,1 -(4-Bromobenzyl)-2,3-dioxo-2,3-dihydro-1 - -indole-5-carbonitryl, 1 -(4- Bromobenzyl)-2,3-dioxo-2,3-dihydro-1 - -indole-5-carboxamide, Sodium 1 -(4-bromobenzyl)- 2,3-dioxo-2,3-dihydro-1 7-indole-5-sulphonate, 1 -(4-Bromobenzyl)-2,3-dioxo-2,3-dihydro-1 H- indole-5-sulphonamide, 1 -(4-Bromobenzyl)-7-metoxy-1 H-indole-2,3-dione,1 -(4-
Bromobenzyl)-5-fluoro-6-chloro-1 H-indole-2,3-dione,1 -(4-Bromobenzyl)-5-chloro-7-methyl- 1 H-indole-2,3-dione,1 -(4-Bromobenzyl)-5,7-dichloro-1 - -indole-2,3-dione.
In an application of the present invention, the compounds shown by Formula II are selected from 1 -(4-iyodobenzyl)-1 H-indole-2,3-dione
Figure imgf000022_0002
and from its derivatives, for instance 1 -(4-iyodobenzyl)- 5-(propane-2-yl)-1 H-indole-2,3- dionel -(4-iyodobenzyl)- 5-t-butyl-1 H-indole-2,3-dione,1 -(4-iyodobenzyl)-5-trifluorometoxy- 1 H-indole-2,3-dione,1 -(4-iyodobenzyl)-5-iyodo-1 7-indole-2,3-dione,1 -(4-iyodobenzyl)-5-nitro- 1 H-indole-2,3-dione,1 -(4-iyodobenzyl)-2,3-dioxo-2,3-dihydro-1 - -indole-5-carbonitryl, 1 -(4- iyodobenzyl)-2,3-dioxo-2,3-dihydro-1 7-indole-5-carboxamide, Sodium 1 -(4-iyodobenzyl)-2,3- dioxo-2,3-dihydro-1 7-indole-5-sulphonate, 1 -(4-iyodobenzyl)-2,3-dioxo-2,3-dihydro-1 H- indole-5-sulphonamide, 1 -(4-iyodobenzyl)-7-trif luoromethyl-1 H-indole-2,3-dione,1 -(4- iyodobenzyl)-7-metoxyl-1 - -indole-2,3-dione,1 -(4-iyodobenzyl)-5-chloro-7-methyl-1 H-indole- 2,3-dione,1 -(4-iyodobenzyl)-5-fluoro-6-chloro-1 7-indole-2,3-dione,1 -(4-iyodobenzyl)-5,7- dichloro-1 H-indole-2,3-dione. In an application of the present invention, the compounds shown by Formula II are selected from 1 -(4-Nitrobenzyl)-1 H-indole-2,3-dione
Figure imgf000023_0001
and from its derivatives, for instance 1-(4-Nitrobenzyl)-5-(propane-2-yl)-1H-indole-2,3- dione,1-(4-Nitrobenzyl)-5-t-butyl-1H-indole-2,3-dione,1-(4-Nitrobenzyl)-2,3-dioxo-2,3-dihydro- 1 H-indole-5-carbonitryl, 1 -(4-Nitrobenzyl)-2,3-dioxo-2,3-dihydro-1 7-indole-5-carboxamide, Sodium 1-(4-nitrobenzyl)-2,3-dioxo-2,3-dihydro-1 --indole-5-sulphonate, 1-(4-Nitrobenzyl)- 2,3-dioxo-2,3-dihydro-1 H-indole-5-sulphonamide, 1 -(4-Nitrobenzyl)-6-chloro-1 H-indole-2,3- dione,1-(4-Nitrobenzyl)-7-methyl-1H-indole-2,3-dione,1-(4-Nitrobenzyl)-7-trifluoromethyl-1H- indole-2,3-dione,1-(4-Nitrobenzyl)-7-metoxy-1 --indole-2,3-dione,1-(4-Nitrobenzyl)-7-fluoro- 1H-indole-2,3-dione,1-(4-Nitrobenzyl)-7-chloro-1H-indole-2,3-dione,1-(4-Nitrobenzyl)-5- fluoro-6-chloro-1H-indole-2,3-dione.1-(4-Nitrobenzyl)-5-chloro-7-methyl-1H-indole-2,3- dione,1 -(4-Nitrobenzyl)-5,7-dichloro-1 H-indole-2,3-dione.
In an application of the present invention, the compounds shown by Formula II are selected from 1 -(4-Cyanobenzyl)-1 H-indole-2,3-dione
Figure imgf000023_0002
and from its derivatives, for instance 1-(4-Cyanobenzyl)-5-(propane-2-yl)-1H-indole-2,3- dione,1-(4-Cyanobenzyl)-5-t-butyl-1 --indole-2,3-dione,1-(4-Cyanobenzyl)-5-metoxy-1 -- indole-2,3-dione,1-(4-Cyanobenzyl)-5-trifluorometoxy-1 --indole-2,3-dione,1-(4- Cyanobenzyl)-5-iyodo-1 H-indole-2,3-dione,1 -(4-Cyanobenzyl)-2,3-dioxo-2,3-dihydro-1 H- indole-5-carbonitryl, 1 -(4-Cyanobenzyl)-2,3-dioxo-2,3-dihydro-1 7-indole-5-carboxamide, Sodium 1 -(4-cyanobenzyl)-2,3-dioxo-2,3-dihydro-1 7-indole-5-sulphonate, 1 -(4-
Cyanobenzyl)-2,3-dioxo-2,3-dihydro-1 H-indole-5-sulphonamide, 1 -(4-Cyanobenzyl)-7- trifluoromethyl-1H-indole-2,3-dione,1-(4-Cyanobenzyl)-7-metoxy-1 H-indole-2,3-dione,1-(4- Cyanobenzyl)-5-fluoro-6-chloro-1 --indole-2,3-dione,1-(4-Cyanobenzyl)-5-chloro-7-methyl- 1H-indole-2,3-dione,1-(4-Cyanobenzyl)-5,7-dichloro-1 7-indole-2,3-dione,1-(4-Cyanobenzyl)- 5,7-dibromo-1 H-indole-2,3-dione. In an application of the present invention, the compounds shown by Formula II are selected nzyl)-1 H-indole-2,3-dione
Figure imgf000024_0001
and from its derivatives, for instance 1-(4-Ethylbenzyl)-5-(propane-2-yl)-1H-indole-2,3- dione,1-(4-Ethylbenzyl)-5-t-butyl-1 --indole-2,3-dione,1-(4-Ethylbenzyl)-5-metoxy-1 --indole- 2,3-dione,1-(4-Ethylbenzyl)-5-trifluorometoxy-1 H-indole-2,3-dione,1-(4-Ethylbenzyl)-5-iyodo- 1H-indole-2,3-dione,1-(4-Ethylbenzyl)-5-nitro-1H-indole-2,3-dione,1-(4-Ethylbenzyl)-2,3- dioxo-2,3-dihydro-1 7-indole-5-carbonitryl, 1 -(4-Ethylbenzyl)-2,3-dioxo-2,3-dihydro-1 H-indole- 5-carboxamide, Sodium 1-(4-Ethylbenzyl)-2,3-dioxo-2,3-dihydro-1 7-indole-5-sulphonate, 1- (4-Ethylbenzyl)-2,3-dioxo-2,3-dihydro-1 H-indole-5-sulphonamide, 1 -(4-Ethylbenzyl)-6-fluoro- 1H-indole-2,3-dione,1-(4-Ethylbenzyl)-7-trifluoromethyl-1H-indole-2,3-dione,1-(4- Ethylbenzyl)-7-metoxy-1 --indole-2,3-dione,1-(4-Ethylbenzyl)-5-fluoro-6-chloro-1 --indole-2,3- dione,1-(4-Ethylbenzyl)-5-chloro-7-methyl-1 H-indole-2,3-dione,1-(4-Ethylbenzyl)-5,7- dichloro-1 --indole-2,3-dione,1-(4-Ethylbenzyl)-5,7-dibromo-1 H-indole-2,3-dione.
In an application of the present invention, the compounds shown by Formula II are selected e-2-yl)benzyl]-1 H-indole-2,3-dione
Figure imgf000024_0002
and from its derivatives, for instance 1-[4-(propane-2-yl)benzyl]-5-methyl-1 H-indole-2,3- dione,1-[4-(propane-2-yl)benzyl]-5-(propane-2-yl)-1H-indole-2,3-dione,1-[4-(propane-2- yl)benzyl]-5-t-butyl-1H-indole-2,3-dione,1-[4-(propane-2-yl)benzyl]-5-metoxy-1H-indole-2,3- dione,1-[4-(propane-2-yl)benzyl]-5-trifluorometoxy-1H-indole-2,3-dione,1-[4-(propane-2- yl)benzyl]-5-fluoro-1 7-indole-2,3-dione,1-[4-(propane-2-yl)benzyl]-5-chloro-1 H-indole-2,3- dione,1-[4-(propane-2-yl)benzyl]-5-bromo-1H-indole-2,3-dione,1-[4-(propane-2-yl)benzyl]-5- iyodo-1 7-indole-2,3-dione,1-[4-(propane-2-yl)benzyl]-5-nitro-1 --indole-2,3-dione,1-[4- (propane-2-yl)benzyl]-2,3-dioxo-2,3-dihydro-1H-indole-5-carbonitryl, 1-[4-(propane-2- yl)benzyl]-2,3-dioxo-2,3-dihydro-1 H-indole-5-carboxamide, Sodium 1 -[4-(propane-2- yl)benzyl]-2,3-dioxo-2,3-dihydro-1H-indole-5-sulphonate, 1-[4-(propane-2-yl)benzyl]-2,3- dioxo-2,3-dihydro-1 H-indole-5-sulphonamide, 1 -[4-(propane-2-yl)benzyl]-6-fluoro-1 H-indole- 2,3-dione -[4-(propane-2-yl)benzyl]-6-chloro-1H-indole-2,3-dione,1-[4-(propane-2-yl)benzyl]- 6-bromo-1 H-indole-2,3-dione,1-[4-(propane-2-yl)benzyl]-7-methyl-1H-indole-2,3-dione,1-[4- (propane-2-yl)benzyl]-7-trifluoromethyl-1H-indole-2,3-dione,1-[4-(propane-2-yl)benzyl]-7- metoxy-1Hindole-2,3-dione,1-[4-(propane-2-yl)benzyl]-7-fluoro-1 --indole-2,3-dione,1-[4- (propane-2-yl)benzyl]-7-chloro-1 H-indole-2,3-dione,1 -[4-(propane-2-yl)benzyl]-7-bromo-1 H- indole-2,3-dione,1-[4-(propane-2-yl)benzyl]-5-fluoro-6-chloro-1 H-indole-2,3-dione,1-[4-
(propane-2-yl)benzyl]-5-chloro-7-methyl-1H-indole-2,3-dione,1-[4-(propane-2-yl)benzyl]-5,7- dichloro-1 --indole-2,3-dione,1-[4-(propane-2-yl)benzyl]-5,7-dibromo-1 H-indole-2,3-dione.
In an application of the present invention, the compounds shown by Formula II are selected nzyl)-1H-indole-2,3-dione
Figure imgf000025_0001
and from its derivatives, for instance 1-(4-t-butylbenzyl)-5-methyl-1H-indole-2,3-dione,1-(4-t- butylbenzyl)-5-(propane-2-yl)-1Hindole-2,3-dione,1-(4-t-butylbenzyl)-5-t-butyl-1H-indole-2,3- dione,1-(4- t-butylbenzyl)-5-metoxy-1 --indole-2,3-dione,1-(4- t-butylbenzyl)-5- trifluorometoxy-1 H-indole-2,3-dione,1-(4- t-butylbenzyl)-5-chloro-1 7-indole-2,3-dione,1-(4- t- butylbenzyl)-5-bromo-1 --indole-2,3-dione,1-(4- t-butylbenzyl)-5-iyodo-1 H-indole-2,3-dione,1- (4-t-butylbenzyl)-2,3-dioxo-2,3-dihydro-1 7-indole-5-carbonitryl, 1-(4-t-butylbenzyl)-2,3-dioxo- 2,3-dihydro-1 7-indole-5-carboxamide, Sodium 1 -(4-t-butylbenzyl)-2,3-dioxo-2,3-dihydro-1 H- indole-5-sulphonate, 1 -(4-t-butylbenzyl)-2,3-dioxo-2,3-dihydro-1 H-indole-5-sulphonamide, 1 - (4-t-butylbenzyl)-6-fluoro1H-indole-2,3-dione,1-(4-t-butylbenzyl)-6-chloro-1H-indole-2,3- dione,1-(4-t-butylbenzyl)-7-methyl-1 H-indole-2,3-dione,1-(4-t-butylbenzyl)-7-metoxy-1 -- indole-2,3-dione,1-(4-t-butylbenzyl)-7-fluoro1 --indole-2,3-dione,1-(4-t-butylbenzyl)-7-chloro- 1H-indole-2,3-dione,1-(4-t-butylbenzyl)-5-fluoro-6-chloro-1H-indole-2,3-dione,1-(4- t- butylbenzyl)-5-chloro-7-methyl-1 H-indole-2,3-dione,1 -(4-t-butylbenzyl)-5,7-dichloro-1 H- indole-2,3-dione. In an application of the present invention, the compounds shown by Formula II are selected ,3-dihydro-1 H-indole-1 -yl)methyl]benzoic acid
Figure imgf000026_0001
and from its derivatives, for instance 4-[(5-(Propane-2-yl)-2,3-dioxo-2,3-dihydro-1 H-indole-1 - yl)methyl]benzoic acid,4-[(5-t-Butyl-2,3-dioxo-2,3-dihydro-1 H-indole-1 -yl)methyl]benzoic acid,4-[(5-Metoxy-2,3-dioxo-2,3-dihydro-1 H-indole-1 -yl)methyl]benzoic acid,4-[(5- Trif luorometoxy-2,3-dioxo-2,3-dihydro-1 H-indole-1 -yl)methyl]benzoic acid,4-[(5-Chloro-2,3- dioxo-2,3-dihydro-1 H-indole-1 -yl)methyl]benzoic acid,4-[(5-Bromo-2,3-dioxo-2,3-dihydro-1 H- indole-1 -yl)methyl]benzoic acid,4-[(5-iyodo-2,3-dioxo-2,3-dihydro-1 H-indole-1 - yl)methyl]benzoic acid,4-[(5-Nitro-2,3-dioxo-2,3-dihydro-1 H-indole-1 -yl)methyl]benzoic acid,4-[(5-Cyano-2,3-dioxo-2,3-dihydro-1 H-indole-1 -yl)methyl]benzoic acid,4-[(5-Karbamoil- 2, 3-dioxo-2,3-dihydro-1 H-indole-1 -yl)methyl]benzoic acid, Sodium 1 -(4-carboxybenzyl)-2,3- dioxo-2,3-dihydro-1 H-indole-5-sulphonate, 4-[(5-Sulphamoil-2,3-dioxo-2,3-dihydro-1 H-indole- 1 -yl)methyl]benzoic acid,4-[(6-Chloro-2,3-dioxo-2,3-dihydro-1 H-indole-1 -yl)methyl]benzoic acid,4-[(6-Bromo-2,3-dioxo-2,3-dihydro-1 H-indole-1 -yl)methyl]benzoic acid,4-[(7-Methyl-2,3- dioxo-2,3-dihydro-1 H-indole-1 -yl)methyl]benzoic acid,4-[(7-Trifluoromethyl-2,3-dioxo-2,3- dihydro-1 H-indole-1 -yl)methyl]benzoic acid,4-[(7-Metoxy-2,3-dioxo-2,3-dihydro-1 H-indole-1 - yl)methyl]benzoic acid,4-[(7-Fluoro-2,3-dioxo-2,3-dihydro-1 H-indole-1 -yl)methyl]benzoic acid,4-[(7-Chloro-2,3-dioxo-2,3-dihydro-1 H-indole-1 -yl)methyl]benzoic acid,4-[(5-Fluoro-6- chloro-2,3-dioxo-2,3-dihydro-1 H-indole-1 -yl)methyl]benzoic acid,4-[(5-Chloro-7-methyl-2,3- dioxo-2,3-dihydro-1 H-indole-1 -yl)methyl]benzoic acid,4-[(5,7-Dichloro-2,3-dioxo-2,3-dihydro- 1 H-indole-1 -yl)methyl]benzoic acid.
In an application of the present invention, the compounds shown by Formula II are selected benzyl)-1 H-indole-2,3-dione
Figure imgf000026_0002
and from its derivatives, for instance 1 -(4-Hydroxybenzyl)-5-(propane-2-yl)-1 H-indole-2,3- dione,1 -(4-Hydroxybenzyl)-5-t-butyl-1 H-indole-2,3-dione,1 -(4-Hydroxybenzyl)-5- trifluorometoxy-1 H-indole-2,3-dione, 1 -(4-Hydroxybenzyl)-5-iyodo-1 - -indole-2,3-dione,1 -(4- Hydroxybenzyl)-2,3-dioxo-2,3-dihydro-1 A7-indole-5-carbonitryl, 1 -(4-Hydroxybenzyl)-2,3- dioxo-2,3-dihydro-1 H-indole-5-carboxamide, Sodium 1 -(4-hydroxybenzyl)-2,3-dioxo-2,3- dihydro-1 7-indole-5-sulphonate, 1 -(4-Hydroxybenzyl)-2,3-dioxo-2,3-dihydro-1 H-indole-5- sulphonamide, 1 -(4-Hydroxybenzyl)-7-trifluoromethyl-1 H-indole-2,3-dione,1 -(4- Hydroxybenzyl)-7-metoxy-1 H-indole-2,3-dione,1 -(4-Hydroxybenzyl)-5-fluoro-6-chloro-1 - - indole-2,3-dione,1 -(4-Hydroxybenzyl)-5-chloro-7-methyl-1 H-indole-2,3-dione,1 -(4- Hydroxybenzyl)-5,7-dichloro-1 H-indole-2,3-dione,1 -(4-Hydroxybenzyl)-5,7-dibromo-1 H- indole-2,3-dione.
In an application of the present invention, the compounds shown by Formula II are selected lbenzyl)-1 H-indole-2,3-dione
Figure imgf000027_0001
and from its derivatives, for instance 1 -(3-Methylbenzyl)-5-(propane-2-yl)-1 H-indole-2,3- dione,1 -(3-Methylbenzyl)-5-t-butyl-1 H-indole-2,3-dione,1 -(3-Methylbenzyl)-5-trifluorometoxy- 1 H-indole-2,3-dione,1 -(3-Methylbenzyl)-5-iyodo-1 H-indole-2,3-dione,1 -(3-Methylbenzyl)-2,3- dioxo-2,3-dihydro-1 H-indole-5-carbonitryl,1 -(3-Methylbenzyl)-2,3-dioxo-2,3-dihydro-1 H- indole-5-carboxamide, Sodium 1 -(3-methylbenzyl)-2,3-dioxo-2,3-dihydro-1 - -indole-5- sulphonate, 1 -(3-Methylbenzyl)-2,3-dioxo-2,3-dihydro-1 H-indole-5-sulphonamide, 1 -(3- Methylbenzyl)-7-trifluoromethyl-1 H-indole-2,3-dione, 1 -(3-Methylbenzyl)-7-metoxy-1 H-indole- 2,3-dione,1 -(3-Methylbenzyl)-5-fluoro-6-chloro-1 H-indole-2,3-dione,1 -(3-Methylbenzyl)-5- chloro-7-methyl-1 H-indole-2,3-dione,1 -(3-Methylbenzyl)-5,7-dichloro-1 - -indole-2,3-dione,1 - (3-Methylbenzyl)-5,7-dibromo-1 H-indole-2,3-dione.
In an application of the present invention, the compounds shown by Formula II are selected from 1 -(3-Trif luoromethylbenzyl)-1 H-indole-2,3-dione
Figure imgf000028_0001
and from its derivatives, for instance 1-(3-Trifluoromethylbenzyl)-5-(propane-2-yl)-1H-indole- 2,3-dione,1-(3-Trifluoromethylbenzyl)-5-t-butyl-1H-indole-2,3-dione,1-(3- Trifluoromethylbenzyl)-5-metoxy-1 --indole-2,3-dione,1-(3-Trifluoromethylbenzyl)-5- trifluorometoxy-1 H-indole-2,3-dione,1-(3-Trifluoromethylbenzyl)-5-bromo-1 --indole-2,3- dione,1-(3-Trifluoromethylbenzyl)-2,3-dioxo-2,3-dihydro-1 --indole-5-carbonitryl,1-(3- Trif luoromethylbenzyl)-2,3-dioxo-2,3-dihydro-1 7-indole-5-carboxamide, sodium 1 -(3- trifluoromethylbenzyl)-2,3, dioxo-2,3-dihydro-1 7-indole-5-sulphonate, 1 -(3-
Trif luoromethylbenzyl)-2,3-dioxo-2,3-dihydro-1 H-indole-5-sulphonamide, 1 -(3- Trifluoromethylbenzyl)-6-fluoro-1 --indole-2,3-dione,1-(3-Trifluoromethylbenzyl)-6-chloro-1 -- indole-2,3-dione,1-(3-Trifluoromethylbenzyl)-6-bromo-1 --indole-2,3-dione,1-(3- Trifluoromethylbenzyl)-7-trifluoromethyl-1H-indole-2,3-dione,1-(3-Trifluoromethylbenzyl)-7- metoxy-1 --indole-2,3-dione,1-(3-Trifluoromethylbenzyl)-7-bromo-1 --indole-2,3-dione.1-(3- Trifluoromethylbenzyl)-5-fluoro-6-chloro-1 --indole-2,3-dione,1-(3-Trifluoromethylbenzyl)-5- chloro-7-methyl-1H-indole-2,3-dione,1-(3-Trifluoromethylbenzyl)-5,7-dichloro-1 H-indole-2,3- dione,1-(3-Trifluoromethylbenzyl)-5,7-dibromo-1 --indole-2,3-dione.
In an application of the present invention, the compounds shown by Formula II are selected enzyl)-1 H-indole-2,3-dione
Figure imgf000028_0002
and from its derivatives, for instance 1-(3-Metoxybenzyl)-5-(propane-2-yl)-1H-indole-2,3- dione,1-(3-Metoxybenzyl)-5-t-butyl-1 H-indole-2,3-dione,1-(3-Metoxybenzyl)-5-metoxy-1 7- indole-2,3-dione,1-(3-Metoxybenzyl)-5-iyodo-1 --indole-2,3-dione,1-(3-Metoxybenzyl)-5-nitro- 1H-indole-2,3-dione,1-(3-Metoxybenzyl)-2,3-dioxo-2,3-dihydro-1 --indole-5-carbonitryl, Sodium 1 -(3-metoxybenzyl)-2,3-dioxo-2,3-dihydro-1 7-indole-5-sulphonate, 1 -(3- Metoxybenzyl)-2,3-dioxo-2,3-dihydro-1 Hindole-5-sulphonamide, 1 -(3-Metoxybenzyl)-7- trifluoromethyl-1 H-indole-2,3-dione -(3-Metoxybenzyl)-7-metoxy-1 Hindole-2,3-dione,1 -(3- Metoxybenzyl)-5 luoro-6-chloro-1 Hindole-2,3-dione -(3-Metoxybenzyl)-5-chloro-7-methyl- 1 H-indole-2,3-dione,1 -(3-Metoxybenzyl)-5,7-dichloro-1 H-indole-2,3-dione.
In an application of the present invention, the compounds shown by Formula II are selected ometoxybenzyl)-1 H-indole-2,3-dione
Figure imgf000029_0001
and from its derivatives, for instance 1 -(3-Trifluorometoxybenzyl)-1 H-indole-2,3-dione,1 -(3- Trifluorometoxybenzyl)-5-methyl-1 H-indole-2,3-dione,1 -(3-Trif luorometoxybenzyl)-5- (propane-2-yl)-1 H-indole-2,3-dione,1 -(3-Trifluorometoxybenzyl)-5-t-butyl-1 - -indole-2,3- dione,1 -(3-Trifluorometoxybenzyl)-5-metoxy-1 - -indole-2,3-dione,1 -(3- Trifluorometoxybenzyl)-5-trifluorometoxy-1 H-indole-2,3-dione,1 -(3-Trif luorometoxybenzyl)-5- fluoro-1 H-indole-2,3-dione,1 -(3-Trifluorometoxybenzyl)-5-chloro-1 - -indole-2,3-dione,1 -(3- Trifluorometoxybenzyl)-5-bromo-1 H-indole-2,3-dione,1 -(3-Trif luorometoxybenzyl)-5-iyodo- 1 H-indole-2,3-dione,1 -(3-Trifluorometoxybenzyl)-5-nitro-1 H-indole-2,3-dione,1 -(3- Trifluorometoxybenzyl)-2,3-dioxo-2,3-dihydro-1 7-indole-5-carbonitryl,1 -(3- Trif luorometoxybenzyl)-2,3-dioxo-2,3-dihydro-1 7-indole-5-carboxamide, Sodium 1 -(3- trifluorometoxybenzyl)-2,3-dioxo-2,3-dihydro-1 7-indole-5-sulphonate, 1 -(3-
Trif luorometoxybenzyl)-2,3-dioxo-2,3-dihydro-1 H-indole-5-sulphonamide, 1 -(3-
Trifluorometoxybenzyl)-6-fluoro-1 H-indole-2,3-dione,1 -(3-Trif luorometoxybenzyl)-6-chloro- 1 H-indole-2,3-dione,1 -(3-Trifluorometoxybenzyl)-7-methyl-1 H-indole-2,3-dione. 1 -(3- Trifluorometoxybenzyl)-7-trifluoromethyl-1 H-indole-2,3-dione. 1 -(3-Trifluorometoxybenzyl)-7- metoxy-1 - -indole-2,3-dione,1 -(3-Trifluorometoxybenzyl)-7-fluoro-1 - -indole-2,3-dione,1 -(3- Trifluorometoxybenzyl)-7-chloro-1 H-indole-2,3-dione,1 -(3-Trif luorometoxybenzyl)-7-bromo- 1 H-indole-2,3-dione,1 -(3-Trifluorometoxybenzyl)-5-fluoro-6-chloro-1 - -indole-2,3-dione,1 -(3- Trifluorometoxybenzyl)-5-chloro-7-methyl-1 H-indole-2,3-dione,1 -(3-Trif luorometoxybenzyl)- 5,7-dichloro-1 H-indole-2,3-dione,1 -(3-Trifluorometoxybenzyl)-5,7-dibromo-1 - -indole-2,3- dione. In an application of the present invention, the compounds shown by Formula II are selected benzyl)-1 H-indole-2,3-dione
Figure imgf000030_0001
and from its derivatives, for instance 1 -(3-Fluorobenzyl)-5-(propane-2-yl)-1 H-indole-2,3- dione,1 -(3-Fluorobenzyl)-5-t-butyl-1 H-indole-2,3-dione,1 -(3-Fluorobenzyl)-5-trifluorometoxy- 1 H-indole-2,3-dione,1 -(3-Fluorobenzyl)-5-iyodo-1 H-indole-2,3-dione,1 -(3-Fluorobenzyl)-2,3- dioxo-2,3-dihydro-1 7-indole-5-carbonitryl, 1 -(3-Fluorobenzyl)-2,3-dioxo-2,3-dihydro-1 H- indole-5-carboxamide, Sodium 1 -(3-f luorobenzyl)-2,3-dioxo-2,3-dihydro-1 H-indole-5- sulphonate, 1 -(3-Fluorobenzyl)-7-trifluoromethyl-1 H-indole-2,3-dione, 1 -(3-Fluorobenzyl)-7- metoxy-1 - -indole-2,3-dione,1 -(3-Fluorobenzyl)-5-fluoro-6-chloro-1 H-indole-2,3-dione,1 -(3- Fluorobenzyl)-5-chloro-7-methyl-1 H-indole-2,3-dione,1 -(3-Fluorobenzyl)-5,7-dichloro-1 H- indole-2,3-dione.
In an application of the present invention, the compounds shown by Formula II are selected enzyl)-1 H-indole-2,3-dione
Figure imgf000030_0002
and from its derivatives, for instance 1 -(3-Chlorobenzyl)-5-(propane-2-yl)-1 H-indole-2,3- dione,1 -(3-Chlorobenzyl)-5-t-butyl-1 H-indole-2,3-dione,1 -(3-Chlorobenzyl)-5-trifluorometoxy- 1 H-indole-2,3-dione,1 -(3-Chlorobenzyl)-2,3-dioxo-2,3-dihydro-1 H-indole-5-carbonitryl, 1 -(3- Chlorobenzyl)-2,3-dioxo-2,3-dihydro-1 7-indole-5-carboxamide, Sodium 1 -(3-chlorobenzyl)- 2,3-dioxo-2,3-dihydro-1 H-indole-5-sulphonate, 1 -(3-Chlorobenzyl)-2,3-dioxo-2,3-dihydro-1 H- indole-5-sulphonamide, 1 -(3-Chlorobenzyl)-7-metoxy-1 H-indole-2,3-dione,1 -(3-
Chlorobenzyl)-5-fluoro-6-chloro-1 H-indole-2,3-dione,1 -(3-Chlorobenzyl)-5-chloro-7-methyl- 1H-indole-2,3-dione,1-(3-Chlorobenzyl)-57-dichloro-1H-indole-2,3-dione,1-(3-Chlo
5,7-dibromo-1 H-indole-2,3-dione.
In an application of the present invention, the compounds shown by Formula II are selected mobenzyl)-1H-indole-2,3-dione
Figure imgf000031_0001
and from its derivatives, for instance 1-(3-Bromobenzyl)-5-(propane-2-yl)-1H-indole-2,3- dione,1-(3-Bromobenzyl)-5-t-butyl-1 H-indole-2,3-dione,1-(3-Bromobenzyl)-5-trifluorometoxy- 1H-indole-2,3-dione,1-(3-Bromobenzyl)-5-iyodo-1 --indole-2,3-dione,1-(3-Bromobenzyl)-5- nitro-1 7-indole-2,3-dione,1-(3-Bromobenzyl)-2,3-dioxo-2,3-dihydro-1 7-indole-5-carbonitryl, 1 -(3-Bromobenzyl)-2,3-dioxo-2,3-dihydro-1 7-indole-5-carboxamide, Sodium 1 -(3- bromobenzyl)-2,3-dioxo-2,3-dihydro-1 7-indole-5-sulphonate, 1 -(3-Bromobenzyl)-2,3-dioxo- 2,3-dihydro-1 H-indole-5-sulphonamide, 1 -(3-Bromobenzyl)-7-trifluoromethyl-1 H-indole-2,3- dione,1-(3-Bromobenzyl)-7-metoxy-1 H-indole-2,3-dione,1-(3-Bromobenzyl)-5-fluoro-6-chloro- 1H-indole-2,3-dione,1-(3-Bromobenzyl)-5-chloro-7-methyl-1H-indole-2,3-dione,1-(3-
Bromobenzyl)-5,7-dichloro-1 H-indole-2,3-dione,1 -(3-Bromobenzyl)-5,7-dibromo-1 H-indole- 2,3-dione.
In an application of the present invention, the compounds shown by Formula II are selected from 1 -(3-iyodobenzyl)-1 H-indole-2,3-dione
Figure imgf000031_0002
and from its derivatives, for instance 1-(3-iyodobenzyl)-5-methyl-1H-indole-2,3-dione,1-(3- lyodobenzyl)-5-(propane-2-yl)-1H-indole-2,3-dione,1-(3-iyodobenzyl)-5-t-butyl-1H-indole-2,3- dione,1-(3-iyodobenzyl)-5-metoxy-1 H-indole-2,3-dione,1-(3-iyodobenzyl)-5-trifluorometoxy- 1H-indole-2,3-dione,1-(3-iyodobenzyl)-5-fluoro-1 --indole-2,3-dione,1-(3-iyodobenzyl)-5- chloro-1 H-indole-2,3-dione,1-(3-iyodobenzyl)-5-bromo-1 --indole-2,3-dione,1-(3- iyodobenzyl)-5-iyodo-1Hindole-2,3-dione,1-(3-iyodobenzyl)-5-nitro-1 H-indole-2,3-dione,1-(3- iyodobenzyl)-2,3-dioxo-2,3-dihydro-1 --indole-5-carbonitryl, 1 -(3-iyodobenzyl)- 2,3-dioxo-2,3- dihydro-1 --indole-5-carboxamide, Sodium 1 -(3-iyodobenzyl)- 2,3-dioxo-2,3-dihydro-1 H- indole-5-sulphonate, 1 -(3-iyodobenzyl)- 2,3-dioxo-2,3-dihydro-1Hindole-5-sulphonamide, 1- (3-iyodobenzyl)-6-fluoro-1H-indole-2,3-dione,1-(3-iyodobenzyl)-6-chloro-1H-indole-2,3- dione,1-(3-iyodobenzyl)-6-bromo-1 --indole-2,3-dione,1-(3-iyodobenzyl)-7-methyl-1 H-indole- 2,3-dione,1-(3-iyodobenzyl)-7-trifluoromethyl-1H-indole-2,3-dione,1-(3-iyodobenzyl)-7- metoxy-1 --indole-2,3-dione,1-(3-iyodobenzyl)-7-fluoro-1 --indole-2,3-dione,1-(3- iyodobenzyl)-7-chloro-1 --indole-2,3-dione,1-(3-iyodobenzyl)-5-fluoro-6-chloro-1 --indole-2,3- dione,1-(3-iyodobenzyl)-5-chloro-7-methyl-1 H-indole-2,3-dione,1-(3-iyodobenzyl)-5,7- dichloro-1 --indole-2,3-dione,1-(3-iyodobenzyl)-5,7-dibromo-1 H-indole-2,3-dione.
In an application of the present invention, the compounds shown by Formula II are selected from 1 -(3-Nitrobenzyl)-1 H-indole-2,3-dione
Figure imgf000032_0001
and from its derivatives, for instance 1-(3-Nitrobenzyl)-5-(propane-2-yl)-1H-indole-2,3- dione,1-(3-Nitrobenzyl)-5-t-butyl-1 --indole-2,3-dione,1-(3-Nitrobenzyl)-5-trifluorometoxy-1 7- indole-2,3-dione,1-(3-Nitrobenzyl)-5-chloro-1 7-indole-2,3-dione,1-(3-Nitrobenzyl)-5-iyodo- 1H-indole-2,3-dione,1-(3-Nitrobenzyl)-2,3-dioxo-2,3-dihydro-1H-indole-5-carbonitryl, 1-(3- Nitrobenzyl)-2,3-dioxo-2,3-dihydro-1 7-indole-5-carboxamide, Sodium 1-(3-nitrobenzyl)-2,3- dioxo-2,3-dihydro-1 7-indole-5-sulphonate, 1 -(3-Nitrobenzyl)-2,3-dioxo-2,3-dihydro-1 H-indole- 5-sulphonamide, 1-(3-Nitrobenzyl)-6-chloro-1 H-indole-2,3-dione,1-(3-Nitrobenzyl)-6-bromo- 1H-indole-2,3-dione,1-(3-Nitrobenzyl)-7-trifluoromethyl-1H-indole-2,3-dione,1-(3-Nitrobenzyl)- 7-metoxy-1 H-indole-2,3-dione,1 -(3-Nitrobenzyl)-7-fluoro-1 H-indole-2,3-dione,1 -(3- Nitrobenzyl)-7-chloro-1 --indole-2,3-dione,1-(3-Nitrobenzyl)-7-bromo-1 --indole-2,3-dione,1- (3-Nitrobenzyl)-5-fluoro-6-chloro-1 H-indole-2,3-dione 1 -(3-Nitrobenzyl)-5-chloro-7-methyl-1 H- indole-2,3-dione,1-(3-Nitrobenzyl)-5,7-dichloro-1H-indole-2,3-dione,1-(3-Nitrobenzyl)-5,7- dibromo-1 H-indole-2,3-dione. In an application of the present invention, the compounds shown by Formula II are selected from 1 -(3-Cyanobenzyl)-1 H-indole-2,3-dione
Figure imgf000033_0001
and from its derivatives, for instance 1-(3-Cyanobenzyl)-5-(propane-2-yl)-1H-indole-2,3- dione,1-(3-Cyanobenzyl)-5-t-butyl-1H-indole-2,3-dione,1-(3-Cyanobenzyl)-5-metoxy-1H- indole-2,3-dione,1-(3-Cyanobenzyl)-5-trifluorometoxy-1 --indole-2,3-dione,1-(3- Cyanobenzyl)-5-iyodo-1 --indole-2,3-dione,1-(3-Cyanobenzyl)-5-nitro-1 H-indole-2,3-dione,1- (3-Cyanobenzyl)-2,3-dioxo-2,3-dihydro-1 H-indole-5-carbonitryl, 1 -(3-Cyanobenzyl)-2,3-dioxo- 2,3-dihydro-1 7-indole-5-carboxamide, Sodium 1 -(3-cyanobenzyl)-2,3-dioxo-2,3-dihydro-1 H- indole-5-sulphonate, 1 -(3-Cyanobenzyl)-2,3-dioxo-2,3-dihydro-1 H-indole-5-sulphonamide, 1 - (3-Cyanobenzyl)-7-trifluoromethyl-1 H-indole-2,3-dione,1-(3-Cyanobenzyl)-7-metoxy-1 -- indole-2,3-dione,1-(3-Cyanobenzyl)-5-fluoro-6-chloro-1H-indole-2,3-dione,1-(3-
Cyanobenzyl)-5-chloro-7-methyl-1H-indole-2,3-dione,1-(3-Cyanobenzyl)-5,7-dichloro-1 H- indole-2,3-dione,1-(3-Cyanobenzyl)-5,7-dibromo-1 H-indole-2,3-dione.
In an application of the present invention, the compounds shown by Formula II are selected from 1-(3-Ethylbenzyl)-1H-indole-2,3-dione
Figure imgf000033_0002
and from its derivatives, for instance 1-(3-Ethylbenzyl)-1H-indole-2,3-dione,1-(3-Ethylbenzyl)- 5-methyl-1H-indole-2,3-dione,1-(3-Ethylbenzyl)-5-(propane-2-yl)-1H-indole-2,3-dione,1-(3- Ethylbenzyl)-5-t-butyl-1H-indole-2,3-dione,1-(3-Ethylbenzyl)-5-metoxy-1H-indole-2,3-dione,1- (3-Ethylbenzyl)-5-trifluorometoxy-1 --indole-2,3-dione,1-(3-Ethylbenzyl)-5-fluoro-1 --indole- 2,3-dione,1-(3-Ethylbenzyl)-5-chloro-1H-indole-2,3-dione,1-(3-Ethylbenzyl)-5-bromo-1H- indole-2,3-dione,1-(3-Ethylbenzyl)-5-iyodo-1H-indole-2,3-dione,1-(3-Ethylbenzyl)-5-nitro-1H- indole-2,3-dione,1-(3-Ethylbenzyl)-2,3-dioxo-2,3-dihydro-1H-indole-5-carbonitryl, 1-(3- Ethylbenzyl)-2,3-dioxo-2,3-dihydro-1 7-indole-5-carboxamide, Sodium 1 -(3-ethylbenzyl)-2,3- dioxo-2,3-dihydro-1 7-indole-5-sulphonate, 1 -(3-Ethylbenzyl)-2,3-dioxo-2,3-dihydro-1 H- indole-5-sulphonamide, 1 -(3-Ethylbenzyl)-6-fluoro-1 7-indole-2,3-dione,1 -(3-Ethylbenzyl)-6- chloro-1 H-indole-2,3-dione -(3-Ethylbenzyl)-6-bromo-1 H-indole-2,3-dione -(3-Eth
7-methyl-1 H-indole-2,3-dione,1 -(3-Ethylbenzyl)-7-trifluoromethyl-1 H-ind
Ethylbenzyl)-7-metoxy-1 H-indole-2,3-dione,1 -(3-Ethylbenzyl)-7-fluoro-1 H-indole-2,3-di (3-Ethylbenzyl)-7-chloro-1 H-indole-2,3-dione,1 -(3-E ^
dione,1 -(3-Ethylbenzyl)-5-fluoro-6-chloro-1 H-indole-2,3-dione,1 -(3-Ethylbenzyl)-5-chloro-7- methyl-1 H-indole-2,3-dione,1 -(3-Ethylbenzyl)-5,7-dichloro-1 H-indole-2,3-dione. In an application of the present invention, the compounds shown by Formula II are selected from 1 -[3-(Propane-2-yl)benzyl]-1 H-indole-2,3-dione
Figure imgf000034_0001
and from its derivatives, for instance 1 -[3-(Propane-2-yl)benzyl]-1 H-indole-2,3-dione,1 -[3- (Propane-2-yl)benzyl]-5-methyl-1 H-indole-2,3-dione,1 -[3-(Propane-2-yl)benzyl]-5-(propane-2- yl)-1 H-indole-2,3-dione,1 -[3-(Propane-2-yllbenzyl]-5-t-butyl-1 H-indole-2,3-dione,1 -[3- (Propane-2-yl)benzyl]-5-metoxy-1 H-indole-2,3-dione,1 -[3-(Propane-2-yl)benzyl]-5- trifluorometoxy-1 H-indole-2,3-dione, 1 -[3-(Propane-2-yl)benzyl]-5-fluoro-1 - -indole-2,3- dione,1 -[3-(Propane-2-yl)benzyl]-5-chloro-1 H-indole-2,3-dione,1 -[3-(Propane-2-yl)benzyl]-5- iyodo-1 H-indole-2,3-dione,1 -[3-(Propane-2-yl)benzyl]-5-nitro-1 H-indole-2,3-dione,1 -[3- (Propane-2-yl)benzyl]-2,3-dioxo-2,3-dihydro-1 H-indole-5-carbonitryl, 1 -[3-(Propane-2- yl)benzyl]-2,3-dioxo-2,3-dihydro-1 H-indole-5-carboxamide, Sodium 1 -[3-(propane-2- yl)benzyl]-2,3-dioxo-2,3-dihydro-1 H-indole-5-sulphonate, 1 -[3-(Propane-2-yl)benzyl]-2,3- dioxo-2,3-dihydro-1 H-indole-5-sulphonamide, 1 -[3-(Propane-2-yl)benzyl]-6-fluoro-1 H-indole- 2,3-dione,1 -[3-(Propane-2-yl)benzyl]-6-chloro-1 H-indole-2,3-dione,1 -[3-(Propane-2- yl)benzyl]-6-bromo-1 H-indole-2,3-dione,1 -[3-(Propane-2-yl)benzyl]-7-methyl-1 H-indole-2,3- dione,1 -[3-(Propane-2-yl)benzyl]-7-trifluoromethyl-1 H-indole-2,3-dione,1 -[3-(Propane-2- yl)benzyl]-7-metoxy-1 - -indole-2,3-dione,1 -[3-(Propane-2-yl)benzyl]-7-fluoro-1 H-indole-2,3- dione,1 -[3-(Propane-2-yl)benzyl]-7-chloro-1 7-indole-2,3-dione,1 -[3-(Propane-2-yl)benzyl]-7- bromo-1 H-indole-2,3-dione,1 -[3-(Propane-2-yl)benzyl]-5-fluoro-6-chloro-1 H-indole-2,3- dione,1 -[3-(Propane-2-yl)benzyl]-5-chloro-7-methyl-1 H-indole-2,3-dione,1 -[3-(Propane-2- yl)benzyl]-5,7-dichloro-1Hindole-2,3-dione,1-[3-(Propane-2-yl)benzyl]^ indole-2,3-dione.
In an application of the present invention, the compounds shown by Formula II are selected benzyl)-1H-indole-2,3-dione
Figure imgf000035_0001
and from its derivatives, for instance 1-(3-t-Butylbenzyl)-1H-indole-2,3-dione,1-(3-t- Butylbenzyl)-5-methyl-1 H-indole-2,3-dione,1-(3-t-Butylbenzyl)-5-(propane-2-yl)-1H-indole- 2,3-dione,1-(3-t-Butylbenzyl)-5-t-butyl-1H-indole-2,3-dione,1-(3-t-Butylbenzyl)-5-metoxy-1H- indole-2,3-dione,1-(3-t-Butylbenzyl)-5-trifluorometoxy-1H-indole-2,3-dione,1-(3-t-
Butylbenzyl)-5 luoro-1H-indole-2,3-dione,1-(3-t-Butylbenzyl)-5-chloro-1H-indole-2,3-dione,1- (3-t-Butylbenzyl)-5-bromo-1H-indole-2,3-dione,1-(3-t-Butylbenzyl)-5-iyodo-1H-indole-2,3- dione,1-(3-t-Butylbenzyl)-2,3-dioxo-2,3-dihydro-1H-indole-5-carbonitryl, 1-(3-t-Butylbenzyl)- 2,3-dioxo-2,3-dihydro-1 7-indole-5-carboxamide, Sodium 1 -(3-t-butylbenzyl)-2,3-dioxo-2,3- dihydro-1 H-indole-5-sulphonate, 1 -(3-t-Butylbenzyl)-2,3-dioxo-2,3-dihydro-1 H-indole-5- sulphonamide, 1-(3-t-Butylbenzyl)-6-fluoro-1 H-indole-2,3-dione,1-(3-t-Butylbenzyl)-6-chloro- 1H-indole-2,3-dione,1-(3-t-Butylbenzyl)-6-bromo-1H-indole-2,3-dione,1-(3-t-Butylbenzyl)-7- methyl-1H-indole-2,3-dione,1-(3-t-Butylbenzyl)-7-trifluoromethyl-1H-indole-2,3-dione,1-(3-t- Butylbenzyl)-7-metoxy-1H-indole-2,3-dione,1-(3-t-Butylbenzyl)-7-fluoro-1H-indole-2,3- dione,1-(3-t-Butylbenzyl)-7-chloro-1H-indole-2,3-dione,1-(3-t-Butylbenzyl)-7-bromo-1H- indole-2,3-dione,1-(3-t-Butylbenzyl)-5-fluoro-6-chloro-1H-indole-2,3-dione,1-(3-t-Butylbenzyl)- 5-chloro-7-methyl-1H-indole-2,3-dione,1-(3-t-Butylbenzyl)-5,7-dichloro-1H-indole-2,3-dione,1- (3-t-Butylbenzyl)-5,7-dibromo-1H-indole-2,3-dione. In an application of the present invention, the compounds shown by Formula II are selected from 3-[(2,3-dioxo-2,3-dihydro-1 H-indole-1 -yl)methyl]benzoic acid
Figure imgf000036_0001
and from its derivatives, for instance 3-[(5-(Propane-2-yl)-2,3-dioxo-2,3-dihydro-1 H-indole-1 - yl)methyl]benzoic acid,3-[(5-t-Butyl-2,3-dioxo-2,3-dihydro-1 H-indole-1 -yl)methyl]benzoic acid,3-[(5-Metoxy-2,3-dioxo-2,3-dihydro-1 H-indole-1 -yl)methyl]benzoic acid,3-[(5- Trif luorometoxy-2,3-dioxo-2,3-dihydro-1 H-indole-1 -yl)methyl]benzoic acid,3-[(5-Chloro-2,3- dioxo-2,3-dihydro-1 H-indole-1 -yl)methyl]benzoic acid,3-[(5-Bromo-2,3-dioxo-2,3-dihydro-1 H- indole-1 -yl)methyl]benzoic acid,3-[(5-iyodo-2,3-dioxo-2,3-dihydro-1 H-indole-1 - yl)methyl]benzoic acid,3-[(5-Nitro-2,3-dioxo-2,3-dihydro-1 H-indole-1 -yl)methyl]benzoic acid,3-[(5-Cyano-2,3-dioxo-2,3-dihydro-1 H-indole-1 -yl)methyl]benzoic acid,3-[(5-Karbamoil- 2,3-dioxo-2,3-dihydro-1 H-indole-1 -yl)methyl]benzoic acid,3-[(5-Cyano-2,3-dioxo-2,3-dihydro- 1 H-indole-1 -yl)methyl]benzoic acid, Sodium 1 -(3-carboxybenzyl)-2,3-dioxo-2,3-dihydro-1 H- indole-5-sulphonate, 3-[(5-Sulphamoil-2,3-dioxo-2,3-dihydro-1 H-indole-1 -yl)methyl]benzoic acid,3-[(6-Chloro-2,3-dioxo-2,3-dihydro-1 H-indole-1 -yl)methyl]benzoic acid,3-[(6-Bromo-2,3- dioxo-2,3-dihydro-1 H-indole-1 -yl)methyl]benzoic acid,3-[(7-Methyl-2,3-dioxo-2,3-dihydro-1 H- indole-1 -yl)methyl]benzoic acid,3-[(7-Trif luoromethyl-2,3-dioxo-2,3-dihydro-1 H-indole-1 - yl)methyl]benzoic acid,3-[(7-Trifluoromethyl-2,3-dioxo-2,3-dihydro-1 H-indole-1 - yl)methyl]benzoic acid,3-[(7-Metoxy-2,3-dioxo-2,3-dihydro-1 H-indole-1 -yl)methyl]benzoic acid, 3-[(7-Chloro-2,3-dioxo-2,3-dihydro-1 H-indole-1 -yl)methyl]benzoic acid,3-[(7-Bromo-2,3- dioxo-2,3-dihydro-1 H-indole-1 -yl)methyl]benzoic acid, 3-[(5-Fluoro-6-chloro-2,3-dioxo-2,3- dihydro-1 H-indole-1 -yl)methyl]benzoic acid,3-[(5-Chloro-7-methyl-2,3-dioxo-2,3-dihydro-1 H- indole-1 -yl)methyl]benzoic acid,3-[(5,7-Dichloro-2,3-dioxo-2,3-dihydro-1 H-indole-1 - yl)methyl]benzoic acid,3-[(5,7-Dibromo-2,3-dioxo-2,3-dihydro-1 H-indole-1 -yl)methyl]benzoic acid. In an application of the present invention, the compounds shown by Formula II are selected from 1 -(3-Hydroxybenzyl)-1 H-indole-2,3-dione
Figure imgf000037_0001
and from its derivatives, for instance 1 -(3-Hydroxybenzyl)-5-(propane-2-yl)-1 H-indole-2,3- dione,1 -(3-Hydroxybenzyl)-5-t-butyl-1 H-indole-2,3-dione,1 -(3-Hydroxybenzyl)-5- trifluorometoxy-1 H-indole-2,3-dione, 1 -(3-Hydroxybenzyl)-5-iyodo-1 - -indole-2,3-dione,1 -(3- Hydroxybenzyl)-5-nitro-1 - -indole-2,3-dione,1 -(3-Hydroxybenzyl)-2,3-dioxo-2,3-dihydro-1 H- indole-5-carbonitryl, Sodium 1 -(3-hydroxybenzyl)-2,3-dioxo-2,3-dihydro-1 H-indole-5- sulphonate, 1 -(3-Hydroxybenzyl)-2,3-dioxo-2,3-dihydro-1 H-indole-5-sulphonamide, 1 -(3- Hydroxybenzyl)-7-trifluoromethyl-1 H-indole-2,3-dione,1 -(3-Hydroxybenzyl)-7-metoxy-1 - - indole-2,3-dione,1 -(3-Hydroxybenzyl)-5-fluoro-6-chloro-1 - -indole-2,3-dione,1 -(3- Hydroxybenzyl)-5-chloro-7-methyl-1 H-indole-2,3-dione,1 -(3-Hydroxybenzyl)-5,7-dichloro-1 H- indole-2,3-dione,1 -(3-Hydroxybenzyl)-5,7-dibromo-1 - -indole-2,3-dione.
In an application of the present invention, the compounds shown by Formula II are selected hylbenzyl)-1 H-indole-2,3-dione
Figure imgf000037_0002
and from its derivatives, for instance 1 -(2-Methylbenzyl)-5-(propane-2-yl)-1 H-indole-2,3- dione,1 -(2-Methylbenzyl)-5-t-butyl-1 H-indole-2,3-dione,1 -(2-Methylbenzyl)-5-iyodo-1 H-indole- 2,3-dione,1 -(2-Methylbenzyl)-2,3-dioxo-2,3-dihydro-1 H-indole-5-carbonitryl, 1 -(2- Methylbenzyl)-2,3-dioxo-2,3-dihydro-1 7-indole-5-carboxamide, Sodium 1 -(2-methylbenzyl)- 2,3-dioxo-2,3-dihydro-1 H-indole-5-sulphonate, 1 -(2-Methylbenzyl)-2,3-dioxo-2,3-dihydro-1 H- indole-5-sulphonamide, 1 -(2-Methylbenzyl)-7-trif luoromethyl-1 H-indole-2,3-dione,1 -(2-
Methylbenzyl)-7-metoxy-1 - -indole-2,3-dione,1 -(2-Methylbenzyl)-5-fluoro-6-chloro-1 H-indole- 2,3-dione,1 -(2-Methylbenzyl)-5-chloro-7-methyl-1 H-indole-2,3-dione,1 -(2-Methylbenzyl)-5,7- dichloro-1 - -indole-2,3-dione,1 -(2-Methylbenzyl)-5,7-dibromo-1 - -indole-2,3-dione.
In an application of the present invention, the compounds shown by Formula II are selected from 1 -(2-Trif luoromethylbenzyl)-1 H-indole-2,3-dione
Figure imgf000038_0001
and from its derivatives, for instance 1-(2-Trifluoromethylbenzyl)-5-(propane-2-yl)-1H-indole- 2,3-dione,1-(2-Trifluoromethylbenzyl)-5-t-butyl-1H-indole-2,3-dione,1-(2- Trifluoromethylbenzyl)-5-metoxy-1 --indole-2,3-dione,1-(2-Trifluoromethylbenzyl)-5-bromo- 1H-indole-2,3-dione,1-(2-Trifluoromethylbenzyl)-5-iyodo-1 H-indole-2,3-dione,1-(2-
Trifluoromethylbenzyl)-5-nitro-1 H-indole-2,3-dione,1-(2-Trifluoromethylbenzyl)-2,3-dioxo-2,3- dihydro-1 --indole-5-carbonitryl, 1 -(2-Trifluoromethylbenzyl)-2,3-dioxo-2,3-dihydro-1 H-indole- 5-carboxamide, Sodium 1 -(2-trifluoromethylbenzyl)-2,3-dioxo-2,3-dihydro-1 H-indole-5- sulphonate, 1 -(2-Trifluoromethylbenzyl)-2,3-dioxo-2,3-dihydro-1 H-indole-5-sulphonamide, 1 - (2-Trifluoromethylbenzyl)-6-fluoro-1 --indole-2,3-dione,1-(2-Trifluoromethylbenzyl)-6-chloro- 1H-indole-2,3-dione,1-(2-Trifluoromethylbenzyl)-6-bromo-1 --indole-2,3-dione,1-(2- Trifluoromethylbenzyl)-7-methyl-1 H-indole-2,3-dione,1-(2-Trifluoromethylbenzyl)-7- trifluoromethyl-1H-indole-2,3-dione,1-(2-Trifluoromethylbenzyl)-7-metoxy-1 H-indole-2,3- dione,1-(2-Trifluoromethylbenzyl)-7-bromo-1 --indole-2,3-dione,1-(2-Trifluoromethylbenzyl)- 5-fluoro-6-chloro-1 H-indole-2,3-dione,1-(2-Trifluoromethylbenzyl)-5-chloro-7-methyl-1H- indole-2,3-dione,1-(2-Trifluoromethylbenzyl)-5,7-dichloro-1 H-indole-2,3-dione,1-(2- Trifluoromethylbenzyl)-5,7-dibromo-1 --indole-2,3-dione.
In an application of the present invention, the compounds shown by Formula II are selected from 1-(2-Metoxybenzyl)-1H-indole-2,3-dione
Figure imgf000038_0002
and from its derivatives, for instance 1-(2-Metoxybenzyl)-5-(propane-2-yl)-1H-indole-2,3- dione,1-(2-Metoxybenzyl)-5-t-butyl-1 H-indole-2,3-dione,1-(2-Metoxybenzyl)-5-metoxy-1 H- indole-2,3-dione,1-(2-Metoxybenzyl)-5-trifluorometoxy-1 H-indole-2,3-dione,1-(2- Metoxybenzyl)-5-iyodo-1 H-indole-2,3-dione,1-(2-Metoxybenzyl)-5-nitro-1 --indole-2,3- dione,1-(2-Metoxybenzyl)-2,3-dioxo-2,3-dihydro-1 7-indole-5-carbonitryl, 1-(2-Metoxybenzyl)- 2,3-dioxo-2,3-dihydro-1 7-indole-5-carboxamide, Sodium 1 -(2-metoxybenzyl)-2,3-dioxo-2,3- dihydro-1 H-indole-5-sulphonate, 1 -(2-Metoxybenzyl)-2,3-dioxo-2,3-dihydro-1 H-indole-5- sulphonamide, 1 -(2-Metoxybenzyl)-7-trifluoromethyl-1 H-indole-2,3-dione,1 -(2-Metoxybenzyl)- 7-metoxy-1 H-indole-2,3-dione,1 -(2-Metoxybenzyl)-5-fluoro-6-chloro-1 H-indole-2,3-dione,1 - (2-Metoxybenzyl)-5,7-dichloro-1 H-indole-2, 3-dione.
In an application of the present invention, the compounds shown by Formula II are selected from 1 -(2-Trif luorometoxybenzyl)-1 H-indole-2, 3-dione
Figure imgf000039_0001
and from its derivatives, for instance 1 -(2-Trifluorometoxybenzyl)-1 H-indole-2, 3-dione, 1 -(2- Trifluorometoxybenzyl)-5-methyl-1 H-indole-2,3-dione,1 -(2-Trifluorometoxybenzyl)-5- (propane-2-yl)-1 H-indole-2,3-dione,1 -(2-Trifluorometoxybenzyl)-5-t-butyl-1 - -indole-2,3- dione,1 -(2-Trifluorometoxybenzyl)-5-metoxy-1 - -indole-2,3-dione,1 -(2- Trifluorometoxybenzyl)-5-trifluorometoxy-1 H-indole-2,3-dione,1 -(2-Trif luorometoxybenzyl)-5- fluoro-1 H-indole-2,3-dione,1 -(2-Trifluorometoxybenzyl)-5-chloro-1 - -indole-2,3-dione,1 -(2- Trifluorometoxybenzyl)-5-bromo-1 H-indole-2, 3-dione, 1 -(2-Trifluorometoxybenzyl)-5-iyodo- 1 H-indole-2, 3-dione, 1 -(2-Trifluorometoxybenzyl)-5-nitro-1 H-indole-2,3-dione,1 -(2- Trifluorometoxybenzyl)-2,3-dioxo-2,3-dihydro-1 H-indole-5-carbonitryl,1 -(2- Trif luorometoxybenzyl)-2,3-dioxo-2,3-dihydro-1 7-indole-5-carboxamide, sodium 1 -(2- trifluorometoxybenzyl)-2,3-dioxo-2,3-dihydro-1 7-indole-5-sulphonate,1 -(2- Trif luorometoxybenzyl)-2,3-dioxo-2,3-dihydro-1 H-indole-5-sulphonamide, 1 -(2-
Trifluorometoxybenzyl)-6-fluoro-1 H-indole-2, 3-dione,1 -(2-Trif luorometoxybenzyl)-6-chloro- 1 H-indole-2,3-dione,1 -(2-Trif luorometoxybenzyl)-6-bromo-1 - -indole-2,3-dione, 1 -(2- Trifluorometoxybenzyl)-7-methyl-1 H-indole-2, 3-dione,1 -(2-Trif luorometoxybenzyl)-7- trifluoromethyl-1 H-indole-2, 3-dione,1 -(2-Trif luorometoxybenzyl)-7-metoxy-1 H-indole-2, 3- dione,1 -(2-Trifluorometoxybenzyl)-7-fluoro-1 H-indole-2,3-dione,1 -(2-Trifluorometoxybenzyl)- 7-chloro-1 H-indole-2, 3-dione,1 -(2-Trifluorometoxybenzyl)-7-bromo-1 H-indole-2, 3-dione,1 -(2- Trifluorometoxybenzyl)-5-fluoro-6-chloro-1 H-indole-2, 3-dione,1 -(2-Trif luorometoxybenzyl)-5- chloro-7-methyl-1 H-indole-2, 3-dione,1 -(2-Trifluorometoxybenzyl)-5,7-dichloro-1 H-indole-2,3- dione,1 -(2-Trif luorometoxybenzyl)-5,7-dibromo-1 H-indole-2, 3-dione.
In an application of the present invention, the compounds shown by Formula II are selected from 1 -(2-Fluorobenzyl)-1 H-indole-2, 3-dione
Figure imgf000040_0001
and from its derivatives, for instance1 -(2-Fluorobenzyl)-5-(propane-2-yl)-1 H-indole-2,3- dione,1 -(2-Fluorobenzyl)-5-t-butyl-1 H-indole-2,3-dione,1 -(2-Fluorobenzyl)-5-iyodo-1 - -indole- 2,3-dione,1 -(2-Fluorobenzyl)-2,3-dioxo-2,3-dihydro-1 H-indole-5-carbonitryl, 1 -(2- Fluorobenzyl)-2,3-dioxo-2,3-dihydro-1 - -indole-5-carboxamide, Sodium 1 -(2-fluorobenzyl)- 2,3-dioxo-2,3-dihydro-1 H-indole-5-sulphonate, 1 -(2-Fluorobenzyl)-2,3-dioxo-2,3-dihydro-1 H- indole-5-sulphonamide, 1 -(2-Fluorobenzyl)-7-metoxy-1 H-indole-2,3-dione,1 -(2-Fluorobenzyl)- 5-fluoro-6-chloro-1 H-indole-2,3-dione, 1 -(2-Fluorobenzyl)-5-chloro-7-methyl-1 H-indole-2,3- dione,1 -(2-Fluorobenzyl)-5,7-dichloro-1 H-indole-2,3-dione,1 -(2-Fluorobenzyl)-5,7-dibromo- 1 H-indole-2,3-dione.
In an application of the present invention, the compounds shown by Formula II are selected obenzyl)-1 H-indole-2,3-dione
Figure imgf000040_0002
and from its derivatives, for instance 1 -(2-Chlorobenzyl)-5-(propane-2-yl)-1 H-indole-2,3- dione,1 -(2-Chlorobenzyl)-5-t-butyl-1 H-indole-2,3-dione,1 -(2-Chlorobenzyl)-5-iyodo-1 - -indole- 2,3-dione,1 -(2-Chlorobenzyl)-2,3-dioxo-2,3-dihydro-1 H-indole-5-carbonitryl, 1 -(2- Chlorobenzyl)-2,3-dioxo-2,3-dihydro-1 7-indole-5-carboxamide, Sodium 1 -(2-chlorobenzyl)- 2,3-dioxo-2,3-dihydro-1 H-indole-5-sulphonate, 1 -(2-Chlorobenzyl)-2,3-dioxo-2,3-dihydro-1 H- indole-5-sulphonamide, 1 -(2-Chlorobenzyl)-7-metoxy-1 H-indole-2,3-dione,1 -(2-
Chlorobenzyl)-5-fluoro-6-chloro-1 H-indole-2,3-dione,1 -(2-Chlorobenzyl)-5-chloro-7-methyl- 1 H-indole-2,3-dione,1 -(2-Chlorobenzyl)-5,7-dichloro-1 H-indole-2,3-dione,1 -(2-Chlorobenzyl)- 5,7-dibromo-1 H-indole-2,3-dione.
In an application of the present invention, the compounds shown by Formula II are selected from 1 -(2-Bromobenzyl)-1 H-indole-2,3-dione
Figure imgf000041_0001
and from its derivatives, for instance 1-(2-Bromobenzyl)-5-(propane-2-yl)-1H-indole-2,3- dione,1-(2-Bromobenzyl)-5-t-butyl-1 H-indole-2,3-dione,1-(2-Bromobenzyl)-5-trifluorometoxy- 1H-indole-2,3-dione,1-(2-Bromobenzyl)-5-nitro-1H-indole-2,3-dione,1-(2-Bromobenzyl)-2,3- dioxo-2,3-dihydro-1 Hindole-5-carbonitryl, 1 -(2-Bromobenzyl)-2,3-dioxo-2,3-dihydro-1 H- indole-5-carboxamide, Sodium 1 -(2-bromobenzyl)-2,3-dioxo-2,3-dihydro-1 H-indole-5- sulphonate, 1 -(2-Bromobenzyl)-2,3-dioxo-2,3-dihydro-1 H-indole-5-sulphonamide, 1 -(2- Bromobenzyl)-7-trifluoromethyl-1 H-indole-2,3-dione,1-(2-Bromobenzyl)-7-metoxy-1 H-indole- 2,3-dione,1-(2-Bromobenzyl)-5-fluoro-6-chloro-1 --indole-2,3-dione,1-(2-Bromobenzyl)-5- chloro-7-methyl-1H-indole-2,3-dione,1-(2-Bromobenzyl)-5,7-dichloro-1 --indole-2,3-dione,1- (2-Bromobenzyl)-5,7-dibromo-1 --indole-2,3-dione.
In an application of the present invention, the compounds shown by Formula II are selected from 1 -(2-iodobenzyl)-1 H-indole-2,3-dione
Figure imgf000041_0002
and from its derivatives, for instance 1-(2-iyodobenzyl)-5-methyl-1H-indole-2,3-dione,1-(2- iyodobenzyl)-5-(propane-2-yl)-1H-indole-2,3-dione,1-(2-iyodobenzyl)-5-t-butyl-1H-indole-2,3- dione,1-(2-iyodobenzyl)-5-metoxy-1 H-indole-2,3-dione,1-(2-iyodobenzyl)-5-trifluorometoxy- 1H-indole-2,3-dione,1-(2-iyodobenzyl)-5-fluoro-1 --indole-2,3-dione,1-(2-iyodobenzyl)-5- chloro-1 H-indole-2,3-dione,1-(2-iyodobenzyl)-5-bromo-1 --indole-2,3-dione,1-(2- iyodobenzyl)-5-iyodo-1 7-indole-2,3-dione,1-(2-iyodobenzyl)-5-nitro-1 H-indole-2,3-dione,1-(2- iyodobenzyl)-2,3-dioxo-2,3-dihydro-1 7-indole-5-carbonitryl, 1 -(2-iyodobenzyl)-2,3-dioxo-2,3- dihydro-1 7-indole-5-carboxamide, Sodium 1 -(2-iyodobenzyl)-2,3-dioxo-2,3-dihydro-1 H- indole-5-sulphonate, 1 -(2-iyodobenzyl)-2,3-dioxo-2,3-dihydro-1 H-indole-5-sulphonamide, 1 - (2-iyodobenzyl)-6-bromo-1H-indole-2,3-dione,1-(2-iyodobenzyl)-7-methyl-1H-indole-2,3- dione,1-(2-iyodobenzyl)-7-trifluoromethyl-1 H-indole-2,3-dione,1-(2-iyodobenzyl)-7-metoxy- 1H-indole-2,3-dione,1-(2-iyodobenzyl)-7-fluoro-1 --indole-2,3-dione,1-(2-iyodobenzyl)-7- chloro-1 H-indole-2,3-dione -(2-iyodobenzyl)-7-bromo-1Hindole-2,3-dione,1-(2- iyodobenzyl)-5-fluoro-6-chloro-1 H-indole-2,3-dione ,1 -(2-iyodobenzyl)-5-chloro-7-methyl-1 H- indole-2,3-dione -(2-iyodobenzyl)-57-dichloro-1Hindole-2,3-dione,1-(2-iyodobenzyl)-5,7- dibromo-1 H-indole-2,3-dione.
In an application of the present invention, the compounds shown by Formula II are selected from 1 -(2-Nitrobenzyl)-1 H-indole-2,3-dione
Figure imgf000042_0001
and from its derivatives, for instance 1-(2-Nitrobenzyl)-5-(propane-2-yl)-1H-indole-2,3- dione,1-(2-Nitrobenzyl)-5-t-butyl-1H-indole-2,3-dione,1-(2-Nitrobenzyl)-5-trifluorometoxy-1H- indole-2,3-dione,1-(2-Nitrobenzyl)-5-iyodo-1H-indole-2,3-dione,1-(2-Nitrobenzyl)-2,3-dioxo- 2,3-dihydro-1 H-indole-5-carbonitryl, 1 -(2-Nitrobenzyl)-2,3-dioxo-2,3-dihydro-1 H-indole-5- carboxamide, Sodium 1-(2-nitrobenzyl)-2,3-dioxo-2,3-dihydro-1 7-indole-5-sulphonate, 1-(2- Nitrobenzyl)-2,3-dioxo-2,3-dihydro-1 H-indole-5-sulphonamide, 1 -(2-Nitrobenzyl)-6-chloro-1 H- indole-2,3-dione,1-(2-Nitrobenzyl)-6-bromo-1H-indole-2,3-dione,1-(2-Nitrobenzyl)-7- trifluoromethyl-1H-indole-2,3-dione,1-(2-Nitrobenzyl)-7-metoxy-1 H-indole-2,3-dione,1-(2- Nitrobenzyl)-7-fluoro-1H-indole-2,3-dione,1-(2-Nitrobenzyl)-7-chloro-1H-indole-2,3-dione,1- (2-Nitrobenzyl)-7-bromo-1 --indole-2,3-dione,1-(2-Nitrobenzyl)-5-fluoro-6-chloro-1 --indole- 2,3-dione,1-(2-Nitrobenzyl)-5-chloro-7-methyl-1H-indole-2,3-dione,1-(2-Nitrobenzyl)-5,7- dichloro-1 7-indole-2,3-dione.
In an application of the present invention, the compounds shown by Formula II are selected obenzyl)-1 H-indole-2,3-dione
Figure imgf000042_0002
and from its derivatives, for instance 1-(2-Cyanobenzyl)-5-(propane-2-yl)-1H-indole-2,3- dione,1-(2-Cyanobenzyl)-5-t-butyl-1 --indole-2,3-dione,1-(2-Cyanobenzyl)-5-metoxy-1 -- indole-2,3-dione,1-(2-Cyanobenzyl)-5-trifluorometoxy-1 --indole-2,3-dione,1-(2- Cyanobenzyl)-5-iyodo-1 7-indole-2,3-dione,1-(2-Cyanobenzyl)-5-nitro-1 H-indole-2,3-dione,1- (2-Cyanobenzyl)-2,3-dioxo-2,3-dihydro-1 --indole-5-carbonitryl, 1 -(2-Cyanobenzyl)-2,3-dioxo- 2,3-dihydro-1 --indole-5-carboxamide, Sodium 1 -(2-cyanobenzyl)-2,3-dioxo-2,3-dihydro-1 H- indole-5-sulphonate, 1 -(2-Cyanobenzyl)-2,3-dioxo-2,3-dihydro-1 H-indole-5-sulphonamide, 1 - (2-Cyanobenzyl)-7-trifluoromethyl-1 H-indole-2,3-dione,1-(2-Cyanobenzyl)-7-metoxy-1 -- indole-2,3-dione,1-(2-Cyanobenzyl)-5-fluoro-6-chloro-1 H-indole-2,3-dione,1-(2-
Cyanobenzyl)-5-chloro-7-methyl-1H-indole-2,3-dione,1-(2-Cyanobenzyl)-5,7-dichloro-1 H- indole-2,3-dione,1-(2-Cyanobenzyl)-5,7-dibromo-1 H-indole-2,3-dione.
In an application of the present invention, the compounds shown by Formula II are selected from 1-(2-Ethylbenzyl)-1H-indole-2,3-dione
Figure imgf000043_0001
and from its derivatives, for instance 1-(2-Ethylbenzyl)-1H-indole-2,3-dione,1-(2-Ethylbenzyl)-
5-methyl-1H-indole-2,3-dione,1-(2-Ethylbenzyl)-5-(propane-2-yl)-1H-indole-2,3-dione,1-(2-
Ethylbenzyl)-5-t-butyl-1H-indole-2,3-dione,1-(2-Ethylbenzyl)-5-metoxy-1H-indole-2,3-dione,1- (2-Ethylbenzyl)-5-trifluorometoxy-1H-indole-2,3-dione,1-(2-Ethylbenzyl)-5-fluoro-1H-indole- 2,3-dione,1-(2-Ethylbenzyl)-5-chloro-1H-indole-2,3-dione,1-(2-Ethylbenzyl)-5-bromo-1H- indole-2,3-dione,1-(2-Ethylbenzyl)-5-iyodo-1H-indole-2,3-dione,1-(2-Ethylbenzyl)-5-nitro-1H- indole-2,3-dione,1-(2-Ethylbenzyl)-2,3-dioxo-2,3-dihydro-1H-indole-5-carbonitryl, 1-(2- Ethylbenzyl)-2,3-dioxo-2,3-dihydro-1 7-indole-5-carboxamide, Sodium 1 -(2-ethylbenzyl)-2,3- dioxo-2,3-dihydro-1 H-indole-5-sulphonate, 1 -(2-Ethylbenzyl)-2,3-dioxo-2,3-dihydro-1 H- indole-5-sulphonamide, 1 -(2-Ethylbenzyl)-6-fluoro-1 H-indole-2,3-dione,1 -(2-Ethylbenzyl)-6- chloro-1H-indole-2,3-dione,1-(2-Ethylbenzyl)-6-bromo-1H-indole-2,3-dione,1-(2-Ethylbenzyl)- 7-methyl-1H-indole-2,3-dione,1-(2-Ethylbenzyl)-7-trifluoromethyl-1H-indole-2,3-dione,1-(2- Ethylbenzyl)-7-metoxy-1 --indole-2,3-dione,1-(2-Ethylbenzyl)-7-fluoro-1 --indole-2,3-dione,1- (2-Ethylbenzyl)-7-chloro-1H-indole-2,3-dione,1-(2-Ethylbenzyl)-7-bromo-1H-indole-2,3- dione,1-(2-Ethylbenzyl)-5-fluoro-6-chloro-1H-indole-2,3-dione,1-(2-Ethylbenzyl)-5-chloro-7- methyl-1 H-indole-2,3-dione,1 -(2-Ethylbenzyl)-5,7-dichloro-1 H-indole-2,3-dione,1 -(2- Ethylbenzyl)-5.7-dibromo-1 --indole-2,3-dione. In an application of the present invention, the compounds shown by Formula II are selected from 1 -[2-(Propane-2-yl)benzyl]-1 H-indole-2,3-dione
Figure imgf000044_0001
and from its derivatives, for instance 1-[2-(Propane-2-yl)benzyl]-1H-indole-2,3-dione,1-[2- (Propane-2-yl)benzyl]-5-methyl-1H-indole-2,3-dione,1-[2-(Propane-2-yl)benzyl]-5-(propane-2- yl)-1H-indole-2,3-dione,1-[2-(Propane-2-yl)benzyl]-5-t-butyl-1H-indole-2,3-dione,1-[2- (Propane-2-yl)benzyl]-5-metoxy-1 --indole-2,3-dione,1-[2-(Propane-2-yl)benzyl]-5- trifluorometoxy-1 H-indole-2,3-dione,1-[2-(Propane-2-yl)benzyl]-5-fluoro-1 --indole-2,3- dione,1-[2-(Propane-2-yl)benzyl]-5-chloro-1 A7-indole-2,3-dione,1-[2-(Propane-2-yl)benzyl]-5- bromo-1 --indole-2,3-dione,1-[2-(Propane-2-yl)benzyl]-5-iyodo-1 H-indole-2,3-dione,1-[2- (Propane-2-yl)benzyl]-5-nitro-1H-indole-2,3-dione,1-[2-(Propane-2-yl)benzyl]-2,3-dioxo-2,3- dihydro-1H-indole-5-carbonitryl, 1-[2-(Propane-2-yl)benzyl]-2,3-dioxo-2,3-dihydro-1H-indole- 5-carboxamide, Sodium 1 -[2-(propane-2-yl)benzyl]-2,3-dioxo-2,3-dihydro-1 H-indole-5- sulphonate, 1-[2-(Propane-2-yl)benzyl]-2,3-dioxo-2,3-dihydro-1H-indole-5-sulphonamide, 1- [2-(Propane-2-yl)benzyl]-6-fluoro-1H-indole-2,3-dione,1-[2-(Propane-2-yl)benzyl]-6-chloro- 1H-indole-2,3-dione,1-[2-(Propane-2-yl)benzyl]-6-bromo-1 --indole-2,3-dione,1-[2-(Propane- 2-yl)benzyl]-7-methyl-1 H-indole-2,3-dione,1 -[2-(Propane-2-yl)benzyl]-7-trifluoromethyl-1 H- indole-2,3-dione,1-[2-(Propane-2-yl)benzyl]-7-metoxy-1 7-indole-2,3-dione,1-[2-(Propane-2- yl)benzyl]-7-fluoro-1H-indole-2,3-dione,1-[2-(Propane-2-yl)benzyl]-7-chloro-1H-indole-2,3- dione,1-[2-(Propane-2-yl)benzyl]-7-bromo-1 --indole-2,3-dione,1-[2-(Propane-2-yl)benzyl]-5- fluoro-6-chloro-1 --indole-2,3-dione,1-[2-(Propane-2-yl)benzyl]-5-chloro-7-methyl-1H-indole- 2,3-dione,1-[2-(Propane-2-yl)benzyl]-5,7-dichloro-1H-indole-2,3-dione,1-[2-(Propane-2- yl)benzyl]-5,7-dibromo-1 --indole-2,3-dione.
In an application of the present invention, the compounds shown by Formula II are selected from 1 -(2-t-butylbenzyl)-1 H-indole-2,3-dione
Figure imgf000044_0002
and from its derivatives, for instance 1-(2-t-butylbenzyl)-1H-indole-2,3-dione,1-(2-t- butylbenzyl)-5-methyl-1Hindole-2,3-dione,1-(2-t-butylbenzyl)-5-(propane-2-yl)-1Hindole-2,3- dione -(2-t-butylbenzyl)-5-t-buty
indole-2,3-dione,1 -(2-t-butylbenzyl)-5-trifluorometoxy-1 H-indole-2,3-dione,1 -(2-t-butylbenzyl)- 5 luoro-1 H-indole-2,3-dione -(2-t-butylbenzyl)-5-chloro-1 H-indole-2,3-dione,1 -(2-t- butylbenzyl)-5-bromo-1 Hindole-2,3-dione,1 -(2-t-butylbenzyl)-5-iyodo-1 H-indole-2,3-dione,1 - (2-t-butylbenzyl)-2,3-dioxo-2,3-dihydro-1 H-indole-5-carbonitryl, 1 -(2-t-butylbenzyl)-2,3-dioxo- 2,3-dihydro-1 Hindole-5-carboxamide, Sodium 1 -(2-t-butylbenzyl)-2,3-dioxo-2,3-dihydro-1 H- indole-5-sulphonate, 1 -(2-t-butylbenzyl)-2,3-dioxo-2,3-dihydro-1 H-indole-5-sulphonamide, 1 - (2-t-butylbenzyl)-6-fluoro-1 H-indole-2,3-dione,1 -(2-t-butylbenzyl)-6-chloro-1 H-indole-2,3- dione ,1 -(2-t-butylbenzyl)-6-bromo-1 H-indole-2,3-dione,1 -(2-t-butylbenzyl)-7-methyl-1 H- indole-2,3-dione,1 -(2-t-butylbenzyl)-7-triflu^
7-metoxy-1 H-indole-2,3-dione,1 -(2-t-butylbenzyl)-7-fluoro-1 H-indole-2,3-dione,1 -(2-t- butylbenzyl)-7-chloro-1 Hindole-2,3-dione,1 -(2-t-butylbenzyl)-7-bromo-1 H-indole-2,3-dione,1 - (2-t-butylbenzyl)-5 luoro-6-chloro-1 Hindole-2,3-dione -(2-t-butylbenzyl)-5-chloro-7-methyl^ 1 H-indole-2,3-dione -(2-t-butylbenzyl)-57-dichloro-1 H-indole-2,3-dione -(2-t-butylben 5,7-dibromo-1 H-indole-2,3-dione.
In an application of the present invention, the compounds shown by Formula II are selected xo-2,3-dihydro-1 H-indole-1 -yl)methyl]benzoic acid
Figure imgf000045_0001
and from its derivatives, for instance 2-[(5-Methyl-2,3-dioxo-2,3-dihydro-1 7-indole-1 - yl)methyl]benzoic acid, 2-[(5-(Propane-2-yl)-2,3-dioxo-2,3-dihydro-1 H-indole-1 - yl)methyl]benzoic acid, 2-[(5-t-Butyl-2,3-dioxo-2,3-dihydro-1 H-indole-1 -yl)methyl]benzoic acid, 2-[(5-Metoxy-2,3-dioxo-2,3-dihydro-1 H-indole-1 -yl)methyl]benzoic acid, 2-[(5- Trif luorometoxy-2,3-dioxo-2,3-dihydro-1 H-indole-1 -yl)methyl]benzoic acid, 2-[(5-Fluoro-2,3- dioxo-2,3-dihydro-1 H-indole-1 -yl)methyl]benzoic acid, 2-[(5-Chloro-2,3-dioxo-2,3-dihydro-1 H- indole-1 -yl)methyl]benzoic acid, 2-[(5-Bromo-2,3-dioxo-2,3-dihydro-1 H-indole-1 - yl)methyl]benzoic acid, 2-[(5-iyodo-2,3-dioxo-2,3-dihydro-1 H-indole-1 -yl)methyl]benzoic acid, 2-[(5-Nitro-2,3-dioxo-2,3-dihydro-1 H-indole-1 -yl)methyl]benzoic acid, 2-[(5-Cyano-2,3-dioxo- 2,3-dihydro-1 H-indole-1 -yl)methyl]benzoic acid, 2-[(5-Karbamoil-2,3-dioxo-2,3-dihydro-1 H- indole-1 -yl)methyl]benzoic acid, sodium 1 -(2-carboxybenzyl)-2,3-dioxo-2,3-dihydro-1 H- indole-5-sulphonate,2-[(5-Sulphamoil-2,3-dioxo-2,3-dihydro-1 H-indole-1 -yl)methyl]benzoic acid, 2-[(6-Fluoro-2,3-dioxo-2,3-dihydro-1 H-indole-1 -yl)methyl]benzoic acid, 2-[(6-Chloro-2,3- dioxo-2,3-dihydro-1 H-indole-1 -yl)methyl]benzoic acid, 2-[(6-Bromo-2,3-dioxo-2,3-dihydro-1 H- indole-1 -yl)methyl]benzoic acid, 2-[(7-Methyl-2,3-dioxo-2,3-dihydro-1 H-indole-1 - yl)methyl]benzoic acid, 2-[(7-Trifluoromethyl-2,3-dioxo-2,3-dihydro-1 H-indole-1 - yl)methyl]benzoic acid, 2-[(7-Metoxy-2,3-dioxo-2,3-dihydro-1 H-indole-1 -yl)methyl]benzoic acid, 2-[(7-Fluoro-2,3-dioxo-2,3-dihydro-1 H-indole-1 -yl)methyl]benzoic acid, 2-[(7-Chloro-2,3- dioxo-2,3-dihydro-1 H-indole-1 -yl)methyl]benzoic acid, 2-[(7-Bromo-2,3-dioxo-2,3-dihydro-1 H- indole-1 -yl)methyl]benzoic acid, 2-[(5-Fluoro-6-chloro-2,3-dioxo-2,3-dihydro-1 H-indole-1 - yl)methyl]benzoic acid, 2-[(5-Chloro-7-methyl-2,3-dioxo-2,3-dihydro-1 H-indole-1 - yl)methyl]benzoic acid, 2-[(5,7-Dichloro-2,3-dioxo-2,3-dihydro-1 H-indole-1 -yl)methyl]benzoic acid, 2-[(5,7-Dibromo-2,3-dioxo-2,3-dihydro-1 H-indole-1 -yl)methyl]benzoic acid.
In an application of the present invention, the compounds shown by Formula II are selected oxybenzyl)-1 H-indole-2,3-dione
Figure imgf000046_0001
and from its derivatives, for instance 1 -(2-Hydroxybenzyl)-5-methyl-1 H-indole-2,3-dione,1 -(2- Hydroxybenzyl)-5-(propane-2-yl)-1 H-indole-2,3-dione,1 -(2-Hydroxybenzyl)-5-t-butyl-1 H- indole-2,3-dione,1 -(2-Hydroxybenzyl)-5-metoxy-1 H-indole-2,3-dione,1 -(2-Hydroxybenzyl)-5- trifluorometoxy-1 H-indole-2,3-dione, 1 -(2-Hydroxybenzyl)-5-fluoro-1 H-indole-2,3-dione,1 -(2- Hydroxybenzyl)-5-chloro-1 H-indole-2,3-dione,1 -(2-Hydroxybenzyl)-5-bromo-1 H-indole-2,3- dionel -(2-Hydroxybenzyl)-5-iyodo-1 H-indole-2,3-dione,1 -(2-Hydroxybenzyl)-5-nitro-1 H- indole-2,3-dione,1 -(2-Hydroxybenzyl)-2,3-dioxo-2,3-dihydro-1 H-indole-5-carbonitryl, 1 -(2- Hydroxybenzyl)-2,3-dioxo-2,3-dihydro-1 H-indole-5-carboxamide, Sodium 1 -(2- hydroxybenzyl)-2,3-dioxo-2,3-dihydro-1 H-indole-5-sulphonate, 1 -(2-Hydroxybenzyl)-2,3- dioxo-2,3-dihydro-1 H-indole-5-sulphonamide, 1 -(2-Hydroxybenzyl)-6-f luoro-1 H-indole-2,3- dione,1 -(2-Hydroxybenzyl)-6-chloro-1 H-indole-2,3-dione,1 -(2-Hydroxybenzyl)-6-bromo-1 H indole-2,3-dione,1 -(2-Hydroxybenzyl)-7-methyl-1 H-indole-2,3-dione,1 -(2-Hydroxybenzyl)-7- trifluoromethyl-1 H-indole-2,3-dione,1 -(2-Hydroxybenzyl)-7-metoxy-1 H-indole-2,3-dione, 1 -(2- Hydroxybenzyl)-7-f luoro-1 H-indole-2,3-dione, 1 -(2-Hydroxybenzyl)-7-chloro-1 H-indole-2,3- dione,1 -(2-Hydroxybenzyl)-7-bromo-1 H-indole-2,3-dione,1 -(2-Hydroxybenzyl)-5-fluoro-6- chloro-1 H-indole-2,3-dione,1 -(2-Hydroxybenzyl)-5-chloro-7-methyl-1 H-indole-2,3-dione,1 -(2- Hydroxybenzyl)-5,7-dichloro-1 H-indole-2,3-dione,1 -(2-Hydroxybenzyl)-5,7-dibromo-1 H- indole-2,3-dione. In an application of the present invention, the compounds shown by Formula II are selected from 1 -(2,4-Dimethylbenzyl)-1 H-indole-2,3-dione
Figure imgf000047_0001
and from its derivatives, for instance 1-(2,4-Dimethylbenzyl)-5-methyl-1H-indole-2,3-dione,1- (2,4-Dimethylbenzyl)-5-(propane-2-yl)-1H-indole-2,3-dione,1-(2,4-Dimethylbenzyl)-5-t-butyl- 1H-indole-2,3-dione,1-(2,4-Dimethylbenzyl)-5-metoxy-1H-indole-2,3-dione,1-(2,4- Dimethylbenzyl)-5-trifluorometoxy-1 --indole-2,3-dione,1-(2,4-Dimethylbenzyl)-5-iyodo-1 -- indole-2,3-dione,1-(2,4-Dimethylbenzyl)-5-nitro-1 --indole-2,3-dione,1-(2,4-Dimethylbenzyl)- 2,3-dioxo-2,3-dihydro-1 H-indole-5-carbonitryl, 1 -(2,4-Dimethylbenzyl)-2,3-dioxo-2,3-dihydro- 1H-indole-5-carboxamide, Sodium 1-(2,4-Dimethylbenzyl)-2,3-dioxo-2,3-dihydro-1 H-indole-5- sulphonate, 1 -(2,4-Dimethylbenzyl)-2,3-dioxo-2,3-dihydro-1 H-indole-5-sulphonamide, 1 -(2,4- Dimethylbenzyl)-6-fluoro-1 H-indole-2,3-dione,1 -(2,4-Dimethylbenzyl)-6-chloro-1 H-indole-2,3- dione,1-(2,4-Dimethylbenzyl)-6-bromo-1 --indole-2,3-dione,1-(2,4-Dimethylbenzyl)-7-methyl- 1H-indole-2,3-dione,1-(2,4-Dimethylbenzyl)-7-trifluoromethyl-1H-indole-2,3-dione,1-(2,4- Dimethylbenzyl)-7-metoxy-1 H-indole-2,3-dione,1-(2,4-Dimethylbenzyl)-7-fluoro-1 --indole- 2,3-dione,1-(2,4-Dimethylbenzyl)-7-chloro-1H-indole-2,3-dione,1-(2,4-Dimethylbenzyl)-7- bromo-1 --indole-2,3-dione,1-(2,4-Dimethylbenzyl)-5-fluoro-6-chloro-1 H-indole-2,3-dione,1- (2,4-Dimethylbenzyl)-5-chloro-7-methyl-1H-indole-2,3-dione,1-(2,4-Dimethylbenzyl)-5,7- dichloro-1 --indole-2,3-dione,1-(2,4-Dimethylbenzyl)-5,7-dibromo-1 H-indole-2,3-dione.
In an application of the present invention, the compounds shown by Formula II are selected from 1 -(2,5-Dimethylbenzyl)-1 H-indole-2,3-dione
Figure imgf000047_0002
and from its derivatives, for instance 1-(2,5-Dimethylbenzyl)-5-(propane-2-yl)-1H-indole-2,3- dione,1-(2,5-Dimethylbenzyl)-5-t-butyl-1 H-indole-2,3-dione,1-(2,5-Dimethylbenzyl)-5-metoxy- 1H-indole-2,3-dione,1-(2,5-Dimethylbenzyl)-5-trifluorometoxy-1 7-indole-2,3-dione,1-(2,5- Dimethylbenzyl)-5-iyodo-1 H-indole-2,3-dione,1-(2,5-Dimethylbenzyl)-5-nitro-1 --indole-2,3- dione -(2,5-Dimethylbenzyl)-2,3-dioxo 1 -(2,5- Dimethylbenzyl)-2,3-dioxo-2,3-dihydro-1 - -indole-5-carboxamide, Sodium 1 -(2,5- Dimethylbenzyl)-2,3-dioxo-2,3-dihydro-1 H-indole-5-sulphonate, 1 -(2,5-Dimethylbenzyl)-2,3- dioxo-2,3-dihydro-1 H-indole-5-sulphonamide, 1 -(2,5-Dimethylbenzyl)-7-trifluoromethyl-1 H- indole-2,3-dione,1 -(2,5-Dimethylbenzyl)-7-metoxy-1 H-indole-2,3-dione,1 -(2,5-
Dimethylbenzyl)-5-fluoro-6-chloro-1 - -indole-2,3-dione, 1 -(2,5-Dimethylbenzyl)-5-chloro-7- methyl-1 H-indole-2,3-dione,1 -(2,5-Dimethylbenzyl)-5,7-dichloro-1 H-indole-2,3-dione,1 -(2,5- Dimethylbenzyl)-5,7-dibromo-1 H-indole-2,3-dione.
In an application of the present invention, the compounds shown by Formula II are selected ethylbenzyl)-1 H-indole-2,3-dione
Figure imgf000048_0001
and from its derivatives, for instance 1 -(2,6-Dimethylbenzyl)-5-(propane-2-yl)-1 H-indole-2,3- dione,1 -(2,6-Dimethylbenzyl)-5-t-butyl-1 H-indole-2,3-dione,1 -(2,6-Dimethylbenzyl)-5-metoxy- 1 H-indole-2,3-dione,1 -(2,6-Dimethylbenzyl)-5-trifluorometoxy-1 H-indole-2,3-dione,1 -(2,6- Dimethylbenzyl)-5-iyodo-1 H-indole-2,3-dione, 1 -(2,6-Dimethylbenzyl)-5-nitro-1 H-indole-2,3- dione,1 -(2,6-Dimethylbenzyl)-2,3-dioxo-2,3-dihydro-1 H-indole-5-carbonitryl, 1 -(2,6- Dimethylbenzyl)-2,3-dioxo-2,3-dihydro-1 7-indole-5-carboxamide, sodium 1 -(2,6- dimethylbenzyl)-2,3-dioxo-2,3-dihydro-1 H-indole-5-sulphonate, 1 -(2,6-Dimethylbenzyl)-2,3- dioxo-2,3-dihydro-1 H-indole-5-sulphonamide, 1 -(2,6-Dimethylbenzyl)-7-trifluoromethyl-1 H- indole-2,3-dione,1 -(2,6-Dimethylbenzyl)-7-metoxy-1 H-indole-2,3-dione,1 -(2,6- Dimethylbenzyl)-5-fluoro-6-chloro-1 - -indole-2,3-dione, 1 -(2,6-Dimethylbenzyl)-5-chloro-7- methyl-1 H-indole-2,3-dione,1 -(2,6-Dimethylbenzyl)-5,7-dichloro-1 H-indole-2,3-dione,1 -(2,6- Dimethylbenzyl)-5,7-dibromo-1 H-indole-2,3-dione.
In an application of the present invention, the compounds shown by Formula II are selected f imethylbenzyl)-1 H-indole-2,3-dione
H
Figure imgf000048_0002
and from its derivatives, for instance 1-(3,4-Dimethylbenzyl)-5-(propane-2-yl)-1H-indole-2,3- dione,1-(3,4-Dimethylbenzyl)-5-t-butyl-1 H-indole-2,3-dione,1-(3,4-Dimethylbenzyl)-5-metoxy- 1H-indole-2,3-dione,1-(3,4-Dimethylbenzyl)-5-trifluorometoxy-1 7-indole-2,3-dione,1-(3,4- Dimethylbenzyl)-5-nitro-1H-indole-2,3-dione,1-(3,4-Dimethylbenzyl)-2,3-dioxo-2,3-dihydro- 1H-indole-5-carbonitryl, Sodium 1-(3,4-dimethylbenzyl)-2,3-dioxo-2,3-dihydro-1 --indole-5- sulphonate, 1 -(3,4-Dimethylbenzyl)-2,3-dioxo-2,3-dihydro-1 H-indole-5-sulphonamide, 1 -(3,4- Dimethylbenzyl)-7-trifluoromethyl-1H-indole-2,3-dione,1-(3,4-Dimethylbenzyl)-7-metoxy-1 -- indole-2,3-dione,1-(3,4-Dimethylbenzyl)-5-fluoro-6-chloro-1H-indole-2,3-dione,1-(3,4- Dimethylbenzyl)-5-chloro-7-methyl-1H-indole-2,3-dione,1-(3,4-Dimethylbenzyl)-5,7-dichloro- 1H-indole-2,3-dione,1-(3,4-Dimethylbenzyl)-5,7-dibromo-1H-indole-2,3-dione.
In an application of the present invention, the compounds shown by Formula II are selected thylbenzyl)-1 H-indole-2,3-dione
Figure imgf000049_0001
and from its derivatives, for instance 1-(3,5-Dimethylbenzyl)-5-(propane-2-yl)-1 H-indole-2,3- dione,1-(3,5-Dimethylbenzyl)-5-t-butyl-1 H-indole-2,3-dione,1-(3,5-Dimethylbenzyl)-5-metoxy- 1H-indole-2,3-dione,1-(3,5-Dimethylbenzyl)-5-trifluorometoxy-1 7-indole-2,3-dione,1-(3,5- Dimethylbenzyl)-5-iyodo-1 H-indole-2,3-dione,1-(3,5-Dimethylbenzyl)-5-nitro-1 --indole-2,3- dione,1-(3,5-Dimethylbenzyl)-2,3-dioxo-2,3-dihydro-1 --indole-5-carbonitryl, 1 -(3,5- Dimethylbenzyl)-2,3-dioxo-2,3-dihydro-1 --indole-5-carboxamide, Sodium 1 -(3,5- dimethylbenzyl)-2,3-dioxo-2,3-dihydro-1 7-indole-5-sulphonate, 1 -(3,5-Dimethylbenzyl)-2,3- dioxo-2,3-dihydro-1 H-indole-5-sulphonamide, 1 -(3,5-Dimethylbenzyl)-7-trifluoromethyl-1 H- indole-2,3-dione,1-(3,5-Dimethylbenzyl)-7-metoxy-1 7-indole-2,3-dione,1-(3,5- Dimethylbenzyl)-5-fluoro-6-chloro-1 --indole-2,3-dione,1-(3,5-Dimethylbenzyl)-5-chloro-7- methyl-1H-indole-2,3-dione,1-(3,5-Dimethylbenzyl)-5,7-dichloro-1H-indole-2,3-dione,1-(3,5- Dimethylbenzyl)-5,7-dibromo-1 H-indole-2,3-dione.
In an application of the present invention, the compounds shown by Formula II are selected from 1 -(2,3-Difluorobenzyl)-1 H-indole-2,3-dione
Figure imgf000050_0001
and from its derivatives, for instance 1-(2,3-Difluorobenzyl)-5-(propane-2-yl)-1H-indole-2,3- dione,1-(2,3-Difluorobenzyl)-5-t-butyl-1 --indole-2,3-dione,1-(2,3-Difluorobenzyl)-5-metoxy- 1H-indole-2,3-dione,1-(2,3-Difluorobenzyl)-5-trifluorometoxy-1H-indole-2,3-dione,1-(2,3- Difluorobenzyl)-5-iyodo-1 --indole-2,3-dione,1-(2,3-Difluorobenzyl)-5-nitro-1 --indole-2,3- dione,1-(2,3-Difluorobenzyl)-2,3-dioxo-2,3-dihydro-1H-indole-5-carbonitryl, 1-(2,3- Difluorobenzyl)-2,3-dioxo-2,3-dihydro-1 7-indole-5-carboxamide, Sodium 1 -(2,3- dif luorobenzyl)-2,3-dioxo-2,3-dihydro-1 7-indole-5-sulphonate, 1 -(2,3-Difluorobenzyl)-2,3- dioxo-2,3-dihydro-1 H-indole-5-sulphonamide, 1 -(2,3-Dif luorobenzyl)-7-trifluoromethyl-1 H- indole-2,3-dione,1-(2,3-Difluorobenzyl)-7-metoxy-1H-indole-2,3-dione,1-(2,3-Difluorobenzyl)- 5-fluoro-6-chloro-1H-indole-2,3-dione,1 -(2,3-Dif luorobenzyl)-5-chloro-7-methyl-1H-indole-2,3- dione,1-(2,3-Difluorobenzyl)-5,7-dichloro-1H-indole-2,3-dione,1-(2,3-Difluorobenzyl)-5,7- dibromo-1 H-indole-2,3-dione.
In an application of the present invention, the compounds shown by Formula II are selected fluorobenzyl)-1 H-indole-2,3-dione
Figure imgf000050_0002
and from its derivatives, for instance 1-(2,4-Difluorobenzyl)-5-(propane-2-yl)-1H-indole-2,3- dione,1-(2,4-Difluorobenzyl)-5-t-butyl-1 --indole-2,3-dione,1-(2,4-Difluorobenzyl)-5-metoxy- 1H-indole-2,3-dione,1-(2,4-Difluorobenzyl)-5-iyodo-1H-indole-2,3-dione,1-(2,4-
Difluorobenzyl)-5-nitro-1H-indole-2,3-dione,1-(2,4-Difluorobenzyl)-2,3-dioxo-2,3-dihydro-1H- indole-5-carbonitryl, 1 -(2,4-Difluorobenzyl)-2,3-dioxo-2,3-dihydro-1 7-indole-5-carboxamide, sodium 1 -(2,4-dif luorobenzyl)-2,3-dioxo-2,3-dihydro-1 7-indole-5-sulphonate, 1 -(2,4- Dif luorobenzyl)-2,3-dioxo-2,3-dihydro-1 H-indole-5-sulphonamide, 1 -(2,4-Dif luorobenzyl)-7- trifluoromethyl-1H-indole-2,3-dione,1-(2,4-Difluorobenzyl)-7-metoxy-1 H-indole-2,3-dione,1- (2,4-Difluorobenzyl)-5-fluoro-6-chloro-1 7-indole-2,3-dione,1 -(2,4-Dif luorobenzyl)-5-chloro-7- methyl-1 H-indole-2,3-dione ,1 -(2,4-Difluorobenzyl)-5,7-dichloro-1 H-indole-2,3-dione,1 -(2,4- Difluorobenzyl)-5,7-dibromo-1 H-indole-2,3-dione.
In an application of the present invention, the compounds shown by Formula II are selected robenzyl)-1 H-indole-2,3-dione
Figure imgf000051_0001
and from its derivatives, for instance 1 -(2,5-Difluorobenzyl)-5-(propane-2-yl)-1 H-indole-2,3- dione,1 -(2,5-Difluorobenzyl)-5-t-butyl-1 - -indole-2,3-dione,1 -(2,5-Difluorobenzyl)-5-metoxy-
1 H-indole-2,3-dione,1 -(2,5-Difluorobenzyl)-5-trifluorometoxy-1 - -indole-2,3-dione,1 -(2,5- Difluorobenzyl)-5-iyodo-1 H-indole-2,3-dione,1 -(2,5-Difluorobenzyl)-5-nitro-1 H-indole-2,3- dione,1 -(2,5-Difluorobenzyl)-2,3-dioxo-2,3-dihydro-1 7-indole-5-carbonitryl, 1 -(2,5- Difluorobenzyl)-2,3-dioxo-2,3-dihydro-1 7-indole-5-carboxamide, Sodium 1 -(2,5- dif luorobenzyl)-2,3-dioxo-2,3-dihydro-1 7-indole-5-sulphonate, 1 -(2,5-Difluorobenzyl)-2,3- dioxo-2,3-dihydro-1 H-indole-5-sulphonamide, 1 -(2,5-Dif luorobenzyl)-7-trifluoromethyl-1 H- indole-2,3-dione,1 -(2,5-Difluorobenzyl)-7-metoxy-1 - -indole-2,3-dione,1 -(2,5-Difluorobenzyl)- 5-fluoro-6-chloro-1 H-indole-2,3-dione, 1 -(2,5-Dif luorobenzyl)-5-chloro-7-methyl-1 H-indole-2,3- dione,1 -(2,5-Difluorobenzyl)-5,7-dichloro-1 H-indole-2,3-dione,1 -(2,5-Difluorobenzyl)-5,7- dibromo-1 H-indole-2,3-dione.
In an application of the present invention, the compounds shown by Formula II are selected orobenzyl)-1 H-indole-2,3-dione
Figure imgf000051_0002
and from its derivatives, for instance 1 -(2,6-Difluorobenzyl)-5-methyl-1 H-indole-2,3-dione,1 - (2,6-Difluorobenzyl)-5-(propane-2-yl)-1 H-indole-2,3-dione,1 -(2,6-Difluorobenzyl)-5-t-butyl-1 H- indole-2,3-dione,1 -(2,6-Difluorobenzyl)-5-metoxy-1 - -indole-2,3-dione,1 -(2,6-Difluorobenzyl)- 5-bromo-1 H-indole-2,3-dione,1 -(2,6-Difluorobenzyl)-5-iyodo-1 H-indole-2,3-dione,1 -(2,6- Difluorobenzyl)-5-nitro-1 H-indole-2,3-dione,1 -(2,6-Difluorobenzyl)-2,3-dioxo-2,3-dihydro-1 H- indole-5-carbonitryl, 1 -(2,6-Difluorobenzyl)-2,3-dioxo-2,3-dihydro-1 - -indole-5-carboxamide, Sodium 1 -(2,6-difluorobenzyl)-2,3-dioxo-2,3-dihydro-1 H-indole-5-sulphonate, 1 -(2,6- Dif luorobenzyl)-2,3-dioxo-2,3-dihydro-1 H-indole-5-sulphonamide, 1 -(2,6-Dif luorobenzyl)-6- fluoro-1 H-indole-2,3-dione,1 -(2,6-Difluorobenzyl)-6-chloro-1 H-indole-2,3-dione,1 -(2,6- Difluorobenzyl)-6-bromo-1 H-indole-2,3-dione, 1 -(2,6-Difluorobenzyl)-7-trifluoromethyl-1 H- indole-2,3-dione,1 -(2,6-Dif luorobenzyl)-7-metoxy-1 - -indole-2,3-dione,1 -(2,6-Dif luorobenzyl)- 7-bromo-1 H-indole-2,3-dione,1 -(2,6-Difluorobenzyl)-5-fluoro-6-chloro-1 - -indole-2,3-dione,1 - (2,6-Difluorobenzyl)-5-chloro-7-methyl-1 H-indole-2,3-dione,1 -(2,6-Difluorobenzyl)-5,7- dichloro-1 - -indole-2,3-dione,1 -(2,6-Difluorobenzyl)-5,7-dibromo-1 - -indole-2,3-dione.
In an application of the present invention, the compounds shown by Formula II are selected from 1 -(3,4-Difluorobenzyl)-1 H-indole-2,3-dione
Figure imgf000052_0001
and from its derivatives, for instance 1 -(3,4-Difluorobenzyl)-5-(propane-2-yl)-1 H-indole-2,3- dione,1 -(3,4-Difluorobenzyl)-5-t-butyl-1 - -indole-2,3-dione,1 -(3,4-Difluorobenzyl)-5-metoxy- 1 H-indole-2,3-dione,1 -(3,4-Difluorobenzyl)-5-trifluorometoxy-1 - -indole-2,3-dione,1 -(3,4- Difluorobenzyl)-5-fluoro-1 H-indole-2,3-dione,1 -(3,4-Difluorobenzyl)-5-iyodo-1 - -indole-2,3- dione,1 -(3,4-Difluorobenzyl)-2,3-dioxo-2,3-dihydro-1 7-indole-5-carbonitryl, 1 -(3,4- Difluorobenzyl)-2,3-dioxo-2,3-dihydro-1 7-indole-5-carboxamide, Sodium 1 -(3,4- dif luorobenzyl)-2,3-dioxo-2,3-dihydro-1 7-indole-5-sulphonate, 1 -(3,4-Difluorobenzyl)-2,3- dioxo-2,3-dihydro-1 H-indole-5-sulphonamide, 1 -(3,4-Dif luorobenzyl)-7-trifluoromethyl-1 H- indole-2,3-dione,1 -(3,4-Difluorobenzyl)-7-metoxy-1 - -indole-2,3-dione,1 -(3,4-Difluorobenzyl)- 5-fluoro-6-chloro-1 H-indole-2,3-dione, 1 -(3,4-Dif luorobenzyl)-5-chloro-7-methyl-1 H-indole-2,3- dione,1 -(3,4-Difluorobenzyl)-5,7-dichloro-1 H-indole-2,3-dione,1 -(3,4-Difluorobenzyl)-5,7- dibromo-1 7-indole-2,3-dione.
In an application of the present invention, the compounds shown by Formula II are selected from 1 -(3,5-Difluorobenzyl)-1 H-indole-2,3-dione
Figure imgf000053_0001
and from its derivatives, for instance 1-(3,5-Difluorobenzyl)-1H-indole-2,3-dione,1-(3,5- Difluorobenzyl)-5-methyl-1 H-indole-2,3-dione,1 -(3,5-Difluorobenzyl)-5-(propane-2-yl)-1 H- indole-2,3-dione,1-(3,5-Difluorobenzyl)-5-t-butyl-1H-indole-2,3-dione,1-(3,5-Difluorobenzyl)- 5-metoxy-1 --indole-2,3-dione,1-(3,5-Difluorobenzyl)-5-trifluorometoxy-1 H-indole-2,3-dione,1- (3,5-Difluorobenzyl)-5-fluoro-1 --indole-2,3-dione,1-(3,5-Difluorobenzyl)-5-chloro-1 H-indole- 2,3-dione,1-(3,5-Difluorobenzyl)-5-iyodo-1 --indole-2,3-dione,1-(3,5-Difluorobenzyl)-5-nitro- 1H-indole-2,3-dione,1-(3,5-Difluorobenzyl)-2,3-dioxo-2,3-dihydro-1 --indole-5-carbonitryl,1- (3,5-Difluorobenzyl)-2,3-dioxo-2,3-dihydro-1 7-indole-5-carboxamide, sodium 1 -(3,5- difluorobenzyl)-2,3-dioxo-2,3-dihydro-1H-indole-5-sulphonate,1-(3,5-Difluorobenzyl)-2,3- dioxo-2,3-dihydro-1 H-indole-5-sulphonamide, 1 -(3,5-Difluorobenzyl)-6-fluoro-1 H-indole-2,3- dione,1-(3,5-Difluorobenzyl)-6-chloro-1 --indole-2,3-dione,1-(3,5-Difluorobenzyl)-6-bromo- 1H-indole-2,3-dione,1-(3,5-Difluorobenzyl)-7-methyl-1H-indole-2,3-dione,1-(3,5- Difluorobenzyl)-7-trifluoromethyl-1 H-indole-2,3-dione,1 -(3,5-Difluorobenzyl)-7-metoxy-1 H- indole-2,3-dione,1-(3,5-Difluorobenzyl)-7-fluoro-1H-indole-2,3-dione,1-(3,5-Difluorobenzyl)-7- chloro-1 H-indole-2,3-dione,1-(3,5-Difluorobenzyl)-7-bromo-1 7-indole-2,3-dione,1-(3,5- Difluorobenzyl)-5-fluoro-6-chloro-1 --indole-2,3-dione,1-(3,5-Difluorobenzyl)-5-chloro-7- methyl-1H-indole-2,3-dione,1-(3,5-Difluorobenzyl)-5,7-dichloro-1H-indole-2,3-dione,1-(3,5- Difluorobenzyl)-5,7-dibromo-1 H-indole-2,3-dione.
In an application of the present invention, the compounds shown by Formula II are selected from 1 -(2,3-Dichlorobenzyl)-1 H-indole-2,3-dione
Figure imgf000053_0002
and from its derivatives, for instance 1-(2,3-Dichlorobenzyl)-1H-indole-2,3-dione,1-(2,3- Dichlorobenzyl)-5-methyl-1 H-indole-2,3-dione,1 -(2,3-Dichlorobenzyl)-5-(propane-2-yl)-1 H- indole-2,3-dione,1-(2,3-Dichlorobenzyl)-5-t-butyl-1H-indole-2,3-dione,1-(2,3-Dichlorobenzyl)- 5-metoxy-1 H-indole-2,3-dione,1 -(2,3-Dichlorobenzyl)-5-trifluorometoxy-1 H-indole-2,3- dione,1-(2,3-Dichlorobenzyl)-5-fluoro-1 H-indole-2,3-dione,1-(2,3-Dichlorobenzyl)-5-chloro- 1H-indole-2,3-dione,1-(2,3-Dichlorobenzyl)-5-bromo-1H-indole-2,3-dione,1-(2,3- Dichlorobenzyl)-5-iyodo-1 H-indole-2,3-dione,1 -(2,3-Dichlorobenzyl)-5-nitro-1 H-indole-2,3- dione,1-(2,3-Dichlorobenzyl)-2,3-dioxo-2,3-dihydro-1H-indole-5-carbonitryl, 1-(2,3- Dichlorobenzyl)-2,3-dioxo-2,3-dihydro-1 --indole-5-carboxamide, Sodium 1 -(2,3- dichlorobenzyl)-2,3-dioxo-2,3-dihydro-1 7-indole-5-sulphonate, 1-(2,3-Dichlorobenzyl)-2,3- dioxo-2,3-dihydro-1 H-indole-5-sulphonamide, 1-(2,3-Dichlorobenzyl)-6-bromo-1 --indole-2,3- dione,1-(2,3-Dichlorobenzyl)-7-methyl-1H-indole-2,3-dione,1-(2,3-Dichlorobenzyl)-7- trifluoromethyl-1H-indole-2,3-dione,1-(2,3-Dichlorobenzyl)-7-m
(2,3-Dichlorobenzyl)-7-fluoro-1 H-indole-2,3-dione,1 -(2,3-Dichlorobenzyl)-7-chloro-1 H-indole- 2,3-dione,1-(2,3-Dichlorobenzyl)-7-bromo-1H-indole-2,3-dione,1-(2,3-Dichlorobenzyl)-5- fluoro-6-chloro-1 --indole-2,3-dione,1-(2,3-Dichlorobenzyl)-5-chloro-7-methyl-1 H-indole-2,3- dione,1-(2,3-Dichlorobenzyl)-5,7-dichloro-1H-indole-2,3-dione,1-(2,3-Dichlorobenzyl^ dibromo-1 H-indole-2,3-dione. In an application of the present invention, the compounds shown by Formula II are selected ichlorobenzyl)-1 H-indole-2,3-dione
Figure imgf000054_0001
and from its derivatives, for instance 1-(2,4-Dichlorobenzyl)-5-(propane-2-yl)-1H-indole-2,3- dione,1-(2,4-Dichlorobenzyl)-5-t-butyl-1 --indole-2,3-dione,1-(2,4-Dichlorobenzyl)-5-metoxy- 1H-indole-2,3-dione,1-(2,4-Dichlorobenzyl)-5-trifluorometoxy-1H-indole-2,3-dione,1-(2,4-
Dikorobenzyl)-5-iyodo-1 H-indole-2,3-dione,1 -(2,4-Dichlorobenzyl)-2,3-dioxo-2,3-dihydro-1 H- indole-5-carbonitryl, 1 -(2,4-Dichlorobenzyl)-2,3-dioxo-2,3-dihydro-1 7-indole-5-carboxamide, Sodium1-(2,4-dichlorobenzyl)-2,3-dioxo-2,3-dihydro-1 7-indole-5-sulphonate, 1-(2,4- Dichlorobenzyl)-2,3-dioxo-2,3-dihydro-1 H-indole-5-sulphonamide, 1-(2,4-Dichlorobenzyl)-7- trifluoromethyl-1H-indole-2,3-dione,1-(2,4-Dichlorobenzyl)-7-metoxy-1 --indole-2,3-dione,1- (2,4-Dichlorobenzyl)-5-fluoro-6-chloro-1 H-indole-2,3-dione,1-(2,4-Dichlorobenzyl)-5-chloro-7- methyl-1H-indole-2,3-dione,1-(2,4-Dichlorobenzyl)-5,7-chloro-1H-indole-2,3-dione,1-(2,4- Dichlorobenzyl)-5,7-dibromo-1 --indole-2,3-dione. In an application of the present invention, the compounds shown by Formula II are selected from 1 -(2,6-Dichlorobenzyl)-1 H-indole-2,3-dione
Figure imgf000055_0001
and from its derivatives, for instance 1-(2,6-Dichlorobenzyl)-5-(propane-2-yl)-1H-indole-2,3- dione,1-(2,6-Dichlorobenzyl)-5-t-butyl-1 --indole-2,3-dione,1-(2,6-Dichlorobenzyl)-5-metoxy- 1H-indole-2,3-dione,1-(2,6-Dichlorobenzyl)-5-trifluorometoxy-1H-indole-2,3-dione,1-(2,6- Dichlorobenzyl)-5-iyodo-1 H-indole-2,3-dione,1 -(2,6-Dichlorobenzyl)-5-nitro-1 H-indole-2,3- dione,1-(2,6-Dichlorobenzyl)-2,3-dioxo-2,3-dihydro-1H-indole-5-carbonitryl,1-(2,6- Dichlorobenzyl)-2,3-dioxo-2,3-dihydro-1 7-indole-5-carboxamide, sodium 1 -(2,6- dichlorobenzyl)-2,3-dioxo-2,3-dihydro-1 --indole-5-sulphonate,1-(2,6-Dichlorobenzyl)-2,3- dioxo-2,3-dihydro-1 H-indole-5-sulphonamide, 1 -(2,6-Dichlorobenzyl)-7-trifluoromethyl-1 H- indole-2,3-dione,1-(2,6-Dichlorobenzyl)-7-metoxy-1H-indole-2,3-dione,1-(2,6-
Dichlorobenzyl)-5-fluoro-6-chloro-1 --indole-2,3-dione,1-(2,6-Dichlorobenzyl)-5-chloro-7- methyl-1H-indole-2,3-dione,1-(2,6-Dichlorobenzyl)-5,7-dichloro-1H-indole-2,3-dione,1-(2,6-
Dichlorobenzyl)-5,7-dibromo-1 --indole-2,3-dione. In an application of the present invention, the compounds shown by Formula II are selected from 1 -(3,4-Dichlorobenzyl)-1 H-indole-2,3-dione
Figure imgf000055_0002
and from its derivatives, for instance 1-(3,4-Dichlorobenzyl)-5-(propane-2-yl)-1H-indole-2,3- dione,1-(3,4-Dichlorobenzyl)-5-t-butyl-1H-indole-2,3-dione,1-(3,4-Dichlorobenzyl)-5- trifluorometoxy-1 H-indole-2,3-dione,1-(3,4-Dichlorobenzyl)-5-iyodo-1 --indole-2,3-dione,1- (3,4-Dichlorobenzyl)-2,3-dioxo-2,3-dihydro-1 7-indole-5-carbonitryl, 1-(3,4-Dichlorobenzyl)- 2,3-dioxo-2,3-dihydro-1 7-indole-5-carboxamide, Sodium 1 -(3,4-dichlorobenzyl)-2,3-dioxo- 2,3-dihydro-1 7-indole-5-sulphonate, 1-(3,4-Dichlorobenzyl)-7-metoxy-1 --indole-2,3-dione,1- (3,4-Dichlorobenzyl)-5-fluoro-6-chloro-1 H-indole-2,3-dione,1-(3,4-Dichlorobenzyl)-5,7- dichloro-1 --indole-2,3-dione,1-(3,4-Dichlorobenzyl)-5,7-dibromo-1 --indole-2,3-dione. In an application of the present invention, the compounds shown by Formula II are selected hlorobenzyl)-1 H-indole-2,3-dione
Figure imgf000056_0001
and from its derivatives, for instance 1-(3,5-Dichlorobenzyl)-5-methyl-1H-indole-2,3-dione,1- (3,5-Dichlorobenzyl)-5-(propane-2-yl)-1H-indole-2,3-dione,1-(3,5-Dichlorobenzyl)-5-t-butyl- 1H-indole-2,3-dione,1-(3,5-Dichlorobenzyl)-5-metoxy-1 7-indole-2,3-dione,1-(3,5- Dichlorobenzyl)-5-trifluorometoxy-1 H-indole-2,3-dione,1 -(3,5-Dichlorobenzyl)-5-fluoro-1 7- indole-2,3-dione,1-(3,5-Dichlorobenzyl)-5-chloro-1 --indole-2,3-dione,1-(3,5-Dichlorobenzyl)- 5-bromo-1 H-indole-2,3-dione,1-(3,5-Dichlorobenzyl)-5-iyodo-1 --indole-2,3-dione,1-(3,5- Dichlorobenzyl)-5-nitro-1H-indole-2,3-dione,1-(3,5-Dichlorobenzyl)-2,3-dioxo-2,3-dihydro-1H- indole-5-carbonitryl, 1 -(3,5-Dichlorobenzyl)-2,3-dioxo-2,3-dihydro-1 7-indole-5-carboxamide, Sodium 1 -(3,5-dichlorobenzyl)-2,3-dioxo-2,3-dihydro-1 7-indole-5-sulphonate, 1 -(3,5- Dichlorobenzyl)-2,3-dioxo-2,3-dihydro-1 H-indole-5-sulphonamide, 1-(3,5-Dichlorobenzyl)-6- fluoro-1H-indole-2,3-dione,1-(3,5-Dichlorobenzyl)-6-chloro-1H-indole-2,3-dione,1-(3,5- Dichlorobenzyl)-6-bromo-1H-indole-2,3-dione,1-(3,5-Dichlorobenzyl)-7-methyl-1H-indole-2,3- dione,1-(3,5-Dichlorobenzyl)-7-trifluoromethyl-1H-indole-2,3-dione,1-(3,5-Dichlorobenzyl)-7- metoxy-1 --indole-2,3-dione,1-(3,5-Dichlorobenzyl)-7-fluoro-1 --indole-2,3-dione,1-(3,5- Dichlorobenzyl)-7-chloro-1 H-indole-2,3-dione,1-(3,5-Dichlorobenzyl)-7-bromo-1 --indole-2,3- dione,1-(3,5-Dichlorobenzyl)-5-fluoro-6-chloro-1 --indole-2,3-dione,1-(3,5-Dichlorobenzyl)-5- chloro-7-methyl-1H-indole-2,3-dione,1-(3,5-Dichlorobenzyl)-5,7-dichloro-1H-indole-2,3- dione,1 -(3,5-Dichlorobenzyl)-5,7-dibromo-1 H-indole-2,3-dione.
In an application of the present invention, the compounds shown by Formula II are selected from 1 -(2-Chloro-4-fluorobenzyl)-1 H-indole-2,3-dione
Figure imgf000056_0002
and from its derivatives, for instance 1-(2-Chloro-4-fluorobenzyl)-5-(propane-2-yl)-1H-indole- 2,3-dione,1-(2-Chloro-4-fluorobenzyl)-5-t-butyl-1H-indole-2,3-dione,1-(2-Chloro-4- fluorobenzyl)-5-metoxy-1 Hindole-2,3-dio^
1 H-indole-2,3-dione,1 -(2-Chloro-4-fluorobenzyl)-5-nitro-1 H-indole-2,3-dion^
fluorobenzyl)-2,3-dioxo-2,3-dihydro-1 Hindole-5-carbonitryl, 1 -(2-Chloro-4-fluorobenzyl)-2,3- dioxo-2,3-dihydro-1 - -indole-5-carboxamide, Sodium 1 -(2-chloro-4-fluorobenzyl)-2,3-dioxo- 2,3-dihydro-1 H-indole-5-sulphonate, 1 -(2-Chloro-4-fluorobenzyl)-2,3-dioxo-2,3-dihydro-1 H- indole-5-sulphonamide, 1 -(2-Chloro-4-fluorobenzyl)-7-trifluoromethyl-1 H-indole-2,3-dione,1 - (2-Chloro-4-fluorobenzyl)-7-metoxy-1 -/-indole-2,3-dione,1 -(2-Chloro-4-fluorobenzyl)-5-fluoro- 6-chloro-1 H-indole-2,3-dione,1 -(2-Chloro-4-fluorobenzyl)-5-chloro-7-methyl-1 H
dione,1 -(2-Chloro-4-fluorobenzyl)-5,7-dichloro-1 H-indole-2,3-dione,1 -(2-Chloro-4- fluorobenzyl)-5,7-dibromo-1 H-indole-2,3-dione.
In an application of the present invention, the compounds shown by Formula II are selected oro-6-fluorobenzyl)-1 H-indole-2,3-dione
Figure imgf000057_0001
and from its derivatives, for instance 1 -(2-Chloro-6-fluorobenzyl)-5-(propane-2-yl)-1 H-indole- 2,3-dione,1 -(2-Chloro-6-fluorobenzyl)-5-t-butyl-1 H-indole-2,3-dione,1 -(2-Chloro-6- fluorobenzyl)-5-metoxy-1 - -indole-2,3-dione,1 -(2-Chloro-6-fluorobenzyl)-5-trifluorometoxy- 1 H-indole-2,3-dione,1 -(2-Chloro-6-fluorobenzyl)-5-iyodo-1 H-indole-2,3-dione,1 -(2-Chloro-6- fluorobenzyl)-2,3-dioxo-2,3-dihydro-1 7-indole-5-carbonitryl, 1 -(2-Chloro-6-fluorobenzyl)-2,3- dioxo-2,3-dihydro-1 7-indole-5-carboxamide, Sodium 1 -(2-chloro-6-fluorobenzyl)-2,3-dioxo- 2,3-dihydro-1 H-indole-5-sulphonate, 1 -(2-Chloro-6-fluorobenzyl)-2,3-dioxo-2,3-dihydro-1 H- indole-5-sulphonamide, 1 -(2-Chloro-6-fluorobenzyl)-7-trifluoromethyl-1 H-indole-2,3-dione,1 - (2-Chloro-6-fluorobenzyl)-7-metoxy-1 - -indole-2,3-dione,1 -(2-Chloro-6-fluorobenzyl)-5-fluoro- 6-chloro-1 H-indole-2,3-dione,1 -(2-Chloro-6-fluorobenzyl)-5-chloro-7-methyl-1 H-indole-2,3- dione,1 -(2-Chloro-6-fluorobenzyl)-5,7-dichloro-1 H-indole-2,3-dione,1 -(2-Chloro-6- fluorobenzyl)-5,7-dibromo-1 - -indole-2,3-dione.
In an application of the present invention, the compounds shown by Formula II are selected from 1 -(3,4,5-Trif luorobenzyl)-1 H-indole-2,3-dione
Figure imgf000058_0001
and from its derivatives, for instance 1 -(3,4,5-Trifluorobenzyl)-5-methyl-1 /-/-indole-2,3- dione,1 -(3,4,5-Trifluorobenzyl)-5-(propane-2-yl)-1 /-/-indole-2,3-dione,1 -(3,4,5- Trifluorobenzyl)-5-t-butyl-1 /-/-indole-2,3-dione,1 -(3,4,5-Trifluorobenzyl)-5-metoxy-1 H-indole- 2,3-dione,1 -(3,4,5-Trifluorobenzyl)-5-trifluorometoxy-1 7-indole-2,3-dione,1 -(3,4,5-
Trifluorobenzyl)-5-fluoro-1 - -indole-2,3-dione,1 -(3,4, 5-Trifluorobenzyl)-5-chloro-1 /-/-indole- 2,3-dione,1 -(3,4,5-Trifluorobenzyl)-5-bromo-1 /-/-indole-2,3-dione,1 -(3,4,5-Trifluorobenzyl)-5- iyodo-1 /7-indole-2,3-dione,1 -(3,4,5-Trifluorobenzyl)-2,3-dioxo-2,3-dihydro-1 /-/-indole-5- carbonitryl, 1 -(3,4,5-Trifluorobenzyl)-2,3-dioxo-2,3-dihydro-1 /7-indole-5-carboxamide, Sodium 1 -(3,4,5-trifluorobenzyl)-2,3-dioxo-2,3-dihydro-1 H-indole-5-sulphonate, 1 -(3,4,5-
Trifluorobenzyl)-2,3-dioxo-2,3-dihydro-1 H-indole-5-sulphonamide, 1 -(3,4,5-Trifluorobenzyl)-6- fluoro-1 H-indole-2,3-dione,1 -(3,4,5-Trifluorobenzyl)-6-chloro-1 H-indole-2,3-dione,1 -(3,4,5- Trifluorobenzyl)-6-bromo-1 /7-indole-2,3-dione,1 -(3,4, 5-Trifluorobenzyl)-7-methyl-1 /-/-indole- 2,3-dione,1 -(3,4,5-Trifluorobenzyl)-7-trifluoromethyl-1 H-indole-2,3-dione,1 -(3,4,5- Trifluorobenzyl)-7-metoxy-1 H-indole-2,3-dione,1 -(3,4,5-Trifluorobenzyl)-7-fluoro-1 /-/-indole- 2,3-dione,1 -(3,4,5-Trifluorobenzyl)-7-chloro-1 H-indole-2,3-dione,1 -(3,4,5-Trifluorobenzyl)-7- bromo-1 /-/-indole-2,3-dione,1 -(3,4,5-Trifluorobenzyl)-5-fluoro-6-chloro-1 /-/-indole-2,3-dione,1 - (3,4,5-Trifluorobenzyl)-5-chloro-7-methyl-1 H-indole-2,3-dione,1 -(3,4,5-Trifluorobenzyl)-5,7- dichloro-1 /-/-indole-2,3-dione,1 -(3,4,5-Trifluorobenzyl)-5,7-dibromo-1 H-indole-2,3-dione.
In an application of the present invention, the compounds shown by Formula II are selected
6-Pentafluorobenzyl)-1 H-indole-2,3-dione
Figure imgf000058_0002
and from its derivatives, for instance 1 -(2,3,4,5,6-Pentafluorobenzyl)-5-methyl-1 H-indole-2,3- dione,1 -(2,3,4,5,6-Pentafluorobenzyl)-5-(propane-2-yl)-1 Hindole-2,3-dione,1 -(2,3,4,5,6- Pentafluorobenzyl)-5-t-butyl-1 /-/-indole-2,3-dione,1 -(2,3,4,5,6-Pentafluorobenzyl)-5-metoxy- 1 /-/-indole-2,3-dione,1 -(2,3,4,5,6-Pentafluorobenzyl)-5-trifluorometoxy-1 /7-indole-2,3-dione,1 - (2,3,4,5,6-Pentafluorobenzyl)-5-fluoro-1H-indole-2,3-dione,1-(2,3,4,5,6-Pentafluorobenzyl)-5- chloro-1 H-indole-2,3-dione -(2,3,4,5,6-Pentafluorobenzyl)-5-bromo-1 --indole-2,3-dione,1- (2,3,4,5,6-Pentafluorobenzyl)-5-iyodo-1H-indole-2,3-dione,1-(2,3,4,5,6-Pentafluorobenzyl)-5- nitro-1H-indole-2,3-dione,1-(2,3,4,5,6-Pentafluorobenzyl)-2,3-dioxo-2,3-dihydro-1H-in carbonitryl, 1 -(2,3,4,5,6-Pentafluorobenzyl)-2,3-dioxo-2,3-dihydro-1 --indole-5-carboxamide, Sodium 1 -(2,3,4,5,6-pentaf luorobenzyl)-2,3-dioxo-2,3-dihydro-1 7-indole-5-sulphonate, 1 - (2,3,4,5,6-Pentafluorobenzyl)-2,3-dioxo-2,3-dihydro-1 H-indole-5-sulphonamide, 1 -(2,3,4,5,6- Pentafluorobenzyl)-6-fluoro-1H-indole-2,3-dione,1-(2,3,4,5,6-Pentafluorobenzyl)-6-chloro-1H- indole-2,3-dione,1-(2,3,4,5,6-Pentafluorobenzyl)-6-bromo-1H-indole-2,3-dione,1 -(2,3,4,5,6- Pentafluorobenzyl)-7-methyl-1 H-indole-2,3-dione,1 -(2,3,4,5,6-Pentafluorobenzyl)-7- trifluoromethyl-1H-indole-2,3-dione,1-(2,3,4,5,6-Pentafluorobenzyl)-7-metoxy-1 H-indole-2,3- dione,1-(2,3,4,5,6-Pentafluorobenzyl)-7-fluoro-1H-indole-2,3-dione,1-(2,3, 4,5,6- Pentafluorobenzyl)-7-chloro-1 --indole-2,3-dione,1-(2,3,4,5,6-Pentafluorobenzyl)-7-bromo- 1H-indole-2,3-dione,1-(2,3,4,5,6-Pentafluorobenzyl)-5-fluoro-6-chloro-1H-indole-2,3-dione,1- (2,3,4,5,6-Pentafluorobenzyl)-5-chloro-7-methyl-1 H-indole-2,3-dione,1 -(2,3,4,5,6- Pentafluorobenzyl)-5,7-dichloro-1 --indole-2,3-dione.
In an application of the present invention, the compounds shown by Formula II are selected from 1 -Naphtylmethyl-1 H-indole-2,3-dione
Figure imgf000059_0001
and from its derivatives, for instance 1-(1-naphtylmethyl)-5-methyl-1H-indole-2,3-dione,1-(1- naphtylmethyl)-5-(propane-2-yl)-1H-indole-2,3-dione,1-(1-naphtylmethyl)-5-t-butyl-1H-indole- 2,3-dione,1-(1-naphtylmethyl)-5-metoxy-1 --indole-2,3-dione,1-(1-naphtylmethyl)-5- trifluorometoxy-1 H-indole-2,3-dione, 1 -(1 -naphtylmethyl)-5-fluoro-1 H-indole-2,3-dione,1 -(1 - naphtylmethyl)-2,3-dioxo-2,3-dihydro-1 7-indole-5-carbonitryl, 1-(1-naphtylmethyl)-2,3-dioxo- 2,3-dihydro-1 7-indole-5-carboxamide, Sodium 1 -(1 -naphtylmethyl)-2,3-dioxo-2,3-dihydro-1 H- indole-5-sulphonate, 1 -(1 -naphtylmethyl)-2,3-dioxo-2,3-dihydro-1 H-indole-5-sulphonamide, 1 -(1 -naphtylmethyl)-6-fluoro-1 H-indole-2,3-dione,1 -(1 -naphtylmethyl)-6-chloro-1 H-indole-2,3- dione,1 -(1 -naphtylmethyl)-6-bromo-1 H-indole-2,3-dione,1 -(1 -naphtylmethyl)-7-methyl-1 H- indole-2,3-dione,1-(1-naphtylmethyl)-7-trifluoromethyl-1 H-indole-2,3-dione,1-(1- naphtylmethyl)-7-metoxy-1 --indole-2,3-dione,1-(1-naphtylmethyl)-7-fluoro-1 --indole-2,3- dione,1-(1-naphtylmethyl)-7-chloro-1 --indole-2,3-dione,1-(1-naphtylmethyl)-7-bromo-1 -- indole-2,3-dione,1-(1-naphtylmethyl)-5-fluoro-6-chloro-1 H-indole-2,3-dione,1-(1- naphtylmethyl)-5-chloro-7-methyl-1 H-indole-2,3-dione,1-(1-naphtylmethyl)-5,7-dichloro-1 -- indole-2,3-dione. In an application of the present invention, the compounds shown by Formula II are selected from 2-Na H-indole-2,3-dione
Figure imgf000060_0001
and from its derivatives, for instance 1-(2-naphtylmethyl)-5-methyl-1H-indole-2,3-dione,1-(2- naphtylmethyl)-5-(propane-2-yl)-1H-indole-2,3-dione,1-(2-naphtylmethyl)-5-t-butyl-1H-indole- 2,3-dione,1-(2-naphtylmethyl)-5-metoxy-1H-indole-2,3-dione,1-(2-naphtylmethyl)-5- trifluorometoxy-1 H-indole-2,3-dione,1-(2-naphtylmethyl)-5-fluoro-1 --indole-2,3-dione,1-(2- naphtylmethyl)-5-nitro-1 H-indole-2,3-dione,1 -(2-naphtylmethyl)-2,3-dioxo-2,3-dihydro-1 H- indole-5-carbonitryl, Sodium 1 -(2-naphtylmethyl)-2,3-dioxo-2,3-dihydro-1 H-indole-5- sulphonate, 1-(2-naphtylmethyl)-2,3-dioxo-2,3-dihydro-1 --indole-5-sulphonamide, 1-(2- naphtylmethyl)-6-fluoro-1H-indole-2,3-dione,1-(2-naphtylmethyl)-6-chloro-1H-indole-2,3- dione,1-(2-naphtylmethyl)-6-bromo-1 H-indole-2,3-dione,1-(2-naphtylmethyl)-7-methyl-1 H- indole-2,3-dione,1-(2-naphtylmethyl)-7-trifluoromethyl-1H-indole-2,3-dione,1-(2- naphtylmethyl)-7-metoxy-1 --indole-2,3-dione,1-(2-naphtylmethyl)-7-fluoro-1 --indole-2,3- dione,1-(2-naphtylmethyl)-7-chloro-1 --indole-2,3-dione,1-(2-naphtylmethyl)-7-bromo-1 H- indole-2,3-dione,1-(2-naphtylmethyl)-5-fluoro-6-chloro-1H-indole-2,3-dione,1-(2- naphtylmethyl)-5-chloro-7-methyl-1 H-indole-2,3-dione,1-(2-naphtylmethyl)-5,7-dichloro-1 -- indole-2,3-dione.
From another perspective, the present invention relates to 2-indolinon derivative molecules whose general chemical structure is shown by Formula III:
. Re
■4 ϊϊϊ \
Rv In Formula III;
is hydrogen, alkyl, metoxy, trifluorometoxy, halogen, nitro, carbonitryl, carboxamide, sodium sulphonate, sulphonamide. F>2 represents hydrogen, halogen.
R3 represents hydrogen, alkyl, trifluoromethyl, metoxy, halogen.
R4 represents hydrogen, alkyl, alkenil, aralkyl, alkanoic acid, alkanoic acid alkyl ester.
R5, R6 and R7 represent sulphonamide in an independent manner. In Formula III,
The alkyl substituent in R^ defines methyl, isopropyl and tersiyer butyl groups.
The halogen in R^ is fluor, chlor, bromine and iodine.
The halogen in R2 is fluor, chlor and bromine. The halogen in R3 represents fluor, chlor and bromine.
In a preferred application of the present invention, in R1 : fluor groups are defined and in R2, chlor groups are defined, in R1 : chlor groups are defined and in R3, methyl groups are defined, in R^ and R3, dichlor groups are defined, in R^ and R3, dibromine groups are defined.
R4 represents saturated or unsaturated, branched or unbranched Ci_3 alkyl, branched or unbranched C2.4 alkanoic acid, C2.4 branched or unbranched alkanoic acid, branched or unbranched C2.4 alkyl ester.
In R4, as saturated or unsaturated, branched or unbranched Ci_3 alkyl, methyl, ethyl, n- propyl, isopropyl and allyl are defined.
In R4, branched or unbranched C2.4 alkanoic acid is represented by acetic acid, 2- methylacetic acid, propanonic acid, butanoic acid. In R4, branched or unbranched C2.4 alkyl ester of the C2.4 branched or unbranched alkanoic acid is represented by ethyl acetate, isopropyl acetate, tersiyer butyl acetate, ethyl propanoate, ethyl 2-methylacetate, ethyl butanoate. In R4, substituted benzyl carries Ci_4 straight or branched alkyl, trifluoromethyl, metoxy, trifluorometoxy, fluor, chlor, bromine, iodine, nitro, carbonitryl, carboxy, hydroxy groups in positions 2, 3 or 4 of the phenyl ring. Here, Ci_4 straight or branched alkyl defines methyl, ethyl, isopropyl and tersiyer butyl groups. Substituted benzyl moreover carries 2,4-dimethyl, 2,5-dimethyl, 2,6-dimethyl, 3,4-dimethyl, 3,5-dimethyl, 2,3-difluor, 2,4-difluor, 2,5-difluor, 2,6- difluor, 3,4-difluor, 3,5-difluor, 2,4-dichlor, 2,6-dichlor, 3,4-dichlor, 3,5-dichlor, 2-chlor-4-fluor, 2-chlor-6-fluor, 3,4,5-trifluor, 2,3,4,5,6-pentafluor in the phenyl ring.
In the sulphonamide benzene ring in R5, R6 and R7, when it is placed in R5, hydrogen is provided in R6 and R7, when it is placed in R6, hydrogen is provided in R5 and R7, and when it is placed in R7, hydrogen is provided in R5 and R6.
The general chemical name of the compounds shown by Formula III is 2-(2-oxo-1 ,2-dihydro- 3 - -indole-3-yliden)-/V-(2/3/4-sulphamoilphenyl)hydrazine carbothioamide derivatives. In order to generally describe these molecules within the scope of the present invention, "Formula III" and/or "2-(2-oxo-1 ,2-dihydro-3H-indole-3-yliden)-/V-(2/3/4 sulphamoilphenyl) hydrazine carbothioamide" and/or 1 H-indole-2,3-dione 3-/V-(2/3/4-sulphamoilphenyl) thiosemi-carbazone terms can be interchangeably used.
In an application of the present invention, the compounds shown by Formula III are selected from 2-(2-oxo-1 ,2-dihydro-3W-indole-3-yliden)-A -(2-sulphamoilphenyl) hydrazine- carbothioamide
Figure imgf000062_0001
and from its derivatives, for instance 2-[5-(propane-2-yl)-2-oxo-1 ,2-dihydro-3H-indole-3- yliden]-/V-(2-sulphamoilphenyl)hydrazinecarbothioamide, 2-(5-t-butyl-2-oxo-1 ,2-dihydro-3 7- indole-3-yliden)-/V-(2-sulphamoilphenyl)hydrazinecarbothioamide, 2-(5-metoxy-2-oxo-1 ,2- dihydro-3 - -indole-3-yliden)-/V-(2-sulphamoilphenyl)hydrazinecarbothioamide, 2-(5-iyodo-2- oxo-1 ,2-dihydro-3 - -indole-3-yliden)-/V-(2-sulphamoilphenyl)hydrazinecarbothioamide, 2-(5- cyano-2-oxo-1 ,2-dihydro-3 - -indole-3-yliden)-/V-(2-sulphamoilphenyl) hydrazinecarbothio- amide, 2-(5-karbamoil-2-oxo-1 ,2-dihydro-3 - -indole-3-yliden)-/V-(2-sulphamoilphenyl) hydrazinecarbothioamide, Sodium 3-[2-oxo-3-[2-(sulphamoilphenyl)karbamotioil]hydrazine- yliden]-2,3-dihydro-1 7-indole-5-sulphonate, 2-(5-sulphamoil-2-oxo-1 ,2-dihydro-3 7-indole-3- yliden)-/V-(2-sulphamoilphenyl)hydrazinecarbothioamide, 2-(6-fluoro-2-oxo-1 ,2-dihydro-3 7- indole-3-yliden)-/V-(2-sulphamoilphenyl)hydrazinecarbothioamide, 2-(6-chloro-2-oxo-1 ,2- dihydro-3 - -indole-3-yliden)-/V-(2-sulphamoilphenyl)hydrazinecarbothioamide, 2-(6-bromo-2- oxo-1 ,2-dihydro-3 - -indole-3-yliden)-/V-(2-sulphamoilphenyl)hydrazinecarbothioamide, 2-(7- methyl-2-oxo-1 ,2-dihydro-3 - -indole-3-yliden)-/V-(2-sulphamoilphenyl)
hydrazinecarbothioamide, 2-(7-trifluoromethyl-2-oxo-1 ,2-dihydro-3 - -indole-3-yliden)-/V-(2- sulphamoilphenyl)hydrazinecarbothioamide, 2-(7-metoxy-2-oxo-1 ,2-dihydro-3 7-indole-3- yliden)-/V-(2-sulphamoilphenyl)hydrazinecarbothioamide, 2-(7-fluoro-2-oxo-1 ,2-dihydro-3 7- indole-3-yliden)-/V-(2-sulphamoilphenyl)hydrazinecarbothioamide, 2-(7-chloro-2-oxo-1 ,2- dihydro-3 - -indole-3-yliden)-/V-(2-sulphamoilphenyl) hydrazinecarbothioamide, 2-(7-bromo-2- oxo-1 ,2-dihydro-3 - -indole-3-yliden)-/V-(2-sulphamoilphenyl)hydrazinecarbothioamide, 2-(5- fluoro-6-chloro-2-oxo-1 ,2-dihydro-3 - -indole-3-yliden)-/V-(2-sulphamoilphenyl)
hydrazinecarbothioamide, 2-(5-chloro-7-methyl-2-oxo-1 ,2-dihydro-3 - -indole-3-yliden)-/V-(2- sulphamoilphenyl)hydrazinecarbothioamide, 2-(5,7-dichloro-2-oxo-1 ,2-dihydro-3 7-indole-3- yliden)-/V-(2-sulphamoilphenyl)hydrazinecarbothioamide.
In an application of the present invention, the compounds shown by Formula III are selected from 2-(1-Methyl-2-oxo-1 ,2-dihydro-3W-indole-3-yliden)-A -(2-sulphamoilphenyl) hydrazinecarbothioamide
Figure imgf000063_0001
and from its derivatives, for instance 2-(1 -methyl-2-oxo-1 ,2-dihydro-3H-indole-3-yliden)-/V-(2- sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 ,5-dimethyl-2-oxo-1 ,2-dihydro-3 7-indole-3- yliden)-/V-(2-sulphamoilphenyl)hydrazinecarbothioamide, 2-[1 -methyl-5-(propane-2-yl)-2-oxo- 1 ,2-dihydro-3 - -indole-3-yliden]-/V-(2-sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 - methyl-5-t-butyl-2-oxo-1 ,2-dihydro-3H-indole-3-yliden)-/V-(2- sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 -methyl-5-metoxy-2-oxo-1 ,2-dihydro-3 7- indole-3-yliden)-/V-(2-sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 -methyl-5- trifluorometoxy-2-oxo-1 ,2-dihydro-3H-indole-3-yliden)-/V-(2- sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 -methyl-5-f luoro-2-oxo-1 ,2-dihydro-3 7- indole-3-yliden)-/V-2-sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 -methyl-5-chloro-2-oxo- 1 ,2-dihydro-3 - -indole-3-yliden)-/V-(2-sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 - methyl-5-bromo-2-oxo-1 ,2-dihydro-3 - -indole-3-yliden)-/V-(2-sulphamoilphenyl) hydrazinecarbothioamide, 2-(1 -methyl-5-iyodo-2-oxo-1 ,2-dihydro-3 - -indole-3-yliden)-/V-(2- sulphamoilphenyl) hydrazinecarbothioamide, 2-(1 -methyl-5-nitro-2-oxo-1 ,2-dihydro-3 7- indole-3-yliden)-/V-(2-sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 -methyl-5-cyano-2- oxo-1 ,2-dihydro-3 - -indole-3-yliden)-/V-(2-sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 - methyl-5-karbamoil-2-oxo-1 ,2-dihydro-3H-indole-3-yliden)-/V-(2- sulphamoilphenyl)hydrazinecarbothioamide, Sodium 3-[1 -methyl-2-oxo-3-[2-
(sulphamoilphenyl)karbamotioil]hydrazineiliden]-2,3-dihydro-1 7-indole-5-sulphonate, 2-(1 - methyl-5-sulphamoil-2-oxo-1 ,2-dihydro-3 - -indole-3-yliden)-/V-(2- sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 -methyl-6-f luoro-2-oxo-1 ,2-dihydro-3 7- indole-3-yliden)-/V-(2-sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 -methyl-6-chloro-2- oxo-1 ,2-dihydro-3 - -indole-3-yliden)-/V-(2-sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 - methyl-6-bromo-2-oxo-1 ,2-dihydro-3H-indole-3-yliden)-/V-(2- sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 -methyl-7-methyl-2-oxo-1 ,2-dihydro-3 7- indole-3-yliden)-/V-(2-sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 -methyl-7- trifluoromethyl-2-oxo-1 ,2-dihydro-3H-indole-3-yliden)-/V-(2- sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 -methyl-7-metoxy-2-oxo-1 ,2-dihydro-3 7- indole-3-yliden)-/V-(2-sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 -methyl-7-fluoro-2-oxo- 1 ,2-dihydro-3 - -indole-3-yliden)-/V-(2-sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 - methyl-7-chloro-2-oxo-1 ,2-dihydro-3H-indole-3-yliden)-/V-(2- sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 -methyl-7-bromo-2-oxo-1 ,2-dihydro-3 7- indole-3-yliden)-/V-(2-sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 -methyl-5-fluoro-6- chloro-2-oxo-1 ,2-dihydro-3H-indole-3-yliden)-/V-(2- sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 -methyl-5-chloro-7-methyl-2-oxo-1 ,2- dihydro-3 - -indole-3-yliden)-/V-(2-sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 -methyl- 5,7-dichloro-2-oxo-1 ,2-dihydro-3H-indole-3-yliden)-/V-(2- sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 -methyl-5,7-dibromo-2-oxo-1 ,2-dihydro-3 7- indole-3-yliden)-/V-(2-sulphamoilphenyl)hydrazinecarbothioamide.
In an application of the present invention, the compounds shown by Formula III are selected from 2-(1-Ethyl-2-oxo-1 ,2-dihydro-3W-indole-3-yliden)-A -(2-sulphamoilphenyl) hydrazinecarbothioamide
Figure imgf000064_0001
and from its derivatives, for instance 2-(1 -ethyl-2-oxo-1 ,2-dihydro-3 - -indole-3-yliden)-/V-(2- sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 -ethyl-5-methyl-2-oxo-1 ,2-dihydro-3 7- indole-3-yliden)-/V-(2-sulphamoilphenyl)hydrazinecarbothioamide, 2-[1 -ethyl-5-(propane-2- yl)-2-oxo-1 ,2-dihydro-3 - -indole-3-yliden]-/V-(2-sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 -ethyl-5-t-butyl-2-oxo-1 ,2-dihydro-3H-indole-3-yliden)-/V-(2- sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 -ethyl-5-metoxy-2-oxo-1 ,2-dihydro-3 7- indole-3-yliden)-/V-(2-sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 -ethyl-5- trifluorometoxy-2-oxo-1 ,2-dihydro-3 - -indole-3-yliden)-/V-(2- sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 -ethyl-5-fluoro-2-oxo-1 ,2-dihydro-3 7-indole- 3-yliden)-/V-(2-sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 -ethyl-5-chloro-2-oxo-1 ,2- dihydro-3 - -indole-3-yliden)-/V-(2-sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 -ethyl-5- bromo-2-oxo-1 ,2-dihydro-3H-indole-3-yliden)-/V-(2- sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 -ethyl-5-iyodo-2-oxo-1 ,2-dihydro-3 7-indole- 3-yliden)-/V-(2-sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 -ethyl-5-nitro-2-oxo-1 ,2- dihydro-3 - -indole-3-yliden)-/V-(2-sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 -ethyl-5- cyano-2-oxo-1 ,2-dihydro-3H-indole-3-yliden)-/V-(2- sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 -ethyl-5-karbamoil-2-oxo-1 ,2-dihydro-3 7- indole-3-yliden)-/V-(2-sulphamoilphenyl)hydrazinecarbothioamide, Sodium 3-[1 -ethyl-2-oxo-3- [2-(sulphamoilphenyl)karbamotioil]hydrazineiliden]-2,3-dihydro-1 7-indole-5-sulphonate, 2-(1 - ethyl-5-sulphamoil-2-oxo-1 ,2-dihydro-3H-indole-3-yliden)-/V-(2- sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 -ethyl-6-fluoro-2-oxo-1 ,2-dihydro-3 7-indole- 3-yliden)-/V-(2-sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 -methyl-6-chloro-2-oxo-1 ,2- dihydro-3 - -indole-3-yliden)-/V-(2-sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 -ethyl-6- bromo-2-oxo-1 ,2-dihydro-3H-indole-3-yliden)-/V-(2- sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 -ethyl-7-methyl-2-oxo-1 ,2-dihydro-3 7- indole-3-yliden)-/V-(2-sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 -ethyl-7- trifluoromethyl-2-oxo-1 ,2-dihydro-3H-indole-3-yliden)-/V-(2- sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 -ethyl-7-metoxy-2-oxo-1 ,2-dihydro-3 7- indole-3-yliden)-/V-(2-sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 -ethyl-7-fluoro-2-oxo- 1 ,2-dihydro-3 - -indole-3-yliden)-/V-(2-sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 - methyl-7-chloro-2-oxo-1 ,2-dihydro-3H-indole-3-yliden)-/V-(2- sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 -ethyl-7-bromo-2-oxo-1 ,2-dihydro-3 7-indole- 3-yliden)-/V-(2-sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 -ethyl-5-fluoro-6-chloro-2- oxo-1 ,2-dihydro-3 - -indole-3-yliden)-/V-(2-sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 - ethyl-5-chloro-7-methyl-2-oxo-1 ,2-dihydro-3H-indole-3-yliden)-/V-(2- sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 -ethyl-5,7-dichloro-2-oxo-1 ,2-dihydro-3 7- indole-3-yliden)-N-(2-sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 -ethyl-5,7-dibromo-2- oxo-1 ,2-dihydro-3Hindole-3-yliden)-N-(2-sulphamoilph
In an application of the present invention, the compounds shown by Formula III are selected from 2-(1 -Allyl-2-oxo-1 ,2-dihydro-3W-indole-3-yliden)-A -(2-sulphamoilphenyl) e
Figure imgf000066_0001
and from its derivatives, for instance 2-[1 -(2-propenyl)-2-oxo-1 ,2-dihydro-3 7-indole-3-yliden]- /V-(2-sulphamoilphenyl)hydrazinecarbothioamide, 2-[1 -(2-propenyl)-5-methyl-2-oxo-1 ,2- dihydro-3 - -indole-3-yliden]-/V-(2-sulphamoilphenyl)hydrazinecarbothioamide,2-[1 -(2- propenyl)-5-(propane-2-yl)-2-oxo-1 ,2-dihydro-3H-indole-3-yliden]-/V-(2- sulphamoilphenyl)hydrazinecarbothioamide, 2-[1 -(2-propenyl)-5-t-butyl-2-oxo-1 ,2-dihydro- 3H-indole-3-yliden]-/V-(2-sulphamoilphenyl)hydrazinecarbothioamide, 2-[1 -(2-propenyl)-5- metoxy-2-oxo-1 ,2-dihydro-3H-indole-3-yliden]-/V-(2- sulphamoilphenyl)hydrazinecarbothioamide, 2-[1 -(2-propenyl)-5-trif luorometoxy-2-oxo-1 ,2- dihydro-3 - -indole-3-yliden]-/V-(2-sulphamoilphenyl)hydrazinecarbothioamide, 2-[1 -(2- propenyl)-5-fluoro-2-oxo-1 ,2-dihydro-3 - -indole-3-yliden]-/V-(2- sulphamoilphenyl)hydrazinecarbothioamide, 2-[1 -(2-propenyl)-5-chloro-2-oxo-1 ,2-dihydro- 3H-indole-3-yliden]-/V-(2-sulphamoilphenyl)hydrazinecarbothioamide, 2-[1 -(2-propenyl)-5- bromo-2-oxo-1 ,2-dihydro-3H-indole-3-yliden]-/V-(2- sulphamoilphenyl)hydrazinecarbothioamide, 2-[1 -(2-propenyl)-5-iyodo-2-oxo-1 ,2-dihydro-3H- indole-3-yliden]-/V-(2-sulphamoilphenyl)hydrazinecarbothioamide, 2-[1 -(2-propenyl)-5-nitro-2- oxo-1 ,2-dihydro-3 - -indole-3-yliden]-/V-(2-sulphamoilphenyl)hydrazinecarbothioamide, 2-[1 - (2-propenyl)-5-cyano-2-oxo-1 ,2-dihydro-3H-indole-3-yliden]-/V-(2- sulphamoilphenyl)hydrazinecarbothioamide, 2-[1 -(2-propenyl)-5-karbamoil-2-oxo-1 ,2- dihydro-3 - -indole-3-yliden]-/V-(2-sulphamoilphenyl)hydrazinecarbothioamide, Sodium 3-[1 - (2-propenyl)-2-oxo-3-[2-(sulphamoilphenyl)karbamotioil]hydrazineiliden]-2,3-dihydro-1 H- indole-5-sulphonate, 2-[1 -(2-propenyl)-5-sulphamoil-2-oxo-1 ,2-dihydro-3H-indole-3-yliden]-/V- (2-sulphamoilphenyl)hydrazinecarbothioamide,2-[1 -(2-propenyl)-6-fluoro-2-oxo-1 ,2-dihydro- 3 - -indole-3-yliden]-/V-(2-sulphamoilphenyl)hydrazinecarbothioamide, 2-[1 -(2-propenyl)-6- chloro-2-oxo-1 ,2-dihydro-3H-indole-3-yliden]-/V-(2- sulphamoilphenyl)hydrazinecarbothioamide,2-[1 -(2-propenyl)-6-bromo-2-oxo-1 ,2-dihydro-3 7- indole-3-yliden]-/V-(2-sulphamoilphenyl)hydrazinecarbothioamide,2-[1 -(2-propenyl)-7-methyl- 2-0X0-1 ,2-dihydro-3Hindole-3-yliden]-N-(2-sulphamoilphenyl)hydrazinecarboth
(2-propenyl)-7-trifluoromethyl-2-oxo-1 ,2-dihydro-3H-indole-3-yliden]-/\/-(2- sulphamoilphenyl)hydrazinecarbothioamide,2-[1 -(2-propenyl)-7-metoxy-2-oxo-1 ,2-dihydro- 3H-indole-3-yliden]-N-(2-sulphamoilphenyl)hydrazinecarbothioam
fluoro-2-oxo-1 ,2-dihydro-3H-indole-3-yliden]-/V-(2- sulphamoilphenyl)hydrazinecarbothioamide,2-[1 -(2-propenyl)-7-chloro-2-oxo-1 ,2-dihydro-3H indole-3-yliden]-N-(2-sulphamoilphenyl)hydrazinecarbothioam
2-0X0-1 ,2-dihydro-3Hindole-3-yliden]-N-(2-sulphamoilph
(2-propenyl)-5-fluoro-6-chloro-2-oxo-1 ,2-dihydro-3H-indole-3-yliden]-/V-(2- sulphamoilphenyl)hydrazinecarbothioamide,2-[1 -(2-propenyl)-5-chloro-7-methyl-2-oxo-1 ,2- dihydro-3Hindole-3-yliden]-N-(2-sulphamoilphenyl)hydrazinecarbothioamid
propenyl)-5,7-dichloro-2-oxo-1 ,2-dihydro-3 - -indole-3-yliden]-/V-(2- sulphamoilphenyl)hydrazinecarbothioamide,2-[1 -(2-propenyl)-5J-dibromo-2-oxo-1 ,2-dihydro- 3Hindole-3-yliden]-N-(2-sulphamoilphenyl)hydrazinecarbothioamide.
In an application of the present invention, the compounds shown by Formula III are selected from 2-oxo-3-[2-[(2-sulphamoilphenyl)karbamotioil]hydrazineiliden]-2,3-dihydro-1 H- indole-1-aceticacid
Figure imgf000067_0001
and from its derivatives, for instance 2-oxo-3-[2-[(2- sulphamoilphenyl)karbamotioil]hydrazineiliden]-2,3-dihydro-1 - -indole-1 -aceticacid,5-methyl- 2-oxo-3-[2-[(2-sulphamoilphenyl)karbamotioil]hydrazineiliden]-2,3-dihydro-1 H-indole-1 - aceticacid,5-(propane-2-yl)-2-oxo-3-[2-[(2-sulphamoilphenyl)karbamotioil]hydrazineiliden]- 2,3-dihydro-1 H-indole-1 -aceticacid,5-t-butyl-2-oxo-3-[2-[(2- sulphamoilphenyl)karbamotioil]hydrazineiliden]-2,3-dihydro-1 - -indole-1 -aceticacid,5-metoxy- 2-oxo-3-[2-[(2-sulphamoilphenyl)karbamotioil]hydrazineiliden]-2,3-dihydro-1 H-indole-1 - aceticacid,5-trifluorometoxy-2-oxo-3-[2-[(2-sulphamoilphenyl)karbamotioil]hydrazineiliden]- 2,3-dihydro-1 Hindole-1 -aceticacid,5-f luoro-2-oxo-3-[2-[(2- sulphamoilphenyl)karbamotioil]hydrazineiliden]-2,3-dihydro-1 - -indole-1 -aceticacid,5-chloro- 2-oxo-3-[2-[(2-sulphamoilphenyl)karbamotioil]hydrazineiliden]-2,3-dihydro-1 H-indole-1 - aceticacid,5-bromo-2-oxo-3-[2-[(2-sulphamoilphenyl)karbamotioil]hydrazineiliden]-2,3- dihydro-1 H-indole-1 -aceticacid,5-iyodo-2-oxo-3-[2-[(2- sulphamoilphenyl)karbamotioil]hydrazineiliden]-2,3-dihydro-1 H-indole-1 -aceticacid,5-cyano- 2-oxo-3-[2-[(2-sulphamoilphenyl)karbamoti H-indole-1 - aceticacid,5-karbamoil-2-oxo-3-[2-[(2-sulph
dihydro-1 H-indole-1 -aceticacid, sodium 1 -(carboxymethyl)-2-oxo-3-[2-[(2- sulphamoilphenyl)karbamotioil]hydrazineiliden]-2,3-dihydro-1 Hindole-5-sulphon
2-oxo-3-[2-[(2-sulphamoilphenyl)karbamotioil]hydrazineiliden]-2,3-dihydro-1 H-indole-1 - aceticacid, 6-chloro-2-oxo-3-[2-[(2-sulphamoilphenyl)karbamotioil]hydrazineiliden]-2, 3- dihydro-1 H-indole-1 -aceticacid, 6-bromo-2-oxo-3-[2-[(2- sulphamoilphenyl)karbamotioil]hydrazineiliden]-2,3-dihydro-1 H-indole-1 -aceticacid, 7-methyl- 2-oxo-3-[2-[(2-sulphamoilphenyl)karbamotioil]hydrazineiliden]-2,3-dihydro-1 H-indole-1 - aceticacid, 7-trifluoromethyl-2-oxo-3-[2-[(2-sulphamoilphenyl)karbamotioil]hydrazineiliden]- 2,3-dihydro-1 H-indole-1 -aceticacid, 7-metoxy-2-oxo-3-[2-[(2- sulphamoilphenyl)karbamotioil]hydrazineiliden]-2,3-dihydro-1 H-indole-1 -aceticacid, 7-fluoro-2- oxo-3-[2-[(2-sulphamoilphenyl)karbamotioil]hydrazineiliden]-2,3-dihydro-1 H-indole-1 - aceticacid, 7-chloro-2-oxo-3-[2-[(2-sulphamoilphenyl)karbamotioil]hydrazineiliden]-2, 3- dihydro-1 H-indole-1 -aceticacid, 7-bromo-2-oxo-3-[2-[(2- sulphamoilphenyl)karbamotioil]hydrazineiliden]-2,3-dihydro-1 H-indole-1 -aceticacid, 7-fluoro-2- oxo-3-[2-[(2-sulphamoilphenyl)karbamotioil]hydrazineiliden]-2,3-dihydro-1 H-indole-1 - aceticacid, 5-fluoro-6-chloro-2-oxo-3-[2-[(2-sulphamoilphenyl)karbamotioil]hydrazineiliden]- 2,3-dihydro-1 H-indole-1 -aceticacid, 5-chloro-7-methyl-2-oxo-3-[2-[(2- sulphamoilphenyl)karbamotioil]hydrazineiliden]-2,3-dihydro-1 H-indole-1 -aceticacid, 5,7- dichloro-2-oxo-3-[2-[(2-sulphamoilphenyl)karbamotioil]hydrazineiliden]-2,3-dihydro-1 H-indole- 1 -aceticacid, 5, 7-dibromo-2-oxo-3-[2-[(2-sulphamoilphenyl)karbamotioil]hydrazineiliden]-2, 3- dihydro-1 H-indole-1 -aceticacid. In an application of the present invention, the compounds shown by Formula III are selected from ethyl 2-oxo-3-[2-[(2-sulphamoilphenyl)karbamotioil]hydrazineiliden]-2,3-dihydro- 1 H-indole-1 -acetate
Figure imgf000068_0001
and from its derivatives, for instance ethyl 2-oxo-3-[2-[(2- sulphamoilphenyl)karbamotioil]hydrazineiliden]-2,3-dihydro-1 H-indole-1 -acetate, Ethyl 5- methyl-2-oxo-3-[2-[(2-sulphamoilphenyl)karbamotioil]hydrazineiliden]-2,3-dihydro-1 H-indole- 1 -acetate, ethyl 5-(propane-2-yl)-2-oxo-3-[2-[(2- sulphamoilphenyl)karbamotioil]hydrazineiliden]-2,3-dihydro-1 H-indole-1 -acetate, ethyl 5-t- butyl-2-oxo-3-[2-[(2-sulphamoilphenyl)karbamotioil]hydrazineiliden]-2,3-di acetate, ethyl 5-metoxy-2-oxo-3-[2-[(2-sulphamoilphenyl)karbamotioil]hydrazineiliden]-2,3- dihydro-1 H-indole-1 -acetate, ethyl 5-trif luorometoxy-2-oxo-3-[2-[(2- sulphamoilphenyl)karbamotioil]hydrazineiliden]-2,3-dihydro-1 H-indole-1 -acetate, ethyl 5- fluoro-2-oxo-3-[2-[(2-sulphamoilphenyl)karbamotioil]hydrazineiliden]-2,3-dihydro-1 - -indole-1 - acetate, ethyl 5-chloro-2-oxo-3-[2-[(2-sulphamoilphenyl)karbamotioil]hydrazineiliden]-2,3- dihydro-1 H-indole-1 -acetate, ethyl 5-bromo-2-oxo-3-[2-[(2- sulphamoilphenyl)karbamotioil]hydrazineiliden]-2,3-dihydro-1 H-indole-1 -acetate, ethyl 5- iyodo-2-oxo-3-[2-[(2-sulphamoilphenyl)karbamotioil]hydrazineiliden]-2,3-dihydro-1 H-indole-1 - acetate, ethyl 5-cyano-2-oxo-3-[2-[(2-sulphamoilphenyl)karbamotioil]hydrazineiliden]-2,3- dihydro-1 H-indole-1 -acetate, ethyl 5-karbamoil-2-oxo-3-[2-[(2- sulphamoilphenyl)karbamotioil]hydrazineiliden]-2,3-dihydro-1 H-indole-1 -acetate, Sodium 1 - (2-etoxy-2-oxoethyl)-2-oxo-3-[2-[(2-sulphamoilphenyl)karbamotioil]hydrazineiliden]-2,3- dihydro-1 H-indole-5-sulphonate, ethyl 6-bromo-2-oxo-3-[2-[(2- sulphamoilphenyl)karbamotioil]hydrazineiliden]-2,3-dihydro-1 H-indole-1 -acetate, ethyl 7- methyl-2-oxo-3-[2-[(2-sulphamoilphenyl)karbamotioil]hydrazineiliden]-2,3-dihydro-1 H-indole- 1 -acetate, ethyl 7-trifluoromethyl-2-oxo-3-[2-[(2- sulphamoilphenyl)karbamotioil]hydrazineiliden]-2,3-dihydro-1 H-indole-1 -acetate, ethyl 7- metoxy-2-oxo-3-[2-[(2-sulphamoilphenyl)karbamotioil]hydrazineiliden]-2,3-dihydro-1 H-indole- 1 -acetate, ethyl 7-fluoro-2-oxo-3-[2-[(2-sulphamoilphenyl)karbamotioil]hydrazineiliden]-2,3- dihydro-1 H-indole-1 -acetate, ethyl 7-chloro-2-oxo-3-[2-[(2- sulphamoilphenyl)karbamotioil]hydrazineiliden]-2,3-dihydro-1 H-indole-1 -acetate, ethyl 7- bromo-2-oxo-3-[2-[(2-sulphamoilphenyl)karbamotioil]hydrazineiliden]-2,3-dihydro-1 H-indole- 1 -acetate, ethyl 7-fluoro-2-oxo-3-[2-[(2-sulphamoilphenyl)karbamotioil]hydrazineiliden]-2,3- dihydro-1 H-indole-1 -acetate, ethyl 5-fluoro-6-chloro-2-oxo-3-[2-[(2- sulphamoilphenyl)karbamotioil]hydrazineiliden]-2,3-dihydro-1 H-indole-1 -acetate, ethyl 5- chloro-7-methyl-2-oxo-3-[2-[(2-sulphamoilphenyl)karbamotioil]hydrazineiliden]-2,3-dihydro- 1 H-indole-1 -acetate, ethyl 5,7-dichloro-2-oxo-3-[2-[(2- sulphamoilphenyl)karbamotioil]hydrazineiliden]-2,3-dihydro-1 H-indole-1 -acetate, ethyl 5,7- dibromo-2-oxo-3-[2-[(2-sulphamoilphenyl)karbamotioil]hydrazineiliden]-2,3-dihydro-1 H- indole-1 -acetate.
In an application of the present invention, the compounds shown by Formula III are selected from 2-(1 -Benzyl-2-oxo-1 ,2-dihydro-3H-indole-3-yliden)-A/-(2- sulphamoilphenyl)hydrazinecarbothioamide s
S02NH2
Figure imgf000070_0001
and from its derivatives, for instance2-(1 -benzyl-2-oxo-1 ,2-dihydro-3 - -indole-3-yliden)-/V-(2- sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 -benzyl-5-methyl-2-oxo-1 ,2-dihydro-3 7- indole-3-yliden)-/V-(2-sulphamoilphenyl)hydrazinecarbothioamide, 2-[1 -benzyl-5-(propane-2- yl)-2-oxo-1 ,2-dihydro-3 - -indole-3-yliden]-/V-(2-sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 -benzyl-5-t-butyl-2-oxo-1 ,2-dihydro-3H-indole-3-yliden)-/V-(2- sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 -benzyl-5-metoxy-2-oxo-1 ,2-dihydro-3 7- indole-3-yliden)-/V-(2-sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 -benzyl-5- trifluorometoxy-2-oxo-1 ,2-dihydro-3 - -indole-3-yliden)-/V-(2- sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 -benzyl-5-fluoro-2-oxo-1 ,2-dihydro-3 7- indole-3-yliden)-/V-(2-sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 -benzyl-5-chloro-2- oxo-1 ,2-dihydro-3 - -indole-3-yliden)-/V-(2-sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 - benzyl-5-bromo-2-oxo-1 ,2-dihydro-3H-indole-3-yliden)-/V-(2- sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 -benzyl-5-iyodo-2-oxo-1 ,2-dihydro-3 7- indole-3-yliden)-/V-(2-sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 -benzyl-5-nitro-2-oxo- 1 ,2-dihydro-3 - -indole-3-yliden)-/V-(2-sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 - benzyl-5-cyano-2-oxo-1 ,2-dihydro-3 - -indole-3-yliden)-/V-(2- sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 -benzyl-5-karbamoil-2-oxo-1 ,2-dihydro-3 7- indole-3-yliden)-/V-(2-sulphamoilphenyl)hydrazinecarbothioamide, Sodium 3-[1 -benzyl-2-oxo- 3-[2-(sulphamoilphenyl)karbamotioil]hydrazineiliden]-2,3-dihydro-1 - -indole-5-sulphonate, 2- (1 -benzyl-5-sulphamoil-2-oxo-1 ,2-dihydro-3H-indole-3-yliden)-/V-(2- sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 -benzyl-6-fluoro-2-oxo-1 ,2-dihydro-3 7- indole-3-yliden)-/V-(2-sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 -benzyl-6-chloro-2- oxo-1 ,2-dihydro-3 - -indole-3-yliden)-/V-(2-sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 - benzyl-6-bromo-2-oxo-1 ,2-dihydro-3H-indole-3-yliden)-/V-(2- sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 -benzyl-7-methyl-2-oxo-1 ,2-dihydro-3 7- indole-3-yliden)-/V-(2-sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 -benzyl-7- trifluoromethyl-2-oxo-1 ,2-dihydro-3H-indole-3-yliden)-/V-(2- sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 -benzyl-7-metoxy-2-oxo-1 ,2-dihydro-3 7- indole-3-yliden)-/V-(2-sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 -benzyl-7-fluoro-2-oxo- 1 ,2-dihydro-3 - -indole-3-yliden)-/V-(2-sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 - benzyl-7-chloro-2-oxo-1 ,2-dihydro-3H-indole-3-yliden)-/V-(2- sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 -benzyl-7-bromo-2-oxo-1 ,2-dihydro-3 7- indole-3-yliden)-N-(2-sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 -benzyl-5-fluoro-6- chloro-2-oxo-1 ,2-dihydro-3H-indole-3-yliden)-/V-(2- sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 -benzyl-5-chloro-7-methyl-2-oxo-1 ,2- dihydro-3Hindole-3-yliden)-N-(2-sulphamoilphenyl)hydrazinecarbothioami^ 2-(1 -benzyl- 5,7-dichloro-2-oxo-1 ,2-dihydro-3H-indole-3-yliden)-/V-(2- sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 -benzyl-5,7-dibromo-2-oxo-1 ,2-dihydro-3 7- indole-3-yliden)-N-(2-sulphamoilphenyl)hydrazinecarbothioamide.
In an application of the present invention, the compounds shown by Formula III are selected from 2-[1-(4-trifluoromethylbenzyl)-2-oxo-1 ,2-dihydro-3W-indole-3-yliden]-A -(2- sulphamoilphenyl)hydrazinecarbothioamide
Figure imgf000071_0001
and from its derivatives, for instance2-[1 -(4-trifluoromethylbenzyl)-2-oxo-1 ,2-dihydro-3 7- indole-3-yliden]-/V-(2-sulphamoilphenyl)hydrazinecarbothioamide,2-[1 -(4- trifluoromethylbenzyl)-5-methyl-2-oxo-1 ,2-dihydro-3H-indole-3-yliden]-/V-(2- sulphamoilphenyl)hydrazinecarbothioamide,2-[1 -(4-trifluoromethylbenzyl)-5-(propane-2-yl)-2- oxo-1 ,2-dihydro-3 - -indole-3-yliden]-/V-(2-sulphamoilphenyl)hydrazinecarbothioamide,2-[1 -(4- trifluoromethylbenzyl)-5-t-butyl-2-oxo-1 ,2-dihydro-3H-indole-3-yliden]-/V-(2- sulphamoilphenyl)hydrazinecarbothioamide,2-[1 -(4-trifluoromethylbenzyl)-5-metoxy-2-oxo- 1 ,2-dihydro-3 - -indole-3-yliden]-/V-(2-sulphamoilphenyl)hydrazinecarbothioamide,2-[1 -(4- trifluoromethylbenzyl)-5-trifluorometoxy-2-oxo-1 ,2-dihydro-3 - -indole-3-yliden]-/V-(2- sulphamoilphenyl)hydrazinecarbothioamide,2-[1 -(4-trifluoromethylbenzyl)-5-fluoro-2-oxo-1 ,2- dihydro-3 - -indole-3-yliden]-/V-(2-sulphamoilphenyl)hydrazinecarbothioamide,2-[1 -(4- trifluoromethylbenzyl)-5-chloro-2-oxo-1 ,2-dihydro-3 - -indole-3-yliden]-/V-(2- sulphamoilphenyl)hydrazinecarbothioamide,2-[1 -(4-trifluoromethylbenzyl)-5-bromo-2-oxo- 1 ,2-dihydro-3 - -indole-3-yliden]-/V-(2-sulphamoilphenyl)hydrazinecarbothioamide,2-[1 -(4- trifluoromethylbenzyl)-5-iyodo-2-oxo-1 ,2-dihydro-3 - -indole-3-yliden]-/V-(2- sulphamoilphenyl)hydrazinecarbothioamide,2-[1 -(4-trifluoromethylbenzyl)-5-nitro-2-oxo-1 ,2- dihydro-3 - -indole-3-yliden]-/V-(2-sulphamoilphenyl)hydrazinecarbothioamide,2-[1 -(4- trifluoromethylbenzyl)-5-cyano-2-oxo-1 ,2-dihydro-3 - -indole-3-yliden]-/V-(2- sulphamoilphenyl)hydrazinecarbothioamide,2-[1 -(4-trifluoromethylbenzyl)-5-karbamoil-2-oxo- 1 ,2-dihydro-3 - -indole-3-yliden]-/V-(2-sulphamoilphenyl)hydrazinecarbothioamide, sodium 3- [1 -(4-trifluoromethylbenzyl)-2-oxo-3-[2-(sulphamoilphenyl)karbamotioil]hydrazineiliden]-2,3- dihydro-1 7-indole-5-sulphonate,2-[1 -(4-trif luoromethylbenzyl)-5-sulphamoil-2-oxo-1 ,2- dihydro-3Hindole-3-yliden]-N-(2-sulphamoilphenyl)hydrazinecarbothioam
trifluoromethylbenzyl)-6-fluoro-2-oxo-1 ,2-dihydro-3 - -indole-3-yliden]-/V-(2- sulphamoilphenyl)hydrazinecarbothioamide,2-[1 -(4-trif luoromethylbenzyl)-6-chloro-2-oxo-1 ,2- dihydro-3Hindole-3-yliden]-N-(2-sulphamoilphenyl)hydrazinecarbothioamide,2-[
trifluoromethylbenzyl)-6-bromo-2-oxo-1 ,2-dihydro-3 - -indole-3-yliden]-/V-(2- sulphamoilphenyl)hydrazinecarbothioamide,2-[1 -(4-trif luoromethylbenzyl)-7-methyl-2-oxo- 1 ,2-dihydro-3Hindole-3-yliden]-N-(2-sulphamoilphenyl)hydrazinecarbothioamide,2-[ trifluoromethylbenzyl)-7-trifluoromethyl-2-oxo-1 ,2-dihydro-3 - -indole-3-yliden]-/V-(2- sulphamoilphenyl)hydrazinecarbothioamide,2-[1 -(4-trif luoromethylbenzyl)-7-metoxy-2-oxo- 1 ,2-dihydro-3Hindole-3-yliden]-N-(2-sulphamoilphenyl)hydrazinecarbothioamide,2-[ trifluoromethylbenzyl)-7-fluoro-2-oxo-1 ,2-dihydro-3 - -indole-3-yliden]-/V-(2- sulphamoilphenyl)hydrazinecarbothioamide,2-[1 -(4-trif luoromethylbenzyl)-7-chloro-2-oxo-1 ,2- dihydro-3Hindole-3-yliden]-N-(2-sulphamoilphenyl)hydrazinecarbothioamide,2-[1 -^ trifluoromethylbenzyl)-7-bromo-2-oxo-1 ,2-dihydro-3 - -indole-3-yliden]-/V-(2- sulphamoilphenyl)hydrazinecarbothioamide,2-[1 -(4-trif luoromethylbenzyl)-5-fluoro-6-chloro-2- oxo-1 ,2-dihydro-3Hindole-3-yliden]-N-(2-sulphamoilphenyl)hydrazinecarbothioamide,2-[1 ^ trifluoromethylbenzyl)-5-chloro-7-methyl-2-oxo-1 ,2-dihydro-3 - -indole-3-yliden]-/V-(2- sulphamoilphenyl)hydrazinecarbothioamide, 2-[1 -(4-trif luoromethylbenzyl)-5,7-dichloro-2- oxo-1 ,2-dihydro-3Hindole-3-yliden]-N-(2-sulphamoilphenyl)hydrazinecarbothioamide, 2-[1 - (4-trif luoromethylbenzyl)-5,7-dibromo-2-oxo-1 ,2-dihydro-3 - -indole-3-yliden]-/V-(2- sulphamoilphenyl)hydrazinecarbothioamide.
In an application of the present invention, the compounds shown by Formula III are selected from 2-[1-(3-trifluoromethylbenzyl)-2-oxo-1 ,2-dihydro-3W-indole-3-yliden]-A -(2- sulphamoilphenyl)hydrazinecarbothioamide
Figure imgf000072_0001
and from its derivatives, for instance2-[1 -(3-trifluoromethylbenzyl)-2-oxo-1 ,2-dihydro-3 7- indole-3-yliden]-/V-(2-sulphamoilphenyl)hydrazinecarbothioamide, 2-[1 -(3- trifluoromethylbenzyl)-5-methyl-2-oxo-1 ,2-dihydro-3 - -indole-3-yliden]-/V-(2- sulphamoilphenyl)hydrazinecarbothioamide,2-[1 -(3-trifluoromethylbenzyl)-5-(propane-2-yl)-2- oxo-1 ,2-dihydro-3 - -indole-3-yliden]-/V-(2-sulphamoilphenyl)hydrazinecarbothioamide, 2-[1 (3-trifluoromethylbenzyl)-5-t-butyl-2-oxo-1 ,2-dihydro-3H-indole-3-yliden]-/V-(2- sulphamoilphenyl)hydrazinecarbothioamide, 2-[1 -(3-trifluoromethylbenzyl)-5-metoxy-2-oxo- 1 ,2-dihydro-3Hindole-3-yliden]-N-(2-sulphamoilphenyl)hydrazinecarbothioamide, 2-[1 -(3- trifluoromethylbenzyl)-5-trifluorometoxy-2-oxo-1 ,2-dihydro-3/-/-indole-3-yliden]-/V-(2- sulphamoilphenyl)hydrazinecarbothioamide, 2-[1 -(3-trifluoromethylbenzyl)-5-fluoro-2-oxo-1 ,2- dihydro-3Hindole-3-yliden]-N-(2-sulphamoilphenyl)hydrazinecarbothioamide, 2-[1 -(3- trifluoromethylbenzyl)-5-chloro-2-oxo-1 ,2-dihydro-3 - -indole-3-yliden]-/V-(2- sulphamoilphenyl)hydrazinecarbothioamide, 2-[1 -(3-trifluoromethylbenzyl)-5-bromo-2-oxo- 1 ,2-dihydro-3Hindole-3-yliden]-N-(2-sulphamoilphenyl)hydrazinecarbothioamide, 2-[1 -(3- trifluoromethylbenzyl)-5-iyodo-2-oxo-1 ,2-dihydro-3 - -indole-3-yliden]-/V-(2- sulphamoilphenyl)hydrazinecarbothioamide, 2-[1 -(3-trifluoromethylbenzyl)-5-nitro-2-oxo-1 ,2- dihydro-3Hindole-3-yliden]-N-(2-sulphamoilphenyl)hydrazinecarbothioamide,2-[1 -(3- trifluoromethylbenzyl)-5-cyano-2-oxo-1 ,2-dihydro-3Hindole-3-yliden]-/V-(2- sulphamoilphenyl)hydrazinecarbothioamide, 2-[1 -(3-trifluoromethylbenzyl)-5-karbamoil-2- oxo-1 ,2-dihydro-3Hindole-3-yliden]-N-(2-sulphamoilphenyl)hydrazinecarbothioamide, sodium 3-[1 -(3-trifluoromethylbenzyl)-2-oxo-3-[2- (sulphamoilphenyl)karbamotioil]hydrazineiliden]-2,3-dihydro-1 H-indole-5-sulphonate,^ trifluoromethylbenzyl)-5-sulphamoil-2-oxo-1 ,2-dihydro-3 - -indole-3-yliden]-/V-(2- sulphamoilphenyl)hydrazinecarbothioamide,2-[1 -(3-trifluoromethylbenzyl)-6-fluoro-2-oxo-1 ,2- dihydro-3Hindole-3-yliden]-N-(2-sulphamoilphenyl)hydrazinecarbothioamide,2-[1 -(3- trifluoromethylbenzyl)-6-chloro-2-oxo-1 ,2-dihydro-3H-indole-3-yliden]-/V-(2- sulphamoilphenyl)hydrazinecarbothioamide,2-[1 -(3-trifluoromethylbenzyl)-6-bromo-2-oxo- 1 ,2-dihydro-3Hindole-3-yliden]-N-(2-sulphamoilphenyl)hydrazinecarbothioamide,2-[1 -^ trifluoromethylbenzyl)-7-methyl-2-oxo-1 ,2-dihydro-3 - -indole-3-yliden]-/V-(2- sulphamoilphenyl)hydrazinecarbothioamide, 2-[1 -(3-trifluoromethylbenzyl)-7-trifluoromethyl- 2-0X0-1 ,2-dihydro-3Hindole-3-yliden]-N-(2-sulphamoilphenyl)hydrazinecarbothioamide, 2-[1 - (3-trifluoromethylbenzyl)-7-metoxy-2-oxo-1 ,2-dihydro-3 - -indole-3-yliden]-/V-(2- sulphamoilphenyl)hydrazinecarbothioamide, 2-[1 -(3-trifluoromethylbenzyl)-7-fluoro-2-oxo-1 ,2- dihydro-3Hindole-3-yliden]-N-(2-sulphamoilphenyl)hydrazinecarbothioamide, 2-[1 -(3- trifluoromethylbenzyl)-7-chloro-2-oxo-1 ,2-dihydro-3 - -indole-3-yliden]-/V-(2- sulphamoilphenyl)hydrazinecarbothioamide, 2-[1 -(3-trifluoromethylbenzyl)-7-bromo-2-oxo- 1 ,2-dihydro-3Hindole-3-yliden]-N-(2-sulphamoilphenyl)hydrazinecarbothioamide, 2-[1 -(3- trifluoromethylbenzyl)-5-fluoro-6-chloro-2-oxo-1 ,2-dihydro-3 - -indole-3-yliden]-/V-(2- sulphamoilphenyl)hydrazinecarbothioamide, 2-[1 -(3-trifluoromethylbenzyl)-5-chloro-7-methyl- 2-0X0-1 ,2-dihydro-3Hindole-3-yliden]-N-(2-sulphamoilphenyl)hydrazinecarbothioamide, 2-[1 - (3-trifluoromethylbenzyl)-5,7-dichloro-2-oxo-1 ,2-dihydro-3H-indole-3-yliden]-/V-(2- sulphamoilphenyl)hydrazinecarbothioamide,2-[1 -(3-trifluoromethylbenzyl)-57-dibromo-2-oxo- 1 ,2-dihydro-3Hindole-3-yliden]-N-(2-sulphamoilphenyl)hydrazinecarbothioamide. In an application of the present invention, the compounds shown by Formula III are selected from 2-[1-(2-trifluoromethylbenzyl)-2-oxo-1 ,2-dihydro-3W-indole-3-yliden]-A -(2- sulphamoilphenyl)hydrazinecarbothioamide
Figure imgf000074_0001
and from its derivatives, for instance2-[1 -(2-trifluoromethylbenzyl)-2-oxo-1 ,2-dihydro-3 7- indole-3-yliden]-/V-(2-sulphamoilphenyl)hydrazinecarbothioamide, 2-[1 -(2- trifluoromethylbenzyl)-5-methyl-2-oxo-1 ,2-dihydro-3 - -indole-3-yliden]-/V-(2- sulphamoilphenyl)hydrazinecarbothioamide, 2-[1 -(2-trifluoromethylbenzyl)-5-(propane-2-yl)- 2-0X0-1 ,2-dihydro-3 - -indole-3-yliden]-/V-(2-sulphamoilphenyl)hydrazinecarbothioamide, 2-[1 - (2-trifluoromethylbenzyl)-5-t-butyl-2-oxo-1 ,2-dihydro-3H-indole-3-yliden]-/V-(2- sulphamoilphenyl)hydrazinecarbothioamide, 2-[1 -(2-trif luoromethylbenzyl)-5-metoxy-2-oxo- 1 ,2-dihydro-3 - -indole-3-yliden]-/V-(2-sulphamoilphenyl)hydrazinecarbothioamide,2-[1 -(2- trifluoromethylbenzyl)-5-trifluorometoxy-2-oxo-1 ,2-dihydro-3 - -indole-3-yliden]-/V-(2- sulphamoilphenyl)hydrazinecarbothioamide, 2-[1 -(2-trifluoromethylbenzyl)-5-fluoro-2-oxo-1 ,2- dihydro-3 - -indole-3-yliden]-/V-(2-sulphamoilphenyl)hydrazinecarbothioamide,2-[1 -(2- trifluoromethylbenzyl)-5-chloro-2-oxo-1 ,2-dihydro-3 - -indole-3-yliden]-/V-(2- sulphamoilphenyl)hydrazinecarbothioamide, 2-[1 -(2-trifluoromethylbenzyl)-5-bromo-2-oxo- 1 ,2-dihydro-3 - -indole-3-yliden]-/V-(2-sulphamoilphenyl)hydrazinecarbothioamide, 2-[1 -(2- trifluoromethylbenzyl)-5-iyodo-2-oxo-1 ,2-dihydro-3 - -indole-3-yliden]-/V-(2- sulphamoilphenyl)hydrazinecarbothioamide, 2-[1 -(2-trifluoromethylbenzyl)-5-nitro-2-oxo-1 ,2- dihydro-3 - -indole-3-yliden]-/V-(2-sulphamoilphenyl)hydrazinecarbothioamide, 2-[1 -(2- trifluoromethylbenzyl)-5-cyano-2-oxo-1 ,2-dihydro-3 - -indole-3-yliden]-/V-(2- sulphamoilphenyl)hydrazinecarbothioamide, 2-[1 -(2-trifluoromethylbenzyl)-5-karbamoil-2- oxo-1 ,2-dihydro-3 - -indole-3-yliden]-/V-(2-sulphamoilphenyl)hydrazinecarbothioamide, sodium 3-[1 -(2-trif luoromethylbenzyl)-2-oxo-3-[2-
(sulphamoilphenyl)karbamotioil]hydrazineiliden]-2,3-dihydro-1 - -indole-5-sulphonate, 2-[1 -(2-thfluoromethylbenzyl)-5-sulphamoil-2-oxo-1 ,2-dihydro-3H-indole-3-yliden]-/V-(2- sulphamoilphenyl)hydrazinecarbothioamide,2-[1 -(2-trif luoromethylbenzyl)-6-fluoro-2-oxo-1 ,2- dihydro-3 - -indole-3-yliden]-/V-(2-sulphamoilphenyl)hydrazinecarbothioamide, 2-[1 -(2- trifluoromethylbenzyl)-6-chloro-2-oxo-1 ,2-dihydro-3 - -indole-3-yliden]-/V-(2- sulphamoilphenyl)hydrazinecarbothioamide, 2-[1 -(2-trif luoromethylbenzyl)-6-bromo-2-oxo- 1 ,2-dihydro-3 - -indole-3-yliden]-/V-(2-sulphamoilphenyl)hydrazinecarbothioamide, 2-[1 -(2- trifluoromethylbenzyl)-7-methyl-2-oxo-1 ,2-dihydro-3 - -indole-3-yliden]-/V-(2- sulphamoilphenyl)hydrazinecarbothioamide, 2-[1 -(2-trifluoromethylbenzyl)-7-trifluoromethyl- 2-0X0-1 ,2-dihydro-3Hindole-3-yliden]-N-(2-sulphamoilphenyl)hydrazine 2-[1 -
(2-trifluoromethylbenzyl)-7-metoxy-2-oxo-1 ,2-dihydro-3 - -indole-3-yliden]-/V-(2- sulphamoilphenyl)hydrazinecarbothioamide, 2-[1 -(2-trifluoromethylbenzyl)-7-fluoro-2-oxo-1 ,2- dihydro-3Hindole-3-yliden]-N-(2-sulphamoilphenyl)hydrazinecarbothioamid 2-[1 -(2- trifluoromethylbenzyl)-7-chloro-2-oxo-1 ,2-dihydro-3 - -indole-3-yliden]-/V-(2- sulphamoilphenyl)hydrazinecarbothioamide, 2-[1 -(2-trifluoromethylbenzyl)-7-bromo-2-oxo- 1 ,2-dihydro-3Hindole-3-yliden]-N-(2-sulphamoilphenyl)hydrazinecarbothioam 2-[1 -(2- trifluoromethylbenzyl)-5-fluoro-6-chloro-2-oxo-1 ,2-dihydro-3H-indole-3-yliden]-/V-(2- sulphamoilphenyl)hydrazinecarbothioamide,2-[1 -(2-trifluoromethylbenzyl)-5-ch
2-0X0-1 ,2-dihydro-3Hindole-3-yliden]-N-(2-sulphamoilphenyl)hydrazine 2-[1 -
(2-trifluoromethylbenzyl)-5,7-dichloro-2-oxo-1 ,2-dihydro-3H-indole-3-yliden]-A -(2- sulphamoilphenyl)hydrazinecarbothioamide, 2-[1 -(2-trifluoromethylbenzyl)-5,7-dibromo-2- oxo-1 ,2-dihydro-3Hindole-3-yliden]-N-(2-sulphamoilphenyl)hydrazinecarbothioami
In an application of the present invention, the compounds shown by Formula III are selected from 2-(1-Naphtylmethyl-2-oxo-1 ,2-dihydro-3W-indole-3-yliden)-A -(2-sulphamoilphenyl) mide
Figure imgf000075_0001
and from its derivatives, for instance2-[1 -(1 -naphtylmethyl)-2-oxo-1 ,2-dihydro-3H-indole-3- yliden]-N-(2-sulphamoilphenyl)hydrazinecarbothioamide, 2-[1 -(1 -naphtylmethyl)-5-methyl-2- oxo-1 ,2-dihydro-3H-indole-3-yliden]-N-(2-sulphamoilphenyl)hydrazinecarbothioamide, 2-[1 - (1 -naphtylmethyl)-5-(propane-2-yl)-2-oxo-1 ,2-dihydro-3H-indole-3-yliden]-N-(2- sulphamoilphenyl)hydrazinecarbothioamide, 2-[1 -(1 -naphtylmethyl)-5-t-butyl-2-oxo-1 ,2- dihydro-3H-indole-3-yliden]-N-(2-sulphamoilphenyl)hydrazinecarbothioamide, 2-[1 -(1 - naphtylmethyl)-5-metoxy-2-oxo-1 ,2-dihydro-3H-indole-3-yliden]-N-(2- sulphamoilphenyl)hydrazinecarbothioamide, 2-[1 -(1 -naphtylmethyl)-5-trif luorometoxy-2-oxo- 1 ,2-dihydro-3H-indole-3-yliden]-N-(2-sulphamoilphenyl)hydrazinecarbothioamide, 2-[1 -(1 - naphtylmethyl)-5-trifluorometoxy-2-oxo-1 ,2-dihydro-3H-indole-3-yliden]-N-(2- sulphamoilphenyl)hydrazinecarbothioamide, 2-[1 -(1 -naphtylmethyl)-5-fluoro-2-oxo-1 ,2- dihydro-3H-indole-3-yliden]-N-(2-sulphamoilphenyl)hydrazinecarbothioamide, 2-[1 -(1 - naphtylmethyl)-5-chloro-2-oxo-1 ,2-dihydro-3H-indole-3-yliden]-N-(2- sulphamoilphenyl)hydrazinecarbothioamide, 2-[1 -(1 -naphtylmethyl)-5-bromo-2-oxo-1 ,2- dihydro-3H-indole-3-yliden]-N-(2-sulphamoilphenyl)hydrazinecarbothioami 2-[1 -(1 - naphtylmethyl)-5-iyodo-2-oxo-1 ,2-dihydro-3H-indole-3-yliden]-N-(2- sulphamoilphenyl)hydrazinecarbothioamide, 2-[1 -(1 -naphtylmethyl)-5-nitro-2-oxo-1 ,2- dihydro-3H-indole-3-yliden]-N-(2-sulphamoilphenyl)hydrazinecarbothioami 2-[1 -(1 - naphtylmethyl)-5-cyano-2-oxo-1 ,2-dihydro-3H-indole-3-yliden]-N-(2- sulphamoilphenyl)hydrazinecarbothioamide, 2-[1 -(1 -naphtylmethyl)-5-karbamoil-2-oxo-1 ,2- dihydro-3H-indole-3-yliden]-N-(2-sulphamoilphenyl)hydrazinecarbothioami Sodium 3-[1 - (1 -naphtylmethyl)-2-oxo-3-[2-(sulphamoilphenyl)karbamotioil]hydrazineiliden]-2,3-di
1 H-indole-5-sulphonate, 2-[1 -(1 -naphtylmethyl)-5-sulphamoil-2-oxo-1 ,2-dihydro-3H-indole-3- yliden)-N-(2-sulphamoilphenyl]hydrazinecarbothioamide, 2-[1 -(1 -naphtylmethyl)-6-fluoro-2- oxo-1 ,2-dihydro-3H-indole-3-yliden)-N-(2-sulphamoilphenyl]hydrazinecarbothioamide, 2-[1 - (1 -naphtylmethyl)-6-chloro-2-oxo-1 ,2-dihydro-3H-indole-3-yliden)-N-(2- sulphamoilphenyl]hydrazinecarbothioamide, 2-[1 -(1 -naphtylmethyl)-6-bromo-2-oxo-1 ,2- dihydro-3H-indole-3-yliden)-N-(2-sulphamoilphenyl]hydrazinecarbothioamide, 2-[1 -(1 - naphtylmethyl)-7-methyl-2-oxo-1 ,2-dihydro-3H-indole-3-yliden)-N-(2- sulphamoilphenyl]hydrazinecarbothioamide, 2-[1 -(1 -naphtylmethyl)-7-trifluoromethyl-2-oxo- 1 ,2-dihydro-3H-indole-3-yliden)-N-(2-sulphamoilphenyl]hydrazinecarbothioamide, 2-[1 -(1 - naphtylmethyl)-7-metoxy-2-oxo-1 ,2-dihydro-3H-indole-3-yliden)-N-(2- sulphamoilphenyl]hydrazinecarbothioamide, 2-[1 -(1 -naphtylmethyl)-7-fluoro-2-oxo-1 ,2- dihydro-3H-indole-3-yliden)-N-(2-sulphamoilphenyl]hydrazinecarbothioamide, 2-[1 -(1 - naphtylmethyl)-7-chloro-2-oxo-1 ,2-dihydro-3H-indole-3-yliden)-N-(2- sulphamoilphenyl]hydrazinecarbothioamide, 2-[1 -(1 -naphtylmethyl)-7-bromo-2-oxo-1 ,2- dihydro-3H-indole-3-yliden)-N-(2-sulphamoilphenyl]hydrazinecarbothioamide, 2-[1 -(1 - naphtylmethyl)-5-fluoro-6-chloro-2-oxo-1 ,2-dihydro-3H-indole-3-yliden]-N-(2- sulphamoilphenyl]hydrazinecarbothioamide, 2-[1 -(1 -naphtylmethyl)-5-chloro-7-methyl-2-oxo- 1 ,2-dihydro-3H-indole-3-yliden]-N-(2-sulphamoilphenyl)hydrazinecarbothioamide, 2-[1 -(1 - naphtylmethyl)-5,7-dichloro-2-oxo-1 ,2-dihydro-3H-indole-3-yliden]-N-(2- sulphamoilphenyl)hydrazinecarbothioamide, 2-[1 -(1 -naphtylmethyl)-5,7-dibromo-2-oxo-1 ,2- dihydro-3H-indole-3-yliden]-N-(2-sulphamoilphenyl)hydrazinecarbothioamide.
In an application of the present invention, the compounds shown by Formula III are selected from 2-(2-Naphtylmethyl-2-oxo-1 ,2-dihydro-3W-indole-3-yliden)-A -(2- sulphamoilphenyl)hydrazinecarbothioamide
Figure imgf000077_0001
and from its derivatives, for instance2-[1 -(2-naphtylmethyl)-2-oxo-1 ,2-dihydro-3Hindole-3- yliden]-/V-(2-sulphamoilphenyl)hydrazinecarbothioamide, 2-[1 -(2-naphtylmethyl)-5-methyl-2- oxo-1 ,2-dihydro-3 - -indole-3-yliden]-/V-(2-sulphamoilphenyl)hydrazinecarbothioamide, 2-[1 - (2-naphtylmethyl)-5-(propane-2-yl)-2-oxo-1 ,2-dihydro-3H-indole-3-yliden]-/V-(2- sulphamoilphenyl)hydrazinecarbothioamide, 2-[1 -(2-naphtylmethyl)-5-t-butyl-2-oxo-1 ,2- dihydro-3 - -indole-3-yliden]-/V-(2-sulphamoilphenyl)hydrazinecarbothioamide, 2-[1 -(2- naphtylmethyl)-5-metoxy-2-oxo-1 ,2-dihydro-3 - -indole-3-yliden]-/V-(2- sulphamoilphenyl)hydrazinecarbothioamide, 2-[1 -(2-naphtylmethyl)-5-trifluorometoxy-2-oxo- 1 ,2-dihydro-3 - -indole-3-yliden]-/V-(2-sulphamoilphenyl)hydrazinecarbothioamide, 2-[1 -(2- naphtylmethyl)-5-trifluorometoxy-2-oxo-1 ,2-dihydro-3 - -indole-3-yliden]-/V-(2- sulphamoilphenyl)hydrazinecarbothioamide, 2-[1 -(2-naphtylmethyl)-5-fluoro-2-oxo-1 ,2- dihydro-3 - -indole-3-yliden]-/V-(2-sulphamoilphenyl)hydrazinecarbothioamide, 2-[1 -(2- naphtylmethyl)-5-chloro-2-oxo-1 ,2-dihydro-3H-indole-3-yliden]-/V-(2- sulphamoilphenyl)hydrazinecarbothioamide, 2-[1 -(2-naphtylmethyl)-5-bromo-2-oxo-1 ,2- dihydro-3 - -indole-3-yliden]-/V-(2-sulphamoilphenyl)hydrazinecarbothioamide, 2-[1 -(2- naphtylmethyl)-5-iyodo-2-oxo-1 ,2-dihydro-3 - -indole-3-yliden]-/V-(2- sulphamoilphenyl)hydrazinecarbothioamide, 2-[1 -(2-naphtylmethyl)-5-nitro-2-oxo-1 ,2- dihydro-3 - -indole-3-yliden]-/V-(2-sulphamoilphenyl)hydrazinecarbothioamide, 2-[1 -(2- naphtylmethyl)-5-cyano-2-oxo-1 ,2-dihydro-3H-indole-3-yliden]-/V-(2- sulphamoilphenyl)hydrazinecarbothioamide, 2-[1 -(2-naphtylmethyl)-5-karbamoil-2-oxo-1 ,2- dihydro-3 - -indole-3-yliden]-/V-(2-sulphamoilphenyl)hydrazinecarbothioamide, sodium 3-[1 -(2- naphtylmethyl)-2-oxo-3-[2-(sulphamoilphenyl)karbamotioil]hydrazineiliden]-2,3-dihydro-1 - - indole-5-sulphonate, 2-[1 -(2-naphtylmethyl)-5-sulphamoil-2-oxo-1 ,2-dihydro-3 7-indole-3- yliden)-/V-(2-sulphamoilphenyl]hydrazinecarbothioamide,2-[1 -(2-naphtylmethyl)-6-fluoro-2- oxo-1 ,2-dihydro-3 - -indole-3-yliden)-/V-(2-sulphamoilphenyl]hydrazinecarbothioamide, 2-[1 - (2-naphtylmethyl)-6-chloro-2-oxo-1 ,2-dihydro-3H-indole-3-yliden)-/V-(2- sulphamoilphenyl]hydrazinecarbothioamide, 2-[1 -(2-naphtylmethyl)-6-bromo-2-oxo-1 ,2- dihydro-3 - -indole-3-yliden)-/V-(2-sulphamoilphenyl]hydrazinecarbothioamide, 2-[1 -(2- naphtylmethyl)-7-methyl-2-oxo-1 ,2-dihydro-3H-indole-3-yliden)-/V-(2- sulphamoilphenyl]hydrazinecarbothioamide, 2-[1 -(2-naphtylmethyl)-7-trifluoromethyl-2-oxo- 1 ,2-dihydro-3 - -indole-3-yliden)-/V-(2-sulphamoilphenyl]hydrazinecarbothioamide, 2-[1 -(2- naphtylmethyl)-7-metoxy-2-oxo-1 ,2-dihydro-3 - -indole-3-yliden)-/V-(2- sulphamoilphenyl]hydrazinecarbothioamide, 2-[1 -(2-naphtylmethyl)-7-fluoro-2-oxo-1 ,2- dihydro-3Hindole-3-yliden)-N-(2-sulphamoilphenyl]hydrazinecarbothioami 2-[1 -(2- naphtylmethyl)-7-chloro-2-oxo-1 ,2-dihydro-3H-indole-3-yliden)-/V-(2- sulphamoilphenyl]hydrazinecarbothioamide, 2-[1 -(2-naphtylmethyl)-7-bromo-2-oxo-1 ,2- dihydro-3Hindole-3-yliden)-N-(2-sulphamoilphenyl]hydrazinecarbothioami 2-[1 -(2- naphtylmethyl)-5-fluoro-6-chloro-2-oxo-1 ,2-dihydro-3 - -indole-3-yliden]-/V-(2- sulphamoilphenyl]hydrazinecarbothioamide, 2-[1 -(2-naphtylmethyl)-5-chloro-7-methyl-2-oxo- 1 ,2-dihydro-3Hindole-3-yliden]-N-(2-sulphamoilphenyl)hydrazinecarbothioam 2-[1 -(2- naphtylmethyl)-5,7-dichloro-2-oxo-1 ,2-dihydro-3H-indole-3-yliden]-A -(2- sulphamoilphenyl)hydrazinecarbothioamide, 2-[1 -(2-naphtylmethyl)-5,7-dibromo-2-oxo-1 ,2- dihydro-3Hindole-3-yliden]-N-(2-sulphamoilphenyl)hydrazinecarbothioam
In an application of the present invention, the compounds shown by Formula III are selected from 2-(2-oxo-1 ,2-dihydro-3W-indole-3-yliden)-A -(3-sulphamoilphenyl) hydrazinecarbothioamide
Figure imgf000078_0001
and from its derivatives, for instance2-(2-oxo-1 ,2-dihydro-3 - -indole-3-yliden)-/V-(3- sulphamoilphenyl)hydrazinecarbothioamide, 2-(5-methyl-2-oxo-1 ,2-dihydro-3 7-indole-3- yliden)-/V-(3-sulphamoilphenyl)hydrazinecarbothioamide, 2-[5-(propane-2-yl)-2-oxo-1 ,2- dihydro-3H-indole-3-yliden]-/V-(3-sulphamoilphenyl)hydrazinecarbothioamide, 2-(5-t-butyl-2- oxo-1 ,2-dihydro-3 - -indole-3-yliden)-/V-(3-sulphamoilphenyl)hydrazinecarbothioamide, 2-(5- metoxy-2-oxo-1 ,2-dihydro-3H-indole-3-yliden)-/V-(3- sulphamoilphenyl)hydrazinecarbothioamide, 2-(5-trifluorometoxy-2-oxo-1 ,2-dihydro-3 7- indole-3-yliden)-/V-(3-sulphamoilphenyl)hydrazinecarbothioamide, 2-(5-fluoro-2-oxo-1 ,2- dihydro-3 - -indole-3-yliden)-/V-(3-sulphamoilphenyl)hydrazinecarbothioamide, 2-(5-chloro-2- oxo-1 ,2-dihydro-3 - -indole-3-yliden)-/V-(3-sulphamoilphenylhydrazinecarbothioamide, 2-(5- bromo-2-oxo-1 ,2-dihydro-3H-indole-3-yliden)-/V-(3- sulphamoilphenyl)hydrazinecarbothioamide, 2-(5-iyodo-2-oxo-1 ,2-dihydro-3 7-indole-3- yliden)-/V-(3-sulphamoilphenyl)hydrazinecarbothioamide, 2-(5-nitro-2-oxo-1 ,2-dihydro-3 7- indole-3-yliden)-/V-(3-sulphamoilphenyl)hydrazinecarbothioamide, 2-(5-cyano-2-oxo-1 ,2- dihydro-3 - -indole-3-yliden)-/V-(3-sulphamoilphenyl)hydrazinecarbothioamide, 2-(5- karbamoil-2-oxo-1 ,2-dihydro-3H-indole-3-yliden)-/V-(3- sulphamoilphenyl)hydrazinecarbothioamide, Sodium 3-[2-oxo-3-[3- (sulphamoilphenyl)karbamotioil]hydrazineiliden]-2,3-dihydro-1 H-i
sulphamoil-2-oxo-1 ,2-dihydro-3H-indole-3-yliden)-/V-(3- sulphamoilphenyl)hydrazinecarbothioamide, 2-(6-fluoro-2-oxo-1 ,2-dihydro-3 - -indole-3- yliden)-N-(3-sulphamoilphenyl)hydrazinecarbothioamide, 2-(6-chloro-2-oxo-1 ,2-dihydro-3 7- indole-3-yliden)-N-(3-sulphamoilphenyl)hydrazinecarbothioamide, 2-(6-bromo-2-oxo-1 ,2- dihydro-3Hindole-3-yliden)-N-(3-sulphamoilphenyl)hydrazinecarbothioam 2-(7-methyl-2- oxo-1 ,2-dihydro-3Hindole-3-yliden)-N-(3-sulphamoilphenyl)hydrazinecarbothioam 2-(7- trifluoromethyl-2-oxo-1 ,2-dihydro-3H-indole-3-yliden)-/V-(3- sulphamoilphenyl)hydrazinecarbothioamide, 2-(7-metoxy-2-oxo-1 ,2-dihydro-3 - -indole-3- yliden)-N-(3-sulphamoilphenyl)hydrazinecarbothioamide, 2-(7-fluoro-2-oxo-1 ,2-dihydro-3 7- indole-3-yliden)-N-(3-sulphamoilphenyl)hydrazinecarbothioamide, 2-(7-chloro-2-oxo-1 ,2- dihydro-3Hindole-3-yliden)-N-(3-sulphamoilphenyl)hydrazineca^ 2-(7-bromo-2- oxo-1 ,2-dihydro-3Hindole-3-yliden)-N-(3-sulphamoilphenyl)hydrazinecarbothioam Methyl 3-[2-oxo-3-[3-(sulphamoilphenyl)karbamotioil]hydrazineiliden]-2,3-dihydro-1 H-indole-7- yl]prop-2-enoat, 2-(5-fluoro-6-chloro-2-oxo-1 ,2-dihydro-3H-indole-3-yliden)-/V-(3- sulphamoilphenyl)hydrazinecarbothioamide, 2-(5-chloro-7-methyl-2-oxo-1 ,2-dihydro-3 7- indole-3-yliden)-/V-(3-sulphamoilphenyl)hydrazinecarbothioamide, 2-(5,7-dichloro-2-oxo-1 ,2- dihydro-3Hindole-3-yliden)-N-(3-sulphamoilphenyl)hydrazinecarbothioamide, 2-(5,7- dibromo-2-oxo-1 ,2-dihydro-3H-indole-3-yliden)-/V-(3- sulphamoilphenyl)hydrazinecarbothioamide.
In an application of the present invention, the compounds shown by Formula III are selected from 2-(1-Methyl-2-oxo-1 ,2-dihydro-3H-indole-3-yliden)-A/-(3- sulphamoilphenyl)hydrazinecarbothioamide
Figure imgf000079_0001
and from its derivatives, for instance2-(1 -methyl-2-oxo-1 ,2-dihydro-3 - -indole-3-yliden)-/V-(3- sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 ,5-dimethyl-2-oxo-1 ,2-dihydro-3 7-indole-3- yliden)-/V-(3-sulphamoilphenyl)hydrazinecarbothioamide, 2-[1 -methyl-5-(propane-2-yl)-2-oxo- 1 ,2-dihydro-3 - -indole-3-yliden]-/V-(3-sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 - methyl-5-t-butyl-2-oxo-1 ,2-dihydro-3H-indole-3-yliden)-/V-(3- sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 -methyl-5-metoxy-2-oxo-1 ,2-dihydro-3 7- indole-3-yliden)-/V-(3-sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 -methyl-5- trifluorometoxy-2-oxo-1 ,2-dihydro-3 - -indole-3-yliden)-/V-(3- sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 -methyl-5-f luoro-2-oxo-1 ,2-dihydro-3 7- indole-3-yliden)-N-(3-sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 -methyl-5-chloro-2- oxo-1 ,2-dihydro-3Hindole-3-yliden)-N-(3-sulphamoilphenyl)hydrazinecarbothioam 2-(1 - methyl-5-bromo-2-oxo-1 ,2-dihydro-3H-indole-3-yliden)-/V-(3- sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 -methyl-5-iyodo-2-oxo-1 ,2-dihydro-3 7- indole-3-yliden)-N-(3-sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 -methyl-5-nitro-2-oxo- 1 ,2-dihydro-3Hindole-3-yliden)-N-(3-sulphamoilphenyl)hydrazinecarbothioam 2-(1 - methyl-5-cyano-2-oxo-1 ,2-dihydro-3 - -indole-3-yliden)-/V-(3- sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 -methyl-5-karbamoil-2-oxo-1 ,2-dihydro-3 7- indole-3-yliden)-N-(3-sulphamoilphenyl)hydrazinecarbothioamide, Sodium 3-[1 -methyl-2-oxo- 3-[3-(sulphamoilphenyl)karbamotioil]hydrazineiliden]-2,3-dihydro-1 Hindole-5-sulph 2- (1 -methyl-5-sulphamoil-2-oxo-1 ,2-dihydro-3H-indole-3-yliden)-/V-(3- sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 -methyl-6-f luoro-2-oxo-1 ,2-dihydro-3 7- indole-3-yliden)-/V-(3-sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 -methyl-6-chloro-2- oxo-1 ,2-dihydro-3Hindole-3-yliden)-N-(3-sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 - methyl-6-bromo-2-oxo-1 ,2-dihydro-3H-indole-3-yliden)-/V-(3- sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 -methyl-7-methyl-2-oxo-1 ,2-dihydro-3 7- indole-3-yliden)-/V-(3-sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 -methyl-7- trifluoromethyl-2-oxo-1 ,2-dihydro-3H-indole-3-yliden)-A -(3- sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 -methyl-7-metoxy-2-oxo-1 ,2-dihydro-3 7- indole-3-yliden)-/V-(3-sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 -methyl-7-fluoro-2-oxo- 1 ,2-dihydro-3Hindole-3-yliden)-N-(3-sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 - methyl-7-chloro-2-oxo-1 ,2-dihydro-3H-indole-3-yliden)-/V-(3- sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 -methyl-7-bromo-2-oxo-1 ,2-dihydro-3 7- indole-3-yliden)-/V-(3-sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 -methyl-5-fluoro-6- chloro-2-oxo-1 ,2-dihydro-3H-indole-3-yliden)-/V-(3- sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 -methyl-5-chloro-7-methyl-2-oxo-1 ,2- dihydro-3Hindole-3-yliden)-N-(3-sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 -methyl- 5,7-dichloro-2-oxo-1 ,2-dihydro-3H-indole-3-yliden)-/V-(3- sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 -methyl-5,7-dibromo-2-oxo-1 ,2-dihydro-3 7- indole-3-yliden)-/V-(3-sulphamoilphenyl)hydrazinecarbothioamide.
In an application of the present invention, the compounds shown by Formula III are selected from 2-(1-Ethyl-2-oxo-1 ,2-dihydro-3W-indole-3-yliden)-A -(3-sulphamoilphenyl) hydrazinecarbothioamide
Figure imgf000081_0001
and from its derivatives, for instance2-(1 -ethyl-2-oxo-1 ,2-dihydro-3/-/-indole-3-yliden)-/V-(3- sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 -ethyl-5-methyl-2-oxo-1 ,2-dihydro-3 7- indole-3-yliden)-/V-(3-sulphamoilphenyl)hydrazinecarbothioamide, 2-[1 -ethyl-5-(propane-2- yl)-2-oxo-1 ,2-dihydro-3 - -indole-3-yliden]-/V-(3-sulphamoilphenyl)hydrazinecarbothioamide,
2- (1 -ethyl-5-t-butyl-2-oxo-1 ,2-dihydro-3H-indole-3-yliden)-/V-(3- sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 -ethyl-5-metoxy-2-oxo-1 ,2-dihydro-3 7- indole-3-yliden)-/V-(3-sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 -ethyl-5- trifluorometoxy-2-oxo-1 ,2-dihydro-3 - -indole-3-yliden)-/V-(3- sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 -ethyl-5-fluoro-2-oxo-1 ,2-dihydro-3 7-indole-
3- yliden)-/V-(3-sulphamoilphenyl)hydrazinecarbothioamide,2-(1 -ethyl-5-chloro-2-oxo-1 ,2- dihydro-3 - -indole-3-yliden)-/V-(3-sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 -ethyl-5- bromo-2-oxo-1 ,2-dihydro-3H-indole-3-yliden)-/V-(3- sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 -ethyl-5-iyodo-2-oxo-1 ,2-dihydro-3 7-indole- 3-yliden)-/V-(3-sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 -ethyl-5-nitro-2-oxo-1 ,2- dihydro-3 - -indole-3-yliden)-/V-(3-sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 -ethyl-5- cyano-2-oxo-1 ,2-dihydro-3H-indole-3-yliden)-/V-(3- sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 -ethyl-5-karbamoil-2-oxo-1 ,2-dihydro-3 7- indole-3-yliden)-/V-(3-sulphamoilphenyl)hydrazinecarbothioamide, Sodium 3-[1 -ethyl-2-oxo-3- [3-(sulphamoilphenyl)karbamotioil]hydrazineiliden]-2,3-dihydro-1 7-indole-5-sulphonate, 2-(1 - ethyl-5-sulphamoil-2-oxo-1 ,2-dihydro-3H-indole-3-yliden)-/V-(3- sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 -ethyl-6-fluoro-2-oxo-1 ,2-dihydro-3 7-indole- 3-yliden)-/V-(3-sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 -ethyl-6-chloro-2-oxo-1 ,2- dihydro-3 - -indole-3-yliden)-/V-(3-sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 -ethyl-6- bromo-2-oxo-1 ,2-dihydro-3H-indole-3-yliden)-/V-(3- sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 -ethyl-7-methyl-2-oxo-1 ,2-dihydro-3 7- indole-3-yliden)-/V-(3-sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 -ethyl-7- trifluoromethyl-2-oxo-1 ,2-dihydro-3H-indole-3-yliden)-/V-(3- sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 -ethyl-7-metoxy-2-oxo-1 ,2-dihydro-3 7- indole-3-yliden)-/V-(3-sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 -ethyl-7-f luoro-2-oxo- 1 ,2-dihydro-3 - -indole-3-yliden)-/V-(3-sulphamoilphenyl)hydrazinecarbothioamide:, 2-(1 -ethyl- 7-chloro-2-oxo-1 ,2-dihydro-3H-indole-3-yliden)-/V-(3- sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 -ethyl-7-bromo-2-oxo-1 ,2-dihydro-3 7-indole- 3-yliden)-/V-(3-sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 -ethyl-5-chloro-7-methyl-2- oxo-1 ,2-dihydro-3Hindole-3-yliden)-N-(3-sul^ 2-(1 - ethyl-5,7-dichloro-2-oxo-1 ,2-dihydro-3H-indole-3-yliden)-/V-(3- sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 -ethyl-5,7-dibromo-2-oxo-1 ,2-dihydro-3H indole-3-yliden)-/V-(3-sulphamoilphenyl) hydrazinecarbothioamide.
In an application of the present invention, the compounds shown by Formula III are selected from 2-oxo-3-[2-[(3-sulphamoilphenyl)karbamotioil]hydrazineiliden]-2,3-dihydro-1 H-
Figure imgf000082_0001
and from its derivatives, for instance2-oxo-3-[2-[(3- sulphamoilphenyl)karbamotioil]hydrazineilidene]-2,3-dihydro-1 H-indole-1 -aceticacid,5- methyl-2-oxo-3-[2-[(3-sulphamoilphenyl)karbamotioil]hydrazineilidene]-2,3-dihydro-1 - -indole-
1 - aceticacid,5-(propane-2-yl)-2-oxo-3-[2-[(3-sulphamoilphenyl)karbamotioil]hydrazineilidene]- 2,3-dihydro-1 H-indole-1 -aceticacid,5-t-butyl-2-oxo-3-[2-[(3- sulphamoilphenyl)karbamotioil]hydrazineilidene]-2,3-dihydro-1 H-indole-1 -aceticacid, 5- metoxy-2-oxo-3-[2-[(3-sulphamoilphenyl)karbamotioil]hydrazineilidene]-2,3-dihydro-1 H- indole-1 -aceticacid, 5-trifluorometoxy-2-oxo-3-[2-[(3- sulphamoilphenyl)karbamotioil]hydrazineilidene]-2,3-dihydro-1 H-indole-1 -aceticacid, 5-fluoro-
2- oxo-3-[2-[(3-sulphamoilphenyl)karbamotioil]hydrazineilidene]-2,3-dihydro-1 H-indole-1 - aceticacid, 5-chloro-2-oxo-3-[2-[(3-sulphamoilphenyl)karbamotioil]hydrazineilidene]-2, 3- dihydro-1 H-indole-1 -aceticacid, 5-bromo-2-oxo-3-[2-[(3- sulphamoilphenyl)karbamotioil]hydrazineilidene]-2,3-dihydro-1 H-indole-1 -aceticacid, 5-iyodo- 2-oxo-3-[2-[(3-sulphamoilphenyl)karbamotioil]hydrazineilidene]-2,3-dihydro-1 H-indole-1 - aceticacid, 5-cyano-2-oxo-3-[2-[(3-sulphamoilphenyl)karbamotioil]hydrazineilidene]-2, 3- dihydro-1 H-indole-1 -aceticacid, 5-karbamoil-2-oxo-3-[2-[(3- sulphamoilphenyl)karbamotioil]hydrazineilidene]-2,3-dihydro-1 H-indole-1 -aceticacid, sodium
1 - (carboxymethyl)-2-oxo-3-[2-[(3-sulphamoilphenyl)karbamotioil]hydrazineilidene]-2,3- dihydro-1 H-indole-5-sulphonate,6-fluoro-2-oxo-3-[2-[(3- sulphamoilphenyl)karbamotioil]hydrazineilidene]-2,3-dihydro-1 H-indole-1 -aceticacid, 6-chloro-
2- oxo-3-[2-[(3-sulphamoilphenyl)karbamotioil]hydrazineilidene]-2,3-dihydro-1 H-indole-1 - aceticacid, 6-bromo-2-oxo-3-[2-[(3-sulphamoilphenyl)karbamotioil]hydrazineilidene]-2, 3- dihydro-1 H-indole-1 -aceticacid, 7-methyl-2-oxo-3-[2-[(3- sulphamoilphenyl)karbamotioil]hydrazineilidene]-2,3-dihydro-1 H-indole-1 -aceticacid, 7- trifluoromethyl-2-oxo-3-[2-[(3-sulphamoilphenyl)karbamotioil]hydrazineilidene]-2,3-dihydro- 1 H-indole-1 -aceticacid,7-metoxy-2-oxo-3-[2-[(3- sulphamoilphenyl)karbamotioil]hydrazineilidene]-2,3-dihydro-^
2-oxo-3-[2-[(3-sulphamoilphenyl)karbamotioil]hydrazineilidene]-2,3-dihydro-1 H^
aceticacid,7-chloro-2-oxo-3-[2-[(3-sulphamoilphenyl)karbam
dihydro-1 H-indole-1 -aceticacid,7-bromo-2-oxo-3-[2-[(3- sulphamoilphenyl)karbamotioil]hydrazineilidene]-2,3-dihydro-1 H-indole-1 -aceticacid,7-fluoro- 2-oxo-3-[2-[(3-sulphamoilphenyl)karbamotioil]hydrazineilidene]-2,3-dihydro-1 H-indole-1 - aceticacid,5-fluoro-6-chloro-2-oxo-3-[2-[(3-sulphamoilphenyl)karbamotioil]hydrazineilidene]- 2,3-dihydro-1 H-indole-1 -aceticacid,5-chloro-7-methyl-2-oxo-3-[2-[(3- sulphamoilphenyl)karbamotioil]hydrazineilidene]-2,3-dihydro-1 H-indole-1 -aceticacid,5,7- dichloro-2-oxo-3-[2-[(3-sulphamoilphenyl)karbamotioil]hydrazineilidene]-2,3-dihydro-1 H- indole-1 -aceticacid,5,7-dibromo-2-oxo-3-[2-[(3- sulphamoilphenyl)karbamotioil]hydrazineilidene]-2,3-dihydro-1 H-indole-1 -aceticacid.
In an application of the present invention, the compounds shown by Formula III are selected from 2-(1 -Benzyl-2-oxo-1 ,2-dihydro-3H-indole-3-yliden)-N-(3- sulphamoilphenyl)hydrazinecarbothioamide
Figure imgf000083_0001
and from its derivatives, for instance2-(1 -benzyl-2-oxo-1 ,2-dihydro-3H-indole-3-yliden)-N-(3- sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 -benzyl-5-methyl-2-oxo-1 ,2-dihydro-3H- indole-3-yliden)-N-(3-sulphamoilphenyl)hydrazinecarbothioamide, 2-[1 -benzyl-5-(propane-2- yl)-2-oxo-1 ,2-dihydro-3H-indole-3-yliden]-N-(3-sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 -benzyl-5-t-butyl-2-oxo-1 ,2-dihydro-3H-indole-3-yliden)-N-(3- sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 -benzyl-5-metoxy-2-oxo-1 ,2-dihydro-3H- indole-3-yliden)-N-(3-sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 -benzyl-5- trifluorometoxy-2-oxo-1 ,2-dihydro-3H-indole-3-yliden)-N-(3- sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 -benzyl-5-fluoro-2-oxo-1 ,2-dihydro-3H- indole-3-yliden)-N-(3-sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 -benzyl-5-chloro-2- oxo-1 ,2-dihydro-3H-indole-3-yliden)-N-(3-sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 - benzyl-5-bromo-2-oxo-1 ,2-dihydro-3H-indole-3-yliden)-N-(3- sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 -benzyl-5-iyodo-2-oxo-1 ,2-dihydro-3H- indole-3-yliden)-N-(3-sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 -benzyl-5-nitro-2-oxo- 1 ,2-dihydro-3H-indole-3-yliden)-N-(3-sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 - benzyl-5-cyano-2-oxo-1 ,2-dihydro-3H-indole-3-yliden)-N-(3- sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 -benzyl-5-karbamoil-2-oxo-1 ,2-dihydro-3H- indole-3-yliden)-N-(3-sulphamoilphenyl)hydrazinecarbothioamide, Sodium 3-[1 -benzyl-2-oxo- 3-[3-(sulphamoilphenyl)karbamotioil]hydrazineiliden]-2,3-dihydro-1 H-indole-5-sulp 2- (1 -benzyl-5-sulphamoil-2-oxo-1 ,2-dihydro-3H-indole-3-yliden)-N-(3- sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 -benzyl-6-fluoro-2-oxo-1 ,2-dihydro-3H- indole-3-yliden)-N-(3-sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 -benzyl-6-chloro-2- oxo-1 ,2-dihydro-3H-indole-3-yliden)-N-(3-sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 - benzyl-6-bromo-2-oxo-1 ,2-dihydro-3H-indole-3-yliden)-N-(3- sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 -benzyl-7-methyl-2-oxo-1 ,2-dihydro-3H- indole-3-yliden)-N-(3-sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 -benzyl-7- trifluoromethyl-2-oxo-1 ,2-dihydro-3H-indole-3-yliden)-N-(3- sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 -benzyl-7-metoxy-2-oxo-1 ,2-dihydro-3H- indole-3-yliden)-N-(3-sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 -benzyl-7-fluoro-2-oxo- 1 ,2-dihydro-3H-indole-3-yliden)-N-(3-sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 - benzyl-7-chloro-2-oxo-1 ,2-dihydro-3H-indole-3-yliden)-N-(3- sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 -benzyl-7-bromo-2-oxo-1 ,2-dihydro-3H- indole-3-yliden)-N-(3-sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 -benzyl-5-fluoro-6- chloro-2-oxo-1 ,2-dihydro-3H-indole-3-yliden)-N-(3- sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 -benzyl-5-chloro-7-methyl-2-oxo-1 ,2- dihydro-3H-indole-3-yliden)-N-(3-sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 -benzyl- 5,7-dichloro-2-oxo-1 ,2-dihydro-3H-indole-3-yliden)-N-(3- sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 -benzyl-5,7-dibromo-2-oxo-1 ,2-dihydro-3H- indole-3-yliden)-N-(3-sulphamoilphenyl) hydrazinecarbothioamide.
In an application of the present invention, the compounds shown by Formula III are selected from 2-[1-(1-naphtylmethyl)-2-oxo-1 ,2-dihydro-3W-indole-3-yliden]-A -(3- sulphamoilphenyl) hydrazinecarbothioamide
Figure imgf000084_0001
and from its derivatives, for instance2-[1 -(1 -naphtylmethyl)-2-oxo-1 ,2-dihydro-3 - -indole-3- yliden]-/V-(3-sulphamoilphenyl)hydrazinecarbothioamide, 2-[1 -(1 -naphtylmethyl)-5-methyl-2- oxo-1 ,2-dihydro-3 - -indole-3-yliden]-/V-(3-sulphamoilphenyl)hydrazinecarbothioamide, 2-[1 - (1 -naphtylmethyl)-5-(propane-2-yl)-2-oxo-1 ,2-dihydro-3H-indole-3-yliden]-/V-(3- sulphamoilphenyl)hydrazinecarbothioamide, 2-[1 -(1 -naphtylmethyl)-5-t-butyl-2-oxo-1 ,2- dihydro-3Hindole-3-yliden]-N-(3-sulphamoilphenyl)hydrazinecarbothioamide, 2-[1 -(1 - naphtylmethyl)-5-metoxy-2-oxo-1 ,2-dihydro-3 - -indole-3-yliden]-/V-(3- sulphamoilphenyl)hydrazinecarbothioamide, 2-[1 -(1 -naphtylmethyl)-5-trif luorometoxy-2-oxo- 1 ,2-dihydro-3Hindole-3-yliden]-N-(3-sulphamoilphenyl)hydrazinecarbothioamide, 2-[1 -(1 - naphtylmethyl)-5-trifluorometoxy-2-oxo-1 ,2-dihydro-3 - -indole-3-yliden]-/V-(3- sulphamoilphenyl)hydrazinecarbothioamide, 2-[1 -(1 -naphtylmethyl)-5-fluoro-2-oxo-1 ,2- dihydro-3Hindole-3-yliden]-N-(3-sulphamoilphenyl)hydrazinecarbothioamide, 2-[1 -(1 - naphtylmethyl)-5-chloro-2-oxo-1 ,2-dihydro-3H-indole-3-yliden]-/\/-(3- sulphamoilphenyl)hydrazinecarbothioamide, 2-[1 -(1 -naphtylmethyl)-5-bromo-2-oxo-1 ,2- dihydro-3Hindole-3-yliden]-N-(3-sulphamoilphenyl)hydrazinecarbothioamide, 2-[1 -(1 - naphtylmethyl)-5-iyodo-2-oxo-1 ,2-dihydro-3Hindole-3-yliden]-/V-(3- sulphamoilphenyl)hydrazinecarbothioamide, 2-[1 -(1 -naphtylmethyl)-5-nitro-2-oxo-1 ,2- dihydro-3Hindole-3-yliden]-N-(3-sulphamoilphenyl)hydrazinecarbothioamide, 2-[1 -(1 - naphtylmethyl)-5-cyano-2-oxo-1 ,2-dihydro-3H-indole-3-yliden]-/V-(3- sulphamoilphenyl)hydrazinecarbothioamide, 2-[1 -(1 -naphtylmethyl)-5-karbamoil-2-oxo-1 ,2- dihydro-3Hindole-3-yliden]-N-(3-sulphamoilphenyl)hydrazinecarbothioamide, Sodium 3-[1 -
(1 -naphtylmethyl)-2-oxo-3-[3-(sulphamoilphenyl)karbamotioil]hydrazineiliden]-2,3-di
1 H-indole-5-sulphonate, 2-[1 -(1 -naphtylmethyl)-5-sulphamoil-2-oxo-1 ,2-dihydro-3 7-indole-3- yliden)-/V-(3-sulphamoilphenyl]hydrazinecarbothioamide,2-[1 -(1 -naphtylmethyl)-6-fluoro-2- oxo-1 ,2-dihydro-3Hindole-3-yliden)-N-(3-sulphamoilphenyl]hydrazinecarbothioamide, 2-[1 - (1 -naphtylmethyl)-6-chloro-2-oxo-1 ,2-dihydro-3H-indole-3-yliden)-/V-(3- sulphamoilphenyl]hydrazinecarbothioamide, 2-[1 -(1 -naphtylmethyl)-6-bromo-2-oxo-1 ,2- dihydro-3Hindole-3-yliden)-N-(3-sulphamoilphenyl]hydrazinecarbothioamide, 2-[1 -(1 - naphtylmethyl)-7-methyl-2-oxo-1 ,2-dihydro-3H-indole-3-yliden)-/V-(3- sulphamoilphenyl]hydrazinecarbothioamide, 2-[1 -(1 -naphtylmethyl)-7-trifluoromethyl-2-oxo- 1 ,2-dihydro-3Hindole-3-yliden)-N-(3-sulphamoilphenyl]hydrazinecarbothioamide, 2-[1 -(1 - naphtylmethyl)-7-metoxy-2-oxo-1 ,2-dihydro-3 - -indole-3-yliden)-/V-(3- sulphamoilphenyl]hydrazinecarbothioamide, 2-[1 -(1 -naphtylmethyl)-7-fluoro-2-oxo-1 ,2- dihydro-3Hindole-3-yliden)-N-(3-sulphamoilphenyl]hydrazinecarbothioamide, 2-[1 -(1 - naphtylmethyl)-7-chloro-2-oxo-1 ,2-dihydro-3H-indole-3-yliden)-/V-(3- sulphamoilphenyl]hydrazinecarbothioamide, 2-[1 -(1 -naphtylmethyl)-7-bromo-2-oxo-1 ,2- dihydro-3Hindole-3-yliden)-N-(3-sulphamoilphenyl]hydrazinecarbothioamide, 2-[1 -(1 - naphtylmethyl)-5-fluoro-6-chloro-2-oxo-1 ,2-dihydro-3H-indole-3-yliden]-/V-(3- sulphamoilphenyl]hydrazinecarbothioamide, 2-[1 -(1 -naphtylmethyl)-5-chloro-7-methyl-2-oxo- 1 ,2-dihydro-3Hindole-3-yliden]-N-(3-sulphamoilphenyl)hydrazinecarbothioamide, 2-[1 -(1 - naphtylmethyl)-4,5-dichloro-2-oxo-1 ,2-dihydro-3H-indole-3-yliden]-/V-(3- sulphamoilphenyl)hydrazinecarbothioamide, 2-[1 -(1 -naphtylmethyl)-5,7-dichloro-2-oxo-1 ,2- dihydro-3Hindole-3-yliden]-N-(3-sulphamoilphenyl)hydrazinecarbothioam 2-[1 -(1 - naphtylmethyl)-5,7-dibromo-2-oxo-1 ,2-dihydro-3 - -indole-3-yliden]-/V-(3- sulphamoilphenyl)hydrazinecarbothioamide.
In an application of the present invention, the compounds shown by Formula III are selected from 2-[1-(2-naphtylmethyl)-2-oxo-1 ,2-dihydro-3W-indole-3-yliden]-A -(3- sulphamoilphenyl) hydrazinecarbothioamide
Figure imgf000086_0001
and from its derivatives, for instance2-[1 -(2-naphtylmethyl)-2-oxo-1 ,2-dihydro-3Hindole-3- yliden]-/V-(3-sulphamoilphenyl)hydrazinecarbothioamide, 2-[1 -(2-naphtylmethyl)-5-methyl-2- oxo-1 ,2-dihydro-3 - -indole-3-yliden]-/V-(3-sulphamoilphenyl)hydrazinecarbothioamide, 2-[1 - (2-naphtylmethyl)-5-(propane-2-yl)-2-oxo-1 ,2-dihydro-3H-indole-3-yliden]-/V-(3- sulphamoilphenyl)hydrazinecarbothioamide, 2-[1 -(2-naphtylmethyl)-5-t-butyl-2-oxo-1 ,2- dihydro-3 - -indole-3-yliden]-/V-(3-sulphamoilphenyl)hydrazinecarbothioamide, 2-[1 -(2- naphtylmethyl)-5-metoxy-2-oxo-1 ,2-dihydro-3 - -indole-3-yliden]-/V-(3- sulphamoilphenyl)hydrazinecarbothioamide, 2-[1 -(2-naphtylmethyl)-5-trifluorometoxy-2-oxo- 1 ,2-dihydro-3 - -indole-3-yliden]-/V-(3-sulphamoilphenyl)hydrazinecarbothioamide, 2-[1 -(2- naphtylmethyl)-5-trifluorometoxy-2-oxo-1 ,2-dihydro-3 - -indole-3-yliden]-/V-(3- sulphamoilphenyl)hydrazinecarbothioamide, 2-[1 -(2-naphtylmethyl)-5-fluoro-2-oxo-1 ,2- dihydro-3 - -indole-3-yliden]-/V-(3-sulphamoilphenyl)hydrazinecarbothioamide, 2-[1 -(2- naphtylmethyl)-5-chloro-2-oxo-1 ,2-dihydro-3H-indole-3-yliden]-/V-(3- sulphamoilphenyl)hydrazinecarbothioamide, 2-[1 -(2-naphtylmethyl)-5-bromo-2-oxo-1 ,2- dihydro-3 - -indole-3-yliden]-/V-(3-sulphamoilphenyl)hydrazinecarbothioamide, 2-[1 -(2- naphtylmethyl)-5-iyodo-2-oxo-1 ,2-dihydro-3H-indole-3-yliden]-/V-(3- sulphamoilphenyl)hydrazinecarbothioamide, 2-[1 -(2-naphtylmethyl)-5-nitro-2-oxo-1 ,2- dihydro-3 - -indole-3-yliden]-/V-(3-sulphamoilphenyl)hydrazinecarbothioamide, 2-[1 -(2- naphtylmethyl)-5-cyano-2-oxo-1 ,2-dihydro-3 - -indole-3-yliden]-/V-(3- sulphamoilphenyl)hydrazinecarbothioamide, 2-[1 -(2-naphtylmethyl)-5-karbamoil-2-oxo-1 ,2- dihydro-3 - -indole-3-yliden]-/V-(3-sulphamoilphenyl)hydrazinecarbothioamide, sodium 3-[1 -(2- naphtylmethyl)-2-oxo-3-[3-(sulphamoilphenyl)karbamotioil]hydrazineiliden]-2,3-dihydro-1 - - indole-5-sulphonate, 2-[1 -(2-naphtylmethyl)-5-sulphamoil-2-oxo-1 ,2-dihydro-3 7-indole-3- yliden)-N-(3-sulphamoilphenyl]hydrazinecarbothioamide,2-[1 -(2-naph
oxo-1 ,2-dihydro-3Hindole-3-yliden)-N-(3-sulphamoilph 2-[1 -
(2-naphtylmethyl)-6-chloro-2-oxo-1 ,2-dihydro-3H-indole-3-yliden)-/V-(3- sulphamoilphenyl]hydrazinecarbothioamide, 2-[1 -(2-naphtylmethyl)-6-bromo-2-oxo-1 ,2- dihydro-3Hindole-3-yliden)-N-(3-sulphamoilphenyl]hydrazinecarbothioamide 2-[1 -(2- naphtylmethyl)-7-methyl-2-oxo-1 ,2-dihydro-3H-indole-3-yliden)-/V-(3- sulphamoilphenyl]hydrazinecarbothioamide, 2-[1 -(2-naphtylmethyl)-7-trifluoromethyl-2-oxo- 1 ,2-dihydro-3Hindole-3-yliden)-N-(3-sulphamoilphenyl]hydrazinecarbothioami 2-[1 -(2- naphtylmethyl)-7-metoxy-2-oxo-1 ,2-dihydro-3 - -indole-3-yliden)-/V-(3- sulphamoilphenyl]hydrazinecarbothioamide, 2-[1 -(2-naphtylmethyl)-7-fluoro-2-oxo-1 ,2- dihydro-3Hindole-3-yliden)-N-(3-sulphamoilphenyl]hydrazinecarbothioamide 2-[1 -(2- naphtylmethyl)-7-chloro-2-oxo-1 ,2-dihydro-3 - -indole-3-yliden)-/V-(3- sulphamoilphenyl]hydrazinecarbothioamide, 2-[1 -(2-naphtylmethyl)-7-bromo-2-oxo-1 ,2- dihydro-3Hindole-3-yliden)-N-(3-sulphamoilphenyl]hydrazinecarbothioamide 2-[1 -(2- naphtylmethyl)-5-fluoro-6-chloro-2-oxo-1 ,2-dihydro-3H-indole-3-yliden]-/V-(3- sulphamoilphenyl]hydrazinecarbothioamide, 2-[1 -(2-naphtylmethyl)-5-chloro-7-methyl-2-oxo- 1 ,2-dihydro-3Hindole-3-yliden]-N-(3-sulphamoilphenyl)hydrazinecarbothioam 2-[1 -(2- naphtylmethyl)-5,7-dichloro-2-oxo-1 ,2-dihydro-3H-indole-3-yliden]-/V-(3- sulphamoilphenyl)hydrazinecarbothioamide, 2-[1 -(2-naphtylmethyl)-5,7-dibromo-2-oxo-1 ,2- dihydro-3Hindole-3-yliden]-N-(3-sulphamoilphenyl)hydrazinecarbothioamide
In an application of the present invention, the compounds shown by Formula III are selected from 2-(2-oxo-1 ,2-dihydro-3W-indole-3-yliden)-A -(4-sulphamoilphenyl) hydrazinecarbothioamide
Figure imgf000087_0001
and from its derivatives, for instance2-[5-(propane-2-yl)-2-oxo-1 ,2-dihydro-3H-indole-3- yliden]-/V-(4-sulphamoilphenyl)hydrazinecarbothioamide, 2-(5-t-butyl-2-oxo-1 ,2-dihydro-3 7- indole-3-yliden)-/V-(4-sulphamoilphenyl)hydrazinecarbothioamide, 2-(5-metoxy-2-oxo-1 ,2- dihydro-3 - -indole-3-yliden)-/V-(4-sulphamoilphenyl)hydrazinecarbothioamide, 2-(5-iyodo-2- oxo-1 ,2-dihydro-3 - -indole-3-yliden)-/V-(4-sulphamoilphenyl)hydrazinecarbothioamide, 2-(5- cyano-2-oxo-1 ,2-dihydro-3 - -indole-3-yliden)-/V-(4- sulphamoilphenyl)hydrazinecarbothioamide, 2-(5-karbamoil-2-oxo-1 ,2-dihydro-3 7-indole-3- yliden)-/V-(4-sulphamoilphenyl)hydrazinecarbothioamide, Sodium 3-[2-oxo-3-[4- (sulphamoilphenyl)karbamotioil]hydrazineiliden]-2,3-dihyd 2-(5- sulphamoil-2-oxo-1 ,2-dihydro-3 - -indole-3-yliden)-/V-(4- sulphamoilphenyl)hydrazinecarbothioamide, 2-(6-fluoro-6-chloro-2-oxo-1 ,2-dihydro-3 7- indole-3-yliden)-N-(4-sulphamoilphenyl)hydrazinecarbothioamide, 2-(6-chloro-7-methyl-2- oxo-1 ,2-dihydro-3Hindole-3-yliden)-N-(4-sulphamoilphenyl)hydrazinecarbothioam 2-(6- bromo-2-oxo-1 ,2-dihydro-3H-indole-3-yliden)-/V-(4- sulphamoilphenyl)hydrazinecarbothioamide, 2-(7-methyl-2-oxo-1 ,2-dihydro-3 - -indole-3- yliden)-N-(4-sulphamoilphenyl)hydrazinecarbothioamide, 2-(7-trifluoromethyl-2-oxo-1 ,2- dihydro-3Hindole-3-yliden)-N-(4-sulphamoilphenyl)hydrazinecarbothioam 2-(7-metoxy-2- oxo-1 ,2-dihydro-3Hindole-3-yliden)-N-(4-sulphamoilphenyl)hydrazinecarbothioam 2-(7- fluoro-2-oxo-1 ,2-dihydro-3H-indole-3-yliden)-/V-(4- sulphamoilphenyl)hydrazinecarbothioamide, 2-(7-chloro-2-oxo-1 ,2-dihydro-3 - -indole-3- yliden)-N-(4-sulphamoilphenyl)hydrazinecarbothioamide, 2-(7-bromo-2-oxo-1 ,2-dihydro-3 7- indole-3-yliden)-N-(4-sulphamoilphenyl)hydrazinecarbothioamide, 2-(5-fluoro-6-chloro-2-oxo- 1 ,2-dihydro-3Hindole-3-yliden)-N-(4-sulphamoilphenyl)hydrazinecarbothioami 2-(5- chloro-7-methyl-2-oxo-1 ,2-dihydro-3H-indole-3-yliden)-/V-(4- sulphamoilphenyl)hydrazinecarbothioamide, 2-(5,7-dichloro-2-oxo-1 ,2-dihydro-3 - -indole-3- yliden)-N-(4-sulphamoilphenyl)hydrazinecarbothioamide. In an application of the present invention, the compounds shown by Formula III are selected from 2-(1-Methyl-2-oxo-1 ,2-dihydro-3H-indole-3-yliden)-A/-(4- sulphamoilphenyl)hydrazinecarbothioamide
Figure imgf000088_0001
and from its derivatives, for instance2-(1 -methyl-2-oxo-1 ,2-dihydro-3 - -indole-3-yliden)-/V-(4- sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 ,5-dimethyl-2-oxo-1 ,2-dihydro-3 7-indole-3- yliden)-/V-(4-sulphamoilphenyl)hydrazinecarbothioamide, 2-[1 -methyl-5-(propane-2-yl)-2-oxo- 1 ,2-dihydro-3 - -indole-3-yliden]-/V-(4-sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 - methyl-5-t-butyl-2-oxo-1 ,2-dihydro-3H-indole-3-yliden)-/V-(4- sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 -methyl-5-metoxy-2-oxo-1 ,2-dihydro-3 7- indole-3-yliden)-/V-(4-sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 -methyl-5- trifluorometoxy-2-oxo-1 ,2-dihydro-3 - -indole-3-yliden)-/V-(4- sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 -methyl-5-f luoro-2-oxo-1 ,2-dihydro-3 7- indole-3-yliden)-/V-(4-sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 -methyl-5-chloro-2- oxo-1 ,2-dihydro-3Hindole-3-yliden)-N-(4-sulphamoilphenyl)hydrazineca 2-(1 - methyl-5-bromo-2-oxo-1 ,2-dihydro-3 - -indole-3-yliden)-/V-(4- sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 -methyl-5-iyodo-2-oxo-1 ,2-dihydro-3 7- indole-3-yliden)-N-(4-sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 -methyl-5-nitro-2-oxo- 1 ,2-dihydro-3Hindole-3-yliden)-N-(4-sulphamoilphenyl)hydrazinecarbothioam 2-(1 - methyl-5-cyano-2-oxo-1 ,2-dihydro-3 - -indole-3-yliden)-/V-(4- sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 -methyl-5-karbamoil-2-oxo-1 ,2-dihydro-3 7- indole-3-yliden)-N-(4-sulphamoilphenyl)hydrazinecarbothioamide, Sodium 3-[1 -methyl-2-oxo- 3-[4-(sulphamoilphenyl)karbamotioil]hydrazineiliden]-2,3-dihydro-1 Hindole-5-sulp 2- (1 -methyl-5-sulphamoil-2-oxo-1 ,2-dihydro-3H-indole-3-yliden)-/V-(4- sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 -methyl-6-f luoro-2-oxo-1 ,2-dihydro-3 7- indole-3-yliden)-/V-(4-sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 -methyl-6-chloro-2- oxo-1 ,2-dihydro-3Hindole-3-yliden)-N-(4-sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 - methyl-6-bromo-2-oxo-1 ,2-dihydro-3Hindole-3-yliden)-/V-(4- sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 -methyl-7-methyl-2-oxo-1 ,2-dihydro-3 7- indole-3-yliden)-/V-(4-sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 -methyl-7- trifluoromethyl-2-oxo-1 ,2-dihydro-3 - -indole-3-yliden)-/V-(4- sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 -methyl-7-metoxy-2-oxo-1 ,2-dihydro-3 7- indole-3-yliden)-/V-(4-sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 -methyl-7-fluoro-2-oxo- 1 ,2-dihydro-3Hindole-3-yliden)-N-(4-sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 - methyl-7-chloro-2-oxo-1 ,2-dihydro-3H-indole-3-yliden)-/V-(4- sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 -methyl-7-bromo-2-oxo-1 ,2-dihydro-3 7- indole-3-yliden)-/V-(4-sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 -methyl-5-fluoro-6- chloro-2-oxo-1 ,2-dihydro-3H-indole-3-yliden)-/V-(4- sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 -methyl-5-chloro-7-methyl-2-oxo-1 ,2- dihydro-3Hindole-3-yliden)-N-(4-sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 -methyl- 5,7-dichloro-2-oxo-1 ,2-dihydro-3H-indole-3-yliden)-/V-(4- sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 -methyl-5,7-dibromo-2-oxo-1 ,2-dihydro-3 7- indole-3-yliden)-/V-(4-sulphamoilphenyl)hydrazinecarbothioamide.
In an application of the present invention, the compounds shown by Formula III are selected from 2-(1 -Ethyl-2-oxo-1 ,2-d i hyd ro-3 W-i ndole-3-yl iden)-A -(4- razinecarbothioamide
Figure imgf000089_0001
and from its derivatives, for instance2-(1 -ethyl-2-oxo-1 ,2-dihydro-3/-/-indole-3-yliden)-/V-(4- sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 -ethyl-5-methyl-2-oxo-1 ,2-dihydro-3 7- indole-3-yliden)-/V-(4-sulphamoilphenyl) hydrazinecarbothioamide, 2-(1 -ethyl-5-methyl-2-oxo- 1 ,2-dihydro-3 - -indole-3-yliden)-/V-(4-sulphamoilphenyl) hydrazinecarbothioamide, 2-[1 -ethyl- 5-(propane-2-yl)-2-oxo-1 ,2-dihydro-3H-indole-3-yliden]-/V-(4- sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 -ethyl-5-t-butyl-2-oxo-1 ,2-dihydro-3 7-indole- 3-yliden)-/V-(4-sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 -ethyl-5-metoxy-2-oxo-1 ,2- dihydro-3 - -indole-3-yliden)-/V-(4-sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 -ethyl-5- trifluorometoxy-2-oxo-1 ,2-dihydro-3 - -indole-3-yliden)-/V-(4- sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 -ethyl-5-fluoro-2-oxo-1 ,2-dihydro-3 7-indole- 3-yliden)-/V-(4-sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 -ethyl-5-chloro-2-oxo-1 ,2- dihydro-3 - -indole-3-yliden)-/V-(4-sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 -ethyl-5- bromo-2-oxo-1 ,2-dihydro-3H-indole-3-yliden)-/V-(4- sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 -ethyl-5-iyodo-2-oxo-1 ,2-dihydro-3 7-indole- 3-yliden)-/V-(4-sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 -ethyl-5-nitro-2-oxo-1 ,2- dihydro-3 - -indole-3-yliden)-/V-(4-sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 -ethyl-5- cyano-2-oxo-1 ,2-dihydro-3 - -indole-3-yliden)-/V-(4- sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 -ethyl-5-karbamoil-2-oxo-1 ,2-dihydro-3 7- indole-3-yliden)-/V-(4-sulphamoilphenyl)hydrazinecarbothioamide, Sodium 3-[1 -ethyl-2-oxo-3- [4-(sulphamoilphenyl)karbamotioil]hydrazineiliden]-2,3-dihydro-1 7-indole-5-sulphonate, 2-(1 - ethyl-5-sulphamoil-2-oxo-1 ,2-dihydro-3 - -indole-3-yliden)-/V-(4- sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 -ethyl-6-fluoro-2-oxo-1 ,2-dihydro-3 7-indole- 3-yliden)-/V-(4-sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 -methyl-6-chloro-2-oxo-1 ,2- dihydro-3 - -indole-3-yliden)-/V-(4-sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 -ethyl-6- bromo-2-oxo-1 ,2-dihydro-3H-indole-3-yliden)-/V-(4- sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 -ethyl-7-methyl-2-oxo-1 ,2-dihydro-3 7- indole-3-yliden)-/V-(4-sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 -ethyl-7- trifluoromethyl-2-oxo-1 ,2-dihydro-3 - -indole-3-yliden)-/V-(4- sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 -ethyl-7-metoxy-2-oxo-1 ,2-dihydro-3 7- indole-3-yliden)-/V-(4-sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 -ethyl-7-f luoro-2-oxo- 1 ,2-dihydro-3 - -indole-3-yliden)-/V-(4-sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 - methyl-7-chloro-2-oxo-1 ,2-dihydro-3H-indole-3-yliden)-/V-(4- sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 -ethyl-7-bromo-2-oxo-1 ,2-dihydro-3 7-indole- 3-yliden)-/V-(4-sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 -ethyl-5-fluoro-6-chloro-2- oxo-1 ,2-dihydro-3 - -indole-3-yliden)-/V-(4-sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 - ethyl-5-chloro-7-methyl-2-oxo-1 ,2-dihydro-3H-indole-3-yliden)-/V-(4- sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 -ethyl-5,7-dichloro-2-oxo-1 ,2-dihydro-3 7- indole-3-yliden)-N-(4-sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 -ethyl-5,7-dibromo-2- oxo-1 ,2-dihydro-3Hindole-3-yliden)-N-(4-sulphamoilphenyl)hydrazinecarbothioam
In an application of the present invention, the compounds shown by Formula III are selected from 2-oxo-3-[2-[(4-sulphamoilphenyl)karbamotioil]hydrazineiliden]-2,3-dihydro-1 H- indole-1-aceticacid
Figure imgf000091_0001
and from its derivatives, for instance2-oxo-3-[2-[(4- sulphamoilphenyl)karbamotioil]hydrazineiliden]-2,3-dihydro-1 - -indole-1 -aceticacid,5-methyl- 2-oxo-3-[2-[(4-sulphamoilphenyl)karbamotioil]hydrazineiliden]-2,3-dihydro-1 H-indole-1 - aceticacid,5-(propane-2-yl)-2-oxo-3-[2-[(4-sulphamoilphenyl)karbamotioil]hydrazineiliden]- 2,3-dihydro-1 H-indole-1 -aceticacid, 5-t-butyl-2-oxo-3-[2-[(4- sulphamoilphenyl)karbamotioil]hydrazineiliden]-2,3-dihydro-1 H-indole-1 -aceticacid, 5-metoxy- 2-oxo-3-[2-[(4-sulphamoilphenyl)karbamotioil]hydrazineiliden]-2,3-dihydro-1 H-indole-1 - aceticacid, 5-trifluorometoxy-2-oxo-3-[2-[(4-sulphamoilphenyl)karbamotioil]hydrazineiliden]- 2,3-dihydro-1 H-indole-1 -aceticacid, 5-f luoro-2-oxo-3-[2-[(4- sulphamoilphenyl)karbamotioil]hydrazineiliden]-2,3-dihydro-1 H-indole-1 -aceticacid, 5-chloro- 2-oxo-3-[2-[(4-sulphamoilphenyl)karbamotioil]hydrazineiliden]-2,3-dihydro-1 H-indole-1 - aceticacid, 5-bromo-2-oxo-3-[2-[(4-sulphamoilphenyl)karbamotioil]hydrazineiliden]-2, 3- dihydro-1 H-indole-1 -aceticacid, 5-iyodo-2-oxo-3-[2-[(4- sulphamoilphenyl)karbamotioil]hydrazineiliden]-2,3-dihydro-1 H-indole-1 -aceticacid, 5-cyano- 2-oxo-3-[2-[(4-sulphamoilphenyl)karbamotioil]hydrazineiliden]-2,3-dihydro-1 H-indole-1 - aceticacid, 5-karbamoil-2-oxo-3-[2-[(4-sulphamoilphenyl)karbamotioil]hydrazineiliden]-2, 3- dihydro-1 H-indole-1 -aceticacid, sodium 1 -(carboxymethyl)-2-oxo-3-[2-[(4- sulphamoilphenyl)karbamotioil]hydrazineiliden]-2,3-dihydro-1 H-indole-5-sulphonate, 6-fluoro- 2-oxo-3-[2-[(4-sulphamoilphenyl)karbamotioil]hydrazineiliden]-2,3-dihydro-1 H-indole-1 - aceticacid, 6-chloro-2-oxo-3-[2-[(4-sulphamoilphenyl)karbamotioil]hydrazineiliden]-2, 3- dihydro-1 H-indole-1 -aceticacid, 6-bromo-2-oxo-3-[2-[(4- sulphamoilphenyl)karbamotioil]hydrazineiliden]-2,3-dihydro-1 H-indole-1 -aceticacid, 7-methyl- 2-oxo-3-[2-[(4-sulphamoilphenyl)karbamotioil]hydrazineiliden]-2,3-dihydro-1 H-indole-1 - aceticacid, 7-trifluoromethyl-2-oxo-3-[2-[(4-sulphamoilphenyl)karbamotioil]hydrazineiliden]- 2,3-dihydro-1 H-indole-1 -aceticacid, 7-metoxy-2-oxo-3-[2-[(4- sulphamoilphenyl)karbamotioil]hydrazineiliden]-2,3-dihydro-1 H-indole-1 -aceticacid, 7-fluoro-2- oxo-3-[2-[(4-sulphamoilphenyl)karbam
aceticacid, 7-chloro-2-oxo-3-[2-[(4-sulphamoilphenyl)karbam
dihydro-1 H-indole-1 -aceticacid, 7-bromo-2-oxo-3-[2-[(4- sulphamoilphenyl)karbamotioil]hydrazineiliden]-2,3-dihydro-^
oxo-3-[2-[(4-sulphamoilphenyl)karbamotioil]hydrazineiliden]-2,3-dihydro-1 H-indole-1 - aceticacid,5-fluoro-6-chloro-2-oxo-3-[2-[(4-sulphamoilphenyl)karbamotioil]hydrazineiliden 2,3-dihydro-1 H-indole-1 -aceticacid, 5-chloro-7-methyl-2-oxo-3-[2-[(4- sulphamoilphenyl)karbamotioil]hydrazineiliden]-2,3-dihydro-1 H-indole-1 -aceticacid, 5,7- dichloro-2-oxo-3-[2-[(4-sulphamoilphenyl)karbamotioil]hydrazineiliden]-2,3-dihydro-1 H-indole- 1 -aceticacid, 5, 7-dibromo-2-oxo-3-[2-[(4-sulphamoilphenyl)karbamotioil]hydrazineiliden]-2,3- dihydro-1 H-indole-1 -aceticacid.
In an application of the present invention, the compounds shown by Formula III are selected from 2-(1 -Benzyl-2-oxo-1 ,2-dihydro-3H-indole-3-yliden)-A/-(4- sulphamoilphenyl)hydrazinecarbothioamide
Figure imgf000092_0001
and from its derivatives, for instance2-(1 -benzyl-2-oxo-1 ,2-dihydro-3H-indole-3-yliden)-/V-(4- sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 -benzyl-5-methyl-2-oxo-1 ,2-dihydro-3H- indole-3-yliden)-/V-(4-sulphamoilphenyl)hydrazinecarbothioamide, 2-[1 -benzyl-5-(propane-2- yl)-2-oxo-1 ,2-dihydro-3H-indole-3-yliden]-/V-(4-sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 -benzyl-5-t-butyl-2-oxo-1 ,2-dihydro-3H-indole-3-yliden)-/V-(4- sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 -benzyl-5-metoxy-2-oxo-1 ,2-dihydro-3H- indole-3-yliden)-/V-(4-sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 -benzyl-5- trifluorometoxy-2-oxo-1 ,2-dihydro-3H-indole-3-yliden)-/V-(4- sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 -benzyl-5-fluoro-2-oxo-1 ,2-dihydro-3H- indole-3-yliden)-/V-(4-sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 -benzyl-5-chloro-2- oxo-1 ,2-dihydro-3H-indole-3-yliden)-/V-(4-sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 - benzyl-5-bromo-2-oxo-1 ,2-dihydro-3H-indole-3-yliden)-/V-(4- sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 -benzyl-5-iyodo-2-oxo-1 ,2-dihydro-3H- indole-3-yliden)-/V-(4-sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 -benzyl-5-nitro-2-oxo- 1 ,2-dihydro-3H-indole-3-yliden)-/V-(4-sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 - benzyl-5-cyano-2-oxo-1 ,2-dihydro-3H-indole-3-yliden)-/V-(4- sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 -benzyl-5-karbamoil-2-oxo-1 ,2-dihydro-3H- indole-3-yliden)-N-(4-sulphamoilphenyl)hydrazinecarbothioamide, Sodium 3-[1 -benzyl-2-oxo- 3-[4-(sulphamoilphenyl)karbamotioil]hydrazineiliden]-2,3-dihydro-1 Hindole-5-sul^ 2- (1 -benzyl-5-sulphamoil-2-oxo-1 ,2-dihydro-3 - -indole-3-yliden)-/V-(4- sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 -benzyl-6-fluoro-2-oxo-1 ,2-dihydro-3 7- indole-3-yliden)-/V-(4-sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 -benzyl-6-chloro-2- oxo-1 ,2-dihydro-3Hindole-3-yliden)-N-(4-sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 - benzyl-6-bromo-2-oxo-1 ,2-dihydro-3 - -indole-3-yliden)-/V-(4- sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 -benzyl-7-methyl-2-oxo-1 ,2-dihydro-3 7- indole-3-yliden)-/V-(4-sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 -benzyl-7- trifluoromethyl-2-oxo-1 ,2-dihydro-3H-indole-3-yliden)-/V-(4- sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 -benzyl-7-metoxy-2-oxo-1 ,2-dihydro-3 7- indole-3-yliden)-/V-(4-sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 -benzyl-7-fluoro-2-oxo- 1 ,2-dihydro-3Hindole-3-yliden)-N-(4-sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 - benzyl-7-chloro-2-oxo-1 ,2-dihydro-3 - -indole-3-yliden)-/V-(4- sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 -benzyl-7-bromo-2-oxo-1 ,2-dihydro-3 7- indole-3-yliden)-/V-(4-sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 -benzyl-5-fluoro-6- chloro-2-oxo-1 ,2-dihydro-3H-indole-3-yliden)-/V-(4- sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 -benzyl-5-chloro-7-methyl-2-oxo-1 ,2- dihydro-3Hindole-3-yliden)-N-(4-sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 -benzyl- 5,7-dichloro-2-oxo-1 ,2-dihydro-3H-indole-3-yliden)-/V-(4- sulphamoilphenyl)hydrazinecarbothioamide, 2-(1 -benzyl-5,7-dibromo-2-oxo-1 ,2-dihydro-3 7- indole-3-yliden)-/V-(4-sulphamoilphenyl)hydrazinecarbothioamide.
In an application of the present invention, the compounds shown by Formula III are selected from 2-(1 -Naphtylmethyl-2-oxo-1 ,2-dihydro-3H-indole-3-yliden)-A/-(4- sulphamoilphenyl)hydrazinecarbothioamide
Figure imgf000093_0001
and from its derivatives, for instance2-[1 -(1 -naphtylmethyl)-2-oxo-1 ,2-dihydro-3 - -indole-3- yliden]-/V-(4-sulphamoilphenyl)hydrazinecarbothioamide, 2-[1 -(1 -naphtylmethyl)-5-methyl-2- oxo-1 ,2-dihydro-3 - -indole-3-yliden]-/V-(4-sulphamoilphenyl)hydrazinecarbothioamide, 2-[1 - (1 -naphtylmethyl)-5-(propane-2-yl)-2-oxo-1 ,2-dihydro-3H-indole-3-yliden]-/V-(4- sulphamoilphenyl)hydrazinecarbothioamide, 2-[1 -(1 -naphtylmethyl)-5-t-butyl-2-oxo-1 ,2- dihydro-3Hindole-3-yliden]-N-(4-sulphamoilphenyl)hydrazinecarbothioami 2-[1 -(1 - naphtylmethyl)-5-metoxy-2-oxo-1 ,2-dihydro-3 - -indole-3-yliden]-/V-(4- sulphamoilphenyl)hydrazinecarbothioamide, 2-[1 -(1 -naphtylmethyl)-5-trif luorometoxy-2-oxo- 1 ,2-dihydro-3Hindole-3-yliden]-N-(4-sulphamoilphenyl)hydrazinecarbothioamide, 2-[1 -(1 - naphtylmethyl)-5-trifluorometoxy-2-oxo-1 ,2-dihydro-3 - -indole-3-yliden]-/V-(4- sulphamoilphenyl)hydrazinecarbothioamide, 2-[1 -(1 -naphtylmethyl)-5-fluoro-2-oxo-1 ,2- dihydro-3Hindole-3-yliden]-N-(4-sulphamoilphenyl)hydrazinecarbothioamide, 2-[1 -(1 - naphtylmethyl)-5-chloro-2-oxo-1 ,2-dihydro-3 - -indole-3-yliden]-/V-(4- sulphamoilphenyl)hydrazinecarbothioamide, 2-[1 -(1 -naphtylmethyl)-5-bromo-2-oxo-1 ,2- dihydro-3Hindole-3-yliden]-N-(4-sulphamoilphenyl)hydrazinecarbothioamide, 2-[1 -(1 - naphtylmethyl)-5-iyodo-2-oxo-1 ,2-dihydro-3 - -indole-3-yliden]-/V-(4- sulphamoilphenyl)hydrazinecarbothioamide, 2-[1 -(1 -naphtylmethyl)-5-nitro-2-oxo-1 ,2- dihydro-3Hindole-3-yliden]-N-(4-sulphamoilphenyl)hydrazinecarbothioamide, 2-[1 -(1 - naphtylmethyl)-5-cyano-2-oxo-1 ,2-dihydro-3Hindole-3-yliden]-/V-(4- sulphamoilphenyl)hydrazinecarbothioamide, 2-[1 -(1 -naphtylmethyl)-5-karbamoil-2-oxo-1 ,2- dihydro-3Hindole-3-yliden]-N-(4-sulphamoilphenyl)hydrazinecarbothioamide, sodium 3-[1 -(1 - naphtylmethyl)-2-oxo-3-[4-(sulphamoilphenyl)karbamotioil]hydrazineiliden]-2,3-dihydro-1 - - indole-5-sulphonate, 2-[1 -(1 -naphtylmethyl)-5-sulphamoil-2-oxo-1 ,2-dihydro-3 7-indole-3- yliden)-N-(4-sulphamoilphenyl]hydrazinecarbothioamide,2-[1 -(1 -naphtylmethyl)-6-fluoro-2- oxo-1 ,2-dihydro-3 - -indole-3-yliden)-/V-(4-sulphamoilphenyl]hydrazinecarbothioamide, 2-[1 - (1 -naphtylmethyl)-6-chloro-2-oxo-1 ,2-dihydro-3H-indole-3-yliden)-/V-(4- sulphamoilphenyl]hydrazinecarbothioamide, 2-[1 -(1 -naphtylmethyl)-6-bromo-2-oxo-1 ,2- dihydro-3 - -indole-3-yliden)-/V-(4-sulphamoilphenyl]hydrazinecarbothioamide, 2-[1 -(1 - naphtylmethyl)-7-methyl-2-oxo-1 ,2-dihydro-3 - -indole-3-yliden)-/V-(4- sulphamoilphenyl]hydrazinecarbothioamide, 2-[1 -(1 -naphtylmethyl)-7-trifluoromethyl-2-oxo- 1 ,2-dihydro-3 - -indole-3-yliden)-/V-(4-sulphamoilphenyl]hydrazinecarbothioamide, 2-[1 -(1 - naphtylmethyl)-7-metoxy-2-oxo-1 ,2-dihydro-3 - -indole-3-yliden)-/V-(4- sulphamoilphenyl]hydrazinecarbothioamide, 2-[1 -(1 -naphtylmethyl)-7-fluoro-2-oxo-1 ,2- dihydro-3 - -indole-3-yliden)-/V-(4-sulphamoilphenyl]hydrazinecarbothioamide, 2-[1 -(1 - naphtylmethyl)-7-chloro-2-oxo-1 ,2-dihydro-3H-indole-3-yliden)-/V-(4- sulphamoilphenyl]hydrazinecarbothioamide, 2-[1 -(1 -naphtylmethyl)-7-bromo-2-oxo-1 ,2- dihydro-3 - -indole-3-yliden)-/V-(4-sulphamoilphenyl]hydrazinecarbothioamide, 2-[1 -(1 - naphtylmethyl)-5-fluoro-6-chloro-2-oxo-1 ,2-dihydro-3/-/-indole-3-yliden]-/V-(4- sulphamoilphenyl]hydrazinecarbothioamide, 2-[1 -(1 -naphtylmethyl)-5-chloro-7-methyl-2-oxo- 1 ,2-dihydro-3 - -indole-3-yliden]-/V-(4-sulphamoilphenyl)hydrazinecarbothioamide, 2-[1 -(1 - naphtylmethyl)-5,7-dichloro-2-oxo-1 ,2-dihydro-3 - -indole-3-yliden]-/V-(4- sulphamoilphenyl)hydrazinecarbothioamide, 2-[1 -(1 -naphtylmethyl)-5,7-dibromo-2-oxo-1 ,2- dihydro-3Hindole-3-yliden]-N-(4-sulphamoilphenyl)hydrazinecarbothioam
In an application of the present invention, the compounds shown by Formula III are selected from 2-(2-Naphtylmethyl-2-oxo-1 ,2-dihydro-3W-indole-3-yliden)-A -(4- sulphamoilphenyl)hydrazinecarbothioamide
Figure imgf000095_0001
and from its derivatives, for instance 2-[1 -(2-naphtylmethyl)-2-oxo-1 ,2-dihydro-3 - -indole- 3-yliden]-/V-(4-sulphamoilphenyl)hydrazinecarbothioamide, 2-[1 -(2-naphtylmethyl)-5-methyl- 2-OXO-1 ,2-dihydro-3 - -indole-3-yliden]-/V-(4-sulphamoilphenyl)hydrazinecarbothioamide, 2-[1 - (2-naphtylmethyl)-5-(propane-2-yl)-2-oxo-1 ,2-dihydro-3H-indole-3-yliden]-/V-(4- sulphamoilphenyl)hydrazinecarbothioamide, 2-[1 -(2-naphtylmethyl)-5-t-butyl-2-oxo-1 ,2- dihydro-3 - -indole-3-yliden]-/V-(4-sulphamoilphenyl)hydrazinecarbothioamide, 2-[1 -(2- naphtylmethyl)-5-metoxy-2-oxo-1 ,2-dihydro-3 - -indole-3-yliden]-/V-(4- sulphamoilphenyl)hydrazinecarbothioamide, 2-[1 -(2-naphtylmethyl)-5-trifluorometoxy-2-oxo- 1 ,2-dihydro-3 - -indole-3-yliden]-/V-(4-sulphamoilphenyl)hydrazinecarbothioamide, 2-[1 -(2- naphtylmethyl)-5-trifluorometoxy-2-oxo-1 ,2-dihydro-3 - -indole-3-yliden]-/V-(4- sulphamoilphenyl)hydrazinecarbothioamide, 2-[1 -(2-naphtylmethyl)-5-fluoro-2-oxo-1 ,2- dihydro-3 - -indole-3-yliden]-/V-(4-sulphamoilphenyl)hydrazinecarbothioamide, 2-[1 -(2- naphtylmethyl)-5-chloro-2-oxo-1 ,2-dihydro-3 - -indole-3-yliden]-/V-(4- sulphamoilphenyl)hydrazinecarbothioamide, 2-[1 -(2-naphtylmethyl)-5-bromo-2-oxo-1 ,2- dihydro-3 - -indole-3-yliden]-/V-(4-sulphamoilphenyl)hydrazinecarbothioamide, 2-[1 -(2- naphtylmethyl)-5-iyodo-2-oxo-1 ,2-dihydro-3 - -indole-3-yliden]-/V-(4- sulphamoilphenyl)hydrazinecarbothioamide, 2-[1 -(2-naphtylmethyl)-5-nitro-2-oxo-1 ,2- dihydro-3 - -indole-3-yliden]-/V-(4-sulphamoilphenyl)hydrazinecarbothioamide, 2-[1 -(2- naphtylmethyl)-5-cyano-2-oxo-1 ,2-dihydro-3 - -indole-3-yliden]-/V-(4- sulphamoilphenyl)hydrazinecarbothioamide, 2-[1 -(2-naphtylmethyl)-5-karbamoil-2-oxo-1 ,2- dihydro-3 - -indole-3-yliden]-/V-(4-sulphamoilphenyl)hydrazinecarbothioamide, Sodium 3-[1 - (2-naphtylmethyl)-2-oxo-3-[4-(sulphamoilphenyl)karbamotioil]hydrazineiliden]-2,3-dihydro- 1 H-indole-5-sulphonate, 2-[1 -(2-naphtylmethyl)-5-sulphamoil-2-oxo-1 ,2-dihydro-3 7-indole-3- yliden)-/V-(4-sulphamoilphenyl]hydrazinecarbothioamide,2-[1 -(2-naphtylmethyl)-6-fluoro-2- oxo-1 ,2-dihydro-3 - -indole-3-yliden)-/V-(4-sulphamoilphenyl]hydrazinecarbothioamide, 2-[1 - (2-naphtylmethyl)-6-chloro-2-oxo-1 ,2-dihydro-3H-indole-3-yliden)-/V-(4- sulphamoilphenyl]hydrazinecarbothioamide, 2-[1 -(2-naphtylmethyl)-6-bromo-2-oxo-1 ,2- dihydro-3Hindole-3-yliden)-N-(4-sulphamoilphenyl]hydrazinecarbothioam 2-[1 -(2- naphtylmethyl)-7-methyl-2-oxo-1 ,2-dihydro-3 - -indole-3-yliden)-/V-(4- sulphamoilphenyl]hydrazinecarbothioamide, 2-[1 -(2-naphtylmethyl)-7-trifluoromethyl-2-oxo- 1 ,2-dihydro-3Hindole-3-yliden)-N-(4-sulpham 2-[1 -(2- naphtylmethyl)-7-metoxy-2-oxo-1 ,2-dihydro-3 - -indole-3-yliden)-/V-(4- sulphamoilphenyl]hydrazinecarbothioamide, 2-[1 -(2-naphtylmethyl)-7-fluoro-2-oxo-1 ,2- dihydro-3Hindole-3-yliden)-N-(4-sulphamoilphenyl]hydrazinecarbothioam^ 2-[1 -(2- naphtylmethyl)-7-chloro-2-oxo-1 ,2-dihydro-3 - -indole-3-yliden)-/V-(4- sulphamoilphenyl]hydrazinecarbothioamide, 2-[1 -(2-naphtylmethyl)-7-bromo-2-oxo-1 ,2- dihydro-3Hindole-3-yliden)-N-(4-sulphamoilphenyl]hydrazinecarbothioam^ 2-[1 -(2- naphtylmethyl)-5-fluoro-6-chloro-2-oxo-1 ,2-dihydro-3 - -indole-3-yliden]-/V-(4- sulphamoilphenyl]hydrazinecarbothioamide, 2-[1 -(2-naphtylmethyl)-5-chloro-7-methyl-2-oxo- 1 ,2-dihydro-3Hindole-3-yliden]-N-(4-sulphamoilphenyl)hydrazinecarbothioam 2-[1 -(2- naphtylmethyl)-57-dichloro-2-oxo-1 ,2-dihydro-3H-indole-3-yliden]-/V-(4- sulphamoilphenyl)hydrazinecarbothioamide, 2-[1 -(2-naphtylmethyl)-5,7-dibromo-2-oxo-1 ,2- dihydro-3Hindole-3-yliden]-N-(4-sulphamoilphenyl)hydrazinecarbothioam
Thus, from one perspective, the present invention relates to molecules shown by Formula II and Formula III whose general structures and specific examples are given above.
From another perspective, the present invention relates to a method to be used in preparation of the molecules shown by Formula II. In an application of the present invention, the substances shown by Formula II described in the present invention can be prepared by means of different methods by taking into consideration the beginning substances shown by Formula I.
In order to describe the molecule shown by Formula I, the terms of "Formula I", "1 H-indole- 2,3-dione derivatives", "isatin derivatives" or " can be interchangeably used.
In the subject matter method, the beginning substance shown by Formula I and R4Y are used;
Figure imgf000097_0001
Here;
R1 = H, CH3, CH(CH3)2, C(CH3)3, OCH3, OCF3, F, CI, Br, I, N02, CN, CONH2, S03Na, S02NH2,
Y= CI, Br, I
R2= H, F, CI, Br
R3= H, CH3, CF3, OCH3, F, CI, Br
R1 = F, R2= CI; R1 = CI, R3= CH3; R1 = R3= CI; R1 = R3= Br
R4= H, CH3, C2H5, n-C3H7, CH(CH3)2, CH2CH=CH2, CH2COOH, (CH2)2COOH, CH(CH3)COOH, (CH2)3COOH, CH2COOC2H5, CH2COOCH(CH3)2, CH2COOC(CH3)3, (CH2)2COOC2H5! CH(CH3)COOC2H5! (CH2)3COOC2H5
Figure imgf000098_0001
The specific procedures related to preparation of Formula II molecule by means of the subject matter method are given in examples section, and all of said methods can be applied to the subject matter molecules.
From another perspective, the present invention relates to a method to be used in preparation of the molecules shown by Formula III.
In a method in accordance with the present invention, the Formula III compounds are obtained by means of (i) obtaining substance B from compound A shown below, (ii) afterwards, obtaining compound C from compound B and (iii) reacting this compound C with the compound shown by Formula I or II. Within the scope of the present invention, compound A is mentioned as "A", compound B is mentioned as "B" and compound C is mentioned as "C".
In this method, first of all, compound A is transformed into compound B (i):
Figure imgf000099_0001
Here, it is shown as R5= R6= R7= H, S02NH2. und C (ii):
Figure imgf000099_0002
Here, it is shown as R5= R6= R7= H, S02NH2.
In the final step, this compound C is reacted with the compound shown by Formula I or II,
Figure imgf000099_0003
H, CH3, CH(CH3)2, C(CH3)3, OCH3, OCF3, F, CI, Br, I, N02, CN, CONH2, S03Na, S02NH2, R2= H, F, CI, Br
R3= H, CH3, CF3, OCH3, F, CI, Br
R1 = F, R2= CI; R1 = CI, R3= CH3; R1 = R3= CI; R1 = R3= Br R4= H, CH3, C2H5, n-C3H7, CH(CH3)2, CH2CH=CH2, CH2COOH, (CH2)2COOH, CH(CH3)COOH, (CH2)3COOH, CH2COOC2H5, CH2COOCH(CH3)2, CH2COOC(CH3)3, (CH2)2COOC2H5, CH(CH3)COOC2H5, (CH2)3COOC2H5
R5= R6= R7= H, S02NH2
Y=
Figure imgf000100_0001
By means of the subject matter molecules shown by Formula II and Formula III, it is aimed to blunt the specifically related enzyme or receptor mechanisms against pluralities of diseases including the diseases in the cancer and immunity system. Within this scope, the molecules shown by Formula II and Formula III can be used as medicine in treatment of pluralities of diseases including cancer and the diseases of the immunity system. Now, the present invention will be described with reference to the below mentioned examples which are only for exemplary purposes and which shall not be interpreted to delimit the scope of the present invention in any manner. EXAMPLES:
Example 1 : 1st method which can be used in preparation of the Formula II substances
1 H-indole-2,3-dione (isatin) derivatives are heated and mixed for 1 hour at 40-60°C inside approximately 10 mL dimethyl formamide (DMF) where I (10 mmole) and potassium carbonate (K2C03) (14.5 mmole) are solvents. R4 halogenure (1 1 .0 mmole) and potassium iodure (Kl) (2.0 mmole) as catalyst are added to the formed dark colored suspension. The mixture is continued to be heated and mixed at 40-60°C by being controlled by means of thin layer chromatography such that no I residue remains. The mixture is neutralized with hydrochloric acid (HCI), and it is extracted by means of 20 mL ethyl acetate four times and it is dried with the help of anhydrous sodium sulphate (Na2S04). The solvent is removed from the medium under vacuum. The remaining solid part is purified with the help of column chromatography.
Example 2: 2nd method which can be used in preparation of the Formula II substances
I (0.01 mole) and K2C03 (0.015 mmole) are mixed inside approximately 30 mL DMF as solvent such that I is completely dissolved. R4 halogenure (0.011 moles) is added in the form of small portions to the dark brilliant red colored suspension formed at the end of stirring 30 minutes, and it is stirred 12-14 hours more. The mixture formed at the end of the reaction is diluted with water. It is extracted with dichloromethane (CH2CI2) and it is washed with water, and it is dried with the help of anhydrous Na2S04. The solvent is vaporized in roto vapor under pressure. The remaining solid part is purified and cleaned with the help of column chromatography including silica gel.
Example 3: 3rd method which can be used in preparation of the Formula II substances
I (0.66 mmole) is dissolved in approximately 4 mL DMF with K2C03 or sodium hydride (NaH) (0.92 mmole). The mixture is mixed under nitrogen gas at 4°C for 3 hours. The formed I sodium salt is reacted with suitable R4 halogenure under the Kl catalyst, and it is heated for 18 hours more at 50°C. 80 mL water is added to the formed solution and 1 M HCI (2 mL) is added until pH is 1 . The formed suspension is filtered and the obtained precipitation is washed with water. The solid part is purified and cleaned with the help of flash chromatography.
Example 4: 4th method which can be used in preparation of the Formula II substances I (1 g) is dissolved by mixing in icy medium inside anhydrous DMF. After solid K2C03 (7.2 mmole) is added, the temperature is brought to room temperature, and it is continued to be mixed for 1 hour. At the end of the duration, R4 halogenure (1 g) is added, and the reaction is heated and mixed for 5-24 hours at 80°C under the Kl (6 mmole) catalyst. The end of the reaction is controlled with TLC, and the mixture is poured into 50 ml_ HCI, and it is extracted with 50 ml ethyl acetate. The ethyl acetate layer is washed with salty water, and it is dried with the help of MgS04, and it is removed from the medium under solvent vacuum.
Example 5: 5th method which can be used in preparation of the Formula II substances I (1 mmole) is dissolved in approximately 20 ml_ DMF. Anhydrous K2C03 (3 mmole) is added to the reaction medium. The mixture is mixed at room temperature such that there remains no I residue. The solvent is removed from the medium under vacuum. The remaining solid part is purified and cleaned with the help of column chromatography. Example 6: 6th method which can be used in preparation of the Formula II substances
Γ (34 mmole) is added to solution in approximately 100 ml_ tetra hydrofuran (THF) with tersiyer potassium butoxide (tert-BuOK) (43.8 mmole) at 0°C. After the mixture is stirred for 30 minutes, R4 halogenure (40.8 mmole) is added drop by drop to the reaction medium at 0°C within duration of 20 minutes. The reaction temperature is brought to room temperature and it is stirred for 16 hours more. Afterwards, it is concentrated under low pressure. The remaining residue is dissolved in ethyl acetate. It is washed with water and it is dried with the help of MgS04.The solid part is purified and cleaned with the help of flash chromatography.
Example 7: 7th method which can be used in preparation of the Formula II substances I (1 equiv.), Γ in 0.1 mmole corresponding to 1 ml_ is dissolved in anhydrous DMF. It is cooled and stirred in ice. Solid K2C03 or cesium carbonate (Cs2C03) (1 .2 equiv.) is added to the medium. The dark colored suspension formed is stirred for 1 hour at room temperature. R4 halogenure (1 .1 equiv.) and Kl (0.2 equiv.) are added thereon, and the reaction is heated and mixed for 5-24 hours at 80°C until there remains no I residue in the medium. The reaction mixture is poured into HCI (0.5 M, 50 ml_) and it is extracted with ethyl acetate. The ethyl acetate layer is washed with salty water. It is dried with the help of MgS04. The solvent is removed from the medium and it is purified and cleaned with the help of solid flash chromatography. Example 8: 8th method which can be used in preparation of the Formula II substances
5 ml_ DMF is added to I (3 mmole) and calcium hydride (CaH2) (10 mmole) mixture. The obtained solution or suspension is stirred at 40-50°C and it is heated for 15-30 minutes. At the end of the duration, R4 halogenure is added to the reaction medium. Stirring continues at room temperature or at low temperature such that no I residue remains. The reaction mixture is poured into 10% NaCI (50 ml) aqueous solution acidified with 0.2 M HCI, and afterwards, it is extracted three times with 25 ml_ ethyl acetate. The part with ethyl acetate is separated, and it is washed with 25 ml_ salty water, and it is dried and filtered with the help of anhydrous Na2S04. The solvent is removed from the medium and solid part is purified and cleaned with the help of column chromatography.
Example 9: 9th method which can be used in preparation of the Formula II substances I (0.10 mmole) and CaH2 (0.10 mole) are stirred in 50 ml_ DMF. The reaction mixture is heated in oil bath for 1 hour at 100°C. At the end of the duration, the mixture is cooled down to approximately 40°C. Afterwards, R4 halogenure (1 10-150 mmole) is slowly added to medium. After the adding process is completed, the mixture is heated for 2-4 hours by being controlled chromatographically with ITK until there remains no isatin residue in the oil bath at 100°C. When it is cooled, the part precipitating in the medium is separated, and it is poured in watery HCI (200 ml_, 0.5 M). The watery solution is filtered and the remaining residue is washed with water. It is recommended to extract the watery part with ethyl acetate for increasing efficiency. The formed solid product is crystallized and cleaned from the hexane/ CHCI2 mixture.
Example 10: 10th method which can be used in preparation of the Formula II substances
NaH (13.19 mmol; in 60% dispersion mineral oil) at 0°C is added to the solution in I (10.99 mmole) 30 ml_ anhydrous DMF. The heterogeneous mixture is stirred for 1 hour at room temperature. R4 halogenure is added to the mixture at the end of the duration, and the mixture is continued to the stirred at room temperature for a night. At the end of the duration, cold icy water is added to the medium, and the precipitating solid part is filtered, and it is removed from the medium. It is washed with water and petrol ether and it is dried under vacuum.
Example 11 : 11th method which can be used in preparation of the Formula II substances
I (1 mmole), a suitable base (1 .3 mmole) (Na2C03, K2C03, Cs2C03, CaH2, TEA, LiOH, NMM, NaEt) and R4 halogenure (1 .1 mmole) mixture is subjected to microwave rays under 160-400 watt energy for duration between 2-7 minutes inside polar aprotic solvent (DMF, DMA, HMPT, MeCN, DMSO, NMP). The reaction is cooled until room temperature. The compound, formed when it is substantially stirred with icy water, is filtered and removed from the medium.
Example 12: 12th method which can be used in preparation of the Formula II substances
The solution of sodium (0.8 g) in 16 ml_ absolute ethanol is added to I provided in suspension form in 24 ml_ absolute alcohol. The sodium salt of the formed purple-black colored I is removed from the medium. It is substantially washed with alcohol and benzene and dried. The sodium salt (1 mmole) of the obtained I and R4 halogenure (1 .1 mmole) are heated by being subject to microwave rays under 200-500 watt energy in durations changing between 3-5 minutes. The reaction is cooled down to room temperature. The compound formed when substantially mixed with icy water is filtered and removed from the medium.
Example 13: 13th method which can be used in preparation of the Formula II substances
Neutral aluminum (400 mg) is added to the solution of sodium salt (Na ) (1 mmole) of I in very small amount of water. The excessive portion of the solvent is vaporized in rato vapor, and the solid portion is dried at 1 10°C for one hour and the R4 halogenure (1 .1 mmole) is absorbed to the aluminum in I. The reaction is subjected to microwave rays under 400-800 watt energy in durations changing between 4-10 minutes. The mixture is extracted with CH2CI2 after it is cooled down to room temperature. The solid part is purified after the solvent is vaporized.
Example 14: 14th method which can be used in preparation of the Formula II substances
I (2.1 1 mmole) is put into 1 ,8-diazabicyclo[5.4.0]undec-7-en (DBU) (1.1 eq) and R4 halogenure (1 .1 eq) 3 ml_ ethanol selected as base. With the help of a magnetic stirrer, the reaction is subjected to microwave radiation under power of 300 watt in durations changing between 10-25 minutes at 120-140°C and the reaction is heated. Afterwards the reaction is cooled down to room temperature. It is waited in a deep freezer for a night and it is filtered with the help of vacuum. The filtered portion is vaporized under low pressure. The greasy part is purified with the help of solid column chromatography.
Example 15: General Synthesis Method for 2/3/4-lsothiocyanato benzensulphonamide Derivatives (B)
10 g 2/3/4-aminobenzensulphonamide A (60 mmole)is dissolved in 100 ml water including 25 ml concentrated HCI. 6.79 g (60 mmole) thiophosgene is added to the mixture and afterwards, the mixture is stirred until the red color of the thiophosgene is removed. The formed white crystallized sulphamoil phenyl isothiocyanate is filtered and it is washed with water. Example 16: General Synthesis Method for [N-(2/3/4-Sulphamoil)phenyl]thiosemi carbazide Derivatives (C)
The solution of 10.7 g 2/3/4-isothiocyanatobenzene sulphonamide B (50 mmole) in 20 ml ethanol is added drop by drop to the solution of 2.4 ml (50 mmole) hydrazine hydrate which was cooled in icy water by stirring continuously. The precipitated product is filtered immediately, and it is crystallized from ethanol.
Example 17: 1st method which can be used in preparation of the Formula III substances
The solution of non-substituted/1 -substituted 1 H-indole-2,3-dione I or II (2 mmole) in 10 ml ethanol is heated and dissolved in water bath. 0.49 g [N-(2/3/4-sulphamoil)phenyl]thiosemi carbazide C (2 mmole) is added thereon. The mixture is heated under cooler which returns 2-6 hours and it is waited for a night. The formed product is filtered, and it is washed in ethanol or it is purified by means of crystallization. Example 18: 2nd method which can be used in preparation of the Formula III substances
The solution of I or II and C, having equal molar amount, in ethanol or anhydrous ethanol is heated under the cooler which returns to 2-8 hours in the presence of acid (H2S04, p-toluene sulphonic acid) added as catalyst. The formed product is filtered from the medium. It is cleaned by being washed with a suitable solvent and by being crystallized.
Example 19: 3rd method which can be used in preparation of the Formula III substances
As catalyst, 1 -2 drops of concentrated hydrochloric acid or glacial acetic acid (HCI, g.CH3COOH) is added to the solution of I or II and C in ethanol, having equal molar amount, and the mixture is continuously stirred and it is heated for between 30 minutes to 1 -5 hours. It is cooled down to room temperature. It is waited for a night. The thiosemicarbazone which precipitates in the reaction medium is filtered and it is cleaned by being washed by cold alcohol. It is crystallized and cleaned from the suitable solvent.
Example 20: 4th method which can be used in preparation of the Formula III substances C is added to the solution of I or II having equal molar amount into the solution of approximately 30 ml_ ethanol. The mixture is heated for approximately 30 minutes - 2 hours. At the end of the duration, it is cooled down to room temperature and it is waited for a night. The precipitated solid substance is filtered and removed from the medium and it is washed by alcohol and dried.
Example 21 : 5th method which can be used in preparation of the Formula III substances
1 -2 drops of concentrated HCI acid is added as catalyst to the solution of I or II and C, having equal molar amount, in 20-30 ml_ ethanol. The reaction is stirred for 1 hour with the help of a magnetic stirrer at room temperature. The precipitating substance in the reaction medium is filtered and removed from the medium, and it is washed three times with 10 ml_ ethanol and it is cleaned. Example 22: 6th method which can be used in preparation of the Formula III substances
The solution of I or II (10 mmole), C (12 mmole) and triethylamin (0.4 mmole) mixture in 10 ml_ ethanol is heated by being mixed for 6 hours at 805C. When the reaction is cooled down to room temperature, the precipitated III is filtered from the medium and it is washed and cleaned by approximately 25 ml_ ethanol.
Example 23: 7th method which can be used in preparation of the Formula III substances
I or II (0.01 mole), C (0.01 1 mole) is subjected to 160 watt microwave radiation for 4 minutes under the catalyst of some drops of glacial acetic acid added to the medium. At the end of the reaction duration, it is controlled with TLC and the mixture is extracted three times by means of 20 ml_ CH2CI2 and the solvent is vaporized and the solid part is crystallized in ethanol. Example 24: 8th method which can be used in preparation of the Formula III substances
I or II (0.01 mole) and C (0.01 1 mole) is subjected to 160 watt microwave radiation for 4 minutes under the catalyst of some drops of glacial acetic acid added in 15 mL ethanol. At the end of the reaction duration, the reaction is cooled down to room temperature. The mixture is filtered and it is washed with 10 mL water, and the precipitating solid part is crystallized in 2 mL ethanol and cleaned.

Claims

1 . 2-indolinon derivative molecule shown by Formula II, characterized in that;
Figure imgf000107_0001
Formula II
R-t is selected from a group consisting of hydrogen, alkyl, metoxy, trifluorometoxy, halogen, nitro, carbonitryl, carboxamide, sodium sulphonate, sulphonamide,
F>2 is selected from a group consisting of hydrogen, halogens,
R3 is selected from a group consisting of hydrogen, methyl, trifluoromethyl, metoxy, halogens,
R4 is independently selected from a group consisting of alkyl, alkenil, alkanoic acid, alkanoic acid alkyl ester, benzyl, substituted benzyl, 1 -naphtylmethyl, 2-naphtylmethyl.
2. Hydrazine carbothioamide derivative molecule shown by Formula III, characterized in that;
Figure imgf000107_0002
Formula III
R1 is selected from a group consisting of hydrogen, alkyl, metoxy, trifluorometoxy, halogen, nitro, carbonitryl, carboxamide, sodium sulphonate, sulphonamide,
R2 is selected from hydrogen, halogen.
R3 is selected from a group consisting of hydrogen, alkyl, trifluoromethyl, metoxy, halogen R4 is selected from a group consisting of hydrogen, alkyl, alkenil, aralkyl, alkanoic acid, alkanoic acid alkyl ester and
R5, R6 and R7 are independently selected as sulphonamide group.
3. A molecule according to Claim 1 or 2, characterized in that in R1 , said alkyl is selected from methyl, isopropyl and tersiyer butyl groups, the halogen in R1 is selected from fluor, chlor, bromine and iodine groups, the halogen in R2 is selected from fluor, chlor and bromine groups and the halogen in R3 is selected from fluor, chlor and bromine groups.
4. A molecule according to Claim 1 or 2, characterized in that in fluor groups are selected and in R2, chlor groups are selected; in chlor groups are selected and in R3, methyl groups are selected; in and R3, dichlor is selected; in and R3, dibromine groups are selected.
5. A molecule according to Claim 1 or 2, characterized in that it is selected from a group consisting of R4 saturated or unsaturated, branched or unbranched Ci_3 alkyl, branched or unbranched C2.4 alkanoic acid, C2.4 branched or unbranched alkanoic acid branched or unbranched C2.4 alkyl ester.
6. A molecule according to Claim 5, characterized in that it is selected from a group consisting of saturated or unsaturated, branched or unbranched Ci_3 alkyl; methyl, ethyl, n-propyl, isopropyl, allyl provided in R4.
7. A molecule according to Claim 5, characterized in that it is selected from a group consisting of branched or unbranched C2.4 alkanoic acid, acetic acid, 2-methylacetic acid, propanonic acid, butanoic acid in R4.
8. A molecule according to Claim 5, characterized in that it is selected from a group consisting of C2.4 branched or unbranched alkanoic acid's branched or unbranched C2.4 alkyl ester, ethyl acetate, isopropyl acetate, tersiyer butyl-acetate, ethyl-propanoate, ethyl 2-methylacetate, ethyl butanoat in R4.
9. A molecule according to Claim 5, characterized in that in R4, it carries a group selected from substituted benzyl Ci_4 straight or branched alkyl, trifluoromethyl, metoxy, trifluorometoxy, fluor, chlor, bromine, iodine, nitro, carbonitryl, carboxy, hydroxy groups in positions 2, 3 or 4 of the phenyl ring.
10. A molecule according to Claim 9, characterized in that it is selected from a group comprising d_4 straight or branched alkyl, methyl, ethyl, isopropyl and tersiyer butyl groups.
11. A molecule according to Claim 9 or 10, characterized in that substituted benzyl moreover comprises a group selected from 2,4-dimethyl, 2,5-dimethyl, 2,6-dimethyl, 3,4-dimethyl, 3,5-dimethyl, 2,3-difluor, 2,4-difluor, 2,5-difluor, 2,6-difluor, 3,4-difluor, 3,5-difluor, 2,4- dichlor, 2,6-dichlor, 3,4-dichlor, 3,5-dichlor, 2-chlor-4-fluor, 2-chlor-6-fluor, 3,4,5-trifluor, 2,3,4,5,6-pentafluor in phenyl ring.
12. A molecule according to any one of the claims between Claim 2 and 1 1 , characterized in that in the sulphonamide benzene ring in R5, R6 and R7, when it is provided in R5, there is hydrogen in R6 and R7, and when it is provided in R6, there is hydrogen in R5 and R7, when it is provided in R7, there is hydrogen in R5 and R6.
13. A method to be used in preparation of the molecules shown by Formula II in accordance with Claim 1 -1 1 , characterized in that the molecule shown by Formula I and the R4Y molecule react with each other, and R1 , R2, R3 and R4 are selected from the groups given below,
H, CH3, CH(CH3)2, C(CH3)3, OCH3, OCF3, F, CI, Br, I, N02, CN, CONH2, S03Na, S02NH2,
Y= CI, Br, I
R2= H, F, CI, Br
R3= H, CH3, CF3, OCH3, F, CI, Br
R1 = F,
Figure imgf000109_0001
CI, R3= CH3; R1 = R3= CI ; R3= Br
R4= H, CH3, C2H5, n-C3H7, CH(CH3)2, CH2CH=CH2, CH2COOH, (CH2)2COOH, CH(CH3)COOH, (CH2)3COOH, CH2COOC2H5, CH2COOCH(CH3)2, CH2COOC(CH3)3,
(CH2)2COOC2H5, CH(CH3)COOC2H5, (CH2)3COOC2H5
Figure imgf000110_0001
14. A method to be used in preparation of the molecule shown by Formula III in accordance with Claim 1 -12, characterized by comprising the steps of;
(i) Transforming compound A into compound B
(ii) Transforming compound B into compound C
(iii) Reacting compound C with Formula I or Formula II and obtaining Formula III compound.
PCT/TR2016/050491 2015-12-11 2016-12-12 N-[(aminosulfonyl)phenyl]-2-(1,2-dihydro-2-oxo-3h-indol-3-ylidene)-hydrazinecarbothioamide derivatives for treating cancer and immunological disorders Ceased WO2017099695A1 (en)

Applications Claiming Priority (4)

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TR2015/15912A TR201515912A2 (en) 2015-12-11 2015-12-11 NEW 1-SUBSTITUTED 1H-INDOL-2,3-DIONE COMPOUNDS AND SYNTHESIS METHODS
TR2015/15912 2015-12-11
TR2015/16135A TR201516135A2 (en) 2015-12-15 2015-12-15 1H-INDOL-2,3-DION3-THIOSEMICARBAZONE DERIVATIVES AND SYNTHESIS METHODS CARRIING NEW SULFAMOIL RESIDUE
TR2015/16135 2015-12-15

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