GB1274521A - Dithiocarbazinic ester derivatives - Google Patents
Dithiocarbazinic ester derivativesInfo
- Publication number
- GB1274521A GB1274521A GB31122/69A GB3112269A GB1274521A GB 1274521 A GB1274521 A GB 1274521A GB 31122/69 A GB31122/69 A GB 31122/69A GB 3112269 A GB3112269 A GB 3112269A GB 1274521 A GB1274521 A GB 1274521A
- Authority
- GB
- United Kingdom
- Prior art keywords
- substituted
- chlorobenzyl
- dimethoxy
- aralkyl
- oxo
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 150000002148 esters Chemical class 0.000 title abstract 3
- 125000000217 alkyl group Chemical group 0.000 abstract 6
- 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 abstract 4
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 abstract 4
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 4
- 150000001875 compounds Chemical class 0.000 abstract 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 abstract 3
- 238000010561 standard procedure Methods 0.000 abstract 3
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 abstract 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 abstract 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 abstract 2
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 abstract 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 abstract 2
- 125000003342 alkenyl group Chemical group 0.000 abstract 2
- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 abstract 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 2
- WMKGGPCROCCUDY-PHEQNACWSA-N dibenzylideneacetone Chemical compound C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 WMKGGPCROCCUDY-PHEQNACWSA-N 0.000 abstract 2
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- 125000005843 halogen group Chemical group 0.000 abstract 2
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 abstract 2
- -1 hydrazinium cation Chemical class 0.000 abstract 2
- 238000011065 in-situ storage Methods 0.000 abstract 2
- LCPDWSOZIOUXRV-UHFFFAOYSA-N phenoxyacetic acid Chemical compound OC(=O)COC1=CC=CC=C1 LCPDWSOZIOUXRV-UHFFFAOYSA-N 0.000 abstract 2
- SATCULPHIDQDRE-UHFFFAOYSA-N piperonal Chemical compound O=CC1=CC=C2OCOC2=C1 SATCULPHIDQDRE-UHFFFAOYSA-N 0.000 abstract 2
- 229910052700 potassium Inorganic materials 0.000 abstract 2
- 239000011591 potassium Substances 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- 229910052708 sodium Inorganic materials 0.000 abstract 2
- 239000011734 sodium Substances 0.000 abstract 2
- JBGJVMVWYWUVOW-UHFFFAOYSA-N 1-(1-hydroxynaphthalen-2-yl)ethanone Chemical compound C1=CC=CC2=C(O)C(C(=O)C)=CC=C21 JBGJVMVWYWUVOW-UHFFFAOYSA-N 0.000 abstract 1
- CVBUKMMMRLOKQR-UHFFFAOYSA-N 1-phenylbutane-1,3-dione Chemical compound CC(=O)CC(=O)C1=CC=CC=C1 CVBUKMMMRLOKQR-UHFFFAOYSA-N 0.000 abstract 1
- VGBMZHFNLYKYBV-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-3-methoxyprop-2-enenitrile Chemical compound COC=C(C#N)C1=CC=C(OC)C(OC)=C1 VGBMZHFNLYKYBV-UHFFFAOYSA-N 0.000 abstract 1
- FNPUMVINNQFVCE-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-3-oxopropanenitrile Chemical compound COC1=CC=C(C(C=O)C#N)C=C1OC FNPUMVINNQFVCE-UHFFFAOYSA-N 0.000 abstract 1
- FQAYODYTZPXLRH-UHFFFAOYSA-N 2-(4-butanoyl-2,3-dichlorophenoxy)acetic acid Chemical compound CCCC(=O)C1=CC=C(OCC(O)=O)C(Cl)=C1Cl FQAYODYTZPXLRH-UHFFFAOYSA-N 0.000 abstract 1
- XSAYZAUNJMRRIR-UHFFFAOYSA-N 2-acetylnaphthalene Chemical class C1=CC=CC2=CC(C(=O)C)=CC=C21 XSAYZAUNJMRRIR-UHFFFAOYSA-N 0.000 abstract 1
- NTCCNERMXRIPTR-UHFFFAOYSA-N 2-hydroxy-1-naphthaldehyde Chemical compound C1=CC=CC2=C(C=O)C(O)=CC=C21 NTCCNERMXRIPTR-UHFFFAOYSA-N 0.000 abstract 1
- WLVPRARCUSRDNI-UHFFFAOYSA-N 2-hydroxy-1-phenyl-1-propanone Chemical compound CC(O)C(=O)C1=CC=CC=C1 WLVPRARCUSRDNI-UHFFFAOYSA-N 0.000 abstract 1
- ZETIVVHRRQLWFW-UHFFFAOYSA-N 3-nitrobenzaldehyde Chemical compound [O-][N+](=O)C1=CC=CC(C=O)=C1 ZETIVVHRRQLWFW-UHFFFAOYSA-N 0.000 abstract 1
- YQYGPGKTNQNXMH-UHFFFAOYSA-N 4-nitroacetophenone Chemical compound CC(=O)C1=CC=C([N+]([O-])=O)C=C1 YQYGPGKTNQNXMH-UHFFFAOYSA-N 0.000 abstract 1
- UMACQLRXHVIXHQ-UHFFFAOYSA-N 6-ethenyl-4-methoxy-1,3-benzodioxole-5-carbaldehyde Chemical compound C=CC1=C(C=O)C(OC)=C2OCOC2=C1 UMACQLRXHVIXHQ-UHFFFAOYSA-N 0.000 abstract 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 abstract 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 abstract 1
- 244000028419 Styrax benzoin Species 0.000 abstract 1
- 235000000126 Styrax benzoin Nutrition 0.000 abstract 1
- 235000008411 Sumatra benzointree Nutrition 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 239000004480 active ingredient Substances 0.000 abstract 1
- 125000002252 acyl group Chemical group 0.000 abstract 1
- 239000003513 alkali Substances 0.000 abstract 1
- 150000001342 alkaline earth metals Chemical class 0.000 abstract 1
- 125000003282 alkyl amino group Chemical group 0.000 abstract 1
- 229910021529 ammonia Inorganic materials 0.000 abstract 1
- 230000000507 anthelmentic effect Effects 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- WURBFLDFSFBTLW-UHFFFAOYSA-N benzil Chemical compound C=1C=CC=CC=1C(=O)C(=O)C1=CC=CC=C1 WURBFLDFSFBTLW-UHFFFAOYSA-N 0.000 abstract 1
- 229960002130 benzoin Drugs 0.000 abstract 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 abstract 1
- 239000012965 benzophenone Substances 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 125000004663 dialkyl amino group Chemical group 0.000 abstract 1
- NZZIMKJIVMHWJC-UHFFFAOYSA-N dibenzoylmethane Chemical compound C=1C=CC=CC=1C(=O)CC(=O)C1=CC=CC=C1 NZZIMKJIVMHWJC-UHFFFAOYSA-N 0.000 abstract 1
- 125000001891 dimethoxy group Chemical group [H]C([H])([H])O* 0.000 abstract 1
- 125000004185 ester group Chemical group 0.000 abstract 1
- 125000002541 furyl group Chemical group 0.000 abstract 1
- 235000019382 gum benzoic Nutrition 0.000 abstract 1
- 125000001072 heteroaryl group Chemical group 0.000 abstract 1
- 150000004677 hydrates Chemical class 0.000 abstract 1
- 125000005638 hydrazono group Chemical group 0.000 abstract 1
- 125000001041 indolyl group Chemical group 0.000 abstract 1
- 230000003993 interaction Effects 0.000 abstract 1
- 125000002950 monocyclic group Chemical group 0.000 abstract 1
- JZXFEEAAHUBNQT-UHFFFAOYSA-N n-[2-(4-nitrophenyl)-2-oxoethyl]acetamide Chemical compound CC(=O)NCC(=O)C1=CC=C([N+]([O-])=O)C=C1 JZXFEEAAHUBNQT-UHFFFAOYSA-N 0.000 abstract 1
- 239000000825 pharmaceutical preparation Substances 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- GCSHUYKULREZSJ-UHFFFAOYSA-N phenyl(pyridin-2-yl)methanone Chemical compound C=1C=CC=NC=1C(=O)C1=CC=CC=C1 GCSHUYKULREZSJ-UHFFFAOYSA-N 0.000 abstract 1
- 229940081310 piperonal Drugs 0.000 abstract 1
- 125000003367 polycyclic group Polymers 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 125000004076 pyridyl group Chemical group 0.000 abstract 1
- 125000005493 quinolyl group Chemical group 0.000 abstract 1
- 239000000376 reactant Substances 0.000 abstract 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 abstract 1
- 239000012312 sodium hydride Substances 0.000 abstract 1
- 229910000104 sodium hydride Inorganic materials 0.000 abstract 1
- 125000001544 thienyl group Chemical group 0.000 abstract 1
- ZWZVWGITAAIFPS-UHFFFAOYSA-N thiophosgene Chemical compound ClC(Cl)=S ZWZVWGITAAIFPS-UHFFFAOYSA-N 0.000 abstract 1
- 125000005208 trialkylammonium group Chemical group 0.000 abstract 1
- HFFLGKNGCAIQMO-UHFFFAOYSA-N trichloroacetaldehyde Chemical compound ClC(Cl)(Cl)C=O HFFLGKNGCAIQMO-UHFFFAOYSA-N 0.000 abstract 1
- 230000001549 tubercolostatic effect Effects 0.000 abstract 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D461/00—Heterocyclic compounds containing indolo [3,2,1-d,e] pyrido [3,2,1,j] [1,5]-naphthyridine ring systems, e.g. vincamine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/08—Vasodilators for multiple indications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C333/00—Derivatives of thiocarbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C333/14—Dithiocarbamic acids; Derivatives thereof
- C07C333/18—Esters of dithiocarbamic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/44—Radicals substituted by doubly-bound oxygen, sulfur, or nitrogen atoms, or by two such atoms singly-bound to the same carbon atom
- C07D213/53—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/04—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to the ring carbon atoms
- C07D215/06—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to the ring carbon atoms having only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached to the ring nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/26—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D307/30—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/32—Oxygen atoms
- C07D307/33—Oxygen atoms in position 2, the oxygen atom being in its keto or unsubstituted enol form
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/52—Radicals substituted by nitrogen atoms not forming part of a nitro radical
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D451/00—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof
- C07D451/02—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof
- C07D451/04—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof with hetero atoms directly attached in position 3 of the 8-azabicyclo [3.2.1] octane or in position 7 of the 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring system
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Cardiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Heart & Thoracic Surgery (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
1,274,521. Compounds containing hydrazono and dithiocarboxylic ester groups. EGYESULT GYOGYSZER ES TAPSZERGYAR. 19 June, 1969 [24 July, 1968], No. 31122/69. Heading C2C. Novel compounds I (including salts and hydrates thereof) wherein R<SP>1</SP> is H, straight or branched chain alkyl, alkenyl, aralkyl or aralkenyl (the aryl moiety embraces heteroaryl) which may be substituted by alkoxy, carboalkoxy, CO 2 H, amino, alkylamino, dialkylamino or trialkylammonium, or R<SP>1</SP> is phenyl, pyridyl, indolyl, quinolyl, thienyl or furyl which may be mono- or poly-substituted with halogen, alkyl, alkoxy, acyl, OH, SO 3 H, carboalkoxy or CO 2 H, R<SP>2</SP> is H, straight or branched chain alkyl or aralkyl which may be substituted as stated for R<SP>1</SP>, CO 2 H or R<SP>1</SP> and R<SP>2</SP> comprise together with the attached carbon a mono- or poly-cyclic radical having at least one of the ring carbons substituted by = O or = NÀNHCSSR<SP>3</SP>, and R<SP>3</SP> is straight or branched chain alkyl, alkenyl or aralkyl which may be mono- or poly-substituted by halogen and straight or branched alkyl, are obtained by reacting: (a) R<SP>1</SP>COR<SP>2</SP> (may be formed in situ) with NH 2 ÀNHÀCSSR<SP>3</SP>; (b) R<SP>1</SP>COR<SP>2</SP> with NH 2 NHÀCSSZ (one or both of the reactants may be formed in situ; Z is alkali or alkaline earth metal, ammonium or hydrazinium cation) and the intermediate compound so obtained is subsequently converted into 1 by standard methods; (c) R<SP>1</SP>R<SP>2</SP>C: NNH 2 with sodium, potassium, sodium amide or sodium hydride to afford R<SP>1</SP>R<SP>2</SP>ÀC: NNHZ 1 (Z 1 is sodium or potassium) which is in turn treated with carbon disulphide to give (converted to I by standard methods); (d) R<SP>1</SP>R<SP>2</SP>C = NNHZ 1 with ClCSSR<SP>3</SP>; (e) R<SP>1</SP>R<SP>2</SP>C = NNHZ 1 with thiophosgene to afford R<SP>1</SP>R<SP>2</SP>C: NNHCSCl which, in turn, is reacted with R<SP>3</SP>SZ to afford I; or (f) R<SP>1</SP>R<SP>2</SP>C: NNH 2 with R<SP>4</SP>SCSSR<SP>4</SP> at below 150 C. (R<SP>4</SP> is alkyl or aralkyl). The invention also encompasses exemplified novel compounds of the structure I but which are not covered by the preceding definitions of R 1 and R 2 . They are made from the following oxo-compounds (R 3 is given in parenthesis): chloral (Me, benzyl or p-chlorobenzyl), acetylacetone (Me), acetobutyrolactone (Me), pnitrobenzaldehyde (Me), piperonal (Me), pnitroacetophenone (Me or Et), p-nitro-α- acetamido - acetophenone (Me), 2 - hydroxy- 1 - naphthaldehyde (Me), 2 - methoxy - 3,4- methylenedioxy - 6 - vinyl - benzaldehyde (Me), α - formyl- or α - methoxymethylene - 3,4 - dimethoxyphenyl - acetonitrile (Me), DL - pnitro - α - acetamido - # hydroxy - propiophenone (Me and benzyl), 2-benzoylpyridine (Me), 2 - acetyl - 1 - naphthol (Me), 1- and 2- acetyl - naphthalenes (Me), 2,3 - dichloro - 4- butyryl - phenoxyacetic acid (Me), benzoylacetone (Me), benzophenone (Me), m-nitrobenzaldehyde (p - chlorobenzyl, 2,3 - dichloro- 4 - (2<SP>1 </SP>- methylenebutyryl) phenoxyacetic acid (Me), benzil (Me), benzoin (Me), #-piperidinopropiophenone (Me), 2-oxo-9,10-dimethoxy-, 2 - oxo - 3 - ethyl - 9,10 dimethoxy and 2-oxo - 4,4 - dimethyl - 9,10 - dimethoxy - 1,2,3,4,6,7- hexahydro - 11b - benzo[a]quinolizines (Me), dibenzal - acetone (Me), α - formyl - 3,4 - dimethoxy - phenyl - acetonitrile (p - chlorobenzyl), dibenzoylmethane (Me) and dibenzalacetone (p-chlorobenzyl). Dithiocarbazinic esters, NH 2 NHÀCSSR<SP>3</SP>, are obtained by reacting hydrazine hydrate with carbon disulphide in the presence of potassium hydroxide, ammonia or excess hydrazine hydrate and converting the dithiocarbazinic acid salt so obtained into the ester utilizing standard methods. Methyl - p - nitrophenyl - ketazin is obtained by the interaction of p-nitroacetophenone and NH 2 NHCSSEt. Pharmaceutical preparations, in particular, showing anthelmintic and tuberculostatic effects contain I as active ingredient; administration is, e.g. topically, orally and parenterally.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HUEE001547 | 1968-07-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1274521A true GB1274521A (en) | 1972-05-17 |
Family
ID=10995263
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB31122/69A Expired GB1274521A (en) | 1968-07-24 | 1969-06-19 | Dithiocarbazinic ester derivatives |
Country Status (8)
| Country | Link |
|---|---|
| AT (1) | AT293432B (en) |
| AU (1) | AU502845B2 (en) |
| CH (1) | CH532556A (en) |
| DE (1) | DE1934809A1 (en) |
| FR (1) | FR2013568A1 (en) |
| GB (1) | GB1274521A (en) |
| NL (1) | NL6911272A (en) |
| PL (1) | PL88879B1 (en) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1985004333A1 (en) * | 1984-03-23 | 1985-10-10 | A/S Cheminova | A biocidal, particularly fungicidal and/or bactericidal, composition |
| US5861526A (en) * | 1996-11-07 | 1999-01-19 | Bayer Corporation | Process for reducing dithiocarbazinate buildup in the preparation of methyl dithiocarbazinate |
| US5877339A (en) * | 1996-11-07 | 1999-03-02 | Bayer Corporation | Process for preparing methyl dithiocarbazinate by reacting methyl bromide with the reaction product of carbon disulfide and hydrazine in an aqueous medium |
| US6025514A (en) * | 1996-11-07 | 2000-02-15 | Bayer Corporation | Process for preparing methyl dithiocarbazinate by reacting methyl bromide with the reaction product of carbon disulfide, hydrazine and an adjunct base |
| EP0841324A3 (en) * | 1996-11-07 | 2001-09-19 | Bayer Corporation | A proces for preparing methyl dithiocarbazinate by reacting methyl bromide with the reaction product of carbon disulfide, hydrazine and an adjunct base |
| EP2530073A4 (en) * | 2010-01-27 | 2014-10-08 | Mitsubishi Rayon Co | NEW CHAIN TRANSFER AGENT AND EMULSION POLYMERIZATION USING THE SAME |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4602099A (en) * | 1973-04-02 | 1986-07-22 | Merrell Dow Pharmaceuticals Inc. | Antirhinovirus agents |
| DE3709414C1 (en) * | 1987-03-21 | 1988-02-18 | Bayer Ag | Process for the preparation of methyl dithiocarbazate |
| CH686642A5 (en) * | 1993-07-27 | 1996-05-15 | Sylvia Hover | Spectacle lens. |
-
1969
- 1969-06-10 FR FR6919045A patent/FR2013568A1/fr not_active Withdrawn
- 1969-06-19 GB GB31122/69A patent/GB1274521A/en not_active Expired
- 1969-07-08 AT AT653469A patent/AT293432B/en not_active IP Right Cessation
- 1969-07-09 DE DE19691934809 patent/DE1934809A1/en active Pending
- 1969-07-17 CH CH1095169A patent/CH532556A/en not_active IP Right Cessation
- 1969-07-21 PL PL1969134961A patent/PL88879B1/en unknown
- 1969-07-23 NL NL6911272A patent/NL6911272A/xx unknown
-
1975
- 1975-09-01 AU AU84444/75A patent/AU502845B2/en not_active Expired
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1985004333A1 (en) * | 1984-03-23 | 1985-10-10 | A/S Cheminova | A biocidal, particularly fungicidal and/or bactericidal, composition |
| US5861526A (en) * | 1996-11-07 | 1999-01-19 | Bayer Corporation | Process for reducing dithiocarbazinate buildup in the preparation of methyl dithiocarbazinate |
| US5877339A (en) * | 1996-11-07 | 1999-03-02 | Bayer Corporation | Process for preparing methyl dithiocarbazinate by reacting methyl bromide with the reaction product of carbon disulfide and hydrazine in an aqueous medium |
| US6025514A (en) * | 1996-11-07 | 2000-02-15 | Bayer Corporation | Process for preparing methyl dithiocarbazinate by reacting methyl bromide with the reaction product of carbon disulfide, hydrazine and an adjunct base |
| EP0841324A3 (en) * | 1996-11-07 | 2001-09-19 | Bayer Corporation | A proces for preparing methyl dithiocarbazinate by reacting methyl bromide with the reaction product of carbon disulfide, hydrazine and an adjunct base |
| EP2530073A4 (en) * | 2010-01-27 | 2014-10-08 | Mitsubishi Rayon Co | NEW CHAIN TRANSFER AGENT AND EMULSION POLYMERIZATION USING THE SAME |
| US9452978B2 (en) | 2010-01-27 | 2016-09-27 | Mitsubishi Rayon Co., Ltd. | Chain transfer agent and emulsion polymerization using the same |
| US9676888B2 (en) | 2010-01-27 | 2017-06-13 | Mitsubishi Chemical Corporation | Chain transfer agent and emulsion polymerization using the same |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2013568A1 (en) | 1970-04-03 |
| NL6911272A (en) | 1970-01-27 |
| AU502845B2 (en) | 1979-08-09 |
| DE1934809A1 (en) | 1970-01-29 |
| AU8444475A (en) | 1977-03-10 |
| CH532556A (en) | 1973-01-15 |
| AT293432B (en) | 1971-10-11 |
| PL88879B1 (en) | 1976-10-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PCNP | Patent ceased through non-payment of renewal fee |