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WO2007105989A3 - 1-oxo-3-(1h-indole)-3-il-1,2,3,4-tetrahydroisoxynolines, methods for the production thereof, combinatoric library and focused library - Google Patents

1-oxo-3-(1h-indole)-3-il-1,2,3,4-tetrahydroisoxynolines, methods for the production thereof, combinatoric library and focused library Download PDF

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Publication number
WO2007105989A3
WO2007105989A3 PCT/RU2007/000116 RU2007000116W WO2007105989A3 WO 2007105989 A3 WO2007105989 A3 WO 2007105989A3 RU 2007000116 W RU2007000116 W RU 2007000116W WO 2007105989 A3 WO2007105989 A3 WO 2007105989A3
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WO
WIPO (PCT)
Prior art keywords
alkyl
indole
aryl
tetrahydroisoxynolines
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.)
Ceased
Application number
PCT/RU2007/000116
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French (fr)
Russian (ru)
Other versions
WO2007105989A2 (en
Inventor
Alexander Vasiliev Ivashchenko
Dmitri Vladimirovic Kravchenko
Marina Vasilievna Loseva
Ilya Matusovich Okun
Sergey Yevgenievich Tkachenko
Alexander Viktorovich Khvat
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Alla Chem LLC
Original Assignee
Alla Chem LLC
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Filing date
Publication date
Application filed by Alla Chem LLC filed Critical Alla Chem LLC
Publication of WO2007105989A2 publication Critical patent/WO2007105989A2/en
Publication of WO2007105989A3 publication Critical patent/WO2007105989A3/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/10—Spiro-condensed systems

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Indole Compounds (AREA)

Abstract

The invention relates to novel 1-oxo-3-(1h-indole)-3-il-1,2,3,4-tetrahydroisoxynolines and to the cis- and trans-isomers thereof exhibiting protein kinase inhibiting properties, to methods for the production thereof and to combinatoric and focused libraries for separating leader compounds. 1-oxo-3-(1h-indole)-3-il-1,2,3,4-tetrahydroisoxynolines correspond to general formulas 1 and 2, wherein R1, R2 and R4, independently from each other are, a cyclic system substituent selected from hydrogen and alkyl, R3 is an aminogroup substituent selected from alkyl, cycloalkyl or alkyl, possibly substituted with an aryl, heteroaryl, heterocyclyl, alkoxy, amine, alkylamine and dialkylamine group, R5 and R6 are, independently from each other, an amino group substituent selected from hydrogen, aryl, heteroaryl, heterocyclyl, cycloalkyl, cycloalkenyl, alkyl or alkyl, possibly substituted with aryl, heteroaryl, heterocyclyl, cycloalkyl, cycloalkenyl, alkoxy, amino, alkylamine, dialkylamine, aryl alkylamine, or R5 and R6 forms, together with a nitrogen atom with which they are bound, a possibly substituted azaheterocycle. A method for obtaining compounds of general formula 1 consists in interacting corresponding indole-3-ilmethylenamines and homophtalic anhydrides in an organic solvent medium. A method for obtaining compounds of general formula 2 consists in treating the compounds of formula 1 with thionyl chloride or with 1,1'-carbonyldiimidazole in such a way that the respective derivatives are obtain and interact with respective amines of general formula 6 in the organic solvent medium.
PCT/RU2007/000116 2006-03-14 2007-03-12 1-oxo-3-(1h-indole)-3-il-1,2,3,4-tetrahydroisoxynolines, methods for the production thereof, combinatoric library and focused library Ceased WO2007105989A2 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
RU2006107658/04A RU2302417C1 (en) 2006-03-14 2006-03-14 1-oxo-3-(1h-indol-3-yl)-1,2,3,4-tetrahydroisoquinolines, methods of preparation thereof, combinatory library, and focused library
RU2006107658 2006-03-14

Publications (2)

Publication Number Publication Date
WO2007105989A2 WO2007105989A2 (en) 2007-09-20
WO2007105989A3 true WO2007105989A3 (en) 2007-11-22

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PCT/RU2007/000116 Ceased WO2007105989A2 (en) 2006-03-14 2007-03-12 1-oxo-3-(1h-indole)-3-il-1,2,3,4-tetrahydroisoxynolines, methods for the production thereof, combinatoric library and focused library

Country Status (2)

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RU (1) RU2302417C1 (en)
WO (1) WO2007105989A2 (en)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US11426412B2 (en) 2017-10-18 2022-08-30 Jubilant Epipad LLC Imidazo-pyridine compounds as PAD inhibitors
US11459338B2 (en) 2017-11-24 2022-10-04 Jubilant Episcribe Llc Heterocyclic compounds as PRMT5 inhibitors
US11529341B2 (en) 2018-03-13 2022-12-20 Jubilant Prodel LLC Bicyclic compounds as inhibitors of PD1/PD-L1 interaction/activation
US11629135B2 (en) 2017-11-06 2023-04-18 Jubilant Prodell Llc Pyrimidine derivatives as inhibitors of PD1/PD-L1 activation
US11833156B2 (en) 2017-09-22 2023-12-05 Jubilant Epipad LLC Heterocyclic compounds as pad inhibitors

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2006115135A1 (en) 2005-04-21 2006-11-02 Astellas Pharma Inc. Therapeutic agent for irritable bowel syndrome
TWI425945B (en) 2007-05-28 2014-02-11 Seldar Pharma Inc Tetrahydroisoquinolin-1-one derivatives or salt thereof
CN101367801B (en) * 2007-08-15 2011-01-12 上海恒瑞医药有限公司 Preparation method for pyrrol-hexahydric N heterocycle hydroxyl morpholine derivants, and medical uses thereof
GB0820856D0 (en) * 2008-11-14 2008-12-24 Univ Leuven Kath Novel inhibitors of flavivirus replication
US9416124B2 (en) * 2011-08-25 2016-08-16 St. Jude Children's Research Hospital Substituted 2-alkyl-1-OXO-N-phenyl-3-heteroaryl-1,2,3,4-tetrahydroisoquinoline-4-carboxamides for antimalarial therapies

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2006097323A1 (en) * 2005-03-18 2006-09-21 Lutz Weber TETRAHYDRO-ISOQUINOLIN-l-ONES FOR THE TREATMENT OF CANCER

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2006097323A1 (en) * 2005-03-18 2006-09-21 Lutz Weber TETRAHYDRO-ISOQUINOLIN-l-ONES FOR THE TREATMENT OF CANCER

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
"Comptes Rendus des Seances de l'Academie des Sciences, Serie C", SCIENCES CHIMIQUES, vol. 285, no. 10, 1977, pages 353 - 356 *
DATABASE ACS [online] KHAIMOVA M. ET AL.: "Synthesis of diastereomeric indole derivatives from azomethines and homophthakic anhydriges. One-step preparation of hexadchydroyohimbans", Database accession no. (ca 88-51065) *
TERENTIEV P.B. ET AL.: "Mass-spectry stereoizomernykh tsis-i trans-2 -alkil-3-aril(getaril)-4-(metoxikarbonil)-3-digidro-1N-izokhinolonov-1 i 1,2,3,4-tetragidroizokhinolinov", KHIMIYA GETEROTSIKLICHESKIKH SOEDINENY, no. 10, 1980, pages 1395 - 1397 *

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US11833156B2 (en) 2017-09-22 2023-12-05 Jubilant Epipad LLC Heterocyclic compounds as pad inhibitors
US12357639B2 (en) 2017-09-22 2025-07-15 Jubilant Epipad LLC Heterocyclic compounds as pad inhibitors
US11426412B2 (en) 2017-10-18 2022-08-30 Jubilant Epipad LLC Imidazo-pyridine compounds as PAD inhibitors
US11629135B2 (en) 2017-11-06 2023-04-18 Jubilant Prodell Llc Pyrimidine derivatives as inhibitors of PD1/PD-L1 activation
US11459338B2 (en) 2017-11-24 2022-10-04 Jubilant Episcribe Llc Heterocyclic compounds as PRMT5 inhibitors
US11529341B2 (en) 2018-03-13 2022-12-20 Jubilant Prodel LLC Bicyclic compounds as inhibitors of PD1/PD-L1 interaction/activation

Also Published As

Publication number Publication date
WO2007105989A2 (en) 2007-09-20
RU2302417C1 (en) 2007-07-10

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