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WO2007105989A3 - 1-oxo-3-(1h-indol-3-yl)-1,2,3,4-tétrahydroisoxynolines, procédés de production associés, bibliothèque combinatoire et bibliothèque ciblée - Google Patents

1-oxo-3-(1h-indol-3-yl)-1,2,3,4-tétrahydroisoxynolines, procédés de production associés, bibliothèque combinatoire et bibliothèque ciblée 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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English (en)
Russian (ru)
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WO2007105989A2 (fr
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
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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/fr
Publication of WO2007105989A3 publication Critical patent/WO2007105989A3/fr
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

La présente invention concerne de nouvelles 1-oxo-3-(1H-indol-3-yl)-1,2,3,4-tétrahydroisoxynolines, ainsi que les cis- et trans-isomères de celles-ci, présentant des propriétés d'inhibition de protéine kinase, des procédés de production associés et des bibliothèques combinatoire et ciblée permettant de séparer des composés principaux. Les 1-oxo-3-(1H-indol-3-yl)-1,2,3,4-tétrahydroisoxynolines sont représentées par les formules générales (1) et (2) dans lesquelles R1, R2 et R4, indépendamment les uns des autres, représentent un substituant de système cyclique sélectionné parmi hydrogène et alkyle, R3 représente un substituant de groupe amino sélectionné parmi alkyle, cycloalkyle ou alkyle, éventuellement substitué par un groupe aryle, hétéroaryle, hétérocyclyle, alcoxy, amino, alkylamine et dialkylamine, R5 et R6 représentent, indépendamment les uns des autres, un substituant de groupe amino sélectionné parmi hydrogène, aryle, hétéroaryle, hétérocyclyle, cycloalkyle, cycloalcényle, alkyle ou alkyle, éventuellement substitué par aryle, hétéroaryle, hétérocyclyle, cycloalkyle, cycloalcényle, alcoxy, amino, alkylamine, dialkylamine, aryle alkylamine, ou R5 et R6 forment, avec un atome d'azote auquel ils sont liés, un azahétérocycle éventuellement substitué. Cette invention concerne également un procédé permettant d'obtenir les composés représentés par la formule générale (1), lequel procédé comprend l'interaction d'indol-3-ylméthylènamines correspondantes et d'anhydrides homophtaliques dans un milieu de solvant organique. Cette invention concerne également un procédé permettant d'obtenir les composés représentés par la formule générale (2), lequel procédé consiste à traiter les composés représentés par la formule (1) avec du chlorure de thionyl ou avec du 1,1'-carbonyldiimidazole de façon que les dérivés correspondants soient produits et qu'ils interagissent avec les amines correspondantes représentées par la formule (6) dans le milieu de solvant organique.
PCT/RU2007/000116 2006-03-14 2007-03-12 1-oxo-3-(1h-indol-3-yl)-1,2,3,4-tétrahydroisoxynolines, procédés de production associés, bibliothèque combinatoire et bibliothèque ciblée Ceased WO2007105989A2 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
RU2006107658/04A RU2302417C1 (ru) 2006-03-14 2006-03-14 1-оксо-3-(1н-индол-3-ил)-1,2,3,4-тетрагидроизохинолины, способы их получения, комбинаторная библиотека и фокусированная библиотека
RU2006107658 2006-03-14

Publications (2)

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

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PCT/RU2007/000116 Ceased WO2007105989A2 (fr) 2006-03-14 2007-03-12 1-oxo-3-(1h-indol-3-yl)-1,2,3,4-tétrahydroisoxynolines, procédés de production associés, bibliothèque combinatoire et bibliothèque ciblée

Country Status (2)

Country Link
RU (1) RU2302417C1 (fr)
WO (1) WO2007105989A2 (fr)

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 (fr) 2005-04-21 2006-11-02 Astellas Pharma Inc. Agent thérapeutique pour le syndrome du côlon irritable
TWI425945B (zh) 2007-05-28 2014-02-11 Seldar Pharma Inc 四氫異喹啉－１－酮衍生物或其鹽
CN101367801B (zh) * 2007-08-15 2011-01-12 上海恒瑞医药有限公司 吡咯并六元n杂环羟基吗啡啉类衍生物的制备方法及其在医药上的应用
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 (fr) * 2005-03-18 2006-09-21 Lutz Weber Tetrahydro-isoquinolin-l-ones de traitement du cancer

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2006097323A1 (fr) * 2005-03-18 2006-09-21 Lutz Weber Tetrahydro-isoquinolin-l-ones de traitement du 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 (fr) 2007-09-20
RU2302417C1 (ru) 2007-07-10

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