AU2001293702A1 - 3-indolyl-4-phenyl-1h-pyrrole-2,5-dione derivatives as inhibitors of glycogen synthase kinase-3beta - Google Patents

3-indolyl-4-phenyl-1h-pyrrole-2,5-dione derivatives as inhibitors of glycogen synthase kinase-3beta

Info

Publication number: AU2001293702A1
Authority: AU; Australia
Prior art keywords: heteroalkyl; compound; hydrogen; dione; alkyl
Prior art date: 2000-07-27
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.): Abandoned

Application number

AU2001293702A

Other languages

English (en)

Inventor

Leyi Gong

Andrew Grupe

Gary Allen Peltz

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

F Hoffmann La Roche AG

Original Assignee

F Hoffmann La Roche AG

Priority date (The priority date 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 date listed.)

2000-07-27

Filing date

2001-07-18

Publication date

2002-02-13

2001-07-18 Application filed by F Hoffmann La Roche AG filed Critical F Hoffmann La Roche AG

2002-02-13 Publication of AU2001293702A1 publication Critical patent/AU2001293702A1/en

Status Abandoned legal-status Critical Current

Links

108010051975 Glycogen Synthase Kinase 3 beta Proteins 0.000 title claims description 53
102000019058 Glycogen Synthase Kinase 3 beta Human genes 0.000 title claims description 52
239000003112 inhibitor Substances 0.000 title claims description 21
LKDTVSJUXXGXKE-UHFFFAOYSA-N 3-(1h-indol-2-yl)-4-phenylpyrrole-2,5-dione Chemical class C=1C2=CC=CC=C2NC=1C=1C(=O)NC(=O)C=1C1=CC=CC=C1 LKDTVSJUXXGXKE-UHFFFAOYSA-N 0.000 title description 5
150000001875 compounds Chemical class 0.000 claims description 231
-1 cyano, nitro, amino Chemical group 0.000 claims description 194
229910052739 hydrogen Inorganic materials 0.000 claims description 82
239000001257 hydrogen Substances 0.000 claims description 78
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 74
125000004404 heteroalkyl group Chemical group 0.000 claims description 66
239000000203 mixture Substances 0.000 claims description 66
125000000217 alkyl group Chemical group 0.000 claims description 63
125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 54
125000000623 heterocyclic group Chemical group 0.000 claims description 51
238000000034 method Methods 0.000 claims description 50
201000010099 disease Diseases 0.000 claims description 44
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 44
125000000753 cycloalkyl group Chemical group 0.000 claims description 34
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 33
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 33
208000006673 asthma Diseases 0.000 claims description 29
229910052736 halogen Inorganic materials 0.000 claims description 21
239000003814 drug Substances 0.000 claims description 19
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 18
150000002367 halogens Chemical class 0.000 claims description 18
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125000004475 heteroaralkyl group Chemical group 0.000 claims description 17
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125000001153 fluoro group Chemical group F* 0.000 claims description 16
239000000546 pharmaceutical excipient Substances 0.000 claims description 16
125000003545 alkoxy group Chemical group 0.000 claims description 15
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 15
125000001309 chloro group Chemical group Cl* 0.000 claims description 13
125000004442 acylamino group Chemical group 0.000 claims description 12
208000026935 allergic disease Diseases 0.000 claims description 12
125000004663 dialkyl amino group Chemical group 0.000 claims description 12
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MZUZXNZGBBUAIM-UHFFFAOYSA-N 3-(1h-indol-3-yl)-4-phenylfuran-2,5-dione Chemical compound C=1NC2=CC=CC=C2C=1C=1C(=O)OC(=O)C=1C1=CC=CC=C1 MZUZXNZGBBUAIM-UHFFFAOYSA-N 0.000 claims 1
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WLJVXDMOQOGPHL-UHFFFAOYSA-N benzyl-alpha-carboxylic acid Natural products OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 14
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BLRHMMGNCXNXJL-UHFFFAOYSA-N 1-methylindole Chemical compound C1=CC=C2N(C)C=CC2=C1 BLRHMMGNCXNXJL-UHFFFAOYSA-N 0.000 description 12
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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- 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
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/02—Nasal agents, e.g. decongestants
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P11/06—Antiasthmatics
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/02—Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
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- A—HUMAN NECESSITIES
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- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 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

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Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
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Diabetes (AREA)
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AU2001293702A 2000-07-27 2001-07-18 3-indolyl-4-phenyl-1h-pyrrole-2,5-dione derivatives as inhibitors of glycogen synthase kinase-3beta Abandoned AU2001293702A1 (en)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
US22105800P	2000-07-27	2000-07-27
US60221058		2000-07-27
PCT/EP2001/008293 WO2002010158A2 (en)	2000-07-27	2001-07-18	3-indolyl-4-phenyl-1h-pyrrole-2,5-dione derivatives as inhibitors of glycogen synthase kinase-3beta

Publications (1)

Publication Number	Publication Date
AU2001293702A1 true AU2001293702A1 (en)	2002-02-13

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AU2001293702A Abandoned AU2001293702A1 (en)	2000-07-27	2001-07-18	3-indolyl-4-phenyl-1h-pyrrole-2,5-dione derivatives as inhibitors of glycogen synthase kinase-3beta

Country Status (31)

Country	Link
US (2)	US6479490B2 (no)
EP (1)	EP1307447B1 (no)
JP (1)	JP3984157B2 (no)
KR (1)	KR20030017655A (no)
CN (1)	CN1185229C (no)
AR (1)	AR033989A1 (no)
AT (1)	ATE284885T1 (no)
AU (1)	AU2001293702A1 (no)
BR (1)	BR0112965A (no)
CA (1)	CA2417277A1 (no)
CZ (1)	CZ2003555A3 (no)
DE (1)	DE60107857T2 (no)
EC (1)	ECSP034452A (no)
ES (1)	ES2233691T3 (no)
GT (1)	GT200100151A (no)
HR (1)	HRP20030030A2 (no)
HU (1)	HUP0301431A2 (no)
IL (1)	IL153851A0 (no)
JO (1)	JO2293B1 (no)
MA (1)	MA26936A1 (no)
MX (1)	MXPA03000695A (no)
NO (1)	NO20030328D0 (no)
NZ (1)	NZ523462A (no)
PA (1)	PA8523001A1 (no)
PE (1)	PE20020338A1 (no)
PL (1)	PL366701A1 (no)
RU (1)	RU2003104796A (no)
UY (1)	UY26857A1 (no)
WO (1)	WO2002010158A2 (no)
YU (1)	YU4403A (no)
ZA (1)	ZA200300216B (no)

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ES2446269T3 (es)	2006-12-19	2014-03-06	The Board Of Trustees Of The University Of Illinois	3-Benzofuranil-4-indolil-maleimidas como potentes inhibidores de GSK-3 para trastornos neurodegenerativos
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EP2474541A1 (en)	2010-12-23	2012-07-11	Johannes- Gutenberg-Universität Mainz	Conjugated 3-(indolyl)- and 3-(azaindolyl)-4-arylmaleimide compounds and their use in tumor treatment
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KR101440724B1 (ko) *	2013-03-29	2014-09-18	중앙대학교 산학협력단	글리코겐 신타아제 키나아제-3베타 억제물질을 유효성분으로 포함하는 난소과립세포종양의 예방 또는 치료용 약학적 조성물 및 건강기능성식품 조성물
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2001
- 2001-07-18 HU HU0301431A patent/HUP0301431A2/hu unknown
- 2001-07-18 CZ CZ2003555A patent/CZ2003555A3/cs unknown
- 2001-07-18 AT AT01974083T patent/ATE284885T1/de not_active IP Right Cessation
- 2001-07-18 HR HR20030030A patent/HRP20030030A2/hr not_active Application Discontinuation
- 2001-07-18 CA CA002417277A patent/CA2417277A1/en not_active Abandoned
- 2001-07-18 WO PCT/EP2001/008293 patent/WO2002010158A2/en not_active Ceased
- 2001-07-18 MX MXPA03000695A patent/MXPA03000695A/es unknown
- 2001-07-18 YU YU4403A patent/YU4403A/sh unknown
- 2001-07-18 IL IL15385101A patent/IL153851A0/xx unknown
- 2001-07-18 NZ NZ523462A patent/NZ523462A/en unknown
- 2001-07-18 EP EP01974083A patent/EP1307447B1/en not_active Expired - Lifetime
- 2001-07-18 BR BR0112965-1A patent/BR0112965A/pt not_active IP Right Cessation
- 2001-07-18 RU RU2003104796/04A patent/RU2003104796A/ru not_active Application Discontinuation
- 2001-07-18 DE DE60107857T patent/DE60107857T2/de not_active Expired - Fee Related
- 2001-07-18 ES ES01974083T patent/ES2233691T3/es not_active Expired - Lifetime
- 2001-07-18 KR KR10-2003-7001111A patent/KR20030017655A/ko not_active Ceased
- 2001-07-18 JP JP2002515887A patent/JP3984157B2/ja not_active Expired - Lifetime
- 2001-07-18 CN CNB018134068A patent/CN1185229C/zh not_active Expired - Fee Related
- 2001-07-18 AU AU2001293702A patent/AU2001293702A1/en not_active Abandoned
- 2001-07-18 PL PL01366701A patent/PL366701A1/xx not_active Application Discontinuation
- 2001-07-23 PE PE2001000742A patent/PE20020338A1/es not_active Application Discontinuation
- 2001-07-24 PA PA20018523001A patent/PA8523001A1/es unknown
- 2001-07-24 JO JO2001126A patent/JO2293B1/en active
- 2001-07-25 AR ARP010103541A patent/AR033989A1/es not_active Application Discontinuation
- 2001-07-26 UY UY26857A patent/UY26857A1/es not_active Application Discontinuation
- 2001-07-26 GT GT200100151A patent/GT200100151A/es unknown
- 2001-07-27 US US09/916,706 patent/US6479490B2/en not_active Expired - Fee Related
2002
- 2002-05-06 US US10/139,410 patent/US20020188018A1/en not_active Abandoned
2003
- 2003-01-08 ZA ZA200300216A patent/ZA200300216B/en unknown
- 2003-01-22 NO NO20030328A patent/NO20030328D0/no not_active Application Discontinuation
- 2003-01-24 EC EC2003004452A patent/ECSP034452A/es unknown
- 2003-01-24 MA MA27013A patent/MA26936A1/fr unknown

Also Published As

Publication number	Publication date
CA2417277A1 (en)	2002-02-07
CN1185229C (zh)	2005-01-19
AR033989A1 (es)	2004-01-21
IL153851A0 (en)	2003-07-31
UY26857A1 (es)	2002-01-31
DE60107857D1 (de)	2005-01-20
NO20030328L (no)	2003-01-22
EP1307447A2 (en)	2003-05-07
ECSP034452A (es)	2003-03-10
CN1444581A (zh)	2003-09-24
MA26936A1 (fr)	2004-12-20
JP2004505078A (ja)	2004-02-19
GT200100151A (es)	2002-05-23
HUP0301431A2 (hu)	2003-08-28
KR20030017655A (ko)	2003-03-03
PE20020338A1 (es)	2002-04-23
US6479490B2 (en)	2002-11-12
DE60107857T2 (de)	2005-12-08
PL366701A1 (en)	2005-02-07
US20020188018A1 (en)	2002-12-12
ES2233691T3 (es)	2005-06-16
HRP20030030A2 (en)	2005-02-28
ATE284885T1 (de)	2005-01-15
BR0112965A (pt)	2003-07-08
CZ2003555A3 (en)	2004-03-17
NO20030328D0 (no)	2003-01-22
YU4403A (sh)	2006-05-25
NZ523462A (en)	2004-09-24
RU2003104796A (ru)	2004-08-20
US20020052397A1 (en)	2002-05-02
MXPA03000695A (es)	2003-06-04
HK1058670A1 (en)	2004-05-28
EP1307447B1 (en)	2004-12-15
JP3984157B2 (ja)	2007-10-03
PA8523001A1 (es)	2002-10-24
ZA200300216B (en)	2004-04-08
WO2002010158A3 (en)	2002-05-16
WO2002010158A2 (en)	2002-02-07
JO2293B1 (en)	2005-09-12

Publication	Publication Date	Title
EP1307447B1 (en)	2004-12-15	3-indolyl-4-phenyl-1h-pyrrole-2,5-dione derivatives as inhibitors of glycogen synthase kinase-3beta
US7625889B2 (en)	2009-12-01	Substituted bis aryl and heteroaryl compounds as selective 5HT2A antagonists
TW492862B (en)	2002-07-01	A pharmaceutical composition for inhibiting production of TNF (tumor necrosis factor) in a mammal
CN105492008B (zh)	2020-11-27	用于抑制fasn的化合物及组合物
EP4132907B1 (en)	2024-04-24	(1h-indol-5-yl)acrylamide derivatives as inhibitors of tead proteins and the hippo-yap1/taz signaling cascade for the treatment of cancer
EP0464604B1 (en)	1995-03-29	1-Indolylalkyl-4-(alkoxy-pyrimidinyl)piperazines
JP2002536362A (ja)	2002-10-29	抗炎症剤としてのインドール誘導体
CA2594777A1 (en)	2006-07-27	Indoles useful in the treatment of inflamation
HK51995A (en)	1995-04-13	Antimigraine alkoxypyrimidine derivatives
EP1465610B1 (en)	2008-12-31	Use of a gsk-3beta inhibitor in the manufacture of a medicament for increasing bone formation
RS63671B1 (sr)	2022-11-30	Supstitutisani derivati triazolo hinoksalina
CN102316738A (zh)	2012-01-11	作为激酶抑制剂的酰胺类
CN102746241B (zh)	2014-11-05	2,3,5-三取代苯甲酰胺类化合物及其制备方法和用途
AU2011336700B2 (en)	2016-12-22	4-substituted-cyclohexylamino-4-piperidinyl-acetamide antagonists of CCR2
Bai et al.	2023	Discovery of novel pyrido [3, 2‐d] pyrimidine derivatives as selective and potent PI3Kδ inhibitors
CA2476490C (en)	2010-08-10	Indole derivatives substituted with long-chain alcohols and medicaments containing them
TW219937B (no)	1994-02-01
JP2004196785A (ja)	2004-07-15	フロピリジン誘導体
CN118047757A (zh)	2024-05-17	吡啶氮氧化物类衍生物及其药物组合物、制备方法和用途
HK1058670B (en)	2005-05-06	3-indolyl-4-phenyl-1h-pyrrole-2,5-dione derivatives as inhibitors of glycogen synthase kinase-3beta
HK40048161A (en)	2021-11-26	Substituted triazolo quinoxaline derivatives
HK40048161B (en)	2023-01-20	Substituted triazolo quinoxaline derivatives