AU2001270944A1 - Imidazole derivatives - Google Patents

Imidazole derivatives

Info

Publication number: AU2001270944A1
Authority: AU; Australia
Prior art keywords: imidazol; cyclobutyl; acetylamino; naphthalen; branched
Prior art date: 2000-07-31
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

AU2001270944A

Other languages

English (en)

Inventor

Michael Kirk Ahlijanian

Christopher Blair Cooper

Christopher John Helal

Lit-Fui Lau

Frank Samuel Menniti

Mark Allen Sanner

Patricia Ann Seymour

Anabella Villalobos

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.)

Pfizer Products Inc

Original Assignee

Pfizer Products Inc

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.)

2000-07-31

Filing date

2001-07-25

Publication date

2002-02-13

2001-07-25 Application filed by Pfizer Products Inc filed Critical Pfizer Products Inc

2002-02-13 Publication of AU2001270944A1 publication Critical patent/AU2001270944A1/en

Status Abandoned legal-status Critical Current

Links

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150000003839 salts Chemical class 0.000 claims description 48
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Classifications

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AU2001270944A 2000-07-31 2001-07-25 Imidazole derivatives Abandoned AU2001270944A1 (en)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
US22172400P	2000-07-31	2000-07-31
US60221724		2000-07-31
PCT/IB2001/001335 WO2002010141A1 (fr)	2000-07-31	2001-07-25	Derives d'imidazole

Publications (1)

Publication Number	Publication Date
AU2001270944A1 true AU2001270944A1 (en)	2002-02-13

Family

ID=22829075

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
AU2001270944A Abandoned AU2001270944A1 (en)	2000-07-31	2001-07-25	Imidazole derivatives

Country Status (35)

Country	Link
EP (1)	EP1305295A1 (fr)
JP (2)	JP4166084B2 (fr)
KR (1)	KR20030019644A (fr)
CN (1)	CN1444567A (fr)
AP (1)	AP2001002232A0 (fr)
AR (1)	AR032629A1 (fr)
AU (1)	AU2001270944A1 (fr)
BG (1)	BG107469A (fr)
BR (1)	BR0112862A (fr)
CA (1)	CA2418115A1 (fr)
CR (1)	CR6861A (fr)
CZ (1)	CZ2003225A3 (fr)
DO (1)	DOP2001000220A (fr)
EA (1)	EA200300097A1 (fr)
EC (1)	ECSP034445A (fr)
EE (1)	EE200300049A (fr)
GT (1)	GT200100147A (fr)
HR (1)	HRP20030048A2 (fr)
HU (1)	HUP0303069A3 (fr)
IL (1)	IL153787A0 (fr)
IS (1)	IS6662A (fr)
MA (1)	MA26932A1 (fr)
MX (1)	MXPA03000939A (fr)
NO (1)	NO20030472L (fr)
NZ (1)	NZ523272A (fr)
OA (1)	OA12345A (fr)
PA (1)	PA8523701A1 (fr)
PE (1)	PE20020337A1 (fr)
PL (1)	PL365134A1 (fr)
SK (1)	SK1042003A3 (fr)
SV (1)	SV2002000571A (fr)
TN (1)	TNSN01114A1 (fr)
UY (1)	UY26862A1 (fr)
WO (1)	WO2002010141A1 (fr)
ZA (1)	ZA200300819B (fr)

Families Citing this family (46)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
HK1042251B (en)	1999-01-13	2012-07-20	Bayer Healthcare Llc	Omega-carboxy aryl substituted diphenyl ureas as p38 kinase inhibitors
ME00275B (fr)	1999-01-13	2011-02-10	Bayer Corp	DIPHENYLUREES A SUBSTITUANTS ω-CARBOXYARYLES, INHIBITRICES DE KINASE RAF
US8124630B2 (en)	1999-01-13	2012-02-28	Bayer Healthcare Llc	ω-carboxyaryl substituted diphenyl ureas as raf kinase inhibitors
AU2003209119A1 (en)	2002-02-11	2003-09-04	Bayer Pharmaceuticals Corporation	Pyridine, quinoline, and isoquinoline n-oxides as kinase inhibitors
EP1478358B1 (fr)	2002-02-11	2013-07-03	Bayer HealthCare LLC	Tosylate de sorafenib pour le traitement des maladies caractérisées par une angiogénèse anormale
WO2003106455A1 (fr)	2002-06-14	2003-12-24	Applied Research Systems Ars Holding N.V.	Derives de cyanure d'azole methylidene et leur utilisation comme modulateurs de proteine kinase
US7141561B2 (en)	2002-07-25	2006-11-28	Sanofi-Aventis Deutschland Gmbh	Substituted diaryl heterocycles, process for their preparation and their use as medicaments
DE10233817A1 (de) *	2002-07-25	2004-02-12	Aventis Pharma Deutschland Gmbh	Substituierte Diarylheterocyclen, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel
GB0308968D0 (en) *	2003-04-17	2003-05-28	Glaxo Group Ltd	Medicaments
PT1626714E (pt)	2003-05-20	2007-08-24	Bayer Pharmaceuticals Corp	Diarilureias para doenças mediadas por pdgfr
DE602004010407T2 (de)	2003-07-23	2008-10-16	Bayer Pharmaceuticals Corp., West Haven	Fluorsubstituierter omega-carboxyaryldiphenylharnstoff zur behandlung und prävention von krankheiten und leiden
US7342118B2 (en)	2004-03-23	2008-03-11	Pfizer Inc	Imidazole compounds for the treatment of neurodegenerative disorders
ATE517885T1 (de)	2004-04-30	2011-08-15	Bayer Healthcare Llc	Substituierte pyrazolyl-harnstoff-derivate zur behandlung von krebs
RU2399614C2 (ru)	2004-09-21	2010-09-20	Астеллас Фарма Инк.	Аминоспиртовые производные
WO2006117212A2 (fr)	2005-05-04	2006-11-09	Develogen Aktiengesellschaft	Utilisation des inhibiteurs gsk-3 dans la prevention et le traitement des maladies auto-immunes pancreatiques
EP2258358A3 (fr)	2005-08-26	2011-09-07	Braincells, Inc.	Neurogenèse avec un inhibiteur de l'acetylcholinestérase
JP2009506069A (ja)	2005-08-26	2009-02-12	ブレインセルス，インコーポレイティド	ムスカリン性受容体調節による神経発生
RS20080139A (sr) *	2005-09-22	2009-05-06	Pfizer Products Inc.,	Jedinjenja imidazola za lečenje neuroloških poremećaja
JP2009512711A (ja)	2005-10-21	2009-03-26	ブレインセルス，インコーポレイティド	Ｐｄｅ阻害による神経新生の調節
JP2009513672A (ja)	2005-10-31	2009-04-02	ブレインセルス，インコーポレイティド	神経発生のｇａｂａ受容体媒介調節
KR20080091369A (ko)	2006-01-18	2008-10-10	암젠 인크	단백질 키나제 ｂ（ｐｋｂ） 억제제로서 티아졸 화합물
US20100216734A1 (en)	2006-03-08	2010-08-26	Braincells, Inc.	Modulation of neurogenesis by nootropic agents
AU2007249399A1 (en)	2006-05-09	2007-11-22	Braincells, Inc.	Neurogenesis by modulating angiotensin
MX2009004140A (es) *	2006-10-21	2009-07-10	Abbott Gmbh & Co Kg	Compuestos heterociclicos y su uso como inhibidores de la glucogeno sintasa quinasa 3.
WO2009017453A1 (fr) *	2007-07-30	2009-02-05	Astrazeneca Ab	Nouvelle combinaison thérapeutique d'antipsychotique et d'inhibiteur de gsk3 958
MX2010011663A (es) *	2008-04-24	2011-01-21	Abbott Gmbh & Co Kg	Derivados de 1-(7-hexahidropirrolo [3,4-c] pirrol-2 (1h)-il) quinolin-3-il)-(pirazin-2-il) urea y compuestos relacionados como glicogeno sintasa quinasa 3 (gsk-3).
WO2010099217A1 (fr)	2009-02-25	2010-09-02	Braincells, Inc.	Modulation de neurogenèse à l'aide de combinaisons de d-cyclosérine
WO2012041814A1 (fr)	2010-09-27	2012-04-05	Abbott Gmbh & Co. Kg	Composés hétérocycliques et leur utilisation en tant qu'inhibiteurs de la glycogène synthase kinase-3
US9090592B2 (en)	2010-12-30	2015-07-28	AbbVie Deutschland GmbH & Co. KG	Heterocyclic compounds and their use as glycogen synthase kinase-3 inhibitors
PT2928474T (pt)	2012-12-07	2019-01-30	Chemocentryx Inc	Diazol lactamas
DK2935227T3 (en) *	2012-12-21	2017-12-04	Chemocentryx Inc	DIAZOLAMIDES AS CCR1 RECEPTOR ANTAGONISTS
JP6616190B2 (ja) *	2014-02-07	2019-12-04	国立大学法人東京医科歯科大学	筋形成促進剤、筋萎縮抑制剤、医薬組成物及びｔａｚ活性化剤
PL3344273T3 (pl)	2015-08-31	2020-06-01	Nutramax Laboratories, Inc.	Kompozycje zawierające magnolię, korkowiec, teaninę i/lub białko serwatkowe
GB201605126D0 (en)	2016-03-24	2016-05-11	Univ Nottingham	Inhibitors and their uses
CN109310677A (zh)	2016-04-07	2019-02-05	凯莫森特里克斯股份有限公司	通过联合施用ccr1拮抗剂与pd-1抑制剂或pd-l1拮抗剂降低肿瘤负荷
CN111018840B (zh) *	2017-10-25	2022-09-09	西南大学	3-咪唑取代的靛红唑醇类化合物及其制备方法和医药应用
JP7482122B2 (ja) *	2018-07-03	2024-05-13	アイエフエムデューインコーポレイテッド	Ｓｔｉｎｇ活性に関連する状態を治療するための化合物および組成物
US20220133740A1 (en)	2019-02-08	2022-05-05	Frequency Therapeutics, Inc.	Valproic acid compounds and wnt agonists for treating ear disorders
GB201908424D0 (en) *	2019-06-12	2019-07-24	Imp College Innovations Ltd	Novel compounds
US11884634B2 (en)	2019-08-09	2024-01-30	Pfizer Inc.	Compositions of solid forms of (S)-2-(((S)-6,8-difluoro-1,2,3,4- tetrahydronaphthalen-2-yl)amino)-N-(1-(2-methyl-1-(neopentylamino)propan-2-yl)-1H-imidazol-4-yl)pentanamide
US10590087B1 (en)	2019-08-09	2020-03-17	Pfizer Inc.	Solid state forms of (S)-2-(((S)-6,8-difluoro-1,2,3,4-tetrahydronaphthalen-2-yl)amino)-N-(1-(2-methyl-1-(neopentylamino)propan-2-yl)-1H-imidazol-4-yl)pentanamide and uses thereof
EP4229037A2 (fr) *	2020-10-16	2023-08-23	CeMM - Forschungszentrum für Molekulare Medizin GmbH	Composés d'ubiquitine ligase cullin ring et utilisations associées
CN112250636A (zh) *	2020-11-09	2021-01-22	广西科技大学	5-氨基咪唑类化合物及其合成方法
JP2024519215A (ja)	2021-05-07	2024-05-09	カイメラセラピューティクス，インコーポレイテッド	Ｃｄｋ２分解剤およびそれらの使用
EP4396159A1 (fr)	2021-09-01	2024-07-10	Springworks Therapeutics, Inc.	Synthèse de nirogacestat
US11504354B1 (en)	2021-09-08	2022-11-22	SpringWorks Therapeutics Inc..	Chlorinated tetralin compounds and pharmaceutical compositions

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5401851A (en) *	1992-06-03	1995-03-28	Eli Lilly And Company	Angiotensin II antagonists
US5760246A (en) *	1996-12-17	1998-06-02	Biller; Scott A.	Conformationally restricted aromatic inhibitors of microsomal triglyceride transfer protein and method
ZA987383B (en) *	1997-08-19	2000-02-17	Lilly Co Eli	Treatment of congestive heart failure with growth hormone secretagogues.
ZA987385B (en) *	1997-08-19	2000-04-18	Lilly Co Eli	Growth hormone secretagogues.
JP4533534B2 (ja) *	1998-06-19	2010-09-01	ノバルティスバクシンズアンドダイアグノスティックス，インコーポレーテッド	グリコーゲンシンターゼキナーゼ３のインヒビター
WO2000021550A2 (fr) *	1998-10-13	2000-04-20	President And Fellows Of Harvard College	Methodes et compositions de traitement des maladies neurodegeneratives
CO5160260A1 (es) *	1999-02-19	2002-05-30	Lilly Co Eli	Secretagogos de la hormona del crecimiento derivados de imi- dazol 1,4- substituido
DE69912808T2 (de) *	1999-12-08	2004-09-30	Centre National De La Recherche Scientifique (C.N.R.S.)	Verwendung von Hymenialdisin und dessen Derivaten zur Herstellung therapeutischer Mittel

2001
- 2001-07-23 GT GT200100147A patent/GT200100147A/es unknown
- 2001-07-25 JP JP2002516273A patent/JP4166084B2/ja not_active Expired - Fee Related
- 2001-07-25 OA OA1200300017A patent/OA12345A/en unknown
- 2001-07-25 KR KR10-2003-7001455A patent/KR20030019644A/ko not_active Ceased
- 2001-07-25 EP EP01949833A patent/EP1305295A1/fr not_active Withdrawn
- 2001-07-25 EA EA200300097A patent/EA200300097A1/ru unknown
- 2001-07-25 PL PL01365134A patent/PL365134A1/xx not_active Application Discontinuation
- 2001-07-25 WO PCT/IB2001/001335 patent/WO2002010141A1/fr not_active Ceased
- 2001-07-25 PE PE2001000752A patent/PE20020337A1/es not_active Application Discontinuation
- 2001-07-25 CN CN01813397A patent/CN1444567A/zh active Pending
- 2001-07-25 CA CA002418115A patent/CA2418115A1/fr not_active Abandoned
- 2001-07-25 MX MXPA03000939A patent/MXPA03000939A/es active IP Right Grant
- 2001-07-25 SK SK104-2003A patent/SK1042003A3/sk not_active Application Discontinuation
- 2001-07-25 IL IL15378701A patent/IL153787A0/xx unknown
- 2001-07-25 EE EEP200300049A patent/EE200300049A/xx unknown
- 2001-07-25 NZ NZ523272A patent/NZ523272A/en unknown
- 2001-07-25 HU HU0303069A patent/HUP0303069A3/hu unknown
- 2001-07-25 CZ CZ2003225A patent/CZ2003225A3/cs unknown
- 2001-07-25 HR HR20030048A patent/HRP20030048A2/hr not_active Application Discontinuation
- 2001-07-25 BR BR0112862-0A patent/BR0112862A/pt not_active IP Right Cessation
- 2001-07-25 AU AU2001270944A patent/AU2001270944A1/en not_active Abandoned
- 2001-07-26 AP APAP/P/2001/002232A patent/AP2001002232A0/en unknown
- 2001-07-27 SV SV2001000571A patent/SV2002000571A/es not_active Application Discontinuation
- 2001-07-27 DO DO2001000220A patent/DOP2001000220A/es unknown
- 2001-07-30 AR ARP010103637A patent/AR032629A1/es unknown
- 2001-07-30 UY UY26862A patent/UY26862A1/es not_active Application Discontinuation
- 2001-07-30 TN TNTNSN01114A patent/TNSN01114A1/fr unknown
- 2001-07-31 PA PA20018523701A patent/PA8523701A1/es unknown
2002
- 2002-12-18 CR CR6861A patent/CR6861A/es not_active Application Discontinuation
- 2002-12-19 IS IS6662A patent/IS6662A/is unknown
2003
- 2003-01-16 BG BG107469A patent/BG107469A/bg unknown
- 2003-01-20 MA MA27004A patent/MA26932A1/fr unknown
- 2003-01-22 EC EC2003004445A patent/ECSP034445A/es unknown
- 2003-01-29 ZA ZA200300819A patent/ZA200300819B/en unknown
- 2003-01-30 NO NO20030472A patent/NO20030472L/no not_active Application Discontinuation
2008
- 2008-05-19 JP JP2008131176A patent/JP2008255123A/ja not_active Withdrawn

Also Published As

Publication number	Publication date
EA200300097A1 (ru)	2003-06-26
NO20030472L (no)	2003-03-27
BG107469A (bg)	2003-09-30
AP2001002232A0 (en)	2001-09-30
PA8523701A1 (es)	2002-04-25
HRP20030048A2 (en)	2003-04-30
NO20030472D0 (no)	2003-01-30
JP2004505111A (ja)	2004-02-19
CR6861A (es)	2004-03-11
NZ523272A (en)	2004-08-27
MXPA03000939A (es)	2003-06-24
PL365134A1 (en)	2004-12-27
WO2002010141A1 (fr)	2002-02-07
PE20020337A1 (es)	2002-05-08
OA12345A (en)	2004-04-13
TNSN01114A1 (fr)	2005-11-10
BR0112862A (pt)	2003-07-01
JP4166084B2 (ja)	2008-10-15
KR20030019644A (ko)	2003-03-06
AR032629A1 (es)	2003-11-19
SK1042003A3 (en)	2004-05-04
ZA200300819B (en)	2004-04-20
IS6662A (is)	2002-12-19
IL153787A0 (en)	2003-07-31
GT200100147A (es)	2002-06-25
DOP2001000220A (es)	2002-05-15
ECSP034445A (es)	2003-03-10
CN1444567A (zh)	2003-09-24
CZ2003225A3 (cs)	2004-02-18
JP2008255123A (ja)	2008-10-23
EE200300049A (et)	2004-10-15
EP1305295A1 (fr)	2003-05-02
MA26932A1 (fr)	2004-12-20
CA2418115A1 (fr)	2002-02-07
UY26862A1 (es)	2002-02-28
SV2002000571A (es)	2002-10-24
HUP0303069A2 (hu)	2004-03-01
HUP0303069A3 (en)	2004-04-28

Publication	Publication Date	Title
AU2001270944A1 (en)	2002-02-13	Imidazole derivatives
US6756385B2 (en)	2004-06-29	Imidazole derivatives
EP1256578B1 (fr)	2006-01-11	Dérivés de thiazole et leur utilisation comme inhibiteurs de cdk
EP1313710A1 (fr)	2003-05-28	Derives pyrazole et leur utilisation en tant qu'inhibiteurs des proteines kinases
US20050209297A1 (en)	2005-09-22	Pyrazole derivatives
MX2011006171A (es)	2011-06-20	Compuestos de carbazol carboxamida utiles como inhibidores de cinasa.
HUE030052T4 (en)	2017-06-28	Benzimidazole derivatives
US20020103185A1 (en)	2002-08-01	Pyrazole derivatives
US20030083352A1 (en)	2003-05-01	Synthesis of imidazole intermediates
HK1055953A (en)	2004-01-30	Imidazole derivatives

Legal Events

Date	Code	Title	Description
2007-03-01	MK4	Application lapsed section 142(2)(d) - no continuation fee paid for the application