HRP20030048A2 - Imidazole derivatives - Google Patents

Imidazole derivatives Download PDF

Info

Publication number: HRP20030048A2
Authority: HR; Croatia
Prior art keywords: imidazol; cyclobutyl; cis; acetylamino; naphthalen
Prior art date: 2000-07-31

Application number

HR20030048A

Other languages

English (en)

Croatian (hr)

Inventor

Michael Kirk Ahlijanian

Christopher Blair Cooper

Cristopher John Helal

Lit-Fui Lau

Frank Samuel Menniti

Mark Allen Sanner

Patricia Ann Seymour

Anabella Villalobos

Original Assignee

Pfizer Prod 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

2003-01-24

Publication date

2003-04-30

2003-01-24 Application filed by Pfizer Prod Inc filed Critical Pfizer Prod Inc

2003-04-30 Publication of HRP20030048A2 publication Critical patent/HRP20030048A2/hr

Links

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239000000460 chlorine Substances 0.000 claims description 57
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150000003839 salts Chemical class 0.000 claims description 46
239000000825 pharmaceutical preparation Substances 0.000 claims description 38
239000000126 substance Substances 0.000 claims description 32
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VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 claims description 28
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125000001072 heteroaryl group Chemical group 0.000 claims description 24
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ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
WRIKHQLVHPKCJU-UHFFFAOYSA-N sodium bis(trimethylsilyl)amide Chemical compound C[Si](C)(C)N([Na])[Si](C)(C)C WRIKHQLVHPKCJU-UHFFFAOYSA-N 0.000 description 1
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125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
150000005621 tetraalkylammonium salts Chemical class 0.000 description 1
JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 description 1
DPKBAXPHAYBPRL-UHFFFAOYSA-M tetrabutylazanium;iodide Chemical compound [I-].CCCC[N+](CCCC)(CCCC)CCCC DPKBAXPHAYBPRL-UHFFFAOYSA-M 0.000 description 1
125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
125000005958 tetrahydrothienyl group Chemical group 0.000 description 1
125000004632 tetrahydrothiopyranyl group Chemical group S1C(CCCC1)* 0.000 description 1
125000003831 tetrazolyl group Chemical group 0.000 description 1
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JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
239000003053 toxin Substances 0.000 description 1
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125000004306 triazinyl group Chemical group 0.000 description 1
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YLGRTLMDMVAFNI-UHFFFAOYSA-N tributyl(prop-2-enyl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)CC=C YLGRTLMDMVAFNI-UHFFFAOYSA-N 0.000 description 1
QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 description 1
COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-UHFFFAOYSA-N 0.000 description 1
229910052722 tritium Inorganic materials 0.000 description 1
229960002004 valdecoxib Drugs 0.000 description 1
LNPDTQAFDNKSHK-UHFFFAOYSA-N valdecoxib Chemical compound CC=1ON=C(C=2C=CC=CC=2)C=1C1=CC=C(S(N)(=O)=O)C=C1 LNPDTQAFDNKSHK-UHFFFAOYSA-N 0.000 description 1
PNVNVHUZROJLTJ-UHFFFAOYSA-N venlafaxine Chemical compound C1=CC(OC)=CC=C1C(CN(C)C)C1(O)CCCCC1 PNVNVHUZROJLTJ-UHFFFAOYSA-N 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
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- 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
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HR20030048A 2000-07-31 2003-01-24 Imidazole derivatives HRP20030048A2 (en)

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US22172400P	2000-07-31	2000-07-31
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JP2002534468A (ja)	1999-01-13	2002-10-15	バイエルコーポレイション	ｐ３８キナーゼ阻害剤としてのω−カルボキシアリール置換ジフェニル尿素
US8124630B2 (en)	1999-01-13	2012-02-28	Bayer Healthcare Llc	ω-carboxyaryl substituted diphenyl ureas as raf kinase inhibitors
WO2003068229A1 (en)	2002-02-11	2003-08-21	Bayer Pharmaceuticals Corporation	Pyridine, quinoline, and isoquinoline n-oxides as kinase inhibitors
WO2003068228A1 (en)	2002-02-11	2003-08-21	Bayer Pharmaceuticals Corporation	Aryl ureas with angiogenesis inhibiting activity
AU2003251721A1 (en)	2002-06-14	2003-12-31	Laboratoires Serono Sa	Azole methylidene cyanide derivatives and their use as protein kinase modulators
DE10233817A1 (de) *	2002-07-25	2004-02-12	Aventis Pharma Deutschland Gmbh	Substituierte Diarylheterocyclen, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel
US7141561B2 (en)	2002-07-25	2006-11-28	Sanofi-Aventis Deutschland Gmbh	Substituted diaryl heterocycles, process for their preparation and their use as medicaments
GB0308968D0 (en) *	2003-04-17	2003-05-28	Glaxo Group Ltd	Medicaments
DE602004011340T2 (de)	2003-05-20	2008-11-06	Bayer Healthcare Llc	Diaryl-harnstoffe mit kinasehemmender wirkung
ME00294B (me)	2003-07-23	2011-05-10	Bayer Pharmaceuticals Corp	Fluoro supstituisana omega-karaboksiaril difenil urea za liječenje i prevenciju bolesti i stanja bolesti
RS50595B (sr) *	2004-03-23	2010-05-07	Pfizer Products Incorporated	Jedinjenja imidazola za lečenje neurodegenerativnih poremećaja
CN101010315A (zh)	2004-04-30	2007-08-01	拜耳制药公司	用于治疗癌症的取代的吡唑基脲衍生物
BRPI0515710A (pt)	2004-09-21	2008-07-29	Astellas Pharma Inc	composto de aminoálcool, uso de um composto de aminoálcool, composição farmacêutica e método para o tratamento profilático e/ou terapêutico
US20080207594A1 (en)	2005-05-04	2008-08-28	Davelogen Aktiengesellschaft	Use of Gsk-3 Inhibitors for Preventing and Treating Pancreatic Autoimmune Disorders
EP2275095A3 (en)	2005-08-26	2011-08-17	Braincells, Inc.	Neurogenesis by muscarinic receptor modulation
EP2258357A3 (en)	2005-08-26	2011-04-06	Braincells, Inc.	Neurogenesis with acetylcholinesterase inhibitor
WO2007034326A2 (en) *	2005-09-22	2007-03-29	Pfizer Products Inc.	Imidazole compounds for the treatment of neurological disorders
EP2377530A3 (en)	2005-10-21	2012-06-20	Braincells, Inc.	Modulation of neurogenesis by PDE inhibition
EP2314289A1 (en)	2005-10-31	2011-04-27	Braincells, Inc.	Gaba receptor mediated modulation of neurogenesis
AU2007207743B2 (en)	2006-01-18	2010-07-08	Amgen Inc.	Thiazole compounds as protein kinase B (PKB) inhibitors
US20100216734A1 (en)	2006-03-08	2010-08-26	Braincells, Inc.	Modulation of neurogenesis by nootropic agents
WO2007134136A2 (en)	2006-05-09	2007-11-22	Braincells, Inc.	Neurogenesis by modulating angiotensin
KR20090071662A (ko) *	2006-10-21	2009-07-01	애보트 게엠베하 운트 콤파니 카게	헤테로사이클릭 화합물 및 글리코겐 신타제 키나제 3 억제제로서의 이의 용도
WO2009017453A1 (en) *	2007-07-30	2009-02-05	Astrazeneca Ab	New therapeutic combination of an antipsychotic and a gsk3 inhibitor 958
EP2297154B1 (en) *	2008-04-24	2013-04-03	Abbott GmbH & Co. KG	1- (7-(hexahydropyrrolo [3, 4-c]pyrrol-2 (1h) -yl) quin0lin-4-yl) -3- (pyrazin-2-yl) urea derivatives and related compounds as glycogen synthase kinase 3 (gsk-3) inhibitors
WO2010099217A1 (en)	2009-02-25	2010-09-02	Braincells, Inc.	Modulation of neurogenesis using d-cycloserine combinations
EP2621914B1 (en)	2010-09-27	2016-12-28	Abbott GmbH & Co. KG	Heterocyclic compounds and their use as glycogen synthase kinase-3 inhibitors
US9090592B2 (en)	2010-12-30	2015-07-28	AbbVie Deutschland GmbH & Co. KG	Heterocyclic compounds and their use as glycogen synthase kinase-3 inhibitors
ES2707323T3 (es)	2012-12-07	2019-04-03	Chemocentryx Inc	Diazol lactamas
WO2014100735A2 (en) *	2012-12-21	2014-06-26	Chemocentryx, Inc.	Diazole amides
US10653672B2 (en)	2014-02-07	2020-05-19	National University Corporation Tokyo Medical And Dental University	Myogenesis promotor, muscle atrophy inhibitor, medical composition and TAZ activator
AU2016317046B2 (en) *	2015-08-31	2022-03-10	Nutramax Laboratories, Inc.	Compositions comprising magnolia, phellodendron, theanine and/or whey protein
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
CN110963996B (zh) *	2017-10-25	2022-09-09	西南大学	含苯乙酮取代基的靛红唑醇类化合物及其制备方法和医药应用
JP2022520671A (ja)	2019-02-08	2022-03-31	フリークエンシー・セラピューティクス・インコーポレイテッド	耳障害を治療するためのバルプロ酸化合物及びｗｎｔ作動薬
GB201908424D0 (en) *	2019-06-12	2019-07-24	Imp College Innovations Ltd	Novel compounds
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
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
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
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
ZA987385B (en) *	1997-08-19	2000-04-18	Lilly Co Eli	Growth hormone secretagogues.
ZA987383B (en) *	1997-08-19	2000-02-17	Lilly Co Eli	Treatment of congestive heart failure with growth hormone secretagogues.
US6489344B1 (en) *	1998-06-19	2002-12-03	Chiron Corporation	Inhibitors of glycogen synthase kinase 3
WO2000021550A2 (en) *	1998-10-13	2000-04-20	President And Fellows Of Harvard College	Methods and compositions for treating neurodegenerative diseases
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

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GT200100147A (es)	2002-06-25
ZA200300819B (en)	2004-04-20
NZ523272A (en)	2004-08-27
CA2418115A1 (en)	2002-02-07
CR6861A (es)	2004-03-11
UY26862A1 (es)	2002-02-28
EP1305295A1 (en)	2003-05-02
MA26932A1 (fr)	2004-12-20
JP2008255123A (ja)	2008-10-23
BG107469A (bg)	2003-09-30
HUP0303069A3 (en)	2004-04-28
AP2001002232A0 (en)	2001-09-30
SK1042003A3 (en)	2004-05-04
KR20030019644A (ko)	2003-03-06
IS6662A (is)	2002-12-19
MXPA03000939A (es)	2003-06-24
HUP0303069A2 (hu)	2004-03-01
EA200300097A1 (ru)	2003-06-26
AU2001270944A1 (en)	2002-02-13
PE20020337A1 (es)	2002-05-08
SV2002000571A (es)	2002-10-24
ECSP034445A (es)	2003-03-10
CN1444567A (zh)	2003-09-24
OA12345A (en)	2004-04-13
NO20030472D0 (no)	2003-01-30
NO20030472L (no)	2003-03-27
DOP2001000220A (es)	2002-05-15
AR032629A1 (es)	2003-11-19
CZ2003225A3 (cs)	2004-02-18
WO2002010141A1 (en)	2002-02-07
TNSN01114A1 (fr)	2005-11-10
JP2004505111A (ja)	2004-02-19
BR0112862A (pt)	2003-07-01
IL153787A0 (en)	2003-07-31
JP4166084B2 (ja)	2008-10-15
PL365134A1 (en)	2004-12-27
EE200300049A (et)	2004-10-15
PA8523701A1 (es)	2002-04-25

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