OA10977A - Substituted 6,5-hetero-bicyclic derivatives - Google Patents

Substituted 6,5-hetero-bicyclic derivatives Download PDF

Info

Publication number: OA10977A
Authority: OA; OAPI
Prior art keywords: phenyl; trimethyl; stress; compounds; ethyl
Prior art date: 1996-08-28

Application number

OA9900035A

Other languages

English (en)

Inventor

Chen Yuhpyng Liang

Original Assignee

Pfizer

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.)

1996-08-28

Filing date

1999-02-17

Publication date

2001-11-02

Family has litigation

First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=21823717&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=OA10977(A) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.

1999-02-17 Application filed by Pfizer filed Critical Pfizer

2001-11-02 Publication of OA10977A publication Critical patent/OA10977A/en

Links

150000001875 compounds Chemical class 0.000 claims abstract description 181
229910052799 carbon Inorganic materials 0.000 claims abstract description 36
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 30
229910052757 nitrogen Inorganic materials 0.000 claims abstract description 19
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 12
230000003042 antagnostic effect Effects 0.000 claims abstract description 3
230000005764 inhibitory process Effects 0.000 claims abstract description 3
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 51
239000000203 mixture Substances 0.000 claims description 42
-1 tri-substitutedphenyl Chemical group 0.000 claims description 35
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 34
125000000217 alkyl group Chemical group 0.000 claims description 27
238000000034 method Methods 0.000 claims description 26
208000035475 disorder Diseases 0.000 claims description 25
125000001309 chloro group Chemical group Cl* 0.000 claims description 24
125000001246 bromo group Chemical group Br* 0.000 claims description 21
229910052684 Cerium Inorganic materials 0.000 claims description 20
102100021752 Corticoliberin Human genes 0.000 claims description 20
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 19
125000001153 fluoro group Chemical group F* 0.000 claims description 16
125000002346 iodo group Chemical group I* 0.000 claims description 15
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239000001257 hydrogen Substances 0.000 claims description 14
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GVGLGOZIDCSQPN-PVHGPHFFSA-N Heroin Chemical compound O([C@H]1[C@H](C=C[C@H]23)OC(C)=O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4OC(C)=O GVGLGOZIDCSQPN-PVHGPHFFSA-N 0.000 claims description 4
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125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
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SVUOLADPCWQTTE-UHFFFAOYSA-N 1h-1,2-benzodiazepine Chemical class N1N=CC=CC2=CC=CC=C12 SVUOLADPCWQTTE-UHFFFAOYSA-N 0.000 claims description 3
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125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
125000004092 methylthiomethyl group Chemical group [H]C([H])([H])SC([H])([H])* 0.000 claims description 2
230000006794 tachycardia Effects 0.000 claims description 2
SGPGESCZOCHFCL-UHFFFAOYSA-N Tilisolol hydrochloride Chemical compound [Cl-].C1=CC=C2C(=O)N(C)C=C(OCC(O)C[NH2+]C(C)(C)C)C2=C1 SGPGESCZOCHFCL-UHFFFAOYSA-N 0.000 claims 16
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230000001314 paroxysmal effect Effects 0.000 claims 1
125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
125000005958 tetrahydrothienyl group Chemical group 0.000 claims 1
ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical group [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 claims 1
229910052760 oxygen Inorganic materials 0.000 abstract description 9
239000001301 oxygen Substances 0.000 abstract description 4
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract description 3
229910052717 sulfur Inorganic materials 0.000 abstract description 3
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 1
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 abstract 1
230000002265 prevention Effects 0.000 abstract 1
239000011593 sulfur Substances 0.000 abstract 1
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 42
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QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 32
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VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 22
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MUJIDPITZJWBSW-UHFFFAOYSA-N palladium(2+) Chemical compound [Pd+2] MUJIDPITZJWBSW-UHFFFAOYSA-N 0.000 description 1
YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
208000019906 panic disease Diseases 0.000 description 1
PQPFFKCJENSZKL-UHFFFAOYSA-N pentan-3-amine Chemical compound CCC(N)CC PQPFFKCJENSZKL-UHFFFAOYSA-N 0.000 description 1
125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
FVZVCSNXTFCBQU-UHFFFAOYSA-N phosphanyl Chemical group [PH2] FVZVCSNXTFCBQU-UHFFFAOYSA-N 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
229920000137 polyphosphoric acid Polymers 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
229910000105 potassium hydride Inorganic materials 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
125000006239 protecting group Chemical group 0.000 description 1
238000000746 purification Methods 0.000 description 1
125000002098 pyridazinyl group Chemical group 0.000 description 1
125000006085 pyrrolopyridyl group Chemical group 0.000 description 1
125000000168 pyrrolyl group Chemical group 0.000 description 1
125000005493 quinolyl group Chemical group 0.000 description 1
238000006268 reductive amination reaction Methods 0.000 description 1
230000002829 reductive effect Effects 0.000 description 1
239000003488 releasing hormone Substances 0.000 description 1
238000007363 ring formation reaction Methods 0.000 description 1
102200073741 rs121909602 Human genes 0.000 description 1
239000008159 sesame oil Substances 0.000 description 1
235000011803 sesame oil Nutrition 0.000 description 1
150000004760 silicates Chemical class 0.000 description 1
239000000377 silicon dioxide Substances 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
239000011780 sodium chloride Substances 0.000 description 1
239000001509 sodium citrate Substances 0.000 description 1
NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
235000019333 sodium laurylsulphate Nutrition 0.000 description 1
235000010288 sodium nitrite Nutrition 0.000 description 1
YHOBGCSGTGDMLF-UHFFFAOYSA-N sodium;di(propan-2-yl)azanide Chemical compound [Na+].CC(C)[N-]C(C)C YHOBGCSGTGDMLF-UHFFFAOYSA-N 0.000 description 1
239000008247 solid mixture Substances 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000007858 starting material Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
125000004434 sulfur atom Chemical group 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
150000003573 thiols Chemical class 0.000 description 1
ZWZVWGITAAIFPS-UHFFFAOYSA-N thiophosgene Chemical compound ClC(Cl)=S ZWZVWGITAAIFPS-UHFFFAOYSA-N 0.000 description 1
101150068774 thyX gene Proteins 0.000 description 1
125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
125000005270 trialkylamine group Chemical group 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
UCPYLLCMEDAXFR-UHFFFAOYSA-N triphosgene Chemical compound ClC(Cl)(Cl)OC(=O)OC(Cl)(Cl)Cl UCPYLLCMEDAXFR-UHFFFAOYSA-N 0.000 description 1
238000001665 trituration Methods 0.000 description 1
230000009385 viral infection Effects 0.000 description 1
238000010626 work up procedure Methods 0.000 description 1

Classifications

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OA9900035A 1996-08-28 1999-02-17 Substituted 6,5-hetero-bicyclic derivatives OA10977A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US2503996P	1996-08-28	1996-08-28

Publications (1)

Publication Number	Publication Date
OA10977A true OA10977A (en)	2001-11-02

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ID=21823717

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
OA9900035A OA10977A (en)	1996-08-28	1999-02-17	Substituted 6,5-hetero-bicyclic derivatives

Country Status (36)

Country	Link
EP (1)	EP0923582B1 (de)
JP (2)	JP3621706B2 (de)
KR (1)	KR20000035934A (de)
CN (1)	CN1227554A (de)
AP (1)	AP762A (de)
AR (1)	AR015103A1 (de)
AT (1)	ATE340176T1 (de)
AU (1)	AU735401B2 (de)
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Families Citing this family (152)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0770080B1 (de)	1995-05-12	1999-07-14	Neurogen Corporation	Neue deazapurinderivate; eine neue klasse von crf1-spezifischen liganden
US6313124B1 (en)	1997-07-23	2001-11-06	Dupont Pharmaceuticals Company	Tetrazine bicyclic compounds
US7094782B1 (en)	1996-07-24	2006-08-22	Bristol-Myers Squibb Company	Azolo triazines and pyrimidines
US6191131B1 (en)	1997-07-23	2001-02-20	Dupont Pharmaceuticals Company	Azolo triazines and pyrimidines
US6060478A (en) *	1996-07-24	2000-05-09	Dupont Pharmaceuticals	Azolo triazines and pyrimidines
US6124289A (en) *	1996-07-24	2000-09-26	Dupont Pharmaceuticals Co.	Azolo triazines and pyrimidines
AU6279598A (en) *	1997-02-18	1998-09-08	Neurocrine Biosciences, Inc.	Biazacyclic CRF antagonists
NZ335823A (en)	1997-04-22	2001-06-29	Neurocrine Biosciences Inc	Thiophenopyridines, preparation as CRF receptor antagonists
PL337888A1 (en) *	1997-07-03	2000-09-11	Du Pont Pharm Co	Imidazoprimidines and imidazopyridines for use in treating neurological disorders
ATE301657T1 (de) *	1998-01-28	2005-08-15	Bristol Myers Squibb Pharma Co	Azolo-pyrimidine
US6187777B1 (en)	1998-02-06	2001-02-13	Amgen Inc.	Compounds and methods which modulate feeding behavior and related diseases
US6472402B1 (en)	1998-04-02	2002-10-29	Neurogen Corporation	Aminoalkyl substituted 5,6,7,8-Tetrahydro-9H-Pyridino [2,3-B]indole derivatives
US6291473B1 (en)	1998-04-02	2001-09-18	Neurogen Corporation	Aminoalkyl substituted 5,6,7,8-tetrahydro-9H-pyridino [2, 3-B] indole and 5,6,7,8-tetrahydro-9H-pyrimidino [4, 5-B] indole derivatives: CRF1 specific ligands
JP2002510695A (ja) *	1998-04-03	2002-04-09	デュポンファーマシューティカルズカンパニー	副腎皮質刺激ホルモン放出因子（ＣＲＦ）拮抗剤としてのチアゾロ［４，５−ｄ］ピリミジンおよびピリジン
DE69907448T2 (de) *	1998-06-09	2004-03-18	Neurogen Corp., Branford	Pyrido[2,3-b]indolizinderivate und aza analoge: crf1 spezifische liganden
US6509338B1 (en)	1998-06-22	2003-01-21	Bristol-Myers Squibb Company	Pyrazolo[1,5-A]triazine corticotropin releasing factor antagonists
EP1105394A1 (de) *	1998-08-21	2001-06-13	Du Pont Pharmaceuticals Company	Isoxazolo[4,5-d]pyrimidine als crf antagonisten
PT1129096E (pt) *	1998-11-12	2003-09-30	Neurocrine Biosciences Inc	Antagonistas de receptor de crf e metodos de tratamento relacionados com os mesmos
ES2180338T3 (es) *	1998-11-12	2003-02-01	Neurocrine Biosciences Inc	Antagonistas del receptor de crf y metodos relacionados.
US6531475B1 (en) *	1998-11-12	2003-03-11	Neurocrine Biosciences, Inc.	CRF receptor antagonists and methods relating thereto
WO2000044754A1 (en) *	1999-01-29	2000-08-03	Sumitomo Chemical Company, Limited	Fat accumulation inhibitory agents
EP1040831A3 (de) *	1999-04-02	2003-05-02	Pfizer Products Inc.	Verwendung von Corticotropin Releasing Factor (CRF) Antagonisten zur Prophylaxe des plötzlichen Todes
AU4331500A (en)	1999-04-06	2000-10-23	Du Pont Pharmaceuticals Company	Pyrazolotriazines as crf antagonists
AU4203500A (en) *	1999-04-06	2000-10-23	Du Pont Pharmaceuticals Company	Pyrazolopyrimidines as crf antagonists
US6982265B1 (en)	1999-05-21	2006-01-03	Bristol Myers Squibb Company	Pyrrolotriazine inhibitors of kinases
EP1669071B1 (de) *	1999-05-21	2009-07-22	Bristol-Myers Squibb Company	Pyrrolotriazine als Kinase Hemmer.
US6432989B1 (en)	1999-08-27	2002-08-13	Pfizer Inc	Use of CRF antagonists to treat circadian rhythm disorders
PL354784A1 (en)	1999-09-30	2004-02-23	Neurogen Corporation	Certain alkylene diamine-substituted heterocycles
CA2379585C (en)	1999-09-30	2006-06-20	James W. Darrow	Certain alkylene diamine-substituted pyrazolo[1,5,-a]-1,5-pyrimidines and pyrazolo[1,5-a]-1,3,5-triazines
SE9903544D0 (sv) *	1999-10-01	1999-10-01	Astra Pharma Prod	Novel compounds
CO5271670A1 (es)	1999-10-29	2003-04-30	Pfizer Prod Inc	Antagonistas del factor de liberacion de corticitropina y composiciones relacionadas
TWI271406B (en)	1999-12-13	2007-01-21	Eisai Co Ltd	Tricyclic condensed heterocyclic compounds, preparation method of the same and pharmaceuticals comprising the same
GB2359078A (en) *	2000-02-11	2001-08-15	Astrazeneca Uk Ltd	Pharmaceutically active pyrimidine derivatives
JP2003522191A (ja) *	2000-02-11	2003-07-22	アストラゼネカ・アクチエボラーグ	ケモカイン受容体活性のモジュレーターとしてのピリミジン化合物およびそれらの使用
GB2359081A (en) *	2000-02-11	2001-08-15	Astrazeneca Uk Ltd	Pharmaceutically active thiazolopyrimidines
AU2001232271A1 (en) *	2000-02-14	2001-08-20	Japan Tobacco Inc.	Preventives/remedies for postoperative stress
GB2359551A (en)	2000-02-23	2001-08-29	Astrazeneca Uk Ltd	Pharmaceutically active pyrimidine derivatives
EP1149583A3 (de) *	2000-04-13	2001-11-14	Pfizer Products Inc.	Kombinationen bestehend aus Antagonisten des Corticotropin freisetzenden Faktors und Stoffen, die die Wachstumshormonsekretion fördern
US6440960B1 (en)	2000-05-18	2002-08-27	Neurocrine Biosciences, Inc.	CRF receptor antagonists and methods relating thereto
JP2004503553A (ja)	2000-06-14	2004-02-05	ワーナー−ランバート・カンパニー、リミテッド、ライアビリティ、カンパニー	６，５−縮合二環式複素環
US6630476B2 (en) *	2000-07-07	2003-10-07	Bristol-Myers Squibb Pharma Company	Pyrrolo [3,4-d] pyrimidines as corticotropin releasing factor (CRF) antagonists
SE0003828D0 (sv)	2000-10-20	2000-10-20	Astrazeneca Ab	Novel compounds
US6867300B2 (en)	2000-11-17	2005-03-15	Bristol-Myers Squibb Company	Methods for the preparation of pyrrolotriazine compounds useful as kinase inhibitors
ATE375345T1 (de)	2000-12-28	2007-10-15	Ono Pharmaceutical Co	Cyclopenta(d)pyrazolo(1,5-a)pyrimidin-verbindun als crf-rezeptor antagonist
GB0100624D0 (en) *	2001-01-10	2001-02-21	Vernalis Res Ltd	Chemical compounds VII
TWI312347B (en) *	2001-02-08	2009-07-21	Eisai R&D Man Co Ltd	Bicyclic nitrogen-containing condensed ring compounds
NZ528207A (en) *	2001-03-13	2006-02-24	Bristol Myers Squibb Pharma Co	4-(2-butylamino)-2,7-dimethyl-8-(2-methyl-6-methoxypyrid-3-yl) pyrazolo-[1,5-A]-1,3,5-triazine, its enantiomers and pharmaceutically acceptable salts as corticotropin releasing factor receptor ligands
SE0101322D0 (sv)	2001-04-12	2001-04-12	Astrazeneca Ab	Novel compounds
HUP0401292A3 (en)	2001-04-27	2011-01-28	Eisai R & D Man Co	Pyrazolo[1,5-a]pyridines, pharmaceutical compositions containing the same and process for preparation thereof
US7446108B2 (en) *	2001-05-21	2008-11-04	Neurocrine, Inc.	Tri-and tetraaza-acenaphthylen derivatives as CRF receptor antagonists
GB0117396D0 (en)	2001-07-17	2001-09-05	Glaxo Group Ltd	Chemical compounds
EP2335700A1 (de)	2001-07-25	2011-06-22	Boehringer Ingelheim (Canada) Ltd.	Hepatitis C Virus Polymerase Inhibitoren mit heterobicylischer Struktur
TW200300350A (en)	2001-11-14	2003-06-01	Bristol Myers Squibb Co	C-5 modified indazolylpyrrolotriazines
DE60301339T2 (de)	2002-03-07	2006-03-09	Smithkline Beecham Corp.	Pyrazolopyrimidin- und pyrazolotriazinderivate und diese enthaltende pharmazeutische zubereitungen
ATE478872T1 (de) *	2002-03-28	2010-09-15	Ustav Ex Botan Av Cr V V I I O	Pyrazoloä4,3-düpyrimidine, verfahren zu ihrer herstellung und therapeutische anwendung
US7119200B2 (en) *	2002-09-04	2006-10-10	Schering Corporation	Pyrazolopyrimidines as cyclin dependent kinase inhibitors
GB0221828D0 (en)	2002-09-20	2002-10-30	Astrazeneca Ab	Novel compound
AR041470A1 (es) *	2002-10-17	2005-05-18	Upjohn Co	Compuestos de pirrolo (1,2 - b) piridazina y sus usos
US7176216B2 (en)	2002-10-22	2007-02-13	Eisai Co., Ltd.	7-phenylpyrazolopyridine compounds
TWI283679B (en)	2002-10-22	2007-07-11	Eisai Co Ltd	7-phenylpyrazolopyridine compounds
TW200420565A (en)	2002-12-13	2004-10-16	Bristol Myers Squibb Co	C-6 modified indazolylpyrrolotriazines
MXPA05007485A (es)	2003-01-14	2006-01-30	Arena Pharm Inc	Derivados de arilo y heteroarilo 1,2,3-trisubstituidos como moduladores del metabolismo y la profilaxis y tratamiento de trastornos relacionados con ello tales como diabetes e hiperglicemia.
US7468376B2 (en) *	2003-02-27	2008-12-23	Palau Pharma, S.A.	Pyrazolopyridine derivates
US7041671B2 (en) *	2003-04-02	2006-05-09	Pfizer Inc	Pyrrolo[1,2-b]pyridazine compounds and their uses
US7056920B2 (en) *	2003-04-04	2006-06-06	Pfizer Inc	Pyrrolo[1,2-B]pyridazine compounds and their uses
US7034023B2 (en) *	2003-04-04	2006-04-25	Pfizer Inc	Pyrrolo[1,2-B]pyridazine compounds and their uses
GB0308208D0 (en)	2003-04-09	2003-05-14	Glaxo Group Ltd	Chemical compounds
EP1615929A1 (de) *	2003-04-15	2006-01-18	Pharmacia & Upjohn Company LLC	Pyrrolo[1,2-b]pyridazin-verbindungen und ihre verwendungen
OA13050A (en)	2003-04-29	2006-11-10	Pfizer Ltd	5,7-diaminopyrazolo [4,3-D] pyrimidines useful in the treatment of hypertension.
CA2523072A1 (en) *	2003-05-07	2004-11-18	Pharmacia & Upjohn Company Llc	Pyrrolo (1,2-b) pyridazine compounds and their use as crf-1 receptor antagonists
WO2004110454A1 (ja) *	2003-06-13	2004-12-23	Ishihara Sangyo Kaisha, Ltd.	アデノシンＡ2ａ受容体アゴニストの投与が必要な疾患を治療又は予防するための組成物
AR045047A1 (es)	2003-07-11	2005-10-12	Arena Pharm Inc	Derivados arilo y heteroarilo trisustituidos como moduladores del metabolismo y de la profilaxis y tratamiento de desordenes relacionados con los mismos
RS20060018A (sr)	2003-07-14	2007-12-31	Arena Pharmaceuticals Inc.,	Derivati spojenih arila i heteroarila kao modulatori metabolizma u profilaksi i lečenju sa njima povezanih stanja
AR045582A1 (es) *	2003-09-05	2005-11-02	Neurogen Corp	Piridinas pirazinas y pirimidinas heteroarilo fusionadas como ligandos receptores de crf1
US7208596B2 (en)	2003-11-25	2007-04-24	Bristol-Myers Squibb Pharma Company	Processes for the preparation of pyrazolo[1,5-a]-1,3,5-triazines and intermediates thereof
US7153961B2 (en)	2003-11-25	2006-12-26	Bristol-Myers Squibb Pharma Co.	Salt and crystalline form thereof of a corticotropin releasing factor receptor antagonist
GB0328243D0 (en)	2003-12-05	2004-01-07	Astrazeneca Ab	Methods
US7102001B2 (en)	2003-12-12	2006-09-05	Bristol-Myers Squibb Company	Process for preparing pyrrolotriazine
MY143499A (en)	2003-12-22	2011-05-31	Sb Pharmco Inc	Crf receptor antagonist and methods relating thereto
US7064203B2 (en)	2003-12-29	2006-06-20	Bristol Myers Squibb Company	Di-substituted pyrrolotriazine compounds
MY145634A (en)	2003-12-29	2012-03-15	Bristol Myers Squibb Co	Pyrrolotriazine compounds as kinase inhibitors
EP1701961A1 (de)	2004-01-06	2006-09-20	Taisho Pharmaceutical Co., Ltd	Mit einer cyclischen aminogruppe substituierte thienopyrimidin- und thienopyridinderivate
CA2552503C (en) *	2004-01-06	2011-09-13	Taisho Pharmaceutical Co., Ltd.	Pyrrolopyrimidine and pyrrolotriazine derivatives
CN102911161A (zh)	2004-02-20	2013-02-06	贝林格尔.英格海姆国际有限公司	病毒聚合酶抑制剂
US7102002B2 (en)	2004-06-16	2006-09-05	Bristol-Myers Squibb Company	Pyrrolotriazine kinase inhibitors
US7102003B2 (en)	2004-07-01	2006-09-05	Bristol-Myers Squibb Company	Pyrrolotriazine compounds
US7504521B2 (en)	2004-08-05	2009-03-17	Bristol-Myers Squibb Co.	Methods for the preparation of pyrrolotriazine compounds
TW200618803A (en)	2004-08-12	2006-06-16	Bristol Myers Squibb Co	Process for preparing pyrrolotriazine aniline compounds useful as kinase inhibitors
GB0519957D0 (en)	2005-09-30	2005-11-09	Sb Pharmco Inc	Chemical compound
US7652035B2 (en) *	2004-10-19	2010-01-26	Neurocrine Bioscience, Inc.	CRF receptor antagonists and methods relating thereto
US7151176B2 (en)	2004-10-21	2006-12-19	Bristol-Myers Squibb Company	Pyrrolotriazine compounds
AU2005302448B2 (en)	2004-10-29	2012-07-19	Biocryst Pharmaceuticals, Inc.	Therapeutic furopyrimidines and thienopyrimidines
US7674822B2 (en)	2004-11-24	2010-03-09	Wyeth	PTP1b inhibitors
WO2006104945A2 (en)	2005-03-29	2006-10-05	Biocryst Pharmaceuticals, Inc.	Hepatitis c therapies
JPWO2006126718A1 (ja) *	2005-05-27	2008-12-25	田辺三菱製薬株式会社	ピラゾロピリミジン誘導体
TW200740820A (en)	2005-07-05	2007-11-01	Takeda Pharmaceuticals Co	Fused heterocyclic derivatives and use thereof
US7932257B2 (en)	2005-07-22	2011-04-26	Sunesis Pharmaceuticals, Inc.	Substituted pyrazolo[4,3-d]pyrimidines as aurora kinase inhibitors
US20070078136A1 (en)	2005-09-22	2007-04-05	Bristol-Myers Squibb Company	Fused heterocyclic compounds useful as kinase modulators
US7514435B2 (en)	2005-11-18	2009-04-07	Bristol-Myers Squibb Company	Pyrrolotriazine kinase inhibitors
US8063208B2 (en)	2006-02-16	2011-11-22	Bristol-Myers Squibb Company	Crystalline forms of (3R,4R)-4-amino-1-[[4-[(3-methoxyphenyl)amino]pyrrolo[2,1-f][1,2,4]triazin-5-yl]methyl]piperidin-3-ol
HRP20100516T1 (hr)	2006-09-20	2010-10-31	Eli Lilly And Company	Tiazolpirazolopirimidini kao antagonisti receptora crf1
JP5184536B2 (ja)	2006-09-20	2013-04-17	イーライリリーアンドカンパニー	チオフェンピラゾロピリミジン化合物
MX337906B (es)	2006-10-19	2016-03-28	Signal Pharm Llc	Compuestos de heteroarilo, composiciones de los mismos, y su uso como inhibidores de proteina cinasas.
CN101932583A (zh)	2007-12-19	2010-12-29	沃泰克斯药物股份有限公司	用作JAK2抑制剂的吡唑并[1,5-a]嘧啶类
US8324241B2 (en)	2008-04-11	2012-12-04	Bristol-Myers Squibb Company	Triazolo compounds useful as DGAT1 inhibitors
US8394823B2 (en)	2008-04-11	2013-03-12	Bristol-Myers Squibb Company	Triazolopyridine compounds useful as DGAT1 inhibitors
EP2266990B1 (de)	2008-04-15	2012-09-26	Eisai R&D Management Co., Ltd.	3-PHENYLPYRAZOL[5,1-b]THIAZOL-VERBINDUNG
GB0906579D0 (en)	2009-04-16	2009-05-20	Vernalis R&D Ltd	Pharmaceuticals, compositions and methods of making and using the same
TWI491610B (zh)	2008-10-09	2015-07-11	必治妥美雅史谷比公司	作為激酶抑制劑之咪唑并嗒腈
AR078521A1 (es)	2009-10-08	2011-11-16	Eisai R&D Man Co Ltd	Compuesto pirazolotiazol
PH12012501662A1 (en) *	2010-02-18	2012-10-22	Centro Nac De Investigaciones Oncologicas Cnio	Triazolo [4,5 - b] pyridin derivatives
US8912184B1 (en)	2010-03-01	2014-12-16	Alzheimer's Institute Of America, Inc.	Therapeutic and diagnostic methods
US8450320B2 (en) *	2010-04-16	2013-05-28	Abbvie Inc.	Pyrrolopyrazinone inhibitors of kinases
EP2563792B1 (de)	2010-04-28	2014-08-27	Bristol-Myers Squibb Company	Imidazopyridazinylverbindungen und ihre verwendung für krebs
TWI541243B (zh)	2010-09-10	2016-07-11	拜耳知識產權公司	經取代咪唑并嗒
EP3323818A1 (de)	2010-09-22	2018-05-23	Arena Pharmaceuticals, Inc.	Modulatoren des gpr119-rezeptors und behandlung von damit assoziierten erkrankungen
WO2012064815A1 (en)	2010-11-12	2012-05-18	Bristol-Myers Squibb Company	Substituted azaindazole compounds
CA2821817A1 (en)	2010-12-17	2012-06-21	Bayer Intellectual Property Gmbh	Substituted 6-imidazopyrazines for use as mps-1 and tkk inhibitors in the treatment of hyperproliferative disorders
JP2014503521A (ja)	2010-12-17	2014-02-13	バイエル・インテレクチュアル・プロパティ・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツング	過増殖性障害の処置におけるｍｐｓ−１およびｔｋｋ阻害剤としての使用のための、イミダゾピラジン類
ES2544609T3 (es)	2010-12-17	2015-09-02	Bayer Intellectual Property Gmbh	Imidazopirazinas 2-sustituidas para uso como inhibidores de Mps-1 y TTK en el tratamiento de trastornos hiper-proliferativos
PT3590928T (pt)	2011-04-08	2021-08-19	Janssen Sciences Ireland Unlimited Co	Derivados de pirimidina para o tratamento de infeções virais
US10953012B2 (en) *	2011-04-26	2021-03-23	Bioenergenix Llc	Heterocyclic compounds for the inhibition of pask
US8969586B2 (en)	2011-09-27	2015-03-03	Bristol-Myers Squibb Company	Substituted bicyclic heteroaryl compounds
JP6349256B2 (ja)	2011-11-09	2018-06-27	ヤンセン・サイエンシズ・アイルランド・ユーシー	ウイルス感染の治療のためのプリン誘導体
WO2013135612A1 (en)	2012-03-14	2013-09-19	Bayer Intellectual Property Gmbh	Substituted imidazopyridazines
AU2013289284B2 (en) *	2012-07-09	2017-03-30	Janssen Pharmaceutica Nv	Inhibitors of phosphodiesterase 10 enzyme
EA035790B1 (ru)	2012-07-13	2020-08-11	Янссен Сайенсиз Айрлэнд Юси	Макроциклические пурины для лечения вирусных инфекций
WO2014020041A1 (en)	2012-08-02	2014-02-06	Bayer Pharma Aktiengesellschaft	Combinations for the treatment of cancer
DK2906563T3 (en)	2012-10-10	2018-06-06	Janssen Sciences Ireland Uc	PYRROLO [3,2-D] PYRIMIDINE DERIVATIVES FOR TREATING VIRUS INFECTIONS AND OTHER DISEASES
US10392389B2 (en)	2012-10-25	2019-08-27	Bioenergenix Llc	Heterocyclic compounds for the inhibition of PASK
WO2014066743A1 (en)	2012-10-25	2014-05-01	Bioenergenix	Heterocyclic compounds for the inhibition of pask
EA035431B1 (ru)	2012-11-16	2020-06-15	Янссен Сайенсиз Айрлэнд Юси	Гетероциклические замещенные производные 2-амино-хиназолина в качестве модуляторов tlr7 и/или tlr8 для лечения вирусных инфекций
SG11201506639XA (en)	2013-02-21	2015-09-29	Janssen Sciences Ireland Uc	2-aminopyrimidine derivatives for the treatment of viral infections
KR20150130491A (ko)	2013-03-13	2015-11-23	제넨테크, 인크.	피라졸로 화합물 및 그것의 용도
CN110590809B (zh)	2013-03-29	2022-04-19	爱尔兰詹森科学公司	用于治疗病毒感染的大环脱氮-嘌呤酮
SG11201509520QA (en)	2013-05-24	2015-12-30	Janssen Sciences Ireland Uc	Pyridone derivatives for the treatment of viral infections and further diseases
AP2015008898A0 (en)	2013-06-11	2015-12-31	Bayer Pharma AG	Prodrug derivatives of substituted triazolopyridines
PT3030563T (pt) *	2013-06-27	2017-11-15	Janssen Sciences Ireland Uc	Derivados de pirrolo[3,2-d]pirimidina para o tratamento de infeções virais e outras doenças
DK3027624T3 (en)	2013-07-30	2019-01-07	Janssen Sciences Ireland Uc	THIENO [3,2-D] PYRIMIDINE DERIVATIVES FOR TREATING VIRUS INFECTIONS
EP2940022B1 (de) *	2014-04-30	2020-09-02	Masarykova Univerzita	Furopyridinen als Inhibitoren von Proteinkinasen
PL3242666T3 (pl)	2015-01-06	2025-02-17	Arena Pharmaceuticals, Inc.	Związek do zastosowania w leczeniu dolegliwości związanych z receptorem s1p1
BR112017027656B1 (pt)	2015-06-22	2023-12-05	Arena Pharmaceuticals, Inc.	Hábito cristalino de placa livre de sal de l-arginina de ácido (r)-2-(7-(4- ciclopentil-3-(trifluorometil)benzilóxi)- 1,2,3,4-tetra-hidrociclo-penta[b]indol-3- il)acético, composição farmacêutica que o compreende, seus usos e método de preparação do mesmo
RU2699568C2 (ru) *	2015-12-21	2019-09-06	Федеральное государственное бюджетное научное учреждение "Научно-исследовательский институт фармакологии имени В.В. Закусова"	Лиганды транслокаторного белка TSPO, обладающие антидепрессивной и ноотропной активностью
MA45539A (fr)	2016-07-01	2019-05-08	Janssen Sciences Ireland Unlimited Co	Dihydropyranopyrimidines pour le traitement d'infections virales
ES2912945T3 (es)	2016-09-29	2022-05-30	Janssen Sciences Ireland Unlimited Co	Profármacos de pirimidina para el tratamiento de infecciones virales y otras enfermedades
WO2019036503A1 (en)	2017-08-14	2019-02-21	Spruce Biosciences, Inc.	CORTICOTROPIN RELEASE FACTOR RECEPTOR ANTAGONISTS
TW201945003A (zh)	2018-03-01	2019-12-01	愛爾蘭商健生科學愛爾蘭無限公司	２，４－二胺基喹唑啉衍生物及其醫學用途
EP4643950A3 (de)	2018-04-27	2026-01-14	Spruce Biosciences, Inc.	Verfahren zur behandlung von hoden- und eierstock-nebennierentumoren
CA3102136A1 (en)	2018-06-06	2019-12-12	Arena Pharmaceuticals, Inc.	Methods of treating conditions related to the s1p1 receptor
CN108812546A (zh) *	2018-09-07	2018-11-16	四川省草原科学研究院	适于青藏高原地区牦牛运输减少应激的药物及使用方法
KR20240023691A (ko)	2020-08-12	2024-02-22	스프루스 바이오사이언시스 인코포레이티드	다낭성 난소 증후군을 치료하기 위한 방법 및 조성물
US11708372B2 (en)	2021-11-19	2023-07-25	Spruce Biosciences, Inc.	Crystalline composition of tildacerfont and methods of use and preparation thereof

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
TW530047B (en) *	1994-06-08	2003-05-01	Pfizer	Corticotropin releasing factor antagonists
EP0770080B1 (de) *	1995-05-12	1999-07-14	Neurogen Corporation	Neue deazapurinderivate; eine neue klasse von crf1-spezifischen liganden

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Also Published As

Publication number	Publication date
ATE340176T1 (de)	2006-10-15
CN1227554A (zh)	1999-09-01
NO313636B1 (no)	2002-11-04
HRP970454A2 (en)	1998-08-31
HUP9903965A2 (hu)	2000-03-28
EP0923582A1 (de)	1999-06-23
NZ333302A (en)	2000-08-25
BR9711970A (pt)	1999-08-24
PL332040A1 (en)	1999-08-16
AP9701077A0 (en)	1997-10-31
DE69736711D1 (de)	2006-11-02
BG103189A (en)	1999-09-30
PA8436201A1 (es)	1999-12-27
TR199900389T2 (xx)	2000-06-21
WO1998008847A1 (en)	1998-03-05
CO4600634A1 (es)	1998-05-08
ES2273369T3 (es)	2007-05-01
AU3456197A (en)	1998-03-19
EA002769B1 (ru)	2002-08-29
JP2005047930A (ja)	2005-02-24
JP3621706B2 (ja)	2005-02-16
PE108898A1 (es)	1999-01-26
JP2000502723A (ja)	2000-03-07
MA26438A1 (fr)	2004-12-20
IS4963A (is)	1999-01-29
GT199700095A (es)	1999-02-16
TW575573B (en)	2004-02-11
ID18249A (id)	1998-03-19
EP0923582B1 (de)	2006-09-20
DE69736711T2 (de)	2007-09-20
EA199900165A1 (ru)	1999-08-26
AP762A (en)	1999-09-13
CA2263566C (en)	2003-09-09
IL127566A0 (en)	1999-10-28
HUP9903965A3 (en)	2002-02-28
SK23399A3 (en)	2000-08-14
NO990927L (no)	1999-02-26
ZA977687B (en)	1999-03-01
CZ68199A3 (cs)	1999-11-17
DZ2300A1 (fr)	2002-12-25
KR20000035934A (ko)	2000-06-26
CA2263566A1 (en)	1998-03-05
TNSN97145A1 (fr)	2005-03-15
AU735401B2 (en)	2001-07-05
NO990927D0 (no)	1999-02-26
AR015103A1 (es)	2001-04-18
HRP970454B1 (en)	2002-10-31

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US3929787A (en)	1975-12-30	6,7,8,9-Tetrahydro-pyrido(1,2-a)pyrimidin-4-ones
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