NO327655B1 - CGRP-reseptorantagonister, farmasoytisk preparat og anvendelse av forbindelsene for fremstilling av et medikament - Google Patents
CGRP-reseptorantagonister, farmasoytisk preparat og anvendelse av forbindelsene for fremstilling av et medikament Download PDFInfo
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- NO327655B1 NO327655B1 NO20055375A NO20055375A NO327655B1 NO 327655 B1 NO327655 B1 NO 327655B1 NO 20055375 A NO20055375 A NO 20055375A NO 20055375 A NO20055375 A NO 20055375A NO 327655 B1 NO327655 B1 NO 327655B1
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- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
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Application Number | Priority Date | Filing Date | Title |
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US46308903P | 2003-04-15 | 2003-04-15 | |
US51035203P | 2003-10-10 | 2003-10-10 | |
PCT/US2004/011280 WO2004092168A1 (en) | 2003-04-15 | 2004-04-09 | Cgrp receptor antagonists |
Publications (2)
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NO20055375L NO20055375L (no) | 2005-11-14 |
NO327655B1 true NO327655B1 (no) | 2009-09-07 |
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NO20055375A NO327655B1 (no) | 2003-04-15 | 2005-11-14 | CGRP-reseptorantagonister, farmasoytisk preparat og anvendelse av forbindelsene for fremstilling av et medikament |
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US (6) | US6953790B2 (de) |
EP (2) | EP2039694B1 (de) |
JP (1) | JP3967766B2 (de) |
KR (1) | KR100769030B1 (de) |
CN (1) | CN100384843C (de) |
AR (1) | AR045887A1 (de) |
AT (1) | ATE413400T1 (de) |
AU (1) | AU2004230926B2 (de) |
BR (1) | BRPI0409601A (de) |
CA (1) | CA2522220C (de) |
CL (1) | CL2004000788A1 (de) |
CO (1) | CO5640130A2 (de) |
CY (1) | CY1108714T1 (de) |
DE (1) | DE602004017608D1 (de) |
DK (1) | DK1638969T3 (de) |
EC (1) | ECSP056097A (de) |
ES (1) | ES2314417T3 (de) |
HK (1) | HK1090922A1 (de) |
HR (1) | HRP20080666T3 (de) |
IS (1) | IS2759B (de) |
JO (1) | JO2355B1 (de) |
MA (1) | MA27728A1 (de) |
MX (1) | MXPA05011166A (de) |
NO (1) | NO327655B1 (de) |
NZ (1) | NZ543357A (de) |
PE (1) | PE20050020A1 (de) |
PL (1) | PL1638969T3 (de) |
PT (1) | PT1638969E (de) |
RU (1) | RU2308458C2 (de) |
SI (1) | SI1638969T1 (de) |
TW (1) | TWI314931B (de) |
UA (1) | UA82877C2 (de) |
WO (2) | WO2004092166A2 (de) |
Families Citing this family (84)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20040063735A1 (en) * | 2002-06-05 | 2004-04-01 | Chaturvedula Prasad V. | Calcitonin gene related peptide receptor antagonists |
US7220862B2 (en) | 2002-06-05 | 2007-05-22 | Bristol-Myers Squibb Company | Calcitonin gene related peptide receptor antagonists |
US7842808B2 (en) | 2002-06-05 | 2010-11-30 | Bristol-Myers Squibb Company | Anti-migraine spirocycles |
JP4705908B2 (ja) * | 2003-04-15 | 2011-06-22 | メルク・シャープ・エンド・ドーム・コーポレイション | Cgrp受容体拮抗薬 |
GB0310881D0 (en) * | 2003-05-12 | 2003-06-18 | Merck Sharp & Dohme | Pharmaceutical formulation |
JP4705911B2 (ja) * | 2003-06-26 | 2011-06-22 | メルク・シャープ・エンド・ドーム・コーポレイション | ベンゾジアゼピンcgrp受容体拮抗物質 |
ATE461196T1 (de) * | 2003-06-26 | 2010-04-15 | Merck Sharp & Dohme | Benzodiazepin-cgrp-rezeptor-antagonisten |
AR046787A1 (es) | 2003-12-05 | 2005-12-21 | Bristol Myers Squibb Co | Agentes antimigrana heterociclicos |
JP4705922B2 (ja) * | 2004-01-29 | 2011-06-22 | メルク・シャープ・エンド・ドーム・コーポレイション | Cgrp受容体拮抗薬 |
JP2007526255A (ja) * | 2004-02-23 | 2007-09-13 | トラスティーズ オブ タフツ カレッジ | コンフォメーション固定ペプチド模倣物阻害剤としてのラクタム類 |
TW200533398A (en) | 2004-03-29 | 2005-10-16 | Bristol Myers Squibb Co | Novel therapeutic agents for the treatment of migraine |
CA2582593A1 (en) * | 2004-10-07 | 2006-04-20 | Merck & Co., Inc. | Cgrp receptor antagonists |
AU2005295855B2 (en) * | 2004-10-14 | 2011-08-18 | Merck Sharp & Dohme Corp. | CGRP receptor antagonists |
JP2008517916A (ja) | 2004-10-22 | 2008-05-29 | メルク エンド カムパニー インコーポレーテッド | Cgrp受容体拮抗薬 |
US7384930B2 (en) * | 2004-11-03 | 2008-06-10 | Bristol-Myers Squibb Company | Constrained compounds as CGRP-receptor antagonists |
US7384931B2 (en) | 2004-11-03 | 2008-06-10 | Bristol-Myers Squibb Company | Constrained compounds as CGRP-receptor antagonists |
US7449586B2 (en) | 2004-12-03 | 2008-11-11 | Bristol-Myers Squibb Company | Processes for the preparation of CGRP-receptor antagonists and intermediates thereof |
GB2423085C (en) | 2005-02-11 | 2011-11-09 | Cambridge Entpr Ltd | Ligands for G-protein coupled receptors |
GB2467060B (en) * | 2005-02-11 | 2010-09-01 | Cambridge Entpr Ltd | Ligands for G-protein coupled receptors |
ATE537170T1 (de) | 2005-03-14 | 2011-12-15 | Merck Sharp & Dohme | Cgrp-rezeptorantagonisten |
US7834007B2 (en) | 2005-08-25 | 2010-11-16 | Bristol-Myers Squibb Company | CGRP antagonists |
US8168592B2 (en) | 2005-10-21 | 2012-05-01 | Amgen Inc. | CGRP peptide antagonists and conjugates |
EA015526B1 (ru) | 2005-11-14 | 2011-08-30 | Ринат Ньюросайенс Корп. | Антагонистические антитела против пептида, связанного с геном кальцитонина, и способы их применения |
CN100371327C (zh) * | 2005-11-17 | 2008-02-27 | 江苏工业学院 | 2-氨基-6-烷氧基-3-硝基吡啶的一步合成法 |
CA2629409A1 (en) * | 2005-11-18 | 2007-05-31 | Merck & Co., Inc. | Spirolactam aryl cgrp receptor antagonists |
US20100286122A1 (en) * | 2006-04-10 | 2010-11-11 | Kevin Belyk | CGRP Antagonist Salt |
DE602007001692D1 (de) * | 2006-04-10 | 2009-09-03 | Merck & Co Inc | Herstellungsverfahren für ein zwischenprodukt eines caprolactam-cgrp-antagonisten |
CA2649158A1 (en) * | 2006-04-10 | 2007-10-25 | Merck & Co., Inc. | Process for the preparation of pyridine heterocycle cgrp antagonist intermediate |
JP2009533439A (ja) * | 2006-04-10 | 2009-09-17 | メルク エンド カムパニー インコーポレーテッド | Cgrp拮抗薬の製造方法 |
EP2013213B1 (de) | 2006-05-02 | 2011-07-27 | Bristol-Myers Squibb Company | Verbindungen mit eingeschränkter konformation als cgrp rezeptor antagonisten. |
US7470680B2 (en) * | 2006-05-03 | 2008-12-30 | Bristol-Myers Squibb Company | Constrained compounds as CGRP-receptor antagonists |
CA2650932C (en) * | 2006-05-09 | 2013-01-22 | Merck & Co., Inc. | Substituted spirocyclic cgrp receptor antagonists |
US8163737B2 (en) | 2006-06-13 | 2012-04-24 | Vertex Pharmaceuticals Incorporated | CGRP receptor antagonists |
US7834000B2 (en) * | 2006-06-13 | 2010-11-16 | Vertex Pharmaceuticals Incorporated | CGRP receptor antagonists |
AR061362A1 (es) * | 2006-06-13 | 2008-08-20 | Vertex Pharma | 4-oxo-tiazoles sustituidos como antagonistas del receptor cgrp, composicion farmaceutica que los comprende y el uso de los mismos en el tratamiento de enfermedades mediadas por el receptor cgrp. |
US8227603B2 (en) | 2006-08-01 | 2012-07-24 | Cytokinetics, Inc. | Modulating skeletal muscle |
KR101410453B1 (ko) * | 2006-08-02 | 2014-06-27 | 싸이토키네틱스, 인코포레이티드 | 소정의 화학 물질, 조성물 및 방법 |
US8299248B2 (en) | 2006-08-02 | 2012-10-30 | Cytokinetics, Incorporated | Certain 1H-imidazo[4,5-b]pyrazin-2(3H)-ones and 1H-imidazo[4,5-b]pyrazin-2-ols and methods for their use |
JP2010502710A (ja) * | 2006-09-08 | 2010-01-28 | メルク エンド カムパニー インコーポレーテッド | Cgrp拮抗薬の経口投与のための液体医薬製剤 |
PT2152690E (pt) | 2007-05-23 | 2012-03-30 | Merck Sharp & Dohme | Antagonistas piridil piperidina de receptor de orexina |
GB0712392D0 (en) * | 2007-06-26 | 2007-08-01 | Glaxo Group Ltd | Novel compounds |
US20090075977A1 (en) * | 2007-09-17 | 2009-03-19 | Protia, Llc | Deuterium-enriched mk0974 |
JP2011511792A (ja) * | 2008-02-05 | 2011-04-14 | メルク・シャープ・エンド・ドーム・コーポレイション | Cgrp受容体アンタゴニストのプロドラッグ |
WO2009105348A1 (en) * | 2008-02-19 | 2009-08-27 | Merck & Co., Inc. | Imidazobenzazepine cgrp receptor antagonists |
KR101304150B1 (ko) | 2008-03-04 | 2013-09-05 | 라브리스 바이올로직스 인코포레이티드 | 만성 통증의 치료 방법 |
US8044043B2 (en) * | 2008-04-11 | 2011-10-25 | Bristol-Myers Squibb Company | CGRP receptor antagonists |
US8143403B2 (en) | 2008-04-11 | 2012-03-27 | Bristol-Myers Squibb Company | CGRP receptor antagonists |
AU2009267145A1 (en) * | 2008-06-30 | 2010-01-07 | Merck Sharp & Dohme Corp. | Solid dosage formulations of telcagepant potassium |
US8623863B2 (en) | 2008-10-21 | 2014-01-07 | Merck Sharp & Dohme Corp. | Disubstituted azepan orexin receptor antagonists |
US8715715B2 (en) | 2008-11-03 | 2014-05-06 | Nal Pharmaceuticals Ltd. | Dosage form for insertion into the mouth |
CN102740884A (zh) | 2009-08-28 | 2012-10-17 | 瑞纳神经科学公司 | 通过施用针对降钙素基因相关肽的拮抗性抗体来治疗内脏痛的方法 |
US8314117B2 (en) | 2009-10-14 | 2012-11-20 | Bristol-Myers Squibb Company | CGRP receptor antagonists |
US8669368B2 (en) | 2010-10-12 | 2014-03-11 | Bristol-Myers Squibb Company | Process for the preparation of cycloheptapyridine CGRP receptor antagonists |
TWI501968B (zh) | 2010-11-12 | 2015-10-01 | Merck Sharp & Dohme | 六氫吡啶酮甲醯胺氮雜茚滿cgrp受體拮抗劑 |
CA2830348A1 (en) * | 2011-03-18 | 2012-09-27 | Merck Sharp & Dohme Corp. | Piperidinone carboxamide spirohydantoin cgrp receptor antagonists |
US8748429B2 (en) | 2011-04-12 | 2014-06-10 | Bristol-Myers Squibb Company | CGRP receptor antagonists |
CA2836800A1 (en) | 2011-05-20 | 2012-11-29 | Alderbio Holdings Llc | Use of anti-cgrp antibodies and antibody fragments to prevent or inhibit photophobia or light aversion in subjects in need thereof, especially migraine sufferers |
HUE055505T2 (hu) | 2011-05-20 | 2021-11-29 | H Lundbeck As | Anti-CGRP készítmények és alkalmazásuk |
NZ717704A (en) | 2011-05-20 | 2022-08-26 | H Lundbeck As | Use of anti-cgrp or anti-cgrp-r antibodies or antibody fragments to treat or prevent chronic and acute forms of diarrhea |
JP6145946B2 (ja) | 2011-07-13 | 2017-06-14 | サイトキネティックス, インコーポレイテッド | 併用als療法 |
AR088352A1 (es) | 2011-10-19 | 2014-05-28 | Merck Sharp & Dohme | Antagonistas del receptor de 2-piridiloxi-4-nitrilo orexina |
ES2642737T3 (es) | 2012-02-27 | 2017-11-17 | Bristol-Myers Squibb Company | Sal de hemisulfato de N-(5S,6S,9R)-5-amino-6-(2,3-difluorofenil)-6,7,8,9-tetrahidro-5H-ciclohepta[b]piridin-9-il-4-(2-oxo-2,3-dihidro-1H-imidazo[4,5-b]piridin-1-il)piperidina-1-carboxilato |
CN104203925A (zh) | 2012-03-29 | 2014-12-10 | 拜耳知识产权有限责任公司 | 5-氨基嘧啶衍生物及其用于防治不希望的植物生长的用途 |
US20170114122A1 (en) | 2015-10-23 | 2017-04-27 | Alderbio Holdings Llc | Regulation of glucose metabolism using anti-cgrp antibodies |
RU2019123406A (ru) | 2014-02-05 | 2019-10-03 | Мерк Шарп И Доум Корп. | Технология приготовления таблеток для cgrp-активных соединений |
US12168004B2 (en) | 2014-02-05 | 2024-12-17 | Merck Sharp & Dohme Llc | Treatment of migraine |
US9896502B2 (en) | 2014-03-21 | 2018-02-20 | Teva Pharmaceuticals International Gmbh | Antagonist antibodies directed against calcitonin gene-related peptide and methods using same |
US10556945B2 (en) | 2014-03-21 | 2020-02-11 | Teva Pharmaceuticals International Gmbh | Antagonist antibodies directed against calcitonin gene-related peptide and methods using same |
GB201417707D0 (en) | 2014-10-07 | 2014-11-19 | Viral Ltd | Pharmaceutical compounds |
WO2017001434A1 (en) * | 2015-06-29 | 2017-01-05 | Galderma Research & Development | Cgrp receptor antagonist compounds for topical treatment of skin disorders |
GB201519194D0 (en) | 2015-10-30 | 2015-12-16 | Heptares Therapeutics Ltd | CGRP receptor antagonists |
GB201519196D0 (en) | 2015-10-30 | 2015-12-16 | Heptares Therapeutics Ltd | CGRP Receptor Antagonists |
GB201519195D0 (en) | 2015-10-30 | 2015-12-16 | Heptares Therapeutics Ltd | CGRP Receptor Antagonists |
JP6937368B2 (ja) | 2016-09-23 | 2021-09-22 | テバ・ファーマシューティカルズ・インターナショナル・ゲー・エム・ベー・ハー | 難治性片頭痛の治療方法 |
EP3366286A1 (de) | 2017-02-22 | 2018-08-29 | Johannes Keller | Verbindungen zur behandlung von sepsis |
GB201707938D0 (en) | 2017-05-17 | 2017-06-28 | Univ Sheffield | Compounds |
US11685729B2 (en) | 2018-01-19 | 2023-06-27 | Idorsia Pharmaceuticals Ltd. | C5a receptor modulators |
CN108892635A (zh) * | 2018-09-07 | 2018-11-27 | 江苏工程职业技术学院 | 一种西沙必利关键中间体的制备方法 |
PH12021551478A1 (en) | 2019-01-08 | 2022-05-02 | H Lundbeck As | Acute treatment and rapid treatment of headache using anti-cgrp antibodies |
GB201908430D0 (en) | 2019-06-12 | 2019-07-24 | Heptares Therapeutics Ltd | Cgrp antagonist compounds |
EP4188375A4 (de) | 2020-07-29 | 2024-07-24 | Allergan Pharmaceuticals International Limited | Behandlung von migräne |
CA3206184A1 (en) | 2020-12-22 | 2022-06-30 | Allergan Pharmaceuticals International Limited | Treatment of migraine |
US20240139171A1 (en) | 2021-03-02 | 2024-05-02 | Cgrp Diagnostics Gmbh | Treatment and/or reduction of occurrence of migraine |
WO2023026205A1 (en) | 2021-08-24 | 2023-03-02 | Cgrp Diagnostics Gmbh | Preventative treatment of migraine |
Family Cites Families (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4166452A (en) | 1976-05-03 | 1979-09-04 | Generales Constantine D J Jr | Apparatus for testing human responses to stimuli |
US4256108A (en) | 1977-04-07 | 1981-03-17 | Alza Corporation | Microporous-semipermeable laminated osmotic system |
US4265874A (en) | 1980-04-25 | 1981-05-05 | Alza Corporation | Method of delivering drug with aid of effervescent activity generated in environment of use |
WO1996035713A1 (en) | 1995-05-08 | 1996-11-14 | Pfizer, Inc. | Dipeptides which promote release of growth hormone |
EP1117662A1 (de) * | 1998-09-30 | 2001-07-25 | Merck Sharp & Dohme Limited | Benzimdazolinylpiperidine als cgrp-liganden |
AU755425B2 (en) | 1998-09-30 | 2002-12-12 | Taisho Pharmaceutical Co., Ltd. | Substituted isoxazolylthiophene compounds |
US20040063735A1 (en) * | 2002-06-05 | 2004-04-01 | Chaturvedula Prasad V. | Calcitonin gene related peptide receptor antagonists |
JP4705908B2 (ja) * | 2003-04-15 | 2011-06-22 | メルク・シャープ・エンド・ドーム・コーポレイション | Cgrp受容体拮抗薬 |
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