UA80298C2 - 1h-1,2,4-triazole-3-carboxamide derivatives as cannabinoid-cb1 receptor ligands - Google Patents
1h-1,2,4-triazole-3-carboxamide derivatives as cannabinoid-cb1 receptor ligands Download PDFInfo
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- UA80298C2 UA80298C2 UAA200503704A UA2005003704A UA80298C2 UA 80298 C2 UA80298 C2 UA 80298C2 UA A200503704 A UAA200503704 A UA A200503704A UA 2005003704 A UA2005003704 A UA 2005003704A UA 80298 C2 UA80298 C2 UA 80298C2
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- heterocyclic group
- triazole
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Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
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- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
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Applications Claiming Priority (2)
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| EP02078966 | 2002-09-19 | ||
| PCT/EP2003/050628 WO2004026301A1 (en) | 2002-09-19 | 2003-09-17 | 1h-1,2,4-triazole-3-carboxamide derivatives as cannabinoid-cb1 receptor ligands |
Publications (1)
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| UA80298C2 true UA80298C2 (en) | 2007-09-10 |
Family
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| UAA200503704A UA80298C2 (en) | 2002-09-19 | 2003-09-17 | 1h-1,2,4-triazole-3-carboxamide derivatives as cannabinoid-cb1 receptor ligands |
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| PT (1) | PT1542678E (ko) |
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| SI (1) | SI1542678T1 (ko) |
| UA (1) | UA80298C2 (ko) |
| WO (1) | WO2004026301A1 (ko) |
| ZA (1) | ZA200500133B (ko) |
Families Citing this family (51)
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| US6897240B2 (en) * | 2002-05-08 | 2005-05-24 | The Regents Of The University Of California | Thio semicarbazone and semicarbazone inhibitors of cysteine proteases and methods of their use |
| CA2522536A1 (en) * | 2003-04-21 | 2004-11-04 | Daiichi Pharmaceutical Co., Ltd. | Five-membered heterocyclic derivative |
| US7223780B2 (en) * | 2003-05-19 | 2007-05-29 | Sanofi-Aventis Deutschland Gmbh | Triazole-derivatives as blood clotting enzyme factor Xa inhibitors |
| JP2007513872A (ja) * | 2003-10-24 | 2007-05-31 | ゾルファイ ファーマスーティカルズ ゲゼルシャフト ミット ベシュレンクテル ハフツング | Ｃｂ１拮抗作用を示す化合物の新規の医学的用途および前記化合物を伴う組み合わせ治療 |
| US7829552B2 (en) * | 2003-11-19 | 2010-11-09 | Metabasis Therapeutics, Inc. | Phosphorus-containing thyromimetics |
| US20060025448A1 (en) | 2004-07-22 | 2006-02-02 | Cadila Healthcare Limited | Hair growth stimulators |
| FR2874012B1 (fr) * | 2004-08-09 | 2008-08-22 | Sanofi Synthelabo | Derives de pyrrole, leur preparation et leur utlisation en therapeutique |
| ES2255834B1 (es) * | 2004-09-14 | 2008-01-16 | Laboratorios Del Dr. Esteve, S.A. | Nuevos derivados 1,2,4-triazol-3-carboxamida. |
| ATE415385T1 (de) * | 2004-10-01 | 2008-12-15 | Hoffmann La Roche | Hexafluorisopropanolsubstituierte etherderivate |
| RU2007119315A (ru) | 2004-10-25 | 2008-11-27 | Зольвай Фармасьютиклз Гмбх (De) | Фармацевтические композиции, содержащие антагонисты каннабиноидного рецептора св1 и открыватели калиевых каналов, предназначенные для лечения сахарного диабета типа i, ожирения и связанных с ними состояний |
| WO2006050472A2 (en) * | 2004-11-03 | 2006-05-11 | Xenoport, Inc. | Acyloxyalkyl carbamate prodrugs of 3-aminopropylphosphonous and -phosphinic acids |
| CN101166529B (zh) * | 2005-04-29 | 2011-11-16 | 詹森药业有限公司 | 作为大麻素受体拮抗剂的苯并三唑衍生物 |
| US7923465B2 (en) | 2005-06-02 | 2011-04-12 | Glenmark Pharmaceuticals S.A. | Cannabinoid receptor ligands, pharmaceutical compositions containing them, and process for their preparation |
| EP1902034B1 (en) | 2005-06-02 | 2011-03-30 | Glenmark Pharmaceuticals S.A. | Novel cannabinoid receptor ligands, pharmaceutical compositions containing them, and process for their preparation |
| TW200726765A (en) * | 2005-06-17 | 2007-07-16 | Bristol Myers Squibb Co | Triazolopyridine cannabinoid receptor 1 antagonists |
| US7632837B2 (en) | 2005-06-17 | 2009-12-15 | Bristol-Myers Squibb Company | Bicyclic heterocycles as cannabinoid-1 receptor modulators |
| US20090012127A1 (en) * | 2005-06-29 | 2009-01-08 | Astrazeneca Ab | Thiophene-2-Carboxamide Derivatives as Alpha 7 Nicotinic Receptor Modulators |
| AU2006264649A1 (en) | 2005-06-30 | 2007-01-11 | Prosidion Limited | GPCR agonists |
| FR2894579B1 (fr) * | 2005-12-12 | 2008-01-18 | Sanofi Aventis Sa | Derives diaryltriazolmethylamine, leur preparation et leur application en therapeutique. |
| WO2008014199A2 (en) | 2006-07-28 | 2008-01-31 | Boehringer Ingelheim International Gmbh | Sulfonyl compounds which modulate the cb2 receptor |
| WO2008033572A1 (en) * | 2006-09-15 | 2008-03-20 | Xenoport, Inc. | Acyloxyalkyl carbamate prodrugs, methods of synthesis and use |
| WO2008081204A1 (en) | 2007-01-04 | 2008-07-10 | Prosidion Limited | Piperidine gpcr agonists |
| GB0700122D0 (en) | 2007-01-04 | 2007-02-14 | Prosidion Ltd | GPCR agonists |
| CL2008000018A1 (es) | 2007-01-04 | 2008-08-01 | Prosidion Ltd | Compuestos derivados de heterociclos de nitrogeno y oxigeno, agonistas de gpcr; composicion farmaceutica que comprende a dicho compuesto; y uso del compuesto para el tratamiento de la obesidad, diabetes, sindrome metabolico, hiperlipidemia, toleranci |
| WO2008081208A1 (en) | 2007-01-04 | 2008-07-10 | Prosidion Limited | Piperidine gpcr agonists |
| AR064736A1 (es) | 2007-01-04 | 2009-04-22 | Prosidion Ltd | Agonistas de gpcr |
| CN101302200B (zh) * | 2007-05-09 | 2011-04-20 | 上海医药工业研究院 | 制备n-哌啶子基-5-(4-氯苯基)-1-(2,4-二氯苯基)-4-甲基吡唑-3-甲酰胺的方法 |
| GB0720389D0 (en) | 2007-10-18 | 2008-11-12 | Prosidion Ltd | G-Protein Coupled Receptor Agonists |
| GB0720390D0 (en) | 2007-10-18 | 2007-11-28 | Prosidion Ltd | G-Protein coupled receptor agonists |
| CA2704684A1 (en) | 2007-11-07 | 2009-05-14 | Boehringer Ingelheim International Gmbh | Compounds which modulate the cb2 receptor |
| EP2265585B1 (en) | 2008-02-21 | 2014-09-17 | Boehringer Ingelheim International GmbH | Amine and ether compounds which modulate the cb2 receptor |
| JP5749162B2 (ja) | 2008-07-10 | 2015-07-15 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | Ｃｂ２受容体を調節するスルホン化合物 |
| CN102164917A (zh) | 2008-09-25 | 2011-08-24 | 贝林格尔.英格海姆国际有限公司 | 选择性调节cb2受体的磺酰基化合物 |
| JP5583694B2 (ja) | 2009-01-05 | 2014-09-03 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | Ｃｂ２受容体を調節するピロリジン化合物 |
| WO2010079241A1 (es) | 2009-01-12 | 2010-07-15 | Fundacion Hospital Nacional De Paraplejicos Para La Investigacion Y La Integracion | Uso de antagonistas y/o agonistas inversos de los receptores cb1 para la preparación de medicamentos que incrementen la excitabilidad de las motoneuronas |
| EP2398771B1 (en) | 2009-02-18 | 2015-07-29 | Boehringer Ingelheim International GmbH | Heterocyclic compounds which modulate the cb2 receptor |
| US8299103B2 (en) | 2009-06-15 | 2012-10-30 | Boehringer Ingelheim International Gmbh | Compounds which selectively modulate the CB2 receptor |
| US8383615B2 (en) | 2009-06-16 | 2013-02-26 | Boehringer Ingelheim International Gmbh | Azetidine 2-carboxamide derivatives which modulate the CB2 receptor |
| WO2011037795A1 (en) | 2009-09-22 | 2011-03-31 | Boehringer Ingelheim International Gmbh | Compounds which selectively modulate the cb2 receptor |
| EP2523936A1 (en) | 2010-01-15 | 2012-11-21 | Boehringer Ingelheim International GmbH | Compounds which modulate the cb2 receptor |
| WO2011109324A1 (en) | 2010-03-05 | 2011-09-09 | Boehringer Ingelheim International Gmbh | Tetrazole compounds which selectively modulate the cb2 receptor |
| JP5746764B2 (ja) | 2010-07-22 | 2015-07-08 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | Ｃｂ２受容体を調節する化合物 |
| CN102558157B (zh) * | 2010-12-20 | 2014-04-30 | 中国科学院上海药物研究所 | 羟乙基三唑类化合物或氨乙基三唑类化合物及其制备方法和用途 |
| CN102731418B (zh) * | 2012-07-15 | 2015-03-11 | 浙江大学 | 1-取代-1h-1,2,4-三氮唑-甲酰胺衍生物及其制备和用途 |
| BR112015001771B1 (pt) * | 2012-09-17 | 2022-08-16 | F. Hoffmann-La Roche Ag | Derivados de carboxamida de triazol, seu uso e composição farmacêutica que os compreende |
| EP2803668A1 (en) | 2013-05-17 | 2014-11-19 | Boehringer Ingelheim International Gmbh | Novel (cyano-dimethyl-methyl)-isoxazoles and -[1,3,4]thiadiazoles |
| CA2949559C (en) | 2014-06-06 | 2023-08-29 | Research Triangle Institute | Apelin receptor (apj) agonists and uses thereof |
| SI3250563T1 (sl) * | 2015-01-30 | 2022-04-29 | Neurocrine Biosciences, Inc. | Substituirani triazoli in z njimi povezani postopki |
| KR20180090852A (ko) | 2015-12-09 | 2018-08-13 | 리써치 트라이앵글 인스티튜트 | 개선된 아펠린 수용체(apj) 효능제 및 이의 용도 |
| CN114507217A (zh) * | 2016-10-12 | 2022-05-17 | 三角研究所 | 杂环爱帕琳肽受体(apj)激动剂及其用途 |
| CN113166068A (zh) * | 2018-11-20 | 2021-07-23 | 上海科技大学 | MmpL3抑制剂、组合物及其用途 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS58194866A (ja) * | 1982-05-07 | 1983-11-12 | Kureha Chem Ind Co Ltd | トリアゾ−ル誘導体及び該誘導体を含有する除草剤 |
| DE3316300A1 (de) * | 1982-05-07 | 1983-11-24 | Kureha Kagaku Kogyo K.K., Tokyo | Heribizide zusammensetzung mit einem gehalt an einem derivat des 1,2,4-triazols als wirkstoff |
| DE3817192A1 (de) * | 1988-05-20 | 1989-11-30 | Hoechst Ag | 1,2,4-triazolderivate enthaltende pflanzenschuetzende mittel sowie neue derivate des 1,2,4-triazols |
| FR2692575B1 (fr) * | 1992-06-23 | 1995-06-30 | Sanofi Elf | Nouveaux derives du pyrazole, procede pour leur preparation et compositions pharmaceutiques les contenant. |
| DE4225778A1 (de) * | 1992-08-04 | 1994-02-17 | Hoechst Ag | 1,2,4-Triazolyl-3-carbonsäure-4-aminopiperidide, Verfahren zu ihrer Herstellung, sie enthaltende Mittel und ihre Verwendung als Schädlingsbekämpfungsmittel, insbesondere Fungizide |
| FR2741621B1 (fr) * | 1995-11-23 | 1998-02-13 | Sanofi Sa | Nouveaux derives de pyrazole, procede pour leur preparation et compositions pharmaceutiques en contenant |
| FR2789079B3 (fr) * | 1999-02-01 | 2001-03-02 | Sanofi Synthelabo | Derive d'acide pyrazolecarboxylique, sa preparation, les compositions pharmaceutiques en contenant |
| JP2003512357A (ja) | 1999-10-18 | 2003-04-02 | ユニバーシティ オブ コネチカット | カンナビノイドレセプタ拮抗物質としてのピラゾール誘導体 |
| JP2004502642A (ja) | 2000-02-11 | 2004-01-29 | ブリストル−マイヤーズ スクイブ カンパニー | カンナビノイドレセプターモジュレーター、それらの製造方法、および呼吸系および非呼吸系疾患の処置のためのカンナビノイドレセプターモジュレーターの使用 |
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2003
- 2003-09-16 US US10/662,477 patent/US7319110B2/en not_active Expired - Fee Related
- 2003-09-16 AR ARP030103347A patent/AR041268A1/es unknown
- 2003-09-17 AT AT03797318T patent/ATE458479T1/de active
- 2003-09-17 CA CA2491394A patent/CA2491394C/en not_active Expired - Fee Related
- 2003-09-17 MX MXPA05002862A patent/MXPA05002862A/es active IP Right Grant
- 2003-09-17 PL PL03375020A patent/PL375020A1/xx not_active Application Discontinuation
- 2003-09-17 RU RU2005103244/04A patent/RU2325382C2/ru not_active IP Right Cessation
- 2003-09-17 KR KR1020057004584A patent/KR100996828B1/ko not_active IP Right Cessation
- 2003-09-17 AU AU2003299024A patent/AU2003299024B2/en not_active Ceased
- 2003-09-17 EP EP03797318A patent/EP1542678B1/en not_active Expired - Lifetime
- 2003-09-17 CN CNB038173522A patent/CN1319529C/zh not_active Expired - Fee Related
- 2003-09-17 SI SI200331803T patent/SI1542678T1/sl unknown
- 2003-09-17 DE DE60331444T patent/DE60331444D1/de not_active Expired - Lifetime
- 2003-09-17 ES ES03797318T patent/ES2341540T3/es not_active Expired - Lifetime
- 2003-09-17 DK DK03797318.7T patent/DK1542678T3/da active
- 2003-09-17 WO PCT/EP2003/050628 patent/WO2004026301A1/en active Application Filing
- 2003-09-17 PT PT03797318T patent/PT1542678E/pt unknown
- 2003-09-17 UA UAA200503704A patent/UA80298C2/uk unknown
- 2003-09-17 BR BR0312020-1A patent/BR0312020A/pt not_active IP Right Cessation
- 2003-09-17 JP JP2004537155A patent/JP2006501275A/ja active Pending
-
2004
- 2004-12-07 IL IL165611A patent/IL165611A/en not_active IP Right Cessation
-
2005
- 2005-01-06 ZA ZA200500133A patent/ZA200500133B/en unknown
- 2005-01-19 HR HR20050053A patent/HRP20050053A2/xx not_active Application Discontinuation
- 2005-04-18 NO NO20051870A patent/NO20051870L/no not_active Application Discontinuation
- 2005-12-01 HK HK05110963A patent/HK1078796A1/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| CA2491394C (en) | 2010-06-15 |
| CN1319529C (zh) | 2007-06-06 |
| ZA200500133B (en) | 2005-11-01 |
| BR0312020A (pt) | 2005-03-22 |
| DK1542678T3 (da) | 2010-06-07 |
| RU2005103244A (ru) | 2005-06-27 |
| AR041268A1 (es) | 2005-05-11 |
| CN1671377A (zh) | 2005-09-21 |
| US20040106614A1 (en) | 2004-06-03 |
| IL165611A (en) | 2010-04-15 |
| SI1542678T1 (sl) | 2010-07-30 |
| RU2325382C2 (ru) | 2008-05-27 |
| AU2003299024B2 (en) | 2008-03-06 |
| NO20051870L (no) | 2005-06-03 |
| PL375020A1 (en) | 2005-11-14 |
| DE60331444D1 (de) | 2010-04-08 |
| MXPA05002862A (es) | 2005-05-27 |
| HK1078796A1 (en) | 2006-03-24 |
| PT1542678E (pt) | 2010-05-25 |
| ES2341540T3 (es) | 2010-06-22 |
| EP1542678A1 (en) | 2005-06-22 |
| HRP20050053A2 (en) | 2005-04-30 |
| US7319110B2 (en) | 2008-01-15 |
| KR100996828B1 (ko) | 2010-11-29 |
| EP1542678B1 (en) | 2010-02-24 |
| WO2004026301A1 (en) | 2004-04-01 |
| ATE458479T1 (de) | 2010-03-15 |
| AU2003299024A1 (en) | 2004-04-08 |
| CA2491394A1 (en) | 2004-04-01 |
| JP2006501275A (ja) | 2006-01-12 |
| IL165611A0 (en) | 2006-01-15 |
| KR20050057399A (ko) | 2005-06-16 |
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