ES2309383T3 - Pirrolil tiazoles y su empleo como agonistas inversos de receptores cb1. - Google Patents
Pirrolil tiazoles y su empleo como agonistas inversos de receptores cb1. Download PDFInfo
- Publication number
- ES2309383T3 ES2309383T3 ES03789381T ES03789381T ES2309383T3 ES 2309383 T3 ES2309383 T3 ES 2309383T3 ES 03789381 T ES03789381 T ES 03789381T ES 03789381 T ES03789381 T ES 03789381T ES 2309383 T3 ES2309383 T3 ES 2309383T3
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- Prior art keywords
- lower alkyl
- lower alkoxy
- fluorinated
- amino
- hydroxy
- Prior art date
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- Expired - Lifetime
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
- C07D417/14—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 containing three or more hetero rings
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/08—Drugs for disorders of the alimentary tract or the digestive system for nausea, cinetosis or vertigo; Antiemetics
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/12—Antidiarrhoeals
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- A—HUMAN NECESSITIES
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- A61P1/14—Prodigestives, e.g. acids, enzymes, appetite stimulants, antidyspeptics, tonics, antiflatulents
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- A61P13/02—Drugs for disorders of the urinary system of urine or of the urinary tract, e.g. urine acidifiers
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- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/08—Drugs for genital or sexual disorders; Contraceptives for gonadal disorders or for enhancing fertility, e.g. inducers of ovulation or of spermatogenesis
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- A61P3/04—Anorexiants; Antiobesity agents
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- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
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- A61P35/00—Antineoplastic agents
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- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/48—Drugs for disorders of the endocrine system of the pancreatic hormones
- A61P5/50—Drugs for disorders of the endocrine system of the pancreatic hormones for increasing or potentiating the activity of insulin
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
- C07D417/02—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 containing two hetero rings
- C07D417/04—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 containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Animal Behavior & Ethology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Psychiatry (AREA)
- Diabetes (AREA)
- Addiction (AREA)
- Pain & Pain Management (AREA)
- Endocrinology (AREA)
- Hematology (AREA)
- Heart & Thoracic Surgery (AREA)
- Reproductive Health (AREA)
- Cardiology (AREA)
- Obesity (AREA)
- Hospice & Palliative Care (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Urology & Nephrology (AREA)
- Rheumatology (AREA)
- Virology (AREA)
- Psychology (AREA)
- Vascular Medicine (AREA)
- Emergency Medicine (AREA)
- Otolaryngology (AREA)
- Gynecology & Obstetrics (AREA)
- Pregnancy & Childbirth (AREA)
Abstract
Compuestos de la fórmula (I) (Ver fórmula) en la que R 1 es hidrógeno o alquilo inferior; R 2 es hidrógeno, alquilo inferior, alquenilo inferior, alcoxi inferior-alquilo inferior, (alcoxi inferior)carbonilamino, -(CH2)m-R 2a o -NHC(O)-R 2a ; o R 1 y R 2 junto con el átomo de nitrógeno al que están unidos forman un anillo heterocíclico saturado de 5 ó 6 eslabones que contiene eventualmente uno o dos heteroátomos adicionales elegidos con independencia entre sí entre nitrógeno, oxígeno y azufre, dicho anillo heterocíclico está eventualmente mono-, di- o trisustituido, con independencia entre sí, por hidroxi, alquilo inferior, alcoxi inferior, amino, (alquilo inferior)amino, alquilo inferior fluorado o alcoxi inferior fluorado; R 2a es cicloalquilo, eventualmente mono-, di-, tri- o tetrasustituido, con independencia entre sí, por hidroxi, alquilo inferior, alcoxi inferior, alquilo inferior fluorado o alcoxi inferior fluorado; cicloalquenilo, eventualmente mono-, di- o trisustituido, con independencia entre sí, por hidroxi, alquilo inferior, alcoxi inferior, alquilo inferior fluorado o alcoxi inferior fluorado; un anillo heterocíclico saturado monovalente de 5 ó 6 eslabones que contiene de uno a tres heteroátomos elegidos con independencia entre sí entre nitrógeno, oxígeno y azufre, dicho anillo heterocíclico está eventualmente mono-, di- o trisustituido, con independencia entre sí, por hidroxi, alquilo inferior, alcoxi inferior, amino, (alquilo inferior)amino, alquilo inferior fluorado o alcoxi inferior fluorado; un anillo heteroaromático monovalente de 5 ó 6 eslabones que contiene de uno a tres heteroátomos elegidos con independencia entre sí entre nitrógeno, oxígeno y azufre, dicho anillo heteroaromático está eventualmente mono-, di- o trisustituido, con independencia entre sí, por hidroxi, alquilo inferior, alcoxi inferior, halógeno, amino, (alquilo inferior)amino; o fenilo, que puede estar eventualmente mono-, di- o trisustituido, con independencia entre sí, por hidroxi, alquilo inferior, alcoxi inferior, halógeno, (alquilo inferior)amino, alquilo inferior halogenado, alcoxi inferior halogenado o nitro; R 3 es alquilo inferior, alquenilo inferior, alcoxi inferior-alquilo inferior, di-fenil-alquilo inferior o -(CH2)n-R 3a ; R 3a es cicloalquilo, que puede estar eventualmente fusionado con un anillo fenilo; o cicloalquilo que puede estar eventualmente mono-, di- o trisustituido, con independencia entre sí, por hidroxi, alquilo inferior, alcoxi inferior, alquilo inferior fluorado o alcoxi inferior fluorado; cicloalquenilo, que puede estar eventualmente mono-, di- o trisustituido, con independencia entre sí, por hidroxi, alquilo inferior, alcoxi inferior, alquilo inferior fluorado o alcoxi inferior fluorado; un anillo heterocíclico saturado monovalente de 5 ó 6 eslabones que contiene de uno a tres heteroátomos elegidos con independencia entre sí entre nitrógeno, oxígeno y azufre, dicho anillo heterocíclico está eventualmente mono-, di- o trisustituido, con independencia entre sí, por hidroxi, alquilo inferior, alcoxi inferior, amino, (alquilo inferior)amino, alquilo inferior fluorado o alcoxi inferior fluorado; un anillo heteroaromático monovalente de 5 ó 6 eslabones que contiene de uno a tres heteroátomos elegidos con independencia entre sí entre nitrógeno, oxígeno y azufre, dicho anillo heteroaromático está eventualmente mono-, di- o trisustituido, con independencia entre sí, por hidroxi, alquilo inferior, alcoxi inferior, halógeno, amino o (alquilo inferior)amino; o fenilo, que puede estar eventualmente mono-, di- o trisustituido, con independencia entre sí, por hidroxi, alquilo inferior, alcoxi inferior, halógeno, (alquilo inferior)amino, alquilo inferior halogenado, alcoxi inferior halogenado o nitro; R 4 es...
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP03000002 | 2003-01-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2309383T3 true ES2309383T3 (es) | 2008-12-16 |
Family
ID=32695581
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES03789381T Expired - Lifetime ES2309383T3 (es) | 2003-01-02 | 2003-12-22 | Pirrolil tiazoles y su empleo como agonistas inversos de receptores cb1. |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US7135488B2 (es) |
| EP (1) | EP1583762B1 (es) |
| JP (1) | JP4271660B2 (es) |
| KR (1) | KR100674769B1 (es) |
| CN (1) | CN100360527C (es) |
| AR (1) | AR042690A1 (es) |
| AT (1) | ATE400571T1 (es) |
| AU (1) | AU2003293968A1 (es) |
| BR (1) | BR0317931A (es) |
| CA (1) | CA2511905A1 (es) |
| CL (1) | CL2003002769A1 (es) |
| DE (1) | DE60322114D1 (es) |
| ES (1) | ES2309383T3 (es) |
| MX (1) | MXPA05007115A (es) |
| PL (1) | PL378244A1 (es) |
| RU (1) | RU2330035C2 (es) |
| TW (1) | TW200412344A (es) |
| WO (1) | WO2004060888A1 (es) |
Families Citing this family (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MXPA05007114A (es) | 2003-01-02 | 2005-08-26 | Hoffmann La Roche | Nuevos agonistas inversos del receptor cb1. |
| ATE386725T1 (de) * | 2003-10-24 | 2008-03-15 | Glaxo Group Ltd | Heterocyclylverbindungen |
| US8026237B2 (en) * | 2004-07-30 | 2011-09-27 | Exelixis, Inc. | Pyrrole derivatives as pharmaceutical agents |
| WO2006060461A1 (en) | 2004-12-03 | 2006-06-08 | Schering Corporation | Substituted piperazines as cb1 antagonists |
| NZ564759A (en) | 2005-06-30 | 2011-08-26 | Prosidion Ltd | GPCR agonists |
| BRPI0706623A2 (pt) * | 2006-01-18 | 2011-04-12 | Schering Corp | moduladores de receptor canabinóide |
| 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 |
| GB0700122D0 (en) | 2007-01-04 | 2007-02-14 | Prosidion Ltd | GPCR agonists |
| WO2008081208A1 (en) | 2007-01-04 | 2008-07-10 | Prosidion Limited | Piperidine gpcr agonists |
| BRPI0806498A2 (pt) | 2007-01-04 | 2014-04-22 | Prosidion Ltd | Agonistas gpcr piperidina |
| AR064736A1 (es) | 2007-01-04 | 2009-04-22 | Prosidion Ltd | Agonistas de gpcr |
| US20100197564A1 (en) * | 2007-04-19 | 2010-08-05 | Schering Corporation | Diaryl morpholines as cb1 modulators |
| EP2548874A3 (en) * | 2007-06-28 | 2013-05-15 | Intervet International B.V. | Substituted piperazines as CB1 antagonists |
| US20100286160A1 (en) * | 2007-06-28 | 2010-11-11 | Intervet Inc. | Substituted piperazines as cb1 antagonists |
| GB0720390D0 (en) | 2007-10-18 | 2007-11-28 | Prosidion Ltd | G-Protein coupled receptor agonists |
| GB0720389D0 (en) | 2007-10-18 | 2008-11-12 | Prosidion Ltd | G-Protein Coupled Receptor Agonists |
| KR100954316B1 (ko) * | 2007-12-05 | 2010-04-21 | 한국화학연구원 | 신규한 1-[1-(3,4-디알콕시벤질)-1h-피롤 화합물, 이의제조방법 및 이를 포함하는 천식 및 만성폐쇄성 폐질환을포함한 염증관련 질환, 관절염, 아토피 피부염, 암 및뇌질환의 치료 및 예방을 위한 약제학적 조성물 |
| AU2010313622B2 (en) | 2009-11-02 | 2014-08-14 | Ahr Pharmaceuticals, Inc. | ITE for cancer intervention and eradication |
| US10632106B2 (en) | 2009-11-02 | 2020-04-28 | Ariagen, Inc. | Methods of cancer treatment with 2-(1′H-Indole-3′-carbonyl)-thiazole-4-carboxylic acid methyl ester |
| PT2718290T (pt) * | 2011-06-07 | 2016-07-14 | Clevexel Pharma | Composições e métodos para modular uma quinase |
| US9815851B2 (en) | 2011-12-02 | 2017-11-14 | Phenex Pharmaceuticals Ag | Pyrrolo carboxamides as modulators of orphan nuclear receptor RAR-related orphan receptor-gamma (RORγ, NR1F3) activity and for the treatment of chronic inflammatory and autoimmune diseases |
| EP3191481B1 (en) * | 2014-09-12 | 2020-11-25 | Ariagen, Inc. | Efficient and scalable systhesis of 2-(1'h-indole-3'-carbonyl)-thiazole-4-carboxylic acid methyl ester and its structural analogs |
| CN113480530A (zh) | 2016-12-26 | 2021-10-08 | 阿里根公司 | 芳香烃受体调节剂 |
| KR20200089718A (ko) | 2017-11-20 | 2020-07-27 | 아리아젠, 인크. | 인돌 화합물 및 이의 용도 |
| CA3137027A1 (en) | 2019-04-15 | 2020-10-22 | Ariagen, Inc. | Chiral indole compounds and their use |
| CN113069451B (zh) * | 2021-04-02 | 2022-08-09 | 苏州大学 | 一种吡咯-2-磺酰胺化合物的制备方法及其在制备抗肿瘤药物中的应用 |
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|---|---|---|---|---|
| US3940418A (en) * | 1972-04-07 | 1976-02-24 | G. D. Searle & Co. | Esters and amides of 4,5-dihydrobenz[g]indazole-3-carboxylic acids and related compounds |
| FR2692575B1 (fr) | 1992-06-23 | 1995-06-30 | Sanofi Elf | Nouveaux derives du pyrazole, procede pour leur preparation et compositions pharmaceutiques les contenant. |
| FR2713225B1 (fr) | 1993-12-02 | 1996-03-01 | Sanofi Sa | N-pipéridino-3-pyrazolecarboxamide substitué. |
| US5342851A (en) * | 1992-10-07 | 1994-08-30 | Mcneil-Ppc, Inc. | Substituted thiazole derivatives useful as platelet aggregation inhibitors |
| FR2714057B1 (fr) | 1993-12-17 | 1996-03-08 | Sanofi Elf | Nouveaux dérivés du 3-pyrazolecarboxamide, procédé pour leur préparation et compositions pharmaceutiques les contenant. |
| IL113112A (en) * | 1994-03-28 | 2000-06-01 | Nissan Chemical Ind Ltd | Pyridine substituted thiazolidinediones and pharmaceutical compositions comprising them |
| US5596106A (en) * | 1994-07-15 | 1997-01-21 | Eli Lilly And Company | Cannabinoid receptor antagonists |
| FR2741621B1 (fr) | 1995-11-23 | 1998-02-13 | Sanofi Sa | Nouveaux derives de pyrazole, procede pour leur preparation et compositions pharmaceutiques en contenant |
| FR2783246B1 (fr) | 1998-09-11 | 2000-11-17 | Aventis Pharma Sa | Derives d'azetidine, leur preparation et les medicaments les contenant |
| FR2789079B3 (fr) * | 1999-02-01 | 2001-03-02 | Sanofi Synthelabo | Derive d'acide pyrazolecarboxylique, sa preparation, les compositions pharmaceutiques en contenant |
| FR2800375B1 (fr) | 1999-11-03 | 2004-07-23 | Sanofi Synthelabo | Derives tricycliques d'acide pyrazolecarboxylique, leur preparation, les compositions pharmaceutiques en contenant |
| AU2001234958A1 (en) | 2000-02-11 | 2001-08-20 | Bristol-Myers Squibb Company | Cannabinoid receptor modulators, their processes of preparation, and use of cannabinoid receptor modulators for treating respiratory and non-respiratory diseases |
| FR2805818B1 (fr) | 2000-03-03 | 2002-04-26 | Aventis Pharma Sa | Derives d'azetidine, leur preparation et les compositions pharmaceutiques les contenant |
| FR2805817B1 (fr) | 2000-03-03 | 2002-04-26 | Aventis Pharma Sa | Compositions pharmaceutiques contenant des derives d'azetidine, les nouveaux derives d'azetidine et leur preparation |
| FR2805810B1 (fr) | 2000-03-03 | 2002-04-26 | Aventis Pharma Sa | Compositions pharmaceutiques contenant des derives de 3- amino-azetidine, les nouveaux derives et leur preparation |
| JP2004500401A (ja) | 2000-03-23 | 2004-01-08 | ソルベイ・フアーマシユーチカルズ・ベー・ブイ | Cb1−拮抗活性を有する4,5−ジヒドロ−1h−ピラゾール誘導体 |
| FR2814678B1 (fr) | 2000-10-04 | 2002-12-20 | Aventis Pharma Sa | Association d'un antagoniste du recepteur cb1 et de sibutramine, les compositions pharmaceutiques les contenant et leur utilisation pour la traitement de l'obesite |
| MXPA05007114A (es) * | 2003-01-02 | 2005-08-26 | Hoffmann La Roche | Nuevos agonistas inversos del receptor cb1. |
-
2003
- 2003-12-22 US US10/743,403 patent/US7135488B2/en not_active Expired - Fee Related
- 2003-12-22 DE DE60322114T patent/DE60322114D1/de not_active Expired - Lifetime
- 2003-12-22 CA CA002511905A patent/CA2511905A1/en not_active Abandoned
- 2003-12-22 JP JP2004564211A patent/JP4271660B2/ja not_active Expired - Fee Related
- 2003-12-22 ES ES03789381T patent/ES2309383T3/es not_active Expired - Lifetime
- 2003-12-22 AT AT03789381T patent/ATE400571T1/de not_active IP Right Cessation
- 2003-12-22 KR KR1020057012514A patent/KR100674769B1/ko not_active Expired - Fee Related
- 2003-12-22 BR BR0317931-1A patent/BR0317931A/pt not_active IP Right Cessation
- 2003-12-22 AU AU2003293968A patent/AU2003293968A1/en not_active Abandoned
- 2003-12-22 PL PL378244A patent/PL378244A1/pl not_active Application Discontinuation
- 2003-12-22 EP EP03789381A patent/EP1583762B1/en not_active Expired - Lifetime
- 2003-12-22 CN CNB2003801082691A patent/CN100360527C/zh not_active Expired - Fee Related
- 2003-12-22 WO PCT/EP2003/014721 patent/WO2004060888A1/en not_active Ceased
- 2003-12-22 TW TW092136398A patent/TW200412344A/zh unknown
- 2003-12-22 RU RU2005124359/04A patent/RU2330035C2/ru not_active IP Right Cessation
- 2003-12-22 MX MXPA05007115A patent/MXPA05007115A/es active IP Right Grant
- 2003-12-29 CL CL200302769A patent/CL2003002769A1/es unknown
- 2003-12-30 AR ARP030104877A patent/AR042690A1/es unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AU2003293968A1 (en) | 2004-07-29 |
| CL2003002769A1 (es) | 2005-01-07 |
| EP1583762B1 (en) | 2008-07-09 |
| US20040147572A1 (en) | 2004-07-29 |
| JP2006513226A (ja) | 2006-04-20 |
| WO2004060888A1 (en) | 2004-07-22 |
| CA2511905A1 (en) | 2004-07-22 |
| RU2005124359A (ru) | 2006-05-27 |
| AR042690A1 (es) | 2005-06-29 |
| PL378244A1 (pl) | 2006-03-20 |
| MXPA05007115A (es) | 2005-11-16 |
| EP1583762A1 (en) | 2005-10-12 |
| KR20050092381A (ko) | 2005-09-21 |
| TW200412344A (en) | 2004-07-16 |
| RU2330035C2 (ru) | 2008-07-27 |
| JP4271660B2 (ja) | 2009-06-03 |
| ATE400571T1 (de) | 2008-07-15 |
| CN100360527C (zh) | 2008-01-09 |
| CN1735611A (zh) | 2006-02-15 |
| BR0317931A (pt) | 2005-11-29 |
| KR100674769B1 (ko) | 2007-02-28 |
| DE60322114D1 (de) | 2008-08-21 |
| US7135488B2 (en) | 2006-11-14 |
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