ES2509922T3 - Inhibidores de diacilglicerol aciltransferasa - Google Patents
Inhibidores de diacilglicerol aciltransferasa Download PDFInfo
- Publication number
- ES2509922T3 ES2509922T3 ES10799154.9T ES10799154T ES2509922T3 ES 2509922 T3 ES2509922 T3 ES 2509922T3 ES 10799154 T ES10799154 T ES 10799154T ES 2509922 T3 ES2509922 T3 ES 2509922T3
- Authority
- ES
- Spain
- Prior art keywords
- benzazepin
- dihydro
- imidazo
- mmol
- cyclopropyl
- Prior art date
- Legal status (The legal status 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 status listed.)
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- 102000002148 Diacylglycerol O-acyltransferase Human genes 0.000 title description 3
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- 239000002404 acyltransferase inhibitor Substances 0.000 title description 2
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- 150000003839 salts Chemical class 0.000 claims abstract description 52
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- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 23
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 13
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims abstract description 12
- 238000011282 treatment Methods 0.000 claims description 17
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- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 29
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- -1 [1,3-bis (2,6-diisopropylphenyl) imidazol-2-ylidene] - (3-chloropyridyl) Chemical group 0.000 description 27
- 238000012360 testing method Methods 0.000 description 27
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- SHSGDXCJYVZFTP-UHFFFAOYSA-N 4-ethoxybenzoic acid Chemical compound CCOC1=CC=C(C(O)=O)C=C1 SHSGDXCJYVZFTP-UHFFFAOYSA-N 0.000 description 10
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- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 8
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- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- GMCFALNLLGSKFA-GOSISDBHSA-N 4-chloro-n-[1-[[(4r)-5,6-dihydro-4h-imidazo[1,2-a][1]benzazepin-4-yl]carbamoyl]cyclopropyl]benzamide Chemical compound C1=CC(Cl)=CC=C1C(=O)NC1(C(=O)N[C@H]2C3=NC=CN3C3=CC=CC=C3CC2)CC1 GMCFALNLLGSKFA-GOSISDBHSA-N 0.000 description 7
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- FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 6
- UMFYXYABQLRNNV-UHFFFAOYSA-N 5,6-dihydro-4h-imidazo[1,2-a][1]benzazepin-4-amine Chemical compound NC1CCC2=CC=CC=C2N2C=CN=C12 UMFYXYABQLRNNV-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
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- JQVSUGPXKLRFKH-QGZVFWFLSA-N benzyl n-[(4r)-5,6-dihydro-4h-imidazo[1,2-a][1]benzazepin-4-yl]carbamate Chemical compound N([C@H]1C2=NC=CN2C2=CC=CC=C2CC1)C(=O)OCC1=CC=CC=C1 JQVSUGPXKLRFKH-QGZVFWFLSA-N 0.000 description 5
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- HIDGENJCVNDYGI-UHFFFAOYSA-N ethyl 3-(2-imidazol-1-ylphenyl)propanoate Chemical compound CCOC(=O)CCC1=CC=CC=C1N1C=NC=C1 HIDGENJCVNDYGI-UHFFFAOYSA-N 0.000 description 3
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/4164—1,3-Diazoles
- A61K31/4188—1,3-Diazoles condensed with other heterocyclic ring systems, e.g. biotin, sorbinil
-
- 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- Diabetes (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Obesity (AREA)
- Hematology (AREA)
- Endocrinology (AREA)
- Emergency Medicine (AREA)
- Epidemiology (AREA)
- Child & Adolescent Psychology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US28531709P | 2009-12-10 | 2009-12-10 | |
| US285317P | 2009-12-10 | ||
| PCT/US2010/059158 WO2011071840A1 (en) | 2009-12-10 | 2010-12-07 | Inhibitors of diacylglycerol acyltransferase |
Publications (1)
| Publication Number | Publication Date |
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| ES2509922T3 true ES2509922T3 (es) | 2014-10-20 |
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| ES10799154.9T Active ES2509922T3 (es) | 2009-12-10 | 2010-12-07 | Inhibidores de diacilglicerol aciltransferasa |
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| US (1) | US8299061B2 (OSRAM) |
| EP (1) | EP2509981B1 (OSRAM) |
| JP (1) | JP5631411B2 (OSRAM) |
| KR (1) | KR101395428B1 (OSRAM) |
| CN (1) | CN102666543B (OSRAM) |
| AR (1) | AR079170A1 (OSRAM) |
| AU (1) | AU2010328410B2 (OSRAM) |
| BR (1) | BR112012013918A2 (OSRAM) |
| CA (1) | CA2783684C (OSRAM) |
| EA (1) | EA020128B1 (OSRAM) |
| ES (1) | ES2509922T3 (OSRAM) |
| MX (1) | MX2012006646A (OSRAM) |
| TW (1) | TWI392680B (OSRAM) |
| WO (1) | WO2011071840A1 (OSRAM) |
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| KR101774742B1 (ko) | 2010-07-16 | 2017-09-11 | 애브비 아일랜드 언리미티드 컴퍼니 | 촉매 반응용 포스핀 리간드 |
| MX2013000623A (es) | 2010-07-16 | 2013-06-13 | Abbvie Inc | Proceso para la preparación de compuestos antivirales. |
| US8975443B2 (en) | 2010-07-16 | 2015-03-10 | Abbvie Inc. | Phosphine ligands for catalytic reactions |
| US9255074B2 (en) | 2010-07-16 | 2016-02-09 | Abbvie Inc. | Process for preparing antiviral compounds |
| WO2015120610A1 (en) * | 2014-02-14 | 2015-08-20 | Eli Lilly And Company | Gpr142 agonist compound |
| CN105153195B (zh) * | 2015-09-01 | 2017-09-26 | 汤文建 | 一种三环吡唑[1,5‑d][1,4]苯并氧氮杂卓酮衍生物及其制备方法与用途 |
| US12351587B2 (en) * | 2019-05-31 | 2025-07-08 | Medshine Discovery Inc. | Bicyclic compound as RIP-1 kinase inhibitor and application thereof |
| TWI824259B (zh) * | 2020-07-01 | 2023-12-01 | 美商雷傑製藥公司 | Rip1k抑制劑 |
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| US4847248A (en) | 1986-12-23 | 1989-07-11 | Merck & Co., Inc. | 1,4-Benzodiazepines with 5- and 6-membered heterocyclic rings and their use as cholecystokinins and gastrin antagonists |
| EP0272866A1 (en) | 1986-12-23 | 1988-06-29 | Merck & Co. Inc. | 1,4-Benzodiazepines with 5-membered heterocyclic rings |
| US4735941A (en) | 1986-12-23 | 1988-04-05 | Merck & Co., Inc. | 1,4-benzodiazepines with 5- and 6-membered heterocyclic rings, useful as gastrointestinal and CNS agents |
| IL101850A (en) * | 1991-06-13 | 1996-01-31 | Janssen Pharmaceutica Nv | 11-(4-Piperidinyl)-imidazo (2,1-b) (3) benzazepine derivatives their preparation and pharmaceutical compositions containing them |
| CA2071092A1 (en) | 1991-06-14 | 1992-12-15 | Roger M. Freidinger | 1,4-benzodiazepines with 5-membered heterocyclic rings |
| US5439906A (en) | 1993-11-22 | 1995-08-08 | Merck & Co., Inc. | Antiarrhythmic benzodiazepines |
| US5696111A (en) | 1993-11-22 | 1997-12-09 | Merck & Co., Inc. | 3-acylaminobenzazepines |
| CA2176020A1 (en) | 1993-11-22 | 1995-06-01 | John J. Baldwin | Benzodiazepines |
| US5834464A (en) | 1994-11-18 | 1998-11-10 | Merck & Co., Inc. | Imidazolinobenzodiazepines |
| DK0951466T3 (da) | 1996-12-23 | 2009-03-16 | Elan Pharm Inc | Cycloalkyl-, lactam, lacton- og beslægtede forbindelser, farmaceutiske sammensætninger, der omfatter samme, og fremgangsmåder til inhibering af beta-amyloidpeptidfrigivelse og/eller dets syntese ved anvendelse af sådanne forbindelser |
| GB0012671D0 (en) | 2000-05-24 | 2000-07-19 | Merck Sharp & Dohme | Therapeutic agents |
| AU2005272627A1 (en) * | 2004-08-13 | 2006-02-23 | Amgen Inc. | Substituted benzofused heterocycles |
| EP1881958B1 (en) * | 2005-05-10 | 2009-09-09 | Via Pharmaceuticals, Inc. | Diacylglycerol acyltransferase inhibitors |
| CN101232887A (zh) | 2005-07-29 | 2008-07-30 | 默克公司 | 杂环苯并二氮杂䓬cgrp受体拮抗剂 |
| US7569590B2 (en) | 2006-09-19 | 2009-08-04 | Bristol-Myers Squibb Company | Use of thianecarboxamides as dgat inhibitors |
| US8324241B2 (en) | 2008-04-11 | 2012-12-04 | Bristol-Myers Squibb Company | Triazolo compounds useful as DGAT1 inhibitors |
| WO2009126861A2 (en) | 2008-04-11 | 2009-10-15 | Bristol-Myers Squibb Company | Triazolopyridine compounds useful as dgat1 inhibitors |
| JP2010116364A (ja) | 2008-11-14 | 2010-05-27 | Banyu Pharmaceut Co Ltd | アゼピノン誘導体 |
| JP2012515713A (ja) | 2009-01-23 | 2012-07-12 | Ｍｓｄ株式会社 | ベンゾジアゼピン−２−オン誘導体 |
| US20120015938A1 (en) | 2009-02-17 | 2012-01-19 | Msd K.K. | 1,4-benzodiazepin-2-on derivatives |
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- 2010-12-02 TW TW099141941A patent/TWI392680B/zh not_active IP Right Cessation
- 2010-12-07 WO PCT/US2010/059158 patent/WO2011071840A1/en not_active Ceased
- 2010-12-07 EP EP10799154.9A patent/EP2509981B1/en not_active Not-in-force
- 2010-12-07 KR KR1020127014795A patent/KR101395428B1/ko not_active Expired - Fee Related
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Also Published As
| Publication number | Publication date |
|---|---|
| AR079170A1 (es) | 2011-12-28 |
| MX2012006646A (es) | 2012-06-25 |
| KR20120099457A (ko) | 2012-09-10 |
| JP5631411B2 (ja) | 2014-11-26 |
| EA201200868A1 (ru) | 2012-12-28 |
| CN102666543A (zh) | 2012-09-12 |
| EP2509981A1 (en) | 2012-10-17 |
| JP2013513607A (ja) | 2013-04-22 |
| BR112012013918A2 (pt) | 2016-04-26 |
| TWI392680B (zh) | 2013-04-11 |
| CA2783684A1 (en) | 2011-06-16 |
| KR101395428B1 (ko) | 2014-05-14 |
| WO2011071840A1 (en) | 2011-06-16 |
| US20110144091A1 (en) | 2011-06-16 |
| CA2783684C (en) | 2014-02-25 |
| AU2010328410A1 (en) | 2012-07-26 |
| AU2010328410B2 (en) | 2014-02-06 |
| US8299061B2 (en) | 2012-10-30 |
| TW201130844A (en) | 2011-09-16 |
| CN102666543B (zh) | 2014-12-24 |
| EP2509981B1 (en) | 2014-08-06 |
| EA020128B1 (ru) | 2014-08-29 |
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