CA2641766A1 - Novel acetyl-coa carboxylase (acc) inhibitors and their use in diabetes, obesity and metabolic syndrome - Google Patents
Novel acetyl-coa carboxylase (acc) inhibitors and their use in diabetes, obesity and metabolic syndrome Download PDFInfo
- Publication number
- CA2641766A1 CA2641766A1 CA002641766A CA2641766A CA2641766A1 CA 2641766 A1 CA2641766 A1 CA 2641766A1 CA 002641766 A CA002641766 A CA 002641766A CA 2641766 A CA2641766 A CA 2641766A CA 2641766 A1 CA2641766 A1 CA 2641766A1
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- CA
- Canada
- Prior art keywords
- alkylenyl
- alkyl
- group
- hydrogen
- prodrug
- 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.)
- Abandoned
Links
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- 235000020824 obesity Nutrition 0.000 title claims description 16
- 208000001145 Metabolic Syndrome Diseases 0.000 title claims description 8
- 201000000690 abdominal obesity-metabolic syndrome Diseases 0.000 title claims description 8
- 108010018763 Biotin carboxylase Proteins 0.000 title description 30
- 102000000452 Acetyl-CoA carboxylase Human genes 0.000 title description 27
- 108010016219 Acetyl-CoA carboxylase Proteins 0.000 title description 27
- 206010012601 diabetes mellitus Diseases 0.000 title description 8
- 239000003112 inhibitor Substances 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims description 177
- 125000000217 alkyl group Chemical group 0.000 claims description 134
- 229910052739 hydrogen Inorganic materials 0.000 claims description 109
- 239000001257 hydrogen Substances 0.000 claims description 109
- -1 or W1 is N(R z) Inorganic materials 0.000 claims description 86
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- 125000001188 haloalkyl group Chemical group 0.000 claims description 47
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 46
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- 238000000034 method Methods 0.000 claims description 27
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- 125000001424 substituent group Chemical group 0.000 claims description 23
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 22
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- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical class ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 230000008685 targeting Effects 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- 125000005958 tetrahydrothienyl group Chemical group 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 125000005304 thiadiazolidinyl group Chemical group 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000001984 thiazolidinyl group Chemical group 0.000 description 1
- 125000002769 thiazolinyl group Chemical group 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000011269 treatment regimen Methods 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- JDPCKSVLQMKJAJ-UHFFFAOYSA-N tributyl-[2-(4-methoxyphenoxy)-1,3-thiazol-5-yl]stannane Chemical compound S1C([Sn](CCCC)(CCCC)CCCC)=CN=C1OC1=CC=C(OC)C=C1 JDPCKSVLQMKJAJ-UHFFFAOYSA-N 0.000 description 1
- PIILXFBHQILWPS-UHFFFAOYSA-N tributyltin Chemical compound CCCC[Sn](CCCC)CCCC PIILXFBHQILWPS-UHFFFAOYSA-N 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- MWKJTNBSKNUMFN-UHFFFAOYSA-N trifluoromethyltrimethylsilane Chemical compound C[Si](C)(C)C(F)(F)F MWKJTNBSKNUMFN-UHFFFAOYSA-N 0.000 description 1
- BPLUKJNHPBNVQL-UHFFFAOYSA-N triphenylarsine Chemical compound C1=CC=CC=C1[As](C=1C=CC=CC=1)C1=CC=CC=C1 BPLUKJNHPBNVQL-UHFFFAOYSA-N 0.000 description 1
- ZDPHROOEEOARMN-UHFFFAOYSA-N undecanoic acid Chemical compound CCCCCCCCCCC(O)=O ZDPHROOEEOARMN-UHFFFAOYSA-N 0.000 description 1
- 241000701447 unidentified baculovirus Species 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D277/34—Oxygen atoms
-
- 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
-
- 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
-
- 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
-
- 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
-
- 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
- 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
-
- 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
- C07D417/02—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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Endocrinology (AREA)
- Urology & Nephrology (AREA)
- Emergency Medicine (AREA)
- Vascular Medicine (AREA)
- Child & Adolescent Psychology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US77351406P | 2006-02-15 | 2006-02-15 | |
| US60/773,514 | 2006-02-15 | ||
| PCT/US2007/062181 WO2007095603A2 (en) | 2006-02-15 | 2007-02-15 | Novel acetyl-coa carboxylase (acc) inhibitors and their use in diabetes, obesity and metabolic syndrome |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2641766A1 true CA2641766A1 (en) | 2007-08-23 |
Family
ID=38330470
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002641766A Abandoned CA2641766A1 (en) | 2006-02-15 | 2007-02-15 | Novel acetyl-coa carboxylase (acc) inhibitors and their use in diabetes, obesity and metabolic syndrome |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US8735595B2 (https=) |
| EP (1) | EP1991536A2 (https=) |
| JP (1) | JP2009526868A (https=) |
| CN (1) | CN101384568B (https=) |
| CA (1) | CA2641766A1 (https=) |
| WO (1) | WO2007095603A2 (https=) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NZ563866A (en) | 2005-05-09 | 2011-03-31 | Achillion Pharmaceuticals Inc | Thiazole compounds and methods of use |
| US8748627B2 (en) * | 2006-02-15 | 2014-06-10 | Abbvie Inc. | Acetyl-CoA carboxylase (ACC) inhibitors and their use in diabetes, obesity and metabolic syndrome |
| US8183263B2 (en) | 2007-05-22 | 2012-05-22 | Achillion Pharmaceuticals, Inc. | Heteroaryl substituted thiazoles |
| EP2025674A1 (de) | 2007-08-15 | 2009-02-18 | sanofi-aventis | Substituierte Tetrahydronaphthaline, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel |
| WO2009144554A1 (en) | 2008-05-28 | 2009-12-03 | Pfizer, Inc. | Pyrazolospiroketone acetyl-c0a carboxylase inhibitors |
| US8106209B2 (en) | 2008-06-06 | 2012-01-31 | Achillion Pharmaceuticals, Inc. | Substituted aminothiazole prodrugs of compounds with anti-HCV activity |
| WO2011058474A1 (en) | 2009-11-10 | 2011-05-19 | Pfizer Inc. | N1-pyrazolospiroketone acetyl-coa carboxylase inhibitors |
| HRP20161178T1 (hr) | 2010-09-30 | 2016-11-04 | Pfizer Inc. | N1-PIRAZOLOSPIROKETONSKI INHIBITORI ACETIL-CoA-KARBOKSILAZE |
| BR112013010310A2 (pt) | 2010-10-29 | 2016-11-29 | Pfizer | inibidores de acetil-coa carboxilase de lactama n1/n2 |
| MY162167A (en) | 2011-04-22 | 2017-05-31 | Pfizer | Substituted acetyl-coa carboxylase inhibitors |
| AU2014262547A1 (en) | 2013-05-10 | 2015-11-26 | Gilead Apollo, Llc | ACC inhibitors and uses thereof |
| EA201591959A1 (ru) * | 2013-05-10 | 2016-03-31 | Нимбус Аполло, Инк. | Ингибиторы акк и их применение |
| MX2015015422A (es) * | 2013-05-10 | 2016-06-21 | Nimbus Apollo Inc | Inhibidores de acetil-coa carboxilasa (acc) y usos de los mismos. |
| SG11201509186TA (en) | 2013-06-27 | 2016-01-28 | Pfizer | Heteroaromatic compounds and their use as dopamine d1 ligands |
| HK1217448A1 (zh) | 2013-09-12 | 2017-01-13 | 辉瑞大药厂 | 乙酰辅酶a羧化酶抑制剂用於治疗寻常痤疮的用途 |
| EP3670496A3 (en) | 2013-10-17 | 2020-09-30 | Shionogi&Co., Ltd. | Acc2 inhibitors |
| JP2016079168A (ja) | 2014-10-17 | 2016-05-16 | 塩野義製薬株式会社 | ９員縮合環誘導体 |
| WO2016084816A1 (ja) * | 2014-11-26 | 2016-06-02 | 武田薬品工業株式会社 | 二環性化合物 |
| US10252997B2 (en) | 2015-03-31 | 2019-04-09 | Takeda Pharmaceutical Company Limited | Monocyclic compound |
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| JPS59196876A (ja) | 1983-04-22 | 1984-11-08 | Sumitomo Chem Co Ltd | １，２，４−オキサジアゾ−ル誘導体、その製造法およびそれを有効成分とする除草剤 |
| WO1986003203A1 (fr) * | 1984-11-22 | 1986-06-05 | Yoshitomi Pharmaceutical Industries, Ltd. | Derives de thienylthiazole |
| CA2044533A1 (en) * | 1990-06-29 | 1991-12-30 | Philippe Guerry | Substituted aminoalkylbiphenyl derivatives |
| WO1995032963A1 (en) * | 1994-06-01 | 1995-12-07 | Yoshitomi Pharmaceutical Industries, Ltd. | Thienylazole compound and thienotriazolodiazepine compound |
| AU3087195A (en) | 1994-08-02 | 1996-03-04 | Nippon Soda Co., Ltd. | Oxazole derivative, process for producing the same, and herbicide |
| AU3264695A (en) * | 1994-08-23 | 1996-03-14 | Nissan Chemical Industries Ltd. | Pyridine derivative |
| DE19536809A1 (de) | 1995-10-02 | 1997-04-03 | Basf Ag | Heterocyclisch substituierte Salicylsäurederivate |
| CA2190699A1 (en) * | 1995-12-08 | 1997-06-09 | Johannes Aebi | Tertiary amines |
| WO1997025319A1 (en) * | 1996-01-05 | 1997-07-17 | Novartis Ag | Substituted 1,2,4,6-thiatriazines useful as herbicides |
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| JPH11171848A (ja) * | 1997-09-26 | 1999-06-29 | Fujirebio Inc | 芳香族アミド誘導体 |
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| EA200400011A1 (ru) | 2001-06-07 | 2004-06-24 | Эли Лилли Энд Компани | Модуляторы рецепторов, активируемых пролифераторами пероксисом (prar) |
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| KR100979988B1 (ko) * | 2001-08-13 | 2010-09-03 | 얀센 파마슈티카 엔.브이. | 2-아미노-4,5-삼치환 티아졸릴 유도체 |
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| JP2005162612A (ja) * | 2002-01-09 | 2005-06-23 | Ajinomoto Co Inc | アシルスルホンアミド誘導体 |
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| NZ534582A (en) * | 2002-02-27 | 2006-03-31 | Pfizer Prod Inc | ACC inhibitors |
| RU2005121907A (ru) * | 2002-12-12 | 2006-02-27 | Галдерма Ресерч Энд Девелопмент, С.Н.С. (Fr) | Новые соединения, являющиеся модуляторами рецепторов типа pparгамма, и их применение в косметических или фармацевтических композициях |
| JP2005272476A (ja) * | 2003-04-09 | 2005-10-06 | Japan Tobacco Inc | 複素芳香５員環化合物及びその医薬用途 |
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| JP2007504229A (ja) * | 2003-09-02 | 2007-03-01 | メルク エンド カムパニー インコーポレーテッド | 代謝調節型グルタミン酸受容体−５のモジュレーターとしてのビピリジルアミン類およびエーテル類 |
| CA2543707A1 (en) | 2003-10-31 | 2005-05-19 | Takeda Pharmaceutical Company Limited | Nitrogen-containing fused heterocyclic compounds |
| WO2005051945A1 (en) | 2003-11-20 | 2005-06-09 | Eli Lilly And Company | Heterocyclic compounds as modulators of peroxisome proliferator activated receptors, useful for the treatment and/or prevention of disorders modulated by a ppar |
| WO2005058876A1 (en) * | 2003-12-16 | 2005-06-30 | Gpc Biotech Ag | Pyrazine derivatives as effective compounds against infectious diseases |
| AU2004309271A1 (en) * | 2003-12-25 | 2005-07-14 | Takeda Pharmaceutical Company Limited | 3-(4-benzyloxyphenyl)propanoic acid derivatives |
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| WO2005113069A2 (en) | 2004-05-14 | 2005-12-01 | Research Development Foundation | Use of circumin and analogues as inhibitors of acc2 |
| KR101195801B1 (ko) | 2004-06-18 | 2012-11-05 | 밀레니엄 파머슈티컬스 인코퍼레이티드 | Ｘａ 인자 억제제 |
| US20050288340A1 (en) * | 2004-06-29 | 2005-12-29 | Pfizer Inc | Substituted heteroaryl- and phenylsulfamoyl compounds |
| JP2006022065A (ja) | 2004-07-09 | 2006-01-26 | Dai Ichi Seiyaku Co Ltd | カルバメート誘導体 |
| DE602005013793D1 (de) * | 2004-07-27 | 2009-05-20 | Astellas Pharma Inc | Thiazolderivate mit vap-1-hemmender wirkung |
| WO2006010637A2 (en) * | 2004-07-30 | 2006-02-02 | Gpc Biotech Ag | Pyridinylamines |
| EP1954696B1 (en) * | 2005-01-19 | 2011-02-23 | Bristol-Myers Squibb Company | 2-phenoxy-n-(1,3,4-thiadizol-2-yl)pyridin-3-amine derivatives and related compounds as p2y1 receptor inhibitors for the treatment of thromboembolic disorders |
| US8748627B2 (en) * | 2006-02-15 | 2014-06-10 | Abbvie Inc. | Acetyl-CoA carboxylase (ACC) inhibitors and their use in diabetes, obesity and metabolic syndrome |
| CA2641673A1 (en) * | 2006-02-15 | 2007-08-23 | Abbott Laboratories | Novel acetyl-coa carboxylase (acc) inhibitors and their use in diabetes, obesity and metabolic syndrome |
| US7928243B2 (en) * | 2006-12-21 | 2011-04-19 | Abbott Laboratories | Acetyl-CoA carboxylase (ACC) inhibitors and their use in diabetes, obesity and metabolic syndrome |
| AU2008287542C1 (en) * | 2007-06-01 | 2015-01-22 | The Trustees Of Princeton University | Treatment of viral infections by modulation of host cell metabolic pathways |
-
2007
- 2007-02-15 CN CN2007800056683A patent/CN101384568B/zh not_active Expired - Fee Related
- 2007-02-15 CA CA002641766A patent/CA2641766A1/en not_active Abandoned
- 2007-02-15 JP JP2008555484A patent/JP2009526868A/ja not_active Ceased
- 2007-02-15 WO PCT/US2007/062181 patent/WO2007095603A2/en not_active Ceased
- 2007-02-15 US US11/675,406 patent/US8735595B2/en not_active Expired - Fee Related
- 2007-02-15 EP EP07757027A patent/EP1991536A2/en not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| CN101384568A (zh) | 2009-03-11 |
| WO2007095603A3 (en) | 2008-03-13 |
| CN101384568B (zh) | 2012-12-12 |
| US8735595B2 (en) | 2014-05-27 |
| WO2007095603A2 (en) | 2007-08-23 |
| EP1991536A2 (en) | 2008-11-19 |
| US20070219251A1 (en) | 2007-09-20 |
| JP2009526868A (ja) | 2009-07-23 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Discontinued |
Effective date: 20150217 |