JP5435592B2 - ピラゾロスピロケトンアセチルＣｏＡカルボキシラーゼ阻害剤 - Google Patents
ピラゾロスピロケトンアセチルＣｏＡカルボキシラーゼ阻害剤 Download PDFInfo
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- JP5435592B2 JP5435592B2 JP2011511101A JP2011511101A JP5435592B2 JP 5435592 B2 JP5435592 B2 JP 5435592B2 JP 2011511101 A JP2011511101 A JP 2011511101A JP 2011511101 A JP2011511101 A JP 2011511101A JP 5435592 B2 JP5435592 B2 JP 5435592B2
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- 229910052739 hydrogen Inorganic materials 0.000 claims description 45
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 42
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 34
- -1 Obinepichido Chemical compound 0.000 claims description 28
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 25
- 150000002431 hydrogen Chemical class 0.000 claims description 23
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 23
- 150000003839 salts Chemical class 0.000 claims description 21
- 238000011282 treatment Methods 0.000 claims description 19
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- 239000000126 substance Substances 0.000 claims description 15
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 12
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
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- ZSBOMTDTBDDKMP-OAHLLOKOSA-N alogliptin Chemical compound C=1C=CC=C(C#N)C=1CN1C(=O)N(C)C(=O)C=C1N1CCC[C@@H](N)C1 ZSBOMTDTBDDKMP-OAHLLOKOSA-N 0.000 claims description 3
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- QCWQNJFTALBBAN-UHFFFAOYSA-N tert-butyl 2-(4-cyano-3-methoxyphenyl)-3-methyl-7-oxospiro[6h-pyrano[3,2-c]pyrazole-5,4'-piperidine]-1'-carboxylate Chemical compound C1=C(C#N)C(OC)=CC(N2C(=C3C(C(CC4(CCN(CC4)C(=O)OC(C)(C)C)O3)=O)=N2)C)=C1 QCWQNJFTALBBAN-UHFFFAOYSA-N 0.000 description 1
- WWCYAKGGKFKHSX-UHFFFAOYSA-N tert-butyl 2-ethyl-3-methyl-7-oxospiro[6h-pyrano[3,2-c]pyrazole-5,4'-piperidine]-1'-carboxylate Chemical compound CC=1N(CC)N=C(C(C2)=O)C=1OC12CCN(C(=O)OC(C)(C)C)CC1 WWCYAKGGKFKHSX-UHFFFAOYSA-N 0.000 description 1
- DYZGSZHJZOSAGW-UHFFFAOYSA-N tert-butyl 2-ethyl-7-oxospiro[6h-pyrano[3,2-c]pyrazole-5,4'-piperidine]-1'-carboxylate Chemical compound C1C(=O)C2=NN(CC)C=C2OC21CCN(C(=O)OC(C)(C)C)CC2 DYZGSZHJZOSAGW-UHFFFAOYSA-N 0.000 description 1
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- MEPJVJVJCPPHRZ-UHFFFAOYSA-N tert-butyl 3-methyl-7-oxo-2-(oxolan-3-yl)spiro[6h-pyrano[3,2-c]pyrazole-5,4'-piperidine]-1'-carboxylate Chemical compound C1C(=O)C2=NN(C3COCC3)C(C)=C2OC21CCN(C(=O)OC(C)(C)C)CC2 MEPJVJVJCPPHRZ-UHFFFAOYSA-N 0.000 description 1
- KYFHAAKLCWNABS-UHFFFAOYSA-N tert-butyl 7-oxo-2-propan-2-ylspiro[6h-pyrano[3,2-c]pyrazole-5,4'-piperidine]-1'-carboxylate Chemical compound C1C(=O)C2=NN(C(C)C)C=C2OC21CCN(C(=O)OC(C)(C)C)CC2 KYFHAAKLCWNABS-UHFFFAOYSA-N 0.000 description 1
- PBALPOBPAIIHQG-UHFFFAOYSA-N tert-butyl 7-oxo-2-propylspiro[6h-pyrano[3,2-c]pyrazole-5,4'-piperidine]-1'-carboxylate Chemical compound C1C(=O)C2=NN(CCC)C=C2OC21CCN(C(=O)OC(C)(C)C)CC2 PBALPOBPAIIHQG-UHFFFAOYSA-N 0.000 description 1
- DDPWVABNMBRBFI-UHFFFAOYSA-N tert-butylhydrazine;hydron;chloride Chemical compound Cl.CC(C)(C)NN DDPWVABNMBRBFI-UHFFFAOYSA-N 0.000 description 1
- WMXCDAVJEZZYLT-UHFFFAOYSA-N tert-butylthiol Chemical compound CC(C)(C)S WMXCDAVJEZZYLT-UHFFFAOYSA-N 0.000 description 1
- CBXCPBUEXACCNR-UHFFFAOYSA-N tetraethylammonium Chemical compound CC[N+](CC)(CC)CC CBXCPBUEXACCNR-UHFFFAOYSA-N 0.000 description 1
- DQLXXYMNINXQSV-QTRRCMKVSA-J tetralithium;[(2r,3s,4r,5r)-5-(6-aminopurin-9-yl)-2-[[[[(3r)-4-[[3-[2-(2-carboxyacetyl)sulfanylethylamino]-3-oxopropyl]amino]-3-hydroxy-2,2-dimethyl-4-oxobutoxy]-oxidophosphoryl]oxy-oxidophosphoryl]oxymethyl]-4-hydroxyoxolan-3-yl] phosphate Chemical compound [Li+].[Li+].[Li+].[Li+].O[C@@H]1[C@H](OP([O-])([O-])=O)[C@@H](COP([O-])(=O)OP([O-])(=O)OCC(C)(C)[C@@H](O)C(=O)NCCC(=O)NCCSC(=O)CC(O)=O)O[C@H]1N1C2=NC=NC(N)=C2N=C1 DQLXXYMNINXQSV-QTRRCMKVSA-J 0.000 description 1
- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
- 238000010257 thawing Methods 0.000 description 1
- 210000001685 thyroid gland Anatomy 0.000 description 1
- AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 1
- 238000003354 tissue distribution assay Methods 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 230000004102 tricarboxylic acid cycle Effects 0.000 description 1
- 150000003627 tricarboxylic acid derivatives Chemical class 0.000 description 1
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
- 229910052905 tridymite Inorganic materials 0.000 description 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-O triethylammonium ion Chemical compound CC[NH+](CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-O 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
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- 208000035408 type 1 diabetes mellitus 1 Diseases 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
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- 230000004584 weight gain Effects 0.000 description 1
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- 230000004580 weight loss Effects 0.000 description 1
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- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/12—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains three hetero rings
- C07D491/20—Spiro-condensed systems
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
-
- 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
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Emergency Medicine (AREA)
- Endocrinology (AREA)
- Child & Adolescent Psychology (AREA)
- Gastroenterology & Hepatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines Containing Plant Substances (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (7)
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| US5665208P | 2008-05-28 | 2008-05-28 | |
| US61/056,652 | 2008-05-28 | ||
| US5868908P | 2008-06-04 | 2008-06-04 | |
| US61/058,689 | 2008-06-04 | ||
| US17151909P | 2009-04-22 | 2009-04-22 | |
| US61/171,519 | 2009-04-22 | ||
| PCT/IB2009/005649 WO2009144554A1 (en) | 2008-05-28 | 2009-05-18 | Pyrazolospiroketone acetyl-c0a carboxylase inhibitors |
Publications (3)
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| JP2011521939A JP2011521939A (ja) | 2011-07-28 |
| JP2011521939A5 JP2011521939A5 (cg-RX-API-DMAC7.html) | 2012-07-05 |
| JP5435592B2 true JP5435592B2 (ja) | 2014-03-05 |
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| ES (1) | ES2545231T3 (cg-RX-API-DMAC7.html) |
| WO (1) | WO2009144554A1 (cg-RX-API-DMAC7.html) |
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| WO2009144554A1 (en) | 2008-05-28 | 2009-12-03 | Pfizer, Inc. | Pyrazolospiroketone acetyl-c0a carboxylase inhibitors |
| PT2499139E (pt) * | 2009-11-10 | 2014-02-10 | Pfizer | Inibidores de n1-pirazolospirocetona acetil-coa carboxilase |
| PL2547679T3 (pl) | 2010-03-19 | 2016-02-29 | Pfizer | Pochodne 2,3-dihydro-1H-inden-1-ylo-2,7-diazaspiro[3.5]nonanu i ich zastosowanie jako antagonistów lub odwrotnych agonistów receptora greliny |
| EP2595989B1 (en) | 2010-05-06 | 2016-07-13 | Vertex Pharmaceuticals Incorporated | Heterocyclic chromene-spirocyclic piperidine amides as modulators of ion channels |
| SI2621493T1 (sl) | 2010-09-30 | 2016-10-28 | Pfizer Inc. | Zaviralci N1-pirazolospiroketon acetil-CoA-karboksilaze |
| MX2013004733A (es) * | 2010-10-29 | 2013-07-02 | Pfizer | Inhibidores de n1/n2-lactama acetil-coa carboxilasa. |
| PL2670752T3 (pl) | 2011-02-02 | 2016-09-30 | Pirolopirazynowe spirocykliczne piperydynoamidy jako modulatory kanałów jonowych | |
| MX2013009393A (es) * | 2011-02-18 | 2013-08-29 | Vertex Pharma | Piperidinamidas cromano-espirociclicas como moduladores de canales de iones. |
| ES2618929T3 (es) | 2011-03-14 | 2017-06-22 | Vertex Pharmaceuticals Incorporated | Morfolina-Spiro piperidina amida cíclica como moduladores del canal iónico |
| HRP20151397T1 (hr) * | 2011-04-22 | 2016-01-15 | Pfizer Inc. | DERIVATI PIRAZOLOSPIROKETONA, NAMIJENJENI UPOTREBI KAO INHIBITORI ACETIL-CoA-KARBOKSILAZE |
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| JP2025541334A (ja) | 2022-12-16 | 2025-12-18 | シンジェンタ クロップ プロテクション アクチェンゲゼルシャフト | ベンズイミダゾール誘導体 |
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| US7105526B2 (en) | 2002-06-28 | 2006-09-12 | Banyu Pharmaceuticals Co., Ltd. | Benzimidazole derivatives |
| WO2004092179A1 (ja) | 2003-04-14 | 2004-10-28 | Nippon Soda Co. Ltd. | スピロ誘導体、製造法および抗酸化薬 |
| JP2005119987A (ja) | 2003-10-15 | 2005-05-12 | Ajinomoto Co Inc | アシルスルホンアミド誘導体 |
| US20050267221A1 (en) | 2004-05-14 | 2005-12-01 | Research Development Foundation | Use of curcumin and analogues thereof as inhibitors of ACC2 |
| BRPI0613427A2 (pt) * | 2005-07-19 | 2012-10-30 | Merck & Co Inc | composto ou seu sal ou éster, composição farmacêutica, agente terapêutico, e , uso do composto ou seu sal ou éster |
| CA2617042A1 (en) | 2005-07-29 | 2007-02-01 | Takeda Pharmaceutical Company Limited | Spiro-cyclic compound |
| DE102006016566B4 (de) * | 2005-09-22 | 2008-06-12 | Beru Ag | Zusammengesetzter Leiter, insbesondere für Glühkerzen für Dieselmotoren |
| ATE493412T1 (de) | 2005-11-18 | 2011-01-15 | Merck Sharp & Dohme | Spirohydantoin-aryl-cgrp-rezeptorantagonisten |
| JP2009526868A (ja) | 2006-02-15 | 2009-07-23 | アボット・ラボラトリーズ | 新規なアセチル−ＣｏＡカルボキシラーゼ（ＡＣＣ）阻害薬およびこれらの糖尿病、肥満および代謝症候群における使用 |
| ATE552262T1 (de) | 2006-11-29 | 2012-04-15 | Pfizer Prod Inc | Spiroketone als inhibitoren von acetyl-coa- carboxylase |
| PE20081559A1 (es) | 2007-01-12 | 2008-11-20 | Merck & Co Inc | DERIVADOS DE ESPIROCROMANONA SUSTITUIDOS COMO INHIBIDORES DE ACETIL CoA CARBOXILASA |
| US20100113418A1 (en) | 2007-02-20 | 2010-05-06 | Takeda Pharmaceutical Company Limited | Heterocyclic compound |
| EP2195321B1 (en) | 2007-04-12 | 2016-10-19 | Pfizer Inc. | 3-amido-pyrrolo[3,4-c]pyrazole-5(1h, 4h,6h) carbaldehyde derivatives as inhibitors of protein kinase c |
| US7981904B2 (en) * | 2008-03-20 | 2011-07-19 | Takeda Pharmaceutical Company Limited | Acetyl CoA carboxylase inhibitors |
| US20110009443A1 (en) | 2008-05-28 | 2011-01-13 | Kevin Daniel Freeman-Cook | Pyrazolospiroketone Acetyl-Coa Carboxylase Inhibitors |
| WO2009144554A1 (en) | 2008-05-28 | 2009-12-03 | Pfizer, Inc. | Pyrazolospiroketone acetyl-c0a carboxylase inhibitors |
| JP5501256B2 (ja) | 2008-07-04 | 2014-05-21 | Ｍｓｄ株式会社 | 新規スピロクロマノンカルボン酸 |
| JP2011528034A (ja) * | 2008-07-14 | 2011-11-10 | クロップソリューション，インコーポレイテッド | アセチル−補酵素カルボキシラーゼの修飾因子およびその使用方法 |
| PT2499139E (pt) | 2009-11-10 | 2014-02-10 | Pfizer | Inibidores de n1-pirazolospirocetona acetil-coa carboxilase |
| WO2011058473A1 (en) | 2009-11-10 | 2011-05-19 | Pfizer Inc. | N2-pyrazolospiroketone acetyl-coa carboxylase inhibitors |
| SI2621493T1 (sl) | 2010-09-30 | 2016-10-28 | Pfizer Inc. | Zaviralci N1-pirazolospiroketon acetil-CoA-karboksilaze |
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| CA2724774C (en) | 2013-06-25 |
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| EP2297163A1 (en) | 2011-03-23 |
| JP2011521939A (ja) | 2011-07-28 |
| EP2297163B1 (en) | 2015-07-08 |
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