RU2540337C2 - N1/N2-ЛАКТАМНЫЕ ИНГИБИТОРЫ АЦЕТИЛ-КоА-КАРБОКСИЛАЗ - Google Patents
N1/N2-ЛАКТАМНЫЕ ИНГИБИТОРЫ АЦЕТИЛ-КоА-КАРБОКСИЛАЗ Download PDFInfo
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- RU2540337C2 RU2540337C2 RU2013116924/04A RU2013116924A RU2540337C2 RU 2540337 C2 RU2540337 C2 RU 2540337C2 RU 2013116924/04 A RU2013116924/04 A RU 2013116924/04A RU 2013116924 A RU2013116924 A RU 2013116924A RU 2540337 C2 RU2540337 C2 RU 2540337C2
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- mmol
- tert
- reaction mixture
- methyl
- carboxylic acid
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- 229940121373 acetyl-coa carboxylase inhibitor Drugs 0.000 title description 6
- 150000001875 compounds Chemical class 0.000 claims abstract description 293
- 150000003839 salts Chemical class 0.000 claims abstract description 52
- 102000000452 Acetyl-CoA carboxylase Human genes 0.000 claims abstract description 27
- 108010016219 Acetyl-CoA carboxylase Proteins 0.000 claims abstract description 27
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 17
- 239000001257 hydrogen Substances 0.000 claims abstract description 15
- 125000001624 naphthyl group Chemical group 0.000 claims abstract description 12
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 9
- 125000001309 chloro group Chemical group Cl* 0.000 claims abstract description 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims abstract description 5
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims abstract description 5
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 5
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims abstract description 5
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims abstract description 4
- 230000002401 inhibitory effect Effects 0.000 claims description 16
- 239000003085 diluting agent Substances 0.000 claims description 13
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- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 432
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- 238000000034 method Methods 0.000 description 68
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- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 56
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- C07D471/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains three hetero rings
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| US11325909B2 (en) | 2017-11-21 | 2022-05-10 | Pfizer Inc. | Crystalline 2-amino-2-(hydroxymethyl)propane-1,3-diol salt of 4-(4-(1-isopropyl-7-OXO-1,4,6,7-tetrahydrospiro[indazole-5,4′-piperidine]-1′-carbonyl)-6-methoxypryridin-2-YL)benzoic acid |
Families Citing this family (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PL2632925T3 (pl) * | 2010-10-29 | 2015-10-30 | Pfizer | N1/N2-laktamowe inhibitory karboksylazy acetylo-CoA |
| PT2953942T (pt) | 2013-02-06 | 2018-01-17 | Bayer Cropscience Ag | Derivados de pirazol substituídos com halogéneo como agentes pesticidas |
| US8652527B1 (en) | 2013-03-13 | 2014-02-18 | Upsher-Smith Laboratories, Inc | Extended-release topiramate capsules |
| US9101545B2 (en) | 2013-03-15 | 2015-08-11 | Upsher-Smith Laboratories, Inc. | Extended-release topiramate capsules |
| CN103214327A (zh) * | 2013-03-22 | 2013-07-24 | 郑州泰基鸿诺药物科技有限公司 | 一种芳香环或芳杂环三氟甲基酮化合物及其制备方法 |
| CN104230922B (zh) | 2013-06-19 | 2016-12-28 | 中国科学院上海药物研究所 | 一类五元杂环并吡啶类化合物及其制备方法和用途 |
| BR112016004118A2 (pt) | 2013-09-12 | 2017-10-17 | Pfizer | uso de inibidores da acetil-coa carboxilase para tratamento de acne vulgar |
| BR112016017527B1 (pt) | 2014-01-03 | 2021-01-05 | Bayer Animal Health Gmbh | compostos, usos de compostos, composições farmacêuticas, processo para produzir composições e método não terapêutico para controlar pragas |
| CN104844509A (zh) * | 2014-02-14 | 2015-08-19 | 河南工业大学 | 一种条件温和无金属参与的胺基喹啉衍生物的制备方法 |
| KR101731624B1 (ko) * | 2014-07-01 | 2017-05-04 | 광주과학기술원 | 세포 리프로그래밍 유도용 조성물 |
| CN106749002A (zh) * | 2015-02-12 | 2017-05-31 | 佛山市赛维斯医药科技有限公司 | 一种含硝基喹啉结构的葡萄糖激酶活化剂及其用途 |
| WO2016142394A1 (de) | 2015-03-10 | 2016-09-15 | Bayer Animal Health Gmbh | Pyrazolyl-derivate als schädlingsbekämpfungsmittel |
| IL243707A0 (en) | 2016-01-20 | 2016-05-01 | Galmed Res And Dev Ltd | Treatment to regulate the microbiota in the intestine |
| US11197870B2 (en) | 2016-11-10 | 2021-12-14 | Galmed Research And Development Ltd | Treatment for hepatic fibrosis |
| UA125592C2 (uk) | 2017-03-16 | 2022-04-27 | Джянгсу Хенгруй Медісін Ко., Лтд. | ПОХІДНА ГЕТЕРОАРИЛ[4,3-c]ПІРИМІДИН-5-АМІНУ, СПОСІБ ЇЇ ОТРИМАННЯ ТА ЇЇ МЕДИЧНІ ЗАСТОСУВАННЯ |
| WO2018170200A1 (en) | 2017-03-16 | 2018-09-20 | Celgene Car Llc | Heteroaryl compounds useful as mk2 inhibitors |
| MX387359B (es) | 2017-03-16 | 2025-03-18 | Bristol Myers Squibb Co | Inhibidores de cinasa activada por mitógeno 2 (mk2), síntesis de los mismos, e intermediarios de los mismos. |
| JP7129420B6 (ja) | 2017-03-30 | 2024-02-02 | エフ・ホフマン-ラ・ロシュ・アクチェンゲゼルシャフト | Hpk1阻害剤としてのイソキノリン |
| TW202019905A (zh) | 2018-07-24 | 2020-06-01 | 瑞士商赫孚孟拉羅股份公司 | 異喹啉化合物及其用途 |
| TW202024053A (zh) | 2018-10-02 | 2020-07-01 | 美商建南德克公司 | 異喹啉化合物及其用途 |
| US11612606B2 (en) | 2018-10-03 | 2023-03-28 | Genentech, Inc. | 8-aminoisoquinoline compounds and uses thereof |
| CN109824669A (zh) * | 2018-12-21 | 2019-05-31 | 西南大学 | 哌啶螺环酒石酸类化合物制备及应用 |
| WO2021231191A1 (en) * | 2020-05-12 | 2021-11-18 | Merck Sharp & Dohme Corp. | Factor xi activation inhibitors |
| CN115666558A (zh) * | 2020-05-21 | 2023-01-31 | 盐野义制药株式会社 | 脂肪性肝病的治疗用药物 |
| CN116670142A (zh) | 2021-02-01 | 2023-08-29 | 细胞基因公司 | Mk2抑制剂、其合成和其中间体 |
| WO2022272036A1 (en) * | 2021-06-25 | 2022-12-29 | Cedilla Therapeutics, Inc. | Tead inhibitors and uses thereof |
| CN120019059A (zh) * | 2022-07-29 | 2025-05-16 | 辉瑞公司 | 新型acc抑制剂 |
| WO2024213044A1 (en) * | 2023-04-14 | 2024-10-17 | Beijing Double-Crane Runchuang Technology Co., Ltd. | Azacyclo-carbonyl-fused ring derivatives and use thereof |
| WO2025036472A1 (en) * | 2023-08-16 | 2025-02-20 | Pharmaengine, Inc. | Spirocyclic mta-cooperative prmts inhibitor |
| WO2025190395A2 (en) * | 2024-03-14 | 2025-09-18 | Pharmaengine, Inc. | Mta-cooperative prmt5 inhibitor |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EA200900613A1 (ru) * | 2006-11-29 | 2009-10-30 | Пфайзер Продактс Инк. | Спирокетоновые ингибиторы ацетил-коа-карбоксилаз |
| EP2123652A1 (en) * | 2007-02-20 | 2009-11-25 | Takeda Pharmaceutical Company Limited | Heterocyclic compound |
Family Cites Families (41)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2002100A (en) | 1932-06-27 | 1935-05-21 | Smith Sheffield | Shock absorber |
| JPS4925673B1 (enExample) * | 1970-05-22 | 1974-07-02 | ||
| EP0901786B1 (en) | 1997-08-11 | 2007-06-13 | Pfizer Products Inc. | Solid pharmaceutical dispersions with enhanced bioavailability |
| JP4104983B2 (ja) | 2001-02-28 | 2008-06-18 | メルク エンド カムパニー インコーポレーテッド | メラノコルチン−4受容体作動薬としてのアシル化ピペリジン誘導体 |
| BR0212123A (pt) | 2001-08-24 | 2004-07-20 | Upjohn Co | 7-aza[2.2.1]biciclo-heptanos substituìdos com arila para o tratamento de doenças |
| MXPA04007083A (es) | 2002-02-20 | 2004-10-29 | Upjohn Co | Compuestos azabiciclicos para el tratamiento de enfermedades. |
| EP1478437B1 (en) | 2002-02-27 | 2005-08-31 | Pfizer Products Inc. | Acc inhibitors |
| US7105526B2 (en) | 2002-06-28 | 2006-09-12 | Banyu Pharmaceuticals Co., Ltd. | Benzimidazole derivatives |
| JPWO2004092179A1 (ja) | 2003-04-14 | 2006-07-06 | 日本曹達株式会社 | 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 |
| ES2327857T3 (es) | 2004-05-12 | 2009-11-04 | Pfizer Products Inc. | Derivados de prolina y su uso como inhibidores de la dipeptidil peptidasa iv. |
| US20050267221A1 (en) | 2004-05-14 | 2005-12-01 | Research Development Foundation | Use of curcumin and analogues thereof as inhibitors of ACC2 |
| BRPI0510273A (pt) | 2004-05-25 | 2007-10-30 | Pfizer Prod Inc | derivados de tetraazabenzo[e]azuleno e análogos destes |
| PA8660701A1 (es) | 2005-02-04 | 2006-09-22 | Pfizer Prod Inc | Agonistas de pyy y sus usos |
| US7410976B2 (en) | 2005-07-19 | 2008-08-12 | Merck & Co., Inc. | Spirochromanone derivatives |
| EP1911753A1 (en) | 2005-07-29 | 2008-04-16 | Takeda Pharmaceutical Company Limited | Spiro-cyclic compound |
| EP1951251B1 (en) | 2005-11-18 | 2010-12-29 | Merck Sharp & Dohme Corp. | Spirohydantoin aryl cgrp receptor antagonists |
| CN101384568B (zh) | 2006-02-15 | 2012-12-12 | 雅培制药有限公司 | 乙酰辅酶a羧化酶(acc)抑制剂及其在糖尿病、肥胖症和代谢综合征中的应用 |
| NL2000581C2 (nl) | 2006-04-20 | 2008-01-03 | Pfizer Prod Inc | Aangecondenseerde fenylamidoheterocyclische verbindingen. |
| PE20081559A1 (es) | 2007-01-12 | 2008-11-20 | Merck & Co Inc | DERIVADOS DE ESPIROCROMANONA SUSTITUIDOS COMO INHIBIDORES DE ACETIL CoA CARBOXILASA |
| JP5404601B2 (ja) | 2007-04-12 | 2014-02-05 | ファイザー・インク | 新規な3−アミド−ピロロ[3,4−c]ピラゾール−5(1H,4H,6H)カルバルデヒド誘導体 |
| US20090036425A1 (en) | 2007-08-02 | 2009-02-05 | Pfizer Inc | Substituted bicyclolactam compounds |
| US7981904B2 (en) | 2008-03-20 | 2011-07-19 | Takeda Pharmaceutical Company Limited | Acetyl CoA carboxylase inhibitors |
| EP2297164A1 (en) | 2008-05-28 | 2011-03-23 | Pfizer Inc. | Pyrazolospiroketone acetyl-coa carboxylase inhibitors |
| EP2297163B1 (en) | 2008-05-28 | 2015-07-08 | Pfizer Inc. | Pyrazolospiroketone acetyl-CoA carboxylase inhibitors |
| WO2010002010A1 (en) | 2008-07-04 | 2010-01-07 | Banyu Pharmaceutical Co.,Ltd. | Novel spirochromanone carboxylic acids |
| US8110570B2 (en) | 2008-07-14 | 2012-02-07 | Cropsolution, Inc. | Modulators of acetyl-coenzyme A carboxylase and methods of use thereof |
| WO2010013161A1 (en) | 2008-07-29 | 2010-02-04 | Pfizer Inc. | Fluorinated heteroaryls |
| ATE540040T1 (de) | 2008-08-28 | 2012-01-15 | Pfizer | Dioxabicycloä3.2.1üoctan-2,3,4-triolderivate |
| WO2010086820A1 (en) | 2009-02-02 | 2010-08-05 | Pfizer Inc. | 4-amino-5-oxo-7, 8-dihydropyrimido [5,4-f] [1,4] oxazepin-6 (5h) -yl) phenyl derivatives, pharmaceutical compositions and uses thereof |
| EP2406230A1 (en) | 2009-03-11 | 2012-01-18 | Pfizer Inc. | Substituted indazole amides and their use as glucokinase activators |
| UA99882C2 (uk) | 2009-03-11 | 2012-10-10 | Пфайзер Інк. | Похідні бензофуранілу, фармацевтична композиція та спосіб лікування захворювань (варіанти) |
| WO2010106457A2 (en) | 2009-03-20 | 2010-09-23 | Pfizer Inc. | 3-oxa-7-azabicyclo[3.3.1]nonanes |
| EP2427448A1 (en) | 2009-05-08 | 2012-03-14 | Pfizer Inc. | Gpr 119 modulators |
| WO2010128425A1 (en) | 2009-05-08 | 2010-11-11 | Pfizer Inc. | Gpr 119 modulators |
| NZ596467A (en) | 2009-06-05 | 2014-01-31 | Pfizer | L- ( piperidin-4-yl) -pyrazole derivatives as gpr 119 modulators |
| WO2011005611A1 (en) | 2009-07-09 | 2011-01-13 | Merck Sharp & Dohme Corp. | Neuromedin u receptor agonists and uses thereof |
| CA2778886C (en) | 2009-11-10 | 2014-01-07 | Pfizer Inc. | N1-pyrazolospiroketone acetyl-coa carboxylase inhibitors |
| CA2778316A1 (en) * | 2009-11-10 | 2011-05-19 | Pfizer Inc. | N-2 pyrazolospiroketone acetyl-coa carboxylase inhibitors |
| PT2621493T (pt) | 2010-09-30 | 2016-11-14 | Pfizer | Inibidores de n1-pirazolospirocetona acetil-coa carboxilase |
| PL2632925T3 (pl) * | 2010-10-29 | 2015-10-30 | Pfizer | N1/N2-laktamowe inhibitory karboksylazy acetylo-CoA |
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Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EA200900613A1 (ru) * | 2006-11-29 | 2009-10-30 | Пфайзер Продактс Инк. | Спирокетоновые ингибиторы ацетил-коа-карбоксилаз |
| EP2123652A1 (en) * | 2007-02-20 | 2009-11-25 | Takeda Pharmaceutical Company Limited | Heterocyclic compound |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US11325909B2 (en) | 2017-11-21 | 2022-05-10 | Pfizer Inc. | Crystalline 2-amino-2-(hydroxymethyl)propane-1,3-diol salt of 4-(4-(1-isopropyl-7-OXO-1,4,6,7-tetrahydrospiro[indazole-5,4′-piperidine]-1′-carbonyl)-6-methoxypryridin-2-YL)benzoic acid |
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