RU2445957C2 - Аналоги тиазолидиндиона - Google Patents
Аналоги тиазолидиндиона Download PDFInfo
- Publication number
- RU2445957C2 RU2445957C2 RU2008140943/15A RU2008140943A RU2445957C2 RU 2445957 C2 RU2445957 C2 RU 2445957C2 RU 2008140943/15 A RU2008140943/15 A RU 2008140943/15A RU 2008140943 A RU2008140943 A RU 2008140943A RU 2445957 C2 RU2445957 C2 RU 2445957C2
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- RU
- Russia
- Prior art keywords
- group
- compound
- alkyl
- aliphatic
- heteroaryl
- Prior art date
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- 150000001467 thiazolidinediones Chemical class 0.000 title abstract description 9
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 24
- 238000000034 method Methods 0.000 claims description 21
- 229940125904 compound 1 Drugs 0.000 claims description 12
- 208000032928 Dyslipidaemia Diseases 0.000 claims description 7
- 208000017170 Lipid metabolism disease Diseases 0.000 claims description 7
- 150000001875 compounds Chemical class 0.000 abstract description 142
- 102000000536 PPAR gamma Human genes 0.000 abstract description 45
- 108010016731 PPAR gamma Proteins 0.000 abstract description 45
- 230000000694 effects Effects 0.000 abstract description 22
- 238000011282 treatment Methods 0.000 abstract description 22
- 230000004913 activation Effects 0.000 abstract description 21
- 239000003814 drug Substances 0.000 abstract description 15
- 239000000126 substance Substances 0.000 abstract description 15
- 102000040945 Transcription factor Human genes 0.000 abstract description 4
- 108091023040 Transcription factor Proteins 0.000 abstract description 4
- 239000000556 agonist Substances 0.000 abstract description 4
- 230000002411 adverse Effects 0.000 abstract description 2
- 230000003247 decreasing effect Effects 0.000 abstract 1
- -1 DPP-4 Chemical compound 0.000 description 94
- 125000001931 aliphatic group Chemical group 0.000 description 75
- 125000001072 heteroaryl group Chemical group 0.000 description 66
- 125000000217 alkyl group Chemical group 0.000 description 64
- 125000003118 aryl group Chemical group 0.000 description 63
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 45
- 239000000203 mixture Substances 0.000 description 40
- NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 description 34
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 33
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- 125000001424 substituent group Chemical group 0.000 description 27
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- 229910052736 halogen Inorganic materials 0.000 description 22
- 150000002367 halogens Chemical class 0.000 description 22
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 21
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- NVBFHJWHLNUMCV-UHFFFAOYSA-N sulfamide Chemical compound NS(N)(=O)=O NVBFHJWHLNUMCV-UHFFFAOYSA-N 0.000 description 10
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 10
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- 206010022489 Insulin Resistance Diseases 0.000 description 9
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 9
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 9
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- 150000003626 triacylglycerols Chemical class 0.000 description 9
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 description 8
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- 125000002541 furyl group Chemical group 0.000 description 8
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 8
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- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 7
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- 125000000392 cycloalkenyl group Chemical group 0.000 description 7
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- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 5
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| US8304441B2 (en) | 2007-09-14 | 2012-11-06 | Metabolic Solutions Development Company, Llc | Thiazolidinedione analogues for the treatment of metabolic diseases |
| US8722710B2 (en) | 2007-09-26 | 2014-05-13 | Deuterx, Llc | Deuterium-enriched pioglitazone |
| US8846315B2 (en) | 2008-08-12 | 2014-09-30 | Zinfandel Pharmaceuticals, Inc. | Disease risk factors and methods of use |
| PE20110565A1 (es) | 2008-08-12 | 2011-09-02 | Zinfandel Pharmaceuticals Inc | Metodo de identificacion de factores de riesgo de la enfermedad |
| CA2783556C (en) * | 2009-12-15 | 2017-12-12 | Metabolic Solutions Development Company, Llc | Ppar-sparing thiazolidinediones and combinations for the treatment of neurodegenerative diseases |
| HUE038042T2 (hu) * | 2009-12-15 | 2018-09-28 | Cirius Therapeutics Inc | PPAR helyettesítõ tiazolidindion sók metabolikus betegségek kezelésére |
| KR20120092712A (ko) * | 2009-12-15 | 2012-08-21 | 메타볼릭 솔루션스 디벨롭먼트 컴퍼니, 엘엘씨 | 진성 당뇨병 및 다른 대사성 질환의 치료를 위한 ｐｐａｒ 절약형 티아졸리딘디온 및 복합제 |
| AU2014202074B2 (en) * | 2009-12-15 | 2016-01-07 | Cirius Therapeutics, Inc. | PPAR-sparing thiazolidinediones and combinations for the treatment of neurodegenerative diseases |
| GB201002224D0 (en) | 2010-02-10 | 2010-03-31 | Argenta Therapeutics Ltd | Respiratory disease treatment |
| GB2477743A (en) * | 2010-02-10 | 2011-08-17 | Argenta Therapeutics Ltd | Enantiomers of 5-methyl-thiazolidine-2,4-dione glitazone compounds |
| AU2011242955A1 (en) * | 2010-04-19 | 2012-11-01 | Metabolic Solutions Development Company, Llc | Novel synthesis for thiazolidinedione compounds |
| EP2560956B1 (en) | 2010-04-19 | 2016-10-26 | Octeta Therapeutics, LLC | Novel synthesis for thiazolidinedione compounds |
| HUE031424T2 (en) | 2010-08-10 | 2017-07-28 | Octeta Therapeutics Llc | New synthesis of thiazolidinedione compounds |
| PL2603507T3 (pl) * | 2010-08-10 | 2016-12-30 | Synteza związków tiazolidynodionu | |
| EA201391017A1 (ru) | 2011-01-10 | 2014-04-30 | Зинфандел Фармасьютикалз, Инк. | Способы и готовые лекарственные формы для лечения болезни альцгеймера |
| US20140065099A1 (en) * | 2011-02-15 | 2014-03-06 | Ecole Polytechnique Federale De Lausanne (Epfl) | Methods of Treating Mitochondrial Dysfunction |
| WO2012149083A1 (en) * | 2011-04-28 | 2012-11-01 | Metabolic Solutions Development Company, Llc | Ppar-sparing thiazolidinediones for the treatment of kidney related diseases |
| KR20130015932A (ko) * | 2011-08-05 | 2013-02-14 | 연세대학교 산학협력단 | 저용량의 치아졸리딘다이온을 포함하는 알츠하이머 병 치료용 약학조성물 |
| KR101501375B1 (ko) | 2012-09-21 | 2015-03-10 | 가톨릭대학교 산학협력단 | 메트포민을 유효성분으로 함유하는 염증성 장질환의 예방 또는 치료용 조성물 |
| WO2014046474A2 (ko) * | 2012-09-21 | 2014-03-27 | 가톨릭대학교 산학협력단 | 메트포민을 유효성분으로 함유하는 염증성 장질환의 예방 또는 치료용 조성물 |
| EP2931274A1 (en) * | 2012-12-11 | 2015-10-21 | Metabolic Solutions Development Company LLC | Ppar-sparing thiazolidinediones and combinations for the treatment of neurodegenerative diseases |
| JP6800013B2 (ja) * | 2013-03-14 | 2020-12-16 | ポクセル・ソシエテ・アノニムＰｏｘｅｌ ＳＡ | 重水素化２，４−チアゾリジンジオン及び治療方法 |
| JP6498195B2 (ja) | 2013-07-22 | 2019-04-10 | メタボリック ソリューションズ ディベロップメント カンパニー， エルエルシー | 代謝疾患を処置するためのｐｐａｒ節約化合物 |
| US10188639B2 (en) | 2014-01-15 | 2019-01-29 | Deuterx, Llc | Methods of treating neurological, metabolic, and other disorders using enantiopure deuterium-enriched pioglitazone |
| SG11201608218QA (en) * | 2014-04-02 | 2016-10-28 | Minoryx Therapeutics S L | 2,4-thiazolidinedione derivatives in the treatment of central nervous system disorders |
| AU2017370003B2 (en) | 2016-12-01 | 2023-04-13 | Minoryx Therapeutics S.L. | 5-[[4-[2-[5-(1-hydroxyethyl)pyridin-2-yl]ethoxy]phenyl]methyl]-1,3-thiazolidine- 2,4-dione for treating nonalcoholic fatty liver disease |
| US11767317B1 (en) | 2020-06-30 | 2023-09-26 | Poxel Sa | Methods of synthesizing enantiopure deuterium-enriched pioglitazone |
| US11319313B2 (en) | 2020-06-30 | 2022-05-03 | Poxel Sa | Crystalline forms of deuterium-enriched pioglitazone |
| GB202210503D0 (en) | 2022-07-18 | 2022-08-31 | Univ Court Univ Of Glasgow | Materials and methods for treatment of chronic myeloid leukemia (CML) |
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| RU2195282C2 (ru) * | 1993-09-15 | 2002-12-27 | Санкио Компани Лимитед | Применение тиазолидиндионов для предотвращения или отдаления наступления инсулиннезависимого сахарного диабета (niddm) |
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| JPS5522636A (en) | 1978-08-04 | 1980-02-18 | Takeda Chem Ind Ltd | Thiazoliding derivative |
| WO1985004170A1 (fr) * | 1984-03-21 | 1985-09-26 | Takeda Chemical Industries, Ltd. | Derives de thiazolidinedione, leur procede de preparation et compositions medicinales les contenant |
| US4582839A (en) * | 1984-03-21 | 1986-04-15 | Takeda Chemical Industries, Ltd. | 2,4-thiazolidinediones |
| CN1003445B (zh) * | 1984-10-03 | 1989-03-01 | 武田药品工业株式会社 | 噻唑烷二酮衍生物，其制备方法和用途 |
| WO1986002073A1 (fr) | 1984-10-03 | 1986-04-10 | Takeda Chemical Industries, Ltd. | Derives de thiazolidinedione, procede de preparation et composition pharmaceutique les contenant |
| AR240698A1 (es) * | 1985-01-19 | 1990-09-28 | Takeda Chemical Industries Ltd | Procedimiento para preparar compuestos de 5-(4-(2-(5-etil-2-piridil)-etoxi)benzil)-2,4-tiazolidindiona y sus sales |
| US5167228A (en) * | 1987-06-26 | 1992-12-01 | Brigham And Women's Hospital | Assessment and modification of endogenous circadian phase and amplitude |
| US5304121A (en) | 1990-12-28 | 1994-04-19 | Boston Scientific Corporation | Drug delivery system making use of a hydrogel polymer coating |
| US5441971A (en) * | 1991-04-11 | 1995-08-15 | The Upjohn Company | Thiazolidinedione derivatives, production and use thereof |
| WO1992018501A1 (en) * | 1991-04-11 | 1992-10-29 | The Upjohn Company | Thiazolidinedione derivatives, production and use thereof |
| NO302471B1 (no) | 1991-12-26 | 1998-03-09 | Sankyo Co | Tiazolidinforbindelser og farmasöytisk preparat |
| US5716981A (en) | 1993-07-19 | 1998-02-10 | Angiogenesis Technologies, Inc. | Anti-angiogenic compositions and methods of use |
| US6099562A (en) | 1996-06-13 | 2000-08-08 | Schneider (Usa) Inc. | Drug coating with topcoat |
| TW438587B (en) | 1995-06-20 | 2001-06-07 | Takeda Chemical Industries Ltd | A pharmaceutical composition for prophylaxis and treatment of diabetes |
| US5798375A (en) | 1995-07-03 | 1998-08-25 | Sankyo Company, Limited | Treatment of arteriosclerosis and xanthoma |
| GB0030845D0 (en) * | 2000-12-18 | 2001-01-31 | Smithkline Beecham Plc | Novel treatment |
| AU2002311057A1 (en) | 2001-04-26 | 2002-11-11 | Leciva, A.S. | Method for obtaining pioglitazone as an antidiabetic agent |
| US20070054902A1 (en) * | 2003-12-02 | 2007-03-08 | Shionogi & Co., Ltd. | Isoxazole derivatives as peroxisome proliferator-activated receptors agonists |
| MX2008011870A (es) * | 2006-03-16 | 2009-02-10 | Metabolic Solutions Dev Compan | Terapias de combinacion de analogos de tiazolidindiona y agonistas glucocorticoides. |
| ES2388555T3 (es) | 2006-03-16 | 2012-10-16 | Metabolic Solutions Development Company Llc | Análogos de tiazolidindiona |
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| NZ597381A (en) | 2007-09-14 | 2013-03-28 | Metabolic Solutions Dev Co Llc | Thiazolidinedione analogues for the treatment of diabetes and inflammatory diseases |
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- 2007-03-14 AU AU2007227581A patent/AU2007227581B2/en not_active Ceased
- 2007-03-14 MX MX2012009905A patent/MX356584B/es unknown
- 2007-03-14 ES ES15151582.2T patent/ES2654908T3/es active Active
- 2007-03-14 NZ NZ571871A patent/NZ571871A/en not_active IP Right Cessation
- 2007-03-14 MX MX2008011871A patent/MX2008011871A/es active IP Right Grant
- 2007-03-14 HU HUE15151582A patent/HUE035314T2/en unknown
- 2007-03-14 UA UAA200812193A patent/UA96441C2/ru unknown
- 2007-03-14 PL PL15151582T patent/PL2902026T3/pl unknown
- 2007-03-14 WO PCT/US2007/006321 patent/WO2007109024A2/en not_active Ceased
- 2007-03-14 PL PL07752982T patent/PL2001468T3/pl unknown
- 2007-03-14 EP EP12166539A patent/EP2486926A1/en not_active Withdrawn
- 2007-03-14 RU RU2008140943/15A patent/RU2445957C2/ru active
- 2007-03-14 EP EP07752982A patent/EP2001468B1/en not_active Not-in-force
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2008
- 2008-09-16 US US12/283,811 patent/US20090143442A1/en not_active Abandoned
- 2008-10-15 KR KR1020087025221A patent/KR101475955B1/ko not_active Expired - Fee Related
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2011
- 2011-05-18 US US13/068,708 patent/US8389556B2/en not_active Expired - Fee Related
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2013
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2014
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Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2195282C2 (ru) * | 1993-09-15 | 2002-12-27 | Санкио Компани Лимитед | Применение тиазолидиндионов для предотвращения или отдаления наступления инсулиннезависимого сахарного диабета (niddm) |
Non-Patent Citations (2)
| Title |
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| CAMPBELL I.W. Pioglitazone - an oral antidiabetic agent and metabolic syndrome modulator. Can theory translate into practice? // British Journal of Diabetes & Vascular Disease, 2005, vol.5, №4, p.209-216. * |
| HARRIGAN G.G. et al. PNU-91325 increases fatty acid synthesis from glucose and mitochondrial long chain fatty acid degradation: a comparative tracer-based metabolomics study with rosiglitazone and pioglitazone in HepG2 cells // Metabolomics, 2006, vol.2, №1, p.21-29. TANIS S.P. et al. Synthesis and Biological Activity of Metabolites of the Antidiabetic, Antihyperglycemic Agent Pioglitazone // J. Med. Chem. 1996, 39, p.5053-5063. * |
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