ES2350608T3 - Derivados de spiro imidazoles como moduladores de ppar. - Google Patents
Derivados de spiro imidazoles como moduladores de ppar. Download PDFInfo
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- ES2350608T3 ES2350608T3 ES07717085T ES07717085T ES2350608T3 ES 2350608 T3 ES2350608 T3 ES 2350608T3 ES 07717085 T ES07717085 T ES 07717085T ES 07717085 T ES07717085 T ES 07717085T ES 2350608 T3 ES2350608 T3 ES 2350608T3
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- Prior art keywords
- phenyl
- dec
- dioxo
- spiro
- ethyl
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- 102000003728 Peroxisome Proliferator-Activated Receptors Human genes 0.000 title abstract description 12
- 108090000029 Peroxisome Proliferator-Activated Receptors Proteins 0.000 title abstract description 12
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- 150000001875 compounds Chemical class 0.000 claims abstract description 166
- 238000000034 method Methods 0.000 claims abstract description 44
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- -1 3-methyl-but-2-enyl Chemical group 0.000 claims description 125
- 239000002253 acid Substances 0.000 claims description 77
- 239000001257 hydrogen Substances 0.000 claims description 54
- 229910052739 hydrogen Inorganic materials 0.000 claims description 54
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- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 44
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 37
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 36
- 150000003839 salts Chemical class 0.000 claims description 27
- 239000003112 inhibitor Substances 0.000 claims description 25
- 238000011282 treatment Methods 0.000 claims description 22
- 125000000173 4-trifluoromethoxy benzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC(F)(F)F)C([H])([H])* 0.000 claims description 19
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
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- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 6
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- YASAKCUCGLMORW-UHFFFAOYSA-N Rosiglitazone Chemical compound C=1C=CC=NC=1N(C)CCOC(C=C1)=CC=C1CC1SC(=O)NC1=O YASAKCUCGLMORW-UHFFFAOYSA-N 0.000 claims description 6
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- PQUSVJVVRXWKDG-UHFFFAOYSA-N methyl 2-bromo-2-methylpropanoate Chemical compound COC(=O)C(C)(C)Br PQUSVJVVRXWKDG-UHFFFAOYSA-N 0.000 description 1
- DJJHVPBMUQLOCB-UHFFFAOYSA-N methyl 3-(3-bromophenyl)propanoate Chemical compound COC(=O)CCC1=CC=CC(Br)=C1 DJJHVPBMUQLOCB-UHFFFAOYSA-N 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
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- 229910052757 nitrogen Inorganic materials 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- MXQOYLRVSVOCQT-UHFFFAOYSA-N palladium;tritert-butylphosphane Chemical compound [Pd].CC(C)(C)P(C(C)(C)C)C(C)(C)C.CC(C)(C)P(C(C)(C)C)C(C)(C)C MXQOYLRVSVOCQT-UHFFFAOYSA-N 0.000 description 1
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- USISRUCGEISZIB-UHFFFAOYSA-N piperidin-3-one Chemical class O=C1CCCNC1 USISRUCGEISZIB-UHFFFAOYSA-N 0.000 description 1
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- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
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- 230000005855 radiation Effects 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 239000002464 receptor antagonist Substances 0.000 description 1
- 229940044551 receptor antagonist Drugs 0.000 description 1
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- 239000011347 resin Substances 0.000 description 1
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- 238000007127 saponification reaction Methods 0.000 description 1
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- 238000013207 serial dilution Methods 0.000 description 1
- 239000012679 serum free medium Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- MNWBNISUBARLIT-UHFFFAOYSA-N sodium cyanide Chemical compound [Na+].N#[C-] MNWBNISUBARLIT-UHFFFAOYSA-N 0.000 description 1
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- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
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- 229960005322 streptomycin Drugs 0.000 description 1
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- YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical class OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 description 1
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- HLUWHCDBGMUJTQ-UHFFFAOYSA-N tert-butyl 2-[3-(2,4-dioxo-1,3,8-triazaspiro[4.5]decan-8-yl)phenyl]acetate Chemical compound CC(C)(C)OC(=O)CC1=CC=CC(N2CCC3(CC2)C(NC(=O)N3)=O)=C1 HLUWHCDBGMUJTQ-UHFFFAOYSA-N 0.000 description 1
- PFSPANRLWBNSCN-UHFFFAOYSA-N tert-butyl 2-[3-[3-(cyclopropylmethyl)-2,4-dioxo-1,3,8-triazaspiro[4.5]decan-8-yl]phenyl]acetate Chemical compound CC(C)(C)OC(=O)CC1=CC=CC(N2CCC3(CC2)C(N(CC2CC2)C(=O)N3)=O)=C1 PFSPANRLWBNSCN-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
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- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C07D471/02—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 two hetero rings
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- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
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- A61P9/12—Antihypertensives
Landscapes
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| EP2091328B1 (en) | 2006-10-30 | 2011-12-28 | Merck Sharp & Dohme Corp. | Spiropiperidine beta-secretase inhibitors for the treatment of alzheimer's disease |
| EP2025674A1 (de) | 2007-08-15 | 2009-02-18 | sanofi-aventis | Substituierte Tetrahydronaphthaline, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel |
| GB0720126D0 (en) * | 2007-10-15 | 2007-11-28 | Syngenta Participations Ag | Chemical compounds |
| PE20110598A1 (es) | 2008-10-02 | 2011-08-31 | Respivert Ltd | Inhibidores de las enzimas de proteina cinasa activadas por mitogeno p38 |
| MX2011006220A (es) | 2008-12-11 | 2011-06-28 | Respivert Ltd | Inhibidores de la proteina cinasa activada por el mitogeno p38. |
| GB0905955D0 (en) | 2009-04-06 | 2009-05-20 | Respivert Ltd | Novel compounds |
| FR2944524B1 (fr) * | 2009-04-17 | 2012-11-30 | Ipsen Pharma Sas | Derives d'imidazolidine-2,4-dione et leur utilisation comme medicament |
| GB0921731D0 (en) | 2009-12-11 | 2010-01-27 | Respivert Ltd | Theraputic uses |
| GB0921730D0 (en) | 2009-12-11 | 2010-01-27 | Respivert Ltd | Method of treatment |
| WO2011107494A1 (de) | 2010-03-03 | 2011-09-09 | Sanofi | Neue aromatische glykosidderivate, diese verbindungen enthaltende arzneimittel und deren verwendung |
| GB201005589D0 (en) | 2010-04-01 | 2010-05-19 | Respivert Ltd | Novel compounds |
| JP5787977B2 (ja) | 2010-04-08 | 2015-09-30 | レスピバート・リミテツド | Ｐ３８ｍａｐキナーゼ阻害剤 |
| US9260410B2 (en) | 2010-04-08 | 2016-02-16 | Respivert Ltd. | P38 MAP kinase inhibitors |
| BR112012030408A2 (pt) * | 2010-05-31 | 2015-09-29 | Syngenta Participations Ag | método de melhoramento de culturas |
| US8933024B2 (en) | 2010-06-18 | 2015-01-13 | Sanofi | Azolopyridin-3-one derivatives as inhibitors of lipases and phospholipases |
| US8530413B2 (en) | 2010-06-21 | 2013-09-10 | Sanofi | Heterocyclically substituted methoxyphenyl derivatives with an oxo group, processes for preparation thereof and use thereof as medicaments |
| WO2011163539A2 (en) * | 2010-06-25 | 2011-12-29 | The Johns Hopkins University | nAChRα7 AGONISTS AND nAChRα7 ANTAGONISTS FOR TREATING ULCERATIVE COLITIS (UC) AND CROHN'S DISEASE (CD) |
| TW201215387A (en) | 2010-07-05 | 2012-04-16 | Sanofi Aventis | Spirocyclically substituted 1,3-propane dioxide derivatives, processes for preparation thereof and use thereof as a medicament |
| TW201215388A (en) | 2010-07-05 | 2012-04-16 | Sanofi Sa | (2-aryloxyacetylamino)phenylpropionic acid derivatives, processes for preparation thereof and use thereof as medicaments |
| TW201221505A (en) | 2010-07-05 | 2012-06-01 | Sanofi Sa | Aryloxyalkylene-substituted hydroxyphenylhexynoic acids, process for preparation thereof and use thereof as a medicament |
| KR101898610B1 (ko) | 2010-08-31 | 2018-09-14 | 서울대학교산학협력단 | ＰＰＡＲδ 활성물질의 태자 재프로그래밍 용도 |
| WO2012120052A1 (de) | 2011-03-08 | 2012-09-13 | Sanofi | Mit carbozyklen oder heterozyklen substituierte oxathiazinderivate, verfahren zu deren herstellung, diese verbindungen enthaltende arzneimittel und deren verwendung |
| WO2012120056A1 (de) | 2011-03-08 | 2012-09-13 | Sanofi | Tetrasubstituierte oxathiazinderivate, verfahren zu deren herstellung, ihre verwendung als medikament sowie sie enthaltendes arzneimittel und deren verwendung |
| EP2683705B1 (de) | 2011-03-08 | 2015-04-22 | Sanofi | Di- und trisubstituierte oxathiazinderivate, verfahren zu deren herstellung, ihre verwendung als medikament sowie sie enthaltendes arzneimittel und deren verwendung |
| WO2012120053A1 (de) | 2011-03-08 | 2012-09-13 | Sanofi | Verzweigte oxathiazinderivate, verfahren zu deren herstellung, ihre verwendung als medikament sowie sie enthaltendes arzneimittel und deren verwendung |
| US8710050B2 (en) | 2011-03-08 | 2014-04-29 | Sanofi | Di and tri- substituted oxathiazine derivatives, method for the production, method for the production thereof, use thereof as medicine and drug containing said derivatives and use thereof |
| WO2013037390A1 (en) | 2011-09-12 | 2013-03-21 | Sanofi | 6-(4-hydroxy-phenyl)-3-styryl-1h-pyrazolo[3,4-b]pyridine-4-carboxylic acid amide derivatives as kinase inhibitors |
| WO2013045413A1 (en) | 2011-09-27 | 2013-04-04 | Sanofi | 6-(4-hydroxy-phenyl)-3-alkyl-1h-pyrazolo[3,4-b]pyridine-4-carboxylic acid amide derivatives as kinase inhibitors |
| WO2014076484A1 (en) | 2012-11-16 | 2014-05-22 | Respivert Limited | Kinase inhibitors |
| 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 |
| CN113461572B (zh) * | 2021-06-30 | 2023-09-19 | 江苏慧聚药业股份有限公司 | 2-(3-溴-5-甲基苯基)乙腈的合成 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2378179A (en) | 2001-08-03 | 2003-02-05 | Pantherix Ltd | Aromatic sulfonamides and their use in treating bacterial diseases |
| JP4710606B2 (ja) * | 2003-04-18 | 2011-06-29 | 小野薬品工業株式会社 | スピロピペリジン化合物およびその医薬用途 |
-
2007
- 2007-01-25 WO PCT/US2007/002315 patent/WO2007087448A1/en not_active Ceased
- 2007-01-25 US US12/160,302 patent/US20090137610A1/en not_active Abandoned
- 2007-01-25 CA CA002627692A patent/CA2627692A1/en not_active Abandoned
- 2007-01-25 KR KR1020087018697A patent/KR20080081359A/ko not_active Ceased
- 2007-01-25 EP EP07717085A patent/EP1979355B1/en not_active Not-in-force
- 2007-01-25 RU RU2008135128/04A patent/RU2008135128A/ru not_active Application Discontinuation
- 2007-01-25 ES ES07717085T patent/ES2350608T3/es active Active
- 2007-01-25 JP JP2008552477A patent/JP2009525279A/ja active Pending
- 2007-01-25 AT AT07717085T patent/ATE478072T1/de active
- 2007-01-25 DE DE602007008524T patent/DE602007008524D1/de active Active
- 2007-01-25 PT PT07717085T patent/PT1979355E/pt unknown
- 2007-01-25 AU AU2007208156A patent/AU2007208156A1/en not_active Abandoned
- 2007-01-25 PL PL07717085T patent/PL1979355T3/pl unknown
- 2007-01-25 BR BRPI0706771-2A patent/BRPI0706771A2/pt not_active IP Right Cessation
- 2007-01-25 CN CNA2007800031722A patent/CN101374841A/zh active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| PL1979355T3 (pl) | 2011-04-29 |
| US20090137610A1 (en) | 2009-05-28 |
| DE602007008524D1 (de) | 2010-09-30 |
| EP1979355B1 (en) | 2010-08-18 |
| PT1979355E (pt) | 2010-10-27 |
| ATE478072T1 (de) | 2010-09-15 |
| CA2627692A1 (en) | 2007-08-02 |
| AU2007208156A1 (en) | 2007-08-02 |
| JP2009525279A (ja) | 2009-07-09 |
| WO2007087448A1 (en) | 2007-08-02 |
| BRPI0706771A2 (pt) | 2011-04-05 |
| CN101374841A (zh) | 2009-02-25 |
| RU2008135128A (ru) | 2010-03-10 |
| EP1979355A1 (en) | 2008-10-15 |
| KR20080081359A (ko) | 2008-09-09 |
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