JP5377284B2 - グルコキナーゼアクチベーターとしての2−アミノピリジンアナログ - Google Patents
グルコキナーゼアクチベーターとしての2−アミノピリジンアナログ Download PDFInfo
- Publication number
- JP5377284B2 JP5377284B2 JP2009501610A JP2009501610A JP5377284B2 JP 5377284 B2 JP5377284 B2 JP 5377284B2 JP 2009501610 A JP2009501610 A JP 2009501610A JP 2009501610 A JP2009501610 A JP 2009501610A JP 5377284 B2 JP5377284 B2 JP 5377284B2
- Authority
- JP
- Japan
- Prior art keywords
- pyridin
- ylamino
- amine
- ylthio
- alkyl
- 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.)
- Expired - Fee Related
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- 0 CC(CC1)C*N1C(O)O*1CC1 Chemical compound CC(CC1)C*N1C(O)O*1CC1 0.000 description 47
- KRGGYECGWFIFCA-UHFFFAOYSA-N Brc(cc1Oc2ccccc2)cnc1Nc1nc(CNc2ccccc2)c[s]1 Chemical compound Brc(cc1Oc2ccccc2)cnc1Nc1nc(CNc2ccccc2)c[s]1 KRGGYECGWFIFCA-UHFFFAOYSA-N 0.000 description 1
- UIKOKYHZNDQRRV-QXMHVHEDSA-N C/C(/N)=C/SC(CNc1ncccc1OC1CCCC1)=C Chemical compound C/C(/N)=C/SC(CNc1ncccc1OC1CCCC1)=C UIKOKYHZNDQRRV-QXMHVHEDSA-N 0.000 description 1
- NQRYJNQNLNOLGT-UHFFFAOYSA-N C1CCNCC1 Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 1
- PAWOKIFAYFWVFW-UQQQWYQISA-N C=C(O)O/C(/CCc1c[s]c(Nc(c(Oc2ccccc2)c2)ncc2Br)n1)=N\N Chemical compound C=C(O)O/C(/CCc1c[s]c(Nc(c(Oc2ccccc2)c2)ncc2Br)n1)=N\N PAWOKIFAYFWVFW-UQQQWYQISA-N 0.000 description 1
- MUKWMXPIYBOQJU-UHFFFAOYSA-N CC(C)(C)OC(NCC(N(CC1)CCC1c1n[s]c(Nc(c(Oc2ccccc2)c2)ncc2Sc2ccccn2)n1)=O)=O Chemical compound CC(C)(C)OC(NCC(N(CC1)CCC1c1n[s]c(Nc(c(Oc2ccccc2)c2)ncc2Sc2ccccn2)n1)=O)=O MUKWMXPIYBOQJU-UHFFFAOYSA-N 0.000 description 1
- GQRZLHABFOGPDK-UHFFFAOYSA-N CC(C)N(CC1)C=CC1C(c1cccc(C(C2)NCCC2C(c2cnccn2)SS)n1)SC Chemical compound CC(C)N(CC1)C=CC1C(c1cccc(C(C2)NCCC2C(c2cnccn2)SS)n1)SC GQRZLHABFOGPDK-UHFFFAOYSA-N 0.000 description 1
- SZZWZYCAXOGNDI-UHFFFAOYSA-N CC(C)NC(N(CC1)CC1Oc1cc(Br)cnc1Nc1nc(C)c[s]1)=O Chemical compound CC(C)NC(N(CC1)CC1Oc1cc(Br)cnc1Nc1nc(C)c[s]1)=O SZZWZYCAXOGNDI-UHFFFAOYSA-N 0.000 description 1
- XBBJJVPRSBCRAJ-UHFFFAOYSA-N CC(C1)=C1C(N(CC1)CCC1c1n[s]c(Nc(c(Oc2ccccc2)c2)ncc2Sc2ncccc2)n1)=O Chemical compound CC(C1)=C1C(N(CC1)CCC1c1n[s]c(Nc(c(Oc2ccccc2)c2)ncc2Sc2ncccc2)n1)=O XBBJJVPRSBCRAJ-UHFFFAOYSA-N 0.000 description 1
- HVIAVANLCAFGJD-UHFFFAOYSA-O CC(CC1)CC[NH+]1C(N(C)C)=O Chemical compound CC(CC1)CC[NH+]1C(N(C)C)=O HVIAVANLCAFGJD-UHFFFAOYSA-O 0.000 description 1
- ZEVYELQKTSIDKI-UHFFFAOYSA-N CC(Cc1c[s]c(Nc(c(Oc2ccccc2)c2)ncc2Br)n1)(C(OC)=O)OC Chemical compound CC(Cc1c[s]c(Nc(c(Oc2ccccc2)c2)ncc2Br)n1)(C(OC)=O)OC ZEVYELQKTSIDKI-UHFFFAOYSA-N 0.000 description 1
- WTEUDCWQXUJIDU-UHFFFAOYSA-N CC(N1CCC(Cc2n[s]c(Nc(c(Oc(cc3)ccc3F)c3)ncc3Sc3c4[s]ccc4ncc3)n2)CC1)=O Chemical compound CC(N1CCC(Cc2n[s]c(Nc(c(Oc(cc3)ccc3F)c3)ncc3Sc3c4[s]ccc4ncc3)n2)CC1)=O WTEUDCWQXUJIDU-UHFFFAOYSA-N 0.000 description 1
- BQSMHKFOKZYEIC-UHFFFAOYSA-N CC(c1ncccc1)Sc(cc1Oc2ccccc2)cnc1Nc1nc(C)c[s]1 Chemical compound CC(c1ncccc1)Sc(cc1Oc2ccccc2)cnc1Nc1nc(C)c[s]1 BQSMHKFOKZYEIC-UHFFFAOYSA-N 0.000 description 1
- URKQBROHEGCVFW-UHFFFAOYSA-N CC1(C(C2CCNCC2)SC)NC=CC=C1 Chemical compound CC1(C(C2CCNCC2)SC)NC=CC=C1 URKQBROHEGCVFW-UHFFFAOYSA-N 0.000 description 1
- WYBDDJHLPSHHHQ-UHFFFAOYSA-N CCC(CC[Tc](C)=O)C(c1ccccn1)SC Chemical compound CCC(CC[Tc](C)=O)C(c1ccccn1)SC WYBDDJHLPSHHHQ-UHFFFAOYSA-N 0.000 description 1
- SOIYMABYOQVGNR-YWEYNIOJSA-N CSC(C1CCN(CCO)CC1)C(CC/C=C\N)=C Chemical compound CSC(C1CCN(CCO)CC1)C(CC/C=C\N)=C SOIYMABYOQVGNR-YWEYNIOJSA-N 0.000 description 1
- HHFODWILAJWBMN-UHFFFAOYSA-N C[n]1c(S(C)C)ncc1C1OC1OC Chemical compound C[n]1c(S(C)C)ncc1C1OC1OC HHFODWILAJWBMN-UHFFFAOYSA-N 0.000 description 1
- WYHBENDEZDFJNU-UHFFFAOYSA-N Cc(c(C)c1)ccc1F Chemical compound Cc(c(C)c1)ccc1F WYHBENDEZDFJNU-UHFFFAOYSA-N 0.000 description 1
- DVFVNJHIVAPTMS-UHFFFAOYSA-N Cc1c(C(F)(F)F)cccc1 Chemical compound Cc1c(C(F)(F)F)cccc1 DVFVNJHIVAPTMS-UHFFFAOYSA-N 0.000 description 1
- FINKAQNDPOLHCG-UHFFFAOYSA-N Cc1c[s]c(Nc(c(Oc2ccccc2)c2)ncc2SC(C2CCN(CCO)CC2)C2=NC(C)=CCCCO2)n1 Chemical compound Cc1c[s]c(Nc(c(Oc2ccccc2)c2)ncc2SC(C2CCN(CCO)CC2)C2=NC(C)=CCCCO2)n1 FINKAQNDPOLHCG-UHFFFAOYSA-N 0.000 description 1
- DRXPIVANAGWFRX-UHFFFAOYSA-N Cc1c[s]c(Nc(c(Oc2ccccc2)c2)ncc2Sc(cc(cc2)OC)c2Cl)n1 Chemical compound Cc1c[s]c(Nc(c(Oc2ccccc2)c2)ncc2Sc(cc(cc2)OC)c2Cl)n1 DRXPIVANAGWFRX-UHFFFAOYSA-N 0.000 description 1
- CERJITPTQCALBF-UHFFFAOYSA-N Cc1c[s]c(Nc(c(Oc2ccccc2)c2)ncc2Sc2cc(OCC(O)=O)ccc2)n1 Chemical compound Cc1c[s]c(Nc(c(Oc2ccccc2)c2)ncc2Sc2cc(OCC(O)=O)ccc2)n1 CERJITPTQCALBF-UHFFFAOYSA-N 0.000 description 1
- QNDGXFOQZILMJP-UHFFFAOYSA-N Cc1c[s]c(Nc(c(Oc2ccccc2)c2)ncc2Sc2cccc(Cl)c2)n1 Chemical compound Cc1c[s]c(Nc(c(Oc2ccccc2)c2)ncc2Sc2cccc(Cl)c2)n1 QNDGXFOQZILMJP-UHFFFAOYSA-N 0.000 description 1
- ODBIGGBFMSXVMF-UHFFFAOYSA-N Cc1c[s]c(Nc(c(Oc2ccccc2)c2)ncc2Sc2ccccc2)n1 Chemical compound Cc1c[s]c(Nc(c(Oc2ccccc2)c2)ncc2Sc2ccccc2)n1 ODBIGGBFMSXVMF-UHFFFAOYSA-N 0.000 description 1
- ZXZSKFDROQWYBM-UHFFFAOYSA-N Cc1c[s]c(Nc(c(Sc2ccccc2)c2)ncc2OCc2ccccc2)n1 Chemical compound Cc1c[s]c(Nc(c(Sc2ccccc2)c2)ncc2OCc2ccccc2)n1 ZXZSKFDROQWYBM-UHFFFAOYSA-N 0.000 description 1
- MOXLUWMOEDVNJB-UHFFFAOYSA-N Cc1c[s]c(Nc(c(Sc2ccccc2Cl)c2)ncc2Br)n1 Chemical compound Cc1c[s]c(Nc(c(Sc2ccccc2Cl)c2)ncc2Br)n1 MOXLUWMOEDVNJB-UHFFFAOYSA-N 0.000 description 1
- JAVCMWCFDMXTLK-UHFFFAOYSA-N Cc1c[s]c(Nc2ncccc2OC2C=CCCC2)n1 Chemical compound Cc1c[s]c(Nc2ncccc2OC2C=CCCC2)n1 JAVCMWCFDMXTLK-UHFFFAOYSA-N 0.000 description 1
- IYPOXHYQGDSWNJ-UHFFFAOYSA-N Cc1c[s]c(Nc2ncccc2Sc2ccccc2C(F)(F)F)n1 Chemical compound Cc1c[s]c(Nc2ncccc2Sc2ccccc2C(F)(F)F)n1 IYPOXHYQGDSWNJ-UHFFFAOYSA-N 0.000 description 1
- LRLRAYMYEXQKID-UHFFFAOYSA-N Cc1ccc(C(F)(F)F)cc1 Chemical compound Cc1ccc(C(F)(F)F)cc1 LRLRAYMYEXQKID-UHFFFAOYSA-N 0.000 description 1
- CISHHWIYBOSLHY-UHFFFAOYSA-N Cc1ncc(CO)[n]1C Chemical compound Cc1ncc(CO)[n]1C CISHHWIYBOSLHY-UHFFFAOYSA-N 0.000 description 1
- GIWQSPITLQVMSG-UHFFFAOYSA-N Cc1ncc[n]1C Chemical compound Cc1ncc[n]1C GIWQSPITLQVMSG-UHFFFAOYSA-N 0.000 description 1
- WETQJZMTBPNLTP-UHFFFAOYSA-N Fc(cc1)ccc1Oc1cc(Br)cnc1Nc1nc(cccn2)c2[s]1 Chemical compound Fc(cc1)ccc1Oc1cc(Br)cnc1Nc1nc(cccn2)c2[s]1 WETQJZMTBPNLTP-UHFFFAOYSA-N 0.000 description 1
- DDDYRKBUYLIUCK-UHFFFAOYSA-N O=C1NCCC1Cc1c[s]c(Nc(c(S)c2)ncc2Br)n1 Chemical compound O=C1NCCC1Cc1c[s]c(Nc(c(S)c2)ncc2Br)n1 DDDYRKBUYLIUCK-UHFFFAOYSA-N 0.000 description 1
- BUGOPWGPQGYYGR-UHFFFAOYSA-N O=S1(CCCCC1)=O Chemical compound O=S1(CCCCC1)=O BUGOPWGPQGYYGR-UHFFFAOYSA-N 0.000 description 1
- JCSZXBIMTCZGOX-UHFFFAOYSA-N OCC(N(CC1)CCC1c1n[s]c(Nc(c(Oc2ccccc2)c2)ncc2Sc2ncccc2)n1)=O Chemical compound OCC(N(CC1)CCC1c1n[s]c(Nc(c(Oc2ccccc2)c2)ncc2Sc2ncccc2)n1)=O JCSZXBIMTCZGOX-UHFFFAOYSA-N 0.000 description 1
Classifications
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- 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
- C07D417/12—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 linked by a chain containing hetero atoms as chain links
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- C07D491/02—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 two hetero rings
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| RS53981B1 (sr) | 2006-03-24 | 2015-10-30 | Array Biopharma Inc. | Analozi 2-aminopiridina kao aktivatori glukokinaze |
| US8431713B2 (en) * | 2007-01-24 | 2013-04-30 | Array Biopharma, Inc. | 2-aminopyridine derivatives as glucokinase activators |
| JP5450108B2 (ja) * | 2007-03-23 | 2014-03-26 | アレイ バイオファーマ、インコーポレイテッド | グルコキナーゼ活性化剤としての2−アミノピリジン類似体 |
| EP2025674A1 (de) | 2007-08-15 | 2009-02-18 | sanofi-aventis | Substituierte Tetrahydronaphthaline, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel |
| EA019104B1 (ru) * | 2007-09-21 | 2014-01-30 | Эррей Биофарма Инк. | Активаторы глюкокиназы |
| KR20100090250A (ko) | 2007-10-09 | 2010-08-13 | 메르크 파텐트 게엠베하 | 글루코키나제 활성체로서 유용한 피리딘 유도체 |
| CN102015637B (zh) * | 2008-02-06 | 2014-05-21 | 第一三共株式会社 | 苯基吡咯衍生物 |
| US7741327B2 (en) | 2008-04-16 | 2010-06-22 | Hoffmann-La Roche Inc. | Pyrrolidinone glucokinase activators |
| WO2011107494A1 (de) | 2010-03-03 | 2011-09-09 | Sanofi | Neue aromatische glykosidderivate, diese verbindungen enthaltende arzneimittel und deren verwendung |
| CA2800498C (en) | 2010-03-31 | 2021-11-16 | The Scripps Research Institute | Reprogramming cells |
| US8178689B2 (en) | 2010-06-17 | 2012-05-15 | Hoffman-La Roche Inc. | Tricyclic compounds |
| EP2582709B1 (de) | 2010-06-18 | 2018-01-24 | Sanofi | Azolopyridin-3-on-derivate als inhibitoren von lipasen und phospholipasen |
| 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 |
| TW201221505A (en) | 2010-07-05 | 2012-06-01 | Sanofi Sa | Aryloxyalkylene-substituted hydroxyphenylhexynoic acids, process for preparation thereof and use thereof as a medicament |
| 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 |
| WO2012120054A1 (de) | 2011-03-08 | 2012-09-13 | Sanofi | Di- und trisubstituierte oxathiazinderivate, verfahren zu deren herstellung, ihre verwendung als medikament sowie sie enthaltendes arzneimittel und deren verwendung |
| EP2766349B1 (de) | 2011-03-08 | 2016-06-01 | Sanofi | Mit carbozyklen oder heterozyklen substituierte oxathiazinderivate, verfahren zu deren herstellung, diese verbindungen enthaltende arzneimittel und deren verwendung |
| EP2683704B1 (de) | 2011-03-08 | 2014-12-17 | Sanofi | Verzweigte oxathiazinderivate, verfahren zu deren herstellung, ihre verwendung als medikament sowie sie enthaltendes 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 |
| WO2012120055A1 (de) | 2011-03-08 | 2012-09-13 | Sanofi | Di- und trisubstituierte oxathiazinderivate, verfahren zu deren herstellung, ihre verwendung als medikament sowie sie enthaltendes arzneimittel und deren verwendung |
| KR20140051834A (ko) | 2011-03-09 | 2014-05-02 | 다이이찌 산쿄 가부시키가이샤 | 디피리딜아민 유도체 |
| 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 |
| EP2760862B1 (en) | 2011-09-27 | 2015-10-21 | Sanofi | 6-(4-hydroxy-phenyl)-3-alkyl-1h-pyrazolo[3,4-b]pyridine-4-carboxylic acid amide derivatives as kinase inhibitors |
| EP2850057A4 (en) | 2012-05-18 | 2016-01-27 | Amgen Inc | PROCESS FOR THE PREPARATION OF THIADIAZOLENE |
| US20150299182A1 (en) * | 2012-11-09 | 2015-10-22 | Amgen Inc. | Crystalline forms of (1s)-1-[5-(amino)-1,2,4-thiadiazol-3-yl]ethane-1,2-diol |
| HUE038820T2 (hu) | 2013-11-13 | 2018-11-28 | Vertex Pharma | Eljárás influenzavírusok replikációjának inhibitorai elõállítására |
| EP3383848B1 (en) | 2015-12-01 | 2020-01-08 | Basf Se | Pyridine compounds as fungicides |
| BR112018010316A2 (pt) | 2015-12-01 | 2018-12-04 | Basf Se | compostos de fórmula, composição, utilização de um composto de fórmula, método para o combate de fungos fitopatogênicos e semente |
| CN108329330B (zh) * | 2017-01-20 | 2021-05-04 | 复旦大学 | 2-苄氧苯基噁唑并吡啶类化合物及其药物用途 |
| UA126679C2 (uk) | 2017-05-30 | 2023-01-11 | Басф Се | Піридинові та піразинові сполуки |
| GB201714777D0 (en) | 2017-09-14 | 2017-11-01 | Univ London Queen Mary | Agent |
| BR112020008727A2 (pt) | 2017-10-30 | 2020-10-20 | Neuropore Therapies, Inc. | fenil sulfonil fenil triazol tionas substituídas e usos destas |
| EP3846793B1 (en) | 2018-09-07 | 2024-01-24 | PIC Therapeutics, Inc. | Eif4e inhibitors and uses thereof |
| BR112022012153A2 (pt) | 2019-12-19 | 2022-08-30 | Curia Spain S A U | Processo para preparar um composto e composto |
| AR121506A1 (es) | 2020-03-03 | 2022-06-08 | Pic Therapeutics Inc | Inhibidores del eif4e y sus usos |
| US12157732B2 (en) | 2021-08-25 | 2024-12-03 | PIC Therapeutics, Inc. | eIF4E inhibitors and uses thereof |
| IL310924A (en) | 2021-08-25 | 2024-04-01 | Pic Therapeutics Inc | Eif4e inhibitors and uses thereof |
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| US3773919A (en) | 1969-10-23 | 1973-11-20 | Du Pont | Polylactide-drug mixtures |
| NZ225999A (en) | 1987-09-10 | 1992-04-28 | Merck Sharp & Dohme | Azacyclic- or azabicyclic-substituted thiadiazole derivatives and pharmaceutical compositions |
| AU7193394A (en) | 1993-08-13 | 1995-03-14 | Zeneca Limited | Thia- and oxadiazole derivatives and their use as fungicides or insecticides |
| IL113112A (en) * | 1994-03-28 | 2000-06-01 | Nissan Chemical Ind Ltd | Pyridine substituted thiazolidinediones and pharmaceutical compositions comprising them |
| US5543523A (en) | 1994-11-15 | 1996-08-06 | Regents Of The University Of Minnesota | Method and intermediates for the synthesis of korupensamines |
| MXPA02002559A (es) | 1999-09-10 | 2002-07-30 | Merck & Co Inc | Inhibidores de tirosina cinasa. |
| US20050043545A1 (en) | 2001-11-02 | 2005-02-24 | Gianpalol Bravi | 4-(5-Membered)-heteroaryl acyl pyrrolidine derivatives as hcv inhibitors |
| WO2003062224A1 (en) | 2002-01-17 | 2003-07-31 | Eli Lilly And Company | Aza-cyclic compounds as modulators of acetylcholine receptors |
| US6846928B2 (en) | 2002-03-15 | 2005-01-25 | Vertex Pharmaceuticals Incorporated | Compositions useful as inhibitors of protein kinases |
| BRPI0407283A (pt) * | 2003-02-13 | 2006-01-31 | Banyu Pharma Co Ltd | Composto, composição farmacêutica, e, agente ativador de glucoquinase, agentes terapêuticos e/ou agentes preventivos para diabetes melito e obesidade |
| AR049418A1 (es) | 2004-02-27 | 2006-08-02 | Bayer Pharmaceuticals Corp | Derivados de heteroarilaminopirazol y composiciones farmaceuticas para el tratamiento de la diabetes. |
| AU2005223610B2 (en) * | 2004-03-23 | 2008-05-29 | Banyu Pharmaceutical Co., Ltd. | Substituted quinazoline or pyridopyrimidine derivative |
| KR20070052207A (ko) * | 2005-11-16 | 2007-05-21 | 주식회사 엘지생명과학 | 신규한 kdr 억제제 |
| RS53981B1 (sr) | 2006-03-24 | 2015-10-30 | Array Biopharma Inc. | Analozi 2-aminopiridina kao aktivatori glukokinaze |
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| JP5236499B2 (ja) | グルコキナーゼ活性化剤 | |
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