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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| SI2013204T1 (sl) | 2006-03-24 | 2015-06-30 | Array Biopharma, Inc. | Analogi 2-aminopriridina kot aktivatorji glukokinaze |
| WO2008091770A1 (en) * | 2007-01-24 | 2008-07-31 | Array Biopharma Inc. | 2-aminopyridine derivatives as glucokinase activators |
| CA2681695A1 (en) * | 2007-03-23 | 2008-10-02 | Array Biopharma Inc. | 2-aminopyridine analogs as glucokinase activators |
| EP2025674A1 (de) | 2007-08-15 | 2009-02-18 | sanofi-aventis | Substituierte Tetrahydronaphthaline, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel |
| SI2209778T1 (sl) * | 2007-09-21 | 2012-12-31 | Array Biopharma, Inc. | Piridin-2-il-amino-I, 2,4-tiadiazol derivati kot aktivatorji glukokinaze za zdravljenje sladkorne bolezni |
| AU2008310097B2 (en) | 2007-10-09 | 2013-05-16 | Merck Patent Gmbh | Pyridine derivatives useful as glucokinase activators |
| BRPI0908124A2 (pt) | 2008-02-06 | 2015-08-04 | Daiichi Sankyo Co Ltd | Composto, ativador de glucoquinase, composição farmacêutica, uso de um composto ou sal farmacologicamente aceitavél do mesmo, e, métodos de ativação da glucoquinase, e para tratar e/ou prevenir uma doença |
| 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 |
| TW201215388A (en) | 2010-07-05 | 2012-04-16 | Sanofi Sa | (2-aryloxyacetylamino)phenylpropionic acid derivatives, processes for preparation thereof and use thereof as medicaments |
| 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 |
| EP2683699B1 (de) | 2011-03-08 | 2015-06-24 | 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 |
| 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 |
| 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 |
| 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 |
| JPWO2012121314A1 (ja) | 2011-03-09 | 2014-07-17 | 第一三共株式会社 | ジピリジルアミン誘導体 |
| 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 |
| JP6177894B2 (ja) | 2012-05-18 | 2017-08-09 | アムジェン インコーポレイテッド | チアジアゾールの調製方法 |
| CN105164123A (zh) * | 2012-11-09 | 2015-12-16 | 安进股份有限公司 | (1s)-1-[5-({3-[(2-甲基吡啶-3-基)氧基]-5-(吡啶-2-基硫基)吡啶-2-基}氨基)-1,2,4-噻二唑-3-基]乙烷-1,2-二醇的结晶形式 |
| EP3421468B1 (en) | 2013-11-13 | 2020-11-04 | Vertex Pharmaceuticals Incorporated | Methods of preparing inhibitors of influenza viruses replication |
| WO2017093167A1 (en) | 2015-12-01 | 2017-06-08 | Basf Se | Pyridine compounds as fungicides |
| EP3383848B1 (en) | 2015-12-01 | 2020-01-08 | Basf Se | Pyridine compounds as fungicides |
| 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 |
| CN110691776A (zh) | 2017-05-30 | 2020-01-14 | 巴斯夫欧洲公司 | 吡啶和吡嗪化合物 |
| GB201714777D0 (en) | 2017-09-14 | 2017-11-01 | Univ London Queen Mary | Agent |
| CN111372579B (zh) | 2017-10-30 | 2023-08-22 | 神经孔疗法股份有限公司 | 取代的苯基磺酰基苯基三唑硫酮和其用途 |
| EP3846793B1 (en) | 2018-09-07 | 2024-01-24 | PIC Therapeutics, Inc. | Eif4e inhibitors and uses thereof |
| AU2021230289A1 (en) | 2020-03-03 | 2022-09-29 | PIC Therapeutics, Inc. | eIF4E inhibitors and uses thereof |
| JP2024532276A (ja) | 2021-08-25 | 2024-09-05 | ピク セラピューティクス, インコーポレイテッド | eIF4E阻害剤及びその使用 |
| CA3229560A1 (en) | 2021-08-25 | 2023-03-02 | Christopher L. Vandeusen | Eif4e inhibitors and uses thereof |
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| AU7193394A (en) | 1993-08-13 | 1995-03-14 | Zeneca Limited | Thia- and oxadiazole derivatives and their use as fungicides or insecticides |
| TW420669B (en) * | 1994-03-28 | 2001-02-01 | Nissan Chemical Ind Ltd | Pyridine type thiazolidines |
| US5543523A (en) | 1994-11-15 | 1996-08-06 | Regents Of The University Of Minnesota | Method and intermediates for the synthesis of korupensamines |
| HUP0202682A3 (en) * | 1999-09-10 | 2003-03-28 | Merck & Co Inc | Tyrosine kinase inhibitors, pharmaceutical compositions containing them and their use |
| JP2005511573A (ja) | 2001-11-02 | 2005-04-28 | グラクソ グループ リミテッド | Hcv阻害剤としての4−(5−員)−ヘテロアリールアシルピロリジン誘導体 |
| WO2003062224A1 (en) | 2002-01-17 | 2003-07-31 | Eli Lilly And Company | Aza-cyclic compounds as modulators of acetylcholine receptors |
| ES2289279T3 (es) * | 2002-03-15 | 2008-02-01 | Vertex Pharmaceuticals Incorporated | Composiciones utiles como inhibidores de proteinquinasas. |
| MXPA05008619A (es) * | 2003-02-13 | 2005-11-04 | Banyu Pharma Co Ltd | Derivados novedosos de 2-piridincarboxamida. |
| AR049418A1 (es) | 2004-02-27 | 2006-08-02 | Bayer Pharmaceuticals Corp | Derivados de heteroarilaminopirazol y composiciones farmaceuticas para el tratamiento de la diabetes. |
| EP1734040A4 (en) * | 2004-03-23 | 2007-11-28 | Banyu Pharma Co Ltd | SUBSTITUTED CHINAZOLINE OR PYRIDOPYRIMIDINE DERIVATIVE |
| WO2007058482A1 (en) * | 2005-11-16 | 2007-05-24 | Lg Life Sciences, Ltd. | Novel inhibitors of protein kinase |
| SI2013204T1 (sl) | 2006-03-24 | 2015-06-30 | Array Biopharma, Inc. | Analogi 2-aminopriridina kot aktivatorji glukokinaze |
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| JP5377284B2 (ja) | 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 | |
| JP5236499B2 (ja) | グルコキナーゼ活性化剤 | |
| JP5137207B2 (ja) | グルコキナーゼ活性化因子 | |
| HK1128130B (en) | 2-aminopyridine analogs as glucokinase activators | |
| HK1178901A (en) | 2-aminopyridine analogs as glucokinase activators |
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