JP2008508188A5 - - Google Patents
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- Publication number
- JP2008508188A5 JP2008508188A5 JP2007504792A JP2007504792A JP2008508188A5 JP 2008508188 A5 JP2008508188 A5 JP 2008508188A5 JP 2007504792 A JP2007504792 A JP 2007504792A JP 2007504792 A JP2007504792 A JP 2007504792A JP 2008508188 A5 JP2008508188 A5 JP 2008508188A5
- Authority
- JP
- Japan
- Prior art keywords
- thiazol
- ethyl
- phenyl
- amino
- methyl
- 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.)
- Granted
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- 150000001875 compounds Chemical class 0.000 claims description 176
- 239000011780 sodium chloride Substances 0.000 claims description 52
- 150000003839 salts Chemical class 0.000 claims description 48
- CEMZPAYDPVUXTQ-UHFFFAOYSA-N 2-[4-[2-(2-acetamido-1,3-thiazol-4-yl)ethyl]phenyl]-N-(diaminomethylidene)acetamide Chemical compound S1C(NC(=O)C)=NC(CCC=2C=CC(CC(=O)NC(N)=N)=CC=2)=C1 CEMZPAYDPVUXTQ-UHFFFAOYSA-N 0.000 claims description 6
- PQEFJKLVFBMTHJ-MRXNPFEDSA-N (3R)-1-[[2-acetamido-4-[2-[4-(diaminomethylideneamino)phenyl]ethyl]-1,3-thiazol-5-yl]methyl]-N,N-dimethylpyrrolidine-3-carboxamide Chemical compound C1[C@H](C(=O)N(C)C)CCN1CC1=C(CCC=2C=CC(NC(N)=N)=CC=2)N=C(NC(C)=O)S1 PQEFJKLVFBMTHJ-MRXNPFEDSA-N 0.000 claims description 5
- PQEFJKLVFBMTHJ-INIZCTEOSA-N (3S)-1-[[2-acetamido-4-[2-[4-(diaminomethylideneamino)phenyl]ethyl]-1,3-thiazol-5-yl]methyl]-N,N-dimethylpyrrolidine-3-carboxamide Chemical compound C1[C@@H](C(=O)N(C)C)CCN1CC1=C(CCC=2C=CC(NC(N)=N)=CC=2)N=C(NC(C)=O)S1 PQEFJKLVFBMTHJ-INIZCTEOSA-N 0.000 claims description 5
- ILFPDJANERMNPA-UHFFFAOYSA-N N-[4-[2-[4-(diaminomethylideneamino)phenyl]ethyl]-5-[(4-sulfamoylphenyl)methyl]-1,3-thiazol-2-yl]acetamide Chemical compound C=1C=C(S(N)(=O)=O)C=CC=1CC=1SC(NC(=O)C)=NC=1CCC1=CC=C(NC(N)=N)C=C1 ILFPDJANERMNPA-UHFFFAOYSA-N 0.000 claims description 5
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- FQXLIWSJRXSZBZ-UHFFFAOYSA-N N-[[2-acetamido-4-[2-[4-(diaminomethylideneamino)phenyl]ethyl]-1,3-thiazol-5-yl]methyl]-N-methyl-4-nitrobenzamide Chemical compound C=1C=C([N+]([O-])=O)C=CC=1C(=O)N(C)CC=1SC(NC(C)=O)=NC=1CCC1=CC=C(NC(N)=N)C=C1 FQXLIWSJRXSZBZ-UHFFFAOYSA-N 0.000 claims description 3
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 36
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 35
- 238000002360 preparation method Methods 0.000 description 35
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 35
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- 230000002194 synthesizing Effects 0.000 description 29
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 29
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- 201000010230 macular retinal edema Diseases 0.000 description 26
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 26
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 22
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 22
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- 239000002253 acid Substances 0.000 description 20
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 20
- 239000000460 chlorine Substances 0.000 description 20
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N Triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 19
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 19
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- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 19
- 125000002947 alkylene group Chemical group 0.000 description 16
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- CSNNHWWHGAXBCP-UHFFFAOYSA-L mgso4 Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 15
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- 235000019441 ethanol Nutrition 0.000 description 14
- 235000011054 acetic acid Nutrition 0.000 description 13
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- 238000010898 silica gel chromatography Methods 0.000 description 12
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- YVYPEAZIGLTXSP-DJWKRKHSSA-N N-[4-[(Z)-2-(4-nitrophenyl)ethenyl]-1,3-thiazol-2-yl]acetamide Chemical compound S1C(NC(=O)C)=NC(\C=C/C=2C=CC(=CC=2)[N+]([O-])=O)=C1 YVYPEAZIGLTXSP-DJWKRKHSSA-N 0.000 description 7
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EP1999119A2 (en) | 2006-02-15 | 2008-12-10 | Abbott Laboratories | Novel acetyl-coa carboxylase (acc) inhibitors and their use in diabetes, obesity and metabolic syndrome |
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 |
KR20100034024A (ko) * | 2007-06-25 | 2010-03-31 | 가부시키가이샤 아루떼꾸 우에노 | 저산소 또는 허혈에 따른 안질환용 조성물 |
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-
2005
- 2005-07-27 DE DE602005013793T patent/DE602005013793D1/de active Active
- 2005-07-27 JP JP2007504792A patent/JP4978464B2/ja not_active Expired - Fee Related
- 2005-07-27 CA CA002575411A patent/CA2575411A1/en not_active Abandoned
- 2005-07-27 WO PCT/JP2005/014136 patent/WO2006011631A2/en active Application Filing
- 2005-07-27 ES ES05768525T patent/ES2324922T3/es active Active
- 2005-07-27 EP EP05768525A patent/EP1786792B1/en not_active Not-in-force
- 2005-07-27 AT AT05768525T patent/ATE427941T1/de not_active IP Right Cessation
- 2005-07-27 US US11/572,772 patent/US20070254931A1/en not_active Abandoned
- 2005-07-27 KR KR1020077004487A patent/KR20070050932A/ko not_active Application Discontinuation
- 2005-07-27 CN CNA200580031703XA patent/CN101031555A/zh active Pending
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