TW200524944A - Novel cyanothiazolides, process for their preparation and their use as medicaments - Google Patents

Info

Publication number

TW200524944A

TW200524944A TW093121831A TW93121831A TW200524944A TW 200524944 A TW200524944 A TW 200524944A TW 093121831 A TW093121831 A TW 093121831A TW 93121831 A TW93121831 A TW 93121831A TW 200524944 A TW200524944 A TW 200524944A

Authority

TW

Taiwan

Prior art keywords

alkylene

alkyl

aryl

heterocyclyl

cycloalkyl

Prior art date

2003-07-25

Links

• Espacenet
• Global Dossier
• Discuss

• 238000000034 method Methods 0.000 title claims abstract description 20
• 239000003814 drug Substances 0.000 title claims description 6
• 238000002360 preparation method Methods 0.000 title abstract description 9
• QWGPPXMQCPMFRR-UHFFFAOYSA-N 2H-1,3-thiazol-2-ide-4-carbonitrile Chemical class C(#N)C=1N=[C-]SC=1 QWGPPXMQCPMFRR-UHFFFAOYSA-N 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims abstract description 112
• 229910052740 iodine Inorganic materials 0.000 claims abstract description 38
• 150000003839 salts Chemical class 0.000 claims abstract description 21
• 208000001072 type 2 diabetes mellitus Diseases 0.000 claims abstract description 5
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 4
• -1 CN Inorganic materials 0.000 claims description 147
• 125000000623 heterocyclic group Chemical group 0.000 claims description 135
• 125000003118 aryl group Chemical group 0.000 claims description 129
• 239000000203 mixture Substances 0.000 claims description 108
• 125000000217 alkyl group Chemical group 0.000 claims description 94
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 54
• 229910052794 bromium Inorganic materials 0.000 claims description 45
• 229910052731 fluorine Inorganic materials 0.000 claims description 38
• 101100295738 Gallus gallus COR3 gene Proteins 0.000 claims description 37
• 239000004480 active ingredient Substances 0.000 claims description 34
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• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 26
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 24
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 23
• 125000003342 alkenyl group Chemical group 0.000 claims description 18
• 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 17
• 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 claims description 17
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• 125000000041 C6-C10 aryl group Chemical group 0.000 claims description 10
• NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 10
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• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
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• 208000024891 symptom Diseases 0.000 claims description 5
• HSINOMROUCMIEA-FGVHQWLLSA-N (2s,4r)-4-[(3r,5s,6r,7r,8s,9s,10s,13r,14s,17r)-6-ethyl-3,7-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-17-yl]-2-methylpentanoic acid Chemical compound C([C@@]12C)C[C@@H](O)C[C@H]1[C@@H](CC)[C@@H](O)[C@@H]1[C@@H]2CC[C@]2(C)[C@@H]([C@H](C)C[C@H](C)C(O)=O)CC[C@H]21 HSINOMROUCMIEA-FGVHQWLLSA-N 0.000 claims description 4
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• 125000005842 heteroatom Chemical group 0.000 claims description 4
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• QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 claims description 4
• 229940123208 Biguanide Drugs 0.000 claims description 3
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• 229940123464 Thiazolidinedione Drugs 0.000 claims description 3
• 102000005630 Urocortins Human genes 0.000 claims description 3
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• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 3
• 239000000777 urocortin Substances 0.000 claims description 3
• SWLAMJPTOQZTAE-UHFFFAOYSA-N 4-[2-[(5-chloro-2-methoxybenzoyl)amino]ethyl]benzoic acid Chemical class COC1=CC=C(Cl)C=C1C(=O)NCCC1=CC=C(C(O)=O)C=C1 SWLAMJPTOQZTAE-UHFFFAOYSA-N 0.000 claims description 2
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