JP6088425B2 - チトクロームp450阻害剤およびその使用 - Google Patents
チトクロームp450阻害剤およびその使用 Download PDFInfo
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- JP6088425B2 JP6088425B2 JP2013513284A JP2013513284A JP6088425B2 JP 6088425 B2 JP6088425 B2 JP 6088425B2 JP 2013513284 A JP2013513284 A JP 2013513284A JP 2013513284 A JP2013513284 A JP 2013513284A JP 6088425 B2 JP6088425 B2 JP 6088425B2
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- JP
- Japan
- Prior art keywords
- alkyl
- alkenyl
- alkynyl
- halo
- imidazol
- 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.)
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- 208000003311 Cytochrome P-450 Enzyme Inhibitors Diseases 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 claims description 1408
- 125000000304 alkynyl group Chemical group 0.000 claims description 655
- 125000005843 halogen group Chemical group 0.000 claims description 614
- 125000003342 alkenyl group Chemical group 0.000 claims description 447
- 125000001424 substituent group Chemical group 0.000 claims description 317
- -1 4-pyridinyl Chemical group 0.000 claims description 308
- 125000000623 heterocyclic group Chemical group 0.000 claims description 271
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 262
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 222
- 125000003118 aryl group Chemical group 0.000 claims description 215
- 229920006395 saturated elastomer Polymers 0.000 claims description 208
- 125000003545 alkoxy group Chemical group 0.000 claims description 176
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 176
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims description 137
- WMFYOYKPJLRMJI-UHFFFAOYSA-N Lercanidipine hydrochloride Chemical compound Cl.COC(=O)C1=C(C)NC(C)=C(C(=O)OC(C)(C)CN(C)CCC(C=2C=CC=CC=2)C=2C=CC=CC=2)C1C1=CC=CC([N+]([O-])=O)=C1 WMFYOYKPJLRMJI-UHFFFAOYSA-N 0.000 claims description 127
- 150000001875 compounds Chemical class 0.000 claims description 126
- 125000004414 alkyl thio group Chemical group 0.000 claims description 114
- 229910052739 hydrogen Inorganic materials 0.000 claims description 94
- 239000001257 hydrogen Substances 0.000 claims description 90
- 125000001072 heteroaryl group Chemical group 0.000 claims description 80
- 229910052799 carbon Inorganic materials 0.000 claims description 75
- 125000002883 imidazolyl group Chemical group 0.000 claims description 66
- 125000001425 triazolyl group Chemical group 0.000 claims description 66
- 229910052757 nitrogen Inorganic materials 0.000 claims description 58
- 150000003839 salts Chemical class 0.000 claims description 53
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 45
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 44
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 43
- 201000010099 disease Diseases 0.000 claims description 41
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 41
- 125000005842 heteroatom Chemical group 0.000 claims description 38
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 35
- 125000004432 carbon atom Chemical group C* 0.000 claims description 32
- 238000011282 treatment Methods 0.000 claims description 32
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 claims description 29
- 125000006619 (C1-C6) dialkylamino group Chemical group 0.000 claims description 28
- UOTCXIMRODXHSV-UHFFFAOYSA-N [2,3-dihydroxy-4-(2-methylsulfonyloxyethylazaniumyl)butyl]-(2-methylsulfonyloxyethyl)azanium;dichloride Chemical group [Cl-].[Cl-].CS(=O)(=O)OCC[NH2+]CC(O)C(O)C[NH2+]CCOS(C)(=O)=O UOTCXIMRODXHSV-UHFFFAOYSA-N 0.000 claims description 26
- KPCZJLGGXRGYIE-UHFFFAOYSA-N [C]1=CC=CN=C1 Chemical group [C]1=CC=CN=C1 KPCZJLGGXRGYIE-UHFFFAOYSA-N 0.000 claims description 24
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 23
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 20
- 239000008194 pharmaceutical composition Substances 0.000 claims description 18
- 206010016654 Fibrosis Diseases 0.000 claims description 17
- 229940095102 methyl benzoate Drugs 0.000 claims description 15
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 13
- 230000004761 fibrosis Effects 0.000 claims description 13
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 12
- 125000004585 polycyclic heterocycle group Chemical group 0.000 claims description 12
- 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 claims description 11
- 229910052736 halogen Inorganic materials 0.000 claims description 11
- 150000002367 halogens Chemical group 0.000 claims description 11
- 125000002911 monocyclic heterocycle group Chemical group 0.000 claims description 11
- 239000005711 Benzoic acid Substances 0.000 claims description 10
- 102100039282 Cytochrome P450 26A1 Human genes 0.000 claims description 10
- 101000745891 Homo sapiens Cytochrome P450 26A1 Proteins 0.000 claims description 10
- 235000010233 benzoic acid Nutrition 0.000 claims description 10
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 10
- 230000003463 hyperproliferative effect Effects 0.000 claims description 10
- 229910052717 sulfur Inorganic materials 0.000 claims description 10
- 150000001602 bicycloalkyls Chemical group 0.000 claims description 9
- 102000014654 Aromatase Human genes 0.000 claims description 8
- 108010078554 Aromatase Proteins 0.000 claims description 8
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 8
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 8
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 8
- 102000001854 Steroid 17-alpha-Hydroxylase Human genes 0.000 claims description 7
- 108010015330 Steroid 17-alpha-Hydroxylase Proteins 0.000 claims description 7
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 7
- 239000003937 drug carrier Substances 0.000 claims description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 6
- MUMGGOZAMZWBJJ-DYKIIFRCSA-N Testostosterone Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 MUMGGOZAMZWBJJ-DYKIIFRCSA-N 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 6
- 125000000524 functional group Chemical group 0.000 claims description 6
- 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 claims description 6
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 6
- FEXQDZTYJVXMOS-UHFFFAOYSA-N Isopropyl benzoate Chemical compound CC(C)OC(=O)C1=CC=CC=C1 FEXQDZTYJVXMOS-UHFFFAOYSA-N 0.000 claims description 5
- 150000001412 amines Chemical class 0.000 claims description 5
- 208000027866 inflammatory disease Diseases 0.000 claims description 5
- SHGAZHPCJJPHSC-YCNIQYBTSA-N all-trans-retinoic acid Chemical compound OC(=O)\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C SHGAZHPCJJPHSC-YCNIQYBTSA-N 0.000 claims description 4
- 239000003085 diluting agent Substances 0.000 claims description 4
- MTZQAGJQAFMTAQ-UHFFFAOYSA-N ethyl benzoate Chemical compound CCOC(=O)C1=CC=CC=C1 MTZQAGJQAFMTAQ-UHFFFAOYSA-N 0.000 claims description 4
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 4
- 229930002330 retinoic acid Natural products 0.000 claims description 4
- 125000004434 sulfur atom Chemical group 0.000 claims description 4
- VQYZRLAVRNGKHW-UHFFFAOYSA-N 1-[[6-[2-(dimethylamino)-1-imidazol-1-ylbutyl]-1,3-benzothiazol-2-yl]carbamoyl]cyclopentane-1-carboxylic acid Chemical compound C1=CN=CN1C(C(CC)N(C)C)C(C=C1S2)=CC=C1N=C2NC(=O)C1(C(O)=O)CCCC1 VQYZRLAVRNGKHW-UHFFFAOYSA-N 0.000 claims description 3
- 229960003604 testosterone Drugs 0.000 claims description 3
- SSUFLXZQDNLPKQ-UHFFFAOYSA-N 1-(1,3-benzothiazol-6-yl)-1-imidazol-1-yl-n,n-dimethylbutan-2-amine Chemical compound C=1C=C2N=CSC2=CC=1C(C(CC)N(C)C)N1C=CN=C1 SSUFLXZQDNLPKQ-UHFFFAOYSA-N 0.000 claims description 2
- GKHPQTACWCSBAN-UHFFFAOYSA-N 1-(2-bromo-1,3-benzothiazol-6-yl)-1-imidazol-1-yl-n,n-dimethylbutan-2-amine Chemical compound C=1C=C2N=C(Br)SC2=CC=1C(C(CC)N(C)C)N1C=CN=C1 GKHPQTACWCSBAN-UHFFFAOYSA-N 0.000 claims description 2
- JPDQUBBDOLHXSU-UHFFFAOYSA-N 1-(2-bromo-1,3-benzothiazol-6-yl)-n-ethyl-1-imidazol-1-yl-n-methylbutan-2-amine Chemical compound C=1C=C2N=C(Br)SC2=CC=1C(C(CC)N(C)CC)N1C=CN=C1 JPDQUBBDOLHXSU-UHFFFAOYSA-N 0.000 claims description 2
- JCKDYXIELCUBEV-UHFFFAOYSA-N 1-(2-chloro-1,3-benzothiazol-6-yl)-1-imidazol-1-yl-n,n-dimethylbutan-2-amine Chemical compound C=1C=C2N=C(Cl)SC2=CC=1C(C(CC)N(C)C)N1C=CN=C1 JCKDYXIELCUBEV-UHFFFAOYSA-N 0.000 claims description 2
- JGYYFGDZCOAZOP-UHFFFAOYSA-N 1-[6-(2-ethyl-1-imidazol-1-ylbutyl)-1,3-benzothiazol-2-yl]-2,2,2-trifluoroethanone Chemical compound C=1C=C2N=C(C(=O)C(F)(F)F)SC2=CC=1C(C(CC)CC)N1C=CN=C1 JGYYFGDZCOAZOP-UHFFFAOYSA-N 0.000 claims description 2
- QGCDRPBXUYQIBS-UHFFFAOYSA-N 1-[[6-[2-(dimethylamino)-1-imidazol-1-ylbutyl]-1,3-benzothiazol-2-yl]carbamoyl]cyclobutane-1-carboxylic acid Chemical compound C1=CN=CN1C(C(CC)N(C)C)C(C=C1S2)=CC=C1N=C2NC(=O)C1(C(O)=O)CCC1 QGCDRPBXUYQIBS-UHFFFAOYSA-N 0.000 claims description 2
- NHWGJSDAMWJWHN-UHFFFAOYSA-N 1-[[6-[2-(dimethylamino)-1-imidazol-1-ylbutyl]-1,3-benzothiazol-2-yl]carbamoyl]cyclohexane-1-carboxylic acid Chemical compound C1=CN=CN1C(C(CC)N(C)C)C(C=C1S2)=CC=C1N=C2NC(=O)C1(C(O)=O)CCCCC1 NHWGJSDAMWJWHN-UHFFFAOYSA-N 0.000 claims description 2
- LJRYOVRPNXTGEC-UHFFFAOYSA-N 1-imidazol-1-yl-1-(2-methoxy-1,3-benzothiazol-6-yl)-n,n-dimethylbutan-2-amine Chemical compound C=1C=C2N=C(OC)SC2=CC=1C(C(CC)N(C)C)N1C=CN=C1 LJRYOVRPNXTGEC-UHFFFAOYSA-N 0.000 claims description 2
- RCCLPZBYJMYUJS-UHFFFAOYSA-N 1-imidazol-1-yl-n,n-dimethyl-1-(2-methyl-1,3-benzothiazol-6-yl)butan-2-amine Chemical compound C=1C=C2N=C(C)SC2=CC=1C(C(CC)N(C)C)N1C=CN=C1 RCCLPZBYJMYUJS-UHFFFAOYSA-N 0.000 claims description 2
- VULULFSTJUFKHG-UHFFFAOYSA-N 1-imidazol-1-yl-n,n-dimethyl-1-(2-phenyl-1,3-benzothiazol-6-yl)butan-2-amine Chemical compound C1=CN=CN1C(C(CC)N(C)C)C(C=C1S2)=CC=C1N=C2C1=CC=CC=C1 VULULFSTJUFKHG-UHFFFAOYSA-N 0.000 claims description 2
- GNBKLPOTMKWAJC-UHFFFAOYSA-N 2-[6-[2-(dimethylamino)-1-imidazol-1-ylbutyl]-1,3-benzothiazol-2-yl]acetic acid Chemical compound C=1C=C2N=C(CC(O)=O)SC2=CC=1C(C(CC)N(C)C)N1C=CN=C1 GNBKLPOTMKWAJC-UHFFFAOYSA-N 0.000 claims description 2
- LDYAJRGZEQBWIK-UHFFFAOYSA-N 2-bromo-6-(2-ethyl-1-imidazol-1-ylbutyl)-1,3-benzothiazole Chemical compound C=1C=C2N=C(Br)SC2=CC=1C(C(CC)CC)N1C=CN=C1 LDYAJRGZEQBWIK-UHFFFAOYSA-N 0.000 claims description 2
- BFHLQEKBYQJQKB-UHFFFAOYSA-N 2-chloro-4-[6-[2-(dimethylamino)-1-imidazol-1-ylbutyl]-1,3-benzothiazol-2-yl]benzoic acid Chemical compound C1=CN=CN1C(C(CC)N(C)C)C(C=C1S2)=CC=C1N=C2C1=CC=C(C(O)=O)C(Cl)=C1 BFHLQEKBYQJQKB-UHFFFAOYSA-N 0.000 claims description 2
- FQJDZAPDELSHIS-UHFFFAOYSA-N 3-[6-(2-ethyl-1-imidazol-1-ylbutyl)-1,3-benzothiazol-2-yl]benzoic acid Chemical compound C1=CN=CN1C(C(CC)CC)C(C=C1S2)=CC=C1N=C2C1=CC=CC(C(O)=O)=C1 FQJDZAPDELSHIS-UHFFFAOYSA-N 0.000 claims description 2
- OEIQLHWNMUJYHS-UHFFFAOYSA-N 3-[6-[2-(dimethylamino)-1-imidazol-1-ylbutyl]-1,3-benzothiazol-2-yl]-5-(trifluoromethyl)benzoic acid Chemical compound C1=CN=CN1C(C(CC)N(C)C)C(C=C1S2)=CC=C1N=C2C1=CC(C(O)=O)=CC(C(F)(F)F)=C1 OEIQLHWNMUJYHS-UHFFFAOYSA-N 0.000 claims description 2
- ZDVOWUOODNSXJO-UHFFFAOYSA-N 3-[6-[2-(dimethylamino)-1-imidazol-1-ylbutyl]-1,3-benzothiazol-2-yl]-5-fluorobenzoic acid Chemical compound C1=CN=CN1C(C(CC)N(C)C)C(C=C1S2)=CC=C1N=C2C1=CC(F)=CC(C(O)=O)=C1 ZDVOWUOODNSXJO-UHFFFAOYSA-N 0.000 claims description 2
- KPUAYWZGXUAEBE-UHFFFAOYSA-N 3-[6-[2-(dimethylamino)-1-imidazol-1-ylbutyl]-1,3-benzothiazol-2-yl]benzoic acid Chemical compound C1=CN=CN1C(C(CC)N(C)C)C(C=C1S2)=CC=C1N=C2C1=CC=CC(C(O)=O)=C1 KPUAYWZGXUAEBE-UHFFFAOYSA-N 0.000 claims description 2
- FKDCHUXQDDCAEJ-UHFFFAOYSA-N 3-[6-[2-[ethyl(methyl)amino]-1-imidazol-1-ylbutyl]-1,3-benzothiazol-2-yl]benzoic acid Chemical compound C1=CN=CN1C(C(CC)N(C)CC)C(C=C1S2)=CC=C1N=C2C1=CC=CC(C(O)=O)=C1 FKDCHUXQDDCAEJ-UHFFFAOYSA-N 0.000 claims description 2
- LOOHZLWDUCGPBR-UHFFFAOYSA-N 3-[[6-[2-(dimethylamino)-1-imidazol-1-ylbutyl]-1,3-benzothiazol-2-yl]amino]-2,2-dimethylpropanoic acid Chemical compound C=1C=C2N=C(NCC(C)(C)C(O)=O)SC2=CC=1C(C(CC)N(C)C)N1C=CN=C1 LOOHZLWDUCGPBR-UHFFFAOYSA-N 0.000 claims description 2
- OOAWVDIGJDERNR-UHFFFAOYSA-N 3-[[6-[2-(dimethylamino)-1-imidazol-1-ylbutyl]-1,3-benzothiazol-2-yl]oxy]benzoic acid Chemical compound C1=CN=CN1C(C(CC)N(C)C)C(C=C1S2)=CC=C1N=C2OC1=CC=CC(C(O)=O)=C1 OOAWVDIGJDERNR-UHFFFAOYSA-N 0.000 claims description 2
- UJGGYRIRLWGBMG-UHFFFAOYSA-N 3-[[[6-[2-(dimethylamino)-1-imidazol-1-ylbutyl]-1,3-benzothiazol-2-yl]amino]methyl]benzoic acid Chemical compound C1=CN=CN1C(C(CC)N(C)C)C(C=C1S2)=CC=C1N=C2NCC1=CC=CC(C(O)=O)=C1 UJGGYRIRLWGBMG-UHFFFAOYSA-N 0.000 claims description 2
- ZEIPRKIQOOCGLI-UHFFFAOYSA-N 4-[6-(1-pyridin-3-ylbutyl)-1,3-benzothiazol-2-yl]benzoic acid Chemical compound C=1C=C2N=C(C=3C=CC(=CC=3)C(O)=O)SC2=CC=1C(CCC)C1=CC=CN=C1 ZEIPRKIQOOCGLI-UHFFFAOYSA-N 0.000 claims description 2
- WHPYXXUMTGCWCS-UHFFFAOYSA-N 4-[6-[2-(dimethylamino)-1-imidazol-1-ylbutyl]-1,3-benzothiazol-2-yl]benzoic acid Chemical compound C1=CN=CN1C(C(CC)N(C)C)C(C=C1S2)=CC=C1N=C2C1=CC=C(C(O)=O)C=C1 WHPYXXUMTGCWCS-UHFFFAOYSA-N 0.000 claims description 2
- KSWQNQUJQMLYOB-UHFFFAOYSA-N 4-[6-[2-[ethyl(methyl)amino]-1-imidazol-1-ylbutyl]-1,3-benzothiazol-2-yl]benzoic acid Chemical compound C1=CN=CN1C(C(CC)N(C)CC)C(C=C1S2)=CC=C1N=C2C1=CC=C(C(O)=O)C=C1 KSWQNQUJQMLYOB-UHFFFAOYSA-N 0.000 claims description 2
- KYJVJNHAIFMYSS-UHFFFAOYSA-N 4-[[6-[2-(dimethylamino)-1-imidazol-1-ylbutyl]-1,3-benzothiazol-2-yl]amino]benzoic acid Chemical compound C1=CN=CN1C(C(CC)N(C)C)C(C=C1S2)=CC=C1N=C2NC1=CC=C(C(O)=O)C=C1 KYJVJNHAIFMYSS-UHFFFAOYSA-N 0.000 claims description 2
- OGZDCMDCBFXSCG-UHFFFAOYSA-N 5-[6-[2-(dimethylamino)-1-imidazol-1-ylbutyl]-1,3-benzothiazol-2-yl]-2-fluorobenzoic acid Chemical compound C1=CN=CN1C(C(CC)N(C)C)C(C=C1S2)=CC=C1N=C2C1=CC=C(F)C(C(O)=O)=C1 OGZDCMDCBFXSCG-UHFFFAOYSA-N 0.000 claims description 2
- UYSJFJHNKLFGEC-UHFFFAOYSA-N 5-[[6-[2-(dimethylamino)-1-imidazol-1-ylbutyl]-1,3-benzothiazol-2-yl]amino]-2,2-dimethyl-5-oxopentanoic acid Chemical compound C=1C=C2N=C(NC(=O)CCC(C)(C)C(O)=O)SC2=CC=1C(C(CC)N(C)C)N1C=CN=C1 UYSJFJHNKLFGEC-UHFFFAOYSA-N 0.000 claims description 2
- FZSGKXIMHTXRHT-UHFFFAOYSA-N 6-(2-ethyl-1-imidazol-1-ylbutyl)-1,3-benzothiazol-2-amine Chemical compound C=1C=C2N=C(N)SC2=CC=1C(C(CC)CC)N1C=CN=C1 FZSGKXIMHTXRHT-UHFFFAOYSA-N 0.000 claims description 2
- QIVZMHJMGXZVDW-UHFFFAOYSA-N 6-(2-ethyl-1-imidazol-1-ylbutyl)-2-methoxy-1,3-benzothiazole Chemical compound C=1C=C2N=C(OC)SC2=CC=1C(C(CC)CC)N1C=CN=C1 QIVZMHJMGXZVDW-UHFFFAOYSA-N 0.000 claims description 2
- FPMSDQMOARJLDT-UHFFFAOYSA-N 6-(2-ethyl-1-imidazol-1-ylbutyl)-2-methyl-1,3-benzothiazole Chemical compound C=1C=C2N=C(C)SC2=CC=1C(C(CC)CC)N1C=CN=C1 FPMSDQMOARJLDT-UHFFFAOYSA-N 0.000 claims description 2
- NKIYHLAXRAPEAD-UHFFFAOYSA-N 6-(2-ethyl-1-imidazol-1-ylbutyl)-2-phenyl-1,3-benzothiazole Chemical compound C1=CN=CN1C(C(CC)CC)C(C=C1S2)=CC=C1N=C2C1=CC=CC=C1 NKIYHLAXRAPEAD-UHFFFAOYSA-N 0.000 claims description 2
- KSWNDVYYKAZRBO-UHFFFAOYSA-N 6-(2-ethyl-1-imidazol-1-ylbutyl)-3h-1,3-benzothiazol-2-one Chemical compound C=1C=C2NC(=O)SC2=CC=1C(C(CC)CC)N1C=CN=C1 KSWNDVYYKAZRBO-UHFFFAOYSA-N 0.000 claims description 2
- WMNCAFNXKGXTAZ-UHFFFAOYSA-N 6-[2-(dimethylamino)-1-imidazol-1-ylbutyl]-1,3-benzothiazole-2-carboxylic acid Chemical compound C=1C=C2N=C(C(O)=O)SC2=CC=1C(C(CC)N(C)C)N1C=CN=C1 WMNCAFNXKGXTAZ-UHFFFAOYSA-N 0.000 claims description 2
- BBFRANNPLCDNLZ-UHFFFAOYSA-N 6-[2-(dimethylamino)-1-imidazol-1-ylbutyl]-3h-1,3-benzothiazol-2-one Chemical compound C=1C=C2NC(=O)SC2=CC=1C(C(CC)N(C)C)N1C=CN=C1 BBFRANNPLCDNLZ-UHFFFAOYSA-N 0.000 claims description 2
- KROYNGOCCMKBOS-UHFFFAOYSA-N [6-[2-(dimethylamino)-1-imidazol-1-ylbutyl]-1,3-benzothiazol-2-yl]urea Chemical compound C=1C=C2N=C(NC(N)=O)SC2=CC=1C(C(CC)N(C)C)N1C=CN=C1 KROYNGOCCMKBOS-UHFFFAOYSA-N 0.000 claims description 2
- 239000003098 androgen Substances 0.000 claims description 2
- 230000003510 anti-fibrotic effect Effects 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 229940011871 estrogen Drugs 0.000 claims description 2
- 239000000262 estrogen Substances 0.000 claims description 2
- TZZJJANDAVVBND-UHFFFAOYSA-N methyl 6-[2-(dimethylamino)-1-imidazol-1-ylbutyl]-1,3-benzothiazole-2-carboximidate Chemical compound C=1C=C2N=C(C(=N)OC)SC2=CC=1C(C(CC)N(C)C)N1C=CN=C1 TZZJJANDAVVBND-UHFFFAOYSA-N 0.000 claims description 2
- OCHXMGXJQSBNGG-UHFFFAOYSA-N n-[6-[2-(dimethylamino)-1-imidazol-1-ylbutyl]-1,3-benzothiazol-2-yl]bicyclo[2.2.1]heptane-3-carboxamide Chemical compound C=1C=C2N=C(NC(=O)C3C4CCC(C4)C3)SC2=CC=1C(C(CC)N(C)C)N1C=CN=C1 OCHXMGXJQSBNGG-UHFFFAOYSA-N 0.000 claims description 2
- NLZSGUJHCRCXRU-UHFFFAOYSA-N n-[6-[2-[ethyl(methyl)amino]-1-imidazol-1-ylbutyl]-1,3-benzothiazol-2-yl]acetamide Chemical compound C=1C=C2N=C(NC(C)=O)SC2=CC=1C(C(CC)N(C)CC)N1C=CN=C1 NLZSGUJHCRCXRU-UHFFFAOYSA-N 0.000 claims description 2
- HNBDRPTVWVGKBR-UHFFFAOYSA-N n-pentanoic acid methyl ester Natural products CCCCC(=O)OC HNBDRPTVWVGKBR-UHFFFAOYSA-N 0.000 claims description 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 2
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| EP2760854B1 (en) * | 2011-09-30 | 2017-08-30 | Asana BioSciences, LLC | Imidazole derivatives as cyp17 inhibitors for the treatment of cancer |
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| JP2018501279A (ja) | 2014-12-31 | 2018-01-18 | アンギオン バイオメディカ コーポレイション | 疾患を治療するための方法及び薬剤 |
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| JP7160487B2 (ja) | 2017-05-04 | 2022-10-25 | ビーエーエスエフ ソシエタス・ヨーロピア | 植物病原菌を駆除するための置換5-(ハロアルキル)-5-ヒドロキシ-イソオキサゾール |
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| FR2860235A1 (fr) * | 2003-09-29 | 2005-04-01 | Yang Ji Chemical Company Ltd | Utilisation d'un compose de formule (i) inhibiteur de l'aromatase a des fins therapeutiques et composes de formule (i) en tant que tels |
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