JP2013527238A5 - - Google Patents
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- JP2013527238A5 JP2013527238A5 JP2013513284A JP2013513284A JP2013527238A5 JP 2013527238 A5 JP2013527238 A5 JP 2013527238A5 JP 2013513284 A JP2013513284 A JP 2013513284A JP 2013513284 A JP2013513284 A JP 2013513284A JP 2013527238 A5 JP2013527238 A5 JP 2013527238A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- alkenyl
- imidazol
- butyl
- benzo
- 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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- 125000000217 alkyl group Chemical group 0.000 claims 127
- 125000000304 alkynyl group Chemical group 0.000 claims 66
- 125000005843 halogen group Chemical group 0.000 claims 56
- -1 4-pyridinyl Chemical group 0.000 claims 53
- 125000003342 alkenyl group Chemical group 0.000 claims 41
- 125000001424 substituent group Chemical group 0.000 claims 24
- 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 22
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 22
- 125000003118 aryl group Chemical group 0.000 claims 21
- 150000001875 compounds Chemical class 0.000 claims 19
- 125000004093 cyano group Chemical group *C#N 0.000 claims 19
- 125000003545 alkoxy group Chemical group 0.000 claims 17
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 17
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 16
- 125000000623 heterocyclic group Chemical group 0.000 claims 16
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 claims 15
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims 12
- 125000004414 alkyl thio group Chemical group 0.000 claims 12
- 229920006395 saturated elastomer Polymers 0.000 claims 11
- 125000001072 heteroaryl group Chemical group 0.000 claims 9
- 229910052739 hydrogen Inorganic materials 0.000 claims 9
- 239000001257 hydrogen Substances 0.000 claims 9
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 9
- 229940095102 methyl benzoate Drugs 0.000 claims 9
- 125000006620 amino-(C1-C6) alkyl group Chemical group 0.000 claims 8
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims 8
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 8
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 7
- 229910052757 nitrogen Inorganic materials 0.000 claims 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 6
- 206010016654 Fibrosis Diseases 0.000 claims 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 6
- 239000005711 Benzoic acid Substances 0.000 claims 5
- 235000010233 benzoic acid Nutrition 0.000 claims 5
- 230000004761 fibrosis Effects 0.000 claims 5
- 210000000056 organ Anatomy 0.000 claims 5
- 125000004432 carbon atom Chemical group C* 0.000 claims 4
- 201000010099 disease Diseases 0.000 claims 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 4
- 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 claims 4
- 238000000034 method Methods 0.000 claims 4
- 206010063837 Reperfusion injury Diseases 0.000 claims 3
- UOTCXIMRODXHSV-UHFFFAOYSA-N [2,3-dihydroxy-4-(2-methylsulfonyloxyethylazaniumyl)butyl]-(2-methylsulfonyloxyethyl)azanium;dichloride Chemical compound [Cl-].[Cl-].CS(=O)(=O)OCC[NH2+]CC(O)C(O)C[NH2+]CCOS(C)(=O)=O UOTCXIMRODXHSV-UHFFFAOYSA-N 0.000 claims 3
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims 3
- 125000002877 alkyl aryl group Chemical group 0.000 claims 3
- 229910052799 carbon Inorganic materials 0.000 claims 3
- 230000001684 chronic effect Effects 0.000 claims 3
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 3
- 230000000302 ischemic effect Effects 0.000 claims 3
- 125000002950 monocyclic group Chemical group 0.000 claims 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- 125000003367 polycyclic group Chemical group 0.000 claims 3
- 125000006619 (C1-C6) dialkylamino group Chemical group 0.000 claims 2
- RNKWNTBATDIXFT-UHFFFAOYSA-N 2-chloro-4-[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=C(C(O)=O)C(Cl)=C1 RNKWNTBATDIXFT-UHFFFAOYSA-N 0.000 claims 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 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 2
- FEXQDZTYJVXMOS-UHFFFAOYSA-N Isopropyl benzoate Chemical compound CC(C)OC(=O)C1=CC=CC=C1 FEXQDZTYJVXMOS-UHFFFAOYSA-N 0.000 claims 2
- KPCZJLGGXRGYIE-UHFFFAOYSA-N [C]1=CC=CN=C1 Chemical group [C]1=CC=CN=C1 KPCZJLGGXRGYIE-UHFFFAOYSA-N 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 2
- 125000005090 alkenylcarbonyl group Chemical group 0.000 claims 2
- 125000005087 alkynylcarbonyl group Chemical group 0.000 claims 2
- 125000005605 benzo group Chemical group 0.000 claims 2
- 208000026106 cerebrovascular disease Diseases 0.000 claims 2
- 208000019425 cirrhosis of liver Diseases 0.000 claims 2
- 206010012601 diabetes mellitus Diseases 0.000 claims 2
- MTZQAGJQAFMTAQ-UHFFFAOYSA-N ethyl benzoate Chemical compound CCOC(=O)C1=CC=CC=C1 MTZQAGJQAFMTAQ-UHFFFAOYSA-N 0.000 claims 2
- 229910052736 halogen Inorganic materials 0.000 claims 2
- 150000002367 halogens Chemical class 0.000 claims 2
- 125000002883 imidazolyl group Chemical group 0.000 claims 2
- 208000014674 injury Diseases 0.000 claims 2
- 208000028867 ischemia Diseases 0.000 claims 2
- 210000003734 kidney Anatomy 0.000 claims 2
- 208000017169 kidney disease Diseases 0.000 claims 2
- 210000004185 liver Anatomy 0.000 claims 2
- 208000031225 myocardial ischemia Diseases 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- BHRZNVHARXXAHW-UHFFFAOYSA-N sec-butylamine Chemical compound CCC(C)N BHRZNVHARXXAHW-UHFFFAOYSA-N 0.000 claims 2
- 230000008733 trauma Effects 0.000 claims 2
- 125000001425 triazolyl group Chemical group 0.000 claims 2
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 1
- QWEWLLNSJDTOKH-UHFFFAOYSA-N 1,3-thiazole-2-carboxamide Chemical compound NC(=O)C1=NC=CS1 QWEWLLNSJDTOKH-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- ZWUSOMDXGBKQQR-UHFFFAOYSA-N 1-(2-chloro-1,3-benzothiazol-6-yl)-n-ethyl-1-imidazol-1-yl-n-methylbutan-2-amine Chemical compound C=1C=C2N=C(Cl)SC2=CC=1C(C(CC)N(C)CC)N1C=CN=C1 ZWUSOMDXGBKQQR-UHFFFAOYSA-N 0.000 claims 1
- AYULVHVIIWSOBL-OMOCHNIRSA-N 1-[[6-[(1r)-2-(dimethylamino)-1-imidazol-1-ylbutyl]-1,3-benzothiazol-2-yl]carbamoyl]cyclopropane-1-carboxylic acid Chemical compound S1C2=CC([C@H](C(CC)N(C)C)N3C=NC=C3)=CC=C2N=C1NC(=O)C1(C(O)=O)CC1 AYULVHVIIWSOBL-OMOCHNIRSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- XLUXAKJPHJEFKL-UHFFFAOYSA-N 1-ethylcyclobutane-1-carboxylic acid Chemical compound CCC1(C(O)=O)CCC1 XLUXAKJPHJEFKL-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- XEWQDSIIUGLDRX-UHFFFAOYSA-N 1-imidazol-1-yl-n,n-dimethyl-1-[2-[3-(2h-tetrazol-5-yl)phenyl]-1,3-benzothiazol-6-yl]butan-2-amine Chemical compound C1=CN=CN1C(C(CC)N(C)C)C(C=C1S2)=CC=C1N=C2C(C=1)=CC=CC=1C=1N=NNN=1 XEWQDSIIUGLDRX-UHFFFAOYSA-N 0.000 claims 1
- QGQJQAKOVICLQZ-UHFFFAOYSA-N 1-imidazol-1-yl-n,n-dimethyl-1-[2-[4-(2h-tetrazol-5-yl)phenyl]-1,3-benzothiazol-6-yl]butan-2-amine Chemical compound C1=CN=CN1C(C(CC)N(C)C)C(C=C1S2)=CC=C1N=C2C(C=C1)=CC=C1C=1N=NNN=1 QGQJQAKOVICLQZ-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- GSXIVQKLNBAZSE-UHFFFAOYSA-N 2-[6-[2-(dimethylamino)-1-imidazol-1-ylbutyl]-1,3-benzothiazol-2-yl]benzoic acid Chemical compound CCC(C(c1ccc2nc(sc2c1)-c1ccccc1C(O)=O)n1ccnc1)N(C)C GSXIVQKLNBAZSE-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- XYMXCVVUSOSGRG-UHFFFAOYSA-N 2-chloro-5-[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=C(Cl)C(C(O)=O)=C1 XYMXCVVUSOSGRG-UHFFFAOYSA-N 0.000 claims 1
- WXIKZYNGZGRVRO-UHFFFAOYSA-N 2-chloro-5-[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(Cl)C(C(O)=O)=C1 WXIKZYNGZGRVRO-UHFFFAOYSA-N 0.000 claims 1
- DEOUZFWSQWEPGE-UHFFFAOYSA-N 2-methylheptanamide Chemical compound CCCCCC(C)C(N)=O DEOUZFWSQWEPGE-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- AJGLDNVLIGGCIM-UHFFFAOYSA-N 3-[[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=CC(C(O)=O)=C1 AJGLDNVLIGGCIM-UHFFFAOYSA-N 0.000 claims 1
- AUCZUUGNMKGAHR-UHFFFAOYSA-N 3-[[6-[2-(dimethylamino)-1-imidazol-1-ylbutyl]-1,3-benzothiazol-2-yl]carbamoyl]benzoic acid Chemical compound C1=CN=CN1C(C(CC)N(C)C)C(C=C1S2)=CC=C1N=C2NC(=O)C1=CC=CC(C(O)=O)=C1 AUCZUUGNMKGAHR-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- URHMHWOYSYSNNF-UHFFFAOYSA-N 4-[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=C(C(O)=O)C=C1 URHMHWOYSYSNNF-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- DFUMDGZPTOOHPY-UHFFFAOYSA-N 4-[[6-[2-(dimethylamino)-1-imidazol-1-ylbutyl]-1,3-benzothiazol-2-yl]carbamoyl]benzoic acid Chemical compound C1=CN=CN1C(C(CC)N(C)C)C(C=C1S2)=CC=C1N=C2NC(=O)C1=CC=C(C(O)=O)C=C1 DFUMDGZPTOOHPY-UHFFFAOYSA-N 0.000 claims 1
- DMYUSYNHOWDVBR-UHFFFAOYSA-N 4-[[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=C(C(O)=O)C=C1 DMYUSYNHOWDVBR-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- QZHFPESYLONIMY-UHFFFAOYSA-N 6-(2-ethyl-1-imidazol-1-ylbutyl)-1,3-benzothiazole-2-carboxylic acid Chemical compound C=1C=C2N=C(C(O)=O)SC2=CC=1C(C(CC)CC)N1C=CN=C1 QZHFPESYLONIMY-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- OTTGUSLSDBMAJI-UHFFFAOYSA-N 6-[2-(dimethylamino)-1-imidazol-1-ylbutyl]-1,3-benzothiazol-2-amine Chemical compound C=1C=C2N=C(N)SC2=CC=1C(C(CC)N(C)C)N1C=CN=C1 OTTGUSLSDBMAJI-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- LRRVGYBBMPKZIM-UHFFFAOYSA-N 6-[2-[ethyl(methyl)amino]-1-imidazol-1-ylbutyl]-1,3-benzothiazol-2-amine Chemical compound C=1C=C2N=C(N)SC2=CC=1C(C(CC)N(C)CC)N1C=CN=C1 LRRVGYBBMPKZIM-UHFFFAOYSA-N 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims 1
- 208000007848 Alcoholism Diseases 0.000 claims 1
- 208000011403 Alexander disease Diseases 0.000 claims 1
- 208000024827 Alzheimer disease Diseases 0.000 claims 1
- 102100022146 Arylsulfatase A Human genes 0.000 claims 1
- 201000001320 Atherosclerosis Diseases 0.000 claims 1
- 208000008439 Biliary Liver Cirrhosis Diseases 0.000 claims 1
- 208000015163 Biliary Tract disease Diseases 0.000 claims 1
- 208000033222 Biliary cirrhosis primary Diseases 0.000 claims 1
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| US10414760B2 (en) | 2016-11-29 | 2019-09-17 | Angion Biomedica Corp. | Cytochrome P450 inhibitors and uses thereof |
| US8809372B2 (en) | 2011-09-30 | 2014-08-19 | Asana Biosciences, Llc | Pyridine derivatives |
| WO2013049565A1 (en) * | 2011-09-30 | 2013-04-04 | Endo Pharmaceuticals Inc. | Imidazole derivatives as cyp17 inhibitors for the treatment of cancer |
| US9199975B2 (en) | 2011-09-30 | 2015-12-01 | Asana Biosciences, Llc | Biaryl imidazole derivatives for regulating CYP17 |
| AU2012322095B2 (en) | 2011-10-14 | 2017-06-29 | Ambit Biosciences Corporation | Heterocyclic compounds and use thereof as modulators of type III receptor tyrosine kinases |
| WO2014015137A2 (en) * | 2012-07-18 | 2014-01-23 | Angion Biomedica Corp. | Compositions and methods for treating dysproliferative diseases |
| JO3225B1 (ar) * | 2012-11-27 | 2018-03-08 | Lilly Co Eli | 6-((s)-1-{1-[5-(2-هيدروكسي-إيثوكسي)-بيريدين-2-يل]-1h-بيرازول-3-يل}إيثيل)-3h-1 ، 3-بنزو ثيازول-2- أون باعتباره مضاد مستقبل ampa يعتمد على tarp- جاما 8 |
| WO2014093960A1 (en) * | 2012-12-16 | 2014-06-19 | Angion Biomedica Corp. | Compositions and methods for treating disease |
| EP3180335B1 (en) | 2014-08-11 | 2021-05-05 | Angion Biomedica Corporation | Cytochrome p450 inhibitors and uses thereof |
| CA2970819A1 (en) * | 2014-12-31 | 2016-07-07 | Angion Biomedica Corp. | Methods and agents for treating disease |
| GB201602572D0 (en) * | 2016-02-12 | 2016-03-30 | Eriksson Leif And Strid Ake And Sirsjö Allan | New compound and uses |
| 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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| KR20020084116A (ko) * | 2000-02-07 | 2002-11-04 | 애보트 게엠베하 운트 콤파니 카게 | 2-벤조티아졸릴 우레아 유도체 및 이의 단백질 키나제억제제로서의 용도 |
| CA2415169C (en) | 2000-07-11 | 2010-06-01 | University Of Maryland, Baltimore | Novel c-4 substituted retinoids |
| WO2002051821A1 (en) * | 2000-12-22 | 2002-07-04 | Astrazeneca Ab | Therapeutic compounds |
| TWI286476B (en) * | 2001-12-12 | 2007-09-11 | Tibotec Pharm Ltd | Combination of cytochrome P450 dependent protease inhibitors |
| CN1742007A (zh) * | 2003-01-22 | 2006-03-01 | 伊莱利利公司 | 甾族激素核受体的吲哚衍生物调控剂 |
| GB0314733D0 (en) * | 2003-06-24 | 2003-07-30 | Glaxo Group Ltd | Medicaments |
| MXPA06000401A (es) | 2003-07-10 | 2006-03-17 | Osi Pharm Inc | Derivados de naftileno como inhibidores de citocromo p450. |
| 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 |
| KR101160368B1 (ko) * | 2004-05-19 | 2012-06-26 | 클라리언트 파이넌스 (비브이아이)리미티드 | 연결된 모노아조 염료 |
| KR101083177B1 (ko) * | 2006-10-23 | 2011-11-11 | 에스지엑스 파마슈티컬스, 인코포레이티드 | 트리아졸로-피리다진 단백질 키나제 조정제 |
| CA2693232A1 (en) * | 2007-07-18 | 2009-01-22 | Novartis Ag | Bicyclic heteroaryl compounds and their use as kinase inhibitors |
| TW200911798A (en) * | 2007-08-02 | 2009-03-16 | Amgen Inc | PI3 kinase modulators and methods of use |
| BRPI0818003A2 (pt) * | 2007-10-18 | 2019-09-24 | Novartis Ag | inibidores de csf-1r, composições e métodos de uso |
| WO2010036404A2 (en) | 2008-05-09 | 2010-04-01 | University Of Maryland, Baltimore | Novel retinamide retinoic acid metabolism blocking agents |
| GB0811091D0 (en) | 2008-06-17 | 2008-07-23 | Cancer Rec Tech Ltd | CYP26 Inhibitors |
| US8987315B2 (en) | 2009-12-31 | 2015-03-24 | Innocrin Pharmaceuticals, Inc. | Metalloenzyme inhibitor compounds |
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- 2011-06-01 US US13/700,730 patent/US8513291B2/en not_active Expired - Fee Related
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- 2011-06-01 CN CN201180034394.7A patent/CN102985420B/zh not_active Expired - Fee Related
- 2011-06-01 JP JP2013513284A patent/JP6088425B2/ja not_active Expired - Fee Related
- 2011-06-01 AU AU2011261586A patent/AU2011261586B2/en not_active Ceased
- 2011-06-01 WO PCT/US2011/038695 patent/WO2011153192A2/en not_active Ceased
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2012
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2013
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2014
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