JP2008517976A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2008517976A5 JP2008517976A5 JP2007538405A JP2007538405A JP2008517976A5 JP 2008517976 A5 JP2008517976 A5 JP 2008517976A5 JP 2007538405 A JP2007538405 A JP 2007538405A JP 2007538405 A JP2007538405 A JP 2007538405A JP 2008517976 A5 JP2008517976 A5 JP 2008517976A5
- Authority
- JP
- Japan
- Prior art keywords
- chlorophenyl
- carboxamide
- dichlorophenyl
- phenyl
- pyrazole
- 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.)
- Pending
Links
- 108091006146 Channels Proteins 0.000 claims 34
- 150000001875 compounds Chemical class 0.000 claims 21
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 21
- 239000005557 antagonist Substances 0.000 claims 20
- 239000008194 pharmaceutical composition Substances 0.000 claims 16
- FCTRVTQZOUKUIV-MCDZGGTQSA-M potassium;[[[(2r,3s,4r,5r)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-hydroxyphosphoryl] hydrogen phosphate Chemical compound [K+].C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)OP(O)([O-])=O)[C@@H](O)[C@H]1O FCTRVTQZOUKUIV-MCDZGGTQSA-M 0.000 claims 16
- 230000003042 antagnostic effect Effects 0.000 claims 14
- 230000009977 dual effect Effects 0.000 claims 11
- 239000003814 drug Substances 0.000 claims 9
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 8
- 208000001145 Metabolic Syndrome Diseases 0.000 claims 7
- 239000002552 dosage form Substances 0.000 claims 7
- 238000004519 manufacturing process Methods 0.000 claims 7
- 230000002265 prevention Effects 0.000 claims 7
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims 7
- 230000002422 KATP channel opening effect Effects 0.000 claims 6
- 208000008589 Obesity Diseases 0.000 claims 6
- 229910052739 hydrogen Inorganic materials 0.000 claims 6
- 239000001257 hydrogen Substances 0.000 claims 6
- 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 6
- 235000020824 obesity Nutrition 0.000 claims 6
- -1 propionyloxy Chemical group 0.000 claims 6
- 201000000690 abdominal obesity-metabolic syndrome Diseases 0.000 claims 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 5
- 230000001629 suppression Effects 0.000 claims 5
- 102100021177 ATP-sensitive inward rectifier potassium channel 11 Human genes 0.000 claims 4
- 101000614701 Homo sapiens ATP-sensitive inward rectifier potassium channel 11 Proteins 0.000 claims 4
- 241000124008 Mammalia Species 0.000 claims 4
- 206010012601 diabetes mellitus Diseases 0.000 claims 4
- 150000002431 hydrogen Chemical class 0.000 claims 4
- 230000004580 weight loss Effects 0.000 claims 4
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims 3
- 102100024645 ATP-binding cassette sub-family C member 8 Human genes 0.000 claims 3
- 101000760570 Homo sapiens ATP-binding cassette sub-family C member 8 Proteins 0.000 claims 3
- 102000004877 Insulin Human genes 0.000 claims 3
- 108090001061 Insulin Proteins 0.000 claims 3
- 206010022489 Insulin Resistance Diseases 0.000 claims 3
- 239000013543 active substance Substances 0.000 claims 3
- 125000000217 alkyl group Chemical group 0.000 claims 3
- 229940125396 insulin Drugs 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- 239000000203 mixture Substances 0.000 claims 3
- 125000004076 pyridyl group Chemical group 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- 208000011580 syndromic disease Diseases 0.000 claims 3
- AXJQVVLKUYCICH-OAQYLSRUSA-N (4s)-5-(4-chlorophenyl)-n-(4-chlorophenyl)sulfonyl-n'-methyl-4-phenyl-3,4-dihydropyrazole-2-carboximidamide Chemical compound C=1C=C(Cl)C=CC=1C([C@H](C1)C=2C=CC=CC=2)=NN1C(=NC)NS(=O)(=O)C1=CC=C(Cl)C=C1 AXJQVVLKUYCICH-OAQYLSRUSA-N 0.000 claims 2
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 2
- HMXDWDSNPRNUKI-UHFFFAOYSA-N 5-(4-bromophenyl)-1-(2,4-dichlorophenyl)-4-ethyl-N-(1-piperidinyl)-3-pyrazolecarboxamide Chemical group CCC=1C(C(=O)NN2CCCCC2)=NN(C=2C(=CC(Cl)=CC=2)Cl)C=1C1=CC=C(Br)C=C1 HMXDWDSNPRNUKI-UHFFFAOYSA-N 0.000 claims 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 102000004895 Lipoproteins Human genes 0.000 claims 2
- 108090001030 Lipoproteins Proteins 0.000 claims 2
- 206010067584 Type 1 diabetes mellitus Diseases 0.000 claims 2
- 201000010390 abdominal obesity-metabolic syndrome 1 Diseases 0.000 claims 2
- 230000005856 abnormality Effects 0.000 claims 2
- 239000000654 additive Substances 0.000 claims 2
- 230000000996 additive effect Effects 0.000 claims 2
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 claims 2
- GDLBFKVLRPITMI-UHFFFAOYSA-N diazoxide Chemical compound ClC1=CC=C2NC(C)=NS(=O)(=O)C2=C1 GDLBFKVLRPITMI-UHFFFAOYSA-N 0.000 claims 2
- 229960004042 diazoxide Drugs 0.000 claims 2
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 claims 2
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- 230000002401 inhibitory effect Effects 0.000 claims 2
- 208000011661 metabolic syndrome X Diseases 0.000 claims 2
- XWCFBKQZEWEFOD-UHFFFAOYSA-N n-(3-methylbutan-2-yl)-1,1-dioxo-4h-pyrido[4,3-e][1,2,4]thiadiazin-3-amine Chemical compound N1=CC=C2NC(NC(C)C(C)C)=NS(=O)(=O)C2=C1 XWCFBKQZEWEFOD-UHFFFAOYSA-N 0.000 claims 2
- 125000001624 naphthyl group Chemical group 0.000 claims 2
- 239000000651 prodrug Substances 0.000 claims 2
- 229940002612 prodrug Drugs 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- 125000001544 thienyl group Chemical group 0.000 claims 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
- YQGMUJQPKFBZLT-BPARTEKVSA-N (2s)-2-amino-1-[5-(4-chlorophenyl)-4-phenyl-3,4-dihydropyrazol-2-yl]-3-(3,4-dichlorophenyl)propan-1-one Chemical compound C([C@H](N)C(=O)N1N=C(C(C1)C=1C=CC=CC=1)C=1C=CC(Cl)=CC=1)C1=CC=C(Cl)C(Cl)=C1 YQGMUJQPKFBZLT-BPARTEKVSA-N 0.000 claims 1
- IQWVGXPEIYCTSM-OAQYLSRUSA-N (4s)-5-(4-chlorophenyl)-n'-(4-chlorophenyl)sulfonyl-4-(3-fluorophenyl)-n-methoxy-3,4-dihydropyrazole-2-carboximidamide Chemical compound C=1C=C(Cl)C=CC=1C([C@H](C1)C=2C=C(F)C=CC=2)=NN1C(NOC)=NS(=O)(=O)C1=CC=C(Cl)C=C1 IQWVGXPEIYCTSM-OAQYLSRUSA-N 0.000 claims 1
- IROXUEHWMXXEAF-HXUWFJFHSA-N (4s)-5-(4-chlorophenyl)-n'-(4-chlorophenyl)sulfonyl-4-phenyl-3,4-dihydropyrazole-2-carboximidamide Chemical compound C=1C=C(Cl)C=CC=1C([C@H](C1)C=2C=CC=CC=2)=NN1C(N)=NS(=O)(=O)C1=CC=C(Cl)C=C1 IROXUEHWMXXEAF-HXUWFJFHSA-N 0.000 claims 1
- VXVYAAXIGIEBPP-HXUWFJFHSA-N (4s)-5-(4-chlorophenyl)-n'-methyl-4-phenyl-n-piperidin-1-ylsulfonyl-3,4-dihydropyrazole-2-carboximidamide Chemical compound C=1C=C(Cl)C=CC=1C([C@H](C1)C=2C=CC=CC=2)=NN1C(NC)=NS(=O)(=O)N1CCCCC1 VXVYAAXIGIEBPP-HXUWFJFHSA-N 0.000 claims 1
- AFBXAMDVJUKHMK-UHFFFAOYSA-N 1-(4-bromophenyl)-2-(2,4-dichlorophenyl)-5-ethyl-n-piperidin-1-ylimidazole-4-carboxamide Chemical compound C=1C=C(Br)C=CC=1N1C(CC)=C(C(=O)NN2CCCCC2)N=C1C1=CC=C(Cl)C=C1Cl AFBXAMDVJUKHMK-UHFFFAOYSA-N 0.000 claims 1
- SHLMKTXWDGEQRU-UHFFFAOYSA-N 1-(4-bromophenyl)-5-chloro-2-(2,4-dichlorophenyl)-n-piperidin-1-ylimidazole-4-carboxamide Chemical compound C=1C=C(Br)C=CC=1N1C(Cl)=C(C(=O)NN2CCCCC2)N=C1C1=CC=C(Cl)C=C1Cl SHLMKTXWDGEQRU-UHFFFAOYSA-N 0.000 claims 1
- XWUCVTHIHTTWIK-UHFFFAOYSA-N 1-(4-bromophenyl)-n-cyclohexyl-2-(2,4-dichlorophenyl)-5-ethylimidazole-4-carboxamide Chemical compound C=1C=C(Br)C=CC=1N1C(CC)=C(C(=O)NC2CCCCC2)N=C1C1=CC=C(Cl)C=C1Cl XWUCVTHIHTTWIK-UHFFFAOYSA-N 0.000 claims 1
- RYVRPEABVWJUDF-UHFFFAOYSA-N 1-(4-chlorophenyl)-2-(2,4-dichlorophenyl)-5-(fluoromethyl)-n-piperidin-1-ylimidazole-4-carboxamide Chemical compound C=1C=C(Cl)C=CC=1N1C(CF)=C(C(=O)NN2CCCCC2)N=C1C1=CC=C(Cl)C=C1Cl RYVRPEABVWJUDF-UHFFFAOYSA-N 0.000 claims 1
- PHWDIDWKGGEYRL-UHFFFAOYSA-N 1-(4-chlorophenyl)-2-(2,4-dichlorophenyl)-5-(hydroxymethyl)-n-piperidin-1-ylimidazole-4-carboxamide Chemical compound C=1C=C(Cl)C=CC=1N1C(CO)=C(C(=O)NN2CCCCC2)N=C1C1=CC=C(Cl)C=C1Cl PHWDIDWKGGEYRL-UHFFFAOYSA-N 0.000 claims 1
- RQFDHAZJXWQQBK-UHFFFAOYSA-N 1-(4-chlorophenyl)-2-(2,4-dichlorophenyl)-5-ethyl-n-piperidin-1-ylimidazole-4-carboxamide Chemical compound C=1C=C(Cl)C=CC=1N1C(CC)=C(C(=O)NN2CCCCC2)N=C1C1=CC=C(Cl)C=C1Cl RQFDHAZJXWQQBK-UHFFFAOYSA-N 0.000 claims 1
- RTBUUAHDJIUXEM-UHFFFAOYSA-N 1-(4-chlorophenyl)-2-(2,4-dichlorophenyl)-5-methyl-4-pentylimidazole Chemical compound C=1C=C(Cl)C=CC=1N1C(C)=C(CCCCC)N=C1C1=CC=C(Cl)C=C1Cl RTBUUAHDJIUXEM-UHFFFAOYSA-N 0.000 claims 1
- HQHBPIPKHVSEIN-UHFFFAOYSA-N 1-(4-chlorophenyl)-2-(2,4-dichlorophenyl)-5-methyl-n-[[4-(trifluoromethyl)phenyl]methyl]imidazole-4-carboxamide Chemical compound C=1C=C(Cl)C=CC=1N1C(C)=C(C(=O)NCC=2C=CC(=CC=2)C(F)(F)F)N=C1C1=CC=C(Cl)C=C1Cl HQHBPIPKHVSEIN-UHFFFAOYSA-N 0.000 claims 1
- XHUGETFAQBCPHR-UHFFFAOYSA-N 1-(4-chlorophenyl)-2-(2,4-dichlorophenyl)-5-methylsulfonyl-n-piperidin-1-ylimidazole-4-carboxamide Chemical compound C=1C=C(Cl)C=CC=1N1C(S(=O)(=O)C)=C(C(=O)NN2CCCCC2)N=C1C1=CC=C(Cl)C=C1Cl XHUGETFAQBCPHR-UHFFFAOYSA-N 0.000 claims 1
- XBQPLQNMIBRBCV-UHFFFAOYSA-N 1-(4-chlorophenyl)-2-(2,4-dichlorophenyl)-n,n-diethylimidazole-4-carboxamide Chemical compound N=1C(C(=O)N(CC)CC)=CN(C=2C=CC(Cl)=CC=2)C=1C1=CC=C(Cl)C=C1Cl XBQPLQNMIBRBCV-UHFFFAOYSA-N 0.000 claims 1
- QODRGVWMWOLMTE-UHFFFAOYSA-N 1-(4-chlorophenyl)-2-(2,4-dichlorophenyl)-n-(4-hydroxycyclohexyl)-5-methylimidazole-4-carboxamide Chemical compound C=1C=C(Cl)C=CC=1N1C(C)=C(C(=O)NC2CCC(O)CC2)N=C1C1=CC=C(Cl)C=C1Cl QODRGVWMWOLMTE-UHFFFAOYSA-N 0.000 claims 1
- CPZFFCWPBSKKAF-UHFFFAOYSA-N 1-(4-chlorophenyl)-2-(2,4-dichlorophenyl)-n-piperidin-1-ylimidazole-4-carboxamide Chemical compound C1=CC(Cl)=CC=C1N1C(C=2C(=CC(Cl)=CC=2)Cl)=NC(C(=O)NN2CCCCC2)=C1 CPZFFCWPBSKKAF-UHFFFAOYSA-N 0.000 claims 1
- GCDAJTOSQPKCQT-UHFFFAOYSA-N 1-(4-chlorophenyl)-5-ethyl-2-(3-methylpyridin-2-yl)-n-piperidin-1-ylimidazole-4-carboxamide Chemical compound C=1C=C(Cl)C=CC=1N1C(CC)=C(C(=O)NN2CCCCC2)N=C1C1=NC=CC=C1C GCDAJTOSQPKCQT-UHFFFAOYSA-N 0.000 claims 1
- NBQXCVVEMNZLJB-UHFFFAOYSA-N 1-(4-chlorophenyl)-n-cyclohexyl-2-(2,4-dichlorophenyl)-5-methylsulfanylimidazole-4-carboxamide Chemical compound C=1C=C(Cl)C=CC=1N1C(SC)=C(C(=O)NC2CCCCC2)N=C1C1=CC=C(Cl)C=C1Cl NBQXCVVEMNZLJB-UHFFFAOYSA-N 0.000 claims 1
- KIEZSIFWBNHHIO-UHFFFAOYSA-N 1-(4-chlorophenyl)-n-cyclohexyl-5-ethyl-2-(3-methylpyridin-2-yl)imidazole-4-carboxamide Chemical compound C=1C=C(Cl)C=CC=1N1C(CC)=C(C(=O)NC2CCCCC2)N=C1C1=NC=CC=C1C KIEZSIFWBNHHIO-UHFFFAOYSA-N 0.000 claims 1
- TUMUOLDYJYUKOV-UHFFFAOYSA-N 1-(4-imidazol-1-ylbenzoyl)-n-methylcyclobutane-1-carbothioamide Chemical compound C=1C=C(N2C=NC=C2)C=CC=1C(=O)C1(C(=S)NC)CCC1 TUMUOLDYJYUKOV-UHFFFAOYSA-N 0.000 claims 1
- YHQHXOAFYVHYLC-UHFFFAOYSA-N 1-(5-chloropyridin-2-yl)-2-(2,4-dichlorophenyl)-5-ethyl-n-piperidin-1-ylimidazole-4-carboxamide Chemical compound C=1C=C(Cl)C=NC=1N1C(CC)=C(C(=O)NN2CCCCC2)N=C1C1=CC=C(Cl)C=C1Cl YHQHXOAFYVHYLC-UHFFFAOYSA-N 0.000 claims 1
- RAVRTQMDHKJJIW-UHFFFAOYSA-N 1-[bis(4-chlorophenyl)methyl]-3-[(3,5-difluorophenyl)-methylsulfonylmethylidene]azetidine Chemical compound C=1C(F)=CC(F)=CC=1C(S(=O)(=O)C)=C(C1)CN1C(C=1C=CC(Cl)=CC=1)C1=CC=C(Cl)C=C1 RAVRTQMDHKJJIW-UHFFFAOYSA-N 0.000 claims 1
- IVVNZDGDKPTYHK-JTQLQIEISA-N 1-cyano-2-[(2s)-3,3-dimethylbutan-2-yl]-3-pyridin-4-ylguanidine Chemical compound CC(C)(C)[C@H](C)N=C(NC#N)NC1=CC=NC=C1 IVVNZDGDKPTYHK-JTQLQIEISA-N 0.000 claims 1
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims 1
- OAEPVONARXVFSR-UHFFFAOYSA-N 2-(2,4-dichlorophenyl)-5-methyl-n-piperidin-1-yl-1-pyridin-2-ylimidazole-4-carboxamide Chemical compound C=1C=CC=NC=1N1C(C)=C(C(=O)NN2CCCCC2)N=C1C1=CC=C(Cl)C=C1Cl OAEPVONARXVFSR-UHFFFAOYSA-N 0.000 claims 1
- AKBXJIUPMNNRQQ-UHFFFAOYSA-N 2-(2,4-dichlorophenyl)-n'-methyl-n-morpholin-4-ylsulfonyl-3-phenyl-3,4-dihydropyrazole-5-carboximidamide Chemical compound N=1N(C=2C(=CC(Cl)=CC=2)Cl)C(C=2C=CC=CC=2)CC=1C(NC)=NS(=O)(=O)N1CCOCC1 AKBXJIUPMNNRQQ-UHFFFAOYSA-N 0.000 claims 1
- RJMNZCAGYIQAGQ-UHFFFAOYSA-N 2-(2,5-dichlorophenyl)-5-ethyl-1-phenyl-n-piperidin-1-ylimidazole-4-carboxamide Chemical compound C=1C=CC=CC=1N1C(CC)=C(C(=O)NN2CCCCC2)N=C1C1=CC(Cl)=CC=C1Cl RJMNZCAGYIQAGQ-UHFFFAOYSA-N 0.000 claims 1
- YQMHKKGEPPGEDI-UHFFFAOYSA-N 2-(2-chlorophenyl)-1-(5-chloropyridin-2-yl)-5-ethyl-n-piperidin-1-ylimidazole-4-carboxamide Chemical compound C=1C=C(Cl)C=NC=1N1C(CC)=C(C(=O)NN2CCCCC2)N=C1C1=CC=CC=C1Cl YQMHKKGEPPGEDI-UHFFFAOYSA-N 0.000 claims 1
- KQSDDZVJCRFEQJ-UHFFFAOYSA-N 2-(4-chlorophenyl)-3-phenyl-3,4-dihydropyrazole-5-carboximidamide Chemical compound C1C(C(=N)N)=NN(C=2C=CC(Cl)=CC=2)C1C1=CC=CC=C1 KQSDDZVJCRFEQJ-UHFFFAOYSA-N 0.000 claims 1
- NOVHFEZWIDENIS-UHFFFAOYSA-N 2-(4-chlorophenyl)-n'-methyl-3-phenyl-n-piperidin-1-ylsulfonyl-3,4-dihydropyrazole-5-carboximidamide Chemical compound N=1N(C=2C=CC(Cl)=CC=2)C(C=2C=CC=CC=2)CC=1C(NC)=NS(=O)(=O)N1CCCCC1 NOVHFEZWIDENIS-UHFFFAOYSA-N 0.000 claims 1
- YNZFFALZMRAPHQ-SYYKKAFVSA-N 2-[(1r,2r,5r)-5-hydroxy-2-(3-hydroxypropyl)cyclohexyl]-5-(2-methyloctan-2-yl)phenol Chemical compound OC1=CC(C(C)(C)CCCCCC)=CC=C1[C@H]1[C@H](CCCO)CC[C@@H](O)C1 YNZFFALZMRAPHQ-SYYKKAFVSA-N 0.000 claims 1
- UCLHOGAWSFTWIO-UHFFFAOYSA-N 2-[1-(4-chlorophenyl)-2-(2,4-dichlorophenyl)-5-methylimidazol-4-yl]hexan-2-ol Chemical compound C=1C=C(Cl)C=CC=1N1C(C)=C(C(C)(O)CCCC)N=C1C1=CC=C(Cl)C=C1Cl UCLHOGAWSFTWIO-UHFFFAOYSA-N 0.000 claims 1
- ITFMVOAAUUEOJT-UHFFFAOYSA-N 2-[1-[bis(4-chlorophenyl)methyl]azetidin-3-yl]-1,1-dioxo-1,2-benzothiazol-3-one Chemical compound C1=CC(Cl)=CC=C1C(C=1C=CC(Cl)=CC=1)N1CC(N2S(C3=CC=CC=C3C2=O)(=O)=O)C1 ITFMVOAAUUEOJT-UHFFFAOYSA-N 0.000 claims 1
- 125000004211 3,5-difluorophenyl group Chemical group [H]C1=C(F)C([H])=C(*)C([H])=C1F 0.000 claims 1
- BBKPNYHSDCZFPA-UHFFFAOYSA-N 4-(4-chlorophenyl)-5-(2,4-dichlorophenyl)-n-piperidin-1-yl-1,3-thiazole-2-carboxamide Chemical compound C1=CC(Cl)=CC=C1C1=C(C=2C(=CC(Cl)=CC=2)Cl)SC(C(=O)NN2CCCCC2)=N1 BBKPNYHSDCZFPA-UHFFFAOYSA-N 0.000 claims 1
- XLCPMQYEPILYFO-UHFFFAOYSA-N 4-(4-chlorophenyl)-n-cyclohexyl-5-(2,4-dichlorophenyl)-1-methylimidazole-2-carboxamide Chemical compound CN1C(C(=O)NC2CCCCC2)=NC(C=2C=CC(Cl)=CC=2)=C1C1=CC=C(Cl)C=C1Cl XLCPMQYEPILYFO-UHFFFAOYSA-N 0.000 claims 1
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims 1
- CDUPDHIKBBMHET-UHFFFAOYSA-N 5-(4-bromophenyl)-1-(2,4-dichlorophenyl)pyrazole-3-carbonitrile Chemical compound ClC1=CC(Cl)=CC=C1N1C(C=2C=CC(Br)=CC=2)=CC(C#N)=N1 CDUPDHIKBBMHET-UHFFFAOYSA-N 0.000 claims 1
- PBAUKLFWDKWSSN-UHFFFAOYSA-N 5-(4-bromophenyl)-n-(4-chlorophenyl)sulfonyl-1-(2,4-dichlorophenyl)pyrazole-3-carboxamide Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)NC(=O)C1=NN(C=2C(=CC(Cl)=CC=2)Cl)C(C=2C=CC(Br)=CC=2)=C1 PBAUKLFWDKWSSN-UHFFFAOYSA-N 0.000 claims 1
- ONYKENLNZNVNBN-UHFFFAOYSA-N 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-n-pyrrolidin-1-yl-1,2,4-triazole-3-carboxamide Chemical compound C1=CC(Cl)=CC=C1C1=NC(C(=O)NN2CCCC2)=NN1C1=CC=C(Cl)C=C1Cl ONYKENLNZNVNBN-UHFFFAOYSA-N 0.000 claims 1
- OJCCUUBHNGTDNN-UHFFFAOYSA-N 5-(4-chlorophenyl)-4-(2,4-dichlorophenyl)-n-piperidin-1-yl-1,3-thiazole-2-carboxamide Chemical compound C1=CC(Cl)=CC=C1C1=C(C=2C(=CC(Cl)=CC=2)Cl)N=C(C(=O)NN2CCCCC2)S1 OJCCUUBHNGTDNN-UHFFFAOYSA-N 0.000 claims 1
- ODXVSZMDIXVEOF-UHFFFAOYSA-N 5-(4-chlorophenyl)-4-(2,5-dichlorophenyl)-1-methyl-n-piperidin-1-ylimidazole-2-carboxamide Chemical compound CN1C(C(=O)NN2CCCCC2)=NC(C=2C(=CC=C(Cl)C=2)Cl)=C1C1=CC=C(Cl)C=C1 ODXVSZMDIXVEOF-UHFFFAOYSA-N 0.000 claims 1
- YJSQWROTEOJGRH-UHFFFAOYSA-N 5-(4-chlorophenyl)-4-(3-fluorophenyl)-n'-methyl-n-piperidin-1-ylsulfonyl-3,4-dihydropyrazole-2-carboximidamide Chemical compound C1C(C=2C=C(F)C=CC=2)C(C=2C=CC(Cl)=CC=2)=NN1C(NC)=NS(=O)(=O)N1CCCCC1 YJSQWROTEOJGRH-UHFFFAOYSA-N 0.000 claims 1
- IROXUEHWMXXEAF-UHFFFAOYSA-N 5-(4-chlorophenyl)-n'-(4-chlorophenyl)sulfonyl-4-phenyl-3,4-dihydropyrazole-2-carboximidamide Chemical compound C1C(C=2C=CC=CC=2)C(C=2C=CC(Cl)=CC=2)=NN1C(N)=NS(=O)(=O)C1=CC=C(Cl)C=C1 IROXUEHWMXXEAF-UHFFFAOYSA-N 0.000 claims 1
- BNQDRYKKHGWDIP-UHFFFAOYSA-N 5-(4-chlorophenyl)-n'-methyl-4-pyridin-3-yl-n-[4-(trifluoromethyl)phenyl]sulfonyl-3,4-dihydropyrazole-2-carboximidamide Chemical compound C1C(C=2C=NC=CC=2)C(C=2C=CC(Cl)=CC=2)=NN1C(NC)=NS(=O)(=O)C1=CC=C(C(F)(F)F)C=C1 BNQDRYKKHGWDIP-UHFFFAOYSA-N 0.000 claims 1
- RMXLQPIAIKDVTP-UHFFFAOYSA-N 5-(4-chlorophenyl)-n'-methyl-n-morpholin-4-ylsulfonyl-4-phenyl-3,4-dihydropyrazole-2-carboximidamide Chemical compound C1C(C=2C=CC=CC=2)C(C=2C=CC(Cl)=CC=2)=NN1C(NC)=NS(=O)(=O)N1CCOCC1 RMXLQPIAIKDVTP-UHFFFAOYSA-N 0.000 claims 1
- LICMEVITAAEDBQ-UHFFFAOYSA-N 5-(4-chlorophenyl)-n-(4-chlorophenyl)sulfonyl-4-phenyl-n'-(pyridin-3-ylmethyl)-3,4-dihydropyrazole-2-carboximidamide Chemical compound C1=CC(Cl)=CC=C1C1=NN(C(NCC=2C=NC=CC=2)=NS(=O)(=O)C=2C=CC(Cl)=CC=2)CC1C1=CC=CC=C1 LICMEVITAAEDBQ-UHFFFAOYSA-N 0.000 claims 1
- WCPNRDSDKJMYOH-UHFFFAOYSA-N 5-(4-chlorophenyl)-n-(4-chlorophenyl)sulfonyl-n'-(2-fluoroethyl)-4-phenyl-3,4-dihydropyrazole-2-carboximidamide Chemical compound C1C(C=2C=CC=CC=2)C(C=2C=CC(Cl)=CC=2)=NN1C(NCCF)=NS(=O)(=O)C1=CC=C(Cl)C=C1 WCPNRDSDKJMYOH-UHFFFAOYSA-N 0.000 claims 1
- NVJVDZMNNYMORJ-UHFFFAOYSA-N 5-(4-chlorophenyl)-n-(4-chlorophenyl)sulfonyl-n'-methyl-4-pyridin-3-yl-3,4-dihydropyrazole-2-carboximidamide Chemical compound C1C(C=2C=NC=CC=2)C(C=2C=CC(Cl)=CC=2)=NN1C(NC)=NS(=O)(=O)C1=CC=C(Cl)C=C1 NVJVDZMNNYMORJ-UHFFFAOYSA-N 0.000 claims 1
- XPLMPPFFGGAAIU-UHFFFAOYSA-N 5-(4-chlorophenyl)-n-(4-hydroxypiperidin-1-yl)sulfonyl-n'-methyl-4-phenyl-3,4-dihydropyrazole-2-carboximidamide Chemical compound C1C(C=2C=CC=CC=2)C(C=2C=CC(Cl)=CC=2)=NN1C(NC)=NS(=O)(=O)N1CCC(O)CC1 XPLMPPFFGGAAIU-UHFFFAOYSA-N 0.000 claims 1
- KQISGJONOJYTTB-UHFFFAOYSA-N 5-(4-chlorophenyl)-n-(diethylsulfamoyl)-4-hydroxy-n'-methyl-4-phenyl-3h-pyrazole-2-carboximidamide Chemical compound N=1N(C(NC)=NS(=O)(=O)N(CC)CC)CC(O)(C=2C=CC=CC=2)C=1C1=CC=C(Cl)C=C1 KQISGJONOJYTTB-UHFFFAOYSA-N 0.000 claims 1
- OGOZQPPGAOHMPY-UHFFFAOYSA-N 5-(4-chlorophenyl)-n-(dimethylsulfamoyl)-4-(3-fluorophenyl)-n'-methyl-3,4-dihydropyrazole-2-carboximidamide Chemical compound N=1N(C(=NS(=O)(=O)N(C)C)NC)CC(C=2C=C(F)C=CC=2)C=1C1=CC=C(Cl)C=C1 OGOZQPPGAOHMPY-UHFFFAOYSA-N 0.000 claims 1
- TTZXAXHSJKDNRO-UHFFFAOYSA-N 5-(4-chlorophenyl)-n-(dimethylsulfamoyl)-n'-(2-fluoroethyl)-4-phenyl-3,4-dihydropyrazole-2-carboximidamide Chemical compound N=1N(C(NCCF)=NS(=O)(=O)N(C)C)CC(C=2C=CC=CC=2)C=1C1=CC=C(Cl)C=C1 TTZXAXHSJKDNRO-UHFFFAOYSA-N 0.000 claims 1
- GBDFEQIOMVIYPX-UHFFFAOYSA-N 5-(4-chlorophenyl)-n-[methyl(propan-2-yl)sulfamoyl]-4-phenyl-3,4-dihydropyrazole-2-carbothioamide Chemical compound N=1N(C(=S)NS(=O)(=O)N(C)C(C)C)CC(C=2C=CC=CC=2)C=1C1=CC=C(Cl)C=C1 GBDFEQIOMVIYPX-UHFFFAOYSA-N 0.000 claims 1
- ZXURDRUYXLVWSH-UHFFFAOYSA-N 5-(4-chlorophenyl)-n-cyclohexyl-4-(2,4-dichlorophenyl)-1-methylimidazole-2-carboxamide Chemical compound CN1C(C(=O)NC2CCCCC2)=NC(C=2C(=CC(Cl)=CC=2)Cl)=C1C1=CC=C(Cl)C=C1 ZXURDRUYXLVWSH-UHFFFAOYSA-N 0.000 claims 1
- 102100021240 ATP-sensitive inward rectifier potassium channel 8 Human genes 0.000 claims 1
- TVZCRIROJQEVOT-CABCVRRESA-N Cromakalim Chemical compound N1([C@@H]2C3=CC(=CC=C3OC([C@H]2O)(C)C)C#N)CCCC1=O TVZCRIROJQEVOT-CABCVRRESA-N 0.000 claims 1
- 208000002705 Glucose Intolerance Diseases 0.000 claims 1
- 206010018429 Glucose tolerance impaired Diseases 0.000 claims 1
- 101000614717 Homo sapiens ATP-sensitive inward rectifier potassium channel 8 Proteins 0.000 claims 1
- 206010020772 Hypertension Diseases 0.000 claims 1
- 201000001431 Hyperuricemia Diseases 0.000 claims 1
- QMHAHUAQAJVBIW-UHFFFAOYSA-N [methyl(sulfamoyl)amino]methane Chemical compound CN(C)S(N)(=O)=O QMHAHUAQAJVBIW-UHFFFAOYSA-N 0.000 claims 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 1
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims 1
- 239000002671 adjuvant Substances 0.000 claims 1
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims 1
- 208000037849 arterial hypertension Diseases 0.000 claims 1
- KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 239000002775 capsule Substances 0.000 claims 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 235000012000 cholesterol Nutrition 0.000 claims 1
- 229950004210 cromakalim Drugs 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 208000035475 disorder Diseases 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 125000004705 ethylthio group Chemical group C(C)S* 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 208000006575 hypertriglyceridemia Diseases 0.000 claims 1
- 125000000814 indol-3-yl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([H])=C([*])C2=C1[H] 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims 1
- 125000002757 morpholinyl group Chemical group 0.000 claims 1
- DDXCXWQYPAKFPH-UHFFFAOYSA-N n-(1-adamantyl)-4-pentyl-5-phenyl-1,3-thiazole-2-carboxamide Chemical compound CCCCCC=1N=C(C(=O)NC23CC4CC(CC(C4)C2)C3)SC=1C1=CC=CC=C1 DDXCXWQYPAKFPH-UHFFFAOYSA-N 0.000 claims 1
- PIOOGLCSKDHBDL-UHFFFAOYSA-N n-(1-adamantyl)-5-pentyl-4-phenyl-1,3-thiazole-2-carboxamide Chemical compound CCCCCC=1SC(C(=O)NC23CC4CC(CC(C4)C2)C3)=NC=1C1=CC=CC=C1 PIOOGLCSKDHBDL-UHFFFAOYSA-N 0.000 claims 1
- SMEFNROEYLLVDY-UHFFFAOYSA-N n-(azepan-1-yl)-1-(4-chlorophenyl)-2-(2,4-dichlorophenyl)-5-methylimidazole-4-carboxamide Chemical compound C=1C=C(Cl)C=CC=1N1C(C)=C(C(=O)NN2CCCCCC2)N=C1C1=CC=C(Cl)C=C1Cl SMEFNROEYLLVDY-UHFFFAOYSA-N 0.000 claims 1
- NMGAZBYNTMTIMB-UHFFFAOYSA-N n-[5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methylpyrazol-3-yl]piperidine-1-carboxamide Chemical compound N=1N(C=2C(=CC(Cl)=CC=2)Cl)C(C=2C=CC(Cl)=CC=2)=C(C)C=1NC(=O)N1CCCCC1 NMGAZBYNTMTIMB-UHFFFAOYSA-N 0.000 claims 1
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims 1
- 229960002310 pinacidil Drugs 0.000 claims 1
- 125000003386 piperidinyl group Chemical group 0.000 claims 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 1
- WMMMJGKFKKBRQR-UHFFFAOYSA-N rosonabant Chemical compound C1=CC(Cl)=CC=C1C1N(C=2C(=CC(Cl)=CC=2)Cl)N=C(C(=O)NN2CCCCC2)C1 WMMMJGKFKKBRQR-UHFFFAOYSA-N 0.000 claims 1
- 238000012216 screening Methods 0.000 claims 1
- 239000000725 suspension Substances 0.000 claims 1
- 235000020357 syrup Nutrition 0.000 claims 1
- 239000006188 syrup Substances 0.000 claims 1
- 239000003826 tablet Substances 0.000 claims 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-N triethylamine Natural products CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims 1
- 125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 claims 1
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 claims 1
- 229920002554 vinyl polymer Polymers 0.000 claims 1
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US62107704P | 2004-10-25 | 2004-10-25 | |
| EP04105265 | 2004-10-25 | ||
| US65162505P | 2005-02-11 | 2005-02-11 | |
| PCT/EP2005/055534 WO2006045799A2 (en) | 2004-10-25 | 2005-10-25 | Pharmaceutical compositions comprising cb1 cannabinoid receptor antagonists and potassium channel openers for the treatment of diabetes mellitus type i, obesity and related conditions |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2008517976A JP2008517976A (ja) | 2008-05-29 |
| JP2008517976A5 true JP2008517976A5 (enExample) | 2008-09-11 |
Family
ID=34929757
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2007538405A Pending JP2008517976A (ja) | 2004-10-25 | 2005-10-25 | Ｃｂ１カンナビノイド受容体拮抗薬及びカリウムチャンネルオープナーから成る、真性糖尿病１型、肥満及び関連症状の治療用の医薬組成物 |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US8058264B2 (enExample) |
| EP (1) | EP1807063A2 (enExample) |
| JP (1) | JP2008517976A (enExample) |
| AU (1) | AU2005298692A1 (enExample) |
| BR (1) | BRPI0517434A (enExample) |
| CA (1) | CA2585175A1 (enExample) |
| MX (1) | MX2007004889A (enExample) |
| RU (1) | RU2007119315A (enExample) |
| WO (1) | WO2006045799A2 (enExample) |
Families Citing this family (32)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7271189B2 (en) * | 2003-10-20 | 2007-09-18 | Solvay Pharmaceuticals, Inc. | 1H-imidazole derivatives as cannabinoid receptor modulators |
| US7745476B2 (en) * | 2004-01-30 | 2010-06-29 | Solvay Pharmaceuticals B.V. | 1,3,5-trisubstituted 4,5-dihydro-1H-pyrazole derivatives having CB1-antagonistic activity |
| TW200533657A (en) | 2004-02-17 | 2005-10-16 | Esteve Labor Dr | Substituted pyrazoline compounds, their preparation and use as medicaments |
| EP2404605B1 (en) * | 2004-08-25 | 2015-04-22 | Essentialis, Inc. | Pharmaceutical formulations of potassium ATP channel openers and uses thereof |
| WO2006060192A2 (en) * | 2004-11-30 | 2006-06-08 | Bayer Pharmaceuticals Corporation | Pyrazole derivatives |
| US9757384B2 (en) | 2005-04-06 | 2017-09-12 | Essentialis, Inc. | Methods for treating subjects with Prader-Willi syndrome or Smith-Magenis syndrome |
| EP1757587A1 (en) * | 2005-07-15 | 2007-02-28 | Laboratorios Del Dr. Esteve, S.A. | Substituted pyrazoline compounds, their preparation and use as medicaments |
| US7897589B2 (en) * | 2005-07-15 | 2011-03-01 | Laboratorios Del Dr. Esteve, S.A. | Substituted pyrazoline compounds, their preparation and use as medicaments |
| EP1743892A1 (en) | 2005-07-15 | 2007-01-17 | Laboratorios del Dr. Esteve S.A. | Substituted pyrazoline compounds, their preparation and use as medicaments |
| EP1743890A1 (en) | 2005-07-15 | 2007-01-17 | Laboratorios Del Dr. Esteve, S.A. | 4,5-Dihydro-1H-pyrazole derivatives, their preparation and use as medicaments |
| WO2007020286A2 (en) * | 2005-08-17 | 2007-02-22 | Solvay Pharmaceuticals Gmbh | Method of using potassium channel inhibiting compounds |
| ES2984297T3 (es) | 2006-01-05 | 2024-10-29 | Essentialis Inc | Sales de abertura de canales ATP de potasio y usos de las mismas |
| US7763607B2 (en) | 2006-04-27 | 2010-07-27 | Solvay Pharmaceuticals Gmbh | Pharmaceutical compositions comprising CBx cannabinoid receptor modulators and potassium channel modulators |
| EP2026798A1 (en) * | 2006-04-27 | 2009-02-25 | Solvay Pharmaceuticals GmbH | Pharmaceutical compositions comprising cbx cannabinoid receptor modulators and potassium channel modulators |
| EP2083799A1 (en) * | 2006-10-20 | 2009-08-05 | Solvay Pharmaceuticals B.V. | Micellar nanoparticles of chemical substances |
| US7923026B2 (en) * | 2006-10-20 | 2011-04-12 | Solvay Pharmaceuticals B.V. | Embedded micellar nanoparticles |
| DE102007005045B4 (de) | 2007-01-26 | 2008-12-18 | Sanofi-Aventis | Phenothiazin Derivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel |
| CN101896465A (zh) * | 2007-12-10 | 2010-11-24 | 7Tm制药联合股份有限公司 | 大麻素受体调节剂 |
| WO2009099820A2 (en) * | 2008-02-01 | 2009-08-13 | Mayo Foundation For Medical Education And Research | Modulating body weight |
| EP2151234A1 (en) * | 2008-07-28 | 2010-02-10 | Laboratorios Del. Dr. Esteve, S.A. | Pharmaceutical formulation comprising a CB1-receptor compound in a solid solution and/or solid dispersion |
| US20120053172A1 (en) | 2009-02-12 | 2012-03-01 | Cooperatieve Mirzorg U.A. | Use of a combination of diazoxide and metformin for treating obesity or obesity related disorders |
| CN105743556B (zh) | 2009-11-24 | 2019-03-22 | 韩国电子通信研究院 | 用于在无线通信系统中接收数据的方法和装置 |
| EP2683702B1 (de) | 2011-03-08 | 2014-12-24 | Sanofi | Neue substituierte phenyl-oxathiazinderivate, verfahren zu deren herstellung, diese verbindungen enthaltende arzneimittel und deren verwendung |
| EP2683698B1 (de) | 2011-03-08 | 2017-10-04 | Sanofi | Mit adamantan- oder noradamantan substituierte benzyl-oxathiazinderivate, diese verbindungen enthaltende arzneimittel und deren verwendung |
| US8895547B2 (en) | 2011-03-08 | 2014-11-25 | Sanofi | Substituted phenyl-oxathiazine derivatives, method for producing them, drugs containing said compounds and the use thereof |
| EP2683701B1 (de) | 2011-03-08 | 2014-12-24 | Sanofi | Mit benzyl- oder heteromethylengruppen substituierte oxathiazinderivate, verfahren zu deren herstellung, ihre verwendung als medikament sowie sie enthaltendes arzneimittel und deren verwendung |
| KR20150113762A (ko) * | 2014-03-31 | 2015-10-08 | 한미약품 주식회사 | 황 작용기를 포함하는 4,5-다이하이드로-1h-피라졸-3-카복스이미드아마이드 유도체, 이의 제조방법 및 이를 포함하는 약학 조성물 |
| MY187610A (en) | 2014-11-14 | 2021-10-04 | Essentialis Inc | Methods for treating subjects with prader-willi syndrome or smith-magenis syndrome |
| WO2020130836A1 (en) * | 2018-12-21 | 2020-06-25 | ACADEMISCH ZIEKENHUIS LEIDEN (h.o.d.n. LUMC) | Compound for use in treatment and prevention of type i diabetes |
| NL2022291B1 (en) * | 2018-12-21 | 2020-07-21 | Academisch Ziekenhuis Leiden | Compound for Use in Treatment and Prevention of Type I Diabetes |
| WO2021178271A1 (en) * | 2020-03-02 | 2021-09-10 | Goldfinch Bio, Inc. | 1,2,4-triazolinoe cb1 inhibitors |
| EP4305039A1 (en) * | 2021-03-12 | 2024-01-17 | Bionanosim (BNS) Ltd | Peripherally restricted cb1 receptor blockers and uses thereof |
Family Cites Families (43)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4156007A (en) * | 1974-07-12 | 1979-05-22 | U.S. Philips Corporation | Pyrazoline compounds |
| NL158178B (nl) * | 1974-07-12 | 1978-10-16 | Philips Nv | Werkwijze ter bereiding van insekticide preparaten die een pyrazolinederivaat bevatten, aldus verkregen gevormde preparaten, en werkwijze ter bereiding van pyrazolinederivaten met insekticide werking. |
| US4174393A (en) * | 1975-07-09 | 1979-11-13 | Duphar International Research B.V. | 1,3,4-Substituted pyrazoline derivatives |
| ATE4593T1 (de) | 1979-07-03 | 1983-09-15 | Duphar International Research B.V | Pyrazolin-derivate, verfahren zur herstellung dieser verbindungen sowie insektizide zusammensetzung auf der basis dieser verbindungen. |
| JPS56128774A (en) * | 1980-03-14 | 1981-10-08 | Microbial Chem Res Found | New physiologically active substance ebelactone and its preparation |
| CA1247547A (en) | 1983-06-22 | 1988-12-28 | Paul Hadvary | Leucine derivatives |
| NZ209876A (en) | 1983-10-17 | 1988-03-30 | Duphar Int Res | Piperazines and pharmaceutical compositions |
| JP3003148B2 (ja) | 1989-01-05 | 2000-01-24 | 藤沢薬品工業株式会社 | チアゾール化合物、その製造法およびそれを含有する医薬組成物 |
| AU3201095A (en) | 1994-07-27 | 1996-02-22 | G.D. Searle & Co. | Substituted thiazoles for the treatment of inflammation |
| US5616601A (en) | 1994-07-28 | 1997-04-01 | Gd Searle & Co | 1,2-aryl and heteroaryl substituted imidazolyl compounds for the treatment of inflammation |
| FR2758723B1 (fr) * | 1997-01-28 | 1999-04-23 | Sanofi Sa | Utilisation des antagonistes des recepteurs aux cannabinoides centraux pour la preparation de medicaments |
| US6267952B1 (en) * | 1998-01-09 | 2001-07-31 | Geltex Pharmaceuticals, Inc. | Lipase inhibiting polymers |
| AR022204A1 (es) | 1999-01-08 | 2002-09-04 | Norgine Bv | Compuesto, proceso para su preparacion, composicion farmaceutica y producto comestible que lo comprende. |
| GB9900416D0 (en) | 1999-01-08 | 1999-02-24 | Alizyme Therapeutics Ltd | Inhibitors |
| US6492516B1 (en) | 1999-05-14 | 2002-12-10 | Merck & Co., Inc. | Compounds having cytokine inhibitory activity |
| US6197765B1 (en) * | 1999-06-08 | 2001-03-06 | Pnina Vardi | Use of diazoxide for the treatment of metabolic syndrome and diabetes complications |
| US6352949B1 (en) * | 1999-06-15 | 2002-03-05 | Peter Willems | Fluoro glass ceramic showing photostimulable properties |
| GB9914744D0 (en) | 1999-06-24 | 1999-08-25 | Knoll Ag | Therapeutic agents |
| MXPA02005100A (es) | 1999-10-18 | 2003-09-25 | Alexipharma Inc | Derivados de pirazol antagonistas de receptor de canabinoide. |
| HK1052349B (zh) * | 2000-03-23 | 2005-09-23 | 索尔瓦药物有限公司 | 具有cb1-拮抗活性的4，5-二氢-1h-吡唑衍生物 |
| US20020091114A1 (en) * | 2000-10-04 | 2002-07-11 | Odile Piot-Grosjean | Combination of a CB1 receptor antagonist and of sibutramine, the pharmaceutical compositions comprising them and their use in the treatment of obesity |
| FR2814678B1 (fr) | 2000-10-04 | 2002-12-20 | Aventis Pharma Sa | Association d'un antagoniste du recepteur cb1 et de sibutramine, les compositions pharmaceutiques les contenant et leur utilisation pour la traitement de l'obesite |
| JP4373675B2 (ja) * | 2001-03-22 | 2009-11-25 | ソルベイ・フアーマシユーチカルズ・ベー・ブイ | Ｃｂ１−拮抗活性を有する４，５−ジヒドロ−１ｈ−ピラゾール誘導体 |
| WO2003007887A2 (en) | 2001-07-20 | 2003-01-30 | Merck & Co., Inc. | Substituted imidazoles as cannabinoid receptor modulators |
| BR0212044A (pt) * | 2001-09-21 | 2004-08-17 | Solvay Pharm Bv | Compostos, composições farmacêuticas, método de preparação das mesmas, e, uso de um composto |
| US7109216B2 (en) * | 2001-09-21 | 2006-09-19 | Solvay Pharmaceuticals B.V. | 1H-imidazole derivatives having CB1 agonistic, CB1 partial agonistic or CB1-antagonistic activity |
| PL367814A1 (en) | 2001-09-21 | 2005-03-07 | Solvay Pharmaceuticals B.V. | 4,5-dihydro-1h-pyrazole derivatives having potent cb1-antagonistic activity |
| TWI231757B (en) | 2001-09-21 | 2005-05-01 | Solvay Pharm Bv | 1H-Imidazole derivatives having CB1 agonistic, CB1 partial agonistic or CB1-antagonistic activity |
| PE20030547A1 (es) | 2001-09-24 | 2003-08-18 | Bayer Corp | Derivados de imidazol para el tratamiento de la obesidad |
| EP1441732A2 (en) | 2001-11-08 | 2004-08-04 | Fujisawa Pharmaceutical Co., Ltd. | Thiazole derivative and pharmaceutical use thereof |
| TW200407110A (en) | 2001-11-23 | 2004-05-16 | Astrazeneca Ab | New use for the treatment of gastroesophageal reflux disease |
| SE0104330D0 (sv) | 2001-12-19 | 2001-12-19 | Astrazeneca Ab | Therapeutic agents |
| GB0202015D0 (en) | 2002-01-29 | 2002-03-13 | Hoffmann La Roche | Piperazine Derivatives |
| AU2003209388A1 (en) | 2002-01-29 | 2003-09-02 | Merck And Co., Inc. | Substituted imidazoles as cannabinoid receptor modulators |
| US6900233B2 (en) * | 2002-02-28 | 2005-05-31 | Aventis Pharma Deutschland Gmbh | Substituted 3-phenyl-5-alkoxy-3H-(1,3,4)-oxadiazol-2-ones, pharmaceutical composition and method for treating obesity thereof |
| DE10208987A1 (de) | 2002-02-28 | 2003-09-11 | Aventis Pharma Gmbh | Substituierte 3-Phenyl-5-alkoxi-1,3,4-oxidiazol-2-one, ihre Herstellung und Verwendung in Arzneistoffen |
| US20030236288A1 (en) * | 2002-02-28 | 2003-12-25 | Karl Schoenafinger | Use of substituted 3-phenyl-5-alkoxy-3H-(1,3,4)-oxadizol-2-ones for inhibiting pancreatic lipase |
| DE10208986A1 (de) | 2002-02-28 | 2003-09-11 | Aventis Pharma Gmbh | Verwendung substituierter 3-Phenyl-5-alkoxi-1,3,4-oxdiazol-2-one zur Herstellung von Arzneimitteln mit hemmender Wirkung an der pankreatischen Lipase |
| AR038966A1 (es) * | 2002-03-18 | 2005-02-02 | Solvay Pharm Bv | Derivados de tiazol que tienen actividad antagonista, agonista o agonista parcial de cb1 |
| TW200412942A (en) | 2002-08-06 | 2004-08-01 | Abbott Lab | Appetite control method |
| HRP20050053A2 (en) | 2002-09-19 | 2005-04-30 | Solvay Pharmaceuticals B.V. | 1 h-1,2,4-triazole-3-carboxamide derivatives as cannabinoid-cb1 receptor ligands |
| GB0230087D0 (en) | 2002-12-24 | 2003-01-29 | Astrazeneca Ab | Therapeutic agents |
| US20050239859A2 (en) * | 2003-09-03 | 2005-10-27 | Solvay Pharmaceuticals Gmbh | Novel medical uses of 4,5-dihydro-1h-pyrazole derivatives having cb1- antagonistic activity |
-
2005
- 2005-10-25 WO PCT/EP2005/055534 patent/WO2006045799A2/en not_active Ceased
- 2005-10-25 JP JP2007538405A patent/JP2008517976A/ja active Pending
- 2005-10-25 US US11/257,056 patent/US8058264B2/en not_active Expired - Fee Related
- 2005-10-25 RU RU2007119315/15A patent/RU2007119315A/ru unknown
- 2005-10-25 MX MX2007004889A patent/MX2007004889A/es unknown
- 2005-10-25 CA CA002585175A patent/CA2585175A1/en not_active Abandoned
- 2005-10-25 BR BRPI0517434-1A patent/BRPI0517434A/pt not_active IP Right Cessation
- 2005-10-25 EP EP05801545A patent/EP1807063A2/en not_active Withdrawn
- 2005-10-25 AU AU2005298692A patent/AU2005298692A1/en not_active Abandoned
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2008517976A5 (enExample) | ||
| RU2007119315A (ru) | Фармацевтические композиции, содержащие антагонисты каннабиноидного рецептора св1 и открыватели калиевых каналов, предназначенные для лечения сахарного диабета типа i, ожирения и связанных с ними состояний | |
| RU2013143028A (ru) | Тиазолилфенилбензолсульфонамидопроизводные в качестве ингибиторов киназ | |
| RU2223116C2 (ru) | Применение производных арил (или гетероарил) азолилкарбинолов в приготовлении лекарственного средства для лечения нарушений, опосредованных избытком вещества p | |
| JP2014511869A5 (enExample) | ||
| JP2006525298A5 (enExample) | ||
| JP2019507179A5 (enExample) | ||
| RU2013138569A (ru) | Антагонисты рецептора минералокортикоидов | |
| RU2005109561A (ru) | Новые производные аминоиндазолов в качестве лекарственных средств и содержащие их фармацевтические композиции | |
| SI3075726T1 (en) | DERIVATIVES OF UREA OR ITS PHARMACOLOGICAL RECRUITABLE SALTS USED AS FORMIL PEPTIDAL RECEPTOR LIKE 1 (FPRL-1) AGONISTS | |
| RU2008146591A (ru) | Применение модуляторов каннабиноидного рецептора свх в качестве модуляторов калиевых каналов | |
| JP2021501179A5 (enExample) | ||
| RU2011109435A (ru) | Пиперидиновые соединения, содержащая их фармацевтическая композиция и ее применение | |
| RU2003132445A (ru) | Применение селективных ингибиторов сох-2 для лечения недержания мочи | |
| EP4338751B1 (en) | Combination of sepetaprost and netarsudil for use in the prophylaxis or treatment of glaucoma or ocular hypertension | |
| RU2007127864A (ru) | Производные n-[(4, 5-дифенил-3-алкил-2-тиенил)метил]амина (амид, сульфонамид, карбамат и карбамид) в качестве антагонистов рецепторов св1 каннабиноидов | |
| JPWO2020216766A5 (enExample) | ||
| JP2006513222A5 (enExample) | ||
| KR20090007606A (ko) | ＣＢｘ 칸나비노이드 수용체 조절제들 및 칼륨 채널 조절제들을 포함하는 약학적 조성물들 | |
| JP2020524660A5 (enExample) | ||
| JPWO2020179859A5 (enExample) | ||
| JP2003516975A5 (enExample) | ||
| US11918580B2 (en) | Use of a combinational therapy of LSD1 inhibitors with P21 activators in the treatment of cancer | |
| JP2006516266A5 (enExample) | ||
| RU2025102588A (ru) | Фармацевтические композиции, содержащие ингибиторы геликазы wrn |