HRP20100283T1 - Derivati n-'(1,5-difenil-1h-pirazol-3-il)sulfonamida s afinitetom za cb1 receptor - Google Patents
Derivati n-'(1,5-difenil-1h-pirazol-3-il)sulfonamida s afinitetom za cb1 receptor Download PDFInfo
- Publication number
- HRP20100283T1 HRP20100283T1 HR20100283T HRP20100283T HRP20100283T1 HR P20100283 T1 HRP20100283 T1 HR P20100283T1 HR 20100283 T HR20100283 T HR 20100283T HR P20100283 T HRP20100283 T HR P20100283T HR P20100283 T1 HRP20100283 T1 HR P20100283T1
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- HR
- Croatia
- Prior art keywords
- methyl
- pyrazol
- dichlorophenyl
- bromophenyl
- ethyl
- Prior art date
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- XVRKANGSLUFNSF-UHFFFAOYSA-N 1,5-diphenylpyrazole-3-sulfonamide Chemical compound C=1C=CC=CC=1N1N=C(S(=O)(=O)N)C=C1C1=CC=CC=C1 XVRKANGSLUFNSF-UHFFFAOYSA-N 0.000 title 1
- -1 trifluoromethyl radicals Chemical class 0.000 claims abstract 20
- 150000001875 compounds Chemical class 0.000 claims abstract 14
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract 11
- 125000005843 halogen group Chemical group 0.000 claims abstract 9
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims abstract 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract 7
- 150000003839 salts Chemical class 0.000 claims abstract 6
- 239000012453 solvate Substances 0.000 claims abstract 6
- WZKSXHQDXQKIQJ-UHFFFAOYSA-N F[C](F)F Chemical compound F[C](F)F WZKSXHQDXQKIQJ-UHFFFAOYSA-N 0.000 claims abstract 5
- 239000002253 acid Substances 0.000 claims abstract 5
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims abstract 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract 4
- 125000001424 substituent group Chemical group 0.000 claims abstract 4
- 125000000217 alkyl group Chemical group 0.000 claims abstract 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract 2
- 125000006701 (C1-C7) alkyl group Chemical group 0.000 claims abstract 2
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims abstract 2
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims abstract 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract 2
- 125000004981 cycloalkylmethyl group Chemical group 0.000 claims abstract 2
- 125000000842 isoxazolyl group Chemical group 0.000 claims abstract 2
- 125000001544 thienyl group Chemical group 0.000 claims abstract 2
- 229910052801 chlorine Inorganic materials 0.000 claims 3
- 229910052731 fluorine Inorganic materials 0.000 claims 3
- 125000001153 fluoro group Chemical group F* 0.000 claims 3
- 208000007848 Alcoholism Diseases 0.000 claims 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 2
- 239000000460 chlorine Substances 0.000 claims 2
- 229940079593 drug Drugs 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- SRZYRMZGMFNLMI-UHFFFAOYSA-N n-[[5-(4-bromophenyl)-1-(2,4-dichlorophenyl)-4-methylpyrazol-3-yl]methyl]-3-methoxybenzenesulfonamide Chemical compound COC1=CC=CC(S(=O)(=O)NCC=2C(=C(N(N=2)C=2C(=CC(Cl)=CC=2)Cl)C=2C=CC(Br)=CC=2)C)=C1 SRZYRMZGMFNLMI-UHFFFAOYSA-N 0.000 claims 2
- SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 claims 1
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims 1
- 125000004847 2-fluorobenzyl group Chemical group [H]C1=C([H])C(F)=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims 1
- HPLUEFJWTVSDMP-UHFFFAOYSA-N 3-acetyl-n-[[5-(4-bromophenyl)-1-(2,4-dichlorophenyl)-4-ethylpyrazol-3-yl]methyl]benzenesulfonamide Chemical compound N=1N(C=2C(=CC(Cl)=CC=2)Cl)C(C=2C=CC(Br)=CC=2)=C(CC)C=1CNS(=O)(=O)C1=CC=CC(C(C)=O)=C1 HPLUEFJWTVSDMP-UHFFFAOYSA-N 0.000 claims 1
- RGTANBGVXROVFS-UHFFFAOYSA-N 3-chloro-n-[[1-(2,4-dichlorophenyl)-5-(4-methoxyphenyl)-4-methylpyrazol-3-yl]methyl]benzenesulfonamide Chemical compound C1=CC(OC)=CC=C1C1=C(C)C(CNS(=O)(=O)C=2C=C(Cl)C=CC=2)=NN1C1=CC=C(Cl)C=C1Cl RGTANBGVXROVFS-UHFFFAOYSA-N 0.000 claims 1
- LSTUMOSGJMWODV-UHFFFAOYSA-N 3-chloro-n-[[1-(2-chlorophenyl)-5-(4-chlorophenyl)-4-methylpyrazol-3-yl]methyl]benzenesulfonamide Chemical compound N=1N(C=2C(=CC=CC=2)Cl)C(C=2C=CC(Cl)=CC=2)=C(C)C=1CNS(=O)(=O)C1=CC=CC(Cl)=C1 LSTUMOSGJMWODV-UHFFFAOYSA-N 0.000 claims 1
- DQHGEWKJQCQNIC-UHFFFAOYSA-N 3-chloro-n-[[5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methylpyrazol-3-yl]methyl]-4-fluorobenzenesulfonamide Chemical compound N=1N(C=2C(=CC(Cl)=CC=2)Cl)C(C=2C=CC(Cl)=CC=2)=C(C)C=1CNS(=O)(=O)C1=CC=C(F)C(Cl)=C1 DQHGEWKJQCQNIC-UHFFFAOYSA-N 0.000 claims 1
- BNWPRRPXPODVTN-UHFFFAOYSA-N 3-chloro-n-[[5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methylpyrazol-3-yl]methyl]benzenesulfonamide Chemical compound N=1N(C=2C(=CC(Cl)=CC=2)Cl)C(C=2C=CC(Cl)=CC=2)=C(C)C=1CNS(=O)(=O)C1=CC=CC(Cl)=C1 BNWPRRPXPODVTN-UHFFFAOYSA-N 0.000 claims 1
- 125000003852 3-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(Cl)=C1[H])C([H])([H])* 0.000 claims 1
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims 1
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims 1
- JDCHTUIRFBVEMD-UHFFFAOYSA-N 4-bromo-n-[[5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methylpyrazol-3-yl]methyl]-2-ethylbenzenesulfonamide Chemical compound CCC1=CC(Br)=CC=C1S(=O)(=O)NCC1=NN(C=2C(=CC(Cl)=CC=2)Cl)C(C=2C=CC(Cl)=CC=2)=C1C JDCHTUIRFBVEMD-UHFFFAOYSA-N 0.000 claims 1
- 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 claims 1
- 125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 claims 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 1
- AQDBCUGXOROMII-UHFFFAOYSA-N 4-tert-butyl-n-[[5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methylpyrazol-3-yl]methyl]benzenesulfonamide Chemical compound N=1N(C=2C(=CC(Cl)=CC=2)Cl)C(C=2C=CC(Cl)=CC=2)=C(C)C=1CNS(=O)(=O)C1=CC=C(C(C)(C)C)C=C1 AQDBCUGXOROMII-UHFFFAOYSA-N 0.000 claims 1
- WCVQNCIUCMIIEJ-UHFFFAOYSA-N 5-bromo-n-[[5-(4-bromophenyl)-1-(2,4-dichlorophenyl)-4-ethylpyrazol-3-yl]methyl]thiophene-2-sulfonamide Chemical compound N=1N(C=2C(=CC(Cl)=CC=2)Cl)C(C=2C=CC(Br)=CC=2)=C(CC)C=1CNS(=O)(=O)C1=CC=C(Br)S1 WCVQNCIUCMIIEJ-UHFFFAOYSA-N 0.000 claims 1
- 208000027559 Appetite disease Diseases 0.000 claims 1
- 208000019454 Feeding and Eating disease Diseases 0.000 claims 1
- 208000018522 Gastrointestinal disease Diseases 0.000 claims 1
- 208000028017 Psychotic disease Diseases 0.000 claims 1
- ZUSWDTWYONAOPH-UHFFFAOYSA-N [2-(trifluoromethyl)phenyl]hydrazine;hydrochloride Chemical group [Cl-].[NH3+]NC1=CC=CC=C1C(F)(F)F ZUSWDTWYONAOPH-UHFFFAOYSA-N 0.000 claims 1
- 201000007930 alcohol dependence Diseases 0.000 claims 1
- 239000012752 auxiliary agent Substances 0.000 claims 1
- 125000006269 biphenyl-2-yl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C1=C(*)C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- 125000006268 biphenyl-3-yl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C1=C([H])C(*)=C([H])C([H])=C1[H] 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 1
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- 210000000987 immune system Anatomy 0.000 claims 1
- 230000002757 inflammatory effect Effects 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- LJRQNUDBXHLKOI-UHFFFAOYSA-N n-[[1-(2,4-dichlorophenyl)-5-(4-methoxyphenyl)-4-methylpyrazol-3-yl]methyl]-3-methylbenzenesulfonamide Chemical compound C1=CC(OC)=CC=C1C1=C(C)C(CNS(=O)(=O)C=2C=C(C)C=CC=2)=NN1C1=CC=C(Cl)C=C1Cl LJRQNUDBXHLKOI-UHFFFAOYSA-N 0.000 claims 1
- BQNDUAPQKUBXCN-UHFFFAOYSA-N n-[[1-(2-chlorophenyl)-5-(4-chlorophenyl)-4-methylpyrazol-3-yl]methyl]-2-fluorobenzenesulfonamide Chemical compound N=1N(C=2C(=CC=CC=2)Cl)C(C=2C=CC(Cl)=CC=2)=C(C)C=1CNS(=O)(=O)C1=CC=CC=C1F BQNDUAPQKUBXCN-UHFFFAOYSA-N 0.000 claims 1
- OGJROFWDAAEFHC-UHFFFAOYSA-N n-[[1-(2-chlorophenyl)-5-(4-chlorophenyl)-4-methylpyrazol-3-yl]methyl]-3-cyanobenzenesulfonamide Chemical compound N=1N(C=2C(=CC=CC=2)Cl)C(C=2C=CC(Cl)=CC=2)=C(C)C=1CNS(=O)(=O)C1=CC=CC(C#N)=C1 OGJROFWDAAEFHC-UHFFFAOYSA-N 0.000 claims 1
- JARKOOMINHJYRJ-UHFFFAOYSA-N n-[[1-(2-chlorophenyl)-5-(4-chlorophenyl)-4-methylpyrazol-3-yl]methyl]-3-methoxybenzenesulfonamide Chemical compound COC1=CC=CC(S(=O)(=O)NCC=2C(=C(N(N=2)C=2C(=CC=CC=2)Cl)C=2C=CC(Cl)=CC=2)C)=C1 JARKOOMINHJYRJ-UHFFFAOYSA-N 0.000 claims 1
- XRLWNCVRSAYOFN-UHFFFAOYSA-N n-[[5-(4-bromophenyl)-1-(2,4-dichlorophenyl)-4-ethylpyrazol-3-yl]methyl]-1-(2-fluorophenyl)methanesulfonamide Chemical compound N=1N(C=2C(=CC(Cl)=CC=2)Cl)C(C=2C=CC(Br)=CC=2)=C(CC)C=1CNS(=O)(=O)CC1=CC=CC=C1F XRLWNCVRSAYOFN-UHFFFAOYSA-N 0.000 claims 1
- OWDWZIXUQSUSQQ-UHFFFAOYSA-N n-[[5-(4-bromophenyl)-1-(2,4-dichlorophenyl)-4-ethylpyrazol-3-yl]methyl]-1-(4-fluorophenyl)methanesulfonamide Chemical compound N=1N(C=2C(=CC(Cl)=CC=2)Cl)C(C=2C=CC(Br)=CC=2)=C(CC)C=1CNS(=O)(=O)CC1=CC=C(F)C=C1 OWDWZIXUQSUSQQ-UHFFFAOYSA-N 0.000 claims 1
- AYVZXPLSURSYSZ-UHFFFAOYSA-N n-[[5-(4-bromophenyl)-1-(2,4-dichlorophenyl)-4-ethylpyrazol-3-yl]methyl]-1-[3-(trifluoromethyl)phenyl]methanesulfonamide Chemical compound N=1N(C=2C(=CC(Cl)=CC=2)Cl)C(C=2C=CC(Br)=CC=2)=C(CC)C=1CNS(=O)(=O)CC1=CC=CC(C(F)(F)F)=C1 AYVZXPLSURSYSZ-UHFFFAOYSA-N 0.000 claims 1
- QLJFRPXSYPVMFK-UHFFFAOYSA-N n-[[5-(4-bromophenyl)-1-(2,4-dichlorophenyl)-4-ethylpyrazol-3-yl]methyl]-1-[4-(trifluoromethyl)phenyl]methanesulfonamide Chemical compound N=1N(C=2C(=CC(Cl)=CC=2)Cl)C(C=2C=CC(Br)=CC=2)=C(CC)C=1CNS(=O)(=O)CC1=CC=C(C(F)(F)F)C=C1 QLJFRPXSYPVMFK-UHFFFAOYSA-N 0.000 claims 1
- TVYBGBTYFKGFLT-UHFFFAOYSA-N n-[[5-(4-bromophenyl)-1-(2,4-dichlorophenyl)-4-ethylpyrazol-3-yl]methyl]-1-cyclohexylmethanesulfonamide Chemical compound N=1N(C=2C(=CC(Cl)=CC=2)Cl)C(C=2C=CC(Br)=CC=2)=C(CC)C=1CNS(=O)(=O)CC1CCCCC1 TVYBGBTYFKGFLT-UHFFFAOYSA-N 0.000 claims 1
- YBSCHHYRZNPCNZ-UHFFFAOYSA-N n-[[5-(4-bromophenyl)-1-(2,4-dichlorophenyl)-4-ethylpyrazol-3-yl]methyl]-2-(trifluoromethoxy)benzenesulfonamide Chemical compound N=1N(C=2C(=CC(Cl)=CC=2)Cl)C(C=2C=CC(Br)=CC=2)=C(CC)C=1CNS(=O)(=O)C1=CC=CC=C1OC(F)(F)F YBSCHHYRZNPCNZ-UHFFFAOYSA-N 0.000 claims 1
- FFKUTHKBMPBBFN-UHFFFAOYSA-N n-[[5-(4-bromophenyl)-1-(2,4-dichlorophenyl)-4-ethylpyrazol-3-yl]methyl]-2-(trifluoromethyl)benzenesulfonamide Chemical compound N=1N(C=2C(=CC(Cl)=CC=2)Cl)C(C=2C=CC(Br)=CC=2)=C(CC)C=1CNS(=O)(=O)C1=CC=CC=C1C(F)(F)F FFKUTHKBMPBBFN-UHFFFAOYSA-N 0.000 claims 1
- SDUCGBCBYBXGFP-UHFFFAOYSA-N n-[[5-(4-bromophenyl)-1-(2,4-dichlorophenyl)-4-ethylpyrazol-3-yl]methyl]-2-chlorobenzenesulfonamide Chemical compound N=1N(C=2C(=CC(Cl)=CC=2)Cl)C(C=2C=CC(Br)=CC=2)=C(CC)C=1CNS(=O)(=O)C1=CC=CC=C1Cl SDUCGBCBYBXGFP-UHFFFAOYSA-N 0.000 claims 1
- DLVSVWBGBSBTDJ-UHFFFAOYSA-N n-[[5-(4-bromophenyl)-1-(2,4-dichlorophenyl)-4-ethylpyrazol-3-yl]methyl]-3,5-bis(trifluoromethyl)benzenesulfonamide Chemical compound N=1N(C=2C(=CC(Cl)=CC=2)Cl)C(C=2C=CC(Br)=CC=2)=C(CC)C=1CNS(=O)(=O)C1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 DLVSVWBGBSBTDJ-UHFFFAOYSA-N 0.000 claims 1
- YUPXHJHFQPRQOV-UHFFFAOYSA-N n-[[5-(4-bromophenyl)-1-(2,4-dichlorophenyl)-4-ethylpyrazol-3-yl]methyl]-3,5-dimethylbenzenesulfonamide Chemical compound N=1N(C=2C(=CC(Cl)=CC=2)Cl)C(C=2C=CC(Br)=CC=2)=C(CC)C=1CNS(=O)(=O)C1=CC(C)=CC(C)=C1 YUPXHJHFQPRQOV-UHFFFAOYSA-N 0.000 claims 1
- RSGXXTGLSKICRH-UHFFFAOYSA-N n-[[5-(4-bromophenyl)-1-(2,4-dichlorophenyl)-4-ethylpyrazol-3-yl]methyl]-3-(trifluoromethoxy)benzenesulfonamide Chemical compound N=1N(C=2C(=CC(Cl)=CC=2)Cl)C(C=2C=CC(Br)=CC=2)=C(CC)C=1CNS(=O)(=O)C1=CC=CC(OC(F)(F)F)=C1 RSGXXTGLSKICRH-UHFFFAOYSA-N 0.000 claims 1
- IHTJRSZCEYSAPG-UHFFFAOYSA-N n-[[5-(4-bromophenyl)-1-(2,4-dichlorophenyl)-4-ethylpyrazol-3-yl]methyl]-3-(trifluoromethyl)benzenesulfonamide Chemical compound N=1N(C=2C(=CC(Cl)=CC=2)Cl)C(C=2C=CC(Br)=CC=2)=C(CC)C=1CNS(=O)(=O)C1=CC=CC(C(F)(F)F)=C1 IHTJRSZCEYSAPG-UHFFFAOYSA-N 0.000 claims 1
- TXFKZCSPIUBYDA-UHFFFAOYSA-N n-[[5-(4-bromophenyl)-1-(2,4-dichlorophenyl)-4-ethylpyrazol-3-yl]methyl]-3-chlorobenzenesulfonamide Chemical compound N=1N(C=2C(=CC(Cl)=CC=2)Cl)C(C=2C=CC(Br)=CC=2)=C(CC)C=1CNS(=O)(=O)C1=CC=CC(Cl)=C1 TXFKZCSPIUBYDA-UHFFFAOYSA-N 0.000 claims 1
- PTGODCFEBVUTMC-UHFFFAOYSA-N n-[[5-(4-bromophenyl)-1-(2,4-dichlorophenyl)-4-ethylpyrazol-3-yl]methyl]-3-methoxybenzenesulfonamide Chemical compound N=1N(C=2C(=CC(Cl)=CC=2)Cl)C(C=2C=CC(Br)=CC=2)=C(CC)C=1CNS(=O)(=O)C1=CC=CC(OC)=C1 PTGODCFEBVUTMC-UHFFFAOYSA-N 0.000 claims 1
- ZUZDGRUIQFKYIP-UHFFFAOYSA-N n-[[5-(4-bromophenyl)-1-(2,4-dichlorophenyl)-4-ethylpyrazol-3-yl]methyl]-3-methylbenzenesulfonamide Chemical compound N=1N(C=2C(=CC(Cl)=CC=2)Cl)C(C=2C=CC(Br)=CC=2)=C(CC)C=1CNS(=O)(=O)C1=CC=CC(C)=C1 ZUZDGRUIQFKYIP-UHFFFAOYSA-N 0.000 claims 1
- MANDWSVTAGXLPO-UHFFFAOYSA-N n-[[5-(4-bromophenyl)-1-(2,4-dichlorophenyl)-4-ethylpyrazol-3-yl]methyl]-3-phenylbenzenesulfonamide Chemical compound N=1N(C=2C(=CC(Cl)=CC=2)Cl)C(C=2C=CC(Br)=CC=2)=C(CC)C=1CNS(=O)(=O)C(C=1)=CC=CC=1C1=CC=CC=C1 MANDWSVTAGXLPO-UHFFFAOYSA-N 0.000 claims 1
- XLDLALZOGONXNU-UHFFFAOYSA-N n-[[5-(4-bromophenyl)-1-(2,4-dichlorophenyl)-4-ethylpyrazol-3-yl]methyl]-4-(trifluoromethyl)benzenesulfonamide Chemical compound N=1N(C=2C(=CC(Cl)=CC=2)Cl)C(C=2C=CC(Br)=CC=2)=C(CC)C=1CNS(=O)(=O)C1=CC=C(C(F)(F)F)C=C1 XLDLALZOGONXNU-UHFFFAOYSA-N 0.000 claims 1
- BOWCHYPUUIJMMW-UHFFFAOYSA-N n-[[5-(4-bromophenyl)-1-(2,4-dichlorophenyl)-4-ethylpyrazol-3-yl]methyl]-4-methoxybenzenesulfonamide Chemical compound N=1N(C=2C(=CC(Cl)=CC=2)Cl)C(C=2C=CC(Br)=CC=2)=C(CC)C=1CNS(=O)(=O)C1=CC=C(OC)C=C1 BOWCHYPUUIJMMW-UHFFFAOYSA-N 0.000 claims 1
- SHEXCFSHGAXSOA-UHFFFAOYSA-N n-[[5-(4-bromophenyl)-1-(2,4-dichlorophenyl)-4-ethylpyrazol-3-yl]methyl]-4-tert-butylbenzenesulfonamide Chemical compound N=1N(C=2C(=CC(Cl)=CC=2)Cl)C(C=2C=CC(Br)=CC=2)=C(CC)C=1CNS(=O)(=O)C1=CC=C(C(C)(C)C)C=C1 SHEXCFSHGAXSOA-UHFFFAOYSA-N 0.000 claims 1
- ULZWLSMZNGVDPO-UHFFFAOYSA-N n-[[5-(4-bromophenyl)-1-(2,4-dichlorophenyl)-4-ethylpyrazol-3-yl]methyl]-5-(1,2-oxazol-3-yl)thiophene-2-sulfonamide Chemical compound N=1N(C=2C(=CC(Cl)=CC=2)Cl)C(C=2C=CC(Br)=CC=2)=C(CC)C=1CNS(=O)(=O)C(S1)=CC=C1C=1C=CON=1 ULZWLSMZNGVDPO-UHFFFAOYSA-N 0.000 claims 1
- KWMICWOMEBTJNP-UHFFFAOYSA-N n-[[5-(4-bromophenyl)-1-(2,4-dichlorophenyl)-4-ethylpyrazol-3-yl]methyl]butane-1-sulfonamide Chemical compound CCC=1C(CNS(=O)(=O)CCCC)=NN(C=2C(=CC(Cl)=CC=2)Cl)C=1C1=CC=C(Br)C=C1 KWMICWOMEBTJNP-UHFFFAOYSA-N 0.000 claims 1
- JNHRAHLUUFJXSZ-UHFFFAOYSA-N n-[[5-(4-bromophenyl)-1-(2,4-dichlorophenyl)-4-ethylpyrazol-3-yl]methyl]cyclohexanesulfonamide Chemical compound N=1N(C=2C(=CC(Cl)=CC=2)Cl)C(C=2C=CC(Br)=CC=2)=C(CC)C=1CNS(=O)(=O)C1CCCCC1 JNHRAHLUUFJXSZ-UHFFFAOYSA-N 0.000 claims 1
- FOYHAVVGHCBVKL-UHFFFAOYSA-N n-[[5-(4-bromophenyl)-1-(2,4-dichlorophenyl)-4-ethylpyrazol-3-yl]methyl]ethanesulfonamide Chemical compound CCC=1C(CNS(=O)(=O)CC)=NN(C=2C(=CC(Cl)=CC=2)Cl)C=1C1=CC=C(Br)C=C1 FOYHAVVGHCBVKL-UHFFFAOYSA-N 0.000 claims 1
- BUHWGWGXGXAYST-UHFFFAOYSA-N n-[[5-(4-bromophenyl)-1-(2,4-dichlorophenyl)-4-ethylpyrazol-3-yl]methyl]propane-2-sulfonamide Chemical compound CCC=1C(CNS(=O)(=O)C(C)C)=NN(C=2C(=CC(Cl)=CC=2)Cl)C=1C1=CC=C(Br)C=C1 BUHWGWGXGXAYST-UHFFFAOYSA-N 0.000 claims 1
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- SDJTZFCUQMFMER-UHFFFAOYSA-N n-[[5-(4-bromophenyl)-1-(2,4-dichlorophenyl)-4-methylpyrazol-3-yl]methyl]-1-cyclohexylmethanesulfonamide Chemical compound N=1N(C=2C(=CC(Cl)=CC=2)Cl)C(C=2C=CC(Br)=CC=2)=C(C)C=1CNS(=O)(=O)CC1CCCCC1 SDJTZFCUQMFMER-UHFFFAOYSA-N 0.000 claims 1
- MPAPXHXEMLDPMP-UHFFFAOYSA-N n-[[5-(4-bromophenyl)-1-(2,4-dichlorophenyl)-4-methylpyrazol-3-yl]methyl]-2-methylsulfonylbenzenesulfonamide Chemical compound N=1N(C=2C(=CC(Cl)=CC=2)Cl)C(C=2C=CC(Br)=CC=2)=C(C)C=1CNS(=O)(=O)C1=CC=CC=C1S(C)(=O)=O MPAPXHXEMLDPMP-UHFFFAOYSA-N 0.000 claims 1
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- BEINBPUJJBXEAD-UHFFFAOYSA-N n-[[5-(4-bromophenyl)-1-(2,4-dichlorophenyl)-4-methylpyrazol-3-yl]methyl]-3-chlorobenzenesulfonamide Chemical compound N=1N(C=2C(=CC(Cl)=CC=2)Cl)C(C=2C=CC(Br)=CC=2)=C(C)C=1CNS(=O)(=O)C1=CC=CC(Cl)=C1 BEINBPUJJBXEAD-UHFFFAOYSA-N 0.000 claims 1
- HNNBLYIVRHQOQA-UHFFFAOYSA-N n-[[5-(4-bromophenyl)-1-(2,4-dichlorophenyl)-4-methylpyrazol-3-yl]methyl]-3-cyanobenzenesulfonamide Chemical compound N=1N(C=2C(=CC(Cl)=CC=2)Cl)C(C=2C=CC(Br)=CC=2)=C(C)C=1CNS(=O)(=O)C1=CC=CC(C#N)=C1 HNNBLYIVRHQOQA-UHFFFAOYSA-N 0.000 claims 1
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- LIISJAFYPFEXQI-UHFFFAOYSA-N n-[[5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methylpyrazol-3-yl]methyl]-2-methylsulfonylbenzenesulfonamide Chemical compound N=1N(C=2C(=CC(Cl)=CC=2)Cl)C(C=2C=CC(Cl)=CC=2)=C(C)C=1CNS(=O)(=O)C1=CC=CC=C1S(C)(=O)=O LIISJAFYPFEXQI-UHFFFAOYSA-N 0.000 claims 1
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- BNAQXKIYCAYJQX-UHFFFAOYSA-N n-[[5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methylpyrazol-3-yl]methyl]-4-(trifluoromethyl)benzenesulfonamide Chemical compound N=1N(C=2C(=CC(Cl)=CC=2)Cl)C(C=2C=CC(Cl)=CC=2)=C(C)C=1CNS(=O)(=O)C1=CC=C(C(F)(F)F)C=C1 BNAQXKIYCAYJQX-UHFFFAOYSA-N 0.000 claims 1
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Classifications
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Abstract
Spoj koji odgovara formuli (I): naznačen time što: R1 predstavlja (C1-C6)alkil; (C3-C7)cikloalkil koji je nesupstituiran ili supstituiran jednom ili nekoliko puta s (C1-C3)alkil skupinom; (C3-C7)cikloalkilmetil koji je nesupstituiran ili supstituiran jednom ili nekoliko puta na karbociklu s (C1-C3)alkilom; fenil koji je nesupstituiran ili mono-, di- ili trisupstituiran sa supstituentom nezavisno odabranim od atoma halogena, (C1-C4)alkila, (C1-C3)alkoksi, cijano, trifluormetil radikala, trifluormetoksi radikala, S(O)nAlk skupine, (C1-C3)alkilkarbonil skupine, fenila; benzil koji je nesupstituiran ili mono- ili disupstituiran sa supstituentom nezavisno odabranim od atoma halogena, (C1-C3)alkila, (C1-C3)alkoksi; trifluormetil radikala; tienil koji je nesupstituiran ili supstituiran s atomom halogena ili s izoksazolilom; R2 predstavlja atom vodika ili (C1-C3)alkil; R3 predstavlja atom vodika ili (C1-C5)alkil; R4, R5, R6, R7, R8 i R9 svaki nezavisno predstavljaju atom vodika, atom halogena, (C1-C7)alkil, (C1-C5)alkoksi, trifluormetil radikal ili S(O)nAlk skupinu; n predstavlja 0, 1 ili 2; Alk predstavlja (C1-C4)alkil, u obliku baze ili adicijske soli s kiselinom, i u obliku hidrata ili solvata. Patent sadrži još 6 patentnih zahtjeva.
Claims (7)
1. Spoj koji odgovara formuli (I):
[image]
naznačen time što:
R1 predstavlja
(C1-C6)alkil;
(C3-C7)cikloalkil koji je nesupstituiran ili supstituiran jednom ili nekoliko puta s (C1-C3)alkil skupinom;
(C3-C7)cikloalkilmetil koji je nesupstituiran ili supstituiran jednom ili nekoliko puta na karbociklu s (C1-C3)alkilom;
fenil koji je nesupstituiran ili mono-, di- ili trisupstituiran sa supstituentom nezavisno odabranim od atoma halogena, (C1-C4)alkila, (C1-C3)alkoksi, cijano, trifluormetil radikala, trifluormetoksi radikala, S(O)nAlk skupine, (C1-C3)alkilkarbonil skupine, fenila;
benzil koji je nesupstituiran ili mono- ili disupstituiran sa supstituentom nezavisno odabranim od atoma halogena, (C1-C3)alkila, (C1-C3)alkoksi; trifluormetil radikala;
tienil koji je nesupstituiran ili supstituiran s atomom halogena ili s izoksazolilom;
R2 predstavlja atom vodika ili (C1-C3)alkil;
R3 predstavlja atom vodika ili (C1-C5)alkil;
R4, R5, R6, R7, R8 i R9 svaki nezavisno predstavljaju atom vodika, atom halogena, (C1-C7)alkil, (C1-C5)alkoksi, trifluormetil radikal ili S(O)nAlk skupinu;
n predstavlja 0, 1 ili 2;
Alk predstavlja (C1-C4)alkil,
u obliku baze ili adicijske soli s kiselinom, i u obliku hidrata ili solvata.
2. Spoj formule (I) prema zahtjevu 1, naznačen time što:
R1 predstavlja
etil, izopropil, n-butil;
cikloheksil;
cikloheksilmetil;
2-klorfenil, 3-klorfenil, 2-fluorfenil, 3-klor-4-fluorfenil, 4-bromo-2-etilfenil, 3-metilfenil, 4-terc-butilfenil, 3,5-dimetilfenil, 3-metoksifenil, 4-metoksifenil, 3-cijanofenil, 4-cijanofenil, 2-(trifluormetil)fenil, 3-(trifluormetil)fenil, 4-(trifluormetil)fenil, 3,5-bis(trifluormetil)fenil, 2-(trifluormetoksi)fenil, 3-(trifluormetoksi)fenil, 2-(metilsulfonil)-fenil, 3-(metilsulfonil)fenil, 3-acetilfenil, 3-bifenil, 2-bifenil;
3-klorbenzil, 2-fluorbenzil, 4-fluorbenzil, 3-(trifluormetil)benzil, 4-(trifluormetil)benzil;
5-brom-2-tienil; 5-izoksazol-3-il-2-tienil;
R2 predstavlja atom vodika ili metil;
R3 predstavlja metil ili etil;
R4 predstavlja atom vodika;
R5 je na položaju 4 fenila i predstavlja atom broma, klora ili fluora, ili metoksi;
R6 predstavlja atom vodika;
R7 predstavlja atom vodika;
R8 je na položaju 4 fenila i predstavlja atom vodika, atom klora, atom fluora;
R9 je na položaju 2 fenila i predstavlja atom klora ili fluora;
u obliku baze ili adicijske soli s kiselinom, i u obliku hidrata ili solvata.
3. Spoj formule (I) prema zahtjevu 1, naznačen time što je odabran iz sljedeće skupine:
N-[[5-(4-bromfenil)-1-(2,4-diklorfenil)-4-metil-1H-pirazol-3-il]metil]butan-1-sulfonamid;
N-[[5-(4-bromfenil)-1-(2,4-diklorfenil)-4-metil-1H-pirazol-3-il]metil]-cikloheksansulfonamid;
N-[[5-(4-bromfenil)-1-(2,4-diklorfenil)-4-metil-1H-pirazol-3-il]metil]-cikloheksilmetansulfonamid;
N-[[5-(4-bromfenil)-1-(2,4-diklorfenil)-4-metil-1H-pirazol-3-il]metil]-3-klorbenzensulfonamid;
N-[[5-(4-bromfenil)-1-(2,4-diklorfenil)-4-metil-1H-pirazol-3-il]metil]-4-terc-butilbenzensulfonamid;
N-[[5-(4-bromfenil)-1-(2,4-diklorfenil)-4-metil-1H-pirazol-3-il]metil]-3-metoksibenzensulfonamid;
N-[[5-(4-bromfenil)-1-(2,4-diklorfenil)-4-metil-1H-pirazol-3-il]metil]-4-metoksibenzensulfonamid;
N-[[5-(4-bromfenil)-1-(2,4-diklorfenil)-4-metil-1H-pirazol-3-il]metil]-4-(trifluormetil)benzensulfonamid;
N-[[5-(4-bromfenil)-1-(2,4-diklorfenil)-4-metil-1H-pirazol-3-il]metil]-2-(metilsulfonil)benzensulfonamid;
N-[[5-(4-bromfenil)-1-(2,4-diklorfenil)-4-metil-1H-pirazol-3-il]metil]-1-(3-klorfenil)metansulfonamid;
N-[[5-(4-bromfenil)-1-(2,4-diklorfenil)-4-metil-1H-pirazol-3-il]metil]-1-[3-(trifluormetil)fenil]metansulfonamid;
N-[[5-(4-bromfenil)-1-(2,4-diklorfenil)-4-metil-1H-pirazol-3-il]metil]-3-klor-4-fluorbenzensulfonamid;
N-[[5-(4-klorfenil)-1-(2,4-diklorfenil)-4-metil-1H-pirazol-3-il]metil]-butan-1-sulfonamid;
3-klor-N-[[5-(4-klorfenil)-1-(2,4-diklorfenil)-4-metil-1H-pirazol-3-il]metil]benzensulfonamid;
4-terc-butil-N-[[5-(4-klorfenil)-1-(2,4-diklorfenil)-4-metil-1H-pirazol-3-il]metil]benzensulfonamid;
N-[[5-(4-klorfenil)-1-(2,4-diklorfenil)-4-metil-1H-pirazol-3-il]metil]-3-metoksibenzensulfonamid;
N-[[5-(4-klorfenil)-1-(2,4-diklorfenil)-4-metil-1H-pirazol-3-il]metil]-3-cijanobenzensulfonamid;
N-[[5-(4-klorfenil)-1-(2,4-diklorfenil)-4-metil-1H-pirazol-3-il]metil]-4-(trifluormetil)benzensulfonamid;
N-[[5-(4-klorfenil)-1-(2,4-diklorfenil)-4-metil-1H-pirazol-3-il]metil]-2-(trifluormetoksi)benzensulfonamid;
N-[[5-(4-klorfenil)-1-(2,4-diklorfenil)-4-metil-1H-pirazol-3-il]metil]-2-(metilsulfonil)benzensulfonamid;
3-klor-N-[[5-(4-klorfenil)-1-(2,4-diklorfenil)-4-metil-1H-pirazol-3-il]metil]-4-fluorbenzensulfonamid;
4-bromo-N-[[5-(4-klorfenil)-1-(2,4-diklorfenil)-4-metil-1H-pirazol-3-il]metil]-2-etilbenzensulfonamid;
N-[[5-(4-bromfenil)-1-(2,4-diklorfenil)-4-etil-1H-pirazol-3-il]metil]etansulfonamid;
N-[[5-(4-bromfenil)-1-(2,4-diklorfenil)-4-etil-1H-pirazol-3-il]metil]propan-2-sulfonamid;
N-[[5-(4-bromfenil)-1-(2,4-diklorfenil)-4-etil-1H-pirazol-3-il]metil]butan-1-sulfonamid;
N-[[5-(4-bromfenil)-1-(2,4-diklorfenil)-4-etil-1H-pirazol-3-il]metil]-cikloheksansulfonamid;
N-[[5-(4-bromfenil)-1-(2,4-diklorfenil)-4-etil-1H-pirazol-3-il]metil]-1-cikloheksilmetansulfonamid;
N-[[5-(4-bromfenil)-1-(2,4-diklorfenil)-4-etil-1H-pirazol-3-il]metil]-3-klorbenzensulfonamid;
N-[[5-(4-bromfenil)-1-(2,4-diklorfenil)-4-etil-1H-pirazol-3-il]metil]-2-klorbenzensulfonamid;
N-[[5-(4-bromfenil)-1-(2,4-diklorfenil)-4-etil-1H-pirazol-3-il]metil]-3-metilbenzensulfonamid;
N-[[5-(4-bromfenil)-1-(2,4-diklorfenil)-4-etil-1H-pirazol-3-il]metil]-4-terc-butilbenzensulfonamid;
N-[[5-(4-bromfenil)-1-(2,4-diklorfenil)-4-etil-1H-pirazol-3-il]metil]-4-metoksibenzensulfonamid;
N-[[5-(4-bromfenil)-1-(2,4-diklorfenil)-4-etil-1H-pirazol-3-il]metil]-3-metoksibenzensulfonamid;
N-[[5-(4-bromfenil)-1-(2,4-diklorfenil)-4-etil-1H-pirazol-3-il]metil]-4-(trifluormetil)benzensulfonamid;
N-[[5-(4-bromfenil)-1-(2,4-diklorfenil)-4-etil-1H-pirazol-3-il]metil]-3-(trifluormetil)benzensulfonamid;
N-[[5-(4-bromfenil)-1-(2,4-diklorfenil)-4-etil-1H-pirazol-3-il]metil]-2-(trifluormetil)benzensulfonamid;
N-[[5-(4-bromfenil)-1-(2,4-diklorfenil)-4-etil-1H-pirazol-3-il]metil]-3-(trifluormetoksi)benzensulfonamid;
N-[[5-(4-bromfenil)-1-(2,4-diklorfenil)-4-etil-1H-pirazol-3-il]metil]-2-(trifluormetoksi)benzensulfonamid;
3-acetil-N-[[5-(4-bromfenil)-1-(2,4-diklorfenil)-4-etil-1H-pirazol-3-il]metil]benzensulfonamid;
N-[[5-(4-bromfenil)-1-(2,4-diklorfenil)-4-etil-1H-pirazol-3-il]metil]bifenil-3-sulfonamid;
N-[[5-(4-bromfenil)-1-(2,4-diklorfenil)-4-etil-1H-pirazol-3-il]metil]-1-[4-(trifluormetil)fenil]metansulfonamid;
N-[[5-(4-bromfenil)-1-(2,4-diklorfenil)-4-etil-1H-pirazol-3-il]metil]-1-[3-(trifluormetil)fenil]metansulfonamid;
N-[[5-(4-bromfenil)-1-(2,4-diklorfenil)-4-etil-1H-pirazol-3-il]metil]-3,5-dimetilbenzensulfonamid;
N-[[5-(4-bromfenil)-1-(2,4-diklorfenil)-4-etil-1H-pirazol-3-il]metil]-3,5-bis(trifluormetil)benzensulfonamid;
3-klor-N-[[1-(2-klorfenil)-5-(4-klorfenil)-4-metil-1H-pirazol-3-il]metil]benzensulfonamid;
N-[[1-(2-klorfenil)-5-(4-klorfenil)-4-metil-1H-pirazol-3-il]metil]-2-fluorbenzensulfonamid;
N-[[1-(2-klorfenil)-5-(4-klorfenil)-4-metil-1H-pirazol-3-il]metil]-3-cijanobenzensulfonamid;
N-[[1-(2-klorfenil)-5-(4-klorfenil)-4-metil-1H-pirazol-3-il]metil]-3-metoksibenzensulfonamid;
N-[[5-(4-bromfenil)-1-(2,4-diklorfenil)-4-metil-1H-pirazol-3-il]metil]-3-metoksibenzensulfonamid;
N-[[5-(4-bromfenil)-1-(2,4-diklorfenil)-4-metil-1H-pirazol-3-il]metil]-3-cijanobenzensulfonamid;
N-[[5-(4-bromfenil)-1-(2,4-diklorfenil)-4-etil-1H-pirazol-3-il]metil]-1-(2-fluorfenil)metansulfonamid;
N-[[5-(4-bromfenil)-1-(2,4-diklorfenil)-4-etil-1H-pirazol-3-il]metil]-1-(4-fluorfenil)metansulfonamid;
5-bromo-N-[[5-(4-bromfenil)-1-(2,4-diklorfenil)-4-etil-1H-pirazol-3-il]metil]tiofen-2-sulfonamid;
N-[[5-(4-bromfenil)-1-(2,4-diklorfenil)-4-etil-1H-pirazol-3-il]metil]-5-izoksazol-3-iltiofen-2-sulfonamid;
3-klor-N-[[1-(2,4-diklorfenil)-5-(4-metoksifenil)-4-metil-1H-pirazol-3-il]metil]benzensulfonamid;
N-[[1-(2,4-diklorfenil)-5-(4-metoksifenil)-4-metil-1H-pirazol-3-il]metil]-3-metilbenzensulfonamid;
u obliku baze ili adicijske soli s kiselinom, i u obliku hidrata ili solvata.
4. Postupak za dobivanje spojeva formule (I) prema zahtjevu 1, naznačen time što:
spoj formule:
[image]
u kojoj R2, R3, R4, R5, R6, R7, R8 i R9 su kao što je definirano za spoj formule (I) u zahtjevu 1, reagira, u prisutnosti baze i u otapalu, sa sulfonil halogenidom formule:
[image]
u kojoj R1 je kao što je definirano za spoj formule (I) u zahtjevu 1 i Hal predstavlja atom halogena.
5. Lijek, naznačen time što sadržava spoj formule (I) prema bilo kojem od zahtjeva 1 do 3, ili adicijske soli ovog spoja s farmaceutski prihvatljivom kiselinom, ili hidrat ili solvat spoja formule (I).
6. Farmaceutski pripravak, naznačen time što sadržava spoj formule (I) prema bilo kojem od zahtjeva 1 do 3, ili farmaceutski prihvatljivu sol, hidrat ili solvat ovog spoja, i najmanje jedno farmaceutski prihvatljivo pomoćno sredstvo.
7. Upotreba spoja formule (I) prema bilo kojem od zahtjeva 1 do 3, naznačena time što se upotrebljava za dobivanje lijeka namijenjenog liječenju i prevenciji poremećaja apetita, gastrointestinalnih poremećaja, upalnih fenomena, bolesti imunološkog sustava, psihotičnih poremećaja, ovisnosti o alkoholu i ovisnosti o nikotinu.
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PCT/FR2005/000031 WO2005073197A1 (fr) | 2004-01-12 | 2005-01-07 | Derives de n-` (1,5-diphenyl-1h-pyrazol-3-yl) sulfonamide avec une affinite pour les recepteurs cb1 |
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FR2880890B1 (fr) * | 2005-01-19 | 2007-03-30 | Sanofi Aventis Sa | Derives de n-[(4,5-diphenyl-2-thienyl)methyl]sulfonamide, leur preparation et leur application en therapeutique |
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FR2899899A1 (fr) * | 2006-04-14 | 2007-10-19 | Sanofi Aventis Sa | Derives d'aminomethyl pyridine, leur preparation et leur application en therapeutique |
ATE469129T1 (de) * | 2006-07-11 | 2010-06-15 | Sanofi Aventis | N-ä(1,5-diphenyl-1h-pyrazol-3- yl)methylüsulfonamid-derivate antagonisten der cb1 rezeptoren der cannabinoide |
JP2008019205A (ja) * | 2006-07-12 | 2008-01-31 | Sanofi-Aventis | N−[(1,5−ジフェニル−1h−ピラゾール−3−イル)メチル]スルホンアミド誘導体、その調製法および治療におけるその応用 |
US7297710B1 (en) * | 2006-07-12 | 2007-11-20 | Sanofi-Aventis | Derivatives of N-[(1,5-diphenyl-1H-pyrazol-3-yl)methyl]sulfonamide, their preparation and their application in therapeutics |
WO2008062424A2 (en) * | 2006-07-31 | 2008-05-29 | Cadila Healthcare Limited | Substituted 4,5-dihydro-1h-pyrazole derivatives as cannabinoid modulators |
US7875647B2 (en) | 2006-09-29 | 2011-01-25 | Green Cross Corporation | Heteroaryl-pyrazole derivatives as cannabinoid CB1 receptor antagonists |
EP1911747A1 (en) * | 2006-10-11 | 2008-04-16 | Laboratorios del Dr. Esteve S.A. | Sulfonamide substituted pyrazoline compounds, their preparation and use as CB1 modulators |
FR2911136B1 (fr) | 2007-01-05 | 2009-02-20 | Sanofi Aventis Sa | Derives de n-(4-cyano-1h-pyrazol-3-yl)methylamine substitues leur preparation et leur application en therapeutique. |
FR2919184A1 (fr) * | 2007-07-26 | 2009-01-30 | Sanofi Aventis Sa | L'acide 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4- methylpyrazole-3-carboxylique, ses esters, ses sels pharmaceutiquement acceptables et leurs solvates pour leur utilisation comme medicament. |
MX2015002036A (es) | 2012-08-16 | 2016-01-22 | Janssen Pharmaceutica Nv | Pirazoles sustituidos como bloqueadores del canal de calcio tipo n. |
MX2015002039A (es) * | 2012-08-16 | 2016-01-22 | Janssen Pharmaceutica Nv | Pirrolopirazoles como bloqueadores del canal de calcio tipo n. |
BR112015016323A2 (pt) * | 2013-01-17 | 2017-07-11 | Hoffmann La Roche | agonistas de receptor de oxitocina para tratamento de doenças de cns |
US9453002B2 (en) | 2013-08-16 | 2016-09-27 | Janssen Pharmaceutica Nv | Substituted imidazoles as N-type calcium channel blockers |
KR101685993B1 (ko) * | 2014-05-15 | 2016-12-13 | 한국과학기술연구원 | 전압개폐 칼슘이온채널 억제 활성화능을 갖는 n-(피라졸릴메틸)아릴설폰아마이드 화합물 및 이를 포함하는 약학적 조성물 |
WO2022109292A1 (en) * | 2020-11-20 | 2022-05-27 | University Of Pittsburgh - Of The Commonwealth System Of Higher Education | Methods and materials for inhibiting cb1 activity |
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FR2692575B1 (fr) * | 1992-06-23 | 1995-06-30 | Sanofi Elf | Nouveaux derives du pyrazole, procede pour leur preparation et compositions pharmaceutiques les contenant. |
FR2713225B1 (fr) * | 1993-12-02 | 1996-03-01 | Sanofi Sa | N-pipéridino-3-pyrazolecarboxamide substitué. |
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