JP2013538198A - フェナルキルアミン誘導体、それを含有する医薬組成物及び治療におけるその使用 - Google Patents
フェナルキルアミン誘導体、それを含有する医薬組成物及び治療におけるその使用 Download PDFInfo
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- JP2013538198A JP2013538198A JP2013523638A JP2013523638A JP2013538198A JP 2013538198 A JP2013538198 A JP 2013538198A JP 2013523638 A JP2013523638 A JP 2013523638A JP 2013523638 A JP2013523638 A JP 2013523638A JP 2013538198 A JP2013538198 A JP 2013538198A
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- Prior art keywords
- alkyl
- ethyl
- methyl
- benzyl
- sulfonic acid
- Prior art date
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- 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 16
- 238000002560 therapeutic procedure Methods 0.000 title claims description 5
- 229940085239 selective calcium channel blockers with direct cardiac effects phenylalkylamine derivative Drugs 0.000 title 1
- 150000003839 salts Chemical class 0.000 claims abstract description 16
- -1 C 1 -C 6 -alkoxy Chemical group 0.000 claims description 643
- 150000001875 compounds Chemical class 0.000 claims description 222
- 229910052739 hydrogen Inorganic materials 0.000 claims description 183
- 239000001257 hydrogen Substances 0.000 claims description 183
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 140
- 125000004432 carbon atom Chemical group C* 0.000 claims description 113
- 238000011282 treatment Methods 0.000 claims description 80
- 208000002193 Pain Diseases 0.000 claims description 78
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 68
- 239000003814 drug Substances 0.000 claims description 58
- 238000000034 method Methods 0.000 claims description 45
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 42
- 229910052736 halogen Inorganic materials 0.000 claims description 38
- 125000002947 alkylene group Chemical group 0.000 claims description 37
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 36
- 108010063380 Glycine Plasma Membrane Transport Proteins Proteins 0.000 claims description 35
- 102000010726 Glycine Plasma Membrane Transport Proteins Human genes 0.000 claims description 35
- 150000002367 halogens Chemical class 0.000 claims description 33
- 125000000623 heterocyclic group Chemical group 0.000 claims description 32
- 125000004429 atom Chemical group 0.000 claims description 30
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 29
- 238000004519 manufacturing process Methods 0.000 claims description 27
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 21
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 20
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 19
- 208000035475 disorder Diseases 0.000 claims description 16
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 16
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 14
- 229910052799 carbon Inorganic materials 0.000 claims description 14
- 208000020016 psychiatric disease Diseases 0.000 claims description 14
- 125000003118 aryl group Chemical group 0.000 claims description 13
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 12
- 201000000980 schizophrenia Diseases 0.000 claims description 11
- 125000006296 sulfonyl amino group Chemical group [H]N(*)S(*)(=O)=O 0.000 claims description 11
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 10
- 208000019901 Anxiety disease Diseases 0.000 claims description 10
- 206010012289 Dementia Diseases 0.000 claims description 10
- 208000012902 Nervous system disease Diseases 0.000 claims description 10
- 208000010877 cognitive disease Diseases 0.000 claims description 10
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 9
- 230000000926 neurological effect Effects 0.000 claims description 9
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 8
- 230000002401 inhibitory effect Effects 0.000 claims description 8
- SMMSWRPABQHXRV-UHFFFAOYSA-N n-[2-[3-(3-benzylpyrrolidin-3-yl)phenoxy]ethyl]-1-methylimidazole-4-sulfonamide Chemical compound CN1C=NC(S(=O)(=O)NCCOC=2C=C(C=CC=2)C2(CC=3C=CC=CC=3)CNCC2)=C1 SMMSWRPABQHXRV-UHFFFAOYSA-N 0.000 claims description 8
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims description 7
- 125000003282 alkyl amino group Chemical group 0.000 claims description 7
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 7
- 125000004845 (C1-C6) alkylsulfonylamino group Chemical group 0.000 claims description 6
- 208000025966 Neurological disease Diseases 0.000 claims description 6
- 125000004419 alkynylene group Chemical group 0.000 claims description 6
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 5
- 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims description 5
- 208000020925 Bipolar disease Diseases 0.000 claims description 5
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 5
- 241000124008 Mammalia Species 0.000 claims description 5
- 208000015802 attention deficit-hyperactivity disease Diseases 0.000 claims description 5
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 5
- SEPPVOUBHWNCAW-FNORWQNLSA-N (E)-4-oxonon-2-enal Chemical compound CCCCCC(=O)\C=C\C=O SEPPVOUBHWNCAW-FNORWQNLSA-N 0.000 claims description 4
- JLMQINUOMQKYQB-UHFFFAOYSA-N 2-[3-[(cyclopropylmethylsulfonylamino)methyl]phenyl]-3-phenylpropanamide Chemical compound C=1C=CC(CNS(=O)(=O)CC2CC2)=CC=1C(C(=O)N)CC1=CC=CC=C1 JLMQINUOMQKYQB-UHFFFAOYSA-N 0.000 claims description 4
- 208000019022 Mood disease Diseases 0.000 claims description 4
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 4
- 230000004064 dysfunction Effects 0.000 claims description 4
- 230000005764 inhibitory process Effects 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 125000006413 ring segment Chemical group 0.000 claims description 4
- LRTPEYUVINTMGW-UHFFFAOYSA-N tert-butyl n-[2-[1-(4-chlorophenyl)cyclobutyl]-2-[3-[[methyl(propylsulfonyl)amino]methyl]phenyl]ethyl]carbamate Chemical compound CCCS(=O)(=O)N(C)CC1=CC=CC(C(CNC(=O)OC(C)(C)C)C2(CCC2)C=2C=CC(Cl)=CC=2)=C1 LRTPEYUVINTMGW-UHFFFAOYSA-N 0.000 claims description 4
- GBXQPDCOMJJCMJ-UHFFFAOYSA-M trimethyl-[6-(trimethylazaniumyl)hexyl]azanium;bromide Chemical compound [Br-].C[N+](C)(C)CCCCCC[N+](C)(C)C GBXQPDCOMJJCMJ-UHFFFAOYSA-M 0.000 claims description 4
- 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 claims description 3
- KSZCAGWHZCZJLZ-UHFFFAOYSA-N 1-methylimidazole-4-sulfonic acid Chemical compound CN1C=NC(S(O)(=O)=O)=C1 KSZCAGWHZCZJLZ-UHFFFAOYSA-N 0.000 claims description 3
- 125000003320 C2-C6 alkenyloxy group Chemical group 0.000 claims description 3
- 150000001408 amides Chemical class 0.000 claims description 3
- PQSAQCVJELMITK-UHFFFAOYSA-N ethyl 3-benzyl-3-[3-[2-(cyclopropylmethylsulfonylamino)ethoxy]phenyl]azetidine-1-carboxylate Chemical compound C1N(C(=O)OCC)CC1(C=1C=C(OCCNS(=O)(=O)CC2CC2)C=CC=1)CC1=CC=CC=C1 PQSAQCVJELMITK-UHFFFAOYSA-N 0.000 claims description 3
- 125000005549 heteroarylene group Chemical group 0.000 claims description 3
- VWYDDIGQGBFYCZ-UHFFFAOYSA-N n-[2-[3-(1-amino-3-phenylpropan-2-yl)phenoxy]ethyl]-1-methylimidazole-4-sulfonamide Chemical compound CN1C=NC(S(=O)(=O)NCCOC=2C=C(C=CC=2)C(CN)CC=2C=CC=CC=2)=C1 VWYDDIGQGBFYCZ-UHFFFAOYSA-N 0.000 claims description 3
- REUMXPBOWOBHQD-UHFFFAOYSA-N n-[2-[3-(3-benzyl-1-methylpiperidin-3-yl)phenoxy]ethyl]-1-methylimidazole-4-sulfonamide Chemical compound C1N(C)CCCC1(C=1C=C(OCCNS(=O)(=O)C=2N=CN(C)C=2)C=CC=1)CC1=CC=CC=C1 REUMXPBOWOBHQD-UHFFFAOYSA-N 0.000 claims description 3
- OSKPYFWBFJONLR-UHFFFAOYSA-N n-[2-[3-(3-benzyl-5-oxopyrrolidin-3-yl)phenoxy]ethyl]-1-cyclopropylmethanesulfonamide Chemical compound C1NC(=O)CC1(C=1C=C(OCCNS(=O)(=O)CC2CC2)C=CC=1)CC1=CC=CC=C1 OSKPYFWBFJONLR-UHFFFAOYSA-N 0.000 claims description 3
- ZPYOWFUKZRMFLZ-UHFFFAOYSA-N n-[2-[3-(3-benzyl-5-oxopyrrolidin-3-yl)phenoxy]ethyl]-1-methylimidazole-4-sulfonamide Chemical compound CN1C=NC(S(=O)(=O)NCCOC=2C=C(C=CC=2)C2(CC=3C=CC=CC=3)CC(=O)NC2)=C1 ZPYOWFUKZRMFLZ-UHFFFAOYSA-N 0.000 claims description 3
- QGSIOHCMIXWVQS-UHFFFAOYSA-N n-[2-[3-(3-benzylazetidin-3-yl)phenoxy]ethyl]-1-methylimidazole-4-sulfonamide Chemical compound CN1C=NC(S(=O)(=O)NCCOC=2C=C(C=CC=2)C2(CC=3C=CC=CC=3)CNC2)=C1 QGSIOHCMIXWVQS-UHFFFAOYSA-N 0.000 claims description 3
- YUEYKOAMVDQBAX-UHFFFAOYSA-N n-[2-[3-(3-benzylazetidin-3-yl)phenoxy]ethyl]-1-methylpyrazole-4-sulfonamide Chemical compound C1=NN(C)C=C1S(=O)(=O)NCCOC1=CC=CC(C2(CC=3C=CC=CC=3)CNC2)=C1 YUEYKOAMVDQBAX-UHFFFAOYSA-N 0.000 claims description 3
- MWDMPXOTEHTCSL-UHFFFAOYSA-N n-[2-[3-[(benzylamino)-[1-(4-chlorophenyl)cyclobutyl]methyl]phenoxy]ethyl]propane-1-sulfonamide Chemical compound CCCS(=O)(=O)NCCOC1=CC=CC(C(NCC=2C=CC=CC=2)C2(CCC2)C=2C=CC(Cl)=CC=2)=C1 MWDMPXOTEHTCSL-UHFFFAOYSA-N 0.000 claims description 3
- MTZHVAHBLJFAHL-UHFFFAOYSA-N n-[2-[3-[1-amino-3-(3,5-difluorophenyl)propan-2-yl]phenoxy]ethyl]-1-methylpyrazole-4-sulfonamide Chemical compound C1=NN(C)C=C1S(=O)(=O)NCCOC1=CC=CC(C(CN)CC=2C=C(F)C=C(F)C=2)=C1 MTZHVAHBLJFAHL-UHFFFAOYSA-N 0.000 claims description 3
- LCCOIUSPPDYVKE-UHFFFAOYSA-N n-[2-[3-[3-benzyl-1-(2-fluoroethyl)azetidin-3-yl]phenoxy]ethyl]-1-methylimidazole-4-sulfonamide Chemical compound CN1C=NC(S(=O)(=O)NCCOC=2C=C(C=CC=2)C2(CC=3C=CC=CC=3)CN(CCF)C2)=C1 LCCOIUSPPDYVKE-UHFFFAOYSA-N 0.000 claims description 3
- DRPPFVAIHWQKOO-UHFFFAOYSA-N n-[2-[5-(3-benzyl-1-methylazetidin-3-yl)-2-fluorophenoxy]ethyl]-1-methylimidazole-4-sulfonamide Chemical compound C1N(C)CC1(C=1C=C(OCCNS(=O)(=O)C=2N=CN(C)C=2)C(F)=CC=1)CC1=CC=CC=C1 DRPPFVAIHWQKOO-UHFFFAOYSA-N 0.000 claims description 3
- URILZVILCGHFJP-UHFFFAOYSA-N n-[[3-(3-benzyl-5-oxopyrrolidin-3-yl)phenyl]methyl]-1-methylimidazole-4-sulfonamide Chemical compound CN1C=NC(S(=O)(=O)NCC=2C=C(C=CC=2)C2(CC=3C=CC=CC=3)CC(=O)NC2)=C1 URILZVILCGHFJP-UHFFFAOYSA-N 0.000 claims description 3
- FSONNASPZTXNNS-UHFFFAOYSA-N n-[[3-(3-benzylpyrrolidin-3-yl)phenyl]methyl]-1-methylpyrazole-4-sulfonamide Chemical compound C1=NN(C)C=C1S(=O)(=O)NCC1=CC=CC(C2(CC=3C=CC=CC=3)CNCC2)=C1 FSONNASPZTXNNS-UHFFFAOYSA-N 0.000 claims description 3
- 208000033808 peripheral neuropathy Diseases 0.000 claims description 3
- QHKGGFXROLLYIK-UHFFFAOYSA-N tert-butyl n-[2-[1-(4-chlorophenyl)cyclobutyl]-2-[3-[[methyl-(1-methylpyrazol-4-yl)sulfonylamino]methyl]phenyl]ethyl]carbamate Chemical compound C1=NN(C)C=C1S(=O)(=O)N(C)CC(C=1)=CC=CC=1C(CNC(=O)OC(C)(C)C)C1(C=2C=CC(Cl)=CC=2)CCC1 QHKGGFXROLLYIK-UHFFFAOYSA-N 0.000 claims description 3
- UXIOOCXFWZVFHA-UHFFFAOYSA-N 1-cyclopropyl-n-[[3-(1-morpholin-4-yl-3-phenylpropan-2-yl)phenyl]methyl]methanesulfonamide Chemical compound C=1C=CC(C(CN2CCOCC2)CC=2C=CC=CC=2)=CC=1CNS(=O)(=O)CC1CC1 UXIOOCXFWZVFHA-UHFFFAOYSA-N 0.000 claims description 2
- ADWQNYPZFCWFJT-UHFFFAOYSA-N 1-methyl-n-[2-[3-(1-phenyl-3-pyrrolidin-1-ylpropan-2-yl)phenoxy]ethyl]imidazole-4-sulfonamide Chemical compound CN1C=NC(S(=O)(=O)NCCOC=2C=C(C=CC=2)C(CN2CCCC2)CC=2C=CC=CC=2)=C1 ADWQNYPZFCWFJT-UHFFFAOYSA-N 0.000 claims description 2
- RGZQWLFZGIRJMF-UHFFFAOYSA-N 1-methyl-n-[[3-(1-morpholin-4-yl-1-oxo-3-phenylpropan-2-yl)phenyl]methyl]imidazole-4-sulfonamide Chemical compound CN1C=NC(S(=O)(=O)NCC=2C=C(C=CC=2)C(CC=2C=CC=CC=2)C(=O)N2CCOCC2)=C1 RGZQWLFZGIRJMF-UHFFFAOYSA-N 0.000 claims description 2
- DMKZOFYTZBUHGZ-UHFFFAOYSA-N 1-methyl-n-[[3-(1-morpholin-4-yl-3-phenylpropan-2-yl)phenyl]methyl]imidazole-4-sulfonamide Chemical compound CN1C=NC(S(=O)(=O)NCC=2C=C(C=CC=2)C(CN2CCOCC2)CC=2C=CC=CC=2)=C1 DMKZOFYTZBUHGZ-UHFFFAOYSA-N 0.000 claims description 2
- FMXDGIFSBYAIOK-UHFFFAOYSA-N 1-methyl-n-[[3-(1-morpholin-4-yl-3-phenylpropan-2-yl)phenyl]methyl]pyrazole-4-sulfonamide Chemical compound C1=NN(C)C=C1S(=O)(=O)NCC1=CC=CC(C(CN2CCOCC2)CC=2C=CC=CC=2)=C1 FMXDGIFSBYAIOK-UHFFFAOYSA-N 0.000 claims description 2
- WHYASBKVZHKQTN-UHFFFAOYSA-N 1-methylpyrazole-4-sulfonic acid Chemical compound CN1C=C(S(O)(=O)=O)C=N1 WHYASBKVZHKQTN-UHFFFAOYSA-N 0.000 claims description 2
- FZCRCUPHHLNAON-UHFFFAOYSA-N 2-[3-[[(1-methylimidazol-4-yl)sulfonylamino]methyl]phenyl]-3-phenylpropanamide Chemical compound CN1C=NC(S(=O)(=O)NCC=2C=C(C=CC=2)C(CC=2C=CC=CC=2)C(N)=O)=C1 FZCRCUPHHLNAON-UHFFFAOYSA-N 0.000 claims description 2
- HJBAFMRHRSTANB-UHFFFAOYSA-N 2-[3-[[(1-methylpyrazol-4-yl)sulfonylamino]methyl]phenyl]-3-phenylpropanamide Chemical compound C1=NN(C)C=C1S(=O)(=O)NCC1=CC=CC(C(CC=2C=CC=CC=2)C(N)=O)=C1 HJBAFMRHRSTANB-UHFFFAOYSA-N 0.000 claims description 2
- OYTBMOZGOUDYTI-UHFFFAOYSA-N ethyl 3-benzyl-3-[3-[2-[(1-methylimidazol-4-yl)sulfonylamino]ethoxy]phenyl]azetidine-1-carboxylate Chemical compound C1N(C(=O)OCC)CC1(C=1C=C(OCCNS(=O)(=O)C=2N=CN(C)C=2)C=CC=1)CC1=CC=CC=C1 OYTBMOZGOUDYTI-UHFFFAOYSA-N 0.000 claims description 2
- PKUCOECXEYLXBZ-UHFFFAOYSA-N n-[2-[3-(1-amino-3-phenylpropan-2-yl)-4-fluorophenoxy]ethyl]-1-methylimidazole-4-sulfonamide Chemical compound CN1C=NC(S(=O)(=O)NCCOC=2C=C(C(F)=CC=2)C(CN)CC=2C=CC=CC=2)=C1 PKUCOECXEYLXBZ-UHFFFAOYSA-N 0.000 claims description 2
- MZBQASAPYIATSP-UHFFFAOYSA-N n-[2-[3-(1-amino-3-phenylpropan-2-yl)phenoxy]ethyl]-1-methylpyrazole-4-sulfonamide Chemical compound C1=NN(C)C=C1S(=O)(=O)NCCOC1=CC=CC(C(CN)CC=2C=CC=CC=2)=C1 MZBQASAPYIATSP-UHFFFAOYSA-N 0.000 claims description 2
- DOQKGALNCBHDBJ-UHFFFAOYSA-N n-[2-[3-(3-benzyl-1-methylpiperidin-3-yl)phenoxy]ethyl]-1-cyclopropylmethanesulfonamide Chemical compound C1N(C)CCCC1(C=1C=C(OCCNS(=O)(=O)CC2CC2)C=CC=1)CC1=CC=CC=C1 DOQKGALNCBHDBJ-UHFFFAOYSA-N 0.000 claims description 2
- DSXNXHSTAJFSMS-UHFFFAOYSA-N n-[2-[3-(3-benzyl-1-methylpiperidin-3-yl)phenoxy]ethyl]-1-methylpyrazole-4-sulfonamide Chemical compound C1N(C)CCCC1(C=1C=C(OCCNS(=O)(=O)C2=CN(C)N=C2)C=CC=1)CC1=CC=CC=C1 DSXNXHSTAJFSMS-UHFFFAOYSA-N 0.000 claims description 2
- MCGLETVIBZJYLF-UHFFFAOYSA-N n-[2-[3-(3-benzyl-1-methylpyrrolidin-3-yl)phenoxy]ethyl]-1-methylimidazole-4-sulfonamide Chemical compound C1N(C)CCC1(C=1C=C(OCCNS(=O)(=O)C=2N=CN(C)C=2)C=CC=1)CC1=CC=CC=C1 MCGLETVIBZJYLF-UHFFFAOYSA-N 0.000 claims description 2
- PKUNQFTZTCBZGM-UHFFFAOYSA-N n-[2-[3-(3-benzyl-1-methylpyrrolidin-3-yl)phenoxy]ethyl]-n,1-dimethylimidazole-4-sulfonamide Chemical compound C=1N(C)C=NC=1S(=O)(=O)N(C)CCOC(C=1)=CC=CC=1C1(CC=2C=CC=CC=2)CCN(C)C1 PKUNQFTZTCBZGM-UHFFFAOYSA-N 0.000 claims description 2
- RJMXPCSRWXTANQ-UHFFFAOYSA-N n-[2-[3-(3-benzyl-1-propan-2-ylpyrrolidin-3-yl)phenoxy]ethyl]-1-methylimidazole-4-sulfonamide Chemical compound C1N(C(C)C)CCC1(C=1C=C(OCCNS(=O)(=O)C=2N=CN(C)C=2)C=CC=1)CC1=CC=CC=C1 RJMXPCSRWXTANQ-UHFFFAOYSA-N 0.000 claims description 2
- MQFRFPIYIFJECT-UHFFFAOYSA-N n-[2-[3-(3-benzyl-5-oxopyrrolidin-3-yl)phenoxy]ethyl]-1-methylpyrazole-4-sulfonamide Chemical compound C1=NN(C)C=C1S(=O)(=O)NCCOC1=CC=CC(C2(CC=3C=CC=CC=3)CC(=O)NC2)=C1 MQFRFPIYIFJECT-UHFFFAOYSA-N 0.000 claims description 2
- UBLSYMJIAYDMPF-UHFFFAOYSA-N n-[2-[3-(3-benzylazetidin-3-yl)phenoxy]ethyl]-1-cyclopropylmethanesulfonamide Chemical compound C=1C=CC(C2(CC=3C=CC=CC=3)CNC2)=CC=1OCCNS(=O)(=O)CC1CC1 UBLSYMJIAYDMPF-UHFFFAOYSA-N 0.000 claims description 2
- KOMIOKKXRGKQFZ-UHFFFAOYSA-N n-[2-[3-(3-benzylpyrrolidin-3-yl)phenoxy]ethyl]-1-cyclopropylmethanesulfonamide Chemical compound C=1C=CC(C2(CC=3C=CC=CC=3)CNCC2)=CC=1OCCNS(=O)(=O)CC1CC1 KOMIOKKXRGKQFZ-UHFFFAOYSA-N 0.000 claims description 2
- CFTHJDDWWCKSQB-UHFFFAOYSA-N n-[2-[3-(3-benzylpyrrolidin-3-yl)phenoxy]ethyl]-1-methylpyrazole-4-sulfonamide Chemical compound C1=NN(C)C=C1S(=O)(=O)NCCOC1=CC=CC(C2(CC=3C=CC=CC=3)CNCC2)=C1 CFTHJDDWWCKSQB-UHFFFAOYSA-N 0.000 claims description 2
- TYSSRHFFJQXYGK-UHFFFAOYSA-N n-[2-[3-[1-(azetidin-1-yl)-3-phenylpropan-2-yl]phenoxy]ethyl]-1-methylpyrazole-4-sulfonamide Chemical compound C1=NN(C)C=C1S(=O)(=O)NCCOC1=CC=CC(C(CN2CCC2)CC=2C=CC=CC=2)=C1 TYSSRHFFJQXYGK-UHFFFAOYSA-N 0.000 claims description 2
- KQHLMNNUVYBWTO-UHFFFAOYSA-N n-[2-[3-[1-(dimethylamino)-3-[3-(trifluoromethyl)phenyl]propan-2-yl]phenoxy]ethyl]-1-methylimidazole-4-sulfonamide Chemical compound C=1C=CC(OCCNS(=O)(=O)C=2N=CN(C)C=2)=CC=1C(CN(C)C)CC1=CC=CC(C(F)(F)F)=C1 KQHLMNNUVYBWTO-UHFFFAOYSA-N 0.000 claims description 2
- IAGZMVOWQPSWDX-UHFFFAOYSA-N n-[2-[3-[1-(dimethylamino)-3-[3-(trifluoromethyl)phenyl]propan-2-yl]phenoxy]ethyl]-1-methylpyrazole-4-sulfonamide Chemical compound C=1C=CC(OCCNS(=O)(=O)C2=CN(C)N=C2)=CC=1C(CN(C)C)CC1=CC=CC(C(F)(F)F)=C1 IAGZMVOWQPSWDX-UHFFFAOYSA-N 0.000 claims description 2
- HQMRYTKVVGMYIS-UHFFFAOYSA-N n-[2-[3-[1-(dimethylamino)-3-phenylpropan-2-yl]-4-fluorophenoxy]ethyl]-1-methylimidazole-4-sulfonamide Chemical compound C=1C(OCCNS(=O)(=O)C=2N=CN(C)C=2)=CC=C(F)C=1C(CN(C)C)CC1=CC=CC=C1 HQMRYTKVVGMYIS-UHFFFAOYSA-N 0.000 claims description 2
- BEUJACZOHGUWES-UHFFFAOYSA-N n-[2-[3-[1-(dimethylamino)-3-phenylpropan-2-yl]-4-fluorophenoxy]ethyl]-1-methylpyrazole-4-sulfonamide Chemical compound C=1C(OCCNS(=O)(=O)C2=CN(C)N=C2)=CC=C(F)C=1C(CN(C)C)CC1=CC=CC=C1 BEUJACZOHGUWES-UHFFFAOYSA-N 0.000 claims description 2
- JVJZPQXPPCKFEZ-UHFFFAOYSA-N n-[2-[3-[1-(dimethylamino)-3-phenylpropan-2-yl]phenoxy]ethyl]-1-methylimidazole-4-sulfonamide Chemical compound C=1C=CC(OCCNS(=O)(=O)C=2N=CN(C)C=2)=CC=1C(CN(C)C)CC1=CC=CC=C1 JVJZPQXPPCKFEZ-UHFFFAOYSA-N 0.000 claims description 2
- JRJOEONTFKCOPP-UHFFFAOYSA-N n-[2-[3-[1-(dimethylamino)-3-phenylpropan-2-yl]phenoxy]ethyl]-1-methylpyrazole-4-sulfonamide Chemical compound C=1C=CC(OCCNS(=O)(=O)C2=CN(C)N=C2)=CC=1C(CN(C)C)CC1=CC=CC=C1 JRJOEONTFKCOPP-UHFFFAOYSA-N 0.000 claims description 2
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Classifications
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- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
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- C07D205/00—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom
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- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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- C07D207/263—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
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- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
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- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
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- C07D295/135—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
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- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
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- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C—CHEMISTRY; METALLURGY
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- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/02—Systems containing only non-condensed rings with a three-membered ring
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/04—Systems containing only non-condensed rings with a four-membered ring
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| US37352610P | 2010-08-13 | 2010-08-13 | |
| US61/373,526 | 2010-08-13 | ||
| PCT/EP2011/063971 WO2012020130A1 (en) | 2010-08-13 | 2011-08-12 | Phenalkylamine derivatives, pharmaceutical compositions containing them, and their use in therapy |
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| JP2013538198A true JP2013538198A (ja) | 2013-10-10 |
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| MX (1) | MX2013001790A (enExample) |
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| AR075442A1 (es) | 2009-02-16 | 2011-03-30 | Abbott Gmbh & Co Kg | Derivados de aminotetralina, composiciones farmaceuticas que las contienen y sus usos en terapia |
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| US9656955B2 (en) | 2013-03-15 | 2017-05-23 | Abbvie Inc. | Pyrrolidine derivatives, pharmaceutical compositions containing them, and their use in therapy |
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-
2011
- 2011-08-10 US US13/206,937 patent/US8877794B2/en not_active Expired - Fee Related
- 2011-08-11 TW TW100128764A patent/TW201211031A/zh unknown
- 2011-08-12 EP EP11748621.7A patent/EP2603487A1/en not_active Withdrawn
- 2011-08-12 WO PCT/EP2011/063971 patent/WO2012020130A1/en not_active Ceased
- 2011-08-12 MX MX2013001790A patent/MX2013001790A/es active IP Right Grant
- 2011-08-12 JP JP2013523638A patent/JP2013538198A/ja active Pending
- 2011-08-12 CA CA2806643A patent/CA2806643A1/en not_active Abandoned
- 2011-08-12 CN CN201180039735XA patent/CN103237788A/zh active Pending
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2014
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Also Published As
| Publication number | Publication date |
|---|---|
| CA2806643A1 (en) | 2012-02-16 |
| US9238619B2 (en) | 2016-01-19 |
| EP2603487A1 (en) | 2013-06-19 |
| US20120077796A1 (en) | 2012-03-29 |
| US8877794B2 (en) | 2014-11-04 |
| US20140256701A1 (en) | 2014-09-11 |
| WO2012020130A1 (en) | 2012-02-16 |
| TW201211031A (en) | 2012-03-16 |
| MX2013001790A (es) | 2013-10-03 |
| CN103237788A (zh) | 2013-08-07 |
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