JP2013538198A5 - - Google Patents
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- JP2013538198A5 JP2013538198A5 JP2013523638A JP2013523638A JP2013538198A5 JP 2013538198 A5 JP2013538198 A5 JP 2013538198A5 JP 2013523638 A JP2013523638 A JP 2013523638A JP 2013523638 A JP2013523638 A JP 2013523638A JP 2013538198 A5 JP2013538198 A5 JP 2013538198A5
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- JP
- Japan
- Prior art keywords
- alkyl
- ethyl
- methyl
- benzyl
- sulfonic acid
- 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
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- 229910052739 hydrogen Inorganic materials 0.000 claims 37
- 239000001257 hydrogen Substances 0.000 claims 37
- 150000001875 compounds Chemical class 0.000 claims 19
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 15
- 150000002431 hydrogen Chemical class 0.000 claims 14
- 125000002947 alkylene group Chemical group 0.000 claims 9
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 8
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 8
- 125000004430 oxygen atom Chemical group O* 0.000 claims 7
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims 6
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 6
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 6
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims 5
- -1 C 1 -C 6 -alkoxy Chemical group 0.000 claims 5
- 125000000623 heterocyclic group Chemical group 0.000 claims 5
- SEPPVOUBHWNCAW-FNORWQNLSA-N (E)-4-oxonon-2-enal Chemical compound CCCCCC(=O)\C=C\C=O SEPPVOUBHWNCAW-FNORWQNLSA-N 0.000 claims 4
- 125000006296 sulfonyl amino group Chemical group [H]N(*)S(*)(=O)=O 0.000 claims 4
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims 3
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 3
- 229910052736 halogen Inorganic materials 0.000 claims 3
- 150000002367 halogens Chemical class 0.000 claims 3
- 125000004845 (C1-C6) alkylsulfonylamino group Chemical group 0.000 claims 2
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 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 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 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 2
- 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 claims 1
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- KSZCAGWHZCZJLZ-UHFFFAOYSA-N 1-methylimidazole-4-sulfonic acid Chemical compound CN1C=NC(S(O)(=O)=O)=C1 KSZCAGWHZCZJLZ-UHFFFAOYSA-N 0.000 claims 1
- WHYASBKVZHKQTN-UHFFFAOYSA-N 1-methylpyrazole-4-sulfonic acid Chemical compound CN1C=C(S(O)(=O)=O)C=N1 WHYASBKVZHKQTN-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- 125000003320 C2-C6 alkenyloxy group Chemical group 0.000 claims 1
- 208000012902 Nervous system disease Diseases 0.000 claims 1
- 208000002193 Pain Diseases 0.000 claims 1
- 125000003282 alkyl amino group Chemical group 0.000 claims 1
- 125000004419 alkynylene group Chemical group 0.000 claims 1
- 150000001408 amides Chemical class 0.000 claims 1
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 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 1
- 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 1
- 125000005549 heteroarylene group Chemical group 0.000 claims 1
- 150000002391 heterocyclic compounds Chemical class 0.000 claims 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- OUJINOAVBIQSRB-UHFFFAOYSA-N n-[2-[3-[1-amino-3-(3,5-difluorophenyl)propan-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=C(F)C=C(F)C=2)=C1 OUJINOAVBIQSRB-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- LMEZXEOCQVSTPY-UHFFFAOYSA-N n-[2-[3-[1-amino-3-(3-chlorophenyl)propan-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=C(Cl)C=CC=2)=C1 LMEZXEOCQVSTPY-UHFFFAOYSA-N 0.000 claims 1
- VGYSKYKJEAUUFY-UHFFFAOYSA-N n-[2-[3-[1-amino-3-(3-chlorophenyl)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(Cl)C=CC=2)=C1 VGYSKYKJEAUUFY-UHFFFAOYSA-N 0.000 claims 1
- QKQRCZOFDCTJEI-UHFFFAOYSA-N n-[2-[3-[1-amino-3-(4-chlorophenyl)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=CC(Cl)=CC=2)=C1 QKQRCZOFDCTJEI-UHFFFAOYSA-N 0.000 claims 1
- NSHUYSXZUJRBBM-UHFFFAOYSA-N n-[2-[3-[1-amino-3-[3-(trifluoromethyl)phenyl]propan-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=C(C=CC=2)C(F)(F)F)=C1 NSHUYSXZUJRBBM-UHFFFAOYSA-N 0.000 claims 1
- RCAWJWRNXYTGTP-UHFFFAOYSA-N n-[2-[3-[1-amino-3-[3-(trifluoromethyl)phenyl]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(C=CC=2)C(F)(F)F)=C1 RCAWJWRNXYTGTP-UHFFFAOYSA-N 0.000 claims 1
- OBDPJNWADSEKSU-UHFFFAOYSA-N n-[2-[3-[3-benzyl-1-(2,2-difluoroacetyl)pyrrolidin-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(CC2)C(=O)C(F)F)=C1 OBDPJNWADSEKSU-UHFFFAOYSA-N 0.000 claims 1
- HGSLOXWYEMKWHX-UHFFFAOYSA-N n-[2-[3-[3-benzyl-1-(2,2-difluoroethyl)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(CC(F)F)C2)=C1 HGSLOXWYEMKWHX-UHFFFAOYSA-N 0.000 claims 1
- DZYLUNISZUPZNH-UHFFFAOYSA-N n-[2-[3-[3-benzyl-1-(2,2-dimethylpropyl)pyrrolidin-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(CC(C)(C)C)CC2)=C1 DZYLUNISZUPZNH-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- RIHPVPXINBTIQI-UHFFFAOYSA-N n-[2-[3-[3-benzyl-1-(2-fluoroethyl)pyrrolidin-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)CC2)=C1 RIHPVPXINBTIQI-UHFFFAOYSA-N 0.000 claims 1
- PSEPDAHDYDEDNC-UHFFFAOYSA-N n-[2-[3-[3-benzyl-1-(2-methoxyethyl)azetidin-3-yl]phenoxy]ethyl]-1-methylimidazole-4-sulfonamide Chemical compound C1N(CCOC)CC1(C=1C=C(OCCNS(=O)(=O)C=2N=CN(C)C=2)C=CC=1)CC1=CC=CC=C1 PSEPDAHDYDEDNC-UHFFFAOYSA-N 0.000 claims 1
- XAOTZCGJNCMQTI-UHFFFAOYSA-N n-[2-[4-chloro-3-[1-(dimethylamino)-3-phenylpropan-2-yl]phenoxy]ethyl]-1-methylpyrazole-4-sulfonamide Chemical compound C=1C(OCCNS(=O)(=O)C2=CN(C)N=C2)=CC=C(Cl)C=1C(CN(C)C)CC1=CC=CC=C1 XAOTZCGJNCMQTI-UHFFFAOYSA-N 0.000 claims 1
- QQSQJTIMNPKWSG-UHFFFAOYSA-N n-[2-[5-(1-amino-3-phenylpropan-2-yl)-2-fluorophenoxy]ethyl]-1-methylimidazole-4-sulfonamide Chemical compound CN1C=NC(S(=O)(=O)NCCOC=2C(=CC=C(C=2)C(CN)CC=2C=CC=CC=2)F)=C1 QQSQJTIMNPKWSG-UHFFFAOYSA-N 0.000 claims 1
- MJBGPNPKELCMGC-UHFFFAOYSA-N n-[2-[5-(1-amino-3-phenylpropan-2-yl)-2-fluorophenoxy]ethyl]-1-methylpyrazole-4-sulfonamide Chemical compound C1=NN(C)C=C1S(=O)(=O)NCCOC1=CC(C(CN)CC=2C=CC=CC=2)=CC=C1F MJBGPNPKELCMGC-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- ZLOGEPWQDUFPRX-UHFFFAOYSA-N n-[2-[5-(3-benzyl-1-methylazetidin-3-yl)-2-fluorophenoxy]ethyl]-n,1-dimethylimidazole-4-sulfonamide Chemical compound C=1N(C)C=NC=1S(=O)(=O)N(C)CCOC(C(=CC=1)F)=CC=1C1(CC=2C=CC=CC=2)CN(C)C1 ZLOGEPWQDUFPRX-UHFFFAOYSA-N 0.000 claims 1
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- BRSSHYRDXFAGBU-UHFFFAOYSA-N n-[[3-(1-amino-3-phenylpropan-2-yl)phenyl]methyl]-1-methylimidazole-4-sulfonamide Chemical compound CN1C=NC(S(=O)(=O)NCC=2C=C(C=CC=2)C(CN)CC=2C=CC=CC=2)=C1 BRSSHYRDXFAGBU-UHFFFAOYSA-N 0.000 claims 1
- KGBATTRBSMKHMW-UHFFFAOYSA-N n-[[3-(1-amino-3-phenylpropan-2-yl)phenyl]methyl]-1-methylpyrazole-4-sulfonamide Chemical compound C1=NN(C)C=C1S(=O)(=O)NCC1=CC=CC(C(CN)CC=2C=CC=CC=2)=C1 KGBATTRBSMKHMW-UHFFFAOYSA-N 0.000 claims 1
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- XBVOZHLSEUNVSM-UHFFFAOYSA-N n-[[3-[2-amino-1-[1-(4-chlorophenyl)cyclobutyl]ethyl]phenyl]methyl]-n,1-dimethylpyrazole-4-sulfonamide Chemical compound C1=NN(C)C=C1S(=O)(=O)N(C)CC(C=1)=CC=CC=1C(CN)C1(C=2C=CC(Cl)=CC=2)CCC1 XBVOZHLSEUNVSM-UHFFFAOYSA-N 0.000 claims 1
- GTQCWMOGRXRAJI-UHFFFAOYSA-N n-[[3-[2-amino-1-[1-(4-chlorophenyl)cyclobutyl]ethyl]phenyl]methyl]-n-methylpropane-1-sulfonamide Chemical compound CCCS(=O)(=O)N(C)CC1=CC=CC(C(CN)C2(CCC2)C=2C=CC(Cl)=CC=2)=C1 GTQCWMOGRXRAJI-UHFFFAOYSA-N 0.000 claims 1
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- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
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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 |
| US8883839B2 (en) | 2010-08-13 | 2014-11-11 | Abbott Laboratories | Tetraline and indane derivatives, pharmaceutical compositions containing them, and their use in therapy |
| US8877794B2 (en) | 2010-08-13 | 2014-11-04 | Abbott Laboratories | Phenalkylamine derivatives, pharmaceutical compositions containing them, and their use in therapy |
| US9051280B2 (en) | 2010-08-13 | 2015-06-09 | AbbVie Deutschland GmbH & Co. KG | Tetraline and indane derivatives, pharmaceutical compositions containing them, and their use in therapy |
| US8846743B2 (en) | 2010-08-13 | 2014-09-30 | Abbott Laboratories | Aminoindane derivatives, pharmaceutical compositions containing them, and their use in therapy |
| US9045459B2 (en) | 2010-08-13 | 2015-06-02 | AbbVie Deutschland GmbH & Co. KG | Phenalkylamine derivatives, pharmaceutical compositions containing them, and their use in therapy |
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| US9365512B2 (en) | 2012-02-13 | 2016-06-14 | AbbVie Deutschland GmbH & Co. KG | Isoindoline 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 MX MX2013001790A patent/MX2013001790A/es active IP Right Grant
- 2011-08-12 JP JP2013523638A patent/JP2013538198A/ja active Pending
- 2011-08-12 WO PCT/EP2011/063971 patent/WO2012020130A1/en not_active Ceased
- 2011-08-12 EP EP11748621.7A patent/EP2603487A1/en not_active Withdrawn
- 2011-08-12 CA CA2806643A patent/CA2806643A1/en not_active Abandoned
- 2011-08-12 CN CN201180039735XA patent/CN103237788A/zh active Pending
-
2014
- 2014-05-20 US US14/282,712 patent/US9238619B2/en not_active Expired - Fee Related
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