JP2010509280A5 - - Google Patents
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- JP2010509280A5 JP2010509280A5 JP2009535719A JP2009535719A JP2010509280A5 JP 2010509280 A5 JP2010509280 A5 JP 2010509280A5 JP 2009535719 A JP2009535719 A JP 2009535719A JP 2009535719 A JP2009535719 A JP 2009535719A JP 2010509280 A5 JP2010509280 A5 JP 2010509280A5
- Authority
- JP
- Japan
- Prior art keywords
- triazol
- methyl
- dichlorophenyl
- ethyl
- ylthio
- 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 25
- 239000001257 hydrogen Substances 0.000 claims 25
- 150000001875 compounds Chemical class 0.000 claims 19
- 150000002431 hydrogen Chemical class 0.000 claims 14
- -1 1- (3,4-dichlorophenyl) -5-methyl-1H-1,2,4-triazol-3-yl-thio Chemical group 0.000 claims 13
- 125000000623 heterocyclic group Chemical group 0.000 claims 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 11
- 229910052736 halogen Inorganic materials 0.000 claims 11
- 150000002367 halogens Chemical class 0.000 claims 11
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 7
- 238000000034 method Methods 0.000 claims 7
- 229910052757 nitrogen Inorganic materials 0.000 claims 7
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 6
- 229940002612 prodrug Drugs 0.000 claims 6
- 239000000651 prodrug Substances 0.000 claims 6
- 150000003839 salts Chemical class 0.000 claims 6
- 239000012453 solvate Substances 0.000 claims 6
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims 5
- 125000003545 alkoxy group Chemical group 0.000 claims 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims 5
- 125000001072 heteroaryl group Chemical group 0.000 claims 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 5
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 5
- ZKSZSWJQBXLNMN-UHFFFAOYSA-N morpholine;oxalic acid Chemical compound C1COCCN1.OC(=O)C(O)=O ZKSZSWJQBXLNMN-UHFFFAOYSA-N 0.000 claims 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 5
- 229910052760 oxygen Inorganic materials 0.000 claims 5
- 239000008194 pharmaceutical composition Substances 0.000 claims 5
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 4
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 4
- 229940100198 alkylating agent Drugs 0.000 claims 3
- 239000002168 alkylating agent Substances 0.000 claims 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 3
- 201000010099 disease Diseases 0.000 claims 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 3
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims 3
- 229910052717 sulfur Inorganic materials 0.000 claims 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 2
- 208000004454 Hyperalgesia Diseases 0.000 claims 2
- 208000002193 Pain Diseases 0.000 claims 2
- 150000001412 amines Chemical class 0.000 claims 2
- ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 claims 2
- 238000006243 chemical reaction Methods 0.000 claims 2
- ZPUCINDJVBIVPJ-LJISPDSOSA-N cocaine Chemical compound O([C@H]1C[C@@H]2CC[C@@H](N2C)[C@H]1C(=O)OC)C(=O)C1=CC=CC=C1 ZPUCINDJVBIVPJ-LJISPDSOSA-N 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- WLCAJVVSNAVBSM-UHFFFAOYSA-N oxalic acid;piperidine Chemical compound C1CCNCC1.OC(=O)C(O)=O WLCAJVVSNAVBSM-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
- KWTSXDURSIMDCE-QMMMGPOBSA-N (S)-amphetamine Chemical compound C[C@H](N)CC1=CC=CC=C1 KWTSXDURSIMDCE-QMMMGPOBSA-N 0.000 claims 1
- NXLSPZQNUCQULT-UHFFFAOYSA-N 1-(3,4-dichlorophenyl)-5-methyl-3-(2-pyrrolidin-1-ylethoxy)-1,2,4-triazole Chemical compound N=1N(C=2C=C(Cl)C(Cl)=CC=2)C(C)=NC=1OCCN1CCCC1 NXLSPZQNUCQULT-UHFFFAOYSA-N 0.000 claims 1
- LFFGAUAMYWZXGF-UHFFFAOYSA-N 1-(3,4-dichlorophenyl)-5-methyl-3-(2-pyrrolidin-1-ylethylsulfinyl)-1,2,4-triazole Chemical compound CC1=NC(S(=O)CCN2CCCC2)=NN1C1=CC=C(Cl)C(Cl)=C1 LFFGAUAMYWZXGF-UHFFFAOYSA-N 0.000 claims 1
- XWBARDOVDMNKNI-UHFFFAOYSA-N 1-(3,4-dichlorophenyl)-5-methyl-3-(4-pyrrolidin-1-ylbutylsulfanyl)-1,2,4-triazole Chemical compound N=1N(C=2C=C(Cl)C(Cl)=CC=2)C(C)=NC=1SCCCCN1CCCC1 XWBARDOVDMNKNI-UHFFFAOYSA-N 0.000 claims 1
- ATGGFLBUYMNDBU-UHFFFAOYSA-N 1-(3,4-dichlorophenyl)-5-methyl-3-(5-pyrrolidin-1-ylpentylsulfanyl)-1,2,4-triazole Chemical compound N=1N(C=2C=C(Cl)C(Cl)=CC=2)C(C)=NC=1SCCCCCN1CCCC1 ATGGFLBUYMNDBU-UHFFFAOYSA-N 0.000 claims 1
- YHSQQUFLTWNQTI-UHFFFAOYSA-N 1-(3-chlorophenyl)-5-methyl-3-(2-pyrrolidin-1-ium-3-ylethylsulfanyl)-1,2,4-triazole;oxalate Chemical compound [O-]C(=O)C([O-])=O.N=1N(C=2C=C(Cl)C=CC=2)C(C)=NC=1SCCC1CC[NH2+]C1.N=1N(C=2C=C(Cl)C=CC=2)C(C)=NC=1SCCC1CC[NH2+]C1 YHSQQUFLTWNQTI-UHFFFAOYSA-N 0.000 claims 1
- HHNGOHDMEJQNCX-UHFFFAOYSA-N 1-(3-chlorophenyl)-5-methyl-3-(2-pyrrolidin-1-ylethylsulfinyl)-1,2,4-triazole Chemical compound CC1=NC(S(=O)CCN2CCCC2)=NN1C1=CC=CC(Cl)=C1 HHNGOHDMEJQNCX-UHFFFAOYSA-N 0.000 claims 1
- BEXCQNGPNGUAQD-UHFFFAOYSA-N 1-(3-chlorophenyl)-5-methyl-3-(2-pyrrolidin-1-ylethylsulfonyl)-1,2,4-triazole Chemical compound CC1=NC(S(=O)(=O)CCN2CCCC2)=NN1C1=CC=CC(Cl)=C1 BEXCQNGPNGUAQD-UHFFFAOYSA-N 0.000 claims 1
- KORKFWDBUXWXLI-UHFFFAOYSA-N 1-(3-chlorophenyl)-5-methyl-3-(2-pyrrolidin-3-ylethylsulfanyl)-1,2,4-triazole Chemical compound N=1N(C=2C=C(Cl)C=CC=2)C(C)=NC=1SCCC1CCNC1 KORKFWDBUXWXLI-UHFFFAOYSA-N 0.000 claims 1
- GGIJKFGRFULFRU-UHFFFAOYSA-N 1-[2-[(5-methyl-1-phenyl-1,2,4-triazol-3-yl)oxy]ethyl]piperidine Chemical compound N=1N(C=2C=CC=CC=2)C(C)=NC=1OCCN1CCCCC1 GGIJKFGRFULFRU-UHFFFAOYSA-N 0.000 claims 1
- QFHUZCSOVBOOBX-UHFFFAOYSA-N 1-[2-[[1-(3,4-dichlorophenyl)-5-methyl-1,2,4-triazol-3-yl]sulfanyl]ethyl]-4-methylpiperidin-1-ium;oxalate Chemical compound [O-]C(=O)C([O-])=O.C1CC(C)CC[NH+]1CCSC1=NN(C=2C=C(Cl)C(Cl)=CC=2)C(C)=N1.C1CC(C)CC[NH+]1CCSC1=NN(C=2C=C(Cl)C(Cl)=CC=2)C(C)=N1 QFHUZCSOVBOOBX-UHFFFAOYSA-N 0.000 claims 1
- JLQRVNKZOIPSRO-UHFFFAOYSA-N 1-[2-[[1-(3,4-dichlorophenyl)-5-methyl-1,2,4-triazol-3-yl]sulfanyl]ethyl]-4-methylpiperidine Chemical compound C1CC(C)CCN1CCSC1=NN(C=2C=C(Cl)C(Cl)=CC=2)C(C)=N1 JLQRVNKZOIPSRO-UHFFFAOYSA-N 0.000 claims 1
- JOIRGPHBEYWITB-UHFFFAOYSA-N 1-[2-[[1-(3,4-dichlorophenyl)-5-methyl-1,2,4-triazol-3-yl]sulfanyl]ethyl]azepane Chemical compound N=1N(C=2C=C(Cl)C(Cl)=CC=2)C(C)=NC=1SCCN1CCCCCC1 JOIRGPHBEYWITB-UHFFFAOYSA-N 0.000 claims 1
- BURWSKNHDFFSMI-UHFFFAOYSA-N 1-[2-[[1-(3-chlorophenyl)-5-methyl-1,2,4-triazol-3-yl]sulfanyl]ethyl]piperidin-1-ium;oxalate Chemical compound [O-]C(=O)C([O-])=O.N=1N(C=2C=C(Cl)C=CC=2)C(C)=NC=1SCC[NH+]1CCCCC1.N=1N(C=2C=C(Cl)C=CC=2)C(C)=NC=1SCC[NH+]1CCCCC1 BURWSKNHDFFSMI-UHFFFAOYSA-N 0.000 claims 1
- ZLNQEUFJYRVBOM-UHFFFAOYSA-N 1-[2-[[1-(3-chlorophenyl)-5-methyl-1,2,4-triazol-3-yl]sulfanyl]ethyl]piperidine Chemical compound N=1N(C=2C=C(Cl)C=CC=2)C(C)=NC=1SCCN1CCCCC1 ZLNQEUFJYRVBOM-UHFFFAOYSA-N 0.000 claims 1
- QVDZYEFHPSECDL-UHFFFAOYSA-N 1-[2-[[2-(3,4-dichlorophenyl)-5-methyl-1,3-dihydro-1,2,4-triazol-3-yl]sulfanyl]ethyl]piperidine Chemical compound C=1C=C(Cl)C(Cl)=CC=1N1NC(C)=NC1SCCN1CCCCC1 QVDZYEFHPSECDL-UHFFFAOYSA-N 0.000 claims 1
- VGVPARJWFWRFOI-UHFFFAOYSA-N 1-[3-[[1-(3,4-dichlorophenyl)-5-methyl-1,2,4-triazol-3-yl]sulfanyl]propyl]-4-phenylpiperidine Chemical compound N=1N(C=2C=C(Cl)C(Cl)=CC=2)C(C)=NC=1SCCCN(CC1)CCC1C1=CC=CC=C1 VGVPARJWFWRFOI-UHFFFAOYSA-N 0.000 claims 1
- CTJADQLHTIKHRI-UHFFFAOYSA-N 1-[4-[[1-(3,4-dichlorophenyl)-5-methyl-1,2,4-triazol-3-yl]sulfanyl]butyl]-4-phenylpiperidine Chemical compound N=1N(C=2C=C(Cl)C(Cl)=CC=2)C(C)=NC=1SCCCCN(CC1)CCC1C1=CC=CC=C1 CTJADQLHTIKHRI-UHFFFAOYSA-N 0.000 claims 1
- KYQUZVISAYTPSC-UHFFFAOYSA-N 1-[4-[[1-(3,4-dichlorophenyl)-5-methyl-1,2,4-triazol-3-yl]sulfanyl]butyl]piperidine Chemical compound N=1N(C=2C=C(Cl)C(Cl)=CC=2)C(C)=NC=1SCCCCN1CCCCC1 KYQUZVISAYTPSC-UHFFFAOYSA-N 0.000 claims 1
- GCGRWQQYYVFRGG-UHFFFAOYSA-N 1-[5-[[1-(3,4-dichlorophenyl)-5-methyl-1,2,4-triazol-3-yl]sulfanyl]pentyl]piperidine Chemical compound N=1N(C=2C=C(Cl)C(Cl)=CC=2)C(C)=NC=1SCCCCCN1CCCCC1 GCGRWQQYYVFRGG-UHFFFAOYSA-N 0.000 claims 1
- GVSQXAKSBRJRRJ-UHFFFAOYSA-N 2-(3,4-dichlorophenyl)-5-methyl-3-(2-pyrrolidin-1-ylethylsulfanyl)-1,3-dihydro-1,2,4-triazole Chemical compound C=1C=C(Cl)C(Cl)=CC=1N1NC(C)=NC1SCCN1CCCC1 GVSQXAKSBRJRRJ-UHFFFAOYSA-N 0.000 claims 1
- LARBHPBCWVOBHV-UHFFFAOYSA-N 2-(3,4-dichlorophenyl)-5-methyl-3-(2-pyrrolidin-1-ylethylsulfanyl)-1,3-dihydro-1,2,4-triazole;oxalic acid Chemical compound OC(=O)C(O)=O.C=1C=C(Cl)C(Cl)=CC=1N1NC(C)=NC1SCCN1CCCC1 LARBHPBCWVOBHV-UHFFFAOYSA-N 0.000 claims 1
- MRBXRBPCYXJAQM-UHFFFAOYSA-N 2-[[1-(3,4-dichlorophenyl)-5-methyl-1,2,4-triazol-3-yl]oxy]-n,n-diethylethanamine Chemical compound N1=C(OCCN(CC)CC)N=C(C)N1C1=CC=C(Cl)C(Cl)=C1 MRBXRBPCYXJAQM-UHFFFAOYSA-N 0.000 claims 1
- UGIMFWGDHJPAHR-UHFFFAOYSA-N 2-[[1-(3,4-dichlorophenyl)-5-methyl-1,2,4-triazol-3-yl]sulfanyl]-n,n-diethylethanamine Chemical compound N1=C(SCCN(CC)CC)N=C(C)N1C1=CC=C(Cl)C(Cl)=C1 UGIMFWGDHJPAHR-UHFFFAOYSA-N 0.000 claims 1
- TYEXKKGYEQAEJP-UHFFFAOYSA-N 2-[[1-(3,4-dichlorophenyl)-5-methyl-1,2,4-triazol-3-yl]sulfanyl]-n,n-diethylethanamine;oxalic acid Chemical compound OC(=O)C(O)=O.N1=C(SCCN(CC)CC)N=C(C)N1C1=CC=C(Cl)C(Cl)=C1 TYEXKKGYEQAEJP-UHFFFAOYSA-N 0.000 claims 1
- IYKOADSEMAMUKI-UHFFFAOYSA-N 2-[[1-(3,4-dichlorophenyl)-5-methyl-1,2,4-triazol-3-yl]sulfinyl]-n,n-diethylethanamine Chemical compound N1=C(S(=O)CCN(CC)CC)N=C(C)N1C1=CC=C(Cl)C(Cl)=C1 IYKOADSEMAMUKI-UHFFFAOYSA-N 0.000 claims 1
- BRQPGJPCTBIDMW-UHFFFAOYSA-N 2-[[1-(3-chlorophenyl)-5-methyl-1,2,4-triazol-3-yl]sulfanyl]-n,n-diethylethanamine Chemical compound N1=C(SCCN(CC)CC)N=C(C)N1C1=CC=CC(Cl)=C1 BRQPGJPCTBIDMW-UHFFFAOYSA-N 0.000 claims 1
- DPJMLRMPJVNGAL-UHFFFAOYSA-L 2-[[1-(3-chlorophenyl)-5-methyl-1,2,4-triazol-3-yl]sulfanyl]ethyl-tri(propan-2-yl)azanium;oxalate Chemical compound [O-]C(=O)C([O-])=O.N1=C(SCC[N+](C(C)C)(C(C)C)C(C)C)N=C(C)N1C1=CC=CC(Cl)=C1.N1=C(SCC[N+](C(C)C)(C(C)C)C(C)C)N=C(C)N1C1=CC=CC(Cl)=C1 DPJMLRMPJVNGAL-UHFFFAOYSA-L 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
- FWENBLLNTLQCPV-UHFFFAOYSA-N 4-[2-[(5-methyl-1-phenyl-1,2,4-triazol-3-yl)oxy]ethyl]morpholine Chemical compound N=1N(C=2C=CC=CC=2)C(C)=NC=1OCCN1CCOCC1 FWENBLLNTLQCPV-UHFFFAOYSA-N 0.000 claims 1
- AJFUQYJBIQPMLY-UHFFFAOYSA-N 4-[2-[(5-methyl-1-phenyl-1,2,4-triazol-3-yl)sulfanyl]ethyl]morpholin-4-ium;oxalate Chemical compound [O-]C(=O)C([O-])=O.N=1N(C=2C=CC=CC=2)C(C)=NC=1SCC[NH+]1CCOCC1.N=1N(C=2C=CC=CC=2)C(C)=NC=1SCC[NH+]1CCOCC1 AJFUQYJBIQPMLY-UHFFFAOYSA-N 0.000 claims 1
- JZWSWKIJXGMJEQ-UHFFFAOYSA-N 4-[2-[(5-methyl-1-phenyl-1,2,4-triazol-3-yl)sulfanyl]ethyl]morpholine Chemical compound N=1N(C=2C=CC=CC=2)C(C)=NC=1SCCN1CCOCC1 JZWSWKIJXGMJEQ-UHFFFAOYSA-N 0.000 claims 1
- JKCAQTJINYQGRJ-UHFFFAOYSA-N 4-[2-[[1-(3,4-dichlorophenyl)-5-methyl-1,2,4-triazol-3-yl]oxy]ethyl]morpholine Chemical compound N=1N(C=2C=C(Cl)C(Cl)=CC=2)C(C)=NC=1OCCN1CCOCC1 JKCAQTJINYQGRJ-UHFFFAOYSA-N 0.000 claims 1
- MIHAUBABWBPGBV-UHFFFAOYSA-N 4-[2-[[1-(3,4-dichlorophenyl)-5-methyl-1,2,4-triazol-3-yl]sulfinyl]ethyl]morpholine Chemical compound CC1=NC(S(=O)CCN2CCOCC2)=NN1C1=CC=C(Cl)C(Cl)=C1 MIHAUBABWBPGBV-UHFFFAOYSA-N 0.000 claims 1
- YLRNQMHOZSNVRQ-UHFFFAOYSA-N 4-[2-[[1-(3-chlorophenyl)-5-methyl-1,2,4-triazol-3-yl]sulfanyl]ethyl]morpholin-4-ium;oxalate Chemical compound [O-]C(=O)C([O-])=O.N=1N(C=2C=C(Cl)C=CC=2)C(C)=NC=1SCC[NH+]1CCOCC1.N=1N(C=2C=C(Cl)C=CC=2)C(C)=NC=1SCC[NH+]1CCOCC1 YLRNQMHOZSNVRQ-UHFFFAOYSA-N 0.000 claims 1
- FDHAJRAFJPMTMK-UHFFFAOYSA-N 4-[2-[[1-(3-chlorophenyl)-5-methyl-1,2,4-triazol-3-yl]sulfanyl]ethyl]morpholine Chemical compound N=1N(C=2C=C(Cl)C=CC=2)C(C)=NC=1SCCN1CCOCC1 FDHAJRAFJPMTMK-UHFFFAOYSA-N 0.000 claims 1
- KBFONAOSJSMHAG-UHFFFAOYSA-N 4-[2-[[1-(4-chlorophenyl)-5-methyl-1,2,4-triazol-3-yl]sulfanyl]ethyl]morpholin-4-ium;oxalate Chemical compound [O-]C(=O)C([O-])=O.N=1N(C=2C=CC(Cl)=CC=2)C(C)=NC=1SCC[NH+]1CCOCC1.N=1N(C=2C=CC(Cl)=CC=2)C(C)=NC=1SCC[NH+]1CCOCC1 KBFONAOSJSMHAG-UHFFFAOYSA-N 0.000 claims 1
- NGXFMDGDPJHOKU-UHFFFAOYSA-N 4-[2-[[1-(4-chlorophenyl)-5-methyl-1,2,4-triazol-3-yl]sulfanyl]ethyl]morpholine Chemical compound N=1N(C=2C=CC(Cl)=CC=2)C(C)=NC=1SCCN1CCOCC1 NGXFMDGDPJHOKU-UHFFFAOYSA-N 0.000 claims 1
- MFWNUCMVZDVEHF-UHFFFAOYSA-N 4-[2-[[2-(3,4-dichlorophenyl)-5-methyl-1,3-dihydro-1,2,4-triazol-3-yl]sulfanyl]ethyl]morpholine Chemical compound C=1C=C(Cl)C(Cl)=CC=1N1NC(C)=NC1SCCN1CCOCC1 MFWNUCMVZDVEHF-UHFFFAOYSA-N 0.000 claims 1
- WERFZLKTIYRAGG-UHFFFAOYSA-N 4-[3-[[1-(3,4-dichlorophenyl)-5-methyl-1,2,4-triazol-3-yl]sulfanyl]propyl]morpholine Chemical compound N=1N(C=2C=C(Cl)C(Cl)=CC=2)C(C)=NC=1SCCCN1CCOCC1 WERFZLKTIYRAGG-UHFFFAOYSA-N 0.000 claims 1
- RYDIEIBMAJGRGB-UHFFFAOYSA-N 4-[4-[(5-methyl-1-phenyl-1,2,4-triazol-3-yl)oxy]butyl]morpholine Chemical compound N=1N(C=2C=CC=CC=2)C(C)=NC=1OCCCCN1CCOCC1 RYDIEIBMAJGRGB-UHFFFAOYSA-N 0.000 claims 1
- DODIZWKJOHUZKA-UHFFFAOYSA-N 4-[4-[[1-(3,4-dichlorophenyl)-5-methyl-1,2,4-triazol-3-yl]sulfanyl]butyl]morpholine Chemical compound N=1N(C=2C=C(Cl)C(Cl)=CC=2)C(C)=NC=1SCCCCN1CCOCC1 DODIZWKJOHUZKA-UHFFFAOYSA-N 0.000 claims 1
- LCNCXCAYTGWGSO-UHFFFAOYSA-N 4-[5-[[1-(3,4-dichlorophenyl)-5-methyl-1,2,4-triazol-3-yl]sulfanyl]pentyl]morpholine Chemical compound N=1N(C=2C=C(Cl)C(Cl)=CC=2)C(C)=NC=1SCCCCCN1CCOCC1 LCNCXCAYTGWGSO-UHFFFAOYSA-N 0.000 claims 1
- QPPCCXPUWHYNFN-UHFFFAOYSA-N 4-[[1-(3-chlorophenyl)-5-methyl-1,2,4-triazol-3-yl]sulfinyl]-n-ethylbutan-2-amine Chemical compound N1=C(S(=O)CCC(C)NCC)N=C(C)N1C1=CC=CC(Cl)=C1 QPPCCXPUWHYNFN-UHFFFAOYSA-N 0.000 claims 1
- JDCPSHKMNXPPJF-UHFFFAOYSA-N 4-[[1-(3-chlorophenyl)-5-methyl-1,2,4-triazol-3-yl]sulfonyl]-n-ethylbutan-2-amine Chemical compound N1=C(S(=O)(=O)CCC(C)NCC)N=C(C)N1C1=CC=CC(Cl)=C1 JDCPSHKMNXPPJF-UHFFFAOYSA-N 0.000 claims 1
- BTSGXCRYUPVNMM-UHFFFAOYSA-N 5-methyl-1-phenyl-3-(2-pyrrolidin-1-ylethoxy)-1,2,4-triazole Chemical compound N=1N(C=2C=CC=CC=2)C(C)=NC=1OCCN1CCCC1 BTSGXCRYUPVNMM-UHFFFAOYSA-N 0.000 claims 1
- 208000019901 Anxiety disease Diseases 0.000 claims 1
- 208000023275 Autoimmune disease Diseases 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- SWGHZPAEZLHNRD-UHFFFAOYSA-N ClC=1C=C(C=CC=1)N1N=C(N=C1C)S(=O)(=O)CCC(C)(C)NC(C)C Chemical compound ClC=1C=C(C=CC=1)N1N=C(N=C1C)S(=O)(=O)CCC(C)(C)NC(C)C SWGHZPAEZLHNRD-UHFFFAOYSA-N 0.000 claims 1
- 208000028698 Cognitive impairment Diseases 0.000 claims 1
- 208000016192 Demyelinating disease Diseases 0.000 claims 1
- 206010012735 Diarrhoea Diseases 0.000 claims 1
- 208000012661 Dyskinesia Diseases 0.000 claims 1
- 208000032928 Dyslipidaemia Diseases 0.000 claims 1
- 208000010412 Glaucoma Diseases 0.000 claims 1
- 208000035150 Hypercholesterolemia Diseases 0.000 claims 1
- 208000035154 Hyperesthesia Diseases 0.000 claims 1
- 206010020772 Hypertension Diseases 0.000 claims 1
- 206010061218 Inflammation Diseases 0.000 claims 1
- 206010065390 Inflammatory pain Diseases 0.000 claims 1
- 206010060840 Ischaemic cerebral infarction Diseases 0.000 claims 1
- 208000017170 Lipid metabolism disease Diseases 0.000 claims 1
- 102000004895 Lipoproteins Human genes 0.000 claims 1
- 108090001030 Lipoproteins Proteins 0.000 claims 1
- 208000019695 Migraine disease Diseases 0.000 claims 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-N N,N-Diethylethanamine Substances CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 claims 1
- 208000008589 Obesity Diseases 0.000 claims 1
- 206010036790 Productive cough Diseases 0.000 claims 1
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| GB0507602D0 (en) * | 2005-04-14 | 2005-05-18 | Glaxo Group Ltd | Compounds |
| EP2116539A1 (en) | 2008-04-25 | 2009-11-11 | Laboratorios Del. Dr. Esteve, S.A. | 1-aryl-3-aminoalkoxy-pyrazoles as sigma ligands enhancing analgesic effects of opioids and attenuating the dependency thereof |
| US20100273805A1 (en) * | 2009-04-23 | 2010-10-28 | Astrazeneca Ab | Sulphide bridged derivatives as modulators of mglur5 733 |
| EP2353598A1 (en) | 2010-02-04 | 2011-08-10 | Laboratorios Del. Dr. Esteve, S.A. | Sigma ligands for use in the prevention and/or treatment of postoperative pain |
| EP2353591A1 (en) | 2010-02-04 | 2011-08-10 | Laboratorios Del. Dr. Esteve, S.A. | Sigma ligands for potentiating the analgesic effect of opioids and opiates in post-operative pain and attenuating the dependency thereof |
| EP2388005A1 (en) | 2010-05-21 | 2011-11-23 | Laboratorios Del. Dr. Esteve, S.A. | Sigma ligands for the prevention and/or treatment of emesis induced by chemotherapy or radiotherapy |
| EP2415471A1 (en) | 2010-08-03 | 2012-02-08 | Laboratorios Del. Dr. Esteve, S.A. | Use of sigma ligands in opioid-induced hyperalgesia |
| EP2524694A1 (en) | 2011-05-19 | 2012-11-21 | Laboratorios Del. Dr. Esteve, S.A. | Use of sigma ligands in diabetes type-2 associated pain |
| EP2567959B1 (en) | 2011-09-12 | 2014-04-16 | Sanofi | 6-(4-hydroxy-phenyl)-3-styryl-1h-pyrazolo[3,4-b]pyridine-4-carboxylic acid amide derivatives as kinase inhibitors |
| EP2897963A4 (en) * | 2012-09-21 | 2016-03-30 | Uwm Res Foundation Inc | Novel GABAA AGONISTS AND METHOD FOR USE TO COMBAT AIRWAY HYPER REAGIBILITY AND IGNITIONS IN ASTHMA |
| EP2752411A1 (en) | 2013-01-07 | 2014-07-09 | Laboratorios Del Dr. Esteve, S.A. | 1,2,3-triazole-4-amine derivatives for the treatment of sigma receptor related diseases and disorders |
| US9963453B2 (en) | 2013-04-23 | 2018-05-08 | Laboratorios Del Dr. Esteve S.A. | Substituted pyrazino[1,2-a]indoles as sigma receptor activity modulators |
| US9879015B2 (en) | 2013-04-23 | 2018-01-30 | Laboratorios Del Dr. Esteve S.A. | Pyrazino[1,2-a]indole compounds, their preparation and use in medicaments |
| EP2832720A1 (en) | 2013-07-30 | 2015-02-04 | Laboratorios Del. Dr. Esteve, S.A. | 1,2-disubstituted cyclobutyl compounds |
| MX2016007285A (es) | 2013-12-17 | 2016-08-04 | Esteve Labor Dr | Combinaciones de inhibidores de la captacion de serotonina-norepinefrina (irsn) y ligandos de receptores sigma. |
| MA41177A (fr) * | 2014-12-15 | 2017-10-24 | Esteve Labor Dr | Utilisation de ligands des récepteurs sigma dans l'arthrose |
| MX378932B (es) | 2015-01-30 | 2025-03-10 | Neurocrine Biosciences Inc | Triazoles sustituidos y métodos relacionados a estos. |
| EP3302465A1 (en) * | 2015-06-05 | 2018-04-11 | Vertex Pharmaceuticals Incorporated | Triazoles for the treatment of demyelinating diseases |
| US11389429B2 (en) | 2017-11-14 | 2022-07-19 | Sk Biopharmaceuticals Co., Ltd. | Use of carbamate compound for preventing, alleviating or treating myotonia |
| US11116751B2 (en) | 2017-11-14 | 2021-09-14 | Sk Biopharmaceuticals Co., Ltd. | Blend containing carbamate compound for prevention, mitigation, or treatment of schizophrenia |
| WO2019098630A1 (ko) * | 2017-11-14 | 2019-05-23 | 에스케이바이오팜 주식회사 | 취약 x 증후군, 엔젤만 증후군 또는 렛 증후군을 포함하는 발달 장애의 경감 또는 치료를 위한 카바메이트 화합물의 용도 |
| ES3027977T3 (en) * | 2017-11-14 | 2025-06-17 | Sk Biopharmaceuticals Co Ltd | Use of a carbamate compound to prevent, alleviate or treat visceralgia or pain arising from visceral disease |
| WO2020123847A1 (en) * | 2018-12-12 | 2020-06-18 | Rutgers, The State University Of New Jersey | Organic compounds |
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| DE1547640A1 (de) * | 1967-04-10 | 1969-12-04 | Agfa Gevaert Ag | Verbessertes photographisches Material |
| WO1991009594A1 (en) | 1989-12-28 | 1991-07-11 | Virginia Commonwealth University | Sigma receptor ligands and the use thereof |
| AU2002224478A1 (en) * | 2000-11-02 | 2002-05-15 | K And K Biosciences, Inc. | Delta2,-1,2,3-triazoline anticonvulsants and their active metabolite analogues, the aminoalkylpyridines, are excitatory amino acid antagonists and antiischemic agents, useful in the treatment of cerebral ischemia resulting from stroke |
| US6797722B2 (en) | 2002-05-03 | 2004-09-28 | Sigma-Tau Industrie Farmaceutiche Riunite S.P.A. | Use of 3-(2-ethylphenyl)-5-(3-methoxyphenyl)-1H-1,2,4-triazole for the treatment of autoimmune diseases |
| SE0301232D0 (sv) | 2003-04-25 | 2003-04-25 | Astrazeneca Ab | Novel use |
| EP1677786A1 (en) | 2003-10-18 | 2006-07-12 | Bayer HealthCare AG | 5-substituted 2-(phenylmethyl)thio-4-phenyl-4h-1,2,4-triazole derivatives and related compounds as gaba-agonists for the treatment of urinary incontinence and related diseases |
| JP2007513872A (ja) | 2003-10-24 | 2007-05-31 | ゾルファイ ファーマスーティカルズ ゲゼルシャフト ミット ベシュレンクテル ハフツング | Ｃｂ１拮抗作用を示す化合物の新規の医学的用途および前記化合物を伴う組み合わせ治療 |
| DE102005007304A1 (de) * | 2005-02-17 | 2006-08-24 | Merck Patent Gmbh | Triazolderivate |
| GB0504556D0 (en) | 2005-03-04 | 2005-04-13 | Pfizer Ltd | Novel pharmaceuticals |
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