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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| PCT/EP2007/062006 WO2008055932A1 (en) | 2006-11-10 | 2007-11-07 | 1,2,4-triazole derivatives as sigma receptor inhibitors |
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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 |
| WO2014047413A1 (en) * | 2012-09-21 | 2014-03-27 | Uwm Research Foundation, Inc. | Novel gabaa agonists and methods of using to control airway hyperresponsiveness and inflammation 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 |
| EP2989105B1 (en) | 2013-04-23 | 2020-03-11 | Esteve Pharmaceuticals, S.A. | Pyrazino[1,2-a]indole compounds, their preparation and use in medicaments |
| MA38569A1 (fr) | 2013-04-23 | 2017-03-31 | Esteve Labor Dr | Composés pyrazino[1,2-a]indole, leur préparation et utilisation dans des médicaments |
| EP2832720A1 (en) | 2013-07-30 | 2015-02-04 | Laboratorios Del. Dr. Esteve, S.A. | 1,2-disubstituted cyclobutyl compounds |
| SG11201604480PA (en) | 2013-12-17 | 2016-07-28 | Esteve Labor Dr | SEROTONIN-NOREPINEPHRINE REUPTAKE INHIBITORS (SNRIs) AND SIGMA RECEPTOR LIGANDS COMBINATIONS |
| MA41177A (fr) * | 2014-12-15 | 2017-10-24 | Esteve Labor Dr | Utilisation de ligands des récepteurs sigma dans l'arthrose |
| HUE058156T2 (hu) | 2015-01-30 | 2022-07-28 | Neurocrine Biosciences Inc | Helyettesített triazolok és ezekkel kapcsolatos eljárások |
| US10118904B2 (en) | 2015-06-05 | 2018-11-06 | Vertex Pharmaceuticals Incorporated | Triazoles for the treatment of Demyelinating Diseases |
| CN111432813B (zh) | 2017-11-14 | 2024-01-09 | 爱思开生物制药株式会社 | 用于预防、减轻、或治疗精神分裂症的包含氨基甲酸酯化合物的共混物 |
| CN111432814B (zh) * | 2017-11-14 | 2024-05-14 | 爱思开生物制药株式会社 | 用于减轻或治疗包括脆性X染色体综合征、Angelman综合征或Rett综合征的发育障碍的氨基甲酸酯化合物的用途 |
| 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 |
| EP3711756A4 (en) | 2017-11-14 | 2021-11-24 | SK Biopharmaceuticals Co., Ltd. | USE OF A CARBAMATE COMPOUND TO PREVENT, RELAX, OR TREAT MYOTONIA |
| 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 |
| CA2542682A1 (en) | 2003-10-18 | 2005-05-06 | 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 |
| WO2005039550A2 (en) | 2003-10-24 | 2005-05-06 | Solvay Pharmaceuticals Gmbh | Novel medical uses of compounds showing cb1-antagonistic activity and combination treatment involving said compounds |
| 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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- 2007-11-07 NZ NZ577557A patent/NZ577557A/en not_active IP Right Cessation
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2011
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