JP2007508395A5 - - Google Patents
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- Publication number
- JP2007508395A5 JP2007508395A5 JP2006535619A JP2006535619A JP2007508395A5 JP 2007508395 A5 JP2007508395 A5 JP 2007508395A5 JP 2006535619 A JP2006535619 A JP 2006535619A JP 2006535619 A JP2006535619 A JP 2006535619A JP 2007508395 A5 JP2007508395 A5 JP 2007508395A5
- Authority
- JP
- Japan
- Prior art keywords
- ethyl
- cyclohexanol
- phenyl
- dihydrochloride
- chlorophenyl
- 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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- 150000001875 compounds Chemical class 0.000 claims 26
- -1 methylenedioxy, benzyloxy Chemical group 0.000 claims 25
- 125000004432 carbon atom Chemical group C* 0.000 claims 15
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 10
- 229910052757 nitrogen Inorganic materials 0.000 claims 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 8
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 7
- 125000005843 halogen group Chemical group 0.000 claims 6
- 125000000217 alkyl group Chemical group 0.000 claims 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 5
- 229910052760 oxygen Inorganic materials 0.000 claims 5
- 229910052717 sulfur Inorganic materials 0.000 claims 5
- 125000003545 alkoxy group Chemical group 0.000 claims 4
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims 4
- 125000001624 naphthyl group Chemical group 0.000 claims 4
- 150000003839 salts Chemical class 0.000 claims 4
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical class O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 3
- 125000004423 acyloxy group Chemical group 0.000 claims 3
- 125000003342 alkenyl group Chemical group 0.000 claims 3
- 125000000304 alkynyl group Chemical group 0.000 claims 3
- 125000004429 atom Chemical group 0.000 claims 3
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims 3
- 150000001721 carbon Chemical group 0.000 claims 3
- 229910052799 carbon Inorganic materials 0.000 claims 3
- WVSAVJBOUPZGJG-UHFFFAOYSA-N cyclohexanol;dihydrochloride Chemical compound Cl.Cl.OC1CCCCC1 WVSAVJBOUPZGJG-UHFFFAOYSA-N 0.000 claims 3
- 125000002541 furyl group Chemical group 0.000 claims 3
- 125000001072 heteroaryl group Chemical group 0.000 claims 3
- 125000005553 heteroaryloxy group Chemical group 0.000 claims 3
- 125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 0.000 claims 3
- 125000001041 indolyl group Chemical group 0.000 claims 3
- 125000001977 isobenzofuranyl group Chemical group C=1(OC=C2C=CC=CC12)* 0.000 claims 3
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 claims 3
- 125000005186 naphthyloxy group Chemical group C1(=CC=CC2=CC=CC=C12)O* 0.000 claims 3
- 150000002825 nitriles Chemical class 0.000 claims 3
- 125000000109 phenylethoxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])O* 0.000 claims 3
- 125000004076 pyridyl group Chemical group 0.000 claims 3
- 125000000168 pyrrolyl group Chemical group 0.000 claims 3
- 125000001424 substituent group Chemical group 0.000 claims 3
- 229940124530 sulfonamide Drugs 0.000 claims 3
- 150000003456 sulfonamides Chemical class 0.000 claims 3
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 3
- 150000003462 sulfoxides Chemical class 0.000 claims 3
- 125000001544 thienyl group Chemical group 0.000 claims 3
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 3
- 125000001834 xanthenyl group Chemical group C1=CC=CC=2OC3=CC=CC=C3C(C12)* 0.000 claims 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- 125000004981 cycloalkylmethyl group Chemical group 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- 238000000034 method Methods 0.000 claims 2
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims 2
- TTYCOWSNRXQRHZ-NNAHLOSHSA-N (3r)-3-methyl-1-[2-(4-piperidin-1-ylpiperidin-1-yl)-1-[3-(trifluoromethoxy)phenyl]ethyl]cyclopentan-1-ol Chemical compound C1[C@H](C)CCC1(O)C(C=1C=C(OC(F)(F)F)C=CC=1)CN1CCC(N2CCCCC2)CC1 TTYCOWSNRXQRHZ-NNAHLOSHSA-N 0.000 claims 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
- CJKRQTWROJVNCL-UHFFFAOYSA-N 1-(2-cyclohexyl-2-naphthalen-1-ylethyl)piperidin-4-amine Chemical compound C1CC(N)CCN1CC(C=1C2=CC=CC=C2C=CC=1)C1CCCCC1 CJKRQTWROJVNCL-UHFFFAOYSA-N 0.000 claims 1
- IAWXIOLZWOAIRG-NDEPHWFRSA-N 1-[(1r)-1-(6-methoxynaphthalen-2-yl)-2-(4-piperidin-1-ylpiperidin-1-yl)ethyl]cyclohexan-1-ol Chemical compound C([C@@H](C1=CC2=CC=C(C=C2C=C1)OC)C1(O)CCCCC1)N(CC1)CCC1N1CCCCC1 IAWXIOLZWOAIRG-NDEPHWFRSA-N 0.000 claims 1
- VDPDOGLTRRKDGH-IRXDYDNUSA-N 1-[(1r)-2-[(3s)-3-aminopyrrolidin-1-yl]-1-(3-chlorophenyl)ethyl]cyclohexan-1-ol Chemical compound C1[C@@H](N)CCN1C[C@H](C1(O)CCCCC1)C1=CC=CC(Cl)=C1 VDPDOGLTRRKDGH-IRXDYDNUSA-N 0.000 claims 1
- IAWXIOLZWOAIRG-MUUNZHRXSA-N 1-[(1s)-1-(6-methoxynaphthalen-2-yl)-2-(4-piperidin-1-ylpiperidin-1-yl)ethyl]cyclohexan-1-ol Chemical compound C([C@H](C1=CC2=CC=C(C=C2C=C1)OC)C1(O)CCCCC1)N(CC1)CCC1N1CCCCC1 IAWXIOLZWOAIRG-MUUNZHRXSA-N 0.000 claims 1
- MBVYZDRQJYTINU-HSZRJFAPSA-N 1-[(1s)-2-(4-piperidin-1-ylpiperidin-1-yl)-1-[3-(trifluoromethoxy)phenyl]ethyl]cyclohexan-1-ol Chemical compound OC1([C@H](CN2CCC(CC2)N2CCCCC2)C=2C=C(OC(F)(F)F)C=CC=2)CCCCC1 MBVYZDRQJYTINU-HSZRJFAPSA-N 0.000 claims 1
- DCOXRBWGYKLYDY-JOCHJYFZSA-N 1-[(1s)-2-(4-pyrrolidin-1-ylpiperidin-1-yl)-1-[3-(trifluoromethoxy)phenyl]ethyl]cyclohexan-1-ol Chemical compound OC1([C@H](CN2CCC(CC2)N2CCCC2)C=2C=C(OC(F)(F)F)C=CC=2)CCCCC1 DCOXRBWGYKLYDY-JOCHJYFZSA-N 0.000 claims 1
- VDPDOGLTRRKDGH-DLBZAZTESA-N 1-[(1s)-2-[(3s)-3-aminopyrrolidin-1-yl]-1-(3-chlorophenyl)ethyl]cyclohexan-1-ol Chemical compound C1[C@@H](N)CCN1C[C@@H](C1(O)CCCCC1)C1=CC=CC(Cl)=C1 VDPDOGLTRRKDGH-DLBZAZTESA-N 0.000 claims 1
- JFMRJASBESMEIE-HXUWFJFHSA-N 1-[(1s)-2-[4-(dimethylamino)piperidin-1-yl]-1-[3-(trifluoromethoxy)phenyl]ethyl]cyclohexan-1-ol Chemical compound C1CC(N(C)C)CCN1C[C@@H](C1(O)CCCCC1)C1=CC=CC(OC(F)(F)F)=C1 JFMRJASBESMEIE-HXUWFJFHSA-N 0.000 claims 1
- UJEFNHICRIJKPJ-LJQANCHMSA-N 1-[(1s)-2-[4-(methylamino)piperidin-1-yl]-1-[3-(trifluoromethoxy)phenyl]ethyl]cyclohexan-1-ol Chemical compound C1CC(NC)CCN1C[C@@H](C1(O)CCCCC1)C1=CC=CC(OC(F)(F)F)=C1 UJEFNHICRIJKPJ-LJQANCHMSA-N 0.000 claims 1
- IIURQCNVGVEJRY-HXUWFJFHSA-N 1-[(2r)-2-(3-chlorophenyl)-2-cyclohexylethyl]-n-methylpiperidin-4-amine Chemical compound C1CC(NC)CCN1C[C@@H](C=1C=C(Cl)C=CC=1)C1CCCCC1 IIURQCNVGVEJRY-HXUWFJFHSA-N 0.000 claims 1
- IIURQCNVGVEJRY-FQEVSTJZSA-N 1-[(2s)-2-(3-chlorophenyl)-2-cyclohexylethyl]-n-methylpiperidin-4-amine Chemical compound C1CC(NC)CCN1C[C@H](C=1C=C(Cl)C=CC=1)C1CCCCC1 IIURQCNVGVEJRY-FQEVSTJZSA-N 0.000 claims 1
- SRZVCJDLOUJRQP-UHFFFAOYSA-N 1-[1-(3,4-dichlorophenyl)-2-(4-pyrrolidin-1-ylpiperidin-1-yl)ethyl]cyclohexan-1-ol;dihydrochloride Chemical compound Cl.Cl.C1CC(N2CCCC2)CCN1CC(C=1C=C(Cl)C(Cl)=CC=1)C1(O)CCCCC1 SRZVCJDLOUJRQP-UHFFFAOYSA-N 0.000 claims 1
- MFWGKFYEILSNQN-UHFFFAOYSA-N 1-[1-(3,4-dichlorophenyl)-2-[4-(dimethylamino)piperidin-1-yl]ethyl]cyclohexan-1-ol;dihydrochloride Chemical compound Cl.Cl.C1CC(N(C)C)CCN1CC(C1(O)CCCCC1)C1=CC=C(Cl)C(Cl)=C1 MFWGKFYEILSNQN-UHFFFAOYSA-N 0.000 claims 1
- PPVIWCCBXKMCER-UHFFFAOYSA-N 1-[1-(3,4-dichlorophenyl)-2-[4-(methylamino)piperidin-1-yl]ethyl]cyclohexan-1-ol;dihydrochloride Chemical compound Cl.Cl.C1CC(NC)CCN1CC(C1(O)CCCCC1)C1=CC=C(Cl)C(Cl)=C1 PPVIWCCBXKMCER-UHFFFAOYSA-N 0.000 claims 1
- BVCSLVPUUKBSRR-UHFFFAOYSA-N 1-[1-(3-bromo-4-methoxyphenyl)-2-(4-piperidin-1-ylpiperidin-1-yl)ethyl]cyclohexan-1-ol;dihydrochloride Chemical compound Cl.Cl.C1=C(Br)C(OC)=CC=C1C(C1(O)CCCCC1)CN1CCC(N2CCCCC2)CC1 BVCSLVPUUKBSRR-UHFFFAOYSA-N 0.000 claims 1
- MHAAJMKNAODMGC-UHFFFAOYSA-N 1-[1-(3-bromo-4-methoxyphenyl)-2-(4-pyrrolidin-1-ylpiperidin-1-yl)ethyl]cyclohexan-1-ol;dihydrochloride Chemical compound Cl.Cl.C1=C(Br)C(OC)=CC=C1C(C1(O)CCCCC1)CN1CCC(N2CCCC2)CC1 MHAAJMKNAODMGC-UHFFFAOYSA-N 0.000 claims 1
- TZKIWCHJJIEHRF-UHFFFAOYSA-N 1-[1-(3-bromo-4-methoxyphenyl)-2-[4-(dimethylamino)piperidin-1-yl]ethyl]cyclohexan-1-ol;dihydrochloride Chemical compound Cl.Cl.C1=C(Br)C(OC)=CC=C1C(C1(O)CCCCC1)CN1CCC(N(C)C)CC1 TZKIWCHJJIEHRF-UHFFFAOYSA-N 0.000 claims 1
- JZGJRBJPBPBLPD-UHFFFAOYSA-N 1-[1-(3-bromo-4-methoxyphenyl)-2-[4-(methylamino)piperidin-1-yl]ethyl]cyclohexan-1-ol;dihydrochloride Chemical compound Cl.Cl.C1CC(NC)CCN1CC(C1(O)CCCCC1)C1=CC=C(OC)C(Br)=C1 JZGJRBJPBPBLPD-UHFFFAOYSA-N 0.000 claims 1
- GYOPETZBXPUTFN-UHFFFAOYSA-N 1-[1-(3-bromophenyl)-2-(4-piperidin-1-ylpiperidin-1-yl)ethyl]cyclohexan-1-ol;dihydrochloride Chemical compound Cl.Cl.C1CC(N2CCCCC2)CCN1CC(C=1C=C(Br)C=CC=1)C1(O)CCCCC1 GYOPETZBXPUTFN-UHFFFAOYSA-N 0.000 claims 1
- QQMFGZVXHOYHFF-UHFFFAOYSA-N 1-[1-(3-bromophenyl)-2-(4-pyrrolidin-1-ylpiperidin-1-yl)ethyl]cyclohexan-1-ol;dihydrochloride Chemical compound Cl.Cl.C1CC(N2CCCC2)CCN1CC(C=1C=C(Br)C=CC=1)C1(O)CCCCC1 QQMFGZVXHOYHFF-UHFFFAOYSA-N 0.000 claims 1
- VZIJXZCJZQJVIJ-UHFFFAOYSA-N 1-[1-(3-bromophenyl)-2-[4-(dimethylamino)piperidin-1-yl]ethyl]cyclohexan-1-ol;dihydrochloride Chemical compound Cl.Cl.C1CC(N(C)C)CCN1CC(C1(O)CCCCC1)C1=CC=CC(Br)=C1 VZIJXZCJZQJVIJ-UHFFFAOYSA-N 0.000 claims 1
- BVHSFKQXXOILDZ-UHFFFAOYSA-N 1-[1-(3-bromophenyl)-2-[4-(methylamino)piperidin-1-yl]ethyl]cyclohexan-1-ol;dihydrochloride Chemical compound Cl.Cl.C1CC(NC)CCN1CC(C1(O)CCCCC1)C1=CC=CC(Br)=C1 BVHSFKQXXOILDZ-UHFFFAOYSA-N 0.000 claims 1
- AWBKQEAFRBCNRO-UHFFFAOYSA-N 1-[1-(3-chloro-4-methoxyphenyl)-2-(4-piperidin-1-ylpiperidin-1-yl)ethyl]cyclohexan-1-ol Chemical compound C1=C(Cl)C(OC)=CC=C1C(C1(O)CCCCC1)CN1CCC(N2CCCCC2)CC1 AWBKQEAFRBCNRO-UHFFFAOYSA-N 0.000 claims 1
- FSKRAXWGFULMLI-UHFFFAOYSA-N 1-[1-(3-chloro-4-phenylmethoxyphenyl)-2-(4-methoxypiperidin-1-yl)ethyl]cyclohexan-1-ol Chemical compound C1CC(OC)CCN1CC(C1(O)CCCCC1)C(C=C1Cl)=CC=C1OCC1=CC=CC=C1 FSKRAXWGFULMLI-UHFFFAOYSA-N 0.000 claims 1
- OUOMBEXRGSKOSY-UHFFFAOYSA-N 1-[1-(3-chloro-4-phenylmethoxyphenyl)-2-(4-methoxypiperidin-1-yl)ethyl]cyclohexan-1-ol;hydrochloride Chemical compound Cl.C1CC(OC)CCN1CC(C1(O)CCCCC1)C(C=C1Cl)=CC=C1OCC1=CC=CC=C1 OUOMBEXRGSKOSY-UHFFFAOYSA-N 0.000 claims 1
- ZGJKAFRMONTUAK-BPEOLHRYSA-N 1-[1-(3-chloro-4-phenylmethoxyphenyl)-2-[(3r)-3-(dimethylamino)piperidin-1-yl]ethyl]cyclohexan-1-ol;dihydrochloride Chemical compound Cl.Cl.C1[C@H](N(C)C)CCCN1CC(C1(O)CCCCC1)C(C=C1Cl)=CC=C1OCC1=CC=CC=C1 ZGJKAFRMONTUAK-BPEOLHRYSA-N 0.000 claims 1
- GJGWEUSAOCZOFY-MIHMCVIASA-N 1-[1-(3-chloro-4-phenylmethoxyphenyl)-2-[(3r)-3-(dimethylamino)pyrrolidin-1-yl]ethyl]cyclohexan-1-ol Chemical compound C1[C@H](N(C)C)CCN1CC(C1(O)CCCCC1)C(C=C1Cl)=CC=C1OCC1=CC=CC=C1 GJGWEUSAOCZOFY-MIHMCVIASA-N 0.000 claims 1
- HDTVWXNGWVETDJ-WTQRLHSKSA-N 1-[1-(3-chloro-4-phenylmethoxyphenyl)-2-[(3r)-3-(methylamino)pyrrolidin-1-yl]ethyl]cyclohexan-1-ol Chemical compound C1[C@H](NC)CCN1CC(C1(O)CCCCC1)C(C=C1Cl)=CC=C1OCC1=CC=CC=C1 HDTVWXNGWVETDJ-WTQRLHSKSA-N 0.000 claims 1
- ZGJKAFRMONTUAK-ALSOZGBCSA-N 1-[1-(3-chloro-4-phenylmethoxyphenyl)-2-[(3s)-3-(dimethylamino)piperidin-1-yl]ethyl]cyclohexan-1-ol;dihydrochloride Chemical compound Cl.Cl.C1[C@@H](N(C)C)CCCN1CC(C1(O)CCCCC1)C(C=C1Cl)=CC=C1OCC1=CC=CC=C1 ZGJKAFRMONTUAK-ALSOZGBCSA-N 0.000 claims 1
- WVJJYKHGGSDVQE-VZBZPWRVSA-N 1-[1-(3-chloro-4-phenylmethoxyphenyl)-2-[(3s)-3-(dimethylamino)pyrrolidin-1-yl]ethyl]cyclohexan-1-ol;dihydrochloride Chemical compound Cl.Cl.C1[C@@H](N(C)C)CCN1CC(C1(O)CCCCC1)C(C=C1Cl)=CC=C1OCC1=CC=CC=C1 WVJJYKHGGSDVQE-VZBZPWRVSA-N 0.000 claims 1
- XANIWQSKECPOAC-VZBZPWRVSA-N 1-[1-(3-chloro-4-phenylmethoxyphenyl)-2-[(3s)-3-(methylamino)piperidin-1-yl]ethyl]cyclohexan-1-ol;dihydrochloride Chemical compound Cl.Cl.C1[C@@H](NC)CCCN1CC(C1(O)CCCCC1)C(C=C1Cl)=CC=C1OCC1=CC=CC=C1 XANIWQSKECPOAC-VZBZPWRVSA-N 0.000 claims 1
- KORRHYJQPWWYEA-DRYXINTFSA-N 1-[1-(3-chloro-4-phenylmethoxyphenyl)-2-[(3s)-3-(methylamino)pyrrolidin-1-yl]ethyl]cyclohexan-1-ol;dihydrochloride Chemical compound Cl.Cl.C1[C@@H](NC)CCN1CC(C1(O)CCCCC1)C(C=C1Cl)=CC=C1OCC1=CC=CC=C1 KORRHYJQPWWYEA-DRYXINTFSA-N 0.000 claims 1
- SGEYKMREGUSCGG-UHFFFAOYSA-N 1-[1-(3-chloro-4-phenylmethoxyphenyl)-2-[4-(dimethylamino)piperidin-1-yl]ethyl]cyclohexan-1-ol Chemical compound C1CC(N(C)C)CCN1CC(C1(O)CCCCC1)C(C=C1Cl)=CC=C1OCC1=CC=CC=C1 SGEYKMREGUSCGG-UHFFFAOYSA-N 0.000 claims 1
- ZPBKQBHZQNKRIU-UHFFFAOYSA-N 1-[1-(3-chlorophenyl)-2-(4-piperidin-1-ylpiperidin-1-yl)ethyl]cyclohexan-1-ol;dihydrochloride Chemical compound Cl.Cl.C1CC(N2CCCCC2)CCN1CC(C=1C=C(Cl)C=CC=1)C1(O)CCCCC1 ZPBKQBHZQNKRIU-UHFFFAOYSA-N 0.000 claims 1
- NFENJUSJENXBEO-UHFFFAOYSA-N 1-[1-(3-chlorophenyl)-2-(4-pyrrolidin-1-ylpiperidin-1-yl)ethyl]cyclohexan-1-ol;dihydrochloride Chemical compound Cl.Cl.C1CC(N2CCCC2)CCN1CC(C=1C=C(Cl)C=CC=1)C1(O)CCCCC1 NFENJUSJENXBEO-UHFFFAOYSA-N 0.000 claims 1
- CWIPOWUTMHBBMH-HQDRINPVSA-N 1-[1-(3-chlorophenyl)-2-[(3r)-3-(dimethylamino)pyrrolidin-1-yl]ethyl]cyclohexan-1-ol;dihydrochloride Chemical compound Cl.Cl.C1[C@H](N(C)C)CCN1CC(C1(O)CCCCC1)C1=CC=CC(Cl)=C1 CWIPOWUTMHBBMH-HQDRINPVSA-N 0.000 claims 1
- IHVWEKYKMLMEDS-FFDAWYENSA-N 1-[1-(3-chlorophenyl)-2-[(3r)-3-(methylamino)pyrrolidin-1-yl]ethyl]cyclohexan-1-ol;dihydrochloride Chemical compound Cl.Cl.C1[C@H](NC)CCN1CC(C1(O)CCCCC1)C1=CC=CC(Cl)=C1 IHVWEKYKMLMEDS-FFDAWYENSA-N 0.000 claims 1
- CWIPOWUTMHBBMH-XMWICJOTSA-N 1-[1-(3-chlorophenyl)-2-[(3s)-3-(dimethylamino)pyrrolidin-1-yl]ethyl]cyclohexan-1-ol;dihydrochloride Chemical compound Cl.Cl.C1[C@@H](N(C)C)CCN1CC(C1(O)CCCCC1)C1=CC=CC(Cl)=C1 CWIPOWUTMHBBMH-XMWICJOTSA-N 0.000 claims 1
- IHVWEKYKMLMEDS-SEFHDJSNSA-N 1-[1-(3-chlorophenyl)-2-[(3s)-3-(methylamino)pyrrolidin-1-yl]ethyl]cyclohexan-1-ol;dihydrochloride Chemical compound Cl.Cl.C1[C@@H](NC)CCN1CC(C1(O)CCCCC1)C1=CC=CC(Cl)=C1 IHVWEKYKMLMEDS-SEFHDJSNSA-N 0.000 claims 1
- XKOCQKZDILHUDH-UHFFFAOYSA-N 1-[1-(3-chlorophenyl)-2-[4-(dimethylamino)piperidin-1-yl]ethyl]cyclohexan-1-ol;dihydrochloride Chemical compound Cl.Cl.C1CC(N(C)C)CCN1CC(C1(O)CCCCC1)C1=CC=CC(Cl)=C1 XKOCQKZDILHUDH-UHFFFAOYSA-N 0.000 claims 1
- DYNDQFJHGGEBFZ-UHFFFAOYSA-N 1-[1-(3-chlorophenyl)-2-[4-(methylamino)piperidin-1-yl]ethyl]cyclohexan-1-ol;dihydrochloride Chemical compound Cl.Cl.C1CC(NC)CCN1CC(C1(O)CCCCC1)C1=CC=CC(Cl)=C1 DYNDQFJHGGEBFZ-UHFFFAOYSA-N 0.000 claims 1
- GZXOGSFTBFMIER-UHFFFAOYSA-N 1-[1-(3-phenoxyphenyl)-2-(4-pyrrolidin-1-ylpiperidin-1-yl)ethyl]cyclohexan-1-ol;dihydrochloride Chemical compound Cl.Cl.C1CC(N2CCCC2)CCN1CC(C=1C=C(OC=2C=CC=CC=2)C=CC=1)C1(O)CCCCC1 GZXOGSFTBFMIER-UHFFFAOYSA-N 0.000 claims 1
- IAWXIOLZWOAIRG-UHFFFAOYSA-N 1-[1-(6-methoxynaphthalen-2-yl)-2-(4-piperidin-1-ylpiperidin-1-yl)ethyl]cyclohexan-1-ol Chemical compound C1=CC2=CC(OC)=CC=C2C=C1C(C1(O)CCCCC1)CN(CC1)CCC1N1CCCCC1 IAWXIOLZWOAIRG-UHFFFAOYSA-N 0.000 claims 1
- HWPQQDOUGOSTBY-UHFFFAOYSA-N 1-[1-(6-methoxynaphthalen-2-yl)-2-[4-(methylamino)piperidin-1-yl]ethyl]cyclohexan-1-ol Chemical compound C1CC(NC)CCN1CC(C1(O)CCCCC1)C1=CC=C(C=C(OC)C=C2)C2=C1 HWPQQDOUGOSTBY-UHFFFAOYSA-N 0.000 claims 1
- FJEFSULYEQYQGY-UHFFFAOYSA-N 1-[1-[3-chloro-4-(naphthalen-2-ylmethoxy)phenyl]-2-[4-(dimethylamino)piperidin-1-yl]ethyl]cyclohexan-1-ol Chemical compound C1CC(N(C)C)CCN1CC(C1(O)CCCCC1)C(C=C1Cl)=CC=C1OCC1=CC=C(C=CC=C2)C2=C1 FJEFSULYEQYQGY-UHFFFAOYSA-N 0.000 claims 1
- ZSNJDAAEELXBNP-UHFFFAOYSA-N 1-[1-[4-(2-phenylethoxy)phenyl]-2-(4-piperidin-1-ylpiperidin-1-yl)ethyl]cyclohexan-1-ol Chemical compound C1CC(N2CCCCC2)CCN1CC(C=1C=CC(OCCC=2C=CC=CC=2)=CC=1)C1(O)CCCCC1 ZSNJDAAEELXBNP-UHFFFAOYSA-N 0.000 claims 1
- RWDZGCQTWDMBHW-UHFFFAOYSA-N 1-[1-[4-[2-(4-methoxyphenyl)ethoxy]phenyl]-2-(4-piperidin-1-ylpiperidin-1-yl)ethyl]cyclohexan-1-ol Chemical compound C1=CC(OC)=CC=C1CCOC1=CC=C(C(CN2CCC(CC2)N2CCCCC2)C2(O)CCCCC2)C=C1 RWDZGCQTWDMBHW-UHFFFAOYSA-N 0.000 claims 1
- CWDDOYNJPSEQHR-UHFFFAOYSA-N 1-[1-naphthalen-2-yl-2-(4-piperidin-1-ylpiperidin-1-yl)ethyl]cyclohexan-1-ol;dihydrochloride Chemical compound Cl.Cl.C1CC(N2CCCCC2)CCN1CC(C=1C=C2C=CC=CC2=CC=1)C1(O)CCCCC1 CWDDOYNJPSEQHR-UHFFFAOYSA-N 0.000 claims 1
- MGSUTQBUGDWZKK-UHFFFAOYSA-N 1-[1-naphthalen-2-yl-2-(4-pyrrolidin-1-ylpiperidin-1-yl)ethyl]cyclohexan-1-ol;dihydrochloride Chemical compound Cl.Cl.C1CC(N2CCCC2)CCN1CC(C=1C=C2C=CC=CC2=CC=1)C1(O)CCCCC1 MGSUTQBUGDWZKK-UHFFFAOYSA-N 0.000 claims 1
- DJPZSDRVVABZMY-UHFFFAOYSA-N 1-[2-(1-hydroxycyclohexyl)-2-[3-(trifluoromethoxy)phenyl]ethyl]piperidin-4-ol;hydrochloride Chemical compound Cl.C1CC(O)CCN1CC(C1(O)CCCCC1)C1=CC=CC(OC(F)(F)F)=C1 DJPZSDRVVABZMY-UHFFFAOYSA-N 0.000 claims 1
- INDZFJNPDMNGBX-UHFFFAOYSA-N 1-[2-(3-chloro-4-phenylmethoxyphenyl)-2-(1-hydroxycyclohexyl)ethyl]piperidin-4-ol;hydrochloride Chemical compound Cl.C1CC(O)CCN1CC(C1(O)CCCCC1)C(C=C1Cl)=CC=C1OCC1=CC=CC=C1 INDZFJNPDMNGBX-UHFFFAOYSA-N 0.000 claims 1
- BLCWDRHQNANBLZ-UHFFFAOYSA-N 1-[2-(3-chlorophenyl)-2-cycloheptylethyl]-n,n-dimethylpiperidin-4-amine;dihydrochloride Chemical compound Cl.Cl.C1CC(N(C)C)CCN1CC(C=1C=C(Cl)C=CC=1)C1CCCCCC1 BLCWDRHQNANBLZ-UHFFFAOYSA-N 0.000 claims 1
- KYGOYSZJECEPMA-UHFFFAOYSA-N 1-[2-(3-chlorophenyl)-2-cycloheptylethyl]-n-methylpiperidin-4-amine;dihydrochloride Chemical compound Cl.Cl.C1CC(NC)CCN1CC(C=1C=C(Cl)C=CC=1)C1CCCCCC1 KYGOYSZJECEPMA-UHFFFAOYSA-N 0.000 claims 1
- OQTNFUIQBHMILJ-UHFFFAOYSA-N 1-[2-(3-chlorophenyl)-2-cyclohexylethyl]-n,n-dimethylpiperidin-4-amine;dihydrochloride Chemical compound Cl.Cl.C1CC(N(C)C)CCN1CC(C=1C=C(Cl)C=CC=1)C1CCCCC1 OQTNFUIQBHMILJ-UHFFFAOYSA-N 0.000 claims 1
- DVHITDBRGKLHMG-UHFFFAOYSA-N 1-[2-(3-chlorophenyl)-2-cyclohexylethyl]-n-methylpiperidin-4-amine;dihydrochloride Chemical compound Cl.Cl.C1CC(NC)CCN1CC(C=1C=C(Cl)C=CC=1)C1CCCCC1 DVHITDBRGKLHMG-UHFFFAOYSA-N 0.000 claims 1
- YNBXOMCBZWSFAZ-UHFFFAOYSA-N 1-[2-(3-chlorophenyl)-2-cyclopentylethyl]-n,n-dimethylpiperidin-4-amine;dihydrochloride Chemical compound Cl.Cl.C1CC(N(C)C)CCN1CC(C=1C=C(Cl)C=CC=1)C1CCCC1 YNBXOMCBZWSFAZ-UHFFFAOYSA-N 0.000 claims 1
- OFUWCTAPSJQHPU-UHFFFAOYSA-N 1-[2-(3-chlorophenyl)-2-cyclopentylethyl]-n-methylpiperidin-4-amine;dihydrochloride Chemical compound Cl.Cl.C1CC(NC)CCN1CC(C=1C=C(Cl)C=CC=1)C1CCCC1 OFUWCTAPSJQHPU-UHFFFAOYSA-N 0.000 claims 1
- RVYNLWCURWSQHX-UHFFFAOYSA-N 1-[2-(4-aminopiperidin-1-yl)-1-(3,4-dichlorophenyl)ethyl]cyclohexan-1-ol;dihydrochloride Chemical compound Cl.Cl.C1CC(N)CCN1CC(C1(O)CCCCC1)C1=CC=C(Cl)C(Cl)=C1 RVYNLWCURWSQHX-UHFFFAOYSA-N 0.000 claims 1
- HVQWIUXGTPPNJI-UHFFFAOYSA-N 1-[2-(4-aminopiperidin-1-yl)-1-(3-bromo-4-methoxyphenyl)ethyl]cyclohexan-1-ol;dihydrochloride Chemical compound Cl.Cl.C1=C(Br)C(OC)=CC=C1C(C1(O)CCCCC1)CN1CCC(N)CC1 HVQWIUXGTPPNJI-UHFFFAOYSA-N 0.000 claims 1
- UWYYRZMKEQAYMC-UHFFFAOYSA-N 1-[2-(4-aminopiperidin-1-yl)-1-(3-bromophenyl)ethyl]cyclohexan-1-ol;dihydrochloride Chemical compound Cl.Cl.C1CC(N)CCN1CC(C1(O)CCCCC1)C1=CC=CC(Br)=C1 UWYYRZMKEQAYMC-UHFFFAOYSA-N 0.000 claims 1
- KAGXSGIXHYOZNL-UHFFFAOYSA-N 1-[2-(4-aminopiperidin-1-yl)-1-(3-chloro-4-phenylmethoxyphenyl)ethyl]cyclohexan-1-ol Chemical compound C1CC(N)CCN1CC(C1(O)CCCCC1)C(C=C1Cl)=CC=C1OCC1=CC=CC=C1 KAGXSGIXHYOZNL-UHFFFAOYSA-N 0.000 claims 1
- CAODEKOFILDNTI-UHFFFAOYSA-N 1-[2-(4-aminopiperidin-1-yl)-1-(3-chlorophenyl)ethyl]-4-methylcyclohexan-1-ol;dihydrochloride Chemical compound Cl.Cl.C1CC(C)CCC1(O)C(C=1C=C(Cl)C=CC=1)CN1CCC(N)CC1 CAODEKOFILDNTI-UHFFFAOYSA-N 0.000 claims 1
- RRFKJAVCBRGKSM-UHFFFAOYSA-N 1-[2-(4-aminopiperidin-1-yl)-1-(3-chlorophenyl)ethyl]cyclohexan-1-ol;dihydrochloride Chemical compound Cl.Cl.C1CC(N)CCN1CC(C1(O)CCCCC1)C1=CC=CC(Cl)=C1 RRFKJAVCBRGKSM-UHFFFAOYSA-N 0.000 claims 1
- DNBPJNAVOUURTN-UHFFFAOYSA-N 1-[2-(4-aminopiperidin-1-yl)-1-(3-methoxy-4-phenylmethoxyphenyl)ethyl]cyclohexan-1-ol Chemical compound COC1=CC(C(CN2CCC(N)CC2)C2(O)CCCCC2)=CC=C1OCC1=CC=CC=C1 DNBPJNAVOUURTN-UHFFFAOYSA-N 0.000 claims 1
- LTGDKKXOMQJMIU-UHFFFAOYSA-N 1-[2-(4-aminopiperidin-1-yl)-1-(5-methoxy-1-benzothiophen-3-yl)ethyl]cyclohexan-1-ol;dihydrochloride Chemical compound Cl.Cl.C12=CC(OC)=CC=C2SC=C1C(C1(O)CCCCC1)CN1CCC(N)CC1 LTGDKKXOMQJMIU-UHFFFAOYSA-N 0.000 claims 1
- WXTDXCCEOAQFOA-UHFFFAOYSA-N 1-[2-(4-aminopiperidin-1-yl)-1-(6-methoxynaphthalen-2-yl)ethyl]cyclohexan-1-ol Chemical compound C1=CC2=CC(OC)=CC=C2C=C1C(C1(O)CCCCC1)CN1CCC(N)CC1 WXTDXCCEOAQFOA-UHFFFAOYSA-N 0.000 claims 1
- GEBCWEHNEZYLNG-UHFFFAOYSA-N 1-[2-(4-aminopiperidin-1-yl)-1-[3-(trifluoromethyl)phenyl]ethyl]cyclohexan-1-ol;dihydrochloride Chemical compound Cl.Cl.C1CC(N)CCN1CC(C1(O)CCCCC1)C1=CC=CC(C(F)(F)F)=C1 GEBCWEHNEZYLNG-UHFFFAOYSA-N 0.000 claims 1
- OHICOTWFVNHIBT-UHFFFAOYSA-N 1-[2-(4-aminopiperidin-1-yl)-1-[3-chloro-4-(naphthalen-2-ylmethoxy)phenyl]ethyl]cyclohexan-1-ol Chemical compound C1CC(N)CCN1CC(C1(O)CCCCC1)C(C=C1Cl)=CC=C1OCC1=CC=C(C=CC=C2)C2=C1 OHICOTWFVNHIBT-UHFFFAOYSA-N 0.000 claims 1
- AIGZXOUFYPSSKG-UHFFFAOYSA-N 1-[2-(4-aminopiperidin-1-yl)-1-[4-(trifluoromethoxy)phenyl]ethyl]cyclobutan-1-ol;dihydrochloride Chemical compound Cl.Cl.C1CC(N)CCN1CC(C1(O)CCC1)C1=CC=C(OC(F)(F)F)C=C1 AIGZXOUFYPSSKG-UHFFFAOYSA-N 0.000 claims 1
- SFOWKBVDHIQPIY-UHFFFAOYSA-N 1-[2-(4-aminopiperidin-1-yl)-1-[4-(trifluoromethoxy)phenyl]ethyl]cyclohexan-1-ol;dihydrochloride Chemical compound Cl.Cl.C1CC(N)CCN1CC(C1(O)CCCCC1)C1=CC=C(OC(F)(F)F)C=C1 SFOWKBVDHIQPIY-UHFFFAOYSA-N 0.000 claims 1
- VEALBBNLMSGRDL-UHFFFAOYSA-N 1-[2-(4-aminopiperidin-1-yl)-1-naphthalen-1-ylethyl]cyclobutan-1-ol;dihydrochloride Chemical compound Cl.Cl.C1CC(N)CCN1CC(C1(O)CCC1)C1=CC=CC2=CC=CC=C12 VEALBBNLMSGRDL-UHFFFAOYSA-N 0.000 claims 1
- XDXQQZIFDMNDQQ-UHFFFAOYSA-N 1-[2-(4-aminopiperidin-1-yl)-1-naphthalen-2-ylethyl]cyclohexan-1-ol;dihydrochloride Chemical compound Cl.Cl.C1CC(N)CCN1CC(C1(O)CCCCC1)C1=CC=C(C=CC=C2)C2=C1 XDXQQZIFDMNDQQ-UHFFFAOYSA-N 0.000 claims 1
- ITRDPYOXHPOVBA-UHFFFAOYSA-N 1-[2-(4-morpholin-4-ylpiperidin-1-yl)-1-[3-(trifluoromethoxy)phenyl]ethyl]cyclohexan-1-ol Chemical compound C1CC(N2CCOCC2)CCN1CC(C=1C=C(OC(F)(F)F)C=CC=1)C1(O)CCCCC1 ITRDPYOXHPOVBA-UHFFFAOYSA-N 0.000 claims 1
- AANYYRCJLCRSAF-UHFFFAOYSA-N 1-[2-(4-piperidin-1-ylpiperidin-1-yl)-1-[3-(trifluoromethyl)phenyl]ethyl]cyclohexan-1-ol;dihydrochloride Chemical compound Cl.Cl.C1CC(N2CCCCC2)CCN1CC(C=1C=C(C=CC=1)C(F)(F)F)C1(O)CCCCC1 AANYYRCJLCRSAF-UHFFFAOYSA-N 0.000 claims 1
- OVDUXQXVMKDHRB-UHFFFAOYSA-N 1-[2-(4-piperidin-1-ylpiperidin-1-yl)-1-[4-(trifluoromethoxy)phenyl]ethyl]cyclohexan-1-ol;dihydrochloride Chemical compound Cl.Cl.C1CC(N2CCCCC2)CCN1CC(C=1C=CC(OC(F)(F)F)=CC=1)C1(O)CCCCC1 OVDUXQXVMKDHRB-UHFFFAOYSA-N 0.000 claims 1
- BENZXZNVCRSBQF-UHFFFAOYSA-N 1-[2-(4-pyrrolidin-1-ylpiperidin-1-yl)-1-[3-(trifluoromethyl)phenyl]ethyl]cyclohexan-1-ol;dihydrochloride Chemical compound Cl.Cl.C1CC(N2CCCC2)CCN1CC(C=1C=C(C=CC=1)C(F)(F)F)C1(O)CCCCC1 BENZXZNVCRSBQF-UHFFFAOYSA-N 0.000 claims 1
- PJKNQNUFBRIEMZ-VBUDHXPUSA-N 1-[2-[(3r)-3-(dimethylamino)piperidin-1-yl]-1-[3-(trifluoromethoxy)phenyl]ethyl]cyclohexan-1-ol;dihydrochloride Chemical compound Cl.Cl.C1[C@H](N(C)C)CCCN1CC(C1(O)CCCCC1)C1=CC=CC(OC(F)(F)F)=C1 PJKNQNUFBRIEMZ-VBUDHXPUSA-N 0.000 claims 1
- MUVGSTXLQZBKFL-RMVMEJTISA-N 1-[2-[(3r)-3-(dimethylamino)pyrrolidin-1-yl]-1-(4-phenylmethoxyphenyl)ethyl]cyclohexan-1-ol Chemical compound C1[C@H](N(C)C)CCN1CC(C1(O)CCCCC1)C(C=C1)=CC=C1OCC1=CC=CC=C1 MUVGSTXLQZBKFL-RMVMEJTISA-N 0.000 claims 1
- JMHZMEDTNOMXMV-JGUWFSKSSA-N 1-[2-[(3r)-3-(dimethylamino)pyrrolidin-1-yl]-1-[3-(trifluoromethoxy)phenyl]ethyl]cyclohexan-1-ol;dihydrochloride Chemical compound Cl.Cl.C1[C@H](N(C)C)CCN1CC(C1(O)CCCCC1)C1=CC=CC(OC(F)(F)F)=C1 JMHZMEDTNOMXMV-JGUWFSKSSA-N 0.000 claims 1
- BYEGKMVVOCMTOJ-HQDRINPVSA-N 1-[2-[(3r)-3-(dimethylamino)pyrrolidin-1-yl]-1-[3-(trifluoromethyl)phenyl]ethyl]cyclohexan-1-ol;dihydrochloride Chemical compound Cl.Cl.C1[C@H](N(C)C)CCN1CC(C1(O)CCCCC1)C1=CC=CC(C(F)(F)F)=C1 BYEGKMVVOCMTOJ-HQDRINPVSA-N 0.000 claims 1
- WHMRLHZYHWUSOQ-PPUHSXQSSA-N 1-[2-[(3r)-3-(dimethylamino)pyrrolidin-1-yl]-1-naphthalen-1-ylethyl]cyclohexan-1-ol Chemical compound C1[C@H](N(C)C)CCN1CC(C1(O)CCCCC1)C1=CC=CC2=CC=CC=C12 WHMRLHZYHWUSOQ-PPUHSXQSSA-N 0.000 claims 1
- HEHGCEADLICPKX-WTQRLHSKSA-N 1-[2-[(3r)-3-(dimethylamino)pyrrolidin-1-yl]-1-naphthalen-2-ylethyl]cyclohexan-1-ol Chemical compound C1[C@H](N(C)C)CCN1CC(C1(O)CCCCC1)C1=CC=C(C=CC=C2)C2=C1 HEHGCEADLICPKX-WTQRLHSKSA-N 0.000 claims 1
- TXANBTQNSKIIPJ-JGUWFSKSSA-N 1-[2-[(3r)-3-(methylamino)piperidin-1-yl]-1-[3-(trifluoromethoxy)phenyl]ethyl]cyclohexan-1-ol;dihydrochloride Chemical compound Cl.Cl.C1[C@H](NC)CCCN1CC(C1(O)CCCCC1)C1=CC=CC(OC(F)(F)F)=C1 TXANBTQNSKIIPJ-JGUWFSKSSA-N 0.000 claims 1
- DLDRVDRDOQTYDC-XQZUBTRRSA-N 1-[2-[(3r)-3-(methylamino)pyrrolidin-1-yl]-1-(4-phenylmethoxyphenyl)ethyl]cyclohexan-1-ol Chemical compound C1[C@H](NC)CCN1CC(C1(O)CCCCC1)C(C=C1)=CC=C1OCC1=CC=CC=C1 DLDRVDRDOQTYDC-XQZUBTRRSA-N 0.000 claims 1
- JOGUGUKTWLKIEF-HCLBTYMISA-N 1-[2-[(3r)-3-(methylamino)pyrrolidin-1-yl]-1-[3-(trifluoromethoxy)phenyl]ethyl]cyclohexan-1-ol;dihydrochloride Chemical compound Cl.Cl.C1[C@H](NC)CCN1CC(C1(O)CCCCC1)C1=CC=CC(OC(F)(F)F)=C1 JOGUGUKTWLKIEF-HCLBTYMISA-N 0.000 claims 1
- ZGYZJSXWGSDMFQ-LCQOSCCDSA-N 1-[2-[(3r)-3-(methylamino)pyrrolidin-1-yl]-1-naphthalen-1-ylethyl]cyclohexan-1-ol Chemical compound C1[C@H](NC)CCN1CC(C1(O)CCCCC1)C1=CC=CC2=CC=CC=C12 ZGYZJSXWGSDMFQ-LCQOSCCDSA-N 0.000 claims 1
- HAGZEKHSCZIFMZ-ZMFCMNQTSA-N 1-[2-[(3r)-3-(methylamino)pyrrolidin-1-yl]-1-naphthalen-2-ylethyl]cyclohexan-1-ol Chemical compound C1[C@H](NC)CCN1CC(C1(O)CCCCC1)C1=CC=C(C=CC=C2)C2=C1 HAGZEKHSCZIFMZ-ZMFCMNQTSA-N 0.000 claims 1
- YPKJERLBYISXIG-OEJMRNKDSA-N 1-[2-[(3r)-3-aminopiperidin-1-yl]-1-(3-chloro-4-phenylmethoxyphenyl)ethyl]cyclohexan-1-ol;dihydrochloride Chemical compound Cl.Cl.C1[C@H](N)CCCN1CC(C1(O)CCCCC1)C(C=C1Cl)=CC=C1OCC1=CC=CC=C1 YPKJERLBYISXIG-OEJMRNKDSA-N 0.000 claims 1
- NDZMYSOZHKSXLU-HCLBTYMISA-N 1-[2-[(3r)-3-aminopiperidin-1-yl]-1-[3-(trifluoromethoxy)phenyl]ethyl]cyclohexan-1-ol;dihydrochloride Chemical compound Cl.Cl.C1[C@H](N)CCCN1CC(C1(O)CCCCC1)C1=CC=CC(OC(F)(F)F)=C1 NDZMYSOZHKSXLU-HCLBTYMISA-N 0.000 claims 1
- XHVULMOUPAEUNC-ZMFCMNQTSA-N 1-[2-[(3r)-3-aminopyrrolidin-1-yl]-1-(3-chloro-4-phenylmethoxyphenyl)ethyl]cyclohexan-1-ol Chemical compound C1[C@H](N)CCN1CC(C1(O)CCCCC1)C(C=C1Cl)=CC=C1OCC1=CC=CC=C1 XHVULMOUPAEUNC-ZMFCMNQTSA-N 0.000 claims 1
- DVHUSLPVEFQUIF-JAYLRORVSA-N 1-[2-[(3r)-3-aminopyrrolidin-1-yl]-1-(3-chlorophenyl)ethyl]cyclohexan-1-ol;dihydrochloride Chemical compound Cl.Cl.C1[C@H](N)CCN1CC(C1(O)CCCCC1)C1=CC=CC(Cl)=C1 DVHUSLPVEFQUIF-JAYLRORVSA-N 0.000 claims 1
- PRZFZENFKPQGSQ-LETIRJCYSA-N 1-[2-[(3r)-3-aminopyrrolidin-1-yl]-1-(4-phenylmethoxyphenyl)ethyl]cyclohexan-1-ol Chemical compound C1[C@H](N)CCN1CC(C1(O)CCCCC1)C(C=C1)=CC=C1OCC1=CC=CC=C1 PRZFZENFKPQGSQ-LETIRJCYSA-N 0.000 claims 1
- IKRRMRWHRBSRTL-LDCVWXEPSA-N 1-[2-[(3r)-3-aminopyrrolidin-1-yl]-1-[3-(trifluoromethoxy)phenyl]ethyl]cyclohexan-1-ol Chemical compound C1[C@H](N)CCN1CC(C1(O)CCCCC1)C1=CC=CC(OC(F)(F)F)=C1 IKRRMRWHRBSRTL-LDCVWXEPSA-N 0.000 claims 1
- CGRAUPGXOYQYDQ-JAYLRORVSA-N 1-[2-[(3r)-3-aminopyrrolidin-1-yl]-1-[3-(trifluoromethyl)phenyl]ethyl]cyclohexan-1-ol;dihydrochloride Chemical compound Cl.Cl.C1[C@H](N)CCN1CC(C1(O)CCCCC1)C1=CC=CC(C(F)(F)F)=C1 CGRAUPGXOYQYDQ-JAYLRORVSA-N 0.000 claims 1
- ZTIFKHRRBDYPLJ-ITUIMRKVSA-N 1-[2-[(3r)-3-aminopyrrolidin-1-yl]-1-naphthalen-1-ylethyl]cyclohexan-1-ol Chemical compound C1[C@H](N)CCN1CC(C1(O)CCCCC1)C1=CC=CC2=CC=CC=C12 ZTIFKHRRBDYPLJ-ITUIMRKVSA-N 0.000 claims 1
- ZSEXILAFGNBAHS-VQCQRNETSA-N 1-[2-[(3r)-3-aminopyrrolidin-1-yl]-1-naphthalen-2-ylethyl]cyclohexan-1-ol Chemical compound C1[C@H](N)CCN1CC(C1(O)CCCCC1)C1=CC=C(C=CC=C2)C2=C1 ZSEXILAFGNBAHS-VQCQRNETSA-N 0.000 claims 1
- PJKNQNUFBRIEMZ-VHUZWAOLSA-N 1-[2-[(3s)-3-(dimethylamino)piperidin-1-yl]-1-[3-(trifluoromethoxy)phenyl]ethyl]cyclohexan-1-ol;dihydrochloride Chemical compound Cl.Cl.C1[C@@H](N(C)C)CCCN1CC(C1(O)CCCCC1)C1=CC=CC(OC(F)(F)F)=C1 PJKNQNUFBRIEMZ-VHUZWAOLSA-N 0.000 claims 1
- MNJYBOCMFOUNIW-QTTLMUINSA-N 1-[2-[(3s)-3-(dimethylamino)pyrrolidin-1-yl]-1-(4-phenylmethoxyphenyl)ethyl]cyclohexan-1-ol;dihydrochloride Chemical compound Cl.Cl.C1[C@@H](N(C)C)CCN1CC(C1(O)CCCCC1)C(C=C1)=CC=C1OCC1=CC=CC=C1 MNJYBOCMFOUNIW-QTTLMUINSA-N 0.000 claims 1
- JMHZMEDTNOMXMV-DXGWAKCESA-N 1-[2-[(3s)-3-(dimethylamino)pyrrolidin-1-yl]-1-[3-(trifluoromethoxy)phenyl]ethyl]cyclohexan-1-ol;dihydrochloride Chemical compound Cl.Cl.C1[C@@H](N(C)C)CCN1CC(C1(O)CCCCC1)C1=CC=CC(OC(F)(F)F)=C1 JMHZMEDTNOMXMV-DXGWAKCESA-N 0.000 claims 1
- BYEGKMVVOCMTOJ-XMWICJOTSA-N 1-[2-[(3s)-3-(dimethylamino)pyrrolidin-1-yl]-1-[3-(trifluoromethyl)phenyl]ethyl]cyclohexan-1-ol;dihydrochloride Chemical compound Cl.Cl.C1[C@@H](N(C)C)CCN1CC(C1(O)CCCCC1)C1=CC=CC(C(F)(F)F)=C1 BYEGKMVVOCMTOJ-XMWICJOTSA-N 0.000 claims 1
- IQFOLKYJKYTXEV-MYULVRAQSA-N 1-[2-[(3s)-3-(dimethylamino)pyrrolidin-1-yl]-1-naphthalen-1-ylethyl]cyclohexan-1-ol;dihydrochloride Chemical compound Cl.Cl.C1[C@@H](N(C)C)CCN1CC(C1(O)CCCCC1)C1=CC=CC2=CC=CC=C12 IQFOLKYJKYTXEV-MYULVRAQSA-N 0.000 claims 1
- RKZVQRXSTUFVJB-DRYXINTFSA-N 1-[2-[(3s)-3-(dimethylamino)pyrrolidin-1-yl]-1-naphthalen-2-ylethyl]cyclohexan-1-ol;dihydrochloride Chemical compound Cl.Cl.C1[C@@H](N(C)C)CCN1CC(C1(O)CCCCC1)C1=CC=C(C=CC=C2)C2=C1 RKZVQRXSTUFVJB-DRYXINTFSA-N 0.000 claims 1
- TXANBTQNSKIIPJ-DXGWAKCESA-N 1-[2-[(3s)-3-(methylamino)piperidin-1-yl]-1-[3-(trifluoromethoxy)phenyl]ethyl]cyclohexan-1-ol;dihydrochloride Chemical compound Cl.Cl.C1[C@@H](NC)CCCN1CC(C1(O)CCCCC1)C1=CC=CC(OC(F)(F)F)=C1 TXANBTQNSKIIPJ-DXGWAKCESA-N 0.000 claims 1
- BRBDOHFZYATBNK-LXTUAOQPSA-N 1-[2-[(3s)-3-(methylamino)pyrrolidin-1-yl]-1-(4-phenylmethoxyphenyl)ethyl]cyclohexan-1-ol;dihydrochloride Chemical compound Cl.Cl.C1[C@@H](NC)CCN1CC(C1(O)CCCCC1)C(C=C1)=CC=C1OCC1=CC=CC=C1 BRBDOHFZYATBNK-LXTUAOQPSA-N 0.000 claims 1
- JOGUGUKTWLKIEF-OCCQCILZSA-N 1-[2-[(3s)-3-(methylamino)pyrrolidin-1-yl]-1-[3-(trifluoromethoxy)phenyl]ethyl]cyclohexan-1-ol;dihydrochloride Chemical compound Cl.Cl.C1[C@@H](NC)CCN1CC(C1(O)CCCCC1)C1=CC=CC(OC(F)(F)F)=C1 JOGUGUKTWLKIEF-OCCQCILZSA-N 0.000 claims 1
- QWIQHGBHAWRTTI-SEFHDJSNSA-N 1-[2-[(3s)-3-(methylamino)pyrrolidin-1-yl]-1-[3-(trifluoromethyl)phenyl]ethyl]cyclohexan-1-ol;dihydrochloride Chemical compound Cl.Cl.C1[C@@H](NC)CCN1CC(C1(O)CCCCC1)C1=CC=CC(C(F)(F)F)=C1 QWIQHGBHAWRTTI-SEFHDJSNSA-N 0.000 claims 1
- ZOZTZJBVFDBSRP-NCNDTFMYSA-N 1-[2-[(3s)-3-(methylamino)pyrrolidin-1-yl]-1-naphthalen-1-ylethyl]cyclohexan-1-ol;dihydrochloride Chemical compound Cl.Cl.C1[C@@H](NC)CCN1CC(C1(O)CCCCC1)C1=CC=CC2=CC=CC=C12 ZOZTZJBVFDBSRP-NCNDTFMYSA-N 0.000 claims 1
- XTMCOVIFTUCZCQ-JIPKYUQLSA-N 1-[2-[(3s)-3-(methylamino)pyrrolidin-1-yl]-1-naphthalen-2-ylethyl]cyclohexan-1-ol;dihydrochloride Chemical compound Cl.Cl.C1[C@@H](NC)CCN1CC(C1(O)CCCCC1)C1=CC=C(C=CC=C2)C2=C1 XTMCOVIFTUCZCQ-JIPKYUQLSA-N 0.000 claims 1
- YPKJERLBYISXIG-DRYXINTFSA-N 1-[2-[(3s)-3-aminopiperidin-1-yl]-1-(3-chloro-4-phenylmethoxyphenyl)ethyl]cyclohexan-1-ol;dihydrochloride Chemical compound Cl.Cl.C1[C@@H](N)CCCN1CC(C1(O)CCCCC1)C(C=C1Cl)=CC=C1OCC1=CC=CC=C1 YPKJERLBYISXIG-DRYXINTFSA-N 0.000 claims 1
- NDZMYSOZHKSXLU-OCCQCILZSA-N 1-[2-[(3s)-3-aminopiperidin-1-yl]-1-[3-(trifluoromethoxy)phenyl]ethyl]cyclohexan-1-ol;dihydrochloride Chemical compound Cl.Cl.C1[C@@H](N)CCCN1CC(C1(O)CCCCC1)C1=CC=CC(OC(F)(F)F)=C1 NDZMYSOZHKSXLU-OCCQCILZSA-N 0.000 claims 1
- WEKDEHPGMMKXAX-JIPKYUQLSA-N 1-[2-[(3s)-3-aminopyrrolidin-1-yl]-1-(3-chloro-4-phenylmethoxyphenyl)ethyl]cyclohexan-1-ol;dihydrochloride Chemical compound Cl.Cl.C1[C@@H](N)CCN1CC(C1(O)CCCCC1)C(C=C1Cl)=CC=C1OCC1=CC=CC=C1 WEKDEHPGMMKXAX-JIPKYUQLSA-N 0.000 claims 1
- DVHUSLPVEFQUIF-VEEDUFMYSA-N 1-[2-[(3s)-3-aminopyrrolidin-1-yl]-1-(3-chlorophenyl)ethyl]cyclohexan-1-ol;dihydrochloride Chemical compound Cl.Cl.C1[C@@H](N)CCN1CC(C1(O)CCCCC1)C1=CC=CC(Cl)=C1 DVHUSLPVEFQUIF-VEEDUFMYSA-N 0.000 claims 1
- SEWPCNWNHBAWJU-LIPLMRRRSA-N 1-[2-[(3s)-3-aminopyrrolidin-1-yl]-1-(4-phenylmethoxyphenyl)ethyl]cyclohexan-1-ol;dihydrochloride Chemical compound Cl.Cl.C1[C@@H](N)CCN1CC(C1(O)CCCCC1)C(C=C1)=CC=C1OCC1=CC=CC=C1 SEWPCNWNHBAWJU-LIPLMRRRSA-N 0.000 claims 1
- FNWBBOBGVZJBDF-CTAXNUCUSA-N 1-[2-[(3s)-3-aminopyrrolidin-1-yl]-1-[3-(trifluoromethoxy)phenyl]ethyl]cyclohexan-1-ol;dihydrochloride Chemical compound Cl.Cl.C1[C@@H](N)CCN1CC(C1(O)CCCCC1)C1=CC=CC(OC(F)(F)F)=C1 FNWBBOBGVZJBDF-CTAXNUCUSA-N 0.000 claims 1
- CGRAUPGXOYQYDQ-VEEDUFMYSA-N 1-[2-[(3s)-3-aminopyrrolidin-1-yl]-1-[3-(trifluoromethyl)phenyl]ethyl]cyclohexan-1-ol;dihydrochloride Chemical compound Cl.Cl.C1[C@@H](N)CCN1CC(C1(O)CCCCC1)C1=CC=CC(C(F)(F)F)=C1 CGRAUPGXOYQYDQ-VEEDUFMYSA-N 0.000 claims 1
- DMVLYQQWORENHP-SANRYGKWSA-N 1-[2-[(3s)-3-aminopyrrolidin-1-yl]-1-naphthalen-1-ylethyl]cyclohexan-1-ol;dihydrochloride Chemical compound Cl.Cl.C1[C@@H](N)CCN1CC(C1(O)CCCCC1)C1=CC=CC2=CC=CC=C12 DMVLYQQWORENHP-SANRYGKWSA-N 0.000 claims 1
- HNUCUFSLWRTWHI-OAQMNXJYSA-N 1-[2-[(3s)-3-aminopyrrolidin-1-yl]-1-naphthalen-2-ylethyl]cyclohexan-1-ol;dihydrochloride Chemical compound Cl.Cl.C1[C@@H](N)CCN1CC(C1(O)CCCCC1)C1=CC=C(C=CC=C2)C2=C1 HNUCUFSLWRTWHI-OAQMNXJYSA-N 0.000 claims 1
- INJPFJRUQCHSNH-UHFFFAOYSA-N 1-[2-[4-(dimethylamino)piperidin-1-yl]-1-(3-methoxy-4-phenylmethoxyphenyl)ethyl]cyclohexan-1-ol Chemical compound COC1=CC(C(CN2CCC(CC2)N(C)C)C2(O)CCCCC2)=CC=C1OCC1=CC=CC=C1 INJPFJRUQCHSNH-UHFFFAOYSA-N 0.000 claims 1
- CJZZWMSHMCFIFZ-UHFFFAOYSA-N 1-[2-[4-(dimethylamino)piperidin-1-yl]-1-(6-methoxynaphthalen-2-yl)ethyl]cyclohexan-1-ol Chemical compound C1=CC2=CC(OC)=CC=C2C=C1C(C1(O)CCCCC1)CN1CCC(N(C)C)CC1 CJZZWMSHMCFIFZ-UHFFFAOYSA-N 0.000 claims 1
- XXFJFINPJXQOSV-UHFFFAOYSA-N 1-[2-[4-(dimethylamino)piperidin-1-yl]-1-[3-(trifluoromethyl)phenyl]ethyl]cyclohexan-1-ol;dihydrochloride Chemical compound Cl.Cl.C1CC(N(C)C)CCN1CC(C1(O)CCCCC1)C1=CC=CC(C(F)(F)F)=C1 XXFJFINPJXQOSV-UHFFFAOYSA-N 0.000 claims 1
- PVFPKFDQGKIHEO-UHFFFAOYSA-N 1-[2-[4-(dimethylamino)piperidin-1-yl]-1-naphthalen-2-ylethyl]cyclohexan-1-ol;dihydrochloride Chemical compound Cl.Cl.C1CC(N(C)C)CCN1CC(C1(O)CCCCC1)C1=CC=C(C=CC=C2)C2=C1 PVFPKFDQGKIHEO-UHFFFAOYSA-N 0.000 claims 1
- SLEOPZXYTNHYRW-UHFFFAOYSA-N 1-[2-[4-(methylamino)piperidin-1-yl]-1-[3-(trifluoromethyl)phenyl]ethyl]cyclohexan-1-ol;dihydrochloride Chemical compound Cl.Cl.C1CC(NC)CCN1CC(C1(O)CCCCC1)C1=CC=CC(C(F)(F)F)=C1 SLEOPZXYTNHYRW-UHFFFAOYSA-N 0.000 claims 1
- IAFXHRKVXPTGNQ-UHFFFAOYSA-N 1-[2-[4-(methylamino)piperidin-1-yl]-1-naphthalen-2-ylethyl]cyclohexan-1-ol;dihydrochloride Chemical compound Cl.Cl.C1CC(NC)CCN1CC(C1(O)CCCCC1)C1=CC=C(C=CC=C2)C2=C1 IAFXHRKVXPTGNQ-UHFFFAOYSA-N 0.000 claims 1
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
- OVDYNHQMVJQLRT-UHFFFAOYSA-N 2-[2-(4-aminopiperidin-1-yl)-1-(3-chlorophenyl)ethyl]-3,4,4a,5,6,7,8,8a-octahydro-1h-naphthalen-2-ol;dihydrochloride Chemical compound Cl.Cl.C1CC(N)CCN1CC(C1(O)CC2CCCCC2CC1)C1=CC=CC(Cl)=C1 OVDYNHQMVJQLRT-UHFFFAOYSA-N 0.000 claims 1
- JQHZBTSQZPJDKD-UHFFFAOYSA-N 2-[2-(4-aminopiperidin-1-yl)-1-(3-chlorophenyl)ethyl]cyclohexan-1-ol;dihydrochloride Chemical compound Cl.Cl.C1CC(N)CCN1CC(C=1C=C(Cl)C=CC=1)C1C(O)CCCC1 JQHZBTSQZPJDKD-UHFFFAOYSA-N 0.000 claims 1
- ICBHEQTZYPYWKG-UHFFFAOYSA-N 3-(3-chlorophenyl)-4-[4-(dimethylamino)piperidin-1-yl]-2-methylbutan-2-ol;dihydrochloride Chemical compound Cl.Cl.C1CC(N(C)C)CCN1CC(C(C)(C)O)C1=CC=CC(Cl)=C1 ICBHEQTZYPYWKG-UHFFFAOYSA-N 0.000 claims 1
- LRWUBGJDMZNXHP-UHFFFAOYSA-N 4-(4-aminopiperidin-1-yl)-3-(3-chlorophenyl)-2-methylbutan-2-ol;dihydrochloride Chemical compound Cl.Cl.C=1C=CC(Cl)=CC=1C(C(C)(O)C)CN1CCC(N)CC1 LRWUBGJDMZNXHP-UHFFFAOYSA-N 0.000 claims 1
- NKVNWUYMGRJGEZ-UHFFFAOYSA-N 4-[2-(4-aminopiperidin-1-yl)-1-(3-chlorophenyl)ethyl]heptan-4-ol;dihydrochloride Chemical compound Cl.Cl.C=1C=CC(Cl)=CC=1C(C(O)(CCC)CCC)CN1CCC(N)CC1 NKVNWUYMGRJGEZ-UHFFFAOYSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 239000002168 alkylating agent Substances 0.000 claims 1
- 229940100198 alkylating agent Drugs 0.000 claims 1
- 230000002152 alkylating effect Effects 0.000 claims 1
- 230000001668 ameliorated effect Effects 0.000 claims 1
- 150000007514 bases Chemical class 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims 1
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 claims 1
- HPXRVTGHNJAIIH-PTQBSOBMSA-N cyclohexanol Chemical group O[13CH]1CCCCC1 HPXRVTGHNJAIIH-PTQBSOBMSA-N 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 125000004923 naphthylmethyl group Chemical group C1(=CC=CC2=CC=CC=C12)C* 0.000 claims 1
- 230000000966 norepinephrine reuptake Effects 0.000 claims 1
- 125000003386 piperidinyl group Chemical group 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- 0 CCC(C*CN(C*)C(CC(C(C)C(*)(*)C=C)=O)=C)C(*)C[U](*)* Chemical compound CCC(C*CN(C*)C(CC(C(C)C(*)(*)C=C)=O)=C)C(*)C[U](*)* 0.000 description 1
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| PCT/US2004/033732 WO2005037279A1 (en) | 2003-10-14 | 2004-10-13 | 1- 2’ (1, 4’-biperidin-1’-yl)-1- (phenyl) -ethyl cyclohexanol derivatives as monoamine reuptake modulators for the treatment of visomotor symptoms |
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| US7517899B2 (en) * | 2004-03-30 | 2009-04-14 | Wyeth | Phenylaminopropanol derivatives and methods of their use |
| US7414052B2 (en) * | 2004-03-30 | 2008-08-19 | Wyeth | Phenylaminopropanol derivatives and methods of their use |
| WO2006017468A2 (en) | 2004-08-02 | 2006-02-16 | Glaxo Group Limited | Antibacterial agents |
| AU2006321947A1 (en) * | 2005-12-05 | 2007-06-14 | Wyeth | Process for preparing substituted aryl cycloalkanol derivatives |
| EP2089389A2 (en) | 2006-11-01 | 2009-08-19 | Bristol-Myers Squibb Company | Heterocyclic compounds as modulators of glucocorticoid receptor, ap-1, and/or nf-kappa-b activity |
| UY32858A (es) * | 2009-08-31 | 2011-03-31 | Abbott Healthcare Products Bv | Derivados de (tio)morfolina como moduladores de sip |
| JP5752691B2 (ja) | 2009-09-29 | 2015-07-22 | グラクソ グループ リミテッドＧｌａｘｏ Ｇｒｏｕｐ Ｌｉｍｉｔｅｄ | 新規化合物 |
| KR20130010460A (ko) * | 2010-02-02 | 2013-01-28 | 에이전시 포 사이언스, 테크놀로지 앤드 리서치 | 기능화 오염방지 화합물 및 이의 사용 |
| TWI522361B (zh) | 2010-07-09 | 2016-02-21 | 艾伯維公司 | 作為s1p調節劑的稠合雜環衍生物 |
| TW201206893A (en) * | 2010-07-09 | 2012-02-16 | Abbott Healthcare Products Bv | Bisaryl (thio) morpholine derivatives as S1P modulators |
| TW201643169A (zh) | 2010-07-09 | 2016-12-16 | 艾伯維股份有限公司 | 作為s1p調節劑的螺-哌啶衍生物 |
| US11535632B2 (en) | 2019-10-31 | 2022-12-27 | ESCAPE Bio, Inc. | Solid forms of an S1P-receptor modulator |
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| US1963458A (en) * | 1930-01-22 | 1934-06-19 | George M Holley | Carburetor |
| US1962880A (en) * | 1931-06-20 | 1934-06-12 | Schwab Max | Electric drive for household sewing machines |
| US1962897A (en) * | 1931-11-03 | 1934-06-12 | Edward J Duffy | Printing press |
| US1963111A (en) * | 1932-01-08 | 1934-06-19 | Backes Henry | Dispensing attachment for liquid cement containers |
| US1962899A (en) * | 1932-07-30 | 1934-06-12 | Charles S Hagy | Sectional portable bowling alley |
| US1962881A (en) * | 1932-11-04 | 1934-06-12 | Connor B Shanley | Manhole cover and anchoring means therefor |
| US1963064A (en) * | 1933-03-21 | 1934-06-19 | American Steel & Wire Co | Adjustable die-holder |
| US3454554A (en) * | 1960-10-14 | 1969-07-08 | Colgate Palmolive Co | Aminoalkyliminodibenzyl compounds |
| CS175831B1 (enExample) | 1974-12-17 | 1977-05-31 | ||
| IL56369A (en) * | 1978-01-20 | 1984-05-31 | Erba Farmitalia | Alpha-phenoxybenzyl propanolamine derivatives,their preparation and pharmaceutical compositions comprising them |
| US4310524A (en) * | 1980-04-11 | 1982-01-12 | Richardson-Merrell, Inc. | TCA Composition and method for rapid onset antidepressant therapy |
| PH18686A (en) | 1981-05-26 | 1985-08-29 | Merck & Co Inc | 1-(3 halo-2-pyridinyl) piperazine |
| US4535186A (en) * | 1983-04-19 | 1985-08-13 | American Home Products Corporation | 2-Phenyl-2-(1-hydroxycycloalkyl or 1-hydroxycycloalk-2-enyl)ethylamine derivatives |
| ZA864772B (en) | 1985-07-02 | 1987-02-25 | Merrell Dow Pharma | Novel chemical compounds |
| CA1327795C (en) | 1987-08-14 | 1994-03-15 | Jules Freedman | Antidepressants which are aryloxy inadanamines |
| US4826844A (en) * | 1987-09-30 | 1989-05-02 | American Home Products Corporation | Substituted 1-(aralkyl-piperazinoalkyl) cycloalkanols |
| CA2083698C (en) | 1990-06-01 | 1997-11-04 | Albert A. Carr | (+)-alpha-(2,3-dimethoxyphenyl)-1- [2-(4-fluorophenyl) ethyl]-4-piperidinemethanol |
| US5502047A (en) * | 1993-03-22 | 1996-03-26 | Kavey; Neil B. | Treatment for insomnia |
| UA48219C2 (uk) | 1996-03-25 | 2002-08-15 | Елі Ліллі Енд Компані | Композиція для вгамування болю (варіанти) та спосіб вгамування болю |
| AU3306399A (en) | 1998-03-02 | 1999-09-20 | Eli Lilly And Company | Fluoxetine hydrochloride for decreasing hot flashes |
| PL350924A1 (en) | 1999-04-06 | 2003-02-10 | Sepracor Inc | Derivatives of venlafaxine and methods of preparing and using the same |
| TW564247B (en) * | 1999-04-08 | 2003-12-01 | Akzo Nobel Nv | Bicyclic heteraromatic compound |
| DE60022692T2 (de) | 1999-07-01 | 2006-06-22 | Pharmacia & Upjohn Co. Llc, Kalamazoo | (S,S)-Reboxetin zur Behandlung von Migränekopfschmerzen |
| AU6640800A (en) * | 1999-08-11 | 2001-03-05 | Vermeer Manufacturing Company | Automated lubricant dispensing system and method for a horizontal directional drilling machine |
| JP2004516239A (ja) * | 2000-07-06 | 2004-06-03 | ニューロジェン コーポレイション | メラニン凝集ホルモン受容体リガンド |
| DE60119047D1 (de) | 2000-08-31 | 2006-06-01 | Pfizer | Phenoxyphenylheterozyklen als Serotonin-Wiederaufnahmehemmer |
| CN100398103C (zh) | 2000-10-13 | 2008-07-02 | 神经研究公司 | 通过烟碱性受体激动剂和单胺能物质的联合作用治疗情感性精神障碍 |
| AU2002250058B2 (en) | 2001-02-12 | 2007-08-16 | Wyeth Llc | Novel succinate salt of O-desmethyl-venlafaxine |
| US6557831B2 (en) * | 2001-03-05 | 2003-05-06 | Erwin Industries, Inc. | Fence bracket |
| CA2442410A1 (en) | 2001-03-29 | 2002-10-10 | Owen Brendan Wallace | Duloxetine for treatment of hot flashes |
| GB0108046D0 (en) | 2001-03-30 | 2001-05-23 | Astrazeneca Ab | Chemical compounds |
| EP1266659A1 (en) | 2001-06-11 | 2002-12-18 | Pantarhei Bioscience B.V. | Pyridoxal in combination with serotonin re-uptake inhibitor for the treatment of hot flushes |
| WO2003037334A1 (en) | 2001-10-31 | 2003-05-08 | Merck & Co., Inc. | Method for treating or preventing symptoms of hormonal variation including hot flashes |
| US6602911B2 (en) | 2001-11-05 | 2003-08-05 | Cypress Bioscience, Inc. | Methods of treating fibromyalgia |
| SE0103818D0 (sv) * | 2001-11-15 | 2001-11-15 | Astrazeneca Ab | Chemical compounds |
| EP1478356A4 (en) | 2002-02-08 | 2005-03-16 | Harvard College | THERAPEUTIC COMPOUNDS |
| CA2479350A1 (en) | 2002-03-15 | 2003-09-25 | Cypress Bioscience, Inc. | Ne and 5-ht reuptake inhibitors for treating visceral pain syndromes |
| TW200402289A (en) * | 2002-05-17 | 2004-02-16 | Wyeth Corp | Methods of treating gastrointestinary and genitourinary pain disorders |
| KR20050049476A (ko) | 2002-08-14 | 2005-05-25 | 파마시아 앤드 업존 캄파니 엘엘씨 | 홍조를 치료하기 위한 레복세틴의 용도 |
| US20040152710A1 (en) * | 2002-10-15 | 2004-08-05 | Deecher Darlene Coleman | Use of norepinephrine reuptake modulators for preventing and treating vasomotor symptoms |
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| US20040180879A1 (en) * | 2002-10-15 | 2004-09-16 | Deecher Darlene Coleman | Novel method of treating vasomotor symptoms |
-
2004
- 2004-10-12 US US10/962,971 patent/US7550485B2/en not_active Expired - Fee Related
- 2004-10-13 BR BRPI0415294-8A patent/BRPI0415294A/pt not_active IP Right Cessation
- 2004-10-13 CA CA002540191A patent/CA2540191A1/en not_active Abandoned
- 2004-10-13 WO PCT/US2004/033732 patent/WO2005037279A1/en not_active Ceased
- 2004-10-13 DE DE602004014955T patent/DE602004014955D1/de not_active Expired - Fee Related
- 2004-10-13 EP EP04794958A patent/EP1673084B1/en not_active Expired - Lifetime
- 2004-10-13 KR KR1020067007312A patent/KR20070026326A/ko not_active Withdrawn
- 2004-10-13 AU AU2004281746A patent/AU2004281746A1/en not_active Withdrawn
- 2004-10-13 TW TW093131002A patent/TW200526619A/zh unknown
- 2004-10-13 AT AT04794958T patent/ATE400273T1/de not_active IP Right Cessation
- 2004-10-13 JP JP2006535619A patent/JP2007508395A/ja active Pending
- 2004-10-13 MX MXPA06003880A patent/MXPA06003880A/es active IP Right Grant
- 2004-10-14 PA PA20048615001A patent/PA8615001A1/es unknown
- 2004-10-14 AR ARP040103715A patent/AR046283A1/es unknown
- 2004-10-14 PE PE2004000995A patent/PE20050440A1/es not_active Application Discontinuation
-
2006
- 2006-03-21 IL IL174472A patent/IL174472A0/en unknown
- 2006-04-12 EC EC2006006506A patent/ECSP066506A/es unknown
-
2009
- 2009-05-18 US US12/467,594 patent/US20090227585A1/en not_active Abandoned
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