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
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
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| US56144804P | 2004-04-12 | 2004-04-12 | |
| US57002604P | 2004-05-11 | 2004-05-11 | |
| US10/962,971 US7550485B2 (en) | 2003-10-14 | 2004-10-12 | Substituted N-heterocycle derivatives and methods of their use |
| 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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| JP2007508395A JP2007508395A (ja) | 2007-04-05 |
| JP2007508395A5 true JP2007508395A5 (OSRAM) | 2007-11-29 |
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| JP (1) | JP2007508395A (OSRAM) |
| KR (1) | KR20070026326A (OSRAM) |
| AR (1) | AR046283A1 (OSRAM) |
| AT (1) | ATE400273T1 (OSRAM) |
| AU (1) | AU2004281746A1 (OSRAM) |
| BR (1) | BRPI0415294A (OSRAM) |
| CA (1) | CA2540191A1 (OSRAM) |
| DE (1) | DE602004014955D1 (OSRAM) |
| EC (1) | ECSP066506A (OSRAM) |
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| MX (1) | MXPA06003880A (OSRAM) |
| PA (1) | PA8615001A1 (OSRAM) |
| PE (1) | PE20050440A1 (OSRAM) |
| TW (1) | TW200526619A (OSRAM) |
| WO (1) | WO2005037279A1 (OSRAM) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
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| US7414052B2 (en) * | 2004-03-30 | 2008-08-19 | Wyeth | Phenylaminopropanol derivatives and methods of their use |
| US7517899B2 (en) * | 2004-03-30 | 2009-04-14 | Wyeth | Phenylaminopropanol derivatives and methods of their use |
| JP2008508359A (ja) | 2004-08-02 | 2008-03-21 | グラクソ グループ リミテッド | 抗菌剤 |
| EP1957473A2 (en) * | 2005-12-05 | 2008-08-20 | Wyeth a Corporation of the State of Delaware | Process for preparing substituted aryl cycloalkanol derivatives |
| WO2008057855A2 (en) | 2006-11-01 | 2008-05-15 | Bristol-Myers Squibb Company | Heterocyclic compounds as modulators of glucocorticoid receptor, ap-i, and/or np-kappa-b activity |
| AR077969A1 (es) | 2009-08-31 | 2011-10-05 | Abbott Healthcare Products Bv | Derivados de (tio)morfolina comomoduladores de s1p |
| EP2483254B1 (en) | 2009-09-29 | 2014-08-13 | Glaxo Group Limited | Novel compounds |
| SG183158A1 (en) * | 2010-02-02 | 2012-09-27 | Agency Science Tech & Res | Functionalised antifouling compounds and use thereof |
| 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 |
| TWI543984B (zh) | 2010-07-09 | 2016-08-01 | 艾伯維公司 | 作為s1p調節劑的螺-哌啶衍生物 |
| TW201206893A (en) * | 2010-07-09 | 2012-02-16 | Abbott Healthcare Products Bv | Bisaryl (thio) morpholine derivatives as S1P modulators |
| BR112022008113A2 (pt) | 2019-10-31 | 2022-07-19 | Escape Bio Inc | Formas sólidas de um modulador de receptor s1p |
Family Cites Families (42)
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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 (OSRAM) * | 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 |
| CA1280421C (en) | 1985-07-02 | 1991-02-19 | Albert A. Carr | 1,4-disubstituted piperidinyl derivatives |
| ZA885824B (en) | 1987-08-14 | 1989-04-26 | Merrell Dow Pharma | Novel antidepressants |
| US4826844A (en) * | 1987-09-30 | 1989-05-02 | American Home Products Corporation | Substituted 1-(aralkyl-piperazinoalkyl) cycloalkanols |
| ES2067937T3 (es) | 1990-06-01 | 1995-04-01 | Merrell Dow Pharma | (+)-alfa-(2,3-dimetoxifenil)-1-(2-(4-fluorofenil)etil)-4-piperidinametanol. |
| US5502047A (en) * | 1993-03-22 | 1996-03-26 | Kavey; Neil B. | Treatment for insomnia |
| CN1494907A (zh) | 1996-03-25 | 2004-05-12 | 治疗疼痛的药物组合物 | |
| 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 |
| WO2001001973A2 (en) * | 1999-07-01 | 2001-01-11 | Pharmacia & Upjohn Company | Highly selective norepinephrine reuptake inhibitors and methods of using the same |
| US6557651B1 (en) * | 1999-08-11 | 2003-05-06 | Vermeer Manufacturing Company | Automated lubricant dispensing system and method for a horizontal directional drilling machine |
| CA2414198A1 (en) * | 2000-07-06 | 2002-01-17 | Neurogen Corporation | Melanin concentrating hormone receptor ligands |
| ATE324365T1 (de) | 2000-08-31 | 2006-05-15 | Pfizer | Phenoxyphenylheterozyklen als serotonin- wiederaufnahmehemmer |
| AU9543601A (en) | 2000-10-13 | 2002-04-22 | Neurosearch As | Treatment of affective disorders by the combined action of a nicotinic receptor agonist and a monoaminergic substance |
| JP4220243B2 (ja) | 2001-02-12 | 2009-02-04 | ワイス | Ｏ−デスメチル−ベンラファキシンの新規コハク酸塩 |
| US6557831B2 (en) * | 2001-03-05 | 2003-05-06 | Erwin Industries, Inc. | Fence bracket |
| EP1383495A1 (en) | 2001-03-29 | 2004-01-28 | Eli Lilly And Company | 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 |
| WO2003066004A2 (en) | 2002-02-08 | 2003-08-14 | President And Fellows Of Harvard College | Therapeutic compounds |
| PL223471B1 (pl) | 2002-03-15 | 2016-10-31 | Cypress Bioscience Inc | Kompozycja farmaceutyczna zawierająca milnacypran do stosowania w leczeniu zespołu nadwrażliwości jelita grubego |
| 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 |
| US7345096B2 (en) * | 2002-10-15 | 2008-03-18 | Wyeth | Use of norepinephrine reuptake modulators for preventing and treating vasomotor symptoms |
| US20040152710A1 (en) * | 2002-10-15 | 2004-08-05 | Deecher Darlene Coleman | Use of norepinephrine reuptake modulators for preventing and treating vasomotor symptoms |
| 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 EP EP04794958A patent/EP1673084B1/en not_active Expired - Lifetime
- 2004-10-13 KR KR1020067007312A patent/KR20070026326A/ko not_active Withdrawn
- 2004-10-13 DE DE602004014955T patent/DE602004014955D1/de not_active Expired - Fee Related
- 2004-10-13 MX MXPA06003880A patent/MXPA06003880A/es active IP Right Grant
- 2004-10-13 AT AT04794958T patent/ATE400273T1/de not_active IP Right Cessation
- 2004-10-13 TW TW093131002A patent/TW200526619A/zh unknown
- 2004-10-13 CA CA002540191A patent/CA2540191A1/en not_active Abandoned
- 2004-10-13 AU AU2004281746A patent/AU2004281746A1/en not_active Withdrawn
- 2004-10-13 JP JP2006535619A patent/JP2007508395A/ja active Pending
- 2004-10-13 BR BRPI0415294-8A patent/BRPI0415294A/pt not_active IP Right Cessation
- 2004-10-13 WO PCT/US2004/033732 patent/WO2005037279A1/en not_active Ceased
- 2004-10-14 PE PE2004000995A patent/PE20050440A1/es not_active Application Discontinuation
- 2004-10-14 PA PA20048615001A patent/PA8615001A1/es unknown
- 2004-10-14 AR ARP040103715A patent/AR046283A1/es unknown
-
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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