JP2007509076A5 - - Google Patents
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- Publication number
- JP2007509076A5 JP2007509076A5 JP2006535675A JP2006535675A JP2007509076A5 JP 2007509076 A5 JP2007509076 A5 JP 2007509076A5 JP 2006535675 A JP2006535675 A JP 2006535675A JP 2006535675 A JP2006535675 A JP 2006535675A JP 2007509076 A5 JP2007509076 A5 JP 2007509076A5
- Authority
- JP
- Japan
- Prior art keywords
- cyclohexanol
- ethyl
- phenyl
- piperazin
- ylethyl
- 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.)
- Withdrawn
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- 150000001875 compounds Chemical class 0.000 claims 22
- 125000000217 alkyl group Chemical group 0.000 claims 21
- -1 benzyloxy, phenoxy, naphthyloxy, phenylethoxy, phenoxyethoxy, naphthylmethoxy, naphthylethoxy, phenylcarbonylamino, phenylaminocarbonyl Chemical group 0.000 claims 21
- 125000003545 alkoxy group Chemical group 0.000 claims 16
- 125000001475 halogen functional group Chemical group 0.000 claims 16
- 229910052757 nitrogen Inorganic materials 0.000 claims 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 12
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 11
- 125000004423 acyloxy group Chemical group 0.000 claims 11
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 11
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 11
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims 10
- 229910052799 carbon Inorganic materials 0.000 claims 10
- 125000003342 alkenyl group Chemical group 0.000 claims 9
- 125000000304 alkynyl group Chemical group 0.000 claims 9
- 150000001721 carbon Chemical group 0.000 claims 9
- 125000004981 cycloalkylmethyl group Chemical group 0.000 claims 9
- 229910052760 oxygen Inorganic materials 0.000 claims 9
- 229910052717 sulfur Inorganic materials 0.000 claims 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 8
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 8
- 150000002825 nitriles Chemical class 0.000 claims 8
- 125000001072 heteroaryl group Chemical group 0.000 claims 6
- 125000001624 naphthyl group Chemical group 0.000 claims 6
- 229940124530 sulfonamide Drugs 0.000 claims 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 5
- 150000003839 salts Chemical class 0.000 claims 5
- 125000001424 substituent group Chemical group 0.000 claims 5
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 5
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 4
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 claims 4
- 229910052739 hydrogen Inorganic materials 0.000 claims 4
- 125000004923 naphthylmethyl group Chemical group C1(=CC=CC2=CC=CC=C12)C* 0.000 claims 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 4
- 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 3
- 239000001257 hydrogen Substances 0.000 claims 3
- 238000000034 method Methods 0.000 claims 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 3
- 150000003456 sulfonamides Chemical class 0.000 claims 3
- FNCDVSLUAJJDIL-UHFFFAOYSA-N 1-[1-(3-phenylmethoxyphenyl)-2-piperazin-1-ylethyl]cyclobutan-1-ol Chemical compound C1CNCCN1CC(C=1C=C(OCC=2C=CC=CC=2)C=CC=1)C1(O)CCC1 FNCDVSLUAJJDIL-UHFFFAOYSA-N 0.000 claims 2
- SVZKEABVRKMFDN-UHFFFAOYSA-N 1-[1-[3-(3,4-dichlorophenyl)phenyl]-2-piperazin-1-ylethyl]cyclobutan-1-ol Chemical compound C1CNCCN1CC(C=1C=C(C=CC=1)C=1C=C(Cl)C(Cl)=CC=1)C1(O)CCC1 SVZKEABVRKMFDN-UHFFFAOYSA-N 0.000 claims 2
- SPUKGMZQGMYJTQ-UHFFFAOYSA-N 1-[1-[3-(3,4-dichlorophenyl)phenyl]-2-piperazin-1-ylethyl]cyclohexan-1-ol Chemical compound C1CNCCN1CC(C=1C=C(C=CC=1)C=1C=C(Cl)C(Cl)=CC=1)C1(O)CCCCC1 SPUKGMZQGMYJTQ-UHFFFAOYSA-N 0.000 claims 2
- SFRUDVVIRONFKI-UHFFFAOYSA-N 1-[1-[3-(4-chlorophenyl)phenyl]-2-piperazin-1-ylethyl]cyclohexan-1-ol Chemical compound C1CNCCN1CC(C=1C=C(C=CC=1)C=1C=CC(Cl)=CC=1)C1(O)CCCCC1 SFRUDVVIRONFKI-UHFFFAOYSA-N 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 2
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims 2
- 125000001589 carboacyl group Chemical group 0.000 claims 2
- 229910021386 carbon form Inorganic materials 0.000 claims 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
- 125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 claims 2
- MIGOEQDERWIFGH-VNCLNFNDSA-N (3r)-3-methyl-1-[2-(4-methylpiperazin-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)CN1CCN(C)CC1 MIGOEQDERWIFGH-VNCLNFNDSA-N 0.000 claims 1
- HJDBMAJSZQLORS-RWBZWWBESA-N (3r)-3-methyl-1-[2-piperazin-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)CN1CCNCC1 HJDBMAJSZQLORS-RWBZWWBESA-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
- FWQHJBAJMBRTFN-QHCPKHFHSA-N 1-[(1r)-1-(3-chloro-4-phenylmethoxyphenyl)-2-(4-methylpiperazin-1-yl)ethyl]cyclohexan-1-ol Chemical compound C1CN(C)CCN1C[C@H](C1(O)CCCCC1)C(C=C1Cl)=CC=C1OCC1=CC=CC=C1 FWQHJBAJMBRTFN-QHCPKHFHSA-N 0.000 claims 1
- WDTHRPXYILRWIK-QFIPXVFZSA-N 1-[(1r)-1-(3-chloro-4-phenylmethoxyphenyl)-2-piperazin-1-ylethyl]cyclohexan-1-ol Chemical compound OC1([C@@H](CN2CCNCC2)C=2C=C(Cl)C(OCC=3C=CC=CC=3)=CC=2)CCCCC1 WDTHRPXYILRWIK-QFIPXVFZSA-N 0.000 claims 1
- HSHSYQHQVDIHLN-QHCPKHFHSA-N 1-[(1r)-1-(3-phenoxyphenyl)-2-piperazin-1-ylethyl]cyclohexan-1-ol Chemical compound OC1([C@@H](CN2CCNCC2)C=2C=C(OC=3C=CC=CC=3)C=CC=2)CCCCC1 HSHSYQHQVDIHLN-QHCPKHFHSA-N 0.000 claims 1
- JJXPZXGSLYLWJI-VWLOTQADSA-N 1-[(1r)-2-(4-methylpiperazin-1-yl)-1-(4-phenylmethoxyphenyl)ethyl]cyclohexan-1-ol Chemical compound C1CN(C)CCN1C[C@H](C1(O)CCCCC1)C(C=C1)=CC=C1OCC1=CC=CC=C1 JJXPZXGSLYLWJI-VWLOTQADSA-N 0.000 claims 1
- AKRIZMRTOCYSRB-SFHVURJKSA-N 1-[(1r)-2-(4-methylpiperazin-1-yl)-1-[3-(trifluoromethoxy)phenyl]ethyl]cyclohexan-1-ol Chemical compound C1CN(C)CCN1C[C@H](C1(O)CCCCC1)C1=CC=CC(OC(F)(F)F)=C1 AKRIZMRTOCYSRB-SFHVURJKSA-N 0.000 claims 1
- MRQDQHDPSBHAEH-KRWDZBQOSA-N 1-[(1r)-2-piperazin-1-yl-1-[3-(trifluoromethoxy)phenyl]ethyl]cyclohexan-1-ol Chemical compound OC1([C@@H](CN2CCNCC2)C=2C=C(OC(F)(F)F)C=CC=2)CCCCC1 MRQDQHDPSBHAEH-KRWDZBQOSA-N 0.000 claims 1
- FWQHJBAJMBRTFN-HSZRJFAPSA-N 1-[(1s)-1-(3-chloro-4-phenylmethoxyphenyl)-2-(4-methylpiperazin-1-yl)ethyl]cyclohexan-1-ol Chemical compound C1CN(C)CCN1C[C@@H](C1(O)CCCCC1)C(C=C1Cl)=CC=C1OCC1=CC=CC=C1 FWQHJBAJMBRTFN-HSZRJFAPSA-N 0.000 claims 1
- WDTHRPXYILRWIK-JOCHJYFZSA-N 1-[(1s)-1-(3-chloro-4-phenylmethoxyphenyl)-2-piperazin-1-ylethyl]cyclohexan-1-ol Chemical compound OC1([C@H](CN2CCNCC2)C=2C=C(Cl)C(OCC=3C=CC=CC=3)=CC=2)CCCCC1 WDTHRPXYILRWIK-JOCHJYFZSA-N 0.000 claims 1
- HSHSYQHQVDIHLN-HSZRJFAPSA-N 1-[(1s)-1-(3-phenoxyphenyl)-2-piperazin-1-ylethyl]cyclohexan-1-ol Chemical compound OC1([C@H](CN2CCNCC2)C=2C=C(OC=3C=CC=CC=3)C=CC=2)CCCCC1 HSHSYQHQVDIHLN-HSZRJFAPSA-N 0.000 claims 1
- OKSPPUMZNMXVNV-FUHIMQAGSA-N 1-[(1s)-1-[3-(trifluoromethoxy)phenyl]-2-[(3r,5s)-3,4,5-trimethylpiperazin-1-yl]ethyl]cyclohexan-1-ol Chemical compound C1[C@@H](C)N(C)[C@@H](C)CN1C[C@@H](C1(O)CCCCC1)C1=CC=CC(OC(F)(F)F)=C1 OKSPPUMZNMXVNV-FUHIMQAGSA-N 0.000 claims 1
- VEGUBVILWWVPIP-VGAJERRHSA-N 1-[(1s)-2-(1,3,4,6,7,8,9,9a-octahydropyrido[1,2-a]pyrazin-2-yl)-1-[3-(trifluoromethoxy)phenyl]ethyl]cyclohexan-1-ol Chemical compound OC1([C@H](CN2CC3CCCCN3CC2)C=2C=C(OC(F)(F)F)C=CC=2)CCCCC1 VEGUBVILWWVPIP-VGAJERRHSA-N 0.000 claims 1
- LSXZYZNTIJZJDO-WHCXFUJUSA-N 1-[(1s)-2-(3-ethylpiperazin-1-yl)-1-[3-(trifluoromethoxy)phenyl]ethyl]cyclohexan-1-ol Chemical compound C1CNC(CC)CN1C[C@@H](C1(O)CCCCC1)C1=CC=CC(OC(F)(F)F)=C1 LSXZYZNTIJZJDO-WHCXFUJUSA-N 0.000 claims 1
- JJXPZXGSLYLWJI-RUZDIDTESA-N 1-[(1s)-2-(4-methylpiperazin-1-yl)-1-(4-phenylmethoxyphenyl)ethyl]cyclohexan-1-ol Chemical compound C1CN(C)CCN1C[C@@H](C1(O)CCCCC1)C(C=C1)=CC=C1OCC1=CC=CC=C1 JJXPZXGSLYLWJI-RUZDIDTESA-N 0.000 claims 1
- AKRIZMRTOCYSRB-GOSISDBHSA-N 1-[(1s)-2-(4-methylpiperazin-1-yl)-1-[3-(trifluoromethoxy)phenyl]ethyl]cyclohexan-1-ol Chemical compound C1CN(C)CCN1C[C@@H](C1(O)CCCCC1)C1=CC=CC(OC(F)(F)F)=C1 AKRIZMRTOCYSRB-GOSISDBHSA-N 0.000 claims 1
- ADLYVQUVEYKOBB-UYAOXDASSA-N 1-[(1s)-2-[(3r)-3-ethyl-4-methylpiperazin-1-yl]-1-[3-(trifluoromethoxy)phenyl]ethyl]cyclohexan-1-ol Chemical compound C1CN(C)[C@H](CC)CN1C[C@@H](C1(O)CCCCC1)C1=CC=CC(OC(F)(F)F)=C1 ADLYVQUVEYKOBB-UYAOXDASSA-N 0.000 claims 1
- OSXAMTXRMHMDAZ-CRAIPNDOSA-N 1-[(1s)-2-[(3r)-3-methylpiperazin-1-yl]-1-[3-(trifluoromethoxy)phenyl]ethyl]cyclohexan-1-ol Chemical compound C1CN[C@H](C)CN1C[C@@H](C1(O)CCCCC1)C1=CC=CC(OC(F)(F)F)=C1 OSXAMTXRMHMDAZ-CRAIPNDOSA-N 0.000 claims 1
- IZKKWMODPZOVDT-QFBILLFUSA-N 1-[(1s)-2-[(3s)-3,4-dimethylpiperazin-1-yl]-1-[3-(trifluoromethoxy)phenyl]ethyl]cyclohexan-1-ol Chemical compound C1CN(C)[C@@H](C)CN1C[C@@H](C1(O)CCCCC1)C1=CC=CC(OC(F)(F)F)=C1 IZKKWMODPZOVDT-QFBILLFUSA-N 0.000 claims 1
- ADLYVQUVEYKOBB-AZUAARDMSA-N 1-[(1s)-2-[(3s)-3-ethyl-4-methylpiperazin-1-yl]-1-[3-(trifluoromethoxy)phenyl]ethyl]cyclohexan-1-ol Chemical compound C1CN(C)[C@@H](CC)CN1C[C@@H](C1(O)CCCCC1)C1=CC=CC(OC(F)(F)F)=C1 ADLYVQUVEYKOBB-AZUAARDMSA-N 0.000 claims 1
- OSXAMTXRMHMDAZ-MAUKXSAKSA-N 1-[(1s)-2-[(3s)-3-methylpiperazin-1-yl]-1-[3-(trifluoromethoxy)phenyl]ethyl]cyclohexan-1-ol Chemical compound C1CN[C@@H](C)CN1C[C@@H](C1(O)CCCCC1)C1=CC=CC(OC(F)(F)F)=C1 OSXAMTXRMHMDAZ-MAUKXSAKSA-N 0.000 claims 1
- ZNDZJNVJUAKEQC-JTDSTZFVSA-N 1-[(1s)-2-[(3s,5r)-3,5-dimethylpiperazin-1-yl]-1-[3-(trifluoromethoxy)phenyl]ethyl]cyclohexan-1-ol Chemical compound C1[C@@H](C)N[C@@H](C)CN1C[C@@H](C1(O)CCCCC1)C1=CC=CC(OC(F)(F)F)=C1 ZNDZJNVJUAKEQC-JTDSTZFVSA-N 0.000 claims 1
- BIZFBDLWOHKGIL-IQHZPMLTSA-N 1-[(1s)-2-[4-(3-phenylbutyl)piperazin-1-yl]-1-[3-(trifluoromethoxy)phenyl]ethyl]cyclohexan-1-ol Chemical compound C1([C@@H](CN2CCN(CC2)CCC(C)C=2C=CC=CC=2)C2(O)CCCCC2)=CC=CC(OC(F)(F)F)=C1 BIZFBDLWOHKGIL-IQHZPMLTSA-N 0.000 claims 1
- SFWSWJBTDXTORQ-PXDATVDWSA-N 1-[(1s)-2-[4-[(1r)-1-phenylethyl]piperazin-1-yl]-1-[3-(trifluoromethoxy)phenyl]ethyl]cyclohexan-1-ol Chemical compound C1([C@@H](CN2CCN(CC2)[C@H](C)C=2C=CC=CC=2)C2(O)CCCCC2)=CC=CC(OC(F)(F)F)=C1 SFWSWJBTDXTORQ-PXDATVDWSA-N 0.000 claims 1
- SFWSWJBTDXTORQ-SQJMNOBHSA-N 1-[(1s)-2-[4-[(1s)-1-phenylethyl]piperazin-1-yl]-1-[3-(trifluoromethoxy)phenyl]ethyl]cyclohexan-1-ol Chemical compound C1([C@@H](CN2CCN(CC2)[C@@H](C)C=2C=CC=CC=2)C2(O)CCCCC2)=CC=CC(OC(F)(F)F)=C1 SFWSWJBTDXTORQ-SQJMNOBHSA-N 0.000 claims 1
- MRQDQHDPSBHAEH-QGZVFWFLSA-N 1-[(1s)-2-piperazin-1-yl-1-[3-(trifluoromethoxy)phenyl]ethyl]cyclohexan-1-ol Chemical compound OC1([C@H](CN2CCNCC2)C=2C=C(OC(F)(F)F)C=CC=2)CCCCC1 MRQDQHDPSBHAEH-QGZVFWFLSA-N 0.000 claims 1
- HRPUOOXLTLERRJ-UHFFFAOYSA-N 1-[1-(2-phenylphenyl)-2-piperazin-1-ylethyl]cyclohexan-1-ol Chemical compound C1CNCCN1CC(C=1C(=CC=CC=1)C=1C=CC=CC=1)C1(O)CCCCC1 HRPUOOXLTLERRJ-UHFFFAOYSA-N 0.000 claims 1
- CTXCQCBTNXHXPL-UHFFFAOYSA-N 1-[1-(3,5-dibromo-4-phenylmethoxyphenyl)-2-(4-methylpiperazin-1-yl)ethyl]cyclohexan-1-ol Chemical compound C1CN(C)CCN1CC(C1(O)CCCCC1)C(C=C1Br)=CC(Br)=C1OCC1=CC=CC=C1 CTXCQCBTNXHXPL-UHFFFAOYSA-N 0.000 claims 1
- JCMJQBMDOARXEX-UHFFFAOYSA-N 1-[1-(3,5-dibromo-4-phenylmethoxyphenyl)-2-piperazin-1-ylethyl]cyclohexan-1-ol Chemical compound C1CNCCN1CC(C=1C=C(Br)C(OCC=2C=CC=CC=2)=C(Br)C=1)C1(O)CCCCC1 JCMJQBMDOARXEX-UHFFFAOYSA-N 0.000 claims 1
- XUMIFXVHIUORRL-UHFFFAOYSA-N 1-[1-(3-bromo-4-phenylmethoxyphenyl)-2-(4-methylpiperazin-1-yl)ethyl]cyclohexan-1-ol Chemical compound C1CN(C)CCN1CC(C1(O)CCCCC1)C(C=C1Br)=CC=C1OCC1=CC=CC=C1 XUMIFXVHIUORRL-UHFFFAOYSA-N 0.000 claims 1
- DDBBAKXMCAMLIZ-UHFFFAOYSA-N 1-[1-(3-bromo-5-methoxy-4-phenylmethoxyphenyl)-2-(4-methylpiperazin-1-yl)ethyl]cyclohexan-1-ol Chemical compound COC1=CC(C(CN2CCN(C)CC2)C2(O)CCCCC2)=CC(Br)=C1OCC1=CC=CC=C1 DDBBAKXMCAMLIZ-UHFFFAOYSA-N 0.000 claims 1
- AHLRYGSMARHDCC-UHFFFAOYSA-N 1-[1-(3-bromo-5-methoxy-4-phenylmethoxyphenyl)-2-piperazin-1-ylethyl]cyclohexan-1-ol Chemical compound COC1=CC(C(CN2CCNCC2)C2(O)CCCCC2)=CC(Br)=C1OCC1=CC=CC=C1 AHLRYGSMARHDCC-UHFFFAOYSA-N 0.000 claims 1
- FWQHJBAJMBRTFN-UHFFFAOYSA-N 1-[1-(3-chloro-4-phenylmethoxyphenyl)-2-(4-methylpiperazin-1-yl)ethyl]cyclohexan-1-ol Chemical compound C1CN(C)CCN1CC(C1(O)CCCCC1)C(C=C1Cl)=CC=C1OCC1=CC=CC=C1 FWQHJBAJMBRTFN-UHFFFAOYSA-N 0.000 claims 1
- WDTHRPXYILRWIK-UHFFFAOYSA-N 1-[1-(3-chloro-4-phenylmethoxyphenyl)-2-piperazin-1-ylethyl]cyclohexan-1-ol Chemical compound C1CNCCN1CC(C=1C=C(Cl)C(OCC=2C=CC=CC=2)=CC=1)C1(O)CCCCC1 WDTHRPXYILRWIK-UHFFFAOYSA-N 0.000 claims 1
- HRFQBXHJHFYKGF-UHFFFAOYSA-N 1-[1-(3-ethenylphenyl)-2-piperazin-1-ylethyl]cyclohexan-1-ol Chemical compound C1CNCCN1CC(C=1C=C(C=C)C=CC=1)C1(O)CCCCC1 HRFQBXHJHFYKGF-UHFFFAOYSA-N 0.000 claims 1
- JAKZCRIYEXNKDR-UHFFFAOYSA-N 1-[1-(3-ethynylphenyl)-2-(4-methylpiperazin-1-yl)ethyl]cyclohexan-1-ol Chemical compound C1CN(C)CCN1CC(C1(O)CCCCC1)C1=CC=CC(C#C)=C1 JAKZCRIYEXNKDR-UHFFFAOYSA-N 0.000 claims 1
- AUTMHPRFYAAANQ-UHFFFAOYSA-N 1-[1-(3-ethynylphenyl)-2-piperazin-1-ylethyl]cyclohexan-1-ol Chemical compound C1CNCCN1CC(C=1C=C(C=CC=1)C#C)C1(O)CCCCC1 AUTMHPRFYAAANQ-UHFFFAOYSA-N 0.000 claims 1
- ZLRZQGHUXMTTCB-UHFFFAOYSA-N 1-[1-(3-fluoro-4-phenylmethoxyphenyl)-2-(4-methylpiperazin-1-yl)ethyl]cyclohexan-1-ol Chemical compound C1CN(C)CCN1CC(C1(O)CCCCC1)C(C=C1F)=CC=C1OCC1=CC=CC=C1 ZLRZQGHUXMTTCB-UHFFFAOYSA-N 0.000 claims 1
- LVSYRVWSIVWTFL-UHFFFAOYSA-N 1-[1-(3-fluoro-4-phenylmethoxyphenyl)-2-piperazin-1-ylethyl]cyclohexan-1-ol Chemical compound C1CNCCN1CC(C=1C=C(F)C(OCC=2C=CC=CC=2)=CC=1)C1(O)CCCCC1 LVSYRVWSIVWTFL-UHFFFAOYSA-N 0.000 claims 1
- MGDXBYQVGPLIKK-UHFFFAOYSA-N 1-[1-(3-methoxy-4-phenylmethoxyphenyl)-2-(4-methylpiperazin-1-yl)ethyl]cyclohexan-1-ol Chemical compound COC1=CC(C(CN2CCN(C)CC2)C2(O)CCCCC2)=CC=C1OCC1=CC=CC=C1 MGDXBYQVGPLIKK-UHFFFAOYSA-N 0.000 claims 1
- XDKDKPVYMZPDQK-UHFFFAOYSA-N 1-[1-(3-methoxy-4-phenylmethoxyphenyl)-2-piperazin-1-ylethyl]cyclohexan-1-ol Chemical compound COC1=CC(C(CN2CCNCC2)C2(O)CCCCC2)=CC=C1OCC1=CC=CC=C1 XDKDKPVYMZPDQK-UHFFFAOYSA-N 0.000 claims 1
- HSHSYQHQVDIHLN-UHFFFAOYSA-N 1-[1-(3-phenoxyphenyl)-2-piperazin-1-ylethyl]cyclohexan-1-ol Chemical compound C1CNCCN1CC(C=1C=C(OC=2C=CC=CC=2)C=CC=1)C1(O)CCCCC1 HSHSYQHQVDIHLN-UHFFFAOYSA-N 0.000 claims 1
- VJKAJDQXAJICET-UHFFFAOYSA-N 1-[1-(3-phenylmethoxyphenyl)-2-piperazin-1-ylethyl]cyclohexan-1-ol Chemical compound C1CNCCN1CC(C=1C=C(OCC=2C=CC=CC=2)C=CC=1)C1(O)CCCCC1 VJKAJDQXAJICET-UHFFFAOYSA-N 0.000 claims 1
- TVOMFOLPLCBTHH-UHFFFAOYSA-N 1-[1-(3-phenylphenyl)-2-piperazin-1-ylethyl]cyclohexan-1-ol Chemical compound C1CNCCN1CC(C=1C=C(C=CC=1)C=1C=CC=CC=1)C1(O)CCCCC1 TVOMFOLPLCBTHH-UHFFFAOYSA-N 0.000 claims 1
- BXXJXLDQQQUCND-UHFFFAOYSA-N 1-[1-(4-ethenylphenyl)-2-piperazin-1-ylethyl]cyclohexan-1-ol Chemical compound C1CNCCN1CC(C=1C=CC(C=C)=CC=1)C1(O)CCCCC1 BXXJXLDQQQUCND-UHFFFAOYSA-N 0.000 claims 1
- YZXAGGXYULXKIG-UHFFFAOYSA-N 1-[1-(4-methoxy-3-phenylphenyl)-2-piperazin-1-ylethyl]cyclohexan-1-ol Chemical compound COC1=CC=C(C(CN2CCNCC2)C2(O)CCCCC2)C=C1C1=CC=CC=C1 YZXAGGXYULXKIG-UHFFFAOYSA-N 0.000 claims 1
- GVGBQXWKBNVOBI-UHFFFAOYSA-N 1-[1-(4-naphthalen-1-yloxyphenyl)-2-piperazin-1-ylethyl]cyclohexan-1-ol Chemical compound C1CNCCN1CC(C=1C=CC(OC=2C3=CC=CC=C3C=CC=2)=CC=1)C1(O)CCCCC1 GVGBQXWKBNVOBI-UHFFFAOYSA-N 0.000 claims 1
- RTJGASNBFSLWHD-UHFFFAOYSA-N 1-[1-(4-phenoxyphenyl)-2-piperazin-1-ylethyl]cyclohexan-1-ol Chemical compound C1CNCCN1CC(C=1C=CC(OC=2C=CC=CC=2)=CC=1)C1(O)CCCCC1 RTJGASNBFSLWHD-UHFFFAOYSA-N 0.000 claims 1
- FOSCHCXRTMXZEJ-UHFFFAOYSA-N 1-[1-(4-phenylmethoxyphenyl)-2-piperazin-1-ylethyl]cyclobutan-1-ol Chemical compound C1CNCCN1CC(C=1C=CC(OCC=2C=CC=CC=2)=CC=1)C1(O)CCC1 FOSCHCXRTMXZEJ-UHFFFAOYSA-N 0.000 claims 1
- OQMAIACSJPFEHL-UHFFFAOYSA-N 1-[1-(4-phenylmethoxyphenyl)-2-piperazin-1-ylethyl]cyclohexan-1-ol Chemical compound C1CNCCN1CC(C=1C=CC(OCC=2C=CC=CC=2)=CC=1)C1(O)CCCCC1 OQMAIACSJPFEHL-UHFFFAOYSA-N 0.000 claims 1
- HQBQBZKEEMANPN-UHFFFAOYSA-N 1-[1-[2-(1,3-benzodioxol-5-yl)phenyl]-2-piperazin-1-ylethyl]cyclohexan-1-ol Chemical compound C1CNCCN1CC(C=1C(=CC=CC=1)C=1C=C2OCOC2=CC=1)C1(O)CCCCC1 HQBQBZKEEMANPN-UHFFFAOYSA-N 0.000 claims 1
- OVOXVCGLRYMTSR-UHFFFAOYSA-N 1-[1-[2-(3,4-dichlorophenyl)phenyl]-2-piperazin-1-ylethyl]cyclohexan-1-ol Chemical compound C1CNCCN1CC(C=1C(=CC=CC=1)C=1C=C(Cl)C(Cl)=CC=1)C1(O)CCCCC1 OVOXVCGLRYMTSR-UHFFFAOYSA-N 0.000 claims 1
- MCXVDZVAZGVDLO-UHFFFAOYSA-N 1-[1-[2-(3-chlorophenyl)phenyl]-2-piperazin-1-ylethyl]cyclohexan-1-ol Chemical compound C1CNCCN1CC(C=1C(=CC=CC=1)C=1C=C(Cl)C=CC=1)C1(O)CCCCC1 MCXVDZVAZGVDLO-UHFFFAOYSA-N 0.000 claims 1
- RMUAVSAMIIXPDD-UHFFFAOYSA-N 1-[1-[3-(2-fluorophenyl)phenyl]-2-piperazin-1-ylethyl]cyclohexan-1-ol Chemical compound C1CNCCN1CC(C=1C=C(C=CC=1)C=1C(=CC=CC=1)F)C1(O)CCCCC1 RMUAVSAMIIXPDD-UHFFFAOYSA-N 0.000 claims 1
- MCCRHCRBWYHGGZ-UHFFFAOYSA-N 1-[1-[3-(3,4-dichlorophenyl)-4-methoxyphenyl]-2-(4-methylpiperazin-1-yl)ethyl]cyclohexan-1-ol Chemical compound COC1=CC=C(C(CN2CCN(C)CC2)C2(O)CCCCC2)C=C1C1=CC=C(Cl)C(Cl)=C1 MCCRHCRBWYHGGZ-UHFFFAOYSA-N 0.000 claims 1
- NSVWSLUATRBHRL-UHFFFAOYSA-N 1-[1-[3-(3,4-dichlorophenyl)-4-methoxyphenyl]-2-piperazin-1-ylethyl]cyclohexan-1-ol Chemical compound COC1=CC=C(C(CN2CCNCC2)C2(O)CCCCC2)C=C1C1=CC=C(Cl)C(Cl)=C1 NSVWSLUATRBHRL-UHFFFAOYSA-N 0.000 claims 1
- AAMIWLKGDAMCRJ-UHFFFAOYSA-N 1-[1-[3-(3,4-dichlorophenyl)phenyl]-2-(4-methylpiperazin-1-yl)ethyl]cyclohexan-1-ol Chemical compound C1CN(C)CCN1CC(C1(O)CCCCC1)C1=CC=CC(C=2C=C(Cl)C(Cl)=CC=2)=C1 AAMIWLKGDAMCRJ-UHFFFAOYSA-N 0.000 claims 1
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- PRHJTLWEXLWKKY-UHFFFAOYSA-N 1-[1-[3-(3,4-dimethoxyphenyl)phenyl]-2-piperazin-1-ylethyl]cyclohexan-1-ol Chemical compound C1=C(OC)C(OC)=CC=C1C1=CC=CC(C(CN2CCNCC2)C2(O)CCCCC2)=C1 PRHJTLWEXLWKKY-UHFFFAOYSA-N 0.000 claims 1
- BYJZOOHEEDGSGD-UHFFFAOYSA-N 1-[1-[3-(3-chlorophenyl)phenyl]-2-piperazin-1-ylethyl]cyclohexan-1-ol Chemical compound C1CNCCN1CC(C=1C=C(C=CC=1)C=1C=C(Cl)C=CC=1)C1(O)CCCCC1 BYJZOOHEEDGSGD-UHFFFAOYSA-N 0.000 claims 1
- VOWWSARGLBPCNF-UHFFFAOYSA-N 1-[1-[3-chloro-4-(2-phenylethoxy)phenyl]-2-(4-methylpiperazin-1-yl)ethyl]cyclohexan-1-ol Chemical compound C1CN(C)CCN1CC(C1(O)CCCCC1)C(C=C1Cl)=CC=C1OCCC1=CC=CC=C1 VOWWSARGLBPCNF-UHFFFAOYSA-N 0.000 claims 1
- QFAZLWMSVXDDPF-UHFFFAOYSA-N 1-[1-[3-chloro-4-(2-phenylethoxy)phenyl]-2-piperazin-1-ylethyl]cyclohexan-1-ol Chemical compound C1CNCCN1CC(C=1C=C(Cl)C(OCCC=2C=CC=CC=2)=CC=1)C1(O)CCCCC1 QFAZLWMSVXDDPF-UHFFFAOYSA-N 0.000 claims 1
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- QAKSCDSQISZQGG-UHFFFAOYSA-N 1-[1-[3-chloro-4-[(3-methoxyphenyl)methoxy]phenyl]-2-(4-methylpiperazin-1-yl)ethyl]cyclohexan-1-ol Chemical compound COC1=CC=CC(COC=2C(=CC(=CC=2)C(CN2CCN(C)CC2)C2(O)CCCCC2)Cl)=C1 QAKSCDSQISZQGG-UHFFFAOYSA-N 0.000 claims 1
- XOYTUSLGEZOIJL-UHFFFAOYSA-N 1-[1-[3-chloro-4-[(3-methoxyphenyl)methoxy]phenyl]-2-piperazin-1-ylethyl]cyclohexan-1-ol Chemical compound COC1=CC=CC(COC=2C(=CC(=CC=2)C(CN2CCNCC2)C2(O)CCCCC2)Cl)=C1 XOYTUSLGEZOIJL-UHFFFAOYSA-N 0.000 claims 1
- XAEBSQSPZJDXNC-UHFFFAOYSA-N 1-[1-[3-chloro-4-[[2-(trifluoromethyl)phenyl]methoxy]phenyl]-2-piperazin-1-ylethyl]cyclohexan-1-ol Chemical compound C1CNCCN1CC(C=1C=C(Cl)C(OCC=2C(=CC=CC=2)C(F)(F)F)=CC=1)C1(O)CCCCC1 XAEBSQSPZJDXNC-UHFFFAOYSA-N 0.000 claims 1
- RCMCPQAYSSLTTO-UHFFFAOYSA-N 1-[1-[3-chloro-4-[[3-(trifluoromethyl)phenyl]methoxy]phenyl]-2-(4-methylpiperazin-1-yl)ethyl]cyclohexan-1-ol Chemical compound C1CN(C)CCN1CC(C1(O)CCCCC1)C(C=C1Cl)=CC=C1OCC1=CC=CC(C(F)(F)F)=C1 RCMCPQAYSSLTTO-UHFFFAOYSA-N 0.000 claims 1
- ZOZXFUXGNAWQSO-UHFFFAOYSA-N 1-[1-[3-chloro-4-[[3-(trifluoromethyl)phenyl]methoxy]phenyl]-2-piperazin-1-ylethyl]cyclohexan-1-ol Chemical compound C1CNCCN1CC(C=1C=C(Cl)C(OCC=2C=C(C=CC=2)C(F)(F)F)=CC=1)C1(O)CCCCC1 ZOZXFUXGNAWQSO-UHFFFAOYSA-N 0.000 claims 1
- TXTDOUXTZJVLDD-UHFFFAOYSA-N 1-[1-[3-chloro-4-[[4-(trifluoromethyl)phenyl]methoxy]phenyl]-2-(4-methylpiperazin-1-yl)ethyl]cyclohexan-1-ol Chemical compound C1CN(C)CCN1CC(C1(O)CCCCC1)C(C=C1Cl)=CC=C1OCC1=CC=C(C(F)(F)F)C=C1 TXTDOUXTZJVLDD-UHFFFAOYSA-N 0.000 claims 1
- LPNXFZLHHYIAIW-UHFFFAOYSA-N 1-[1-[3-chloro-4-[[4-(trifluoromethyl)phenyl]methoxy]phenyl]-2-piperazin-1-ylethyl]cyclohexan-1-ol Chemical compound C1CNCCN1CC(C=1C=C(Cl)C(OCC=2C=CC(=CC=2)C(F)(F)F)=CC=1)C1(O)CCCCC1 LPNXFZLHHYIAIW-UHFFFAOYSA-N 0.000 claims 1
- VDNIAMREZBGXMY-UHFFFAOYSA-N 1-[1-[3-fluoro-4-[(4-methylphenyl)methoxy]phenyl]-2-(4-methylpiperazin-1-yl)ethyl]cyclohexan-1-ol Chemical compound C1CN(C)CCN1CC(C1(O)CCCCC1)C(C=C1F)=CC=C1OCC1=CC=C(C)C=C1 VDNIAMREZBGXMY-UHFFFAOYSA-N 0.000 claims 1
- SNEMXMKEYCKQPS-UHFFFAOYSA-N 1-[1-[3-fluoro-4-[(4-methylphenyl)methoxy]phenyl]-2-piperazin-1-ylethyl]cyclohexan-1-ol Chemical compound C1=CC(C)=CC=C1COC1=CC=C(C(CN2CCNCC2)C2(O)CCCCC2)C=C1F SNEMXMKEYCKQPS-UHFFFAOYSA-N 0.000 claims 1
- RXODNKVIPCCWCH-UHFFFAOYSA-N 1-[1-[3-fluoro-4-[[4-(trifluoromethyl)phenyl]methoxy]phenyl]-2-(4-methylpiperazin-1-yl)ethyl]cyclohexan-1-ol Chemical compound C1CN(C)CCN1CC(C1(O)CCCCC1)C(C=C1F)=CC=C1OCC1=CC=C(C(F)(F)F)C=C1 RXODNKVIPCCWCH-UHFFFAOYSA-N 0.000 claims 1
- MJNLCCKELMSEOY-UHFFFAOYSA-N 1-[1-[3-fluoro-4-[[4-(trifluoromethyl)phenyl]methoxy]phenyl]-2-piperazin-1-ylethyl]cyclohexan-1-ol Chemical compound C1CNCCN1CC(C=1C=C(F)C(OCC=2C=CC(=CC=2)C(F)(F)F)=CC=1)C1(O)CCCCC1 MJNLCCKELMSEOY-UHFFFAOYSA-N 0.000 claims 1
- QBUHGBJFQCJQHV-UHFFFAOYSA-N 1-[1-[3-methoxy-4-(naphthalen-2-ylmethoxy)phenyl]-2-(4-methylpiperazin-1-yl)ethyl]cyclohexan-1-ol Chemical compound C=1C=C(OCC=2C=C3C=CC=CC3=CC=2)C(OC)=CC=1C(C1(O)CCCCC1)CN1CCN(C)CC1 QBUHGBJFQCJQHV-UHFFFAOYSA-N 0.000 claims 1
- DLNPMEWEDASHCP-UHFFFAOYSA-N 1-[1-[3-methoxy-4-(naphthalen-2-ylmethoxy)phenyl]-2-piperazin-1-ylethyl]cyclohexan-1-ol Chemical compound C=1C=C(OCC=2C=C3C=CC=CC3=CC=2)C(OC)=CC=1C(C1(O)CCCCC1)CN1CCNCC1 DLNPMEWEDASHCP-UHFFFAOYSA-N 0.000 claims 1
- LFOODVNGQPPUHZ-UHFFFAOYSA-N 1-[1-[3-methoxy-4-[[4-(trifluoromethyl)phenyl]methoxy]phenyl]-2-(4-methylpiperazin-1-yl)ethyl]cyclohexan-1-ol Chemical compound COC1=CC(C(CN2CCN(C)CC2)C2(O)CCCCC2)=CC=C1OCC1=CC=C(C(F)(F)F)C=C1 LFOODVNGQPPUHZ-UHFFFAOYSA-N 0.000 claims 1
- TVSYBCAJYFUDQY-UHFFFAOYSA-N 1-[1-[3-methoxy-4-[[4-(trifluoromethyl)phenyl]methoxy]phenyl]-2-piperazin-1-ylethyl]cyclohexan-1-ol Chemical compound COC1=CC(C(CN2CCNCC2)C2(O)CCCCC2)=CC=C1OCC1=CC=C(C(F)(F)F)C=C1 TVSYBCAJYFUDQY-UHFFFAOYSA-N 0.000 claims 1
- MDMKEQXBIYECSP-UHFFFAOYSA-N 1-[1-[4-(2-chlorophenyl)phenyl]-2-(4-methylpiperazin-1-yl)ethyl]cyclohexan-1-ol Chemical compound C1CN(C)CCN1CC(C1(O)CCCCC1)C1=CC=C(C=2C(=CC=CC=2)Cl)C=C1 MDMKEQXBIYECSP-UHFFFAOYSA-N 0.000 claims 1
- BANAVMQZRYRDSK-UHFFFAOYSA-N 1-[1-[4-(2-chlorophenyl)phenyl]-2-piperazin-1-ylethyl]cyclohexan-1-ol Chemical compound C1CNCCN1CC(C=1C=CC(=CC=1)C=1C(=CC=CC=1)Cl)C1(O)CCCCC1 BANAVMQZRYRDSK-UHFFFAOYSA-N 0.000 claims 1
- SRVNDNNQMUBLHQ-UHFFFAOYSA-N 1-[1-[4-(2-fluorophenyl)phenyl]-2-piperazin-1-ylethyl]cyclohexan-1-ol Chemical compound C1CNCCN1CC(C=1C=CC(=CC=1)C=1C(=CC=CC=1)F)C1(O)CCCCC1 SRVNDNNQMUBLHQ-UHFFFAOYSA-N 0.000 claims 1
- XZAVXFBAGQMEFJ-UHFFFAOYSA-N 1-[1-[4-(2-methylpropoxy)-3-(trifluoromethoxy)phenyl]-2-piperazin-1-ylethyl]cyclohexan-1-ol Chemical compound C1=C(OC(F)(F)F)C(OCC(C)C)=CC=C1C(C1(O)CCCCC1)CN1CCNCC1 XZAVXFBAGQMEFJ-UHFFFAOYSA-N 0.000 claims 1
- RCOSSBDCOLEVKX-UHFFFAOYSA-N 1-[1-[4-(2-naphthalen-1-ylethoxy)phenyl]-2-piperazin-1-ylethyl]cyclohexan-1-ol Chemical compound C1CNCCN1CC(C=1C=CC(OCCC=2C3=CC=CC=C3C=CC=2)=CC=1)C1(O)CCCCC1 RCOSSBDCOLEVKX-UHFFFAOYSA-N 0.000 claims 1
- WQHZXZZOAWQOPK-UHFFFAOYSA-N 1-[1-[4-(2-phenylethoxy)phenyl]-2-piperazin-1-ylethyl]cyclohexan-1-ol Chemical compound C1CNCCN1CC(C=1C=CC(OCCC=2C=CC=CC=2)=CC=1)C1(O)CCCCC1 WQHZXZZOAWQOPK-UHFFFAOYSA-N 0.000 claims 1
- PGUSAUBRWLQDTH-UHFFFAOYSA-N 1-[1-[4-(2-phenylethyl)phenyl]-2-piperazin-1-ylethyl]cyclohexan-1-ol Chemical compound C1CNCCN1CC(C=1C=CC(CCC=2C=CC=CC=2)=CC=1)C1(O)CCCCC1 PGUSAUBRWLQDTH-UHFFFAOYSA-N 0.000 claims 1
- SJEPPRLUECGLBR-UHFFFAOYSA-N 1-[1-[4-(3,4-dichlorophenyl)phenyl]-2-(4-methylpiperazin-1-yl)ethyl]cyclobutan-1-ol Chemical compound C1CN(C)CCN1CC(C1(O)CCC1)C1=CC=C(C=2C=C(Cl)C(Cl)=CC=2)C=C1 SJEPPRLUECGLBR-UHFFFAOYSA-N 0.000 claims 1
- OGULWIGVVKTNMT-UHFFFAOYSA-N 1-[1-[4-(3,4-dichlorophenyl)phenyl]-2-piperazin-1-ylethyl]cyclobutan-1-ol Chemical compound C1CNCCN1CC(C=1C=CC(=CC=1)C=1C=C(Cl)C(Cl)=CC=1)C1(O)CCC1 OGULWIGVVKTNMT-UHFFFAOYSA-N 0.000 claims 1
- CJIQAGYAJGKUSN-UHFFFAOYSA-N 1-[1-[4-(3,4-dichlorophenyl)phenyl]-2-piperazin-1-ylethyl]cyclohexan-1-ol Chemical compound C1CNCCN1CC(C=1C=CC(=CC=1)C=1C=C(Cl)C(Cl)=CC=1)C1(O)CCCCC1 CJIQAGYAJGKUSN-UHFFFAOYSA-N 0.000 claims 1
- HWAFFFACAZSEHS-UHFFFAOYSA-N 1-[1-[4-(3,5-dichlorophenyl)phenyl]-2-(4-methylpiperazin-1-yl)ethyl]cyclobutan-1-ol Chemical compound C1CN(C)CCN1CC(C1(O)CCC1)C1=CC=C(C=2C=C(Cl)C=C(Cl)C=2)C=C1 HWAFFFACAZSEHS-UHFFFAOYSA-N 0.000 claims 1
- NFYJPYOLXCTCLC-UHFFFAOYSA-N 1-[1-[4-(3,5-dichlorophenyl)phenyl]-2-piperazin-1-ylethyl]cyclobutan-1-ol Chemical compound C1CNCCN1CC(C=1C=CC(=CC=1)C=1C=C(Cl)C=C(Cl)C=1)C1(O)CCC1 NFYJPYOLXCTCLC-UHFFFAOYSA-N 0.000 claims 1
- QTHIUNHDCUHODQ-UHFFFAOYSA-N 1-[1-[4-(3-chlorophenyl)phenyl]-2-(4-methylpiperazin-1-yl)ethyl]cyclobutan-1-ol Chemical compound C1CN(C)CCN1CC(C1(O)CCC1)C1=CC=C(C=2C=C(Cl)C=CC=2)C=C1 QTHIUNHDCUHODQ-UHFFFAOYSA-N 0.000 claims 1
- OWFTULGQMGDQJY-UHFFFAOYSA-N 1-[1-[4-(3-chlorophenyl)phenyl]-2-piperazin-1-ylethyl]cyclobutan-1-ol Chemical compound C1CNCCN1CC(C=1C=CC(=CC=1)C=1C=C(Cl)C=CC=1)C1(O)CCC1 OWFTULGQMGDQJY-UHFFFAOYSA-N 0.000 claims 1
- AOLDSUJCYTVQPY-UHFFFAOYSA-N 1-[1-[4-(3-chlorophenyl)phenyl]-2-piperazin-1-ylethyl]cyclohexan-1-ol Chemical compound C1CNCCN1CC(C=1C=CC(=CC=1)C=1C=C(Cl)C=CC=1)C1(O)CCCCC1 AOLDSUJCYTVQPY-UHFFFAOYSA-N 0.000 claims 1
- NLUNJGKVRXTIQR-UHFFFAOYSA-N 1-[1-[4-(3-fluorophenyl)phenyl]-2-piperazin-1-ylethyl]cyclohexan-1-ol Chemical compound C1CNCCN1CC(C=1C=CC(=CC=1)C=1C=C(F)C=CC=1)C1(O)CCCCC1 NLUNJGKVRXTIQR-UHFFFAOYSA-N 0.000 claims 1
- ADEBBTHVOJOCKN-UHFFFAOYSA-N 1-[1-[4-(3-methoxyphenyl)phenyl]-2-(4-methylpiperazin-1-yl)ethyl]cyclohexan-1-ol Chemical compound COC1=CC=CC(C=2C=CC(=CC=2)C(CN2CCN(C)CC2)C2(O)CCCCC2)=C1 ADEBBTHVOJOCKN-UHFFFAOYSA-N 0.000 claims 1
- VHJJBYITROGTCC-UHFFFAOYSA-N 1-[1-[4-(3-methoxyphenyl)phenyl]-2-piperazin-1-ylethyl]cyclohexan-1-ol Chemical compound COC1=CC=CC(C=2C=CC(=CC=2)C(CN2CCNCC2)C2(O)CCCCC2)=C1 VHJJBYITROGTCC-UHFFFAOYSA-N 0.000 claims 1
- SLNSEFPHYOUOPS-UHFFFAOYSA-N 1-[1-[4-(3-nitrophenyl)phenyl]-2-piperazin-1-ylethyl]cyclohexan-1-ol Chemical compound C1CNCCN1CC(C=1C=CC(=CC=1)C=1C=C(C=CC=1)[N+]([O-])=O)C1(O)CCCCC1 SLNSEFPHYOUOPS-UHFFFAOYSA-N 0.000 claims 1
- XEFXJOUFQQIEGR-UHFFFAOYSA-N 1-[1-[4-(4-chlorophenyl)phenyl]-2-piperazin-1-ylethyl]cyclohexan-1-ol Chemical compound C1CNCCN1CC(C=1C=CC(=CC=1)C=1C=CC(Cl)=CC=1)C1(O)CCCCC1 XEFXJOUFQQIEGR-UHFFFAOYSA-N 0.000 claims 1
- VUECDYMILMFQFF-UHFFFAOYSA-N 1-[1-[4-(4-fluorophenyl)phenyl]-2-(4-methylpiperazin-1-yl)ethyl]cyclohexan-1-ol Chemical compound C1CN(C)CCN1CC(C1(O)CCCCC1)C1=CC=C(C=2C=CC(F)=CC=2)C=C1 VUECDYMILMFQFF-UHFFFAOYSA-N 0.000 claims 1
- FMBJFEFKTVVARM-UHFFFAOYSA-N 1-[1-[4-(4-methylphenyl)phenyl]-2-(4-methylpiperazin-1-yl)ethyl]cyclohexan-1-ol Chemical compound C1CN(C)CCN1CC(C1(O)CCCCC1)C1=CC=C(C=2C=CC(C)=CC=2)C=C1 FMBJFEFKTVVARM-UHFFFAOYSA-N 0.000 claims 1
- FRKAKPDTDXVBCL-UHFFFAOYSA-N 1-[1-[4-(cyclohexylmethoxy)phenyl]-2-(4-methylpiperazin-1-yl)ethyl]cyclohexan-1-ol Chemical compound C1CN(C)CCN1CC(C1(O)CCCCC1)C(C=C1)=CC=C1OCC1CCCCC1 FRKAKPDTDXVBCL-UHFFFAOYSA-N 0.000 claims 1
- INTSICUEQXDLLK-UHFFFAOYSA-N 1-[1-[4-(naphthalen-2-ylmethoxy)phenyl]-2-piperazin-1-ylethyl]cyclohexan-1-ol Chemical compound C1CNCCN1CC(C=1C=CC(OCC=2C=C3C=CC=CC3=CC=2)=CC=1)C1(O)CCCCC1 INTSICUEQXDLLK-UHFFFAOYSA-N 0.000 claims 1
- DYELLDPBYGVXEU-UHFFFAOYSA-N 1-[1-[4-[(4-bromo-2-fluorophenyl)methoxy]-3-chlorophenyl]-2-(4-methylpiperazin-1-yl)ethyl]cyclohexan-1-ol Chemical compound C1CN(C)CCN1CC(C1(O)CCCCC1)C(C=C1Cl)=CC=C1OCC1=CC=C(Br)C=C1F DYELLDPBYGVXEU-UHFFFAOYSA-N 0.000 claims 1
- ZURWYUIAKVWINR-UHFFFAOYSA-N 1-[1-[4-[(4-bromo-2-fluorophenyl)methoxy]-3-chlorophenyl]-2-piperazin-1-ylethyl]cyclohexan-1-ol Chemical compound C1CNCCN1CC(C=1C=C(Cl)C(OCC=2C(=CC(Br)=CC=2)F)=CC=1)C1(O)CCCCC1 ZURWYUIAKVWINR-UHFFFAOYSA-N 0.000 claims 1
- PYGHAVXKUIYELT-UHFFFAOYSA-N 1-[1-[4-[(4-bromo-2-fluorophenyl)methoxy]-3-methoxyphenyl]-2-(4-methylpiperazin-1-yl)ethyl]cyclohexan-1-ol Chemical compound COC1=CC(C(CN2CCN(C)CC2)C2(O)CCCCC2)=CC=C1OCC1=CC=C(Br)C=C1F PYGHAVXKUIYELT-UHFFFAOYSA-N 0.000 claims 1
- GUAXBKPOFMQNLS-UHFFFAOYSA-N 1-[1-[4-[(4-bromo-2-fluorophenyl)methoxy]-3-methoxyphenyl]-2-piperazin-1-ylethyl]cyclohexan-1-ol Chemical compound COC1=CC(C(CN2CCNCC2)C2(O)CCCCC2)=CC=C1OCC1=CC=C(Br)C=C1F GUAXBKPOFMQNLS-UHFFFAOYSA-N 0.000 claims 1
- UZQKTBGZTJNWLO-UHFFFAOYSA-N 1-[1-[4-[(4-bromo-2-fluorophenyl)methoxy]phenyl]-2-(4-methylpiperazin-1-yl)ethyl]cyclohexan-1-ol Chemical compound C1CN(C)CCN1CC(C1(O)CCCCC1)C(C=C1)=CC=C1OCC1=CC=C(Br)C=C1F UZQKTBGZTJNWLO-UHFFFAOYSA-N 0.000 claims 1
- IXWLIPFBYUHRMC-UHFFFAOYSA-N 1-[1-[4-[(4-bromo-2-fluorophenyl)methoxy]phenyl]-2-piperazin-1-ylethyl]cyclohexan-1-ol Chemical compound C1CNCCN1CC(C=1C=CC(OCC=2C(=CC(Br)=CC=2)F)=CC=1)C1(O)CCCCC1 IXWLIPFBYUHRMC-UHFFFAOYSA-N 0.000 claims 1
- WSJJAYDMOYAEJK-UHFFFAOYSA-N 1-[1-[4-[2-(4-fluorophenyl)ethoxy]phenyl]-2-(4-methylpiperazin-1-yl)ethyl]cyclohexan-1-ol Chemical compound C1CN(C)CCN1CC(C1(O)CCCCC1)C(C=C1)=CC=C1OCCC1=CC=C(F)C=C1 WSJJAYDMOYAEJK-UHFFFAOYSA-N 0.000 claims 1
- JSLCGHYATRHTHQ-UHFFFAOYSA-N 1-[1-[4-[2-(4-fluorophenyl)ethoxy]phenyl]-2-piperazin-1-ylethyl]cyclohexan-1-ol Chemical compound C1CNCCN1CC(C=1C=CC(OCCC=2C=CC(F)=CC=2)=CC=1)C1(O)CCCCC1 JSLCGHYATRHTHQ-UHFFFAOYSA-N 0.000 claims 1
- SXZKHCDZDKNTSX-UHFFFAOYSA-N 1-[1-[4-ethoxy-3-(trifluoromethoxy)phenyl]-2-(4-methylpiperazin-1-yl)ethyl]cyclohexan-1-ol Chemical compound C1=C(OC(F)(F)F)C(OCC)=CC=C1C(C1(O)CCCCC1)CN1CCN(C)CC1 SXZKHCDZDKNTSX-UHFFFAOYSA-N 0.000 claims 1
- KTBVXKVTNZHLQB-UHFFFAOYSA-N 1-[1-[4-ethoxy-3-(trifluoromethoxy)phenyl]-2-piperazin-1-ylethyl]cyclohexan-1-ol Chemical compound C1=C(OC(F)(F)F)C(OCC)=CC=C1C(C1(O)CCCCC1)CN1CCNCC1 KTBVXKVTNZHLQB-UHFFFAOYSA-N 0.000 claims 1
- PYPCNHGPAOIXQW-UHFFFAOYSA-N 1-[1-[4-methoxy-3-(trifluoromethoxy)phenyl]-2-(4-methylpiperazin-1-yl)ethyl]cyclohexan-1-ol Chemical compound C1=C(OC(F)(F)F)C(OC)=CC=C1C(C1(O)CCCCC1)CN1CCN(C)CC1 PYPCNHGPAOIXQW-UHFFFAOYSA-N 0.000 claims 1
- XGVPDSFGZMQZOG-UHFFFAOYSA-N 1-[1-[4-methoxy-3-(trifluoromethoxy)phenyl]-2-piperazin-1-ylethyl]cyclohexan-1-ol Chemical compound C1=C(OC(F)(F)F)C(OC)=CC=C1C(C1(O)CCCCC1)CN1CCNCC1 XGVPDSFGZMQZOG-UHFFFAOYSA-N 0.000 claims 1
- OFERULCRQIMYIJ-UHFFFAOYSA-N 1-[1-[4-methoxy-3-[3-(trifluoromethoxy)phenyl]phenyl]-2-(4-methylpiperazin-1-yl)ethyl]cyclohexan-1-ol Chemical compound COC1=CC=C(C(CN2CCN(C)CC2)C2(O)CCCCC2)C=C1C1=CC=CC(OC(F)(F)F)=C1 OFERULCRQIMYIJ-UHFFFAOYSA-N 0.000 claims 1
- XFNZVBJRBWNEPC-UHFFFAOYSA-N 1-[1-[4-methoxy-3-[3-(trifluoromethoxy)phenyl]phenyl]-2-piperazin-1-ylethyl]cyclohexan-1-ol Chemical compound COC1=CC=C(C(CN2CCNCC2)C2(O)CCCCC2)C=C1C1=CC=CC(OC(F)(F)F)=C1 XFNZVBJRBWNEPC-UHFFFAOYSA-N 0.000 claims 1
- DVJHRHZVKDADIW-UHFFFAOYSA-N 1-[1-[4-methoxy-3-[4-(trifluoromethyl)phenyl]phenyl]-2-(4-methylpiperazin-1-yl)ethyl]cyclohexan-1-ol Chemical compound COC1=CC=C(C(CN2CCN(C)CC2)C2(O)CCCCC2)C=C1C1=CC=C(C(F)(F)F)C=C1 DVJHRHZVKDADIW-UHFFFAOYSA-N 0.000 claims 1
- NLASOTUEBXLGBY-UHFFFAOYSA-N 1-[1-[4-methoxy-3-[4-(trifluoromethyl)phenyl]phenyl]-2-piperazin-1-ylethyl]cyclohexan-1-ol Chemical compound COC1=CC=C(C(CN2CCNCC2)C2(O)CCCCC2)C=C1C1=CC=C(C(F)(F)F)C=C1 NLASOTUEBXLGBY-UHFFFAOYSA-N 0.000 claims 1
- JVFJKZPKZJSJGP-UHFFFAOYSA-N 1-[1-[4-phenylmethoxy-3-(trifluoromethoxy)phenyl]-2-piperazin-1-ylethyl]cyclohexan-1-ol Chemical compound C1CNCCN1CC(C=1C=C(OC(F)(F)F)C(OCC=2C=CC=CC=2)=CC=1)C1(O)CCCCC1 JVFJKZPKZJSJGP-UHFFFAOYSA-N 0.000 claims 1
- WTHZXMVFGUWMDJ-UHFFFAOYSA-N 1-[1-[4-phenylmethoxy-3-(trifluoromethyl)phenyl]-2-piperazin-1-ylethyl]cyclohexan-1-ol Chemical compound C1CNCCN1CC(C=1C=C(C(OCC=2C=CC=CC=2)=CC=1)C(F)(F)F)C1(O)CCCCC1 WTHZXMVFGUWMDJ-UHFFFAOYSA-N 0.000 claims 1
- PIPGDGKLVZUSKG-UHFFFAOYSA-N 1-[2-(4-aminopiperidin-1-yl)-1-[3-(3,4-dichlorophenyl)phenyl]ethyl]cyclohexan-1-ol Chemical compound C1CC(N)CCN1CC(C1(O)CCCCC1)C1=CC=CC(C=2C=C(Cl)C(Cl)=CC=2)=C1 PIPGDGKLVZUSKG-UHFFFAOYSA-N 0.000 claims 1
- NMKFVSKZZUWFCB-UHFFFAOYSA-N 1-[2-(4-benzyl-1,4-diazepan-1-yl)-1-[4-(trifluoromethoxy)phenyl]ethyl]cyclohexan-1-ol Chemical compound C1CCN(CC=2C=CC=CC=2)CCN1CC(C=1C=CC(OC(F)(F)F)=CC=1)C1(O)CCCCC1 NMKFVSKZZUWFCB-UHFFFAOYSA-N 0.000 claims 1
- HNSOGGNCLHASJS-UHFFFAOYSA-N 1-[2-(4-ethylpiperazin-1-yl)-1-[4-(trifluoromethoxy)phenyl]ethyl]cyclohexan-1-ol Chemical compound C1CN(CC)CCN1CC(C1(O)CCCCC1)C1=CC=C(OC(F)(F)F)C=C1 HNSOGGNCLHASJS-UHFFFAOYSA-N 0.000 claims 1
- BIIUIJOENQXLKS-UHFFFAOYSA-N 1-[2-(4-methyl-1,4-diazepan-1-yl)-1-[4-(trifluoromethoxy)phenyl]ethyl]cyclobutan-1-ol Chemical compound C1CN(C)CCCN1CC(C1(O)CCC1)C1=CC=C(OC(F)(F)F)C=C1 BIIUIJOENQXLKS-UHFFFAOYSA-N 0.000 claims 1
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- MYBVWQRJURFZLC-UHFFFAOYSA-N 1-[2-(4-methylpiperazin-1-yl)-1-(3-phenylmethoxyphenyl)ethyl]cyclohexan-1-ol Chemical compound C1CN(C)CCN1CC(C1(O)CCCCC1)C1=CC=CC(OCC=2C=CC=CC=2)=C1 MYBVWQRJURFZLC-UHFFFAOYSA-N 0.000 claims 1
- SMNJOSJGXQIUCX-UHFFFAOYSA-N 1-[2-(4-methylpiperazin-1-yl)-1-(3-prop-1-ynylphenyl)ethyl]cyclohexan-1-ol Chemical compound CC#CC1=CC=CC(C(CN2CCN(C)CC2)C2(O)CCCCC2)=C1 SMNJOSJGXQIUCX-UHFFFAOYSA-N 0.000 claims 1
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- GSJOHNREAMQVOJ-UHFFFAOYSA-N 1-[2-(4-methylpiperazin-1-yl)-1-(4-phenoxyphenyl)ethyl]cyclohexan-1-ol Chemical compound C1CN(C)CCN1CC(C1(O)CCCCC1)C(C=C1)=CC=C1OC1=CC=CC=C1 GSJOHNREAMQVOJ-UHFFFAOYSA-N 0.000 claims 1
- YUVFGXBDRRGYLU-UHFFFAOYSA-N 1-[2-(4-methylpiperazin-1-yl)-1-(4-phenylmethoxyphenyl)ethyl]cyclobutan-1-ol Chemical compound C1CN(C)CCN1CC(C1(O)CCC1)C(C=C1)=CC=C1OCC1=CC=CC=C1 YUVFGXBDRRGYLU-UHFFFAOYSA-N 0.000 claims 1
- IJQIDWNPOSADGE-UHFFFAOYSA-N 1-[2-(4-methylpiperazin-1-yl)-1-[3-(trifluoromethoxy)phenyl]ethyl]cyclobutan-1-ol Chemical compound C1CN(C)CCN1CC(C1(O)CCC1)C1=CC=CC(OC(F)(F)F)=C1 IJQIDWNPOSADGE-UHFFFAOYSA-N 0.000 claims 1
- AKRIZMRTOCYSRB-UHFFFAOYSA-N 1-[2-(4-methylpiperazin-1-yl)-1-[3-(trifluoromethoxy)phenyl]ethyl]cyclohexan-1-ol Chemical compound C1CN(C)CCN1CC(C1(O)CCCCC1)C1=CC=CC(OC(F)(F)F)=C1 AKRIZMRTOCYSRB-UHFFFAOYSA-N 0.000 claims 1
- FFXIHCLSIWJFHQ-UHFFFAOYSA-N 1-[2-(4-methylpiperazin-1-yl)-1-[4-(2-methylpropoxy)-3-(trifluoromethoxy)phenyl]ethyl]cyclohexan-1-ol Chemical compound C1=C(OC(F)(F)F)C(OCC(C)C)=CC=C1C(C1(O)CCCCC1)CN1CCN(C)CC1 FFXIHCLSIWJFHQ-UHFFFAOYSA-N 0.000 claims 1
- IHFOBHKPSYBGMW-UHFFFAOYSA-N 1-[2-(4-methylpiperazin-1-yl)-1-[4-(2-naphthalen-1-ylethoxy)phenyl]ethyl]cyclohexan-1-ol Chemical compound C1CN(C)CCN1CC(C1(O)CCCCC1)C(C=C1)=CC=C1OCCC1=CC=CC2=CC=CC=C12 IHFOBHKPSYBGMW-UHFFFAOYSA-N 0.000 claims 1
- JRXLLPCLCUEPIY-UHFFFAOYSA-N 1-[2-(4-methylpiperazin-1-yl)-1-[4-(2-phenylethoxy)phenyl]ethyl]cyclohexan-1-ol Chemical compound C1CN(C)CCN1CC(C1(O)CCCCC1)C(C=C1)=CC=C1OCCC1=CC=CC=C1 JRXLLPCLCUEPIY-UHFFFAOYSA-N 0.000 claims 1
- LKGBVMALJJMXKK-UHFFFAOYSA-N 1-[2-(4-methylpiperazin-1-yl)-1-[4-(2-phenylethyl)phenyl]ethyl]cyclohexan-1-ol Chemical compound C1CN(C)CCN1CC(C1(O)CCCCC1)C(C=C1)=CC=C1CCC1=CC=CC=C1 LKGBVMALJJMXKK-UHFFFAOYSA-N 0.000 claims 1
- AIIOFBPCJNWQMW-UHFFFAOYSA-N 1-[2-(4-methylpiperazin-1-yl)-1-[4-(3-nitrophenyl)phenyl]ethyl]cyclohexan-1-ol Chemical compound C1CN(C)CCN1CC(C1(O)CCCCC1)C1=CC=C(C=2C=C(C=CC=2)[N+]([O-])=O)C=C1 AIIOFBPCJNWQMW-UHFFFAOYSA-N 0.000 claims 1
- JJEMQMYJMYOISE-UHFFFAOYSA-N 1-[2-(4-methylpiperazin-1-yl)-1-[4-(naphthalen-2-ylmethoxy)phenyl]ethyl]cyclohexan-1-ol Chemical compound C1CN(C)CCN1CC(C1(O)CCCCC1)C(C=C1)=CC=C1OCC1=CC=C(C=CC=C2)C2=C1 JJEMQMYJMYOISE-UHFFFAOYSA-N 0.000 claims 1
- UNGFHUJRDWWHSN-UHFFFAOYSA-N 1-[2-(4-methylpiperazin-1-yl)-1-[4-(trifluoromethoxy)phenyl]ethyl]cyclohexan-1-ol Chemical compound C1CN(C)CCN1CC(C1(O)CCCCC1)C1=CC=C(OC(F)(F)F)C=C1 UNGFHUJRDWWHSN-UHFFFAOYSA-N 0.000 claims 1
- BXFSKZGLRKVPAT-FPSALIRRSA-N 1-[2-(4-methylpiperazin-1-yl)-1-[4-[(1r)-1-phenylethoxy]phenyl]ethyl]cyclohexan-1-ol Chemical compound O([C@H](C)C=1C=CC=CC=1)C(C=C1)=CC=C1C(C1(O)CCCCC1)CN1CCN(C)CC1 BXFSKZGLRKVPAT-FPSALIRRSA-N 0.000 claims 1
- BXFSKZGLRKVPAT-CHQVSRGASA-N 1-[2-(4-methylpiperazin-1-yl)-1-[4-[(1s)-1-phenylethoxy]phenyl]ethyl]cyclohexan-1-ol Chemical compound O([C@@H](C)C=1C=CC=CC=1)C(C=C1)=CC=C1C(C1(O)CCCCC1)CN1CCN(C)CC1 BXFSKZGLRKVPAT-CHQVSRGASA-N 0.000 claims 1
- UAHKAIYEVWZKNK-UHFFFAOYSA-N 1-[2-(4-methylpiperazin-1-yl)-1-[4-[3-(trifluoromethoxy)phenyl]phenyl]ethyl]cyclobutan-1-ol Chemical compound C1CN(C)CCN1CC(C1(O)CCC1)C1=CC=C(C=2C=C(OC(F)(F)F)C=CC=2)C=C1 UAHKAIYEVWZKNK-UHFFFAOYSA-N 0.000 claims 1
- GEHMZOZDDSRCCU-UHFFFAOYSA-N 1-[2-(4-methylpiperazin-1-yl)-1-[4-[[2-(trifluoromethyl)phenyl]methoxy]phenyl]ethyl]cyclohexan-1-ol Chemical compound C1CN(C)CCN1CC(C1(O)CCCCC1)C(C=C1)=CC=C1OCC1=CC=CC=C1C(F)(F)F GEHMZOZDDSRCCU-UHFFFAOYSA-N 0.000 claims 1
- VBUDMVQQWMPGTI-UHFFFAOYSA-N 1-[2-(4-methylpiperazin-1-yl)-1-[4-[[3-(trifluoromethyl)phenyl]methoxy]phenyl]ethyl]cyclohexan-1-ol Chemical compound C1CN(C)CCN1CC(C1(O)CCCCC1)C(C=C1)=CC=C1OCC1=CC=CC(C(F)(F)F)=C1 VBUDMVQQWMPGTI-UHFFFAOYSA-N 0.000 claims 1
- DBODFEWUVFEWEO-UHFFFAOYSA-N 1-[2-(4-methylpiperazin-1-yl)-1-[4-[[4-(trifluoromethyl)phenyl]methoxy]phenyl]ethyl]cyclohexan-1-ol Chemical compound C1CN(C)CCN1CC(C1(O)CCCCC1)C(C=C1)=CC=C1OCC1=CC=C(C(F)(F)F)C=C1 DBODFEWUVFEWEO-UHFFFAOYSA-N 0.000 claims 1
- ACPYTJQRQFEOMI-UHFFFAOYSA-N 1-[2-(4-methylpiperazin-1-yl)-1-[4-phenylmethoxy-3-(trifluoromethoxy)phenyl]ethyl]cyclohexan-1-ol Chemical compound C1CN(C)CCN1CC(C1(O)CCCCC1)C(C=C1OC(F)(F)F)=CC=C1OCC1=CC=CC=C1 ACPYTJQRQFEOMI-UHFFFAOYSA-N 0.000 claims 1
- INDWAODVCUCVAL-UHFFFAOYSA-N 1-[2-(4-methylpiperazin-1-yl)-1-[4-phenylmethoxy-3-(trifluoromethyl)phenyl]ethyl]cyclohexan-1-ol Chemical compound C1CN(C)CCN1CC(C1(O)CCCCC1)C(C=C1C(F)(F)F)=CC=C1OCC1=CC=CC=C1 INDWAODVCUCVAL-UHFFFAOYSA-N 0.000 claims 1
- UUZZFWKLFUPHBB-UHFFFAOYSA-N 1-[2-(4-propan-2-ylpiperazin-1-yl)-1-[3-(trifluoromethoxy)phenyl]ethyl]cyclohexan-1-ol Chemical compound C1CN(C(C)C)CCN1CC(C1(O)CCCCC1)C1=CC=CC(OC(F)(F)F)=C1 UUZZFWKLFUPHBB-UHFFFAOYSA-N 0.000 claims 1
- XWKWNAZJQUMBLY-MCPYQZEQSA-N 1-[2-[(3r,5s)-3,5-dimethylpiperazin-1-yl]-1-[4-(trifluoromethoxy)phenyl]ethyl]cyclohexan-1-ol Chemical compound C1[C@@H](C)N[C@@H](C)CN1CC(C1(O)CCCCC1)C1=CC=C(OC(F)(F)F)C=C1 XWKWNAZJQUMBLY-MCPYQZEQSA-N 0.000 claims 1
- FWRGTVFNHXVOCG-UHFFFAOYSA-N 1-[2-[4-(1-hydroxy-2-methylpropan-2-yl)piperazin-1-yl]-1-[3-(trifluoromethoxy)phenyl]ethyl]cyclohexan-1-ol Chemical compound C1CN(C(C)(CO)C)CCN1CC(C1(O)CCCCC1)C1=CC=CC(OC(F)(F)F)=C1 FWRGTVFNHXVOCG-UHFFFAOYSA-N 0.000 claims 1
- UAUCZMBQJGBNAD-UHFFFAOYSA-N 1-[2-[4-(2-hydroxy-2-methylpropyl)piperazin-1-yl]-1-[3-(trifluoromethoxy)phenyl]ethyl]cyclohexan-1-ol Chemical compound C1CN(CC(C)(O)C)CCN1CC(C1(O)CCCCC1)C1=CC=CC(OC(F)(F)F)=C1 UAUCZMBQJGBNAD-UHFFFAOYSA-N 0.000 claims 1
- OLFNVMSZWXRUHS-UHFFFAOYSA-N 1-[2-[4-(cyclohexylmethyl)piperazin-1-yl]-1-(3-phenoxyphenyl)ethyl]cyclohexan-1-ol Chemical compound C1CN(CC2CCCCC2)CCN1CC(C=1C=C(OC=2C=CC=CC=2)C=CC=1)C1(O)CCCCC1 OLFNVMSZWXRUHS-UHFFFAOYSA-N 0.000 claims 1
- DNTKIXRZVHOTIK-UHFFFAOYSA-N 1-[2-[4-(cyclohexylmethyl)piperazin-1-yl]-1-(4-phenoxyphenyl)ethyl]cyclohexan-1-ol Chemical compound C1CN(CC2CCCCC2)CCN1CC(C=1C=CC(OC=2C=CC=CC=2)=CC=1)C1(O)CCCCC1 DNTKIXRZVHOTIK-UHFFFAOYSA-N 0.000 claims 1
- SKYKTINPHGPQHR-UHFFFAOYSA-N 1-[2-[4-(cyclohexylmethyl)piperazin-1-yl]-1-[4-(trifluoromethoxy)phenyl]ethyl]cyclohexan-1-ol Chemical compound C1CN(CC2CCCCC2)CCN1CC(C=1C=CC(OC(F)(F)F)=CC=1)C1(O)CCCCC1 SKYKTINPHGPQHR-UHFFFAOYSA-N 0.000 claims 1
- XFBVHRKLWFEXDI-UHFFFAOYSA-N 1-[2-piperazin-1-yl-1-(3-prop-1-ynylphenyl)ethyl]cyclohexan-1-ol Chemical compound CC#CC1=CC=CC(C(CN2CCNCC2)C2(O)CCCCC2)=C1 XFBVHRKLWFEXDI-UHFFFAOYSA-N 0.000 claims 1
- PRDNJZHVBFERHV-UHFFFAOYSA-N 1-[2-piperazin-1-yl-1-(4-prop-1-ynylphenyl)ethyl]cyclohexan-1-ol Chemical compound C1=CC(C#CC)=CC=C1C(C1(O)CCCCC1)CN1CCNCC1 PRDNJZHVBFERHV-UHFFFAOYSA-N 0.000 claims 1
- MBBDNVKWELRTOX-UHFFFAOYSA-N 1-[2-piperazin-1-yl-1-(4-thiophen-3-ylphenyl)ethyl]cyclohexan-1-ol Chemical compound C1CNCCN1CC(C=1C=CC(=CC=1)C1=CSC=C1)C1(O)CCCCC1 MBBDNVKWELRTOX-UHFFFAOYSA-N 0.000 claims 1
- NEHUOIKTKJKISZ-UHFFFAOYSA-N 1-[2-piperazin-1-yl-1-[3-(trifluoromethoxy)phenyl]ethyl]cyclobutan-1-ol Chemical compound C1CNCCN1CC(C=1C=C(OC(F)(F)F)C=CC=1)C1(O)CCC1 NEHUOIKTKJKISZ-UHFFFAOYSA-N 0.000 claims 1
- MRQDQHDPSBHAEH-UHFFFAOYSA-N 1-[2-piperazin-1-yl-1-[3-(trifluoromethoxy)phenyl]ethyl]cyclohexan-1-ol Chemical compound C1CNCCN1CC(C=1C=C(OC(F)(F)F)C=CC=1)C1(O)CCCCC1 MRQDQHDPSBHAEH-UHFFFAOYSA-N 0.000 claims 1
- IOFKGZLFJDPILD-UHFFFAOYSA-N 1-[2-piperazin-1-yl-1-[3-[3-(trifluoromethoxy)phenyl]phenyl]ethyl]cyclohexan-1-ol Chemical compound C1CNCCN1CC(C=1C=C(C=CC=1)C=1C=C(OC(F)(F)F)C=CC=1)C1(O)CCCCC1 IOFKGZLFJDPILD-UHFFFAOYSA-N 0.000 claims 1
- SJYQLVUMTVRKCW-UHFFFAOYSA-N 1-[2-piperazin-1-yl-1-[3-[4-(trifluoromethyl)phenyl]phenyl]ethyl]cyclohexan-1-ol Chemical compound C1CNCCN1CC(C=1C=C(C=CC=1)C=1C=CC(=CC=1)C(F)(F)F)C1(O)CCCCC1 SJYQLVUMTVRKCW-UHFFFAOYSA-N 0.000 claims 1
- OHMTWGZXZSRAPD-UHFFFAOYSA-N 1-[2-piperazin-1-yl-1-[4-(trifluoromethoxy)phenyl]ethyl]cyclobutan-1-ol Chemical compound C1CNCCN1CC(C=1C=CC(OC(F)(F)F)=CC=1)C1(O)CCC1 OHMTWGZXZSRAPD-UHFFFAOYSA-N 0.000 claims 1
- UTQUIHWPWAIHSN-UHFFFAOYSA-N 1-[2-piperazin-1-yl-1-[4-(trifluoromethoxy)phenyl]ethyl]cyclohexan-1-ol Chemical compound C1CNCCN1CC(C=1C=CC(OC(F)(F)F)=CC=1)C1(O)CCCCC1 UTQUIHWPWAIHSN-UHFFFAOYSA-N 0.000 claims 1
- BMNXSZZJIWUMMT-UHFFFAOYSA-N 1-[2-piperazin-1-yl-1-[4-[3-(trifluoromethoxy)phenyl]phenyl]ethyl]cyclobutan-1-ol Chemical compound C1CNCCN1CC(C=1C=CC(=CC=1)C=1C=C(OC(F)(F)F)C=CC=1)C1(O)CCC1 BMNXSZZJIWUMMT-UHFFFAOYSA-N 0.000 claims 1
- UUGJJOMSRCNIFA-UHFFFAOYSA-N 1-[2-piperazin-1-yl-1-[4-[3-(trifluoromethoxy)phenyl]phenyl]ethyl]cyclohexan-1-ol Chemical compound C1CNCCN1CC(C=1C=CC(=CC=1)C=1C=C(OC(F)(F)F)C=CC=1)C1(O)CCCCC1 UUGJJOMSRCNIFA-UHFFFAOYSA-N 0.000 claims 1
- DWMRXADZITWMQX-UHFFFAOYSA-N 1-[2-piperazin-1-yl-1-[4-[[2-(trifluoromethyl)phenyl]methoxy]phenyl]ethyl]cyclohexan-1-ol Chemical compound C1CNCCN1CC(C=1C=CC(OCC=2C(=CC=CC=2)C(F)(F)F)=CC=1)C1(O)CCCCC1 DWMRXADZITWMQX-UHFFFAOYSA-N 0.000 claims 1
- GIWZLFHCEGXSSF-UHFFFAOYSA-N 1-[2-piperazin-1-yl-1-[4-[[3-(trifluoromethyl)phenyl]methoxy]phenyl]ethyl]cyclohexan-1-ol Chemical compound C1CNCCN1CC(C=1C=CC(OCC=2C=C(C=CC=2)C(F)(F)F)=CC=1)C1(O)CCCCC1 GIWZLFHCEGXSSF-UHFFFAOYSA-N 0.000 claims 1
- SUXAWUWOXWHPNR-UHFFFAOYSA-N 1-[2-piperazin-1-yl-1-[4-[[4-(trifluoromethyl)phenyl]methoxy]phenyl]ethyl]cyclohexan-1-ol Chemical compound C1CNCCN1CC(C=1C=CC(OCC=2C=CC(=CC=2)C(F)(F)F)=CC=1)C1(O)CCCCC1 SUXAWUWOXWHPNR-UHFFFAOYSA-N 0.000 claims 1
- VNFJMNWIUNEWQB-UHFFFAOYSA-N 2,2-dimethyl-1-[2-(4-methylpiperazin-1-yl)-1-[3-(trifluoromethoxy)phenyl]ethyl]cyclopentan-1-ol Chemical compound C1CN(C)CCN1CC(C1(O)C(CCC1)(C)C)C1=CC=CC(OC(F)(F)F)=C1 VNFJMNWIUNEWQB-UHFFFAOYSA-N 0.000 claims 1
- XEHBSLOWUJPAHA-UHFFFAOYSA-N 2,2-dimethyl-1-[2-piperazin-1-yl-1-[3-(trifluoromethoxy)phenyl]ethyl]cyclopentan-1-ol Chemical compound CC1(C)CCCC1(O)C(C=1C=C(OC(F)(F)F)C=CC=1)CN1CCNCC1 XEHBSLOWUJPAHA-UHFFFAOYSA-N 0.000 claims 1
- RGSPUUZCWJENKS-UHFFFAOYSA-N 2-[4-[1-(1-hydroxycyclohexyl)-2-piperazin-1-ylethyl]phenyl]benzonitrile Chemical compound C1CNCCN1CC(C=1C=CC(=CC=1)C=1C(=CC=CC=1)C#N)C1(O)CCCCC1 RGSPUUZCWJENKS-UHFFFAOYSA-N 0.000 claims 1
- BXXQKADVEIJTPF-UHFFFAOYSA-N 3-[1-(1-hydroxycyclohexyl)-2-(4-methylpiperazin-1-yl)ethyl]benzonitrile Chemical compound C1CN(C)CCN1CC(C1(O)CCCCC1)C1=CC=CC(C#N)=C1 BXXQKADVEIJTPF-UHFFFAOYSA-N 0.000 claims 1
- UXERPKJQDAPBAM-UHFFFAOYSA-N 3-[1-(1-hydroxycyclohexyl)-2-piperazin-1-ylethyl]benzonitrile Chemical compound C1CNCCN1CC(C=1C=C(C=CC=1)C#N)C1(O)CCCCC1 UXERPKJQDAPBAM-UHFFFAOYSA-N 0.000 claims 1
- NAECKIPERDGEEQ-UHFFFAOYSA-N 3-[4-[1-(1-hydroxycyclohexyl)-2-(4-methylpiperazin-1-yl)ethyl]phenyl]benzonitrile Chemical compound C1CN(C)CCN1CC(C1(O)CCCCC1)C1=CC=C(C=2C=C(C=CC=2)C#N)C=C1 NAECKIPERDGEEQ-UHFFFAOYSA-N 0.000 claims 1
- QXKMHDQDKSKPCF-UHFFFAOYSA-N 3-[4-[1-(1-hydroxycyclohexyl)-2-piperazin-1-ylethyl]phenyl]benzonitrile Chemical compound C1CNCCN1CC(C=1C=CC(=CC=1)C=1C=C(C=CC=1)C#N)C1(O)CCCCC1 QXKMHDQDKSKPCF-UHFFFAOYSA-N 0.000 claims 1
- OYEWHHQBTAIYSE-UHFFFAOYSA-N 4-[1-(1-hydroxycyclohexyl)-2-(4-methylpiperazin-1-yl)ethyl]-2-(trifluoromethoxy)phenol Chemical compound C1CN(C)CCN1CC(C1(O)CCCCC1)C1=CC=C(O)C(OC(F)(F)F)=C1 OYEWHHQBTAIYSE-UHFFFAOYSA-N 0.000 claims 1
- XWKDFKSBYLBMNC-UHFFFAOYSA-N 4-[1-(1-hydroxycyclohexyl)-2-piperazin-1-ylethyl]-2-(trifluoromethoxy)phenol Chemical compound C1=C(OC(F)(F)F)C(O)=CC=C1C(C1(O)CCCCC1)CN1CCNCC1 XWKDFKSBYLBMNC-UHFFFAOYSA-N 0.000 claims 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 1
- CHGHYVOXOBUNLT-UHFFFAOYSA-N 5-[1-(1-hydroxycyclohexyl)-2-(4-methylpiperazin-1-yl)ethyl]-2-phenylmethoxybenzonitrile Chemical compound C1CN(C)CCN1CC(C1(O)CCCCC1)C(C=C1C#N)=CC=C1OCC1=CC=CC=C1 CHGHYVOXOBUNLT-UHFFFAOYSA-N 0.000 claims 1
- ABGKKZSURWGNON-UHFFFAOYSA-N 5-[1-(1-hydroxycyclohexyl)-2-piperazin-1-ylethyl]-2-phenylmethoxybenzonitrile Chemical compound C1CNCCN1CC(C=1C=C(C(OCC=2C=CC=CC=2)=CC=1)C#N)C1(O)CCCCC1 ABGKKZSURWGNON-UHFFFAOYSA-N 0.000 claims 1
- 229940100198 alkylating agent Drugs 0.000 claims 1
- 239000002168 alkylating agent Substances 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
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 125000005186 naphthyloxy group Chemical group C1(=CC=CC2=CC=CC=C12)O* 0.000 claims 1
- 230000000966 norepinephrine reuptake Effects 0.000 claims 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 1
- 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 1
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- 125000006239 protecting group Chemical group 0.000 claims 1
- 125000001544 thienyl group Chemical group 0.000 claims 1
- 0 C*(CC(C*)c1ccccc1)N1CC(*)CN(*)CC1 Chemical compound C*(CC(C*)c1ccccc1)N1CC(*)CN(*)CC1 0.000 description 1
Applications Claiming Priority (5)
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| US51094303P | 2003-10-14 | 2003-10-14 | |
| US56130104P | 2004-04-12 | 2004-04-12 | |
| US56999604P | 2004-05-11 | 2004-05-11 | |
| US10/963,111 US7365076B2 (en) | 2003-10-14 | 2004-10-12 | Substituted aryl cycloalkanol derivatives and methods of their use |
| PCT/US2004/033990 WO2005037809A1 (en) | 2003-10-14 | 2004-10-13 | Substituted aryl cycloalkanol derivatives and methods of their use |
Publications (2)
| Publication Number | Publication Date |
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| JP2007509076A JP2007509076A (ja) | 2007-04-12 |
| JP2007509076A5 true JP2007509076A5 (https=) | 2007-11-29 |
Family
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| JP2006535675A Withdrawn JP2007509076A (ja) | 2003-10-14 | 2004-10-13 | 置換アリールシクロアルカノイル誘導体およびその使用方法 |
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| EP (1) | EP1687288B1 (https=) |
| JP (1) | JP2007509076A (https=) |
| KR (1) | KR20070026323A (https=) |
| AT (1) | ATE384055T1 (https=) |
| AU (1) | AU2004282193A1 (https=) |
| BR (1) | BRPI0415380A (https=) |
| CA (1) | CA2540207A1 (https=) |
| CR (1) | CR8313A (https=) |
| DE (1) | DE602004011385T2 (https=) |
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| EC (1) | ECSP066505A (https=) |
| ES (1) | ES2300841T3 (https=) |
| IL (1) | IL174539A0 (https=) |
| MX (1) | MXPA06003882A (https=) |
| NO (1) | NO20061383L (https=) |
| PE (1) | PE20050478A1 (https=) |
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| TW (1) | TW200526602A (https=) |
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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 |
| GB0513702D0 (en) | 2005-07-04 | 2005-08-10 | Sterix Ltd | Compound |
| CA2629807A1 (en) * | 2005-12-05 | 2007-06-14 | Wyeth | Process for preparing substituted aryl cycloalkanol derivatives |
| US7612210B2 (en) | 2005-12-05 | 2009-11-03 | Wyeth | Process for selective synthesis of enantiomers of substituted 1-(2-amino-1-phenyl-ethyl)-cyclohexanols |
| WO2007123636A2 (en) * | 2006-03-27 | 2007-11-01 | Children's Hospital & Regional Medical Center | Compositions and methods comprising the use of cell surface displayed homing endonucleases |
| WO2026027375A1 (de) | 2024-07-29 | 2026-02-05 | Bayer Aktiengesellschaft | Hydroxy-dihydropyridinon carboxamide als schädlingsbekämpfungsmittel |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3454554A (en) * | 1960-10-14 | 1969-07-08 | Colgate Palmolive Co | Aminoalkyliminodibenzyl compounds |
| CS175831B1 (https=) * | 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 |
| 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 |
| KR100211713B1 (ko) | 1990-06-01 | 1999-08-02 | 슈테펜 엘. 네스비트 | (+)-알파-(2,3-디메톡시페닐)-1-[2-(4-플루오로페닐)에틸]-4-피페리딘메탄올 |
| US5502047A (en) * | 1993-03-22 | 1996-03-26 | Kavey; Neil B. | Treatment for insomnia |
| WO1997035586A1 (en) | 1996-03-25 | 1997-10-02 | Eli Lilly And Company | Method for treating pain |
| EA200000890A1 (ru) | 1998-03-02 | 2001-02-26 | Эли Лилли Энд Компани | Гидрохлорид флуоксетина для уменьшения "приливов" (приступообразных ощущений жара (при климактерическом синдроме)) |
| DE60039132D1 (de) | 1999-04-06 | 2008-07-17 | Sepracor Inc | O-Desmethylvenlafaxin-Succinat |
| US6465458B1 (en) * | 1999-07-01 | 2002-10-15 | Pharmacia & Upjohn Company | Method of treating or preventing chronic pain with a highly selective norepinephrine reuptake inhibitor |
| EP1864967A1 (en) | 2001-02-12 | 2007-12-12 | Wyeth | Method for preparing O-desmethyl-venlafaxine |
| EP1383495A1 (en) | 2001-03-29 | 2004-01-28 | Eli Lilly And Company | Duloxetine for treatment of hot flashes |
| 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 |
| JP2005526079A (ja) | 2002-03-15 | 2005-09-02 | サイプレス バイオサイエンス， インコーポレイテッド | 内蔵痛症候群を処置するためのｎｅおよび５−ｈｔ再取り込み阻害剤 |
| TW200402289A (en) * | 2002-05-17 | 2004-02-16 | Wyeth Corp | Methods of treating gastrointestinary and genitourinary pain disorders |
| ITMI20021328A1 (it) | 2002-06-14 | 2003-12-15 | Recordati Ind Chimica E Farma | Nuove piperazine 1,4 - disostituite |
| ITMI20021327A1 (it) | 2002-06-14 | 2003-12-15 | Recordati Chem Pharm | Nuove ossialchilpiperazine |
| EP1530476A1 (en) | 2002-08-14 | 2005-05-18 | Pharmacia & Upjohn Company LLC | Use of reboxetine for the treatment of hot flashes |
| US20040152710A1 (en) | 2002-10-15 | 2004-08-05 | Deecher Darlene Coleman | Use of norepinephrine reuptake modulators for preventing and treating vasomotor symptoms |
| US7345096B2 (en) * | 2002-10-15 | 2008-03-18 | Wyeth | 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 |
| JP2005336172A (ja) | 2004-04-26 | 2005-12-08 | Japan Tobacco Inc | 腎虚血再灌流障害治療又は予防薬 |
| WO2006055854A2 (en) | 2004-11-17 | 2006-05-26 | Cypress Bioscience, Inc. | Methods for reducing the side effects associated with mirtazapine treatment |
-
2004
- 2004-10-12 US US10/963,111 patent/US7365076B2/en not_active Expired - Fee Related
- 2004-10-13 KR KR1020067007287A patent/KR20070026323A/ko not_active Withdrawn
- 2004-10-13 WO PCT/US2004/033990 patent/WO2005037809A1/en not_active Ceased
- 2004-10-13 AU AU2004282193A patent/AU2004282193A1/en not_active Withdrawn
- 2004-10-13 EP EP04795187A patent/EP1687288B1/en not_active Expired - Lifetime
- 2004-10-13 MX MXPA06003882A patent/MXPA06003882A/es active IP Right Grant
- 2004-10-13 DK DK04795187T patent/DK1687288T3/da active
- 2004-10-13 JP JP2006535675A patent/JP2007509076A/ja not_active Withdrawn
- 2004-10-13 ES ES04795187T patent/ES2300841T3/es not_active Expired - Lifetime
- 2004-10-13 AT AT04795187T patent/ATE384055T1/de not_active IP Right Cessation
- 2004-10-13 DE DE602004011385T patent/DE602004011385T2/de not_active Expired - Fee Related
- 2004-10-13 CA CA002540207A patent/CA2540207A1/en not_active Abandoned
- 2004-10-13 BR BRPI0415380-4A patent/BRPI0415380A/pt not_active IP Right Cessation
- 2004-10-13 PL PL04795187T patent/PL1687288T3/pl unknown
- 2004-10-13 TW TW093131003A patent/TW200526602A/zh unknown
- 2004-10-14 PE PE2004000996A patent/PE20050478A1/es not_active Application Discontinuation
-
2006
- 2006-03-23 IL IL174539A patent/IL174539A0/en unknown
- 2006-03-23 CR CR8313A patent/CR8313A/es unknown
- 2006-03-27 NO NO20061383A patent/NO20061383L/no not_active Application Discontinuation
- 2006-04-12 EC EC2006006505A patent/ECSP066505A/es unknown
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2008
- 2008-02-14 US US12/031,187 patent/US7550456B2/en not_active Expired - Fee Related
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