JP2008504278A5 - - Google Patents
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- Publication number
- JP2008504278A5 JP2008504278A5 JP2007518299A JP2007518299A JP2008504278A5 JP 2008504278 A5 JP2008504278 A5 JP 2008504278A5 JP 2007518299 A JP2007518299 A JP 2007518299A JP 2007518299 A JP2007518299 A JP 2007518299A JP 2008504278 A5 JP2008504278 A5 JP 2008504278A5
- Authority
- JP
- Japan
- Prior art keywords
- methylpropanoyl
- spiro
- benzofuran
- pyrrolidin
- 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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- 125000000753 cycloalkyl group Chemical group 0.000 claims 42
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 42
- 150000001875 compounds Chemical class 0.000 claims 41
- 125000003118 aryl group Chemical group 0.000 claims 38
- 125000000217 alkyl group Chemical group 0.000 claims 37
- 125000001072 heteroaryl group Chemical group 0.000 claims 26
- 125000005843 halogen group Chemical group 0.000 claims 22
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 18
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 18
- 229910052760 oxygen Inorganic materials 0.000 claims 18
- 229910052717 sulfur Inorganic materials 0.000 claims 14
- 125000003710 aryl alkyl group Chemical group 0.000 claims 13
- 229910052799 carbon Inorganic materials 0.000 claims 13
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims 12
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 12
- 125000003545 alkoxy group Chemical group 0.000 claims 12
- 229910052739 hydrogen Inorganic materials 0.000 claims 12
- 125000003282 alkyl amino group Chemical group 0.000 claims 11
- 125000004663 dialkyl amino group Chemical group 0.000 claims 11
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 11
- 125000005466 alkylenyl group Chemical group 0.000 claims 10
- 125000004432 carbon atom Chemical group C* 0.000 claims 10
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 10
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 9
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 8
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 7
- -1 3- (trifluoromethyl) -phenyl Chemical group 0.000 claims 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 6
- 125000005018 aryl alkenyl group Chemical group 0.000 claims 4
- 125000005015 aryl alkynyl group Chemical group 0.000 claims 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims 4
- 125000004966 cyanoalkyl group Chemical group 0.000 claims 4
- 201000010099 disease Diseases 0.000 claims 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 4
- 125000004447 heteroarylalkenyl group Chemical group 0.000 claims 4
- 125000005312 heteroarylalkynyl group Chemical group 0.000 claims 4
- 125000005885 heterocycloalkylalkyl group Chemical group 0.000 claims 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 4
- ATQVDTHJHUFVMS-UHFFFAOYSA-N 1'-[2-(4-chlorophenyl)-2-methylpropanoyl]spiro[2-benzofuran-3,3'-pyrrolidine]-1-one Chemical compound C1CC2(C3=CC=CC=C3C(=O)O2)CN1C(=O)C(C)(C)C1=CC=C(Cl)C=C1 ATQVDTHJHUFVMS-UHFFFAOYSA-N 0.000 claims 3
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 3
- 125000004429 atom Chemical group 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 3
- UODMYZNRUHKUJO-NRFANRHFSA-N (3r)-1'-[2-(2,4-dichlorophenoxy)-2-methylpropanoyl]spiro[2-benzofuran-3,3'-pyrrolidine]-1-one Chemical compound C([C@@]1(CC2)C3=CC=CC=C3C(=O)O1)N2C(=O)C(C)(C)OC1=CC=C(Cl)C=C1Cl UODMYZNRUHKUJO-NRFANRHFSA-N 0.000 claims 2
- OCYPMIJRVBVYSZ-NRFANRHFSA-N (3r)-1'-[2-(4-chlorophenoxy)-2-methylpropanoyl]spiro[2-benzofuran-3,3'-pyrrolidine]-1-one Chemical compound C([C@@]1(CC2)C3=CC=CC=C3C(=O)O1)N2C(=O)C(C)(C)OC1=CC=C(Cl)C=C1 OCYPMIJRVBVYSZ-NRFANRHFSA-N 0.000 claims 2
- ATQVDTHJHUFVMS-NRFANRHFSA-N (3r)-1'-[2-(4-chlorophenyl)-2-methylpropanoyl]spiro[2-benzofuran-3,3'-pyrrolidine]-1-one Chemical compound C([C@@]1(CC2)C3=CC=CC=C3C(=O)O1)N2C(=O)C(C)(C)C1=CC=C(Cl)C=C1 ATQVDTHJHUFVMS-NRFANRHFSA-N 0.000 claims 2
- 125000006648 (C1-C8) haloalkyl group Chemical group 0.000 claims 2
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims 2
- WQFSFVIUMVGPLM-UHFFFAOYSA-N 1'-[2-[4-(4-fluorophenyl)phenoxy]-2-methylpropanoyl]spiro[2-benzofuran-3,3'-pyrrolidine]-1-one Chemical compound C1CC2(C3=CC=CC=C3C(=O)O2)CN1C(=O)C(C)(C)OC(C=C1)=CC=C1C1=CC=C(F)C=C1 WQFSFVIUMVGPLM-UHFFFAOYSA-N 0.000 claims 2
- KAHYZHUJHHQKIT-UHFFFAOYSA-N 1'-[2-methyl-2-(4-pyridin-2-ylphenoxy)propanoyl]spiro[2-benzofuran-3,3'-pyrrolidine]-1-one Chemical compound C1CC2(C3=CC=CC=C3C(=O)O2)CN1C(=O)C(C)(C)OC(C=C1)=CC=C1C1=CC=CC=N1 KAHYZHUJHHQKIT-UHFFFAOYSA-N 0.000 claims 2
- XTJCDJOXIGHEGM-UHFFFAOYSA-N 2-[4-(2-methyl-1-oxo-1-spiro[1h-2-benzofuran-3,3'-pyrrolidine]-1'-ylpropan-2-yl)oxyphenyl]acetonitrile Chemical compound C1CC2(C3=CC=CC=C3CO2)CN1C(=O)C(C)(C)OC1=CC=C(CC#N)C=C1 XTJCDJOXIGHEGM-UHFFFAOYSA-N 0.000 claims 2
- KUUUQRYJGLQMNG-UHFFFAOYSA-N 2-[4-[2-methyl-1-oxo-1-(3-oxospiro[2-benzofuran-1,3'-pyrrolidine]-1'-yl)propan-2-yl]oxyphenyl]acetonitrile Chemical compound C1CC2(C3=CC=CC=C3C(=O)O2)CN1C(=O)C(C)(C)OC1=CC=C(CC#N)C=C1 KUUUQRYJGLQMNG-UHFFFAOYSA-N 0.000 claims 2
- HDSHKTDCDJGBTD-UHFFFAOYSA-N 4-[2-methyl-1-oxo-1-(3-oxospiro[2-benzofuran-1,3'-pyrrolidine]-1'-yl)propan-2-yl]oxybenzonitrile Chemical compound C1CC2(C3=CC=CC=C3C(=O)O2)CN1C(=O)C(C)(C)OC1=CC=C(C#N)C=C1 HDSHKTDCDJGBTD-UHFFFAOYSA-N 0.000 claims 2
- 208000024172 Cardiovascular disease Diseases 0.000 claims 2
- 208000032928 Dyslipidaemia Diseases 0.000 claims 2
- 208000031226 Hyperlipidaemia Diseases 0.000 claims 2
- 208000017170 Lipid metabolism disease Diseases 0.000 claims 2
- 125000003342 alkenyl group Chemical group 0.000 claims 2
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims 2
- 125000005160 aryl oxy alkyl group Chemical group 0.000 claims 2
- 125000004104 aryloxy group Chemical group 0.000 claims 2
- 125000005356 cycloalkylalkenyl group Chemical group 0.000 claims 2
- 125000005357 cycloalkylalkynyl group Chemical group 0.000 claims 2
- 125000005114 heteroarylalkoxy group Chemical group 0.000 claims 2
- 125000005326 heteroaryloxy alkyl group Chemical group 0.000 claims 2
- 125000005553 heteroaryloxy group Chemical group 0.000 claims 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 239000000651 prodrug Substances 0.000 claims 2
- 229940002612 prodrug Drugs 0.000 claims 2
- 125000004076 pyridyl group Chemical group 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- QPVPSYUMCRZFBK-FQEVSTJZSA-N (1r)-1'-[2-(4-chlorophenyl)-2-methylpropanoyl]spiro[furo[3,4-c]pyridine-1,3'-pyrrolidine]-3-one Chemical compound C([C@@]1(CC2)C3=CC=NC=C3C(=O)O1)N2C(=O)C(C)(C)C1=CC=C(Cl)C=C1 QPVPSYUMCRZFBK-FQEVSTJZSA-N 0.000 claims 1
- SHTGXPCSYKYFQC-NRFANRHFSA-N (3r)-1'-(2-methyl-2-phenoxypropanoyl)spiro[2-benzofuran-3,3'-pyrrolidine]-1-one Chemical compound C([C@@]1(CC2)C3=CC=CC=C3C(=O)O1)N2C(=O)C(C)(C)OC1=CC=CC=C1 SHTGXPCSYKYFQC-NRFANRHFSA-N 0.000 claims 1
- WHTOUDPYVXVMCR-FQEVSTJZSA-N (3r)-1'-(2-methyl-2-pyridin-3-ylpropanoyl)spiro[2-benzofuran-3,3'-pyrrolidine]-1-one Chemical compound C([C@@]1(CC2)C3=CC=CC=C3C(=O)O1)N2C(=O)C(C)(C)C1=CC=CN=C1 WHTOUDPYVXVMCR-FQEVSTJZSA-N 0.000 claims 1
- WKQZRRUPYUBDNC-NRFANRHFSA-N (3r)-1'-[2-(3,4-dichlorophenoxy)-2-methylpropanoyl]spiro[2-benzofuran-3,3'-pyrrolidine]-1-one Chemical compound C([C@@]1(CC2)C3=CC=CC=C3C(=O)O1)N2C(=O)C(C)(C)OC1=CC=C(Cl)C(Cl)=C1 WKQZRRUPYUBDNC-NRFANRHFSA-N 0.000 claims 1
- XJOUTPBUJBTIQV-QFIPXVFZSA-N (3r)-1'-[2-(4-chloro-2-methylphenoxy)-2-methylpropanoyl]spiro[2-benzofuran-3,3'-pyrrolidine]-1-one Chemical compound CC1=CC(Cl)=CC=C1OC(C)(C)C(=O)N1C[C@]2(C3=CC=CC=C3C(=O)O2)CC1 XJOUTPBUJBTIQV-QFIPXVFZSA-N 0.000 claims 1
- WPQOTWRUSHIAGI-NRFANRHFSA-N (3r)-1'-[2-(4-chloro-3-fluorophenoxy)-2-methylpropanoyl]spiro[2-benzofuran-3,3'-pyrrolidine]-1-one Chemical compound C([C@@]1(CC2)C3=CC=CC=C3C(=O)O1)N2C(=O)C(C)(C)OC1=CC=C(Cl)C(F)=C1 WPQOTWRUSHIAGI-NRFANRHFSA-N 0.000 claims 1
- CYIOSJYCVGCCNI-MHZLTWQESA-N (3r)-1'-[2-[4-(4-acetylpiperazin-1-yl)phenyl]-2-methylpropanoyl]spiro[2-benzofuran-3,3'-pyrrolidine]-1-one Chemical compound C1CN(C(=O)C)CCN1C1=CC=C(C(C)(C)C(=O)N2C[C@@]3(CC2)C2=CC=CC=C2C(=O)O3)C=C1 CYIOSJYCVGCCNI-MHZLTWQESA-N 0.000 claims 1
- QISWPTPETJRXDN-LJAQVGFWSA-N (3r)-1'-[2-[4-(4-butylsulfonylpiperazin-1-yl)phenyl]-2-methylpropanoyl]spiro[2-benzofuran-3,3'-pyrrolidine]-1-one Chemical compound C1CN(S(=O)(=O)CCCC)CCN1C1=CC=C(C(C)(C)C(=O)N2C[C@@]3(CC2)C2=CC=CC=C2C(=O)O3)C=C1 QISWPTPETJRXDN-LJAQVGFWSA-N 0.000 claims 1
- XBKRVULTJYHCTL-MHZLTWQESA-N (3r)-1'-[2-[4-(4-ethylsulfonylpiperazin-1-yl)phenyl]-2-methylpropanoyl]spiro[2-benzofuran-3,3'-pyrrolidine]-1-one Chemical compound C1CN(S(=O)(=O)CC)CCN1C1=CC=C(C(C)(C)C(=O)N2C[C@@]3(CC2)C2=CC=CC=C2C(=O)O3)C=C1 XBKRVULTJYHCTL-MHZLTWQESA-N 0.000 claims 1
- QTBLOBNFNZPKFF-LJAQVGFWSA-N (3r)-1'-[2-[4-[4-(cyclopropanecarbonyl)piperazin-1-yl]phenyl]-2-methylpropanoyl]spiro[2-benzofuran-3,3'-pyrrolidine]-1-one Chemical compound C([C@@]1(CC2)C3=CC=CC=C3C(=O)O1)N2C(=O)C(C)(C)C(C=C1)=CC=C1N(CC1)CCN1C(=O)C1CC1 QTBLOBNFNZPKFF-LJAQVGFWSA-N 0.000 claims 1
- WKMNTSOSEMOOSV-NRFANRHFSA-N (3r)-1'-[2-[4-chloro-3-(trifluoromethyl)phenoxy]-2-methylpropanoyl]spiro[2-benzofuran-3,3'-pyrrolidine]-1-one Chemical compound C([C@@]1(CC2)C3=CC=CC=C3C(=O)O1)N2C(=O)C(C)(C)OC1=CC=C(Cl)C(C(F)(F)F)=C1 WKMNTSOSEMOOSV-NRFANRHFSA-N 0.000 claims 1
- OARNQOCYJNZBGM-UQIIZPHYSA-N (3r)-1'-[2-methyl-2-(4-piperazin-1-ylphenoxy)propanoyl]spiro[2-benzofuran-3,3'-pyrrolidine]-1-one;hydrochloride Chemical compound Cl.C([C@@]1(CC2)C3=CC=CC=C3C(=O)O1)N2C(=O)C(C)(C)OC(C=C1)=CC=C1N1CCNCC1 OARNQOCYJNZBGM-UQIIZPHYSA-N 0.000 claims 1
- KAFHHDHKQMCYLH-VWLOTQADSA-N (3r)-1'-[2-methyl-2-[4-(2-oxopyrrolidin-1-yl)phenyl]propanoyl]spiro[2-benzofuran-3,3'-pyrrolidine]-1-one Chemical compound C([C@@]1(CC2)C3=CC=CC=C3C(=O)O1)N2C(=O)C(C)(C)C(C=C1)=CC=C1N1CCCC1=O KAFHHDHKQMCYLH-VWLOTQADSA-N 0.000 claims 1
- WKSOZARXYWMGOZ-SANMLTNESA-N (3r)-1'-[2-methyl-2-[4-(4-methylsulfonylpiperazin-1-yl)phenyl]propanoyl]spiro[2-benzofuran-3,3'-pyrrolidine]-1-one Chemical compound C([C@@]1(CC2)C3=CC=CC=C3C(=O)O1)N2C(=O)C(C)(C)C(C=C1)=CC=C1N1CCN(S(C)(=O)=O)CC1 WKSOZARXYWMGOZ-SANMLTNESA-N 0.000 claims 1
- ZYAMOJQZDATXKO-NDEPHWFRSA-N (3r)-1'-[2-methyl-2-[4-(4-propanoylpiperazin-1-yl)phenyl]propanoyl]spiro[2-benzofuran-3,3'-pyrrolidine]-1-one Chemical compound C1CN(C(=O)CC)CCN1C1=CC=C(C(C)(C)C(=O)N2C[C@@]3(CC2)C2=CC=CC=C2C(=O)O3)C=C1 ZYAMOJQZDATXKO-NDEPHWFRSA-N 0.000 claims 1
- OSAGKDILXRGDAP-NRFANRHFSA-N (3r)-1'-[2-methyl-2-[4-(trifluoromethyl)phenoxy]propanoyl]spiro[2-benzofuran-3,3'-pyrrolidine]-1-one Chemical compound C([C@@]1(CC2)C3=CC=CC=C3C(=O)O1)N2C(=O)C(C)(C)OC1=CC=C(C(F)(F)F)C=C1 OSAGKDILXRGDAP-NRFANRHFSA-N 0.000 claims 1
- RFBWJNWKFHATCE-LJAQVGFWSA-N (3r)-1'-[2-methyl-2-[4-[4-(2-methylpropanoyl)piperazin-1-yl]phenyl]propanoyl]spiro[2-benzofuran-3,3'-pyrrolidine]-1-one Chemical compound C1CN(C(=O)C(C)C)CCN1C1=CC=C(C(C)(C)C(=O)N2C[C@@]3(CC2)C2=CC=CC=C2C(=O)O3)C=C1 RFBWJNWKFHATCE-LJAQVGFWSA-N 0.000 claims 1
- VJOXVBDGUVIAHF-QFIPXVFZSA-N (3r)-1'-[3-(4-chlorophenyl)-2,2-dimethylpropanoyl]spiro[2-benzofuran-3,3'-pyrrolidine]-1-one Chemical compound C([C@@]1(CC2)C3=CC=CC=C3C(=O)O1)N2C(=O)C(C)(C)CC1=CC=C(Cl)C=C1 VJOXVBDGUVIAHF-QFIPXVFZSA-N 0.000 claims 1
- XSXBMTIKWSOBJL-UHFFFAOYSA-N 1'-(2-methyl-2-phenylsulfanylpropanoyl)spiro[2-benzofuran-3,3'-pyrrolidine]-1-one Chemical compound C1CC2(C3=CC=CC=C3C(=O)O2)CN1C(=O)C(C)(C)SC1=CC=CC=C1 XSXBMTIKWSOBJL-UHFFFAOYSA-N 0.000 claims 1
- FTAZPXUDJIEEOG-UHFFFAOYSA-N 1'-[2-(4-chlorophenoxy)-2-methylpropanoyl]-7-fluorospiro[furo[3,4-c]pyridine-1,3'-pyrrolidine]-3-one Chemical compound C1CC2(C3=C(F)C=NC=C3C(=O)O2)CN1C(=O)C(C)(C)OC1=CC=C(Cl)C=C1 FTAZPXUDJIEEOG-UHFFFAOYSA-N 0.000 claims 1
- FJMMQAIXYYITHQ-UHFFFAOYSA-N 1'-[2-(4-chlorophenoxy)-2-methylpropanoyl]spiro[furo[3,4-c]pyridine-1,3'-pyrrolidine]-3-one Chemical compound C1CC2(C3=CC=NC=C3C(=O)O2)CN1C(=O)C(C)(C)OC1=CC=C(Cl)C=C1 FJMMQAIXYYITHQ-UHFFFAOYSA-N 0.000 claims 1
- MADYXNAGNKDPJM-UHFFFAOYSA-N 1'-[2-(4-chlorophenyl)-2-methylpropanoyl]spiro[furo[3,4-b]pyridine-5,3'-pyrrolidine]-7-one Chemical compound C1CC2(C3=CC=CN=C3C(=O)O2)CN1C(=O)C(C)(C)C1=CC=C(Cl)C=C1 MADYXNAGNKDPJM-UHFFFAOYSA-N 0.000 claims 1
- QPVPSYUMCRZFBK-UHFFFAOYSA-N 1'-[2-(4-chlorophenyl)-2-methylpropanoyl]spiro[furo[3,4-c]pyridine-1,3'-pyrrolidine]-3-one Chemical compound C1CC2(C3=CC=NC=C3C(=O)O2)CN1C(=O)C(C)(C)C1=CC=C(Cl)C=C1 QPVPSYUMCRZFBK-UHFFFAOYSA-N 0.000 claims 1
- UNNPELYFYFEOQG-UHFFFAOYSA-N 1'-[2-(4-chlorophenyl)sulfanyl-2-methylpropanoyl]spiro[2-benzofuran-3,3'-pyrrolidine]-1-one Chemical compound C1CC2(C3=CC=CC=C3C(=O)O2)CN1C(=O)C(C)(C)SC1=CC=C(Cl)C=C1 UNNPELYFYFEOQG-UHFFFAOYSA-N 0.000 claims 1
- HYLXSIXWZDGVCD-UHFFFAOYSA-N 1'-[2-[(2-chlorophenyl)methylsulfanyl]-2-methylpropanoyl]spiro[2-benzofuran-3,3'-pyrrolidine]-1-one Chemical compound C1CC2(C3=CC=CC=C3C(=O)O2)CN1C(=O)C(C)(C)SCC1=CC=CC=C1Cl HYLXSIXWZDGVCD-UHFFFAOYSA-N 0.000 claims 1
- FPZZQJXSHICZJG-UHFFFAOYSA-N 1-(1,3,3a,4,5,9b-hexahydrobenzo[e]isoindol-2-yl)-2-(4-chlorophenyl)-2-methylpropan-1-one Chemical compound C1C2CCC3=CC=CC=C3C2CN1C(=O)C(C)(C)C1=CC=C(Cl)C=C1 FPZZQJXSHICZJG-UHFFFAOYSA-N 0.000 claims 1
- BXXWSPXPCHFATD-UHFFFAOYSA-N 1-(1,3,3a,4,5,9b-hexahydrobenzo[e]isoindol-2-yl)-2-[(2-chlorophenyl)methylsulfanyl]-2-methylpropan-1-one Chemical compound C1C2CCC3=CC=CC=C3C2CN1C(=O)C(C)(C)SCC1=CC=CC=C1Cl BXXWSPXPCHFATD-UHFFFAOYSA-N 0.000 claims 1
- NKNZXAVPKLICKD-UHFFFAOYSA-N 1-(1,3,3a,4,5,9b-hexahydrobenzo[e]isoindol-2-yl)-2-methyl-2-phenylsulfanylpropan-1-one Chemical compound C1C2CCC3=CC=CC=C3C2CN1C(=O)C(C)(C)SC1=CC=CC=C1 NKNZXAVPKLICKD-UHFFFAOYSA-N 0.000 claims 1
- XUHUPPIWAHHSPH-UHFFFAOYSA-N 1-(3,3a,4,9b-tetrahydro-1h-chromeno[3,4-c]pyrrol-2-yl)-2-(4-chlorophenyl)-2-methylpropan-1-one Chemical compound C1C2COC3=CC=CC=C3C2CN1C(=O)C(C)(C)C1=CC=C(Cl)C=C1 XUHUPPIWAHHSPH-UHFFFAOYSA-N 0.000 claims 1
- OJYHKAKOEVHLFT-UHFFFAOYSA-N 1-(3,4-dihydro-1h-isoquinolin-2-yl)-2-methyl-2-phenylsulfanylpropan-1-one Chemical compound C1CC2=CC=CC=C2CN1C(=O)C(C)(C)SC1=CC=CC=C1 OJYHKAKOEVHLFT-UHFFFAOYSA-N 0.000 claims 1
- CWHBIQYCDHYJHZ-UHFFFAOYSA-N 1-(5,7-dihydro-4h-thieno[2,3-c]pyridin-6-yl)-2-methyl-2-phenylsulfanylpropan-1-one Chemical compound C1CC=2C=CSC=2CN1C(=O)C(C)(C)SC1=CC=CC=C1 CWHBIQYCDHYJHZ-UHFFFAOYSA-N 0.000 claims 1
- HXMVJVGBGOOARQ-UHFFFAOYSA-N 1-(azepan-1-yl)-2-(4-chlorophenyl)-2-methylpropan-1-one Chemical compound C=1C=C(Cl)C=CC=1C(C)(C)C(=O)N1CCCCCC1 HXMVJVGBGOOARQ-UHFFFAOYSA-N 0.000 claims 1
- VWJSJMJXFRGAAE-HUUCEWRRSA-N 1-[(4ar,8as)-3,4,4a,5,6,7,8,8a-octahydro-1h-isoquinolin-2-yl]-2-(4-chlorophenyl)sulfanyl-2-methylpropan-1-one Chemical compound C([C@H]1CCCC[C@@H]1CC1)N1C(=O)C(C)(C)SC1=CC=C(Cl)C=C1 VWJSJMJXFRGAAE-HUUCEWRRSA-N 0.000 claims 1
- CQHBTIPERVSBFF-UHFFFAOYSA-N 1-[3-(3-chlorophenyl)pyrrolidin-1-yl]-2-(3,4-dichlorophenyl)-2-methylpropan-1-one Chemical compound C=1C=C(Cl)C(Cl)=CC=1C(C)(C)C(=O)N(C1)CCC1C1=CC=CC(Cl)=C1 CQHBTIPERVSBFF-UHFFFAOYSA-N 0.000 claims 1
- WOTTZQOYHYRMDU-UHFFFAOYSA-N 1-[3-(3-fluorophenyl)pyrrolidin-1-yl]-2-methyl-2-phenylsulfanylpropan-1-one Chemical compound C1CC(C=2C=C(F)C=CC=2)CN1C(=O)C(C)(C)SC1=CC=CC=C1 WOTTZQOYHYRMDU-UHFFFAOYSA-N 0.000 claims 1
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| US20050288317A1 (en) * | 2004-06-24 | 2005-12-29 | Wenqing Yao | Amido compounds and their use as pharmaceuticals |
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-
2005
- 2005-06-23 CA CA002571258A patent/CA2571258A1/en not_active Abandoned
- 2005-06-23 MX MXPA06014572A patent/MXPA06014572A/es not_active Application Discontinuation
- 2005-06-23 WO PCT/US2005/022411 patent/WO2006002349A1/en not_active Ceased
- 2005-06-23 BR BRPI0512410-7A patent/BRPI0512410A/pt not_active IP Right Cessation
- 2005-06-23 KR KR1020067027142A patent/KR20070024639A/ko not_active Ceased
- 2005-06-23 EP EP05762543A patent/EP1758582A4/en not_active Withdrawn
- 2005-06-23 EA EA200700118A patent/EA200700118A1/ru unknown
- 2005-06-23 US US11/159,724 patent/US20060009471A1/en not_active Abandoned
- 2005-06-23 SG SG201004456-8A patent/SG163518A1/en unknown
- 2005-06-23 AU AU2005258248A patent/AU2005258248A1/en not_active Abandoned
- 2005-06-23 JP JP2007518299A patent/JP2008504278A/ja active Pending
- 2005-06-23 NZ NZ551602A patent/NZ551602A/en not_active IP Right Cessation
-
2006
- 2006-11-23 IL IL179519A patent/IL179519A/en not_active IP Right Cessation
- 2006-12-06 CR CR8796A patent/CR8796A/es not_active Application Discontinuation
- 2006-12-26 EC EC2006007113A patent/ECSP067113A/es unknown
-
2007
- 2007-01-19 NO NO20070372A patent/NO20070372L/no not_active Application Discontinuation
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