JP2007530698A5 - - Google Patents
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- Publication number
- JP2007530698A5 JP2007530698A5 JP2007506412A JP2007506412A JP2007530698A5 JP 2007530698 A5 JP2007530698 A5 JP 2007530698A5 JP 2007506412 A JP2007506412 A JP 2007506412A JP 2007506412 A JP2007506412 A JP 2007506412A JP 2007530698 A5 JP2007530698 A5 JP 2007530698A5
- Authority
- JP
- Japan
- Prior art keywords
- pyrrolidin
- ylmethyl
- methanone
- biphenyl
- fluoro
- 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.)
- Granted
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 33
- 229910052757 nitrogen Inorganic materials 0.000 claims 20
- 150000001875 compounds Chemical class 0.000 claims 12
- 229910052736 halogen Inorganic materials 0.000 claims 12
- 150000003839 salts Chemical class 0.000 claims 11
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 7
- 229910052799 carbon Inorganic materials 0.000 claims 7
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 7
- -1 6-amino-5-hydroxy-pyridin-3-yl Chemical group 0.000 claims 5
- 239000003937 drug carrier Substances 0.000 claims 5
- 239000008194 pharmaceutical composition Substances 0.000 claims 5
- 125000006555 (C3-C5) cycloalkyl group Chemical group 0.000 claims 4
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 3
- 125000004429 atom Chemical group 0.000 claims 3
- PJMFIOFUKNHHPR-UGNFMNBCSA-N [(2s)-2-[(2-methylpyrrolidin-1-yl)methyl]pyrrolidin-1-yl]-[4-[4-(trifluoromethyl)phenyl]phenyl]methanone Chemical class CC1CCCN1C[C@H]1N(C(=O)C=2C=CC(=CC=2)C=2C=CC(=CC=2)C(F)(F)F)CCC1 PJMFIOFUKNHHPR-UGNFMNBCSA-N 0.000 claims 2
- GNDSNTWJRKRRHP-XLIONFOSSA-N [2-fluoro-4-(4-methylsulfonylphenyl)phenyl]-[(2s)-2-[[(2r)-2-methylpyrrolidin-1-yl]methyl]pyrrolidin-1-yl]methanone Chemical compound C[C@@H]1CCCN1C[C@H]1N(C(=O)C=2C(=CC(=CC=2)C=2C=CC(=CC=2)S(C)(=O)=O)F)CCC1 GNDSNTWJRKRRHP-XLIONFOSSA-N 0.000 claims 2
- 125000005842 heteroatom Chemical group 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 125000006413 ring segment Chemical group 0.000 claims 2
- 229910052717 sulfur Inorganic materials 0.000 claims 2
- PLQRZIDCUXKNKH-KRWDZBQOSA-N (2,6-difluoro-4-pyridin-3-ylphenyl)-[(2s)-2-(pyrrolidin-1-ylmethyl)pyrrolidin-1-yl]methanone Chemical compound C([C@@H]1CCCN1C(=O)C1=C(F)C=C(C=C1F)C=1C=NC=CC=1)N1CCCC1 PLQRZIDCUXKNKH-KRWDZBQOSA-N 0.000 claims 1
- WEEOUXRRVMQJTQ-KRWDZBQOSA-N (2,6-difluoro-4-pyridin-4-ylphenyl)-[(2s)-2-(pyrrolidin-1-ylmethyl)pyrrolidin-1-yl]methanone Chemical compound C([C@@H]1CCCN1C(=O)C1=C(F)C=C(C=C1F)C=1C=CN=CC=1)N1CCCC1 WEEOUXRRVMQJTQ-KRWDZBQOSA-N 0.000 claims 1
- SMQQBMYGVOGVIL-INIZCTEOSA-N (2,6-difluoro-4-pyrimidin-5-ylphenyl)-[(2s)-2-(pyrrolidin-1-ylmethyl)pyrrolidin-1-yl]methanone Chemical compound C([C@@H]1CCCN1C(=O)C1=C(F)C=C(C=C1F)C=1C=NC=NC=1)N1CCCC1 SMQQBMYGVOGVIL-INIZCTEOSA-N 0.000 claims 1
- NTTBOTMVBUMIQF-KRWDZBQOSA-N (2-fluoro-3-pyridin-4-ylphenyl)-[(2s)-2-(pyrrolidin-1-ylmethyl)pyrrolidin-1-yl]methanone Chemical compound FC1=C(C(=O)N2[C@@H](CCC2)CN2CCCC2)C=CC=C1C1=CC=NC=C1 NTTBOTMVBUMIQF-KRWDZBQOSA-N 0.000 claims 1
- QWLCBUMYDXLAAJ-FYZYNONXSA-N (2-fluoro-4-phenylphenyl)-[(2s)-2-(pyrrolidin-1-ylmethyl)pyrrolidin-1-yl]methanone;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C([C@@H]1CCCN1C(=O)C1=CC=C(C=C1F)C=1C=CC=CC=1)N1CCCC1 QWLCBUMYDXLAAJ-FYZYNONXSA-N 0.000 claims 1
- MLEVLKCXZPTQBP-SFHVURJKSA-N (2-fluoro-4-pyridin-4-ylphenyl)-[(2s)-2-(pyrrolidin-1-ylmethyl)pyrrolidin-1-yl]methanone Chemical compound C([C@@H]1CCCN1C(=O)C1=CC=C(C=C1F)C=1C=CN=CC=1)N1CCCC1 MLEVLKCXZPTQBP-SFHVURJKSA-N 0.000 claims 1
- JRDHVNBHNKIBQP-KRWDZBQOSA-N (2-fluoro-4-pyrimidin-5-ylphenyl)-[(2s)-2-(pyrrolidin-1-ylmethyl)pyrrolidin-1-yl]methanone Chemical compound C([C@@H]1CCCN1C(=O)C1=CC=C(C=C1F)C=1C=NC=NC=1)N1CCCC1 JRDHVNBHNKIBQP-KRWDZBQOSA-N 0.000 claims 1
- MXSNXPDWRUGJOF-NRFANRHFSA-N (2-fluoro-4-quinolin-3-ylphenyl)-[(2s)-2-(pyrrolidin-1-ylmethyl)pyrrolidin-1-yl]methanone Chemical compound C([C@@H]1CCCN1C(=O)C1=CC=C(C=C1F)C=1C=C2C=CC=CC2=NC=1)N1CCCC1 MXSNXPDWRUGJOF-NRFANRHFSA-N 0.000 claims 1
- LHSDPCDXBLDRIT-NRFANRHFSA-N (4-phenylphenyl)-[(2s)-2-(pyrrolidin-1-ylmethyl)pyrrolidin-1-yl]methanone Chemical compound C([C@@H]1CCCN1C(=O)C=1C=CC(=CC=1)C=1C=CC=CC=1)N1CCCC1 LHSDPCDXBLDRIT-NRFANRHFSA-N 0.000 claims 1
- ZIBWARZVWDOGFS-NRFANRHFSA-N 1-[6-[4-[(2s)-2-(pyrrolidin-1-ylmethyl)pyrrolidine-1-carbonyl]phenyl]pyridin-3-yl]ethanone Chemical compound N1=CC(C(=O)C)=CC=C1C1=CC=C(C(=O)N2[C@@H](CCC2)CN2CCCC2)C=C1 ZIBWARZVWDOGFS-NRFANRHFSA-N 0.000 claims 1
- CYYUHAKXILOQMV-FQEVSTJZSA-N 3-[3-fluoro-4-[(2s)-2-(pyrrolidin-1-ylmethyl)pyrrolidine-1-carbonyl]phenyl]benzonitrile Chemical compound C([C@@H]1CCCN1C(=O)C1=CC=C(C=C1F)C=1C=C(C=CC=1)C#N)N1CCCC1 CYYUHAKXILOQMV-FQEVSTJZSA-N 0.000 claims 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-L L-tartrate(2-) Chemical compound [O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O FEWJPZIEWOKRBE-JCYAYHJZSA-L 0.000 claims 1
- KSBRXIIIMJZMGM-OAQYLSRUSA-N [(2r)-2-(pyrrolidin-1-ylmethyl)pyrrolidin-1-yl]-[4-[4-(trifluoromethyl)phenyl]phenyl]methanone Chemical compound C1=CC(C(F)(F)F)=CC=C1C1=CC=C(C(=O)N2[C@H](CCC2)CN2CCCC2)C=C1 KSBRXIIIMJZMGM-OAQYLSRUSA-N 0.000 claims 1
- QTWICQKEEXWQML-IBGZPJMESA-N [(2s)-2-(pyrrolidin-1-ylmethyl)pyrrolidin-1-yl]-[4-[2-(trifluoromethyl)phenyl]phenyl]methanone Chemical compound FC(F)(F)C1=CC=CC=C1C1=CC=C(C(=O)N2[C@@H](CCC2)CN2CCCC2)C=C1 QTWICQKEEXWQML-IBGZPJMESA-N 0.000 claims 1
- KSBRXIIIMJZMGM-NRFANRHFSA-N [(2s)-2-(pyrrolidin-1-ylmethyl)pyrrolidin-1-yl]-[4-[4-(trifluoromethyl)phenyl]phenyl]methanone Chemical compound C1=CC(C(F)(F)F)=CC=C1C1=CC=C(C(=O)N2[C@@H](CCC2)CN2CCCC2)C=C1 KSBRXIIIMJZMGM-NRFANRHFSA-N 0.000 claims 1
- DBXFOIYEWSXWAL-BDQAORGHSA-N [(2s)-2-(pyrrolidin-1-ylmethyl)pyrrolidin-1-yl]-[4-[4-(trifluoromethylsulfonyl)phenyl]phenyl]methanone;hydrochloride Chemical compound Cl.C1=CC(S(=O)(=O)C(F)(F)F)=CC=C1C1=CC=C(C(=O)N2[C@@H](CCC2)CN2CCCC2)C=C1 DBXFOIYEWSXWAL-BDQAORGHSA-N 0.000 claims 1
- WQECGUXLWDXWHD-PKTZIBPZSA-N [(2s)-2-[[(2r)-2-ethylpyrrolidin-1-yl]methyl]pyrrolidin-1-yl]-[4-[4-(trifluoromethyl)phenyl]phenyl]methanone Chemical compound CC[C@@H]1CCCN1C[C@H]1N(C(=O)C=2C=CC(=CC=2)C=2C=CC(=CC=2)C(F)(F)F)CCC1 WQECGUXLWDXWHD-PKTZIBPZSA-N 0.000 claims 1
- ICVWKDPNTRYDRZ-GCJKJVERSA-N [(2s)-2-[[(2r)-2-methylpyrrolidin-1-yl]methyl]pyrrolidin-1-yl]-[4-(4-methylsulfonylphenyl)phenyl]methanone Chemical compound C[C@@H]1CCCN1C[C@H]1N(C(=O)C=2C=CC(=CC=2)C=2C=CC(=CC=2)S(C)(=O)=O)CCC1 ICVWKDPNTRYDRZ-GCJKJVERSA-N 0.000 claims 1
- WBWCHXFUIHTKGT-VXKWHMMOSA-N [(2s)-2-[[(2s)-2-(fluoromethyl)pyrrolidin-1-yl]methyl]pyrrolidin-1-yl]-[4-[4-(trifluoromethyl)phenyl]phenyl]methanone Chemical compound FC[C@@H]1CCCN1C[C@H]1N(C(=O)C=2C=CC(=CC=2)C=2C=CC(=CC=2)C(F)(F)F)CCC1 WBWCHXFUIHTKGT-VXKWHMMOSA-N 0.000 claims 1
- IBMAUCIQOHEEHD-INIZCTEOSA-N [2,6-difluoro-4-(2-methoxypyrimidin-5-yl)phenyl]-[(2s)-2-(pyrrolidin-1-ylmethyl)pyrrolidin-1-yl]methanone Chemical compound C1=NC(OC)=NC=C1C(C=C1F)=CC(F)=C1C(=O)N1[C@H](CN2CCCC2)CCC1 IBMAUCIQOHEEHD-INIZCTEOSA-N 0.000 claims 1
- BVWTYNOQPTUUDF-RZQQEOIVSA-N [2,6-difluoro-4-(4-methylsulfinylphenyl)phenyl]-[(2s)-2-(pyrrolidin-1-ylmethyl)pyrrolidin-1-yl]methanone Chemical compound C1=CC(S(=O)C)=CC=C1C(C=C1F)=CC(F)=C1C(=O)N1[C@H](CN2CCCC2)CCC1 BVWTYNOQPTUUDF-RZQQEOIVSA-N 0.000 claims 1
- FHLMKHSMTQOPAX-SFHVURJKSA-N [2,6-difluoro-4-(4-methylsulfonylphenyl)phenyl]-[(2s)-2-(pyrrolidin-1-ylmethyl)pyrrolidin-1-yl]methanone Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C(C=C1F)=CC(F)=C1C(=O)N1[C@H](CN2CCCC2)CCC1 FHLMKHSMTQOPAX-SFHVURJKSA-N 0.000 claims 1
- LNWHCAWQRWNDKO-KRWDZBQOSA-N [2,6-difluoro-4-(5-methoxypyridin-3-yl)phenyl]-[(2s)-2-(pyrrolidin-1-ylmethyl)pyrrolidin-1-yl]methanone Chemical compound COC1=CN=CC(C=2C=C(F)C(C(=O)N3[C@@H](CCC3)CN3CCCC3)=C(F)C=2)=C1 LNWHCAWQRWNDKO-KRWDZBQOSA-N 0.000 claims 1
- UYYBSCVYBZOYEA-NHJWOMDBSA-N [2-[[(2r,5s)-2,5-dimethylpyrrolidin-1-yl]methyl]pyrrolidin-1-yl]-[4-[4-(trifluoromethyl)phenyl]phenyl]methanone Chemical compound C[C@H]1CC[C@@H](C)N1CC1N(C(=O)C=2C=CC(=CC=2)C=2C=CC(=CC=2)C(F)(F)F)CCC1 UYYBSCVYBZOYEA-NHJWOMDBSA-N 0.000 claims 1
- UYYBSCVYBZOYEA-JOHXPNBHSA-N [2-[[(2s,5s)-2,5-dimethylpyrrolidin-1-yl]methyl]pyrrolidin-1-yl]-[4-[4-(trifluoromethyl)phenyl]phenyl]methanone Chemical compound C[C@H]1CC[C@H](C)N1CC1N(C(=O)C=2C=CC(=CC=2)C=2C=CC(=CC=2)C(F)(F)F)CCC1 UYYBSCVYBZOYEA-JOHXPNBHSA-N 0.000 claims 1
- XMCQIRZVZSNINQ-FQEVSTJZSA-N [2-fluoro-4-(1h-indol-5-yl)phenyl]-[(2s)-2-(pyrrolidin-1-ylmethyl)pyrrolidin-1-yl]methanone Chemical compound C([C@@H]1CCCN1C(=O)C1=CC=C(C=C1F)C=1C=C2C=CNC2=CC=1)N1CCCC1 XMCQIRZVZSNINQ-FQEVSTJZSA-N 0.000 claims 1
- RRAVZDOQYSUWBR-LMOVPXPDSA-N [2-fluoro-4-(2-fluorophenyl)phenyl]-[(2s)-2-(pyrrolidin-1-ylmethyl)pyrrolidin-1-yl]methanone;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C([C@@H]1CCCN1C(=O)C1=CC=C(C=C1F)C=1C(=CC=CC=1)F)N1CCCC1 RRAVZDOQYSUWBR-LMOVPXPDSA-N 0.000 claims 1
- ZJSRCQLBIWSSMO-KRWDZBQOSA-N [2-fluoro-4-(2-methoxypyrimidin-5-yl)phenyl]-[(2s)-2-(pyrrolidin-1-ylmethyl)pyrrolidin-1-yl]methanone Chemical compound C1=NC(OC)=NC=C1C(C=C1F)=CC=C1C(=O)N1[C@H](CN2CCCC2)CCC1 ZJSRCQLBIWSSMO-KRWDZBQOSA-N 0.000 claims 1
- KTQDHTSFNXNJLU-IBGZPJMESA-N [2-fluoro-4-(3-methylsulfonylphenyl)phenyl]-[(2s)-2-(pyrrolidin-1-ylmethyl)pyrrolidin-1-yl]methanone Chemical compound CS(=O)(=O)C1=CC=CC(C=2C=C(F)C(C(=O)N3[C@@H](CCC3)CN3CCCC3)=CC=2)=C1 KTQDHTSFNXNJLU-IBGZPJMESA-N 0.000 claims 1
- XBUDVRVZJMQMCH-QHCPKHFHSA-N [2-fluoro-4-(3-pyrrolidin-1-ylphenyl)phenyl]-[(2s)-2-(pyrrolidin-1-ylmethyl)pyrrolidin-1-yl]methanone Chemical compound C([C@@H]1CCCN1C(=O)C1=CC=C(C=C1F)C=1C=C(C=CC=1)N1CCCC1)N1CCCC1 XBUDVRVZJMQMCH-QHCPKHFHSA-N 0.000 claims 1
- XIZLDGLFESJLKD-IBGZPJMESA-N [2-fluoro-4-(4-fluorophenyl)phenyl]-[(2s)-2-(pyrrolidin-1-ylmethyl)pyrrolidin-1-yl]methanone Chemical compound C1=CC(F)=CC=C1C(C=C1F)=CC=C1C(=O)N1[C@H](CN2CCCC2)CCC1 XIZLDGLFESJLKD-IBGZPJMESA-N 0.000 claims 1
- GFDUTEZRBVSPIS-IBGZPJMESA-N [2-fluoro-4-(4-methoxyphenyl)phenyl]-[(2s)-2-(pyrrolidin-1-ylmethyl)pyrrolidin-1-yl]methanone Chemical compound C1=CC(OC)=CC=C1C(C=C1F)=CC=C1C(=O)N1[C@H](CN2CCCC2)CCC1 GFDUTEZRBVSPIS-IBGZPJMESA-N 0.000 claims 1
- ASTWNAYIKLYFGW-KCHZNAQISA-N [2-fluoro-4-(4-methylsulfinylphenyl)phenyl]-[(2s)-2-(pyrrolidin-1-ylmethyl)pyrrolidin-1-yl]methanone Chemical compound C1=CC(S(=O)C)=CC=C1C(C=C1F)=CC=C1C(=O)N1[C@H](CN2CCCC2)CCC1 ASTWNAYIKLYFGW-KCHZNAQISA-N 0.000 claims 1
- IPCPNGSAHHVVRF-IBGZPJMESA-N [2-fluoro-4-(4-methylsulfonylphenyl)phenyl]-[(2s)-2-(pyrrolidin-1-ylmethyl)pyrrolidin-1-yl]methanone Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C(C=C1F)=CC=C1C(=O)N1[C@H](CN2CCCC2)CCC1 IPCPNGSAHHVVRF-IBGZPJMESA-N 0.000 claims 1
- HNDITORXFHBYEO-QAPCUYQASA-N [2-fluoro-4-(6-fluoropyridin-3-yl)phenyl]-[(2s)-2-[[(2r)-2-methylpyrrolidin-1-yl]methyl]pyrrolidin-1-yl]methanone Chemical compound C[C@@H]1CCCN1C[C@H]1N(C(=O)C=2C(=CC(=CC=2)C=2C=NC(F)=CC=2)F)CCC1 HNDITORXFHBYEO-QAPCUYQASA-N 0.000 claims 1
- DSWRQPXQPBYGIV-SFHVURJKSA-N [2-fluoro-4-(6-methoxypyridin-3-yl)phenyl]-[(2s)-2-(pyrrolidin-1-ylmethyl)pyrrolidin-1-yl]methanone Chemical compound C1=NC(OC)=CC=C1C(C=C1F)=CC=C1C(=O)N1[C@H](CN2CCCC2)CCC1 DSWRQPXQPBYGIV-SFHVURJKSA-N 0.000 claims 1
- VEJIBCQWXYUBOA-SFHVURJKSA-N [2-fluoro-4-[3-(trifluoromethoxy)phenyl]phenyl]-[(2s)-2-(pyrrolidin-1-ylmethyl)pyrrolidin-1-yl]methanone Chemical compound C([C@@H]1CCCN1C(=O)C1=CC=C(C=C1F)C=1C=C(OC(F)(F)F)C=CC=1)N1CCCC1 VEJIBCQWXYUBOA-SFHVURJKSA-N 0.000 claims 1
- PTMZTEUBPMVBHY-IBGZPJMESA-N [2-fluoro-4-[3-(trifluoromethyl)phenyl]phenyl]-[(2s)-2-(pyrrolidin-1-ylmethyl)pyrrolidin-1-yl]methanone Chemical compound C([C@@H]1CCCN1C(=O)C1=CC=C(C=C1F)C=1C=C(C=CC=1)C(F)(F)F)N1CCCC1 PTMZTEUBPMVBHY-IBGZPJMESA-N 0.000 claims 1
- AEVVCVDEMSQIBX-SFHVURJKSA-N [2-fluoro-4-[4-(trifluoromethoxy)phenyl]phenyl]-[(2s)-2-(pyrrolidin-1-ylmethyl)pyrrolidin-1-yl]methanone Chemical compound C([C@@H]1CCCN1C(=O)C1=CC=C(C=C1F)C=1C=CC(OC(F)(F)F)=CC=1)N1CCCC1 AEVVCVDEMSQIBX-SFHVURJKSA-N 0.000 claims 1
- NAAQRMNMDYOWEI-IBGZPJMESA-N [2-fluoro-4-[4-(trifluoromethyl)phenyl]phenyl]-[(2s)-2-(pyrrolidin-1-ylmethyl)pyrrolidin-1-yl]methanone Chemical compound C([C@@H]1CCCN1C(=O)C1=CC=C(C=C1F)C=1C=CC(=CC=1)C(F)(F)F)N1CCCC1 NAAQRMNMDYOWEI-IBGZPJMESA-N 0.000 claims 1
- SLEYABHRQRUZPG-SFHVURJKSA-N [4-(1,3-benzodioxol-5-yl)-2-fluorophenyl]-[(2s)-2-(pyrrolidin-1-ylmethyl)pyrrolidin-1-yl]methanone Chemical compound C([C@@H]1CCCN1C(=O)C1=CC=C(C=C1F)C=1C=C2OCOC2=CC=1)N1CCCC1 SLEYABHRQRUZPG-SFHVURJKSA-N 0.000 claims 1
- JACGMOZGMGDXPN-FQEVSTJZSA-N [4-(1,3-benzodioxol-5-yl)phenyl]-[(2s)-2-(pyrrolidin-1-ylmethyl)pyrrolidin-1-yl]methanone Chemical compound C([C@@H]1CCCN1C(=O)C=1C=CC(=CC=1)C=1C=C2OCOC2=CC=1)N1CCCC1 JACGMOZGMGDXPN-FQEVSTJZSA-N 0.000 claims 1
- BJCBPJMJWSVDEP-IBGZPJMESA-N [4-(2,3-dihydro-1,4-benzodioxin-6-yl)-2-fluorophenyl]-[(2s)-2-(pyrrolidin-1-ylmethyl)pyrrolidin-1-yl]methanone Chemical compound C([C@@H]1CCCN1C(=O)C1=CC=C(C=C1F)C=1C=C2OCCOC2=CC=1)N1CCCC1 BJCBPJMJWSVDEP-IBGZPJMESA-N 0.000 claims 1
- ZOHUOSVXRFDECX-NRFANRHFSA-N [4-(2,3-dihydro-1,4-benzodioxin-6-yl)phenyl]-[(2s)-2-(pyrrolidin-1-ylmethyl)pyrrolidin-1-yl]methanone Chemical compound C([C@@H]1CCCN1C(=O)C=1C=CC(=CC=1)C=1C=C2OCCOC2=CC=1)N1CCCC1 ZOHUOSVXRFDECX-NRFANRHFSA-N 0.000 claims 1
- VMBVTDIVRMXERD-SFHVURJKSA-N [4-(2,4-dimethoxyphenyl)-2-fluorophenyl]-[(2s)-2-(pyrrolidin-1-ylmethyl)pyrrolidin-1-yl]methanone Chemical compound COC1=CC(OC)=CC=C1C(C=C1F)=CC=C1C(=O)N1[C@H](CN2CCCC2)CCC1 VMBVTDIVRMXERD-SFHVURJKSA-N 0.000 claims 1
- MYYGFCVYYLDBBD-IBGZPJMESA-N [4-(2-chlorophenyl)phenyl]-[(2s)-2-(pyrrolidin-1-ylmethyl)pyrrolidin-1-yl]methanone Chemical compound ClC1=CC=CC=C1C1=CC=C(C(=O)N2[C@@H](CCC2)CN2CCCC2)C=C1 MYYGFCVYYLDBBD-IBGZPJMESA-N 0.000 claims 1
- HMXDCLIIQWIKST-FYZYNONXSA-N [4-(2-fluorophenyl)phenyl]-[(2s)-2-(pyrrolidin-1-ylmethyl)pyrrolidin-1-yl]methanone;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.FC1=CC=CC=C1C1=CC=C(C(=O)N2[C@@H](CCC2)CN2CCCC2)C=C1 HMXDCLIIQWIKST-FYZYNONXSA-N 0.000 claims 1
- JZVSLPZAINVTTC-IBGZPJMESA-N [4-(2-methoxypyrimidin-5-yl)phenyl]-[(2s)-2-(pyrrolidin-1-ylmethyl)pyrrolidin-1-yl]methanone Chemical compound C1=NC(OC)=NC=C1C1=CC=C(C(=O)N2[C@@H](CCC2)CN2CCCC2)C=C1 JZVSLPZAINVTTC-IBGZPJMESA-N 0.000 claims 1
- AHTZFGBYQWTHHB-IBGZPJMESA-N [4-(2-nitrophenyl)phenyl]-[(2s)-2-(pyrrolidin-1-ylmethyl)pyrrolidin-1-yl]methanone Chemical compound [O-][N+](=O)C1=CC=CC=C1C1=CC=C(C(=O)N2[C@@H](CCC2)CN2CCCC2)C=C1 AHTZFGBYQWTHHB-IBGZPJMESA-N 0.000 claims 1
- ZQXNNBKKWBTNNT-IBGZPJMESA-N [4-(3,4-dimethoxyphenyl)-2-fluorophenyl]-[(2s)-2-(pyrrolidin-1-ylmethyl)pyrrolidin-1-yl]methanone Chemical compound C1=C(OC)C(OC)=CC=C1C(C=C1F)=CC=C1C(=O)N1[C@H](CN2CCCC2)CCC1 ZQXNNBKKWBTNNT-IBGZPJMESA-N 0.000 claims 1
- SXFPXDYUDWSAAI-NRFANRHFSA-N [4-(3-methylsulfonylphenyl)phenyl]-[(2s)-2-(pyrrolidin-1-ylmethyl)pyrrolidin-1-yl]methanone Chemical compound CS(=O)(=O)C1=CC=CC(C=2C=CC(=CC=2)C(=O)N2[C@@H](CCC2)CN2CCCC2)=C1 SXFPXDYUDWSAAI-NRFANRHFSA-N 0.000 claims 1
- SKRIIIUNXFPJJU-NRFANRHFSA-N [4-(4-aminophenyl)phenyl]-[(2s)-2-(pyrrolidin-1-ylmethyl)pyrrolidin-1-yl]methanone Chemical compound C1=CC(N)=CC=C1C1=CC=C(C(=O)N2[C@@H](CCC2)CN2CCCC2)C=C1 SKRIIIUNXFPJJU-NRFANRHFSA-N 0.000 claims 1
- HZZLGIABKDRYIN-NRFANRHFSA-N [4-(4-bromophenyl)phenyl]-[(2s)-2-(pyrrolidin-1-ylmethyl)pyrrolidin-1-yl]methanone Chemical compound C1=CC(Br)=CC=C1C1=CC=C(C(=O)N2[C@@H](CCC2)CN2CCCC2)C=C1 HZZLGIABKDRYIN-NRFANRHFSA-N 0.000 claims 1
- DDBYOGZYTLVLFJ-NRFANRHFSA-N [4-(4-chlorophenyl)phenyl]-[(2s)-2-(pyrrolidin-1-ylmethyl)pyrrolidin-1-yl]methanone Chemical compound C1=CC(Cl)=CC=C1C1=CC=C(C(=O)N2[C@@H](CCC2)CN2CCCC2)C=C1 DDBYOGZYTLVLFJ-NRFANRHFSA-N 0.000 claims 1
- RAIASSYATNVMMB-QHCPKHFHSA-N [4-(4-ethylphenyl)phenyl]-[(2s)-2-(pyrrolidin-1-ylmethyl)pyrrolidin-1-yl]methanone Chemical compound C1=CC(CC)=CC=C1C1=CC=C(C(=O)N2[C@@H](CCC2)CN2CCCC2)C=C1 RAIASSYATNVMMB-QHCPKHFHSA-N 0.000 claims 1
- BDINHQQHQLSSSO-FQEVSTJZSA-N [4-(4-ethylsulfonylphenyl)-2-fluorophenyl]-[(2s)-2-(pyrrolidin-1-ylmethyl)pyrrolidin-1-yl]methanone Chemical compound C1=CC(S(=O)(=O)CC)=CC=C1C(C=C1F)=CC=C1C(=O)N1[C@H](CN2CCCC2)CCC1 BDINHQQHQLSSSO-FQEVSTJZSA-N 0.000 claims 1
- ZHWLCVXGEJFPCA-NQIIRXRSSA-N [4-(4-ethylsulfonylphenyl)-2-fluorophenyl]-[(2s)-2-[[(2r)-2-methylpyrrolidin-1-yl]methyl]pyrrolidin-1-yl]methanone Chemical compound C1=CC(S(=O)(=O)CC)=CC=C1C(C=C1F)=CC=C1C(=O)N1[C@H](CN2[C@@H](CCC2)C)CCC1 ZHWLCVXGEJFPCA-NQIIRXRSSA-N 0.000 claims 1
- RTPNDRZHCVMDPD-QFIPXVFZSA-N [4-(4-ethylsulfonylphenyl)phenyl]-[(2s)-2-(pyrrolidin-1-ylmethyl)pyrrolidin-1-yl]methanone Chemical compound C1=CC(S(=O)(=O)CC)=CC=C1C1=CC=C(C(=O)N2[C@@H](CCC2)CN2CCCC2)C=C1 RTPNDRZHCVMDPD-QFIPXVFZSA-N 0.000 claims 1
- PCYZOINYSVUPEC-BOXHHOBZSA-N [4-(4-fluorophenyl)phenyl]-[(2s)-2-(pyrrolidin-1-ylmethyl)pyrrolidin-1-yl]methanone;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=CC(F)=CC=C1C1=CC=C(C(=O)N2[C@@H](CCC2)CN2CCCC2)C=C1 PCYZOINYSVUPEC-BOXHHOBZSA-N 0.000 claims 1
- CHLACRDVRGSTPD-MHZLTWQESA-N [4-(4-hexylphenyl)phenyl]-[(2s)-2-(pyrrolidin-1-ylmethyl)pyrrolidin-1-yl]methanone Chemical compound C1=CC(CCCCCC)=CC=C1C1=CC=C(C(=O)N2[C@@H](CCC2)CN2CCCC2)C=C1 CHLACRDVRGSTPD-MHZLTWQESA-N 0.000 claims 1
- OGRRNOLKPLMRMX-NRFANRHFSA-N [4-(4-methoxyphenyl)phenyl]-[(2s)-2-(pyrrolidin-1-ylmethyl)pyrrolidin-1-yl]methanone Chemical compound C1=CC(OC)=CC=C1C1=CC=C(C(=O)N2[C@@H](CCC2)CN2CCCC2)C=C1 OGRRNOLKPLMRMX-NRFANRHFSA-N 0.000 claims 1
- FXXLLUCXESDHLP-NRFANRHFSA-N [4-(4-nitrophenyl)phenyl]-[(2s)-2-(pyrrolidin-1-ylmethyl)pyrrolidin-1-yl]methanone Chemical compound C1=CC([N+](=O)[O-])=CC=C1C1=CC=C(C(=O)N2[C@@H](CCC2)CN2CCCC2)C=C1 FXXLLUCXESDHLP-NRFANRHFSA-N 0.000 claims 1
- ALJPRIDVMFNMLX-DEOSSOPVSA-N [4-(4-propylphenyl)phenyl]-[(2s)-2-(pyrrolidin-1-ylmethyl)pyrrolidin-1-yl]methanone Chemical compound C1=CC(CCC)=CC=C1C1=CC=C(C(=O)N2[C@@H](CCC2)CN2CCCC2)C=C1 ALJPRIDVMFNMLX-DEOSSOPVSA-N 0.000 claims 1
- KQJWFVQMQIABDM-DEOSSOPVSA-N [4-(4-tert-butylphenyl)phenyl]-[(2s)-2-(pyrrolidin-1-ylmethyl)pyrrolidin-1-yl]methanone Chemical compound C1=CC(C(C)(C)C)=CC=C1C1=CC=C(C(=O)N2[C@@H](CCC2)CN2CCCC2)C=C1 KQJWFVQMQIABDM-DEOSSOPVSA-N 0.000 claims 1
- ASWJGEKBAOWDPS-KJHBKDRRSA-N [4-(6-ethylsulfonylpyridin-3-yl)-2-fluorophenyl]-[(2s)-2-[[(2r)-2-methylpyrrolidin-1-yl]methyl]pyrrolidin-1-yl]methanone;dihydrochloride Chemical compound Cl.Cl.C1=NC(S(=O)(=O)CC)=CC=C1C(C=C1F)=CC=C1C(=O)N1[C@H](CN2[C@@H](CCC2)C)CCC1 ASWJGEKBAOWDPS-KJHBKDRRSA-N 0.000 claims 1
- VQTCYYDBASZVFC-FGJQBABTSA-N [4-(6-ethylsulfonylpyridin-3-yl)phenyl]-[(2s)-2-(pyrrolidin-1-ylmethyl)pyrrolidin-1-yl]methanone;dihydrochloride Chemical compound Cl.Cl.C1=NC(S(=O)(=O)CC)=CC=C1C1=CC=C(C(=O)N2[C@@H](CCC2)CN2CCCC2)C=C1 VQTCYYDBASZVFC-FGJQBABTSA-N 0.000 claims 1
- YIHZHUYBGMHCMU-UZLBHIALSA-N [4-(6-fluoropyridin-3-yl)phenyl]-[(2s)-2-[[(2r)-2-methylpyrrolidin-1-yl]methyl]pyrrolidin-1-yl]methanone Chemical compound C[C@@H]1CCCN1C[C@H]1N(C(=O)C=2C=CC(=CC=2)C=2C=NC(F)=CC=2)CCC1 YIHZHUYBGMHCMU-UZLBHIALSA-N 0.000 claims 1
- UASUHHKGKIDLJT-XLIONFOSSA-N [4-(6-methoxypyridin-2-yl)phenyl]-[(2s)-2-[[(2r)-2-methylpyrrolidin-1-yl]methyl]pyrrolidin-1-yl]methanone Chemical compound COC1=CC=CC(C=2C=CC(=CC=2)C(=O)N2[C@@H](CCC2)CN2[C@@H](CCC2)C)=N1 UASUHHKGKIDLJT-XLIONFOSSA-N 0.000 claims 1
- CDBHJSWRZZCXQQ-FQEVSTJZSA-N [4-(6-methoxypyridin-3-yl)phenyl]-[(2s)-2-(pyrrolidin-1-ylmethyl)pyrrolidin-1-yl]methanone Chemical compound C1=NC(OC)=CC=C1C1=CC=C(C(=O)N2[C@@H](CCC2)CN2CCCC2)C=C1 CDBHJSWRZZCXQQ-FQEVSTJZSA-N 0.000 claims 1
- RLUCKRDBFYPAKA-XLIONFOSSA-N [4-(6-methylpyridazin-3-yl)phenyl]-[(2s)-2-[[(2r)-2-methylpyrrolidin-1-yl]methyl]pyrrolidin-1-yl]methanone Chemical compound C[C@@H]1CCCN1C[C@H]1N(C(=O)C=2C=CC(=CC=2)C=2N=NC(C)=CC=2)CCC1 RLUCKRDBFYPAKA-XLIONFOSSA-N 0.000 claims 1
- PFIBYJGBGHVLRS-FQEVSTJZSA-N [4-(6-methylpyridin-2-yl)phenyl]-[(2s)-2-(pyrrolidin-1-ylmethyl)pyrrolidin-1-yl]methanone Chemical compound CC1=CC=CC(C=2C=CC(=CC=2)C(=O)N2[C@@H](CCC2)CN2CCCC2)=N1 PFIBYJGBGHVLRS-FQEVSTJZSA-N 0.000 claims 1
- YMZZYTZPDZWZSJ-MHZLTWQESA-N [4-[4-(2-piperidin-1-ylethoxy)phenyl]phenyl]-[(2s)-2-(pyrrolidin-1-ylmethyl)pyrrolidin-1-yl]methanone Chemical compound C([C@@H]1CCCN1C(=O)C=1C=CC(=CC=1)C=1C=CC(OCCN2CCCCC2)=CC=1)N1CCCC1 YMZZYTZPDZWZSJ-MHZLTWQESA-N 0.000 claims 1
- PZAWVULYSVCWTR-UHFFFAOYSA-N [4-[4-(5-methyl-1,3,4-oxadiazol-2-yl)phenyl]phenyl]-[2-(pyrrolidin-1-ylmethyl)pyrrolidin-1-yl]methanone Chemical compound O1C(C)=NN=C1C1=CC=C(C=2C=CC(=CC=2)C(=O)N2C(CCC2)CN2CCCC2)C=C1 PZAWVULYSVCWTR-UHFFFAOYSA-N 0.000 claims 1
- QWYBYOVYQUCGSF-IBGZPJMESA-N [5-(4-methylsulfonylphenyl)-2-(trifluoromethyl)phenyl]-[(2s)-2-(pyrrolidin-1-ylmethyl)pyrrolidin-1-yl]methanone Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=CC=C(C(F)(F)F)C(C(=O)N2[C@@H](CCC2)CN2CCCC2)=C1 QWYBYOVYQUCGSF-IBGZPJMESA-N 0.000 claims 1
- ISHTYTQWKPNYJE-SFHVURJKSA-N [5-pyridin-4-yl-2-(trifluoromethyl)phenyl]-[(2s)-2-(pyrrolidin-1-ylmethyl)pyrrolidin-1-yl]methanone Chemical compound C([C@@H]1CCCN1C(=O)C1=CC(=CC=C1C(F)(F)F)C=1C=CN=CC=1)N1CCCC1 ISHTYTQWKPNYJE-SFHVURJKSA-N 0.000 claims 1
- HAJMBLCESYQOCZ-QFIPXVFZSA-N cyclopropyl-[4-[3-fluoro-4-[(2s)-2-(pyrrolidin-1-ylmethyl)pyrrolidine-1-carbonyl]phenyl]phenyl]methanone Chemical compound C([C@@H]1CCCN1C(=O)C1=CC=C(C=C1F)C=1C=CC(=CC=1)C(=O)C1CC1)N1CCCC1 HAJMBLCESYQOCZ-QFIPXVFZSA-N 0.000 claims 1
- WBHWUEHIZFVQED-JPYJTQIMSA-N cyclopropyl-[4-[3-fluoro-4-[(2s)-2-[[(2r)-2-methylpyrrolidin-1-yl]methyl]pyrrolidine-1-carbonyl]phenyl]phenyl]methanone Chemical compound C[C@@H]1CCCN1C[C@H]1N(C(=O)C=2C(=CC(=CC=2)C=2C=CC(=CC=2)C(=O)C2CC2)F)CCC1 WBHWUEHIZFVQED-JPYJTQIMSA-N 0.000 claims 1
- QKIUAMUSENSFQQ-UHFFFAOYSA-N dimethylazanide Chemical compound C[N-]C QKIUAMUSENSFQQ-UHFFFAOYSA-N 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- MGJXBDMLVWIYOQ-UHFFFAOYSA-N methylazanide Chemical compound [NH-]C MGJXBDMLVWIYOQ-UHFFFAOYSA-N 0.000 claims 1
- ZQGJEUVBUVKZKS-UHFFFAOYSA-N n,2-dimethylpropan-2-amine Chemical compound CNC(C)(C)C ZQGJEUVBUVKZKS-UHFFFAOYSA-N 0.000 claims 1
- SORJGGNGBZQNJY-BQAIUKQQSA-N n,n-dimethyl-4-[4-[(2s)-2-(pyrrolidin-1-ylmethyl)pyrrolidine-1-carbonyl]phenyl]benzamide;hydrochloride Chemical compound Cl.C1=CC(C(=O)N(C)C)=CC=C1C1=CC=C(C(=O)N2[C@@H](CCC2)CN2CCCC2)C=C1 SORJGGNGBZQNJY-BQAIUKQQSA-N 0.000 claims 1
- OAXYMGCKABHLIM-FQEVSTJZSA-N n-[2-fluoro-4-[4-[(2s)-2-(pyrrolidin-1-ylmethyl)pyrrolidine-1-carbonyl]phenyl]phenyl]methanesulfonamide Chemical compound C1=C(F)C(NS(=O)(=O)C)=CC=C1C1=CC=C(C(=O)N2[C@@H](CCC2)CN2CCCC2)C=C1 OAXYMGCKABHLIM-FQEVSTJZSA-N 0.000 claims 1
- QGZHIQSJYSTPJP-QFIPXVFZSA-N n-[3-[4-[(2s)-2-(pyrrolidin-1-ylmethyl)pyrrolidine-1-carbonyl]phenyl]phenyl]methanesulfonamide Chemical compound CS(=O)(=O)NC1=CC=CC(C=2C=CC(=CC=2)C(=O)N2[C@@H](CCC2)CN2CCCC2)=C1 QGZHIQSJYSTPJP-QFIPXVFZSA-N 0.000 claims 1
- XNFSBCWBSKMEAT-NRFANRHFSA-N n-[4-[3-fluoro-4-[(2s)-2-(pyrrolidin-1-ylmethyl)pyrrolidine-1-carbonyl]phenyl]phenyl]-n-methylmethanesulfonamide Chemical compound C1=CC(N(C)S(C)(=O)=O)=CC=C1C(C=C1F)=CC=C1C(=O)N1[C@H](CN2CCCC2)CCC1 XNFSBCWBSKMEAT-NRFANRHFSA-N 0.000 claims 1
- FDUZRCBLAHNILK-FQEVSTJZSA-N n-[4-[3-fluoro-4-[(2s)-2-(pyrrolidin-1-ylmethyl)pyrrolidine-1-carbonyl]phenyl]phenyl]methanesulfonamide Chemical compound C1=CC(NS(=O)(=O)C)=CC=C1C(C=C1F)=CC=C1C(=O)N1[C@H](CN2CCCC2)CCC1 FDUZRCBLAHNILK-FQEVSTJZSA-N 0.000 claims 1
- JTXQSZWLHDXUEX-QFIPXVFZSA-N n-[4-[4-[(2s)-2-(pyrrolidin-1-ylmethyl)pyrrolidine-1-carbonyl]phenyl]phenyl]methanesulfonamide Chemical compound C1=CC(NS(=O)(=O)C)=CC=C1C1=CC=C(C(=O)N2[C@@H](CCC2)CN2CCCC2)C=C1 JTXQSZWLHDXUEX-QFIPXVFZSA-N 0.000 claims 1
- TYOWKTGZIHVYFF-FJSYBICCSA-N n-[5-[4-[(2s)-2-(pyrrolidin-1-ylmethyl)pyrrolidine-1-carbonyl]phenyl]pyridin-2-yl]methanesulfonamide;dihydrochloride Chemical compound Cl.Cl.C1=NC(NS(=O)(=O)C)=CC=C1C1=CC=C(C(=O)N2[C@@H](CCC2)CN2CCCC2)C=C1 TYOWKTGZIHVYFF-FJSYBICCSA-N 0.000 claims 1
- WJEQMTHNCAOAHE-FTBISJDPSA-N n-methyl-4-[4-[(2s)-2-(pyrrolidin-1-ylmethyl)pyrrolidine-1-carbonyl]phenyl]benzamide;hydrochloride Chemical compound Cl.C1=CC(C(=O)NC)=CC=C1C1=CC=C(C(=O)N2[C@@H](CCC2)CN2CCCC2)C=C1 WJEQMTHNCAOAHE-FTBISJDPSA-N 0.000 claims 1
- CFERZIHLVDUVPA-VWLOTQADSA-N pyrrolidin-1-yl-[4-[4-[(2s)-2-(pyrrolidin-1-ylmethyl)pyrrolidine-1-carbonyl]phenyl]phenyl]methanone Chemical compound C=1C=C(C=2C=CC(=CC=2)C(=O)N2[C@@H](CCC2)CN2CCCC2)C=CC=1C(=O)N1CCCC1 CFERZIHLVDUVPA-VWLOTQADSA-N 0.000 claims 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 claims 1
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| US8008301B2 (en) * | 2004-04-01 | 2011-08-30 | Eli Lilly And Company | Histamine H3 receptor agents, preparation and therapeutic uses |
| EP1784400B1 (en) * | 2004-08-23 | 2015-01-14 | Eli Lilly And Company | Histamine h3 receptor agents, preparation and therapeutic uses |
| GT200600042A (es) * | 2005-02-10 | 2006-09-27 | Aventis Pharma Inc | Compuestos de bis arilo y heteroarilo sustituido como antagonistas selectivos de 5ht2a |
| CN101151244B (zh) * | 2005-04-01 | 2014-09-03 | 伊莱利利公司 | 组胺h3受体活性剂、制备和治疗用途 |
| JP5193033B2 (ja) * | 2005-07-01 | 2013-05-08 | イーライ リリー アンド カンパニー | ヒスタミンｈ３受容体薬剤、製剤及び治療的使用 |
| US8158673B2 (en) * | 2005-10-27 | 2012-04-17 | Pfizer Inc. | Histamine-3 receptor antagonists |
| WO2007055418A1 (ja) * | 2005-11-10 | 2007-05-18 | Banyu Pharmaceutical Co., Ltd. | アザ置換スピロ誘導体 |
| ATE485294T1 (de) | 2005-11-18 | 2010-11-15 | Hoffmann La Roche | Azaindol-2-carboxamid-derivate |
| US7351708B2 (en) | 2005-12-16 | 2008-04-01 | Hoffmann-La Roche Inc. | Pyrrolo [2,3-b] pyridine derivatives |
| AU2007227681A1 (en) * | 2006-03-15 | 2007-09-27 | Wyeth | N-substituted-azacyclylamines as histamine-3 antagonists |
| WO2008005338A1 (en) * | 2006-06-29 | 2008-01-10 | Arena Pharmaceuticals, Inc. | Modulators of the histamine h3-receptor useful for the treatment of disorders related thereto |
| TW200823204A (en) * | 2006-10-17 | 2008-06-01 | Arena Pharm Inc | Biphenyl sulfonyl and phenyl-heteroaryl sulfonyl modulators of the histamine H3-receptor useful for the treatment of disorders related thereto |
| JP2010529130A (ja) * | 2007-06-08 | 2010-08-26 | アリーナ ファーマシューティカルズ， インコーポレイテッド | （ｒ）−１−｛２−［４’−（３−メトキシ−プロパン−１−スルホニル）−ビフェニル−４−イル］−エチル｝−２−メチル−ピロリジンの結晶形、およびその組成物ならびにそれに関連する方法 |
| CA2700691A1 (en) * | 2007-10-01 | 2009-04-09 | F. Hoffmann-La Roche Ag | New biaryl derivatives |
| ES2479440T3 (es) * | 2008-01-30 | 2014-07-24 | Cephalon, Inc. | Derivados de piridazina sustituidos que tienen actividad antagonista de histamina H3 |
| JP5805792B2 (ja) * | 2011-02-23 | 2015-11-10 | スヴェン・ライフ・サイエンシズ・リミテッド | ヒスタミンｈ３レセプターリガンドとしての新規な化合物 |
| WO2013151982A1 (en) | 2012-04-03 | 2013-10-10 | Arena Pharmaceuticals, Inc. | Methods and compounds useful in treating pruritus, and methods for identifying such compounds |
| MD20140130A2 (ro) | 2012-06-29 | 2015-04-30 | Pfizer Inc. | 4-(amino-substituite)-7H-pirolo[2,3-d]pirimidine noi ca inhibitori de LRRK2 |
| CN112521369A (zh) | 2013-03-13 | 2021-03-19 | 福马治疗股份有限公司 | 用于抑制fasn的化合物及组合物 |
| WO2015092592A1 (en) | 2013-12-17 | 2015-06-25 | Pfizer Inc. | Novel 3,4-disubstituted-1h-pyrrolo[2,3-b]pyridines and 4,5-disubstituted-7h-pyrrolo[2,3-c]pyridazines as lrrk2 inhibitors |
| JP6633618B2 (ja) * | 2014-08-21 | 2020-01-22 | ブリストル−マイヤーズ スクイブ カンパニーＢｒｉｓｔｏｌ−Ｍｙｅｒｓ Ｓｑｕｉｂｂ Ｃｏｍｐａｎｙ | 強力なｒｏｃｋ阻害剤としてのタイドバックのベンズアミド誘導体 |
| MY189453A (en) | 2015-06-03 | 2022-02-14 | Bristol Myers Squibb Co | 4-hydroxy-3-(heteroaryl)pyridine-2-one apj agonists for use in the treatment of cardiovascular disorders |
| RS62639B1 (sr) | 2015-07-06 | 2021-12-31 | Alkermes Inc | Hetero-halo inhibitori histonskih deacetilaza |
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| RU2722149C1 (ru) | 2015-09-14 | 2020-05-27 | Пфайзер Инк. | Новые производные имидазо[4,5-c] хинолинов и имидазо[4,5-c][1,5] нафтиридинов в качестве ингибиторов LRRK2 |
| JP6756925B2 (ja) | 2017-01-11 | 2020-09-16 | ロダン・セラピューティクス，インコーポレーテッド | ヒストンデアセチラーゼの二環式阻害剤 |
| ES2914355T3 (es) | 2017-08-07 | 2022-06-09 | Alkermes Inc | Inhibidores bicíclicos de la histona desacetilasa |
| TWI767148B (zh) | 2018-10-10 | 2022-06-11 | 美商弗瑪治療公司 | 抑制脂肪酸合成酶(fasn) |
| WO2020092395A1 (en) | 2018-10-29 | 2020-05-07 | Forma Therapeutics, Inc. | SOLID FORMS OF (4-(2-FLUORO-4-(1-METHYL-1 H-BENZO[d]IMIDAZOL-5-YL)BENZOYL) PIPERAZIN-1-YL)(1-HYDROXYCYCLOPROPYL)METHANONE |
| US20230257357A1 (en) * | 2020-06-29 | 2023-08-17 | Bacainn Biotherapeutics, Ltd. | Probenecid compounds for the treatment of inflammasome-mediated lung disease |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2579596B1 (fr) | 1985-03-26 | 1987-11-20 | Inst Nat Sante Rech Med | (imidazolyl-4) piperidines, leur preparation et leur application en therapeutique |
| FR2671083B1 (fr) | 1990-12-31 | 1994-12-23 | Inst Nat Sante Rech Med | Nouvelles 4-(4-imidazolyl) piperidines substituees en 1, leur preparation ainsi que leurs applications therapeutiques. |
| US5652258A (en) | 1995-05-30 | 1997-07-29 | Gliatech, Inc. | 2-(4-imidazoyl) cyclopropyl derivatives |
| CA2222099A1 (en) | 1995-05-30 | 1996-12-05 | Gliatech, Inc. | 1h-4(5)-substituted imidazole derivatives |
| PL328369A1 (en) | 1996-02-09 | 1999-01-18 | Black James Foundation | Ligands of histamin h receptor |
| US6620839B2 (en) * | 2000-07-13 | 2003-09-16 | Abbott Laboratories | 1,3-disubstituted and 1,3,3-trisubstituted pyrrolidines as histamine-3 receptor ligands and their therapeutic applications |
| AU2002254114A1 (en) | 2001-03-23 | 2002-10-08 | Eli Lilly And Company | Non-imidazole aryl alkylamines compounds as histamine h3 receptor antagonists, preparation and therapeutic uses |
| PL371435A1 (en) * | 2002-02-01 | 2005-06-13 | Novo Nordisk A/S | Amides of aminoalkyl-substituted azetidines, pyrrolidines, piperidines and azepanes |
| AU2004215428B2 (en) * | 2003-02-26 | 2009-08-27 | Sugen LLC | Aminoheteroaryl compounds as protein kinase inhibitors |
| EP1720861A2 (en) | 2004-02-25 | 2006-11-15 | Eli Lilly And Company | Histamine h3 receptor antagonists, preparation and therapeutic uses |
-
2005
- 2005-03-25 CA CA2561628A patent/CA2561628C/en not_active Expired - Fee Related
- 2005-03-25 SI SI200530961T patent/SI1735278T1/sl unknown
- 2005-03-25 DE DE602005018758T patent/DE602005018758D1/de not_active Expired - Lifetime
- 2005-03-25 PT PT05730691T patent/PT1735278E/pt unknown
- 2005-03-25 US US10/599,488 patent/US7632857B2/en not_active Expired - Fee Related
- 2005-03-25 MX MXPA06011167A patent/MXPA06011167A/es active IP Right Grant
- 2005-03-25 AU AU2005230881A patent/AU2005230881B9/en not_active Ceased
- 2005-03-25 CN CN2005800171466A patent/CN1960969B/zh not_active Expired - Lifetime
- 2005-03-25 PL PL05730691T patent/PL1735278T3/pl unknown
- 2005-03-25 BR BRPI0509298-1A patent/BRPI0509298A/pt not_active IP Right Cessation
- 2005-03-25 ES ES05730691T patent/ES2337376T3/es not_active Expired - Lifetime
- 2005-03-25 WO PCT/US2005/010240 patent/WO2005097740A1/en not_active Ceased
- 2005-03-25 JP JP2007506412A patent/JP4777974B2/ja not_active Expired - Fee Related
- 2005-03-25 EP EP05730691A patent/EP1735278B1/en not_active Expired - Lifetime
- 2005-03-25 DK DK05730691.2T patent/DK1735278T3/da active
- 2005-03-25 AT AT05730691T patent/ATE454372T1/de active
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2010
- 2010-02-25 CY CY20101100183T patent/CY1109860T1/el unknown
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