JP2012525332A5 - - Google Patents
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- Publication number
- JP2012525332A5 JP2012525332A5 JP2012507460A JP2012507460A JP2012525332A5 JP 2012525332 A5 JP2012525332 A5 JP 2012525332A5 JP 2012507460 A JP2012507460 A JP 2012507460A JP 2012507460 A JP2012507460 A JP 2012507460A JP 2012525332 A5 JP2012525332 A5 JP 2012525332A5
- Authority
- JP
- Japan
- Prior art keywords
- phenyl
- piperazin
- pyrimidin
- pyrrolo
- alkyl
- 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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- -1 —S (O) n CH 3 Chemical group 0.000 claims 52
- 125000000217 alkyl group Chemical group 0.000 claims 34
- 125000004093 cyano group Chemical group *C#N 0.000 claims 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 12
- 150000003839 salts Chemical class 0.000 claims 12
- 150000001875 compounds Chemical class 0.000 claims 11
- 125000003545 alkoxy group Chemical group 0.000 claims 10
- 125000001072 heteroaryl group Chemical group 0.000 claims 9
- 229910052736 halogen Inorganic materials 0.000 claims 8
- 150000002367 halogens Chemical class 0.000 claims 8
- 125000004076 pyridyl group Chemical group 0.000 claims 8
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims 7
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 7
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 6
- 125000003118 aryl group Chemical group 0.000 claims 6
- KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims 6
- 125000004043 oxo group Chemical group O=* 0.000 claims 6
- 125000000623 heterocyclic group Chemical group 0.000 claims 5
- 125000002883 imidazolyl group Chemical group 0.000 claims 5
- 125000001041 indolyl group Chemical group 0.000 claims 5
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 claims 5
- 125000003226 pyrazolyl group Chemical group 0.000 claims 5
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 4
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 4
- 125000002252 acyl group Chemical group 0.000 claims 4
- 125000003342 alkenyl group Chemical group 0.000 claims 4
- 125000000304 alkynyl group Chemical group 0.000 claims 4
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 4
- 229910052799 carbon Inorganic materials 0.000 claims 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 4
- 229910052739 hydrogen Inorganic materials 0.000 claims 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 4
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 4
- 125000000168 pyrrolyl group Chemical group 0.000 claims 4
- 125000001113 thiadiazolyl group Chemical group 0.000 claims 4
- 125000000335 thiazolyl group Chemical group 0.000 claims 4
- 125000001544 thienyl group Chemical group 0.000 claims 4
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N 1H-imidazole Chemical compound C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 3
- 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 claims 3
- 239000001257 hydrogen Substances 0.000 claims 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 3
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims 3
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims 3
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 2
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims 2
- 125000002541 furyl group Chemical group 0.000 claims 2
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 2
- 125000001786 isothiazolyl group Chemical group 0.000 claims 2
- 125000000842 isoxazolyl group Chemical group 0.000 claims 2
- 125000002757 morpholinyl group Chemical group 0.000 claims 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 2
- 125000002971 oxazolyl group Chemical group 0.000 claims 2
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 125000004193 piperazinyl group Chemical group 0.000 claims 2
- 125000003386 piperidinyl group Chemical group 0.000 claims 2
- 125000003373 pyrazinyl group Chemical group 0.000 claims 2
- 125000002098 pyridazinyl group Chemical group 0.000 claims 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 2
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims 2
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims 1
- WXAYGXGWQNSLGW-UHFFFAOYSA-N 1-[2-[4-[2-(2-morpholin-4-ylpyrimidin-5-yl)phenyl]piperazin-1-yl]-2-oxoethyl]imidazolidin-2-one Chemical compound C1CN(C=2C(=CC=CC=2)C=2C=NC(=NC=2)N2CCOCC2)CCN1C(=O)CN1CCNC1=O WXAYGXGWQNSLGW-UHFFFAOYSA-N 0.000 claims 1
- VYCPWUDBKFORQP-UHFFFAOYSA-N 1-[2-methyl-4-[2-[2-(4-methylsulfonylpiperidin-1-yl)pyrimidin-5-yl]phenyl]piperazin-1-yl]-2-pyrrolo[2,3-c]pyridin-1-ylethanone Chemical compound C1CN(C(=O)CN2C3=CN=CC=C3C=C2)C(C)CN1C1=CC=CC=C1C(C=N1)=CN=C1N1CCC(S(C)(=O)=O)CC1 VYCPWUDBKFORQP-UHFFFAOYSA-N 0.000 claims 1
- RDYDUKMIMQRBFN-UHFFFAOYSA-N 1-[4-(2-phenylphenyl)piperazin-1-yl]-2-piperidin-1-ylethanone Chemical compound C1CN(C=2C(=CC=CC=2)C=2C=CC=CC=2)CCN1C(=O)CN1CCCCC1 RDYDUKMIMQRBFN-UHFFFAOYSA-N 0.000 claims 1
- TVIXOCCKWVNECQ-UHFFFAOYSA-N 1-[4-[2-(2-methoxypyrimidin-5-yl)phenyl]piperazin-1-yl]-2-pyrrolo[2,3-b]pyridin-1-ylethanone Chemical compound C1=NC(OC)=NC=C1C1=CC=CC=C1N1CCN(C(=O)CN2C3=NC=CC=C3C=C2)CC1 TVIXOCCKWVNECQ-UHFFFAOYSA-N 0.000 claims 1
- YITXQTQOTWOFER-UHFFFAOYSA-N 1-[4-[2-(2-methylsulfanylpyrimidin-5-yl)phenyl]piperazin-1-yl]-2-pyrrolo[2,3-b]pyridin-1-ylethanone Chemical compound C1=NC(SC)=NC=C1C1=CC=CC=C1N1CCN(C(=O)CN2C3=NC=CC=C3C=C2)CC1 YITXQTQOTWOFER-UHFFFAOYSA-N 0.000 claims 1
- KPWISRQIHOZXCI-UHFFFAOYSA-N 1-[4-[2-(2-morpholin-4-ylpyrimidin-5-yl)phenyl]piperazin-1-yl]-2-pyrrolo[2,3-b]pyridin-1-ylethanone Chemical compound C1=CC2=CC=CN=C2N1CC(=O)N(CC1)CCN1C1=CC=CC=C1C(C=N1)=CN=C1N1CCOCC1 KPWISRQIHOZXCI-UHFFFAOYSA-N 0.000 claims 1
- OHQQBEBGBRXYAV-UHFFFAOYSA-N 1-[4-[2-[2-(2,6-dimethylmorpholin-4-yl)pyrimidin-5-yl]phenyl]piperazin-1-yl]-2-(3,5-dimethylpyrazol-1-yl)ethanone Chemical compound C1C(C)OC(C)CN1C1=NC=C(C=2C(=CC=CC=2)N2CCN(CC2)C(=O)CN2C(=CC(C)=N2)C)C=N1 OHQQBEBGBRXYAV-UHFFFAOYSA-N 0.000 claims 1
- MYOBPFLZCAHSMA-UHFFFAOYSA-N 1-[4-[2-[2-(4-hydroxypiperidin-1-yl)pyrimidin-5-yl]-4-(trifluoromethyl)phenyl]-2-methylpiperazin-1-yl]-2-pyrrolo[2,3-b]pyridin-1-ylethanone Chemical compound C1CN(C(=O)CN2C3=NC=CC=C3C=C2)C(C)CN1C1=CC=C(C(F)(F)F)C=C1C(C=N1)=CN=C1N1CCC(O)CC1 MYOBPFLZCAHSMA-UHFFFAOYSA-N 0.000 claims 1
- UDQJQMGNOVCCLA-UHFFFAOYSA-N 1-[4-[2-[2-(4-hydroxypiperidin-1-yl)pyrimidin-5-yl]-4-(trifluoromethyl)phenyl]-2-methylpiperazin-1-yl]-2-pyrrolo[2,3-c]pyridin-1-ylethanone Chemical compound C1CN(C(=O)CN2C3=CN=CC=C3C=C2)C(C)CN1C1=CC=C(C(F)(F)F)C=C1C(C=N1)=CN=C1N1CCC(O)CC1 UDQJQMGNOVCCLA-UHFFFAOYSA-N 0.000 claims 1
- IHZGEJITWJFEGM-UHFFFAOYSA-N 1-[4-[2-[2-(4-hydroxypiperidin-1-yl)pyrimidin-5-yl]phenyl]-2-methylpiperazin-1-yl]-2-pyrrolo[2,3-b]pyridin-1-ylethanone Chemical compound C1CN(C(=O)CN2C3=NC=CC=C3C=C2)C(C)CN1C1=CC=CC=C1C(C=N1)=CN=C1N1CCC(O)CC1 IHZGEJITWJFEGM-UHFFFAOYSA-N 0.000 claims 1
- NNAZPTCJEDKZLT-UHFFFAOYSA-N 1-[4-[2-[2-(4-hydroxypiperidin-1-yl)pyrimidin-5-yl]phenyl]-2-methylpiperazin-1-yl]-2-pyrrolo[2,3-c]pyridin-1-ylethanone Chemical compound C1CN(C(=O)CN2C3=CN=CC=C3C=C2)C(C)CN1C1=CC=CC=C1C(C=N1)=CN=C1N1CCC(O)CC1 NNAZPTCJEDKZLT-UHFFFAOYSA-N 0.000 claims 1
- UCFPDSLVZZRGNC-UHFFFAOYSA-N 1-[4-[2-[2-(dimethylamino)pyrimidin-5-yl]phenyl]piperazin-1-yl]-2-pyrrolo[2,3-b]pyridin-1-ylethanone Chemical compound C1=NC(N(C)C)=NC=C1C1=CC=CC=C1N1CCN(C(=O)CN2C3=NC=CC=C3C=C2)CC1 UCFPDSLVZZRGNC-UHFFFAOYSA-N 0.000 claims 1
- UUFPARHWBWDJEL-UHFFFAOYSA-N 1-[4-[2-[4-[(dimethylamino)methyl]phenyl]phenyl]piperazin-1-yl]-2-(3,5-dimethylpyrazol-1-yl)ethanone Chemical compound C1=CC(CN(C)C)=CC=C1C1=CC=CC=C1N1CCN(C(=O)CN2C(=CC(C)=N2)C)CC1 UUFPARHWBWDJEL-UHFFFAOYSA-N 0.000 claims 1
- XLSBVSNXSCACQJ-UHFFFAOYSA-N 1-[4-[4-fluoro-2-[2-(4-hydroxypiperidin-1-yl)pyrimidin-5-yl]phenyl]piperazin-1-yl]-2-imidazo[4,5-b]pyridin-3-ylethanone Chemical compound C1CC(O)CCN1C1=NC=C(C=2C(=CC=C(F)C=2)N2CCN(CC2)C(=O)CN2C3=NC=CC=C3N=C2)C=N1 XLSBVSNXSCACQJ-UHFFFAOYSA-N 0.000 claims 1
- XKZTYHWRHFJSGM-UHFFFAOYSA-N 1-[4-[4-fluoro-2-[2-(4-hydroxypiperidin-1-yl)pyrimidin-5-yl]phenyl]piperazin-1-yl]-2-pyrrolo[2,3-b]pyridin-1-ylethanone Chemical compound C1CC(O)CCN1C1=NC=C(C=2C(=CC=C(F)C=2)N2CCN(CC2)C(=O)CN2C3=NC=CC=C3C=C2)C=N1 XKZTYHWRHFJSGM-UHFFFAOYSA-N 0.000 claims 1
- DYTKSFKHKHTAKS-UHFFFAOYSA-N 1-[4-[4-fluoro-2-[2-(4-hydroxypiperidin-1-yl)pyrimidin-5-yl]phenyl]piperazin-1-yl]-2-pyrrolo[2,3-c]pyridin-1-ylethanone Chemical compound C1CC(O)CCN1C1=NC=C(C=2C(=CC=C(F)C=2)N2CCN(CC2)C(=O)CN2C3=CN=CC=C3C=C2)C=N1 DYTKSFKHKHTAKS-UHFFFAOYSA-N 0.000 claims 1
- NYDDBKINLWXGLH-UHFFFAOYSA-N 1-[4-[4-fluoro-2-[2-(4-methylsulfonylpiperidin-1-yl)pyrimidin-5-yl]phenyl]piperazin-1-yl]-2-imidazo[4,5-b]pyridin-3-ylethanone Chemical compound C1CC(S(=O)(=O)C)CCN1C1=NC=C(C=2C(=CC=C(F)C=2)N2CCN(CC2)C(=O)CN2C3=NC=CC=C3N=C2)C=N1 NYDDBKINLWXGLH-UHFFFAOYSA-N 0.000 claims 1
- JOVVYNPSVAXDBO-UHFFFAOYSA-N 1-[4-[4-fluoro-2-[2-(4-methylsulfonylpiperidin-1-yl)pyrimidin-5-yl]phenyl]piperazin-1-yl]-2-pyrrolo[2,3-b]pyridin-1-ylethanone Chemical compound C1CC(S(=O)(=O)C)CCN1C1=NC=C(C=2C(=CC=C(F)C=2)N2CCN(CC2)C(=O)CN2C3=NC=CC=C3C=C2)C=N1 JOVVYNPSVAXDBO-UHFFFAOYSA-N 0.000 claims 1
- NTFRDZBMZATPQE-UHFFFAOYSA-N 1-[4-[4-fluoro-2-[2-(4-methylsulfonylpiperidin-1-yl)pyrimidin-5-yl]phenyl]piperazin-1-yl]-2-pyrrolo[2,3-c]pyridin-1-ylethanone Chemical compound C1CC(S(=O)(=O)C)CCN1C1=NC=C(C=2C(=CC=C(F)C=2)N2CCN(CC2)C(=O)CN2C3=CN=CC=C3C=C2)C=N1 NTFRDZBMZATPQE-UHFFFAOYSA-N 0.000 claims 1
- IDNSGBNSMGDPOY-UHFFFAOYSA-N 1-methyl-n-[2-oxo-2-[4-(2-phenylphenyl)piperazin-1-yl]ethyl]imidazole-2-carboxamide Chemical compound CN1C=CN=C1C(=O)NCC(=O)N1CCN(C=2C(=CC=CC=2)C=2C=CC=CC=2)CC1 IDNSGBNSMGDPOY-UHFFFAOYSA-N 0.000 claims 1
- AIMNNNATIMKKJX-UHFFFAOYSA-N 1-pyrrolo[2,3-b]pyridin-1-ylethanone Chemical compound C1=CN=C2N(C(=O)C)C=CC2=C1 AIMNNNATIMKKJX-UHFFFAOYSA-N 0.000 claims 1
- LSPSNBLONACXGF-UHFFFAOYSA-N 2-(3,5-dimethylpyrazol-1-yl)-1-[2-methyl-4-[2-[2-(4-methylsulfonylpiperidin-1-yl)pyrimidin-5-yl]-4-(trifluoromethyl)phenyl]piperazin-1-yl]ethanone Chemical compound CC1CN(C=2C(=CC(=CC=2)C(F)(F)F)C=2C=NC(=NC=2)N2CCC(CC2)S(C)(=O)=O)CCN1C(=O)CN1N=C(C)C=C1C LSPSNBLONACXGF-UHFFFAOYSA-N 0.000 claims 1
- YPPZFUXRYPNEIT-UHFFFAOYSA-N 2-(3,5-dimethylpyrazol-1-yl)-1-[2-methyl-4-[2-[2-(4-methylsulfonylpiperidin-1-yl)pyrimidin-5-yl]phenyl]piperazin-1-yl]ethanone Chemical compound CC1CN(C=2C(=CC=CC=2)C=2C=NC(=NC=2)N2CCC(CC2)S(C)(=O)=O)CCN1C(=O)CN1N=C(C)C=C1C YPPZFUXRYPNEIT-UHFFFAOYSA-N 0.000 claims 1
- SIVOEXRHOFVHMZ-UHFFFAOYSA-N 2-(3,5-dimethylpyrazol-1-yl)-1-[4-(2-naphthalen-1-ylphenyl)piperazin-1-yl]ethanone Chemical compound N1=C(C)C=C(C)N1CC(=O)N1CCN(C=2C(=CC=CC=2)C=2C3=CC=CC=C3C=CC=2)CC1 SIVOEXRHOFVHMZ-UHFFFAOYSA-N 0.000 claims 1
- LZDSDKNDVWRRID-UHFFFAOYSA-N 2-(3,5-dimethylpyrazol-1-yl)-1-[4-[2-(2-pyrrolidin-1-ylpyrimidin-5-yl)phenyl]piperazin-1-yl]ethanone Chemical compound N1=C(C)C=C(C)N1CC(=O)N1CCN(C=2C(=CC=CC=2)C=2C=NC(=NC=2)N2CCCC2)CC1 LZDSDKNDVWRRID-UHFFFAOYSA-N 0.000 claims 1
- ISSKAEZMRMQJLH-UHFFFAOYSA-N 2-(3,5-dimethylpyrazol-1-yl)-1-[4-[2-[2-(4-hydroxypiperidin-1-yl)pyrimidin-5-yl]-4-(trifluoromethyl)phenyl]-2-methylpiperazin-1-yl]ethanone Chemical compound CC1CN(C=2C(=CC(=CC=2)C(F)(F)F)C=2C=NC(=NC=2)N2CCC(O)CC2)CCN1C(=O)CN1N=C(C)C=C1C ISSKAEZMRMQJLH-UHFFFAOYSA-N 0.000 claims 1
- PUTFTNTZMOPNFO-UHFFFAOYSA-N 2-(3,5-dimethylpyrazol-1-yl)-1-[4-[4-fluoro-2-[2-(4-hydroxypiperidin-1-yl)pyrimidin-5-yl]phenyl]piperazin-1-yl]ethanone Chemical compound N1=C(C)C=C(C)N1CC(=O)N1CCN(C=2C(=CC(F)=CC=2)C=2C=NC(=NC=2)N2CCC(O)CC2)CC1 PUTFTNTZMOPNFO-UHFFFAOYSA-N 0.000 claims 1
- FJCGYTHBYOSAEA-UHFFFAOYSA-N 2-(3,5-dimethylpyrazol-1-yl)-1-[4-[4-fluoro-2-[2-(4-methylsulfonylpiperidin-1-yl)pyrimidin-5-yl]phenyl]-2-methylpiperazin-1-yl]ethanone Chemical compound CC1CN(C=2C(=CC(F)=CC=2)C=2C=NC(=NC=2)N2CCC(CC2)S(C)(=O)=O)CCN1C(=O)CN1N=C(C)C=C1C FJCGYTHBYOSAEA-UHFFFAOYSA-N 0.000 claims 1
- FMMQCFATKIDWIV-UHFFFAOYSA-N 2-[(3,4-dimethoxyphenyl)methylamino]-1-[4-(2-phenylphenyl)piperazin-1-yl]ethanone Chemical compound C1=C(OC)C(OC)=CC=C1CNCC(=O)N1CCN(C=2C(=CC=CC=2)C=2C=CC=CC=2)CC1 FMMQCFATKIDWIV-UHFFFAOYSA-N 0.000 claims 1
- PTRMTOCFPBKUDE-UHFFFAOYSA-N 2-[2-[2-methyl-4-[2-[2-(4-methylsulfonylpiperidin-1-yl)pyrimidin-5-yl]-4-(trifluoromethyl)phenyl]piperazin-1-yl]-2-oxoethyl]-3h-isoindol-1-one Chemical compound C1CN(C(=O)CN2C(C3=CC=CC=C3C2)=O)C(C)CN1C1=CC=C(C(F)(F)F)C=C1C(C=N1)=CN=C1N1CCC(S(C)(=O)=O)CC1 PTRMTOCFPBKUDE-UHFFFAOYSA-N 0.000 claims 1
- MOSKQNKJQGPJLU-UHFFFAOYSA-N 2-[2-[4-[2-[2-(4-hydroxypiperidin-1-yl)pyrimidin-5-yl]-4-(trifluoromethyl)phenyl]-2-methylpiperazin-1-yl]-2-oxoethyl]-3h-isoindol-1-one Chemical compound C1CN(C(=O)CN2C(C3=CC=CC=C3C2)=O)C(C)CN1C1=CC=C(C(F)(F)F)C=C1C(C=N1)=CN=C1N1CCC(O)CC1 MOSKQNKJQGPJLU-UHFFFAOYSA-N 0.000 claims 1
- NQRFCQHDNGHHDP-UHFFFAOYSA-N 2-[2-[4-[2-[2-(4-hydroxypiperidin-1-yl)pyrimidin-5-yl]phenyl]-2-methylpiperazin-1-yl]-2-oxoethyl]-3h-isoindol-1-one Chemical compound C1CN(C(=O)CN2C(C3=CC=CC=C3C2)=O)C(C)CN1C1=CC=CC=C1C(C=N1)=CN=C1N1CCC(O)CC1 NQRFCQHDNGHHDP-UHFFFAOYSA-N 0.000 claims 1
- KGEUNAZEQRRDLP-UHFFFAOYSA-N 2-[2-[4-[4-fluoro-2-[2-(4-hydroxypiperidin-1-yl)pyrimidin-5-yl]phenyl]piperazin-1-yl]-2-oxoethyl]-3h-isoindol-1-one Chemical compound C1CC(O)CCN1C1=NC=C(C=2C(=CC=C(F)C=2)N2CCN(CC2)C(=O)CN2C(C3=CC=CC=C3C2)=O)C=N1 KGEUNAZEQRRDLP-UHFFFAOYSA-N 0.000 claims 1
- PRZGZEXTKYKASO-UHFFFAOYSA-N 2-[2-[4-[4-fluoro-2-[2-(4-methylsulfonylpiperidin-1-yl)pyrimidin-5-yl]phenyl]-2-methylpiperazin-1-yl]-2-oxoethyl]-3h-isoindol-1-one Chemical compound C1CN(C(=O)CN2C(C3=CC=CC=C3C2)=O)C(C)CN1C1=CC=C(F)C=C1C(C=N1)=CN=C1N1CCC(S(C)(=O)=O)CC1 PRZGZEXTKYKASO-UHFFFAOYSA-N 0.000 claims 1
- GLWMODWQRYHHAQ-UHFFFAOYSA-N 2-[2-[4-[4-fluoro-2-[2-(4-methylsulfonylpiperidin-1-yl)pyrimidin-5-yl]phenyl]piperazin-1-yl]-2-oxoethyl]-3h-isoindol-1-one Chemical compound C1CC(S(=O)(=O)C)CCN1C1=NC=C(C=2C(=CC=C(F)C=2)N2CCN(CC2)C(=O)CN2C(C3=CC=CC=C3C2)=O)C=N1 GLWMODWQRYHHAQ-UHFFFAOYSA-N 0.000 claims 1
- HTPJNFALKQCYCW-UHFFFAOYSA-N 2-imidazo[4,5-b]pyridin-3-yl-1-[2-methyl-4-[2-[2-(4-methylsulfonylpiperidin-1-yl)pyrimidin-5-yl]-4-(trifluoromethyl)phenyl]piperazin-1-yl]ethanone Chemical compound C1CN(C(=O)CN2C3=NC=CC=C3N=C2)C(C)CN1C1=CC=C(C(F)(F)F)C=C1C(C=N1)=CN=C1N1CCC(S(C)(=O)=O)CC1 HTPJNFALKQCYCW-UHFFFAOYSA-N 0.000 claims 1
- IXTWSPDCJBNIHE-UHFFFAOYSA-N 3-(2-methylsulfanylpyrimidin-5-yl)-4-[4-(2-pyrrolo[2,3-b]pyridin-1-ylacetyl)piperazin-1-yl]benzonitrile Chemical compound C1=NC(SC)=NC=C1C1=CC(C#N)=CC=C1N1CCN(C(=O)CN2C3=NC=CC=C3C=C2)CC1 IXTWSPDCJBNIHE-UHFFFAOYSA-N 0.000 claims 1
- UVXFDEFMNVFGDK-UHFFFAOYSA-N 3-[2-[2-methyl-4-[2-[2-(4-methylsulfonylpiperidin-1-yl)pyrimidin-5-yl]-4-(trifluoromethyl)phenyl]piperazin-1-yl]-2-oxoethyl]-1h-benzimidazol-2-one Chemical compound C1CN(C(=O)CN2C(NC3=CC=CC=C32)=O)C(C)CN1C1=CC=C(C(F)(F)F)C=C1C(C=N1)=CN=C1N1CCC(S(C)(=O)=O)CC1 UVXFDEFMNVFGDK-UHFFFAOYSA-N 0.000 claims 1
- NMDSQLZUHSXBRA-UHFFFAOYSA-N 3-[2-[4-[2-[2-(4-hydroxypiperidin-1-yl)pyrimidin-5-yl]-4-(trifluoromethyl)phenyl]-2-methylpiperazin-1-yl]-2-oxoethyl]-1h-benzimidazol-2-one Chemical compound C1CN(C(=O)CN2C(NC3=CC=CC=C32)=O)C(C)CN1C1=CC=C(C(F)(F)F)C=C1C(C=N1)=CN=C1N1CCC(O)CC1 NMDSQLZUHSXBRA-UHFFFAOYSA-N 0.000 claims 1
- WFGPYAXJLMOMCN-UHFFFAOYSA-N 3-[2-[4-[2-[2-(4-hydroxypiperidin-1-yl)pyrimidin-5-yl]phenyl]-2-methylpiperazin-1-yl]-2-oxoethyl]-1h-benzimidazol-2-one Chemical compound C1CN(C(=O)CN2C(NC3=CC=CC=C32)=O)C(C)CN1C1=CC=CC=C1C(C=N1)=CN=C1N1CCC(O)CC1 WFGPYAXJLMOMCN-UHFFFAOYSA-N 0.000 claims 1
- GDPWWOUZDHKUHD-UHFFFAOYSA-N 3-[2-[4-[4-fluoro-2-[2-(4-hydroxypiperidin-1-yl)pyrimidin-5-yl]phenyl]piperazin-1-yl]-2-oxoethyl]-1h-benzimidazol-2-one Chemical compound C1CC(O)CCN1C1=NC=C(C=2C(=CC=C(F)C=2)N2CCN(CC2)C(=O)CN2C(NC3=CC=CC=C32)=O)C=N1 GDPWWOUZDHKUHD-UHFFFAOYSA-N 0.000 claims 1
- XWHFJZMECLOYOK-UHFFFAOYSA-N 3-[2-[4-[4-fluoro-2-[2-(4-methylsulfonylpiperidin-1-yl)pyrimidin-5-yl]phenyl]-2-methylpiperazin-1-yl]-2-oxoethyl]-1h-benzimidazol-2-one Chemical compound C1CN(C(=O)CN2C(NC3=CC=CC=C32)=O)C(C)CN1C1=CC=C(F)C=C1C(C=N1)=CN=C1N1CCC(S(C)(=O)=O)CC1 XWHFJZMECLOYOK-UHFFFAOYSA-N 0.000 claims 1
- JVNDDBDHDJVWQQ-UHFFFAOYSA-N 3-[2-[4-[4-fluoro-2-[2-(4-methylsulfonylpiperidin-1-yl)pyrimidin-5-yl]phenyl]piperazin-1-yl]-2-oxoethyl]-1h-benzimidazol-2-one Chemical compound C1CC(S(=O)(=O)C)CCN1C1=NC=C(C=2C(=CC=C(F)C=2)N2CCN(CC2)C(=O)CN2C(NC3=CC=CC=C32)=O)C=N1 JVNDDBDHDJVWQQ-UHFFFAOYSA-N 0.000 claims 1
- MGMLCTNFCUTSAM-UHFFFAOYSA-N 4,5-dimethyl-n-[2-oxo-2-[4-(2-phenylphenyl)piperazin-1-yl]ethyl]furan-2-carboxamide Chemical compound O1C(C)=C(C)C=C1C(=O)NCC(=O)N1CCN(C=2C(=CC=CC=2)C=2C=CC=CC=2)CC1 MGMLCTNFCUTSAM-UHFFFAOYSA-N 0.000 claims 1
- JZYCBTIVIGFYPC-UHFFFAOYSA-N 4-amino-3-methoxy-n-[2-oxo-2-[4-(2-phenylphenyl)piperazin-1-yl]ethyl]benzamide Chemical compound C1=C(N)C(OC)=CC(C(=O)NCC(=O)N2CCN(CC2)C=2C(=CC=CC=2)C=2C=CC=CC=2)=C1 JZYCBTIVIGFYPC-UHFFFAOYSA-N 0.000 claims 1
- ZWQLSSCUWNHOJX-UHFFFAOYSA-N 5-[2-[4-(2-pyrrolo[2,3-b]pyridin-1-ylacetyl)piperazin-1-yl]phenyl]pyridine-2-carbonitrile Chemical compound C1=CC2=CC=CN=C2N1CC(=O)N(CC1)CCN1C1=CC=CC=C1C1=CC=C(C#N)N=C1 ZWQLSSCUWNHOJX-UHFFFAOYSA-N 0.000 claims 1
- 208000023275 Autoimmune disease Diseases 0.000 claims 1
- 102100028990 C-X-C chemokine receptor type 3 Human genes 0.000 claims 1
- 208000024172 Cardiovascular disease Diseases 0.000 claims 1
- 101000916050 Homo sapiens C-X-C chemokine receptor type 3 Proteins 0.000 claims 1
- 230000001548 androgenic effect Effects 0.000 claims 1
- 230000001363 autoimmune Effects 0.000 claims 1
- 125000002393 azetidinyl group Chemical group 0.000 claims 1
- 125000005872 benzooxazolyl group Chemical group 0.000 claims 1
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 125000005509 dibenzothiophenyl group Chemical group 0.000 claims 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- 208000035475 disorder Diseases 0.000 claims 1
- RWTNPBWLLIMQHL-UHFFFAOYSA-N fexofenadine Chemical compound C1=CC(C(C)(C(O)=O)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 RWTNPBWLLIMQHL-UHFFFAOYSA-N 0.000 claims 1
- 125000003630 glycyl group Chemical group [H]N([H])C([H])([H])C(*)=O 0.000 claims 1
- 125000005553 heteroaryloxy group Chemical group 0.000 claims 1
- 208000027866 inflammatory disease Diseases 0.000 claims 1
- 230000002757 inflammatory effect Effects 0.000 claims 1
- 230000001404 mediated effect Effects 0.000 claims 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims 1
- IWBUEIRRSIAYTD-UHFFFAOYSA-N n-[2-oxo-2-[4-(2-phenylphenyl)piperazin-1-yl]ethyl]-1,3-thiazole-2-carboxamide Chemical compound C1CN(C=2C(=CC=CC=2)C=2C=CC=CC=2)CCN1C(=O)CNC(=O)C1=NC=CS1 IWBUEIRRSIAYTD-UHFFFAOYSA-N 0.000 claims 1
- WTCBWXXSMFOXSM-UHFFFAOYSA-N n-[2-oxo-2-[4-(2-phenylphenyl)piperazin-1-yl]ethyl]isoquinoline-6-carboxamide Chemical compound C=1C=C2C=NC=CC2=CC=1C(=O)NCC(=O)N(CC1)CCN1C1=CC=CC=C1C1=CC=CC=C1 WTCBWXXSMFOXSM-UHFFFAOYSA-N 0.000 claims 1
- YOFASPLHQSWAJD-UHFFFAOYSA-N n-[2-oxo-2-[4-(2-phenylphenyl)piperazin-1-yl]ethyl]isoquinoline-7-carboxamide Chemical compound C=1C=C2C=CN=CC2=CC=1C(=O)NCC(=O)N(CC1)CCN1C1=CC=CC=C1C1=CC=CC=C1 YOFASPLHQSWAJD-UHFFFAOYSA-N 0.000 claims 1
- 125000004930 octahydroisoquinolinyl group Chemical group C1(NCCC2CCCC=C12)* 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
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 claims 1
- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 claims 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims 1
- 125000004306 triazinyl group Chemical group 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
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| US61/319,482 | 2010-03-31 | ||
| PCT/US2010/032347 WO2010126811A1 (en) | 2009-04-27 | 2010-04-26 | Cxcr3 receptor antagonists |
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| ES2620027T3 (es) | 2008-09-03 | 2017-06-27 | Biomarin Pharmaceutical Inc. | Composiciones que incluyen derivados del ácido 6-aminohexanoico como inhibidores de HDAC |
| JP5807971B2 (ja) | 2009-04-27 | 2015-11-10 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | Ｃｘｃｒ３受容体アンタゴニスト |
| US8362249B2 (en) * | 2009-04-27 | 2013-01-29 | Boehringer Ingelheim International Gmbh | CXCR3 receptor antagonists |
| JP2011057661A (ja) * | 2009-08-14 | 2011-03-24 | Bayer Cropscience Ag | 殺虫性カルボキサミド類 |
| WO2011084985A1 (en) | 2010-01-07 | 2011-07-14 | Boehringer Ingelheim International Gmbh | Cxcr3 receptor antagonists |
| US10059723B2 (en) | 2011-02-28 | 2018-08-28 | Biomarin Pharmaceutical Inc. | Histone deacetylase inhibitors |
| US8957066B2 (en) | 2011-02-28 | 2015-02-17 | Biomarin Pharmaceutical Inc. | Histone deacetylase inhibitors |
| US9540395B2 (en) | 2011-02-28 | 2017-01-10 | Biomarin Pharmaceutical Inc. | Histone deacetylase inhibitors |
| US8822464B2 (en) | 2011-11-28 | 2014-09-02 | Boehringer Ingelheim International Gmbh | N-aryl-piperazine derivatives and their use as positive allosteric modulators of mGluR5 receptors |
| US8741892B2 (en) | 2011-12-05 | 2014-06-03 | Boehringer Ingelheim International Gmbh | Compounds |
| US8642774B2 (en) | 2011-12-08 | 2014-02-04 | Boehringer Ingelheim International Gmbh | Compounds |
| US8796467B2 (en) | 2011-12-13 | 2014-08-05 | Boehringer Ingelheim International Gmbh | Compounds |
| US8846948B2 (en) * | 2011-12-13 | 2014-09-30 | Boehringer Ingelheim International Gmbh | Compounds |
| US8883789B2 (en) | 2011-12-14 | 2014-11-11 | Boehringer Ingelheim International Gmbh | Piperazine derivatives and their use as positive allosteric modulators of mGluR5 receptors |
| US8937176B2 (en) | 2011-12-14 | 2015-01-20 | Boehringer Ingelheim International Gmbh | Compounds |
| US8716277B2 (en) | 2011-12-14 | 2014-05-06 | Boehringer Ingelheim International Gmbh | Substituted imidazole compounds useful as positive allosteric modulators of mGlu5 receptor activity |
| US8889677B2 (en) | 2012-01-17 | 2014-11-18 | Boehringer Ingellheim International GmbH | Substituted triazoles useful as mGlu5 receptor modulators |
| KR101800607B1 (ko) * | 2012-02-02 | 2017-11-23 | 액테리온 파마슈티칼 리미티드 | ４-(벤조이미다졸-２-일)-티아졸 화합물 및 관련 아자 유도체 |
| KR20150132345A (ko) | 2013-03-15 | 2015-11-25 | 바이오마린 파머수티컬 인크. | Hdac 저해제 |
| JP6330040B2 (ja) | 2013-07-22 | 2018-05-23 | イドーシア ファーマシューティカルズ リミテッドＩｄｏｒｓｉａ Ｐｈａｒｍａｃｅｕｔｉｃａｌｓ Ｌｔｄ | １−（ピペラジン−１−イル）−２−（［１，２，４］トリアゾール−１−イル）−エタノン誘導体 |
| AR099789A1 (es) * | 2014-03-24 | 2016-08-17 | Actelion Pharmaceuticals Ltd | Derivados de 8-(piperazin-1-il)-1,2,3,4-tetrahidro-isoquinolina |
| AR103399A1 (es) | 2015-01-15 | 2017-05-10 | Actelion Pharmaceuticals Ltd | Derivados de (r)-2-metil-piperazina como moduladores del receptor cxcr3 |
| PT3245203T (pt) | 2015-01-15 | 2019-02-08 | Idorsia Pharmaceuticals Ltd | Derivados de hidroxialquil-piperazina como modeladores do recetor cxcr3 |
| WO2018011265A1 (en) | 2016-07-13 | 2018-01-18 | Idorsia Pharmaceuticals Ltd | Hydroxyalkyl-piperazine derivatives as cxcr3 receptor modulators |
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| US5948786A (en) * | 1996-04-12 | 1999-09-07 | Sumitomo Pharmaceuticals Company, Limited | Piperidinylpyrimidine derivatives |
| AU2521597A (en) * | 1996-04-12 | 1997-11-07 | Sumitomo Pharmaceuticals Company, Limited | Piperidinylpyramidine derivatives |
| AR038366A1 (es) * | 2001-11-30 | 2005-01-12 | Schering Corp | Compuestos de 1,2,4-triazolo [1,5-c] pirimidinas sustituidas, antagonistas del receptor de adenosina a2a, composiciones farmaceuticas, el uso de dichos compuestos para la manufactura de un medicamento para el tratamiento de enfermedades del sistema nervioso central y un kit que comprende combinacion |
| KR20040097375A (ko) | 2002-04-23 | 2004-11-17 | 시오노기 앤드 컴파니, 리미티드 | 피라졸로[1, 5-에이]피리미딘 유도체 및 이를 함유한엔에이디(피)에이취 산화효소 저해제 |
| ES2329356T3 (es) * | 2002-06-12 | 2009-11-25 | Chemocentryx, Inc. | Derivados de piperazina 1-arilo-4-sustituidos utilizados como antagonistas de ccr1 para el tratamiento de enfermedades inflamatorias e inmunitarias. |
| CA2514940A1 (en) * | 2003-02-03 | 2004-08-19 | Janssen Pharmaceutica N.V. | Quinoline-derived amide modulators of vanilloid vr1 receptor |
| ES2543714T3 (es) * | 2005-06-22 | 2015-08-21 | Chemocentryx, Inc. | Compuestos de azaindazol y métodos de uso |
| US20080312215A1 (en) | 2005-06-28 | 2008-12-18 | Pharmacopeia Drug Discovery, Inc. | Substituted [1,4]-diazepanes as CXCR3 antagonists and their use in the treatment of inflammatory disorders |
| US7790726B2 (en) * | 2005-08-16 | 2010-09-07 | Chemocentryx, Inc. | Monocyclic and bicyclic compounds and methods of use |
| US20090030012A1 (en) * | 2006-02-23 | 2009-01-29 | Adams Alan D | Pyridine, Pyrimidine and Pyrazine Derivatives as Cxcr3 Receptor Modulators |
| CN101426774B (zh) | 2006-04-19 | 2012-04-25 | 安斯泰来制药有限公司 | 唑类甲酰胺衍生物 |
| US7807671B2 (en) * | 2006-04-25 | 2010-10-05 | Bristol-Myers Squibb Company | Diketo-piperazine and piperidine derivatives as antiviral agents |
| AU2007314342B2 (en) | 2006-10-31 | 2013-02-21 | Merck Sharp & Dohme Corp. | Anilinopiperazine Derivatives and methods of use thereof |
| US20090099201A1 (en) * | 2007-05-22 | 2009-04-16 | David Robert Bolin | Diacylglycerol Acyltransferase Inhibitors |
| JO2972B1 (en) | 2007-06-08 | 2016-03-15 | جانسين فارماسوتيكا ان. في | Piperidine / piperazine derivatives |
| CN101896472A (zh) * | 2007-12-13 | 2010-11-24 | 锡耶纳生物技术股份公司 | Hedgehog途径拮抗剂及其治疗应用 |
| PE20091576A1 (es) | 2008-02-19 | 2009-11-05 | Sanofi Aventis | DERIVADOS DE 3-(AMIDO O SULFAMIDO)-4-(4-AZINIL SUSTITUIDO)BENZAMIDA COMO INHIBIDORES DEL RECEPTOR DE QUIMIOQUINAS CxCR3 |
| US8362249B2 (en) | 2009-04-27 | 2013-01-29 | Boehringer Ingelheim International Gmbh | CXCR3 receptor antagonists |
| JP5807971B2 (ja) | 2009-04-27 | 2015-11-10 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | Ｃｘｃｒ３受容体アンタゴニスト |
| WO2011084985A1 (en) | 2010-01-07 | 2011-07-14 | Boehringer Ingelheim International Gmbh | Cxcr3 receptor antagonists |
-
2010
- 2010-04-26 JP JP2012507460A patent/JP5807971B2/ja active Active
- 2010-04-26 EP EP10715470.0A patent/EP2424840B1/en active Active
- 2010-04-26 WO PCT/US2010/032347 patent/WO2010126811A1/en not_active Ceased
- 2010-04-27 US US12/768,268 patent/US8450317B2/en active Active
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