JP5498374B2 - ２−シアノフェニル縮合複素環式化合物および組成物、ならびにその使用 - Google Patents
２−シアノフェニル縮合複素環式化合物および組成物、ならびにその使用 Download PDFInfo
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- JP5498374B2 JP5498374B2 JP2010504040A JP2010504040A JP5498374B2 JP 5498374 B2 JP5498374 B2 JP 5498374B2 JP 2010504040 A JP2010504040 A JP 2010504040A JP 2010504040 A JP2010504040 A JP 2010504040A JP 5498374 B2 JP5498374 B2 JP 5498374B2
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- JP
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- Prior art keywords
- pyrimidin
- pyrido
- dihydro
- benzonitrile
- methyl
- 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.)
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- -1 2-Cyanophenyl Chemical group 0.000 title claims description 202
- 239000000203 mixture Substances 0.000 title claims description 193
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- 150000001875 compounds Chemical class 0.000 claims description 302
- 125000000217 alkyl group Chemical group 0.000 claims description 83
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 75
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 72
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- 229910052739 hydrogen Inorganic materials 0.000 claims description 50
- 230000036407 pain Effects 0.000 claims description 47
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Substances N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 46
- 239000008194 pharmaceutical composition Substances 0.000 claims description 43
- 238000011282 treatment Methods 0.000 claims description 42
- 239000001257 hydrogen Substances 0.000 claims description 36
- 150000003839 salts Chemical class 0.000 claims description 34
- 125000003545 alkoxy group Chemical group 0.000 claims description 32
- 239000012453 solvate Substances 0.000 claims description 30
- 229910052801 chlorine Inorganic materials 0.000 claims description 23
- 229910052731 fluorine Inorganic materials 0.000 claims description 23
- 230000000155 isotopic effect Effects 0.000 claims description 23
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 claims description 23
- 208000035475 disorder Diseases 0.000 claims description 22
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 20
- 230000001404 mediated effect Effects 0.000 claims description 20
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- 125000004943 pyrimidin-6-yl group Chemical group N1=CN=CC=C1* 0.000 claims description 18
- 208000023275 Autoimmune disease Diseases 0.000 claims description 17
- 208000037765 diseases and disorders Diseases 0.000 claims description 17
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 17
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 17
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- NWPNXBQSRGKSJB-UHFFFAOYSA-N 2-methylbenzonitrile Chemical compound CC1=CC=CC=C1C#N NWPNXBQSRGKSJB-UHFFFAOYSA-N 0.000 claims description 14
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- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 9
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- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 8
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- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 6
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- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
- PFTSILFRTYLFOO-UHFFFAOYSA-N 2-[4-[1-(1,3-benzodioxol-5-yl)ethylamino]-7,8-dihydro-5h-pyrido[4,3-d]pyrimidin-6-yl]-5-methylbenzonitrile Chemical compound C=1C=C2OCOC2=CC=1C(C)NC(C=1C2)=NC=NC=1CCN2C1=CC=C(C)C=C1C#N PFTSILFRTYLFOO-UHFFFAOYSA-N 0.000 claims description 5
- PFTSILFRTYLFOO-MRXNPFEDSA-N 2-[4-[[(1r)-1-(1,3-benzodioxol-5-yl)ethyl]amino]-7,8-dihydro-5h-pyrido[4,3-d]pyrimidin-6-yl]-5-methylbenzonitrile Chemical compound N([C@H](C)C=1C=C2OCOC2=CC=1)C(C=1C2)=NC=NC=1CCN2C1=CC=C(C)C=C1C#N PFTSILFRTYLFOO-MRXNPFEDSA-N 0.000 claims description 5
- IUVDXBRGFXCMBT-MRXNPFEDSA-N 2-[4-[[(1r)-1-(4-chloro-3-methylsulfonylphenyl)ethyl]amino]-7,8-dihydro-5h-pyrido[4,3-d]pyrimidin-6-yl]-5-methylbenzonitrile Chemical compound N([C@H](C)C=1C=C(C(Cl)=CC=1)S(C)(=O)=O)C(C=1C2)=NC=NC=1CCN2C1=CC=C(C)C=C1C#N IUVDXBRGFXCMBT-MRXNPFEDSA-N 0.000 claims description 5
- IUVDXBRGFXCMBT-INIZCTEOSA-N 2-[4-[[(1s)-1-(4-chloro-3-methylsulfonylphenyl)ethyl]amino]-7,8-dihydro-5h-pyrido[4,3-d]pyrimidin-6-yl]-5-methylbenzonitrile Chemical compound N([C@@H](C)C=1C=C(C(Cl)=CC=1)S(C)(=O)=O)C(C=1C2)=NC=NC=1CCN2C1=CC=C(C)C=C1C#N IUVDXBRGFXCMBT-INIZCTEOSA-N 0.000 claims description 5
- QNHMPCGUVCJNLG-LJQANCHMSA-N 2-[4-[[(1s)-2-hydroxy-1-(2-methoxypyrimidin-5-yl)ethyl]amino]-7,8-dihydro-5h-pyrido[4,3-d]pyrimidin-6-yl]-5-methylbenzonitrile Chemical compound C1=NC(OC)=NC=C1[C@@H](CO)NC1=NC=NC2=C1CN(C=1C(=CC(C)=CC=1)C#N)CC2 QNHMPCGUVCJNLG-LJQANCHMSA-N 0.000 claims description 5
- HDTMYJRQEISETD-HXUWFJFHSA-N 2-[4-[[(1s)-2-hydroxy-1-(2-methylpyrimidin-5-yl)ethyl]amino]-7,8-dihydro-5h-pyrido[4,3-d]pyrimidin-6-yl]-5-methylbenzonitrile Chemical compound N#CC1=CC(C)=CC=C1N1CC2=C(N[C@H](CO)C=3C=NC(C)=NC=3)N=CN=C2CC1 HDTMYJRQEISETD-HXUWFJFHSA-N 0.000 claims description 5
- DFGOJQUEWDGMKI-UHFFFAOYSA-N 5-chloro-2-[4-[(6-methoxypyridin-3-yl)methylamino]-7,8-dihydro-5h-pyrido[4,3-d]pyrimidin-6-yl]benzonitrile Chemical compound C1=NC(OC)=CC=C1CNC1=NC=NC2=C1CN(C=1C(=CC(Cl)=CC=1)C#N)CC2 DFGOJQUEWDGMKI-UHFFFAOYSA-N 0.000 claims description 5
- ZBNNSVNQQSLELF-CYBMUJFWSA-N 5-chloro-2-[4-[[(1r)-1-[6-(trifluoromethyl)pyridin-3-yl]ethyl]amino]-7,8-dihydro-5h-pyrido[4,3-d]pyrimidin-6-yl]benzonitrile Chemical compound N([C@H](C)C=1C=NC(=CC=1)C(F)(F)F)C(C=1C2)=NC=NC=1CCN2C1=CC=C(Cl)C=C1C#N ZBNNSVNQQSLELF-CYBMUJFWSA-N 0.000 claims description 5
- SBBMJIATEIOEIQ-OAHLLOKOSA-N 5-methyl-2-[4-[[(1r)-1-[6-(trifluoromethyl)pyridin-3-yl]ethyl]amino]-7,8-dihydro-5h-pyrido[4,3-d]pyrimidin-6-yl]benzonitrile Chemical compound N([C@H](C)C=1C=NC(=CC=1)C(F)(F)F)C(C=1C2)=NC=NC=1CCN2C1=CC=C(C)C=C1C#N SBBMJIATEIOEIQ-OAHLLOKOSA-N 0.000 claims description 5
- FJEGDSNOOKRLRP-QGZVFWFLSA-N 5-methyl-2-[4-[[(1r)-1-quinoxalin-6-ylethyl]amino]-7,8-dihydro-5h-pyrido[4,3-d]pyrimidin-6-yl]benzonitrile Chemical compound N([C@H](C)C=1C=C2N=CC=NC2=CC=1)C(C=1C2)=NC=NC=1CCN2C1=CC=C(C)C=C1C#N FJEGDSNOOKRLRP-QGZVFWFLSA-N 0.000 claims description 5
- NMFJPJCALUOMRM-UHFFFAOYSA-N 5-methyl-2-[4-[[6-(trifluoromethyl)pyridin-3-yl]methylamino]-7,8-dihydro-5h-pyrido[4,3-d]pyrimidin-6-yl]benzonitrile Chemical compound N#CC1=CC(C)=CC=C1N1CC2=C(NCC=3C=NC(=CC=3)C(F)(F)F)N=CN=C2CC1 NMFJPJCALUOMRM-UHFFFAOYSA-N 0.000 claims description 5
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- 229910052794 bromium Inorganic materials 0.000 claims description 5
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- 125000002757 morpholinyl group Chemical group 0.000 claims description 5
- 206010044652 trigeminal neuralgia Diseases 0.000 claims description 5
- XSSBBWWYALHHHM-UHFFFAOYSA-N 2-[4-(1,3-benzoxazol-5-ylmethylamino)-7,8-dihydro-5h-pyrido[4,3-d]pyrimidin-6-yl]-5-methylbenzonitrile Chemical compound N#CC1=CC(C)=CC=C1N1CC2=C(NCC=3C=C4N=COC4=CC=3)N=CN=C2CC1 XSSBBWWYALHHHM-UHFFFAOYSA-N 0.000 claims description 4
- QYKQWICOAQCEFR-UHFFFAOYSA-N 2-[4-(imidazo[1,2-a]pyridin-7-ylmethylamino)-7,8-dihydro-5h-pyrido[4,3-d]pyrimidin-6-yl]-5-methylbenzonitrile Chemical compound N#CC1=CC(C)=CC=C1N1CC2=C(NCC3=CC4=NC=CN4C=C3)N=CN=C2CC1 QYKQWICOAQCEFR-UHFFFAOYSA-N 0.000 claims description 4
- UZBQPRXVKUBNPY-UHFFFAOYSA-N 2-[4-[(5-cyclopropylpyridin-2-yl)methylamino]-7,8-dihydro-5h-pyrido[4,3-d]pyrimidin-6-yl]-5-methylbenzonitrile Chemical compound N#CC1=CC(C)=CC=C1N1CC2=C(NCC=3N=CC(=CC=3)C3CC3)N=CN=C2CC1 UZBQPRXVKUBNPY-UHFFFAOYSA-N 0.000 claims description 4
- RVOHPYXQEZNVMH-UHFFFAOYSA-N 2-[4-[(6-methoxypyridin-3-yl)methylamino]-7,8-dihydro-5h-pyrido[4,3-d]pyrimidin-6-yl]-5-methylbenzonitrile Chemical compound C1=NC(OC)=CC=C1CNC1=NC=NC2=C1CN(C=1C(=CC(C)=CC=1)C#N)CC2 RVOHPYXQEZNVMH-UHFFFAOYSA-N 0.000 claims description 4
- IUVDXBRGFXCMBT-UHFFFAOYSA-N 2-[4-[1-(4-chloro-3-methylsulfonylphenyl)ethylamino]-7,8-dihydro-5h-pyrido[4,3-d]pyrimidin-6-yl]-5-methylbenzonitrile Chemical compound C=1C=C(Cl)C(S(C)(=O)=O)=CC=1C(C)NC(C=1C2)=NC=NC=1CCN2C1=CC=C(C)C=C1C#N IUVDXBRGFXCMBT-UHFFFAOYSA-N 0.000 claims description 4
- OSQOURHXWJQPNS-OAHLLOKOSA-N 2-[4-[[(1r)-1-(2-methoxypyrimidin-5-yl)ethyl]amino]-7,8-dihydro-5h-pyrido[4,3-d]pyrimidin-6-yl]-5-methylbenzonitrile Chemical compound C1=NC(OC)=NC=C1[C@@H](C)NC1=NC=NC2=C1CN(C=1C(=CC(C)=CC=1)C#N)CC2 OSQOURHXWJQPNS-OAHLLOKOSA-N 0.000 claims description 4
- WDRMEYJAYGWMTR-OAQYLSRUSA-N 2-[4-[[(1r)-3-hydroxy-1-(6-methylpyridin-3-yl)propyl]amino]-7,8-dihydro-5h-pyrido[4,3-d]pyrimidin-6-yl]-5-methylbenzonitrile Chemical compound N#CC1=CC(C)=CC=C1N1CC2=C(N[C@H](CCO)C=3C=NC(C)=CC=3)N=CN=C2CC1 WDRMEYJAYGWMTR-OAQYLSRUSA-N 0.000 claims description 4
- MPEWWUPGWDTWHF-LJQANCHMSA-N 2-[4-[[(1r)-3-hydroxy-1-[6-(trifluoromethyl)pyridin-3-yl]propyl]amino]-7,8-dihydro-5h-pyrido[4,3-d]pyrimidin-6-yl]-5-methylbenzonitrile Chemical compound N#CC1=CC(C)=CC=C1N1CC2=C(N[C@H](CCO)C=3C=NC(=CC=3)C(F)(F)F)N=CN=C2CC1 MPEWWUPGWDTWHF-LJQANCHMSA-N 0.000 claims description 4
- PFTSILFRTYLFOO-INIZCTEOSA-N 2-[4-[[(1s)-1-(1,3-benzodioxol-5-yl)ethyl]amino]-7,8-dihydro-5h-pyrido[4,3-d]pyrimidin-6-yl]-5-methylbenzonitrile Chemical compound N([C@@H](C)C=1C=C2OCOC2=CC=1)C(C=1C2)=NC=NC=1CCN2C1=CC=C(C)C=C1C#N PFTSILFRTYLFOO-INIZCTEOSA-N 0.000 claims description 4
- RXZNFBASJKIFOC-LJQANCHMSA-N 2-[4-[[(1s)-2-hydroxy-1-[6-(trifluoromethyl)pyridin-3-yl]ethyl]amino]-7,8-dihydro-5h-pyrido[4,3-d]pyrimidin-6-yl]-5-methylbenzonitrile Chemical compound N#CC1=CC(C)=CC=C1N1CC2=C(N[C@H](CO)C=3C=NC(=CC=3)C(F)(F)F)N=CN=C2CC1 RXZNFBASJKIFOC-LJQANCHMSA-N 0.000 claims description 4
- DPWHSCNGPJHQJY-UHFFFAOYSA-N 5-(trifluoromethyl)-2-[4-[[6-(trifluoromethyl)pyridin-3-yl]methylamino]-7,8-dihydro-5h-pyrido[4,3-d]pyrimidin-6-yl]benzonitrile Chemical compound N#CC1=CC(C(F)(F)F)=CC=C1N1CC2=C(NCC=3C=NC(=CC=3)C(F)(F)F)N=CN=C2CC1 DPWHSCNGPJHQJY-UHFFFAOYSA-N 0.000 claims description 4
- VFJLLZUKLXBDGQ-UHFFFAOYSA-N 5-bromo-2-[4-[(6-methoxypyridin-3-yl)methylamino]-7,8-dihydro-5h-pyrido[4,3-d]pyrimidin-6-yl]benzonitrile Chemical compound C1=NC(OC)=CC=C1CNC1=NC=NC2=C1CN(C=1C(=CC(Br)=CC=1)C#N)CC2 VFJLLZUKLXBDGQ-UHFFFAOYSA-N 0.000 claims description 4
- OMDXBHIZMDEQDL-CYBMUJFWSA-N 5-bromo-2-[4-[[(1r)-1-[6-(trifluoromethyl)pyridin-3-yl]ethyl]amino]-7,8-dihydro-5h-pyrido[4,3-d]pyrimidin-6-yl]benzonitrile Chemical compound N([C@H](C)C=1C=NC(=CC=1)C(F)(F)F)C(C=1C2)=NC=NC=1CCN2C1=CC=C(Br)C=C1C#N OMDXBHIZMDEQDL-CYBMUJFWSA-N 0.000 claims description 4
- ONLFWKIEMKGZBZ-UHFFFAOYSA-N 5-bromo-2-[4-[[6-(trifluoromethyl)pyridin-3-yl]methylamino]-7,8-dihydro-5h-pyrido[4,3-d]pyrimidin-6-yl]benzonitrile Chemical compound C1=NC(C(F)(F)F)=CC=C1CNC1=NC=NC2=C1CN(C=1C(=CC(Br)=CC=1)C#N)CC2 ONLFWKIEMKGZBZ-UHFFFAOYSA-N 0.000 claims description 4
- RWDLAWFZWCCWPB-UHFFFAOYSA-N 5-chloro-2-[4-(imidazo[1,2-a]pyridin-7-ylmethylamino)-7,8-dihydro-5h-pyrido[4,3-d]pyrimidin-6-yl]benzonitrile Chemical compound N#CC1=CC(Cl)=CC=C1N1CC2=C(NCC3=CC4=NC=CN4C=C3)N=CN=C2CC1 RWDLAWFZWCCWPB-UHFFFAOYSA-N 0.000 claims description 4
- DEYKZLFOASXYJB-CYBMUJFWSA-N 5-chloro-2-[4-[[(1r)-1-(2-methoxypyrimidin-5-yl)ethyl]amino]-7,8-dihydro-5h-pyrido[4,3-d]pyrimidin-6-yl]benzonitrile Chemical compound C1=NC(OC)=NC=C1[C@@H](C)NC1=NC=NC2=C1CN(C=1C(=CC(Cl)=CC=1)C#N)CC2 DEYKZLFOASXYJB-CYBMUJFWSA-N 0.000 claims description 4
- CYOUZCALCGKRHO-LJQANCHMSA-N 5-chloro-2-[4-[[(1s)-2-hydroxy-1-(2-methylpyrimidin-5-yl)ethyl]amino]-7,8-dihydro-5h-pyrido[4,3-d]pyrimidin-6-yl]benzonitrile Chemical compound C1=NC(C)=NC=C1[C@@H](CO)NC1=NC=NC2=C1CN(C=1C(=CC(Cl)=CC=1)C#N)CC2 CYOUZCALCGKRHO-LJQANCHMSA-N 0.000 claims description 4
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- WCJJIANNMBQADZ-UHFFFAOYSA-N 5-chloro-2-[4-[[3-(1,2,4-triazol-4-yl)phenyl]methylamino]-7,8-dihydro-5h-pyrido[4,3-d]pyrimidin-6-yl]benzonitrile Chemical compound N#CC1=CC(Cl)=CC=C1N1CC2=C(NCC=3C=C(C=CC=3)N3C=NN=C3)N=CN=C2CC1 WCJJIANNMBQADZ-UHFFFAOYSA-N 0.000 claims description 4
- LHUYOPDVSCBYGR-UHFFFAOYSA-N 5-chloro-2-[4-[[6-(dimethylamino)pyridin-3-yl]methylamino]-7,8-dihydro-5h-pyrido[4,3-d]pyrimidin-6-yl]benzonitrile Chemical compound C1=NC(N(C)C)=CC=C1CNC1=NC=NC2=C1CN(C=1C(=CC(Cl)=CC=1)C#N)CC2 LHUYOPDVSCBYGR-UHFFFAOYSA-N 0.000 claims description 4
- YSDMEQRYDFBWMF-UHFFFAOYSA-N 5-chloro-2-[4-[[6-(trifluoromethyl)pyridin-3-yl]methylamino]-7,8-dihydro-5h-pyrido[4,3-d]pyrimidin-6-yl]benzonitrile Chemical compound C1=NC(C(F)(F)F)=CC=C1CNC1=NC=NC2=C1CN(C=1C(=CC(Cl)=CC=1)C#N)CC2 YSDMEQRYDFBWMF-UHFFFAOYSA-N 0.000 claims description 4
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
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- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Animal Behavior & Ethology (AREA)
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- Biomedical Technology (AREA)
- Immunology (AREA)
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- Pulmonology (AREA)
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- Otolaryngology (AREA)
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Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US92510907P | 2007-04-17 | 2007-04-17 | |
| US60/925,109 | 2007-04-17 | ||
| US1051208P | 2008-01-08 | 2008-01-08 | |
| US61/010,512 | 2008-01-08 | ||
| PCT/US2008/004208 WO2008130481A1 (en) | 2007-04-17 | 2008-03-31 | 2-cyanophenyl fused heterocyclic compounds, and compositions and uses thereof |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2010524930A JP2010524930A (ja) | 2010-07-22 |
| JP2010524930A5 JP2010524930A5 (enExample) | 2011-04-07 |
| JP5498374B2 true JP5498374B2 (ja) | 2014-05-21 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
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| JP2010504040A Expired - Fee Related JP5498374B2 (ja) | 2007-04-17 | 2008-03-31 | ２−シアノフェニル縮合複素環式化合物および組成物、ならびにその使用 |
Country Status (12)
| Country | Link |
|---|---|
| US (2) | US8076345B2 (enExample) |
| EP (1) | EP2139334B1 (enExample) |
| JP (1) | JP5498374B2 (enExample) |
| CN (1) | CN101677569B (enExample) |
| CA (1) | CA2682692A1 (enExample) |
| CY (1) | CY1114382T1 (enExample) |
| DK (1) | DK2139334T3 (enExample) |
| ES (1) | ES2427999T3 (enExample) |
| HR (1) | HRP20130867T1 (enExample) |
| PL (1) | PL2139334T3 (enExample) |
| PT (1) | PT2139334E (enExample) |
| WO (1) | WO2008130481A1 (enExample) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5539235B2 (ja) | 2008-02-29 | 2014-07-02 | エボテック・アーゲー | アミド化合物、組成物およびそれらの使用 |
| WO2010066629A2 (en) * | 2008-12-09 | 2010-06-17 | F. Hoffmann-La Roche Ag | Novel azaindoles |
| UA112517C2 (uk) | 2010-07-06 | 2016-09-26 | Новартіс Аг | Тетрагідропіридопіримідинові похідні |
| AU2014253493B2 (en) * | 2010-07-06 | 2016-04-14 | Novartis Ag | Tetrahydro-pyrido-pyrimidine derivatives |
| JP2014518256A (ja) * | 2011-06-27 | 2014-07-28 | ノバルティス アーゲー | テトラヒドロ−ピリド−ピリミジン誘導体の固体形態および塩類 |
| PL2790705T3 (pl) | 2011-12-15 | 2018-06-29 | Novartis Ag | Zastosowanie inhibitorów czynności lub funkcji PI3K |
| CN103497149A (zh) * | 2013-10-08 | 2014-01-08 | 南京复兴生物科技有限公司 | 一种5-氨甲基吡啶衍生物的制备方法 |
| US10183937B2 (en) | 2014-12-09 | 2019-01-22 | Bayer Aktiengesellschaft | 1,3-thiazol-2-yl substituted benzamides |
| HUE055290T2 (hu) | 2014-12-09 | 2021-11-29 | Bayer Ag | 1,3-Tiazol-2-il-csoporttal szubsztituált benzamid-származékok |
| WO2017049498A1 (zh) * | 2015-09-23 | 2017-03-30 | 前湾医药科技（深圳）有限公司 | 一种咪唑并吡啶类化合物与在制备pi3k抑制剂中的应用 |
| US20230096028A1 (en) * | 2019-03-01 | 2023-03-30 | Revolution Medicines, Inc. | Bicyclic heterocyclyl compounds and uses thereof |
| BR112021022099A2 (pt) | 2019-05-31 | 2021-12-28 | Chiesi Farm Spa | Derivados de amino quinazolina como inibidores de p2x3 |
| KR20220016074A (ko) | 2019-05-31 | 2022-02-08 | 키에시 파르마슈티시 엣스. 피. 에이. | P2x3 억제제로서 피리도피리미딘 유도체 |
| TWI793704B (zh) * | 2020-08-06 | 2023-02-21 | 大陸商北京泰德製藥股份有限公司 | Sos1抑制劑、包含其的藥物組合物及其用途 |
| CA3196335A1 (en) | 2020-11-27 | 2022-06-02 | Chiesi Farmaceutici S.P.A. | Phthalazine derivatives as p2x3 inhibitors |
| CN116601149A (zh) | 2020-11-27 | 2023-08-15 | 奇斯药制品公司 | 作为p2x3抑制剂的氨基喹唑啉衍生物 |
| AU2021386684A1 (en) | 2020-11-27 | 2023-05-25 | Chiesi Farmaceutici S.P.A. | (aza)quinoline 4-amines derivatives as p2x3 inhibitors |
| KR20250110929A (ko) | 2022-12-02 | 2025-07-21 | 뉴모라 테라퓨틱스, 인코포레이티드 | 신경학적 장애를 치료하는 방법 |
Family Cites Families (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3424761A (en) * | 1966-03-07 | 1969-01-28 | Robins Co Inc A H | 3-ureidopyrrolidines |
| US3424760A (en) * | 1966-03-07 | 1969-01-28 | Robins Co Inc A H | 3-ureidopyrrolidines |
| DE2502588A1 (de) | 1975-01-23 | 1976-07-29 | Troponwerke Dinklage & Co | Basisch substituierte derivate des 7-amino-2-chinolons, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel |
| CA2373510A1 (en) | 1999-05-12 | 2000-11-23 | Ortho-Mcneil Pharmaceutical, Inc. | Pyrazole carboxamides useful for the treatment of obesity and other disorders |
| DE60122285D1 (de) * | 2000-01-14 | 2006-09-28 | Us Gov Health & Human Serv | Methonocarbacycloalkylanaloga von nucleosiden |
| US6531478B2 (en) | 2000-02-24 | 2003-03-11 | Cheryl P. Kordik | Amino pyrazole derivatives useful for the treatment of obesity and other disorders |
| KR20030024799A (ko) | 2000-07-20 | 2003-03-26 | 뉴로젠 코포레이션 | 캡사이신 수용체 리간드 |
| BR0116662A (pt) | 2001-01-02 | 2003-09-23 | Hoffmann La Roche | Derivados de quinazolona como antagonistas receptores alfa 1a/b adrenérgicos |
| WO2002088079A2 (en) | 2001-05-01 | 2002-11-07 | Bristol-Myers Squibb Company | Dual inhibitors of pde 7 and pde 4 |
| GB0206033D0 (en) | 2002-03-14 | 2002-04-24 | Pfizer Ltd | Compounds useful in therapy |
| AU2003242252A1 (en) | 2002-06-07 | 2003-12-22 | Kyowa Hakko Kogyo Co., Ltd. | Bicyclic pyrimidine derivatives |
| GB0225908D0 (en) | 2002-11-06 | 2002-12-11 | Pfizer Ltd | Treatment of female sexual dysfunction |
| CA2510471A1 (en) | 2002-12-19 | 2004-07-08 | Neurogen Corporation | Substituted biphenyl-4-carboxylic acid arylamide analogues as capsaicin receptor modulators |
| TW200530235A (en) * | 2003-12-24 | 2005-09-16 | Renovis Inc | Bicycloheteroarylamine compounds as ion channel ligands and uses thereof |
| US7297700B2 (en) * | 2005-03-24 | 2007-11-20 | Renovis, Inc. | Bicycloheteroaryl compounds as P2X7 modulators and uses thereof |
| EP1885369B1 (en) * | 2005-05-04 | 2015-09-23 | Evotec AG | Fused heterocyclic compounds, and compositions and uses thereof |
| JP5396379B2 (ja) * | 2007-04-02 | 2014-01-22 | エボテック・アーゲー | ピリド−２−イル縮合複素環式化合物ならびにその組成物および使用 |
| US8546388B2 (en) * | 2008-10-24 | 2013-10-01 | Purdue Pharma L.P. | Heterocyclic TRPV1 receptor ligands |
-
2008
- 2008-03-31 PT PT87424305T patent/PT2139334E/pt unknown
- 2008-03-31 ES ES08742430T patent/ES2427999T3/es active Active
- 2008-03-31 EP EP08742430.5A patent/EP2139334B1/en not_active Not-in-force
- 2008-03-31 US US12/080,253 patent/US8076345B2/en not_active Expired - Fee Related
- 2008-03-31 HR HRP20130867AT patent/HRP20130867T1/hr unknown
- 2008-03-31 JP JP2010504040A patent/JP5498374B2/ja not_active Expired - Fee Related
- 2008-03-31 PL PL08742430T patent/PL2139334T3/pl unknown
- 2008-03-31 DK DK08742430.5T patent/DK2139334T3/da active
- 2008-03-31 CN CN200880016706.XA patent/CN101677569B/zh not_active Expired - Fee Related
- 2008-03-31 WO PCT/US2008/004208 patent/WO2008130481A1/en not_active Ceased
- 2008-03-31 CA CA002682692A patent/CA2682692A1/en not_active Abandoned
-
2011
- 2011-12-12 US US13/323,748 patent/US20120149700A1/en not_active Abandoned
-
2013
- 2013-09-16 CY CY20131100796T patent/CY1114382T1/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| PT2139334E (pt) | 2013-10-02 |
| CN101677569B (zh) | 2014-01-22 |
| HRP20130867T1 (hr) | 2013-10-25 |
| JP2010524930A (ja) | 2010-07-22 |
| DK2139334T3 (da) | 2013-09-23 |
| US8076345B2 (en) | 2011-12-13 |
| EP2139334A1 (en) | 2010-01-06 |
| PL2139334T3 (pl) | 2013-11-29 |
| EP2139334A4 (en) | 2011-06-22 |
| WO2008130481A1 (en) | 2008-10-30 |
| CN101677569A (zh) | 2010-03-24 |
| CA2682692A1 (en) | 2008-10-30 |
| ES2427999T3 (es) | 2013-11-05 |
| US20120149700A1 (en) | 2012-06-14 |
| EP2139334B1 (en) | 2013-07-03 |
| US20080275037A1 (en) | 2008-11-06 |
| CY1114382T1 (el) | 2016-08-31 |
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