JP2016525142A5 - - Google Patents
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- Publication number
- JP2016525142A5 JP2016525142A5 JP2016528556A JP2016528556A JP2016525142A5 JP 2016525142 A5 JP2016525142 A5 JP 2016525142A5 JP 2016528556 A JP2016528556 A JP 2016528556A JP 2016528556 A JP2016528556 A JP 2016528556A JP 2016525142 A5 JP2016525142 A5 JP 2016525142A5
- Authority
- JP
- Japan
- Prior art keywords
- naphthyridine
- carboxamide
- formula
- disorder
- compound
- 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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- 150000001875 compounds Chemical class 0.000 claims description 24
- ZPUCINDJVBIVPJ-LJISPDSOSA-N cocaine Chemical compound O([C@H]1C[C@@H]2CC[C@@H](N2C)[C@H]1C(=O)OC)C(=O)C1=CC=CC=C1 ZPUCINDJVBIVPJ-LJISPDSOSA-N 0.000 claims description 10
- 208000027104 Chemotherapy-Related Cognitive Impairment Diseases 0.000 claims description 6
- 206010061323 Optic neuropathy Diseases 0.000 claims description 6
- 208000002780 macular degeneration Diseases 0.000 claims description 6
- -1 opiates Chemical compound 0.000 claims description 6
- 208000020911 optic nerve disease Diseases 0.000 claims description 6
- 208000024827 Alzheimer disease Diseases 0.000 claims description 5
- 208000019901 Anxiety disease Diseases 0.000 claims description 5
- 102000014461 Ataxins Human genes 0.000 claims description 5
- 108010078286 Ataxins Proteins 0.000 claims description 5
- 208000020925 Bipolar disease Diseases 0.000 claims description 5
- 206010008025 Cerebellar ataxia Diseases 0.000 claims description 5
- 208000028698 Cognitive impairment Diseases 0.000 claims description 5
- 206010011878 Deafness Diseases 0.000 claims description 5
- 206010012289 Dementia Diseases 0.000 claims description 5
- 201000010374 Down Syndrome Diseases 0.000 claims description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 5
- 208000023105 Huntington disease Diseases 0.000 claims description 5
- 208000018737 Parkinson disease Diseases 0.000 claims description 5
- 201000007737 Retinal degeneration Diseases 0.000 claims description 5
- 208000009415 Spinocerebellar Ataxias Diseases 0.000 claims description 5
- 208000006011 Stroke Diseases 0.000 claims description 5
- 208000009205 Tinnitus Diseases 0.000 claims description 5
- 208000030886 Traumatic Brain injury Diseases 0.000 claims description 5
- 230000032683 aging Effects 0.000 claims description 5
- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims description 5
- 208000029560 autism spectrum disease Diseases 0.000 claims description 5
- 201000004562 autosomal dominant cerebellar ataxia Diseases 0.000 claims description 5
- 230000037326 chronic stress Effects 0.000 claims description 5
- 229960003920 cocaine Drugs 0.000 claims description 5
- 208000010877 cognitive disease Diseases 0.000 claims description 5
- 206010015037 epilepsy Diseases 0.000 claims description 5
- 230000010370 hearing loss Effects 0.000 claims description 5
- 231100000888 hearing loss Toxicity 0.000 claims description 5
- 208000016354 hearing loss disease Diseases 0.000 claims description 5
- 229960001252 methamphetamine Drugs 0.000 claims description 5
- MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 claims description 5
- 201000006417 multiple sclerosis Diseases 0.000 claims description 5
- 208000030459 obsessive-compulsive personality disease Diseases 0.000 claims description 5
- 208000019906 panic disease Diseases 0.000 claims description 5
- JTJMJGYZQZDUJJ-UHFFFAOYSA-N phencyclidine Chemical compound C1CCCCN1C1(C=2C=CC=CC=2)CCCCC1 JTJMJGYZQZDUJJ-UHFFFAOYSA-N 0.000 claims description 5
- 229950010883 phencyclidine Drugs 0.000 claims description 5
- 208000028173 post-traumatic stress disease Diseases 0.000 claims description 5
- 238000001959 radiotherapy Methods 0.000 claims description 5
- 230000004258 retinal degeneration Effects 0.000 claims description 5
- 201000000980 schizophrenia Diseases 0.000 claims description 5
- 208000020431 spinal cord injury Diseases 0.000 claims description 5
- 231100000886 tinnitus Toxicity 0.000 claims description 5
- 230000009529 traumatic brain injury Effects 0.000 claims description 5
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 229940127240 opiate Drugs 0.000 claims description 4
- 201000009032 substance abuse Diseases 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims 6
- 150000002367 halogens Chemical class 0.000 claims 6
- 229910052739 hydrogen Inorganic materials 0.000 claims 4
- 239000001257 hydrogen Substances 0.000 claims 4
- 125000003386 piperidinyl group Chemical group 0.000 claims 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- 239000002253 acid Substances 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- KOEDUOJFTQPVFV-UHFFFAOYSA-N 5-(4-chloro-2-fluorophenyl)-1,7-naphthyridine-3-carboxamide 5-(4-chlorophenyl)-2-methyl-1,7-naphthyridine-3-carboxamide 5-[4-(trifluoromethyl)phenyl]-1,7-naphthyridine-3-carboxamide Chemical compound ClC1=CC(=C(C=C1)C1=C2C=C(C=NC2=CN=C1)C(=O)N)F.ClC1=CC=C(C=C1)C1=C2C=C(C(=NC2=CN=C1)C)C(=O)N.FC(C1=CC=C(C=C1)C1=C2C=C(C=NC2=CN=C1)C(=O)N)(F)F KOEDUOJFTQPVFV-UHFFFAOYSA-N 0.000 claims 2
- LFWAFNHIZJQQEA-UHFFFAOYSA-N 5-(4-chlorophenyl)-1,7-naphthyridine-3-carboxamide 5-(2-fluorophenyl)-1,7-naphthyridine-3-carboxamide 5-[4-(trifluoromethoxy)phenyl]-1,7-naphthyridine-3-carboxamide Chemical compound FC1=C(C=CC=C1)C1=C2C=C(C=NC2=CN=C1)C(=O)N.FC(OC1=CC=C(C=C1)C1=C2C=C(C=NC2=CN=C1)C(=O)N)(F)F.ClC1=CC=C(C=C1)C1=C2C=C(C=NC2=CN=C1)C(=O)N LFWAFNHIZJQQEA-UHFFFAOYSA-N 0.000 claims 2
- KRTVGKLRIOHLJA-UHFFFAOYSA-N CS(=O)(=O)C1=CC=C(C=C1)C1=C2C=CC(=NC2=CN=C1)C(=O)N.C(#N)C1=CC=C(C=C1)C1=C2C=C(C=NC2=CN=C1)C(=O)N.FC1=C(C=CC(=C1)F)C1=C2C=C(C=NC2=CN=C1)C(=O)N Chemical compound CS(=O)(=O)C1=CC=C(C=C1)C1=C2C=CC(=NC2=CN=C1)C(=O)N.C(#N)C1=CC=C(C=C1)C1=C2C=C(C=NC2=CN=C1)C(=O)N.FC1=C(C=CC(=C1)F)C1=C2C=C(C=NC2=CN=C1)C(=O)N KRTVGKLRIOHLJA-UHFFFAOYSA-N 0.000 claims 2
- FXBCOCUINVUCRH-UHFFFAOYSA-N FC=1C=C(C=CC1F)C1=C2C=C(C=NC2=CN=C1)C(=O)N.FC1=CC=C(C=C1)C1=C2C=C(C=NC2=CN=C1)C(=O)N.FC=1C=C(C=C(C1F)F)C1=C2C=C(C=NC2=CN=C1)C(=O)N Chemical compound FC=1C=C(C=CC1F)C1=C2C=C(C=NC2=CN=C1)C(=O)N.FC1=CC=C(C=C1)C1=C2C=C(C=NC2=CN=C1)C(=O)N.FC=1C=C(C=C(C1F)F)C1=C2C=C(C=NC2=CN=C1)C(=O)N FXBCOCUINVUCRH-UHFFFAOYSA-N 0.000 claims 2
- OSBMCAAGAMWTHR-UHFFFAOYSA-N NC(=O)c1cnc2cncc(-c3ccc(Cl)cc3Cl)c2c1 Chemical compound NC(=O)c1cnc2cncc(-c3ccc(Cl)cc3Cl)c2c1 OSBMCAAGAMWTHR-UHFFFAOYSA-N 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims 2
- 125000005043 dihydropyranyl group Chemical group O1C(CCC=C1)* 0.000 claims 2
- 125000004438 haloalkoxy group Chemical group 0.000 claims 2
- 125000002757 morpholinyl group Chemical group 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 125000004076 pyridyl group Chemical group 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 1
- APRUAPSIJAMGDL-UHFFFAOYSA-N 5-(4-chloro-2-fluorophenyl)-N-(2-methylsulfonylethyl)-1,7-naphthyridine-3-carboxamide 5-(2-fluorophenyl)-N-(2,2,2-trifluoroethyl)-1,7-naphthyridine-3-carboxamide Chemical compound FC1=C(C=CC=C1)C1=C2C=C(C=NC2=CN=C1)C(=O)NCC(F)(F)F.ClC1=CC(=C(C=C1)C1=C2C=C(C=NC2=CN=C1)C(=O)NCCS(=O)(=O)C)F APRUAPSIJAMGDL-UHFFFAOYSA-N 0.000 claims 1
- ISVMIRRKFYRKPP-UHFFFAOYSA-N ClC1=CC=C(C=C1)C1=C2C=C(C=NC2=CN=C1)C(=O)NCC1=CC(=CC=C1)S(=O)(=O)C.ClC1=CC=C(C=C1)C1=C2C=C(C=NC2=CN=C1)C(=O)NCC1=CC=C(C=C1)S(=O)(=O)C Chemical compound ClC1=CC=C(C=C1)C1=C2C=C(C=NC2=CN=C1)C(=O)NCC1=CC(=CC=C1)S(=O)(=O)C.ClC1=CC=C(C=C1)C1=C2C=C(C=NC2=CN=C1)C(=O)NCC1=CC=C(C=C1)S(=O)(=O)C ISVMIRRKFYRKPP-UHFFFAOYSA-N 0.000 claims 1
- OVDGKEBJUCDVGD-UHFFFAOYSA-N ClC1=CC=C(C=C1)C1=C2C=C(C=NC2=CN=C1)C(=O)NCCOC.ClC1=CC=C(C=C1)C1=C2C=C(C=NC2=CN=C1)C(=O)NCC1CC1 Chemical compound ClC1=CC=C(C=C1)C1=C2C=C(C=NC2=CN=C1)C(=O)NCCOC.ClC1=CC=C(C=C1)C1=C2C=C(C=NC2=CN=C1)C(=O)NCC1CC1 OVDGKEBJUCDVGD-UHFFFAOYSA-N 0.000 claims 1
- NJNWTXRGVFJHBM-UHFFFAOYSA-N FC(OC=1C=C(C=CC1)C1=C2C=C(C=NC2=CN=C1)C(=O)N)(F)F.COC=1C=C(C=CC1)C1=C2C=C(C=NC2=CN=C1)C(=O)N Chemical compound FC(OC=1C=C(C=CC1)C1=C2C=C(C=NC2=CN=C1)C(=O)N)(F)F.COC=1C=C(C=CC1)C1=C2C=C(C=NC2=CN=C1)C(=O)N NJNWTXRGVFJHBM-UHFFFAOYSA-N 0.000 claims 1
- TUBCTAWYBBNRER-UHFFFAOYSA-N FC(OC=1C=C(C=CC1)C1=C2C=C(C=NC2=CN=C1)C(=O)N)(F)F.COC=1C=C(C=CC1)C1=C2C=C(C=NC2=CN=C1)C(=O)N.O1CCN(CC1)C1=C2C=C(C=NC2=CN=C1)C(=O)N Chemical compound FC(OC=1C=C(C=CC1)C1=C2C=C(C=NC2=CN=C1)C(=O)N)(F)F.COC=1C=C(C=CC1)C1=C2C=C(C=NC2=CN=C1)C(=O)N.O1CCN(CC1)C1=C2C=C(C=NC2=CN=C1)C(=O)N TUBCTAWYBBNRER-UHFFFAOYSA-N 0.000 claims 1
- XOJIQGXEDOQAHA-UHFFFAOYSA-N FC1(CCN(CC1)C1=C2C=C(C=NC2=CN=C1)C(=O)N)F.O1CCC(=CC1)C1=C2C=C(C=NC2=CN=C1)C(=O)N.C(N)(=O)C=1C=NC=2C=NC=C(C2C1)C(=O)O Chemical compound FC1(CCN(CC1)C1=C2C=C(C=NC2=CN=C1)C(=O)N)F.O1CCC(=CC1)C1=C2C=C(C=NC2=CN=C1)C(=O)N.C(N)(=O)C=1C=NC=2C=NC=C(C2C1)C(=O)O XOJIQGXEDOQAHA-UHFFFAOYSA-N 0.000 claims 1
- KDJLKIGCBTUVSC-UHFFFAOYSA-N FC1=C(C=CC(=C1)F)C1=C2C=C(C=NC2=CN=C1)C(=O)NCC(F)(F)F Chemical compound FC1=C(C=CC(=C1)F)C1=C2C=C(C=NC2=CN=C1)C(=O)NCC(F)(F)F KDJLKIGCBTUVSC-UHFFFAOYSA-N 0.000 claims 1
- ZDALSMRPVOYRDZ-UHFFFAOYSA-N NC(=O)c1cnc2cncc(-c3ccc(Cl)nc3)c2c1 Chemical compound NC(=O)c1cnc2cncc(-c3ccc(Cl)nc3)c2c1 ZDALSMRPVOYRDZ-UHFFFAOYSA-N 0.000 claims 1
- YJBZLDPYHDRXJD-UHFFFAOYSA-N NC(=O)c1cnc2cncc(N3CCC(F)(F)CC3)c2c1 Chemical compound NC(=O)c1cnc2cncc(N3CCC(F)(F)CC3)c2c1 YJBZLDPYHDRXJD-UHFFFAOYSA-N 0.000 claims 1
- PQEYTUYVILPEDQ-UHFFFAOYSA-N O1CCC(=CC1)C1=C2C=C(C=NC2=CN=C1)C(=O)N.C(N)(=O)C=1C=NC=2C=NC=C(C2C1)C(=O)O.O1CCN(CC1)C1=C2C=C(C=NC2=CN=C1)C(=O)N Chemical compound O1CCC(=CC1)C1=C2C=C(C=NC2=CN=C1)C(=O)N.C(N)(=O)C=1C=NC=2C=NC=C(C2C1)C(=O)O.O1CCN(CC1)C1=C2C=C(C=NC2=CN=C1)C(=O)N PQEYTUYVILPEDQ-UHFFFAOYSA-N 0.000 claims 1
- 239000013543 active substance Substances 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 125000003784 fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 claims 1
- 125000001188 haloalkyl group Chemical group 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 6
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- 239000000908 ammonium hydroxide Substances 0.000 description 2
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 2
- 229910000024 caesium carbonate Inorganic materials 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 208000024714 major depressive disease Diseases 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- ZDZHCHYQNPQSGG-UHFFFAOYSA-N 1-naphthalen-1-ylnaphthalene Chemical compound C1=CC=C2C(C=3C4=CC=CC=C4C=CC=3)=CC=CC2=C1 ZDZHCHYQNPQSGG-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- PUCJUHHOCNHVIT-UHFFFAOYSA-N Cc1nc2cncc(Br)c2cc1C(N)=O Chemical compound Cc1nc2cncc(Br)c2cc1C(N)=O PUCJUHHOCNHVIT-UHFFFAOYSA-N 0.000 description 1
- WRUONPSVNKFOJO-UHFFFAOYSA-N Cc1nc2cncc(Br)c2cc1C(O)=O Chemical compound Cc1nc2cncc(Br)c2cc1C(O)=O WRUONPSVNKFOJO-UHFFFAOYSA-N 0.000 description 1
- 206010013654 Drug abuse Diseases 0.000 description 1
- FPCROTRSDYPPNZ-UHFFFAOYSA-N NC(=O)c1cnc2cncc(-c3ccc(OC(F)(F)F)cc3)c2c1 Chemical compound NC(=O)c1cnc2cncc(-c3ccc(OC(F)(F)F)cc3)c2c1 FPCROTRSDYPPNZ-UHFFFAOYSA-N 0.000 description 1
- NXBVXAAXKATQNQ-UHFFFAOYSA-N NC(=O)c1cnc2cncc(N3CCOCC3)c2c1 Chemical compound NC(=O)c1cnc2cncc(N3CCOCC3)c2c1 NXBVXAAXKATQNQ-UHFFFAOYSA-N 0.000 description 1
- ULJYIUDMOUUCKH-UHFFFAOYSA-N OC(=O)c1cnc2cncc(N3CCOCC3)c2c1 Chemical compound OC(=O)c1cnc2cncc(N3CCOCC3)c2c1 ULJYIUDMOUUCKH-UHFFFAOYSA-N 0.000 description 1
- 239000008896 Opium Substances 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 206010044688 Trisomy 21 Diseases 0.000 description 1
- HUOFUOCSQCYFPW-UHFFFAOYSA-N [4-(trifluoromethoxy)phenyl]boronic acid Chemical compound OB(O)C1=CC=C(OC(F)(F)F)C=C1 HUOFUOCSQCYFPW-UHFFFAOYSA-N 0.000 description 1
- MUALRAIOVNYAIW-UHFFFAOYSA-N binap Chemical compound C1=CC=CC=C1P(C=1C(=C2C=CC=CC2=CC=1)C=1C2=CC=CC=C2C=CC=1P(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 MUALRAIOVNYAIW-UHFFFAOYSA-N 0.000 description 1
- NXQGGXCHGDYOHB-UHFFFAOYSA-L cyclopenta-1,4-dien-1-yl(diphenyl)phosphane;dichloropalladium;iron(2+) Chemical compound [Fe+2].Cl[Pd]Cl.[CH-]1C=CC(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1.[CH-]1C=CC(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 NXQGGXCHGDYOHB-UHFFFAOYSA-L 0.000 description 1
- GPAYUJZHTULNBE-UHFFFAOYSA-N diphenylphosphine Chemical compound C=1C=CC=CC=1PC1=CC=CC=C1 GPAYUJZHTULNBE-UHFFFAOYSA-N 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 230000004766 neurogenesis Effects 0.000 description 1
- 229960001027 opium Drugs 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 230000015284 positive regulation of neurogenesis Effects 0.000 description 1
- 238000002953 preparative HPLC Methods 0.000 description 1
- 230000002207 retinal effect Effects 0.000 description 1
- 208000011117 substance-related disease Diseases 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP13178373.0 | 2013-07-29 | ||
| EP13178373 | 2013-07-29 | ||
| PCT/EP2014/066123 WO2015014768A1 (en) | 2013-07-29 | 2014-07-28 | 1,7-naphthyridine derivatives |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2016525142A JP2016525142A (ja) | 2016-08-22 |
| JP2016525142A5 true JP2016525142A5 (OSRAM) | 2017-04-06 |
| JP6130071B2 JP6130071B2 (ja) | 2017-05-17 |
Family
ID=48874925
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016528556A Active JP6130071B2 (ja) | 2013-07-29 | 2014-07-28 | １，７−ナフチリジン誘導体 |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US9688675B2 (OSRAM) |
| EP (1) | EP3027597B1 (OSRAM) |
| JP (1) | JP6130071B2 (OSRAM) |
| KR (1) | KR101781762B1 (OSRAM) |
| CN (1) | CN105473568B (OSRAM) |
| AR (1) | AR097088A1 (OSRAM) |
| CA (1) | CA2917602A1 (OSRAM) |
| ES (1) | ES2630317T3 (OSRAM) |
| MX (1) | MX362532B (OSRAM) |
| RU (1) | RU2669943C2 (OSRAM) |
| TW (1) | TWI529171B (OSRAM) |
| WO (1) | WO2015014768A1 (OSRAM) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP6229056B2 (ja) * | 2013-11-12 | 2017-11-08 | エフ．ホフマン−ラ ロシュ アーゲーＦ． Ｈｏｆｆｍａｎｎ−Ｌａ Ｒｏｃｈｅ Ａｋｔｉｅｎｇｅｓｅｌｌｓｃｈａｆｔ | 神経変性疾患の処置用の神経新生薬としてのピリド［４，３−ｂ］ピラジン−２−カルボキサミド |
| EP3889145B1 (en) * | 2015-12-17 | 2024-02-21 | Merck Patent GmbH | 8-cyano-5-piperidino-quinolines as tlr7/8 antagonists and their uses for treating immune disorders |
| CN106008487B (zh) | 2015-12-31 | 2019-08-09 | 北京理工大学 | 一种二苯乙烯类衍生物及其制备方法 |
| US11485733B2 (en) | 2017-06-30 | 2022-11-01 | Bayer Animal Health Gmbh | Azaquinoline derivatives |
| AU2018312836B2 (en) * | 2017-08-07 | 2022-12-08 | Joint Stock Company "Biocad" | Novel heterocyclic compounds as CDK8/19 inhibitors |
| RU2739489C2 (ru) * | 2018-03-06 | 2020-12-24 | Закрытое Акционерное Общество "Биокад" | Новые гетероциклические соединения как ингибиторы CDK8/19 |
| JP7491900B2 (ja) * | 2018-07-31 | 2024-05-28 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツング | Ｔｌｒ７／８アンタゴニストおよびそれらの使用 |
| RU2761824C2 (ru) * | 2018-08-03 | 2021-12-13 | Закрытое Акционерное Общество "Биокад" | Ингибиторы CDK8/19 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2624413A1 (en) * | 2005-10-05 | 2007-04-12 | F. Hoffmann-La Roche Ag | Naphthyridin derivatives |
| US20080242694A1 (en) * | 2006-09-18 | 2008-10-02 | D Sidocky Neil R | Amino-substituted heterocycles, compositions thereof, and methods of treatment therewith |
| WO2008046072A2 (en) * | 2006-10-13 | 2008-04-17 | The Board Of Regents Of The University Of Texas System | Chemical inducers of neurogenesis |
| US8415376B2 (en) * | 2008-05-30 | 2013-04-09 | Amgen Inc. | Inhibitors of PI3 kinase |
| WO2010101949A1 (en) * | 2009-03-02 | 2010-09-10 | Sirtris Pharmaceuticals, Inc. | 8-substituted quinolines and related analogs as sirtuin modulators |
| WO2011095196A1 (en) * | 2010-02-05 | 2011-08-11 | Merck Patent Gmbh | Hetaryl-[1,8]naphthyridine derivatives |
| MX2015006364A (es) | 2012-11-20 | 2015-10-05 | Hoffmann La Roche | 1,6-naftiridinas sustituidas. |
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2014
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- 2014-07-28 ES ES14744539.9T patent/ES2630317T3/es active Active
- 2014-07-28 KR KR1020167002439A patent/KR101781762B1/ko not_active Expired - Fee Related
- 2014-07-28 RU RU2016104890A patent/RU2669943C2/ru not_active IP Right Cessation
- 2014-07-28 CN CN201480042466.6A patent/CN105473568B/zh not_active Expired - Fee Related
- 2014-07-28 MX MX2016000895A patent/MX362532B/es active IP Right Grant
- 2014-07-28 EP EP14744539.9A patent/EP3027597B1/en not_active Not-in-force
- 2014-07-28 WO PCT/EP2014/066123 patent/WO2015014768A1/en not_active Ceased
- 2014-07-28 JP JP2016528556A patent/JP6130071B2/ja active Active
- 2014-07-28 CA CA2917602A patent/CA2917602A1/en not_active Abandoned
- 2014-07-28 AR ARP140102800A patent/AR097088A1/es unknown
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2016
- 2016-01-27 US US15/007,631 patent/US9688675B2/en not_active Expired - Fee Related
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