JP2017526705A5 - - Google Patents
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- Publication number
- JP2017526705A5 JP2017526705A5 JP2017513162A JP2017513162A JP2017526705A5 JP 2017526705 A5 JP2017526705 A5 JP 2017526705A5 JP 2017513162 A JP2017513162 A JP 2017513162A JP 2017513162 A JP2017513162 A JP 2017513162A JP 2017526705 A5 JP2017526705 A5 JP 2017526705A5
- Authority
- JP
- Japan
- Prior art keywords
- dicarboxylate
- pyridine
- dimethyl
- diethyl
- phenyl
- 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 5-chloro-2-ethoxyphenyl Chemical group 0.000 claims description 10
- 125000001072 heteroaryl group Chemical group 0.000 claims description 5
- 125000005842 heteroatom Chemical group 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 229910052717 sulfur Chemical group 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 125000000623 heterocyclic group Chemical group 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims 10
- 239000000203 mixture Substances 0.000 claims 9
- 150000003839 salts Chemical class 0.000 claims 9
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 8
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 7
- 125000001424 substituent group Chemical group 0.000 claims 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims 6
- 229910052736 halogen Inorganic materials 0.000 claims 6
- 150000002367 halogens Chemical class 0.000 claims 6
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims 5
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims 5
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 3
- 125000004438 haloalkoxy group Chemical group 0.000 claims 3
- 229910052757 nitrogen Inorganic materials 0.000 claims 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 3
- 239000001301 oxygen Chemical group 0.000 claims 3
- 239000011593 sulfur Chemical group 0.000 claims 3
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- WVYGPHQOKBJYGB-UHFFFAOYSA-N diethyl 4-piperazin-1-ylpyridine-2,6-dicarboxylate Chemical compound CCOC(=O)C1=NC(C(=O)OCC)=CC(N2CCNCC2)=C1 WVYGPHQOKBJYGB-UHFFFAOYSA-N 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 239000002904 solvent Substances 0.000 claims 2
- RYFPCOPRPRDZTC-UHFFFAOYSA-N 2-[2,6-bis(methoxycarbonyl)pyridin-4-yl]acetic acid Chemical compound COC(=O)C1=CC(CC(O)=O)=CC(C(=O)OC)=N1 RYFPCOPRPRDZTC-UHFFFAOYSA-N 0.000 claims 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims 1
- MOMMCXYSWFTKCN-UHFFFAOYSA-N 3-[2,6-bis(ethoxycarbonyl)pyridin-4-yl]propanoic acid Chemical compound CCOC(=O)C1=CC(CCC(O)=O)=CC(C(=O)OCC)=N1 MOMMCXYSWFTKCN-UHFFFAOYSA-N 0.000 claims 1
- IMPBCUNULBVUSD-UHFFFAOYSA-N BrC=1C(=C(C(=CC=1OC)OC)C1=CC(=NC(=C1)C(=O)OCC)C(=O)OCC)OC Chemical compound BrC=1C(=C(C(=CC=1OC)OC)C1=CC(=NC(=C1)C(=O)OCC)C(=O)OCC)OC IMPBCUNULBVUSD-UHFFFAOYSA-N 0.000 claims 1
- KOVPJPKASNBKMO-UHFFFAOYSA-N C(#N)C1=CC=C(C=C1)C1=CC(=NC(=C1)C(=O)OCC)C(=O)OCC Chemical compound C(#N)C1=CC=C(C=C1)C1=CC(=NC(=C1)C(=O)OCC)C(=O)OCC KOVPJPKASNBKMO-UHFFFAOYSA-N 0.000 claims 1
- KCZJCKJSNYWBMR-UHFFFAOYSA-N C(C)(C)(C)C1=CC(=NC(=C1)C(=O)OCC)C(=O)OCC Chemical compound C(C)(C)(C)C1=CC(=NC(=C1)C(=O)OCC)C(=O)OCC KCZJCKJSNYWBMR-UHFFFAOYSA-N 0.000 claims 1
- VBCMVDHJNBCLTB-UHFFFAOYSA-N C(CCCCC)C1=C(SC=C1)C1=CC(=NC(=C1)C(=O)OCC)C(=O)OCC Chemical compound C(CCCCC)C1=C(SC=C1)C1=CC(=NC(=C1)C(=O)OCC)C(=O)OCC VBCMVDHJNBCLTB-UHFFFAOYSA-N 0.000 claims 1
- QOBGRKYBBSHPKQ-UHFFFAOYSA-N CC(C)(C)C1=CC=C(C=C1)C1=CC(=NC(=C1)C(=O)OCC)C(=O)OCC Chemical compound CC(C)(C)C1=CC=C(C=C1)C1=CC(=NC(=C1)C(=O)OCC)C(=O)OCC QOBGRKYBBSHPKQ-UHFFFAOYSA-N 0.000 claims 1
- LZEVIRINDJTQAX-UHFFFAOYSA-N CC1=C(C=CC=C1)C1=CC(=NC(=C1)C(=O)OC)C(=O)OC Chemical compound CC1=C(C=CC=C1)C1=CC(=NC(=C1)C(=O)OC)C(=O)OC LZEVIRINDJTQAX-UHFFFAOYSA-N 0.000 claims 1
- BTEVUXAFTITZNG-UHFFFAOYSA-N CC1=C(C=CN=C1C)CCO Chemical compound CC1=C(C=CN=C1C)CCO BTEVUXAFTITZNG-UHFFFAOYSA-N 0.000 claims 1
- DZZBPKALZIDTIN-UHFFFAOYSA-N CC1=CC=C(C=C1)C1=CC(=NC(=C1)C(=O)OC)C(=O)OC Chemical compound CC1=CC=C(C=C1)C1=CC(=NC(=C1)C(=O)OC)C(=O)OC DZZBPKALZIDTIN-UHFFFAOYSA-N 0.000 claims 1
- KMZYUJFEFABMMM-UHFFFAOYSA-N CC=1C=C(C=CC=1)C1=CC(=NC(=C1)C(=O)OC)C(=O)OC Chemical compound CC=1C=C(C=CC=1)C1=CC(=NC(=C1)C(=O)OC)C(=O)OC KMZYUJFEFABMMM-UHFFFAOYSA-N 0.000 claims 1
- AFMBWGLJYJOJIJ-UHFFFAOYSA-N CCCC(CCCC)OC1=C(C=CC=C1)C1=CC(=NC(=C1)C(=O)OC)C(=O)OC Chemical compound CCCC(CCCC)OC1=C(C=CC=C1)C1=CC(=NC(=C1)C(=O)OC)C(=O)OC AFMBWGLJYJOJIJ-UHFFFAOYSA-N 0.000 claims 1
- GUQDUEHQATZGPL-UHFFFAOYSA-N CCCC(CCCCCCCCCCCCCC)OC1=C(C=CC=C1)C1=CC(=NC(=C1)C(=O)OC)C(=O)OC Chemical compound CCCC(CCCCCCCCCCCCCC)OC1=C(C=CC=C1)C1=CC(=NC(=C1)C(=O)OC)C(=O)OC GUQDUEHQATZGPL-UHFFFAOYSA-N 0.000 claims 1
- VPAJFYDRRUBKDU-UHFFFAOYSA-N CCOC(=O)C1=NC(C(=O)OCC)=CC(C=2C3=CC=CC=C3C=C3C=CC=CC3=2)=C1 Chemical compound CCOC(=O)C1=NC(C(=O)OCC)=CC(C=2C3=CC=CC=C3C=C3C=CC=CC3=2)=C1 VPAJFYDRRUBKDU-UHFFFAOYSA-N 0.000 claims 1
- OPENEUXRTKYWJD-UHFFFAOYSA-N COC(=O)C1=NC(C(=O)OC)=CC(C=2N(C3=CC=CC=C3C=2)C)=C1 Chemical compound COC(=O)C1=NC(C(=O)OC)=CC(C=2N(C3=CC=CC=C3C=2)C)=C1 OPENEUXRTKYWJD-UHFFFAOYSA-N 0.000 claims 1
- ZIVGSDHKFMBPCC-UHFFFAOYSA-N COC1=CC=C(C=C1)C1=CC(=NC(=C1)C(=O)OCC)C(=O)OCC Chemical compound COC1=CC=C(C=C1)C1=CC(=NC(=C1)C(=O)OCC)C(=O)OCC ZIVGSDHKFMBPCC-UHFFFAOYSA-N 0.000 claims 1
- ZUDDHCBZOWTXAV-UHFFFAOYSA-N COC=1C=C(C=CC=1OC)C1=CC(=NC(=C1)C(=O)OC)C(=O)OC Chemical compound COC=1C=C(C=CC=1OC)C1=CC(=NC(=C1)C(=O)OC)C(=O)OC ZUDDHCBZOWTXAV-UHFFFAOYSA-N 0.000 claims 1
- PRGGGVCHECSFBZ-UHFFFAOYSA-N ClC1=CC=C(C=C1)C1=CC(=NC(=C1)C(=O)OCC)C(=O)OCC Chemical compound ClC1=CC=C(C=C1)C1=CC(=NC(=C1)C(=O)OCC)C(=O)OCC PRGGGVCHECSFBZ-UHFFFAOYSA-N 0.000 claims 1
- SHUOUGGCPNBFKU-UHFFFAOYSA-N ClC=1C=C(C=CC=1)C1=CC(=NC(=C1)C(=O)OC)C(=O)OC Chemical compound ClC=1C=C(C=CC=1)C1=CC(=NC(=C1)C(=O)OC)C(=O)OC SHUOUGGCPNBFKU-UHFFFAOYSA-N 0.000 claims 1
- VZTBHZLMFBGYRC-UHFFFAOYSA-N FC(C1=CC(=NC(=C1)C(=O)OC)C(=O)OC)(F)F Chemical compound FC(C1=CC(=NC(=C1)C(=O)OC)C(=O)OC)(F)F VZTBHZLMFBGYRC-UHFFFAOYSA-N 0.000 claims 1
- KFJRKFBSSFSHAD-UHFFFAOYSA-N FC(C=1C=C(C=C(C=1)C(F)(F)F)C1=CC(=NC(=C1)C(=O)OC)C(=O)OC)(F)F Chemical compound FC(C=1C=C(C=C(C=1)C(F)(F)F)C1=CC(=NC(=C1)C(=O)OC)C(=O)OC)(F)F KFJRKFBSSFSHAD-UHFFFAOYSA-N 0.000 claims 1
- ZHSVOIPQRMSXJY-UHFFFAOYSA-N FC1=CC=C(C=C1)C1=CC(=NC(=C1)C(=O)OC)C(=O)OC Chemical compound FC1=CC=C(C=C1)C1=CC(=NC(=C1)C(=O)OC)C(=O)OC ZHSVOIPQRMSXJY-UHFFFAOYSA-N 0.000 claims 1
- DRGORXPZWKWYAI-UHFFFAOYSA-N N1(CCCC1)C1=CC(=NC(=C1)C(=O)OC)C(=O)OC Chemical compound N1(CCCC1)C1=CC(=NC(=C1)C(=O)OC)C(=O)OC DRGORXPZWKWYAI-UHFFFAOYSA-N 0.000 claims 1
- DXDPROZHTSLRJB-UHFFFAOYSA-N N1(CCOCC1)C1=CC(=NC(=C1)C(=O)OCC)C(=O)OCC Chemical compound N1(CCOCC1)C1=CC(=NC(=C1)C(=O)OCC)C(=O)OCC DXDPROZHTSLRJB-UHFFFAOYSA-N 0.000 claims 1
- TWCQQABNABPPTF-UHFFFAOYSA-N O(C)C1=CC=C(C=C1)C1=CC(=NC(=C1)C(=O)OC)C(=O)OC Chemical compound O(C)C1=CC=C(C=C1)C1=CC(=NC(=C1)C(=O)OC)C(=O)OC TWCQQABNABPPTF-UHFFFAOYSA-N 0.000 claims 1
- WZEPKXJJSPXNDV-UHFFFAOYSA-N OC1=CC=C(C=C1)C1=CC(=NC(=C1)C(=O)OC)C(=O)OC Chemical compound OC1=CC=C(C=C1)C1=CC(=NC(=C1)C(=O)OC)C(=O)OC WZEPKXJJSPXNDV-UHFFFAOYSA-N 0.000 claims 1
- KRJXVSLWVHJVNU-UHFFFAOYSA-N [N+](=O)([O-])C1=CC=C(C=C1)C1=CC(=NC(=C1)C(=O)OC)C(=O)OC Chemical compound [N+](=O)([O-])C1=CC=C(C=C1)C1=CC(=NC(=C1)C(=O)OC)C(=O)OC KRJXVSLWVHJVNU-UHFFFAOYSA-N 0.000 claims 1
- 239000002671 adjuvant Substances 0.000 claims 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims 1
- WJHWQBYFNGENBH-UHFFFAOYSA-N diethyl 4-(2,4,6-trimethoxyphenyl)pyridine-2,6-dicarboxylate Chemical compound CCOC(=O)C1=NC(C(=O)OCC)=CC(C=2C(=CC(OC)=CC=2OC)OC)=C1 WJHWQBYFNGENBH-UHFFFAOYSA-N 0.000 claims 1
- MPVQOXAPTGIZRZ-UHFFFAOYSA-N diethyl 4-(4-ethylphenyl)pyridine-2,6-dicarboxylate Chemical compound C(C)C1=CC=C(C=C1)C1=CC(=NC(=C1)C(=O)OCC)C(=O)OCC MPVQOXAPTGIZRZ-UHFFFAOYSA-N 0.000 claims 1
- WEFOFHSJVRMWEB-UHFFFAOYSA-N diethyl 4-(5-chloro-2-methoxyphenyl)pyridine-2,6-dicarboxylate Chemical compound CCOC(=O)C1=NC(C(=O)OCC)=CC(C=2C(=CC=C(Cl)C=2)OC)=C1 WEFOFHSJVRMWEB-UHFFFAOYSA-N 0.000 claims 1
- KKCOILXNNCGATQ-UHFFFAOYSA-N diethyl 4-(furan-2-yl)pyridine-2,6-dicarboxylate Chemical compound CCOC(=O)C1=NC(C(=O)OCC)=CC(C=2OC=CC=2)=C1 KKCOILXNNCGATQ-UHFFFAOYSA-N 0.000 claims 1
- VMKVWNJLYHGSHP-UHFFFAOYSA-N diethyl 4-(hydroxymethyl)pyridine-2,6-dicarboxylate Chemical compound OCC1=CC(=NC(=C1)C(=O)OCC)C(=O)OCC VMKVWNJLYHGSHP-UHFFFAOYSA-N 0.000 claims 1
- ASBYVXZZZSSXHF-UHFFFAOYSA-N diethyl 4-ethylpyridine-2,6-dicarboxylate Chemical compound CCOC(=O)C1=CC(CC)=CC(C(=O)OCC)=N1 ASBYVXZZZSSXHF-UHFFFAOYSA-N 0.000 claims 1
- MFXXSDGZFUOFGH-UHFFFAOYSA-N diethyl 4-methylpyridine-2,6-dicarboxylate Chemical compound CCOC(=O)C1=CC(C)=CC(C(=O)OCC)=N1 MFXXSDGZFUOFGH-UHFFFAOYSA-N 0.000 claims 1
- PQHWPDZSLTUCAJ-UHFFFAOYSA-N diethyl 4-phenylpyridine-2,6-dicarboxylate Chemical compound CCOC(=O)C1=NC(C(=O)OCC)=CC(C=2C=CC=CC=2)=C1 PQHWPDZSLTUCAJ-UHFFFAOYSA-N 0.000 claims 1
- CHMDOTQZHAUCOH-UHFFFAOYSA-N diethyl 4-thiophen-2-ylpyridine-2,6-dicarboxylate Chemical compound CCOC(=O)C1=NC(C(=O)OCC)=CC(C=2SC=CC=2)=C1 CHMDOTQZHAUCOH-UHFFFAOYSA-N 0.000 claims 1
- CNYFCOHQFYPHBW-UHFFFAOYSA-N diethyl 4-thiophen-3-ylpyridine-2,6-dicarboxylate Chemical compound CCOC(=O)C1=NC(C(=O)OCC)=CC(C2=CSC=C2)=C1 CNYFCOHQFYPHBW-UHFFFAOYSA-N 0.000 claims 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- REOMGBOZGUFSTI-UHFFFAOYSA-N dimethyl 4-(2,4-dimethoxyphenyl)pyridine-2,6-dicarboxylate Chemical compound COC(=O)C1=NC(C(=O)OC)=CC(C=2C(=CC(OC)=CC=2)OC)=C1 REOMGBOZGUFSTI-UHFFFAOYSA-N 0.000 claims 1
- YPYCVPFQRZMBJQ-UHFFFAOYSA-N dimethyl 4-(2-hydroxyethyl)pyridine-2,6-dicarboxylate Chemical compound COC(=O)C1=CC(CCO)=CC(C(=O)OC)=N1 YPYCVPFQRZMBJQ-UHFFFAOYSA-N 0.000 claims 1
- FNNKGVCWECPUPR-UHFFFAOYSA-N dimethyl 4-(2-methylpiperidin-1-yl)pyridine-2,6-dicarboxylate Chemical compound COC(=O)C1=NC(C(=O)OC)=CC(N2C(CCCC2)C)=C1 FNNKGVCWECPUPR-UHFFFAOYSA-N 0.000 claims 1
- ZDYPBQDWZFMUEK-UHFFFAOYSA-N dimethyl 4-(3-bromopropyl)pyridine-2,6-dicarboxylate Chemical compound COC(=O)C1=CC(CCCBr)=CC(C(=O)OC)=N1 ZDYPBQDWZFMUEK-UHFFFAOYSA-N 0.000 claims 1
- OEYZUOCOZQJYBC-UHFFFAOYSA-N dimethyl 4-(3-hydroxypropyl)pyridine-2,6-dicarboxylate Chemical compound COC(=O)C1=CC(CCCO)=CC(C(=O)OC)=N1 OEYZUOCOZQJYBC-UHFFFAOYSA-N 0.000 claims 1
- LRFRNKKKWVKEIK-UHFFFAOYSA-N dimethyl 4-(4-hydroxy-2,6-dimethoxyphenyl)pyridine-2,6-dicarboxylate Chemical compound COC(=O)C1=NC(C(=O)OC)=CC(C=2C(=CC(O)=CC=2OC)OC)=C1 LRFRNKKKWVKEIK-UHFFFAOYSA-N 0.000 claims 1
- HSIKPXMYIOSPQK-UHFFFAOYSA-N dimethyl 4-(4-hydroxy-2-methoxyphenyl)pyridine-2,6-dicarboxylate Chemical compound COC(=O)C1=NC(C(=O)OC)=CC(C=2C(=CC(O)=CC=2)OC)=C1 HSIKPXMYIOSPQK-UHFFFAOYSA-N 0.000 claims 1
- GXXFUVXRBZYXMZ-UHFFFAOYSA-N dimethyl 4-(bromomethyl)pyridine-2,6-dicarboxylate Chemical compound COC(=O)C1=CC(CBr)=CC(C(=O)OC)=N1 GXXFUVXRBZYXMZ-UHFFFAOYSA-N 0.000 claims 1
- LIIWGINRIORAFC-UHFFFAOYSA-N dimethyl 4-(chloromethyl)pyridine-2,6-dicarboxylate Chemical compound COC(=O)C1=CC(CCl)=CC(C(=O)OC)=N1 LIIWGINRIORAFC-UHFFFAOYSA-N 0.000 claims 1
- HJYGNWVTSNKHEQ-UHFFFAOYSA-N dimethyl 4-(dimethoxymethyl)pyridine-2,6-dicarboxylate Chemical compound COC(C1=CC(=NC(=C1)C(=O)OC)C(=O)OC)OC HJYGNWVTSNKHEQ-UHFFFAOYSA-N 0.000 claims 1
- UJJJESXBXYFZCR-UHFFFAOYSA-N dimethyl 4-(hydroxymethyl)pyridine-2,6-dicarboxylate Chemical compound COC(=O)C1=CC(CO)=CC(C(=O)OC)=N1 UJJJESXBXYFZCR-UHFFFAOYSA-N 0.000 claims 1
- MFUCSDWCZDCFNF-UHFFFAOYSA-N dimethyl 4-(iodomethyl)pyridine-2,6-dicarboxylate Chemical compound COC(=O)C1=CC(CI)=CC(C(=O)OC)=N1 MFUCSDWCZDCFNF-UHFFFAOYSA-N 0.000 claims 1
- KIEXOSNZNNZTHN-UHFFFAOYSA-N dimethyl 4-cyclohexylpyridine-2,6-dicarboxylate Chemical compound COC(=O)C1=NC(C(=O)OC)=CC(C2CCCCC2)=C1 KIEXOSNZNNZTHN-UHFFFAOYSA-N 0.000 claims 1
- FJXUQXGZPUYBPA-UHFFFAOYSA-N dimethyl 4-ethylpyridine-2,6-dicarboxylate Chemical compound CCC1=CC(C(=O)OC)=NC(C(=O)OC)=C1 FJXUQXGZPUYBPA-UHFFFAOYSA-N 0.000 claims 1
- FMIPAXVAQJKQCV-UHFFFAOYSA-N dimethyl 4-methylpyridine-2,6-dicarboxylate Chemical compound COC(=O)C1=CC(C)=CC(C(=O)OC)=N1 FMIPAXVAQJKQCV-UHFFFAOYSA-N 0.000 claims 1
- CKTZITJFJKDLKQ-UHFFFAOYSA-N dimethyl 4-morpholin-4-ylpyridine-2,6-dicarboxylate Chemical compound COC(=O)C1=NC(C(=O)OC)=CC(N2CCOCC2)=C1 CKTZITJFJKDLKQ-UHFFFAOYSA-N 0.000 claims 1
- OLMHRSWTQCXPGX-UHFFFAOYSA-N dimethyl 4-naphthalen-1-ylpyridine-2,6-dicarboxylate Chemical compound COC(=O)C1=NC(C(=O)OC)=CC(C=2C3=CC=CC=C3C=CC=2)=C1 OLMHRSWTQCXPGX-UHFFFAOYSA-N 0.000 claims 1
- SOTATQHFHGYCJA-UHFFFAOYSA-N dimethyl 4-phenylpyridine-2,6-dicarboxylate Chemical compound COC(=O)C1=NC(C(=O)OC)=CC(C=2C=CC=CC=2)=C1 SOTATQHFHGYCJA-UHFFFAOYSA-N 0.000 claims 1
- VMANFHSKNQAGFT-UHFFFAOYSA-N dimethyl 4-propan-2-ylpyridine-2,6-dicarboxylate Chemical compound COC(=O)C1=CC(C(C)C)=CC(C(=O)OC)=N1 VMANFHSKNQAGFT-UHFFFAOYSA-N 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- MXDSSOZXKAOKEJ-UHFFFAOYSA-N ditert-butyl 4-(bromomethyl)pyridine-2,6-dicarboxylate Chemical compound BrCC1=CC(=NC(=C1)C(=O)OC(C)(C)C)C(=O)OC(C)(C)C MXDSSOZXKAOKEJ-UHFFFAOYSA-N 0.000 claims 1
- WOHIVWYZRAIZQT-UHFFFAOYSA-N ditert-butyl 4-pyridin-4-ylpyridine-2,6-dicarboxylate Chemical compound N1=CC=C(C=C1)C1=CC(=NC(=C1)C(=O)OC(C)(C)C)C(=O)OC(C)(C)C WOHIVWYZRAIZQT-UHFFFAOYSA-N 0.000 claims 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 125000001624 naphthyl group Chemical group 0.000 claims 1
- 230000002062 proliferating effect Effects 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 description 4
- 125000003373 pyrazinyl group Chemical group 0.000 description 3
- 125000003226 pyrazolyl group Chemical group 0.000 description 3
- 125000000714 pyrimidinyl group Chemical group 0.000 description 3
- 125000002541 furyl group Chemical group 0.000 description 2
- 125000000842 isoxazolyl group Chemical group 0.000 description 2
- 125000002971 oxazolyl group Chemical group 0.000 description 2
- 125000002098 pyridazinyl group Chemical group 0.000 description 2
- 0 *C(c1cc(*)cc(C(*)=O)n1)=O Chemical compound *C(c1cc(*)cc(C(*)=O)n1)=O 0.000 description 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000004622 benzoxazinyl group Chemical group O1NC(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- 125000005412 pyrazyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000006413 ring segment Chemical group 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201462048203P | 2014-09-09 | 2014-09-09 | |
| US62/048,203 | 2014-09-09 | ||
| PCT/JP2015/004588 WO2016038890A1 (en) | 2014-09-09 | 2015-09-09 | 4-substituted pyridine-2,6-dicarboxylic acid derivatives and method of preparing same |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2017526705A JP2017526705A (ja) | 2017-09-14 |
| JP2017526705A5 true JP2017526705A5 (https=) | 2019-08-15 |
| JP6567654B2 JP6567654B2 (ja) | 2019-08-28 |
Family
ID=55458659
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017513162A Active JP6567654B2 (ja) | 2014-09-09 | 2015-09-09 | ４−置換ピリジン−２，６−ジカルボン酸誘導体とその製造方法 |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US20170217889A1 (https=) |
| EP (1) | EP3191451B1 (https=) |
| JP (1) | JP6567654B2 (https=) |
| WO (1) | WO2016038890A1 (https=) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115286567B (zh) * | 2022-08-12 | 2024-04-19 | 镇江中智化学科技有限公司 | 一锅法合成3-溴吡啶 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4368576B2 (ja) * | 2002-12-20 | 2009-11-18 | 財団法人くまもとテクノ産業財団 | ジチオール化合物 |
| US8071626B2 (en) * | 2003-12-18 | 2011-12-06 | Wallac Oy | Chelating agents and highly luminescent and stable chelates and their use |
| CN101611007A (zh) * | 2006-12-20 | 2009-12-23 | 先灵公司 | 新颖的jnk抑制剂 |
| CA2825746A1 (en) * | 2011-01-26 | 2012-08-02 | Kyorin Pharmaceutical Co. Ltd. | Pyrazolopyridine derivative or pharmacologically acceptable salt thereof |
| WO2014058078A1 (en) * | 2012-10-12 | 2014-04-17 | Okinawa Institute Of Science And Technology School Corporation | Process for producing dihydro-2h-pyran derivatives |
-
2015
- 2015-09-09 US US15/509,721 patent/US20170217889A1/en not_active Abandoned
- 2015-09-09 EP EP15840917.7A patent/EP3191451B1/en active Active
- 2015-09-09 WO PCT/JP2015/004588 patent/WO2016038890A1/en not_active Ceased
- 2015-09-09 JP JP2017513162A patent/JP6567654B2/ja active Active
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