JP7301758B2 - 縮合二環式化合物、その組成物及び応用 - Google Patents
縮合二環式化合物、その組成物及び応用 Download PDFInfo
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- JP7301758B2 JP7301758B2 JP2019571826A JP2019571826A JP7301758B2 JP 7301758 B2 JP7301758 B2 JP 7301758B2 JP 2019571826 A JP2019571826 A JP 2019571826A JP 2019571826 A JP2019571826 A JP 2019571826A JP 7301758 B2 JP7301758 B2 JP 7301758B2
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- Prior art keywords
- alkyl
- cycloalkyl
- heterocyclyl
- heteroaryl
- haloalkyl
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- 125000002619 bicyclic group Chemical group 0.000 title claims description 107
- 239000000203 mixture Substances 0.000 title description 27
- 125000000217 alkyl group Chemical group 0.000 claims description 491
- 125000000623 heterocyclic group Chemical group 0.000 claims description 381
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 337
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims description 275
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 222
- 150000001875 compounds Chemical class 0.000 claims description 200
- 229910052736 halogen Inorganic materials 0.000 claims description 188
- 239000001257 hydrogen Substances 0.000 claims description 188
- 229910052739 hydrogen Inorganic materials 0.000 claims description 188
- 150000002367 halogens Chemical class 0.000 claims description 186
- 125000003118 aryl group Chemical group 0.000 claims description 168
- 125000002950 monocyclic group Chemical group 0.000 claims description 142
- 125000003545 alkoxy group Chemical group 0.000 claims description 139
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 134
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 134
- 125000005842 heteroatom Chemical group 0.000 claims description 124
- 229910052760 oxygen Inorganic materials 0.000 claims description 119
- 229910052757 nitrogen Inorganic materials 0.000 claims description 118
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 116
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 109
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 100
- 229920006395 saturated elastomer Polymers 0.000 claims description 94
- 150000002431 hydrogen Chemical class 0.000 claims description 89
- 229910052717 sulfur Inorganic materials 0.000 claims description 82
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims description 75
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 74
- 150000003839 salts Chemical class 0.000 claims description 74
- 125000001424 substituent group Chemical group 0.000 claims description 74
- -1 cyano , amino Chemical group 0.000 claims description 61
- 239000012453 solvate Substances 0.000 claims description 61
- 101000879116 Homo sapiens Succinate receptor 1 Proteins 0.000 claims description 53
- 229910003827 NRaRb Inorganic materials 0.000 claims description 52
- 102100037464 Succinate receptor 1 Human genes 0.000 claims description 48
- 150000001540 azides Chemical class 0.000 claims description 45
- 125000003367 polycyclic group Chemical group 0.000 claims description 45
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 38
- 238000000034 method Methods 0.000 claims description 38
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 34
- 125000003342 alkenyl group Chemical group 0.000 claims description 32
- 125000001072 heteroaryl group Chemical group 0.000 claims description 32
- 125000000033 alkoxyamino group Chemical group 0.000 claims description 31
- 125000005189 alkyl hydroxy group Chemical group 0.000 claims description 31
- 125000004432 carbon atom Chemical group C* 0.000 claims description 31
- 239000000243 solution Substances 0.000 claims description 29
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 28
- 125000006555 (C3-C5) cycloalkyl group Chemical group 0.000 claims description 27
- 125000004452 carbocyclyl group Chemical group 0.000 claims description 27
- 229910006069 SO3H Inorganic materials 0.000 claims description 20
- 208000008338 non-alcoholic fatty liver disease Diseases 0.000 claims description 19
- 239000008194 pharmaceutical composition Substances 0.000 claims description 18
- 238000011282 treatment Methods 0.000 claims description 18
- 125000005843 halogen group Chemical group 0.000 claims description 16
- 206010053219 non-alcoholic steatohepatitis Diseases 0.000 claims description 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 13
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 13
- 206010028980 Neoplasm Diseases 0.000 claims description 12
- 201000011510 cancer Diseases 0.000 claims description 12
- 239000013078 crystal Substances 0.000 claims description 12
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 11
- 208000002780 macular degeneration Diseases 0.000 claims description 11
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 10
- KGXDTXLGXHPLEB-UHFFFAOYSA-N 2-[3-[4-isoquinolin-8-yloxy-2-(trifluoromethyl)phenoxy]phenyl]acetic acid Chemical compound C1=NC=CC2=CC=CC(=C12)OC1=CC(=C(OC=2C=C(C=CC=2)CC(=O)O)C=C1)C(F)(F)F KGXDTXLGXHPLEB-UHFFFAOYSA-N 0.000 claims description 10
- 208000007135 Retinal Neovascularization Diseases 0.000 claims description 10
- 229910052799 carbon Inorganic materials 0.000 claims description 10
- 201000010099 disease Diseases 0.000 claims description 9
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 9
- 239000003814 drug Substances 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 9
- RAPBYIQPOZBOOI-UHFFFAOYSA-N 2-[3-[4-(1-chloroisoquinolin-8-yl)oxy-2-(trifluoromethyl)phenoxy]phenyl]acetic acid Chemical compound ClC1=NC=CC2=CC=CC(=C12)OC1=CC(=C(OC=2C=C(C=CC=2)CC(=O)O)C=C1)C(F)(F)F RAPBYIQPOZBOOI-UHFFFAOYSA-N 0.000 claims description 7
- AKVLNZGPZMRENW-UHFFFAOYSA-N 2-[3-[4-(1-methylisoquinolin-8-yl)oxy-2-(trifluoromethyl)phenoxy]phenyl]acetic acid Chemical compound CC1=NC=CC2=CC=CC(=C12)OC1=CC(=C(OC=2C=C(C=CC=2)CC(=O)O)C=C1)C(F)(F)F AKVLNZGPZMRENW-UHFFFAOYSA-N 0.000 claims description 7
- QOKNHPNWSGLMIJ-UHFFFAOYSA-N 2-[3-[4-isoquinolin-8-yloxy-3-(trifluoromethyl)phenoxy]phenyl]acetic acid Chemical compound C1=NC=CC2=CC=CC(=C12)OC1=C(C=C(OC=2C=C(C=CC=2)CC(=O)O)C=C1)C(F)(F)F QOKNHPNWSGLMIJ-UHFFFAOYSA-N 0.000 claims description 7
- LPHICRZKBRICMQ-UHFFFAOYSA-N 3-[3-[4-isoquinolin-8-yloxy-2-(trifluoromethyl)phenoxy]phenyl]propanoic acid Chemical compound C1=NC=CC2=CC=CC(=C12)OC1=CC(=C(OC=2C=C(C=CC=2)CCC(=O)O)C=C1)C(F)(F)F LPHICRZKBRICMQ-UHFFFAOYSA-N 0.000 claims description 7
- PVUCVJNWBKKEBP-UHFFFAOYSA-N 8-[4-[3-[2-(2H-tetrazol-5-yl)ethyl]phenoxy]-3-(trifluoromethyl)phenoxy]isoquinoline Chemical compound N1N=NN=C1CCC=1C=C(OC2=C(C=C(OC=3C=CC=C4C=CN=CC=34)C=C2)C(F)(F)F)C=CC=1 PVUCVJNWBKKEBP-UHFFFAOYSA-N 0.000 claims description 7
- 206010020772 Hypertension Diseases 0.000 claims description 7
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 7
- GQMUSEMFORQZMQ-UHFFFAOYSA-N 2-[3-[4-(1H-indazol-4-yloxy)-2-(trifluoromethyl)phenoxy]phenyl]acetic acid Chemical compound N1N=CC2=C(C=CC=C12)OC1=CC(=C(OC=2C=C(C=CC=2)CC(=O)O)C=C1)C(F)(F)F GQMUSEMFORQZMQ-UHFFFAOYSA-N 0.000 claims description 6
- PDWKHIRXZXHUTD-UHFFFAOYSA-N 2-[3-[4-imidazo[1,5-a]pyridin-5-yloxy-2-(trifluoromethyl)phenoxy]phenyl]acetic acid Chemical compound OC(=O)CC1=CC(OC2=C(C=C(OC3=CC=CC4=CN=CN34)C=C2)C(F)(F)F)=CC=C1 PDWKHIRXZXHUTD-UHFFFAOYSA-N 0.000 claims description 6
- AOZOZASXNMSWLJ-UHFFFAOYSA-N 3-[3-[4-(1H-indazol-5-yloxy)-2-(trifluoromethyl)phenoxy]phenyl]propanoic acid Chemical compound N1N=CC2=CC(=CC=C12)OC1=CC(=C(OC=2C=C(C=CC=2)CCC(=O)O)C=C1)C(F)(F)F AOZOZASXNMSWLJ-UHFFFAOYSA-N 0.000 claims description 6
- 125000004429 atom Chemical group 0.000 claims description 6
- HXBLYGHNTRPYEK-UHFFFAOYSA-N 3-[3-[4-(1,2,3,4-tetrahydroisoquinolin-8-yloxy)-2-(trifluoromethyl)phenoxy]phenyl]propanoic acid Chemical compound C1NCCC2=CC=CC(=C12)OC1=CC(=C(OC=2C=C(C=CC=2)CCC(=O)O)C=C1)C(F)(F)F HXBLYGHNTRPYEK-UHFFFAOYSA-N 0.000 claims description 5
- QQRHEJKWVHFRGN-UHFFFAOYSA-N 8-[4-[3-[2-(1H-1,2,4-triazol-5-yl)ethyl]phenoxy]-3-(trifluoromethyl)phenoxy]isoquinoline Chemical compound N=1N=C(NC=1)CCC=1C=C(OC2=C(C=C(OC=3C=CC=C4C=CN=CC=34)C=C2)C(F)(F)F)C=CC=1 QQRHEJKWVHFRGN-UHFFFAOYSA-N 0.000 claims description 5
- 208000010706 fatty liver disease Diseases 0.000 claims description 5
- 230000001404 mediated effect Effects 0.000 claims description 5
- 230000002265 prevention Effects 0.000 claims description 5
- 230000008569 process Effects 0.000 claims description 5
- 231100000433 cytotoxic Toxicity 0.000 claims description 4
- 229940127089 cytotoxic agent Drugs 0.000 claims description 4
- 239000002254 cytotoxic agent Substances 0.000 claims description 4
- 230000001472 cytotoxic effect Effects 0.000 claims description 4
- 239000002552 dosage form Substances 0.000 claims description 4
- 208000019423 liver disease Diseases 0.000 claims description 4
- 231100000065 noncytotoxic Toxicity 0.000 claims description 4
- 230000002020 noncytotoxic effect Effects 0.000 claims description 4
- 208000024172 Cardiovascular disease Diseases 0.000 claims description 3
- 208000007342 Diabetic Nephropathies Diseases 0.000 claims description 3
- 206010061218 Inflammation Diseases 0.000 claims description 3
- 206010029113 Neovascularisation Diseases 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 208000033679 diabetic kidney disease Diseases 0.000 claims description 3
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 3
- 208000016097 disease of metabolism Diseases 0.000 claims description 3
- 230000002519 immonomodulatory effect Effects 0.000 claims description 3
- 230000004054 inflammatory process Effects 0.000 claims description 3
- 208000030159 metabolic disease Diseases 0.000 claims description 3
- FTNSWYXUIMTNTM-UHFFFAOYSA-N 2-[3-[4-(3,4-dihydro-2H-1,4-benzoxazin-6-yloxy)-2-(trifluoromethyl)phenoxy]phenyl]acetic acid Chemical compound OC(=O)CC1=CC(OC2=C(C=C(OC3=CC4=C(OCCN4)C=C3)C=C2)C(F)(F)F)=CC=C1 FTNSWYXUIMTNTM-UHFFFAOYSA-N 0.000 claims description 2
- QBDALWBIVUJZER-UHFFFAOYSA-N 2-[3-[4-(3-methylimidazo[1,5-a]pyridin-5-yl)oxy-2-(trifluoromethyl)phenoxy]phenyl]acetic acid Chemical compound CC1=NC=C2C=CC=C(OC3=CC(=C(OC4=CC=CC(CC(O)=O)=C4)C=C3)C(F)(F)F)N12 QBDALWBIVUJZER-UHFFFAOYSA-N 0.000 claims description 2
- QJUUVSLRADKZDE-UHFFFAOYSA-N 2-[3-[4-(5-fluoroisoquinolin-8-yl)oxy-2-(trifluoromethyl)phenoxy]phenyl]acetic acid Chemical compound FC1=C2C=CN=CC2=C(C=C1)OC1=CC(=C(OC=2C=C(C=CC=2)CC(=O)O)C=C1)C(F)(F)F QJUUVSLRADKZDE-UHFFFAOYSA-N 0.000 claims description 2
- XTRHBOCAGSVFIW-UHFFFAOYSA-N 2-[3-[4-(8-chlorophthalazin-5-yl)oxy-2-(trifluoromethyl)phenoxy]phenyl]acetic acid Chemical compound ClC=1C=CC(=C2C=NN=CC=12)OC1=CC(=C(OC=2C=C(C=CC=2)CC(=O)O)C=C1)C(F)(F)F XTRHBOCAGSVFIW-UHFFFAOYSA-N 0.000 claims description 2
- GLIPRLRHTCRJEF-UHFFFAOYSA-N 2-[3-[4-([1,2,4]triazolo[4,3-a]pyridin-5-yloxy)-2-(trifluoromethyl)phenoxy]phenyl]acetic acid Chemical compound OC(=O)CC1=CC(OC2=C(C=C(OC3=CC=CC4=NN=CN34)C=C2)C(F)(F)F)=CC=C1 GLIPRLRHTCRJEF-UHFFFAOYSA-N 0.000 claims description 2
- ZOQXCJSKIOEXMX-UHFFFAOYSA-N 2-[3-[4-([1,2,4]triazolo[4,3-a]pyridin-7-yloxy)-2-(trifluoromethyl)phenoxy]phenyl]acetic acid Chemical compound OC(=O)CC1=CC(OC2=C(C=C(OC3=CC4=NN=CN4C=C3)C=C2)C(F)(F)F)=CC=C1 ZOQXCJSKIOEXMX-UHFFFAOYSA-N 0.000 claims description 2
- DSUBAFUIMPPVTG-UHFFFAOYSA-N 2-[3-[4-[(3-cyano-1H-indazol-5-yl)oxy]-2-(trifluoromethyl)phenoxy]phenyl]acetic acid Chemical compound C(#N)C1=NNC2=CC=C(C=C12)OC1=CC(=C(OC=2C=C(C=CC=2)CC(=O)O)C=C1)C(F)(F)F DSUBAFUIMPPVTG-UHFFFAOYSA-N 0.000 claims description 2
- HKDUZIJPVBGYCM-UHFFFAOYSA-N 2-[3-[4-[1-(carboxymethyl)indol-5-yl]oxy-2-(trifluoromethyl)phenoxy]phenyl]acetic acid Chemical compound OC(=O)CN1C=CC2=CC(OC3=CC(=C(OC4=CC=CC(CC(O)=O)=C4)C=C3)C(F)(F)F)=CC=C12 HKDUZIJPVBGYCM-UHFFFAOYSA-N 0.000 claims description 2
- OENUQORUQKUYRD-UHFFFAOYSA-N 2-[3-[4-[1-(carboxymethyl)indol-6-yl]oxy-2-(trifluoromethyl)phenoxy]phenyl]acetic acid Chemical compound OC(=O)CN1C=CC2=CC=C(OC3=CC(=C(OC4=CC=CC(CC(O)=O)=C4)C=C3)C(F)(F)F)C=C12 OENUQORUQKUYRD-UHFFFAOYSA-N 0.000 claims description 2
- FLXKSTZJBPZINJ-UHFFFAOYSA-N 2-[3-[4-[1-(oxetan-3-yl)imidazo[4,5-b]pyridin-6-yl]oxy-2-(trifluoromethyl)phenoxy]phenyl]acetic acid Chemical compound OC(=O)CC1=CC(OC2=C(C=C(OC3=CN=C4N=CN(C5COC5)C4=C3)C=C2)C(F)(F)F)=CC=C1 FLXKSTZJBPZINJ-UHFFFAOYSA-N 0.000 claims description 2
- RAFXHYZOTNZEAZ-UHFFFAOYSA-N 2-[3-[4-[1-(oxetan-3-yl)indazol-5-yl]oxy-2-(trifluoromethyl)phenoxy]phenyl]acetic acid Chemical compound OC(=O)CC1=CC(OC2=C(C=C(OC3=CC=C4N(N=CC4=C3)C3COC3)C=C2)C(F)(F)F)=CC=C1 RAFXHYZOTNZEAZ-UHFFFAOYSA-N 0.000 claims description 2
- VDWXIUFGJFXGNT-UHFFFAOYSA-N 2-[3-[4-[1-(oxetan-3-yl)indazol-6-yl]oxy-2-(trifluoromethyl)phenoxy]phenyl]acetic acid Chemical compound OC(=O)CC1=CC(OC2=C(C=C(OC3=CC=C4C=NN(C5COC5)C4=C3)C=C2)C(F)(F)F)=CC=C1 VDWXIUFGJFXGNT-UHFFFAOYSA-N 0.000 claims description 2
- IQBLKJNHXZRYIT-UHFFFAOYSA-N 2-[3-[4-[1-(oxetan-3-yl)indol-6-yl]oxy-2-(trifluoromethyl)phenoxy]phenyl]acetic acid Chemical compound OC(=O)CC1=CC(OC2=C(C=C(OC3=CC=C4C=CN(C5COC5)C4=C3)C=C2)C(F)(F)F)=CC=C1 IQBLKJNHXZRYIT-UHFFFAOYSA-N 0.000 claims description 2
- FIXVDBMUYKXOPB-UHFFFAOYSA-N 2-[3-[4-[1-(oxetan-3-yl)pyrrolo[2,3-b]pyridin-6-yl]oxy-2-(trifluoromethyl)phenoxy]phenyl]acetic acid Chemical compound OC(=O)CC1=CC(OC2=C(C=C(OC3=CC=C4C=CN(C5COC5)C4=N3)C=C2)C(F)(F)F)=CC=C1 FIXVDBMUYKXOPB-UHFFFAOYSA-N 0.000 claims description 2
- AYTBUZIDBBBQGJ-UHFFFAOYSA-N 2-[3-[4-[2-(oxetan-3-yl)indazol-6-yl]oxy-2-(trifluoromethyl)phenoxy]phenyl]acetic acid Chemical compound O1CC(C1)N1N=C2C=C(C=CC2=C1)OC1=CC(=C(OC=2C=C(C=CC=2)CC(=O)O)C=C1)C(F)(F)F AYTBUZIDBBBQGJ-UHFFFAOYSA-N 0.000 claims description 2
- FXNYRKBXAHDVMR-UHFFFAOYSA-N 2-[3-[4-[3-(oxetan-3-yl)imidazo[1,5-a]pyridin-6-yl]oxy-2-(trifluoromethyl)phenoxy]phenyl]acetic acid Chemical compound OC(=O)CC1=CC(OC2=C(C=C(OC3=CN4C(=CN=C4C4COC4)C=C3)C=C2)C(F)(F)F)=CC=C1 FXNYRKBXAHDVMR-UHFFFAOYSA-N 0.000 claims description 2
- XCRNXGMEZIZDMZ-UHFFFAOYSA-N 2-[3-[4-imidazo[1,5-a]pyridin-8-yloxy-2-(trifluoromethyl)phenoxy]phenyl]acetic acid Chemical compound OC(=O)CC1=CC(OC2=C(C=C(OC3=CC=CN4C=NC=C34)C=C2)C(F)(F)F)=CC=C1 XCRNXGMEZIZDMZ-UHFFFAOYSA-N 0.000 claims description 2
- VVESOPXXJCDYIF-UHFFFAOYSA-N 2-[3-[4-phthalazin-5-yloxy-2-(trifluoromethyl)phenoxy]phenyl]acetic acid Chemical compound C1=NN=CC2=C(C=CC=C12)OC1=CC(=C(OC=2C=C(C=CC=2)CC(=O)O)C=C1)C(F)(F)F VVESOPXXJCDYIF-UHFFFAOYSA-N 0.000 claims description 2
- PWIAIIJGDAWRHA-UHFFFAOYSA-N 2-[3-[4-quinazolin-5-yloxy-2-(trifluoromethyl)phenoxy]phenyl]acetic acid Chemical compound N1=CN=CC2=C(C=CC=C12)OC1=CC(=C(OC=2C=C(C=CC=2)CC(=O)O)C=C1)C(F)(F)F PWIAIIJGDAWRHA-UHFFFAOYSA-N 0.000 claims description 2
- DQYRPSSUUZMLPU-UHFFFAOYSA-N 2-[3-[4-quinolin-6-yloxy-2-(trifluoromethyl)phenoxy]phenyl]acetic acid Chemical compound N1=CC=CC2=CC(=CC=C12)OC1=CC(=C(OC=2C=C(C=CC=2)CC(=O)O)C=C1)C(F)(F)F DQYRPSSUUZMLPU-UHFFFAOYSA-N 0.000 claims description 2
- XEZTXBXTVJBXOL-UHFFFAOYSA-N 2-[3-[5-isoquinolin-8-yloxy-3-(trifluoromethyl)pyridin-2-yl]oxyphenyl]acetic acid Chemical compound C1=NC=CC2=CC=CC(=C12)OC=1C=C(C(=NC=1)OC=1C=C(C=CC=1)CC(=O)O)C(F)(F)F XEZTXBXTVJBXOL-UHFFFAOYSA-N 0.000 claims description 2
- VCQFZVGIFWHEKL-UHFFFAOYSA-N 3-[3-[4-[(2-methyl-3,4-dihydro-1H-isoquinolin-8-yl)oxy]-2-(trifluoromethyl)phenoxy]phenyl]propanoic acid Chemical compound CN1CC2=C(C=CC=C2CC1)OC1=CC(=C(OC=2C=C(C=CC=2)CCC(=O)O)C=C1)C(F)(F)F VCQFZVGIFWHEKL-UHFFFAOYSA-N 0.000 claims description 2
- ZDMDCGLEMMTWFX-UHFFFAOYSA-N 3-[3-[4-imidazo[1,2-a]pyridin-5-yloxy-2-(trifluoromethyl)phenoxy]phenyl]propanoic acid Chemical compound OC(=O)CCC1=CC(OC2=C(C=C(OC3=CC=CC4=NC=CN34)C=C2)C(F)(F)F)=CC=C1 ZDMDCGLEMMTWFX-UHFFFAOYSA-N 0.000 claims description 2
- GQLAQUSXEFCRJC-UHFFFAOYSA-N 3-[3-[4-imidazo[1,2-a]pyridin-8-yloxy-2-(trifluoromethyl)phenoxy]phenyl]propanoic acid Chemical compound OC(=O)CCC1=CC(OC2=C(C=C(OC3=CC=CN4C=CN=C34)C=C2)C(F)(F)F)=CC=C1 GQLAQUSXEFCRJC-UHFFFAOYSA-N 0.000 claims description 2
- YAXVYZJJXRQPCQ-UHFFFAOYSA-N 3-[3-[4-isoquinolin-5-yloxy-2-(trifluoromethyl)phenoxy]phenyl]propanoic acid Chemical compound C1=NC=CC2=C(C=CC=C12)OC1=CC(=C(OC=2C=C(C=CC=2)CCC(=O)O)C=C1)C(F)(F)F YAXVYZJJXRQPCQ-UHFFFAOYSA-N 0.000 claims description 2
- KPINORXHWSPYHQ-UHFFFAOYSA-N 3-[3-[4-phthalazin-5-yloxy-2-(trifluoromethyl)phenoxy]phenyl]propanoic acid Chemical compound C1=NN=CC2=C(C=CC=C12)OC1=CC(=C(OC=2C=C(C=CC=2)CCC(=O)O)C=C1)C(F)(F)F KPINORXHWSPYHQ-UHFFFAOYSA-N 0.000 claims description 2
- LPRORPSBUCCVAF-UHFFFAOYSA-N 3-[3-[4-quinolin-4-yloxy-2-(trifluoromethyl)phenoxy]phenyl]propanoic acid Chemical compound N1=CC=C(C2=CC=CC=C12)OC1=CC(=C(OC=2C=C(C=CC=2)CCC(=O)O)C=C1)C(F)(F)F LPRORPSBUCCVAF-UHFFFAOYSA-N 0.000 claims description 2
- SAUYZGAEUYVXEE-UHFFFAOYSA-N 3-[3-[4-quinolin-8-yloxy-2-(trifluoromethyl)phenoxy]phenyl]propanoic acid Chemical compound N1=CC=CC2=CC=CC(=C12)OC1=CC(=C(OC=2C=C(C=CC=2)CCC(=O)O)C=C1)C(F)(F)F SAUYZGAEUYVXEE-UHFFFAOYSA-N 0.000 claims description 2
- VMGDEZLEWMXJFP-UHFFFAOYSA-N 3-[4-[4-isoquinolin-8-yloxy-2-(trifluoromethyl)phenoxy]phenyl]propanoic acid Chemical compound C1=NC=CC2=CC=CC(=C12)OC1=CC(=C(OC2=CC=C(C=C2)CCC(=O)O)C=C1)C(F)(F)F VMGDEZLEWMXJFP-UHFFFAOYSA-N 0.000 claims description 2
- BZKIJAHFQPGWEH-UHFFFAOYSA-N 5-[4-[3-(carboxymethyl)phenoxy]-3-(trifluoromethyl)phenoxy]-1H-indazole-3-carboxylic acid Chemical compound C(=O)(O)CC=1C=C(OC2=C(C=C(OC=3C=C4C(=NNC4=CC=3)C(=O)O)C=C2)C(F)(F)F)C=CC=1 BZKIJAHFQPGWEH-UHFFFAOYSA-N 0.000 claims description 2
- WQRUNIBAGWNLIV-UHFFFAOYSA-N 8-[4-[3-(2H-tetrazol-5-ylmethyl)phenoxy]-3-(trifluoromethyl)phenoxy]isoquinoline Chemical compound N1N=NN=C1CC=1C=C(OC2=C(C=C(OC=3C=CC=C4C=CN=CC=34)C=C2)C(F)(F)F)C=CC=1 WQRUNIBAGWNLIV-UHFFFAOYSA-N 0.000 claims description 2
- 208000035473 Communicable disease Diseases 0.000 claims description 2
- 239000000443 aerosol Substances 0.000 claims description 2
- 239000002775 capsule Substances 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- 235000019260 propionic acid Nutrition 0.000 claims description 2
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- 230000029865 regulation of blood pressure Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 210000001525 retina Anatomy 0.000 description 1
- 230000004491 retinal development Effects 0.000 description 1
- 210000001116 retinal neuron Anatomy 0.000 description 1
- 239000000790 retinal pigment Substances 0.000 description 1
- 238000004007 reversed phase HPLC Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 229960001860 salicylate Drugs 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 230000019491 signal transduction Effects 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000004055 small Interfering RNA Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 229940074404 sodium succinate Drugs 0.000 description 1
- ZDQYSKICYIVCPN-UHFFFAOYSA-L sodium succinate (anhydrous) Chemical compound [Na+].[Na+].[O-]C(=O)CCC([O-])=O ZDQYSKICYIVCPN-UHFFFAOYSA-L 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical class [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 125000003003 spiro group Chemical group 0.000 description 1
- 210000000130 stem cell Anatomy 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 150000003890 succinate salts Chemical class 0.000 description 1
- IIACRCGMVDHOTQ-UHFFFAOYSA-M sulfamate Chemical compound NS([O-])(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-M 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 150000003892 tartrate salts Chemical class 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229960000814 tetanus toxoid Drugs 0.000 description 1
- WHRNULOCNSKMGB-UHFFFAOYSA-N tetrahydrofuran thf Chemical compound C1CCOC1.C1CCOC1 WHRNULOCNSKMGB-UHFFFAOYSA-N 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000003039 tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 description 1
- 125000004853 tetrahydropyridinyl group Chemical group N1(CCCC=C1)* 0.000 description 1
- 125000000147 tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- WROMPOXWARCANT-UHFFFAOYSA-N tfa trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F WROMPOXWARCANT-UHFFFAOYSA-N 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000002110 toxicologic effect Effects 0.000 description 1
- 231100000759 toxicological effect Toxicity 0.000 description 1
- 230000035897 transcription Effects 0.000 description 1
- 238000013518 transcription Methods 0.000 description 1
- 238000001890 transfection Methods 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 230000005945 translocation Effects 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 230000004102 tricarboxylic acid cycle Effects 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 229940070710 valerate Drugs 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- 230000002792 vascular Effects 0.000 description 1
- 238000001845 vibrational spectrum Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/22—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the nitrogen-containing ring
- C07D217/24—Oxygen atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/20—Oxygen atoms
- C07D215/22—Oxygen atoms attached in position 2 or 4
- C07D215/233—Oxygen atoms attached in position 2 or 4 only one oxygen atom which is attached in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/02—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/54—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings condensed with carbocyclic rings or ring systems
- C07D231/56—Benzopyrazoles; Hydrogenated benzopyrazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
- C07D237/26—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings condensed with carbocyclic rings or ring systems
- C07D237/30—Phthalazines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
- C07D239/72—Quinazolines; Hydrogenated quinazolines
- C07D239/74—Quinazolines; Hydrogenated quinazolines with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached to ring carbon atoms of the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/28—1,4-Oxazines; Hydrogenated 1,4-oxazines
- C07D265/34—1,4-Oxazines; Hydrogenated 1,4-oxazines condensed with carbocyclic rings
- C07D265/36—1,4-Oxazines; Hydrogenated 1,4-oxazines condensed with carbocyclic rings condensed with one six-membered ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/10—1,4-Dioxanes; Hydrogenated 1,4-dioxanes
- C07D319/14—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems
- C07D319/16—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems condensed with one six-membered ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Indole Compounds (AREA)
- Quinoline Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IN201741008624 | 2017-03-13 | ||
| IN201741008624 | 2017-03-13 | ||
| PCT/IN2018/050136 WO2018167800A1 (en) | 2017-03-13 | 2018-03-13 | Fused bicyclic compounds, compositions and applications thereof |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2020515631A JP2020515631A (ja) | 2020-05-28 |
| JP2020515631A5 JP2020515631A5 (enExample) | 2021-04-22 |
| JP7301758B2 true JP7301758B2 (ja) | 2023-07-03 |
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| JP2019571826A Active JP7301758B2 (ja) | 2017-03-13 | 2018-03-13 | 縮合二環式化合物、その組成物及び応用 |
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| EP (1) | EP3596051B1 (enExample) |
| JP (1) | JP7301758B2 (enExample) |
| CA (1) | CA3056551A1 (enExample) |
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| ES3028093T3 (en) * | 2018-06-07 | 2025-06-18 | Disarm Therapeutics Inc | Inhibitors of sarm1 |
| US12391695B2 (en) | 2019-06-10 | 2025-08-19 | Lupin Limited | PRMT5 inhibitors |
| WO2021111322A1 (en) | 2019-12-03 | 2021-06-10 | Lupin Limited | Substituted nucleoside analogs as prmt5 inhibitors |
| WO2021161230A1 (en) * | 2020-02-12 | 2021-08-19 | Curadev Pharma Pvt. Ltd. | Small molecule sting antagonists |
| US20240165108A1 (en) * | 2022-08-09 | 2024-05-23 | Glaxosmithkline Intellectual Property Development Limited | Novel use |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2003528871A (ja) | 2000-03-27 | 2003-09-30 | シエーリング アクチエンゲゼルシャフト | Nosインヒビターとしてのn−複素環式誘導体 |
| JP2014520885A (ja) | 2011-07-19 | 2014-08-25 | 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 | ロイコトリエンa4ヒドロラーゼの阻害剤としてのアリールピラゾールエーテル |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5821672A (ja) * | 1981-07-28 | 1983-02-08 | Nippon Tokushu Noyaku Seizo Kk | ベンゾイソチアゾ−ル誘導体、その製法、及び農業用殺菌剤 |
| US5977117A (en) * | 1996-01-05 | 1999-11-02 | Texas Biotechnology Corporation | Substituted phenyl compounds and derivatives thereof that modulate the activity of endothelin |
| EP2928886B1 (en) * | 2012-12-07 | 2016-11-02 | Boehringer Ingelheim International GmbH | New indanyloxydihydrobenzofuranylacetic acids |
-
2018
- 2018-03-13 EP EP18713373.1A patent/EP3596051B1/en active Active
- 2018-03-13 JP JP2019571826A patent/JP7301758B2/ja active Active
- 2018-03-13 WO PCT/IN2018/050136 patent/WO2018167800A1/en not_active Ceased
- 2018-03-13 US US16/494,239 patent/US11098026B2/en active Active
- 2018-03-13 CA CA3056551A patent/CA3056551A1/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2003528871A (ja) | 2000-03-27 | 2003-09-30 | シエーリング アクチエンゲゼルシャフト | Nosインヒビターとしてのn−複素環式誘導体 |
| JP2014520885A (ja) | 2011-07-19 | 2014-08-25 | 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 | ロイコトリエンa4ヒドロラーゼの阻害剤としてのアリールピラゾールエーテル |
Non-Patent Citations (3)
| Title |
|---|
| Bioorganic & Medicinal Chemistry Letters,2011年,Vol.21,pp.3596-3602 |
| Chemical Abstract,89:146562,Retrieved from STN international [online] ;retrieved on 2 March 2022 |
| Database REGISTRY,2011年,RN 1348552-37-3, 904281-92-1, 904034-97-5, 330561-55-2, 328265-88-9, 328265-86-7, 328265-73-2, 328265-40-3, 313530-69-7, 312759-09-4, 297743-29-4, 294890-77-0,Retrieved from STN international [online] ;retrieved on 2 March 2022 |
Also Published As
| Publication number | Publication date |
|---|---|
| CA3056551A1 (en) | 2018-09-20 |
| JP2020515631A (ja) | 2020-05-28 |
| WO2018167800A1 (en) | 2018-09-20 |
| EP3596051B1 (en) | 2022-04-27 |
| EP3596051A1 (en) | 2020-01-22 |
| US20200087281A1 (en) | 2020-03-19 |
| US11098026B2 (en) | 2021-08-24 |
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