JP2020515631A5 - - Google Patents
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- JP2020515631A5 JP2020515631A5 JP2019571826A JP2019571826A JP2020515631A5 JP 2020515631 A5 JP2020515631 A5 JP 2020515631A5 JP 2019571826 A JP2019571826 A JP 2019571826A JP 2019571826 A JP2019571826 A JP 2019571826A JP 2020515631 A5 JP2020515631 A5 JP 2020515631A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- cycloalkyl
- heterocyclyl
- aryl
- heteroaryl
- 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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- 125000000217 alkyl group Chemical group 0.000 claims 171
- 125000000623 heterocyclic group Chemical group 0.000 claims 111
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 90
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims 82
- 125000003545 alkoxy group Chemical group 0.000 claims 69
- 125000003118 aryl group Chemical group 0.000 claims 64
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 56
- 229910052739 hydrogen Inorganic materials 0.000 claims 49
- 239000001257 hydrogen Substances 0.000 claims 49
- 229910052736 halogen Inorganic materials 0.000 claims 45
- 150000002367 halogens Chemical class 0.000 claims 45
- 125000002950 monocyclic group Chemical group 0.000 claims 38
- 229910052760 oxygen Inorganic materials 0.000 claims 38
- 125000005842 heteroatom Chemical group 0.000 claims 37
- 229910052757 nitrogen Inorganic materials 0.000 claims 37
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 33
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 30
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 30
- 125000004093 cyano group Chemical group *C#N 0.000 claims 30
- 125000002619 bicyclic group Chemical group 0.000 claims 29
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 27
- 125000001424 substituent group Chemical group 0.000 claims 24
- -1 azide Chemical group 0.000 claims 21
- 229910052717 sulfur Inorganic materials 0.000 claims 21
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 20
- 229920006395 saturated elastomer Polymers 0.000 claims 20
- 150000002431 hydrogen Chemical class 0.000 claims 19
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 19
- 150000001875 compounds Chemical class 0.000 claims 15
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 14
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 13
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 12
- 150000003839 salts Chemical class 0.000 claims 11
- 239000012453 solvate Substances 0.000 claims 11
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 10
- 125000000033 alkoxyamino group Chemical group 0.000 claims 10
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 10
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims 9
- 125000003367 polycyclic group Chemical group 0.000 claims 9
- 125000006555 (C3-C5) cycloalkyl group Chemical group 0.000 claims 8
- 125000001072 heteroaryl group Chemical group 0.000 claims 8
- 239000008194 pharmaceutical composition Substances 0.000 claims 8
- 125000003342 alkenyl group Chemical group 0.000 claims 7
- 125000000304 alkynyl group Chemical group 0.000 claims 7
- 150000001540 azides Chemical class 0.000 claims 6
- 125000004452 carbocyclyl group Chemical group 0.000 claims 6
- 125000005189 alkyl hydroxy group Chemical group 0.000 claims 5
- 125000005843 halogen group Chemical group 0.000 claims 5
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 5
- 125000004414 alkyl thio group Chemical group 0.000 claims 4
- 238000004519 manufacturing process Methods 0.000 claims 4
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 3
- 125000004939 6-pyridyl group Chemical group N1=CC=CC=C1* 0.000 claims 3
- 208000010706 fatty liver disease Diseases 0.000 claims 3
- 208000008338 non-alcoholic fatty liver disease Diseases 0.000 claims 3
- MCTWTZJPVLRJOU-UHFFFAOYSA-N 1-methyl-1H-imidazole Chemical compound CN1C=CN=C1 MCTWTZJPVLRJOU-UHFFFAOYSA-N 0.000 claims 2
- QGZKZWMMDBUOKI-UHFFFAOYSA-N 2-[3-[4-[2-(oxetan-3-yl)indazol-5-yl]oxy-2-(trifluoromethyl)phenoxy]phenyl]acetic acid Chemical compound O1CC(C1)N1N=C2C=CC(=CC2=C1)OC1=CC(=C(OC=2C=C(C=CC=2)CC(=O)O)C=C1)C(F)(F)F QGZKZWMMDBUOKI-UHFFFAOYSA-N 0.000 claims 2
- 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 2
- 206010028980 Neoplasm Diseases 0.000 claims 2
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 claims 2
- 201000011510 cancer Diseases 0.000 claims 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims 2
- 150000002460 imidazoles Chemical class 0.000 claims 2
- DUWWHGPELOTTOE-UHFFFAOYSA-N n-(5-chloro-2,4-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC(OC)=C(NC(=O)CC(C)=O)C=C1Cl DUWWHGPELOTTOE-UHFFFAOYSA-N 0.000 claims 2
- 206010053219 non-alcoholic steatohepatitis Diseases 0.000 claims 2
- 235000019260 propionic acid Nutrition 0.000 claims 2
- CPDJEVWCZRMFTB-UHFFFAOYSA-N 2-[3-(2-cyclopropyl-4-isoquinolin-8-yloxyphenoxy)phenyl]acetic acid Chemical compound C1(CC1)C1=C(OC=2C=C(C=CC=2)CC(=O)O)C=CC(=C1)OC=1C=CC=C2C=CN=CC=12 CPDJEVWCZRMFTB-UHFFFAOYSA-N 0.000 claims 1
- NOTXHOUQUHBLJM-UHFFFAOYSA-N 2-[3-[2-cyclopropyl-4-[2-methyl-3-(oxetan-3-yl)benzimidazol-5-yl]oxyphenoxy]phenyl]acetic acid Chemical compound C1(CC1)C1=C(OC=2C=C(C=CC=2)CC(=O)O)C=CC(=C1)OC1=CC2=C(N=C(N2C2COC2)C)C=C1 NOTXHOUQUHBLJM-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- UWIXEEXXLDCDBJ-UHFFFAOYSA-N 3-[3-[4-(2,3-dihydro-1H-inden-1-yloxy)-2-(trifluoromethyl)phenoxy]phenyl]propanoic acid Chemical compound C1(CCC2=CC=CC=C12)OC1=CC(=C(OC=2C=C(C=CC=2)CCC(=O)O)C=C1)C(F)(F)F UWIXEEXXLDCDBJ-UHFFFAOYSA-N 0.000 claims 1
- FWSYYMMZLRDYIG-UHFFFAOYSA-N 3-[3-[4-(2-methylindazol-5-yl)oxy-2-(trifluoromethyl)phenoxy]phenyl]propanoic acid Chemical compound CN1N=C2C=CC(=CC2=C1)OC1=CC(=C(OC=2C=C(C=CC=2)CCC(=O)O)C=C1)C(F)(F)F FWSYYMMZLRDYIG-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 125000004938 5-pyridyl group Chemical group N1=CC=CC(=C1)* 0.000 claims 1
- 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 1
- 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 1
- 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 1
- 208000024172 Cardiovascular disease Diseases 0.000 claims 1
- 208000035473 Communicable disease Diseases 0.000 claims 1
- 208000007342 Diabetic Nephropathies Diseases 0.000 claims 1
- 101000879116 Homo sapiens Succinate receptor 1 Proteins 0.000 claims 1
- 206010020772 Hypertension Diseases 0.000 claims 1
- 206010061218 Inflammation Diseases 0.000 claims 1
- 208000007135 Retinal Neovascularization Diseases 0.000 claims 1
- 102100037464 Succinate receptor 1 Human genes 0.000 claims 1
- 239000000443 aerosol Substances 0.000 claims 1
- 230000001476 alcoholic effect Effects 0.000 claims 1
- 230000033115 angiogenesis Effects 0.000 claims 1
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 claims 1
- 239000002775 capsule Substances 0.000 claims 1
- 239000013078 crystal Substances 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 231100000433 cytotoxic Toxicity 0.000 claims 1
- 229940127089 cytotoxic agent Drugs 0.000 claims 1
- 239000002254 cytotoxic agent Substances 0.000 claims 1
- 230000001472 cytotoxic effect Effects 0.000 claims 1
- 230000007850 degeneration Effects 0.000 claims 1
- 208000033679 diabetic kidney disease Diseases 0.000 claims 1
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 208000016097 disease of metabolism Diseases 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- 239000002552 dosage form Substances 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 239000002955 immunomodulating agent Substances 0.000 claims 1
- 229940121354 immunomodulator Drugs 0.000 claims 1
- 230000004054 inflammatory process Effects 0.000 claims 1
- 208000019423 liver disease Diseases 0.000 claims 1
- 230000001404 mediated effect Effects 0.000 claims 1
- 208000030159 metabolic disease Diseases 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 235000001968 nicotinic acid Nutrition 0.000 claims 1
- 239000011664 nicotinic acid Substances 0.000 claims 1
- 231100000065 noncytotoxic Toxicity 0.000 claims 1
- 230000002020 noncytotoxic effect Effects 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 239000000843 powder Substances 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- 239000000243 solution Substances 0.000 claims 1
- 239000000725 suspension Substances 0.000 claims 1
- 239000006188 syrup Substances 0.000 claims 1
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- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
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| US12391695B2 (en) | 2019-06-10 | 2025-08-19 | Lupin Limited | PRMT5 inhibitors |
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| US20240165108A1 (en) * | 2022-08-09 | 2024-05-23 | Glaxosmithkline Intellectual Property Development Limited | Novel use |
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| 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 |
| US6525051B2 (en) | 2000-03-27 | 2003-02-25 | Schering Aktiengesellschaft | N-heterocyclic derivatives as NOS inhibitors |
| JP5987220B2 (ja) | 2011-07-19 | 2016-09-07 | 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 |
| EP2928886B1 (en) * | 2012-12-07 | 2016-11-02 | Boehringer Ingelheim International GmbH | New indanyloxydihydrobenzofuranylacetic acids |
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