IL207570A - Oxadiazuenteres compounds for the treatment of diabetes - Google Patents
Oxadiazuenteres compounds for the treatment of diabetesInfo
- Publication number
- IL207570A IL207570A IL207570A IL20757010A IL207570A IL 207570 A IL207570 A IL 207570A IL 207570 A IL207570 A IL 207570A IL 20757010 A IL20757010 A IL 20757010A IL 207570 A IL207570 A IL 207570A
- Authority
- IL
- Israel
- Prior art keywords
- phenyl
- cyano
- diaza
- oxa
- oxo
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims 40
- 206010012601 diabetes mellitus Diseases 0.000 title 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims 65
- 125000000217 alkyl group Chemical group 0.000 claims 44
- 125000000753 cycloalkyl group Chemical group 0.000 claims 29
- 125000001424 substituent group Chemical group 0.000 claims 29
- 125000000304 alkynyl group Chemical group 0.000 claims 22
- 229910052739 hydrogen Inorganic materials 0.000 claims 22
- 239000001257 hydrogen Substances 0.000 claims 22
- 125000003118 aryl group Chemical group 0.000 claims 20
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 18
- 125000000623 heterocyclic group Chemical group 0.000 claims 17
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 16
- 125000001072 heteroaryl group Chemical group 0.000 claims 13
- 125000003342 alkenyl group Chemical group 0.000 claims 12
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 10
- 229910052736 halogen Inorganic materials 0.000 claims 10
- 150000003839 salts Chemical class 0.000 claims 10
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 9
- 125000005275 alkylenearyl group Chemical group 0.000 claims 9
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 9
- 125000005842 heteroatom Chemical group 0.000 claims 9
- 229910052757 nitrogen Inorganic materials 0.000 claims 9
- 229910052760 oxygen Inorganic materials 0.000 claims 9
- 239000001301 oxygen Substances 0.000 claims 9
- 229910052717 sulfur Chemical group 0.000 claims 9
- 239000011593 sulfur Chemical group 0.000 claims 9
- 125000004350 aryl cycloalkyl group Chemical group 0.000 claims 8
- 150000002431 hydrogen Chemical class 0.000 claims 7
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 6
- 125000002947 alkylene group Chemical group 0.000 claims 6
- 125000005218 alkyleneheteroaryl group Chemical group 0.000 claims 6
- 125000004429 atom Chemical group 0.000 claims 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 5
- 125000004419 alkynylene group Chemical group 0.000 claims 5
- 125000004367 cycloalkylaryl group Chemical group 0.000 claims 5
- 125000005215 cycloalkylheteroaryl group Chemical group 0.000 claims 5
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 5
- -1 thiopheneyl Chemical group 0.000 claims 4
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 3
- 239000002253 acid Substances 0.000 claims 3
- 125000004450 alkenylene group Chemical group 0.000 claims 3
- 125000002877 alkyl aryl group Chemical group 0.000 claims 3
- 229910052799 carbon Inorganic materials 0.000 claims 3
- 239000003085 diluting agent Substances 0.000 claims 3
- 239000003937 drug carrier Substances 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims 3
- 235000019260 propionic acid Nutrition 0.000 claims 3
- 125000004076 pyridyl group Chemical group 0.000 claims 3
- DLIDOWKXQKFZIN-IKABJYOBSA-N (2s)-2-[[(3s)-7-benzoyl-3-[4-[(3,4-dichlorophenyl)methoxy]phenyl]-2-oxo-1,6,8,9-tetrahydropyrido[4,3-g][1,4]benzoxazine-8-carbonyl]amino]-3-[4-(4-cyanophenyl)phenyl]propanoic acid Chemical compound C([C@@H](C(=O)O)NC(=O)C1N(CC2=CC=3O[C@H](C(=O)NC=3C=C2C1)C=1C=CC(OCC=2C=C(Cl)C(Cl)=CC=2)=CC=1)C(=O)C=1C=CC=CC=1)C(C=C1)=CC=C1C1=CC=C(C#N)C=C1 DLIDOWKXQKFZIN-IKABJYOBSA-N 0.000 claims 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims 2
- 125000000732 arylene group Chemical group 0.000 claims 2
- 125000002541 furyl group Chemical group 0.000 claims 2
- 125000005549 heteroarylene group Chemical group 0.000 claims 2
- 125000002883 imidazolyl group Chemical group 0.000 claims 2
- 125000000842 isoxazolyl group Chemical group 0.000 claims 2
- 125000001624 naphthyl group Chemical group 0.000 claims 2
- 125000002971 oxazolyl group Chemical group 0.000 claims 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 2
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims 2
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims 2
- 125000000335 thiazolyl group Chemical group 0.000 claims 2
- KOKVGGCITQETON-IKABJYOBSA-N (2s)-2-[[(3s)-3-[4-[(3,4-dichlorophenyl)methoxy]phenyl]-2-oxo-7-(pyridin-2-ylmethyl)-1,6,8,9-tetrahydropyrido[4,3-g][1,4]benzoxazine-8-carbonyl]amino]-3-[4-(4-methylphenyl)phenyl]propanoic acid Chemical compound C1=CC(C)=CC=C1C(C=C1)=CC=C1C[C@@H](C(O)=O)NC(=O)C1N(CC=2N=CC=CC=2)CC2=CC(O[C@H](C(=O)N3)C=4C=CC(OCC=5C=C(Cl)C(Cl)=CC=5)=CC=4)=C3C=C2C1 KOKVGGCITQETON-IKABJYOBSA-N 0.000 claims 1
- SIOLMVPINQYTKK-OWCTVJAMSA-N (2s)-2-[[(3s)-7-[(2-cyanophenyl)methyl]-3-[4-[(3,4-dichlorophenyl)methoxy]phenyl]-2-oxo-1,6,8,9-tetrahydropyrido[4,3-g][1,4]benzoxazine-8-carbonyl]amino]-3-[4-(4-cyanophenyl)phenyl]propanoic acid Chemical compound C([C@@H](C(=O)O)NC(=O)C1N(CC2=CC=3O[C@H](C(=O)NC=3C=C2C1)C=1C=CC(OCC=2C=C(Cl)C(Cl)=CC=2)=CC=1)CC=1C(=CC=CC=1)C#N)C(C=C1)=CC=C1C1=CC=C(C#N)C=C1 SIOLMVPINQYTKK-OWCTVJAMSA-N 0.000 claims 1
- OYDVNBOHYSQJHI-NWUFIKPXSA-N (2s)-2-[[(3s)-7-benzoyl-3-[4-[(3,4-dichlorophenyl)methoxy]phenyl]-2-oxo-1,6,8,9-tetrahydropyrido[4,3-g][1,4]benzoxazine-8-carbonyl]amino]-3-(4-pyridin-4-yloxyphenyl)propanoic acid Chemical compound C([C@@H](C(=O)O)NC(=O)C1N(CC2=CC=3O[C@H](C(=O)NC=3C=C2C1)C=1C=CC(OCC=2C=C(Cl)C(Cl)=CC=2)=CC=1)C(=O)C=1C=CC=CC=1)C(C=C1)=CC=C1OC1=CC=NC=C1 OYDVNBOHYSQJHI-NWUFIKPXSA-N 0.000 claims 1
- VBWXZTKGNUDUGJ-NWUFIKPXSA-N (2s)-2-[[(3s)-7-benzoyl-3-[4-[(3,4-dichlorophenyl)methoxy]phenyl]-2-oxo-1,6,8,9-tetrahydropyrido[4,3-g][1,4]benzoxazine-8-carbonyl]amino]-3-(4-pyridin-4-ylphenyl)propanoic acid Chemical compound C([C@@H](C(=O)O)NC(=O)C1N(CC2=CC=3O[C@H](C(=O)NC=3C=C2C1)C=1C=CC(OCC=2C=C(Cl)C(Cl)=CC=2)=CC=1)C(=O)C=1C=CC=CC=1)C(C=C1)=CC=C1C1=CC=NC=C1 VBWXZTKGNUDUGJ-NWUFIKPXSA-N 0.000 claims 1
- SSKHVNIFXWOMPC-QGONPRBCSA-N (2s)-2-[[(3s)-7-benzoyl-3-[4-[(3,4-dichlorophenyl)methoxy]phenyl]-2-oxo-1,6,8,9-tetrahydropyrido[4,3-g][1,4]benzoxazine-8-carbonyl]amino]-3-[4-(4-chlorophenyl)phenyl]propanoic acid Chemical compound C([C@@H](C(=O)O)NC(=O)C1N(CC2=CC=3O[C@H](C(=O)NC=3C=C2C1)C=1C=CC(OCC=2C=C(Cl)C(Cl)=CC=2)=CC=1)C(=O)C=1C=CC=CC=1)C(C=C1)=CC=C1C1=CC=C(Cl)C=C1 SSKHVNIFXWOMPC-QGONPRBCSA-N 0.000 claims 1
- XBULYOFWSBMYQI-IKABJYOBSA-N (2s)-2-[[(3s)-7-benzoyl-3-[4-[(3-chlorophenyl)methoxy]phenyl]-2-oxo-1,6,8,9-tetrahydropyrido[4,3-g][1,4]benzoxazine-8-carbonyl]amino]-3-[4-(4-cyanophenyl)phenyl]propanoic acid Chemical compound C([C@@H](C(=O)O)NC(=O)C1N(CC2=CC=3O[C@H](C(=O)NC=3C=C2C1)C=1C=CC(OCC=2C=C(Cl)C=CC=2)=CC=1)C(=O)C=1C=CC=CC=1)C(C=C1)=CC=C1C1=CC=C(C#N)C=C1 XBULYOFWSBMYQI-IKABJYOBSA-N 0.000 claims 1
- KFKFBIJXIWGJGQ-IKABJYOBSA-N (2s)-2-[[(3s)-7-benzoyl-3-[4-[(4-chlorophenyl)methoxy]phenyl]-2-oxo-1,6,8,9-tetrahydropyrido[4,3-g][1,4]benzoxazine-8-carbonyl]amino]-3-[4-(4-cyanophenyl)phenyl]propanoic acid Chemical compound C([C@@H](C(=O)O)NC(=O)C1N(CC2=CC=3O[C@H](C(=O)NC=3C=C2C1)C=1C=CC(OCC=2C=CC(Cl)=CC=2)=CC=1)C(=O)C=1C=CC=CC=1)C(C=C1)=CC=C1C1=CC=C(C#N)C=C1 KFKFBIJXIWGJGQ-IKABJYOBSA-N 0.000 claims 1
- SZYOKIBLTVRFTM-NWUFIKPXSA-N (2s)-2-[[(3s)-7-benzoyl-3-[4-[(5,6-dichloropyridin-3-yl)methoxy]phenyl]-2-oxo-1,6,8,9-tetrahydropyrido[4,3-g][1,4]benzoxazine-8-carbonyl]amino]-3-[4-(4-cyanophenyl)phenyl]propanoic acid Chemical compound C([C@@H](C(=O)O)NC(=O)C1N(CC2=CC=3O[C@H](C(=O)NC=3C=C2C1)C=1C=CC(OCC=2C=C(Cl)C(Cl)=NC=2)=CC=1)C(=O)C=1C=CC=CC=1)C(C=C1)=CC=C1C1=CC=C(C#N)C=C1 SZYOKIBLTVRFTM-NWUFIKPXSA-N 0.000 claims 1
- GRUBZXUBGMDTOV-IKABJYOBSA-N (2s)-2-[[(3s)-7-benzoyl-3-[4-[[4-chloro-3-(trifluoromethyl)phenyl]methoxy]phenyl]-2-oxo-1,6,8,9-tetrahydropyrido[4,3-g][1,4]benzoxazine-8-carbonyl]amino]-3-[4-(4-cyanophenyl)phenyl]propanoic acid Chemical compound C([C@@H](C(=O)O)NC(=O)C1N(CC2=CC=3O[C@H](C(=O)NC=3C=C2C1)C=1C=CC(OCC=2C=C(C(Cl)=CC=2)C(F)(F)F)=CC=1)C(=O)C=1C=CC=CC=1)C(C=C1)=CC=C1C1=CC=C(C#N)C=C1 GRUBZXUBGMDTOV-IKABJYOBSA-N 0.000 claims 1
- ZKQGQYVAMWKLIU-MESGABPPSA-N (2s)-2-[[(3s)-7-benzyl-3-[4-[(3,4-dichlorophenyl)methoxy]phenyl]-2-oxo-1,6,8,9-tetrahydropyrido[4,3-g][1,4]benzoxazine-8-carbonyl]amino]-3-[4-(4-cyanophenyl)phenyl]propanoic acid Chemical compound C([C@@H](C(=O)O)NC(=O)C1N(CC2=CC=3O[C@H](C(=O)NC=3C=C2C1)C=1C=CC(OCC=2C=C(Cl)C(Cl)=CC=2)=CC=1)CC=1C=CC=CC=1)C(C=C1)=CC=C1C1=CC=C(C#N)C=C1 ZKQGQYVAMWKLIU-MESGABPPSA-N 0.000 claims 1
- WWEDIOLJVSBYRU-IKABJYOBSA-N (2s)-3-[4-(4-cyanophenyl)phenyl]-2-[[(3s)-3-[4-[(3,4-dichlorophenyl)methoxy]phenyl]-2-oxo-7-(pyridin-2-ylmethyl)-1,6,8,9-tetrahydropyrido[4,3-g][1,4]benzoxazine-8-carbonyl]amino]propanoic acid Chemical compound C([C@@H](C(=O)O)NC(=O)C1N(CC2=CC=3O[C@H](C(=O)NC=3C=C2C1)C=1C=CC(OCC=2C=C(Cl)C(Cl)=CC=2)=CC=1)CC=1N=CC=CC=1)C(C=C1)=CC=C1C1=CC=C(C#N)C=C1 WWEDIOLJVSBYRU-IKABJYOBSA-N 0.000 claims 1
- WRBATKFEIYHBCC-QGONPRBCSA-N (2s)-3-[4-(4-cyanophenyl)phenyl]-2-[[(3s)-3-[4-[(3,4-dichlorophenyl)methoxy]phenyl]-2-oxo-7-(pyridine-3-carbonyl)-1,6,8,9-tetrahydropyrido[4,3-g][1,4]benzoxazine-8-carbonyl]amino]propanoic acid Chemical compound C([C@@H](C(=O)O)NC(=O)C1N(CC2=CC=3O[C@H](C(=O)NC=3C=C2C1)C=1C=CC(OCC=2C=C(Cl)C(Cl)=CC=2)=CC=1)C(=O)C=1C=NC=CC=1)C(C=C1)=CC=C1C1=CC=C(C#N)C=C1 WRBATKFEIYHBCC-QGONPRBCSA-N 0.000 claims 1
- QUIJNNGHGSQUNF-MESGABPPSA-N (2s)-3-[4-(4-cyanophenyl)phenyl]-2-[[(3s)-3-[4-[(3,4-dichlorophenyl)methoxy]phenyl]-7-(4-methoxybenzoyl)-2-oxo-1,6,8,9-tetrahydropyrido[4,3-g][1,4]benzoxazine-8-carbonyl]amino]propanoic acid Chemical compound C1=CC(OC)=CC=C1C(=O)N1C(C(=O)N[C@@H](CC=2C=CC(=CC=2)C=2C=CC(=CC=2)C#N)C(O)=O)CC2=CC(NC(=O)[C@@H](O3)C=4C=CC(OCC=5C=C(Cl)C(Cl)=CC=5)=CC=4)=C3C=C2C1 QUIJNNGHGSQUNF-MESGABPPSA-N 0.000 claims 1
- YJBNIMLOCGOANK-UXEWHZQTSA-N (2s)-3-[4-(4-cyanophenyl)phenyl]-2-[[(3s)-3-[4-[(3,4-dichlorophenyl)methoxy]phenyl]-7-(furan-2-carbonyl)-2-oxo-1,6,8,9-tetrahydropyrido[4,3-g][1,4]benzoxazine-8-carbonyl]amino]propanoic acid Chemical compound C([C@@H](C(=O)O)NC(=O)C1N(CC2=CC=3O[C@H](C(=O)NC=3C=C2C1)C=1C=CC(OCC=2C=C(Cl)C(Cl)=CC=2)=CC=1)C(=O)C=1OC=CC=1)C(C=C1)=CC=C1C1=CC=C(C#N)C=C1 YJBNIMLOCGOANK-UXEWHZQTSA-N 0.000 claims 1
- YKJKZJCVIAUGMO-OWCTVJAMSA-N (2s)-3-[4-(4-cyanophenyl)phenyl]-2-[[(3s)-3-[4-[(3,4-dichlorophenyl)methoxy]phenyl]-7-[(2-methylphenyl)methyl]-2-oxo-1,6,8,9-tetrahydropyrido[4,3-g][1,4]benzoxazine-8-carbonyl]amino]propanoic acid Chemical compound CC1=CC=CC=C1CN1C(C(=O)N[C@@H](CC=2C=CC(=CC=2)C=2C=CC(=CC=2)C#N)C(O)=O)CC2=CC(NC(=O)[C@@H](O3)C=4C=CC(OCC=5C=C(Cl)C(Cl)=CC=5)=CC=4)=C3C=C2C1 YKJKZJCVIAUGMO-OWCTVJAMSA-N 0.000 claims 1
- VQFUQWSLCGKJHB-PZKPWUIHSA-N (2s)-3-[4-(4-cyanophenyl)phenyl]-2-[[(3s)-3-[4-[(3,4-dichlorophenyl)methoxy]phenyl]-7-[(2-methylpropan-2-yl)oxycarbonyl]-2-oxo-1,6,8,9-tetrahydropyrido[4,3-g][1,4]benzoxazine-8-carbonyl]amino]propanoic acid Chemical compound C([C@H](NC(=O)C1CC2=CC=3NC(=O)[C@@H](OC=3C=C2CN1C(=O)OC(C)(C)C)C=1C=CC(OCC=2C=C(Cl)C(Cl)=CC=2)=CC=1)C(O)=O)C(C=C1)=CC=C1C1=CC=C(C#N)C=C1 VQFUQWSLCGKJHB-PZKPWUIHSA-N 0.000 claims 1
- WEGSFCATZSEMCW-IKABJYOBSA-N (2s)-3-[4-(4-cyanophenyl)phenyl]-2-[[(3s)-7-(cyclohexanecarbonyl)-3-[4-[(3,4-dichlorophenyl)methoxy]phenyl]-2-oxo-1,6,8,9-tetrahydropyrido[4,3-g][1,4]benzoxazine-8-carbonyl]amino]propanoic acid Chemical compound C([C@@H](C(=O)O)NC(=O)C1N(CC2=CC=3O[C@H](C(=O)NC=3C=C2C1)C=1C=CC(OCC=2C=C(Cl)C(Cl)=CC=2)=CC=1)C(=O)C1CCCCC1)C(C=C1)=CC=C1C1=CC=C(C#N)C=C1 WEGSFCATZSEMCW-IKABJYOBSA-N 0.000 claims 1
- IHEXKIGTDCAISA-QGONPRBCSA-N (2s)-3-[4-(4-cyanophenyl)phenyl]-2-[[(3s)-7-(cyclopentanecarbonyl)-3-[4-[(3,4-dichlorophenyl)methoxy]phenyl]-2-oxo-1,6,8,9-tetrahydropyrido[4,3-g][1,4]benzoxazine-8-carbonyl]amino]propanoic acid Chemical compound C([C@@H](C(=O)O)NC(=O)C1N(CC2=CC=3O[C@H](C(=O)NC=3C=C2C1)C=1C=CC(OCC=2C=C(Cl)C(Cl)=CC=2)=CC=1)C(=O)C1CCCC1)C(C=C1)=CC=C1C1=CC=C(C#N)C=C1 IHEXKIGTDCAISA-QGONPRBCSA-N 0.000 claims 1
- JXKDPYPAECSZDB-WOXDSQMTSA-N (2s)-3-[4-(4-cyanophenyl)phenyl]-2-[[(3s)-7-cyclobutyl-3-[4-[(3,4-dichlorophenyl)methoxy]phenyl]-1-methyl-2-oxo-8,9-dihydro-6h-pyrido[4,3-g][1,4]benzoxazine-8-carbonyl]amino]propanoic acid Chemical compound O([C@H](C(=O)N(C1=CC=2CC3C(=O)N[C@@H](CC=4C=CC(=CC=4)C=4C=CC(=CC=4)C#N)C(O)=O)C)C=4C=CC(OCC=5C=C(Cl)C(Cl)=CC=5)=CC=4)C1=CC=2CN3C1CCC1 JXKDPYPAECSZDB-WOXDSQMTSA-N 0.000 claims 1
- XIQGCFQXNOOKPY-HVMGPMHDSA-N (2s)-3-[4-(4-cyanophenyl)phenyl]-2-[[(3s)-7-cyclohexyl-3-[4-[(3,4-dichlorophenyl)methoxy]phenyl]-1-methyl-2-oxo-8,9-dihydro-6h-pyrido[4,3-g][1,4]benzoxazine-8-carbonyl]amino]propanoic acid Chemical compound O([C@H](C(=O)N(C1=CC=2CC3C(=O)N[C@@H](CC=4C=CC(=CC=4)C=4C=CC(=CC=4)C#N)C(O)=O)C)C=4C=CC(OCC=5C=C(Cl)C(Cl)=CC=5)=CC=4)C1=CC=2CN3C1CCCCC1 XIQGCFQXNOOKPY-HVMGPMHDSA-N 0.000 claims 1
- NOINZHWZSLBLIX-SJFOEYAOSA-N (2s)-3-[4-(4-cyanophenyl)phenyl]-2-[[(3s)-7-cyclopentyl-3-[4-[(3,4-dichlorophenyl)methoxy]phenyl]-1-methyl-2-oxo-8,9-dihydro-6h-pyrido[4,3-g][1,4]benzoxazine-8-carbonyl]amino]propanoic acid Chemical compound O([C@H](C(=O)N(C1=CC=2CC3C(=O)N[C@@H](CC=4C=CC(=CC=4)C=4C=CC(=CC=4)C#N)C(O)=O)C)C=4C=CC(OCC=5C=C(Cl)C(Cl)=CC=5)=CC=4)C1=CC=2CN3C1CCCC1 NOINZHWZSLBLIX-SJFOEYAOSA-N 0.000 claims 1
- MYTKCZRCSJLNLN-HSFMBMOHSA-N (3s)-8-[[(1s)-1-carboxy-2-[4-(4-cyanophenyl)phenyl]ethyl]carbamoyl]-3-[4-[(3,4-dichlorophenyl)methoxy]phenyl]-2-oxo-1,6,8,9-tetrahydropyrido[4,3-g][1,4]benzoxazine-7-carboxylic acid Chemical compound C([C@@H](C(=O)O)NC(=O)C1N(CC2=CC=3O[C@H](C(=O)NC=3C=C2C1)C=1C=CC(OCC=2C=C(Cl)C(Cl)=CC=2)=CC=1)C(O)=O)C(C=C1)=CC=C1C1=CC=C(C#N)C=C1 MYTKCZRCSJLNLN-HSFMBMOHSA-N 0.000 claims 1
- 101100240518 Caenorhabditis elegans nhr-12 gene Proteins 0.000 claims 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims 1
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/04—Ortho-condensed systems
-
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| PCT/US2009/036333 WO2009111700A2 (en) | 2008-03-07 | 2009-03-06 | Oxadiazoanthracene compounds for the treatment of diabetes |
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| ZA (1) | ZA201006367B (https=) |
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| EA018225B1 (ru) | 2008-03-07 | 2013-06-28 | Транстек Фарма, Инк. | Соединения оксадиазоантрацена для лечения диабета |
| CN102378574B (zh) | 2009-03-30 | 2013-11-20 | 转化技术制药公司 | 取代的偶氮蒽衍生物、药物组合物及其使用方法 |
| WO2011107494A1 (de) | 2010-03-03 | 2011-09-09 | Sanofi | Neue aromatische glykosidderivate, diese verbindungen enthaltende arzneimittel und deren verwendung |
| DE102010015123A1 (de) | 2010-04-16 | 2011-10-20 | Sanofi-Aventis Deutschland Gmbh | Benzylamidische Diphenylazetidinone, diese Verbindungen enthaltende Arzneimittel und deren Verwendung |
| US8530413B2 (en) | 2010-06-21 | 2013-09-10 | Sanofi | Heterocyclically substituted methoxyphenyl derivatives with an oxo group, processes for preparation thereof and use thereof as medicaments |
| TW201215387A (en) | 2010-07-05 | 2012-04-16 | Sanofi Aventis | Spirocyclically substituted 1,3-propane dioxide derivatives, processes for preparation thereof and use thereof as a medicament |
| TW201221505A (en) | 2010-07-05 | 2012-06-01 | Sanofi Sa | Aryloxyalkylene-substituted hydroxyphenylhexynoic acids, process for preparation thereof and use thereof as a medicament |
| TW201215388A (en) | 2010-07-05 | 2012-04-16 | Sanofi Sa | (2-aryloxyacetylamino)phenylpropionic acid derivatives, processes for preparation thereof and use thereof as medicaments |
| NZ611529A (en) | 2010-12-23 | 2015-06-26 | Pfizer | Glucagon receptor modulators |
| WO2012096824A1 (en) * | 2011-01-12 | 2012-07-19 | Transtech Pharma, Inc. | Phenylglyoxylic acid derivatives and their preparation and use |
| WO2012107850A1 (en) | 2011-02-08 | 2012-08-16 | Pfizer Inc. | Glucagon receptor modulator |
| US8927577B2 (en) | 2011-07-22 | 2015-01-06 | Pfizer Inc. | Quinolinyl glucagon receptor modulators |
| EP2567959B1 (en) | 2011-09-12 | 2014-04-16 | Sanofi | 6-(4-hydroxy-phenyl)-3-styryl-1h-pyrazolo[3,4-b]pyridine-4-carboxylic acid amide derivatives as kinase inhibitors |
| WO2013037390A1 (en) | 2011-09-12 | 2013-03-21 | Sanofi | 6-(4-hydroxy-phenyl)-3-styryl-1h-pyrazolo[3,4-b]pyridine-4-carboxylic acid amide derivatives as kinase inhibitors |
| WO2013045413A1 (en) | 2011-09-27 | 2013-04-04 | Sanofi | 6-(4-hydroxy-phenyl)-3-alkyl-1h-pyrazolo[3,4-b]pyridine-4-carboxylic acid amide derivatives as kinase inhibitors |
| EA201491749A1 (ru) | 2012-03-22 | 2015-01-30 | ТРАНСТЕК ФАРМА, ЭлЭлСи | Трис-(гидроксиметил)аминометановые соли низкомолекулярного агониста glp1r, их фармацевтические композиции и применение |
| US20150297573A1 (en) | 2012-10-24 | 2015-10-22 | INSERM (Institut National de la Santé et de la Recherche Médicale) | TPL2 KINASE INHIBITORS FOR PREVENTING OR TREATING DIABETES AND FOR PROMOTING Beta-CELL SURVIVAL |
| AU2014207748B2 (en) * | 2013-01-17 | 2018-10-11 | Vtv Therapeutics Llc | Combinations of a GLP1R agonist and metformin and use thereof for the treatment of type 2 diabetes and other disorders |
| CA2955836C (en) * | 2014-07-25 | 2023-02-14 | Celgene International Ii Sarl | Glp-1 receptor modulators |
| US10426818B2 (en) | 2015-03-24 | 2019-10-01 | Inserm (Institut National De La Sante Et De La Recherche Medicale) | Method and pharmaceutical composition for use in the treatment of diabetes |
| JOP20190060A1 (ar) | 2016-09-26 | 2019-03-26 | Chugai Pharmaceutical Co Ltd | مشتق بيرازولو بيريدين له تأثير مساعد لمستقبل glp-1 |
| TW201925204A (zh) * | 2017-11-22 | 2019-07-01 | 日商第一三共股份有限公司 | 稠合三環化合物 |
| MX2020008387A (es) | 2018-05-08 | 2020-12-11 | Vtv Therapeutics Llc | Usos terapeuticos de agonistas glp1r. |
| MA54555A (fr) | 2018-11-22 | 2021-09-29 | Qilu Regor Therapeutics Inc | Agonistes de glp-1r et leurs utilisations |
| EP3953344A4 (en) * | 2019-04-12 | 2023-08-09 | Qilu Regor Therapeutics Inc. | GLP-IR AGONISTS AND THEIR USES |
| EP4048664A1 (en) | 2019-10-25 | 2022-08-31 | Gilead Sciences, Inc. | Glp-1r modulating compounds |
| US12459954B2 (en) | 2020-04-01 | 2025-11-04 | Hangzhou Zhongmei Huadong Pharmaceutical Co., Ltd. | Crystalline form a of GLP-1 receptor agonist and preparation method therefor |
| JP2023528726A (ja) | 2020-04-01 | 2023-07-06 | ハンジョウ ジョンメイ フアドン ファーマシューティカル シーオー．，エルティーディー． | Ｇｌｐ１ｒアゴニスト遊離塩基の薬学的に許容される酸塩類およびその調製法 |
| TW202144340A (zh) | 2020-04-03 | 2021-12-01 | 大陸商江蘇恆瑞醫藥股份有限公司 | 稠合咪唑類衍生物、其製備方法及其在醫藥上的應用 |
| TW202210461A (zh) * | 2020-05-28 | 2022-03-16 | 中國大陸商杭州中美華東製藥有限公司 | 一種（ｓ）—２—胺基—３—（４—（２，３—二甲基吡啶—４—基）苯基）丙酸甲酯二酸鹽的製備方法 |
| EP4159737A4 (en) * | 2020-05-28 | 2024-10-09 | Hangzhou Zhongmeihuadong Pharmaceutical Co., Ltd. | METHOD FOR PREPARING A GLP-1 RECEPTOR AGONIST-FREE BASE |
| CA3188891A1 (en) | 2020-09-01 | 2022-01-13 | Fanglong Yang | Fused imidazole derivative, preparation method therefor, and medical use thereof |
| WO2022078152A1 (zh) | 2020-10-12 | 2022-04-21 | 杭州中美华东制药有限公司 | 苯并咪唑酮类glp-1受体激动剂及其用途 |
| CN116710446B (zh) | 2020-10-14 | 2024-10-18 | 上海齐鲁锐格医药研发有限公司 | Glp-1r激动剂的晶型及其用途 |
| EP4247804A1 (en) | 2020-11-20 | 2023-09-27 | Gilead Sciences, Inc. | Polyheterocyclic glp-1 r modulating compounds |
| MX2023006186A (es) | 2020-11-27 | 2023-08-07 | Shenzhen Salubris Pharm Co Ltd | Derivado de benzimidazol y método de preparación del mismo y uso médico del mismo. |
| US20240208952A1 (en) | 2021-03-22 | 2024-06-27 | Hangzhou Zhongmeihuadong Pharmaceutical Co., Ltd. | Thiophene glp-1 receptor agonist and use thereof |
| JP7772778B2 (ja) | 2021-03-24 | 2025-11-18 | 塩野義製薬株式会社 | 縮合環を有するｇｌｐ－１受容体作動薬を含有する医薬組成物 |
| IL306110A (en) | 2021-04-21 | 2023-11-01 | Gilead Sciences Inc | Carboxy-benzimidazole glp-1r modulating compounds |
| CN117500808B (zh) * | 2021-06-17 | 2026-03-06 | 杭州中美华东制药有限公司 | 蒽类化合物、其制备方法和医药用途 |
| IL309235A (en) | 2021-06-24 | 2024-02-01 | Hangzhou Zhongmeihuadong Pharmaceutical Co Ltd | Glp-1 receptor agonist and composition and use thereof |
| CN115521320B (zh) * | 2021-06-25 | 2023-09-05 | 沈阳兴齐眼药股份有限公司 | 一种制备普拉洛芬的方法 |
| EP4592285A1 (en) | 2022-09-22 | 2025-07-30 | Shionogi & Co., Ltd. | Fused ring compound having glp-1 receptor agonist effect |
| CN120981457A (zh) | 2023-09-14 | 2025-11-18 | 歌礼制药(中国)有限公司 | Glp-1r激动剂及其治疗方法 |
| TW202521534A (zh) | 2023-11-24 | 2025-06-01 | 香港商歌禮製藥(中國)有限公司 | Glp-1r 激動劑及其治療方法 |
| WO2025158275A1 (en) | 2024-01-24 | 2025-07-31 | Pfizer Inc. | Combination therapy using glucose-dependent insulinotropic polypeptide receptor antagonist compounds and glp-1 receptor agonist compounds |
| TW202600132A (zh) | 2024-03-08 | 2026-01-01 | 美商安尼波那生物公司 | 用於治療肥胖症及提高減重之方法 |
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| JPS6345270A (ja) * | 1986-02-11 | 1988-02-26 | Takeda Chem Ind Ltd | １，４−ベンゾオキサジン誘導体，その製造法およびそれを含有する医薬用組成物 |
| EP0233728A1 (en) * | 1986-02-11 | 1987-08-26 | Takeda Chemical Industries, Ltd. | 1,4-Benzoxazine derivatives their production and use |
| WO1997012853A1 (en) * | 1995-10-06 | 1997-04-10 | Ligand Pharmaceuticals Incorporated | Dimer-selective rxr modulators and methods for their use |
| WO2000042026A1 (en) * | 1999-01-15 | 2000-07-20 | Novo Nordisk A/S | Non-peptide glp-1 agonists |
| WO2001040192A1 (en) * | 1999-12-03 | 2001-06-07 | Kyoto Pharmaceutical Industries, Ltd. | Novel heterocyclic compounds and salts thereof and medicinal use of the same |
| EP1125925A1 (en) * | 2000-02-15 | 2001-08-22 | Applied Research Systems ARS Holding N.V. | Amine derivatives for the treatment of apoptosis |
| US20050222036A1 (en) * | 2000-08-24 | 2005-10-06 | Thomas Jefferson University | Peptide compositions with effects on blood glucose |
| ES2327737T3 (es) * | 2003-03-26 | 2009-11-03 | Actelion Pharmaceuticals Ltd. | Derivados de tetrahidroisoquinolil acetamida para uso como antagonistas de receptores de orexina. |
| EA018225B1 (ru) | 2008-03-07 | 2013-06-28 | Транстек Фарма, Инк. | Соединения оксадиазоантрацена для лечения диабета |
| JP2013530963A (ja) | 2010-06-09 | 2013-08-01 | レセプトス インコーポレイテッド | 新規のｇｌｐ−１受容体安定化薬および調節薬 |
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