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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- Health & Medical Sciences (AREA)
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| AU2009221722B2 (en) * | 2008-03-07 | 2014-12-18 | Vtv Therapeutics Llc | Oxadiazoanthracene compounds for the treatment of diabetes |
| EA023430B1 (ru) | 2009-03-30 | 2016-06-30 | виТиви ТЕРАПЬЮТИКС ЭлЭлСи | Замещенные производные азоантрацена, фармацевтические композиции и способы их применения |
| 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 |
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| 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 |
| RU2013127611A (ru) | 2010-12-23 | 2015-01-27 | Пфайзер Инк. | Модуляторы глюкагонового рецептора |
| WO2012096824A1 (en) * | 2011-01-12 | 2012-07-19 | Transtech Pharma, Inc. | Phenylglyoxylic acid derivatives and their preparation and use |
| MX2013009140A (es) | 2011-02-08 | 2013-10-01 | Pfizer | Moduladores del receptor de glucagon. |
| RU2013157388A (ru) | 2011-07-22 | 2015-08-27 | Пфайзер Инк. | Хинолинильные модуляторы глюкагонового рецептора |
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| 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 |
| 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 |
| JP2015510947A (ja) * | 2012-03-22 | 2015-04-13 | トランステック・ファーマ，エルエルシー | 小分子ｇｌｐ１ｒアゴニストのトリス（ヒドロキシメチル）アミノメタン塩ならびにその医薬組成物および使用 |
| IN2015DN03795A (enExample) | 2012-10-24 | 2015-10-02 | Inserm Inst Nat De La Santé Et De La Rech Médicale | |
| CN104968341B (zh) | 2013-01-17 | 2020-06-09 | Vtv治疗有限责任公司 | Glp1r激动剂和二甲双胍的组合及其在制备治疗2型糖尿病和其他障碍的药物中的用途 |
| 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 |
| KR20210005843A (ko) | 2018-05-08 | 2021-01-15 | 브이티브이 테라퓨틱스 엘엘씨 | Glp1r 작용제의 치료적 용도 |
| EA202191432A1 (ru) | 2018-11-22 | 2021-10-14 | Цилу Регор Терапьютикс Инк. | Агонисты glp-1r и их применения |
| WO2020207474A1 (en) * | 2019-04-12 | 2020-10-15 | Qilu Regor Therapeutics Inc. | Glp-1r agonists and uses thereof |
| CN115315426B (zh) | 2020-04-01 | 2023-12-12 | 杭州中美华东制药有限公司 | Glp-1受体激动剂游离碱的药学上可接受的酸式盐及其制备方法 |
| EP4130005A4 (en) | 2020-04-01 | 2024-04-24 | Hangzhou Zhongmeihuadong Pharmaceutical Co., Ltd. | CRYSTALLINE FORM A OF A GLP-1 RECEPTOR AGONIST AND METHOD OF MANUFACTURING THEREOF |
| 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 |
| JP2023539584A (ja) | 2020-09-01 | 2023-09-15 | 江蘇恒瑞医薬股▲ふん▼有限公司 | 縮合イミダゾール誘導体、その調製方法及びその医薬的応用 |
| 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 |
| US20230382899A1 (en) * | 2020-10-14 | 2023-11-30 | Qilu Regor Therapeutics Inc. | Crystal forms of glp-1r agonists and uses thereof |
| EP4247804A1 (en) | 2020-11-20 | 2023-09-27 | Gilead Sciences, Inc. | Polyheterocyclic glp-1 r modulating compounds |
| CA3200245A1 (en) | 2020-11-27 | 2022-06-02 | Junjun Wu | Benzimidazole derivative and preparation method therefor and medical use thereof |
| CN116940561A (zh) | 2021-03-22 | 2023-10-24 | 杭州中美华东制药有限公司 | 噻吩类glp-1受体激动剂及其用途 |
| EP4317145A4 (en) | 2021-03-24 | 2025-03-12 | Shionogi & Co., Ltd | Pharmaceutical composition containing glp-1 receptor agonist having fused ring |
| WO2022262615A1 (zh) * | 2021-06-17 | 2022-12-22 | 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 |
| AU2022300055A1 (en) | 2021-06-24 | 2024-01-18 | 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 |
| WO2024063143A1 (ja) | 2022-09-22 | 2024-03-28 | 塩野義製薬株式会社 | Ｇｌｐ－１受容体アゴニスト作用を有する縮合環化合物 |
| 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 |
| US12291530B1 (en) | 2023-11-24 | 2025-05-06 | Ascletis Pharma (China) Co., Limited | GLP-1R agonist and therapeutic method thereof |
| 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 |
| WO2025189141A1 (en) | 2024-03-08 | 2025-09-12 | Annapurna Bio, Inc. | Methods for treating obesity and increasing weight loss |
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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 |
| EP0873295B1 (en) * | 1995-10-06 | 2003-04-02 | Ligand Pharmaceuticals, Inc. | Dimer-selective rxr modulators and methods for their use |
| EP1147094A1 (en) * | 1999-01-15 | 2001-10-24 | 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 |
| ATE435210T1 (de) * | 2003-03-26 | 2009-07-15 | Actelion Pharmaceuticals Ltd | Tetrahydroisochinolylacetamidderivate zur verwendung als orexinrezeptorantagonisten |
| AU2009221722B2 (en) * | 2008-03-07 | 2014-12-18 | Vtv Therapeutics Llc | Oxadiazoanthracene compounds for the treatment of diabetes |
| EP2579888A2 (en) | 2010-06-09 | 2013-04-17 | Receptos, Inc. | Novel glp-1 receptor stabilizers and modulators |
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2009
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- 2009-03-06 WO PCT/US2009/036333 patent/WO2009111700A2/en not_active Ceased
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- 2009-03-06 BR BRPI0910282-5A patent/BRPI0910282A2/pt not_active Application Discontinuation
- 2009-03-06 KR KR1020107020688A patent/KR101616737B1/ko not_active Expired - Fee Related
- 2009-03-06 EA EA201071045A patent/EA018225B1/ru not_active IP Right Cessation
- 2009-03-06 DK DK09718287.7T patent/DK2262364T3/en active
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- 2009-03-06 ES ES09718287T patent/ES2567451T3/es active Active
- 2009-03-06 JP JP2010549910A patent/JP5382952B2/ja active Active
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- 2009-03-06 EP EP09718287.7A patent/EP2262364B1/en active Active
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2010
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