TWI763733B - 作為αV整合素抑制劑之3-經取代丙酸 - Google Patents
作為αV整合素抑制劑之3-經取代丙酸Info
- Publication number
- TWI763733B TWI763733B TW106138533A TW106138533A TWI763733B TW I763733 B TWI763733 B TW I763733B TW 106138533 A TW106138533 A TW 106138533A TW 106138533 A TW106138533 A TW 106138533A TW I763733 B TWI763733 B TW I763733B
- Authority
- TW
- Taiwan
- Prior art keywords
- tetrahydro
- propionic acid
- naphthyridin
- propyl
- pyrazol
- Prior art date
Links
- 108010044426 integrins Proteins 0.000 title abstract description 26
- 102000006495 integrins Human genes 0.000 title abstract description 26
- 239000003112 inhibitor Substances 0.000 title description 15
- 150000004672 propanoic acids Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 204
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 55
- 150000003839 salts Chemical class 0.000 claims abstract description 44
- 201000010099 disease Diseases 0.000 claims abstract description 25
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 24
- 206010016654 Fibrosis Diseases 0.000 claims abstract description 21
- 230000004761 fibrosis Effects 0.000 claims abstract description 19
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 198
- -1 cyano, hydroxyl Chemical group 0.000 claims description 129
- 235000019260 propionic acid Nutrition 0.000 claims description 98
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims description 93
- 125000000623 heterocyclic group Chemical group 0.000 claims description 75
- 125000003118 aryl group Chemical group 0.000 claims description 59
- 125000000217 alkyl group Chemical group 0.000 claims description 58
- 229910052739 hydrogen Inorganic materials 0.000 claims description 52
- 125000004452 carbocyclyl group Chemical group 0.000 claims description 46
- 239000001257 hydrogen Substances 0.000 claims description 46
- 125000001072 heteroaryl group Chemical group 0.000 claims description 38
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 38
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 37
- 125000003545 alkoxy group Chemical group 0.000 claims description 36
- 125000001188 haloalkyl group Chemical group 0.000 claims description 33
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 28
- FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 claims description 27
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 26
- 125000005843 halogen group Chemical group 0.000 claims description 24
- 208000008338 non-alcoholic fatty liver disease Diseases 0.000 claims description 22
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 21
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 20
- 125000004429 atom Chemical group 0.000 claims description 16
- 208000036971 interstitial lung disease 2 Diseases 0.000 claims description 16
- 229910052717 sulfur Inorganic materials 0.000 claims description 16
- 201000009794 Idiopathic Pulmonary Fibrosis Diseases 0.000 claims description 15
- 206010053219 non-alcoholic steatohepatitis Diseases 0.000 claims description 14
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 13
- 229940124530 sulfonamide Drugs 0.000 claims description 13
- 150000003456 sulfonamides Chemical class 0.000 claims description 13
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 11
- 239000004475 Arginine Substances 0.000 claims description 10
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 10
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 claims description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 10
- 125000003368 amide group Chemical group 0.000 claims description 9
- 208000019425 cirrhosis of liver Diseases 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 9
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 9
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 8
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 7
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 7
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims description 6
- 201000009594 Systemic Scleroderma Diseases 0.000 claims description 6
- 206010042953 Systemic sclerosis Diseases 0.000 claims description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 6
- 230000009787 cardiac fibrosis Effects 0.000 claims description 5
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
- 208000033679 diabetic kidney disease Diseases 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- 201000002793 renal fibrosis Diseases 0.000 claims description 4
- 208000007342 Diabetic Nephropathies Diseases 0.000 claims description 3
- 208000020832 chronic kidney disease Diseases 0.000 claims description 3
- 208000005069 pulmonary fibrosis Diseases 0.000 claims description 3
- UBYJRGAFVQXRIU-IBGZPJMESA-N (3S)-3-(2-methoxypyrimidin-5-yl)-3-[3-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]pyrazol-1-yl]propanoic acid Chemical compound COc1ncc(cn1)[C@H](CC(O)=O)n1ccc(CCCc2ccc3CCCNc3n2)n1 UBYJRGAFVQXRIU-IBGZPJMESA-N 0.000 claims description 2
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 2
- WETNDFFONPZIGS-UHFFFAOYSA-N 3-(6-methoxypyridin-3-yl)-3-[1-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]pyrazol-3-yl]propanoic acid Chemical compound COC1=CC=C(C=N1)C(CC(O)=O)C1=NN(CCCC2=CC=C3CCCNC3=N2)C=C1 WETNDFFONPZIGS-UHFFFAOYSA-N 0.000 claims description 2
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000000437 thiazol-2-yl group Chemical group [H]C1=C([H])N=C(*)S1 0.000 claims 16
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 claims 4
- LUNGOZZVVOHVRP-PKOBYXMFSA-N COC1=CC=C(C=N1)[C@@H](CC(=O)O)C=1SC=C(N=1)CCC[C@@H]1NC2=NC=CC=C2CC1 Chemical compound COC1=CC=C(C=N1)[C@@H](CC(=O)O)C=1SC=C(N=1)CCC[C@@H]1NC2=NC=CC=C2CC1 LUNGOZZVVOHVRP-PKOBYXMFSA-N 0.000 claims 2
- 230000002500 effect on skin Effects 0.000 claims 2
- 239000001294 propane Substances 0.000 claims 2
- RIQIKORYQBMUTL-HXUWFJFHSA-N (2R)-2-(3-fluoro-4-methoxyphenyl)-3-[5-[4-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)butyl]-1,3-thiazol-2-yl]propanoic acid Chemical compound COc1ccc(cc1F)[C@@H](Cc1ncc(CCCCc2ccc3CCCNc3n2)s1)C(O)=O RIQIKORYQBMUTL-HXUWFJFHSA-N 0.000 claims 1
- RIQIKORYQBMUTL-FQEVSTJZSA-N (2S)-2-(3-fluoro-4-methoxyphenyl)-3-[5-[4-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)butyl]-1,3-thiazol-2-yl]propanoic acid Chemical compound COc1ccc(cc1F)[C@H](Cc1ncc(CCCCc2ccc3CCCNc3n2)s1)C(O)=O RIQIKORYQBMUTL-FQEVSTJZSA-N 0.000 claims 1
- QMBVMQULMAFHDB-HXUWFJFHSA-N (3R)-3-(2-ethoxypyrimidin-5-yl)-3-[4-[4-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)butyl]-1,3-thiazol-2-yl]propanoic acid Chemical compound CCOC1=NC=C(C=N1)[C@@H](CC(O)=O)C1=NC(CCCCC2=CC=C3CCCNC3=N2)=CS1 QMBVMQULMAFHDB-HXUWFJFHSA-N 0.000 claims 1
- UBYJRGAFVQXRIU-LJQANCHMSA-N (3R)-3-(2-methoxypyrimidin-5-yl)-3-[3-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]pyrazol-1-yl]propanoic acid Chemical compound COc1ncc(cn1)[C@@H](CC(O)=O)n1ccc(CCCc2ccc3CCCNc3n2)n1 UBYJRGAFVQXRIU-LJQANCHMSA-N 0.000 claims 1
- CBEDCDMHOQWJRM-HXUWFJFHSA-N (3R)-3-(2-methoxypyrimidin-5-yl)-3-[3-[3-(6,7,8,9-tetrahydro-5H-pyrido[2,3-b]azepin-2-yl)propyl]pyrazol-1-yl]propanoic acid Chemical compound COC1=NC=C(C=N1)[C@@H](CC(=O)O)N1N=C(C=C1)CCCC=1C=CC2=C(NCCCC2)N=1 CBEDCDMHOQWJRM-HXUWFJFHSA-N 0.000 claims 1
- DAJVJLDTALOMRU-GOSISDBHSA-N (3R)-3-(2-methoxypyrimidin-5-yl)-3-[4-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]-1,3-thiazol-2-yl]propanoic acid Chemical compound COC1=NC=C(C=N1)[C@@H](CC(O)=O)C1=NC(CCCC2=CC=C3CCCNC3=N2)=CS1 DAJVJLDTALOMRU-GOSISDBHSA-N 0.000 claims 1
- IFPMYGLSHXXRFZ-LJQANCHMSA-N (3R)-3-(2-methoxypyrimidin-5-yl)-3-[4-[4-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)butyl]-1,3-thiazol-2-yl]propanoic acid Chemical compound COC1=NC=C(C=N1)[C@@H](CC(=O)O)C=1SC=C(N=1)CCCCC1=NC=2NCCCC=2C=C1 IFPMYGLSHXXRFZ-LJQANCHMSA-N 0.000 claims 1
- BCBRXDHPNAOLSW-LJQANCHMSA-N (3R)-3-(2-methylpyrimidin-5-yl)-3-[4-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]-1,3-thiazol-2-yl]propanoic acid Chemical compound Cc1ncc(cn1)[C@@H](CC(O)=O)c1nc(CCCc2ccc3CCCNc3n2)cs1 BCBRXDHPNAOLSW-LJQANCHMSA-N 0.000 claims 1
- GDBNGKQEPUAMCI-OAQYLSRUSA-N (3R)-3-(3,4-dimethoxyphenyl)-3-[4-[4-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)butyl]-1,3-thiazol-2-yl]propanoic acid Chemical compound COC=1C=C(C=CC=1OC)[C@@H](CC(=O)O)C=1SC=C(N=1)CCCCC1=NC=2NCCCC=2C=C1 GDBNGKQEPUAMCI-OAQYLSRUSA-N 0.000 claims 1
- YXDUBNYLAAIZFB-HXUWFJFHSA-N (3R)-3-(3-fluoro-4-methoxyphenyl)-3-[4-[4-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)butyl]-1,3-thiazol-2-yl]propanoic acid Chemical compound COC1=C(F)C=C(C=C1)[C@@H](CC(O)=O)C1=NC(CCCCC2=CC=C3CCCNC3=N2)=CS1 YXDUBNYLAAIZFB-HXUWFJFHSA-N 0.000 claims 1
- DDEPDVDAXZTTNI-OAQYLSRUSA-N (3R)-3-(5-methylpyridin-3-yl)-3-[3-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]pyrazol-1-yl]propanoic acid Chemical compound CC=1C=C(C=NC=1)[C@@H](CC(=O)O)N1N=C(C=C1)CCCC1=NC=2NCCCC=2C=C1 DDEPDVDAXZTTNI-OAQYLSRUSA-N 0.000 claims 1
- REHWTMUCNPCVOK-HXUWFJFHSA-N (3R)-3-(5-methylpyridin-3-yl)-3-[4-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]-1,3-thiazol-2-yl]propanoic acid Chemical compound CC1=CN=CC(=C1)[C@@H](CC(O)=O)C1=NC(CCCC2=CC=C3CCCNC3=N2)=CS1 REHWTMUCNPCVOK-HXUWFJFHSA-N 0.000 claims 1
- IABHYNPYOQIKNL-HXUWFJFHSA-N (3R)-3-(6-methoxypyridin-3-yl)-3-[1-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]pyrazol-4-yl]propanoic acid Chemical compound COc1ccc(cn1)[C@@H](CC(O)=O)c1cnn(CCCc2ccc3CCCNc3n2)c1 IABHYNPYOQIKNL-HXUWFJFHSA-N 0.000 claims 1
- VXWFWYADNINHES-HXUWFJFHSA-N (3R)-3-(6-methoxypyridin-3-yl)-3-[3-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]pyrazol-1-yl]propanoic acid Chemical compound COC1=CC=C(C=N1)[C@@H](CC(=O)O)N1N=C(C=C1)CCCC1=NC=2NCCCC=2C=C1 VXWFWYADNINHES-HXUWFJFHSA-N 0.000 claims 1
- CGAASNMVFHAXRP-HXUWFJFHSA-N (3R)-3-(6-methoxypyridin-3-yl)-3-[4-[4-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)butyl]-1,3-thiazol-2-yl]propanoic acid Chemical compound COC1=CC=C(C=N1)[C@@H](CC(=O)O)C=1SC=C(N=1)CCCCC1=NC=2NCCCC=2C=C1 CGAASNMVFHAXRP-HXUWFJFHSA-N 0.000 claims 1
- SXFILBGBIGGRAC-LJQANCHMSA-N (3R)-3-(6-methoxypyridin-3-yl)-3-[5-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]-1,3-thiazol-2-yl]propanoic acid Chemical compound COc1ccc(cn1)[C@@H](CC(O)=O)c1ncc(CCCc2ccc3CCCNc3n2)s1 SXFILBGBIGGRAC-LJQANCHMSA-N 0.000 claims 1
- KWQAOJZTPSJWFI-HXUWFJFHSA-N (3R)-3-(6-methoxypyridin-3-yl)-3-[5-[4-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)butyl]-1,3-thiazol-2-yl]propanoic acid Chemical compound COC1=CC=C(C=N1)[C@@H](CC(=O)O)C=1SC(=CN=1)CCCCC1=NC=2NCCCC=2C=C1 KWQAOJZTPSJWFI-HXUWFJFHSA-N 0.000 claims 1
- PMFSDJYOISLEPP-HXUWFJFHSA-N (3R)-3-[6-(dimethylamino)pyridin-3-yl]-3-[4-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]-1,3-thiazol-2-yl]propanoic acid Chemical compound CN(C)C1=CC=C(C=N1)[C@@H](CC(O)=O)C1=NC(CCCC2=CC=C3CCCNC3=N2)=CS1 PMFSDJYOISLEPP-HXUWFJFHSA-N 0.000 claims 1
- BADLBAKVUVGUCQ-OAQYLSRUSA-N (3R)-3-[6-(dimethylamino)pyridin-3-yl]-3-[4-[4-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)butyl]-1,3-thiazol-2-yl]propanoic acid Chemical compound CN(C)C1=CC=C(C=N1)[C@@H](CC(O)=O)C1=NC(CCCCC2=CC=C3CCCNC3=N2)=CS1 BADLBAKVUVGUCQ-OAQYLSRUSA-N 0.000 claims 1
- JEWVDLUACRWTEW-FQEVSTJZSA-N (3S)-3-(2-ethoxypyrimidin-5-yl)-3-[3-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]pyrazol-1-yl]propanoic acid Chemical compound CCOc1ncc(cn1)[C@H](CC(O)=O)n1ccc(CCCc2ccc3CCCNc3n2)n1 JEWVDLUACRWTEW-FQEVSTJZSA-N 0.000 claims 1
- QMBVMQULMAFHDB-FQEVSTJZSA-N (3S)-3-(2-ethoxypyrimidin-5-yl)-3-[4-[4-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)butyl]-1,3-thiazol-2-yl]propanoic acid Chemical compound C(C)OC1=NC=C(C=N1)[C@H](CC(=O)O)C=1SC=C(N=1)CCCCC1=NC=2NCCCC=2C=C1 QMBVMQULMAFHDB-FQEVSTJZSA-N 0.000 claims 1
- CBEDCDMHOQWJRM-FQEVSTJZSA-N (3S)-3-(2-methoxypyrimidin-5-yl)-3-[3-[3-(6,7,8,9-tetrahydro-5H-pyrido[2,3-b]azepin-2-yl)propyl]pyrazol-1-yl]propanoic acid Chemical compound COC1=NC=C(C=N1)[C@H](CC(=O)O)N1N=C(C=C1)CCCC=1C=CC2=C(NCCCC2)N=1 CBEDCDMHOQWJRM-FQEVSTJZSA-N 0.000 claims 1
- YGUFEJBKMLSYAH-MJGOQNOKSA-N (3S)-3-(2-methoxypyrimidin-5-yl)-3-[3-[3-[(2R)-1,2,3,4-tetrahydro-1,8-naphthyridin-2-yl]propyl]pyrazol-1-yl]propanoic acid Chemical compound COC1=NC=C(C=N1)[C@H](CC(=O)O)N1N=C(C=C1)CCC[C@H]1NC2=NC=CC=C2CC1 YGUFEJBKMLSYAH-MJGOQNOKSA-N 0.000 claims 1
- YGUFEJBKMLSYAH-HKUYNNGSSA-N (3S)-3-(2-methoxypyrimidin-5-yl)-3-[3-[3-[(2S)-1,2,3,4-tetrahydro-1,8-naphthyridin-2-yl]propyl]pyrazol-1-yl]propanoic acid Chemical compound COc1ncc(cn1)[C@H](CC(O)=O)n1ccc(CCC[C@H]2CCc3cccnc3N2)n1 YGUFEJBKMLSYAH-HKUYNNGSSA-N 0.000 claims 1
- IFPMYGLSHXXRFZ-IBGZPJMESA-N (3S)-3-(2-methoxypyrimidin-5-yl)-3-[4-[4-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)butyl]-1,3-thiazol-2-yl]propanoic acid Chemical compound COC1=NC=C(C=N1)[C@H](CC(=O)O)C=1SC=C(N=1)CCCCC1=NC=2NCCCC=2C=C1 IFPMYGLSHXXRFZ-IBGZPJMESA-N 0.000 claims 1
- YZJQEJHDCYMNMO-NRFANRHFSA-N (3S)-3-(2-methylpyrimidin-5-yl)-3-[3-[3-(6,7,8,9-tetrahydro-5H-pyrido[2,3-b]azepin-2-yl)propyl]pyrazol-1-yl]propanoic acid Chemical compound CC1=NC=C(C=N1)[C@H](CC(=O)O)N1N=C(C=C1)CCCC=1C=CC2=C(NCCCC2)N=1 YZJQEJHDCYMNMO-NRFANRHFSA-N 0.000 claims 1
- QUAIYNWNKTYYGL-ICSRJNTNSA-N (3S)-3-(2-methylpyrimidin-5-yl)-3-[3-[3-[(2S)-1,2,3,4-tetrahydro-1,8-naphthyridin-2-yl]propyl]pyrazol-1-yl]propanoic acid Chemical compound CC1=NC=C(C=N1)[C@H](CC(O)=O)N1C=CC(CCC[C@H]2CCC3=CC=CN=C3N2)=N1 QUAIYNWNKTYYGL-ICSRJNTNSA-N 0.000 claims 1
- BCBRXDHPNAOLSW-IBGZPJMESA-N (3S)-3-(2-methylpyrimidin-5-yl)-3-[4-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]-1,3-thiazol-2-yl]propanoic acid Chemical compound CC1=NC=C(C=N1)[C@H](CC(O)=O)C1=NC(CCCC2=CC=C3CCCNC3=N2)=CS1 BCBRXDHPNAOLSW-IBGZPJMESA-N 0.000 claims 1
- WKRYSVJHDZTTJT-SFHVURJKSA-N (3S)-3-(2-oxo-1H-pyrimidin-5-yl)-3-[3-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]pyrazol-1-yl]propanoic acid Chemical compound OC(=O)C[C@H](N1C=CC(CCCC2=CC=C3CCCNC3=N2)=N1)C1=CN=C(O)N=C1 WKRYSVJHDZTTJT-SFHVURJKSA-N 0.000 claims 1
- GDBNGKQEPUAMCI-NRFANRHFSA-N (3S)-3-(3,4-dimethoxyphenyl)-3-[4-[4-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)butyl]-1,3-thiazol-2-yl]propanoic acid Chemical compound COC=1C=C(C=CC=1OC)[C@H](CC(=O)O)C=1SC=C(N=1)CCCCC1=NC=2NCCCC=2C=C1 GDBNGKQEPUAMCI-NRFANRHFSA-N 0.000 claims 1
- IRRAOOUFBQNPFO-SFHVURJKSA-N (3S)-3-(3-fluoro-4-methoxyphenyl)-3-[2-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]-1,3-thiazol-4-yl]propanoic acid Chemical compound COC1=C(F)C=C(C=C1)[C@H](CC(O)=O)C1=CSC(CCCC2=CC=C3CCCNC3=N2)=N1 IRRAOOUFBQNPFO-SFHVURJKSA-N 0.000 claims 1
- ZDRWXUHIAQJLBM-IBGZPJMESA-N (3S)-3-(3-fluoro-4-methoxyphenyl)-3-[4-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]-1,3-thiazol-2-yl]propanoic acid Chemical compound COC1=C(F)C=C(C=C1)[C@H](CC(O)=O)C1=NC(CCCC2=CC=C3CCCNC3=N2)=CS1 ZDRWXUHIAQJLBM-IBGZPJMESA-N 0.000 claims 1
- XIVCRSBEVGNWMB-NRFANRHFSA-N (3S)-3-(5-methoxypyridin-3-yl)-3-[3-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]pyrazol-1-yl]propanoic acid Chemical compound COC1=CN=CC(=C1)[C@H](CC(O)=O)N1C=CC(CCCC2=CC=C3CCCNC3=N2)=N1 XIVCRSBEVGNWMB-NRFANRHFSA-N 0.000 claims 1
- REHWTMUCNPCVOK-FQEVSTJZSA-N (3S)-3-(5-methylpyridin-3-yl)-3-[4-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]-1,3-thiazol-2-yl]propanoic acid Chemical compound CC1=CN=CC(=C1)[C@H](CC(O)=O)C1=NC(CCCC2=CC=C3CCCNC3=N2)=CS1 REHWTMUCNPCVOK-FQEVSTJZSA-N 0.000 claims 1
- IABHYNPYOQIKNL-FQEVSTJZSA-N (3S)-3-(6-methoxypyridin-3-yl)-3-[1-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]pyrazol-4-yl]propanoic acid Chemical compound COc1ccc(cn1)[C@H](CC(O)=O)c1cnn(CCCc2ccc3CCCNc3n2)c1 IABHYNPYOQIKNL-FQEVSTJZSA-N 0.000 claims 1
- VXWFWYADNINHES-FQEVSTJZSA-N (3S)-3-(6-methoxypyridin-3-yl)-3-[3-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]pyrazol-1-yl]propanoic acid Chemical compound COc1ccc(cn1)[C@H](CC(O)=O)n1ccc(CCCc2ccc3CCCNc3n2)n1 VXWFWYADNINHES-FQEVSTJZSA-N 0.000 claims 1
- WWVUBEGMDOTPPR-IBGZPJMESA-N (3S)-3-(6-methoxypyridin-3-yl)-3-[4-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]-1,3-thiazol-2-yl]propanoic acid Chemical compound COC1=CC=C(C=N1)[C@H](CC(O)=O)C1=NC(CCCC2=CC=C3CCCNC3=N2)=CS1 WWVUBEGMDOTPPR-IBGZPJMESA-N 0.000 claims 1
- CGAASNMVFHAXRP-FQEVSTJZSA-N (3S)-3-(6-methoxypyridin-3-yl)-3-[4-[4-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)butyl]-1,3-thiazol-2-yl]propanoic acid Chemical compound COC1=CC=C(C=N1)[C@H](CC(=O)O)C=1SC=C(N=1)CCCCC1=NC=2NCCCC=2C=C1 CGAASNMVFHAXRP-FQEVSTJZSA-N 0.000 claims 1
- SXFILBGBIGGRAC-IBGZPJMESA-N (3S)-3-(6-methoxypyridin-3-yl)-3-[5-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]-1,3-thiazol-2-yl]propanoic acid Chemical compound COC1=CC=C(C=N1)[C@H](CC(=O)O)C=1SC(=CN=1)CCCC1=NC=2NCCCC=2C=C1 SXFILBGBIGGRAC-IBGZPJMESA-N 0.000 claims 1
- KWQAOJZTPSJWFI-FQEVSTJZSA-N (3S)-3-(6-methoxypyridin-3-yl)-3-[5-[4-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)butyl]-1,3-thiazol-2-yl]propanoic acid Chemical compound COC1=CC=C(C=N1)[C@H](CC(=O)O)C=1SC(=CN=1)CCCCC1=NC=2NCCCC=2C=C1 KWQAOJZTPSJWFI-FQEVSTJZSA-N 0.000 claims 1
- VUCPJDQRPNKODR-IBGZPJMESA-N (3S)-3-(6-oxo-1H-pyridin-3-yl)-3-[3-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]pyrazol-1-yl]propanoic acid Chemical compound OC(=O)C[C@@H](c1ccc(=O)[nH]c1)n1ccc(CCCc2ccc3CCCNc3n2)n1 VUCPJDQRPNKODR-IBGZPJMESA-N 0.000 claims 1
- ZGCLOBSDNFKPOK-SANMLTNESA-N (3S)-3-(6-phenylmethoxypyridin-3-yl)-3-[3-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]pyrazol-1-yl]propanoic acid Chemical compound OC(=O)C[C@H](N1C=CC(CCCC2=CC=C3CCCNC3=N2)=N1)C1=CC=C(OCC2=CC=CC=C2)N=C1 ZGCLOBSDNFKPOK-SANMLTNESA-N 0.000 claims 1
- PMFSDJYOISLEPP-FQEVSTJZSA-N (3S)-3-[6-(dimethylamino)pyridin-3-yl]-3-[4-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]-1,3-thiazol-2-yl]propanoic acid Chemical compound CN(C1=CC=C(C=N1)[C@H](CC(=O)O)C=1SC=C(N=1)CCCC1=NC=2NCCCC=2C=C1)C PMFSDJYOISLEPP-FQEVSTJZSA-N 0.000 claims 1
- BADLBAKVUVGUCQ-NRFANRHFSA-N (3S)-3-[6-(dimethylamino)pyridin-3-yl]-3-[4-[4-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)butyl]-1,3-thiazol-2-yl]propanoic acid Chemical compound CN(C)C1=CC=C(C=N1)[C@H](CC(O)=O)C1=NC(CCCCC2=CC=C3CCCNC3=N2)=CS1 BADLBAKVUVGUCQ-NRFANRHFSA-N 0.000 claims 1
- QQAQFYFRKOTFAK-UHFFFAOYSA-N 3-(2,3-dihydro-1-benzofuran-5-yl)-3-[3-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]pyrazol-1-yl]propanoic acid Chemical compound OC(=O)CC(c1ccc2OCCc2c1)n1ccc(CCCc2ccc3CCCNc3n2)n1 QQAQFYFRKOTFAK-UHFFFAOYSA-N 0.000 claims 1
- ZKJMYZGFBDUOAC-UHFFFAOYSA-N 3-(2-methylpyrimidin-5-yl)-3-[3-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]pyrazol-1-yl]propanoic acid Chemical compound Cc1ncc(cn1)C(CC(O)=O)n1ccc(CCCc2ccc3CCCNc3n2)n1 ZKJMYZGFBDUOAC-UHFFFAOYSA-N 0.000 claims 1
- BCBRXDHPNAOLSW-UHFFFAOYSA-N 3-(2-methylpyrimidin-5-yl)-3-[4-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]-1,3-thiazol-2-yl]propanoic acid Chemical compound CC1=NC=C(C=N1)C(CC(O)=O)C1=NC(CCCC2=CC=C3CCCNC3=N2)=CS1 BCBRXDHPNAOLSW-UHFFFAOYSA-N 0.000 claims 1
- PBWFOTQLLPUBFH-LROBGIAVSA-N 3-(2-methylpyrimidin-5-yl)-3-[5-[3-[(2S)-1,2,3,4-tetrahydro-1,8-naphthyridin-2-yl]propyl]pyrazol-1-yl]propanoic acid Chemical compound CC1=NC=C(C=N1)C(CC(O)=O)N1N=CC=C1CCC[C@H]1CCC2=CC=CN=C2N1 PBWFOTQLLPUBFH-LROBGIAVSA-N 0.000 claims 1
- DROJIMZJMWUYJZ-UHFFFAOYSA-N 3-(3-fluoro-4-methoxyphenyl)-3-[1-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]pyrazol-4-yl]propanoic acid Chemical compound COc1ccc(cc1F)C(CC(O)=O)c1cnn(CCCc2ccc3CCCNc3n2)c1 DROJIMZJMWUYJZ-UHFFFAOYSA-N 0.000 claims 1
- PISFUPDRJUNJMG-UHFFFAOYSA-N 3-(3-fluoro-4-methoxyphenyl)-3-[1-[4-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)butyl]pyrazol-4-yl]propanoic acid Chemical compound FC=1C=C(C=CC=1OC)C(CC(=O)O)C=1C=NN(C=1)CCCCC1=NC=2NCCCC=2C=C1 PISFUPDRJUNJMG-UHFFFAOYSA-N 0.000 claims 1
- BKTHKHWQJWMNPX-UHFFFAOYSA-N 3-(3-morpholin-4-ylphenyl)-3-[3-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]pyrazol-1-yl]propanoic acid Chemical compound O1CCN(CC1)C=1C=C(C=CC=1)C(CC(=O)O)N1N=C(C=C1)CCCC1=NC=2NCCCC=2C=C1 BKTHKHWQJWMNPX-UHFFFAOYSA-N 0.000 claims 1
- SPDUOUZUENXLAW-UHFFFAOYSA-N 3-(5-methoxypyrazin-2-yl)-3-[3-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]pyrazol-1-yl]propanoic acid Chemical compound C1CNC2=C(C1)C=CC(=N2)CCCC1=NN(C=C1)C(CC(=O)O)C1=CN=C(OC)C=N1 SPDUOUZUENXLAW-UHFFFAOYSA-N 0.000 claims 1
- BWNFEKCSTXKOQT-UHFFFAOYSA-N 3-(5-methoxypyrazin-2-yl)-3-[5-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]pyrazol-1-yl]propanoic acid Chemical compound COC=1N=CC(=NC=1)C(CC(=O)O)N1N=CC=C1CCCC1=NC=2NCCCC=2C=C1 BWNFEKCSTXKOQT-UHFFFAOYSA-N 0.000 claims 1
- BRLFDRHCJVCAKG-UHFFFAOYSA-N 3-(5-pyrrolidin-1-ylpyridin-3-yl)-3-[3-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]pyrazol-1-yl]propanoic acid Chemical compound N1(CCCC1)C=1C=C(C=NC=1)C(CC(=O)O)N1N=C(C=C1)CCCC1=NC=2NCCCC=2C=C1 BRLFDRHCJVCAKG-UHFFFAOYSA-N 0.000 claims 1
- RAHZUAJLXVILRF-UHFFFAOYSA-N 3-(6-methoxypyridazin-3-yl)-3-[3-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]pyrazol-1-yl]propanoic acid Chemical compound COc1ccc(nn1)C(CC(O)=O)n1ccc(CCCc2ccc3CCCNc3n2)n1 RAHZUAJLXVILRF-UHFFFAOYSA-N 0.000 claims 1
- IABHYNPYOQIKNL-UHFFFAOYSA-N 3-(6-methoxypyridin-3-yl)-3-[1-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]pyrazol-4-yl]propanoic acid Chemical compound COc1ccc(cn1)C(CC(O)=O)c1cnn(CCCc2ccc3CCCNc3n2)c1 IABHYNPYOQIKNL-UHFFFAOYSA-N 0.000 claims 1
- GTSPHCCFRVTHLR-UHFFFAOYSA-N 3-(6-methoxypyridin-3-yl)-3-[1-[4-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)butyl]pyrazol-4-yl]propanoic acid Chemical compound N1(C=C(C(C2=CN=C(OC)C=C2)CC(=O)O)C=N1)CCCCC1=CC=C2CCCNC2=N1 GTSPHCCFRVTHLR-UHFFFAOYSA-N 0.000 claims 1
- VXWFWYADNINHES-UHFFFAOYSA-N 3-(6-methoxypyridin-3-yl)-3-[3-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]pyrazol-1-yl]propanoic acid Chemical compound C1CNC2=C(C=CC(=N2)CCCC2=NN(C=C2)C(CC(=O)O)C2=CC=C(OC)N=C2)C1 VXWFWYADNINHES-UHFFFAOYSA-N 0.000 claims 1
- MBIIFYIIXDIURN-UHFFFAOYSA-N 3-(6-methoxypyridin-3-yl)-3-[3-[3-(6,7,8,9-tetrahydro-5H-pyrido[2,3-b]azepin-2-yl)propyl]pyrazol-1-yl]propanoic acid Chemical compound COc1ccc(cn1)C(CC(O)=O)n1ccc(CCCc2ccc3CCCCNc3n2)n1 MBIIFYIIXDIURN-UHFFFAOYSA-N 0.000 claims 1
- VZKVXHYXNXGQDU-UHFFFAOYSA-N 3-(6-methoxypyridin-3-yl)-3-[3-[4-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)butyl]pyrazol-1-yl]propanoic acid Chemical compound COC1=CC=C(C=N1)C(CC(=O)O)N1N=C(C=C1)CCCCC1=NC=2NCCCC=2C=C1 VZKVXHYXNXGQDU-UHFFFAOYSA-N 0.000 claims 1
- QDOVUPKFDCFBGR-UHFFFAOYSA-N 3-(6-methoxypyridin-3-yl)-3-[4-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]pyrazol-1-yl]propanoic acid Chemical compound COC1=CC=C(C=N1)C(CC(=O)O)N1N=CC(=C1)CCCC1=NC=2NCCCC=2C=C1 QDOVUPKFDCFBGR-UHFFFAOYSA-N 0.000 claims 1
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- CMIVZAUSOHNSFO-UHFFFAOYSA-N 3-[2-(azetidin-1-yl)pyrimidin-5-yl]-3-[5-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]pyrazol-1-yl]propanoic acid Chemical compound OC(=O)CC(c1cnc(nc1)N1CCC1)n1nccc1CCCc1ccc2CCCNc2n1 CMIVZAUSOHNSFO-UHFFFAOYSA-N 0.000 claims 1
- ZVUWHFQRZDKPAU-UHFFFAOYSA-N 3-[5-(2-methoxyethoxy)pyridin-3-yl]-3-[3-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]pyrazol-1-yl]propanoic acid Chemical compound COCCOC=1C=C(C=NC=1)C(CC(=O)O)N1N=C(C=C1)CCCC1=NC=2NCCCC=2C=C1 ZVUWHFQRZDKPAU-UHFFFAOYSA-N 0.000 claims 1
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Classifications
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- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/4353—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems
- A61K31/4375—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a six-membered ring having nitrogen as a ring heteroatom, e.g. quinolizines, naphthyridines, berberine, vincamine
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
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| US201662418848P | 2016-11-08 | 2016-11-08 | |
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| TW201823244A TW201823244A (zh) | 2018-07-01 |
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Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN109996541A (zh) | 2016-09-07 | 2019-07-09 | 普利安特治疗公司 | N-酰基氨基酸化合物及其使用方法 |
| RS63483B1 (sr) * | 2016-11-08 | 2022-09-30 | Bristol Myers Squibb Co | 3-supstituisane propionske kiseline kao inhibitori alfa v integrina |
| CA3042710A1 (en) * | 2016-11-08 | 2018-05-17 | Bristol-Myers Squibb Company | Cyclobutane- and azetidine-containing mono and spirocyclic compounds as .alpha.v integrin inhibitors |
| EA201991121A1 (ru) * | 2016-11-08 | 2019-11-29 | АЗОЛАМИДЫ И АЗОЛАМИНЫ В КАЧЕСТВЕ ИНГИБИТОРОВ ИНТЕГРИНОВ αV | |
| EP3562826A4 (en) | 2016-12-29 | 2020-08-26 | Saint Louis University | INTEGRIN ANTAGONISTS |
| MA52117A (fr) | 2017-02-28 | 2022-04-06 | Morphic Therapeutic Inc | Inhibiteurs de l'intégrine (alpha-v) (bêta-6) |
| AU2018229275B2 (en) | 2017-02-28 | 2021-12-23 | Morphic Therapeutic, Inc. | Inhibitors of (alpha-v)(beta-6) integrin |
| WO2020081154A1 (en) | 2018-08-29 | 2020-04-23 | Morphic Therapeutic, Inc. | INHIBITORS OF ανβ6 INTEGRIN |
| CA3109534A1 (en) | 2018-08-29 | 2020-03-05 | Morphic Therapeutic, Inc. | Inhibiting .alpha.v .beta.6 integrin |
| ES3013256T3 (en) | 2018-10-30 | 2025-04-11 | Gilead Sciences Inc | Imidazo[1,2-a]pyridine derivatives as alpha4beta7 integrin inhibitors for the treatment of inflammatory diseases |
| KR102652797B1 (ko) | 2018-10-30 | 2024-04-02 | 길리애드 사이언시즈, 인코포레이티드 | 알파4베타7 인테그린의 억제를 위한 화합물 |
| CA3115830C (en) | 2018-10-30 | 2023-09-12 | Gilead Sciences, Inc. | Compounds for inhibition of .alpha.4.beta.7 integrin |
| HUE070112T2 (hu) | 2018-10-30 | 2025-05-28 | Gilead Sciences Inc | 3-(Kinolin-8-il)-1,4-dihidropirido[3,4-d]pirimidin-2,4-dion-származékok mint alpha4beta7 integrin gátlók gyulladásos betegségek kezelésére |
| CN109824495B (zh) * | 2019-02-02 | 2022-12-09 | 盐城师范学院 | 一种新型偶联反应在制备碳-碳键结构化合物中的应用 |
| WO2021030438A1 (en) | 2019-08-14 | 2021-02-18 | Gilead Sciences, Inc. | Compounds for inhibition of alpha 4 beta 7 integrin |
| GB202010626D0 (en) | 2020-07-10 | 2020-08-26 | Univ Nottingham | Compound |
| WO2025064802A1 (en) * | 2023-09-21 | 2025-03-27 | Morphic Therapeutic, Inc. | INHIBITING HUMAN INTEGRIN α5β1 |
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| WO1999030709A1 (en) * | 1997-12-17 | 1999-06-24 | Merck & Co., Inc. | Integrin receptor antagonists |
| TW200738671A (en) * | 2006-01-31 | 2007-10-16 | Jerini Ag | Compounds for the inhibition of integrins and use thereof |
| TW200800999A (en) * | 2005-09-06 | 2008-01-01 | Astrazeneca Ab | Novel compounds |
| US20080045521A1 (en) * | 2006-06-09 | 2008-02-21 | Astrazeneca Ab | Phenylalanine derivatives |
| US20080255183A1 (en) * | 2007-04-11 | 2008-10-16 | Astrazeneca Ab | N-[HETEROARYLCARBONYL]-3-THIENYL-L-ALANINE DERIVATIVES AS a5beta1 ANTAGONISTS |
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| EP0451790A1 (de) * | 1990-04-12 | 1991-10-16 | Hoechst Aktiengesellschaft | 3,5-disubstituierte 2-Isoxazoline und Isoxazole, Verfahren zu deren Herstellung, diese enthaltende Mittel und ihre Verwendung |
| US5849736A (en) | 1993-11-24 | 1998-12-15 | The Dupont Merck Pharmaceutical Company | Isoxazoline and isoxazole fibrinogen receptor antagonists |
| ZA972195B (en) | 1996-03-15 | 1998-09-14 | Du Pont Merck Pharma | Spirocycle integrin inhibitors |
| IL136267A0 (en) | 1997-11-26 | 2001-05-20 | Du Pont Pharm Co | 1,3,4-THIADIZOLES AND 1,3,4-OXADIAZOLES AS αVβ3 ANTAGONISTS |
| JP2002522540A (ja) | 1998-08-13 | 2002-07-23 | メルク エンド カムパニー インコーポレーテッド | インテグリン受容体拮抗薬 |
| MXPA03006772A (es) | 2001-01-29 | 2004-10-15 | Dimensional Pharm Inc | Indoles sustituidos y su uso como antogonistas de integrina. |
| US20050043344A1 (en) * | 2002-12-20 | 2005-02-24 | Pharmacia Corporation | Heteroarylalkanoic acids as integrin receptor antagonists derivatives |
| CA2507958A1 (en) * | 2002-12-20 | 2004-07-15 | Pharmacia Corporation | Pyrazole compounds as integrin receptor antagonists derivatives |
| WO2006108040A1 (en) | 2005-04-05 | 2006-10-12 | Janssen Pharmaceutica, N.V. | Substituted indoles and their use as integrin antagonists |
| US7592461B2 (en) | 2005-12-21 | 2009-09-22 | Bristol-Myers Squibb Company | Indane modulators of glucocorticoid receptor, AP-1, and/or NF-κB activity and use thereof |
| US8362271B2 (en) | 2009-09-04 | 2013-01-29 | Basf Se | Process for preparing 1-phenylpyrazoles |
| CA2779303A1 (en) | 2009-10-29 | 2011-05-19 | Sirtris Pharmaceuticals, Inc. | Bicyclic pyridines and analogs as sirtuin modulators |
| ITFI20100019A1 (it) | 2010-02-12 | 2011-08-13 | Univ Firenze | Inibitori peptidomimetici di integrine basati sull'1,2,3-triazolo per la diagnosi e terapia dei tumori. |
| GB201305668D0 (en) | 2013-03-28 | 2013-05-15 | Glaxosmithkline Ip Dev Ltd | Avs6 Integrin Antagonists |
| TWI667233B (zh) | 2013-12-19 | 2019-08-01 | 德商拜耳製藥公司 | 新穎吲唑羧醯胺，其製備方法、含彼等之醫藥製劑及其製造醫藥之用途 |
| GB201417011D0 (en) | 2014-09-26 | 2014-11-12 | Glaxosmithkline Ip Dev Ltd | Novel compounds |
| GB201417094D0 (en) | 2014-09-26 | 2014-11-12 | Glaxosmithkline Ip Dev Ltd | Novel compounds |
| GB201417018D0 (en) | 2014-09-26 | 2014-11-12 | Glaxosmithkline Ip Dev Ltd | Novel compounds |
| GB201417002D0 (en) | 2014-09-26 | 2014-11-12 | Glaxosmithkline Ip Dev Ltd | Novel compound |
| RU2017132433A (ru) | 2015-02-19 | 2019-03-19 | Сайфлуор Лайф Сайенсиз, Инк. | Фторированные производные тетрагидронафтиридинилнонановой кислоты и их применение |
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| RS63483B1 (sr) * | 2016-11-08 | 2022-09-30 | Bristol Myers Squibb Co | 3-supstituisane propionske kiseline kao inhibitori alfa v integrina |
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2017
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- 2017-11-07 AU AU2017359023A patent/AU2017359023B2/en active Active
- 2017-11-07 JP JP2019523576A patent/JP7097358B2/ja active Active
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- 2017-11-07 WO PCT/US2017/060376 patent/WO2018089353A1/en not_active Ceased
- 2017-11-07 MA MA046743A patent/MA46743A/fr unknown
- 2017-11-07 NZ NZ754207A patent/NZ754207A/en unknown
- 2017-11-07 HU HUE17801230A patent/HUE059708T2/hu unknown
- 2017-11-07 US US16/347,844 patent/US10968219B2/en active Active
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2019
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2021
- 2021-02-24 US US17/184,179 patent/US11884661B2/en active Active
Patent Citations (5)
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| WO1999030709A1 (en) * | 1997-12-17 | 1999-06-24 | Merck & Co., Inc. | Integrin receptor antagonists |
| TW200800999A (en) * | 2005-09-06 | 2008-01-01 | Astrazeneca Ab | Novel compounds |
| TW200738671A (en) * | 2006-01-31 | 2007-10-16 | Jerini Ag | Compounds for the inhibition of integrins and use thereof |
| US20080045521A1 (en) * | 2006-06-09 | 2008-02-21 | Astrazeneca Ab | Phenylalanine derivatives |
| US20080255183A1 (en) * | 2007-04-11 | 2008-10-16 | Astrazeneca Ab | N-[HETEROARYLCARBONYL]-3-THIENYL-L-ALANINE DERIVATIVES AS a5beta1 ANTAGONISTS |
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