HRP20161545T1 - Supstituirani derivati 3-heteroaroilamino-propionske kiseline i njihova upotreba kao lijekova - Google Patents
Supstituirani derivati 3-heteroaroilamino-propionske kiseline i njihova upotreba kao lijekova Download PDFInfo
- Publication number
- HRP20161545T1 HRP20161545T1 HRP20161545TT HRP20161545T HRP20161545T1 HR P20161545 T1 HRP20161545 T1 HR P20161545T1 HR P20161545T T HRP20161545T T HR P20161545TT HR P20161545 T HRP20161545 T HR P20161545T HR P20161545 T1 HRP20161545 T1 HR P20161545T1
- Authority
- HR
- Croatia
- Prior art keywords
- phenyl
- methoxy
- carbonyl
- amino
- pyridine
- Prior art date
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- 239000003814 drug Substances 0.000 title claims 2
- 229940111131 antiinflammatory and antirheumatic product propionic acid derivative Drugs 0.000 title 1
- 229910052736 halogen Inorganic materials 0.000 claims 17
- 229910052739 hydrogen Inorganic materials 0.000 claims 16
- 239000001257 hydrogen Substances 0.000 claims 16
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 15
- 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 15
- 125000001424 substituent group Chemical group 0.000 claims 15
- -1 (S)-3-{[6-(2-fluoro-phenyl)-5-methoxy-pyridine-2-carbonyl]-amino}-3-o-tolyl-propanoic acid (S)-3-[(5-methoxy-6-phenyl-pyridine-2-carbonyl)-amino]-3-p-tolyl-propanoic acid Chemical compound 0.000 claims 13
- 150000003839 salts Chemical class 0.000 claims 12
- 239000012453 solvate Substances 0.000 claims 12
- 125000005843 halogen group Chemical group 0.000 claims 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 10
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 8
- 125000005842 heteroatom Chemical group 0.000 claims 8
- 125000002911 monocyclic heterocycle group Chemical group 0.000 claims 8
- 229910052757 nitrogen Inorganic materials 0.000 claims 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 8
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 6
- 229910052799 carbon Inorganic materials 0.000 claims 6
- 150000002367 halogens Chemical group 0.000 claims 6
- 239000000203 mixture Substances 0.000 claims 6
- 229910052760 oxygen Inorganic materials 0.000 claims 6
- 239000001301 oxygen Chemical group 0.000 claims 6
- 229910052717 sulfur Chemical group 0.000 claims 6
- 239000011593 sulfur Chemical group 0.000 claims 6
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 5
- 125000003118 aryl group Chemical group 0.000 claims 5
- 125000000623 heterocyclic group Chemical group 0.000 claims 5
- 150000002431 hydrogen Chemical group 0.000 claims 5
- 125000004432 carbon atom Chemical group C* 0.000 claims 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 4
- 125000001153 fluoro group Chemical group F* 0.000 claims 3
- 229920006395 saturated elastomer Polymers 0.000 claims 3
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims 3
- CSRIDXHGKXZTTL-FQEVSTJZSA-N (3s)-3-(2-chlorophenyl)-3-[[6-(2,3-dimethylphenyl)-5-methoxypyridine-2-carbonyl]amino]propanoic acid Chemical compound COC1=CC=C(C(=O)N[C@@H](CC(O)=O)C=2C(=CC=CC=2)Cl)N=C1C1=CC=CC(C)=C1C CSRIDXHGKXZTTL-FQEVSTJZSA-N 0.000 claims 2
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 2
- FPDGEWZOIOGCRA-ZXNOKPTOSA-N ClC1=C(C=CC(=C1)Cl)[C@H](CC(=O)O)NC(=O)C1=NC(=C(C=C1)OC)C1=CC=CC=C1.COC=1C=CC(=NC1C1=CC=CC=C1)C(=O)N[C@@H](CC(=O)O)C1=C(C=CC=C1)C Chemical compound ClC1=C(C=CC(=C1)Cl)[C@H](CC(=O)O)NC(=O)C1=NC(=C(C=C1)OC)C1=CC=CC=C1.COC=1C=CC(=NC1C1=CC=CC=C1)C(=O)N[C@@H](CC(=O)O)C1=C(C=CC=C1)C FPDGEWZOIOGCRA-ZXNOKPTOSA-N 0.000 claims 2
- 206010019280 Heart failures Diseases 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 239000002934 diuretic Substances 0.000 claims 2
- 239000000825 pharmaceutical preparation Substances 0.000 claims 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
- 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 2
- KEHUXPJSGKEGLT-ZXNOKPTOSA-N (3S)-3-(2-chlorophenyl)-3-[[6-(4-fluorophenyl)-5-methoxypyridine-2-carbonyl]amino]propanoic acid (3S)-3-[[5-methoxy-6-[3-(trifluoromethyl)phenyl]pyridine-2-carbonyl]amino]-3-(2-methylphenyl)propanoic acid Chemical compound COC=1C=CC(=NC1C1=CC(=CC=C1)C(F)(F)F)C(=O)N[C@@H](CC(=O)O)C1=C(C=CC=C1)C.ClC1=C(C=CC=C1)[C@H](CC(=O)O)NC(=O)C1=NC(=C(C=C1)OC)C1=CC=C(C=C1)F KEHUXPJSGKEGLT-ZXNOKPTOSA-N 0.000 claims 1
- QXBCHJHUXFFIIX-KXSSUAHJSA-N (3S)-3-[[6-(2,4-difluorophenyl)-5-methoxypyridine-2-carbonyl]amino]-3-(2-methylphenyl)propanoic acid (3S)-3-[[5-methoxy-6-[2-(trifluoromethyl)phenyl]pyridine-2-carbonyl]amino]-3-(2-methylphenyl)propanoic acid Chemical compound COc1ccc(nc1-c1ccc(F)cc1F)C(=O)N[C@@H](CC(O)=O)c1ccccc1C.COc1ccc(nc1-c1ccccc1C(F)(F)F)C(=O)N[C@@H](CC(O)=O)c1ccccc1C QXBCHJHUXFFIIX-KXSSUAHJSA-N 0.000 claims 1
- FJRNLXAKHWZIHH-KXSSUAHJSA-N (3S)-3-[[6-(3-fluorophenyl)-5-methoxypyridine-2-carbonyl]amino]-3-(4-methylphenyl)propanoic acid (3S)-3-[[5-methoxy-6-(2-methoxyphenyl)pyridine-2-carbonyl]amino]-3-(4-methylphenyl)propanoic acid Chemical compound COc1ccc(nc1-c1cccc(F)c1)C(=O)N[C@@H](CC(O)=O)c1ccc(C)cc1.COc1ccccc1-c1nc(ccc1OC)C(=O)N[C@@H](CC(O)=O)c1ccc(C)cc1 FJRNLXAKHWZIHH-KXSSUAHJSA-N 0.000 claims 1
- LOXIYPUTMZVFCM-HNNXBMFYSA-N (3s)-3-(2-chlorophenyl)-3-[(5-methoxy-6-pyrazin-2-ylpyridine-2-carbonyl)amino]propanoic acid Chemical compound COC1=CC=C(C(=O)N[C@@H](CC(O)=O)C=2C(=CC=CC=2)Cl)N=C1C1=CN=CC=N1 LOXIYPUTMZVFCM-HNNXBMFYSA-N 0.000 claims 1
- OPIUDADBODIHCW-KRWDZBQOSA-N (3s)-3-(2-chlorophenyl)-3-[[5-methoxy-6-(2-methylfuran-3-yl)pyridine-2-carbonyl]amino]propanoic acid Chemical compound COC1=CC=C(C(=O)N[C@@H](CC(O)=O)C=2C(=CC=CC=2)Cl)N=C1C=1C=COC=1C OPIUDADBODIHCW-KRWDZBQOSA-N 0.000 claims 1
- XAFSQLKTKHODRQ-KRWDZBQOSA-N (3s)-3-(2-chlorophenyl)-3-[[6-(2,3-dichlorophenyl)-5-methoxypyridine-2-carbonyl]amino]propanoic acid Chemical compound COC1=CC=C(C(=O)N[C@@H](CC(O)=O)C=2C(=CC=CC=2)Cl)N=C1C1=CC=CC(Cl)=C1Cl XAFSQLKTKHODRQ-KRWDZBQOSA-N 0.000 claims 1
- GZSJTHGNRSJVRE-KRWDZBQOSA-N (3s)-3-(2-chlorophenyl)-3-[[6-(2,3-difluorophenyl)-5-methoxypyridine-2-carbonyl]amino]propanoic acid Chemical compound COC1=CC=C(C(=O)N[C@@H](CC(O)=O)C=2C(=CC=CC=2)Cl)N=C1C1=CC=CC(F)=C1F GZSJTHGNRSJVRE-KRWDZBQOSA-N 0.000 claims 1
- KISATKMEYZEWLV-SFHVURJKSA-N (3s)-3-(2-chlorophenyl)-3-[[6-(2,4-dichlorophenyl)-5-methoxypyridine-2-carbonyl]amino]propanoic acid Chemical compound COC1=CC=C(C(=O)N[C@@H](CC(O)=O)C=2C(=CC=CC=2)Cl)N=C1C1=CC=C(Cl)C=C1Cl KISATKMEYZEWLV-SFHVURJKSA-N 0.000 claims 1
- YIVMVDQFIWWBAZ-SFHVURJKSA-N (3s)-3-(2-chlorophenyl)-3-[[6-(2,4-difluorophenyl)-5-methoxypyridine-2-carbonyl]amino]propanoic acid Chemical compound COC1=CC=C(C(=O)N[C@@H](CC(O)=O)C=2C(=CC=CC=2)Cl)N=C1C1=CC=C(F)C=C1F YIVMVDQFIWWBAZ-SFHVURJKSA-N 0.000 claims 1
- MQGKSKROFSUAOT-SFHVURJKSA-N (3s)-3-(2-chlorophenyl)-3-[[6-(2,5-difluorophenyl)-5-methoxypyridine-2-carbonyl]amino]propanoic acid Chemical compound COC1=CC=C(C(=O)N[C@@H](CC(O)=O)C=2C(=CC=CC=2)Cl)N=C1C1=CC(F)=CC=C1F MQGKSKROFSUAOT-SFHVURJKSA-N 0.000 claims 1
- YFCVWTPHSOMYTI-SFHVURJKSA-N (3s)-3-(2-chlorophenyl)-3-[[6-(2-chlorophenyl)-5-methoxypyridine-2-carbonyl]amino]propanoic acid Chemical compound COC1=CC=C(C(=O)N[C@@H](CC(O)=O)C=2C(=CC=CC=2)Cl)N=C1C1=CC=CC=C1Cl YFCVWTPHSOMYTI-SFHVURJKSA-N 0.000 claims 1
- IIHFCWSBJOMFDL-IBGZPJMESA-N (3s)-3-(2-chlorophenyl)-3-[[6-(2-fluoro-5-methoxyphenyl)-5-methoxypyridine-2-carbonyl]amino]propanoic acid Chemical compound COC1=CC=C(F)C(C=2C(=CC=C(N=2)C(=O)N[C@@H](CC(O)=O)C=2C(=CC=CC=2)Cl)OC)=C1 IIHFCWSBJOMFDL-IBGZPJMESA-N 0.000 claims 1
- GBSIEOJKTGGBKO-IBGZPJMESA-N (3s)-3-(2-chlorophenyl)-3-[[6-(2-fluoro-5-methylphenyl)-5-methoxypyridine-2-carbonyl]amino]propanoic acid Chemical compound COC1=CC=C(C(=O)N[C@@H](CC(O)=O)C=2C(=CC=CC=2)Cl)N=C1C1=CC(C)=CC=C1F GBSIEOJKTGGBKO-IBGZPJMESA-N 0.000 claims 1
- AVGZKIWKXUSBPV-SFHVURJKSA-N (3s)-3-(2-chlorophenyl)-3-[[6-(2-fluorophenyl)-5-methoxypyridine-2-carbonyl]amino]propanoic acid Chemical compound COC1=CC=C(C(=O)N[C@@H](CC(O)=O)C=2C(=CC=CC=2)Cl)N=C1C1=CC=CC=C1F AVGZKIWKXUSBPV-SFHVURJKSA-N 0.000 claims 1
- GBUFPVUTCUTXKB-IBGZPJMESA-N (3s)-3-(2-chlorophenyl)-3-[[6-(3-fluoro-2-methylphenyl)-5-methoxypyridine-2-carbonyl]amino]propanoic acid Chemical compound COC1=CC=C(C(=O)N[C@@H](CC(O)=O)C=2C(=CC=CC=2)Cl)N=C1C1=CC=CC(F)=C1C GBUFPVUTCUTXKB-IBGZPJMESA-N 0.000 claims 1
- ZSRMRQJJIXWKDY-SFHVURJKSA-N (3s)-3-(2-chlorophenyl)-3-[[6-(4-fluoro-2-methoxyphenyl)-5-methoxypyridine-2-carbonyl]amino]propanoic acid Chemical compound COC1=CC=C(C(=O)N[C@@H](CC(O)=O)C=2C(=CC=CC=2)Cl)N=C1C1=CC=C(F)C=C1OC ZSRMRQJJIXWKDY-SFHVURJKSA-N 0.000 claims 1
- LAFMJGDCWHALMS-IBGZPJMESA-N (3s)-3-(2-chlorophenyl)-3-[[6-(4-fluoro-2-methylphenyl)-5-methoxypyridine-2-carbonyl]amino]propanoic acid Chemical compound COC1=CC=C(C(=O)N[C@@H](CC(O)=O)C=2C(=CC=CC=2)Cl)N=C1C1=CC=C(F)C=C1C LAFMJGDCWHALMS-IBGZPJMESA-N 0.000 claims 1
- FBQRJBJYPKBKHI-SFHVURJKSA-N (3s)-3-(2-chlorophenyl)-3-[[6-(5-fluoro-2-methoxyphenyl)-5-methoxypyridine-2-carbonyl]amino]propanoic acid Chemical compound COC1=CC=C(F)C=C1C1=NC(C(=O)N[C@@H](CC(O)=O)C=2C(=CC=CC=2)Cl)=CC=C1OC FBQRJBJYPKBKHI-SFHVURJKSA-N 0.000 claims 1
- MZXGTMLGLDKZPH-IBGZPJMESA-N (3s)-3-(2-chlorophenyl)-3-[[6-(5-fluoro-2-methylphenyl)-5-methoxypyridine-2-carbonyl]amino]propanoic acid Chemical compound COC1=CC=C(C(=O)N[C@@H](CC(O)=O)C=2C(=CC=CC=2)Cl)N=C1C1=CC(F)=CC=C1C MZXGTMLGLDKZPH-IBGZPJMESA-N 0.000 claims 1
- ZFZDLNLPIWZOPO-SFHVURJKSA-N (3s)-3-(2-chlorophenyl)-3-[[6-[2-fluoro-5-(trifluoromethyl)phenyl]-5-methoxypyridine-2-carbonyl]amino]propanoic acid Chemical compound COC1=CC=C(C(=O)N[C@@H](CC(O)=O)C=2C(=CC=CC=2)Cl)N=C1C1=CC(C(F)(F)F)=CC=C1F ZFZDLNLPIWZOPO-SFHVURJKSA-N 0.000 claims 1
- YMHYKJQEGWXPMT-KRWDZBQOSA-N (3s)-3-(2-fluorophenyl)-3-[[5-methoxy-6-(1,3,5-trimethylpyrazol-4-yl)pyridine-2-carbonyl]amino]propanoic acid Chemical class COC1=CC=C(C(=O)N[C@@H](CC(O)=O)C=2C(=CC=CC=2)F)N=C1C=1C(C)=NN(C)C=1C YMHYKJQEGWXPMT-KRWDZBQOSA-N 0.000 claims 1
- KZCOUVBSNMCPRK-SFHVURJKSA-N (3s)-3-(2-fluorophenyl)-3-[[5-methoxy-6-(2-methoxyphenyl)pyridine-2-carbonyl]amino]propanoic acid Chemical compound COC1=CC=CC=C1C1=NC(C(=O)N[C@@H](CC(O)=O)C=2C(=CC=CC=2)F)=CC=C1OC KZCOUVBSNMCPRK-SFHVURJKSA-N 0.000 claims 1
- XHCUNJMCBCIQFI-KRWDZBQOSA-N (3s)-3-(2-fluorophenyl)-3-[[5-methoxy-6-(2-methylfuran-3-yl)pyridine-2-carbonyl]amino]propanoic acid Chemical compound COC1=CC=C(C(=O)N[C@@H](CC(O)=O)C=2C(=CC=CC=2)F)N=C1C=1C=COC=1C XHCUNJMCBCIQFI-KRWDZBQOSA-N 0.000 claims 1
- DTDWFGLSOBMKPM-SFHVURJKSA-N (3s)-3-(2-fluorophenyl)-3-[[5-methoxy-6-[2-(trifluoromethyl)phenyl]pyridine-2-carbonyl]amino]propanoic acid Chemical compound COC1=CC=C(C(=O)N[C@@H](CC(O)=O)C=2C(=CC=CC=2)F)N=C1C1=CC=CC=C1C(F)(F)F DTDWFGLSOBMKPM-SFHVURJKSA-N 0.000 claims 1
- IPEGIOOBMMNEQR-SFHVURJKSA-N (3s)-3-(2-fluorophenyl)-3-[[6-(2-fluorophenyl)-5-methoxypyridine-2-carbonyl]amino]propanoic acid Chemical compound COC1=CC=C(C(=O)N[C@@H](CC(O)=O)C=2C(=CC=CC=2)F)N=C1C1=CC=CC=C1F IPEGIOOBMMNEQR-SFHVURJKSA-N 0.000 claims 1
- IQTZSAYJISWSDG-KRWDZBQOSA-N (3s)-3-[[6-(2,3-dichlorophenyl)-5-methoxypyridine-2-carbonyl]amino]-3-(2-fluorophenyl)propanoic acid Chemical compound COC1=CC=C(C(=O)N[C@@H](CC(O)=O)C=2C(=CC=CC=2)F)N=C1C1=CC=CC(Cl)=C1Cl IQTZSAYJISWSDG-KRWDZBQOSA-N 0.000 claims 1
- JHOZKAAYCMQEJS-KRWDZBQOSA-N (3s)-3-[[6-(2,3-difluorophenyl)-5-methoxypyridine-2-carbonyl]amino]-3-(2-fluorophenyl)propanoic acid Chemical compound COC1=CC=C(C(=O)N[C@@H](CC(O)=O)C=2C(=CC=CC=2)F)N=C1C1=CC=CC(F)=C1F JHOZKAAYCMQEJS-KRWDZBQOSA-N 0.000 claims 1
- SEYXLDWIVZUQNP-FQEVSTJZSA-N (3s)-3-[[6-(2,3-dimethylphenyl)-5-methoxypyridine-2-carbonyl]amino]-3-(2-fluorophenyl)propanoic acid Chemical compound COC1=CC=C(C(=O)N[C@@H](CC(O)=O)C=2C(=CC=CC=2)F)N=C1C1=CC=CC(C)=C1C SEYXLDWIVZUQNP-FQEVSTJZSA-N 0.000 claims 1
- RYIGJZXQPWMMCB-SFHVURJKSA-N (3s)-3-[[6-(2,4-difluorophenyl)-5-methoxypyridine-2-carbonyl]amino]-3-(2-fluorophenyl)propanoic acid Chemical compound COC1=CC=C(C(=O)N[C@@H](CC(O)=O)C=2C(=CC=CC=2)F)N=C1C1=CC=C(F)C=C1F RYIGJZXQPWMMCB-SFHVURJKSA-N 0.000 claims 1
- KKNHUGBOIIJWEY-IBGZPJMESA-N (3s)-3-[[6-(2,5-dichlorophenyl)-5-methoxypyridine-2-carbonyl]amino]-3-(2-methylphenyl)propanoic acid Chemical compound COC1=CC=C(C(=O)N[C@@H](CC(O)=O)C=2C(=CC=CC=2)C)N=C1C1=CC(Cl)=CC=C1Cl KKNHUGBOIIJWEY-IBGZPJMESA-N 0.000 claims 1
- CGFWLDSMNAOHSW-SFHVURJKSA-N (3s)-3-[[6-(2,5-difluorophenyl)-5-methoxypyridine-2-carbonyl]amino]-3-(2-fluorophenyl)propanoic acid Chemical compound COC1=CC=C(C(=O)N[C@@H](CC(O)=O)C=2C(=CC=CC=2)F)N=C1C1=CC(F)=CC=C1F CGFWLDSMNAOHSW-SFHVURJKSA-N 0.000 claims 1
- WYYSOWHMXFCTNG-KRWDZBQOSA-N (3s)-3-[[6-(2-chloro-3-fluorophenyl)-5-methoxypyridine-2-carbonyl]amino]-3-(2-chlorophenyl)propanoic acid Chemical compound COC1=CC=C(C(=O)N[C@@H](CC(O)=O)C=2C(=CC=CC=2)Cl)N=C1C1=CC=CC(F)=C1Cl WYYSOWHMXFCTNG-KRWDZBQOSA-N 0.000 claims 1
- SSSXUNZPXVHSBY-SFHVURJKSA-N (3s)-3-[[6-(2-chloro-3-methylphenyl)-5-methoxypyridine-2-carbonyl]amino]-3-(2-chlorophenyl)propanoic acid Chemical compound COC1=CC=C(C(=O)N[C@@H](CC(O)=O)C=2C(=CC=CC=2)Cl)N=C1C1=CC=CC(C)=C1Cl SSSXUNZPXVHSBY-SFHVURJKSA-N 0.000 claims 1
- MRFAAFGRBFREKJ-SFHVURJKSA-N (3s)-3-[[6-(2-chlorophenyl)-5-methoxypyridine-2-carbonyl]amino]-3-(2-fluorophenyl)propanoic acid Chemical compound COC1=CC=C(C(=O)N[C@@H](CC(O)=O)C=2C(=CC=CC=2)F)N=C1C1=CC=CC=C1Cl MRFAAFGRBFREKJ-SFHVURJKSA-N 0.000 claims 1
- BJJHKCMAJGNGJI-IBGZPJMESA-N (3s)-3-[[6-(2-fluoro-5-methylphenyl)-5-methoxypyridine-2-carbonyl]amino]-3-(2-fluorophenyl)propanoic acid Chemical compound COC1=CC=C(C(=O)N[C@@H](CC(O)=O)C=2C(=CC=CC=2)F)N=C1C1=CC(C)=CC=C1F BJJHKCMAJGNGJI-IBGZPJMESA-N 0.000 claims 1
- BAGKUCVGWOLRNO-INIZCTEOSA-N (3s)-3-[[6-(3,5-dimethyl-1,2-oxazol-4-yl)-5-methoxypyridine-2-carbonyl]amino]-3-(2-fluorophenyl)propanoic acid Chemical compound COC1=CC=C(C(=O)N[C@@H](CC(O)=O)C=2C(=CC=CC=2)F)N=C1C=1C(C)=NOC=1C BAGKUCVGWOLRNO-INIZCTEOSA-N 0.000 claims 1
- QGQBSIZHUOTCGY-KRWDZBQOSA-N (3s)-3-[[6-(3-chloro-2-fluorophenyl)-5-methoxypyridine-2-carbonyl]amino]-3-(2-chlorophenyl)propanoic acid Chemical compound COC1=CC=C(C(=O)N[C@@H](CC(O)=O)C=2C(=CC=CC=2)Cl)N=C1C1=CC=CC(Cl)=C1F QGQBSIZHUOTCGY-KRWDZBQOSA-N 0.000 claims 1
- QMYVIHFJAPEKPX-KRWDZBQOSA-N (3s)-3-[[6-(3-chloro-2-fluorophenyl)-5-methoxypyridine-2-carbonyl]amino]-3-(2-fluorophenyl)propanoic acid Chemical compound COC1=CC=C(C(=O)N[C@@H](CC(O)=O)C=2C(=CC=CC=2)F)N=C1C1=CC=CC(Cl)=C1F QMYVIHFJAPEKPX-KRWDZBQOSA-N 0.000 claims 1
- DJRMBHMJCXEVPL-IBGZPJMESA-N (3s)-3-[[6-(3-chloro-2-methylphenyl)-5-methoxypyridine-2-carbonyl]amino]-3-(2-chlorophenyl)propanoic acid Chemical compound COC1=CC=C(C(=O)N[C@@H](CC(O)=O)C=2C(=CC=CC=2)Cl)N=C1C1=CC=CC(Cl)=C1C DJRMBHMJCXEVPL-IBGZPJMESA-N 0.000 claims 1
- JFEQIYJMSCEIOW-IBGZPJMESA-N (3s)-3-[[6-(3-chloro-2-methylphenyl)-5-methoxypyridine-2-carbonyl]amino]-3-(2-fluorophenyl)propanoic acid Chemical compound COC1=CC=C(C(=O)N[C@@H](CC(O)=O)C=2C(=CC=CC=2)F)N=C1C1=CC=CC(Cl)=C1C JFEQIYJMSCEIOW-IBGZPJMESA-N 0.000 claims 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/44—Radicals substituted by doubly-bound oxygen, sulfur, or nitrogen atoms, or by two such atoms singly-bound to the same carbon atom
- C07D213/46—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- 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
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P11/06—Antiasthmatics
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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Claims (12)
1. Spoj s formulom I, u bilo kojem od njegovih stereoizomernih oblika ili smjesa stereoizomernih oblika u bilo kojem omjeru, ili njegova fiziološki prihvatljiva sol, ili fiziološki prihvatljiv solvat bilo kojeg od njih,
[image]
naznačen time da
A je odabran iz niza koji sadrži C(R1) i N;
D je odabran iz niza koji sadrži C(R2) i N;
E je odabran iz niza koji sadrži C(R3);
L je odabran iz niza koji sadrži C(R4) i N;
gdje barem jedan i najviše dva od A, D ili L je N;
G je odabran iz niza koji sadrži R71-O-C(O)-, R72-N(R73)-C(O)- i tetrazol-5-il;
R1 je odabran iz niza koji sadrži vodik, halogen, (C1-C6)-alkil, HO-, (C1-C6)-alkil-O-, (C1-C6)-alkil-S(O)m- i NC-;
R2 je odabran iz niza koji sadrži vodik, halogen, (C1-C7)-alkil, (C1-C6)-alkil-O-, (C1-C6)-alkil-CO-, (C1-C6)-alkil-CO-HN-, -NR12R13, Het2, (C3-C7)-cikloalkil-CsH2s- i Ar-CsH2s-, pri čemu s je cijeli broj izabran iz niza koji sadrži 0, 1, 2 i 3;
R3 je R11-O-;
R4 je odabran iz niza koji sadrži vodik, halogen, (C1-C6)-alkil, (C1-C6)-alkil-O-, HO-, NR12R13, Het2;
R10 je odabran iz niza koji sadrži vodik, halogen, (C1-C6)-alkil, (C1-C6)-alkil-O-, (C1-C6)-alkil-S(O)m-, HO-, -NR12R13, Het2, fenil-CsH2s-(O)t-, pri čemu s je cijeli broj izabran iz niza koji sadrži 0, 1, 2 i 3, te pri čemu t je cijeli broj izabran iz niza koji sadrži 0 i 1;
uz uvjet da jedan od R1, R2, R3, R4 ili R10 je ciklički supstituent;
R11 je odabran iz niza koji sadrži vodik i (C1-C10)-alkil;
R12 i R13 su međusobno neovisno izabrani iz niza koji sadrži vodik i R15;
R15 je (C1-C6)-alkil koji je proizvoljno supstituiran s jednim ili više istih ili različitih supstituenata odabranih iz niza koji čine halogen, HO- i (C1-C6)-alkil-O-;
R30 je odabran iz niza koji sadrži R31, (C3-C7)-cikloalkil, R32-CuH2u- i Het3-CuH2u-, pri čemu u je cijeli broj izabran iz niza koji sadrži 0, 1, 2 i 3;
R31 je (C1-C10)-alkil koji je proizvoljno supstituiran s jednim ili više jednakih ili različitih supstituenta odabranih iz niza koji čine halogen, (C3-C7)-cikloalkil, HO-, (C1-C6)-alkil-O-, (C1-C6)-alkil-S(O)m- i NC-;
R32 je odabran iz niza koji sadrži fenil i aromatski 5-člani ili 6-člani monociklički heterocikl koji sadrži jedan, dva ili tri jednaka ili različita heteroatoma u prstenu odabrana iz niza koji sadrži dušik, kisik i sumpor i vezan je preko atoma ugljika u prstenu, pri čemu su fenil i heterocikl svi proizvoljno supstituirani s jednim ili više jednakih ili različitih supstituenta odabranih iz niza koji čine halogen, (C1-C6)-alkil, (C3-C7)-cikloalkil, R33, HO-, (C1-C6)-alkil-O-, R33-O-, R33-(C1-C4)-alkil-O-, -O-CH2-O-, -O-CF2-O-, (C1-C6)-alkil-S(O)m-, H2N-S(O)2-, (C1-C4)-alkil-NH-S(O)2-, di((C1-C4)-alkil)N-S(O)2-, H2N-, (C1-C6)-alkil-NH-, di((C1-C6)-alkil)N-, Het1, (C1-C4)-alkil-C(O)-NH-, Ar-C(O)-NH-, (C1-C4)-alkil-S(O)2-NH- i NC-;
R33 je odabran iz niza koji sadrži fenil i aromatski 5-člani ili 6-člani monociklički heterocikl koji sadrži jedan, dva ili tri jednaka ili različita heteroatoma u prstenu odabrana iz niza koji sadrži dušik, kisik i sumpor i vezan je preko atoma ugljika u prstenu, pri čemu su fenil i heterocikl svi proizvoljno supstituirani s jednim ili više jednakih ili različitih supstituenta odabranih iz niza koji čine halogen, (C1-C6)-alkil, (C3-C7)-cikloalkil, HO-, (C1-C6)-alkil-O-, (C1-C6)-alkil-S(O)m-, H2N-S(O)2-, (C1-C4)-alkil-NH-S(O)2-, di((C1-C4)-alkil)N-S(O)2- i NC-;
R40 je odabran iz niza koji sadrži vodik i (C1-C4)-alkil;
ili R30 i R40 zajedno su (CH2)x koji je proizvoljno supstituiran s jednim ili više istih ili različitih (C1-C4)-alkil supstituenata, pri čemu x je cijeli broj izabran iz niza koji sadrži 2, 3, 4 i 5;
R50 je vodik;
R60 je vodik;
R71 je odabran iz niza koji sadrži vodik i (C1-C8)-alkil koji je proizvoljno supstituiran s jednim ili više istih ili različitih supstituenata odabranih iz niza koji čine (C1-C6)-alkil-O- i (C1-C6)-alkil-C(O)-O-;
R72 i R73 su međusobno neovisno izabrani iz niza koji sadrži vodik i (C1-C2)-alkil -;
Ar, neovisno jedna od druge skupine Ar, je odabrana iz niza koji sadrži fenil i aromatski 6-člani monociklički heterocikl koji sadrži jedan, dva ili tri jednaka ili različita heteroatoma u prstenu odabrana iz niza koji sadrži dušik, kisik i sumpor i vezana je preko atoma ugljika u prstenu, pri čemu su fenil i heterocikl svi proizvoljno supstituirani s jednim ili više jednakih ili različitih supstituenta odabranih iz niza koji čine halogen, (C1-C6)-alkil, HO-(C1-C6)-alkil, Het4, -(CH2)x-fenil, (C1-C6)-alkil-O-, (C3-C7)-cikloalkil-(CH2)x-O-, -CF3, -CO-(C1-C6)-alkil, -NR12R13, Het2, -CO-NR12R13, CO-Het2, (C1-C6)-alkil-S(O)m-, H2N-S(O)2- i NC-;
i pri čemu fenil može biti supstituiran s -CH=CH-CH=CH-, -O-CH2-O-, -O-CH2-CH2-O-, -O-CF2-O- ili -N((C1-C3)-alkil)-CH=CH-;
Het1, neovisno jedna od druge skupine Het1, je zasićeni ili nezasićeni 4-člani do 8-člani monociklički heterocikl koji sadrži dušikov atom prstena preko kojeg je Het1 vezan i proizvoljno jedan ili dva ista ili različita dodatna heteroatoma u prstenu odabrana iz niza koji čine dušik, kisik i sumpor, koji je proizvoljno supstituiran s jednim ili više jednakih ili različitih supstituenta odabranih iz niza koji čine halogen, (C1-C4)-alkil, HO-, (C1-C4)-alkil-O-, okso i NC-;
Het2 je zasićeni 4-člani do 7-člani monociklički heterocikl koji sadrži dušikov atom prstena preko kojeg je Het2 vezan i proizvoljno jedan dodatni heteroatom u prstenu odabran iz niza koji čine dušik, kisik i sumpor, koji je proizvoljno supstituiran s jednim ili više jednakih ili različitih supstituenta odabranih iz niza koji čine halogen, (C1-C4)-alkil, HO- i (C1-C4)-alkil-O-;
Het3, neovisno jedna od druge skupine Het3, je zasićeni 4-člani do 7-člani monociklički heterocikl koji sadrži jedan ili dva ista ili različita heteroatoma u prstenu odabrana iz niza koji čine dušik, kisik i sumpor i vezan je preko atoma ugljika u prstenu, koji je proizvoljno supstituiran s jednim ili više jednakih ili različitih supstituenta odabranih iz niza koji čine fluor, (C1-C4)-alkil i okso;
m, međusobno neovisno je broj m, koji je cijeli broj izabran iz niza koji sadrži 0, 1 i 2;
pri čemu sve cikloalkilne skupine, međusobno neovisno, su proizvoljno supstituirane s jednim ili više jednakih ili različitih supstituenta odabranih iz niza koji čine fluor i (C1-C4)-alkil;
pri čemu sve skupine alkil, CsH2s, CuH2u i (CH2)x, međusobno neovisno, i neovisno od bilo kojih drugih supstituenata, su proizvoljno supstituirane s jednim ili više fluorovih supstituenata.
2. Spoj s formulom I, u bilo kojem od njegovih stereoizomernih oblika ili smjesa stereoizomernih oblika u bilo kojem omjeru, ili njegova fiziološki prihvatljiva sol, ili fiziološki prihvatljiv solvat bilo kojeg od njih, kako je zatraženo u zahtjevu 1, naznačen time da
G je odabran iz niza koji sadrži R71-O-C(O)- i R72-N(R73)-C(O)-;
R30 je R32-CuH2u-, pri čemu u je cijeli broj izabran iz niza koji sadrži 0 i 1;
R32 je odabran iz niza koji sadrži fenil i aromatski 6-člani monociklički heterocikl koji sadrži jedan ili dva dušikova atoma kao heteroatome prstena, pri čemu su fenil i heterocikl svi proizvoljno supstituirani s jednim ili više jednakih ili različitih supstituenta odabranih iz niza koji čine halogen, (C1-C6)-alkil, (C3-C7)-cikloalkil, R33, HO-, (C1-C6)-alkil-O-, R33-O-, R33-(C1-C4)-alkil-O-, -O-CH2-O-, -O-CF2-O-, (C1-C6)-alkil-S(O)m-, di((C1-C4)-alkil)N-S(O)2-, H2N-, di((C1-C6)-alkil)N-, Het1, (C1-C4)-alkil-C(O)-NH-, Ar-C(O)-NH- i NC-;
R33 je odabran iz niza koji sadrži fenil i aromatski 6-člani monociklički heterocikl koji sadrži jedan ili dva dušikova atoma kao heteroatome prstena, pri čemu su fenil i heterocikl svi proizvoljno supstituirani s jednim ili više jednakih ili različitih supstituenta odabranih iz niza koji čine halogen, (C1-C6)-alkil, (C3-C7)-cikloalkil, HO-, (C1-C6)-alkil-O-, (C1-C6)-alkil-S(O)m-, H2N-S(O)2-, di((C1-C4)-alkil)N-S(O)2- i NC-;
R40 je vodik.
3. Spoj s formulom I, u bilo kojem od njegovih stereoizomernih oblika ili smjesa stereoizomernih oblika u bilo kojem omjeru, ili njegova fiziološki prihvatljiva sol, ili fiziološki prihvatljiv solvat bilo kojeg od njih, prema bilo kojem ili više od zahtjeva 1 i 2, naznačen time da
G je R71-O-C(O)-;
R30 je R32 -CuH2u-, pri čemu u je 0;
R32 je odabran iz niza koji sadrži fenil, pri čemu je fenil proizvoljno supstituiran s jednim ili više jednakih ili različitih supstituenta odabranih iz niza koji čine halogen, (C1-C6)-alkil, (C3-C7)-cikloalkil, R33, HO-, (C1-C6)-alkil-O-, R33-O-, R33-(C1-C4)-alkil-O-, -O-CH2-O-, -O-CF2-O-, (C1-C6)-alkil-S(O)m-, di((C1-C4)-alkil)N-S(O)2-, H2N-, di((C1-C6)-alkil)N-, Het1, (C1-C4)-alkil-C(O)-NH-, Ar-C(O)-NH-i NC-;
R33 je odabran iz niza koji sadrži fenil, pri čemu je fenil proizvoljno supstituiran s jednim ili više jednakih ili različitih supstituenta odabranih iz niza koji čine halogen, (C1-C6)-alkil, (C3-C7)-cikloalkil, HO-, (C1-C6)-alkil-O-, (C1-C6)-alkil-S(O)m-, H2N-S(O)2-, di((C1-C4)-alkil)N-S(O)2- i NC-;
R40 je vodik.
4. Spoj s formulom I, u bilo kojem od njegovih stereoizomernih oblika ili smjesa stereoizomernih oblika u bilo kojem omjeru, ili njegova fiziološki prihvatljiva sol, ili fiziološki prihvatljiv solvat bilo kojeg od njih, prema bilo kojem ili više od zahtjeva 1 do 3, naznačen time da formula I je odabrana iz niza podformula I-1, I-2, I-4 i I-6
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5. Spoj s formulom I-1, u bilo kojem od njegovih stereoizomernih oblika ili smjesa stereoizomernih oblika u bilo kojem omjeru, ili njegova fiziološki prihvatljiva sol, ili fiziološki prihvatljiv solvat bilo kojeg od njih, kako je zatraženo u zahtjevu 4, naznačen time da
[image]
R2 je Ar-CsH2s-, pri čemu s je cijeli broj izabran iz niza koji sadrži 0;
R3 je odabran iz niza koji sadrži vodik, halogen, R11-O-, HO-, (C1-C6)-alkil i (C1-C6)-alkil-O-; poželjno HO- i (C1-C6)-alkil
R4 je vodik;
R10 je vodik.
6. Spoj s formulom I, u bilo kojem od njegovih stereoizomernih oblika ili smjesa stereoizomernih oblika u bilo kojem omjeru, ili njegova fiziološki prihvatljiva sol, ili fiziološki prihvatljiv solvat bilo kojeg od njih, prema bilo kojem ili više od zahtjeva 4 do 5, naznačen time da
R3 je -O-CH3.
7. Spoj s formulom I, ili njegova fiziološki prihvatljiva sol, ili fiziološki prihvatljiv solvat bilo kojeg od njih, prema bilo kojem ili više od zahtjeva 1 do 6, naznačen time da se bira od:
(S)-3-[(5-metoksi-6-fenil-piridin-2-karbonil)-amino]-3-o-tolil-propanske kiseline
(S)-3-(2,4-diklor-fenil)-3-[(5-metoksi-6-fenil-piridin-2-karbonil)-amino]-propanske kiseline
(S)-3-{[6-(2-fluor-fenil)-5-metoksi-piridin-2-karbonil]-amino}-3-o-tolil-propanske kiseline
(S)-3-[(5-metoksi-6-fenil-piridin-2-karbonil)-amino]-3-p-tolil-propanske kiseline
(S)-3-[(5-metoksi-6-o-tolil-piridin-2-karbonil)-amino]-3-p-tolil-propanske kiseline
(S)-3-{[5-metoksi-6-(2-trifluormetil-fenil)-piridin-2-karbonil]-amino}-3-p-tolil-propanske kiseline
(S)-3-{[6-(3-fluor-fenil)-5-metoksi-piridin-2-karbonil]-amino}-3-p-tolil-propanske kiseline
(S)-3-{[5-metoksi-6-(2-metoksi-fenil)-piridin-2-karbonil]-amino}-3-p-tolil-propanske kiseline
(S)-3-{[6-(2-klor-fenil)-5-metoksi-piridin-2-karbonil]-amino}-3-p-tolil-propanske kiseline
(S)-3-{[6-(2-fluor-fenil)-5-metoksi-piridin-2-karbonil]-amino}-3-p-tolil-propanske kiseline
(S)-3-{[6-(2,4-difluor-fenil)-5-metoksi-piridin-2-karbonil]-amino}-3-p-tolil-propanske kiseline
(S)-3-{[6-(2,3-diklor-fenil)-5-metoksi-piridin-2-karbonil]-amino}-3-p-tolil-propanske kiseline
(S)-3-{[6-(2-klor-5-trifluormetil-fenil)-5-metoksi-piridin-2-karbonil]-amino}-3-p-tolil-propanske kiseline
(S)-3-{[6-(3-fluor-2-metil-fenil)-5-metoksi-piridin-2-karbonil]-amino}-3-(2-fluor-fenil)-propanske kiseline
(S)-3-{[6-(2-klor-5-trifluormetil-fenil)-5-metoksi-piridin-2-karbonil]-amino}-3-(2-fluor-fenil)-propanske kiseline
(S)-3-{[6-(2,3-difluor-fenil)-5-metoksi-piridin-2-karbonil]-amino}-3-p-tolil-propanske kiseline
(S)-3-{[6-(2,5-difluor-fenil)-5-metoksi-piridin-2-karbonil]-amino}-3-p-tolil-propanske kiseline
(S)-3-{[6-(2,5-diklor-fenil)-5-metoksi-piridin-2-karbonil]-amino}-3-p-tolil-propanske kiseline
(S)-3-{[6-(3,5-dimetil-izoksazol-4-il)-5-metoksi-piridin-2-karbonil]-amino}-3-p-tolil-propanske kiseline
(S)-3-{[6-(4-fluor-2-metil-fenil)-5-metoksi-piridin-2-karbonil]-amino}-3-p-tolil-propanske kiseline
(S)-3-{[6-(2,3-dimetil-fenil)-5-metoksi-piridin-2-karbonil]-amino}-3-p-tolil-propanske kiseline
(S)-3-{[6-(5-fluor-2-metil-fenil)-5-metoksi-piridin-2-karbonil]-amino}-3-p-tolil-propanske kiseline
(S)-3-{[6-(4-fluor-2-metoksi-fenil)-5-metoksi-piridin-2-karbonil]-amino}-3-p-tolil-propanske kiseline
(S)-3-{[6-(5-fluor-2-metoksi-fenil)-5-metoksi-piridin-2-karbonil]-amino}-3-p-tolil-propanske kiseline
(S)-3-{[6-(2-fluor-5-metil-fenil)-5-metoksi-piridin-2-karbonil]-amino}-3-p-tolil-propanske kiseline
(S)-3-{[6-(3-klor-2-metil-fenil)-5-metoksi-piridin-2-karbonil]-amino}-3-p-tolil-propanske kiseline
(S)-3-{[6-(3-fluor-2-metil-fenil)-5-metoksi-piridin-2-karbonil]-amino}-3-p-tolil-propanske kiseline
(S)-3-{[6-(5-klor-2-fluor-fenil)-5-metoksi-piridin-2-karbonil]-amino}-3-p-tolil-propanske kiseline
(S)-3-(2-fluor-fenil)-3-[(5-metoksi-6-fenil-piridin-2-karbonil)-amino]-propanske kiseline
(S)-3-{[6-(2,4-diklor-fenil)-5-metoksi-piridin-2-karbonil]-amino}-3-(2-fluor-fenil)-propanske kiseline
(S)-3-(2-fluor-fenil)-3-[(5-metoksi-6-o-tolil-piridin-2-karbonil)-amino]-propanske kiseline
(S)-3-(2-fluor-fenil)-3-{[5-metoksi-6-(2-trifluormetil-fenil)-piridin-2-karbonil]-amino}-propanske kiseline
(S)-3-(2-fluor-fenil)-3-{[5-metoksi-6-(2-metoksi-fenil)-piridin-2-karbonil]-amino}-propanske kiseline
(S)-3-{[6-(2-klor-fenil)-5-metoksi-piridin-2-karbonil]-amino}-3-(2-fluor-fenil)-propanske kiseline
(S)-3-(2-fluor-fenil)-3-{[6-(2-fluor-fenil)-5-metoksi-piridin-2-karbonil]-amino}-propanske kiseline
(S)-3-{[6-(2,4-difluor-fenil)-5-metoksi-piridin-2-karbonil]-amino}-3-(2-fluor-fenil)-propanske kiseline
(S)-3-{[6-(2,3-diklor-fenil)-5-metoksi-piridin-2-karbonil]-amino}-3-(2-fluor-fenil)-propanske kiseline
(S)-3-{[6-(2,3-difluor-fenil)-5-metoksi-piridin-2-karbonil]-amino}-3-(2-fluor-fenil)-propanske kiseline
(S)-3-{[6-(2,5-difluor-fenil)-5-metoksi-piridin-2-karbonil]-amino}-3-(2-fluor-fenil)-propanske kiseline
(S)-3-{[6-(4-fluor-2-metil-fenil)-5-metoksi-piridin-2-karbonil]-amino}-3-(2-fluor-fenil)-propanske kiseline
(S)-3-{[6-(3,5-dimetil-izoksazol-4-il)-5-metoksi-piridin-2-karbonil]-amino}-3-(2-fluor-fenil)-propanske kiseline
(S)-3-{[6-(2,3-dimetil-fenil)-5-metoksi-piridin-2-karbonil]-amino}-3-(2-fluor-fenil)-propanske kiseline
(S)-3-{[6-(5-fluor-2-metil-fenil)-5-metoksi-piridin-2-karbonil]-amino}-3-(2-fluor-fenil)-propanske kiseline
(S)-3-{[6-(4-fluor-2-metoksi-fenil)-5-metoksi-piridin-2-karbonil]-amino}-3-(2-fluor-fenil)-propanske kiseline
(S)-3-{[6-(5-fluor-2-metoksi-fenil)-5-metoksi-piridin-2-karbonil]-amino}-3-(2-fluor-fenil)-propanske kiseline
(S)-3-{[6-(2-fluor-5-metil-fenil)-5-metoksi-piridin-2-karbonil]-amino}-3-(2-fluor-fenil)-propanske kiseline
(S)-3-{[6-(3-klor-2-metil-fenil)-5-metoksi-piridin-2-karbonil]-amino}-3-(2-fluor-fenil)-propanske kiseline
(S)-3-{[6-(5-klor-2-fluor-fenil)-5-metoksi-piridin-2-karbonil]-amino}-3-(2-fluor-fenil)-propanske kiseline
(S)-3-{[6-(3-klor-2-fluor-fenil)-5-metoksi-piridin-2-karbonil]-amino}-3-(2-fluor-fenil)-propanske kiseline
(S)-3-(2-fluor-fenil)-3-{[5-metoksi-6-(2-metil-furan-3-il)-piridin-2-karbonil]-amino}-propanske kiseline
(S)-3-{[6-(2-klor-3-metil-fenil)-5-metoksi-piridin-2-karbonil]-amino}-3-(2-fluor-fenil)-propanske kiseline
(S)-3-(2-klor-fenil)-3-[(5-metoksi-6-fenil-piridin-2-karbonil)-amino]-propanske kiseline
(S)-3-(2-klor-fenil)-3-{[6-(2,4-diklor-fenil)-5-metoksi-piridin-2-karbonil]-amino}-propanske kiseline
(S)-3-(2-klor-fenil)-3-{[6-(4-fluor-fenil)-5-metoksi-piridin-2-karbonil]-amino}-propanske kiseline
(S)-3-{[5-metoksi-6-(3-trifluormetil-fenil)-piridin-2-karbonil]-amino}-3-o-tolil-propanske kiseline
(S)-3-{[6-(2,4-diklor-fenil)-5-metoksi-piridin-2-karbonil]-amino}-3-o-tolil-propanske kiseline
(S)-3-{[6-(4-fluor-fenil)-5-metoksi-piridin-2-karbonil]-amino}-3-o-tolil-propanske kiseline
(S)-3-{[6-(4-klor-fenil)-5-metoksi-piridin-2-karbonil]-amino}-3-o-tolil-propanske kiseline
(S)-3-[(5-metoksi-6-p-tolil-piridin-2-karbonil)-amino]-3-o-tolil-propanske kiseline
(S)-3-{[6-(3-klor-fenil)-5-metoksi-piridin-2-karbonil]-amino}-3-o-tolil-propanske kiseline
(S)-3-{[5-metoksi-6-(2-metoksi-fenil)-piridin-2-karbonil]-amino}-3-o-tolil-propanske kiseline
(S)-3-[(5-metoksi-6-m-tolil-piridin-2-karbonil)-amino]-3-o-tolil-propanske kiseline
(S)-3-{[6-(2-klor-fenil)-5-metoksi-piridin-2-karbonil]-amino}-3-o-tolil-propanske kiseline
(S)-3-{[6-(3,4-difluor-fenil)-5-metoksi-piridin-2-karbonil]-amino}-3-o-tolil-propanske kiseline
(S)-3-{[6-(2,5-difluor-fenil)-5-metoksi-piridin-2-karbonil]-amino}-3-o-tolil-propanske kiseline
(S)-3-{[6-(2,5-diklor-fenil)-5-metoksi-piridin-2-karbonil]-amino}-3-o-tolil-propanske kiseline
(S)-3-{[6-(3,5-dimetil-izoksazol-4-il)-5-metoksi-piridin-2-karbonil]-amino}-3-O-tolil-propanske kiseline
(S)-3-{[6-(2,3-dimetil-fenil)-5-metoksi-piridin-2-karbonil]-amino}-3-o-tolil-propanske kiseline
(S)-3-{[6-(2,4-dimetil-fenil)-5-metoksi-piridin-2-karbonil]-amino}-3-o-tolil-propanske kiseline
(S)-3-{[6-(4-fluor-2-metoksi-fenil)-5-metoksi-piridin-2-karbonil]-amino}-3-O-tolil-propanske kiseline
(S)-3-{[6-(2-klor-5-metil-fenil)-5-metoksi-piridin-2-karbonil]-amino}-3-O-tolil-propanske kiseline
(S)-3-(2-klor-fenil)-3-[(6-metoksi-5-o-tolil-piridin-3-karbonil)-amino]-propanske kiseline
(S)-3-(2-klor-fenil)-3-{[5-metoksi-6-(2-metoksi-fenil)-piridin-2-karbonil]-amino}-propanske kiseline
(S)-3-(2-klor-fenil)-3-[(5-metoksi-6-m-tolil-piridin-2-karbonil)-amino]-propanske kiseline
(S)-3-(2-klor-fenil)-3-{[6-(2-klor-fenil)-5-metoksi-piridin-2-karbonil]-amino}-propanske kiseline
(S)-3-(2-klor-fenil)-3-{[6-(2-fluor-fenil)-5-metoksi-piridin-2-karbonil]-amino}-propanske kiseline
(S)-3-(2-klor-fenil)-3-{[6-(2,4-difluor-fenil)-5-metoksi-piridin-2-karbonil]-amino}-propanske kiseline
(S)-3-(2-klor-fenil)-3-{[6-(2,3-diklor-fenil)-5-metoksi-piridin-2-karbonil]-amino}-propanske kiseline
(S)-3-(2-klor-fenil)-3-{[6-(2,3-difluor-fenil)-5-metoksi-piridin-2-karbonil]-amino}-propanske kiseline
(S)-3-(2-klor-fenil)-3-{[6-(2,5-difluor-fenil)-5-metoksi-piridin-2-karbonil]-amino}-propanske kiseline
(S)-3-(2-klor-fenil)-3-{[6-(4-fluor-2-metil-fenil)-5-metoksi-piridin-2-karbonil]-amino}-propanske kiseline
(S)-3-(2-klor-fenil)-3-{[6-(2,3-dimetil-fenil)-5-metoksi-piridin-2-karbonil]-amino}-propanske kiseline
(S)-3-(2-klor-fenil)-3-{[6-(5-fluor-2-metil-fenil)-5-metoksi-piridin-2-karbonil]-amino}-propanske kiseline
(S)-3-(2-klor-fenil)-3-{[6-(4-fluor-2-metoksi-fenil)-5-metoksi-piridin-2-karbonil]-amino}-propanske kiseline
(S)-3-{[6-(4-klor-2-metoksi-fenil)-5-metoksi-piridin-2-karbonil]-amino}-3-(2-klor-fenil)-propanske kiseline
(S)-3-(2-klor-fenil)-3-{[6-(5-fluor-2-metoksi-fenil)-5-metoksi-piridin-2-karbonil]-amino}-propanske kiseline
(S)-3-(2-klor-fenil)-3-{[6-(2-fluor-5-trifluormetil-fenil)-5-metoksi-piridin-2-karbonil]-amino}-propanske kiseline
(S)-3-{[5-metoksi-6-(2-trifluormetil-fenil)-piridin-2-karbonil]-amino}-3-o-tolil-propanske kiseline
(S)-3-{[6-(2,4-difluor-fenil)-5-metoksi-piridin-2-karbonil]-amino}-3-o-tolil-propanske kiseline
(S)-3-{[6-(4-fluor-2-metil-fenil)-5-metoksi-piridin-2-karbonil]-amino}-3-o-tolil-propanske kiseline
(S)-3-{[6-(4-cijano-2-fluor-fenil)-5-metoksi-piridin-2-karbonil]-amino}-3-O-tolil-propanske kiseline
(S)-3-(2-klor-fenil)-3-{[6-(2-fluor-5-metoksi-fenil)-5-metoksi-piridin-2-karbonil]-amino}-propanske kiseline
(S)-3-(2-klor-fenil)-3-{[6-(2-fluor-5-metil-fenil)-5-metoksi-piridin-2-karbonil]-amino}-propanske kiseline
(S)-3-{[6-(3-klor-2-metil-fenil)-5-metoksi-piridin-2-karbonil]-amino}-3-(2-klor-fenil)-propanske kiseline
(S)-3-(2-klor-fenil)-3-{[6-(3-fluor-2-metil-fenil)-5-metoksi-piridin-2-karbonil]-amino}-propanske kiseline
(S)-3-{[6-(5-klor-2-fluor-fenil)-5-metoksi-piridin-2-karbonil]-amino}-3-(2-klor-fenil)-propanske kiseline
(S)-3-(2-klor-fenil)-3-[(5-metoksi-6-pirazin-2-il-piridin-2-karbonil)-amino]-propanske kiseline
(S)-3-{[6-(3-klor-2-fluor-fenil)-5-metoksi-piridin-2-karbonil]-amino}-3-(2-klor-fenil)-propanske kiseline
(S)-3-(2-klor-fenil)-3-{[5-metoksi-6-(2-metil-furan-3-il)-piridin-2-karbonil]-amino}-propanske kiseline
(S)-3-{[6-(2-klor-3-fluor-fenil)-5-metoksi-piridin-2-karbonil]-amino}-3-(2-klor-fenil)-propanske kiseline
(S)-3-{[6-(2-klor-3-metil-fenil)-5-metoksi-piridin-2-karbonil]-amino}-3-(2-klor-fenil)-propanske kiseline.
8. Spoj s formulom I, ili njegova fiziološki prihvatljiva sol, ili fiziološki prihvatljiv solvat bilo kojeg od njih, prema bilo kojem ili više od zahtjeva 1 do 6, naznačen time da se bira od
(S)-3-[(5-metoksi-6-fenil-piridin-2-karbonil)-amino]-3-o-tolil-propanske kiseline
(S)-3-(2,4-diklor-fenil)-3-[(5-metoksi-6-fenil-piridin-2-karbonil)-amino]-propanske kiseline
(S)-3-[(5-fenil-piridin-2-karbonil)-amino]-3-o-tolil-propanske kiseline
(S)-3-(2-klor-fenil)-3-[(5-metoksi-6-naftalen-2-il-piridin-2-karbonil)-amino]-propanske kiseline
(S)-3-(2-klor-fenil)-3-[(5-metoksi-6-pirazin-2-il-piridin-2-karbonil)-amino]-propanske kiseline
(S)-3-(2-klor-fenil)-3-[(6-metoksi-5-naftalen-2-il-piridin-3-karbonil)-amino]-propanske kiseline
(S)-3-(2-klor-fenil)-3-{[6-(2,3-dimetil-fenil)-5-metoksi-piridin-2-karbonil]-amino}-propanske kiseline
(S)-3-(2-klor-fenil)-3-{[6-(2-klor-fenil)-5-metoksi-piridin-2-karbonil]-amino}-propanske kiseline
(S)-3-(2-fluor-fenil)-3-{[5-metoksi-6-(1,3,5-trimetil-1H-pirazol-4-il)-piridin-2-karbonil]-amino}-propanske kiseline
(S)-3-(2-fluor-fenil)-3-{[5-metoksi-6-(1-metil-1H-indol-5-il)-piridin-2-karbonil]-amino}-propanske kiseline
(S)-3-[(5-metoksi-6-m-tolil-piridin-2-karbonil)-amino]-3-o-tolil-propanske kiseline
(S)-3-{[6-(2-klor-fenil)-5-metoksi-piridin-2-karbonil]-amino}-3-o-tolil-propanske kiseline
(S)-3-{[6-(3,5-dimetil-izoksazol-4-il)-5-metoksi-piridin-2-karbonil]-amino}-3-o-tolil-propanske kiseline
(S)-3-{[6-(4-klor-fenil)-5-metoksi-piridin-2-karbonil]-amino}-3-o-tolil-propanske kiseline
(S)-3-{[6-(4-klor-fenil)-5-metoksi-piridin-2-karbonil]-amino}-3-p-tolil-propanske kiseline
(S)-3-{[6-(5-Acetil-tiofen-2-il)-5-metoksi-piridin-2-karbonil]-amino}-3-(2-klor-fenil)-propanske kiseline
(S)-3-{[6-(2-fluor-fenil)-5-metoksi-piridin-2-karbonil]-amino}-3-o-tolil-propanske kiseline.
9. Postupak za dobivanje spoja s formulom I ili njegove fiziološki prihvatljive soli ili fiziološki prihvatljivog solvata bilo kojeg od njih prema bilo kojem ili više od zahtjeva 1 do 8, koji sadrži reakciju spoja s formulom II sa spojem s formulom III,
[image]
naznačen time da skupine A, D, E, L, G, R10, R30, R40, R50 i R60 u spojevima s formulama II i III su definirane kao u spojevima formule I, te dodatne funkcionalne skupine mogu biti prisutne u zaštićenom obliku ili u obliku prekursorskih skupina, i skupina J u spoju s formulom II je HO-, (C1-C4)-alkil-O- ili halogen.
10. Spoj s formulom I prema bilo kojem ili više od zahtjeva 1 do 8 ili njegova fiziološki prihvatljiva sol ili fiziološki prihvatljiv solvat bilo kojeg od njih naznačen time da je za uporabu kao farmaceutski proizvod.
11. Farmaceutski pripravak, naznačen time da sadrži barem jedan spoj s formulom I prema bilo kojem ili više od zahtjeva 1 do 8 ili njegova fiziološki prihvatljiva sol ili fiziološki prihvatljiv solvat bilo kojeg od njih i farmaceutski prihvatljiv nosač.
12. Uporaba spoja s formulom I prema bilo kojem ili više od zahtjeva 1 do 8 ili njegove fiziološki prihvatljive soli ili fiziološki prihvatljivog solvata bilo kojeg od njih naznačena time da je za proizvodnju lijeka za liječenje zatajenja srca, kongestivnog zatajenja srca, kardiomiopatije, infarkta miokarda, lijeve ventrikularne disfunkcije, srčane hipertrofije, valvularnih bolesti srca, hipertenzije, ateroskleroze, periferne arterijske okluzivne bolesti, restenoze, poremećaja vaskularne propusnosti, liječenje edema, tromboze, reumatoidnog artritisa, osteoartritisa, zatajenja bubrega, cistične fibroze, kroničnog bronhitisa, kronične opstruktivne plućne bolesti, astme, imunoloških bolesti, komplikacija povezanih s dijabetesom, fibroznih bolesti, boli, ishemije ili reperfuzijskog oštećenja ili neurodegenerativnih bolesti, ili za kardioprotekciju ili renoprotekciju ili kao diuretik (sa samostalno liječenje ili u kombinaciji s utvrđenim diureticima).
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WO2014053533A1 (en) | 2012-10-05 | 2014-04-10 | Sanofi | Use of substituted 3-heteroaroylamino-propionic acid derivatives as pharmaceuticals for prevention/treatment of atrial fibrillation |
PT2928881T (pt) * | 2012-12-07 | 2018-05-07 | Hoffmann La Roche | Novos derivados de piridina |
AR095764A1 (es) | 2013-03-28 | 2015-11-11 | Sanofi Sa | Derivados de ácido biaril-propiónico y su uso como productos farmacéuticos |
AU2014243070B2 (en) | 2013-03-28 | 2017-12-21 | Sanofi | Biaryl-propionic acid derivatives and their use as pharmaceuticals |
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US20200085810A1 (en) * | 2018-07-26 | 2020-03-19 | Hoffmann-La Roche Inc. | Compounds for use in treating kidney disorders |
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