HRP20000917A2 - Non-peptidyl inhibitors of vla-4 dependent cell binding useful in treating inflammatory, autoimmune, and respiratory diseases - Google Patents
Non-peptidyl inhibitors of vla-4 dependent cell binding useful in treating inflammatory, autoimmune, and respiratory diseases Download PDFInfo
- Publication number
- HRP20000917A2 HRP20000917A2 HR20000917A HRP20000917A HRP20000917A2 HR P20000917 A2 HRP20000917 A2 HR P20000917A2 HR 20000917 A HR20000917 A HR 20000917A HR P20000917 A HRP20000917 A HR P20000917A HR P20000917 A2 HRP20000917 A2 HR P20000917A2
- Authority
- HR
- Croatia
- Prior art keywords
- phenyl
- ureido
- methyl
- butyl
- propionic acid
- Prior art date
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- 230000002757 inflammatory effect Effects 0.000 title claims description 13
- 208000023275 Autoimmune disease Diseases 0.000 title claims description 12
- 208000027866 inflammatory disease Diseases 0.000 title claims description 12
- 208000023504 respiratory system disease Diseases 0.000 title claims description 10
- 230000001363 autoimmune Effects 0.000 title claims description 9
- 230000027455 binding Effects 0.000 title description 18
- 239000003112 inhibitor Substances 0.000 title description 17
- 230000001419 dependent effect Effects 0.000 title description 8
- 150000001875 compounds Chemical class 0.000 claims description 223
- -1 triaznyl Chemical group 0.000 claims description 129
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 124
- 230000036961 partial effect Effects 0.000 claims description 77
- 125000000623 heterocyclic group Chemical group 0.000 claims description 65
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical group FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 63
- 125000003118 aryl group Chemical group 0.000 claims description 61
- 108010008212 Integrin alpha4beta1 Proteins 0.000 claims description 54
- 125000001424 substituent group Chemical group 0.000 claims description 52
- 238000000034 method Methods 0.000 claims description 47
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 45
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 41
- 125000001072 heteroaryl group Chemical group 0.000 claims description 35
- 239000001257 hydrogen Substances 0.000 claims description 35
- 229910052739 hydrogen Inorganic materials 0.000 claims description 35
- 125000000217 alkyl group Chemical group 0.000 claims description 27
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 23
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 22
- 239000002253 acid Substances 0.000 claims description 19
- 239000008194 pharmaceutical composition Substances 0.000 claims description 19
- 125000004432 carbon atom Chemical group C* 0.000 claims description 18
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 18
- 150000003839 salts Chemical class 0.000 claims description 18
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 claims description 17
- 239000004202 carbamide Substances 0.000 claims description 17
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 16
- 229910052799 carbon Inorganic materials 0.000 claims description 14
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 13
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- 229910052757 nitrogen Chemical group 0.000 claims description 12
- 230000008569 process Effects 0.000 claims description 12
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- 235000019260 propionic acid Nutrition 0.000 claims description 11
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- 125000004076 pyridyl group Chemical group 0.000 claims description 10
- 229910052717 sulfur Inorganic materials 0.000 claims description 10
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- 150000001721 carbon Chemical group 0.000 claims description 8
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 8
- 150000002431 hydrogen Chemical class 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
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- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 7
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- 125000004414 alkyl thio group Chemical group 0.000 claims description 7
- 125000002837 carbocyclic group Chemical group 0.000 claims description 7
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 7
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 7
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- 125000000168 pyrrolyl group Chemical group 0.000 claims description 6
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- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 5
- BBBSYNRZZATAHL-UHFFFAOYSA-N 3-[2-[1-[[2-[4-[(2,6-dichlorophenyl)carbamoylamino]phenyl]acetyl]amino]-3-methylbutyl]-1,3-thiazol-5-yl]propanoic acid Chemical compound N=1C=C(CCC(O)=O)SC=1C(CC(C)C)NC(=O)CC(C=C1)=CC=C1NC(=O)NC1=C(Cl)C=CC=C1Cl BBBSYNRZZATAHL-UHFFFAOYSA-N 0.000 claims description 5
- RZLHHEMDVRXMLF-UHFFFAOYSA-N 3-[2-[1-[[2-[4-[(2-fluorophenyl)carbamoylamino]phenyl]acetyl]amino]-3-methylbutyl]-1,3-thiazol-5-yl]propanoic acid Chemical compound N=1C=C(CCC(O)=O)SC=1C(CC(C)C)NC(=O)CC(C=C1)=CC=C1NC(=O)NC1=CC=CC=C1F RZLHHEMDVRXMLF-UHFFFAOYSA-N 0.000 claims description 5
- YVUDZGKPSPCYKB-UHFFFAOYSA-N 3-[3-[3-methyl-1-[[2-[4-[(2-methylphenyl)carbamoylamino]phenyl]acetyl]amino]butyl]-1,2-oxazol-5-yl]propanoic acid Chemical compound C1=C(CCC(O)=O)ON=C1C(CC(C)C)NC(=O)CC(C=C1)=CC=C1NC(=O)NC1=CC=CC=C1C YVUDZGKPSPCYKB-UHFFFAOYSA-N 0.000 claims description 5
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 5
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 5
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 5
- 230000003110 anti-inflammatory effect Effects 0.000 claims description 5
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- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 5
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- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 5
- 239000003937 drug carrier Substances 0.000 claims description 5
- 125000004494 ethyl ester group Chemical group 0.000 claims description 5
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- 125000002541 furyl group Chemical group 0.000 claims description 5
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- 229960003444 immunosuppressant agent Drugs 0.000 claims description 5
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- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 5
- 239000011593 sulfur Chemical group 0.000 claims description 5
- 125000001544 thienyl group Chemical group 0.000 claims description 5
- FXAUFLVCVWYGLK-UHFFFAOYSA-N 3-[2-[1-[[2-[4-[(2-methoxyphenyl)carbamoylamino]phenyl]acetyl]amino]-3-methylbutyl]-1,3-thiazol-5-yl]propanoic acid Chemical compound COC1=CC=CC=C1NC(=O)NC(C=C1)=CC=C1CC(=O)NC(CC(C)C)C1=NC=C(CCC(O)=O)S1 FXAUFLVCVWYGLK-UHFFFAOYSA-N 0.000 claims description 4
- BFSPATRZTOUXBI-UHFFFAOYSA-N 3-[2-[1-[[2-[4-[(2-methylphenyl)carbamoylamino]phenyl]acetyl]amino]butyl]-1,3-thiazol-5-yl]propanoic acid Chemical compound N=1C=C(CCC(O)=O)SC=1C(CCC)NC(=O)CC(C=C1)=CC=C1NC(=O)NC1=CC=CC=C1C BFSPATRZTOUXBI-UHFFFAOYSA-N 0.000 claims description 4
- RTTRCNDKNNRWCA-UHFFFAOYSA-N 3-[2-[3-methyl-1-[[2-[4-[(2-methylphenyl)carbamoylamino]phenyl]acetyl]amino]butyl]-1,3-oxazol-5-yl]propanoic acid Chemical compound N=1C=C(CCC(O)=O)OC=1C(CC(C)C)NC(=O)CC(C=C1)=CC=C1NC(=O)NC1=CC=CC=C1C RTTRCNDKNNRWCA-UHFFFAOYSA-N 0.000 claims description 4
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- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 4
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
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- MDSLYHPULFIAMH-UHFFFAOYSA-N 3-[2-[1-[[2-[4-[(2,6-dimethylphenyl)carbamoylamino]phenyl]acetyl]amino]-3-methylbutyl]-1,3-thiazol-5-yl]propanoic acid Chemical compound N=1C=C(CCC(O)=O)SC=1C(CC(C)C)NC(=O)CC(C=C1)=CC=C1NC(=O)NC1=C(C)C=CC=C1C MDSLYHPULFIAMH-UHFFFAOYSA-N 0.000 claims description 3
- KEAXJEQRYYKKFH-UHFFFAOYSA-N 3-[2-[1-[[2-[4-[(2-chloro-6-methylphenyl)carbamoylamino]phenyl]acetyl]amino]-3-methylbutyl]-1,3-thiazol-5-yl]propanoic acid Chemical compound N=1C=C(CCC(O)=O)SC=1C(CC(C)C)NC(=O)CC(C=C1)=CC=C1NC(=O)NC1=C(C)C=CC=C1Cl KEAXJEQRYYKKFH-UHFFFAOYSA-N 0.000 claims description 3
- RMWCQFDACWYJLG-UHFFFAOYSA-N 3-[2-[1-[[2-[4-[(2-chlorophenyl)carbamoylamino]phenyl]acetyl]amino]-3-methylbutyl]-1,3-thiazol-5-yl]propanoic acid Chemical compound N=1C=C(CCC(O)=O)SC=1C(CC(C)C)NC(=O)CC(C=C1)=CC=C1NC(=O)NC1=CC=CC=C1Cl RMWCQFDACWYJLG-UHFFFAOYSA-N 0.000 claims description 3
- QKPOGBUYUXZUJA-UHFFFAOYSA-N 3-[2-[3-methyl-1-[[2-[4-[(2-methylphenyl)carbamoylamino]phenyl]acetyl]amino]butyl]-1,3-thiazol-5-yl]-n-methylsulfonylpropanamide Chemical compound N=1C=C(CCC(=O)NS(C)(=O)=O)SC=1C(CC(C)C)NC(=O)CC(C=C1)=CC=C1NC(=O)NC1=CC=CC=C1C QKPOGBUYUXZUJA-UHFFFAOYSA-N 0.000 claims description 3
- WSDUIYINORQGPC-UHFFFAOYSA-N 3-[5-[1-[[2-[4-[(3-cyclopentylpyridin-2-yl)carbamoylamino]-3-methoxyphenyl]acetyl]amino]-3-methylbutyl]-1h-imidazol-2-yl]propanoic acid Chemical compound C=1C=C(NC(=O)NC=2C(=CC=CN=2)C2CCCC2)C(OC)=CC=1CC(=O)NC(CC(C)C)C1=CNC(CCC(O)=O)=N1 WSDUIYINORQGPC-UHFFFAOYSA-N 0.000 claims description 3
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- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
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- ZSWFCLXCOIISFI-UHFFFAOYSA-N endo-cyclopentadiene Natural products C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 claims description 3
- 125000006517 heterocyclyl carbonyl group Chemical group 0.000 claims description 3
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- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims description 3
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims description 3
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- XHPVQRLTDCIBIC-UHFFFAOYSA-N n-hydroxy-3-[2-[3-methyl-1-[[2-[4-[(2-methylphenyl)carbamoylamino]phenyl]acetyl]amino]butyl]-1,3-thiazol-5-yl]propanamide Chemical compound N=1C=C(CCC(=O)NO)SC=1C(CC(C)C)NC(=O)CC(C=C1)=CC=C1NC(=O)NC1=CC=CC=C1C XHPVQRLTDCIBIC-UHFFFAOYSA-N 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
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- OVXCRIQYLIKODD-UHFFFAOYSA-N 3-[2-[1-[2-[4-[(2-methylphenyl)carbamoylamino]phenyl]acetyl]-3,6-dihydro-2h-pyridin-2-yl]-1,3-thiazol-5-yl]propanoic acid Chemical compound CC1=CC=CC=C1NC(=O)NC(C=C1)=CC=C1CC(=O)N1C(C=2SC(CCC(O)=O)=CN=2)CC=CC1 OVXCRIQYLIKODD-UHFFFAOYSA-N 0.000 claims description 2
- YGEXROMPQRXWFF-UHFFFAOYSA-N 3-[2-[1-[2-[4-[(2-methylphenyl)carbamoylamino]phenyl]acetyl]-4-oxopyrrolidin-2-yl]-1,3-oxazol-5-yl]propanoic acid Chemical compound CC1=CC=CC=C1NC(=O)NC(C=C1)=CC=C1CC(=O)N1C(C=2OC(CCC(O)=O)=CN=2)CC(=O)C1 YGEXROMPQRXWFF-UHFFFAOYSA-N 0.000 claims description 2
- OOOOEAQYOYXRAG-UHFFFAOYSA-N 3-[2-[1-[2-[4-[(2-methylphenyl)carbamoylamino]phenyl]acetyl]-4-oxopyrrolidin-2-yl]-1,3-thiazol-5-yl]propanoic acid Chemical compound CC1=CC=CC=C1NC(=O)NC(C=C1)=CC=C1CC(=O)N1C(C=2SC(CCC(O)=O)=CN=2)CC(=O)C1 OOOOEAQYOYXRAG-UHFFFAOYSA-N 0.000 claims description 2
- WSSBXMIOMQEUNH-UHFFFAOYSA-N 3-[2-[1-[2-[4-[(2-methylphenyl)carbamoylamino]phenyl]acetyl]azepan-2-yl]-1,3-oxazol-5-yl]propanoic acid Chemical compound CC1=CC=CC=C1NC(=O)NC(C=C1)=CC=C1CC(=O)N1C(C=2OC(CCC(O)=O)=CN=2)CCCCC1 WSSBXMIOMQEUNH-UHFFFAOYSA-N 0.000 claims description 2
- BZYGOAXWORSNJE-UHFFFAOYSA-N 3-[2-[1-[2-[4-[(2-methylphenyl)carbamoylamino]phenyl]acetyl]azepan-2-yl]-1,3-thiazol-5-yl]propanoic acid Chemical compound CC1=CC=CC=C1NC(=O)NC(C=C1)=CC=C1CC(=O)N1C(C=2SC(CCC(O)=O)=CN=2)CCCCC1 BZYGOAXWORSNJE-UHFFFAOYSA-N 0.000 claims description 2
- AQBDBLGEEJMJTQ-UHFFFAOYSA-N 3-[2-[1-[2-[4-[(2-methylphenyl)carbamoylamino]phenyl]acetyl]azetidin-2-yl]-1,3-oxazol-5-yl]propanoic acid Chemical compound CC1=CC=CC=C1NC(=O)NC(C=C1)=CC=C1CC(=O)N1C(C=2OC(CCC(O)=O)=CN=2)CC1 AQBDBLGEEJMJTQ-UHFFFAOYSA-N 0.000 claims description 2
- CKEIFTKSXLGCGV-UHFFFAOYSA-N 3-[2-[1-[2-[4-[(2-methylphenyl)carbamoylamino]phenyl]acetyl]azetidin-2-yl]-1,3-thiazol-5-yl]propanoic acid Chemical compound CC1=CC=CC=C1NC(=O)NC(C=C1)=CC=C1CC(=O)N1C(C=2SC(CCC(O)=O)=CN=2)CC1 CKEIFTKSXLGCGV-UHFFFAOYSA-N 0.000 claims description 2
- WUUFSFYYMDIAOS-UHFFFAOYSA-N 3-[2-[1-[2-[4-[(2-methylphenyl)carbamoylamino]phenyl]acetyl]piperidin-2-yl]-1,3-oxazol-5-yl]propanoic acid Chemical compound CC1=CC=CC=C1NC(=O)NC(C=C1)=CC=C1CC(=O)N1C(C=2OC(CCC(O)=O)=CN=2)CCCC1 WUUFSFYYMDIAOS-UHFFFAOYSA-N 0.000 claims description 2
- KUNOQVYVRWSOST-UHFFFAOYSA-N 3-[2-[1-[2-[4-[(2-methylphenyl)carbamoylamino]phenyl]acetyl]piperidin-2-yl]-1,3-thiazol-5-yl]propanoic acid Chemical compound CC1=CC=CC=C1NC(=O)NC(C=C1)=CC=C1CC(=O)N1C(C=2SC(CCC(O)=O)=CN=2)CCCC1 KUNOQVYVRWSOST-UHFFFAOYSA-N 0.000 claims description 2
- VBVCKPWBLMDHKX-UHFFFAOYSA-N 3-[2-[1-[2-[4-[(2-methylphenyl)carbamoylamino]phenyl]acetyl]pyrrolidin-2-yl]-1,3-oxazol-5-yl]propanoic acid Chemical compound CC1=CC=CC=C1NC(=O)NC(C=C1)=CC=C1CC(=O)N1C(C=2OC(CCC(O)=O)=CN=2)CCC1 VBVCKPWBLMDHKX-UHFFFAOYSA-N 0.000 claims description 2
- NKUOOPQLEOZHLO-UHFFFAOYSA-N 3-[2-[1-[2-[4-[(2-methylphenyl)carbamoylamino]phenyl]acetyl]pyrrolidin-2-yl]-1,3-thiazol-5-yl]propanoic acid Chemical compound CC1=CC=CC=C1NC(=O)NC(C=C1)=CC=C1CC(=O)N1C(C=2SC(CCC(O)=O)=CN=2)CCC1 NKUOOPQLEOZHLO-UHFFFAOYSA-N 0.000 claims description 2
- TTXXWZBESOGCGO-UHFFFAOYSA-N 3-[2-[1-[[2-[3-cyclopentyl-4-[(3-methylpyridin-2-yl)carbamoylamino]phenyl]acetyl]amino]-3-methylbutyl]-1h-imidazol-5-yl]propanoic acid Chemical compound N=1C=C(CCC(O)=O)NC=1C(CC(C)C)NC(=O)CC(C=C1C2CCCC2)=CC=C1NC(=O)NC1=NC=CC=C1C TTXXWZBESOGCGO-UHFFFAOYSA-N 0.000 claims description 2
- BVCQFTCEFZFPPH-UHFFFAOYSA-N 3-[2-[1-[[2-[3-fluoro-4-[(2-methylphenyl)carbamoylamino]phenyl]acetyl]amino]-3-methylbutyl]-1,3-oxazol-5-yl]propanoic acid Chemical compound N=1C=C(CCC(O)=O)OC=1C(CC(C)C)NC(=O)CC(C=C1F)=CC=C1NC(=O)NC1=CC=CC=C1C BVCQFTCEFZFPPH-UHFFFAOYSA-N 0.000 claims description 2
- YQADRBXDPQSVOG-UHFFFAOYSA-N 3-[2-[1-[[2-[3-methoxy-4-(pyridin-2-ylcarbamoylamino)phenyl]acetyl]amino]-3-methylbutyl]-1,3-thiazol-5-yl]propanoic acid Chemical compound C=1C=C(NC(=O)NC=2N=CC=CC=2)C(OC)=CC=1CC(=O)NC(CC(C)C)C1=NC=C(CCC(O)=O)S1 YQADRBXDPQSVOG-UHFFFAOYSA-N 0.000 claims description 2
- OXXWTEQYSNSHGF-UHFFFAOYSA-N 3-[2-[1-[[2-[3-methoxy-4-[(2-methylphenyl)carbamoylamino]phenyl]acetyl]amino]-3-methylbutyl]-1,3-oxazol-4-yl]propanoic acid Chemical compound C=1C=C(NC(=O)NC=2C(=CC=CC=2)C)C(OC)=CC=1CC(=O)NC(CC(C)C)C1=NC(CCC(O)=O)=CO1 OXXWTEQYSNSHGF-UHFFFAOYSA-N 0.000 claims description 2
- SYHBDPRCKKBBOL-UHFFFAOYSA-N 3-[2-[1-[[2-[3-methoxy-4-[(3-methoxypyridin-2-yl)carbamoylamino]phenyl]acetyl]amino]-3-methylbutyl]-1,1-dioxo-4,5-dihydro-1,3-thiazol-5-yl]propanoic acid Chemical compound COC1=CC=CN=C1NC(=O)NC(C(=C1)OC)=CC=C1CC(=O)NC(CC(C)C)C1=NCC(CCC(O)=O)S1(=O)=O SYHBDPRCKKBBOL-UHFFFAOYSA-N 0.000 claims description 2
- GRTPXUVKOKVLRJ-UHFFFAOYSA-N 3-[2-[1-[[2-[4-[(2-fluorophenyl)carbamoylamino]phenyl]acetyl]amino]-3-methylbutyl]-4,5-dihydro-1,3-oxazol-5-yl]propanoic acid Chemical compound N=1CC(CCC(O)=O)OC=1C(CC(C)C)NC(=O)CC(C=C1)=CC=C1NC(=O)NC1=CC=CC=C1F GRTPXUVKOKVLRJ-UHFFFAOYSA-N 0.000 claims description 2
- QNOKXJYHJKRMAS-UHFFFAOYSA-N 3-[2-[1-[[2-[4-[(2-methoxyphenyl)carbamoylamino]phenyl]acetyl]amino]-3-methylbutyl]-1,3-oxazol-5-yl]propanoic acid Chemical compound COC1=CC=CC=C1NC(=O)NC(C=C1)=CC=C1CC(=O)NC(CC(C)C)C1=NC=C(CCC(O)=O)O1 QNOKXJYHJKRMAS-UHFFFAOYSA-N 0.000 claims description 2
- XGPZIWHMWJLJFK-UHFFFAOYSA-N 3-[2-[1-[[2-[4-[(2-methylphenyl)carbamoylamino]phenyl]acetyl]amino]but-3-enyl]-1,3-thiazol-5-yl]propanoic acid Chemical compound CC1=CC=CC=C1NC(=O)NC(C=C1)=CC=C1CC(=O)NC(CC=C)C1=NC=C(CCC(O)=O)S1 XGPZIWHMWJLJFK-UHFFFAOYSA-N 0.000 claims description 2
- REZNXIFSUNEWLW-UHFFFAOYSA-N 3-[2-[1-[[2-[4-[(3-cyclopentylpyridin-2-yl)carbamoylamino]-3-methoxyphenyl]acetyl]amino]-3-methylbutyl]-1h-imidazol-5-yl]propanoic acid Chemical compound C=1C=C(NC(=O)NC=2C(=CC=CN=2)C2CCCC2)C(OC)=CC=1CC(=O)NC(CC(C)C)C1=NC=C(CCC(O)=O)N1 REZNXIFSUNEWLW-UHFFFAOYSA-N 0.000 claims description 2
- PAFDGPKDDLQEEI-UHFFFAOYSA-N 3-[2-[1-[[2-[4-[(3-cyclopentylpyridin-2-yl)carbamoylamino]-3-methylphenyl]acetyl]amino]-3-methylbutyl]-4,5-dihydro-1h-imidazol-5-yl]propanoic acid Chemical compound N=1CC(CCC(O)=O)NC=1C(CC(C)C)NC(=O)CC(C=C1C)=CC=C1NC(=O)NC1=NC=CC=C1C1CCCC1 PAFDGPKDDLQEEI-UHFFFAOYSA-N 0.000 claims description 2
- WPPQXZAEBFKILN-UHFFFAOYSA-N 3-[2-[1-[[2-[4-[(3-cyclopentylpyridin-2-yl)carbamoylamino]phenyl]acetyl]amino]-3-methylbutyl]-4,5-dihydro-1,3-oxazol-5-yl]propanoic acid Chemical compound N=1CC(CCC(O)=O)OC=1C(CC(C)C)NC(=O)CC(C=C1)=CC=C1NC(=O)NC1=NC=CC=C1C1CCCC1 WPPQXZAEBFKILN-UHFFFAOYSA-N 0.000 claims description 2
- LQZIXUPIMJTKFX-UHFFFAOYSA-N 3-[2-[2-[2-[4-[(2-methylphenyl)carbamoylamino]phenyl]acetyl]-3,4-dihydro-1h-isoquinolin-3-yl]-1,3-oxazol-5-yl]propanoic acid Chemical compound CC1=CC=CC=C1NC(=O)NC(C=C1)=CC=C1CC(=O)N1C(C=2OC(CCC(O)=O)=CN=2)CC2=CC=CC=C2C1 LQZIXUPIMJTKFX-UHFFFAOYSA-N 0.000 claims description 2
- RWCPRALTHYQQAB-UHFFFAOYSA-N 3-[2-[2-[2-[4-[(2-methylphenyl)carbamoylamino]phenyl]acetyl]-3,4-dihydro-1h-isoquinolin-3-yl]-1,3-thiazol-5-yl]propanoic acid Chemical compound CC1=CC=CC=C1NC(=O)NC(C=C1)=CC=C1CC(=O)N1C(C=2SC(CCC(O)=O)=CN=2)CC2=CC=CC=C2C1 RWCPRALTHYQQAB-UHFFFAOYSA-N 0.000 claims description 2
- XEXWNSNTWQDNRP-UHFFFAOYSA-N 3-[2-[2-methyl-1-[2-[4-[(2-methylphenyl)carbamoylamino]phenyl]acetyl]pyrrolidin-2-yl]-1,3-oxazol-5-yl]propanoic acid Chemical compound CC1=CC=CC=C1NC(=O)NC(C=C1)=CC=C1CC(=O)N1C(C=2OC(CCC(O)=O)=CN=2)(C)CCC1 XEXWNSNTWQDNRP-UHFFFAOYSA-N 0.000 claims description 2
- LIODMWHVPRHDPS-UHFFFAOYSA-N 3-[2-[2-methyl-1-[2-[4-[(2-methylphenyl)carbamoylamino]phenyl]acetyl]pyrrolidin-2-yl]-1,3-thiazol-5-yl]propanoic acid Chemical compound CC1=CC=CC=C1NC(=O)NC(C=C1)=CC=C1CC(=O)N1C(C=2SC(CCC(O)=O)=CN=2)(C)CCC1 LIODMWHVPRHDPS-UHFFFAOYSA-N 0.000 claims description 2
- VMAIZGOIPYPSBA-UHFFFAOYSA-N 3-[2-[3,3-dimethyl-1-[2-[4-[(2-methylphenyl)carbamoylamino]phenyl]acetyl]pyrrolidin-2-yl]-1,3-oxazol-5-yl]propanoic acid Chemical compound CC1=CC=CC=C1NC(=O)NC(C=C1)=CC=C1CC(=O)N1C(C=2OC(CCC(O)=O)=CN=2)C(C)(C)CC1 VMAIZGOIPYPSBA-UHFFFAOYSA-N 0.000 claims description 2
- JEIVQTRZARKZSG-UHFFFAOYSA-N 3-[2-[3,3-dimethyl-1-[2-[4-[(2-methylphenyl)carbamoylamino]phenyl]acetyl]pyrrolidin-2-yl]-1,3-thiazol-5-yl]propanoic acid Chemical compound CC1=CC=CC=C1NC(=O)NC(C=C1)=CC=C1CC(=O)N1C(C=2SC(CCC(O)=O)=CN=2)C(C)(C)CC1 JEIVQTRZARKZSG-UHFFFAOYSA-N 0.000 claims description 2
- FJPWUMKJFSFKCE-UHFFFAOYSA-N 3-[2-[3-[2-[4-[(2-methylphenyl)carbamoylamino]phenyl]acetyl]-1,3-oxazolidin-4-yl]-1,3-thiazol-5-yl]propanoic acid Chemical compound CC1=CC=CC=C1NC(=O)NC(C=C1)=CC=C1CC(=O)N1C(C=2SC(CCC(O)=O)=CN=2)COC1 FJPWUMKJFSFKCE-UHFFFAOYSA-N 0.000 claims description 2
- TXPZILOCEZPRTC-UHFFFAOYSA-N 3-[2-[3-[2-[4-[(2-methylphenyl)carbamoylamino]phenyl]acetyl]-1,3-thiazolidin-4-yl]-1,3-oxazol-5-yl]propanoic acid Chemical compound CC1=CC=CC=C1NC(=O)NC(C=C1)=CC=C1CC(=O)N1C(C=2OC(CCC(O)=O)=CN=2)CSC1 TXPZILOCEZPRTC-UHFFFAOYSA-N 0.000 claims description 2
- IAMZQOBQJSODKL-UHFFFAOYSA-N 3-[2-[3-methyl-1-[2-[4-[(2-methylphenyl)carbamoylamino]phenyl]acetyl]pyrrolidin-2-yl]-1,3-oxazol-5-yl]propanoic acid Chemical compound CC1CCN(C(=O)CC=2C=CC(NC(=O)NC=3C(=CC=CC=3)C)=CC=2)C1C1=NC=C(CCC(O)=O)O1 IAMZQOBQJSODKL-UHFFFAOYSA-N 0.000 claims description 2
- JQTLRJXOAJHBMW-UHFFFAOYSA-N 3-[2-[3-methyl-1-[2-[4-[(2-methylphenyl)carbamoylamino]phenyl]acetyl]pyrrolidin-2-yl]-1,3-thiazol-5-yl]propanoic acid Chemical compound CC1CCN(C(=O)CC=2C=CC(NC(=O)NC=3C(=CC=CC=3)C)=CC=2)C1C1=NC=C(CCC(O)=O)S1 JQTLRJXOAJHBMW-UHFFFAOYSA-N 0.000 claims description 2
- FHEZXSCKPAOZPI-UHFFFAOYSA-N 3-[2-[3-methyl-1-[[2-[3-methyl-4-(pyridin-2-ylcarbamoylamino)phenyl]acetyl]amino]butyl]-4,5-dihydro-1,3-thiazol-4-yl]propanoic acid Chemical compound N=1C(CCC(O)=O)CSC=1C(CC(C)C)NC(=O)CC(C=C1C)=CC=C1NC(=O)NC1=CC=CC=N1 FHEZXSCKPAOZPI-UHFFFAOYSA-N 0.000 claims description 2
- GBDSSALQXWQVIW-UHFFFAOYSA-N 3-[2-[3-methyl-1-[[2-[3-methyl-4-(pyridin-2-ylcarbamoylamino)phenyl]acetyl]amino]butyl]-4,5-dihydro-1,3-thiazol-5-yl]propanoic acid Chemical compound N=1CC(CCC(O)=O)SC=1C(CC(C)C)NC(=O)CC(C=C1C)=CC=C1NC(=O)NC1=CC=CC=N1 GBDSSALQXWQVIW-UHFFFAOYSA-N 0.000 claims description 2
- UBKWCDVUBRNKBE-UHFFFAOYSA-N 3-[2-[3-methyl-1-[[2-[3-methyl-4-[(3-methylpyridin-2-yl)carbamoylamino]phenyl]acetyl]amino]butyl]-4,5-dihydro-1h-imidazol-5-yl]propanoic acid Chemical compound N=1CC(CCC(O)=O)NC=1C(CC(C)C)NC(=O)CC(C=C1C)=CC=C1NC(=O)NC1=NC=CC=C1C UBKWCDVUBRNKBE-UHFFFAOYSA-N 0.000 claims description 2
- UBDLHZOGVNEPRO-UHFFFAOYSA-N 3-[2-[3-methyl-1-[[2-[4-(pyridin-2-ylcarbamoylamino)phenyl]acetyl]amino]butyl]-1,3-oxazol-5-yl]propanoic acid Chemical compound N=1C=C(CCC(O)=O)OC=1C(CC(C)C)NC(=O)CC(C=C1)=CC=C1NC(=O)NC1=CC=CC=N1 UBDLHZOGVNEPRO-UHFFFAOYSA-N 0.000 claims description 2
- BKEYTGRISNFZOL-UHFFFAOYSA-N 3-[2-[3-methyl-1-[[2-[4-[(2-methylphenyl)carbamoylamino]phenyl]acetyl]amino]butyl]-1,3-oxazol-4-yl]propanoic acid Chemical compound N=1C(CCC(O)=O)=COC=1C(CC(C)C)NC(=O)CC(C=C1)=CC=C1NC(=O)NC1=CC=CC=C1C BKEYTGRISNFZOL-UHFFFAOYSA-N 0.000 claims description 2
- VJRNPNOHAFDGOX-UHFFFAOYSA-N 3-[2-[3-methyl-1-[[2-[4-[(2-methylphenyl)carbamoylamino]phenyl]acetyl]amino]butyl]-4,5-dihydro-1,3-oxazol-4-yl]propanoic acid Chemical compound N=1C(CCC(O)=O)COC=1C(CC(C)C)NC(=O)CC(C=C1)=CC=C1NC(=O)NC1=CC=CC=C1C VJRNPNOHAFDGOX-UHFFFAOYSA-N 0.000 claims description 2
- SOYJYGKAABRXEF-UHFFFAOYSA-N 3-[2-[3-methyl-1-[[2-[4-[(2-methylphenyl)carbamoylamino]phenyl]acetyl]amino]butyl]-4,5-dihydro-1,3-oxazol-5-yl]propanoic acid Chemical compound N=1CC(CCC(O)=O)OC=1C(CC(C)C)NC(=O)CC(C=C1)=CC=C1NC(=O)NC1=CC=CC=C1C SOYJYGKAABRXEF-UHFFFAOYSA-N 0.000 claims description 2
- PQKVHTPFCCCSQI-UHFFFAOYSA-N 3-[2-[4-(methylamino)-1-[2-[4-[(2-methylphenyl)carbamoylamino]phenyl]acetyl]pyrrolidin-2-yl]-1,3-oxazol-5-yl]propanoic acid Chemical compound C1C(NC)CC(C=2OC(CCC(O)=O)=CN=2)N1C(=O)CC(C=C1)=CC=C1NC(=O)NC1=CC=CC=C1C PQKVHTPFCCCSQI-UHFFFAOYSA-N 0.000 claims description 2
- CDZHQVMPXJJLNN-UHFFFAOYSA-N 3-[2-[4-(methylamino)-1-[2-[4-[(2-methylphenyl)carbamoylamino]phenyl]acetyl]pyrrolidin-2-yl]-1,3-thiazol-5-yl]propanoic acid Chemical compound C1C(NC)CC(C=2SC(CCC(O)=O)=CN=2)N1C(=O)CC(C=C1)=CC=C1NC(=O)NC1=CC=CC=C1C CDZHQVMPXJJLNN-UHFFFAOYSA-N 0.000 claims description 2
- KSARLWHBIDJEMO-UHFFFAOYSA-N 3-[2-[4-[ethyl(methyl)amino]-1-[2-[4-[(2-methylphenyl)carbamoylamino]phenyl]acetyl]pyrrolidin-2-yl]-1,3-thiazol-5-yl]propanoic acid Chemical compound C1C(N(C)CC)CC(C=2SC(CCC(O)=O)=CN=2)N1C(=O)CC(C=C1)=CC=C1NC(=O)NC1=CC=CC=C1C KSARLWHBIDJEMO-UHFFFAOYSA-N 0.000 claims description 2
- DTTWFONMOZZMBM-UHFFFAOYSA-N 3-[2-[4-amino-1-[2-[4-[(2-methylphenyl)carbamoylamino]phenyl]acetyl]pyrrolidin-2-yl]-1,3-oxazol-5-yl]propanoic acid Chemical compound CC1=CC=CC=C1NC(=O)NC(C=C1)=CC=C1CC(=O)N1C(C=2OC(CCC(O)=O)=CN=2)CC(N)C1 DTTWFONMOZZMBM-UHFFFAOYSA-N 0.000 claims description 2
- NPDHLKIQNQXBBG-UHFFFAOYSA-N 3-[2-[4-amino-1-[2-[4-[(2-methylphenyl)carbamoylamino]phenyl]acetyl]pyrrolidin-2-yl]-1,3-thiazol-5-yl]propanoic acid Chemical compound CC1=CC=CC=C1NC(=O)NC(C=C1)=CC=C1CC(=O)N1C(C=2SC(CCC(O)=O)=CN=2)CC(N)C1 NPDHLKIQNQXBBG-UHFFFAOYSA-N 0.000 claims description 2
- WAOFXRZHVRXLOH-UHFFFAOYSA-N 3-[2-[4-hydroxy-1-[2-[4-[(2-methylphenyl)carbamoylamino]phenyl]acetyl]pyrrolidin-2-yl]-1,3-oxazol-5-yl]propanoic acid Chemical compound CC1=CC=CC=C1NC(=O)NC(C=C1)=CC=C1CC(=O)N1C(C=2OC(CCC(O)=O)=CN=2)CC(O)C1 WAOFXRZHVRXLOH-UHFFFAOYSA-N 0.000 claims description 2
- ZWJDWVDJUGLXHM-UHFFFAOYSA-N 3-[2-[4-hydroxy-1-[2-[4-[(2-methylphenyl)carbamoylamino]phenyl]acetyl]pyrrolidin-2-yl]-1,3-thiazol-5-yl]propanoic acid Chemical compound CC1=CC=CC=C1NC(=O)NC(C=C1)=CC=C1CC(=O)N1C(C=2SC(CCC(O)=O)=CN=2)CC(O)C1 ZWJDWVDJUGLXHM-UHFFFAOYSA-N 0.000 claims description 2
- MRNHJCQSUAFKFC-UHFFFAOYSA-N 3-[2-[4-hydroxy-4-methyl-1-[2-[4-[(2-methylphenyl)carbamoylamino]phenyl]acetyl]pyrrolidin-2-yl]-1,3-oxazol-5-yl]propanoic acid Chemical compound CC1=CC=CC=C1NC(=O)NC(C=C1)=CC=C1CC(=O)N1C(C=2OC(CCC(O)=O)=CN=2)CC(C)(O)C1 MRNHJCQSUAFKFC-UHFFFAOYSA-N 0.000 claims description 2
- BFCLVYJXYNERGR-UHFFFAOYSA-N 3-[2-[4-hydroxy-4-methyl-1-[2-[4-[(2-methylphenyl)carbamoylamino]phenyl]acetyl]pyrrolidin-2-yl]-1,3-thiazol-5-yl]propanoic acid Chemical compound CC1=CC=CC=C1NC(=O)NC(C=C1)=CC=C1CC(=O)N1C(C=2SC(CCC(O)=O)=CN=2)CC(C)(O)C1 BFCLVYJXYNERGR-UHFFFAOYSA-N 0.000 claims description 2
- KNZKEYGBXFDQRG-UHFFFAOYSA-N 3-[2-[4-methyl-1-[2-[4-[(2-methylphenyl)carbamoylamino]phenyl]acetyl]pyrrolidin-2-yl]-1,3-oxazol-5-yl]propanoic acid Chemical compound C1C(C)CC(C=2OC(CCC(O)=O)=CN=2)N1C(=O)CC(C=C1)=CC=C1NC(=O)NC1=CC=CC=C1C KNZKEYGBXFDQRG-UHFFFAOYSA-N 0.000 claims description 2
- LRIWSKOJZQRLEW-UHFFFAOYSA-N 3-[2-[4-methyl-1-[2-[4-[(2-methylphenyl)carbamoylamino]phenyl]acetyl]pyrrolidin-2-yl]-1,3-thiazol-5-yl]propanoic acid Chemical compound C1C(C)CC(C=2SC(CCC(O)=O)=CN=2)N1C(=O)CC(C=C1)=CC=C1NC(=O)NC1=CC=CC=C1C LRIWSKOJZQRLEW-UHFFFAOYSA-N 0.000 claims description 2
- CDSKGEDQGNMWMK-UHFFFAOYSA-N 3-[2-[5,5-dimethyl-1-[2-[4-[(2-methylphenyl)carbamoylamino]phenyl]acetyl]pyrrolidin-2-yl]-1,3-oxazol-5-yl]propanoic acid Chemical compound CC1=CC=CC=C1NC(=O)NC(C=C1)=CC=C1CC(=O)N1C(C)(C)CCC1C1=NC=C(CCC(O)=O)O1 CDSKGEDQGNMWMK-UHFFFAOYSA-N 0.000 claims description 2
- MZNIOVGJBMHBII-UHFFFAOYSA-N 3-[2-[5,5-dimethyl-1-[2-[4-[(2-methylphenyl)carbamoylamino]phenyl]acetyl]pyrrolidin-2-yl]-1,3-thiazol-5-yl]propanoic acid Chemical compound CC1=CC=CC=C1NC(=O)NC(C=C1)=CC=C1CC(=O)N1C(C)(C)CCC1C1=NC=C(CCC(O)=O)S1 MZNIOVGJBMHBII-UHFFFAOYSA-N 0.000 claims description 2
- TUZOIXXJFYDJCL-UHFFFAOYSA-N 3-[2-[5-methyl-1-[2-[4-[(2-methylphenyl)carbamoylamino]phenyl]acetyl]pyrrolidin-2-yl]-1,3-oxazol-5-yl]propanoic acid Chemical compound CC1CCC(C=2OC(CCC(O)=O)=CN=2)N1C(=O)CC(C=C1)=CC=C1NC(=O)NC1=CC=CC=C1C TUZOIXXJFYDJCL-UHFFFAOYSA-N 0.000 claims description 2
- FZTAWKODGKJRID-UHFFFAOYSA-N 3-[2-[[[2-[4-[(2-chlorophenyl)carbamoylamino]phenyl]acetyl]amino]methyl]-1,3-thiazol-5-yl]propanoic acid Chemical compound S1C(CCC(=O)O)=CN=C1CNC(=O)CC(C=C1)=CC=C1NC(=O)NC1=CC=CC=C1Cl FZTAWKODGKJRID-UHFFFAOYSA-N 0.000 claims description 2
- GJPULSPYFFISLO-UHFFFAOYSA-N 3-[3-(2-methylpropyl)-2-oxo-4-[2-[4-(pyridin-2-ylcarbamoylamino)phenyl]acetyl]piperazin-1-yl]propanoic acid Chemical compound C1CN(CCC(O)=O)C(=O)C(CC(C)C)N1C(=O)CC(C=C1)=CC=C1NC(=O)NC1=CC=CC=N1 GJPULSPYFFISLO-UHFFFAOYSA-N 0.000 claims description 2
- IVRNBILFGWNELI-UHFFFAOYSA-N 3-[3-[1-[2-[4-[(2-methylphenyl)carbamoylamino]phenyl]acetyl]-3,6-dihydro-2h-pyridin-2-yl]-1,2-oxazol-5-yl]propanoic acid Chemical compound CC1=CC=CC=C1NC(=O)NC(C=C1)=CC=C1CC(=O)N1C(C2=NOC(CCC(O)=O)=C2)CC=CC1 IVRNBILFGWNELI-UHFFFAOYSA-N 0.000 claims description 2
- NKSYTVAHKMENLT-UHFFFAOYSA-N 3-[3-[1-[2-[4-[(2-methylphenyl)carbamoylamino]phenyl]acetyl]-4-oxopyrrolidin-2-yl]-1,2-oxazol-5-yl]propanoic acid Chemical compound CC1=CC=CC=C1NC(=O)NC(C=C1)=CC=C1CC(=O)N1C(C2=NOC(CCC(O)=O)=C2)CC(=O)C1 NKSYTVAHKMENLT-UHFFFAOYSA-N 0.000 claims description 2
- XVASUWDWKXEGLL-UHFFFAOYSA-N 3-[3-[1-[2-[4-[(2-methylphenyl)carbamoylamino]phenyl]acetyl]azepan-2-yl]-1,2-oxazol-5-yl]propanoic acid Chemical compound CC1=CC=CC=C1NC(=O)NC(C=C1)=CC=C1CC(=O)N1C(C2=NOC(CCC(O)=O)=C2)CCCCC1 XVASUWDWKXEGLL-UHFFFAOYSA-N 0.000 claims description 2
- RANXAGPUOQGLBX-UHFFFAOYSA-N 3-[3-[1-[2-[4-[(2-methylphenyl)carbamoylamino]phenyl]acetyl]azetidin-2-yl]-1,2-oxazol-5-yl]propanoic acid Chemical compound CC1=CC=CC=C1NC(=O)NC(C=C1)=CC=C1CC(=O)N1C(C2=NOC(CCC(O)=O)=C2)CC1 RANXAGPUOQGLBX-UHFFFAOYSA-N 0.000 claims description 2
- ROIHQGQZUMHJOQ-UHFFFAOYSA-N 3-[3-[1-[2-[4-[(2-methylphenyl)carbamoylamino]phenyl]acetyl]piperidin-2-yl]-1,2-oxazol-5-yl]propanoic acid Chemical compound CC1=CC=CC=C1NC(=O)NC(C=C1)=CC=C1CC(=O)N1C(C2=NOC(CCC(O)=O)=C2)CCCC1 ROIHQGQZUMHJOQ-UHFFFAOYSA-N 0.000 claims description 2
- SMMKUWNIMVNLHW-UHFFFAOYSA-N 3-[3-[1-[2-[4-[(2-methylphenyl)carbamoylamino]phenyl]acetyl]pyrrolidin-2-yl]-1,2-oxazol-5-yl]propanoic acid Chemical compound CC1=CC=CC=C1NC(=O)NC(C=C1)=CC=C1CC(=O)N1C(C2=NOC(CCC(O)=O)=C2)CCC1 SMMKUWNIMVNLHW-UHFFFAOYSA-N 0.000 claims description 2
- USEDUTJSKDZBGX-UHFFFAOYSA-N 3-[3-[1-[[2-[3-methoxy-4-[(2-methylphenyl)carbamoylamino]phenyl]acetyl]amino]-3-methylbutyl]-1,2-oxazol-5-yl]propanoic acid Chemical compound C=1C=C(NC(=O)NC=2C(=CC=CC=2)C)C(OC)=CC=1CC(=O)NC(CC(C)C)C=1C=C(CCC(O)=O)ON=1 USEDUTJSKDZBGX-UHFFFAOYSA-N 0.000 claims description 2
- WNGIJWWXPVEZIA-UHFFFAOYSA-N 3-[3-[1-[[2-[4-[(2-fluorophenyl)carbamoylamino]phenyl]acetyl]amino]-3-methylbutyl]-1,2,4-oxadiazol-5-yl]propanoic acid Chemical compound N=1OC(CCC(O)=O)=NC=1C(CC(C)C)NC(=O)CC(C=C1)=CC=C1NC(=O)NC1=CC=CC=C1F WNGIJWWXPVEZIA-UHFFFAOYSA-N 0.000 claims description 2
- NDAOQILPGCTKAO-UHFFFAOYSA-N 3-[3-[1-[[2-[4-[(2-fluorophenyl)carbamoylamino]phenyl]acetyl]amino]-3-methylbutyl]-1,2-oxazol-5-yl]propanoic acid Chemical compound C1=C(CCC(O)=O)ON=C1C(CC(C)C)NC(=O)CC(C=C1)=CC=C1NC(=O)NC1=CC=CC=C1F NDAOQILPGCTKAO-UHFFFAOYSA-N 0.000 claims description 2
- FECUIVMNWPGAHF-UHFFFAOYSA-N 3-[3-[1-[[2-[4-[(2-fluorophenyl)carbamoylamino]phenyl]acetyl]amino]-3-methylbutyl]-4,5-dihydro-1,2-oxazol-5-yl]propanoic acid Chemical compound N=1OC(CCC(O)=O)CC=1C(CC(C)C)NC(=O)CC(C=C1)=CC=C1NC(=O)NC1=CC=CC=C1F FECUIVMNWPGAHF-UHFFFAOYSA-N 0.000 claims description 2
- NUIGIOAOIIEMLJ-UHFFFAOYSA-N 3-[3-[1-[[2-[4-[(2-methoxyphenyl)carbamoylamino]phenyl]acetyl]amino]-3-methylbutyl]pyrazol-1-yl]propanoic acid Chemical compound COC1=CC=CC=C1NC(=O)NC(C=C1)=CC=C1CC(=O)NC(CC(C)C)C1=NN(CCC(O)=O)C=C1 NUIGIOAOIIEMLJ-UHFFFAOYSA-N 0.000 claims description 2
- SADWDDUVTQJJOQ-UHFFFAOYSA-N 3-[3-[1-[[2-[4-[(3-cyclopentylpyridin-2-yl)carbamoylamino]phenyl]acetyl]amino]-3-methylbutyl]-1,2-oxazol-5-yl]propanoic acid Chemical compound C1=C(CCC(O)=O)ON=C1C(CC(C)C)NC(=O)CC(C=C1)=CC=C1NC(=O)NC1=NC=CC=C1C1CCCC1 SADWDDUVTQJJOQ-UHFFFAOYSA-N 0.000 claims description 2
- CPYREOPRIFPIDU-UHFFFAOYSA-N 3-[3-[2-[2-[4-[(2-methylphenyl)carbamoylamino]phenyl]acetyl]-3,4-dihydro-1h-isoquinolin-3-yl]-1,2-oxazol-5-yl]propanoic acid Chemical compound CC1=CC=CC=C1NC(=O)NC(C=C1)=CC=C1CC(=O)N1C(C2=NOC(CCC(O)=O)=C2)CC2=CC=CC=C2C1 CPYREOPRIFPIDU-UHFFFAOYSA-N 0.000 claims description 2
- TXORLPKSRYMYPT-UHFFFAOYSA-N 3-[3-[2-methyl-1-[2-[4-[(2-methylphenyl)carbamoylamino]phenyl]acetyl]pyrrolidin-2-yl]-1,2-oxazol-5-yl]propanoic acid Chemical compound CC1=CC=CC=C1NC(=O)NC(C=C1)=CC=C1CC(=O)N1C(C2=NOC(CCC(O)=O)=C2)(C)CCC1 TXORLPKSRYMYPT-UHFFFAOYSA-N 0.000 claims description 2
- OJDDKEYLGQPWDS-UHFFFAOYSA-N 3-[3-[3,3-dimethyl-1-[2-[4-[(2-methylphenyl)carbamoylamino]phenyl]acetyl]pyrrolidin-2-yl]-1,2-oxazol-5-yl]propanoic acid Chemical compound CC1=CC=CC=C1NC(=O)NC(C=C1)=CC=C1CC(=O)N1C(C2=NOC(CCC(O)=O)=C2)C(C)(C)CC1 OJDDKEYLGQPWDS-UHFFFAOYSA-N 0.000 claims description 2
- FBWKPNCVKWNTMZ-UHFFFAOYSA-N 3-[3-[3-[2-[4-[(2-methylphenyl)carbamoylamino]phenyl]acetyl]-1,3-oxazolidin-4-yl]-1,2-oxazol-5-yl]propanoic acid Chemical compound CC1=CC=CC=C1NC(=O)NC(C=C1)=CC=C1CC(=O)N1C(C2=NOC(CCC(O)=O)=C2)COC1 FBWKPNCVKWNTMZ-UHFFFAOYSA-N 0.000 claims description 2
- RGUDMEVSXGALPZ-UHFFFAOYSA-N 3-[3-[3-[2-[4-[(2-methylphenyl)carbamoylamino]phenyl]acetyl]-1,3-thiazolidin-4-yl]-1,2-oxazol-5-yl]propanoic acid Chemical compound CC1=CC=CC=C1NC(=O)NC(C=C1)=CC=C1CC(=O)N1C(C2=NOC(CCC(O)=O)=C2)CSC1 RGUDMEVSXGALPZ-UHFFFAOYSA-N 0.000 claims description 2
- OQYAOHRTBOZRDJ-UHFFFAOYSA-N 3-[3-[3-methyl-1-[2-[4-[(2-methylphenyl)carbamoylamino]phenyl]acetyl]pyrrolidin-2-yl]-1,2-oxazol-5-yl]propanoic acid Chemical compound CC1CCN(C(=O)CC=2C=CC(NC(=O)NC=3C(=CC=CC=3)C)=CC=2)C1C=1C=C(CCC(O)=O)ON=1 OQYAOHRTBOZRDJ-UHFFFAOYSA-N 0.000 claims description 2
- BAKRWGCOTCJFCK-UHFFFAOYSA-N 3-[3-[3-methyl-1-[[2-[4-[(2-methylphenyl)carbamoylamino]phenyl]acetyl]amino]butyl]-1,2,4-oxadiazol-5-yl]propanoic acid Chemical compound N=1OC(CCC(O)=O)=NC=1C(CC(C)C)NC(=O)CC(C=C1)=CC=C1NC(=O)NC1=CC=CC=C1C BAKRWGCOTCJFCK-UHFFFAOYSA-N 0.000 claims description 2
- PWPUACJNJUPNMA-UHFFFAOYSA-N 3-[3-[4-(methylamino)-1-[2-[4-[(2-methylphenyl)carbamoylamino]phenyl]acetyl]pyrrolidin-2-yl]-1,2-oxazol-5-yl]propanoic acid Chemical compound C1C(NC)CC(C2=NOC(CCC(O)=O)=C2)N1C(=O)CC(C=C1)=CC=C1NC(=O)NC1=CC=CC=C1C PWPUACJNJUPNMA-UHFFFAOYSA-N 0.000 claims description 2
- PUPRDEGNEUYWIR-UHFFFAOYSA-N 3-[3-[4-amino-1-[2-[4-[(2-methylphenyl)carbamoylamino]phenyl]acetyl]pyrrolidin-2-yl]-1,2-oxazol-5-yl]propanoic acid Chemical compound CC1=CC=CC=C1NC(=O)NC(C=C1)=CC=C1CC(=O)N1C(C2=NOC(CCC(O)=O)=C2)CC(N)C1 PUPRDEGNEUYWIR-UHFFFAOYSA-N 0.000 claims description 2
- BNJAGPGSINHKFN-UHFFFAOYSA-N 3-[3-[4-hydroxy-1-[2-[4-[(2-methylphenyl)carbamoylamino]phenyl]acetyl]pyrrolidin-2-yl]-1,2-oxazol-5-yl]propanoic acid Chemical compound CC1=CC=CC=C1NC(=O)NC(C=C1)=CC=C1CC(=O)N1C(C2=NOC(CCC(O)=O)=C2)CC(O)C1 BNJAGPGSINHKFN-UHFFFAOYSA-N 0.000 claims description 2
- ZYQRSODTOULYMV-UHFFFAOYSA-N 3-[3-[4-methyl-1-[2-[4-[(2-methylphenyl)carbamoylamino]phenyl]acetyl]pyrrolidin-2-yl]-1,2-oxazol-5-yl]propanoic acid Chemical compound C1C(C)CC(C2=NOC(CCC(O)=O)=C2)N1C(=O)CC(C=C1)=CC=C1NC(=O)NC1=CC=CC=C1C ZYQRSODTOULYMV-UHFFFAOYSA-N 0.000 claims description 2
- VDYXCQIYWYJORO-UHFFFAOYSA-N 3-[3-[5-methyl-1-[2-[4-[(2-methylphenyl)carbamoylamino]phenyl]acetyl]pyrrolidin-2-yl]-1,2-oxazol-5-yl]propanoic acid Chemical compound CC1CCC(C2=NOC(CCC(O)=O)=C2)N1C(=O)CC(C=C1)=CC=C1NC(=O)NC1=CC=CC=C1C VDYXCQIYWYJORO-UHFFFAOYSA-N 0.000 claims description 2
- ONJSTYHGGGDHFG-UHFFFAOYSA-N 3-[4-[1-[[2-[3-cyclopentyl-4-[(3-methylpyridin-2-yl)carbamoylamino]phenyl]acetyl]amino]-3-methylbutyl]-3h-1,2,4-triazol-2-yl]propanoic acid Chemical compound C1N(CCC(O)=O)N=CN1C(CC(C)C)NC(=O)CC(C=C1C2CCCC2)=CC=C1NC(=O)NC1=NC=CC=C1C ONJSTYHGGGDHFG-UHFFFAOYSA-N 0.000 claims description 2
- HZVQGESZIRPWMS-UHFFFAOYSA-N 3-[4-[1-[[2-[3-cyclopentyl-4-[(3-methylpyridin-2-yl)carbamoylamino]phenyl]acetyl]amino]-3-methylbutyl]-5h-tetrazol-1-yl]propanoic acid Chemical compound C1N(CCC(O)=O)N=NN1C(CC(C)C)NC(=O)CC(C=C1C2CCCC2)=CC=C1NC(=O)NC1=NC=CC=C1C HZVQGESZIRPWMS-UHFFFAOYSA-N 0.000 claims description 2
- RFYCZJUGAHKEFT-UHFFFAOYSA-N 3-[4-[1-[[2-[3-methoxy-4-(pyridin-2-ylcarbamoylamino)phenyl]acetyl]amino]-3-methylbutyl]-1,3-thiazol-2-yl]propanoic acid Chemical compound C=1C=C(NC(=O)NC=2N=CC=CC=2)C(OC)=CC=1CC(=O)NC(CC(C)C)C1=CSC(CCC(O)=O)=N1 RFYCZJUGAHKEFT-UHFFFAOYSA-N 0.000 claims description 2
- QMHGJGPKZYHUCW-UHFFFAOYSA-N 3-[4-[1-[[2-[3-methoxy-4-(pyridin-2-ylcarbamoylamino)phenyl]acetyl]amino]-3-methylbutyl]-3h-1,2,4-triazol-2-yl]propanoic acid Chemical compound C=1C=C(NC(=O)NC=2N=CC=CC=2)C(OC)=CC=1CC(=O)NC(CC(C)C)N1CN(CCC(O)=O)N=C1 QMHGJGPKZYHUCW-UHFFFAOYSA-N 0.000 claims description 2
- DZYDLVFEJZAFTB-UHFFFAOYSA-N 3-[4-[1-[[2-[3-methoxy-4-(pyridin-2-ylcarbamoylamino)phenyl]acetyl]amino]-3-methylbutyl]-5h-tetrazol-1-yl]propanoic acid Chemical compound C=1C=C(NC(=O)NC=2N=CC=CC=2)C(OC)=CC=1CC(=O)NC(CC(C)C)N1CN(CCC(O)=O)N=N1 DZYDLVFEJZAFTB-UHFFFAOYSA-N 0.000 claims description 2
- VQHWVJDNBDWGKE-UHFFFAOYSA-N 3-[4-[1-[[2-[3-methoxy-4-[(3-methylpyridin-2-yl)carbamoylamino]phenyl]acetyl]amino]-3-methylbutyl]-3h-1,2,4-triazol-2-yl]propanoic acid Chemical compound C=1C=C(NC(=O)NC=2C(=CC=CN=2)C)C(OC)=CC=1CC(=O)NC(CC(C)C)N1CN(CCC(O)=O)N=C1 VQHWVJDNBDWGKE-UHFFFAOYSA-N 0.000 claims description 2
- VECDKSXKQKNUSG-UHFFFAOYSA-N 3-[4-[1-[[2-[3-methoxy-4-[(3-methylpyridin-2-yl)carbamoylamino]phenyl]acetyl]amino]-3-methylbutyl]-5h-tetrazol-1-yl]propanoic acid Chemical compound C=1C=C(NC(=O)NC=2C(=CC=CN=2)C)C(OC)=CC=1CC(=O)NC(CC(C)C)N1CN(CCC(O)=O)N=N1 VECDKSXKQKNUSG-UHFFFAOYSA-N 0.000 claims description 2
- UMJKIVZGIFTIDK-UHFFFAOYSA-N 3-[4-[1-[[2-[3-methoxy-4-[(3-methylpyridin-2-yl)carbamoylamino]phenyl]acetyl]amino]-3-methylbutyl]imidazol-1-yl]propanoic acid Chemical compound C=1C=C(NC(=O)NC=2C(=CC=CN=2)C)C(OC)=CC=1CC(=O)NC(CC(C)C)C1=CN(CCC(O)=O)C=N1 UMJKIVZGIFTIDK-UHFFFAOYSA-N 0.000 claims description 2
- KALHXHLPENMEFZ-UHFFFAOYSA-N 3-[4-[1-[[2-[4-[(2-methoxyphenyl)carbamoylamino]phenyl]acetyl]amino]-3-methylbutyl]-3h-1,2,4-triazol-2-yl]propanoic acid Chemical compound COC1=CC=CC=C1NC(=O)NC(C=C1)=CC=C1CC(=O)NC(CC(C)C)N1C=NN(CCC(O)=O)C1 KALHXHLPENMEFZ-UHFFFAOYSA-N 0.000 claims description 2
- PGTOFLKFTMTKGW-UHFFFAOYSA-N 3-[4-[1-[[2-[4-[(3-cyclopentylpyridin-2-yl)carbamoylamino]-3-(trifluoromethyl)phenyl]acetyl]amino]-3-methylbutyl]-5h-tetrazol-1-yl]propanoic acid Chemical compound C1N(CCC(O)=O)N=NN1C(CC(C)C)NC(=O)CC(C=C1C(F)(F)F)=CC=C1NC(=O)NC1=NC=CC=C1C1CCCC1 PGTOFLKFTMTKGW-UHFFFAOYSA-N 0.000 claims description 2
- JNBCCDKHITYYLN-UHFFFAOYSA-N 3-[4-[1-[[2-[4-[(3-cyclopentylpyridin-2-yl)carbamoylamino]-3-methoxyphenyl]acetyl]amino]-3-methylbutyl]-3h-1,2,4-triazol-2-yl]propanoic acid Chemical compound C=1C=C(NC(=O)NC=2C(=CC=CN=2)C2CCCC2)C(OC)=CC=1CC(=O)NC(CC(C)C)N1CN(CCC(O)=O)N=C1 JNBCCDKHITYYLN-UHFFFAOYSA-N 0.000 claims description 2
- JTRHOUGVQBQZDV-UHFFFAOYSA-N 3-[4-[1-[[2-[4-[(3-cyclopentylpyridin-2-yl)carbamoylamino]-3-methoxyphenyl]acetyl]amino]-3-methylbutyl]-5h-tetrazol-1-yl]propanoic acid Chemical compound C=1C=C(NC(=O)NC=2C(=CC=CN=2)C2CCCC2)C(OC)=CC=1CC(=O)NC(CC(C)C)N1CN(CCC(O)=O)N=N1 JTRHOUGVQBQZDV-UHFFFAOYSA-N 0.000 claims description 2
- RAUKOZAWRORVFI-UHFFFAOYSA-N 3-[4-[1-[[2-[4-[(3-methoxypyridin-2-yl)carbamoylamino]-3-methylphenyl]acetyl]amino]-3-methylbutyl]-1,1-dioxo-1,3-thiazol-2-yl]propanoic acid Chemical compound COC1=CC=CN=C1NC(=O)NC(C(=C1)C)=CC=C1CC(=O)NC(CC(C)C)C1=CS(=O)(=O)C(CCC(O)=O)=N1 RAUKOZAWRORVFI-UHFFFAOYSA-N 0.000 claims description 2
- VHXLSJBXWHGIQV-UHFFFAOYSA-N 3-[4-[2-[3-cyclopentyl-4-[(3-methylpyridin-2-yl)carbamoylamino]phenyl]acetyl]-3-(2-methylpropyl)-2-oxopiperazin-1-yl]propanoic acid Chemical compound C1CN(CCC(O)=O)C(=O)C(CC(C)C)N1C(=O)CC(C=C1C2CCCC2)=CC=C1NC(=O)NC1=NC=CC=C1C VHXLSJBXWHGIQV-UHFFFAOYSA-N 0.000 claims description 2
- YMGABLQDYSLOCO-UHFFFAOYSA-N 3-[4-[2-[3-cyclopentyl-4-[(3-methylpyridin-2-yl)carbamoylamino]phenyl]acetyl]-5-(2-methylpropyl)-2-oxopiperazin-1-yl]propanoic acid Chemical compound CC(C)CC1CN(CCC(O)=O)C(=O)CN1C(=O)CC(C=C1C2CCCC2)=CC=C1NC(=O)NC1=NC=CC=C1C YMGABLQDYSLOCO-UHFFFAOYSA-N 0.000 claims description 2
- XNTXPZBEHNQMKJ-UHFFFAOYSA-N 3-[4-[2-[3-fluoro-4-[(2-methylphenyl)carbamoylamino]phenyl]acetyl]-3-(2-methylpropyl)-2-oxopiperazin-1-yl]propanoic acid Chemical compound C1CN(CCC(O)=O)C(=O)C(CC(C)C)N1C(=O)CC(C=C1F)=CC=C1NC(=O)NC1=CC=CC=C1C XNTXPZBEHNQMKJ-UHFFFAOYSA-N 0.000 claims description 2
- GXTOANWOJIJYAX-UHFFFAOYSA-N 3-[4-[2-[3-fluoro-4-[(2-methylphenyl)carbamoylamino]phenyl]acetyl]-5-(2-methylpropyl)-2-oxopiperazin-1-yl]propanoic acid Chemical compound CC(C)CC1CN(CCC(O)=O)C(=O)CN1C(=O)CC(C=C1F)=CC=C1NC(=O)NC1=CC=CC=C1C GXTOANWOJIJYAX-UHFFFAOYSA-N 0.000 claims description 2
- NVBOGTVSBDXNFP-UHFFFAOYSA-N 3-[4-[2-[3-methoxy-4-(pyridin-2-ylcarbamoylamino)phenyl]acetyl]-3-(2-methylpropyl)-2-oxopiperazin-1-yl]propanoic acid Chemical compound C=1C=C(NC(=O)NC=2N=CC=CC=2)C(OC)=CC=1CC(=O)N1CCN(CCC(O)=O)C(=O)C1CC(C)C NVBOGTVSBDXNFP-UHFFFAOYSA-N 0.000 claims description 2
- HSMYBTMFJUDUFX-UHFFFAOYSA-N 3-[4-[2-[3-methoxy-4-(pyridin-2-ylcarbamoylamino)phenyl]acetyl]-5-(2-methylpropyl)-2-oxopiperazin-1-yl]propanoic acid Chemical compound C=1C=C(NC(=O)NC=2N=CC=CC=2)C(OC)=CC=1CC(=O)N1CC(=O)N(CCC(O)=O)CC1CC(C)C HSMYBTMFJUDUFX-UHFFFAOYSA-N 0.000 claims description 2
- BRIVWOYWSBAOCF-UHFFFAOYSA-N 3-[4-[2-[3-methoxy-4-[(3-methylpyridin-2-yl)carbamoylamino]phenyl]acetyl]-3-(2-methylpropyl)-2-oxopiperazin-1-yl]propanoic acid Chemical compound C=1C=C(NC(=O)NC=2C(=CC=CN=2)C)C(OC)=CC=1CC(=O)N1CCN(CCC(O)=O)C(=O)C1CC(C)C BRIVWOYWSBAOCF-UHFFFAOYSA-N 0.000 claims description 2
- VPNPXXJZRDUNGA-UHFFFAOYSA-N 3-[4-[2-[3-methoxy-4-[(3-methylpyridin-2-yl)carbamoylamino]phenyl]acetyl]-5-(2-methylpropyl)-2-oxopiperazin-1-yl]propanoic acid Chemical compound C=1C=C(NC(=O)NC=2C(=CC=CN=2)C)C(OC)=CC=1CC(=O)N1CC(=O)N(CCC(O)=O)CC1CC(C)C VPNPXXJZRDUNGA-UHFFFAOYSA-N 0.000 claims description 2
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- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
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- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- BSVBQGMMJUBVOD-UHFFFAOYSA-N trisodium borate Chemical compound [Na+].[Na+].[Na+].[O-]B([O-])[O-] BSVBQGMMJUBVOD-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/33—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/333—Radicals substituted by oxygen or sulfur atoms
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- A61P37/02—Immunomodulators
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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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- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
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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
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- 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
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US6992107B1 (en) | 1995-03-10 | 2006-01-31 | Photocure Asa | Esters of 5-aminolevulinic acid and their use as photosensitizing compounds in photochemotherapy |
ATE279396T1 (de) | 1998-06-12 | 2004-10-15 | Sod Conseils Rech Applic | Imidazolderivate und ihre verwendung als somatostatin rezeptorliganden |
CN1308616A (zh) * | 1998-06-30 | 2001-08-15 | 辉瑞产品公司 | 用于治疗炎性、自身免疫和呼吸疾病的依赖于vla-4的细胞结合的非肽基抑制剂 |
US6518292B1 (en) * | 1999-03-12 | 2003-02-11 | Bristol-Myers Squibb Co. | Heterocyclic aromatic compounds usefuls as growth hormone secretagogues |
IL146288A0 (en) * | 1999-06-30 | 2002-07-25 | Daiichi Seiyaku Co | Vla-4 inhibitor compounds |
US6756378B2 (en) * | 1999-06-30 | 2004-06-29 | Pharmacopeia Drug Discovery, Inc. | VLA-4 inhibitor compounds |
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