NO324421B1 - Karboksylsyrederivater som hemmer binding av integriner til deres reseptorer og farmasoytiske preparater som omfatter dem - Google Patents

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Publication number

NO324421B1

NO324421B1 NO20015418A NO20015418A NO324421B1 NO 324421 B1 NO324421 B1 NO 324421B1 NO 20015418 A NO20015418 A NO 20015418A NO 20015418 A NO20015418 A NO 20015418A NO 324421 B1 NO324421 B1 NO 324421B1

Authority

NO

Norway

Prior art keywords

amino

methyl

carbonyl

oxo

dihydro

Prior art date

1999-05-07

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• 102000005962 receptors Human genes 0.000 title abstract description 3
• 108020003175 receptors Proteins 0.000 title abstract description 3
• 108010044426 integrins Proteins 0.000 title description 12
• 102000006495 integrins Human genes 0.000 title description 12
• 239000008194 pharmaceutical composition Substances 0.000 title description 3
• 150000001732 carboxylic acid derivatives Chemical class 0.000 title description 2
• 150000001875 compounds Chemical class 0.000 claims abstract description 103
• -1 hydrogen- Chemical class 0.000 claims description 153
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 86
• 125000000217 alkyl group Chemical group 0.000 claims description 61
• 125000003118 aryl group Chemical group 0.000 claims description 45
• XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 38
• 239000001257 hydrogen Substances 0.000 claims description 35
• 229910052739 hydrogen Inorganic materials 0.000 claims description 35
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 34
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 33
• 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 28
• 229910052799 carbon Inorganic materials 0.000 claims description 23
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 23
• 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 22
• 150000002367 halogens Chemical class 0.000 claims description 21
• 229910052736 halogen Inorganic materials 0.000 claims description 20
• 150000003839 salts Chemical class 0.000 claims description 20
• 235000019260 propionic acid Nutrition 0.000 claims description 19
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 17
• GBXQPDCOMJJCMJ-UHFFFAOYSA-M trimethyl-[6-(trimethylazaniumyl)hexyl]azanium;bromide Chemical compound [Br-].C[N+](C)(C)CCCCCC[N+](C)(C)C GBXQPDCOMJJCMJ-UHFFFAOYSA-M 0.000 claims description 17
• IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims description 16
• 150000002431 hydrogen Chemical class 0.000 claims description 15
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 15
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
• 125000006575 electron-withdrawing group Chemical group 0.000 claims description 13
• 229910052757 nitrogen Inorganic materials 0.000 claims description 13
• 125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 claims description 13
• 125000004104 aryloxy group Chemical group 0.000 claims description 10
• 150000002148 esters Chemical class 0.000 claims description 10
• 125000004642 (C1-C12) alkoxy group Chemical group 0.000 claims description 9
• 239000000825 pharmaceutical preparation Substances 0.000 claims description 9
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
• 150000001408 amides Chemical class 0.000 claims description 8
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
• 230000003287 optical effect Effects 0.000 claims description 6
• 150000004657 carbamic acid derivatives Chemical class 0.000 claims description 5
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
• LPMXAWSSWLCPMJ-SFHVURJKSA-N (3s)-3-[[1-[(2-chlorophenyl)methyl]-4-hydroxy-2-oxopyridin-3-yl]carbamoylamino]-3-(4-methylphenyl)propanoic acid Chemical compound C1=CC(C)=CC=C1[C@H](CC(O)=O)NC(=O)NC(C1=O)=C(O)C=CN1CC1=CC=CC=C1Cl LPMXAWSSWLCPMJ-SFHVURJKSA-N 0.000 claims description 4
• JIYRLYKPKAOWDE-QFIPXVFZSA-N (3s)-3-[[1-benzyl-2-methyl-4-(2-methylpropyl)-6-oxopyrimidin-5-yl]carbamoylamino]-3-(4-methylphenyl)propanoic acid Chemical compound O=C1C(NC(=O)N[C@@H](CC(O)=O)C=2C=CC(C)=CC=2)=C(CC(C)C)N=C(C)N1CC1=CC=CC=C1 JIYRLYKPKAOWDE-QFIPXVFZSA-N 0.000 claims description 4
• XNJBPXQBMAWTHQ-FQEVSTJZSA-N (3s)-3-[[4-amino-1-[(2-chlorophenyl)methyl]-6-methyl-2-oxopyridin-3-yl]carbamoylamino]-3-(4-methylphenyl)propanoic acid Chemical compound C1=CC(C)=CC=C1[C@H](CC(O)=O)NC(=O)NC(C1=O)=C(N)C=C(C)N1CC1=CC=CC=C1Cl XNJBPXQBMAWTHQ-FQEVSTJZSA-N 0.000 claims description 4
• 241001465754 Metazoa Species 0.000 claims description 4
• 150000007854 aminals Chemical class 0.000 claims description 4
• 239000003937 drug carrier Substances 0.000 claims description 4
• LLPUNNOFVNYJJQ-VWLOTQADSA-N (3s)-3-[[1-[(2-chlorophenyl)methyl]-2-oxo-4-phenylpyridin-3-yl]carbamoylamino]-3-(4-methylphenyl)propanoic acid Chemical compound C1=CC(C)=CC=C1[C@H](CC(O)=O)NC(=O)NC(C1=O)=C(C=2C=CC=CC=2)C=CN1CC1=CC=CC=C1Cl LLPUNNOFVNYJJQ-VWLOTQADSA-N 0.000 claims description 3
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• XEHDSQSMOHDBQB-FQEVSTJZSA-N (3s)-3-[[1-[(2-chlorophenyl)methyl]-5-methyl-2-oxopyridin-3-yl]carbamoylamino]-3-(4-methylphenyl)propanoic acid Chemical compound C1=CC(C)=CC=C1[C@H](CC(O)=O)NC(=O)NC(C1=O)=CC(C)=CN1CC1=CC=CC=C1Cl XEHDSQSMOHDBQB-FQEVSTJZSA-N 0.000 claims description 3
• YJBZUNGDVIZBHK-FQEVSTJZSA-N (3s)-3-(1,3-benzodioxol-5-yl)-3-[(1-benzyl-2-oxo-4-propylpyridin-3-yl)carbamoylamino]propanoic acid Chemical compound O=C1C(NC(=O)N[C@@H](CC(O)=O)C=2C=C3OCOC3=CC=2)=C(CCC)C=CN1CC1=CC=CC=C1 YJBZUNGDVIZBHK-FQEVSTJZSA-N 0.000 claims description 2
• CEAOPVIFGJTFDW-SFHVURJKSA-N (3s)-3-[[1-[(2-chloro-6-fluorophenyl)methyl]-4-hydroxy-2-oxopyridin-3-yl]carbamoylamino]-3-(4-methylphenyl)propanoic acid Chemical compound C1=CC(C)=CC=C1[C@H](CC(O)=O)NC(=O)NC(C1=O)=C(O)C=CN1CC1=C(F)C=CC=C1Cl CEAOPVIFGJTFDW-SFHVURJKSA-N 0.000 claims description 2
• YFSGACWYJRMDHV-NRFANRHFSA-N (3s)-3-[[1-[(2-chlorophenyl)methyl]-4-ethyl-2-oxopyridin-3-yl]carbamoylamino]-3-(4-methylphenyl)propanoic acid Chemical compound O=C1C(NC(=O)N[C@@H](CC(O)=O)C=2C=CC(C)=CC=2)=C(CC)C=CN1CC1=CC=CC=C1Cl YFSGACWYJRMDHV-NRFANRHFSA-N 0.000 claims description 2
• RIXSHRQWXXIBFX-SFHVURJKSA-N (3s)-3-[[1-[(2-chlorophenyl)methyl]-4-hydroxy-2-oxopyridin-3-yl]carbamoylamino]-3-(3-methoxyphenyl)propanoic acid Chemical compound COC1=CC=CC([C@H](CC(O)=O)NC(=O)NC=2C(N(CC=3C(=CC=CC=3)Cl)C=CC=2O)=O)=C1 RIXSHRQWXXIBFX-SFHVURJKSA-N 0.000 claims description 2
• JNBGWQREIHPHSK-SFHVURJKSA-N (3s)-3-[[1-[(2-chlorophenyl)methyl]-4-hydroxy-2-oxopyridin-3-yl]carbamoylamino]-3-(4-methoxy-3-methylphenyl)propanoic acid Chemical compound C1=C(C)C(OC)=CC=C1[C@H](CC(O)=O)NC(=O)NC(C1=O)=C(O)C=CN1CC1=CC=CC=C1Cl JNBGWQREIHPHSK-SFHVURJKSA-N 0.000 claims description 2
• ICYAAIQHXXAWGE-SFHVURJKSA-N (3s)-3-[[1-[(2-chlorophenyl)methyl]-4-hydroxy-2-oxopyridin-3-yl]carbamoylamino]-3-(4-methoxyphenyl)propanoic acid Chemical compound C1=CC(OC)=CC=C1[C@H](CC(O)=O)NC(=O)NC(C1=O)=C(O)C=CN1CC1=CC=CC=C1Cl ICYAAIQHXXAWGE-SFHVURJKSA-N 0.000 claims description 2
• SVJORHDCZSSIIV-KRWDZBQOSA-N (3s)-3-[[1-[(2-chlorophenyl)methyl]-4-hydroxy-2-oxopyridin-3-yl]carbamoylamino]-3-phenylpropanoic acid Chemical compound N([C@@H](CC(=O)O)C=1C=CC=CC=1)C(=O)NC(C1=O)=C(O)C=CN1CC1=CC=CC=C1Cl SVJORHDCZSSIIV-KRWDZBQOSA-N 0.000 claims description 2
• DTSFNLOQTZNOMO-FQEVSTJZSA-N (3s)-3-[[1-[(2-chlorophenyl)methyl]-4-methyl-2-oxopyridin-3-yl]carbamoylamino]-3-(4-methoxyphenyl)propanoic acid Chemical compound C1=CC(OC)=CC=C1[C@H](CC(O)=O)NC(=O)NC(C1=O)=C(C)C=CN1CC1=CC=CC=C1Cl DTSFNLOQTZNOMO-FQEVSTJZSA-N 0.000 claims description 2
• FCRNFQMIFLZTMG-FQEVSTJZSA-N (3s)-3-[[1-[(2-chlorophenyl)methyl]-4-methyl-2-oxopyridin-3-yl]carbamoylamino]-3-(4-methylphenyl)propanoic acid Chemical compound C1=CC(C)=CC=C1[C@H](CC(O)=O)NC(=O)NC(C1=O)=C(C)C=CN1CC1=CC=CC=C1Cl FCRNFQMIFLZTMG-FQEVSTJZSA-N 0.000 claims description 2
• YYPZHWRKAVHZNN-SFHVURJKSA-N (3s)-3-[[1-[(2-fluorophenyl)methyl]-4-hydroxy-2-oxopyridin-3-yl]carbamoylamino]-3-(4-methylphenyl)propanoic acid Chemical compound C1=CC(C)=CC=C1[C@H](CC(O)=O)NC(=O)NC(C1=O)=C(O)C=CN1CC1=CC=CC=C1F YYPZHWRKAVHZNN-SFHVURJKSA-N 0.000 claims description 2
• MGZUXMWNUQSKLO-NRFANRHFSA-N (3s)-3-[[4-(azetidin-1-yl)-1-[(2-chlorophenyl)methyl]-2-oxopyridin-3-yl]carbamoylamino]-3-(4-methylphenyl)propanoic acid Chemical compound C1=CC(C)=CC=C1[C@H](CC(O)=O)NC(=O)NC(C1=O)=C(N2CCC2)C=CN1CC1=CC=CC=C1Cl MGZUXMWNUQSKLO-NRFANRHFSA-N 0.000 claims description 2
• HDTUNALIEDCJGZ-IBGZPJMESA-N (3s)-3-[[4-amino-1-[(2-chlorophenyl)methyl]-2-oxopyridin-3-yl]carbamoylamino]-3-(4-methylphenyl)propanoic acid Chemical compound C1=CC(C)=CC=C1[C@H](CC(O)=O)NC(=O)NC(C1=O)=C(N)C=CN1CC1=CC=CC=C1Cl HDTUNALIEDCJGZ-IBGZPJMESA-N 0.000 claims description 2
• 125000004076 pyridyl group Chemical group 0.000 claims description 2
• QQWKDWJISNTBNF-FQEVSTJZSA-N (3s)-3-[[1-[(2-bromophenyl)methyl]-2-oxopyridin-3-yl]carbamoylamino]-3-(4-methylphenyl)propanoic acid Chemical compound C1=CC(C)=CC=C1[C@H](CC(O)=O)NC(=O)NC(C1=O)=CC=CN1CC1=CC=CC=C1Br QQWKDWJISNTBNF-FQEVSTJZSA-N 0.000 claims 1
• YJWVXVQDHAQWSO-FQEVSTJZSA-N (3s)-3-[[1-[(2-chlorophenyl)methyl]-2,4-dimethyl-6-oxopyrimidin-5-yl]carbamoylamino]-3-(4-methylphenyl)propanoic acid Chemical compound C1=CC(C)=CC=C1[C@H](CC(O)=O)NC(=O)NC(C1=O)=C(C)N=C(C)N1CC1=CC=CC=C1Cl YJWVXVQDHAQWSO-FQEVSTJZSA-N 0.000 claims 1
• KZNYVVVWALITCR-QHCPKHFHSA-N (3s)-3-[[1-[(2-chlorophenyl)methyl]-4-(4-methylpiperazin-1-yl)-2-oxopyridin-3-yl]carbamoylamino]-3-(4-methylphenyl)propanoic acid Chemical compound C1CN(C)CCN1C1=C(NC(=O)N[C@@H](CC(O)=O)C=2C=CC(C)=CC=2)C(=O)N(CC=2C(=CC=CC=2)Cl)C=C1 KZNYVVVWALITCR-QHCPKHFHSA-N 0.000 claims 1
• JPEASVDUPDPZHB-IBGZPJMESA-N (3s)-3-[[1-[(2-chlorophenyl)methyl]-4-hydroxy-2-oxopyridin-3-yl]carbamoylamino]-3-(3,5-dimethylphenyl)propanoic acid Chemical compound CC1=CC(C)=CC([C@H](CC(O)=O)NC(=O)NC=2C(N(CC=3C(=CC=CC=3)Cl)C=CC=2O)=O)=C1 JPEASVDUPDPZHB-IBGZPJMESA-N 0.000 claims 1
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• 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims 1
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