SK288186B6 - Deriváty kyseliny propiónovej, ktoré inhibujú väzbu integrínov na ich receptory, farmaceutické kompozície s ich obsahom a ich použitie - Google Patents

Info

Publication number

SK288186B6

SK288186B6 SK1609-2001A SK16092001A SK288186B6 SK 288186 B6 SK288186 B6 SK 288186B6 SK 16092001 A SK16092001 A SK 16092001A SK 288186 B6 SK288186 B6 SK 288186B6

Authority

SK

Slovakia

Prior art keywords

oxo

pyridyl

propanoic acid

amino

benzodioxol

Prior art date

1999-05-07

Links

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• 102000005962 receptors Human genes 0.000 title claims abstract description 5
• 108020003175 receptors Proteins 0.000 title claims abstract description 5
• XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical class CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 title claims description 33
• 108010044426 integrins Proteins 0.000 title claims description 16
• 102000006495 integrins Human genes 0.000 title claims description 16
• 150000001875 compounds Chemical class 0.000 claims abstract description 96
• -1 1,3-benzodioxol-5-yl Chemical group 0.000 claims description 183
• 125000000217 alkyl group Chemical group 0.000 claims description 58
• 125000003118 aryl group Chemical group 0.000 claims description 34
• DUWWHGPELOTTOE-UHFFFAOYSA-N n-(5-chloro-2,4-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC(OC)=C(NC(=O)CC(C)=O)C=C1Cl DUWWHGPELOTTOE-UHFFFAOYSA-N 0.000 claims description 32
• 235000019260 propionic acid Nutrition 0.000 claims description 32
• 239000003814 drug Substances 0.000 claims description 15
• 150000003839 salts Chemical class 0.000 claims description 15
• 229910052739 hydrogen Inorganic materials 0.000 claims description 14
• 239000001257 hydrogen Substances 0.000 claims description 14
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 12
• 230000002401 inhibitory effect Effects 0.000 claims description 12
• 201000010099 disease Diseases 0.000 claims description 9
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 9
• 238000002360 preparation method Methods 0.000 claims description 9
• 125000003104 hexanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 8
• 150000002148 esters Chemical class 0.000 claims description 6
• INEVELMGVMOTKD-NQCNTLBGSA-N (3s)-3-(1,3-benzodioxol-5-yl)-3-[2-(5-benzyl-2-oxopyridin-1-yl)hexanoylamino]propanoic acid Chemical compound N([C@@H](CC(O)=O)C=1C=C2OCOC2=CC=1)C(=O)C(CCCC)N(C(C=C1)=O)C=C1CC1=CC=CC=C1 INEVELMGVMOTKD-NQCNTLBGSA-N 0.000 claims description 5
• KRZJRNZICWNMOA-GXSJLCMTSA-N (3s,4r)-4,8-dihydroxy-3-methoxy-3,4-dihydro-2h-naphthalen-1-one Chemical compound C1=CC=C2[C@@H](O)[C@@H](OC)CC(=O)C2=C1O KRZJRNZICWNMOA-GXSJLCMTSA-N 0.000 claims description 5
• KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 5
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
• 150000001408 amides Chemical class 0.000 claims description 5
• 208000010247 contact dermatitis Diseases 0.000 claims description 4
• 230000001225 therapeutic effect Effects 0.000 claims description 4
• KXOSRTYMJGXFKD-HMTLIYDFSA-N (3s)-3-(1,3-benzodioxol-5-yl)-3-[2-(3-benzyl-2-oxopyridin-1-yl)pentanoylamino]propanoic acid Chemical compound N([C@@H](CC(O)=O)C=1C=C2OCOC2=CC=1)C(=O)C(CCC)N(C1=O)C=CC=C1CC1=CC=CC=C1 KXOSRTYMJGXFKD-HMTLIYDFSA-N 0.000 claims description 3
• ZJKSFHCOCPHFQY-GOTSBHOMSA-N (3s)-3-(1,3-benzodioxol-5-yl)-3-[[(2s)-2-(3-benzyl-2-oxopyridin-1-yl)hexanoyl]amino]propanoic acid Chemical compound O=C1N([C@H](C(=O)N[C@@H](CC(O)=O)C=2C=C3OCOC3=CC=2)CCCC)C=CC=C1CC1=CC=CC=C1 ZJKSFHCOCPHFQY-GOTSBHOMSA-N 0.000 claims description 3
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• 206010039073 rheumatoid arthritis Diseases 0.000 claims description 3
• BRFZHFYKBOLOAR-BGERDNNASA-N (3s)-3-(1,3-benzodioxol-5-yl)-3-[2-(3-benzyl-2-oxopyridin-1-yl)butanoylamino]propanoic acid Chemical compound N([C@@H](CC(O)=O)C=1C=C2OCOC2=CC=1)C(=O)C(CC)N(C1=O)C=CC=C1CC1=CC=CC=C1 BRFZHFYKBOLOAR-BGERDNNASA-N 0.000 claims description 2
• TYZLXAWLBLEXOT-UXMRNZNESA-N (3s)-3-(1,3-benzodioxol-5-yl)-3-[2-[3-[(2-chlorophenyl)methyl]-5-methyl-2-oxopyridin-1-yl]hexanoylamino]propanoic acid Chemical compound N([C@@H](CC(O)=O)C=1C=C2OCOC2=CC=1)C(=O)C(CCCC)N(C1=O)C=C(C)C=C1CC1=CC=CC=C1Cl TYZLXAWLBLEXOT-UXMRNZNESA-N 0.000 claims description 2
• CIMQDLWDFWYYIA-QHCPKHFHSA-N (3s)-3-(1,3-benzodioxol-5-yl)-3-[[1-(3-benzyl-2-oxopyridin-1-yl)cyclohexanecarbonyl]amino]propanoic acid Chemical compound N([C@@H](CC(=O)O)C=1C=C2OCOC2=CC=1)C(=O)C1(N2C(C(CC=3C=CC=CC=3)=CC=C2)=O)CCCCC1 CIMQDLWDFWYYIA-QHCPKHFHSA-N 0.000 claims description 2
• FTNJQNQLEGKTGD-UHFFFAOYSA-N 1,3-benzodioxole Chemical compound C1=CC=C2OCOC2=C1 FTNJQNQLEGKTGD-UHFFFAOYSA-N 0.000 claims description 2
• 125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 claims description 2
• 241000124008 Mammalia Species 0.000 claims description 2
• 206010052779 Transplant rejections Diseases 0.000 claims description 2
• 125000005129 aryl carbonyl group Chemical group 0.000 claims description 2
• 201000011510 cancer Diseases 0.000 claims description 2
• 208000032839 leukemia Diseases 0.000 claims description 2
• 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 2
• GKICTZIFSOZAQL-ZEQRLZLVSA-N (3s)-3-(1,3-benzodioxol-5-yl)-3-[[(2s)-2-(3-benzyl-5-methyl-2-oxopyridin-1-yl)hexanoyl]amino]propanoic acid Chemical compound O=C1N([C@H](C(=O)N[C@@H](CC(O)=O)C=2C=C3OCOC3=CC=2)CCCC)C=C(C)C=C1CC1=CC=CC=C1 GKICTZIFSOZAQL-ZEQRLZLVSA-N 0.000 claims 1
• 125000006181 4-methyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])C([H])([H])* 0.000 claims 1
• 150000007854 aminals Chemical class 0.000 claims 1
• 125000001475 halogen functional group Chemical group 0.000 claims 1
• 239000000203 mixture Substances 0.000 abstract description 52
• 108010008212 Integrin alpha4beta1 Proteins 0.000 abstract description 3
• 238000009472 formulation Methods 0.000 abstract description 2
• 230000006806 disease prevention Effects 0.000 abstract 1
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 66
• 239000000243 solution Substances 0.000 description 29
• 210000004027 cell Anatomy 0.000 description 28
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 26
• 235000019439 ethyl acetate Nutrition 0.000 description 22
• 238000000034 method Methods 0.000 description 20
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 19
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 19
• 108010000134 Vascular Cell Adhesion Molecule-1 Proteins 0.000 description 17
• 102100023543 Vascular cell adhesion protein 1 Human genes 0.000 description 17
• 125000003342 alkenyl group Chemical group 0.000 description 17
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 17
• 210000000265 leukocyte Anatomy 0.000 description 16
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
• 125000000304 alkynyl group Chemical group 0.000 description 15
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
• 125000003545 alkoxy group Chemical group 0.000 description 14
• 125000000623 heterocyclic group Chemical group 0.000 description 13
• 239000010410 layer Substances 0.000 description 13
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• 235000019198 oils Nutrition 0.000 description 13
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 12
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 12
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• 125000001424 substituent group Chemical group 0.000 description 11
• 125000001544 thienyl group Chemical group 0.000 description 11
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• 235000019441 ethanol Nutrition 0.000 description 8
• 239000000706 filtrate Substances 0.000 description 8
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• 150000001412 amines Chemical class 0.000 description 7
• 125000003710 aryl alkyl group Chemical group 0.000 description 7
• 125000004432 carbon atom Chemical group C* 0.000 description 7
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 7
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• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 7
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• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
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