MX2008002117A - Indoles sustituidos y metodos de uso de estos. - Google Patents

Info

Publication number

MX2008002117A

MX2008002117A MX2008002117A MX2008002117A MX2008002117A MX 2008002117 A MX2008002117 A MX 2008002117A MX 2008002117 A MX2008002117 A MX 2008002117A MX 2008002117 A MX2008002117 A MX 2008002117A MX 2008002117 A MX2008002117 A MX 2008002117A

Authority

MX

Mexico

Prior art keywords

amino

indol

phenyl

acid

alkyl

Prior art date

2005-08-17

Links

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• 150000002475 indoles Chemical class 0.000 title abstract description 18
• 150000001875 compounds Chemical class 0.000 claims description 133
• -1 { [[1- (4-tert-butylbenzyl) -1 H -indol-5-yl] (phenylsulfonyl) amino] methyl} benzoic acid Chemical compound 0.000 claims description 99
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 84
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 83
• 238000000034 method Methods 0.000 claims description 79
• 108010022233 Plasminogen Activator Inhibitor 1 Proteins 0.000 claims description 72
• 125000000217 alkyl group Chemical group 0.000 claims description 63
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 55
• 125000000623 heterocyclic group Chemical group 0.000 claims description 53
• 230000000694 effects Effects 0.000 claims description 45
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 45
• 239000002253 acid Substances 0.000 claims description 42
• 125000005010 perfluoroalkyl group Chemical group 0.000 claims description 42
• 150000003839 salts Chemical class 0.000 claims description 36
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 36
• 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 31
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 30
• 229960005190 phenylalanine Drugs 0.000 claims description 30
• 229940024606 amino acid Drugs 0.000 claims description 28
• 150000001413 amino acids Chemical class 0.000 claims description 27
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 27
• 229910052739 hydrogen Inorganic materials 0.000 claims description 26
• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 25
• 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 25
• 229910052736 halogen Inorganic materials 0.000 claims description 21
• 150000002367 halogens Chemical class 0.000 claims description 21
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 21
• 239000001257 hydrogen Substances 0.000 claims description 20
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 19
• 229910052757 nitrogen Inorganic materials 0.000 claims description 17
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 14
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• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 12
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• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 8
• 125000004429 atom Chemical group 0.000 claims description 7
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• PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 5
• COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 claims description 5
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• NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 claims description 4
• 230000009424 thromboembolic effect Effects 0.000 claims description 4
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 3
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• 101100516554 Caenorhabditis elegans nhr-5 gene Proteins 0.000 claims description 2
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• 229940000635 beta-alanine Drugs 0.000 claims description 2
• 230000001419 dependent effect Effects 0.000 claims description 2
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• 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 2
• 230000007505 plaque formation Effects 0.000 claims description 2
• 125000004185 ester group Chemical group 0.000 claims 6
• 102100039418 Plasminogen activator inhibitor 1 Human genes 0.000 claims 5
• FTXPWRLJYLZQJJ-VWLOTQADSA-N (2s)-2-[[2-[5-[(4-tert-butylphenyl)sulfonylamino]indol-1-yl]acetyl]amino]-3-phenylpropanoic acid Chemical compound C1=CC(C(C)(C)C)=CC=C1S(=O)(=O)NC1=CC=C(N(CC(=O)N[C@@H](CC=2C=CC=CC=2)C(O)=O)C=C2)C2=C1 FTXPWRLJYLZQJJ-VWLOTQADSA-N 0.000 claims 1
• CRYVNOZRRWLQHX-UHFFFAOYSA-N 1-[2-[5-[(4-phenylphenyl)sulfonylamino]indol-1-yl]acetyl]piperidine-4-carboxylic acid Chemical compound C1CC(C(=O)O)CCN1C(=O)CN1C2=CC=C(NS(=O)(=O)C=3C=CC(=CC=3)C=3C=CC=CC=3)C=C2C=C1 CRYVNOZRRWLQHX-UHFFFAOYSA-N 0.000 claims 1
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