TW200848024A - Dipeptide analogs as coagulation factor inhibitors - Google Patents

Info

Publication number

TW200848024A

TW200848024A TW097121816A TW97121816A TW200848024A TW 200848024 A TW200848024 A TW 200848024A TW 097121816 A TW097121816 A TW 097121816A TW 97121816 A TW97121816 A TW 97121816A TW 200848024 A TW200848024 A TW 200848024A

Authority

TW

Taiwan

Prior art keywords

substituted

methyl

group

alkyl

phenyl

Prior art date

2007-06-13

Links

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• 239000003112 inhibitor Substances 0.000 title abstract description 59
• 108010016626 Dipeptides Proteins 0.000 title abstract description 5
• 102000015081 Blood Coagulation Factors Human genes 0.000 title description 5
• 108010039209 Blood Coagulation Factors Proteins 0.000 title description 5
• 239000003114 blood coagulation factor Substances 0.000 title description 5
• 150000001875 compounds Chemical class 0.000 claims abstract description 193
• 238000000034 method Methods 0.000 claims abstract description 135
• 208000007536 Thrombosis Diseases 0.000 claims abstract description 97
• 150000003839 salts Chemical class 0.000 claims abstract description 72
• 239000000203 mixture Substances 0.000 claims abstract description 71
• 238000011282 treatment Methods 0.000 claims abstract description 31
• -1 1,2,3,4-tetrahydroindenyl Chemical group 0.000 claims description 336
• 125000000217 alkyl group Chemical group 0.000 claims description 91
• 125000000623 heterocyclic group Chemical group 0.000 claims description 90
• 125000002496 methyl group Chemical group [H]C([H])([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 74
• 229910052799 carbon Inorganic materials 0.000 claims description 69
• OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 56
• 125000005842 heteroatom Chemical group 0.000 claims description 55
• 150000001721 carbon Chemical group 0.000 claims description 52
• 239000003814 drug Substances 0.000 claims description 42
• 229910052757 nitrogen Inorganic materials 0.000 claims description 41
• 229910052731 fluorine Inorganic materials 0.000 claims description 40
• 229910052801 chlorine Inorganic materials 0.000 claims description 37
• 239000008280 blood Substances 0.000 claims description 34
• 210000004369 blood Anatomy 0.000 claims description 32
• NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 31
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 30
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 29
• 229910052794 bromium Inorganic materials 0.000 claims description 28
• 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 26
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 26
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 25
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 25
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 25
• 125000004429 atom Chemical group 0.000 claims description 24
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• 206010047249 Venous thrombosis Diseases 0.000 claims description 21
• 239000007789 gas Substances 0.000 claims description 21
• 125000003118 aryl group Chemical group 0.000 claims description 20
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 19
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• 150000002602 lanthanoids Chemical class 0.000 claims description 18
• 125000001424 substituent group Chemical group 0.000 claims description 18
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• 125000001072 heteroaryl group Chemical group 0.000 claims description 17
• 229910052739 hydrogen Inorganic materials 0.000 claims description 17
• 125000004076 pyridyl group Chemical group 0.000 claims description 17
• 125000004432 carbon atom Chemical group C* 0.000 claims description 16
• 125000003396 thiol group Chemical group [H]S* 0.000 claims description 15
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• 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 14
• 238000004519 manufacturing process Methods 0.000 claims description 14
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 13
• 239000000126 substance Substances 0.000 claims description 13
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• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 12
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• 125000003342 alkenyl group Chemical group 0.000 claims description 11
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• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 10
• 125000002971 oxazolyl group Chemical group 0.000 claims description 10
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• 125000003545 alkoxy group Chemical group 0.000 claims description 9
• 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 9
• 239000007943 implant Substances 0.000 claims description 9
• AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 claims description 8
• 200000000007 Arterial disease Diseases 0.000 claims description 8
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 8
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 8
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• 238000006467 substitution reaction Methods 0.000 claims description 8
• 229910052717 sulfur Inorganic materials 0.000 claims description 8
• 125000004847 2-fluorobenzyl group Chemical group [H]C1=C([H])C(F)=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
• 125000006284 3-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(F)=C1[H])C([H])([H])* 0.000 claims description 7
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• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 7
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• 230000002526 effect on cardiovascular system Effects 0.000 claims description 7
• 125000001188 haloalkyl group Chemical group 0.000 claims description 7
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• 206010036790 Productive cough Diseases 0.000 claims description 6
• 206010008118 cerebral infarction Diseases 0.000 claims description 6
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• 208000002528 coronary thrombosis Diseases 0.000 claims description 6
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 6
• 229910052760 oxygen Inorganic materials 0.000 claims description 6
• 210000003802 sputum Anatomy 0.000 claims description 6
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• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 5
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 5
• 125000002541 furyl group Chemical group 0.000 claims description 5
• 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 5
• 125000004299 tetrazol-5-yl group Chemical group [H]N1N=NC(*)=N1 0.000 claims description 5
• 125000001544 thienyl group Chemical group 0.000 claims description 5
• 125000003626 1,2,4-triazol-1-yl group Chemical group [*]N1N=C([H])N=C1[H] 0.000 claims description 4
• SJAACDLJWHJJFO-UHFFFAOYSA-N 1-(1h-imidazol-2-yl)-n,n-dimethylmethanamine Chemical compound CN(C)CC1=NC=CN1 SJAACDLJWHJJFO-UHFFFAOYSA-N 0.000 claims description 4
• 125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 claims description 4
• 208000030831 Peripheral arterial occlusive disease Diseases 0.000 claims description 4
• WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 4
• 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 4
• 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 4
• 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
• 125000004438 haloalkoxy group Chemical group 0.000 claims description 4
• 125000004458 methylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])[H] 0.000 claims description 4
• 239000001301 oxygen Substances 0.000 claims description 4
• 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 3
• 125000001607 1,2,3-triazol-1-yl group Chemical group [*]N1N=NC([H])=C1[H] 0.000 claims description 3
• 125000003341 7 membered heterocyclic group Chemical group 0.000 claims description 3
• 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims description 3
• 241000689227 Cora <basidiomycete fungus> Species 0.000 claims description 3
• QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 claims description 3
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
• 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 3
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 3
• 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
• 125000000565 sulfonamide group Chemical group 0.000 claims description 3
• XXJGBENTLXFVFI-UHFFFAOYSA-N 1-amino-methylene Chemical compound N[CH2] XXJGBENTLXFVFI-UHFFFAOYSA-N 0.000 claims description 2
• 125000003287 1H-imidazol-4-ylmethyl group Chemical group [H]N1C([H])=NC(C([H])([H])[*])=C1[H] 0.000 claims description 2
• BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 claims description 2
• KIAPWMKFHIKQOZ-UHFFFAOYSA-N 2-[[(4-fluorophenyl)-oxomethyl]amino]benzoic acid methyl ester Chemical compound COC(=O)C1=CC=CC=C1NC(=O)C1=CC=C(F)C=C1 KIAPWMKFHIKQOZ-UHFFFAOYSA-N 0.000 claims description 2
• WLXYHLHNIRJAIG-UHFFFAOYSA-N 2h-benzo[e]isoindole Chemical compound C1=CC=C2C3=CNC=C3C=CC2=C1 WLXYHLHNIRJAIG-UHFFFAOYSA-N 0.000 claims description 2
• OSKSVLBJJXQUPI-UHFFFAOYSA-N 2h-triazole-4-carboxamide Chemical compound NC(=O)C1=CNN=N1 OSKSVLBJJXQUPI-UHFFFAOYSA-N 0.000 claims description 2
• JNCMHMUGTWEVOZ-UHFFFAOYSA-N F[CH]F Chemical compound F[CH]F JNCMHMUGTWEVOZ-UHFFFAOYSA-N 0.000 claims description 2
• 108010081348 HRT1 protein Hairy Proteins 0.000 claims description 2
• 102100021881 Hairy/enhancer-of-split related with YRPW motif protein 1 Human genes 0.000 claims description 2
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• 101100091494 Mus musculus Rorc gene Proteins 0.000 claims description 2
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• 125000004603 benzisoxazolyl group Chemical group O1N=C(C2=C1C=CC=C2)* 0.000 claims description 2
• 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 2
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
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