CA2449844A1 - Naphthyl benzofuran derivatives as inhibitors of plasminogen activator inhibitor-1 (pai-1) - Google Patents

Info

Publication number

CA2449844A1

CA2449844A1 CA002449844A CA2449844A CA2449844A1 CA 2449844 A1 CA2449844 A1 CA 2449844A1 CA 002449844 A CA002449844 A CA 002449844A CA 2449844 A CA2449844 A CA 2449844A CA 2449844 A1 CA2449844 A1 CA 2449844A1

Authority

CA

Canada

Prior art keywords

benzofuran

naphthyl

compound

pharmaceutically acceptable

acceptable salt

Prior art date

2001-06-20

Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)

Abandoned

Links

• Espacenet
• Global Dossier
• CIPO
• Discuss

• -1 Naphthyl benzofuran derivatives Chemical class 0.000 title claims abstract description 36
• 108010022233 Plasminogen Activator Inhibitor 1 Proteins 0.000 title abstract description 34
• 102000012335 Plasminogen Activator Inhibitor 1 Human genes 0.000 title abstract description 33
• 239000003112 inhibitor Substances 0.000 title abstract description 7
• 150000001875 compounds Chemical class 0.000 claims abstract description 221
• 238000000034 method Methods 0.000 claims abstract description 140
• 150000003839 salts Chemical class 0.000 claims abstract description 65
• 125000000217 alkyl group Chemical group 0.000 claims abstract description 39
• 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 35
• 125000003118 aryl group Chemical group 0.000 claims abstract description 22
• 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 16
• 239000002253 acid Substances 0.000 claims abstract description 14
• 125000003545 alkoxy group Chemical group 0.000 claims abstract description 14
• 125000005010 perfluoroalkyl group Chemical group 0.000 claims abstract description 14
• 125000003107 substituted aryl group Chemical group 0.000 claims abstract description 14
• 230000008569 process Effects 0.000 claims abstract description 11
• 239000003527 fibrinolytic agent Substances 0.000 claims abstract description 10
• 230000003480 fibrinolytic effect Effects 0.000 claims abstract description 10
• 125000003342 alkenyl group Chemical group 0.000 claims abstract description 9
• 206010047249 Venous thrombosis Diseases 0.000 claims abstract description 8
• 238000002360 preparation method Methods 0.000 claims abstract description 8
• 206010051055 Deep vein thrombosis Diseases 0.000 claims abstract description 6
• 125000005024 alkenyl aryl group Chemical group 0.000 claims abstract description 6
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 6
• 208000005069 pulmonary fibrosis Diseases 0.000 claims abstract description 6
• 125000002877 alkyl aryl group Chemical group 0.000 claims abstract description 5
• 230000003278 mimic effect Effects 0.000 claims abstract description 5
• 229920001774 Perfluoroether Polymers 0.000 claims abstract description 3
• 125000001589 carboacyl group Chemical group 0.000 claims abstract description 3
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 3
• 125000001475 halogen functional group Chemical group 0.000 claims abstract 2
• 125000004356 hydroxy functional group Chemical group O* 0.000 claims abstract 2
• 239000000203 mixture Substances 0.000 claims description 62
• 150000002148 esters Chemical group 0.000 claims description 57
• 125000004432 carbon atom Chemical group C* 0.000 claims description 48
• 229910052739 hydrogen Inorganic materials 0.000 claims description 30
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 25
• 239000001257 hydrogen Substances 0.000 claims description 21
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 21
• 238000011282 treatment Methods 0.000 claims description 19
• 229910052736 halogen Inorganic materials 0.000 claims description 18
• 150000002367 halogens Chemical class 0.000 claims description 18
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 15
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 14
• 241000124008 Mammalia Species 0.000 claims description 9
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 8
• 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 8
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 8
• 150000003536 tetrazoles Chemical class 0.000 claims description 7
• QAJLAJGOUHWOEW-UHFFFAOYSA-N 5-[[6-(3-pentyl-1-benzofuran-2-yl)naphthalen-2-yl]oxymethyl]-2h-tetrazole Chemical compound O1C2=CC=CC=C2C(CCCCC)=C1C(C=C1C=C2)=CC=C1C=C2OCC1=NN=NN1 QAJLAJGOUHWOEW-UHFFFAOYSA-N 0.000 claims description 6
• 208000007536 Thrombosis Diseases 0.000 claims description 6
• 239000003814 drug Substances 0.000 claims description 6
• 125000000392 cycloalkenyl group Chemical group 0.000 claims description 5
• 239000011734 sodium Chemical class 0.000 claims description 5
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
• 230000015271 coagulation Effects 0.000 claims description 4
• 238000005345 coagulation Methods 0.000 claims description 4
• 230000006735 deficit Effects 0.000 claims description 4
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
• 229910052708 sodium Inorganic materials 0.000 claims description 4
• GCCRMGSORMLMMU-UHFFFAOYSA-N 1-[2-[5-bromo-6-(2h-tetrazol-5-ylmethoxy)naphthalen-2-yl]-1-benzofuran-3-yl]-2-cyclopentylethanone Chemical compound C1=CC2=CC(C3=C(C4=CC=CC=C4O3)C(=O)CC3CCCC3)=CC=C2C(Br)=C1OCC1=NN=NN1 GCCRMGSORMLMMU-UHFFFAOYSA-N 0.000 claims description 3
• YHPGEYLQEPRXGK-UHFFFAOYSA-N 1-[2-[5-bromo-6-(2h-tetrazol-5-ylmethoxy)naphthalen-2-yl]-1-benzofuran-3-yl]-3-methylbutan-1-one Chemical compound O1C2=CC=CC=C2C(C(=O)CC(C)C)=C1C(C=C1C=C2)=CC=C1C(Br)=C2OCC1=NN=NN1 YHPGEYLQEPRXGK-UHFFFAOYSA-N 0.000 claims description 3
• GAYZBHFSLMXJGY-UHFFFAOYSA-N 1-[2-[5-bromo-6-(2h-tetrazol-5-ylmethoxy)naphthalen-2-yl]-5-chloro-1-benzofuran-3-yl]pentan-1-one Chemical compound O1C2=CC=C(Cl)C=C2C(C(=O)CCCC)=C1C(C=C1C=C2)=CC=C1C(Br)=C2OCC1=NN=NN1 GAYZBHFSLMXJGY-UHFFFAOYSA-N 0.000 claims description 3
• BJRCALOQHCTLDY-UHFFFAOYSA-N 2-[1-bromo-6-(3-pentanoyl-1-benzofuran-2-yl)naphthalen-2-yl]oxy-3-phenylpropanoic acid Chemical compound O1C2=CC=CC=C2C(C(=O)CCCC)=C1C(C=C1C=C2)=CC=C1C(Br)=C2OC(C(O)=O)CC1=CC=CC=C1 BJRCALOQHCTLDY-UHFFFAOYSA-N 0.000 claims description 3
• ZBPITDNNHOZZKP-UHFFFAOYSA-N 2-[1-bromo-6-(3-pentyl-1-benzofuran-2-yl)naphthalen-2-yl]oxyacetic acid Chemical compound BrC1=C(OCC(O)=O)C=CC2=CC(C3=C(C4=CC=CC=C4O3)CCCCC)=CC=C21 ZBPITDNNHOZZKP-UHFFFAOYSA-N 0.000 claims description 3
• YUDAZDZELHZKAG-UHFFFAOYSA-N 2-[1-bromo-6-(5-chloro-3-pentanoyl-1-benzofuran-2-yl)naphthalen-2-yl]oxyacetic acid Chemical compound BrC1=C(OCC(O)=O)C=CC2=CC(C3=C(C4=CC(Cl)=CC=C4O3)C(=O)CCCC)=CC=C21 YUDAZDZELHZKAG-UHFFFAOYSA-N 0.000 claims description 3
• LSFUNZSHLQEMQY-UHFFFAOYSA-N 2-[1-methyl-6-(3-pentanoyl-1-benzofuran-2-yl)naphthalen-2-yl]oxy-3-phenylpropanoic acid Chemical compound O1C2=CC=CC=C2C(C(=O)CCCC)=C1C(C=C1C=C2)=CC=C1C(C)=C2OC(C(O)=O)CC1=CC=CC=C1 LSFUNZSHLQEMQY-UHFFFAOYSA-N 0.000 claims description 3
• ZIGSNVGQWSWNHV-UHFFFAOYSA-N 2-[4-bromo-6-[3-(3-methylbutanoyl)-1-benzofuran-2-yl]naphthalen-2-yl]oxyacetic acid Chemical compound C1=C(OCC(O)=O)C=C(Br)C2=CC(C3=C(C4=CC=CC=C4O3)C(=O)CC(C)C)=CC=C21 ZIGSNVGQWSWNHV-UHFFFAOYSA-N 0.000 claims description 3
• RHBUDCNKVWPXAA-UHFFFAOYSA-N 2-[6-(3-pentanoyl-1-benzofuran-2-yl)-1-[4-(trifluoromethyl)phenyl]naphthalen-2-yl]oxyacetic acid Chemical compound O1C2=CC=CC=C2C(C(=O)CCCC)=C1C(C=C1C=CC=2OCC(O)=O)=CC=C1C=2C1=CC=C(C(F)(F)F)C=C1 RHBUDCNKVWPXAA-UHFFFAOYSA-N 0.000 claims description 3
• FDQBGIKIDBWUMY-UHFFFAOYSA-N 2-[6-(3-pentanoyl-1-benzofuran-2-yl)-1-phenylnaphthalen-2-yl]oxyacetic acid Chemical class O1C2=CC=CC=C2C(C(=O)CCCC)=C1C(C=C1C=CC=2OCC(O)=O)=CC=C1C=2C1=CC=CC=C1 FDQBGIKIDBWUMY-UHFFFAOYSA-N 0.000 claims description 3
• RCLVYHIXCSLQDS-UHFFFAOYSA-N 2-[6-(3-pentyl-1-benzofuran-2-yl)naphthalen-2-yl]oxyacetic acid Chemical compound C1=C(OCC(O)=O)C=CC2=CC(C3=C(C4=CC=CC=C4O3)CCCCC)=CC=C21 RCLVYHIXCSLQDS-UHFFFAOYSA-N 0.000 claims description 3
• CJSQHIFLZRAIEE-UHFFFAOYSA-N 2-[6-(5-chloro-3-pentanoyl-1-benzofuran-2-yl)naphthalen-2-yl]oxyacetic acid Chemical compound C1=C(OCC(O)=O)C=CC2=CC(C3=C(C4=CC(Cl)=CC=C4O3)C(=O)CCCC)=CC=C21 CJSQHIFLZRAIEE-UHFFFAOYSA-N 0.000 claims description 3
• 208000031104 Arterial Occlusive disease Diseases 0.000 claims description 3
• 206010003658 Atrial Fibrillation Diseases 0.000 claims description 3
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
• 125000005213 alkyl heteroaryl group Chemical group 0.000 claims description 3
• 208000021328 arterial occlusion Diseases 0.000 claims description 3
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 3
• 230000015572 biosynthetic process Effects 0.000 claims description 3
• 239000003937 drug carrier Substances 0.000 claims description 3
• 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
• 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 3
• 230000002093 peripheral effect Effects 0.000 claims description 3
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 3
• 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
• 208000011580 syndromic disease Diseases 0.000 claims description 3
• UEWNJOGCIKIMKV-UHFFFAOYSA-N 1-[2-[5-bromo-6-(2h-tetrazol-5-ylmethoxy)naphthalen-2-yl]-1-benzofuran-3-yl]pentan-1-one Chemical compound O1C2=CC=CC=C2C(C(=O)CCCC)=C1C(C=C1C=C2)=CC=C1C(Br)=C2OCC1=NN=NN1 UEWNJOGCIKIMKV-UHFFFAOYSA-N 0.000 claims description 2
• IXOJJTIEHSBORU-UHFFFAOYSA-N 1-[2-[5-chloro-6-(2h-tetrazol-5-ylmethoxy)naphthalen-2-yl]-1-benzofuran-3-yl]pentan-1-one Chemical compound O1C2=CC=CC=C2C(C(=O)CCCC)=C1C(C=C1C=C2)=CC=C1C(Cl)=C2OCC1=NN=NN1 IXOJJTIEHSBORU-UHFFFAOYSA-N 0.000 claims description 2
• GDOVWWPNAFFFFT-UHFFFAOYSA-N 1-[2-[5-methyl-6-(2h-tetrazol-5-ylmethoxy)naphthalen-2-yl]-1-benzofuran-3-yl]pentan-1-one Chemical compound O1C2=CC=CC=C2C(C(=O)CCCC)=C1C(C=C1C=C2)=CC=C1C(C)=C2OCC1=NN=NN1 GDOVWWPNAFFFFT-UHFFFAOYSA-N 0.000 claims description 2
• ROHSDCNFIMAFOH-UHFFFAOYSA-N 1-[2-[5-phenyl-6-(2h-tetrazol-5-ylmethoxy)naphthalen-2-yl]-1-benzofuran-3-yl]pentan-1-one Chemical compound O1C2=CC=CC=C2C(C(=O)CCCC)=C1C(C=C1C=C2)=CC=C1C(C=1C=CC=CC=1)=C2OCC1=NN=NN1 ROHSDCNFIMAFOH-UHFFFAOYSA-N 0.000 claims description 2
• PXJPBYNUIYJCHT-UHFFFAOYSA-N 1-[2-[6-(2h-tetrazol-5-ylmethoxy)-5-[4-(trifluoromethyl)phenyl]naphthalen-2-yl]-1-benzofuran-3-yl]pentan-1-one Chemical compound O1C2=CC=CC=C2C(C(=O)CCCC)=C1C(C=C1C=C2)=CC=C1C(C=1C=CC(=CC=1)C(F)(F)F)=C2OCC1=NN=NN1 PXJPBYNUIYJCHT-UHFFFAOYSA-N 0.000 claims description 2
• ZUXXIOLMGTUAPP-UHFFFAOYSA-N 1-[2-[6-(2h-tetrazol-5-ylmethoxy)naphthalen-2-yl]-1-benzofuran-3-yl]pentan-1-one Chemical compound O1C2=CC=CC=C2C(C(=O)CCCC)=C1C(C=C1C=C2)=CC=C1C=C2OCC1=NN=NN1 ZUXXIOLMGTUAPP-UHFFFAOYSA-N 0.000 claims description 2
• XJBAYJHTLTVEAE-UHFFFAOYSA-N 2-[1-bromo-6-[3-(2-cyclopentylethyl)-1-benzofuran-2-yl]naphthalen-2-yl]oxyacetic acid Chemical compound C1=CC2=C(Br)C(OCC(=O)O)=CC=C2C=C1C=1OC2=CC=CC=C2C=1CCC1CCCC1 XJBAYJHTLTVEAE-UHFFFAOYSA-N 0.000 claims description 2
• PVBZXRNDBMTFCC-UHFFFAOYSA-N 2-[1-methyl-6-(3-pentanoyl-1-benzofuran-2-yl)naphthalen-2-yl]oxyacetic acid Chemical compound CC1=C(OCC(O)=O)C=CC2=CC(C3=C(C4=CC=CC=C4O3)C(=O)CCCC)=CC=C21 PVBZXRNDBMTFCC-UHFFFAOYSA-N 0.000 claims description 2
• ZQFRYDYKEOYUNS-UHFFFAOYSA-N 2-[6-(3-pentanoyl-1-benzofuran-2-yl)naphthalen-2-yl]oxyacetic acid Chemical compound C1=C(OCC(O)=O)C=CC2=CC(C3=C(C4=CC=CC=C4O3)C(=O)CCCC)=CC=C21 ZQFRYDYKEOYUNS-UHFFFAOYSA-N 0.000 claims description 2
• QPYMFRMUFAADMV-UHFFFAOYSA-N 2-[6-[3-(2-cyclopentylacetyl)-1-benzofuran-2-yl]naphthalen-2-yl]oxyacetic acid Chemical compound C1=CC2=CC(OCC(=O)O)=CC=C2C=C1C=1OC2=CC=CC=C2C=1C(=O)CC1CCCC1 QPYMFRMUFAADMV-UHFFFAOYSA-N 0.000 claims description 2
• QDPHVPNHTBBJNC-UHFFFAOYSA-N 5-[[1-bromo-6-[3-(2-cyclopentylethyl)-1-benzofuran-2-yl]naphthalen-2-yl]oxymethyl]-2h-tetrazole Chemical compound C1=CC2=CC(C3=C(C4=CC=CC=C4O3)CCC3CCCC3)=CC=C2C(Br)=C1OCC1=NN=NN1 QDPHVPNHTBBJNC-UHFFFAOYSA-N 0.000 claims description 2
• HDYRFLFOMDPGQT-UHFFFAOYSA-N 5-[[1-methyl-6-(3-pentyl-1-benzofuran-2-yl)naphthalen-2-yl]oxymethyl]-2h-tetrazole Chemical compound O1C2=CC=CC=C2C(CCCCC)=C1C(C=C1C=C2)=CC=C1C(C)=C2OCC1=NN=NN1 HDYRFLFOMDPGQT-UHFFFAOYSA-N 0.000 claims description 2
• 206010003178 Arterial thrombosis Diseases 0.000 claims description 2
• 208000037260 Atherosclerotic Plaque Diseases 0.000 claims description 2
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 2
• 206010008132 Cerebral thrombosis Diseases 0.000 claims description 2
• 201000001429 Intracranial Thrombosis Diseases 0.000 claims description 2
• 150000001540 azides Chemical class 0.000 claims description 2
• PGRHXDWITVMQBC-UHFFFAOYSA-N dehydroacetic acid Natural products CC(=O)C1C(=O)OC(C)=CC1=O PGRHXDWITVMQBC-UHFFFAOYSA-N 0.000 claims description 2
• 230000003301 hydrolyzing effect Effects 0.000 claims description 2
• 208000031225 myocardial ischemia Diseases 0.000 claims description 2
• PEQJBOMPGWYIRO-UHFFFAOYSA-N n-ethyl-3,4-dimethoxyaniline Chemical compound CCNC1=CC=C(OC)C(OC)=C1 PEQJBOMPGWYIRO-UHFFFAOYSA-N 0.000 claims description 2
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
• 238000001356 surgical procedure Methods 0.000 claims description 2
• 230000009424 thromboembolic effect Effects 0.000 claims description 2
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 10
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 4
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 3
• 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims 3
• 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 1
• SRNBELZVNZWFDY-UHFFFAOYSA-N 1-[5-chloro-2-[6-(2h-tetrazol-5-ylmethoxy)naphthalen-2-yl]-1-benzofuran-3-yl]pentan-1-one Chemical compound O1C2=CC=C(Cl)C=C2C(C(=O)CCCC)=C1C(C=C1C=C2)=CC=C1C=C2OCC1=NN=NN1 SRNBELZVNZWFDY-UHFFFAOYSA-N 0.000 claims 1
• WVSXKFKZKFPGSD-UHFFFAOYSA-N 2-[1-bromo-6-(3-bromo-1-benzofuran-2-yl)naphthalen-2-yl]oxy-3-phenylpropanoic acid Chemical compound C=1C=C2C=C(C3=C(C4=CC=CC=C4O3)Br)C=CC2=C(Br)C=1OC(C(=O)O)CC1=CC=CC=C1 WVSXKFKZKFPGSD-UHFFFAOYSA-N 0.000 claims 1
• KKXPVEAUYBUNSF-UHFFFAOYSA-N 2-[1-bromo-6-(3-pentanoyl-1-benzofuran-2-yl)naphthalen-2-yl]oxyacetic acid Chemical compound BrC1=C(OCC(O)=O)C=CC2=CC(C3=C(C4=CC=CC=C4O3)C(=O)CCCC)=CC=C21 KKXPVEAUYBUNSF-UHFFFAOYSA-N 0.000 claims 1
• GSFUDKCDLAJEGV-UHFFFAOYSA-N 2-[1-bromo-6-[3-(2-cyclopentylacetyl)-1-benzofuran-2-yl]naphthalen-2-yl]oxyacetic acid Chemical compound C1=CC2=C(Br)C(OCC(=O)O)=CC=C2C=C1C=1OC2=CC=CC=C2C=1C(=O)CC1CCCC1 GSFUDKCDLAJEGV-UHFFFAOYSA-N 0.000 claims 1
• MTJFCIIDAQCXHQ-UHFFFAOYSA-N 2-[1-bromo-6-[3-(3,3-dimethylbutanoyl)-1-benzofuran-2-yl]naphthalen-2-yl]oxyacetic acid Chemical compound BrC1=C(OCC(O)=O)C=CC2=CC(C3=C(C4=CC=CC=C4O3)C(=O)CC(C)(C)C)=CC=C21 MTJFCIIDAQCXHQ-UHFFFAOYSA-N 0.000 claims 1
• YBCYPFGPKUKYKH-UHFFFAOYSA-N 2-[1-chloro-6-(3-pentanoyl-1-benzofuran-2-yl)naphthalen-2-yl]oxyacetic acid Chemical compound ClC1=C(OCC(O)=O)C=CC2=CC(C3=C(C4=CC=CC=C4O3)C(=O)CCCC)=CC=C21 YBCYPFGPKUKYKH-UHFFFAOYSA-N 0.000 claims 1
• KMYZMZRQCOUXCL-UHFFFAOYSA-N 2-[1-phenyl-6-(3-phenyl-1-benzofuran-2-yl)naphthalen-2-yl]oxyacetic acid Chemical compound OC(=O)COC1=CC=C2C=C(C3=C(C4=CC=CC=C4O3)C=3C=CC=CC=3)C=CC2=C1C1=CC=CC=C1 KMYZMZRQCOUXCL-UHFFFAOYSA-N 0.000 claims 1
• SQWABVRSODAVEX-UHFFFAOYSA-N 2-[6-(3-benzoyl-1-benzofuran-2-yl)naphthalen-2-yl]oxyacetic acid Chemical compound C1=CC2=CC(OCC(=O)O)=CC=C2C=C1C=1OC2=CC=CC=C2C=1C(=O)C1=CC=CC=C1 SQWABVRSODAVEX-UHFFFAOYSA-N 0.000 claims 1
• DMPFULRNBDUSCQ-UHFFFAOYSA-N 2-[6-(3-pentanoyl-1-benzofuran-2-yl)naphthalen-2-yl]oxy-3-phenylpropanoic acid Chemical compound O1C2=CC=CC=C2C(C(=O)CCCC)=C1C(C=C1C=C2)=CC=C1C=C2OC(C(O)=O)CC1=CC=CC=C1 DMPFULRNBDUSCQ-UHFFFAOYSA-N 0.000 claims 1
• LAGOGXVTWHRRQZ-UHFFFAOYSA-N 2-[6-[3-(3,3-dimethylbutanoyl)-1-benzofuran-2-yl]naphthalen-2-yl]oxyacetic acid Chemical compound C1=C(OCC(O)=O)C=CC2=CC(C3=C(C4=CC=CC=C4O3)C(=O)CC(C)(C)C)=CC=C21 LAGOGXVTWHRRQZ-UHFFFAOYSA-N 0.000 claims 1
• 229910018828 PO3H2 Inorganic materials 0.000 claims 1
• 229910006069 SO3H Inorganic materials 0.000 claims 1
• FDEMZMDJNCQRGX-UHFFFAOYSA-N [2-[5-bromo-6-(2h-tetrazol-5-ylmethoxy)naphthalen-2-yl]-1-benzofuran-3-yl]-phenylmethanone Chemical compound C1=CC2=CC(C3=C(C4=CC=CC=C4O3)C(=O)C=3C=CC=CC=3)=CC=C2C(Br)=C1OCC1=NN=NN1 FDEMZMDJNCQRGX-UHFFFAOYSA-N 0.000 claims 1
• 150000001735 carboxylic acids Chemical class 0.000 claims 1
• 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims 1
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• 208000029078 coronary artery disease Diseases 0.000 abstract description 6
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• 125000004185 ester group Chemical group 0.000 abstract 1
• 125000000896 monocarboxylic acid group Chemical group 0.000 abstract 1
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• 239000007787 solid Substances 0.000 description 108
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 81
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 81
• WEVYAHXRMPXWCK-UHFFFAOYSA-N methyl cyanide Natural products CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 77
• 238000001819 mass spectrum Methods 0.000 description 73
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• 238000000921 elemental analysis Methods 0.000 description 62
• 235000019439 ethyl acetate Nutrition 0.000 description 58
• IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 54
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