JP2008515971A5 - - Google Patents
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- JP2008515971A5 JP2008515971A5 JP2007536680A JP2007536680A JP2008515971A5 JP 2008515971 A5 JP2008515971 A5 JP 2008515971A5 JP 2007536680 A JP2007536680 A JP 2007536680A JP 2007536680 A JP2007536680 A JP 2007536680A JP 2008515971 A5 JP2008515971 A5 JP 2008515971A5
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- Prior art keywords
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- lower alkyl
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- substituted
- Prior art date
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- 150000001875 compounds Chemical class 0.000 claims 49
- 125000000217 alkyl group Chemical group 0.000 claims 39
- 125000004122 cyclic group Chemical group 0.000 claims 15
- -1 methylenedioxy group Chemical group 0.000 claims 15
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 13
- SIKJAQJRHWYJAI-UHFFFAOYSA-N benzopyrrole Natural products C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims 9
- 125000003282 alkyl amino group Chemical group 0.000 claims 8
- 125000001072 heteroaryl group Chemical group 0.000 claims 8
- 125000003545 alkoxy group Chemical group 0.000 claims 7
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims 6
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims 6
- 125000002252 acyl group Chemical group 0.000 claims 5
- 125000003277 amino group Chemical group 0.000 claims 5
- 125000003118 aryl group Chemical group 0.000 claims 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 5
- 239000003814 drug Substances 0.000 claims 5
- 125000003709 fluoroalkyl group Chemical group 0.000 claims 5
- 125000005843 halogen group Chemical group 0.000 claims 5
- 125000000623 heterocyclic group Chemical group 0.000 claims 5
- QNLOWBMKUIXCOW-UHFFFAOYSA-N indol-2-one Chemical compound C1=CC=CC2=NC(=O)C=C21 QNLOWBMKUIXCOW-UHFFFAOYSA-N 0.000 claims 5
- 239000008194 pharmaceutical composition Substances 0.000 claims 5
- 125000006163 5-membered heteroaryl group Chemical group 0.000 claims 4
- 125000005354 acylalkyl group Chemical group 0.000 claims 4
- 125000000278 alkyl amino alkyl group Chemical group 0.000 claims 4
- 125000005360 alkyl sulfoxide group Chemical group 0.000 claims 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 4
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims 4
- 125000005392 carboxamide group Chemical group NC(=O)* 0.000 claims 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 4
- 150000002148 esters Chemical class 0.000 claims 4
- 125000001153 fluoro group Chemical group F* 0.000 claims 4
- 125000001207 fluorophenyl group Chemical group 0.000 claims 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 4
- 125000001041 indolyl group Chemical group 0.000 claims 4
- 238000004519 manufacturing process Methods 0.000 claims 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 4
- 125000002092 orthoester group Chemical group 0.000 claims 4
- 125000004043 oxo group Chemical group O=* 0.000 claims 4
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 4
- 125000001424 substituent group Chemical group 0.000 claims 4
- 125000003107 substituted aryl group Chemical group 0.000 claims 4
- 125000001174 sulfone group Chemical group 0.000 claims 4
- 208000002193 Pain Diseases 0.000 claims 3
- 125000004442 acylamino group Chemical group 0.000 claims 3
- 201000010099 disease Diseases 0.000 claims 3
- 238000011282 treatment Methods 0.000 claims 3
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 claims 2
- 201000001320 Atherosclerosis Diseases 0.000 claims 2
- 208000005171 Dysmenorrhea Diseases 0.000 claims 2
- 206010013935 Dysmenorrhoea Diseases 0.000 claims 2
- 229940121710 HMGCoA reductase inhibitor Drugs 0.000 claims 2
- 101001117517 Homo sapiens Prostaglandin E2 receptor EP3 subtype Proteins 0.000 claims 2
- 206010061218 Inflammation Diseases 0.000 claims 2
- 229940127218 antiplatelet drug Drugs 0.000 claims 2
- 125000004429 atom Chemical group 0.000 claims 2
- 208000035475 disorder Diseases 0.000 claims 2
- 239000002471 hydroxymethylglutaryl coenzyme A reductase inhibitor Substances 0.000 claims 2
- 238000000338 in vitro Methods 0.000 claims 2
- 230000004054 inflammatory process Effects 0.000 claims 2
- JXDYKVIHCLTXOP-UHFFFAOYSA-N isatin Chemical compound C1=CC=C2C(=O)C(=O)NC2=C1 JXDYKVIHCLTXOP-UHFFFAOYSA-N 0.000 claims 2
- 239000003446 ligand Substances 0.000 claims 2
- 238000000034 method Methods 0.000 claims 2
- 208000010125 myocardial infarction Diseases 0.000 claims 2
- 125000001624 naphthyl group Chemical group 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- 201000008482 osteoarthritis Diseases 0.000 claims 2
- 239000000106 platelet aggregation inhibitor Substances 0.000 claims 2
- 239000002599 prostaglandin synthase inhibitor Substances 0.000 claims 2
- 229940127293 prostanoid Drugs 0.000 claims 2
- 150000003814 prostanoids Chemical class 0.000 claims 2
- 238000012216 screening Methods 0.000 claims 2
- 238000006467 substitution reaction Methods 0.000 claims 2
- 208000019553 vascular disease Diseases 0.000 claims 2
- FJLGEFLZQAZZCD-MCBHFWOFSA-N (3R,5S)-fluvastatin Chemical compound C12=CC=CC=C2N(C(C)C)C(\C=C\[C@@H](O)C[C@@H](O)CC(O)=O)=C1C1=CC=C(F)C=C1 FJLGEFLZQAZZCD-MCBHFWOFSA-N 0.000 claims 1
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 1
- GFOOVKOSROWXAZ-UHFFFAOYSA-N 1,3,3a,4,5,6,7,7a-octahydroindol-2-one Chemical compound C1CCCC2NC(=O)CC21 GFOOVKOSROWXAZ-UHFFFAOYSA-N 0.000 claims 1
- YJJUTLWYXYQJNJ-UHFFFAOYSA-N 1,3,3a,4-tetrahydroindol-2-one Chemical compound C1C=CC=C2NC(=O)CC21 YJJUTLWYXYQJNJ-UHFFFAOYSA-N 0.000 claims 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims 1
- BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 claims 1
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims 1
- ASSKVPFEZFQQNQ-UHFFFAOYSA-N 2-benzoxazolinone Chemical compound C1=CC=C2OC(O)=NC2=C1 ASSKVPFEZFQQNQ-UHFFFAOYSA-N 0.000 claims 1
- 125000004008 6 membered carbocyclic group Chemical group 0.000 claims 1
- 206010049589 Afterbirth pain Diseases 0.000 claims 1
- 208000024827 Alzheimer disease Diseases 0.000 claims 1
- 206010002556 Ankylosing Spondylitis Diseases 0.000 claims 1
- XUKUURHRXDUEBC-KAYWLYCHSA-N Atorvastatin Chemical compound C=1C=CC=CC=1C1=C(C=2C=CC(F)=CC=2)N(CC[C@@H](O)C[C@@H](O)CC(O)=O)C(C(C)C)=C1C(=O)NC1=CC=CC=C1 XUKUURHRXDUEBC-KAYWLYCHSA-N 0.000 claims 1
- XUKUURHRXDUEBC-UHFFFAOYSA-N Atorvastatin Natural products C=1C=CC=CC=1C1=C(C=2C=CC(F)=CC=2)N(CCC(O)CC(O)CC(O)=O)C(C(C)C)=C1C(=O)NC1=CC=CC=C1 XUKUURHRXDUEBC-UHFFFAOYSA-N 0.000 claims 1
- 208000023275 Autoimmune disease Diseases 0.000 claims 1
- 239000005552 B01AC04 - Clopidogrel Substances 0.000 claims 1
- 239000005528 B01AC05 - Ticlopidine Substances 0.000 claims 1
- 208000008035 Back Pain Diseases 0.000 claims 1
- 206010065687 Bone loss Diseases 0.000 claims 1
- 206010006002 Bone pain Diseases 0.000 claims 1
- 206010006811 Bursitis Diseases 0.000 claims 1
- 208000018380 Chemical injury Diseases 0.000 claims 1
- 206010053567 Coagulopathies Diseases 0.000 claims 1
- 206010009900 Colitis ulcerative Diseases 0.000 claims 1
- 208000033131 Congenital factor II deficiency Diseases 0.000 claims 1
- 208000034656 Contusions Diseases 0.000 claims 1
- 229940122204 Cyclooxygenase inhibitor Drugs 0.000 claims 1
- 101000783577 Dendroaspis angusticeps Thrombostatin Proteins 0.000 claims 1
- 101000783578 Dendroaspis jamesoni kaimosae Dendroaspin Proteins 0.000 claims 1
- 206010012689 Diabetic retinopathy Diseases 0.000 claims 1
- 208000004232 Enteritis Diseases 0.000 claims 1
- 208000007882 Gastritis Diseases 0.000 claims 1
- 208000018522 Gastrointestinal disease Diseases 0.000 claims 1
- 208000012671 Gastrointestinal haemorrhages Diseases 0.000 claims 1
- 208000010412 Glaucoma Diseases 0.000 claims 1
- 201000005569 Gout Diseases 0.000 claims 1
- 206010019233 Headaches Diseases 0.000 claims 1
- 208000031220 Hemophilia Diseases 0.000 claims 1
- 208000009292 Hemophilia A Diseases 0.000 claims 1
- 208000032843 Hemorrhage Diseases 0.000 claims 1
- 208000007646 Hypoprothrombinemias Diseases 0.000 claims 1
- 206010064912 Malignant transformation Diseases 0.000 claims 1
- ZRVUJXDFFKFLMG-UHFFFAOYSA-N Meloxicam Chemical compound OC=1C2=CC=CC=C2S(=O)(=O)N(C)C=1C(=O)NC1=NC=C(C)S1 ZRVUJXDFFKFLMG-UHFFFAOYSA-N 0.000 claims 1
- 208000019695 Migraine disease Diseases 0.000 claims 1
- PCZOHLXUXFIOCF-UHFFFAOYSA-N Monacolin X Natural products C12C(OC(=O)C(C)CC)CC(C)C=C2C=CC(C)C1CCC1CC(O)CC(=O)O1 PCZOHLXUXFIOCF-UHFFFAOYSA-N 0.000 claims 1
- 201000002481 Myositis Diseases 0.000 claims 1
- 206010028836 Neck pain Diseases 0.000 claims 1
- 208000010191 Osteitis Deformans Diseases 0.000 claims 1
- 208000001132 Osteoporosis Diseases 0.000 claims 1
- 208000027868 Paget disease Diseases 0.000 claims 1
- 208000008469 Peptic Ulcer Diseases 0.000 claims 1
- TUZYXOIXSAXUGO-UHFFFAOYSA-N Pravastatin Natural products C1=CC(C)C(CCC(O)CC(O)CC(O)=O)C2C(OC(=O)C(C)CC)CC(O)C=C21 TUZYXOIXSAXUGO-UHFFFAOYSA-N 0.000 claims 1
- 208000006399 Premature Obstetric Labor Diseases 0.000 claims 1
- 102100024447 Prostaglandin E2 receptor EP3 subtype Human genes 0.000 claims 1
- 206010037660 Pyrexia Diseases 0.000 claims 1
- RYMZZMVNJRMUDD-UHFFFAOYSA-N SJ000286063 Natural products C12C(OC(=O)C(C)(C)CC)CC(C)C=C2C=CC(C)C1CCC1CC(O)CC(=O)O1 RYMZZMVNJRMUDD-UHFFFAOYSA-N 0.000 claims 1
- AJLFOPYRIVGYMJ-UHFFFAOYSA-N SJ000287055 Natural products C12C(OC(=O)C(C)CC)CCC=C2C=CC(C)C1CCC1CC(O)CC(=O)O1 AJLFOPYRIVGYMJ-UHFFFAOYSA-N 0.000 claims 1
- 208000010040 Sprains and Strains Diseases 0.000 claims 1
- 208000006011 Stroke Diseases 0.000 claims 1
- 206010042496 Sunburn Diseases 0.000 claims 1
- 208000007536 Thrombosis Diseases 0.000 claims 1
- 201000006704 Ulcerative Colitis Diseases 0.000 claims 1
- 208000036142 Viral infection Diseases 0.000 claims 1
- 239000003524 antilipemic agent Substances 0.000 claims 1
- 206010003246 arthritis Diseases 0.000 claims 1
- 208000006673 asthma Diseases 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- 229960005370 atorvastatin Drugs 0.000 claims 1
- 230000000740 bleeding effect Effects 0.000 claims 1
- 208000015294 blood coagulation disease Diseases 0.000 claims 1
- 229960000590 celecoxib Drugs 0.000 claims 1
- RZEKVGVHFLEQIL-UHFFFAOYSA-N celecoxib Chemical compound C1=CC(C)=CC=C1C1=CC(C(F)(F)F)=NN1C1=CC=C(S(N)(=O)=O)C=C1 RZEKVGVHFLEQIL-UHFFFAOYSA-N 0.000 claims 1
- 230000001413 cellular effect Effects 0.000 claims 1
- 229960005110 cerivastatin Drugs 0.000 claims 1
- SEERZIQQUAZTOL-ANMDKAQQSA-N cerivastatin Chemical compound COCC1=C(C(C)C)N=C(C(C)C)C(\C=C\[C@@H](O)C[C@@H](O)CC(O)=O)=C1C1=CC=C(F)C=C1 SEERZIQQUAZTOL-ANMDKAQQSA-N 0.000 claims 1
- KYXDNECMRLFQMZ-UHFFFAOYSA-N cimicoxib Chemical compound C1=C(F)C(OC)=CC=C1C1=C(Cl)N=CN1C1=CC=C(S(N)(=O)=O)C=C1 KYXDNECMRLFQMZ-UHFFFAOYSA-N 0.000 claims 1
- 229950010851 cimicoxib Drugs 0.000 claims 1
- 229960003009 clopidogrel Drugs 0.000 claims 1
- GKTWGGQPFAXNFI-HNNXBMFYSA-N clopidogrel Chemical compound C1([C@H](N2CC=3C=CSC=3CC2)C(=O)OC)=CC=CC=C1Cl GKTWGGQPFAXNFI-HNNXBMFYSA-N 0.000 claims 1
- 230000005494 condensation Effects 0.000 claims 1
- 238000009833 condensation Methods 0.000 claims 1
- 230000009519 contusion Effects 0.000 claims 1
- 230000001120 cytoprotective effect Effects 0.000 claims 1
- 229960001259 diclofenac Drugs 0.000 claims 1
- DCOPUUMXTXDBNB-UHFFFAOYSA-N diclofenac Chemical compound OC(=O)CC1=CC=CC=C1NC1=C(Cl)C=CC=C1Cl DCOPUUMXTXDBNB-UHFFFAOYSA-N 0.000 claims 1
- 229960002768 dipyridamole Drugs 0.000 claims 1
- IZEKFCXSFNUWAM-UHFFFAOYSA-N dipyridamole Chemical compound C=12N=C(N(CCO)CCO)N=C(N3CCCCC3)C2=NC(N(CCO)CCO)=NC=1N1CCCCC1 IZEKFCXSFNUWAM-UHFFFAOYSA-N 0.000 claims 1
- 208000007784 diverticulitis Diseases 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 210000003979 eosinophil Anatomy 0.000 claims 1
- 229960005293 etodolac Drugs 0.000 claims 1
- XFBVBWWRPKNWHW-UHFFFAOYSA-N etodolac Chemical compound C1COC(CC)(CC(O)=O)C2=N[C]3C(CC)=CC=CC3=C21 XFBVBWWRPKNWHW-UHFFFAOYSA-N 0.000 claims 1
- 229960004945 etoricoxib Drugs 0.000 claims 1
- MNJVRJDLRVPLFE-UHFFFAOYSA-N etoricoxib Chemical compound C1=NC(C)=CC=C1C1=NC=C(Cl)C=C1C1=CC=C(S(C)(=O)=O)C=C1 MNJVRJDLRVPLFE-UHFFFAOYSA-N 0.000 claims 1
- 229960003765 fluvastatin Drugs 0.000 claims 1
- 208000030304 gastrointestinal bleeding Diseases 0.000 claims 1
- 231100000869 headache Toxicity 0.000 claims 1
- 125000005842 heteroatom Chemical group 0.000 claims 1
- 102000052791 human PTGER3 Human genes 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 208000026278 immune system disease Diseases 0.000 claims 1
- FGFUBBNNYLNVLJ-UHFFFAOYSA-N indolone Natural products C1=CC=C2C(=O)C=NC2=C1 FGFUBBNNYLNVLJ-UHFFFAOYSA-N 0.000 claims 1
- 206010022000 influenza Diseases 0.000 claims 1
- DKYWVDODHFEZIM-UHFFFAOYSA-N ketoprofen Chemical compound OC(=O)C(C)C1=CC=CC(C(=O)C=2C=CC=CC=2)=C1 DKYWVDODHFEZIM-UHFFFAOYSA-N 0.000 claims 1
- 229960000991 ketoprofen Drugs 0.000 claims 1
- 229960004752 ketorolac Drugs 0.000 claims 1
- OZWKMVRBQXNZKK-UHFFFAOYSA-N ketorolac Chemical compound OC(=O)C1CCN2C1=CC=C2C(=O)C1=CC=CC=C1 OZWKMVRBQXNZKK-UHFFFAOYSA-N 0.000 claims 1
- 208000017169 kidney disease Diseases 0.000 claims 1
- 229960004844 lovastatin Drugs 0.000 claims 1
- PCZOHLXUXFIOCF-BXMDZJJMSA-N lovastatin Chemical group C([C@H]1[C@@H](C)C=CC2=C[C@H](C)C[C@@H]([C@H]12)OC(=O)[C@@H](C)CC)C[C@@H]1C[C@@H](O)CC(=O)O1 PCZOHLXUXFIOCF-BXMDZJJMSA-N 0.000 claims 1
- QLJODMDSTUBWDW-UHFFFAOYSA-N lovastatin hydroxy acid Natural products C1=CC(C)C(CCC(O)CC(O)CC(O)=O)C2C(OC(=O)C(C)CC)CC(C)C=C21 QLJODMDSTUBWDW-UHFFFAOYSA-N 0.000 claims 1
- 229960000994 lumiracoxib Drugs 0.000 claims 1
- KHPKQFYUPIUARC-UHFFFAOYSA-N lumiracoxib Chemical compound OC(=O)CC1=CC(C)=CC=C1NC1=C(F)C=CC=C1Cl KHPKQFYUPIUARC-UHFFFAOYSA-N 0.000 claims 1
- 230000036212 malign transformation Effects 0.000 claims 1
- 208000027202 mammary Paget disease Diseases 0.000 claims 1
- 230000001404 mediated effect Effects 0.000 claims 1
- 229960001929 meloxicam Drugs 0.000 claims 1
- 206010061289 metastatic neoplasm Diseases 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 229950009116 mevastatin Drugs 0.000 claims 1
- AJLFOPYRIVGYMJ-INTXDZFKSA-N mevastatin Chemical compound C([C@H]1[C@@H](C)C=CC2=CCC[C@@H]([C@H]12)OC(=O)[C@@H](C)CC)C[C@@H]1C[C@@H](O)CC(=O)O1 AJLFOPYRIVGYMJ-INTXDZFKSA-N 0.000 claims 1
- BOZILQFLQYBIIY-UHFFFAOYSA-N mevastatin hydroxy acid Natural products C1=CC(C)C(CCC(O)CC(O)CC(O)=O)C2C(OC(=O)C(C)CC)CCC=C21 BOZILQFLQYBIIY-UHFFFAOYSA-N 0.000 claims 1
- 206010027599 migraine Diseases 0.000 claims 1
- 208000004296 neuralgia Diseases 0.000 claims 1
- 229910017464 nitrogen compound Inorganic materials 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- 230000011164 ossification Effects 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 239000001301 oxygen Chemical group 0.000 claims 1
- 229960004662 parecoxib Drugs 0.000 claims 1
- TZRHLKRLEZJVIJ-UHFFFAOYSA-N parecoxib Chemical compound C1=CC(S(=O)(=O)NC(=O)CC)=CC=C1C1=C(C)ON=C1C1=CC=CC=C1 TZRHLKRLEZJVIJ-UHFFFAOYSA-N 0.000 claims 1
- 208000011906 peptic ulcer disease Diseases 0.000 claims 1
- 229960002702 piroxicam Drugs 0.000 claims 1
- QYSPLQLAKJAUJT-UHFFFAOYSA-N piroxicam Chemical compound OC=1C2=CC=CC=C2S(=O)(=O)N(C)C=1C(=O)NC1=CC=CC=N1 QYSPLQLAKJAUJT-UHFFFAOYSA-N 0.000 claims 1
- 229960002797 pitavastatin Drugs 0.000 claims 1
- VGYFMXBACGZSIL-MCBHFWOFSA-N pitavastatin Chemical compound OC(=O)C[C@H](O)C[C@H](O)\C=C\C1=C(C2CC2)N=C2C=CC=CC2=C1C1=CC=C(F)C=C1 VGYFMXBACGZSIL-MCBHFWOFSA-N 0.000 claims 1
- 229940096701 plain lipid modifying drug hmg coa reductase inhibitors Drugs 0.000 claims 1
- 229960002965 pravastatin Drugs 0.000 claims 1
- TUZYXOIXSAXUGO-PZAWKZKUSA-N pravastatin Chemical compound C1=C[C@H](C)[C@H](CC[C@@H](O)C[C@@H](O)CC(O)=O)[C@H]2[C@@H](OC(=O)[C@@H](C)CC)C[C@H](O)C=C21 TUZYXOIXSAXUGO-PZAWKZKUSA-N 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- 238000011321 prophylaxis Methods 0.000 claims 1
- 150000003180 prostaglandins Chemical class 0.000 claims 1
- 108050007059 prostanoid receptors Proteins 0.000 claims 1
- 102000017953 prostanoid receptors Human genes 0.000 claims 1
- 201000007183 prothrombin deficiency Diseases 0.000 claims 1
- 230000005855 radiation Effects 0.000 claims 1
- 108020003175 receptors Proteins 0.000 claims 1
- 102000005962 receptors Human genes 0.000 claims 1
- 201000003068 rheumatic fever Diseases 0.000 claims 1
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 1
- 229960000371 rofecoxib Drugs 0.000 claims 1
- RZJQGNCSTQAWON-UHFFFAOYSA-N rofecoxib Chemical group C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=CC=CC=2)C(=O)OC1 RZJQGNCSTQAWON-UHFFFAOYSA-N 0.000 claims 1
- 229960000672 rosuvastatin Drugs 0.000 claims 1
- BPRHUIZQVSMCRT-VEUZHWNKSA-N rosuvastatin Chemical compound CC(C)C1=NC(N(C)S(C)(=O)=O)=NC(C=2C=CC(F)=CC=2)=C1\C=C\[C@@H](O)C[C@@H](O)CC(O)=O BPRHUIZQVSMCRT-VEUZHWNKSA-N 0.000 claims 1
- 229960002855 simvastatin Drugs 0.000 claims 1
- RYMZZMVNJRMUDD-HGQWONQESA-N simvastatin Chemical compound C([C@H]1[C@@H](C)C=CC2=C[C@H](C)C[C@@H]([C@H]12)OC(=O)C(C)(C)CC)C[C@@H]1C[C@@H](O)CC(=O)O1 RYMZZMVNJRMUDD-HGQWONQESA-N 0.000 claims 1
- 230000016160 smooth muscle contraction Effects 0.000 claims 1
- 125000003003 spiro group Chemical group 0.000 claims 1
- 125000004434 sulfur atom Chemical group 0.000 claims 1
- MLKXDPUZXIRXEP-MFOYZWKCSA-N sulindac Chemical compound CC1=C(CC(O)=O)C2=CC(F)=CC=C2\C1=C/C1=CC=C(S(C)=O)C=C1 MLKXDPUZXIRXEP-MFOYZWKCSA-N 0.000 claims 1
- 229960000894 sulindac Drugs 0.000 claims 1
- 238000001356 surgical procedure Methods 0.000 claims 1
- 201000004595 synovitis Diseases 0.000 claims 1
- 229940124597 therapeutic agent Drugs 0.000 claims 1
- 230000001225 therapeutic effect Effects 0.000 claims 1
- 125000001984 thiazolidinyl group Chemical group 0.000 claims 1
- 229960005001 ticlopidine Drugs 0.000 claims 1
- PHWBOXQYWZNQIN-UHFFFAOYSA-N ticlopidine Chemical compound ClC1=CC=CC=C1CN1CC(C=CS2)=C2CC1 PHWBOXQYWZNQIN-UHFFFAOYSA-N 0.000 claims 1
- 229960003425 tirofiban Drugs 0.000 claims 1
- COKMIXFXJJXBQG-NRFANRHFSA-N tirofiban Chemical compound C1=CC(C[C@H](NS(=O)(=O)CCCC)C(O)=O)=CC=C1OCCCCC1CCNCC1 COKMIXFXJJXBQG-NRFANRHFSA-N 0.000 claims 1
- 208000004371 toothache Diseases 0.000 claims 1
- 230000005747 tumor angiogenesis Effects 0.000 claims 1
- 230000004614 tumor growth Effects 0.000 claims 1
- 229960002004 valdecoxib Drugs 0.000 claims 1
- LNPDTQAFDNKSHK-UHFFFAOYSA-N valdecoxib Chemical compound CC=1ON=C(C=2C=CC=CC=2)C=1C1=CC=C(S(N)(=O)=O)C=C1 LNPDTQAFDNKSHK-UHFFFAOYSA-N 0.000 claims 1
- 230000002792 vascular Effects 0.000 claims 1
- 230000009385 viral infection Effects 0.000 claims 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US61817204P | 2004-10-12 | 2004-10-12 | |
| PCT/US2005/023009 WO2006044000A1 (en) | 2004-10-12 | 2005-06-27 | Sulfonamide pert-substituted bicyclics for occlusive artery disease |
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| JP (1) | JP2008515971A (enExample) |
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| EP1715921B1 (en) * | 2003-09-25 | 2013-04-24 | Abraxis BioScience, Inc. | Tetrahydroindolone derivatives for treatment of neurological conditions |
| DE602005026553D1 (de) * | 2004-10-12 | 2011-04-07 | Decode Genetics Ehf | Peri-substituierte bicyclische sulfonamide gegen arterielle verschlusskrankheit |
| CN101076531A (zh) * | 2004-10-12 | 2007-11-21 | 解码遗传学公司 | 用于阻塞性血管疾病的羧酸迫位取代的双环化合物 |
| TW200740435A (en) * | 2005-08-10 | 2007-11-01 | Takeda Pharmaceuticals Co | Therapeutic agent for diabetes |
| US20080125477A1 (en) * | 2006-05-16 | 2008-05-29 | Decode Genetics, Ehf. | 7-(acryloyl) indole compositions and methods of making and using same |
| CA2652152A1 (en) * | 2006-05-16 | 2007-11-29 | Decode Genetics Ehf | Process for preparing 7-(acryloyl)indoles |
| WO2007143825A1 (en) * | 2006-06-12 | 2007-12-21 | Merck Frosst Canada Ltd. | Indoline amide derivatives as ep4 receptor ligands |
| WO2008127274A2 (en) * | 2006-09-22 | 2008-10-23 | Ptc Therapeutics, Inc. | Heterocyclic inhibitors of bacterial peptidyl trna hydrolase and uses thereof |
| TW200843739A (en) * | 2007-03-30 | 2008-11-16 | Shionogi & Co | Novel pyrrolinone derivative and composition containing the same |
| EP2219648A4 (en) * | 2007-11-09 | 2010-11-03 | Cenomed Biosciences Llc | TREATMENT OF POSTRAUMATIC STRESS WITH TETRAHYDROINDOLONE ARYLPIPERAZINE COMPOUNDS |
| US20090264443A1 (en) * | 2008-04-18 | 2009-10-22 | David Helton | Treatment of organophosphate exposure with tetrahydroindolone arylpiperazine compounds |
| PE20110946A1 (es) * | 2008-11-21 | 2012-01-05 | Iroko Cardio Llc | Metodo para reducir la trombocitopenia y mortalidad asociada a la trombocitopenia |
| AR086411A1 (es) | 2011-05-20 | 2013-12-11 | Nippon Soda Co | Compuesto heterociclico conteniendo nitrogeno y fungicida para el uso en agricultura y jardineria |
| JP5841361B2 (ja) * | 2011-06-29 | 2016-01-13 | 壽製薬株式会社 | 三環性化合物及びそれを含有する医薬組成物 |
| WO2014005274A1 (zh) * | 2012-07-03 | 2014-01-09 | 海南卫康制药(潜山)有限公司 | 多取代的8-氮杂环【3.2.1】辛烷化合物 |
| BR112018007664B1 (pt) | 2015-10-16 | 2023-12-19 | Eisai R&D Management Co., Ltd | Compostos antagonistas de ep4, composição compreendendo o composto e uso dos mesmos para tratar câncer |
| WO2020008317A1 (en) * | 2018-07-03 | 2020-01-09 | Janssen Pharmaceutica Nv | Acylsufonamide compounds useful as ep3 receptor antagonists |
| CN112552450A (zh) * | 2019-09-10 | 2021-03-26 | 天津大学 | 一种单离子交替共聚物锂盐及其制备方法 |
| WO2024206284A2 (en) * | 2023-03-27 | 2024-10-03 | Rutgers, The State University Of New Jersey | Therapeutic compounds |
| CN119100992B (zh) * | 2023-06-02 | 2025-09-16 | 帕潘纳(北京)科技有限公司 | 一种特戈拉赞中间体及其衍生物的制备方法 |
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| JPS5030632B2 (enExample) * | 1971-11-29 | 1975-10-02 | ||
| DK151884C (da) * | 1979-03-07 | 1988-06-13 | Pfizer | Analogifremgangsmaade til fremstilling af 3-(1-imidazolylalkyl)indolderivater eller farmaceutisk acceptable syreadditionssalte deraf |
| GB8927981D0 (en) * | 1989-12-11 | 1990-02-14 | Ici Plc | Carbamoyl derivative |
| US5545644A (en) * | 1990-10-15 | 1996-08-13 | Pfizer Inc. | Indole derivatives |
| EP0511477B1 (en) * | 1991-03-11 | 1996-07-10 | Kyowa Hakko Kogyo Co., Ltd. | Indole derivatives |
| GB9122590D0 (en) * | 1991-10-24 | 1991-12-04 | Lilly Industries Ltd | Pharmaceutical compounds |
| JPH06297860A (ja) * | 1993-04-14 | 1994-10-25 | New Oji Paper Co Ltd | 感熱記録体 |
| GB9412719D0 (en) * | 1994-06-24 | 1994-08-17 | Erba Carlo Spa | Substituted azaindolylidene compounds and process for their preparation |
| WO1996010569A1 (en) * | 1994-09-30 | 1996-04-11 | Nippon Chemiphar Co., Ltd. | Quinoline derivative |
| EP0845451A4 (en) * | 1995-07-26 | 1999-10-13 | Ono Pharmaceutical Co | NAPHTHYLOXYACETIC ACID DERIVATIVES AND MEDICINAL PRODUCTS INTEGRATING THESE DERIVATIVES AS ACTIVE INGREDIENTS |
| WO1997024334A1 (en) | 1995-12-28 | 1997-07-10 | Fujisawa Pharmaceutical Co., Ltd. | Benzimidazole derivatives |
| CN1209809A (zh) * | 1996-01-22 | 1999-03-03 | 藤泽药品工业株式会社 | 新化合物 |
| JP4373497B2 (ja) * | 1996-06-19 | 2009-11-25 | ローン−プーラン・ロレ・リミテツド | 置換されたアザビシクロ化合物、ならびにtnfおよびサイクリックampホスホジエステラーゼ産生の阻害剤としてのそれらの使用 |
| ZA984040B (en) * | 1997-05-15 | 1998-11-20 | Ono Pharmaceutical Co | Benzenesulfonamide compounds |
| AU745081B2 (en) * | 1997-06-27 | 2002-03-14 | Fujisawa Pharmaceutical Co., Ltd. | Sulfonamide compounds and medicinal use thereof |
| JP3256513B2 (ja) * | 1998-02-11 | 2002-02-12 | ファイザー製薬株式会社 | ベンゾイミダゾールシクロオキシゲナーゼ−2阻害剤 |
| US6242493B1 (en) * | 1998-03-13 | 2001-06-05 | Merck Frosst Canada & Co. | Carboxylic acids and acylsulfonamides, compositions containing such compounds and methods of treatment |
| EP1123091A1 (en) * | 1998-10-23 | 2001-08-16 | Merck Frosst Canada & Co. | Combination product comprising an e-type prostaglandin ligand and a cox-2 selective inhibitor and methods of use |
| US6348032B1 (en) * | 1998-11-23 | 2002-02-19 | Cell Pathways, Inc. | Method of inhibiting neoplastic cells with benzimidazole derivatives |
| EP1312601A4 (en) * | 2000-08-22 | 2005-09-21 | Ono Pharmaceutical Co | CARBOXYLENE DERIVATIVES, METHOD FOR THE PRODUCTION THEREOF, AND MEDICAMENTS CONTAINING THEM AS AN ACTIVE SUBSTANCE |
| TWI314457B (enExample) | 2001-03-19 | 2009-09-11 | Shionogi & Co | |
| CN101284773A (zh) * | 2001-08-09 | 2008-10-15 | 小野药品工业株式会社 | 羧酸衍生物及以它为活性成分的药剂 |
| DE602005026553D1 (de) * | 2004-10-12 | 2011-04-07 | Decode Genetics Ehf | Peri-substituierte bicyclische sulfonamide gegen arterielle verschlusskrankheit |
| US20080125477A1 (en) * | 2006-05-16 | 2008-05-29 | Decode Genetics, Ehf. | 7-(acryloyl) indole compositions and methods of making and using same |
-
2005
- 2005-06-27 DE DE602005026553T patent/DE602005026553D1/de not_active Expired - Lifetime
- 2005-06-27 CN CNA2005800426037A patent/CN101142184A/zh active Pending
- 2005-06-27 RU RU2007115410/04A patent/RU2403240C2/ru not_active IP Right Cessation
- 2005-06-27 NZ NZ554491A patent/NZ554491A/en not_active IP Right Cessation
- 2005-06-27 CA CA002583667A patent/CA2583667A1/en not_active Abandoned
- 2005-06-27 KR KR1020077010837A patent/KR20070091607A/ko not_active Ceased
- 2005-06-27 MX MX2007004525A patent/MX2007004525A/es active IP Right Grant
- 2005-06-27 BR BRPI0516003-0A patent/BRPI0516003A/pt not_active IP Right Cessation
- 2005-06-27 EP EP05769472A patent/EP1812388B1/en not_active Expired - Lifetime
- 2005-06-27 WO PCT/US2005/023009 patent/WO2006044000A1/en not_active Ceased
- 2005-06-27 JP JP2007536680A patent/JP2008515971A/ja active Pending
- 2005-06-27 US US11/169,161 patent/US7598397B2/en not_active Expired - Fee Related
- 2005-06-27 AT AT05769472T patent/ATE499344T1/de not_active IP Right Cessation
- 2005-06-27 AU AU2005296305A patent/AU2005296305A1/en not_active Abandoned
-
2007
- 2007-04-11 IL IL182488A patent/IL182488A0/en unknown
- 2007-05-02 NO NO20072288A patent/NO20072288L/no not_active Application Discontinuation
-
2009
- 2009-08-03 US US12/534,390 patent/US20090291948A1/en not_active Abandoned
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