OA11261A - Method of using cyclooxygenase-2 inhibitors in theprevention of cardiovascular disorders - Google Patents

Method of using cyclooxygenase-2 inhibitors in theprevention of cardiovascular disorders Download PDF

Info

Publication number: OA11261A
Authority: OA; OAPI
Prior art keywords: phenyl; benzenesulfonamide; methylsulfonyl; fluorophenyl; trifluoromethyl
Prior art date: 1997-04-18

Application number

OA9900228A

Other languages

English (en)

Inventor

Barbara Roniker

Richard J Lachapell

Daniel T Connolly

Karen Seibert

Philip Needleman

Original Assignee

Searle & Co

Priority date (The priority date 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 date listed.)

1997-04-18

Filing date

1999-10-18

Publication date

2003-07-24

1999-10-18 Application filed by Searle & Co filed Critical Searle & Co

2003-07-24 Publication of OA11261A publication Critical patent/OA11261A/en

Links

208000024172 Cardiovascular disease Diseases 0.000 title claims abstract description 17
238000000034 method Methods 0.000 title claims description 17
239000003255 cyclooxygenase 2 inhibitor Substances 0.000 title abstract description 8
-1 cyano, carboxyl Chemical group 0.000 claims description 197
150000003254 radicals Chemical class 0.000 claims description 74
KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims description 54
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 43
150000001875 compounds Chemical class 0.000 claims description 35
125000000217 alkyl group Chemical group 0.000 claims description 26
125000005843 halogen group Chemical group 0.000 claims description 24
206010061218 Inflammation Diseases 0.000 claims description 22
230000004054 inflammatory process Effects 0.000 claims description 22
125000000623 heterocyclic group Chemical group 0.000 claims description 19
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 18
125000003118 aryl group Chemical group 0.000 claims description 17
125000000753 cycloalkyl group Chemical group 0.000 claims description 16
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 15
125000003545 alkoxy group Chemical group 0.000 claims description 15
125000004093 cyano group Chemical group *C#N 0.000 claims description 14
125000002768 hydroxyalkyl group Chemical group 0.000 claims description 14
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 13
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 12
125000001188 haloalkyl group Chemical group 0.000 claims description 12
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 12
150000003839 salts Chemical class 0.000 claims description 12
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 11
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 11
125000003282 alkyl amino group Chemical group 0.000 claims description 10
125000000392 cycloalkenyl group Chemical group 0.000 claims description 10
125000001145 hydrido group Chemical group *[H] 0.000 claims description 10
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 10
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 10
125000004181 carboxyalkyl group Chemical group 0.000 claims description 9
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 9
125000004414 alkyl thio group Chemical group 0.000 claims description 8
125000003342 alkenyl group Chemical group 0.000 claims description 7
125000004438 haloalkoxy group Chemical group 0.000 claims description 7
201000001320 Atherosclerosis Diseases 0.000 claims description 6
125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 6
125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 6
ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 6
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 6
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
125000002971 oxazolyl group Chemical group 0.000 claims description 6
238000001356 surgical procedure Methods 0.000 claims description 6
125000001544 thienyl group Chemical group 0.000 claims description 6
125000002252 acyl group Chemical group 0.000 claims description 5
125000004103 aminoalkyl group Chemical group 0.000 claims description 5
125000005097 aminocarbonylalkyl group Chemical group 0.000 claims description 5
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 description 5
125000004966 cyanoalkyl group Chemical group 0.000 claims description 5
125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 5
230000002526 effect on cardiovascular system Effects 0.000 claims description 5
125000001153 fluoro group Chemical group F* 0.000 claims description 5
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 5
125000004076 pyridyl group Chemical group 0.000 claims description 5
125000003003 spiro group Chemical group 0.000 claims description 5
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 4
125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
125000005100 aryl amino carbonyl group Chemical group 0.000 claims description 4
230000001580 bacterial effect Effects 0.000 claims description 4
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 4
239000004305 biphenyl Substances 0.000 claims description 4
125000002541 furyl group Chemical group 0.000 claims description 4
125000004043 oxo group Chemical group O=* 0.000 claims description 4
125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 4
PWULVHYHVZUTFR-UHFFFAOYSA-N spiro[2.4]hept-5-ene Chemical compound C1CC11CC=CC1 PWULVHYHVZUTFR-UHFFFAOYSA-N 0.000 claims description 4
125000000335 thiazolyl group Chemical group 0.000 claims description 4
NSRMOHFGSWCCFK-UHFFFAOYSA-N 4-[2-(5-methylpyridin-3-yl)-4-(trifluoromethyl)imidazol-1-yl]benzenesulfonamide Chemical compound CC1=CN=CC(C=2N(C=C(N=2)C(F)(F)F)C=2C=CC(=CC=2)S(N)(=O)=O)=C1 NSRMOHFGSWCCFK-UHFFFAOYSA-N 0.000 claims description 3
UUGSJYRNELHGOL-UHFFFAOYSA-N 4-[3-cyano-5-(4-fluorophenyl)pyrazol-1-yl]benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1N1C(C=2C=CC(F)=CC=2)=CC(C#N)=N1 UUGSJYRNELHGOL-UHFFFAOYSA-N 0.000 claims description 3
IYPAUZQRSAWCBH-UHFFFAOYSA-N 4-[5-(4-chlorophenyl)-3-(hydroxymethyl)pyrazol-1-yl]benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1N1C(C=2C=CC(Cl)=CC=2)=CC(CO)=N1 IYPAUZQRSAWCBH-UHFFFAOYSA-N 0.000 claims description 3
UJSFKTUZOASIPA-UHFFFAOYSA-N 4-[5-(hydroxymethyl)-3-phenyl-1,2-oxazol-4-yl]benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1C1=C(CO)ON=C1C1=CC=CC=C1 UJSFKTUZOASIPA-UHFFFAOYSA-N 0.000 claims description 3
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 3
206010002329 Aneurysm Diseases 0.000 claims description 3
206010002383 Angina Pectoris Diseases 0.000 claims description 3
206010002388 Angina unstable Diseases 0.000 claims description 3
208000005189 Embolism Diseases 0.000 claims description 3
208000006011 Stroke Diseases 0.000 claims description 3
FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 3
208000007814 Unstable Angina Diseases 0.000 claims description 3
238000002399 angioplasty Methods 0.000 claims description 3
210000001367 artery Anatomy 0.000 claims description 3
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
235000010290 biphenyl Nutrition 0.000 claims description 3
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
208000029078 coronary artery disease Diseases 0.000 claims description 3
210000004351 coronary vessel Anatomy 0.000 claims description 3
238000013171 endarterectomy Methods 0.000 claims description 3
201000004332 intermediate coronary syndrome Diseases 0.000 claims description 3
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 3
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 claims description 3
208000010125 myocardial infarction Diseases 0.000 claims description 3
125000001624 naphthyl group Chemical group 0.000 claims description 3
125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 claims description 3
125000003373 pyrazinyl group Chemical group 0.000 claims description 3
125000000168 pyrrolyl group Chemical group 0.000 claims description 3
230000000250 revascularization Effects 0.000 claims description 3
230000002792 vascular Effects 0.000 claims description 3
230000003612 virological effect Effects 0.000 claims description 3
LWIFWMYFVZYWMS-UHFFFAOYSA-N 1,2-difluoro-3-[2-(4-methylsulfonylphenyl)cyclopenten-1-yl]benzene Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C(=C(F)C=CC=2)F)CCC1 LWIFWMYFVZYWMS-UHFFFAOYSA-N 0.000 claims description 2
GWMFOHRUWPDLIP-UHFFFAOYSA-N 1-(4-methylsulfonylphenyl)-2-phenyl-4-(trifluoromethyl)imidazole Chemical compound C1=CC(S(=O)(=O)C)=CC=C1N1C(C=2C=CC=CC=2)=NC(C(F)(F)F)=C1 GWMFOHRUWPDLIP-UHFFFAOYSA-N 0.000 claims description 2
MBUIIOVYVHAZOU-UHFFFAOYSA-N 1-[2-(4-chlorophenyl)cyclopenten-1-yl]-4-methylsulfonylbenzene Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=CC(Cl)=CC=2)CCC1 MBUIIOVYVHAZOU-UHFFFAOYSA-N 0.000 claims description 2
SZHKSRZKPUOAGO-UHFFFAOYSA-N 1-[2-(4-methylsulfonylphenyl)cyclopenten-1-yl]-4-(trifluoromethyl)benzene Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=CC(=CC=2)C(F)(F)F)CCC1 SZHKSRZKPUOAGO-UHFFFAOYSA-N 0.000 claims description 2
VKUCTHVTLJBHDT-UHFFFAOYSA-N 1-[4,4-dimethyl-2-(4-methylsulfonylphenyl)cyclopenten-1-yl]-4-fluorobenzene Chemical compound C1C(C)(C)CC(C=2C=CC(F)=CC=2)=C1C1=CC=C(S(C)(=O)=O)C=C1 VKUCTHVTLJBHDT-UHFFFAOYSA-N 0.000 claims description 2
RAUHMMADXJJVRP-UHFFFAOYSA-N 1-methoxy-4-[2-(4-methylsulfonylphenyl)cyclopenten-1-yl]benzene Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=CC(=CC=2)S(C)(=O)=O)CCC1 RAUHMMADXJJVRP-UHFFFAOYSA-N 0.000 claims description 2
NWVGCEQIXKQQPS-UHFFFAOYSA-N 2-(3,4-difluorophenyl)-1-(4-methylsulfonylphenyl)-4-(trifluoromethyl)imidazole Chemical compound C1=CC(S(=O)(=O)C)=CC=C1N1C(C=2C=C(F)C(F)=CC=2)=NC(C(F)(F)F)=C1 NWVGCEQIXKQQPS-UHFFFAOYSA-N 0.000 claims description 2
SOOKCKQNOCMHPV-UHFFFAOYSA-N 2-(3-chloro-4-fluorophenyl)-4-(4-fluorophenyl)-5-(4-methylsulfonylphenyl)-1,3-thiazole Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=CC(F)=CC=2)N=C(C=2C=C(Cl)C(F)=CC=2)S1 SOOKCKQNOCMHPV-UHFFFAOYSA-N 0.000 claims description 2
AGCRHVNIFLDQNI-UHFFFAOYSA-N 2-[4-(4-fluorophenyl)-5-(4-methylsulfonylphenyl)-1,3-oxazol-2-yl]acetic acid Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=CC(F)=CC=2)N=C(CC(O)=O)O1 AGCRHVNIFLDQNI-UHFFFAOYSA-N 0.000 claims description 2
NECDCTAHUMBLQG-UHFFFAOYSA-N 2-bromo-6-(4-fluorophenyl)-5-(4-methylsulfonylphenyl)pyridine-3-carbonitrile Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=CC(C#N)=C(Br)N=C1C1=CC=C(F)C=C1 NECDCTAHUMBLQG-UHFFFAOYSA-N 0.000 claims description 2
KYNAWJZJGXEMMS-UHFFFAOYSA-N 2-chloro-1-methoxy-4-[2-(4-methylsulfonylphenyl)cyclopenten-1-yl]benzene Chemical compound C1=C(Cl)C(OC)=CC=C1C1=C(C=2C=CC(=CC=2)S(C)(=O)=O)CCC1 KYNAWJZJGXEMMS-UHFFFAOYSA-N 0.000 claims description 2
AMTZZFUBJIWXKB-UHFFFAOYSA-N 2-tert-butyl-4-(4-fluorophenyl)-5-(4-methylsulfonylphenyl)-1,3-oxazole Chemical compound O1C(C(C)(C)C)=NC(C=2C=CC(F)=CC=2)=C1C1=CC=C(S(C)(=O)=O)C=C1 AMTZZFUBJIWXKB-UHFFFAOYSA-N 0.000 claims description 2
OCROGSYJFYKXMO-UHFFFAOYSA-N 3-(4-fluorophenyl)-4-(4-methylsulfonylphenyl)-6-prop-2-ynoxy-2-(trifluoromethyl)pyridine Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=CC(OCC#C)=NC(C(F)(F)F)=C1C1=CC=C(F)C=C1 OCROGSYJFYKXMO-UHFFFAOYSA-N 0.000 claims description 2
VTXIMXSYKSVSGP-UHFFFAOYSA-N 3-(4-fluorophenyl)-6-methoxy-4-(4-methylsulfonylphenyl)-2-(trifluoromethyl)pyridine Chemical compound C=1C=C(F)C=CC=1C=1C(C(F)(F)F)=NC(OC)=CC=1C1=CC=C(S(C)(=O)=O)C=C1 VTXIMXSYKSVSGP-UHFFFAOYSA-N 0.000 claims description 2
IQHFIMRYUJFZQW-UHFFFAOYSA-N 4-(3-ethyl-5-phenyl-1,2-oxazol-4-yl)benzenesulfonamide Chemical compound CCC1=NOC(C=2C=CC=CC=2)=C1C1=CC=C(S(N)(=O)=O)C=C1 IQHFIMRYUJFZQW-UHFFFAOYSA-N 0.000 claims description 2
AJYWXMJXJSEWLW-UHFFFAOYSA-N 4-(4-chloro-5-phenylpyrazol-1-yl)benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1N1C(C=2C=CC=CC=2)=C(Cl)C=N1 AJYWXMJXJSEWLW-UHFFFAOYSA-N 0.000 claims description 2
FQJOALWXRJKJFW-UHFFFAOYSA-N 4-(4-fluorophenyl)-2-methyl-5-(4-methylsulfonylphenyl)-1,3-oxazole Chemical compound O1C(C)=NC(C=2C=CC(F)=CC=2)=C1C1=CC=C(S(C)(=O)=O)C=C1 FQJOALWXRJKJFW-UHFFFAOYSA-N 0.000 claims description 2
KHZNXVYATAUMBJ-UHFFFAOYSA-N 4-(4-fluorophenyl)-5-(4-methylsulfonylphenyl)-1-phenyl-3-(trifluoromethyl)pyrazole Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=CC(F)=CC=2)C(C(F)(F)F)=NN1C1=CC=CC=C1 KHZNXVYATAUMBJ-UHFFFAOYSA-N 0.000 claims description 2
SAVMISCIBLZUAE-UHFFFAOYSA-N 4-(4-fluorophenyl)-5-(4-methylsulfonylphenyl)-2-(trifluoromethyl)-1,3-thiazole Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=CC(F)=CC=2)N=C(C(F)(F)F)S1 SAVMISCIBLZUAE-UHFFFAOYSA-N 0.000 claims description 2
DEXPHZXXTBGSGZ-UHFFFAOYSA-N 4-(4-fluorophenyl)-5-(4-methylsulfonylphenyl)-n-propyl-1,3-thiazol-2-amine Chemical compound S1C(NCCC)=NC(C=2C=CC(F)=CC=2)=C1C1=CC=C(S(C)(=O)=O)C=C1 DEXPHZXXTBGSGZ-UHFFFAOYSA-N 0.000 claims description 2
JPWKLILKLRXARO-UHFFFAOYSA-N 4-[2-(2-methylpyridin-3-yl)-4-(trifluoromethyl)imidazol-1-yl]benzenesulfonamide Chemical compound CC1=NC=CC=C1C1=NC(C(F)(F)F)=CN1C1=CC=C(S(N)(=O)=O)C=C1 JPWKLILKLRXARO-UHFFFAOYSA-N 0.000 claims description 2
MSULOQJDYOQZPZ-UHFFFAOYSA-N 4-[2-(3-chloro-4-methoxyphenyl)-4,5-difluorophenyl]benzenesulfonamide Chemical compound C1=C(Cl)C(OC)=CC=C1C1=CC(F)=C(F)C=C1C1=CC=C(S(N)(=O)=O)C=C1 MSULOQJDYOQZPZ-UHFFFAOYSA-N 0.000 claims description 2
PHBYRHUAGNXCFU-UHFFFAOYSA-N 4-[2-(3-chloro-4-methylphenyl)-4-(trifluoromethyl)imidazol-1-yl]benzenesulfonamide Chemical compound C1=C(Cl)C(C)=CC=C1C1=NC(C(F)(F)F)=CN1C1=CC=C(S(N)(=O)=O)C=C1 PHBYRHUAGNXCFU-UHFFFAOYSA-N 0.000 claims description 2
QFKFDESGBPKPPL-UHFFFAOYSA-N 4-[2-(3-fluoro-5-methylphenyl)-4-(trifluoromethyl)imidazol-1-yl]benzenesulfonamide Chemical compound CC1=CC(F)=CC(C=2N(C=C(N=2)C(F)(F)F)C=2C=CC(=CC=2)S(N)(=O)=O)=C1 QFKFDESGBPKPPL-UHFFFAOYSA-N 0.000 claims description 2
FQZPECQXBKABHG-UHFFFAOYSA-N 4-[2-phenyl-4-(trifluoromethyl)imidazol-1-yl]benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1N1C(C=2C=CC=CC=2)=NC(C(F)(F)F)=C1 FQZPECQXBKABHG-UHFFFAOYSA-N 0.000 claims description 2
JSMWYOPCPZTWAA-UHFFFAOYSA-N 4-[3,5-bis(4-methoxyphenyl)pyrazol-1-yl]benzenesulfonamide Chemical compound C1=CC(OC)=CC=C1C1=NN(C=2C=CC(=CC=2)S(N)(=O)=O)C(C=2C=CC(OC)=CC=2)=C1 JSMWYOPCPZTWAA-UHFFFAOYSA-N 0.000 claims description 2
WLSNEFWMXKIPHE-UHFFFAOYSA-N 4-[3,5-bis(4-methylphenyl)pyrazol-1-yl]benzenesulfonamide;4-[5-(4-chlorophenyl)-3-(4-methoxyphenyl)pyrazol-1-yl]benzenesulfonamide Chemical compound C1=CC(C)=CC=C1C1=NN(C=2C=CC(=CC=2)S(N)(=O)=O)C(C=2C=CC(C)=CC=2)=C1.C1=CC(OC)=CC=C1C1=NN(C=2C=CC(=CC=2)S(N)(=O)=O)C(C=2C=CC(Cl)=CC=2)=C1 WLSNEFWMXKIPHE-UHFFFAOYSA-N 0.000 claims description 2
ZFFYQVIHYPYXPI-UHFFFAOYSA-N 4-[3-(difluoromethyl)-5-phenylpyrazol-1-yl]benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1N1C(C=2C=CC=CC=2)=CC(C(F)F)=N1 ZFFYQVIHYPYXPI-UHFFFAOYSA-N 0.000 claims description 2
SZDMSAGZJBRJNW-UHFFFAOYSA-N 4-[5-(4-chlorophenyl)-3-(4-methylphenyl)pyrazol-1-yl]benzenesulfonamide Chemical compound C1=CC(C)=CC=C1C1=NN(C=2C=CC(=CC=2)S(N)(=O)=O)C(C=2C=CC(Cl)=CC=2)=C1 SZDMSAGZJBRJNW-UHFFFAOYSA-N 0.000 claims description 2
KJIAFIBHGWAADR-UHFFFAOYSA-N 4-[5-(4-chlorophenyl)-3-(4-nitrophenyl)pyrazol-1-yl]benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1N1C(C=2C=CC(Cl)=CC=2)=CC(C=2C=CC(=CC=2)[N+]([O-])=O)=N1 KJIAFIBHGWAADR-UHFFFAOYSA-N 0.000 claims description 2
KBNOHTKUNAPKEI-UHFFFAOYSA-N 4-[5-(4-chlorophenyl)-3-(5-chlorothiophen-2-yl)pyrazol-1-yl]benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1N1C(C=2C=CC(Cl)=CC=2)=CC(C=2SC(Cl)=CC=2)=N1 KBNOHTKUNAPKEI-UHFFFAOYSA-N 0.000 claims description 2
JDCWOBTUQSMXDU-UHFFFAOYSA-N 4-[5-(4-chlorophenyl)-3-(difluoromethyl)pyrazol-1-yl]benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1N1C(C=2C=CC(Cl)=CC=2)=CC(C(F)F)=N1 JDCWOBTUQSMXDU-UHFFFAOYSA-N 0.000 claims description 2
YDUQOLMYSBDZFO-UHFFFAOYSA-N 4-[5-(4-chlorophenyl)-3-phenylpyrazol-1-yl]benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1N1C(C=2C=CC(Cl)=CC=2)=CC(C=2C=CC=CC=2)=N1 YDUQOLMYSBDZFO-UHFFFAOYSA-N 0.000 claims description 2
DVSOGWILWKEIDD-UHFFFAOYSA-N 4-[5-(difluoromethyl)-3-phenyl-1,2-oxazol-4-yl]benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1C1=C(C(F)F)ON=C1C1=CC=CC=C1 DVSOGWILWKEIDD-UHFFFAOYSA-N 0.000 claims description 2
CHJMEHVGESAPSR-UHFFFAOYSA-N 4-fluoro-2-methyl-1-[2-(4-methylsulfonylphenyl)cyclopenten-1-yl]benzene Chemical compound CC1=CC(F)=CC=C1C1=C(C=2C=CC(=CC=2)S(C)(=O)=O)CCC1 CHJMEHVGESAPSR-UHFFFAOYSA-N 0.000 claims description 2
ZPMVBXDFUCFRLF-UHFFFAOYSA-N 5-(4-fluorophenyl)-2-methyl-4-(4-methylsulfonylphenyl)-1,3-thiazole Chemical compound S1C(C)=NC(C=2C=CC(=CC=2)S(C)(=O)=O)=C1C1=CC=C(F)C=C1 ZPMVBXDFUCFRLF-UHFFFAOYSA-N 0.000 claims description 2
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Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
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Animal Behavior & Ethology (AREA)
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Rheumatology (AREA)
Vascular Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Thiazole And Isothizaole Compounds (AREA)
Furan Compounds (AREA)
Pyridine Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

OA9900228A 1997-04-18 1999-10-18 Method of using cyclooxygenase-2 inhibitors in theprevention of cardiovascular disorders OA11261A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US4462697P	1997-04-18	1997-04-18

Publications (1)

Publication Number	Publication Date
OA11261A true OA11261A (en)	2003-07-24

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ID=21933403

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
OA9900228A OA11261A (en)	1997-04-18	1999-10-18	Method of using cyclooxygenase-2 inhibitors in theprevention of cardiovascular disorders

Country Status (26)

Country	Link
EP (2)	EP0979077A1 (is)
JP (1)	JP2001527542A (is)
KR (1)	KR20010006443A (is)
CN (1)	CN1253502A (is)
AP (1)	AP9901674A0 (is)
AU (1)	AU745797B2 (is)
BG (1)	BG103803A (is)
BR (1)	BR9808932A (is)
CA (1)	CA2286673A1 (is)
EA (1)	EA199900837A1 (is)
EE (2)	EE200300169A (is)
GE (1)	GEP20022812B (is)
HU (1)	HUP0001777A3 (is)
ID (1)	ID23687A (is)
IL (1)	IL132163A0 (is)
IS (1)	IS5203A (is)
NO (1)	NO995077L (is)
NZ (1)	NZ500141A (is)
OA (1)	OA11261A (is)
PL (1)	PL337098A1 (is)
SK (1)	SK138799A3 (is)
TR (1)	TR199902545T2 (is)
UA (1)	UA68348C2 (is)
WO (1)	WO1998047509A1 (is)
YU (1)	YU53899A (is)
ZA (1)	ZA983249B (is)

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1998
- 1998-04-16 WO PCT/US1998/007318 patent/WO1998047509A1/en not_active Ceased
- 1998-04-16 EE EEP200300169A patent/EE200300169A/xx unknown
- 1998-04-16 AP APAP/P/1999/001674A patent/AP9901674A0/en unknown
- 1998-04-16 EA EA199900837A patent/EA199900837A1/ru unknown
- 1998-04-16 YU YU53899A patent/YU53899A/sh unknown
- 1998-04-16 TR TR1999/02545T patent/TR199902545T2/xx unknown
- 1998-04-16 SK SK1387-99A patent/SK138799A3/sk unknown
- 1998-04-16 EE EEP199900517A patent/EE9900517A/xx unknown
- 1998-04-16 GE GEAP19985037A patent/GEP20022812B/en unknown
- 1998-04-16 JP JP54611398A patent/JP2001527542A/ja not_active Withdrawn
- 1998-04-16 AU AU74662/98A patent/AU745797B2/en not_active Ceased
- 1998-04-16 UA UA99105689A patent/UA68348C2/uk unknown
- 1998-04-16 EP EP98922028A patent/EP0979077A1/en not_active Withdrawn
- 1998-04-16 KR KR1019997009533A patent/KR20010006443A/ko not_active Ceased
- 1998-04-16 CN CN98804252A patent/CN1253502A/zh active Pending
- 1998-04-16 IL IL13216398A patent/IL132163A0/xx not_active IP Right Cessation
- 1998-04-16 HU HU0001777A patent/HUP0001777A3/hu unknown
- 1998-04-16 BR BR9808932-3A patent/BR9808932A/pt not_active Application Discontinuation
- 1998-04-16 ID IDW991219A patent/ID23687A/id unknown
- 1998-04-16 NZ NZ500141A patent/NZ500141A/en unknown
- 1998-04-16 PL PL98337098A patent/PL337098A1/xx unknown
- 1998-04-16 EP EP04023890A patent/EP1498140A2/en not_active Withdrawn
- 1998-04-16 CA CA002286673A patent/CA2286673A1/en not_active Abandoned
- 1998-04-17 ZA ZA983249A patent/ZA983249B/xx unknown
1999
- 1999-09-30 IS IS5203A patent/IS5203A/is unknown
- 1999-10-13 BG BG103803A patent/BG103803A/bg unknown
- 1999-10-18 OA OA9900228A patent/OA11261A/en unknown
- 1999-10-18 NO NO995077A patent/NO995077L/no not_active Application Discontinuation

Also Published As

Publication number	Publication date
HUP0001777A3 (en)	2001-07-30
ZA983249B (en)	1999-04-19
HUP0001777A2 (hu)	2001-05-28
EE200300169A (et)	2003-06-16
IS5203A (is)	1999-09-30
KR20010006443A (ko)	2001-01-26
NO995077L (no)	1999-12-17
YU53899A (sh)	2002-10-18
NO995077D0 (no)	1999-10-18
EA199900837A1 (ru)	2000-10-30
AU7466298A (en)	1998-11-13
BG103803A (bg)	2000-05-31
JP2001527542A (ja)	2001-12-25
SK138799A3 (en)	2001-01-18
BR9808932A (pt)	2000-08-01
EP1498140A2 (en)	2005-01-19
EP0979077A1 (en)	2000-02-16
PL337098A1 (en)	2000-07-31
AU745797B2 (en)	2002-03-28
CN1253502A (zh)	2000-05-17
GEP20022812B (en)	2002-10-25
IL132163A0 (en)	2001-03-19
WO1998047509A1 (en)	1998-10-29
TR199902545T2 (xx)	2000-01-21
ID23687A (id)	2000-05-11
EE9900517A (et)	2000-06-15
AP9901674A0 (en)	1999-12-31
NZ500141A (en)	2002-05-31
CA2286673A1 (en)	1998-10-29
UA68348C2 (en)	2004-08-16

Publication	Publication Date	Title
OA11261A (en)	2003-07-24	Method of using cyclooxygenase-2 inhibitors in theprevention of cardiovascular disorders
US6342510B1 (en)	2002-01-29	Treatment of inflammation and inflammation-related disorders with a combination of a cyclooxygenase-2 inhibitors and a leukotriene B4 receptor antagonist
US5990148A (en)	1999-11-23	Treatment of inflammation and inflammation-related disorders with a combination of a cyclooxygenase-2 inhibitor and a leukotriene A4 hydrolase inhibitor
US6136839A (en)	2000-10-24	Treatment of inflammation and inflammation-related disorders with a combination of a cyclooxygenase-2 inhibitor and a 5-lipoxygenase inhibitor
RU99110192A (ru)	2001-03-27	Способ применения ингибиторов циклооксигеназы-2 для лечения и профилактики неоплазии
EP1526869A1 (en)	2005-05-04	Compositions of a cyclooxygenase-2 selective inhibitor and a carbonic anhydrase inhibitor for the treatment of neoplasia
MXPA04010888A (es)	2005-07-14	Combinacion de inhibidores de ciclooxigenasa-2 y talidomida para el tratamiento de neoplasia.
EP1365753A2 (en)	2003-12-03	Uroguanylin and cyclooxygenase-2 inhibitor combinations for inhibition of intestinal cancer
US20020035156A1 (en)	2002-03-21	Combination therapy in the prevention of cardiovascular disorders
JP2005501850A5 (is)	2006-01-12
JP2005507871A5 (is)	2006-01-05
US20040121961A1 (en)	2004-06-24	Uroguanylin and cyclooxygenase-2 inhibitor combinations for inhibition of intestinal cancer
US20070072861A1 (en)	2007-03-29	Method of using cyclooxygenase-2 inhibitors in the prevention of cardiovascular disorders
ZA200308822B (en)	2005-02-14	Compositions of cyclooxygenase-2 selective inhibitors and radiation for inhibition or prevention of cardiovascular disease.
MXPA99009495A (en)	2000-12-06	Method of using cyclooxygenase-2 inhibitors in the prevention of cardiovascular disorders
US20050004224A1 (en)	2005-01-06	Treatment of Alzheimer's disease with the R(-) isomer of a 2-arylpropionic acid non-steroidal anti-inflammatory drug alone or in combination with a cyclooxygenase-2 selective inhibitor
CZ9903642A3 (cs)	2000-10-11	Použití inhibitorů cyklooxygenasy-2 pro prevenci kardiovaskulárních onemocnění
EP1027048A2 (en)	2000-08-16	Selective cyclooxygenase-2 inhibitors against premature labor