ZA200308822B - Compositions of cyclooxygenase-2 selective inhibitors and radiation for inhibition or prevention of cardiovascular disease. - Google Patents
Compositions of cyclooxygenase-2 selective inhibitors and radiation for inhibition or prevention of cardiovascular disease. Download PDFInfo
- Publication number
- ZA200308822B ZA200308822B ZA200308822A ZA200308822A ZA200308822B ZA 200308822 B ZA200308822 B ZA 200308822B ZA 200308822 A ZA200308822 A ZA 200308822A ZA 200308822 A ZA200308822 A ZA 200308822A ZA 200308822 B ZA200308822 B ZA 200308822B
- Authority
- ZA
- South Africa
- Prior art keywords
- trifluoromethyl
- phenyl
- cyclooxygenase
- radiation
- substance
- Prior art date
Links
- 108010037462 Cyclooxygenase 2 Proteins 0.000 title claims description 120
- 230000005855 radiation Effects 0.000 title claims description 116
- 229940124639 Selective inhibitor Drugs 0.000 title claims description 114
- 239000000203 mixture Substances 0.000 title claims description 93
- 230000002265 prevention Effects 0.000 title claims description 88
- 208000024172 Cardiovascular disease Diseases 0.000 title claims description 20
- 102000010907 Cyclooxygenase 2 Human genes 0.000 title claims 91
- 230000005764 inhibitory process Effects 0.000 title description 11
- -1 bromine-80m Chemical compound 0.000 claims description 209
- 238000000034 method Methods 0.000 claims description 179
- 150000003839 salts Chemical class 0.000 claims description 90
- 229940002612 prodrug Drugs 0.000 claims description 89
- 239000000651 prodrug Substances 0.000 claims description 89
- 238000011282 treatment Methods 0.000 claims description 88
- 150000003254 radicals Chemical group 0.000 claims description 71
- 125000004432 carbon atom Chemical group C* 0.000 claims description 44
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 35
- 125000000217 alkyl group Chemical group 0.000 claims description 33
- 150000001875 compounds Chemical class 0.000 claims description 32
- 125000003118 aryl group Chemical group 0.000 claims description 20
- 125000001188 haloalkyl group Chemical group 0.000 claims description 20
- 125000005843 halogen group Chemical group 0.000 claims description 20
- 125000003545 alkoxy group Chemical group 0.000 claims description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims description 17
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 16
- 206010020718 hyperplasia Diseases 0.000 claims description 15
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 15
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 14
- 125000003282 alkyl amino group Chemical group 0.000 claims description 14
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 14
- 238000002725 brachytherapy Methods 0.000 claims description 14
- 210000004351 coronary vessel Anatomy 0.000 claims description 14
- 150000002148 esters Chemical class 0.000 claims description 14
- 125000000623 heterocyclic group Chemical group 0.000 claims description 13
- 229910052717 sulfur Inorganic materials 0.000 claims description 13
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 12
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 12
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
- 206010061218 Inflammation Diseases 0.000 claims description 11
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 11
- 230000004054 inflammatory process Effects 0.000 claims description 11
- 239000002245 particle Substances 0.000 claims description 11
- 125000004414 alkyl thio group Chemical group 0.000 claims description 10
- 125000001153 fluoro group Chemical group F* 0.000 claims description 10
- 230000002792 vascular Effects 0.000 claims description 10
- 208000007536 Thrombosis Diseases 0.000 claims description 9
- 125000005099 aryl alkyl carbonyl group Chemical group 0.000 claims description 9
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 9
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 9
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 9
- 125000004471 alkyl aminosulfonyl group Chemical group 0.000 claims description 8
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 8
- 125000001769 aryl amino group Chemical group 0.000 claims description 8
- 150000001562 benzopyrans Chemical class 0.000 claims description 8
- 239000000460 chlorine Substances 0.000 claims description 8
- VFLDPWHFBUODDF-FCXRPNKRSA-N curcumin Chemical compound C1=C(O)C(OC)=CC(\C=C\C(=O)CC(=O)\C=C\C=2C=C(OC)C(O)=CC=2)=C1 VFLDPWHFBUODDF-FCXRPNKRSA-N 0.000 claims description 8
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 8
- KYNSBQPICQTCGU-UHFFFAOYSA-N Benzopyrane Chemical compound C1=CC=C2C=CCOC2=C1 KYNSBQPICQTCGU-UHFFFAOYSA-N 0.000 claims description 7
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 7
- 230000003110 anti-inflammatory effect Effects 0.000 claims description 7
- 125000005129 aryl carbonyl group Chemical group 0.000 claims description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- 125000001072 heteroaryl group Chemical group 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- 230000002285 radioactive effect Effects 0.000 claims description 7
- 125000003342 alkenyl group Chemical group 0.000 claims description 6
- 125000004104 aryloxy group Chemical group 0.000 claims description 6
- 125000004181 carboxyalkyl group Chemical group 0.000 claims description 6
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 6
- 238000007634 remodeling Methods 0.000 claims description 6
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 5
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 5
- 125000001691 aryl alkyl amino group Chemical group 0.000 claims description 5
- IIUZTXTZRGLYTI-UHFFFAOYSA-N Dihydrogriseofulvin Natural products COC1CC(=O)CC(C)C11C(=O)C(C(OC)=CC(OC)=C2Cl)=C2O1 IIUZTXTZRGLYTI-UHFFFAOYSA-N 0.000 claims description 4
- UXWOXTQWVMFRSE-UHFFFAOYSA-N Griseoviridin Natural products O=C1OC(C)CC=C(C(NCC=CC=CC(O)CC(O)C2)=O)SCC1NC(=O)C1=COC2=N1 UXWOXTQWVMFRSE-UHFFFAOYSA-N 0.000 claims description 4
- UETNIIAIRMUTSM-UHFFFAOYSA-N Jacareubin Natural products CC1(C)OC2=CC3Oc4c(O)c(O)ccc4C(=O)C3C(=C2C=C1)O UETNIIAIRMUTSM-UHFFFAOYSA-N 0.000 claims description 4
- DDUHZTYCFQRHIY-UHFFFAOYSA-N Negwer: 6874 Natural products COC1=CC(=O)CC(C)C11C(=O)C(C(OC)=CC(OC)=C2Cl)=C2O1 DDUHZTYCFQRHIY-UHFFFAOYSA-N 0.000 claims description 4
- 102000004005 Prostaglandin-endoperoxide synthases Human genes 0.000 claims description 4
- 108090000459 Prostaglandin-endoperoxide synthases Proteins 0.000 claims description 4
- 125000002252 acyl group Chemical group 0.000 claims description 4
- 125000006350 alkyl thio alkyl group Chemical group 0.000 claims description 4
- 125000000304 alkynyl group Chemical group 0.000 claims description 4
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 4
- 125000005141 aryl amino sulfonyl group Chemical group 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 239000003246 corticosteroid Substances 0.000 claims description 4
- 229940109262 curcumin Drugs 0.000 claims description 4
- 235000012754 curcumin Nutrition 0.000 claims description 4
- 239000004148 curcumin Substances 0.000 claims description 4
- VFLDPWHFBUODDF-UHFFFAOYSA-N diferuloylmethane Natural products C1=C(O)C(OC)=CC(C=CC(=O)CC(=O)C=CC=2C=C(OC)C(O)=CC=2)=C1 VFLDPWHFBUODDF-UHFFFAOYSA-N 0.000 claims description 4
- 125000005044 dihydroquinolinyl group Chemical group N1(CC=CC2=CC=CC=C12)* 0.000 claims description 4
- DDUHZTYCFQRHIY-RBHXEPJQSA-N griseofulvin Chemical compound COC1=CC(=O)C[C@@H](C)[C@@]11C(=O)C(C(OC)=CC(OC)=C2Cl)=C2O1 DDUHZTYCFQRHIY-RBHXEPJQSA-N 0.000 claims description 4
- 229960002867 griseofulvin Drugs 0.000 claims description 4
- 125000005241 heteroarylamino group Chemical group 0.000 claims description 4
- 125000005223 heteroarylcarbonyl group Chemical group 0.000 claims description 4
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 4
- NCEXYHBECQHGNR-QZQOTICOSA-N sulfasalazine Chemical compound C1=C(O)C(C(=O)O)=CC(\N=N\C=2C=CC(=CC=2)S(=O)(=O)NC=2N=CC=CC=2)=C1 NCEXYHBECQHGNR-QZQOTICOSA-N 0.000 claims description 4
- 229960001940 sulfasalazine Drugs 0.000 claims description 4
- NCEXYHBECQHGNR-UHFFFAOYSA-N sulfasalazine Natural products C1=C(O)C(C(=O)O)=CC(N=NC=2C=CC(=CC=2)S(=O)(=O)NC=2N=CC=CC=2)=C1 NCEXYHBECQHGNR-UHFFFAOYSA-N 0.000 claims description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
- 229960005342 tranilast Drugs 0.000 claims description 4
- NZHGWWWHIYHZNX-CSKARUKUSA-N tranilast Chemical compound C1=C(OC)C(OC)=CC=C1\C=C\C(=O)NC1=CC=CC=C1C(O)=O NZHGWWWHIYHZNX-CSKARUKUSA-N 0.000 claims description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims description 3
- 125000000278 alkyl amino alkyl group Chemical group 0.000 claims description 3
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 3
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 3
- 125000005097 aminocarbonylalkyl group Chemical group 0.000 claims description 3
- 125000005160 aryl oxy alkyl group Chemical group 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 125000005842 heteroatom Chemical group 0.000 claims description 3
- 125000004415 heterocyclylalkyl group Chemical group 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
- 125000001624 naphthyl group Chemical group 0.000 claims description 3
- 125000004999 nitroaryl group Chemical group 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 3
- 125000004043 oxo group Chemical group O=* 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 claims description 3
- 125000003107 substituted aryl group Chemical group 0.000 claims description 3
- 239000011593 sulfur Substances 0.000 claims description 3
- 238000002560 therapeutic procedure Methods 0.000 claims description 3
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 claims description 3
- 125000004689 alkyl amino carbonyl alkyl group Chemical group 0.000 claims description 2
- 125000004659 aryl alkyl thio group Chemical group 0.000 claims description 2
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 2
- 125000005110 aryl thio group Chemical group 0.000 claims description 2
- 125000002837 carbocyclic group Chemical group 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 claims description 2
- 125000004966 cyanoalkyl group Chemical group 0.000 claims description 2
- 125000004772 dichloromethyl group Chemical group [H]C(Cl)(Cl)* 0.000 claims description 2
- 125000006001 difluoroethyl group Chemical group 0.000 claims description 2
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims description 2
- 125000002541 furyl group Chemical group 0.000 claims description 2
- 125000006343 heptafluoro propyl group Chemical group 0.000 claims description 2
- 125000005844 heterocyclyloxy group Chemical group 0.000 claims description 2
- 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 2
- 125000001145 hydrido group Chemical group *[H] 0.000 claims description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 2
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
- 125000001544 thienyl group Chemical group 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims 88
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims 11
- 238000002360 preparation method Methods 0.000 claims 11
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 10
- 239000001257 hydrogen Substances 0.000 claims 8
- ZFKBWSREWJOSSJ-VIFPVBQESA-N (2s)-6,8-dichloro-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound ClC1=CC(Cl)=C2O[C@H](C(F)(F)F)C(C(=O)O)=CC2=C1 ZFKBWSREWJOSSJ-VIFPVBQESA-N 0.000 claims 6
- WUAPFZMCVAUBPE-NJFSPNSNSA-N 188Re Chemical compound [188Re] WUAPFZMCVAUBPE-NJFSPNSNSA-N 0.000 claims 6
- OAICVXFJPJFONN-OUBTZVSYSA-N Phosphorus-32 Chemical compound [32P] OAICVXFJPJFONN-OUBTZVSYSA-N 0.000 claims 6
- CIOAGBVUUVVLOB-NJFSPNSNSA-N Strontium-90 Chemical compound [90Sr] CIOAGBVUUVVLOB-NJFSPNSNSA-N 0.000 claims 6
- FHNFHKCVQCLJFQ-NJFSPNSNSA-N Xenon-133 Chemical compound [133Xe] FHNFHKCVQCLJFQ-NJFSPNSNSA-N 0.000 claims 6
- 210000004204 blood vessel Anatomy 0.000 claims 6
- 229940097886 phosphorus 32 Drugs 0.000 claims 6
- WUAPFZMCVAUBPE-IGMARMGPSA-N rhenium-186 Chemical compound [186Re] WUAPFZMCVAUBPE-IGMARMGPSA-N 0.000 claims 6
- 229940106670 xenon-133 Drugs 0.000 claims 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 5
- GKLVYJBZJHMRIY-OUBTZVSYSA-N Technetium-99 Chemical compound [99Tc] GKLVYJBZJHMRIY-OUBTZVSYSA-N 0.000 claims 5
- 125000004145 cyclopenten-1-yl group Chemical group [H]C1=C(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 5
- GKOZUEZYRPOHIO-IGMARMGPSA-N iridium-192 Chemical compound [192Ir] GKOZUEZYRPOHIO-IGMARMGPSA-N 0.000 claims 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 5
- 229940056501 technetium 99m Drugs 0.000 claims 5
- 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 4
- NONBXOPYDWLZGR-UHFFFAOYSA-N 6-chloro-8-methyl-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound C1=C(C(O)=O)C(C(F)(F)F)OC2=C1C=C(Cl)C=C2C NONBXOPYDWLZGR-UHFFFAOYSA-N 0.000 claims 3
- QGCKNIAMHUUUDI-UHFFFAOYSA-N 7-tert-butyl-6-chloro-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound O1C(C(F)(F)F)C(C(O)=O)=CC2=C1C=C(C(C)(C)C)C(Cl)=C2 QGCKNIAMHUUUDI-UHFFFAOYSA-N 0.000 claims 3
- 229940122204 Cyclooxygenase inhibitor Drugs 0.000 claims 3
- 101000783577 Dendroaspis angusticeps Thrombostatin Proteins 0.000 claims 3
- 101000783578 Dendroaspis jamesoni kaimosae Dendroaspin Proteins 0.000 claims 3
- 239000003146 anticoagulant agent Substances 0.000 claims 3
- 229940127218 antiplatelet drug Drugs 0.000 claims 3
- 229960004676 antithrombotic agent Drugs 0.000 claims 3
- 230000005670 electromagnetic radiation Effects 0.000 claims 3
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 3
- 150000002431 hydrogen Chemical class 0.000 claims 3
- JCDWETOKTFWTHA-UHFFFAOYSA-N methylsulfonylbenzene Chemical compound CS(=O)(=O)C1=CC=CC=C1 JCDWETOKTFWTHA-UHFFFAOYSA-N 0.000 claims 3
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical class OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 claims 3
- 239000000106 platelet aggregation inhibitor Substances 0.000 claims 3
- 239000002599 prostaglandin synthase inhibitor Substances 0.000 claims 3
- 229930195734 saturated hydrocarbon Natural products 0.000 claims 3
- 208000024891 symptom Diseases 0.000 claims 3
- ZJOUYQCSZYKGKU-UHFFFAOYSA-N 3-[1-(4-methylsulfonylphenyl)-4-(trifluoromethyl)imidazol-2-yl]pyridine Chemical compound C1=CC(S(=O)(=O)C)=CC=C1N1C(C=2C=NC=CC=2)=NC(C(F)(F)F)=C1 ZJOUYQCSZYKGKU-UHFFFAOYSA-N 0.000 claims 2
- NSQNZEUFHPTJME-UHFFFAOYSA-N 4-[5-(4-chlorophenyl)-3-(trifluoromethyl)pyrazol-1-yl]benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1N1C(C=2C=CC(Cl)=CC=2)=CC(C(F)(F)F)=N1 NSQNZEUFHPTJME-UHFFFAOYSA-N 0.000 claims 2
- XCTHXVRBSIHBAC-UHFFFAOYSA-N 6-chloro-2-(trifluoromethyl)-2h-thiochromene-3-carboxylic acid Chemical compound ClC1=CC=C2SC(C(F)(F)F)C(C(=O)O)=CC2=C1 XCTHXVRBSIHBAC-UHFFFAOYSA-N 0.000 claims 2
- GZVGBJIOQBOCCF-UHFFFAOYSA-N 6-nitro-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound [O-][N+](=O)C1=CC=C2OC(C(F)(F)F)C(C(=O)O)=CC2=C1 GZVGBJIOQBOCCF-UHFFFAOYSA-N 0.000 claims 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 2
- HYWYRSMBCFDLJT-UHFFFAOYSA-N nimesulide Chemical compound CS(=O)(=O)NC1=CC=C([N+]([O-])=O)C=C1OC1=CC=CC=C1 HYWYRSMBCFDLJT-UHFFFAOYSA-N 0.000 claims 2
- 125000003003 spiro group Chemical group 0.000 claims 2
- PWULVHYHVZUTFR-UHFFFAOYSA-N spiro[2.4]hept-5-ene Chemical compound C1CC11CC=CC1 PWULVHYHVZUTFR-UHFFFAOYSA-N 0.000 claims 2
- 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 2
- PCHJSUWPFVWCPO-NJFSPNSNSA-N (199au)gold Chemical compound [199Au] PCHJSUWPFVWCPO-NJFSPNSNSA-N 0.000 claims 1
- AVCMFIJXDZYZOT-VIFPVBQESA-N (2s)-6-chloro-2-(trifluoromethyl)-1,2-dihydroquinoline-3-carboxylic acid Chemical compound ClC1=CC=C2N[C@H](C(F)(F)F)C(C(=O)O)=CC2=C1 AVCMFIJXDZYZOT-VIFPVBQESA-N 0.000 claims 1
- FLBAYUMRQUHISI-UHFFFAOYSA-N 1,8-naphthyridine Chemical compound N1=CC=CC2=CC=CN=C21 FLBAYUMRQUHISI-UHFFFAOYSA-N 0.000 claims 1
- RFPZMXMBYMEQHZ-UHFFFAOYSA-N 1-(4-fluorophenyl)-2-(4-methylsulfonylphenyl)benzene Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=CC=CC=C1C1=CC=C(F)C=C1 RFPZMXMBYMEQHZ-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- HUVCBGHNHBHJBX-UHFFFAOYSA-N 1-[2-(4-chlorophenyl)-4,4-dimethylcyclopenten-1-yl]-4-methylsulfonylbenzene Chemical compound C1C(C)(C)CC(C=2C=CC(Cl)=CC=2)=C1C1=CC=C(S(C)(=O)=O)C=C1 HUVCBGHNHBHJBX-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- XKSNSSNGFIQSFK-UHFFFAOYSA-N 1-ethyl-4-(4-fluorophenyl)-3-(4-methylsulfonylphenyl)-5-(trifluoromethyl)pyrazole Chemical compound FC(F)(F)C=1N(CC)N=C(C=2C=CC(=CC=2)S(C)(=O)=O)C=1C1=CC=C(F)C=C1 XKSNSSNGFIQSFK-UHFFFAOYSA-N 0.000 claims 1
- JQDLRYPRLMZWFM-UHFFFAOYSA-N 1-methylsulfanyl-4-[2-(4-methylsulfonylphenyl)cyclopenten-1-yl]benzene Chemical compound C1=CC(SC)=CC=C1C1=C(C=2C=CC(=CC=2)S(C)(=O)=O)CCC1 JQDLRYPRLMZWFM-UHFFFAOYSA-N 0.000 claims 1
- PNDPGZBMCMUPRI-HVTJNCQCSA-N 10043-66-0 Chemical compound [131I][131I] PNDPGZBMCMUPRI-HVTJNCQCSA-N 0.000 claims 1
- 125000004869 2,2-dimethylpropylcarbonyl group Chemical group CC(CC(=O)*)(C)C 0.000 claims 1
- VCLNQQUCGTWUKD-UHFFFAOYSA-N 2-(2-chlorophenyl)-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(=CC=CC=2)Cl)S1 VCLNQQUCGTWUKD-UHFFFAOYSA-N 0.000 claims 1
- 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 1
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Landscapes
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US20040063697A1 (en) * | 2002-07-02 | 2004-04-01 | Isakson Peter C. | Compositions of cyclooxygenase-2 selective inhibitors and thrombolytic agents for the treatment or prevention of a vaso-occlusive event |
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US7259266B2 (en) | 2003-03-31 | 2007-08-21 | Pharmacia Corporation | Benzopyran compounds useful for treating inflammatory conditions |
TWI646091B (zh) * | 2012-12-28 | 2019-01-01 | 日商衛斯克慧特股份有限公司 | 鹽類及晶形 |
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US5116864A (en) * | 1991-04-09 | 1992-05-26 | Indiana University Foundation | Method for preventing restenosis following reconfiguration of body vessels |
US5380738A (en) * | 1993-05-21 | 1995-01-10 | Monsanto Company | 2-substituted oxazoles further substituted by 4-fluorophenyl and 4-methylsulfonylphenyl as antiinflammatory agents |
US5474995A (en) * | 1993-06-24 | 1995-12-12 | Merck Frosst Canada, Inc. | Phenyl heterocycles as cox-2 inhibitors |
US6196996B1 (en) * | 1993-07-15 | 2001-03-06 | Paul S. Teirstein | Irradiation catheter and method of use |
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-
2002
- 2002-05-23 US US10/154,275 patent/US20030153801A1/en not_active Abandoned
- 2002-05-29 MX MXPA03011055A patent/MXPA03011055A/es unknown
- 2002-05-29 KR KR10-2003-7015571A patent/KR20040032100A/ko not_active Application Discontinuation
- 2002-05-29 CA CA002447657A patent/CA2447657A1/en not_active Abandoned
- 2002-05-29 PL PL02367028A patent/PL367028A1/xx not_active Application Discontinuation
- 2002-05-29 CN CNA028109910A patent/CN1561246A/zh active Pending
- 2002-05-29 JP JP2002593022A patent/JP2004536073A/ja not_active Withdrawn
- 2002-05-29 EA EA200301197A patent/EA200301197A1/ru unknown
- 2002-05-29 IL IL15911102A patent/IL159111A0/xx unknown
- 2002-05-29 EP EP02739651A patent/EP1406696A1/en not_active Withdrawn
- 2002-05-29 WO PCT/US2002/017552 patent/WO2002096516A1/en not_active Application Discontinuation
- 2002-05-29 AU AU2002312291A patent/AU2002312291B2/en not_active Expired - Fee Related
- 2002-05-29 CZ CZ20033258A patent/CZ20033258A3/cs unknown
- 2002-05-29 BR BR0209776-1A patent/BR0209776A/pt not_active IP Right Cessation
-
2003
- 2003-11-12 ZA ZA200308822A patent/ZA200308822B/en unknown
- 2003-11-25 CO CO03103981A patent/CO5540374A2/es not_active Application Discontinuation
- 2003-11-28 NO NO20035299A patent/NO20035299D0/no not_active Application Discontinuation
Also Published As
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PL367028A1 (en) | 2005-02-07 |
CA2447657A1 (en) | 2002-12-05 |
BR0209776A (pt) | 2004-07-13 |
EP1406696A1 (en) | 2004-04-14 |
CN1561246A (zh) | 2005-01-05 |
NO20035299D0 (no) | 2003-11-28 |
KR20040032100A (ko) | 2004-04-14 |
WO2002096516A1 (en) | 2002-12-05 |
JP2004536073A (ja) | 2004-12-02 |
IL159111A0 (en) | 2004-05-12 |
CO5540374A2 (es) | 2005-07-29 |
CZ20033258A3 (cs) | 2004-12-15 |
WO2002096516A8 (en) | 2003-02-20 |
AU2002312291B2 (en) | 2006-03-16 |
US20030153801A1 (en) | 2003-08-14 |
MXPA03011055A (es) | 2004-12-06 |
EA200301197A1 (ru) | 2004-08-26 |
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