JP2005501850A5 - - Google Patents
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- Publication number
- JP2005501850A5 JP2005501850A5 JP2003520758A JP2003520758A JP2005501850A5 JP 2005501850 A5 JP2005501850 A5 JP 2005501850A5 JP 2003520758 A JP2003520758 A JP 2003520758A JP 2003520758 A JP2003520758 A JP 2003520758A JP 2005501850 A5 JP2005501850 A5 JP 2005501850A5
- Authority
- JP
- Japan
- Prior art keywords
- trifluoromethyl
- phenyl
- benzenesulfonamide
- methylsulfonyl
- alkyl
- Prior art date
- 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.)
- Withdrawn
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- RQUCIYUYJHVVIL-UHFFFAOYSA-N 3-[[5-(4-chlorobenzoyl)-1,4-dimethylpyrrol-2-yl]methyl]-1h-pyridazin-6-one Chemical compound CN1C(C(=O)C=2C=CC(Cl)=CC=2)=C(C)C=C1CC=1C=CC(=O)NN=1 RQUCIYUYJHVVIL-UHFFFAOYSA-N 0.000 claims description 2
- -1 C 1 -C 6 -alkoxy Chemical group 0.000 claims 78
- 239000003814 drug Substances 0.000 claims 58
- 108010037462 Cyclooxygenase 2 Proteins 0.000 claims 47
- 102100038280 Prostaglandin G/H synthase 2 Human genes 0.000 claims 47
- 229940124639 Selective inhibitor Drugs 0.000 claims 40
- 239000000651 prodrug Substances 0.000 claims 29
- 229940002612 prodrug Drugs 0.000 claims 29
- 125000003118 aryl group Chemical group 0.000 claims 26
- 150000003839 salts Chemical class 0.000 claims 22
- SQDAZGGFXASXDW-UHFFFAOYSA-N 5-bromo-2-(trifluoromethoxy)pyridine Chemical compound FC(F)(F)OC1=CC=C(Br)C=N1 SQDAZGGFXASXDW-UHFFFAOYSA-N 0.000 claims 21
- 229920001287 Chondroitin sulfate Polymers 0.000 claims 21
- 206010061218 Inflammation Diseases 0.000 claims 21
- 125000000217 alkyl group Chemical group 0.000 claims 21
- 229940059329 chondroitin sulfate Drugs 0.000 claims 21
- 230000004054 inflammatory process Effects 0.000 claims 21
- 125000001188 haloalkyl group Chemical group 0.000 claims 16
- 150000004678 hydrides Chemical class 0.000 claims 16
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 15
- 208000035475 disorder Diseases 0.000 claims 15
- 125000005843 halogen group Chemical group 0.000 claims 15
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 12
- 208000002193 Pain Diseases 0.000 claims 11
- 125000003710 aryl alkyl group Chemical group 0.000 claims 11
- 125000001072 heteroaryl group Chemical group 0.000 claims 11
- 230000036407 pain Effects 0.000 claims 11
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 10
- 125000001309 chloro group Chemical group Cl* 0.000 claims 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 10
- MSWZFWKMSRAUBD-IVMDWMLBSA-N 2-amino-2-deoxy-D-glucopyranose Chemical compound N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O MSWZFWKMSRAUBD-IVMDWMLBSA-N 0.000 claims 9
- 125000003545 alkoxy group Chemical group 0.000 claims 9
- MSWZFWKMSRAUBD-UHFFFAOYSA-N beta-D-galactosamine Natural products NC1C(O)OC(CO)C(O)C1O MSWZFWKMSRAUBD-UHFFFAOYSA-N 0.000 claims 9
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 9
- 229960002442 glucosamine Drugs 0.000 claims 9
- 125000001624 naphthyl group Chemical group 0.000 claims 9
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims 8
- 125000001153 fluoro group Chemical group F* 0.000 claims 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 8
- 229910052760 oxygen Inorganic materials 0.000 claims 8
- 229910052717 sulfur Inorganic materials 0.000 claims 8
- 125000003282 alkyl amino group Chemical group 0.000 claims 7
- 125000004471 alkyl aminosulfonyl group Chemical group 0.000 claims 7
- 125000004438 haloalkoxy group Chemical group 0.000 claims 7
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 6
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims 6
- 125000005099 aryl alkyl carbonyl group Chemical group 0.000 claims 6
- 125000001769 aryl amino group Chemical group 0.000 claims 6
- 125000004104 aryloxy group Chemical group 0.000 claims 6
- 230000037396 body weight Effects 0.000 claims 6
- 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 6
- 125000001145 hydrido group Chemical group *[H] 0.000 claims 6
- 229910052739 hydrogen Inorganic materials 0.000 claims 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 6
- 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 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims 5
- 125000004414 alkyl thio group Chemical group 0.000 claims 5
- 125000005141 aryl amino sulfonyl group Chemical group 0.000 claims 5
- 125000005129 aryl carbonyl group Chemical group 0.000 claims 5
- 125000005241 heteroarylamino group Chemical group 0.000 claims 5
- 125000005223 heteroarylcarbonyl group Chemical group 0.000 claims 5
- 125000005553 heteroaryloxy group Chemical group 0.000 claims 5
- 239000001257 hydrogen Substances 0.000 claims 5
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 4
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 4
- 108010037464 Cyclooxygenase 1 Proteins 0.000 claims 4
- 102100038277 Prostaglandin G/H synthase 1 Human genes 0.000 claims 4
- 229910052799 carbon Inorganic materials 0.000 claims 4
- 229960000590 celecoxib Drugs 0.000 claims 4
- 150000001875 compounds Chemical class 0.000 claims 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims 4
- 230000005764 inhibitory process Effects 0.000 claims 4
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims 4
- 239000000203 mixture Substances 0.000 claims 4
- 230000002265 prevention Effects 0.000 claims 4
- 229960002004 valdecoxib Drugs 0.000 claims 4
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 3
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 3
- 239000002253 acid Substances 0.000 claims 3
- 125000002252 acyl group Chemical group 0.000 claims 3
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims 3
- 125000001691 aryl alkyl amino group Chemical group 0.000 claims 3
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims 3
- 125000005110 aryl thio group Chemical group 0.000 claims 3
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 3
- 125000005044 dihydroquinolinyl group Chemical group N1(CC=CC2=CC=CC=C12)* 0.000 claims 3
- 229940079593 drug Drugs 0.000 claims 3
- 125000000623 heterocyclic group Chemical group 0.000 claims 3
- 150000002431 hydrogen Chemical class 0.000 claims 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 3
- 229960004662 parecoxib Drugs 0.000 claims 3
- 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 3
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 claims 3
- RZJQGNCSTQAWON-UHFFFAOYSA-N rofecoxib Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=CC=CC=2)C(=O)OC1 RZJQGNCSTQAWON-UHFFFAOYSA-N 0.000 claims 3
- 229960000371 rofecoxib Drugs 0.000 claims 3
- 125000003107 substituted aryl group Chemical group 0.000 claims 3
- 230000001629 suppression Effects 0.000 claims 3
- 208000037816 tissue injury Diseases 0.000 claims 3
- 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 claims 2
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims 2
- 125000004750 (C1-C6) alkylaminosulfonyl group Chemical group 0.000 claims 2
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims 2
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims 2
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims 2
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 2
- 125000004749 (C1-C6) haloalkylsulfinyl group Chemical group 0.000 claims 2
- 125000004741 (C1-C6) haloalkylsulfonyl group Chemical group 0.000 claims 2
- 125000006771 (C1-C6) haloalkylthio group Chemical group 0.000 claims 2
- IWTSTYWGRNOWJQ-UHFFFAOYSA-N 2-(trifluoromethyl)-3h-benzo[f]chromene-3-carboxylic acid Chemical compound C1=CC=CC2=C(C=C(C(C(=O)O)O3)C(F)(F)F)C3=CC=C21 IWTSTYWGRNOWJQ-UHFFFAOYSA-N 0.000 claims 2
- 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
- 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 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
- 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 2
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 2
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims 2
- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims 2
- 206010010741 Conjunctivitis Diseases 0.000 claims 2
- 201000004624 Dermatitis Diseases 0.000 claims 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 2
- 206010052128 Glare Diseases 0.000 claims 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims 2
- 206010037660 Pyrexia Diseases 0.000 claims 2
- 208000017442 Retinal disease Diseases 0.000 claims 2
- 206010038910 Retinitis Diseases 0.000 claims 2
- 208000000491 Tendinopathy Diseases 0.000 claims 2
- 206010043255 Tendonitis Diseases 0.000 claims 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims 2
- XCCTYIAWTASOJW-XVFCMESISA-N Uridine-5'-Diphosphate Chemical compound O[C@@H]1[C@H](O)[C@@H](COP(O)(=O)OP(O)(O)=O)O[C@H]1N1C(=O)NC(=O)C=C1 XCCTYIAWTASOJW-XVFCMESISA-N 0.000 claims 2
- 206010046851 Uveitis Diseases 0.000 claims 2
- 230000001154 acute effect Effects 0.000 claims 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 2
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims 2
- 206010003246 arthritis Diseases 0.000 claims 2
- 125000005135 aryl sulfinyl group Chemical group 0.000 claims 2
- 150000008371 chromenes Chemical class 0.000 claims 2
- WAZQAZKAZLXFMK-UHFFFAOYSA-N deracoxib Chemical compound C1=C(F)C(OC)=CC=C1C1=CC(C(F)F)=NN1C1=CC=C(S(N)(=O)=O)C=C1 WAZQAZKAZLXFMK-UHFFFAOYSA-N 0.000 claims 2
- 125000004987 dibenzofuryl group Chemical group C1(=CC=CC=2OC3=C(C21)C=CC=C3)* 0.000 claims 2
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims 2
- 125000006263 dimethyl aminosulfonyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])S(*)(=O)=O 0.000 claims 2
- 239000002552 dosage form Substances 0.000 claims 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims 2
- 230000004313 glare Effects 0.000 claims 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 2
- 125000005956 isoquinolyl group Chemical group 0.000 claims 2
- 230000001404 mediated effect Effects 0.000 claims 2
- 238000000034 method Methods 0.000 claims 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 2
- 229950006780 n-acetylglucosamine Drugs 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- 201000008482 osteoarthritis Diseases 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 2
- 125000005493 quinolyl group Chemical group 0.000 claims 2
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims 2
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 2
- 125000006413 ring segment Chemical group 0.000 claims 2
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 2
- 208000024891 symptom Diseases 0.000 claims 2
- 201000004415 tendinitis Diseases 0.000 claims 2
- 125000001544 thienyl group Chemical group 0.000 claims 2
- KIUKXJAPPMFGSW-DNGZLQJQSA-N (2S,3S,4S,5R,6R)-6-[(2S,3R,4R,5S,6R)-3-Acetamido-2-[(2S,3S,4R,5R,6R)-6-[(2R,3R,4R,5S,6R)-3-acetamido-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-2-carboxy-4,5-dihydroxyoxan-3-yl]oxy-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid Chemical compound CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](O[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@H](O3)C(O)=O)O)[C@H](O)[C@@H](CO)O2)NC(C)=O)[C@@H](C(O)=O)O1 KIUKXJAPPMFGSW-DNGZLQJQSA-N 0.000 claims 1
- 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 1
- 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 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
- BPWDIXPFAHESAF-UHFFFAOYSA-N 1-[3,3-dimethyl-5-(4-methylsulfonylphenyl)cyclopenta-1,4-dien-1-yl]-4-fluorobenzene Chemical compound C=1C(C)(C)C=C(C=2C=CC(F)=CC=2)C=1C1=CC=C(S(C)(=O)=O)C=C1 BPWDIXPFAHESAF-UHFFFAOYSA-N 0.000 claims 1
- 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 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
- 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 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
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims 1
- 125000004869 2,2-dimethylpropylcarbonyl group Chemical group CC(CC(=O)*)(C)C 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
- 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
- YLFBPUKBMRJHLM-UHFFFAOYSA-N 2-(3-chlorophenyl)-1-(4-methylsulfonylphenyl)-4-(trifluoromethyl)imidazole Chemical compound C1=CC(S(=O)(=O)C)=CC=C1N1C(C=2C=C(Cl)C=CC=2)=NC(C(F)(F)F)=C1 YLFBPUKBMRJHLM-UHFFFAOYSA-N 0.000 claims 1
- MEAMLMDMYOLDGW-UHFFFAOYSA-N 2-(3-fluoro-5-methylphenyl)-1-(4-methylsulfonylphenyl)-4-(trifluoromethyl)imidazole Chemical compound CC1=CC(F)=CC(C=2N(C=C(N=2)C(F)(F)F)C=2C=CC(=CC=2)S(C)(=O)=O)=C1 MEAMLMDMYOLDGW-UHFFFAOYSA-N 0.000 claims 1
- RSABMOYFBOLDLO-UHFFFAOYSA-N 2-(3-methylphenyl)-1-(4-methylsulfonylphenyl)-4-(trifluoromethyl)imidazole Chemical compound CC1=CC=CC(C=2N(C=C(N=2)C(F)(F)F)C=2C=CC(=CC=2)S(C)(=O)=O)=C1 RSABMOYFBOLDLO-UHFFFAOYSA-N 0.000 claims 1
- ZZBKFGAUXXMYNA-UHFFFAOYSA-N 2-(4-chlorophenyl)-1-(4-methylsulfonylphenyl)-4-phenylimidazole Chemical compound C1=CC(S(=O)(=O)C)=CC=C1N1C(C=2C=CC(Cl)=CC=2)=NC(C=2C=CC=CC=2)=C1 ZZBKFGAUXXMYNA-UHFFFAOYSA-N 0.000 claims 1
- UPXZCQZUZDWZHE-UHFFFAOYSA-N 2-(4-chlorophenyl)-4-(4-fluorophenyl)-1-(4-methylsulfonylphenyl)imidazole Chemical compound C1=CC(S(=O)(=O)C)=CC=C1N1C(C=2C=CC(Cl)=CC=2)=NC(C=2C=CC(F)=CC=2)=C1 UPXZCQZUZDWZHE-UHFFFAOYSA-N 0.000 claims 1
- RIZFWOPNUQFLEF-UHFFFAOYSA-N 2-(4-chlorophenyl)-4-methyl-1-(4-methylsulfonylphenyl)imidazole Chemical compound N=1C(C)=CN(C=2C=CC(=CC=2)S(C)(=O)=O)C=1C1=CC=C(Cl)C=C1 RIZFWOPNUQFLEF-UHFFFAOYSA-N 0.000 claims 1
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- 125000006261 methyl amino sulfonyl group Chemical group [H]N(C([H])([H])[H])S(*)(=O)=O 0.000 claims 1
- JCDWETOKTFWTHA-UHFFFAOYSA-N methylsulfonylbenzene Chemical compound CS(=O)(=O)C1=CC=CC=C1 JCDWETOKTFWTHA-UHFFFAOYSA-N 0.000 claims 1
- 206010027599 migraine Diseases 0.000 claims 1
- 201000006417 multiple sclerosis Diseases 0.000 claims 1
- 206010028417 myasthenia gravis Diseases 0.000 claims 1
- 208000031225 myocardial ischemia Diseases 0.000 claims 1
- YBCBOXOAJAQPQU-UHFFFAOYSA-N n-(2-cyclohexyloxy-3-nitrophenyl)methanesulfonamide Chemical compound CS(=O)(=O)NC1=CC=CC([N+]([O-])=O)=C1OC1CCCCC1 YBCBOXOAJAQPQU-UHFFFAOYSA-N 0.000 claims 1
- HKYOGYJVZLWKLN-UHFFFAOYSA-N n-[5-(3,4-difluorophenyl)-2-(trifluoromethyl)-1,3-oxazol-4-yl]benzenesulfonamide Chemical compound C1=C(F)C(F)=CC=C1C1=C(NS(=O)(=O)C=2C=CC=CC=2)N=C(C(F)(F)F)O1 HKYOGYJVZLWKLN-UHFFFAOYSA-N 0.000 claims 1
- HCSFFMYIHYYVTK-UHFFFAOYSA-N n-benzyl-4-(4-fluorophenyl)-5-(4-methylsulfonylphenyl)-1,3-thiazol-2-amine Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=CC(F)=CC=2)N=C(NCC=2C=CC=CC=2)S1 HCSFFMYIHYYVTK-UHFFFAOYSA-N 0.000 claims 1
- 229960000965 nimesulide Drugs 0.000 claims 1
- 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 1
- 125000004999 nitroaryl group Chemical group 0.000 claims 1
- 125000004287 oxazol-2-yl group Chemical group [H]C1=C([H])N=C(*)O1 0.000 claims 1
- 125000004043 oxo group Chemical group O=* 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 238000007911 parenteral administration Methods 0.000 claims 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical class OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 claims 1
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims 1
- 208000005987 polymyositis Diseases 0.000 claims 1
- 208000005333 pulmonary edema Diseases 0.000 claims 1
- 201000003068 rheumatic fever Diseases 0.000 claims 1
- 201000000306 sarcoidosis Diseases 0.000 claims 1
- 201000005671 spondyloarthropathy Diseases 0.000 claims 1
- 239000011593 sulfur Substances 0.000 claims 1
- 230000008961 swelling Effects 0.000 claims 1
- 201000000596 systemic lupus erythematosus Diseases 0.000 claims 1
- 230000001225 therapeutic effect Effects 0.000 claims 1
- 229930192474 thiophene Natural products 0.000 claims 1
- 206010043778 thyroiditis Diseases 0.000 claims 1
- MIMJSJSRRDZIPW-UHFFFAOYSA-N tilmacoxib Chemical compound C=1C=C(S(N)(=O)=O)C(F)=CC=1C=1OC(C)=NC=1C1CCCCC1 MIMJSJSRRDZIPW-UHFFFAOYSA-N 0.000 claims 1
- 208000004371 toothache Diseases 0.000 claims 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 claims 1
- 208000019553 vascular disease Diseases 0.000 claims 1
- 230000029663 wound healing Effects 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US31221101P | 2001-08-14 | 2001-08-14 | |
| US10/215,539 US20030114416A1 (en) | 2001-08-14 | 2002-08-09 | Method and compositions for the treatment and prevention of pain and inflammation with a cyclooxygenase-2 selective inhibitor and chondroitin sulfate |
| PCT/US2002/025673 WO2003015799A1 (en) | 2001-08-14 | 2002-08-13 | Compositions for the treatment and prevention of pain and inflammation with a cyclooxygenase-2 selective inhibitor and chondroitin sulfate |
Publications (2)
| Publication Number | Publication Date |
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| JP2005501850A JP2005501850A (ja) | 2005-01-20 |
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Country Status (12)
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| EP1406700A1 (en) * | 2001-07-06 | 2004-04-14 | Sucampo AG | Composition for topical administration comprising an interleukin-2 inhibitor and an antimicrobial agent |
| ES2223291B1 (es) * | 2003-08-06 | 2006-03-16 | Bioiberica, S.A. | Nuevo uso terapeutico de condroitin sulfato. |
| US7276050B2 (en) * | 2004-03-02 | 2007-10-02 | Alan Franklin | Trans-scleral drug delivery method and apparatus |
| CN1953660A (zh) | 2004-04-07 | 2007-04-25 | 佐治亚州大学研究基金会 | 葡糖胺和葡糖胺/抗炎互联体前药、组合物和方法 |
| US8034796B2 (en) * | 2004-04-07 | 2011-10-11 | The University Of Georgia Research Foundation, Inc. | Glucosamine and glucosamine/anti-inflammatory mutual prodrugs, compositions, and methods |
| RU2260432C1 (ru) * | 2004-10-12 | 2005-09-20 | Открытое Акционерное Общество "Нижегородский Химико-Фармацевтический Завод" (Оао "Нижфарм") | Средство для лечения болезней суставов |
| US7335384B2 (en) | 2006-03-17 | 2008-02-26 | 4K Nutripharma International | Nutrient compositions for the treatment and prevention of inflammation and disorders associated therewith |
| ES2658964T3 (es) | 2007-08-03 | 2018-03-13 | Nucitec S.A. De C.V. | Composiciones y métodos para el tratamiento y la prevención de la osteoartritis |
| US20110014308A1 (en) * | 2007-12-12 | 2011-01-20 | Daniel Raederstorff | Novel compositions and use thereof for the treatment, co-treatment or prevention of inflammatory disorders. |
| EP2581090A1 (en) * | 2008-05-13 | 2013-04-17 | Apharm S.r.l. | Glycosaminoglycan oral use and compositions |
| FR2969618B1 (fr) * | 2010-12-28 | 2014-05-16 | Pf Medicament | Procede de preparation de chondroitine sulfate de sodium |
| JP6096550B2 (ja) * | 2012-04-25 | 2017-03-15 | ロート製薬株式会社 | 内服組成物 |
| ES2468665B1 (es) * | 2012-12-14 | 2015-06-11 | Farmalider, S.A. | Composición farmacéutica de sulfato de condroitina y celecoxib |
| WO2015057520A1 (en) * | 2013-10-16 | 2015-04-23 | Novozymes A/S | Processes of producing fermentation products |
| US10076537B2 (en) | 2014-05-02 | 2018-09-18 | Arthrodynamic Holdings, Llc | Glycosaminoglycan composition and method of use for kidney stone removal |
| CN104644665A (zh) * | 2014-06-26 | 2015-05-27 | 黄心诚 | 治疗关节炎的药物 |
| JP6315741B2 (ja) * | 2015-08-18 | 2018-04-25 | 合同会社Ｐｈａｒｍａ Ｓｅｅｄｓ Ｃｒｅａｔｅ | ＮＳＡＩＤｓまたはヘパリン類含有口腔用組成物 |
| CN112870154B (zh) * | 2021-02-03 | 2022-10-18 | 四川农业大学 | 兽用复方塞来昔布纳米脂质体凝胶及其制备方法 |
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| US4590067A (en) * | 1984-10-18 | 1986-05-20 | Peritain, Ltd. | Treatment for periodontal disease |
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-
2002
- 2002-08-09 US US10/215,539 patent/US20030114416A1/en not_active Abandoned
- 2002-08-13 WO PCT/US2002/025673 patent/WO2003015799A1/en not_active Application Discontinuation
- 2002-08-13 BR BR0211977-3A patent/BR0211977A/pt not_active IP Right Cessation
- 2002-08-13 KR KR10-2004-7002126A patent/KR20040047790A/ko not_active Application Discontinuation
- 2002-08-13 MX MXPA04001397A patent/MXPA04001397A/es unknown
- 2002-08-13 CA CA002457452A patent/CA2457452A1/en not_active Abandoned
- 2002-08-13 PL PL02368971A patent/PL368971A1/xx not_active Application Discontinuation
- 2002-08-13 CN CNA028201213A patent/CN1575182A/zh active Pending
- 2002-08-13 AU AU2002336344A patent/AU2002336344A2/en not_active Abandoned
- 2002-08-13 EP EP02773188A patent/EP1416941A1/en not_active Withdrawn
- 2002-08-13 JP JP2003520758A patent/JP2005501850A/ja not_active Withdrawn
- 2002-08-13 IL IL16008702A patent/IL160087A0/xx unknown
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