OA12613A - Skin-permeable composition comprising a selective cyclooxygenase-2 inhibitor a monohydric alcohol. - Google Patents
Skin-permeable composition comprising a selective cyclooxygenase-2 inhibitor a monohydric alcohol. Download PDFInfo
- Publication number
- OA12613A OA12613A OA1200300310A OA1200300310A OA12613A OA 12613 A OA12613 A OA 12613A OA 1200300310 A OA1200300310 A OA 1200300310A OA 1200300310 A OA1200300310 A OA 1200300310A OA 12613 A OA12613 A OA 12613A
- Authority
- OA
- OAPI
- Prior art keywords
- composition
- skin
- perméation
- group
- acid
- Prior art date
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- 239000000203 mixture Substances 0.000 title claims abstract description 285
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 title claims abstract description 39
- 229940093444 Cyclooxygenase 2 inhibitor Drugs 0.000 title description 2
- 239000003255 cyclooxygenase 2 inhibitor Substances 0.000 title description 2
- 239000003814 drug Substances 0.000 claims abstract description 141
- 229940079593 drug Drugs 0.000 claims abstract description 89
- 230000002401 inhibitory effect Effects 0.000 claims abstract description 54
- 229940124597 therapeutic agent Drugs 0.000 claims abstract description 52
- 239000000651 prodrug Substances 0.000 claims abstract description 43
- 229940002612 prodrug Drugs 0.000 claims abstract description 43
- 208000002193 Pain Diseases 0.000 claims abstract description 37
- 230000036407 pain Effects 0.000 claims abstract description 36
- 206010061218 Inflammation Diseases 0.000 claims abstract description 32
- 230000004054 inflammatory process Effects 0.000 claims abstract description 32
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 23
- 208000035475 disorder Diseases 0.000 claims abstract description 17
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 15
- 230000001404 mediated effect Effects 0.000 claims abstract description 10
- 239000003937 drug carrier Substances 0.000 claims abstract description 6
- 102100038280 Prostaglandin G/H synthase 2 Human genes 0.000 claims description 76
- 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 71
- 229960000590 celecoxib Drugs 0.000 claims description 68
- 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 description 56
- 229960002004 valdecoxib Drugs 0.000 claims description 56
- -1 teipenoids Chemical class 0.000 claims description 50
- 229960004662 parecoxib Drugs 0.000 claims description 45
- 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 description 45
- MGSRCZKZVOBKFT-UHFFFAOYSA-N thymol Chemical compound CC(C)C1=CC=C(C)C=C1O MGSRCZKZVOBKFT-UHFFFAOYSA-N 0.000 claims description 44
- 150000001875 compounds Chemical class 0.000 claims description 42
- 239000000499 gel Substances 0.000 claims description 41
- 239000003623 enhancer Substances 0.000 claims description 33
- 125000000217 alkyl group Chemical group 0.000 claims description 27
- 229910052739 hydrogen Inorganic materials 0.000 claims description 24
- 239000001257 hydrogen Substances 0.000 claims description 24
- ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 claims description 22
- 239000005844 Thymol Substances 0.000 claims description 22
- 229940055577 oleyl alcohol Drugs 0.000 claims description 22
- XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 claims description 22
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 claims description 22
- 229960000790 thymol Drugs 0.000 claims description 22
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 21
- 239000002904 solvent Substances 0.000 claims description 21
- ARIWANIATODDMH-UHFFFAOYSA-N rac-1-monolauroylglycerol Chemical compound CCCCCCCCCCCC(=O)OCC(O)CO ARIWANIATODDMH-UHFFFAOYSA-N 0.000 claims description 18
- 150000002191 fatty alcohols Chemical class 0.000 claims description 17
- OSWPMRLSEDHDFF-UHFFFAOYSA-N methyl salicylate Chemical compound COC(=O)C1=CC=CC=C1O OSWPMRLSEDHDFF-UHFFFAOYSA-N 0.000 claims description 17
- 150000003839 salts Chemical class 0.000 claims description 17
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 16
- 230000000475 sunscreen effect Effects 0.000 claims description 16
- 239000000516 sunscreening agent Substances 0.000 claims description 16
- 150000003505 terpenes Chemical class 0.000 claims description 16
- NOOLISFMXDJSKH-UTLUCORTSA-N (+)-Neomenthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@@H]1O NOOLISFMXDJSKH-UTLUCORTSA-N 0.000 claims description 13
- NOOLISFMXDJSKH-UHFFFAOYSA-N DL-menthol Natural products CC(C)C1CCC(C)CC1O NOOLISFMXDJSKH-UHFFFAOYSA-N 0.000 claims description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 12
- 125000003545 alkoxy group Chemical group 0.000 claims description 12
- 125000005907 alkyl ester group Chemical group 0.000 claims description 12
- 239000006071 cream Substances 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 11
- 239000003795 chemical substances by application Substances 0.000 claims description 11
- 239000002674 ointment Substances 0.000 claims description 11
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 claims description 11
- 229960004889 salicylic acid Drugs 0.000 claims description 11
- BAVONGHXFVOKBV-UHFFFAOYSA-N Carveol Chemical compound CC(=C)C1CC=C(C)C(O)C1 BAVONGHXFVOKBV-UHFFFAOYSA-N 0.000 claims description 10
- GLZPCOQZEFWAFX-UHFFFAOYSA-N Geraniol Chemical compound CC(C)=CCCC(C)=CCO GLZPCOQZEFWAFX-UHFFFAOYSA-N 0.000 claims description 10
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 claims description 10
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 10
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 10
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 claims description 10
- ULDHMXUKGWMISQ-UHFFFAOYSA-N carvone Chemical compound CC(=C)C1CC=C(C)C(=O)C1 ULDHMXUKGWMISQ-UHFFFAOYSA-N 0.000 claims description 10
- AZOCECCLWFDTAP-UHFFFAOYSA-N dihydrocarvone Chemical compound CC1CCC(C(C)=C)CC1=O AZOCECCLWFDTAP-UHFFFAOYSA-N 0.000 claims description 10
- ZYTMANIQRDEHIO-KXUCPTDWSA-N isopulegol Chemical compound C[C@@H]1CC[C@@H](C(C)=C)[C@H](O)C1 ZYTMANIQRDEHIO-KXUCPTDWSA-N 0.000 claims description 10
- CDOSHBSSFJOMGT-UHFFFAOYSA-N linalool Chemical compound CC(C)=CCCC(C)(O)C=C CDOSHBSSFJOMGT-UHFFFAOYSA-N 0.000 claims description 10
- 230000001225 therapeutic effect Effects 0.000 claims description 10
- 230000002500 effect on skin Effects 0.000 claims description 9
- 229940068939 glyceryl monolaurate Drugs 0.000 claims description 9
- 229910052736 halogen Inorganic materials 0.000 claims description 9
- 150000002367 halogens Chemical class 0.000 claims description 9
- 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 description 9
- 229960000371 rofecoxib Drugs 0.000 claims description 9
- 235000007586 terpenes Nutrition 0.000 claims description 9
- OQQOAWVKVDAJOI-UHFFFAOYSA-N (2-dodecanoyloxy-3-hydroxypropyl) dodecanoate Chemical compound CCCCCCCCCCCC(=O)OCC(CO)OC(=O)CCCCCCCCCCC OQQOAWVKVDAJOI-UHFFFAOYSA-N 0.000 claims description 8
- ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 claims description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 8
- KRCZYMFUWVJCLI-UHFFFAOYSA-N Dihydrocarveol Chemical compound CC1CCC(C(C)=C)CC1O KRCZYMFUWVJCLI-UHFFFAOYSA-N 0.000 claims description 8
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 8
- 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 description 8
- 229960004945 etoricoxib Drugs 0.000 claims description 8
- 239000000194 fatty acid Substances 0.000 claims description 8
- 229930195729 fatty acid Natural products 0.000 claims description 8
- 229940074049 glyceryl dilaurate Drugs 0.000 claims description 8
- 229940041616 menthol Drugs 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 229960001047 methyl salicylate Drugs 0.000 claims description 8
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 8
- 239000006072 paste Substances 0.000 claims description 8
- 239000002552 dosage form Substances 0.000 claims description 7
- 125000005843 halogen group Chemical group 0.000 claims description 7
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 claims description 7
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 claims description 6
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 claims description 6
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 claims description 6
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 claims description 6
- WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 claims description 6
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 claims description 6
- 229930016911 cinnamic acid Natural products 0.000 claims description 6
- 235000013985 cinnamic acid Nutrition 0.000 claims description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims description 6
- 229960001760 dimethyl sulfoxide Drugs 0.000 claims description 6
- QQQMUBLXDAFBRH-UHFFFAOYSA-N dodecyl 2-hydroxypropanoate Chemical compound CCCCCCCCCCCCOC(=O)C(C)O QQQMUBLXDAFBRH-UHFFFAOYSA-N 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 claims description 6
- 239000006210 lotion Substances 0.000 claims description 6
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 238000007920 subcutaneous administration Methods 0.000 claims description 6
- BORJONZPSTVSFP-UHFFFAOYSA-N tetradecyl 2-hydroxypropanoate Chemical compound CCCCCCCCCCCCCCOC(=O)C(C)O BORJONZPSTVSFP-UHFFFAOYSA-N 0.000 claims description 6
- 239000002562 thickening agent Substances 0.000 claims description 6
- NFLGAXVYCFJBMK-RKDXNWHRSA-N (+)-isomenthone Natural products CC(C)[C@H]1CC[C@@H](C)CC1=O NFLGAXVYCFJBMK-RKDXNWHRSA-N 0.000 claims description 5
- BAVONGHXFVOKBV-ZJUUUORDSA-N (-)-trans-carveol Natural products CC(=C)[C@@H]1CC=C(C)[C@@H](O)C1 BAVONGHXFVOKBV-ZJUUUORDSA-N 0.000 claims description 5
- 239000001871 (1R,2R,5S)-5-methyl-2-prop-1-en-2-ylcyclohexan-1-ol Substances 0.000 claims description 5
- DRAWQKGUORNASA-UHFFFAOYSA-N (2-hydroxy-3-octadec-9-enoyloxypropyl) octadec-9-enoate Chemical compound CCCCCCCCC=CCCCCCCCC(=O)OCC(O)COC(=O)CCCCCCCC=CCCCCCCCC DRAWQKGUORNASA-UHFFFAOYSA-N 0.000 claims description 5
- YFUSUXATWLGGNN-UHFFFAOYSA-N (2-hydroxyacetyl) dodecanoate Chemical compound CCCCCCCCCCCC(=O)OC(=O)CO YFUSUXATWLGGNN-UHFFFAOYSA-N 0.000 claims description 5
- AFGZBIIMQZGNNM-UHFFFAOYSA-N (2-hydroxyacetyl) hexanoate Chemical compound CCCCCC(=O)OC(=O)CO AFGZBIIMQZGNNM-UHFFFAOYSA-N 0.000 claims description 5
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical class OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 claims description 5
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- DSSYKIVIOFKYAU-XCBNKYQSSA-N (R)-camphor Chemical compound C1C[C@@]2(C)C(=O)C[C@@H]1C2(C)C DSSYKIVIOFKYAU-XCBNKYQSSA-N 0.000 claims description 5
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- WEEGYLXZBRQIMU-UHFFFAOYSA-N 1,8-cineole Natural products C1CC2CCC1(C)OC2(C)C WEEGYLXZBRQIMU-UHFFFAOYSA-N 0.000 claims description 5
- NZJXADCEESMBPW-UHFFFAOYSA-N 1-methylsulfinyldecane Chemical compound CCCCCCCCCCS(C)=O NZJXADCEESMBPW-UHFFFAOYSA-N 0.000 claims description 5
- 239000000263 2,3-dihydroxypropyl (Z)-octadec-9-enoate Substances 0.000 claims description 5
- VSXIZXFGQGKZQG-UHFFFAOYSA-N 2-cyano-3,3-diphenylprop-2-enoic acid Chemical compound C=1C=CC=CC=1C(=C(C#N)C(=O)O)C1=CC=CC=C1 VSXIZXFGQGKZQG-UHFFFAOYSA-N 0.000 claims description 5
- RZRNAYUHWVFMIP-GDCKJWNLSA-N 3-oleoyl-sn-glycerol Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@H](O)CO RZRNAYUHWVFMIP-GDCKJWNLSA-N 0.000 claims description 5
- YDIYEOMDOWUDTJ-UHFFFAOYSA-N 4-(dimethylamino)benzoic acid Chemical compound CN(C)C1=CC=C(C(O)=O)C=C1 YDIYEOMDOWUDTJ-UHFFFAOYSA-N 0.000 claims description 5
- HIQIXEFWDLTDED-UHFFFAOYSA-N 4-hydroxy-1-piperidin-4-ylpyrrolidin-2-one Chemical compound O=C1CC(O)CN1C1CCNCC1 HIQIXEFWDLTDED-UHFFFAOYSA-N 0.000 claims description 5
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 5
- JGVWYJDASSSGEK-UHFFFAOYSA-N 5-methyl-2-propan-2-ylidenecyclohexan-1-ol Chemical compound CC1CCC(=C(C)C)C(O)C1 JGVWYJDASSSGEK-UHFFFAOYSA-N 0.000 claims description 5
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 5
- 239000005973 Carvone Substances 0.000 claims description 5
- 241000723346 Cinnamomum camphora Species 0.000 claims description 5
- WEEGYLXZBRQIMU-WAAGHKOSSA-N Eucalyptol Chemical compound C1C[C@H]2CC[C@]1(C)OC2(C)C WEEGYLXZBRQIMU-WAAGHKOSSA-N 0.000 claims description 5
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- RECUKUPTGUEGMW-UHFFFAOYSA-N carvacrol Chemical compound CC(C)C1=CC=C(C)C(O)=C1 RECUKUPTGUEGMW-UHFFFAOYSA-N 0.000 claims description 5
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- WPGPCDVQHXOMQP-UHFFFAOYSA-N carvotanacetone Natural products CC(C)C1CC=C(C)C(=O)C1 WPGPCDVQHXOMQP-UHFFFAOYSA-N 0.000 claims description 5
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- 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
- 125000006165 cyclic alkyl group Chemical group 0.000 claims description 5
- 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 description 5
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- RZRNAYUHWVFMIP-UHFFFAOYSA-N monoelaidin Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC(O)CO RZRNAYUHWVFMIP-UHFFFAOYSA-N 0.000 claims description 5
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
- 230000003381 solubilizing effect Effects 0.000 claims description 5
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 claims description 5
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- HNYLJFVPFNLDRL-UHFFFAOYSA-N (2-hydroxyacetyl) 16-methylheptadecanoate Chemical compound CC(C)CCCCCCCCCCCCCCC(=O)OC(=O)CO HNYLJFVPFNLDRL-UHFFFAOYSA-N 0.000 claims description 4
- WUOACPNHFRMFPN-SECBINFHSA-N (S)-(-)-alpha-terpineol Chemical compound CC1=CC[C@@H](C(C)(C)O)CC1 WUOACPNHFRMFPN-SECBINFHSA-N 0.000 claims description 4
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- 125000004043 oxo group Chemical group O=* 0.000 claims description 4
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims description 4
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Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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US29483801P | 2001-05-31 | 2001-05-31 | |
US35075601P | 2001-11-13 | 2001-11-13 |
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OA12613A true OA12613A (en) | 2006-06-09 |
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OA1200300310A OA12613A (en) | 2001-05-31 | 2002-05-30 | Skin-permeable composition comprising a selective cyclooxygenase-2 inhibitor a monohydric alcohol. |
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US (1) | US20030161867A1 (is) |
EP (1) | EP1404345A2 (is) |
JP (1) | JP2004532871A (is) |
KR (1) | KR20040033286A (is) |
CN (1) | CN1547474A (is) |
AP (1) | AP2003002922A0 (is) |
BR (1) | BR0210104A (is) |
CA (1) | CA2448627A1 (is) |
CO (1) | CO5640125A2 (is) |
CR (1) | CR7173A (is) |
CZ (1) | CZ20033241A3 (is) |
EA (1) | EA200301200A1 (is) |
EC (1) | ECSP034869A (is) |
HU (1) | HUP0600294A2 (is) |
IL (1) | IL159100A0 (is) |
IS (1) | IS7055A (is) |
MA (1) | MA27030A1 (is) |
MX (1) | MXPA03010991A (is) |
NO (1) | NO20035325D0 (is) |
OA (1) | OA12613A (is) |
PL (1) | PL367337A1 (is) |
SK (1) | SK14762003A3 (is) |
TN (1) | TNSN03127A1 (is) |
WO (1) | WO2002096435A2 (is) |
ZA (1) | ZA200309298B (is) |
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JP4283507B2 (ja) * | 2002-08-02 | 2009-06-24 | 久光製薬株式会社 | 経皮投与用貼付剤 |
US20040127531A1 (en) * | 2002-11-21 | 2004-07-01 | Lu Guang Wei | Adhesive coated sheet for dermal delivery of a selective cyclooxygenase-2 inhibitor |
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2002
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- 2002-05-30 CN CNA028149467A patent/CN1547474A/zh active Pending
- 2002-05-30 EA EA200301200A patent/EA200301200A1/ru unknown
- 2002-05-30 CA CA002448627A patent/CA2448627A1/en not_active Abandoned
- 2002-05-30 OA OA1200300310A patent/OA12613A/en unknown
- 2002-05-30 AP APAP/P/2003/002922A patent/AP2003002922A0/en unknown
- 2002-05-30 US US10/158,342 patent/US20030161867A1/en not_active Abandoned
- 2002-05-30 IL IL15910002A patent/IL159100A0/xx unknown
- 2002-05-30 WO PCT/US2002/017067 patent/WO2002096435A2/en not_active Application Discontinuation
- 2002-05-30 SK SK1476-2003A patent/SK14762003A3/sk unknown
- 2002-05-30 MX MXPA03010991A patent/MXPA03010991A/es unknown
- 2002-05-30 CZ CZ20033241A patent/CZ20033241A3/cs unknown
- 2002-05-30 HU HU0600294A patent/HUP0600294A2/hu unknown
- 2002-05-30 JP JP2002592944A patent/JP2004532871A/ja not_active Withdrawn
- 2002-05-30 EP EP02774123A patent/EP1404345A2/en not_active Withdrawn
- 2002-05-30 BR BR0210104-1A patent/BR0210104A/pt not_active IP Right Cessation
- 2002-05-30 TN TNPCT/US2002/017067A patent/TNSN03127A1/fr unknown
- 2002-05-30 KR KR10-2003-7015581A patent/KR20040033286A/ko not_active Application Discontinuation
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- 2003-11-28 ZA ZA200309298A patent/ZA200309298B/xx unknown
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- 2003-11-28 CR CR7173A patent/CR7173A/es not_active Application Discontinuation
- 2003-11-28 MA MA27417A patent/MA27030A1/fr unknown
- 2003-11-28 EC EC2003004869A patent/ECSP034869A/es unknown
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CR7173A (es) | 2004-04-22 |
HUP0600294A2 (en) | 2007-02-28 |
MA27030A1 (fr) | 2004-12-20 |
MXPA03010991A (es) | 2004-02-27 |
EA200301200A1 (ru) | 2004-06-24 |
SK14762003A3 (sk) | 2004-08-03 |
CN1547474A (zh) | 2004-11-17 |
AP2003002922A0 (en) | 2003-12-31 |
CO5640125A2 (es) | 2006-05-31 |
EP1404345A2 (en) | 2004-04-07 |
ZA200309298B (en) | 2004-05-12 |
NO20035325D0 (no) | 2003-11-28 |
TNSN03127A1 (fr) | 2005-12-23 |
CZ20033241A3 (cs) | 2004-08-18 |
JP2004532871A (ja) | 2004-10-28 |
ECSP034869A (es) | 2004-07-23 |
WO2002096435A3 (en) | 2003-05-01 |
PL367337A1 (en) | 2005-02-21 |
US20030161867A1 (en) | 2003-08-28 |
IS7055A (is) | 2003-11-27 |
BR0210104A (pt) | 2004-06-08 |
WO2002096435A2 (en) | 2002-12-05 |
CA2448627A1 (en) | 2002-12-05 |
IL159100A0 (en) | 2004-05-12 |
KR20040033286A (ko) | 2004-04-21 |
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