JP2005522472A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2005522472A5 JP2005522472A5 JP2003581790A JP2003581790A JP2005522472A5 JP 2005522472 A5 JP2005522472 A5 JP 2005522472A5 JP 2003581790 A JP2003581790 A JP 2003581790A JP 2003581790 A JP2003581790 A JP 2003581790A JP 2005522472 A5 JP2005522472 A5 JP 2005522472A5
- Authority
- JP
- Japan
- Prior art keywords
- formula
- acid
- residue
- alkyl
- methyl
- 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.)
- Pending
Links
- 150000001875 compounds Chemical class 0.000 claims 29
- 229910052739 hydrogen Inorganic materials 0.000 claims 20
- 125000000217 alkyl group Chemical group 0.000 claims 16
- -1 sulfretin (EV) Chemical compound 0.000 claims 15
- 229910052799 carbon Inorganic materials 0.000 claims 9
- 239000008194 pharmaceutical composition Substances 0.000 claims 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 8
- 239000002243 precursor Substances 0.000 claims 7
- 229920006395 saturated elastomer Polymers 0.000 claims 7
- 239000002253 acid Substances 0.000 claims 6
- 229910052736 halogen Inorganic materials 0.000 claims 6
- 150000002367 halogens Chemical class 0.000 claims 6
- 150000002148 esters Chemical class 0.000 claims 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 5
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 claims 4
- 229910052801 chlorine Inorganic materials 0.000 claims 4
- 239000000460 chlorine Substances 0.000 claims 4
- XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 claims 4
- 235000018417 cysteine Nutrition 0.000 claims 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims 4
- 229940079593 drug Drugs 0.000 claims 4
- 239000003814 drug Substances 0.000 claims 4
- 239000001257 hydrogen Substances 0.000 claims 4
- 125000003545 alkoxy group Chemical group 0.000 claims 3
- 229910052794 bromium Inorganic materials 0.000 claims 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims 3
- RWSXRVCMGQZWBV-WDSKDSINSA-N glutathione Chemical compound OC(=O)[C@@H](N)CCC(=O)N[C@@H](CS)C(=O)NCC(O)=O RWSXRVCMGQZWBV-WDSKDSINSA-N 0.000 claims 3
- 125000005842 heteroatom Chemical group 0.000 claims 3
- 125000000623 heterocyclic group Chemical group 0.000 claims 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 3
- 229910052757 nitrogen Inorganic materials 0.000 claims 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 3
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical group OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 claims 3
- 229910052717 sulfur Inorganic materials 0.000 claims 3
- WXTMDXOMEHJXQO-UHFFFAOYSA-N 2,5-dihydroxybenzoic acid Chemical compound OC(=O)C1=CC(O)=CC=C1O WXTMDXOMEHJXQO-UHFFFAOYSA-N 0.000 claims 2
- LAQYHRQFABOIFD-UHFFFAOYSA-N 2-methoxyhydroquinone Chemical compound COC1=CC(O)=CC=C1O LAQYHRQFABOIFD-UHFFFAOYSA-N 0.000 claims 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 2
- DZAUWHJDUNRCTF-UHFFFAOYSA-N 3-(3,4-dihydroxyphenyl)propanoic acid Chemical compound OC(=O)CCC1=CC=C(O)C(O)=C1 DZAUWHJDUNRCTF-UHFFFAOYSA-N 0.000 claims 2
- NGSWKAQJJWESNS-UHFFFAOYSA-N 4-coumaric acid Chemical compound OC(=O)C=CC1=CC=C(O)C=C1 NGSWKAQJJWESNS-UHFFFAOYSA-N 0.000 claims 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 2
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 claims 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 claims 2
- DJEIHHYCDCTAAH-UHFFFAOYSA-N Mofezolac (TN) Chemical group C1=CC(OC)=CC=C1C1=NOC(CC(O)=O)=C1C1=CC=C(OC)C=C1 DJEIHHYCDCTAAH-UHFFFAOYSA-N 0.000 claims 2
- ZTHYODDOHIVTJV-UHFFFAOYSA-N Propyl gallate Chemical compound CCCOC(=O)C1=CC(O)=C(O)C(O)=C1 ZTHYODDOHIVTJV-UHFFFAOYSA-N 0.000 claims 2
- REFJWTPEDVJJIY-UHFFFAOYSA-N Quercetin Chemical compound C=1C(O)=CC(O)=C(C(C=2O)=O)C=1OC=2C1=CC=C(O)C(O)=C1 REFJWTPEDVJJIY-UHFFFAOYSA-N 0.000 claims 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 2
- OFCNXPDARWKPPY-UHFFFAOYSA-N allopurinol Chemical compound OC1=NC=NC2=C1C=NN2 OFCNXPDARWKPPY-UHFFFAOYSA-N 0.000 claims 2
- 150000001408 amides Chemical class 0.000 claims 2
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims 2
- 230000003110 anti-inflammatory effect Effects 0.000 claims 2
- 206010003246 arthritis Diseases 0.000 claims 2
- 125000004429 atom Chemical group 0.000 claims 2
- GGNQRNBDZQJCCN-UHFFFAOYSA-N benzene-1,2,4-triol Chemical compound OC1=CC=C(O)C(O)=C1 GGNQRNBDZQJCCN-UHFFFAOYSA-N 0.000 claims 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 2
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims 2
- 235000010290 biphenyl Nutrition 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- DKYWVDODHFEZIM-NSHDSACASA-N dexketoprofen Chemical compound OC(=O)[C@@H](C)C1=CC=CC(C(=O)C=2C=CC=CC=2)=C1 DKYWVDODHFEZIM-NSHDSACASA-N 0.000 claims 2
- DCOPUUMXTXDBNB-UHFFFAOYSA-N diclofenac Chemical compound OC(=O)CC1=CC=CC=C1NC1=C(Cl)C=CC=C1Cl DCOPUUMXTXDBNB-UHFFFAOYSA-N 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 229910052731 fluorine Inorganic materials 0.000 claims 2
- 125000000524 functional group Chemical group 0.000 claims 2
- LNTHITQWFMADLM-UHFFFAOYSA-N gallic acid Chemical compound OC(=O)C1=CC(O)=C(O)C(O)=C1 LNTHITQWFMADLM-UHFFFAOYSA-N 0.000 claims 2
- QBKSWRVVCFFDOT-UHFFFAOYSA-N gossypol Chemical compound CC(C)C1=C(O)C(O)=C(C=O)C2=C(O)C(C=3C(O)=C4C(C=O)=C(O)C(O)=C(C4=CC=3C)C(C)C)=C(C)C=C21 QBKSWRVVCFFDOT-UHFFFAOYSA-N 0.000 claims 2
- IYRMWMYZSQPJKC-UHFFFAOYSA-N kaempferol Chemical compound C1=CC(O)=CC=C1C1=C(O)C(=O)C2=C(O)C=C(O)C=C2O1 IYRMWMYZSQPJKC-UHFFFAOYSA-N 0.000 claims 2
- MWDZOUNAPSSOEL-UHFFFAOYSA-N kaempferol Natural products OC1=C(C(=O)c2cc(O)cc(O)c2O1)c3ccc(O)cc3 MWDZOUNAPSSOEL-UHFFFAOYSA-N 0.000 claims 2
- 125000005647 linker group Chemical group 0.000 claims 2
- HCZKYJDFEPMADG-TXEJJXNPSA-N masoprocol Chemical compound C([C@H](C)[C@H](C)CC=1C=C(O)C(O)=CC=1)C1=CC=C(O)C(O)=C1 HCZKYJDFEPMADG-TXEJJXNPSA-N 0.000 claims 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 2
- 125000003884 phenylalkyl group Chemical group 0.000 claims 2
- 230000003637 steroidlike Effects 0.000 claims 2
- 125000000547 substituted alkyl group Chemical group 0.000 claims 2
- 150000005846 sugar alcohols Polymers 0.000 claims 2
- MLKXDPUZXIRXEP-MFOYZWKCSA-N sulindac Chemical group CC1=C(CC(O)=O)C2=CC(F)=CC=C2\C1=C/C1=CC=C(S(C)=O)C=C1 MLKXDPUZXIRXEP-MFOYZWKCSA-N 0.000 claims 2
- 150000007970 thio esters Chemical class 0.000 claims 2
- QAIPRVGONGVQAS-DUXPYHPUSA-N trans-caffeic acid Chemical compound OC(=O)\C=C\C1=CC=C(O)C(O)=C1 QAIPRVGONGVQAS-DUXPYHPUSA-N 0.000 claims 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
- WKOLLVMJNQIZCI-UHFFFAOYSA-N vanillic acid Chemical compound COC1=CC(C(O)=O)=CC=C1O WKOLLVMJNQIZCI-UHFFFAOYSA-N 0.000 claims 2
- PFTAWBLQPZVEMU-DZGCQCFKSA-N (+)-catechin Chemical compound C1([C@H]2OC3=CC(O)=CC(O)=C3C[C@@H]2O)=CC=C(O)C(O)=C1 PFTAWBLQPZVEMU-DZGCQCFKSA-N 0.000 claims 1
- RJMIEHBSYVWVIN-LLVKDONJSA-N (2r)-2-[4-(3-oxo-1h-isoindol-2-yl)phenyl]propanoic acid Chemical compound C1=CC([C@H](C(O)=O)C)=CC=C1N1C(=O)C2=CC=CC=C2C1 RJMIEHBSYVWVIN-LLVKDONJSA-N 0.000 claims 1
- FDKWRPBBCBCIGA-REOHCLBHSA-N (2r)-2-azaniumyl-3-$l^{1}-selanylpropanoate Chemical compound [Se]C[C@H](N)C(O)=O FDKWRPBBCBCIGA-REOHCLBHSA-N 0.000 claims 1
- RDJGLLICXDHJDY-NSHDSACASA-N (2s)-2-(3-phenoxyphenyl)propanoic acid Chemical group OC(=O)[C@@H](C)C1=CC=CC(OC=2C=CC=CC=2)=C1 RDJGLLICXDHJDY-NSHDSACASA-N 0.000 claims 1
- MDKGKXOCJGEUJW-VIFPVBQESA-N (2s)-2-[4-(thiophene-2-carbonyl)phenyl]propanoic acid Chemical group C1=CC([C@@H](C(O)=O)C)=CC=C1C(=O)C1=CC=CS1 MDKGKXOCJGEUJW-VIFPVBQESA-N 0.000 claims 1
- LJRDOKAZOAKLDU-UDXJMMFXSA-N (2s,3s,4r,5r,6r)-5-amino-2-(aminomethyl)-6-[(2r,3s,4r,5s)-5-[(1r,2r,3s,5r,6s)-3,5-diamino-2-[(2s,3r,4r,5s,6r)-3-amino-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-6-hydroxycyclohexyl]oxy-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl]oxyoxane-3,4-diol;sulfuric ac Chemical compound OS(O)(=O)=O.N[C@@H]1[C@@H](O)[C@H](O)[C@H](CN)O[C@@H]1O[C@H]1[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](N)C[C@@H](N)[C@@H]2O)O[C@@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)N)O[C@@H]1CO LJRDOKAZOAKLDU-UDXJMMFXSA-N 0.000 claims 1
- XTMOQAKCOFLCRZ-UHFFFAOYSA-N (4-acetamidophenyl) 4-nitrooxybutanoate Chemical compound CC(=O)NC1=CC=C(OC(=O)CCCO[N+]([O-])=O)C=C1 XTMOQAKCOFLCRZ-UHFFFAOYSA-N 0.000 claims 1
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims 1
- ACEAELOMUCBPJP-UHFFFAOYSA-N (E)-3,4,5-trihydroxycinnamic acid Natural products OC(=O)C=CC1=CC(O)=C(O)C(O)=C1 ACEAELOMUCBPJP-UHFFFAOYSA-N 0.000 claims 1
- KSEBMYQBYZTDHS-HWKANZROSA-M (E)-Ferulic acid Natural products COC1=CC(\C=C\C([O-])=O)=CC=C1O KSEBMYQBYZTDHS-HWKANZROSA-M 0.000 claims 1
- BZCOSCNPHJNQBP-UPHRSURJSA-N (z)-2,3-dihydroxybut-2-enedioic acid Chemical compound OC(=O)C(\O)=C(\O)C(O)=O BZCOSCNPHJNQBP-UPHRSURJSA-N 0.000 claims 1
- PMRFBLQVGJNGLU-UHFFFAOYSA-N -form-1-(4-Hydroxyphenyl)ethanol Natural products CC(O)C1=CC=C(O)C=C1 PMRFBLQVGJNGLU-UHFFFAOYSA-N 0.000 claims 1
- YCCILVSKPBXVIP-UHFFFAOYSA-N 2-(4-hydroxyphenyl)ethanol Chemical compound OCCC1=CC=C(O)C=C1 YCCILVSKPBXVIP-UHFFFAOYSA-N 0.000 claims 1
- OKNAWFBIOJJTDV-UHFFFAOYSA-N 2-(oxepin-2-yl)acetic acid Chemical compound OC(=O)CC1=CC=CC=CO1 OKNAWFBIOJJTDV-UHFFFAOYSA-N 0.000 claims 1
- AUZUGWXLBGZUPP-UHFFFAOYSA-N 2-[4-[(2-oxocyclohexylidene)methyl]phenyl]propanoic acid Chemical compound C1=CC(C(C(O)=O)C)=CC=C1C=C1C(=O)CCCC1 AUZUGWXLBGZUPP-UHFFFAOYSA-N 0.000 claims 1
- 125000005273 2-acetoxybenzoic acid group Chemical group 0.000 claims 1
- ONIKNECPXCLUHT-UHFFFAOYSA-N 2-chlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1Cl ONIKNECPXCLUHT-UHFFFAOYSA-N 0.000 claims 1
- ODJQKYXPKWQWNK-UHFFFAOYSA-N 3,3'-Thiobispropanoic acid Chemical compound OC(=O)CCSCCC(O)=O ODJQKYXPKWQWNK-UHFFFAOYSA-N 0.000 claims 1
- NGSWKAQJJWESNS-ZZXKWVIFSA-M 4-Hydroxycinnamate Natural products OC1=CC=C(\C=C\C([O-])=O)C=C1 NGSWKAQJJWESNS-ZZXKWVIFSA-M 0.000 claims 1
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 1
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 claims 1
- DFYRUELUNQRZTB-UHFFFAOYSA-N Acetovanillone Natural products COC1=CC(C(C)=O)=CC=C1O DFYRUELUNQRZTB-UHFFFAOYSA-N 0.000 claims 1
- 108010085443 Anserine Proteins 0.000 claims 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- 108010087806 Carnosine Proteins 0.000 claims 1
- FDKWRPBBCBCIGA-UWTATZPHSA-N D-Selenocysteine Natural products [Se]C[C@@H](N)C(O)=O FDKWRPBBCBCIGA-UWTATZPHSA-N 0.000 claims 1
- CIWBSHSKHKDKBQ-DUZGATOHSA-N D-isoascorbic acid Chemical compound OC[C@@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-DUZGATOHSA-N 0.000 claims 1
- UBSCDKPKWHYZNX-UHFFFAOYSA-N Demethoxycapillarisin Natural products C1=CC(O)=CC=C1OC1=CC(=O)C2=C(O)C=C(O)C=C2O1 UBSCDKPKWHYZNX-UHFFFAOYSA-N 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
- 108010024636 Glutathione Proteins 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- HEFNNWSXXWATRW-UHFFFAOYSA-N Ibuprofen Chemical group CC(C)CC1=CC=C(C(C)C(O)=O)C=C1 HEFNNWSXXWATRW-UHFFFAOYSA-N 0.000 claims 1
- PWKSKIMOESPYIA-BYPYZUCNSA-N L-N-acetyl-Cysteine Chemical compound CC(=O)N[C@@H](CS)C(O)=O PWKSKIMOESPYIA-BYPYZUCNSA-N 0.000 claims 1
- SLRNWACWRVGMKD-UHFFFAOYSA-N L-anserine Natural products CN1C=NC(CC(NC(=O)CCN)C(O)=O)=C1 SLRNWACWRVGMKD-UHFFFAOYSA-N 0.000 claims 1
- 101710161955 Mannitol-specific phosphotransferase enzyme IIA component Proteins 0.000 claims 1
- ZRVUJXDFFKFLMG-UHFFFAOYSA-N Meloxicam Chemical compound OC=1C2=CC=CC=C2S(=O)(=O)N(C)C=1C(=O)NC1=NC=C(C)S1 ZRVUJXDFFKFLMG-UHFFFAOYSA-N 0.000 claims 1
- MNNBCKASUFBXCO-YFKPBYRVSA-N N-acetyl-D-penicillamine Chemical compound CC(=O)N[C@@H](C(O)=O)C(C)(C)S MNNBCKASUFBXCO-YFKPBYRVSA-N 0.000 claims 1
- CQOVPNPJLQNMDC-UHFFFAOYSA-N N-beta-alanyl-L-histidine Natural products NCCC(=O)NC(C(O)=O)CC1=CN=CN1 CQOVPNPJLQNMDC-UHFFFAOYSA-N 0.000 claims 1
- BLXXJMDCKKHMKV-UHFFFAOYSA-N Nabumetone Chemical group C1=C(CCC(C)=O)C=CC2=CC(OC)=CC=C21 BLXXJMDCKKHMKV-UHFFFAOYSA-N 0.000 claims 1
- 241000210053 Potentilla elegans Species 0.000 claims 1
- TVQZAMVBTVNYLA-UHFFFAOYSA-N Pranoprofen Chemical group C1=CC=C2CC3=CC(C(C(O)=O)C)=CC=C3OC2=N1 TVQZAMVBTVNYLA-UHFFFAOYSA-N 0.000 claims 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims 1
- ZVOLCUVKHLEPEV-UHFFFAOYSA-N Quercetagetin Natural products C1=C(O)C(O)=CC=C1C1=C(O)C(=O)C2=C(O)C(O)=C(O)C=C2O1 ZVOLCUVKHLEPEV-UHFFFAOYSA-N 0.000 claims 1
- HWTZYBCRDDUBJY-UHFFFAOYSA-N Rhynchosin Natural products C1=C(O)C(O)=CC=C1C1=C(O)C(=O)C2=CC(O)=C(O)C=C2O1 HWTZYBCRDDUBJY-UHFFFAOYSA-N 0.000 claims 1
- RJFAYQIBOAGBLC-BYPYZUCNSA-N Selenium-L-methionine Chemical compound C[Se]CC[C@H](N)C(O)=O RJFAYQIBOAGBLC-BYPYZUCNSA-N 0.000 claims 1
- RJFAYQIBOAGBLC-UHFFFAOYSA-N Selenomethionine Natural products C[Se]CCC(N)C(O)=O RJFAYQIBOAGBLC-UHFFFAOYSA-N 0.000 claims 1
- 229930006000 Sucrose Natural products 0.000 claims 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 claims 1
- QHOPXUFELLHKAS-UHFFFAOYSA-N Thespesin Natural products CC(C)c1c(O)c(O)c2C(O)Oc3c(c(C)cc1c23)-c1c2OC(O)c3c(O)c(O)c(C(C)C)c(cc1C)c23 QHOPXUFELLHKAS-UHFFFAOYSA-N 0.000 claims 1
- MUXFZBHBYYYLTH-UHFFFAOYSA-N Zaltoprofen Chemical group O=C1CC2=CC(C(C(O)=O)C)=CC=C2SC2=CC=CC=C21 MUXFZBHBYYYLTH-UHFFFAOYSA-N 0.000 claims 1
- NZXSNMWOJMIGCF-ZDUSSCGKSA-N [2-methyl-6-(nitrooxymethyl)pyridin-3-yl] (2s)-2-(6-methoxynaphthalen-2-yl)propanoate Chemical compound O=C([C@@H](C)C1=CC2=CC=C(C=C2C=C1)OC)OC1=CC=C(CO[N+]([O-])=O)N=C1C NZXSNMWOJMIGCF-ZDUSSCGKSA-N 0.000 claims 1
- UGXXNPWHJBWMBJ-UHFFFAOYSA-N [2-methyl-6-(nitrooxymethyl)pyridin-3-yl] 2-(3-fluoro-4-phenylphenyl)propanoate Chemical compound C=1C=C(C=2C=CC=CC=2)C(F)=CC=1C(C)C(=O)OC1=CC=C(CO[N+]([O-])=O)N=C1C UGXXNPWHJBWMBJ-UHFFFAOYSA-N 0.000 claims 1
- 229960004308 acetylcysteine Drugs 0.000 claims 1
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims 1
- 125000004849 alkoxymethyl group Chemical group 0.000 claims 1
- 125000003282 alkyl amino group Chemical group 0.000 claims 1
- 125000002947 alkylene group Chemical group 0.000 claims 1
- 229960003459 allopurinol Drugs 0.000 claims 1
- 125000005336 allyloxy group Chemical group 0.000 claims 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims 1
- 125000003277 amino group Chemical group 0.000 claims 1
- LSNWBKACGXCGAJ-UHFFFAOYSA-N ampiroxicam Chemical compound CN1S(=O)(=O)C2=CC=CC=C2C(OC(C)OC(=O)OCC)=C1C(=O)NC1=CC=CC=N1 LSNWBKACGXCGAJ-UHFFFAOYSA-N 0.000 claims 1
- 229950011249 ampiroxicam Drugs 0.000 claims 1
- MYYIAHXIVFADCU-QMMMGPOBSA-N anserine Chemical compound CN1C=NC=C1C[C@H](NC(=O)CC[NH3+])C([O-])=O MYYIAHXIVFADCU-QMMMGPOBSA-N 0.000 claims 1
- 230000001760 anti-analgesic effect Effects 0.000 claims 1
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 235000010323 ascorbic acid Nutrition 0.000 claims 1
- 229960005070 ascorbic acid Drugs 0.000 claims 1
- 239000011668 ascorbic acid Substances 0.000 claims 1
- FKKFMCSXGHRBON-UHFFFAOYSA-N benzo[d][1]benzothiepine Chemical class S1C=CC2=CC=CC=C2C2=CC=CC=C12 FKKFMCSXGHRBON-UHFFFAOYSA-N 0.000 claims 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
- 235000004883 caffeic acid Nutrition 0.000 claims 1
- 229940074360 caffeic acid Drugs 0.000 claims 1
- 125000001589 carboacyl group Chemical group 0.000 claims 1
- CQOVPNPJLQNMDC-ZETCQYMHSA-N carnosine Chemical compound [NH3+]CCC(=O)N[C@H](C([O-])=O)CC1=CNC=N1 CQOVPNPJLQNMDC-ZETCQYMHSA-N 0.000 claims 1
- IVUMCTKHWDRRMH-UHFFFAOYSA-N carprofen Chemical group C1=CC(Cl)=C[C]2C3=CC=C(C(C(O)=O)C)C=C3N=C21 IVUMCTKHWDRRMH-UHFFFAOYSA-N 0.000 claims 1
- ADRVNXBAWSRFAJ-UHFFFAOYSA-N catechin Natural products OC1Cc2cc(O)cc(O)c2OC1c3ccc(O)c(O)c3 ADRVNXBAWSRFAJ-UHFFFAOYSA-N 0.000 claims 1
- 235000005487 catechin Nutrition 0.000 claims 1
- 229950001002 cianidanol Drugs 0.000 claims 1
- QAIPRVGONGVQAS-UHFFFAOYSA-N cis-caffeic acid Natural products OC(=O)C=CC1=CC=C(O)C(O)=C1 QAIPRVGONGVQAS-UHFFFAOYSA-N 0.000 claims 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- 229960001259 diclofenac Drugs 0.000 claims 1
- 235000013681 dietary sucrose Nutrition 0.000 claims 1
- 229960001484 edetic acid Drugs 0.000 claims 1
- 235000010350 erythorbic acid Nutrition 0.000 claims 1
- HCZKYJDFEPMADG-UHFFFAOYSA-N erythro-nordihydroguaiaretic acid Natural products C=1C=C(O)C(O)=CC=1CC(C)C(C)CC1=CC=C(O)C(O)=C1 HCZKYJDFEPMADG-UHFFFAOYSA-N 0.000 claims 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims 1
- XFBVBWWRPKNWHW-UHFFFAOYSA-N etodolac Chemical group C1COC(CC)(CC(O)=O)C2=N[C]3C(CC)=CC=CC3=C21 XFBVBWWRPKNWHW-UHFFFAOYSA-N 0.000 claims 1
- ZPAKPRAICRBAOD-UHFFFAOYSA-N fenbufen Chemical group C1=CC(C(=O)CCC(=O)O)=CC=C1C1=CC=CC=C1 ZPAKPRAICRBAOD-UHFFFAOYSA-N 0.000 claims 1
- 235000001785 ferulic acid Nutrition 0.000 claims 1
- KSEBMYQBYZTDHS-HWKANZROSA-N ferulic acid Chemical compound COC1=CC(\C=C\C(O)=O)=CC=C1O KSEBMYQBYZTDHS-HWKANZROSA-N 0.000 claims 1
- 229940114124 ferulic acid Drugs 0.000 claims 1
- KSEBMYQBYZTDHS-UHFFFAOYSA-N ferulic acid Natural products COC1=CC(C=CC(O)=O)=CC=C1O KSEBMYQBYZTDHS-UHFFFAOYSA-N 0.000 claims 1
- NOOCSNJCXJYGPE-UHFFFAOYSA-N flunixin Chemical compound C1=CC=C(C(F)(F)F)C(C)=C1NC1=NC=CC=C1C(O)=O NOOCSNJCXJYGPE-UHFFFAOYSA-N 0.000 claims 1
- 229960000588 flunixin Drugs 0.000 claims 1
- SYTBZMRGLBWNTM-UHFFFAOYSA-N flurbiprofen Chemical group FC1=CC(C(C(O)=O)C)=CC=C1C1=CC=CC=C1 SYTBZMRGLBWNTM-UHFFFAOYSA-N 0.000 claims 1
- 239000001530 fumaric acid Substances 0.000 claims 1
- 125000002541 furyl group Chemical group 0.000 claims 1
- 229940074391 gallic acid Drugs 0.000 claims 1
- 235000004515 gallic acid Nutrition 0.000 claims 1
- 229960005219 gentisic acid Drugs 0.000 claims 1
- 229960003180 glutathione Drugs 0.000 claims 1
- 229930000755 gossypol Natural products 0.000 claims 1
- 229950005277 gossypol Drugs 0.000 claims 1
- 125000006331 halo benzoyl group Chemical group 0.000 claims 1
- 125000006277 halobenzyl group Chemical group 0.000 claims 1
- 125000001072 heteroaryl group Chemical group 0.000 claims 1
- 125000004464 hydroxyphenyl group Chemical group 0.000 claims 1
- 229960001680 ibuprofen Drugs 0.000 claims 1
- 229960003422 indobufen Drugs 0.000 claims 1
- AYDXAULLCROVIT-UHFFFAOYSA-N indobufen Chemical compound C1=CC(C(C(O)=O)CC)=CC=C1N1C(=O)C2=CC=CC=C2C1 AYDXAULLCROVIT-UHFFFAOYSA-N 0.000 claims 1
- JYGFTBXVXVMTGB-UHFFFAOYSA-N indolin-2-one Chemical compound C1=CC=C2NC(=O)CC2=C1 JYGFTBXVXVMTGB-UHFFFAOYSA-N 0.000 claims 1
- CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical group CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 claims 1
- 229960004187 indoprofen Drugs 0.000 claims 1
- 229940026239 isoascorbic acid Drugs 0.000 claims 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 235000008777 kaempferol Nutrition 0.000 claims 1
- DKYWVDODHFEZIM-UHFFFAOYSA-N ketoprofen Chemical group OC(=O)C(C)C1=CC=CC(C(=O)C=2C=CC=CC=2)=C1 DKYWVDODHFEZIM-UHFFFAOYSA-N 0.000 claims 1
- OZWKMVRBQXNZKK-UHFFFAOYSA-N ketorolac Chemical group OC(=O)C1CCN2C1=CC=C2C(=O)C1=CC=CC=C1 OZWKMVRBQXNZKK-UHFFFAOYSA-N 0.000 claims 1
- OXROWJKCGCOJDO-JLHYYAGUSA-N lornoxicam Chemical compound O=C1C=2SC(Cl)=CC=2S(=O)(=O)N(C)\C1=C(\O)NC1=CC=CC=N1 OXROWJKCGCOJDO-JLHYYAGUSA-N 0.000 claims 1
- 229960002202 lornoxicam Drugs 0.000 claims 1
- BAZQYVYVKYOAGO-UHFFFAOYSA-M loxoprofen sodium hydrate Chemical group O.O.[Na+].C1=CC(C(C([O-])=O)C)=CC=C1CC1C(=O)CCC1 BAZQYVYVKYOAGO-UHFFFAOYSA-M 0.000 claims 1
- 229960003951 masoprocol Drugs 0.000 claims 1
- 229960001929 meloxicam Drugs 0.000 claims 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims 1
- UXOUKMQIEVGVLY-UHFFFAOYSA-N morin Natural products OC1=CC(O)=CC(C2=C(C(=O)C3=C(O)C=C(O)C=C3O2)O)=C1 UXOUKMQIEVGVLY-UHFFFAOYSA-N 0.000 claims 1
- CMWTZPSULFXXJA-VIFPVBQESA-N naproxen Chemical group C1=C([C@H](C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-VIFPVBQESA-N 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 claims 1
- 229960005489 paracetamol Drugs 0.000 claims 1
- 229960001639 penicillamine Drugs 0.000 claims 1
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims 1
- QYSPLQLAKJAUJT-UHFFFAOYSA-N piroxicam Chemical group OC=1C2=CC=CC=C2S(=O)(=O)N(C)C=1C(=O)NC1=CC=CC=N1 QYSPLQLAKJAUJT-UHFFFAOYSA-N 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- 235000010388 propyl gallate Nutrition 0.000 claims 1
- 239000000473 propyl gallate Substances 0.000 claims 1
- 229940075579 propyl gallate Drugs 0.000 claims 1
- YQUVCSBJEUQKSH-UHFFFAOYSA-N protochatechuic acid Natural products OC(=O)C1=CC=C(O)C(O)=C1 YQUVCSBJEUQKSH-UHFFFAOYSA-N 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 235000005875 quercetin Nutrition 0.000 claims 1
- 229960001285 quercetin Drugs 0.000 claims 1
- 229960004889 salicylic acid Drugs 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- ZKZBPNGNEQAJSX-UHFFFAOYSA-N selenocysteine Natural products [SeH]CC(N)C(O)=O ZKZBPNGNEQAJSX-UHFFFAOYSA-N 0.000 claims 1
- 229940055619 selenocysteine Drugs 0.000 claims 1
- 235000016491 selenocysteine Nutrition 0.000 claims 1
- 229960002718 selenomethionine Drugs 0.000 claims 1
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims 1
- 229960004793 sucrose Drugs 0.000 claims 1
- LZNWYQJJBLGYLT-UHFFFAOYSA-N tenoxicam Chemical group OC=1C=2SC=CC=2S(=O)(=O)N(C)C=1C(=O)NC1=CC=CC=N1 LZNWYQJJBLGYLT-UHFFFAOYSA-N 0.000 claims 1
- 125000001544 thienyl group Chemical group 0.000 claims 1
- 229940071127 thioglycolate Drugs 0.000 claims 1
- UPSPUYADGBWSHF-UHFFFAOYSA-N tolmetin Chemical group C1=CC(C)=CC=C1C(=O)C1=CC=C(CC(O)=O)N1C UPSPUYADGBWSHF-UHFFFAOYSA-N 0.000 claims 1
- 238000011200 topical administration Methods 0.000 claims 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims 1
- QURCVMIEKCOAJU-UHFFFAOYSA-N trans-isoferulic acid Natural products COC1=CC=C(C=CC(O)=O)C=C1O QURCVMIEKCOAJU-UHFFFAOYSA-N 0.000 claims 1
- PTNLHDGQWUGONS-OWOJBTEDSA-N trans-p-coumaryl alcohol Chemical compound OC\C=C\C1=CC=C(O)C=C1 PTNLHDGQWUGONS-OWOJBTEDSA-N 0.000 claims 1
- TUUBOHWZSQXCSW-UHFFFAOYSA-N vanillic acid Natural products COC1=CC(O)=CC(C(O)=O)=C1 TUUBOHWZSQXCSW-UHFFFAOYSA-N 0.000 claims 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims 1
- 229920002554 vinyl polymer Polymers 0.000 claims 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT2002MI000773A ITMI20020773A1 (it) | 2002-04-11 | 2002-04-11 | Farmaci per il trattamento dell'artrite |
| PCT/EP2003/003183 WO2003084550A1 (en) | 2002-04-11 | 2003-03-27 | Drugs for the arthritis treatment |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2005522472A JP2005522472A (ja) | 2005-07-28 |
| JP2005522472A5 true JP2005522472A5 (https=) | 2006-04-20 |
Family
ID=11449687
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2003581790A Pending JP2005522472A (ja) | 2002-04-11 | 2003-03-27 | 関節炎の治療用薬剤 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US20070010458A1 (https=) |
| EP (1) | EP1492543A1 (https=) |
| JP (1) | JP2005522472A (https=) |
| AU (1) | AU2003224002A1 (https=) |
| IT (1) | ITMI20020773A1 (https=) |
| WO (1) | WO2003084550A1 (https=) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2393724A1 (en) | 1999-12-23 | 2001-06-28 | Nitromed, Inc. | Nitrosated and nitrosylated cyclooxygenase-2 inhibitors, compositions and methods of use |
| WO2003103602A2 (en) | 2002-06-11 | 2003-12-18 | Nitromed, Inc. | Nitrosated and/or nitrosylated cyclooxygenase-2 selective inhibitors, compositions and methods of use |
| CA2491127A1 (en) | 2002-07-03 | 2004-01-15 | Nitromed, Inc. | Nitrosated nonsteroidal antiinflammatory compounds, compositions and methods of use |
| US8173840B2 (en) | 2003-07-29 | 2012-05-08 | Signature R&D Holdings, Llc | Compounds with high therapeutic index |
| US7589233B2 (en) | 2003-07-29 | 2009-09-15 | Signature R&D Holdings, Llc | L-Threonine derivatives of high therapeutic index |
| WO2005065361A2 (en) * | 2003-12-31 | 2005-07-21 | Khosrow Kashfi | Compounds and compositions for treating dysproliferative diseases, and methods of use thereof |
| EP1711457A4 (en) | 2004-01-27 | 2008-01-09 | Merck Frosst Company | NITROGEN MONOXIDE RELEASING PRODRUGS OF DIARYL-2- (5H) FURANOES AS INHIBITORS OF CYCLOOXYGENASE-2 |
| CN1914169A (zh) | 2004-01-27 | 2007-02-14 | 默克弗罗斯特公司 | 作为环氧合酶－2抑制剂的二芳基－2－(5h)－呋喃酮的氧化氮释放前药 |
| TW200616604A (en) | 2004-08-26 | 2006-06-01 | Nicholas Piramal India Ltd | Nitric oxide releasing prodrugs containing bio-cleavable linker |
| AR054181A1 (es) | 2004-08-26 | 2007-06-06 | Nicholas Piramal India Ltd | Prodrogas que contienen enlaces bio-divisibles. composiiciones farmaceuticas |
| US7586003B2 (en) * | 2005-07-14 | 2009-09-08 | Zinpro Corporation | Derivatives of seleno-amino acids |
| US8236820B2 (en) | 2007-08-10 | 2012-08-07 | Basil Rigas | Anti-inflammatory compounds and uses thereof |
| EP2188245B1 (en) | 2007-08-17 | 2013-11-06 | Council of Scientific & Industrial Research | Nitric oxide releasing derivatives of paracetamol |
| CA2897571C (en) | 2013-01-21 | 2018-12-18 | Apparao Satyam | Nitric oxide releasing prodrugs of therapeutic agents containing at least one carboxylic acid group |
| CN108864008B (zh) * | 2017-05-09 | 2021-10-22 | 江苏康缘药业股份有限公司 | 一种橙酮类化合物及其制备方法与应用 |
| CN111116529A (zh) * | 2020-01-13 | 2020-05-08 | 江苏康缘药业股份有限公司 | 一种具有抗炎作用的化合物及其制备方法和应用 |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2998450A (en) * | 1958-05-19 | 1961-08-29 | Warner Lambert Pharmaceutical | Process of preparing nu-acetyl-p-amino phenol |
| AT290523B (de) * | 1962-01-05 | 1971-06-11 | Merck & Co Inc | Verfahren zur Herstellung neuer α-(3-Indolyl)-carbonsäuren |
| US3600437A (en) * | 1969-05-28 | 1971-08-17 | Lilly Co Eli | Substituted phenylalkanoic acids and derivatives thereof |
| US3591584A (en) * | 1968-08-27 | 1971-07-06 | Pfizer | Benzothiazine dioxides |
| US3784701A (en) * | 1970-09-21 | 1974-01-08 | American Cyanamid Co | Compositions containing substituted benzoylpropionic acids and method of use to treat inflammation and pain |
| US3843681A (en) * | 1971-06-01 | 1974-10-22 | American Home Prod | 1-carboxamido pyrano(thiopyrano)(3,4-6)indole derivatives |
| US4035376A (en) * | 1972-10-24 | 1977-07-12 | Janssen Pharmaceutica N.V. | Aroyl-substituted phenylacetic acid derivatives |
| US3997669A (en) * | 1972-12-26 | 1976-12-14 | Ciba-Geigy Corporation | Tertiary aminoacids |
| US4061779A (en) * | 1973-09-11 | 1977-12-06 | Beecham Group Limited | Naphthalene derivatives having anti-inflammatory activity |
| US4161538A (en) * | 1977-04-05 | 1979-07-17 | Sankyo Company Limited | Substituted phenylacetic acid derivatives and process for the preparation thereof |
| IT1256450B (it) * | 1992-11-26 | 1995-12-05 | Soldato Piero Del | Esteri nitrici con attivita' farmacologica e procedimento per la loro preparazione |
| SI0759899T1 (en) * | 1994-05-10 | 1999-12-31 | Nicox S.A. | Nitro compounds and their compositions having anti-inflammatory, analgesic and anti-thrombotic acitivities |
| DE4420523A1 (de) * | 1994-06-13 | 1995-12-14 | Cassella Ag | Verwendung von NO-freisetzenden Verbindungen zur Behandlung und Vorbeugung von systemischen Entzündungssyndromen |
| JP2004509967A (ja) * | 2000-09-25 | 2004-04-02 | ザ、プロクター、エンド、ギャンブル、カンパニー | 医学及び治療法の適用に使用するための金属錯体 |
| US7125564B2 (en) * | 2001-02-16 | 2006-10-24 | Lavipharm Laboratories, Inc. | Water soluble and palatable complexes |
-
2002
- 2002-04-11 IT IT2002MI000773A patent/ITMI20020773A1/it unknown
-
2003
- 2003-03-27 WO PCT/EP2003/003183 patent/WO2003084550A1/en not_active Ceased
- 2003-03-27 EP EP03720377A patent/EP1492543A1/en not_active Withdrawn
- 2003-03-27 US US10/509,675 patent/US20070010458A1/en not_active Abandoned
- 2003-03-27 JP JP2003581790A patent/JP2005522472A/ja active Pending
- 2003-03-27 AU AU2003224002A patent/AU2003224002A1/en not_active Abandoned
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2005522472A5 (https=) | ||
| JP4043046B2 (ja) | 消炎、鎮痛および抗血栓活性を有するニトロ化合物およびそれらの組成物 | |
| US6207700B1 (en) | Amide derivatives for antiangiogenic and/or antitumorigenic use | |
| US8404749B2 (en) | Method of inhibiting inflammatory pain | |
| US20030004142A1 (en) | Use of NSAIDs for prevention and treatment of cellular abnormalities of the lung or bronchial pathway | |
| WO2004000300A1 (en) | Cyclooxygenase-2 inhibitors | |
| RU2001124271A (ru) | Нитроксироизводные, имеющие противовоспалительную, анальгезирующую и антитромботическую активность | |
| CN1177589C (zh) | 止痛合剂 | |
| JP2014532728A5 (https=) | ||
| JP2002538142A5 (https=) | ||
| JP2009530398A5 (https=) | ||
| JP2001515033A5 (https=) | ||
| JP2002513793A5 (https=) | ||
| JP2005522472A (ja) | 関節炎の治療用薬剤 | |
| JP2002537258A5 (https=) | ||
| JP2002503714A5 (https=) | ||
| RU2004125609A (ru) | Комбинации альфа-2-дельта-лиганда с селективным ингибитором циклооксигеназы-2 | |
| ES2280196T3 (es) | Utilizacion de r-acidos arilpropionicos para la preparacion de medicamentos destinados al tratamiento de enfermedades en seres humanos y animales, sobre las que se puede influir terapeuticamente mediante la inhibicion de la activacion de nf-kb. | |
| ES2296964T3 (es) | Compuestos a base de nitrato organico para el tratamiento de ateroesclerosis y enfermedades vasculares. | |
| JP2006516141A5 (https=) | ||
| CN1227008C (zh) | 将非cox－2选择性抑制剂的cox抑制化合物转化成为cox－2选择性抑制剂的衍生物的方法 | |
| JP2004533462A5 (https=) | ||
| EP0268388B1 (en) | Anti-inflammatory compositions | |
| US6762182B1 (en) | Converting cox inhibition compounds that are not COX-2 selective inhibitors to derivatives that are COX-2 selective inhibitors | |
| RU2005138369A (ru) | Фармацевтически полезные соли производных карбоновой кислоты |