CA2605895A1 - Composes de promedicaments mutuels utilises comme agents anti-inflammatoires a activite gastro-intestinale protectrice - Google Patents

Info

Publication number

CA2605895A1

CA2605895A1 CA002605895A CA2605895A CA2605895A1 CA 2605895 A1 CA2605895 A1 CA 2605895A1 CA 002605895 A CA002605895 A CA 002605895A CA 2605895 A CA2605895 A CA 2605895A CA 2605895 A1 CA2605895 A1 CA 2605895A1

Authority

CA

Canada

Prior art keywords

dimethyl

hydroxy

phenyl

acid

inn

Prior art date

2005-04-29

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.)

Abandoned

Links

• Espacenet
• Global Dossier
• CIPO
• Discuss

• 150000001875 compounds Chemical class 0.000 title claims abstract description 258
• 239000002260 anti-inflammatory agent Substances 0.000 title claims abstract description 16
• 230000001681 protective effect Effects 0.000 title abstract description 7
• 229940002612 prodrug Drugs 0.000 title abstract description 4
• 239000000651 prodrug Substances 0.000 title abstract description 4
• 230000002496 gastric effect Effects 0.000 title description 11
• 229940121363 anti-inflammatory agent Drugs 0.000 title description 2
• -1 analgesic Substances 0.000 claims abstract description 43
• 230000003110 anti-inflammatory effect Effects 0.000 claims abstract description 15
• 230000000202 analgesic effect Effects 0.000 claims abstract description 14
• 230000001741 anti-phlogistic effect Effects 0.000 claims abstract description 14
• 239000002221 antipyretic Substances 0.000 claims abstract description 14
• 230000001754 anti-pyretic effect Effects 0.000 claims abstract description 13
• 230000000968 intestinal effect Effects 0.000 claims abstract description 8
• 150000003839 salts Chemical class 0.000 claims description 55
• 150000002440 hydroxy compounds Chemical class 0.000 claims description 36
• 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 34
• DCOPUUMXTXDBNB-UHFFFAOYSA-N diclofenac Chemical compound OC(=O)CC1=CC=CC=C1NC1=C(Cl)C=CC=C1Cl DCOPUUMXTXDBNB-UHFFFAOYSA-N 0.000 claims description 31
• PWILYDZRJORZDR-MISYRCLQSA-N (7r,8r,9r)-7-(2-methoxyethoxy)-2,3-dimethyl-9-phenyl-7,8,9,10-tetrahydroimidazo[1,2-h][1,7]naphthyridin-8-ol Chemical compound C1([C@@H]2[C@@H](O)[C@@H](C3=C(C4=NC(C)=C(C)N4C=C3)N2)OCCOC)=CC=CC=C1 PWILYDZRJORZDR-MISYRCLQSA-N 0.000 claims description 28
• SYTBZMRGLBWNTM-JTQLQIEISA-N (S)-flurbiprofen Chemical compound FC1=CC([C@@H](C(O)=O)C)=CC=C1C1=CC=CC=C1 SYTBZMRGLBWNTM-JTQLQIEISA-N 0.000 claims description 24
• 239000002253 acid Substances 0.000 claims description 24
• YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 claims description 21
• AELILMBZWCGOSB-UHFFFAOYSA-N 2-[4-(2,6-dichloroanilino)thiophen-3-yl]acetic acid Chemical compound OC(=O)CC1=CSC=C1NC1=C(Cl)C=CC=C1Cl AELILMBZWCGOSB-UHFFFAOYSA-N 0.000 claims description 20
• 239000003814 drug Substances 0.000 claims description 20
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 19
• CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 claims description 18
• 229960001259 diclofenac Drugs 0.000 claims description 16
• 150000003254 radicals Chemical class 0.000 claims description 16
• 238000011282 treatment Methods 0.000 claims description 15
• NIMMYMAJDWUULO-BHIYHBOVSA-N (7r,8r,9r)-7-(2-methoxyethoxy)-2-methyl-9-phenyl-7,8,9,10-tetrahydroimidazo[1,2-h][1,7]naphthyridin-8-ol Chemical compound C1([C@@H]2[C@@H](O)[C@@H](C3=C(C4=NC(C)=CN4C=C3)N2)OCCOC)=CC=CC=C1 NIMMYMAJDWUULO-BHIYHBOVSA-N 0.000 claims description 14
• CMWTZPSULFXXJA-VIFPVBQESA-N naproxen Chemical compound C1=C([C@H](C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-VIFPVBQESA-N 0.000 claims description 14
• CMWTZPSULFXXJA-UHFFFAOYSA-N Naproxen Natural products C1=C(C(C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-UHFFFAOYSA-N 0.000 claims description 12
• 229950009219 eltenac Drugs 0.000 claims description 12
• 229910052739 hydrogen Inorganic materials 0.000 claims description 12
• 229960000905 indomethacin Drugs 0.000 claims description 12
• 229960002009 naproxen Drugs 0.000 claims description 12
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
• 229960004889 salicylic acid Drugs 0.000 claims description 11
• 229950006887 esflurbiprofen Drugs 0.000 claims description 10
• 229960002390 flurbiprofen Drugs 0.000 claims description 10
• FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 claims description 10
• HEFNNWSXXWATRW-UHFFFAOYSA-N Ibuprofen Chemical compound CC(C)CC1=CC=C(C(C)C(O)=O)C=C1 HEFNNWSXXWATRW-UHFFFAOYSA-N 0.000 claims description 8
• GBFLZEXEOZUWRN-VKHMYHEASA-N S-carboxymethyl-L-cysteine Chemical compound OC(=O)[C@@H](N)CSCC(O)=O GBFLZEXEOZUWRN-VKHMYHEASA-N 0.000 claims description 8
• ULUXUUYWEUJPSB-UHFFFAOYSA-N [1-benzyl-7-[(4-fluorophenyl)methoxy]-2-methylpyrrolo[2,3-d]pyridazin-3-yl]methanol Chemical compound C=12N(CC=3C=CC=CC=3)C(C)=C(CO)C2=CN=NC=1OCC1=CC=C(F)C=C1 ULUXUUYWEUJPSB-UHFFFAOYSA-N 0.000 claims description 8
• INSQKNFPRFDNKD-UHFFFAOYSA-N [2-[(1-benzyl-2,3-dimethylpyrrolo[2,3-d]pyridazin-7-yl)oxymethyl]phenyl]methanol Chemical compound C=12N(CC=3C=CC=CC=3)C(C)=C(C)C2=CN=NC=1OCC1=CC=CC=C1CO INSQKNFPRFDNKD-UHFFFAOYSA-N 0.000 claims description 8
• 229960004399 carbocisteine Drugs 0.000 claims description 8
• 230000002860 competitive effect Effects 0.000 claims description 8
• KHPKQFYUPIUARC-UHFFFAOYSA-N lumiracoxib Chemical compound OC(=O)CC1=CC(C)=CC=C1NC1=C(F)C=CC=C1Cl KHPKQFYUPIUARC-UHFFFAOYSA-N 0.000 claims description 8
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 7
• 239000001257 hydrogen Substances 0.000 claims description 7
• PWILYDZRJORZDR-RLLQIKCJSA-N (7s,8r,9r)-7-(2-methoxyethoxy)-2,3-dimethyl-9-phenyl-7,8,9,10-tetrahydroimidazo[1,2-h][1,7]naphthyridin-8-ol Chemical compound C1([C@@H]2[C@@H](O)[C@H](C3=C(C4=NC(C)=C(C)N4C=C3)N2)OCCOC)=CC=CC=C1 PWILYDZRJORZDR-RLLQIKCJSA-N 0.000 claims description 6
• FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims description 6
• 208000002193 Pain Diseases 0.000 claims description 6
• 150000001735 carboxylic acids Chemical class 0.000 claims description 6
• HUPFGZXOMWLGNK-UHFFFAOYSA-N diflunisal Chemical compound C1=C(O)C(C(=O)O)=CC(C=2C(=CC(F)=CC=2)F)=C1 HUPFGZXOMWLGNK-UHFFFAOYSA-N 0.000 claims description 6
• XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 6
• 150000002148 esters Chemical class 0.000 claims description 6
• NNYBQONXHNTVIJ-UHFFFAOYSA-N etodolac Chemical compound C1COC(CC)(CC(O)=O)C2=C1C(C=CC=C1CC)=C1N2 NNYBQONXHNTVIJ-UHFFFAOYSA-N 0.000 claims description 6
• 125000001153 fluoro group Chemical group F* 0.000 claims description 6
• 229960001680 ibuprofen Drugs 0.000 claims description 6
• DKYWVDODHFEZIM-UHFFFAOYSA-N ketoprofen Chemical compound OC(=O)C(C)C1=CC=CC(C(=O)C=2C=CC=CC=2)=C1 DKYWVDODHFEZIM-UHFFFAOYSA-N 0.000 claims description 6
• 229960000994 lumiracoxib Drugs 0.000 claims description 6
• HYYBABOKPJLUIN-UHFFFAOYSA-N mefenamic acid Chemical compound CC1=CC=CC(NC=2C(=CC=CC=2)C(O)=O)=C1C HYYBABOKPJLUIN-UHFFFAOYSA-N 0.000 claims description 6
• OFPXSFXSNFPTHF-UHFFFAOYSA-N oxaprozin Chemical compound O1C(CCC(=O)O)=NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 OFPXSFXSNFPTHF-UHFFFAOYSA-N 0.000 claims description 6
• 150000003109 potassium Chemical class 0.000 claims description 6
• 230000002265 prevention Effects 0.000 claims description 6
• 238000011160 research Methods 0.000 claims description 6
• WVYADZUPLLSGPU-UHFFFAOYSA-N salsalate Chemical compound OC(=O)C1=CC=CC=C1OC(=O)C1=CC=CC=C1O WVYADZUPLLSGPU-UHFFFAOYSA-N 0.000 claims description 6
• MLKXDPUZXIRXEP-MFOYZWKCSA-N sulindac Chemical compound 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 description 6
• UPSPUYADGBWSHF-UHFFFAOYSA-N tolmetin Chemical compound C1=CC(C)=CC=C1C(=O)C1=CC=C(CC(O)=O)N1C UPSPUYADGBWSHF-UHFFFAOYSA-N 0.000 claims description 6
• WGXOIGBJGMBBAQ-MISYRCLQSA-N (7r,8r,9r)-3-(hydroxymethyl)-7-(2-methoxyethoxy)-2-methyl-9-phenyl-7,8,9,10-tetrahydroimidazo[1,2-h][1,7]naphthyridin-8-ol Chemical compound C1([C@@H]2[C@@H](O)[C@@H](C3=C(C4=NC(C)=C(CO)N4C=C3)N2)OCCOC)=CC=CC=C1 WGXOIGBJGMBBAQ-MISYRCLQSA-N 0.000 claims description 5
• CDTUMOAUIVWZCB-RTBURBONSA-N 8-[[(1r,2r)-2-hydroxy-2,3-dihydro-1h-inden-1-yl]amino]-n,n,2,3-tetramethylimidazo[1,2-a]pyridine-6-carboxamide Chemical compound C([C@H]1O)C2=CC=CC=C2[C@H]1NC1=CC(C(=O)N(C)C)=CN2C(C)=C(C)N=C21 CDTUMOAUIVWZCB-RTBURBONSA-N 0.000 claims description 5
• LSYVFKDTISNLIP-IEBWSBKVSA-N 8-[[(1r,2r)-2-hydroxy-2,3-dihydro-1h-inden-1-yl]oxy]-n,n,2,3-tetramethylimidazo[1,2-a]pyridine-6-carboxamide Chemical compound C([C@H]1O)C2=CC=CC=C2[C@H]1OC1=CC(C(=O)N(C)C)=CN2C(C)=C(C)N=C21 LSYVFKDTISNLIP-IEBWSBKVSA-N 0.000 claims description 5
• 102000004005 Prostaglandin-endoperoxide synthases Human genes 0.000 claims description 5
• 108090000459 Prostaglandin-endoperoxide synthases Proteins 0.000 claims description 5
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 5
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
• GUHPRPJDBZHYCJ-SECBINFHSA-N (2s)-2-(5-benzoylthiophen-2-yl)propanoic acid Chemical compound S1C([C@H](C(O)=O)C)=CC=C1C(=O)C1=CC=CC=C1 GUHPRPJDBZHYCJ-SECBINFHSA-N 0.000 claims description 4
• YCHYFHOSGQABSW-RTBURBONSA-N (6ar,10ar)-1-hydroxy-6,6-dimethyl-3-(2-methyloctan-2-yl)-6a,7,10,10a-tetrahydrobenzo[c]chromene-9-carboxylic acid Chemical compound C1C(C(O)=O)=CC[C@H]2C(C)(C)OC3=CC(C(C)(C)CCCCCC)=CC(O)=C3[C@@H]21 YCHYFHOSGQABSW-RTBURBONSA-N 0.000 claims description 4
• PDMSJWFTMGWXBE-MISYRCLQSA-N (7r,8r,9r)-2,3-dimethyl-7-(2-methylsulfanylethoxy)-9-phenyl-7,8,9,10-tetrahydroimidazo[1,2-h][1,7]naphthyridin-8-ol Chemical compound C1([C@@H]2[C@@H](O)[C@@H](C3=C(C4=NC(C)=C(C)N4C=C3)N2)OCCSC)=CC=CC=C1 PDMSJWFTMGWXBE-MISYRCLQSA-N 0.000 claims description 4
• FHHGNULEXOWEKU-DJIMGWMZSA-N (7r,8r,9r)-2,3-dimethyl-9-phenyl-7,8,9,10-tetrahydroimidazo[1,2-h][1,7]naphthyridine-7,8-diol Chemical compound C1([C@H]2NC=3C4=NC(=C(N4C=CC=3[C@@H](O)[C@@H]2O)C)C)=CC=CC=C1 FHHGNULEXOWEKU-DJIMGWMZSA-N 0.000 claims description 4
• RJASEHFHFJEXPR-BHIYHBOVSA-N (7r,8r,9r)-7-ethoxy-2,3-dimethyl-9-phenyl-7,8,9,10-tetrahydroimidazo[1,2-h][1,7]naphthyridin-8-ol Chemical compound C1([C@@H]2[C@@H](O)[C@@H](C3=C(C4=NC(C)=C(C)N4C=C3)N2)OCC)=CC=CC=C1 RJASEHFHFJEXPR-BHIYHBOVSA-N 0.000 claims description 4
• GDQBYAHOQAFREY-KBAYOESNSA-N (7r,8r,9r)-7-methoxy-2,3-dimethyl-9-phenyl-7,8,9,10-tetrahydroimidazo[1,2-h][1,7]naphthyridin-8-ol Chemical compound C1([C@@H]2[C@@H](O)[C@@H](C3=C(C4=NC(C)=C(C)N4C=C3)N2)OC)=CC=CC=C1 GDQBYAHOQAFREY-KBAYOESNSA-N 0.000 claims description 4
• GDQBYAHOQAFREY-NXHRZFHOSA-N (7s,8r,9r)-7-methoxy-2,3-dimethyl-9-phenyl-7,8,9,10-tetrahydroimidazo[1,2-h][1,7]naphthyridin-8-ol Chemical compound C1([C@@H]2[C@@H](O)[C@H](C3=C(C4=NC(C)=C(C)N4C=C3)N2)OC)=CC=CC=C1 GDQBYAHOQAFREY-NXHRZFHOSA-N 0.000 claims description 4
• JCUTZUSPPNNLDC-UHFFFAOYSA-N 2-(thiophene-2-carbonyloxy)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1OC(=O)C1=CC=CS1 JCUTZUSPPNNLDC-UHFFFAOYSA-N 0.000 claims description 4
• MTHORRSSURHQPZ-UHFFFAOYSA-N 2-[(1-benzylindazol-3-yl)methoxy]-2-methylpropanoic acid Chemical compound C12=CC=CC=C2C(COC(C)(C)C(O)=O)=NN1CC1=CC=CC=C1 MTHORRSSURHQPZ-UHFFFAOYSA-N 0.000 claims description 4
• JIEKMACRVQTPRC-UHFFFAOYSA-N 2-[4-(4-chlorophenyl)-2-phenyl-5-thiazolyl]acetic acid Chemical compound OC(=O)CC=1SC(C=2C=CC=CC=2)=NC=1C1=CC=C(Cl)C=C1 JIEKMACRVQTPRC-UHFFFAOYSA-N 0.000 claims description 4
• ITJUVDBADHDNPU-UHFFFAOYSA-N 2-[4-(furan-2-carbonyl)phenyl]propanoic acid Chemical compound C1=CC(C(C(O)=O)C)=CC=C1C(=O)C1=CC=CO1 ITJUVDBADHDNPU-UHFFFAOYSA-N 0.000 claims description 4
• LNXXSBRGLBOASF-UHFFFAOYSA-N 2-[[2-(4-chlorophenyl)-4-methyl-1,3-oxazol-5-yl]methoxy]-2-methylpropanoic acid Chemical compound O1C(COC(C)(C)C(O)=O)=C(C)N=C1C1=CC=C(Cl)C=C1 LNXXSBRGLBOASF-UHFFFAOYSA-N 0.000 claims description 4
• UZIJRRXHBZLMHU-UHFFFAOYSA-N 3-(1-benzyl-2,3-dimethylpyrrolo[2,3-d]pyridazin-7-yl)oxy-3-phenylpropan-1-ol Chemical compound C=12N(CC=3C=CC=CC=3)C(C)=C(C)C2=CN=NC=1OC(CCO)C1=CC=CC=C1 UZIJRRXHBZLMHU-UHFFFAOYSA-N 0.000 claims description 4
• TYNLGDBUJLVSMA-UHFFFAOYSA-N 4,5-diacetyloxy-9,10-dioxo-2-anthracenecarboxylic acid Chemical compound O=C1C2=CC(C(O)=O)=CC(OC(C)=O)=C2C(=O)C2=C1C=CC=C2OC(=O)C TYNLGDBUJLVSMA-UHFFFAOYSA-N 0.000 claims description 4
• FIKVYIRIUOFLLR-UHFFFAOYSA-N 4-[4-(2,4-difluorophenyl)phenyl]-2-methyl-4-oxobutanoic acid Chemical compound C1=CC(C(=O)CC(C)C(O)=O)=CC=C1C1=CC=C(F)C=C1F FIKVYIRIUOFLLR-UHFFFAOYSA-N 0.000 claims description 4
• KLENJEKBEJMESG-UHFFFAOYSA-N 7-[(2,6-dimethylphenyl)methylamino]-n-(2-hydroxyethyl)-2,3-dimethylbenzimidazole-5-carboxamide Chemical compound C1=C(C(=O)NCCO)C=C2N(C)C(C)=NC2=C1NCC1=C(C)C=CC=C1C KLENJEKBEJMESG-UHFFFAOYSA-N 0.000 claims description 4
• SSFWVSVLGNYORI-UHFFFAOYSA-N 7-[(2,6-dimethylphenyl)methylamino]-n-(2-hydroxyethyl)-n,2,3-trimethylbenzimidazole-5-carboxamide Chemical compound C=12N=C(C)N(C)C2=CC(C(=O)N(CCO)C)=CC=1NCC1=C(C)C=CC=C1C SSFWVSVLGNYORI-UHFFFAOYSA-N 0.000 claims description 4
• NHTDEDVRPMLNSE-CRAIPNDOSA-N 7-[[(1r,2r)-5-chloro-2-hydroxy-2,3-dihydro-1h-inden-1-yl]oxy]-2,3-dimethylbenzimidazole-5-carboxylic acid Chemical compound C([C@H]1O)C2=CC(Cl)=CC=C2[C@H]1OC1=C2N=C(C)N(C)C2=CC(C(O)=O)=C1 NHTDEDVRPMLNSE-CRAIPNDOSA-N 0.000 claims description 4
• MROJXXOCABQVEF-UHFFFAOYSA-N Actarit Chemical compound CC(=O)NC1=CC=C(CC(O)=O)C=C1 MROJXXOCABQVEF-UHFFFAOYSA-N 0.000 claims description 4
• OIRAEJWYWSAQNG-UHFFFAOYSA-N Clidanac Chemical compound ClC=1C=C2C(C(=O)O)CCC2=CC=1C1CCCCC1 OIRAEJWYWSAQNG-UHFFFAOYSA-N 0.000 claims description 4
• AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 claims description 4
• SBDNJUWAMKYJOX-UHFFFAOYSA-N Meclofenamic Acid Chemical compound CC1=CC=C(Cl)C(NC=2C(=CC=CC=2)C(O)=O)=C1Cl SBDNJUWAMKYJOX-UHFFFAOYSA-N 0.000 claims description 4
• DJEIHHYCDCTAAH-UHFFFAOYSA-N Mofezolac (TN) Chemical compound C1=CC(OC)=CC=C1C1=NOC(CC(O)=O)=C1C1=CC=C(OC)C=C1 DJEIHHYCDCTAAH-UHFFFAOYSA-N 0.000 claims description 4
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• FVZJDDVKQKWIKE-UHFFFAOYSA-N [2-[[1-(furan-2-ylmethyl)-2,3-dimethylpyrrolo[2,3-d]pyridazin-7-yl]oxymethyl]phenyl]methanol Chemical compound C=12N(CC=3OC=CC=3)C(C)=C(C)C2=CN=NC=1OCC1=CC=CC=C1CO FVZJDDVKQKWIKE-UHFFFAOYSA-N 0.000 claims description 4
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• UULSXYSSHHRCQK-UHFFFAOYSA-N butibufen Chemical compound CCC(C(O)=O)C1=CC=C(CC(C)C)C=C1 UULSXYSSHHRCQK-UHFFFAOYSA-N 0.000 claims description 4
• NKPPORKKCMYYTO-DHZHZOJOSA-N cinmetacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)\C=C\C1=CC=CC=C1 NKPPORKKCMYYTO-DHZHZOJOSA-N 0.000 claims description 4
• UGOFYAXVVVXMQT-UHFFFAOYSA-N clobuzarit Chemical compound C1=CC(COC(C)(C)C(O)=O)=CC=C1C1=CC=C(Cl)C=C1 UGOFYAXVVVXMQT-UHFFFAOYSA-N 0.000 claims description 4
• HEFNNWSXXWATRW-JTQLQIEISA-N dexibuprofen Chemical compound CC(C)CC1=CC=C([C@H](C)C(O)=O)C=C1 HEFNNWSXXWATRW-JTQLQIEISA-N 0.000 claims description 4
• 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 description 4
• 229960000616 diflunisal Drugs 0.000 claims description 4
• HLNLBEFKHHCAMV-UHFFFAOYSA-N enfenamic acid Chemical compound OC(=O)C1=CC=CC=C1NCCC1=CC=CC=C1 HLNLBEFKHHCAMV-UHFFFAOYSA-N 0.000 claims description 4
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