CA2753597A1 - Drug combinations containing pde4-inhibitors and nsaids - Google Patents

Info

Publication number

CA2753597A1

CA2753597A1 CA2753597A CA2753597A CA2753597A1 CA 2753597 A1 CA2753597 A1 CA 2753597A1 CA 2753597 A CA2753597 A CA 2753597A CA 2753597 A CA2753597 A CA 2753597A CA 2753597 A1 CA2753597 A1 CA 2753597A1

Authority

CA

Canada

Prior art keywords

oxo

pyrimidin

piperazin

thieno

dihydro

Prior art date

2009-02-27

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

• 229940123932 Phosphodiesterase 4 inhibitor Drugs 0.000 title claims abstract description 120
• 239000002587 phosphodiesterase IV inhibitor Substances 0.000 title claims abstract description 120
• 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 title claims abstract description 102
• 239000000890 drug combination Substances 0.000 title claims abstract description 61
• 239000000041 non-steroidal anti-inflammatory agent Substances 0.000 claims abstract description 101
• 125000002950 monocyclic group Chemical group 0.000 claims abstract description 46
• 229920006395 saturated elastomer Polymers 0.000 claims abstract description 37
• 125000002619 bicyclic group Chemical group 0.000 claims abstract description 19
• 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 19
• 230000000241 respiratory effect Effects 0.000 claims abstract description 12
• 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims abstract description 10
• 206010009137 Chronic sinusitis Diseases 0.000 claims abstract description 8
• 208000027157 chronic rhinosinusitis Diseases 0.000 claims abstract description 8
• OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Substances OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 73
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 72
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 54
• VUWZPRWSIVNGKG-UHFFFAOYSA-N fluoromethane Chemical compound F[CH2] VUWZPRWSIVNGKG-UHFFFAOYSA-N 0.000 claims description 54
• JNCMHMUGTWEVOZ-UHFFFAOYSA-N F[CH]F Chemical compound F[CH]F JNCMHMUGTWEVOZ-UHFFFAOYSA-N 0.000 claims description 52
• 108010081348 HRT1 protein Hairy Proteins 0.000 claims description 52
• 102100021881 Hairy/enhancer-of-split related with YRPW motif protein 1 Human genes 0.000 claims description 52
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 52
• 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims description 52
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 52
• 125000001072 heteroaryl group Chemical group 0.000 claims description 50
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 48
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 46
• 239000000460 chlorine Substances 0.000 claims description 41
• 229960001259 diclofenac Drugs 0.000 claims description 40
• DCOPUUMXTXDBNB-UHFFFAOYSA-N diclofenac Chemical compound OC(=O)CC1=CC=CC=C1NC1=C(Cl)C=CC=C1Cl DCOPUUMXTXDBNB-UHFFFAOYSA-N 0.000 claims description 39
• 229910052731 fluorine Inorganic materials 0.000 claims description 39
• 229910052801 chlorine Inorganic materials 0.000 claims description 38
• 229910052794 bromium Inorganic materials 0.000 claims description 37
• 125000004043 oxo group Chemical group O=* 0.000 claims description 36
• -1 C1-6-alkanol Chemical group 0.000 claims description 35
• 239000000203 mixture Substances 0.000 claims description 35
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 34
• 201000010099 disease Diseases 0.000 claims description 33
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 33
• 229910052736 halogen Inorganic materials 0.000 claims description 32
• 150000002367 halogens Chemical class 0.000 claims description 32
• 238000009472 formulation Methods 0.000 claims description 28
• 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 28
• 150000001875 compounds Chemical class 0.000 claims description 27
• 229960000994 lumiracoxib Drugs 0.000 claims description 27
• 230000000694 effects Effects 0.000 claims description 26
• 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 21
• 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 description 21
• 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 21
• 229960001138 acetylsalicylic acid Drugs 0.000 claims description 21
• 229960001680 ibuprofen Drugs 0.000 claims description 21
• 229960001929 meloxicam Drugs 0.000 claims description 21
• 229960002009 naproxen Drugs 0.000 claims description 21
• 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 21
• BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 claims description 20
• 125000000041 C6-C10 aryl group Chemical group 0.000 claims description 17
• 125000005842 heteroatom Chemical group 0.000 claims description 16
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 14
• 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 14
• 229910052717 sulfur Inorganic materials 0.000 claims description 11
• MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims description 10
• 229960000590 celecoxib Drugs 0.000 claims description 10
• 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 10
• 229910052757 nitrogen Inorganic materials 0.000 claims description 10
• 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims description 9
• 208000027866 inflammatory disease Diseases 0.000 claims description 9
• NWGGKKGAFZIVBJ-UHFFFAOYSA-N antrafenine Chemical compound FC(F)(F)C1=CC=CC(N2CCN(CCOC(=O)C=3C(=CC=CC=3)NC=3C4=CC=C(C=C4N=CC=3)C(F)(F)F)CC2)=C1 NWGGKKGAFZIVBJ-UHFFFAOYSA-N 0.000 claims description 8
• 210000003169 central nervous system Anatomy 0.000 claims description 8
• 229960000905 indomethacin Drugs 0.000 claims description 8
• 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 8
• 230000002093 peripheral effect Effects 0.000 claims description 8
• 210000001428 peripheral nervous system Anatomy 0.000 claims description 8
• YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 claims description 8
• WVYADZUPLLSGPU-UHFFFAOYSA-N salsalate Chemical compound OC(=O)C1=CC=CC=C1OC(=O)C1=CC=CC=C1O WVYADZUPLLSGPU-UHFFFAOYSA-N 0.000 claims description 8
• YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 7
• 206010028980 Neoplasm Diseases 0.000 claims description 7
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 6
• 208000006673 asthma Diseases 0.000 claims description 6
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 6
• 229960004945 etoricoxib Drugs 0.000 claims description 6
• 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 6
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 6
• 229960004662 parecoxib Drugs 0.000 claims description 6
• 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 6
• 229960000371 rofecoxib Drugs 0.000 claims description 6
• 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 6
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 5
• 206010009900 Colitis ulcerative Diseases 0.000 claims description 5
• 208000011231 Crohn disease Diseases 0.000 claims description 5
• 208000019693 Lung disease Diseases 0.000 claims description 5
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 5
• 201000006704 Ulcerative Colitis Diseases 0.000 claims description 5
• 229940111134 coxibs Drugs 0.000 claims description 5
• 230000002496 gastric effect Effects 0.000 claims description 5
• FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 claims description 5
• 229960002004 valdecoxib Drugs 0.000 claims description 5
• 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 5
• 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 description 4
• RDJGLLICXDHJDY-NSHDSACASA-N (2s)-2-(3-phenoxyphenyl)propanoic acid Chemical compound OC(=O)[C@@H](C)C1=CC=CC(OC=2C=CC=CC=2)=C1 RDJGLLICXDHJDY-NSHDSACASA-N 0.000 claims description 4
• 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
• MDKGKXOCJGEUJW-VIFPVBQESA-N (2s)-2-[4-(thiophene-2-carbonyl)phenyl]propanoic acid Chemical compound C1=CC([C@@H](C(O)=O)C)=CC=C1C(=O)C1=CC=CS1 MDKGKXOCJGEUJW-VIFPVBQESA-N 0.000 claims description 4
• FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 claims description 4
• KLIVRBFRQSOGQI-UHFFFAOYSA-N 2-(11-oxo-6h-benzo[c][1]benzothiepin-3-yl)acetic acid Chemical compound S1CC2=CC=CC=C2C(=O)C2=CC=C(CC(=O)O)C=C12 KLIVRBFRQSOGQI-UHFFFAOYSA-N 0.000 claims description 4
• MYQXHLQMZLTSDB-UHFFFAOYSA-N 2-(2-ethyl-2,3-dihydro-1-benzofuran-5-yl)acetic acid Chemical compound OC(=O)CC1=CC=C2OC(CC)CC2=C1 MYQXHLQMZLTSDB-UHFFFAOYSA-N 0.000 claims description 4
• VARKFMHUVKZOHE-UHFFFAOYSA-N 2-(butan-2-ylamino)-2-oxoacetic acid Chemical compound CCC(C)NC(=O)C(O)=O VARKFMHUVKZOHE-UHFFFAOYSA-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
• XLVXAUNDHWERBM-IVGWJTKZSA-N 2-[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]-n-[(2r,3r,4s,5r)-3,4,5,6-tetrahydroxy-1-oxohexan-2-yl]acetamide Chemical compound CC1=C(CC(=O)N[C@@H](C=O)[C@@H](O)[C@H](O)[C@H](O)CO)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 XLVXAUNDHWERBM-IVGWJTKZSA-N 0.000 claims description 4
• RXZTWBVFHQLTBU-UHFFFAOYSA-N 2-[4-(1,3-thiazol-2-yloxy)phenyl]propanoic acid Chemical compound C1=CC(C(C(O)=O)C)=CC=C1OC1=NC=CS1 RXZTWBVFHQLTBU-UHFFFAOYSA-N 0.000 claims description 4
• 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 4
• YAMFWQIVVMITPG-UHFFFAOYSA-N 2-[4-(4-chlorophenyl)-1-(4-fluorophenyl)pyrazol-3-yl]acetic acid Chemical compound OC(=O)CC1=NN(C=2C=CC(F)=CC=2)C=C1C1=CC=C(Cl)C=C1 YAMFWQIVVMITPG-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
• IQPPOXSMSDPZKU-JQIJEIRASA-N 2-[4-[(3e)-3-hydroxyiminocyclohexyl]phenyl]propanoic acid Chemical compound C1=CC(C(C(O)=O)C)=CC=C1C1CC(=N/O)/CCC1 IQPPOXSMSDPZKU-JQIJEIRASA-N 0.000 claims description 4
• AUZUGWXLBGZUPP-GXDHUFHOSA-N 2-[4-[(e)-(2-oxocyclohexylidene)methyl]phenyl]propanoic acid Chemical compound C1=CC(C(C(O)=O)C)=CC=C1\C=C/1C(=O)CCCC\1 AUZUGWXLBGZUPP-GXDHUFHOSA-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
• XKSAJZSJKURQRX-UHFFFAOYSA-N 2-acetyloxy-5-(4-fluorophenyl)benzoic acid Chemical compound C1=C(C(O)=O)C(OC(=O)C)=CC=C1C1=CC=C(F)C=C1 XKSAJZSJKURQRX-UHFFFAOYSA-N 0.000 claims description 4
• SQVNITZYWXMWOG-UHFFFAOYSA-N 2-cyclohexyl-1-(2-methylquinolin-4-yl)-3-(1,3-thiazol-2-yl)guanidine Chemical compound C=12C=CC=CC2=NC(C)=CC=1NC(=NC1CCCCC1)NC1=NC=CS1 SQVNITZYWXMWOG-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
• SYCHUQUJURZQMO-UHFFFAOYSA-N 4-hydroxy-2-methyl-1,1-dioxo-n-(1,3-thiazol-2-yl)-1$l^{6},2-benzothiazine-3-carboxamide Chemical compound OC=1C2=CC=CC=C2S(=O)(=O)N(C)C=1C(=O)NC1=NC=CS1 SYCHUQUJURZQMO-UHFFFAOYSA-N 0.000 claims description 4
• KWFFVBCJCQQAIV-UHFFFAOYSA-N 4-phenylcyclohexan-1-amine;2-(4-phenylphenyl)butanoic acid Chemical compound C1CC(N)CCC1C1=CC=CC=C1.C1=CC(C(C(O)=O)CC)=CC=C1C1=CC=CC=C1 KWFFVBCJCQQAIV-UHFFFAOYSA-N 0.000 claims description 4
• HEOZYYOUKGGSBJ-UHFFFAOYSA-N 5-(4-methoxybenzoyl)-2,3-dihydro-1h-pyrrolizine-1-carboxylic acid Chemical compound C1=CC(OC)=CC=C1C(=O)C1=CC=C2N1CCC2C(O)=O HEOZYYOUKGGSBJ-UHFFFAOYSA-N 0.000 claims description 4
• DVEQCIBLXRSYPH-UHFFFAOYSA-N 5-butyl-1-cyclohexylbarbituric acid Chemical compound O=C1C(CCCC)C(=O)NC(=O)N1C1CCCCC1 DVEQCIBLXRSYPH-UHFFFAOYSA-N 0.000 claims description 4
• 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 4
• MNIPYSSQXLZQLJ-UHFFFAOYSA-N Biofenac Chemical compound OC(=O)COC(=O)CC1=CC=CC=C1NC1=C(Cl)C=CC=C1Cl MNIPYSSQXLZQLJ-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
• RBBWCVQDXDFISW-UHFFFAOYSA-N Feprazone Chemical compound O=C1C(CC=C(C)C)C(=O)N(C=2C=CC=CC=2)N1C1=CC=CC=C1 RBBWCVQDXDFISW-UHFFFAOYSA-N 0.000 claims description 4
• APQPGQGAWABJLN-UHFFFAOYSA-N Floctafenine Chemical compound OCC(O)COC(=O)C1=CC=CC=C1NC1=CC=NC2=C(C(F)(F)F)C=CC=C12 APQPGQGAWABJLN-UHFFFAOYSA-N 0.000 claims description 4
• ALIVXCSEERJYHU-UHFFFAOYSA-N Flurbiprofen axetil Chemical compound FC1=CC(C(C)C(=O)OC(OC(C)=O)C)=CC=C1C1=CC=CC=C1 ALIVXCSEERJYHU-UHFFFAOYSA-N 0.000 claims description 4
• ACEWLPOYLGNNHV-UHFFFAOYSA-N Ibuprofen piconol Chemical compound C1=CC(CC(C)C)=CC=C1C(C)C(=O)OCC1=CC=CC=N1 ACEWLPOYLGNNHV-UHFFFAOYSA-N 0.000 claims description 4
• SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 4
• CFIGYZZVJNJVDQ-LMJOQDENSA-N Indomethacin farnesil Chemical compound CC1=C(CC(=O)OC\C=C(/C)CC\C=C(/C)CCC=C(C)C)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CFIGYZZVJNJVDQ-LMJOQDENSA-N 0.000 claims description 4
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• 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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• JZFPYUNJRRFVQU-UHFFFAOYSA-N Niflumic acid Chemical compound OC(=O)C1=CC=CN=C1NC1=CC=CC(C(F)(F)F)=C1 JZFPYUNJRRFVQU-UHFFFAOYSA-N 0.000 claims description 4
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• VSQMKHNDXWGCDB-UHFFFAOYSA-N Protizinic acid Chemical compound OC(=O)C(C)C1=CC=C2SC3=CC(OC)=CC=C3N(C)C2=C1 VSQMKHNDXWGCDB-UHFFFAOYSA-N 0.000 claims description 4
• KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 4
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
• KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 4
• SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 4
• SKZKKFZAGNVIMN-UHFFFAOYSA-N Salicilamide Chemical compound NC(=O)C1=CC=CC=C1O SKZKKFZAGNVIMN-UHFFFAOYSA-N 0.000 claims description 4
• YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 4
• JDLSRXWHEBFHNC-UHFFFAOYSA-N Ufenamate Chemical compound CCCCOC(=O)C1=CC=CC=C1NC1=CC=CC(C(F)(F)F)=C1 JDLSRXWHEBFHNC-UHFFFAOYSA-N 0.000 claims description 4
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