BRPI0608636A2 - novos compostos ii derivados de 2-piridina como inibidores de elastase de neutràfilo - Google Patents

Info

Publication number

BRPI0608636A2

BRPI0608636A2 BRPI0608636-5A BRPI0608636A BRPI0608636A2 BR PI0608636 A2 BRPI0608636 A2 BR PI0608636A2 BR PI0608636 A BRPI0608636 A BR PI0608636A BR PI0608636 A2 BRPI0608636 A2 BR PI0608636A2

Authority

BR

Brazil

Prior art keywords

phenyl

oxo

methyl

carboxamide

dihydropyridine

Prior art date

2005-03-16

Links

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• Global Dossier
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• -1 compounds 2-pyridine derivatives Chemical class 0.000 title claims abstract description 112
• 239000003591 leukocyte elastase inhibitor Substances 0.000 title abstract 2
• 102000002255 Secretory Proteinase Inhibitory Proteins Human genes 0.000 title 1
• 108010000303 Secretory Proteinase Inhibitory Proteins Proteins 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims abstract description 113
• 238000000034 method Methods 0.000 claims abstract description 42
• 150000003839 salts Chemical class 0.000 claims abstract description 29
• 230000008569 process Effects 0.000 claims abstract description 18
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 15
• 238000002360 preparation method Methods 0.000 claims abstract description 15
• 201000010099 disease Diseases 0.000 claims abstract description 13
• 239000003814 drug Substances 0.000 claims abstract description 9
• 230000000694 effects Effects 0.000 claims abstract description 9
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 9
• 238000002560 therapeutic procedure Methods 0.000 claims abstract description 7
• 108010028275 Leukocyte Elastase Proteins 0.000 claims abstract description 5
• 102000016799 Leukocyte elastase Human genes 0.000 claims abstract description 5
• 230000009286 beneficial effect Effects 0.000 claims abstract description 5
• 230000005764 inhibitory process Effects 0.000 claims abstract description 4
• 238000004519 manufacturing process Methods 0.000 claims abstract description 4
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 56
• 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 50
• 125000001424 substituent group Chemical group 0.000 claims description 39
• 229910052739 hydrogen Inorganic materials 0.000 claims description 38
• 239000001257 hydrogen Substances 0.000 claims description 32
• 229910052760 oxygen Inorganic materials 0.000 claims description 29
• 125000005842 heteroatom Chemical group 0.000 claims description 27
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 27
• 125000000217 alkyl group Chemical group 0.000 claims description 26
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 25
• 239000001301 oxygen Chemical group 0.000 claims description 25
• 125000003545 alkoxy group Chemical group 0.000 claims description 24
• 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 claims description 23
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 23
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 22
• 229910052736 halogen Inorganic materials 0.000 claims description 22
• 150000002367 halogens Chemical class 0.000 claims description 20
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 19
• 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 19
• 238000006243 chemical reaction Methods 0.000 claims description 18
• 229910052731 fluorine Inorganic materials 0.000 claims description 18
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 17
• 229920006395 saturated elastomer Polymers 0.000 claims description 17
• 229910052757 nitrogen Inorganic materials 0.000 claims description 16
• 229910052717 sulfur Chemical group 0.000 claims description 16
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 15
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 13
• 239000011593 sulfur Chemical group 0.000 claims description 13
• 125000001153 fluoro group Chemical group F* 0.000 claims description 12
• 239000000460 chlorine Substances 0.000 claims description 11
• 229910052801 chlorine Inorganic materials 0.000 claims description 11
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 11
• 125000001072 heteroaryl group Chemical group 0.000 claims description 10
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 10
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 9
• 125000004122 cyclic group Chemical group 0.000 claims description 9
• 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 9
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 9
• 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 8
• 206010014561 Emphysema Diseases 0.000 claims description 8
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 8
• 229910052794 bromium Inorganic materials 0.000 claims description 8
• 125000001589 carboacyl group Chemical group 0.000 claims description 8
• 239000011737 fluorine Substances 0.000 claims description 8
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
• 125000004076 pyridyl group Chemical group 0.000 claims description 8
• 206010001052 Acute respiratory distress syndrome Diseases 0.000 claims description 7
• 229910052799 carbon Inorganic materials 0.000 claims description 7
• 125000001183 hydrocarbyl group Chemical group 0.000 claims description 7
• 230000000302 ischemic effect Effects 0.000 claims description 7
• 238000011282 treatment Methods 0.000 claims description 7
• 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 6
• 125000003341 7 membered heterocyclic group Chemical group 0.000 claims description 6
• 206010028980 Neoplasm Diseases 0.000 claims description 6
• 208000013616 Respiratory Distress Syndrome Diseases 0.000 claims description 6
• 230000001154 acute effect Effects 0.000 claims description 6
• 239000002671 adjuvant Substances 0.000 claims description 6
• 201000000028 adult respiratory distress syndrome Diseases 0.000 claims description 6
• 230000006378 damage Effects 0.000 claims description 6
• 208000027866 inflammatory disease Diseases 0.000 claims description 6
• 125000002950 monocyclic group Chemical group 0.000 claims description 6
• 208000002815 pulmonary hypertension Diseases 0.000 claims description 6
• PWKXYFJXFJCGNY-UHFFFAOYSA-N 6-methyl-n-[(4-methylsulfonylphenyl)methyl]-2-oxo-5-phenylsulfanyl-1-[3-(trifluoromethyl)phenyl]pyridine-3-carboxamide Chemical compound C1=C(C(=O)NCC=2C=CC(=CC=2)S(C)(=O)=O)C(=O)N(C=2C=C(C=CC=2)C(F)(F)F)C(C)=C1SC1=CC=CC=C1 PWKXYFJXFJCGNY-UHFFFAOYSA-N 0.000 claims description 5
• 201000003883 Cystic fibrosis Diseases 0.000 claims description 5
• 206010063837 Reperfusion injury Diseases 0.000 claims description 5
• 208000006673 asthma Diseases 0.000 claims description 5
• 125000004429 atom Chemical group 0.000 claims description 5
• 206010006451 bronchitis Diseases 0.000 claims description 5
• 201000011510 cancer Diseases 0.000 claims description 5
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 5
• 239000003085 diluting agent Substances 0.000 claims description 5
• 201000008482 osteoarthritis Diseases 0.000 claims description 5
• 206010039073 rheumatoid arthritis Diseases 0.000 claims description 5
• 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 4
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 4
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 4
• OKLVQAFLYLIJFE-UHFFFAOYSA-N 6-methyl-5-methylsulfinyl-n-[(4-methylsulfonylphenyl)methyl]-2-oxo-1-[3-(trifluoromethyl)phenyl]pyridine-3-carboxamide Chemical compound O=C1N(C=2C=C(C=CC=2)C(F)(F)F)C(C)=C(S(C)=O)C=C1C(=O)NCC1=CC=C(S(C)(=O)=O)C=C1 OKLVQAFLYLIJFE-UHFFFAOYSA-N 0.000 claims description 4
• 201000001320 Atherosclerosis Diseases 0.000 claims description 4
• DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 claims description 4
• 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 4
• 208000011341 adult acute respiratory distress syndrome Diseases 0.000 claims description 4
• 150000001412 amines Chemical class 0.000 claims description 4
• 201000009267 bronchiectasis Diseases 0.000 claims description 4
• 125000004432 carbon atom Chemical group C* 0.000 claims description 4
• 125000005843 halogen group Chemical group 0.000 claims description 4
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 4
• 206010039083 rhinitis Diseases 0.000 claims description 4
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 3
• 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 3
• 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 claims description 3
• 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims description 3
• 125000004860 4-ethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])C([H])([H])[H] 0.000 claims description 3
• ZUIQRLIQXYYXHV-UHFFFAOYSA-N 5-(4-cyanophenyl)sulfonyl-n,6-dimethyl-2-oxo-1-[3-(trifluoromethyl)phenyl]pyridine-3-carboxamide Chemical compound O=C1C(C(=O)NC)=CC(S(=O)(=O)C=2C=CC(=CC=2)C#N)=C(C)N1C1=CC=CC(C(F)(F)F)=C1 ZUIQRLIQXYYXHV-UHFFFAOYSA-N 0.000 claims description 3
• HKJSUEZLKNIFBH-UHFFFAOYSA-N 5-(benzenesulfonyl)-6-methyl-n-[(4-methylsulfonylphenyl)methyl]-2-oxo-1-[3-(trifluoromethyl)phenyl]pyridine-3-carboxamide Chemical compound O=C1N(C=2C=C(C=CC=2)C(F)(F)F)C(C)=C(S(=O)(=O)C=2C=CC=CC=2)C=C1C(=O)NCC1=CC=C(S(C)(=O)=O)C=C1 HKJSUEZLKNIFBH-UHFFFAOYSA-N 0.000 claims description 3
• MWCQLOAQHBUEMJ-UHFFFAOYSA-N 5-cyclohexylsulfinyl-6-methyl-n-[(4-methylsulfonylphenyl)methyl]-2-oxo-1-[3-(trifluoromethyl)phenyl]pyridine-3-carboxamide Chemical compound O=C1N(C=2C=C(C=CC=2)C(F)(F)F)C(C)=C(S(=O)C2CCCCC2)C=C1C(=O)NCC1=CC=C(S(C)(=O)=O)C=C1 MWCQLOAQHBUEMJ-UHFFFAOYSA-N 0.000 claims description 3
• HMBACIQWRCCXEF-UHFFFAOYSA-N 6-methyl-n-[(4-methylsulfonylphenyl)methyl]-2-oxo-1-[3-(trifluoromethyl)phenyl]-5-[4-(2-trimethylsilylethynyl)phenyl]sulfinylpyridine-3-carboxamide Chemical compound O=C1N(C=2C=C(C=CC=2)C(F)(F)F)C(C)=C(S(=O)C=2C=CC(=CC=2)C#C[Si](C)(C)C)C=C1C(=O)NCC1=CC=C(S(C)(=O)=O)C=C1 HMBACIQWRCCXEF-UHFFFAOYSA-N 0.000 claims description 3
• XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical compound CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 3
• 208000027418 Wounds and injury Diseases 0.000 claims description 3
• 239000002253 acid Substances 0.000 claims description 3
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
• 230000002496 gastric effect Effects 0.000 claims description 3
• 208000014674 injury Diseases 0.000 claims description 3
• 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 3
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
• HQVWMCRXOFKKGL-UHFFFAOYSA-N 5-(4-bromophenyl)sulfinyl-n,6-dimethyl-2-oxo-1-[3-(trifluoromethyl)phenyl]pyridine-3-carboxamide Chemical compound O=C1C(C(=O)NC)=CC(S(=O)C=2C=CC(Br)=CC=2)=C(C)N1C1=CC=CC(C(F)(F)F)=C1 HQVWMCRXOFKKGL-UHFFFAOYSA-N 0.000 claims description 2
• HOGMYIXDMNBBIQ-UHFFFAOYSA-N 5-(4-cyanophenyl)sulfinyl-1-(3,5-dichlorophenyl)-n-[(5-ethylsulfonylpyridin-2-yl)methyl]-6-methyl-2-oxopyridine-3-carboxamide Chemical compound N1=CC(S(=O)(=O)CC)=CC=C1CNC(=O)C(C1=O)=CC(S(=O)C=2C=CC(=CC=2)C#N)=C(C)N1C1=CC(Cl)=CC(Cl)=C1 HOGMYIXDMNBBIQ-UHFFFAOYSA-N 0.000 claims description 2
• VFGWRXNWVNRFEE-UHFFFAOYSA-N 5-(4-cyanophenyl)sulfinyl-1-(3,5-difluorophenyl)-n-[(5-ethylsulfonylpyridin-2-yl)methyl]-6-methyl-2-oxopyridine-3-carboxamide Chemical compound N1=CC(S(=O)(=O)CC)=CC=C1CNC(=O)C(C1=O)=CC(S(=O)C=2C=CC(=CC=2)C#N)=C(C)N1C1=CC(F)=CC(F)=C1 VFGWRXNWVNRFEE-UHFFFAOYSA-N 0.000 claims description 2
• DCBZAYLUTKGUSY-UHFFFAOYSA-N 5-(4-cyanophenyl)sulfinyl-1-(3,5-difluorophenyl)-n-[2-(1h-imidazol-5-yl)ethyl]-6-methyl-2-oxopyridine-3-carboxamide Chemical compound O=C1N(C=2C=C(F)C=C(F)C=2)C(C)=C(S(=O)C=2C=CC(=CC=2)C#N)C=C1C(=O)NCCC1=CNC=N1 DCBZAYLUTKGUSY-UHFFFAOYSA-N 0.000 claims description 2
• GUZFBENKJIRRBH-UHFFFAOYSA-N 5-(4-cyanophenyl)sulfinyl-6-methyl-1-(3-methylphenyl)-n-[(5-methylsulfonylpyridin-2-yl)methyl]-2-oxopyridine-3-carboxamide Chemical compound CC1=CC=CC(N2C(C(C(=O)NCC=3N=CC(=CC=3)S(C)(=O)=O)=CC(=C2C)S(=O)C=2C=CC(=CC=2)C#N)=O)=C1 GUZFBENKJIRRBH-UHFFFAOYSA-N 0.000 claims description 2
• YDYDOJWRRZKZGN-UHFFFAOYSA-N 5-(4-cyanophenyl)sulfinyl-6-methyl-2-oxo-n-[3-(2-oxopyrrolidin-1-yl)propyl]-1-[3-(trifluoromethyl)phenyl]pyridine-3-carboxamide Chemical compound O=C1N(C=2C=C(C=CC=2)C(F)(F)F)C(C)=C(S(=O)C=2C=CC(=CC=2)C#N)C=C1C(=O)NCCCN1CCCC1=O YDYDOJWRRZKZGN-UHFFFAOYSA-N 0.000 claims description 2
• HBSKDMSAWKJSIQ-UHFFFAOYSA-N 5-(4-cyanophenyl)sulfinyl-6-methyl-n-[(3-methyl-1,2-oxazol-5-yl)methyl]-2-oxo-1-[3-(trifluoromethyl)phenyl]pyridine-3-carboxamide Chemical compound O1N=C(C)C=C1CNC(=O)C(C1=O)=CC(S(=O)C=2C=CC(=CC=2)C#N)=C(C)N1C1=CC=CC(C(F)(F)F)=C1 HBSKDMSAWKJSIQ-UHFFFAOYSA-N 0.000 claims description 2
• DMVJCLKVSSYLLR-UHFFFAOYSA-N 5-(4-cyanophenyl)sulfinyl-n,6-dimethyl-2-oxo-1-[3-(trifluoromethyl)phenyl]pyridine-3-carboxamide Chemical compound O=C1C(C(=O)NC)=CC(S(=O)C=2C=CC(=CC=2)C#N)=C(C)N1C1=CC=CC(C(F)(F)F)=C1 DMVJCLKVSSYLLR-UHFFFAOYSA-N 0.000 claims description 2
• AXTKOOUFUDKUHQ-UHFFFAOYSA-N 5-(4-cyanophenyl)sulfinyl-n-(2-hydroxyethyl)-6-methyl-2-oxo-1-[3-(trifluoromethyl)phenyl]pyridine-3-carboxamide Chemical compound CC1=C(S(=O)C=2C=CC(=CC=2)C#N)C=C(C(=O)NCCO)C(=O)N1C1=CC=CC(C(F)(F)F)=C1 AXTKOOUFUDKUHQ-UHFFFAOYSA-N 0.000 claims description 2
• NNFBDDCXLAIGQL-UHFFFAOYSA-N 5-(4-cyanophenyl)sulfinyl-n-(2-hydroxypropyl)-6-methyl-2-oxo-1-[3-(trifluoromethyl)phenyl]pyridine-3-carboxamide Chemical compound O=C1C(C(=O)NCC(O)C)=CC(S(=O)C=2C=CC(=CC=2)C#N)=C(C)N1C1=CC=CC(C(F)(F)F)=C1 NNFBDDCXLAIGQL-UHFFFAOYSA-N 0.000 claims description 2
• SAAHPVSQWALTKK-UHFFFAOYSA-N 5-(4-cyanophenyl)sulfinyl-n-(2-methoxypropyl)-6-methyl-2-oxo-1-[3-(trifluoromethyl)phenyl]pyridine-3-carboxamide Chemical compound O=C1C(C(=O)NCC(C)OC)=CC(S(=O)C=2C=CC(=CC=2)C#N)=C(C)N1C1=CC=CC(C(F)(F)F)=C1 SAAHPVSQWALTKK-UHFFFAOYSA-N 0.000 claims description 2
• LARXSFJKOHJCHT-UHFFFAOYSA-N 5-(4-cyanophenyl)sulfinyl-n-cyclopropyl-6-methyl-2-oxo-1-[3-(trifluoromethyl)phenyl]pyridine-3-carboxamide Chemical compound O=C1N(C=2C=C(C=CC=2)C(F)(F)F)C(C)=C(S(=O)C=2C=CC(=CC=2)C#N)C=C1C(=O)NC1CC1 LARXSFJKOHJCHT-UHFFFAOYSA-N 0.000 claims description 2
• BNPZZXVAJZJQBK-UHFFFAOYSA-N 5-(4-cyanophenyl)sulfonyl-n-(1-hydroxy-2-methylpropan-2-yl)-6-methyl-2-oxo-1-[3-(trifluoromethyl)phenyl]pyridine-3-carboxamide Chemical compound CC1=C(S(=O)(=O)C=2C=CC(=CC=2)C#N)C=C(C(=O)NC(C)(C)CO)C(=O)N1C1=CC=CC(C(F)(F)F)=C1 BNPZZXVAJZJQBK-UHFFFAOYSA-N 0.000 claims description 2
• PLMCTZFMJOVYTF-UHFFFAOYSA-N 5-(4-ethynylphenyl)sulfinyl-6-methyl-n-[(4-methylsulfonylphenyl)methyl]-2-oxo-1-[3-(trifluoromethyl)phenyl]pyridine-3-carboxamide Chemical compound O=C1N(C=2C=C(C=CC=2)C(F)(F)F)C(C)=C(S(=O)C=2C=CC(=CC=2)C#C)C=C1C(=O)NCC1=CC=C(S(C)(=O)=O)C=C1 PLMCTZFMJOVYTF-UHFFFAOYSA-N 0.000 claims description 2
• CXFKPPYWLGFUCG-UHFFFAOYSA-N 5-(4-fluorophenyl)sulfinyl-6-methyl-n-[(4-methylsulfonylphenyl)methyl]-2-oxo-1-[3-(trifluoromethyl)phenyl]pyridine-3-carboxamide Chemical compound O=C1N(C=2C=C(C=CC=2)C(F)(F)F)C(C)=C(S(=O)C=2C=CC(F)=CC=2)C=C1C(=O)NCC1=CC=C(S(C)(=O)=O)C=C1 CXFKPPYWLGFUCG-UHFFFAOYSA-N 0.000 claims description 2
• DCDXMKDDBZQXTO-UHFFFAOYSA-N 5-(4-fluorophenyl)sulfinyl-n,6-dimethyl-2-oxo-1-[3-(trifluoromethyl)phenyl]pyridine-3-carboxamide Chemical compound O=C1C(C(=O)NC)=CC(S(=O)C=2C=CC(F)=CC=2)=C(C)N1C1=CC=CC(C(F)(F)F)=C1 DCDXMKDDBZQXTO-UHFFFAOYSA-N 0.000 claims description 2
• NULYXYLATLMXMU-UHFFFAOYSA-N 5-(benzenesulfinyl)-6-methyl-n-[(4-methylsulfonylphenyl)methyl]-2-oxo-1-[3-(trifluoromethyl)phenyl]pyridine-3-carboxamide Chemical compound O=C1N(C=2C=C(C=CC=2)C(F)(F)F)C(C)=C(S(=O)C=2C=CC=CC=2)C=C1C(=O)NCC1=CC=C(S(C)(=O)=O)C=C1 NULYXYLATLMXMU-UHFFFAOYSA-N 0.000 claims description 2
• MJAGNYSUDIDSHS-UHFFFAOYSA-N 5-(benzenesulfonyl)-2-oxo-n-[3-(2-oxopyrrolidin-1-yl)propyl]-1-[3-(trifluoromethyl)phenyl]pyridine-3-carboxamide Chemical compound FC(F)(F)C1=CC=CC(N2C(C(C(=O)NCCCN3C(CCC3)=O)=CC(=C2)S(=O)(=O)C=2C=CC=CC=2)=O)=C1 MJAGNYSUDIDSHS-UHFFFAOYSA-N 0.000 claims description 2
• LBVGHQVONDHVSL-UHFFFAOYSA-N 5-ethylsulfinyl-6-methyl-n-[(4-methylsulfonylphenyl)methyl]-2-oxo-1-[3-(trifluoromethyl)phenyl]pyridine-3-carboxamide Chemical compound O=C1N(C=2C=C(C=CC=2)C(F)(F)F)C(C)=C(S(=O)CC)C=C1C(=O)NCC1=CC=C(S(C)(=O)=O)C=C1 LBVGHQVONDHVSL-UHFFFAOYSA-N 0.000 claims description 2
• CRANXOCXSWSZPZ-UHFFFAOYSA-N 6-methyl-5-(4-methylphenyl)sulfinyl-n-[(4-methylsulfonylphenyl)methyl]-2-oxo-1-[3-(trifluoromethyl)phenyl]pyridine-3-carboxamide Chemical compound C1=CC(C)=CC=C1S(=O)C1=C(C)N(C=2C=C(C=CC=2)C(F)(F)F)C(=O)C(C(=O)NCC=2C=CC(=CC=2)S(C)(=O)=O)=C1 CRANXOCXSWSZPZ-UHFFFAOYSA-N 0.000 claims description 2
• BXMASAQWMVRPHL-UHFFFAOYSA-N 6-methyl-5-methylsulfonyl-n-[(4-methylsulfonylphenyl)methyl]-2-oxo-1-[3-(trifluoromethyl)phenyl]pyridine-3-carboxamide Chemical compound O=C1N(C=2C=C(C=CC=2)C(F)(F)F)C(C)=C(S(C)(=O)=O)C=C1C(=O)NCC1=CC=C(S(C)(=O)=O)C=C1 BXMASAQWMVRPHL-UHFFFAOYSA-N 0.000 claims description 2
• UBWGDMLOYATERU-UHFFFAOYSA-N 6-methyl-5-methylsulfonyl-n-[(5-methylsulfonylpyridin-2-yl)methyl]-2-oxo-1-[3-(trifluoromethyl)phenyl]pyridine-3-carboxamide Chemical compound O=C1N(C=2C=C(C=CC=2)C(F)(F)F)C(C)=C(S(C)(=O)=O)C=C1C(=O)NCC1=CC=C(S(C)(=O)=O)C=N1 UBWGDMLOYATERU-UHFFFAOYSA-N 0.000 claims description 2
• WXXVHEFUVLYQHK-UHFFFAOYSA-N 6-methyl-n-[(4-methylsulfonylphenyl)methyl]-5-[(6-morpholin-4-ylpyridin-3-yl)sulfamoyl]-2-oxo-1-[3-(trifluoromethyl)phenyl]pyridine-3-carboxamide Chemical compound O=C1N(C=2C=C(C=CC=2)C(F)(F)F)C(C)=C(S(=O)(=O)NC=2C=NC(=CC=2)N2CCOCC2)C=C1C(=O)NCC1=CC=C(S(C)(=O)=O)C=C1 WXXVHEFUVLYQHK-UHFFFAOYSA-N 0.000 claims description 2
• CVXOLEYXDPSSGL-UHFFFAOYSA-N 6-methyl-n-[(4-methylsulfonylphenyl)methyl]-5-morpholin-4-ylsulfonyl-2-oxo-1-[3-(trifluoromethyl)phenyl]pyridine-3-carboxamide Chemical compound O=C1N(C=2C=C(C=CC=2)C(F)(F)F)C(C)=C(S(=O)(=O)N2CCOCC2)C=C1C(=O)NCC1=CC=C(S(C)(=O)=O)C=C1 CVXOLEYXDPSSGL-UHFFFAOYSA-N 0.000 claims description 2
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 2
• 206010003246 arthritis Diseases 0.000 claims description 2
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