CA2327585A1 - Use of a cox-2 inhibitor and a nk-1 receptor antagonist for treating inflammation - Google Patents

Info

Publication number

CA2327585A1

CA2327585A1 CA002327585A CA2327585A CA2327585A1 CA 2327585 A1 CA2327585 A1 CA 2327585A1 CA 002327585 A CA002327585 A CA 002327585A CA 2327585 A CA2327585 A CA 2327585A CA 2327585 A1 CA2327585 A1 CA 2327585A1

Authority

CA

Canada

Prior art keywords

phenyl

trifluoromethyl

methylsulfonyl

fluorophenyl

benzenesulfonamide

Prior art date

1998-05-21

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

• 108010040718 Neurokinin-1 Receptors Proteins 0.000 title claims abstract description 92
• 102000002002 Neurokinin-1 Receptors Human genes 0.000 title claims abstract description 92
• 239000002464 receptor antagonist Substances 0.000 title claims abstract description 84
• 229940044551 receptor antagonist Drugs 0.000 title claims abstract description 84
• 239000003255 cyclooxygenase 2 inhibitor Substances 0.000 title claims abstract description 61
• 229940111134 coxibs Drugs 0.000 title claims abstract description 56
• 206010061218 Inflammation Diseases 0.000 title description 5
• 230000004054 inflammatory process Effects 0.000 title description 5
• 238000000034 method Methods 0.000 claims abstract description 34
• 208000027866 inflammatory disease Diseases 0.000 claims abstract description 31
• 239000003814 drug Substances 0.000 claims abstract description 23
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 11
• 230000002265 prevention Effects 0.000 claims abstract description 10
• 238000004519 manufacturing process Methods 0.000 claims abstract description 8
• 150000001875 compounds Chemical class 0.000 claims description 106
• 239000001257 hydrogen Substances 0.000 claims description 72
• 229910052739 hydrogen Inorganic materials 0.000 claims description 72
• -1 phenoxy, benzyloxy Chemical group 0.000 claims description 61
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 58
• 150000003839 salts Chemical class 0.000 claims description 53
• 239000000203 mixture Substances 0.000 claims description 38
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 38
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 35
• 125000000217 alkyl group Chemical group 0.000 claims description 34
• 125000005843 halogen group Chemical group 0.000 claims description 32
• 150000002431 hydrogen Chemical group 0.000 claims description 32
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 31
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 31
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 29
• 125000001424 substituent group Chemical group 0.000 claims description 28
• 125000004432 carbon atom Chemical group C* 0.000 claims description 24
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 22
• 125000003118 aryl group Chemical group 0.000 claims description 21
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 21
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 21
• 125000001624 naphthyl group Chemical group 0.000 claims description 21
• 125000001072 heteroaryl group Chemical group 0.000 claims description 18
• 229910052760 oxygen Inorganic materials 0.000 claims description 18
• 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 17
• 125000004076 pyridyl group Chemical group 0.000 claims description 17
• 125000001153 fluoro group Chemical group F* 0.000 claims description 16
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 15
• 229910052736 halogen Inorganic materials 0.000 claims description 15
• 150000002367 halogens Chemical class 0.000 claims description 15
• 229910052757 nitrogen Inorganic materials 0.000 claims description 15
• 239000001301 oxygen Substances 0.000 claims description 13
• 230000002829 reductive effect Effects 0.000 claims description 13
• 125000001544 thienyl group Chemical group 0.000 claims description 13
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 12
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 12
• 150000003254 radicals Chemical group 0.000 claims description 12
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 11
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 11
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 11
• 239000011737 fluorine Substances 0.000 claims description 11
• 229910052731 fluorine Inorganic materials 0.000 claims description 11
• 125000000623 heterocyclic group Chemical group 0.000 claims description 11
• 238000002360 preparation method Methods 0.000 claims description 11
• 125000002252 acyl group Chemical group 0.000 claims description 10
• 229910052799 carbon Inorganic materials 0.000 claims description 10
• 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 10
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 10
• 239000003937 drug carrier Substances 0.000 claims description 10
• 125000003386 piperidinyl group Chemical group 0.000 claims description 10
• 125000002541 furyl group Chemical group 0.000 claims description 9
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
• KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims description 8
• 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 8
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 8
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
• ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical group C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 claims description 8
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 8
• 229910052717 sulfur Inorganic materials 0.000 claims description 8
• 125000005493 quinolyl group Chemical group 0.000 claims description 7
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
• 239000005864 Sulphur Substances 0.000 claims description 6
• 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 6
• 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 6
• 125000001041 indolyl group Chemical group 0.000 claims description 6
• 125000001786 isothiazolyl group Chemical group 0.000 claims description 6
• 125000000842 isoxazolyl group Chemical group 0.000 claims description 6
• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 6
• 206010039073 rheumatoid arthritis Diseases 0.000 claims description 6
• 125000006413 ring segment Chemical group 0.000 claims description 6
• 125000003831 tetrazolyl group Chemical group 0.000 claims description 6
• 125000001425 triazolyl group Chemical group 0.000 claims description 6
• 229940093444 Cyclooxygenase 2 inhibitor Drugs 0.000 claims description 5
• 239000000460 chlorine Substances 0.000 claims description 5
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 5
• GLCIVEUJSREFOQ-ORYQWCPZSA-N (3r,5r,10s)-3-[2-methoxy-5-(trifluoromethoxy)phenyl]-10-phenyl-1-oxa-9-azaspiro[4.5]decane Chemical compound COC1=CC=C(OC(F)(F)F)C=C1[C@H]1C[C@]2([C@@H](NCCC2)C=2C=CC=CC=2)OC1 GLCIVEUJSREFOQ-ORYQWCPZSA-N 0.000 claims description 4
• FITTVVADRSOGKC-MXSCXNJPSA-N (3r,5r,10s)-9-benzyl-3-[2-methoxy-5-(trifluoromethoxy)phenyl]-10-phenyl-1-oxa-9-azaspiro[4.5]decane Chemical compound COC1=CC=C(OC(F)(F)F)C=C1[C@H]1C[C@]2([C@@H](N(CC=3C=CC=CC=3)CCC2)C=2C=CC=CC=2)OC1 FITTVVADRSOGKC-MXSCXNJPSA-N 0.000 claims description 4
• ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 claims description 4
• JHBIMJKLBUMNAU-UHFFFAOYSA-N SC-58125 Chemical compound C1=CC(S(=O)(=O)C)=CC=C1N1C(C=2C=CC(F)=CC=2)=CC(C(F)(F)F)=N1 JHBIMJKLBUMNAU-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
• 125000003545 alkoxy group Chemical group 0.000 claims description 4
• 125000002947 alkylene group Chemical group 0.000 claims description 4
• 125000001246 bromo group Chemical group Br* 0.000 claims description 4
• CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 claims description 4
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
• 125000004122 cyclic group Chemical group 0.000 claims description 4
• 125000000000 cycloalkoxy group Chemical group 0.000 claims description 4
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
• 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims description 4
• 125000002346 iodo group Chemical group I* 0.000 claims description 4
• 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 4
• 125000002757 morpholinyl group Chemical group 0.000 claims description 4
• 201000008482 osteoarthritis Diseases 0.000 claims description 4
• 125000002971 oxazolyl group Chemical group 0.000 claims description 4
• 125000004193 piperazinyl group Chemical group 0.000 claims description 4
• 229920006395 saturated elastomer Polymers 0.000 claims description 4
• 125000003003 spiro group Chemical group 0.000 claims description 4
• 125000003107 substituted aryl group Chemical group 0.000 claims description 4
• 239000011593 sulfur Substances 0.000 claims description 4
• 125000000335 thiazolyl group Chemical group 0.000 claims description 4
• 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 4
• 125000000081 (C5-C8) cycloalkenyl group Chemical group 0.000 claims description 3
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
• GJGZQTGPOKPFES-UHFFFAOYSA-N SC-57666 Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=CC(F)=CC=2)CCC1 GJGZQTGPOKPFES-UHFFFAOYSA-N 0.000 claims description 3
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 3
• 125000002837 carbocyclic group Chemical group 0.000 claims description 3
• 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 3
• 229910052801 chlorine Inorganic materials 0.000 claims description 3
• 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 3
• 125000002883 imidazolyl group Chemical group 0.000 claims description 3
• 125000001715 oxadiazolyl group Chemical group 0.000 claims description 3
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 3
• 125000003373 pyrazinyl group Chemical group 0.000 claims description 3
• 125000001113 thiadiazolyl group Chemical group 0.000 claims description 3
• UGIPKCIBIXXIEF-HNAYVOBHSA-N (2s,3s)-3-[[2-methoxy-5-(trifluoromethoxy)phenyl]methyl]-2-phenylpiperidin-1-amine Chemical compound COC1=CC=C(OC(F)(F)F)C=C1C[C@H]1[C@@H](C=2C=CC=CC=2)N(N)CCC1 UGIPKCIBIXXIEF-HNAYVOBHSA-N 0.000 claims description 2
• DTQNEFOKTXXQKV-HKUYNNGSSA-N (2s,3s)-n-[(2-methoxyphenyl)methyl]-2-phenylpiperidin-3-amine Chemical compound COC1=CC=CC=C1CN[C@@H]1[C@H](C=2C=CC=CC=2)NCCC1 DTQNEFOKTXXQKV-HKUYNNGSSA-N 0.000 claims description 2
• DZYPLFAASKBQBS-ICSRJNTNSA-N (2s,3s)-n-[[2-methoxy-5-(tetrazol-1-yl)phenyl]methyl]-2-phenylpiperidin-3-amine Chemical compound C1([C@@H]2NCCC[C@@H]2NCC2=CC(=CC=C2OC)N2N=NN=C2)=CC=CC=C1 DZYPLFAASKBQBS-ICSRJNTNSA-N 0.000 claims description 2
• XILNRORTJVDYRH-HKUYNNGSSA-N (2s,3s)-n-[[2-methoxy-5-[5-(trifluoromethyl)tetrazol-1-yl]phenyl]methyl]-2-phenylpiperidin-3-amine Chemical compound C1([C@@H]2NCCC[C@@H]2NCC2=CC(=CC=C2OC)N2C(=NN=N2)C(F)(F)F)=CC=CC=C1 XILNRORTJVDYRH-HKUYNNGSSA-N 0.000 claims description 2
• WJRYRJACQITXQC-SLFFLAALSA-N (3r,5r,10s)-3,10-diphenyl-1-oxa-9-azaspiro[4.5]decane Chemical compound C1([C@H]2C[C@@]3(OC2)[C@@H](NCCC3)C=2C=CC=CC=2)=CC=CC=C1 WJRYRJACQITXQC-SLFFLAALSA-N 0.000 claims description 2
• ACSJGOJPLODBLW-DZFGPLHGSA-N (3r,5r,10s)-3-(2-methoxyphenyl)-10-phenyl-1-oxa-9-azaspiro[4.5]decane Chemical compound COC1=CC=CC=C1[C@H]1C[C@]2([C@@H](NCCC2)C=2C=CC=CC=2)OC1 ACSJGOJPLODBLW-DZFGPLHGSA-N 0.000 claims description 2
• BGDPHCDFHQZNLQ-ORYQWCPZSA-N (3r,5r,10s)-3-[2-methoxy-5-(trifluoromethyl)phenyl]-10-phenyl-1-oxa-9-azaspiro[4.5]decane Chemical compound COC1=CC=C(C(F)(F)F)C=C1[C@H]1C[C@]2([C@@H](NCCC2)C=2C=CC=CC=2)OC1 BGDPHCDFHQZNLQ-ORYQWCPZSA-N 0.000 claims description 2
• UEXKTMCOJRYCCT-MQNAVGNWSA-N (3s,5r,10s)-3-[2-cyclopropyloxy-5-(trifluoromethoxy)phenyl]-10-phenyl-1-oxa-9-azaspiro[4.5]decane Chemical compound C1([C@@H]2C[C@@]3(OC2)[C@@H](NCCC3)C=2C=CC=CC=2)=CC(OC(F)(F)F)=CC=C1OC1CC1 UEXKTMCOJRYCCT-MQNAVGNWSA-N 0.000 claims description 2
• 125000002861 (C1-C4) alkanoyl group Chemical group 0.000 claims description 2
• LWIFWMYFVZYWMS-UHFFFAOYSA-N 1,2-difluoro-3-[2-(4-methylsulfonylphenyl)cyclopenten-1-yl]benzene Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C(=C(F)C=CC=2)F)CCC1 LWIFWMYFVZYWMS-UHFFFAOYSA-N 0.000 claims description 2
• RFPZMXMBYMEQHZ-UHFFFAOYSA-N 1-(4-fluorophenyl)-2-(4-methylsulfonylphenyl)benzene Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=CC=CC=C1C1=CC=C(F)C=C1 RFPZMXMBYMEQHZ-UHFFFAOYSA-N 0.000 claims description 2
• GWMFOHRUWPDLIP-UHFFFAOYSA-N 1-(4-methylsulfonylphenyl)-2-phenyl-4-(trifluoromethyl)imidazole Chemical compound C1=CC(S(=O)(=O)C)=CC=C1N1C(C=2C=CC=CC=2)=NC(C(F)(F)F)=C1 GWMFOHRUWPDLIP-UHFFFAOYSA-N 0.000 claims description 2
• HUVCBGHNHBHJBX-UHFFFAOYSA-N 1-[2-(4-chlorophenyl)-4,4-dimethylcyclopenten-1-yl]-4-methylsulfonylbenzene Chemical compound C1C(C)(C)CC(C=2C=CC(Cl)=CC=2)=C1C1=CC=C(S(C)(=O)=O)C=C1 HUVCBGHNHBHJBX-UHFFFAOYSA-N 0.000 claims description 2
• MBUIIOVYVHAZOU-UHFFFAOYSA-N 1-[2-(4-chlorophenyl)cyclopenten-1-yl]-4-methylsulfonylbenzene Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=CC(Cl)=CC=2)CCC1 MBUIIOVYVHAZOU-UHFFFAOYSA-N 0.000 claims description 2
• SZHKSRZKPUOAGO-UHFFFAOYSA-N 1-[2-(4-methylsulfonylphenyl)cyclopenten-1-yl]-4-(trifluoromethyl)benzene Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=CC(=CC=2)C(F)(F)F)CCC1 SZHKSRZKPUOAGO-UHFFFAOYSA-N 0.000 claims description 2
• BPWDIXPFAHESAF-UHFFFAOYSA-N 1-[3,3-dimethyl-5-(4-methylsulfonylphenyl)cyclopenta-1,4-dien-1-yl]-4-fluorobenzene Chemical compound C=1C(C)(C)C=C(C=2C=CC(F)=CC=2)C=1C1=CC=C(S(C)(=O)=O)C=C1 BPWDIXPFAHESAF-UHFFFAOYSA-N 0.000 claims description 2
• VKUCTHVTLJBHDT-UHFFFAOYSA-N 1-[4,4-dimethyl-2-(4-methylsulfonylphenyl)cyclopenten-1-yl]-4-fluorobenzene Chemical compound C1C(C)(C)CC(C=2C=CC(F)=CC=2)=C1C1=CC=C(S(C)(=O)=O)C=C1 VKUCTHVTLJBHDT-UHFFFAOYSA-N 0.000 claims description 2
• USRYEHHMJIRICK-ZNZBMKLDSA-N 1-[5-[[(2r,3s)-2-[(1r)-1-[3,5-bis(trifluoromethyl)phenyl]ethoxy]-3-(4-fluorophenyl)morpholin-4-yl]methyl]-2h-triazol-4-yl]-n,n-dimethylmethanamine Chemical compound O([C@@H]([C@@H]1C=2C=CC(F)=CC=2)O[C@H](C)C=2C=C(C=C(C=2)C(F)(F)F)C(F)(F)F)CCN1CC1=NNN=C1CN(C)C USRYEHHMJIRICK-ZNZBMKLDSA-N 0.000 claims description 2
• MFKDAOCUEASALN-QQTNTEGQSA-N 1-[5-[[(2r,3s)-2-[(1r)-1-[3,5-bis(trifluoromethyl)phenyl]ethoxy]-3-phenylmorpholin-4-yl]methyl]-2h-triazol-4-yl]-n,n-dimethylmethanamine Chemical compound O([C@@H]([C@@H]1C=2C=CC=CC=2)O[C@H](C)C=2C=C(C=C(C=2)C(F)(F)F)C(F)(F)F)CCN1CC1=NNN=C1CN(C)C MFKDAOCUEASALN-QQTNTEGQSA-N 0.000 claims description 2
• XKSNSSNGFIQSFK-UHFFFAOYSA-N 1-ethyl-4-(4-fluorophenyl)-3-(4-methylsulfonylphenyl)-5-(trifluoromethyl)pyrazole Chemical compound FC(F)(F)C=1N(CC)N=C(C=2C=CC(=CC=2)S(C)(=O)=O)C=1C1=CC=C(F)C=C1 XKSNSSNGFIQSFK-UHFFFAOYSA-N 0.000 claims description 2
• RAUHMMADXJJVRP-UHFFFAOYSA-N 1-methoxy-4-[2-(4-methylsulfonylphenyl)cyclopenten-1-yl]benzene Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=CC(=CC=2)S(C)(=O)=O)CCC1 RAUHMMADXJJVRP-UHFFFAOYSA-N 0.000 claims description 2
• JQDLRYPRLMZWFM-UHFFFAOYSA-N 1-methylsulfanyl-4-[2-(4-methylsulfonylphenyl)cyclopenten-1-yl]benzene Chemical compound C1=CC(SC)=CC=C1C1=C(C=2C=CC(=CC=2)S(C)(=O)=O)CCC1 JQDLRYPRLMZWFM-UHFFFAOYSA-N 0.000 claims description 2
• YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims description 2
• KSFMAASFLCWROX-UHFFFAOYSA-N 2,4-dichloro-1-[2-(4-methylsulfonylphenyl)cyclopenten-1-yl]benzene Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C(=CC(Cl)=CC=2)Cl)CCC1 KSFMAASFLCWROX-UHFFFAOYSA-N 0.000 claims description 2
• VCLNQQUCGTWUKD-UHFFFAOYSA-N 2-(2-chlorophenyl)-4-(4-fluorophenyl)-5-(4-methylsulfonylphenyl)-1,3-thiazole Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=CC(F)=CC=2)N=C(C=2C(=CC=CC=2)Cl)S1 VCLNQQUCGTWUKD-UHFFFAOYSA-N 0.000 claims description 2
• ULFYMTMZNITFSB-UHFFFAOYSA-N 2-(3,5-difluorophenyl)-3-(4-methylsulfonylphenyl)cyclopent-2-en-1-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=C(F)C=C(F)C=2)C(=O)CC1 ULFYMTMZNITFSB-UHFFFAOYSA-N 0.000 claims description 2
• SOOKCKQNOCMHPV-UHFFFAOYSA-N 2-(3-chloro-4-fluorophenyl)-4-(4-fluorophenyl)-5-(4-methylsulfonylphenyl)-1,3-thiazole Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=CC(F)=CC=2)N=C(C=2C=C(Cl)C(F)=CC=2)S1 SOOKCKQNOCMHPV-UHFFFAOYSA-N 0.000 claims description 2
• YLFBPUKBMRJHLM-UHFFFAOYSA-N 2-(3-chlorophenyl)-1-(4-methylsulfonylphenyl)-4-(trifluoromethyl)imidazole Chemical compound C1=CC(S(=O)(=O)C)=CC=C1N1C(C=2C=C(Cl)C=CC=2)=NC(C(F)(F)F)=C1 YLFBPUKBMRJHLM-UHFFFAOYSA-N 0.000 claims description 2
• MEAMLMDMYOLDGW-UHFFFAOYSA-N 2-(3-fluoro-5-methylphenyl)-1-(4-methylsulfonylphenyl)-4-(trifluoromethyl)imidazole Chemical compound CC1=CC(F)=CC(C=2N(C=C(N=2)C(F)(F)F)C=2C=CC(=CC=2)S(C)(=O)=O)=C1 MEAMLMDMYOLDGW-UHFFFAOYSA-N 0.000 claims description 2
• RSABMOYFBOLDLO-UHFFFAOYSA-N 2-(3-methylphenyl)-1-(4-methylsulfonylphenyl)-4-(trifluoromethyl)imidazole Chemical compound CC1=CC=CC(C=2N(C=C(N=2)C(F)(F)F)C=2C=CC(=CC=2)S(C)(=O)=O)=C1 RSABMOYFBOLDLO-UHFFFAOYSA-N 0.000 claims description 2
• ZZBKFGAUXXMYNA-UHFFFAOYSA-N 2-(4-chlorophenyl)-1-(4-methylsulfonylphenyl)-4-phenylimidazole Chemical compound C1=CC(S(=O)(=O)C)=CC=C1N1C(C=2C=CC(Cl)=CC=2)=NC(C=2C=CC=CC=2)=C1 ZZBKFGAUXXMYNA-UHFFFAOYSA-N 0.000 claims description 2
• UPXZCQZUZDWZHE-UHFFFAOYSA-N 2-(4-chlorophenyl)-4-(4-fluorophenyl)-1-(4-methylsulfonylphenyl)imidazole Chemical compound C1=CC(S(=O)(=O)C)=CC=C1N1C(C=2C=CC(Cl)=CC=2)=NC(C=2C=CC(F)=CC=2)=C1 UPXZCQZUZDWZHE-UHFFFAOYSA-N 0.000 claims description 2
• RIZFWOPNUQFLEF-UHFFFAOYSA-N 2-(4-chlorophenyl)-4-methyl-1-(4-methylsulfonylphenyl)imidazole Chemical compound N=1C(C)=CN(C=2C=CC(=CC=2)S(C)(=O)=O)C=1C1=CC=C(Cl)C=C1 RIZFWOPNUQFLEF-UHFFFAOYSA-N 0.000 claims description 2
• PEUVGLHBVHFKPT-UHFFFAOYSA-N 2-(4-methylphenyl)-1-(4-methylsulfonylphenyl)-4-(trifluoromethyl)imidazole Chemical compound C1=CC(C)=CC=C1C1=NC(C(F)(F)F)=CN1C1=CC=C(S(C)(=O)=O)C=C1 PEUVGLHBVHFKPT-UHFFFAOYSA-N 0.000 claims description 2
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• ZFFYQVIHYPYXPI-UHFFFAOYSA-N 4-[3-(difluoromethyl)-5-phenylpyrazol-1-yl]benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1N1C(C=2C=CC=CC=2)=CC(C(F)F)=N1 ZFFYQVIHYPYXPI-UHFFFAOYSA-N 0.000 claims description 2
• UUGSJYRNELHGOL-UHFFFAOYSA-N 4-[3-cyano-5-(4-fluorophenyl)pyrazol-1-yl]benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1N1C(C=2C=CC(F)=CC=2)=CC(C#N)=N1 UUGSJYRNELHGOL-UHFFFAOYSA-N 0.000 claims description 2
• XRHRZRHLXNWUTF-UHFFFAOYSA-N 4-[4-chloro-5-(4-chlorophenyl)-3-(trifluoromethyl)pyrazol-1-yl]benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1N1C(C=2C=CC(Cl)=CC=2)=C(Cl)C(C(F)(F)F)=N1 XRHRZRHLXNWUTF-UHFFFAOYSA-N 0.000 claims description 2
• ONDHXPGHTRDUMN-UHFFFAOYSA-N 4-[5-(3-fluoro-4-methoxyphenyl)-2-(trifluoromethyl)-1,3-oxazol-4-yl]benzenesulfonamide Chemical compound C1=C(F)C(OC)=CC=C1C1=C(C=2C=CC(=CC=2)S(N)(=O)=O)N=C(C(F)(F)F)O1 ONDHXPGHTRDUMN-UHFFFAOYSA-N 0.000 claims description 2
• GETBJRSHOBBZKB-UHFFFAOYSA-N 4-[5-(3-fluoro-4-methoxyphenyl)-3-(trifluoromethyl)pyrazol-1-yl]benzenesulfonamide Chemical compound C1=C(F)C(OC)=CC=C1C1=CC(C(F)(F)F)=NN1C1=CC=C(S(N)(=O)=O)C=C1 GETBJRSHOBBZKB-UHFFFAOYSA-N 0.000 claims description 2
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• RDVMVFHKIXFZDK-UHFFFAOYSA-N 4-[5-(4-chlorophenyl)-3-(4-methoxyphenyl)pyrazol-1-yl]benzenesulfonamide Chemical compound C1=CC(OC)=CC=C1C1=NN(C=2C=CC(=CC=2)S(N)(=O)=O)C(C=2C=CC(Cl)=CC=2)=C1 RDVMVFHKIXFZDK-UHFFFAOYSA-N 0.000 claims description 2
• SZDMSAGZJBRJNW-UHFFFAOYSA-N 4-[5-(4-chlorophenyl)-3-(4-methylphenyl)pyrazol-1-yl]benzenesulfonamide Chemical compound C1=CC(C)=CC=C1C1=NN(C=2C=CC(=CC=2)S(N)(=O)=O)C(C=2C=CC(Cl)=CC=2)=C1 SZDMSAGZJBRJNW-UHFFFAOYSA-N 0.000 claims description 2
• KJIAFIBHGWAADR-UHFFFAOYSA-N 4-[5-(4-chlorophenyl)-3-(4-nitrophenyl)pyrazol-1-yl]benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1N1C(C=2C=CC(Cl)=CC=2)=CC(C=2C=CC(=CC=2)[N+]([O-])=O)=N1 KJIAFIBHGWAADR-UHFFFAOYSA-N 0.000 claims description 2
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