NZ517424A - Pharmaceutically active sulfonamide derivatives - Google Patents

Info

Publication number

NZ517424A

NZ517424A NZ517424A NZ51742400A NZ517424A NZ 517424 A NZ517424 A NZ 517424A NZ 517424 A NZ517424 A NZ 517424A NZ 51742400 A NZ51742400 A NZ 51742400A NZ 517424 A NZ517424 A NZ 517424A

Authority

NZ

New Zealand

Prior art keywords

sulfonyl

methyl

thien

piperidin

benzamide

Prior art date

1999-09-28

Links

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• Global Dossier
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• 229940124530 sulfonamide Drugs 0.000 title claims abstract description 60
• 150000003456 sulfonamides Chemical class 0.000 title claims abstract description 49
• 150000001875 compounds Chemical class 0.000 claims abstract description 89
• 238000002360 preparation method Methods 0.000 claims abstract description 37
• 230000001537 neural effect Effects 0.000 claims abstract description 12
• 230000000694 effects Effects 0.000 claims abstract description 11
• KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 399
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 258
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 190
• -1 piperazino group Chemical group 0.000 claims description 177
• 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 114
• 238000000034 method Methods 0.000 claims description 49
• 101000950669 Homo sapiens Mitogen-activated protein kinase 9 Proteins 0.000 claims description 46
• 102100037809 Mitogen-activated protein kinase 9 Human genes 0.000 claims description 46
• 125000003118 aryl group Chemical group 0.000 claims description 46
• 125000001072 heteroaryl group Chemical group 0.000 claims description 44
• 229910052739 hydrogen Inorganic materials 0.000 claims description 44
• 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 40
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 40
• 229910052757 nitrogen Inorganic materials 0.000 claims description 33
• 239000000203 mixture Substances 0.000 claims description 32
• 239000001257 hydrogen Substances 0.000 claims description 29
• HFFXLYHRNRKAPM-UHFFFAOYSA-N 2,4,5-trichloro-n-(5-methyl-1,2-oxazol-3-yl)benzenesulfonamide Chemical compound O1C(C)=CC(NS(=O)(=O)C=2C(=CC(Cl)=C(Cl)C=2)Cl)=N1 HFFXLYHRNRKAPM-UHFFFAOYSA-N 0.000 claims description 25
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 25
• 125000001544 thienyl group Chemical group 0.000 claims description 25
• GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 24
• 150000001412 amines Chemical class 0.000 claims description 24
• 229910052760 oxygen Inorganic materials 0.000 claims description 23
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 22
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 22
• 230000037361 pathway Effects 0.000 claims description 22
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 20
• 239000008194 pharmaceutical composition Substances 0.000 claims description 20
• YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 claims description 20
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 20
• 208000035475 disorder Diseases 0.000 claims description 19
• 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims description 19
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 18
• 125000004122 cyclic group Chemical group 0.000 claims description 17
• RWTNPBWLLIMQHL-UHFFFAOYSA-N fexofenadine Chemical compound C1=CC(C(C)(C(O)=O)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 RWTNPBWLLIMQHL-UHFFFAOYSA-N 0.000 claims description 17
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 15
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 15
• 125000002541 furyl group Chemical group 0.000 claims description 15
• 239000001301 oxygen Substances 0.000 claims description 15
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 15
• 150000003839 salts Chemical class 0.000 claims description 15
• 125000000242 4-chlorobenzoyl group Chemical group ClC1=CC=C(C(=O)*)C=C1 0.000 claims description 13
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 13
• 229910052736 halogen Inorganic materials 0.000 claims description 13
• 125000001424 substituent group Chemical group 0.000 claims description 11
• 238000012360 testing method Methods 0.000 claims description 11
• 150000002367 halogens Chemical class 0.000 claims description 10
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 10
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 9
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 9
• 238000005859 coupling reaction Methods 0.000 claims description 9
• 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 9
• 230000008569 process Effects 0.000 claims description 9
• 229920006395 saturated elastomer Polymers 0.000 claims description 9
• 125000003107 substituted aryl group Chemical group 0.000 claims description 9
• 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 8
• HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 8
• 125000005605 benzo group Chemical group 0.000 claims description 8
• 125000005842 heteroatom Chemical group 0.000 claims description 8
• 229910052717 sulfur Inorganic materials 0.000 claims description 8
• 150000001263 acyl chlorides Chemical class 0.000 claims description 7
• 125000004423 acyloxy group Chemical group 0.000 claims description 7
• 150000001408 amides Chemical class 0.000 claims description 7
• 239000003814 drug Substances 0.000 claims description 7
• 125000003396 thiol group Chemical group [H]S* 0.000 claims description 7
• 208000023275 Autoimmune disease Diseases 0.000 claims description 6
• 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 6
• 125000004442 acylamino group Chemical group 0.000 claims description 6
• 210000004556 brain Anatomy 0.000 claims description 6
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 6
• 230000008878 coupling Effects 0.000 claims description 6
• 238000010168 coupling process Methods 0.000 claims description 6
• 239000003085 diluting agent Substances 0.000 claims description 6
• 230000014509 gene expression Effects 0.000 claims description 6
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 6
• 125000004076 pyridyl group Chemical group 0.000 claims description 6
• 125000005309 thioalkoxy group Chemical group 0.000 claims description 6
• 229940015849 thiophene Drugs 0.000 claims description 6
• RBGDLYUEXLWQBZ-UHFFFAOYSA-N 2-chlorobenzamide Chemical compound NC(=O)C1=CC=CC=C1Cl RBGDLYUEXLWQBZ-UHFFFAOYSA-N 0.000 claims description 5
• VATVSEAGDZXHND-UHFFFAOYSA-N 4-nitro-n-[[5-[4-[3-(trifluoromethylsulfonyl)anilino]piperidin-1-yl]sulfonylthiophen-2-yl]methyl]benzamide Chemical compound C1=CC([N+](=O)[O-])=CC=C1C(=O)NCC1=CC=C(S(=O)(=O)N2CCC(CC2)NC=2C=C(C=CC=2)S(=O)(=O)C(F)(F)F)S1 VATVSEAGDZXHND-UHFFFAOYSA-N 0.000 claims description 5
• 108010055717 JNK Mitogen-Activated Protein Kinases Proteins 0.000 claims description 5
• 241001465754 Metazoa Species 0.000 claims description 5
• 206010040070 Septic Shock Diseases 0.000 claims description 5
• PXXJHWLDUBFPOL-UHFFFAOYSA-N benzamidine Chemical compound NC(=N)C1=CC=CC=C1 PXXJHWLDUBFPOL-UHFFFAOYSA-N 0.000 claims description 5
• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 5
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
• 125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 5
• FQUYSHZXSKYCSY-UHFFFAOYSA-N 1,4-diazepane Chemical group C1CNCCNC1 FQUYSHZXSKYCSY-UHFFFAOYSA-N 0.000 claims description 4
• VPKKBWBYGRMALQ-UHFFFAOYSA-N 1-$l^{1}-azanylpyrrolidine Chemical compound [N]N1CCCC1 VPKKBWBYGRMALQ-UHFFFAOYSA-N 0.000 claims description 4
• 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 4
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
• QQQGBUXUGKEYGK-UHFFFAOYSA-N 3-methoxy-n-[[5-[4-(2-nitroanilino)piperidin-1-yl]sulfonylthiophen-2-yl]methyl]benzamide Chemical compound COC1=CC=CC(C(=O)NCC=2SC(=CC=2)S(=O)(=O)N2CCC(CC2)NC=2C(=CC=CC=2)[N+]([O-])=O)=C1 QQQGBUXUGKEYGK-UHFFFAOYSA-N 0.000 claims description 4
• ACBBNXWLABVBQR-UHFFFAOYSA-N 4-chloro-n-[[5-[4-[3-(2-hydroxyethylsulfonyl)anilino]piperidin-1-yl]sulfonylthiophen-2-yl]methyl]benzamide Chemical compound OCCS(=O)(=O)C1=CC=CC(NC2CCN(CC2)S(=O)(=O)C=2SC(CNC(=O)C=3C=CC(Cl)=CC=3)=CC=2)=C1 ACBBNXWLABVBQR-UHFFFAOYSA-N 0.000 claims description 4
• IEYDNUOBCIZCKI-UHFFFAOYSA-N 4-nitro-n-[[5-[4-[3-(trifluoromethylsulfanyl)anilino]piperidin-1-yl]sulfonylthiophen-2-yl]methyl]benzamide Chemical compound C1=CC([N+](=O)[O-])=CC=C1C(=O)NCC1=CC=C(S(=O)(=O)N2CCC(CC2)NC=2C=C(SC(F)(F)F)C=CC=2)S1 IEYDNUOBCIZCKI-UHFFFAOYSA-N 0.000 claims description 4
• 208000024172 Cardiovascular disease Diseases 0.000 claims description 4
• 238000002965 ELISA Methods 0.000 claims description 4
• 206010028980 Neoplasm Diseases 0.000 claims description 4
• 230000002159 abnormal effect Effects 0.000 claims description 4
• ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 claims description 4
• 125000004043 oxo group Chemical group O=* 0.000 claims description 4
• 230000002265 prevention Effects 0.000 claims description 4
• SEWLNURZZLDDAU-UHFFFAOYSA-N 3-nitro-n-[[5-[4-(5,6,7,8-tetrahydronaphthalen-1-ylamino)piperidin-1-yl]sulfonylthiophen-2-yl]methyl]benzamide Chemical compound [O-][N+](=O)C1=CC=CC(C(=O)NCC=2SC(=CC=2)S(=O)(=O)N2CCC(CC2)NC=2C=3CCCCC=3C=CC=2)=C1 SEWLNURZZLDDAU-UHFFFAOYSA-N 0.000 claims description 3
• GPABLHQDHZMQOE-UHFFFAOYSA-N 4-chloro-n-[[5-[4-(2-propylanilino)piperidin-1-yl]sulfonylthiophen-2-yl]methyl]benzamide Chemical compound CCCC1=CC=CC=C1NC1CCN(S(=O)(=O)C=2SC(CNC(=O)C=3C=CC(Cl)=CC=3)=CC=2)CC1 GPABLHQDHZMQOE-UHFFFAOYSA-N 0.000 claims description 3
• UDYGTWABGZUESJ-UHFFFAOYSA-N 4-chloro-n-[[5-[4-(3,5-dichloropyridin-4-yl)piperazin-1-yl]sulfonylthiophen-2-yl]methyl]benzamide Chemical compound C1=CC(Cl)=CC=C1C(=O)NCC1=CC=C(S(=O)(=O)N2CCN(CC2)C=2C(=CN=CC=2Cl)Cl)S1 UDYGTWABGZUESJ-UHFFFAOYSA-N 0.000 claims description 3
• IYZRWZSWTUOPRF-UHFFFAOYSA-N 4-chloro-n-[[5-[4-(3-sulfamoylanilino)piperidin-1-yl]sulfonylthiophen-2-yl]methyl]benzamide Chemical compound NS(=O)(=O)C1=CC=CC(NC2CCN(CC2)S(=O)(=O)C=2SC(CNC(=O)C=3C=CC(Cl)=CC=3)=CC=2)=C1 IYZRWZSWTUOPRF-UHFFFAOYSA-N 0.000 claims description 3
• QXIPYYLJUFUICS-UHFFFAOYSA-N 4-chloro-n-[[5-[4-(4-chloroanilino)piperidin-1-yl]sulfonylthiophen-2-yl]methyl]benzamide Chemical compound C1=CC(Cl)=CC=C1NC1CCN(S(=O)(=O)C=2SC(CNC(=O)C=3C=CC(Cl)=CC=3)=CC=2)CC1 QXIPYYLJUFUICS-UHFFFAOYSA-N 0.000 claims description 3
• YWCKRKNLKAJANS-UHFFFAOYSA-N 4-chloro-n-[[5-[4-(6-chlorobenzotriazol-1-yl)piperidin-1-yl]sulfonylthiophen-2-yl]methyl]benzamide Chemical compound C1=CC(Cl)=CC=C1C(=O)NCC1=CC=C(S(=O)(=O)N2CCC(CC2)N2C3=CC(Cl)=CC=C3N=N2)S1 YWCKRKNLKAJANS-UHFFFAOYSA-N 0.000 claims description 3
• IGTIVZNWECLJKH-UHFFFAOYSA-N 4-chloro-n-[[5-[4-(oxolane-2-carbonyl)piperazin-1-yl]sulfonylthiophen-2-yl]methyl]benzamide Chemical compound C1=CC(Cl)=CC=C1C(=O)NCC1=CC=C(S(=O)(=O)N2CCN(CC2)C(=O)C2OCCC2)S1 IGTIVZNWECLJKH-UHFFFAOYSA-N 0.000 claims description 3
• 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 3
• JTQIDNVQNOJMMS-UHFFFAOYSA-N 4-nitro-n-[[5-[4-[3-(trifluoromethylsulfanyl)anilino]piperidin-1-yl]sulfonylfuran-2-yl]methyl]benzamide Chemical compound C1=CC([N+](=O)[O-])=CC=C1C(=O)NCC1=CC=C(S(=O)(=O)N2CCC(CC2)NC=2C=C(SC(F)(F)F)C=CC=2)O1 JTQIDNVQNOJMMS-UHFFFAOYSA-N 0.000 claims description 3
• 208000024827 Alzheimer disease Diseases 0.000 claims description 3
• 206010019196 Head injury Diseases 0.000 claims description 3
• 208000023105 Huntington disease Diseases 0.000 claims description 3
• 206010061216 Infarction Diseases 0.000 claims description 3
• 208000018737 Parkinson disease Diseases 0.000 claims description 3
• 206010063837 Reperfusion injury Diseases 0.000 claims description 3
• 208000017442 Retinal disease Diseases 0.000 claims description 3
• 206010052779 Transplant rejections Diseases 0.000 claims description 3
• 125000005036 alkoxyphenyl group Chemical group 0.000 claims description 3
• 208000006673 asthma Diseases 0.000 claims description 3
• 201000011510 cancer Diseases 0.000 claims description 3
• 125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
• 206010015037 epilepsy Diseases 0.000 claims description 3
• 210000001320 hippocampus Anatomy 0.000 claims description 3
• 125000004464 hydroxyphenyl group Chemical group 0.000 claims description 3
• 230000007574 infarction Effects 0.000 claims description 3
• 208000028867 ischemia Diseases 0.000 claims description 3
• MWSITTVZPOTQRK-UHFFFAOYSA-N n-[[5-(4-anilinopiperidin-1-yl)sulfonylthiophen-2-yl]methyl]-3-methoxybenzamide Chemical compound COC1=CC=CC(C(=O)NCC=2SC(=CC=2)S(=O)(=O)N2CCC(CC2)NC=2C=CC=CC=2)=C1 MWSITTVZPOTQRK-UHFFFAOYSA-N 0.000 claims description 3
• CNEKKKSOOIREKL-UHFFFAOYSA-N n-[[5-(4-benzoylpiperidin-1-yl)sulfonylthiophen-2-yl]methyl]-4-chlorobenzamide Chemical compound C1=CC(Cl)=CC=C1C(=O)NCC1=CC=C(S(=O)(=O)N2CCC(CC2)C(=O)C=2C=CC=CC=2)S1 CNEKKKSOOIREKL-UHFFFAOYSA-N 0.000 claims description 3
• TWJJKHOHWJDRMH-UHFFFAOYSA-N n-[[5-[4-(2,3-dihydro-1h-inden-5-ylamino)piperidin-1-yl]sulfonylthiophen-2-yl]methyl]-3-methoxybenzamide Chemical compound COC1=CC=CC(C(=O)NCC=2SC(=CC=2)S(=O)(=O)N2CCC(CC2)NC=2C=C3CCCC3=CC=2)=C1 TWJJKHOHWJDRMH-UHFFFAOYSA-N 0.000 claims description 3
• INVPFKSBJXHAMG-UHFFFAOYSA-N n-[[5-[4-(3-carbamimidoylanilino)piperidin-1-yl]sulfonylthiophen-2-yl]methyl]-4-chlorobenzamide Chemical compound NC(=N)C1=CC=CC(NC2CCN(CC2)S(=O)(=O)C=2SC(CNC(=O)C=3C=CC(Cl)=CC=3)=CC=2)=C1 INVPFKSBJXHAMG-UHFFFAOYSA-N 0.000 claims description 3
• ATBQIKQERWETLA-UHFFFAOYSA-N n-[[5-[4-(4-chloroanilino)piperidin-1-yl]sulfonylthiophen-2-yl]methyl]-3-nitrobenzamide Chemical compound [O-][N+](=O)C1=CC=CC(C(=O)NCC=2SC(=CC=2)S(=O)(=O)N2CCC(CC2)NC=2C=CC(Cl)=CC=2)=C1 ATBQIKQERWETLA-UHFFFAOYSA-N 0.000 claims description 3
• SCIQVZLSYBRNNS-UHFFFAOYSA-N n-[[5-[4-[3-(2-hydroxyethylsulfonyl)anilino]piperidin-1-yl]sulfonylthiophen-2-yl]methyl]-3-nitrobenzamide Chemical compound OCCS(=O)(=O)C1=CC=CC(NC2CCN(CC2)S(=O)(=O)C=2SC(CNC(=O)C=3C=C(C=CC=3)[N+]([O-])=O)=CC=2)=C1 SCIQVZLSYBRNNS-UHFFFAOYSA-N 0.000 claims description 3
• XPGVCTFICOZEKS-UHFFFAOYSA-N n-[[5-[4-[3-(dimethylamino)anilino]piperidin-1-yl]sulfonylthiophen-2-yl]methyl]-3-methoxybenzamide Chemical compound COC1=CC=CC(C(=O)NCC=2SC(=CC=2)S(=O)(=O)N2CCC(CC2)NC=2C=C(C=CC=2)N(C)C)=C1 XPGVCTFICOZEKS-UHFFFAOYSA-N 0.000 claims description 3
• KSDVRVLEFMQKRT-UHFFFAOYSA-N n-[[5-[4-[4-(1,3-dithiolan-2-yl)anilino]piperidin-1-yl]sulfonylthiophen-2-yl]methyl]-3-methoxybenzamide Chemical compound COC1=CC=CC(C(=O)NCC=2SC(=CC=2)S(=O)(=O)N2CCC(CC2)NC=2C=CC(=CC=2)C2SCCS2)=C1 KSDVRVLEFMQKRT-UHFFFAOYSA-N 0.000 claims description 3
• 230000009223 neuronal apoptosis Effects 0.000 claims description 3
• 125000006501 nitrophenyl group Chemical group 0.000 claims description 3
• 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 3
• WHMDPDGBKYUEMW-UHFFFAOYSA-N pyridine-2-thiol Chemical compound SC1=CC=CC=N1 WHMDPDGBKYUEMW-UHFFFAOYSA-N 0.000 claims description 3
• 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 3
• 206010039073 rheumatoid arthritis Diseases 0.000 claims description 3
• 230000036303 septic shock Effects 0.000 claims description 3
• 208000020431 spinal cord injury Diseases 0.000 claims description 3
• OWLKOOPYISLPHJ-UHFFFAOYSA-N tert-butyl 4-[5-[[(4-chlorobenzoyl)amino]methyl]thiophen-2-yl]sulfonylpiperazine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCN1S(=O)(=O)C(S1)=CC=C1CNC(=O)C1=CC=C(Cl)C=C1 OWLKOOPYISLPHJ-UHFFFAOYSA-N 0.000 claims description 3
• 239000003981 vehicle Substances 0.000 claims description 3
• JHEYRNNLEOYSFJ-UHFFFAOYSA-N 2-hydroxy-n-[[5-[4-[3-(trifluoromethylsulfonyl)anilino]piperidin-1-yl]sulfonylthiophen-2-yl]methyl]benzamide Chemical compound OC1=CC=CC=C1C(=O)NCC1=CC=C(S(=O)(=O)N2CCC(CC2)NC=2C=C(C=CC=2)S(=O)(=O)C(F)(F)F)S1 JHEYRNNLEOYSFJ-UHFFFAOYSA-N 0.000 claims description 2
• GUOVBFFLXKJFEE-UHFFFAOYSA-N 2h-benzotriazole-5-carboxylic acid Chemical compound C1=C(C(=O)O)C=CC2=NNN=C21 GUOVBFFLXKJFEE-UHFFFAOYSA-N 0.000 claims description 2
• UHCPZMRRVTWDRO-UHFFFAOYSA-N 3-methoxy-n-[[5-[4-(2-methoxyanilino)piperidin-1-yl]sulfonylthiophen-2-yl]methyl]benzamide Chemical compound COC1=CC=CC(C(=O)NCC=2SC(=CC=2)S(=O)(=O)N2CCC(CC2)NC=2C(=CC=CC=2)OC)=C1 UHCPZMRRVTWDRO-UHFFFAOYSA-N 0.000 claims description 2
• MHGWSCDALBVNDX-UHFFFAOYSA-N 3-methoxy-n-[[5-[4-(3-methoxyanilino)piperidin-1-yl]sulfonylthiophen-2-yl]methyl]benzamide Chemical compound COC1=CC=CC(NC2CCN(CC2)S(=O)(=O)C=2SC(CNC(=O)C=3C=C(OC)C=CC=3)=CC=2)=C1 MHGWSCDALBVNDX-UHFFFAOYSA-N 0.000 claims description 2
• PVGNZTSNAGJCPB-UHFFFAOYSA-N 3-methoxy-n-[[5-[4-(3-nitroanilino)piperidin-1-yl]sulfonylthiophen-2-yl]methyl]benzamide Chemical compound COC1=CC=CC(C(=O)NCC=2SC(=CC=2)S(=O)(=O)N2CCC(CC2)NC=2C=C(C=CC=2)[N+]([O-])=O)=C1 PVGNZTSNAGJCPB-UHFFFAOYSA-N 0.000 claims description 2
• KMTYLHRYRPQICV-UHFFFAOYSA-N 3-methoxy-n-[[5-[4-(3-propylanilino)piperidin-1-yl]sulfonylthiophen-2-yl]methyl]benzamide Chemical compound CCCC1=CC=CC(NC2CCN(CC2)S(=O)(=O)C=2SC(CNC(=O)C=3C=C(OC)C=CC=3)=CC=2)=C1 KMTYLHRYRPQICV-UHFFFAOYSA-N 0.000 claims description 2
• ISABLLPEAKALNX-UHFFFAOYSA-N 3-methoxy-n-[[5-[4-[(3-nitropyridin-2-yl)amino]piperidin-1-yl]sulfonylthiophen-2-yl]methyl]benzamide Chemical compound COC1=CC=CC(C(=O)NCC=2SC(=CC=2)S(=O)(=O)N2CCC(CC2)NC=2C(=CC=CN=2)[N+]([O-])=O)=C1 ISABLLPEAKALNX-UHFFFAOYSA-N 0.000 claims description 2
• UWQRKPXBKSKMQC-UHFFFAOYSA-N 3-methoxy-n-[[5-[4-[2-nitro-4-(trifluoromethylsulfonyl)anilino]piperidin-1-yl]sulfonylthiophen-2-yl]methyl]benzamide Chemical compound COC1=CC=CC(C(=O)NCC=2SC(=CC=2)S(=O)(=O)N2CCC(CC2)NC=2C(=CC(=CC=2)S(=O)(=O)C(F)(F)F)[N+]([O-])=O)=C1 UWQRKPXBKSKMQC-UHFFFAOYSA-N 0.000 claims description 2
• AWPWLWYVJHGJIA-UHFFFAOYSA-N 3-methoxy-n-[[5-[4-[3-(trifluoromethylsulfonyl)anilino]piperidin-1-yl]sulfonylthiophen-2-yl]methyl]benzamide Chemical compound COC1=CC=CC(C(=O)NCC=2SC(=CC=2)S(=O)(=O)N2CCC(CC2)NC=2C=C(C=CC=2)S(=O)(=O)C(F)(F)F)=C1 AWPWLWYVJHGJIA-UHFFFAOYSA-N 0.000 claims description 2
• LNHMRTDUIBQUDK-UHFFFAOYSA-N 3-methoxy-n-[[5-[4-[4-(trifluoromethylsulfonyl)anilino]piperidin-1-yl]sulfonylthiophen-2-yl]methyl]benzamide Chemical compound COC1=CC=CC(C(=O)NCC=2SC(=CC=2)S(=O)(=O)N2CCC(CC2)NC=2C=CC(=CC=2)S(=O)(=O)C(F)(F)F)=C1 LNHMRTDUIBQUDK-UHFFFAOYSA-N 0.000 claims description 2
• URDVZZIJYDGVNG-UHFFFAOYSA-N 3-nitro-n-[[5-[4-(2-nitroanilino)piperidin-1-yl]sulfonylthiophen-2-yl]methyl]benzamide Chemical compound [O-][N+](=O)C1=CC=CC(C(=O)NCC=2SC(=CC=2)S(=O)(=O)N2CCC(CC2)NC=2C(=CC=CC=2)[N+]([O-])=O)=C1 URDVZZIJYDGVNG-UHFFFAOYSA-N 0.000 claims description 2
• GZHNYVGYCLTSJM-UHFFFAOYSA-N 3-nitro-n-[[5-[4-(3-phenylpropyl)piperazin-1-yl]sulfonylthiophen-2-yl]methyl]benzamide Chemical compound [O-][N+](=O)C1=CC=CC(C(=O)NCC=2SC(=CC=2)S(=O)(=O)N2CCN(CCCC=3C=CC=CC=3)CC2)=C1 GZHNYVGYCLTSJM-UHFFFAOYSA-N 0.000 claims description 2
• JOPXXSDRUTXQOU-UHFFFAOYSA-N 3-nitro-n-[[5-[4-(3-propylanilino)piperidin-1-yl]sulfonylthiophen-2-yl]methyl]benzamide Chemical compound CCCC1=CC=CC(NC2CCN(CC2)S(=O)(=O)C=2SC(CNC(=O)C=3C=C(C=CC=3)[N+]([O-])=O)=CC=2)=C1 JOPXXSDRUTXQOU-UHFFFAOYSA-N 0.000 claims description 2
• AWWSSRKHDULTMI-UHFFFAOYSA-N 3-nitro-n-[[5-[4-(3-propylphenoxy)piperidin-1-yl]sulfonylthiophen-2-yl]methyl]benzamide Chemical compound CCCC1=CC=CC(OC2CCN(CC2)S(=O)(=O)C=2SC(CNC(=O)C=3C=C(C=CC=3)[N+]([O-])=O)=CC=2)=C1 AWWSSRKHDULTMI-UHFFFAOYSA-N 0.000 claims description 2
• KLQSREQDOJRSTN-UHFFFAOYSA-N 3-nitro-n-[[5-[4-[(3-nitropyridin-2-yl)amino]piperidin-1-yl]sulfonylthiophen-2-yl]methyl]benzamide Chemical compound [O-][N+](=O)C1=CC=CC(C(=O)NCC=2SC(=CC=2)S(=O)(=O)N2CCC(CC2)NC=2C(=CC=CN=2)[N+]([O-])=O)=C1 KLQSREQDOJRSTN-UHFFFAOYSA-N 0.000 claims description 2
• FIHWFWMOCSATJG-UHFFFAOYSA-N 3-nitro-n-[[5-[4-[[4-(trifluoromethyl)pyrimidin-2-yl]amino]piperidin-1-yl]sulfonylthiophen-2-yl]methyl]benzamide Chemical compound [O-][N+](=O)C1=CC=CC(C(=O)NCC=2SC(=CC=2)S(=O)(=O)N2CCC(CC2)NC=2N=C(C=CN=2)C(F)(F)F)=C1 FIHWFWMOCSATJG-UHFFFAOYSA-N 0.000 claims description 2
• CNJWKRMQIHZGGJ-UHFFFAOYSA-N 4-[[1-[5-[[(4-chlorobenzoyl)amino]methyl]furan-2-yl]sulfonylpiperidin-4-yl]amino]benzamide Chemical compound C1=CC(C(=O)N)=CC=C1NC1CCN(S(=O)(=O)C=2OC(CNC(=O)C=3C=CC(Cl)=CC=3)=CC=2)CC1 CNJWKRMQIHZGGJ-UHFFFAOYSA-N 0.000 claims description 2
• MMROKRYETKOHRY-UHFFFAOYSA-N 4-[[1-[5-[[(4-chlorobenzoyl)amino]methyl]thiophen-2-yl]sulfonylpiperidin-4-yl]amino]benzamide Chemical compound C1=CC(C(=O)N)=CC=C1NC1CCN(S(=O)(=O)C=2SC(CNC(=O)C=3C=CC(Cl)=CC=3)=CC=2)CC1 MMROKRYETKOHRY-UHFFFAOYSA-N 0.000 claims description 2
• BHKRSZFGOWKFIT-UHFFFAOYSA-N 4-[[1-[5-[[(4-nitrobenzoyl)amino]methyl]thiophen-2-yl]sulfonylpiperidin-4-yl]amino]benzamide Chemical compound C1=CC(C(=O)N)=CC=C1NC1CCN(S(=O)(=O)C=2SC(CNC(=O)C=3C=CC(=CC=3)[N+]([O-])=O)=CC=2)CC1 BHKRSZFGOWKFIT-UHFFFAOYSA-N 0.000 claims description 2
• ZGQRJIOQKNUSSD-UHFFFAOYSA-N 4-chloro-n-[[5-(4-heptanoylpiperazin-1-yl)sulfonylthiophen-2-yl]methyl]benzamide Chemical compound C1CN(C(=O)CCCCCC)CCN1S(=O)(=O)C(S1)=CC=C1CNC(=O)C1=CC=C(Cl)C=C1 ZGQRJIOQKNUSSD-UHFFFAOYSA-N 0.000 claims description 2
• OHWTTXBZDAOGHF-UHFFFAOYSA-N 4-chloro-n-[[5-(4-hydroxy-4-phenylpiperidin-1-yl)sulfonylthiophen-2-yl]methyl]benzamide Chemical compound C1CC(O)(C=2C=CC=CC=2)CCN1S(=O)(=O)C(S1)=CC=C1CNC(=O)C1=CC=C(Cl)C=C1 OHWTTXBZDAOGHF-UHFFFAOYSA-N 0.000 claims description 2
• RRBCKDKVSCACLX-UHFFFAOYSA-N 4-chloro-n-[[5-(4-phenylpiperazin-1-yl)sulfonylthiophen-2-yl]methyl]benzamide Chemical compound C1=CC(Cl)=CC=C1C(=O)NCC1=CC=C(S(=O)(=O)N2CCN(CC2)C=2C=CC=CC=2)S1 RRBCKDKVSCACLX-UHFFFAOYSA-N 0.000 claims description 2
• WOHCGBAFDZPIHL-UHFFFAOYSA-N 4-chloro-n-[[5-(4-purin-9-ylpiperidin-1-yl)sulfonylthiophen-2-yl]methyl]benzamide Chemical compound C1=CC(Cl)=CC=C1C(=O)NCC1=CC=C(S(=O)(=O)N2CCC(CC2)N2C3=NC=NC=C3N=C2)S1 WOHCGBAFDZPIHL-UHFFFAOYSA-N 0.000 claims description 2
• JHGPMQWTHUEMFP-UHFFFAOYSA-N 4-chloro-n-[[5-(4-pyridin-2-ylpiperazin-1-yl)sulfonylthiophen-2-yl]methyl]benzamide Chemical compound C1=CC(Cl)=CC=C1C(=O)NCC1=CC=C(S(=O)(=O)N2CCN(CC2)C=2N=CC=CC=2)S1 JHGPMQWTHUEMFP-UHFFFAOYSA-N 0.000 claims description 2
• MREDMBHDTRVACC-UHFFFAOYSA-N 4-chloro-n-[[5-[4-(2,4,6-trifluorobenzoyl)piperazin-1-yl]sulfonylthiophen-2-yl]methyl]benzamide Chemical compound FC1=CC(F)=CC(F)=C1C(=O)N1CCN(S(=O)(=O)C=2SC(CNC(=O)C=3C=CC(Cl)=CC=3)=CC=2)CC1 MREDMBHDTRVACC-UHFFFAOYSA-N 0.000 claims description 2
• QOKLRARWPXJWCQ-UHFFFAOYSA-N 4-chloro-n-[[5-[4-(2,4-difluorobenzoyl)piperazin-1-yl]sulfonylthiophen-2-yl]methyl]benzamide Chemical compound FC1=CC(F)=CC=C1C(=O)N1CCN(S(=O)(=O)C=2SC(CNC(=O)C=3C=CC(Cl)=CC=3)=CC=2)CC1 QOKLRARWPXJWCQ-UHFFFAOYSA-N 0.000 claims description 2
• HYJJWJZEQVCURL-UHFFFAOYSA-N 4-chloro-n-[[5-[4-(2,6-dichlorobenzoyl)piperazin-1-yl]sulfonylthiophen-2-yl]methyl]benzamide Chemical compound C1=CC(Cl)=CC=C1C(=O)NCC1=CC=C(S(=O)(=O)N2CCN(CC2)C(=O)C=2C(=CC=CC=2Cl)Cl)S1 HYJJWJZEQVCURL-UHFFFAOYSA-N 0.000 claims description 2
• DBOSNSRCVGFXKK-UHFFFAOYSA-N 4-chloro-n-[[5-[4-(2,6-difluorobenzoyl)piperazin-1-yl]sulfonylthiophen-2-yl]methyl]benzamide Chemical compound FC1=CC=CC(F)=C1C(=O)N1CCN(S(=O)(=O)C=2SC(CNC(=O)C=3C=CC(Cl)=CC=3)=CC=2)CC1 DBOSNSRCVGFXKK-UHFFFAOYSA-N 0.000 claims description 2
• NYJLUKMZRKYHNL-UHFFFAOYSA-N 4-chloro-n-[[5-[4-(2-hydroxyanilino)piperidin-1-yl]sulfonylthiophen-2-yl]methyl]benzamide Chemical compound OC1=CC=CC=C1NC1CCN(S(=O)(=O)C=2SC(CNC(=O)C=3C=CC(Cl)=CC=3)=CC=2)CC1 NYJLUKMZRKYHNL-UHFFFAOYSA-N 0.000 claims description 2
• DUUSKLTYNACOPO-UHFFFAOYSA-N 4-chloro-n-[[5-[4-(2-hydroxyphenyl)piperazin-1-yl]sulfonylthiophen-2-yl]methyl]benzamide Chemical compound OC1=CC=CC=C1N1CCN(S(=O)(=O)C=2SC(CNC(=O)C=3C=CC(Cl)=CC=3)=CC=2)CC1 DUUSKLTYNACOPO-UHFFFAOYSA-N 0.000 claims description 2
• TWEDQMARYYHGLN-UHFFFAOYSA-N 4-chloro-n-[[5-[4-(2-methoxyanilino)piperidin-1-yl]sulfonylthiophen-2-yl]methyl]benzamide Chemical compound COC1=CC=CC=C1NC1CCN(S(=O)(=O)C=2SC(CNC(=O)C=3C=CC(Cl)=CC=3)=CC=2)CC1 TWEDQMARYYHGLN-UHFFFAOYSA-N 0.000 claims description 2
• PRZSAORUVDFXHW-UHFFFAOYSA-N 4-chloro-n-[[5-[4-(2-methoxyphenyl)piperazin-1-yl]sulfonylthiophen-2-yl]methyl]benzamide Chemical compound COC1=CC=CC=C1N1CCN(S(=O)(=O)C=2SC(CNC(=O)C=3C=CC(Cl)=CC=3)=CC=2)CC1 PRZSAORUVDFXHW-UHFFFAOYSA-N 0.000 claims description 2
• ZJTVMISOHUSPLK-UHFFFAOYSA-N 4-chloro-n-[[5-[4-(2-methylphenyl)piperazin-1-yl]sulfonylthiophen-2-yl]methyl]benzamide Chemical compound CC1=CC=CC=C1N1CCN(S(=O)(=O)C=2SC(CNC(=O)C=3C=CC(Cl)=CC=3)=CC=2)CC1 ZJTVMISOHUSPLK-UHFFFAOYSA-N 0.000 claims description 2
• JGVVQMFHAVBWHV-UHFFFAOYSA-N 4-chloro-n-[[5-[4-(2-morpholin-4-yl-2-oxoethyl)piperazin-1-yl]sulfonylthiophen-2-yl]methyl]benzamide Chemical compound C1=CC(Cl)=CC=C1C(=O)NCC1=CC=C(S(=O)(=O)N2CCN(CC(=O)N3CCOCC3)CC2)S1 JGVVQMFHAVBWHV-UHFFFAOYSA-N 0.000 claims description 2
• GUAYZMQYMVRFKM-UHFFFAOYSA-N 4-chloro-n-[[5-[4-(2-nitroanilino)piperidin-1-yl]sulfonylthiophen-2-yl]methyl]benzamide Chemical compound [O-][N+](=O)C1=CC=CC=C1NC1CCN(S(=O)(=O)C=2SC(CNC(=O)C=3C=CC(Cl)=CC=3)=CC=2)CC1 GUAYZMQYMVRFKM-UHFFFAOYSA-N 0.000 claims description 2
• LVNZZUWLRYETEC-UHFFFAOYSA-N 4-chloro-n-[[5-[4-(2-oxo-2-pyrrolidin-1-ylethyl)piperazin-1-yl]sulfonylthiophen-2-yl]methyl]benzamide Chemical compound C1=CC(Cl)=CC=C1C(=O)NCC1=CC=C(S(=O)(=O)N2CCN(CC(=O)N3CCCC3)CC2)S1 LVNZZUWLRYETEC-UHFFFAOYSA-N 0.000 claims description 2
• ZMQZNLCDTYDVIG-UHFFFAOYSA-N 4-chloro-n-[[5-[4-(2-phenylethyl)piperidin-1-yl]sulfonylthiophen-2-yl]methyl]benzamide Chemical compound C1=CC(Cl)=CC=C1C(=O)NCC1=CC=C(S(=O)(=O)N2CCC(CCC=3C=CC=CC=3)CC2)S1 ZMQZNLCDTYDVIG-UHFFFAOYSA-N 0.000 claims description 2
• MNXNODVEBOMXLE-UHFFFAOYSA-N 4-chloro-n-[[5-[4-(3,4,5-trimethoxyphenyl)piperazin-1-yl]sulfonylthiophen-2-yl]methyl]benzamide Chemical compound COC1=C(OC)C(OC)=CC(N2CCN(CC2)S(=O)(=O)C=2SC(CNC(=O)C=3C=CC(Cl)=CC=3)=CC=2)=C1 MNXNODVEBOMXLE-UHFFFAOYSA-N 0.000 claims description 2
• FWQYTGIUAZBABE-UHFFFAOYSA-N 4-chloro-n-[[5-[4-(3-chloroanilino)piperidin-1-yl]sulfonylthiophen-2-yl]methyl]benzamide Chemical compound C1=CC(Cl)=CC=C1C(=O)NCC1=CC=C(S(=O)(=O)N2CCC(CC2)NC=2C=C(Cl)C=CC=2)S1 FWQYTGIUAZBABE-UHFFFAOYSA-N 0.000 claims description 2
• YCCDIANAVWEWLG-UHFFFAOYSA-N 4-chloro-n-[[5-[4-(3-methoxyphenyl)piperazin-1-yl]sulfonylthiophen-2-yl]methyl]benzamide Chemical compound COC1=CC=CC(N2CCN(CC2)S(=O)(=O)C=2SC(CNC(=O)C=3C=CC(Cl)=CC=3)=CC=2)=C1 YCCDIANAVWEWLG-UHFFFAOYSA-N 0.000 claims description 2
• YQJXSQHEVFPNAC-UHFFFAOYSA-N 4-chloro-n-[[5-[4-(3-nitroanilino)piperidin-1-yl]sulfonylfuran-2-yl]methyl]benzamide Chemical compound [O-][N+](=O)C1=CC=CC(NC2CCN(CC2)S(=O)(=O)C=2OC(CNC(=O)C=3C=CC(Cl)=CC=3)=CC=2)=C1 YQJXSQHEVFPNAC-UHFFFAOYSA-N 0.000 claims description 2
• GZYOWTIBNUDSID-UHFFFAOYSA-N 4-chloro-n-[[5-[4-(3-nitroanilino)piperidin-1-yl]sulfonylthiophen-2-yl]methyl]benzamide Chemical compound [O-][N+](=O)C1=CC=CC(NC2CCN(CC2)S(=O)(=O)C=2SC(CNC(=O)C=3C=CC(Cl)=CC=3)=CC=2)=C1 GZYOWTIBNUDSID-UHFFFAOYSA-N 0.000 claims description 2
• KIFZXNYGNILUMS-UHFFFAOYSA-N 4-chloro-n-[[5-[4-(3-phenylpropyl)piperazin-1-yl]sulfonylthiophen-2-yl]methyl]benzamide Chemical compound C1=CC(Cl)=CC=C1C(=O)NCC1=CC=C(S(=O)(=O)N2CCN(CCCC=3C=CC=CC=3)CC2)S1 KIFZXNYGNILUMS-UHFFFAOYSA-N 0.000 claims description 2
• JHZYEWGAKWMEDW-UHFFFAOYSA-N 4-chloro-n-[[5-[4-(3-piperidin-1-ylpropyl)piperazin-1-yl]sulfonylthiophen-2-yl]methyl]benzamide Chemical compound C1=CC(Cl)=CC=C1C(=O)NCC1=CC=C(S(=O)(=O)N2CCN(CCCN3CCCCC3)CC2)S1 JHZYEWGAKWMEDW-UHFFFAOYSA-N 0.000 claims description 2
• BKMWOWVNFIYZLK-UHFFFAOYSA-N 4-chloro-n-[[5-[4-(3-propylphenoxy)piperidin-1-yl]sulfonylthiophen-2-yl]methyl]benzamide Chemical compound CCCC1=CC=CC(OC2CCN(CC2)S(=O)(=O)C=2SC(CNC(=O)C=3C=CC(Cl)=CC=3)=CC=2)=C1 BKMWOWVNFIYZLK-UHFFFAOYSA-N 0.000 claims description 2
• PQXVEEASOSMRPK-UHFFFAOYSA-N 4-chloro-n-[[5-[4-(4-chloro-2-nitrophenyl)piperazin-1-yl]sulfonylthiophen-2-yl]methyl]benzamide Chemical compound [O-][N+](=O)C1=CC(Cl)=CC=C1N1CCN(S(=O)(=O)C=2SC(CNC(=O)C=3C=CC(Cl)=CC=3)=CC=2)CC1 PQXVEEASOSMRPK-UHFFFAOYSA-N 0.000 claims description 2
• XVUHXWCAMOYWOY-UHFFFAOYSA-N 4-chloro-n-[[5-[4-(4-chloroanilino)piperidin-1-yl]sulfonylfuran-2-yl]methyl]benzamide Chemical compound C1=CC(Cl)=CC=C1NC1CCN(S(=O)(=O)C=2OC(CNC(=O)C=3C=CC(Cl)=CC=3)=CC=2)CC1 XVUHXWCAMOYWOY-UHFFFAOYSA-N 0.000 claims description 2
• LCXVZYCGNFRCCJ-UHFFFAOYSA-N 4-chloro-n-[[5-[4-(4-chlorophenyl)piperazin-1-yl]sulfonylthiophen-2-yl]methyl]benzamide Chemical compound C1=CC(Cl)=CC=C1N1CCN(S(=O)(=O)C=2SC(CNC(=O)C=3C=CC(Cl)=CC=3)=CC=2)CC1 LCXVZYCGNFRCCJ-UHFFFAOYSA-N 0.000 claims description 2
• XZOAWSLKNUUGTD-UHFFFAOYSA-N 4-chloro-n-[[5-[4-(4-nitrobenzoyl)piperazin-1-yl]sulfonylthiophen-2-yl]methyl]benzamide Chemical compound C1=CC([N+](=O)[O-])=CC=C1C(=O)N1CCN(S(=O)(=O)C=2SC(CNC(=O)C=3C=CC(Cl)=CC=3)=CC=2)CC1 XZOAWSLKNUUGTD-UHFFFAOYSA-N 0.000 claims description 2
• NHDUAPHOMGHKGS-UHFFFAOYSA-N 4-chloro-n-[[5-[4-(4-nitrophenyl)piperazin-1-yl]sulfonylthiophen-2-yl]methyl]benzamide Chemical compound C1=CC([N+](=O)[O-])=CC=C1N1CCN(S(=O)(=O)C=2SC(CNC(=O)C=3C=CC(Cl)=CC=3)=CC=2)CC1 NHDUAPHOMGHKGS-UHFFFAOYSA-N 0.000 claims description 2
• VXIKKJHVQORQGV-UHFFFAOYSA-N 4-chloro-n-[[5-[4-(4-propylanilino)piperidin-1-yl]sulfonylthiophen-2-yl]methyl]benzamide Chemical compound C1=CC(CCC)=CC=C1NC1CCN(S(=O)(=O)C=2SC(CNC(=O)C=3C=CC(Cl)=CC=3)=CC=2)CC1 VXIKKJHVQORQGV-UHFFFAOYSA-N 0.000 claims description 2
• XMSVEAWVXAZYPI-UHFFFAOYSA-N 4-chloro-n-[[5-[4-(5,6,7,8-tetrahydronaphthalen-1-ylamino)piperidin-1-yl]sulfonylthiophen-2-yl]methyl]benzamide Chemical compound C1=CC(Cl)=CC=C1C(=O)NCC1=CC=C(S(=O)(=O)N2CCC(CC2)NC=2C=3CCCCC=3C=CC=2)S1 XMSVEAWVXAZYPI-UHFFFAOYSA-N 0.000 claims description 2
• PSOIEIGBVVGSFE-UHFFFAOYSA-N 4-chloro-n-[[5-[4-(5-nitropyridin-2-yl)piperazin-1-yl]sulfonylthiophen-2-yl]methyl]benzamide Chemical compound N1=CC([N+](=O)[O-])=CC=C1N1CCN(S(=O)(=O)C=2SC(CNC(=O)C=3C=CC(Cl)=CC=3)=CC=2)CC1 PSOIEIGBVVGSFE-UHFFFAOYSA-N 0.000 claims description 2
• WBQUTRKCZCRIGN-UHFFFAOYSA-N 4-chloro-n-[[5-[4-(8-chlorobenzo[b][1,4]benzoxazepin-6-yl)piperazin-1-yl]sulfonylthiophen-2-yl]methyl]benzamide Chemical compound C1=CC(Cl)=CC=C1C(=O)NCC1=CC=C(S(=O)(=O)N2CCN(CC2)C=2C3=CC(Cl)=CC=C3OC3=CC=CC=C3N=2)S1 WBQUTRKCZCRIGN-UHFFFAOYSA-N 0.000 claims description 2
• SEALGLXOSZBNJE-UHFFFAOYSA-N 4-chloro-n-[[5-[4-(cyclohexylmethyl)piperazin-1-yl]sulfonylthiophen-2-yl]methyl]benzamide Chemical compound C1=CC(Cl)=CC=C1C(=O)NCC1=CC=C(S(=O)(=O)N2CCN(CC3CCCCC3)CC2)S1 SEALGLXOSZBNJE-UHFFFAOYSA-N 0.000 claims description 2
• JNICWLXHBMHJQV-UHFFFAOYSA-N 4-chloro-n-[[5-[4-(furan-2-carbonyl)piperazin-1-yl]sulfonylthiophen-2-yl]methyl]benzamide Chemical compound C1=CC(Cl)=CC=C1C(=O)NCC1=CC=C(S(=O)(=O)N2CCN(CC2)C(=O)C=2OC=CC=2)S1 JNICWLXHBMHJQV-UHFFFAOYSA-N 0.000 claims description 2
• JEYBYCKTBVYXBZ-UHFFFAOYSA-N 4-chloro-n-[[5-[4-(pyridin-4-ylmethyl)piperazin-1-yl]sulfonylthiophen-2-yl]methyl]benzamide Chemical compound C1=CC(Cl)=CC=C1C(=O)NCC1=CC=C(S(=O)(=O)N2CCN(CC=3C=CN=CC=3)CC2)S1 JEYBYCKTBVYXBZ-UHFFFAOYSA-N 0.000 claims description 2
• UWZVGIBPCUQWRW-UHFFFAOYSA-N 4-chloro-n-[[5-[4-(quinolin-8-ylamino)piperidin-1-yl]sulfonylthiophen-2-yl]methyl]benzamide Chemical compound C1=CC(Cl)=CC=C1C(=O)NCC1=CC=C(S(=O)(=O)N2CCC(CC2)NC=2C3=NC=CC=C3C=CC=2)S1 UWZVGIBPCUQWRW-UHFFFAOYSA-N 0.000 claims description 2
• CGXGPDQIKKQVFA-UHFFFAOYSA-N 4-chloro-n-[[5-[4-[(4-fluorophenyl)methyl]piperazin-1-yl]sulfonylthiophen-2-yl]methyl]benzamide Chemical compound C1=CC(F)=CC=C1CN1CCN(S(=O)(=O)C=2SC(CNC(=O)C=3C=CC(Cl)=CC=3)=CC=2)CC1 CGXGPDQIKKQVFA-UHFFFAOYSA-N 0.000 claims description 2
• QVBWKBSATXYLLS-UHFFFAOYSA-N 4-chloro-n-[[5-[4-[2-nitro-4-(trifluoromethylsulfonyl)anilino]piperidin-1-yl]sulfonylthiophen-2-yl]methyl]benzamide Chemical compound [O-][N+](=O)C1=CC(S(=O)(=O)C(F)(F)F)=CC=C1NC1CCN(S(=O)(=O)C=2SC(CNC(=O)C=3C=CC(Cl)=CC=3)=CC=2)CC1 QVBWKBSATXYLLS-UHFFFAOYSA-N 0.000 claims description 2
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• MFZLURIRJZLLKN-UHFFFAOYSA-N 4-chloro-n-[[5-(4-hydroxypiperidin-1-yl)sulfonylthiophen-2-yl]methyl]benzamide;n-(4-chlorophenyl)-2-[5-[4-(2-oxo-3h-benzimidazol-1-yl)piperidin-1-yl]sulfonylthiophen-2-yl]acetamide Chemical compound C1CC(O)CCN1S(=O)(=O)C(S1)=CC=C1CNC(=O)C1=CC=C(Cl)C=C1.C1=CC(Cl)=CC=C1NC(=O)CC1=CC=C(S(=O)(=O)N2CCC(CC2)N2C(NC3=CC=CC=C32)=O)S1 MFZLURIRJZLLKN-UHFFFAOYSA-N 0.000 claims 1
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