SK287058B6 - Sulfónamidové deriváty, spôsob ich prípravy, farmaceutický prostriedok s ich obsahom a ich použitie - Google Patents

Info

Publication number

SK287058B6

SK287058B6 SK580-2002A SK5802002A SK287058B6 SK 287058 B6 SK287058 B6 SK 287058B6 SK 5802002 A SK5802002 A SK 5802002A SK 287058 B6 SK287058 B6 SK 287058B6

Authority

SK

Slovakia

Prior art keywords

sulfonyl

methyl

thien

piperidin

benzamide

Prior art date

1999-09-28

Links

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• 150000003456 sulfonamides Chemical class 0.000 title claims abstract description 64
• 238000000034 method Methods 0.000 title claims abstract description 53
• 238000002360 preparation method Methods 0.000 title claims abstract description 35
• 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 21
• -1 nitro, sulfonyl Chemical group 0.000 claims description 480
• KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 389
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 389
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 288
• 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 244
• 150000001875 compounds Chemical class 0.000 claims description 169
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 76
• 229940124530 sulfonamide Drugs 0.000 claims description 71
• 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 65
• 125000003118 aryl group Chemical group 0.000 claims description 57
• 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 48
• 229910052739 hydrogen Inorganic materials 0.000 claims description 46
• 125000001072 heteroaryl group Chemical group 0.000 claims description 42
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 41
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 38
• 150000001412 amines Chemical class 0.000 claims description 38
• 239000001257 hydrogen Substances 0.000 claims description 31
• 229910052757 nitrogen Inorganic materials 0.000 claims description 31
• 229910052736 halogen Inorganic materials 0.000 claims description 27
• 125000001544 thienyl group Chemical group 0.000 claims description 27
• 150000002367 halogens Chemical class 0.000 claims description 26
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 23
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 23
• 229910052760 oxygen Inorganic materials 0.000 claims description 23
• 125000000242 4-chlorobenzoyl group Chemical group ClC1=CC=C(C(=O)*)C=C1 0.000 claims description 22
• 229910052799 carbon Inorganic materials 0.000 claims description 22
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 20
• YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 claims description 20
• 125000004442 acylamino group Chemical group 0.000 claims description 19
• 125000004423 acyloxy group Chemical group 0.000 claims description 19
• 125000000217 alkyl group Chemical group 0.000 claims description 19
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 19
• 125000001424 substituent group Chemical group 0.000 claims description 19
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 18
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 18
• 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims description 18
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 17
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 16
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 16
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 16
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 16
• 125000002541 furyl group Chemical group 0.000 claims description 16
• 239000001301 oxygen Substances 0.000 claims description 16
• 125000004122 cyclic group Chemical group 0.000 claims description 15
• 150000002431 hydrogen Chemical class 0.000 claims description 15
• 150000003839 salts Chemical class 0.000 claims description 15
• 229920006395 saturated elastomer Polymers 0.000 claims description 15
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 14
• GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 14
• 208000035475 disorder Diseases 0.000 claims description 14
• 230000008569 process Effects 0.000 claims description 14
• 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 13
• 125000005309 thioalkoxy group Chemical group 0.000 claims description 13
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 12
• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 12
• 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 12
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
• 125000003545 alkoxy group Chemical group 0.000 claims description 11
• 125000004076 pyridyl group Chemical group 0.000 claims description 11
• 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 10
• YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 10
• QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 10
• 230000001537 neural effect Effects 0.000 claims description 10
• XMVJITFPVVRMHC-UHFFFAOYSA-N roxarsone Chemical group OC1=CC=C([As](O)(O)=O)C=C1[N+]([O-])=O XMVJITFPVVRMHC-UHFFFAOYSA-N 0.000 claims description 10
• 125000002252 acyl group Chemical group 0.000 claims description 9
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 9
• 239000003814 drug Substances 0.000 claims description 9
• 125000004193 piperazinyl 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
• WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 8
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 8
• 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 8
• 125000002619 bicyclic group Chemical group 0.000 claims description 8
• 125000005842 heteroatom Chemical group 0.000 claims description 8
• 150000003951 lactams Chemical class 0.000 claims description 8
• 150000002596 lactones Chemical class 0.000 claims description 8
• 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 8
• 125000001453 quaternary ammonium group Chemical group 0.000 claims description 8
• 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 claims description 8
• 238000006467 substitution reaction Methods 0.000 claims description 8
• 125000001302 tertiary amino group Chemical group 0.000 claims description 8
• 150000003555 thioacetals Chemical class 0.000 claims description 8
• 125000004953 trihalomethyl group Chemical group 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 7
• 150000001263 acyl chlorides Chemical class 0.000 claims description 7
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
• 125000006165 cyclic alkyl group Chemical group 0.000 claims description 7
• QFFCMSVSOLNBCG-UHFFFAOYSA-N n-[[5-(4-heptanoylpiperidin-1-yl)sulfonylthiophen-2-yl]methyl]-3-methoxybenzamide Chemical compound C1CC(C(=O)CCCCCC)CCN1S(=O)(=O)C(S1)=CC=C1CNC(=O)C1=CC=CC(OC)=C1 QFFCMSVSOLNBCG-UHFFFAOYSA-N 0.000 claims description 7
• 238000007363 ring formation reaction Methods 0.000 claims description 7
• 229910052717 sulfur Inorganic materials 0.000 claims description 7
• 125000006334 2,4-difluoro benzoyl group Chemical group [H]C1=C([H])C(C(*)=O)=C(F)C([H])=C1F 0.000 claims description 6
• XXUNIGZDNWWYED-UHFFFAOYSA-N 2-methylbenzamide Chemical compound CC1=CC=CC=C1C(N)=O XXUNIGZDNWWYED-UHFFFAOYSA-N 0.000 claims description 6
• 125000005605 benzo group Chemical group 0.000 claims description 6
• 239000003085 diluting agent Substances 0.000 claims description 6
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 6
• ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 6
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 6
• 208000023275 Autoimmune disease Diseases 0.000 claims description 5
• 206010040070 Septic Shock Diseases 0.000 claims description 5
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
• 239000000546 pharmaceutical excipient Substances 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
• 229930192474 thiophene Natural products 0.000 claims description 5
• 125000003287 1H-imidazol-4-ylmethyl group Chemical group [H]N1C([H])=NC(C([H])([H])[*])=C1[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
• PABNZKZLNDPPRJ-UHFFFAOYSA-N 2h-isoindol-5-amine Chemical compound C1=C(N)C=CC2=CNC=C21 PABNZKZLNDPPRJ-UHFFFAOYSA-N 0.000 claims description 4
• PTRWZUIFMORETL-UHFFFAOYSA-N 4-azatricyclo[9.4.0.03,8]pentadeca-1(15),2,5,7,9,11,13-heptaene Chemical compound C1=CC2=CC=CC=C2C=C2NC=CC=C21 PTRWZUIFMORETL-UHFFFAOYSA-N 0.000 claims description 4
• RJEOVKLQSXYTMB-UHFFFAOYSA-N 4-chloro-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=CC(Cl)=CC=3)=CC=2)=C1 RJEOVKLQSXYTMB-UHFFFAOYSA-N 0.000 claims description 4
• 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 4
• 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 4
• DZJXKISLUDYJSV-UHFFFAOYSA-N [N].C1CCNC1 Chemical compound [N].C1CCNC1 DZJXKISLUDYJSV-UHFFFAOYSA-N 0.000 claims description 4
• 150000001408 amides Chemical class 0.000 claims description 4
• ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 claims description 4
• PXXJHWLDUBFPOL-UHFFFAOYSA-N benzamidine Chemical compound NC(=N)C1=CC=CC=C1 PXXJHWLDUBFPOL-UHFFFAOYSA-N 0.000 claims description 4
• 230000008878 coupling Effects 0.000 claims description 4
• 238000010168 coupling process Methods 0.000 claims description 4
• 238000005859 coupling reaction Methods 0.000 claims description 4
• 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 4
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
• 125000004043 oxo group Chemical group O=* 0.000 claims description 4
• FQUYSHZXSKYCSY-UHFFFAOYSA-N 1,4-diazepane Chemical group C1CNCCNC1 FQUYSHZXSKYCSY-UHFFFAOYSA-N 0.000 claims description 3
• IQKCSXGNUGNTBI-UHFFFAOYSA-N 2-[4-[5-[[(4-chlorobenzoyl)amino]methyl]thiophen-2-yl]sulfonylpiperazin-1-yl]-8-ethyl-5-oxopyrido[2,3-d]pyrimidine-6-carboxylic acid Chemical compound N1=C2N(CC)C=C(C(O)=O)C(=O)C2=CN=C1N(CC1)CCN1S(=O)(=O)C(S1)=CC=C1CNC(=O)C1=CC=C(Cl)C=C1 IQKCSXGNUGNTBI-UHFFFAOYSA-N 0.000 claims description 3
• 208000006011 Stroke Diseases 0.000 claims description 3
• 150000007854 aminals Chemical class 0.000 claims description 3
• QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 claims description 3
• 235000010290 biphenyl Nutrition 0.000 claims description 3
• 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 claims description 3
• 229910052801 chlorine Inorganic materials 0.000 claims description 3
• 125000001309 chloro group Chemical group Cl* 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
• 150000003840 hydrochlorides Chemical class 0.000 claims description 3
• 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 3
• ROFHAFYHOWVRTC-UHFFFAOYSA-N n-[3-(trifluoromethylsulfonyl)phenyl]piperidin-4-amine Chemical compound FC(F)(F)S(=O)(=O)C1=CC=CC(NC2CCNCC2)=C1 ROFHAFYHOWVRTC-UHFFFAOYSA-N 0.000 claims description 3
• OFUSFMOABADUOT-UHFFFAOYSA-N n-[[5-(4-benzoylpiperazin-1-yl)sulfonylthiophen-2-yl]methyl]-4-chlorobenzamide Chemical compound C1=CC(Cl)=CC=C1C(=O)NCC1=CC=C(S(=O)(=O)N2CCN(CC2)C(=O)C=2C=CC=CC=2)S1 OFUSFMOABADUOT-UHFFFAOYSA-N 0.000 claims description 3
• JBXFYXNBXHXQLT-UHFFFAOYSA-N n-[[5-[4-(2,1,3-benzoxadiazole-5-carbonyl)piperazin-1-yl]sulfonylthiophen-2-yl]methyl]-4-chlorobenzamide Chemical compound C1=CC(Cl)=CC=C1C(=O)NCC1=CC=C(S(=O)(=O)N2CCN(CC2)C(=O)C2=CC3=NON=C3C=C2)S1 JBXFYXNBXHXQLT-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
• OQVPAFGDXBUMJC-UHFFFAOYSA-N n-[[5-[4-[3-(dimethylamino)anilino]piperidin-1-yl]sulfonylthiophen-2-yl]methyl]-3-nitrobenzamide Chemical compound CN(C)C1=CC=CC(NC2CCN(CC2)S(=O)(=O)C=2SC(CNC(=O)C=3C=C(C=CC=3)[N+]([O-])=O)=CC=2)=C1 OQVPAFGDXBUMJC-UHFFFAOYSA-N 0.000 claims description 3
• 229960000581 salicylamide Drugs 0.000 claims description 3
• 230000036303 septic shock Effects 0.000 claims description 3
• DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 3
• 125000003396 thiol group Chemical group [H]S* 0.000 claims description 3
• 125000004098 2,6-dichlorobenzoyl group Chemical group O=C([*])C1=C(Cl)C([H])=C([H])C([H])=C1Cl 0.000 claims description 2
• RBGDLYUEXLWQBZ-UHFFFAOYSA-N 2-chlorobenzamide Chemical compound NC(=O)C1=CC=CC=C1Cl RBGDLYUEXLWQBZ-UHFFFAOYSA-N 0.000 claims description 2
• MNWSGMTUGXNYHJ-UHFFFAOYSA-N 2-methoxybenzamide Chemical compound COC1=CC=CC=C1C(N)=O MNWSGMTUGXNYHJ-UHFFFAOYSA-N 0.000 claims description 2
• 125000005809 3,4,5-trimethoxyphenyl group Chemical group [H]C1=C(OC([H])([H])[H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims description 2
• NPJZEZNSWGSLMI-UHFFFAOYSA-N 3-[[1-[5-[[(3-methoxybenzoyl)amino]methyl]thiophen-2-yl]sulfonylpiperidin-4-yl]amino]benzamide Chemical compound COC1=CC=CC(C(=O)NCC=2SC(=CC=2)S(=O)(=O)N2CCC(CC2)NC=2C=C(C=CC=2)C(N)=O)=C1 NPJZEZNSWGSLMI-UHFFFAOYSA-N 0.000 claims description 2
• 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 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
• 125000006201 3-phenylpropyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])C([H])([H])* 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
• 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
• ROABHMPRRXUDJU-UHFFFAOYSA-N 4-chloro-n-[(5-piperidin-1-ylsulfonylthiophen-2-yl)methyl]benzamide Chemical compound C1=CC(Cl)=CC=C1C(=O)NCC1=CC=C(S(=O)(=O)N2CCCCC2)S1 ROABHMPRRXUDJU-UHFFFAOYSA-N 0.000 claims description 2
• DJUDYCQCDKMWKD-UHFFFAOYSA-N 4-chloro-n-[[5-[4-(3-phenylanilino)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(C=CC=2)C=2C=CC=CC=2)S1 DJUDYCQCDKMWKD-UHFFFAOYSA-N 0.000 claims description 2
• 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 2
• JGWCDTYHEXUMGW-UHFFFAOYSA-N 4-chloro-n-[[5-[4-(naphthalene-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=2C=C3C=CC=CC3=CC=2)S1 JGWCDTYHEXUMGW-UHFFFAOYSA-N 0.000 claims description 2
• AJGFNJHGWZMPFD-UHFFFAOYSA-N 4-chloro-n-[[5-[4-[3-(trifluoromethyl)anilino]piperidin-1-yl]sulfonylfuran-2-yl]methyl]benzamide Chemical compound FC(F)(F)C1=CC=CC(NC2CCN(CC2)S(=O)(=O)C=2OC(CNC(=O)C=3C=CC(Cl)=CC=3)=CC=2)=C1 AJGFNJHGWZMPFD-UHFFFAOYSA-N 0.000 claims description 2
• ISGMKWLOPZZFOX-UHFFFAOYSA-N 4-chloro-n-[[5-[4-[hydroxy(diphenyl)methyl]piperidin-1-yl]sulfonylthiophen-2-yl]methyl]benzamide Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(O)C(CC1)CCN1S(=O)(=O)C(S1)=CC=C1CNC(=O)C1=CC=C(Cl)C=C1 ISGMKWLOPZZFOX-UHFFFAOYSA-N 0.000 claims description 2
• 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
• 208000024827 Alzheimer disease Diseases 0.000 claims description 2
• 206010003210 Arteriosclerosis Diseases 0.000 claims description 2
• 206010006187 Breast cancer Diseases 0.000 claims description 2
• 208000026310 Breast neoplasm Diseases 0.000 claims description 2
• 208000024172 Cardiovascular disease Diseases 0.000 claims description 2
• 206010019196 Head injury Diseases 0.000 claims description 2
• 208000023105 Huntington disease Diseases 0.000 claims description 2
• 208000007201 Myocardial reperfusion injury Diseases 0.000 claims description 2
• 206010028980 Neoplasm Diseases 0.000 claims description 2
• 208000018737 Parkinson disease Diseases 0.000 claims description 2
• 208000017442 Retinal disease Diseases 0.000 claims description 2
• 206010052779 Transplant rejections Diseases 0.000 claims description 2
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• 125000005036 alkoxyphenyl group Chemical group 0.000 claims description 2
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