SK287058B6 - Sulfónamidové deriváty, spôsob ich prípravy, farmaceutický prostriedok s ich obsahom a ich použitie - Google Patents
Sulfónamidové deriváty, spôsob ich prípravy, farmaceutický prostriedok s ich obsahom a ich použitie Download PDFInfo
- 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
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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
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- 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
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Classifications
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- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
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- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/10—Spiro-condensed systems
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- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
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- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Neurology (AREA)
- Immunology (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
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- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Pulmonology (AREA)
- Psychology (AREA)
- Pain & Pain Management (AREA)
- Transplantation (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Urology & Nephrology (AREA)
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- Hospice & Palliative Care (AREA)
- Psychiatry (AREA)
- Vascular Medicine (AREA)
- Physical Education & Sports Medicine (AREA)
- Communicable Diseases (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP99810869A EP1088821A1 (en) | 1999-09-28 | 1999-09-28 | Pharmaceutically active sulfonamide derivatives |
PCT/IB2000/001380 WO2001023378A1 (en) | 1999-09-28 | 2000-09-28 | Pharmaceutically active sulfonamide derivatives |
Publications (2)
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SK5802002A3 SK5802002A3 (en) | 2002-08-06 |
SK287058B6 true SK287058B6 (sk) | 2009-10-07 |
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SK580-2002A SK287058B6 (sk) | 1999-09-28 | 2000-09-28 | Sulfónamidové deriváty, spôsob ich prípravy, farmaceutický prostriedok s ich obsahom a ich použitie |
Country Status (30)
Country | Link |
---|---|
US (1) | US8012995B1 (et) |
EP (2) | EP1088821A1 (et) |
JP (2) | JP5015397B2 (et) |
KR (1) | KR100827533B1 (et) |
CN (1) | CN1189467C (et) |
AR (1) | AR031531A1 (et) |
AT (1) | ATE309998T1 (et) |
AU (1) | AU777708B2 (et) |
BG (1) | BG65797B1 (et) |
BR (1) | BR0014641A (et) |
CA (1) | CA2379575C (et) |
CZ (1) | CZ2002880A3 (et) |
DE (1) | DE60024115T2 (et) |
DK (1) | DK1218374T3 (et) |
EA (1) | EA005368B1 (et) |
EE (1) | EE05109B1 (et) |
ES (1) | ES2248114T3 (et) |
HK (1) | HK1048306B (et) |
HU (1) | HUP0203312A3 (et) |
IL (2) | IL148876A0 (et) |
MX (1) | MXPA02003199A (et) |
NO (1) | NO324792B1 (et) |
NZ (1) | NZ517424A (et) |
PL (1) | PL212237B1 (et) |
SI (1) | SI1218374T1 (et) |
SK (1) | SK287058B6 (et) |
TR (1) | TR200200789T2 (et) |
UA (1) | UA74796C2 (et) |
WO (1) | WO2001023378A1 (et) |
ZA (1) | ZA200201509B (et) |
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EP1088822A1 (en) | 1999-09-28 | 2001-04-04 | Applied Research Systems ARS Holding N.V. | Pharmaceutically active sulfonyl hydrazide derivatives |
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EP1193267A1 (en) * | 2000-09-27 | 2002-04-03 | Applied Research Systems ARS Holding N.V. | Pharmaceutically active hydrophilic sulfonamide derivatives as inhibitors of protein JunKinases |
EP1193268A1 (en) * | 2000-09-27 | 2002-04-03 | Applied Research Systems ARS Holding N.V. | Pharmaceutically active sulfonamide derivatives bearing both lipophilic and ionisable moieties as inhibitors of protein Junkinases |
EP1193256A1 (en) * | 2000-09-27 | 2002-04-03 | Applied Research Systems ARS Holding N.V. | Pharmaceutically active benzsulfonamide derivatives as inhibitors of JNK proteins |
NZ538100A (en) * | 2000-12-13 | 2006-07-28 | Arqule Inc | Heterocyclic sulfonamide inhibitors of beta amyloid production |
US6657070B2 (en) | 2000-12-13 | 2003-12-02 | Wyeth | Production of chirally pure α-amino acids and N-sulfonyl α-amino acids |
JP4535680B2 (ja) | 2001-04-16 | 2010-09-01 | エーザイ・アール・アンド・ディー・マネジメント株式会社 | 新規1h−インダゾール化合物 |
DE60230625D1 (de) * | 2001-07-23 | 2009-02-12 | Serono Lab | Arylsulfonamidderivate als hemmer c-jun-terminaler kinasen (jnk) |
PA8557501A1 (es) | 2001-11-12 | 2003-06-30 | Pfizer Prod Inc | Benzamida, heteroarilamida y amidas inversas |
WO2003042190A1 (en) | 2001-11-12 | 2003-05-22 | Pfizer Products Inc. | N-alkyl-adamantyl derivatives as p2x7-receptor antagonists |
WO2003101968A1 (fr) | 2002-05-31 | 2003-12-11 | Eisai Co., Ltd. | Compose de pyrazole et composition medicinale le contenant |
CA2486581A1 (en) | 2002-06-11 | 2003-12-18 | Wyeth | Substituted phenylsulfonamide inhibitors of beta amyloid production |
PA8591801A1 (es) | 2002-12-31 | 2004-07-26 | Pfizer Prod Inc | Inhibidores benzamidicos del receptor p2x7. |
US7071223B1 (en) | 2002-12-31 | 2006-07-04 | Pfizer, Inc. | Benzamide inhibitors of the P2X7 receptor |
AU2004221812B2 (en) | 2003-03-19 | 2010-02-18 | Exelixis Inc. | Tie-2 modulators and methods of use |
AU2004230844B2 (en) | 2003-03-31 | 2010-12-09 | Wyeth | Fluoro-and trifluoroalkyl-containing heterocyclic sulfonamide inhibitors of beta amyloid production and derivatives thereof |
ATE551997T1 (de) | 2003-09-12 | 2012-04-15 | Merck Serono Sa | Sulfonamid-derivate zur behandlung von diabetes |
JP2007517905A (ja) | 2004-01-16 | 2007-07-05 | ワイス | アゾールを含有するベータアミロイド産生のヘテロ環式スルホンアミド阻害剤 |
WO2005074921A1 (en) * | 2004-02-09 | 2005-08-18 | University Of Zurich | Treatment of atherosclerosis |
CN1660811A (zh) * | 2004-02-27 | 2005-08-31 | 中国科学院上海药物研究所 | 1,4-二取代苯类化合物及其制备方法和用途 |
WO2005118543A1 (ja) * | 2004-06-03 | 2005-12-15 | Ono Pharmaceutical Co., Ltd. | キナーゼ阻害薬およびその用途 |
AU2005258911A1 (en) | 2004-06-29 | 2006-01-12 | Pfizer Products Inc. | Method for preparing 5-`4-(2-hydroxy-propyl)-3,5-dioxo-4,5-dihydro-3H`1,2,4!triazin-2-YL!-benzamide derivatives by deprotecting the hydroxyl-protected precursers |
US20060094753A1 (en) | 2004-10-29 | 2006-05-04 | Alcon, Inc. | Use of inhibitors of Jun N-terminal kinases for the treatment of glaucomatous retinopathy and ocular diseases |
US7803824B2 (en) | 2004-10-29 | 2010-09-28 | Alcon, Inc. | Use of inhibitors of Jun N-terminal kinases to treat glaucoma |
US20060223807A1 (en) | 2005-03-29 | 2006-10-05 | University Of Massachusetts Medical School, A Massachusetts Corporation | Therapeutic methods for type I diabetes |
KR20080044836A (ko) | 2005-07-15 | 2008-05-21 | 라보라뚜와르 세로노 에스. 에이. | 자궁내막증 치료용 jnk 억제제 |
BRPI0613042A2 (pt) | 2005-07-15 | 2010-12-14 | Serono Lab | inibidores de jnk para o tratamento de endometriose |
AU2011265521B9 (en) * | 2005-07-15 | 2014-05-22 | Merck Serono Sa | JNK inhibitors for the treatment of endometreosis |
AU2006332680A1 (en) | 2005-12-29 | 2007-07-12 | Anthrogenesis Corporation | Improved composition for collecting and preserving placental stem cells and methods of using the composition |
WO2007141224A2 (en) * | 2006-06-02 | 2007-12-13 | Laboratoires Serono Sa | Jnk inhibitors for treatment of skin diseases |
US8946197B2 (en) | 2009-11-16 | 2015-02-03 | Chdi Foundation, Inc. | Transglutaminase TG2 inhibitors, pharmaceutical compositions, and methods of use thereof |
US8889716B2 (en) | 2011-05-10 | 2014-11-18 | Chdi Foundation, Inc. | Transglutaminase TG2 inhibitors, pharmaceutical compositions, and methods of use thereof |
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SU1706174A3 (ru) * | 1989-02-08 | 1995-10-10 | Институт биохимии Литовской АН | N-замещенные 5-фталимидонафталин-1-сульфамиды в качестве полупродуктов для получения n-замещенных аминонафталинсульфамидов |
JPH05505599A (ja) | 1990-03-15 | 1993-08-19 | ジ・アップジョン・カンパニー | 治療上有用な複素環インドール化合物類 |
US5106983A (en) | 1990-04-30 | 1992-04-21 | The United States Of America As Represented By The Secretary Of The Army | Process of making carfentanil and related analgesics |
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DE60030741T2 (de) * | 1999-09-23 | 2007-09-06 | Astrazeneca Ab | Chinazoline verbindungen als heilmittel |
EP1088821A1 (en) * | 1999-09-28 | 2001-04-04 | Applied Research Systems ARS Holding N.V. | Pharmaceutically active sulfonamide derivatives |
EP1088822A1 (en) | 1999-09-28 | 2001-04-04 | Applied Research Systems ARS Holding N.V. | Pharmaceutically active sulfonyl hydrazide derivatives |
EP1088815A1 (en) | 1999-09-28 | 2001-04-04 | Applied Research Systems ARS Holding N.V. | Pharmaceutically active sulfonyl amino acid derivatives |
US6506901B2 (en) * | 2000-07-17 | 2003-01-14 | Wyeth | Substituted 2-(S)-hydroxy-3-(piperidin-4-yl-methylamino)-propyl ethers and substituted 2-aryl-2-(R)-hydroxy-1-(piperidin-4-yl-methyl)-ethylamine β-3 adrenergic receptor agonists |
-
1999
- 1999-09-28 EP EP99810869A patent/EP1088821A1/en not_active Withdrawn
-
2000
- 2000-09-26 AR ARP000105044A patent/AR031531A1/es active IP Right Grant
- 2000-09-28 WO PCT/IB2000/001380 patent/WO2001023378A1/en active IP Right Grant
- 2000-09-28 SI SI200030771T patent/SI1218374T1/sl unknown
- 2000-09-28 DK DK00960921T patent/DK1218374T3/da active
- 2000-09-28 EP EP00960921A patent/EP1218374B1/en not_active Expired - Lifetime
- 2000-09-28 EA EA200200417A patent/EA005368B1/ru not_active IP Right Cessation
- 2000-09-28 JP JP2001526530A patent/JP5015397B2/ja not_active Expired - Fee Related
- 2000-09-28 US US10/070,954 patent/US8012995B1/en not_active Expired - Fee Related
- 2000-09-28 AT AT00960921T patent/ATE309998T1/de active
- 2000-09-28 BR BR0014641-2A patent/BR0014641A/pt not_active IP Right Cessation
- 2000-09-28 NZ NZ517424A patent/NZ517424A/en not_active IP Right Cessation
- 2000-09-28 DE DE60024115T patent/DE60024115T2/de not_active Expired - Lifetime
- 2000-09-28 UA UA2002032472A patent/UA74796C2/uk unknown
- 2000-09-28 AU AU73074/00A patent/AU777708B2/en not_active Ceased
- 2000-09-28 KR KR1020027003983A patent/KR100827533B1/ko not_active IP Right Cessation
- 2000-09-28 ES ES00960921T patent/ES2248114T3/es not_active Expired - Lifetime
- 2000-09-28 IL IL14887600A patent/IL148876A0/xx unknown
- 2000-09-28 EE EEP200200165A patent/EE05109B1/et not_active IP Right Cessation
- 2000-09-28 CA CA2379575A patent/CA2379575C/en not_active Expired - Fee Related
- 2000-09-28 PL PL354169A patent/PL212237B1/pl not_active IP Right Cessation
- 2000-09-28 MX MXPA02003199A patent/MXPA02003199A/es active IP Right Grant
- 2000-09-28 TR TR2002/00789T patent/TR200200789T2/xx unknown
- 2000-09-28 CZ CZ2002880A patent/CZ2002880A3/cs unknown
- 2000-09-28 CN CNB008135681A patent/CN1189467C/zh not_active Expired - Fee Related
- 2000-09-28 HU HU0203312A patent/HUP0203312A3/hu unknown
- 2000-09-28 SK SK580-2002A patent/SK287058B6/sk not_active IP Right Cessation
-
2002
- 2002-02-22 ZA ZA200201509A patent/ZA200201509B/xx unknown
- 2002-03-18 BG BG106527A patent/BG65797B1/bg unknown
- 2002-03-25 IL IL148876A patent/IL148876A/en not_active IP Right Cessation
- 2002-03-26 NO NO20021530A patent/NO324792B1/no not_active IP Right Cessation
-
2003
- 2003-01-08 HK HK03100202.1A patent/HK1048306B/zh not_active IP Right Cessation
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2012
- 2012-02-20 JP JP2012033604A patent/JP2012121904A/ja active Pending
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TC4A | Change of owner's name |
Owner name: MERCK SERONO SA, COINSINS, VAUD, CH Effective date: 20120709 |
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MM4A | Patent lapsed due to non-payment of maintenance fees |
Effective date: 20130928 |