CA2817531A1 - Derivatives of heteroarylsulfonamides, their preparation and their application in human therapy - Google Patents
Derivatives of heteroarylsulfonamides, their preparation and their application in human therapy Download PDFInfo
- Publication number
- CA2817531A1 CA2817531A1 CA2817531A CA2817531A CA2817531A1 CA 2817531 A1 CA2817531 A1 CA 2817531A1 CA 2817531 A CA2817531 A CA 2817531A CA 2817531 A CA2817531 A CA 2817531A CA 2817531 A1 CA2817531 A1 CA 2817531A1
- Authority
- CA
- Canada
- Prior art keywords
- compound
- sulfonamide
- phenyl
- pyridine
- thiazol
- Prior art date
- 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
- 238000002360 preparation method Methods 0.000 title claims abstract description 8
- 241000282414 Homo sapiens Species 0.000 title description 12
- 238000002560 therapeutic procedure Methods 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 82
- 150000003839 salts Chemical class 0.000 claims abstract description 32
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 30
- 239000001257 hydrogen Substances 0.000 claims abstract description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 16
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 14
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 13
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 10
- 150000002367 halogens Chemical class 0.000 claims abstract description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 9
- 102000003734 Voltage-Gated Potassium Channels Human genes 0.000 claims abstract description 8
- 108090000013 Voltage-Gated Potassium Channels Proteins 0.000 claims abstract description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 8
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 7
- 239000005864 Sulphur Chemical group 0.000 claims abstract description 7
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 7
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 7
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 7
- 125000001424 substituent group Chemical group 0.000 claims abstract description 7
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims abstract description 7
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 5
- 239000001301 oxygen Substances 0.000 claims abstract description 5
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims abstract description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims abstract description 3
- 239000011737 fluorine Substances 0.000 claims abstract description 3
- 125000004076 pyridyl group Chemical group 0.000 claims abstract description 3
- 125000005493 quinolyl group Chemical group 0.000 claims abstract description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract 7
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims abstract 4
- 238000000034 method Methods 0.000 claims description 47
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 24
- 230000009467 reduction Effects 0.000 claims description 14
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 12
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 12
- 230000015572 biosynthetic process Effects 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 9
- 239000003814 drug Substances 0.000 claims description 7
- 230000022131 cell cycle Effects 0.000 claims description 6
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 claims description 6
- -1 8-quinolyl group Chemical group 0.000 claims description 5
- 206010028980 Neoplasm Diseases 0.000 claims description 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 5
- 208000035475 disorder Diseases 0.000 claims description 5
- 230000007170 pathology Effects 0.000 claims description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims description 5
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
- 201000011510 cancer Diseases 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
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 4
- 230000033764 rhythmic process Effects 0.000 claims description 4
- 206010003658 Atrial Fibrillation Diseases 0.000 claims description 3
- 230000004663 cell proliferation Effects 0.000 claims description 3
- 230000001771 impaired effect Effects 0.000 claims description 3
- 229940072033 potash Drugs 0.000 claims description 3
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 3
- 235000015320 potassium carbonate Nutrition 0.000 claims description 3
- 230000002265 prevention Effects 0.000 claims description 3
- 125000003368 amide group Chemical group 0.000 claims description 2
- 208000037976 chronic inflammation Diseases 0.000 claims description 2
- 230000006020 chronic inflammation Effects 0.000 claims description 2
- CLICSZJJPWIGEX-UHFFFAOYSA-N n-[2-[1-(5-tert-butyl-1,3-benzoxazol-2-yl)piperidin-4-yl]oxyphenyl]pyridine-2-sulfonamide Chemical compound N=1C2=CC(C(C)(C)C)=CC=C2OC=1N(CC1)CCC1OC1=CC=CC=C1NS(=O)(=O)C1=CC=CC=N1 CLICSZJJPWIGEX-UHFFFAOYSA-N 0.000 claims description 2
- 230000008929 regeneration Effects 0.000 claims description 2
- 238000011069 regeneration method Methods 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 6
- 238000009833 condensation Methods 0.000 claims 4
- 230000005494 condensation Effects 0.000 claims 4
- 230000006806 disease prevention Effects 0.000 claims 1
- 230000007062 hydrolysis Effects 0.000 claims 1
- 238000006460 hydrolysis reaction Methods 0.000 claims 1
- VYFOAVADNIHPTR-UHFFFAOYSA-N isatoic anhydride Chemical class NC1=CC=CC=C1CO VYFOAVADNIHPTR-UHFFFAOYSA-N 0.000 claims 1
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 claims 1
- FTCLFVJBYJJMOU-UHFFFAOYSA-N n-[2-[1-(1,3-benzothiazol-2-yl)piperidin-4-yl]oxyphenyl]pyridine-2-sulfonamide Chemical compound C=1C=CC=C(OC2CCN(CC2)C=2SC3=CC=CC=C3N=2)C=1NS(=O)(=O)C1=CC=CC=N1 FTCLFVJBYJJMOU-UHFFFAOYSA-N 0.000 claims 1
- KGWRAHTZPPVCNC-UHFFFAOYSA-N n-[2-[1-(5-chloro-1,3-benzoxazol-2-yl)piperidin-4-yl]oxyphenyl]pyridine-2-sulfonamide Chemical compound N=1C2=CC(Cl)=CC=C2OC=1N(CC1)CCC1OC1=CC=CC=C1NS(=O)(=O)C1=CC=CC=N1 KGWRAHTZPPVCNC-UHFFFAOYSA-N 0.000 claims 1
- RMDVJMZBLGSURX-UHFFFAOYSA-N n-[2-[1-(6-bromo-1,3-benzothiazol-2-yl)piperidin-4-yl]oxyphenyl]pyridine-2-sulfonamide Chemical compound S1C2=CC(Br)=CC=C2N=C1N(CC1)CCC1OC1=CC=CC=C1NS(=O)(=O)C1=CC=CC=N1 RMDVJMZBLGSURX-UHFFFAOYSA-N 0.000 claims 1
- QKVAXWQUEWMOKQ-UHFFFAOYSA-N n-[2-[1-(6-chloro-1,3-benzoxazol-2-yl)piperidin-4-yl]oxyphenyl]pyridine-2-sulfonamide Chemical compound O1C2=CC(Cl)=CC=C2N=C1N(CC1)CCC1OC1=CC=CC=C1NS(=O)(=O)C1=CC=CC=N1 QKVAXWQUEWMOKQ-UHFFFAOYSA-N 0.000 claims 1
- PQUJIYDNCVIJHF-UHFFFAOYSA-N n-[2-[1-(6-methyl-1,3-benzoxazol-2-yl)piperidin-4-yl]oxyphenyl]pyridine-2-sulfonamide Chemical compound O1C2=CC(C)=CC=C2N=C1N(CC1)CCC1OC1=CC=CC=C1NS(=O)(=O)C1=CC=CC=N1 PQUJIYDNCVIJHF-UHFFFAOYSA-N 0.000 claims 1
- JHMDXRSCMBWCAH-UHFFFAOYSA-N n-[2-[4-(4-methyl-1,3-benzothiazol-2-yl)-1,4-diazepane-1-carbonyl]phenyl]quinoline-8-sulfonamide Chemical compound N=1C=2C(C)=CC=CC=2SC=1N(CC1)CCCN1C(=O)C1=CC=CC=C1NS(=O)(=O)C1=CC=CC2=CC=CN=C12 JHMDXRSCMBWCAH-UHFFFAOYSA-N 0.000 claims 1
- ADXGZLMYJHQLJG-UHFFFAOYSA-N n-[2-[4-(4-methyl-1,3-benzothiazol-2-yl)piperazine-1-carbonyl]phenyl]pyridine-2-sulfonamide Chemical compound N=1C=2C(C)=CC=CC=2SC=1N(CC1)CCN1C(=O)C1=CC=CC=C1NS(=O)(=O)C1=CC=CC=N1 ADXGZLMYJHQLJG-UHFFFAOYSA-N 0.000 claims 1
- PGMZZQSBSZSDSF-UHFFFAOYSA-N n-[2-[4-(6-bromo-1,3-benzothiazol-2-yl)piperazine-1-carbonyl]phenyl]-6-methylpyridine-2-sulfonamide;dihydrochloride Chemical compound Cl.Cl.CC1=CC=CC(S(=O)(=O)NC=2C(=CC=CC=2)C(=O)N2CCN(CC2)C=2SC3=CC(Br)=CC=C3N=2)=N1 PGMZZQSBSZSDSF-UHFFFAOYSA-N 0.000 claims 1
- AQQKTRWAWUIXKC-UHFFFAOYSA-N n-[2-[4-(6-bromo-1,3-benzothiazol-2-yl)piperazine-1-carbonyl]phenyl]pyridine-2-sulfonamide Chemical compound S1C2=CC(Br)=CC=C2N=C1N(CC1)CCN1C(=O)C1=CC=CC=C1NS(=O)(=O)C1=CC=CC=N1 AQQKTRWAWUIXKC-UHFFFAOYSA-N 0.000 claims 1
- GJCNMQWRQRJOBX-UHFFFAOYSA-N n-[2-[4-(6-bromo-1,3-benzothiazol-2-yl)piperazine-1-carbonyl]phenyl]pyridine-2-sulfonamide;lithium Chemical compound [Li].S1C2=CC(Br)=CC=C2N=C1N(CC1)CCN1C(=O)C1=CC=CC=C1NS(=O)(=O)C1=CC=CC=N1 GJCNMQWRQRJOBX-UHFFFAOYSA-N 0.000 claims 1
- IARYUWZWGFPBAN-UHFFFAOYSA-N n-[2-[4-(6-bromo-1,3-benzothiazol-2-yl)piperazine-1-carbonyl]phenyl]pyridine-2-sulfonamide;potassium Chemical compound [K].S1C2=CC(Br)=CC=C2N=C1N(CC1)CCN1C(=O)C1=CC=CC=C1NS(=O)(=O)C1=CC=CC=N1 IARYUWZWGFPBAN-UHFFFAOYSA-N 0.000 claims 1
- SUQPFSAUCVYYGV-UHFFFAOYSA-N n-[2-[4-(6-bromo-1,3-benzothiazol-2-yl)piperazine-1-carbonyl]phenyl]pyridine-2-sulfonamide;sodium Chemical compound [Na].S1C2=CC(Br)=CC=C2N=C1N(CC1)CCN1C(=O)C1=CC=CC=C1NS(=O)(=O)C1=CC=CC=N1 SUQPFSAUCVYYGV-UHFFFAOYSA-N 0.000 claims 1
- CHSGLAMFRYTPKF-UHFFFAOYSA-N n-[2-[4-(6-bromo-1,3-benzothiazol-2-yl)piperazine-1-carbonyl]phenyl]quinoline-8-sulfonamide Chemical compound C1=CN=C2C(S(=O)(=O)NC3=CC=CC=C3C(=O)N3CCN(CC3)C3=NC4=CC=C(C=C4S3)Br)=CC=CC2=C1 CHSGLAMFRYTPKF-UHFFFAOYSA-N 0.000 claims 1
- MDMMQTGQVLWRJO-UHFFFAOYSA-N n-[2-[4-(6-chloro-1,3-benzothiazol-2-yl)piperazine-1-carbonyl]phenyl]-5-(trifluoromethyl)pyridine-2-sulfonamide Chemical compound N1=CC(C(F)(F)F)=CC=C1S(=O)(=O)NC1=CC=CC=C1C(=O)N1CCN(C=2SC3=CC(Cl)=CC=C3N=2)CC1 MDMMQTGQVLWRJO-UHFFFAOYSA-N 0.000 claims 1
- LAEYSTYZGLGKBE-UHFFFAOYSA-N n-[2-[4-(6-chloro-1,3-benzothiazol-2-yl)piperazine-1-carbonyl]phenyl]pyridine-2-sulfonamide;hydrochloride Chemical compound Cl.S1C2=CC(Cl)=CC=C2N=C1N(CC1)CCN1C(=O)C1=CC=CC=C1NS(=O)(=O)C1=CC=CC=N1 LAEYSTYZGLGKBE-UHFFFAOYSA-N 0.000 claims 1
- GKZUZTODSKKVLP-UHFFFAOYSA-N n-[2-[4-(6-chloro-1,3-benzothiazol-2-yl)piperazine-1-carbonyl]phenyl]quinoline-8-sulfonamide Chemical compound C1=CN=C2C(S(=O)(=O)NC3=CC=CC=C3C(=O)N3CCN(CC3)C3=NC4=CC=C(C=C4S3)Cl)=CC=CC2=C1 GKZUZTODSKKVLP-UHFFFAOYSA-N 0.000 claims 1
- BLJDLAIEKBEZBH-UHFFFAOYSA-N n-[2-[4-(6-chloro-1,3-benzoxazol-2-yl)piperazine-1-carbonyl]phenyl]quinoline-8-sulfonamide Chemical compound C1=CN=C2C(S(=O)(=O)NC3=CC=CC=C3C(=O)N3CCN(CC3)C3=NC4=CC=C(C=C4O3)Cl)=CC=CC2=C1 BLJDLAIEKBEZBH-UHFFFAOYSA-N 0.000 claims 1
- AZFAWVCGOWVVBJ-UHFFFAOYSA-N n-[2-[4-(6-fluoro-1,3-benzothiazol-2-yl)piperazine-1-carbonyl]phenyl]pyridine-2-sulfonamide Chemical compound S1C2=CC(F)=CC=C2N=C1N(CC1)CCN1C(=O)C1=CC=CC=C1NS(=O)(=O)C1=CC=CC=N1 AZFAWVCGOWVVBJ-UHFFFAOYSA-N 0.000 claims 1
- APIZSXNICKBCMT-UHFFFAOYSA-N n-[2-[4-(6-fluoro-1,3-benzoxazol-2-yl)piperazine-1-carbonyl]phenyl]-5-(trifluoromethyl)pyridine-2-sulfonamide Chemical compound O1C2=CC(F)=CC=C2N=C1N(CC1)CCN1C(=O)C1=CC=CC=C1NS(=O)(=O)C1=CC=C(C(F)(F)F)C=N1 APIZSXNICKBCMT-UHFFFAOYSA-N 0.000 claims 1
- XETPZJGILMXLCR-UHFFFAOYSA-N n-[2-[4-(7-chloro-1,3-benzothiazol-2-yl)piperazine-1-carbonyl]phenyl]pyridine-2-sulfonamide Chemical compound S1C=2C(Cl)=CC=CC=2N=C1N(CC1)CCN1C(=O)C1=CC=CC=C1NS(=O)(=O)C1=CC=CC=N1 XETPZJGILMXLCR-UHFFFAOYSA-N 0.000 claims 1
- VPQNZNHSRCYEJF-UHFFFAOYSA-N n-[2-[4-[5-(trifluoromethyl)-1,3-benzothiazol-2-yl]piperazine-1-carbonyl]phenyl]pyridine-2-sulfonamide Chemical compound N=1C2=CC(C(F)(F)F)=CC=C2SC=1N(CC1)CCN1C(=O)C1=CC=CC=C1NS(=O)(=O)C1=CC=CC=N1 VPQNZNHSRCYEJF-UHFFFAOYSA-N 0.000 claims 1
- VLPMAOQQURVSNS-UHFFFAOYSA-N n-[2-[4-[6-(trifluoromethoxy)-1,3-benzothiazol-2-yl]piperazine-1-carbonyl]phenyl]quinoline-8-sulfonamide Chemical compound C1=CN=C2C(S(=O)(=O)NC3=CC=CC=C3C(=O)N3CCN(CC3)C3=NC4=CC=C(C=C4S3)OC(F)(F)F)=CC=CC2=C1 VLPMAOQQURVSNS-UHFFFAOYSA-N 0.000 claims 1
- VXTMDNUGGBANEZ-UHFFFAOYSA-N n-[2-[[1-(1,3-benzothiazol-2-yl)pyrrolidin-3-yl]methoxy]phenyl]pyridine-2-sulfonamide Chemical compound C=1C=CC=C(OCC2CN(CC2)C=2SC3=CC=CC=C3N=2)C=1NS(=O)(=O)C1=CC=CC=N1 VXTMDNUGGBANEZ-UHFFFAOYSA-N 0.000 claims 1
- UKYIUMLFJHIALD-UHFFFAOYSA-N n-[2-[[1-(4-methoxy-1,3-benzothiazol-2-yl)pyrrolidin-3-yl]methoxy]phenyl]pyridine-2-sulfonamide Chemical compound N=1C=2C(OC)=CC=CC=2SC=1N(C1)CCC1COC1=CC=CC=C1NS(=O)(=O)C1=CC=CC=N1 UKYIUMLFJHIALD-UHFFFAOYSA-N 0.000 claims 1
- FWKRHEQNUAHZOB-UHFFFAOYSA-N n-[2-[[1-(4-methyl-1,3-benzothiazol-2-yl)pyrrolidin-3-yl]methoxy]phenyl]pyridine-2-sulfonamide Chemical compound N=1C=2C(C)=CC=CC=2SC=1N(C1)CCC1COC1=CC=CC=C1NS(=O)(=O)C1=CC=CC=N1 FWKRHEQNUAHZOB-UHFFFAOYSA-N 0.000 claims 1
- HSCTZILYCPRWKA-UHFFFAOYSA-N n-[2-[[1-(6-chloro-1,3-benzothiazol-2-yl)pyrrolidin-3-yl]methoxy]phenyl]pyridine-2-sulfonamide Chemical compound S1C2=CC(Cl)=CC=C2N=C1N(C1)CCC1COC1=CC=CC=C1NS(=O)(=O)C1=CC=CC=N1 HSCTZILYCPRWKA-UHFFFAOYSA-N 0.000 claims 1
- QZTXJRUCNBJKHI-UHFFFAOYSA-N n-[2-[[1-(6-fluoro-1,3-benzothiazol-2-yl)pyrrolidin-3-yl]methoxy]phenyl]pyridine-2-sulfonamide Chemical compound S1C2=CC(F)=CC=C2N=C1N(C1)CCC1COC1=CC=CC=C1NS(=O)(=O)C1=CC=CC=N1 QZTXJRUCNBJKHI-UHFFFAOYSA-N 0.000 claims 1
- HQUPVOAZJDPSBO-UHFFFAOYSA-N n-[3-[4-(6-chloro-1,3-benzothiazol-2-yl)piperazine-1-carbonyl]phenyl]-6-methylpyridine-2-sulfonamide Chemical compound CC1=CC=CC(S(=O)(=O)NC=2C=C(C=CC=2)C(=O)N2CCN(CC2)C=2SC3=CC(Cl)=CC=C3N=2)=N1 HQUPVOAZJDPSBO-UHFFFAOYSA-N 0.000 claims 1
- PRZNECJSFLHDEH-UHFFFAOYSA-N n-[3-[4-(6-chloro-1,3-benzothiazol-2-yl)piperazine-1-carbonyl]phenyl]pyridine-2-sulfonamide Chemical compound S1C2=CC(Cl)=CC=C2N=C1N(CC1)CCN1C(=O)C(C=1)=CC=CC=1NS(=O)(=O)C1=CC=CC=N1 PRZNECJSFLHDEH-UHFFFAOYSA-N 0.000 claims 1
- GHYHGSNORYNIRO-UHFFFAOYSA-N n-[3-[4-(6-chloro-1,3-benzoxazol-2-yl)piperazine-1-carbonyl]phenyl]pyridine-2-sulfonamide Chemical compound O1C2=CC(Cl)=CC=C2N=C1N(CC1)CCN1C(=O)C(C=1)=CC=CC=1NS(=O)(=O)C1=CC=CC=N1 GHYHGSNORYNIRO-UHFFFAOYSA-N 0.000 claims 1
- TZABFPVQEOIMCQ-UHFFFAOYSA-N n-[4-[4-(6-chloro-1,3-benzothiazol-2-yl)piperazine-1-carbonyl]phenyl]pyridine-2-sulfonamide Chemical compound S1C2=CC(Cl)=CC=C2N=C1N(CC1)CCN1C(=O)C(C=C1)=CC=C1NS(=O)(=O)C1=CC=CC=N1 TZABFPVQEOIMCQ-UHFFFAOYSA-N 0.000 claims 1
- ZQNODSHXXVSTIH-UHFFFAOYSA-N n-[4-[4-(6-chloro-1,3-benzoxazol-2-yl)piperazine-1-carbonyl]phenyl]pyridine-2-sulfonamide Chemical compound O1C2=CC(Cl)=CC=C2N=C1N(CC1)CCN1C(=O)C(C=C1)=CC=C1NS(=O)(=O)C1=CC=CC=N1 ZQNODSHXXVSTIH-UHFFFAOYSA-N 0.000 claims 1
- YOFGQVREJHTFCI-UHFFFAOYSA-N n-[4-[4-(6-fluoro-1,3-benzoxazol-2-yl)piperazine-1-carbonyl]phenyl]pyridine-2-sulfonamide Chemical compound O1C2=CC(F)=CC=C2N=C1N(CC1)CCN1C(=O)C(C=C1)=CC=C1NS(=O)(=O)C1=CC=CC=N1 YOFGQVREJHTFCI-UHFFFAOYSA-N 0.000 claims 1
- 238000007127 saponification reaction Methods 0.000 claims 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
- HWCKGOZZJDHMNC-UHFFFAOYSA-M tetraethylammonium bromide Chemical compound [Br-].CC[N+](CC)(CC)CC HWCKGOZZJDHMNC-UHFFFAOYSA-M 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 abstract description 8
- 238000011281 clinical therapy Methods 0.000 abstract description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 description 119
- 238000004809 thin layer chromatography Methods 0.000 description 67
- IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 63
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 46
- 239000007787 solid Substances 0.000 description 39
- 238000005481 NMR spectroscopy Methods 0.000 description 38
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 34
- 238000001308 synthesis method Methods 0.000 description 34
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Substances OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
- WGLUMOCWFMKWIL-UHFFFAOYSA-N dichloromethane;methanol Chemical compound OC.ClCCl WGLUMOCWFMKWIL-UHFFFAOYSA-N 0.000 description 24
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 20
- 239000003208 petroleum Substances 0.000 description 20
- 239000000203 mixture Substances 0.000 description 18
- SRCZQMGIVIYBBJ-UHFFFAOYSA-N ethoxyethane;ethyl acetate Chemical compound CCOCC.CCOC(C)=O SRCZQMGIVIYBBJ-UHFFFAOYSA-N 0.000 description 17
- DWJMBQYORXLGAE-UHFFFAOYSA-N pyridine-2-sulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=N1 DWJMBQYORXLGAE-UHFFFAOYSA-N 0.000 description 16
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- JCBJVAJGLKENNC-UHFFFAOYSA-M potassium ethyl xanthate Chemical compound [K+].CCOC([S-])=S JCBJVAJGLKENNC-UHFFFAOYSA-M 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- 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
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/444—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a six-membered ring with nitrogen as a ring heteroatom, e.g. amrinone
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
- A61K31/4709—Non-condensed quinolines and containing further heterocyclic rings
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- A—HUMAN NECESSITIES
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
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- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/496—Non-condensed piperazines containing further heterocyclic rings, e.g. rifampin, thiothixene or sparfloxacin
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- A61P9/00—Drugs for disorders of the cardiovascular system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- 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
- C07D413/02—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
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Cardiology (AREA)
- Epidemiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Vascular Medicine (AREA)
- Urology & Nephrology (AREA)
- Hospice & Palliative Care (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR1059634A FR2967674B1 (fr) | 2010-11-23 | 2010-11-23 | Derives d'heteroarylsulfonamides, leur preparation et leur application en therapeutique humaine |
| FR1059634 | 2010-11-23 | ||
| PCT/EP2011/070736 WO2012069503A1 (en) | 2010-11-23 | 2011-11-23 | Derivatives of heteroarylsulfonamides, their preparation and their application in human therapy |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2817531A1 true CA2817531A1 (en) | 2012-05-31 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2817531A Abandoned CA2817531A1 (en) | 2010-11-23 | 2011-11-23 | Derivatives of heteroarylsulfonamides, their preparation and their application in human therapy |
Country Status (19)
| Country | Link |
|---|---|
| US (2) | US8846930B2 (enExample) |
| EP (1) | EP2643318A1 (enExample) |
| JP (1) | JP5837085B2 (enExample) |
| KR (1) | KR101838326B1 (enExample) |
| CN (1) | CN103209980B (enExample) |
| AR (1) | AR083903A1 (enExample) |
| AU (1) | AU2011333772B2 (enExample) |
| BR (1) | BR112013012615A2 (enExample) |
| CA (1) | CA2817531A1 (enExample) |
| FR (1) | FR2967674B1 (enExample) |
| IL (1) | IL226495A (enExample) |
| MA (1) | MA34658B1 (enExample) |
| MX (1) | MX352396B (enExample) |
| MY (1) | MY168283A (enExample) |
| NZ (1) | NZ610700A (enExample) |
| RU (1) | RU2582995C2 (enExample) |
| TW (1) | TWI576106B (enExample) |
| UA (1) | UA109295C2 (enExample) |
| WO (1) | WO2012069503A1 (enExample) |
Families Citing this family (14)
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| NZ597379A (en) | 2009-06-29 | 2014-04-30 | Agios Pharmaceuticals Inc | Therapeutic compounds and compositions |
| WO2012151452A1 (en) * | 2011-05-03 | 2012-11-08 | Agios Pharmaceuticals, Inc | Pyruvate kinase activators for use in therapy |
| PH12017501176B1 (en) | 2011-05-03 | 2023-03-08 | Agios Pharmaceuticals Inc | Pyruvate kinase activators for use in therapy |
| WO2014139144A1 (en) | 2013-03-15 | 2014-09-18 | Agios Pharmaceuticals, Inc. | Therapeutic compounds and compositions |
| CN105705495A (zh) * | 2013-10-17 | 2016-06-22 | 巴斯夫欧洲公司 | 制备取代靛红酸酐化合物及其衍生物的方法 |
| WO2015095111A1 (en) * | 2013-12-18 | 2015-06-25 | Merck Sharp & Dohme Corp. | Diazepane orexin receptor antagonists |
| CN104292179A (zh) * | 2014-10-19 | 2015-01-21 | 湖南华腾制药有限公司 | 一种2-氯苯并[d]恶唑-5-甲醛的制备方法 |
| FR3029112A1 (fr) * | 2014-12-02 | 2016-06-03 | Pf Medicament | Dispersion solide a base de derives d'heteroarylsulfonamides a usage pharmaceutique |
| SI3307271T1 (sl) | 2015-06-11 | 2023-11-30 | Agios Pharmaceuticals, Inc. | Postopki za uporabo aktivatorjev piruvat kinaze |
| EP3601273B1 (en) * | 2017-03-24 | 2021-12-01 | Genentech, Inc. | 4-piperidin-n-(pyrimidin-4-yl)chroman-7-sulfonamide derivatives as sodium channel inhibitors |
| CN107556266B (zh) * | 2017-09-12 | 2021-04-23 | 华南农业大学 | 一种2-巯基-4-取代-6-氟苯并噻唑及其制法、应用 |
| US20200131156A1 (en) * | 2018-10-30 | 2020-04-30 | H. Lundbeck A/S | ARYLSULFONYLPYROLECARBOXAMIDE DERIVATIVES AS Kv3 POTASSIUM CHANNEL ACTIVATORS |
| CN113200934B (zh) * | 2021-05-18 | 2022-05-31 | 郑州大学 | 含苯并吗啉酮-联苯骨架化合物及其制备方法和应用 |
| CN113912595B (zh) * | 2021-10-12 | 2024-03-15 | 中国药科大学 | 一类含有噻唑或噻二唑结构的化合物及其应用 |
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| US5149700A (en) * | 1990-05-30 | 1992-09-22 | American Home Products Corporation | Substituted arylsulfonamides and benzamides |
| DE10128331A1 (de) * | 2001-06-12 | 2002-12-19 | Aventis Pharma Gmbh | Anthranilsäureamide mit Heteroarylsulfonyl-Seitenkette, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltende pharmazeutische Zubereitungen |
| ATE430142T1 (de) * | 2004-12-09 | 2009-05-15 | Hoffmann La Roche | Phenylpiperazin-methanon-derivate |
| EP1902051A1 (en) * | 2005-06-09 | 2008-03-26 | Merck Frosst Canada Ltd. | Azacyclohexane derivatives as inhibitors of stearoyl-coenzyme a delta-9 desaturase |
| WO2007023882A1 (ja) * | 2005-08-26 | 2007-03-01 | Shionogi & Co., Ltd. | Ｐｐａｒアゴニスト活性を有する誘導体 |
| WO2009055357A1 (en) * | 2007-10-25 | 2009-04-30 | Boehringer Ingelheim International Gmbh | Diazepane compounds which modulate the cb2 receptor |
| CA2727780A1 (en) * | 2008-06-13 | 2009-12-17 | Bionomics Limited | Novel potassium channel blockers and uses thereof |
| GB0815781D0 (en) * | 2008-08-29 | 2008-10-08 | Xention Ltd | Novel potassium channel blockers |
| CN101503392B (zh) * | 2009-03-31 | 2010-12-29 | 中国药科大学 | 芳甲胺类化合物、其制备方法及其医药用途 |
| WO2010130638A1 (en) * | 2009-05-14 | 2010-11-18 | Evotec Ag | Sulfonamide compounds, pharmaceutical compositions and uses thereof |
| NZ597379A (en) * | 2009-06-29 | 2014-04-30 | Agios Pharmaceuticals Inc | Therapeutic compounds and compositions |
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Also Published As
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| AU2011333772A1 (en) | 2013-06-06 |
| US9156834B2 (en) | 2015-10-13 |
| CN103209980B (zh) | 2015-06-03 |
| JP2014502268A (ja) | 2014-01-30 |
| WO2012069503A1 (en) | 2012-05-31 |
| JP5837085B2 (ja) | 2015-12-24 |
| RU2013126251A (ru) | 2014-12-27 |
| IL226495A0 (en) | 2013-07-31 |
| RU2582995C2 (ru) | 2016-04-27 |
| UA109295C2 (uk) | 2015-08-10 |
| TWI576106B (zh) | 2017-04-01 |
| HK1187345A1 (en) | 2014-04-04 |
| EP2643318A1 (en) | 2013-10-02 |
| AU2011333772B2 (en) | 2016-08-18 |
| US8846930B2 (en) | 2014-09-30 |
| KR20130119943A (ko) | 2013-11-01 |
| MX352396B (es) | 2017-11-22 |
| KR101838326B1 (ko) | 2018-03-13 |
| MX2013005734A (es) | 2013-08-01 |
| AR083903A1 (es) | 2013-04-10 |
| FR2967674B1 (fr) | 2012-12-14 |
| US20130172326A1 (en) | 2013-07-04 |
| NZ610700A (en) | 2014-12-24 |
| IL226495A (en) | 2017-06-29 |
| FR2967674A1 (fr) | 2012-05-25 |
| MA34658B1 (fr) | 2013-11-02 |
| BR112013012615A2 (pt) | 2016-09-06 |
| US20140357624A1 (en) | 2014-12-04 |
| TW201225951A (en) | 2012-07-01 |
| CN103209980A (zh) | 2013-07-17 |
| MY168283A (en) | 2018-10-19 |
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Effective date: 20161027 |
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| FZDE | Discontinued |
Effective date: 20191125 |