DD297817A5 - Benzimidazol-2- und imidazopyridin-2-sulfonamid-derivate, ihre herstellung und verwendung als medikamente oder zwischenprodukte fuer diese - Google Patents
Benzimidazol-2- und imidazopyridin-2-sulfonamid-derivate, ihre herstellung und verwendung als medikamente oder zwischenprodukte fuer diese Download PDFInfo
- Publication number
- DD297817A5 DD297817A5 DD87301968A DD30196887A DD297817A5 DD 297817 A5 DD297817 A5 DD 297817A5 DD 87301968 A DD87301968 A DD 87301968A DD 30196887 A DD30196887 A DD 30196887A DD 297817 A5 DD297817 A5 DD 297817A5
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- radical
- benzimidazole
- sulfonamide
- dihydro
- thiadiazino
- Prior art date
Links
- 229940124530 sulfonamide Drugs 0.000 title claims abstract description 37
- 238000002360 preparation method Methods 0.000 title claims abstract description 29
- 239000003814 drug Substances 0.000 title claims abstract description 10
- 239000000543 intermediate Substances 0.000 title abstract description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 116
- 150000003839 salts Chemical class 0.000 claims abstract description 11
- XRGHQBXKSHAQRB-UHFFFAOYSA-N 1h-benzimidazole-2-sulfonamide Chemical compound C1=CC=C2NC(S(=O)(=O)N)=NC2=C1 XRGHQBXKSHAQRB-UHFFFAOYSA-N 0.000 claims abstract description 8
- 230000027119 gastric acid secretion Effects 0.000 claims abstract description 8
- 208000018522 Gastrointestinal disease Diseases 0.000 claims abstract description 5
- 239000003699 antiulcer agent Substances 0.000 claims abstract description 5
- 230000000767 anti-ulcer Effects 0.000 claims abstract description 4
- -1 alkyl radical Chemical class 0.000 claims description 471
- 150000003254 radicals Chemical class 0.000 claims description 166
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 92
- 229910052757 nitrogen Inorganic materials 0.000 claims description 73
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 65
- 125000004432 carbon atom Chemical group C* 0.000 claims description 63
- 229910052799 carbon Chemical group 0.000 claims description 52
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 45
- 125000004414 alkyl thio group Chemical group 0.000 claims description 44
- 239000000460 chlorine Substances 0.000 claims description 40
- 238000000034 method Methods 0.000 claims description 40
- 238000006243 chemical reaction Methods 0.000 claims description 34
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 34
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 33
- BLNWTAHYTCHDJH-UHFFFAOYSA-O hydroxy(oxo)azanium Chemical compound O[NH+]=O BLNWTAHYTCHDJH-UHFFFAOYSA-O 0.000 claims description 28
- 239000000203 mixture Substances 0.000 claims description 28
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 26
- 239000001257 hydrogen Substances 0.000 claims description 24
- 229910052739 hydrogen Inorganic materials 0.000 claims description 24
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 23
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 22
- 150000005840 aryl radicals Chemical class 0.000 claims description 22
- 239000000243 solution Substances 0.000 claims description 21
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims description 20
- 125000005843 halogen group Chemical group 0.000 claims description 19
- 239000002904 solvent Substances 0.000 claims description 19
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 15
- WZKSXHQDXQKIQJ-UHFFFAOYSA-N F[C](F)F Chemical compound F[C](F)F WZKSXHQDXQKIQJ-UHFFFAOYSA-N 0.000 claims description 15
- 150000002431 hydrogen Chemical class 0.000 claims description 14
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims description 12
- JEVCWSUVFOYBFI-UHFFFAOYSA-N cyanyl Chemical compound N#[C] JEVCWSUVFOYBFI-UHFFFAOYSA-N 0.000 claims description 12
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical compound [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 claims description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- 125000004181 carboxyalkyl group Chemical group 0.000 claims description 10
- 125000002843 carboxylic acid group Chemical group 0.000 claims description 10
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 10
- 125000003277 amino group Chemical group 0.000 claims description 9
- 125000005518 carboxamido group Chemical group 0.000 claims description 9
- 229910052801 chlorine Inorganic materials 0.000 claims description 9
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 9
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 8
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 8
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 8
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims description 8
- 229910052740 iodine Inorganic materials 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 7
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 6
- 150000001298 alcohols Chemical class 0.000 claims description 6
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 claims description 6
- RGICCULPCWNRAB-UHFFFAOYSA-N 2-[2-(2-hexoxyethoxy)ethoxy]ethanol Chemical compound CCCCCCOCCOCCOCCO RGICCULPCWNRAB-UHFFFAOYSA-N 0.000 claims description 5
- 239000007864 aqueous solution Substances 0.000 claims description 5
- 239000003054 catalyst Substances 0.000 claims description 5
- 229920000137 polyphosphoric acid Polymers 0.000 claims description 5
- 239000000725 suspension Substances 0.000 claims description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 4
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- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 4
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- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 125000005842 heteroatom Chemical group 0.000 claims description 4
- 239000003112 inhibitor Substances 0.000 claims description 4
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 claims description 4
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims description 4
- 229920006395 saturated elastomer Polymers 0.000 claims description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 4
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 claims description 4
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims description 3
- 125000006479 2-pyridyl methyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims description 3
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 3
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 3
- 239000003638 chemical reducing agent Substances 0.000 claims description 3
- 229910017604 nitric acid Inorganic materials 0.000 claims description 3
- 235000010288 sodium nitrite Nutrition 0.000 claims description 3
- 150000003456 sulfonamides Chemical class 0.000 claims description 3
- ZWZVWGITAAIFPS-UHFFFAOYSA-N thiophosgene Chemical compound ClC(Cl)=S ZWZVWGITAAIFPS-UHFFFAOYSA-N 0.000 claims description 3
- PDXCOWCINSIDPO-UHFFFAOYSA-N 2h-thiadiazine 1,1-dioxide Chemical compound O=S1(=O)NN=CC=C1 PDXCOWCINSIDPO-UHFFFAOYSA-N 0.000 claims description 2
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 2
- SYBQMBHDNXLOKK-UHFFFAOYSA-N 4-nitro-1h-benzimidazole-2-sulfonamide Chemical compound C1=CC=C2NC(S(=O)(=O)N)=NC2=C1[N+]([O-])=O SYBQMBHDNXLOKK-UHFFFAOYSA-N 0.000 claims description 2
- VORDSNQYLLYANA-UHFFFAOYSA-N 7,8-dichloro-3,4-dihydro-2h-[1,2,5]thiadiazino[5,6-a]benzimidazole 1,1-dioxide Chemical compound C1=2C=C(Cl)C(Cl)=CC=2N=C2N1CCNS2(=O)=O VORDSNQYLLYANA-UHFFFAOYSA-N 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 2
- 239000002841 Lewis acid Substances 0.000 claims description 2
- 125000004442 acylamino group Chemical group 0.000 claims description 2
- 229910021529 ammonia Inorganic materials 0.000 claims description 2
- 150000008064 anhydrides Chemical class 0.000 claims description 2
- 239000007900 aqueous suspension Substances 0.000 claims description 2
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 230000003197 catalytic effect Effects 0.000 claims description 2
- 229910052802 copper Inorganic materials 0.000 claims description 2
- 239000010949 copper Substances 0.000 claims description 2
- 239000012954 diazonium Substances 0.000 claims description 2
- 150000001989 diazonium salts Chemical class 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- 150000004820 halides Chemical class 0.000 claims description 2
- 125000001072 heteroaryl group Chemical group 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 2
- ZBKFYXZXZJPWNQ-UHFFFAOYSA-N isothiocyanate group Chemical group [N-]=C=S ZBKFYXZXZJPWNQ-UHFFFAOYSA-N 0.000 claims description 2
- 150000007517 lewis acids Chemical class 0.000 claims description 2
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims description 2
- ZCAOCTAFKPRLBR-UHFFFAOYSA-N n-(4-fluorophenyl)-4-nitro-1h-benzimidazole-2-sulfonamide Chemical compound N=1C=2C([N+](=O)[O-])=CC=CC=2NC=1S(=O)(=O)NC1=CC=C(F)C=C1 ZCAOCTAFKPRLBR-UHFFFAOYSA-N 0.000 claims description 2
- XMJLTRUWMNFUOL-UHFFFAOYSA-N n-(pyridin-2-ylmethyl)-1h-benzimidazole-2-sulfonamide Chemical compound N=1C2=CC=CC=C2NC=1S(=O)(=O)NCC1=CC=CC=N1 XMJLTRUWMNFUOL-UHFFFAOYSA-N 0.000 claims description 2
- FXVSNEWMKBJWEF-UHFFFAOYSA-N n-[2-(diethylamino)ethyl]-1h-benzimidazole-2-sulfonamide Chemical compound C1=CC=C2NC(S(=O)(=O)NCCN(CC)CC)=NC2=C1 FXVSNEWMKBJWEF-UHFFFAOYSA-N 0.000 claims description 2
- RCVJIVHZSALRIE-UHFFFAOYSA-N n-ethyl-1h-imidazo[4,5-b]pyridine-2-sulfonamide Chemical compound C1=CC=C2NC(S(=O)(=O)NCC)=NC2=N1 RCVJIVHZSALRIE-UHFFFAOYSA-N 0.000 claims description 2
- QEVAYFZTXUBZBS-UHFFFAOYSA-N n-methyl-4-nitro-1h-benzimidazole-2-sulfonamide Chemical compound C1=CC=C2NC(S(=O)(=O)NC)=NC2=C1[N+]([O-])=O QEVAYFZTXUBZBS-UHFFFAOYSA-N 0.000 claims description 2
- 230000000802 nitrating effect Effects 0.000 claims description 2
- 238000006396 nitration reaction Methods 0.000 claims description 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- NVBFHJWHLNUMCV-UHFFFAOYSA-N sulfamide Chemical compound NS(N)(=O)=O NVBFHJWHLNUMCV-UHFFFAOYSA-N 0.000 claims description 2
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Inorganic materials O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 claims description 2
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 claims description 2
- 239000011592 zinc chloride Substances 0.000 claims description 2
- 235000005074 zinc chloride Nutrition 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 2
- TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 claims 1
- PGKVTXJRZRXLIU-UHFFFAOYSA-N 2-(1,1-dioxo-3,4-dihydro-[1,2,5]thiadiazino[5,6-a]benzimidazol-2-yl)-n,n-diethylethanamine Chemical compound C1=CC=C2N3CCN(CCN(CC)CC)S(=O)(=O)C3=NC2=C1 PGKVTXJRZRXLIU-UHFFFAOYSA-N 0.000 claims 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
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- VIGKMYXLKSQYSG-UHFFFAOYSA-N 6-(7-chloro-1,1-dioxo-3,4-dihydro-[1,2,5]thiadiazino[5,6-a]benzimidazol-2-yl)-n,n-diethylhexan-1-amine Chemical compound C1=C(Cl)C=C2N3CCN(CCCCCCN(CC)CC)S(=O)(=O)C3=NC2=C1 VIGKMYXLKSQYSG-UHFFFAOYSA-N 0.000 claims 1
- OWCGSWVKRZFCJD-UHFFFAOYSA-N 6-nitro-1h-benzimidazole-2-sulfonamide Chemical compound C1=C([N+]([O-])=O)C=C2NC(S(=O)(=O)N)=NC2=C1 OWCGSWVKRZFCJD-UHFFFAOYSA-N 0.000 claims 1
- 229910021591 Copper(I) chloride Inorganic materials 0.000 claims 1
- 229910021578 Iron(III) chloride Inorganic materials 0.000 claims 1
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- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
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- 239000013256 coordination polymer Substances 0.000 claims 1
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 claims 1
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- UTCSSFWDNNEEBH-UHFFFAOYSA-N imidazo[1,2-a]pyridine Chemical compound C1=CC=CC2=NC=CN21 UTCSSFWDNNEEBH-UHFFFAOYSA-N 0.000 claims 1
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- JOHLODUKKFLWOA-UHFFFAOYSA-N n-butyl-3h-imidazo[4,5-c]pyridine-2-sulfonamide Chemical compound N1=CC=C2NC(S(=O)(=O)NCCCC)=NC2=C1 JOHLODUKKFLWOA-UHFFFAOYSA-N 0.000 description 1
- ROYXWZQFHTVLEI-UHFFFAOYSA-N n-butyl-4-nitro-1h-benzimidazole-2-sulfonamide Chemical compound C1=CC=C2NC(S(=O)(=O)NCCCC)=NC2=C1[N+]([O-])=O ROYXWZQFHTVLEI-UHFFFAOYSA-N 0.000 description 1
- GKKODFZTEDYDQW-UHFFFAOYSA-N n-ethyl-1-(2-oxo-2-pyridin-2-ylethyl)benzimidazole-2-sulfonamide Chemical compound CCNS(=O)(=O)C1=NC2=CC=CC=C2N1CC(=O)C1=CC=CC=N1 GKKODFZTEDYDQW-UHFFFAOYSA-N 0.000 description 1
- XAXWGFCLOIJJHN-UHFFFAOYSA-N n-ethyl-1-phenacylbenzimidazole-2-sulfonamide Chemical compound CCNS(=O)(=O)C1=NC2=CC=CC=C2N1CC(=O)C1=CC=CC=C1 XAXWGFCLOIJJHN-UHFFFAOYSA-N 0.000 description 1
- RMXVVJGEEUATGV-UHFFFAOYSA-N n-ethyl-4-nitro-1h-benzimidazole-2-sulfonamide Chemical compound C1=CC=C2NC(S(=O)(=O)NCC)=NC2=C1[N+]([O-])=O RMXVVJGEEUATGV-UHFFFAOYSA-N 0.000 description 1
- KNDIGJJAOGBIQL-UHFFFAOYSA-N n-ethyl-6-(trifluoromethyl)-1h-benzimidazole-2-sulfonamide Chemical compound FC(F)(F)C1=CC=C2NC(S(=O)(=O)NCC)=NC2=C1 KNDIGJJAOGBIQL-UHFFFAOYSA-N 0.000 description 1
- YAQRUIGCUSOXLZ-UHFFFAOYSA-N n-ethyl-6-nitro-1h-benzimidazole-2-sulfonamide Chemical compound [O-][N+](=O)C1=CC=C2NC(S(=O)(=O)NCC)=NC2=C1 YAQRUIGCUSOXLZ-UHFFFAOYSA-N 0.000 description 1
- AYDNUGUBVFWSAC-UHFFFAOYSA-N n-ethyl-6-phenoxy-1h-benzimidazole-2-sulfonamide Chemical compound C=1C=C2NC(S(=O)(=O)NCC)=NC2=CC=1OC1=CC=CC=C1 AYDNUGUBVFWSAC-UHFFFAOYSA-N 0.000 description 1
- LPGJZPGTRPOXLL-UHFFFAOYSA-N n-ethyl-n,4-dinitro-1h-benzimidazole-2-sulfonamide Chemical compound C1=CC=C2NC(S(=O)(=O)N([N+]([O-])=O)CC)=NC2=C1[N+]([O-])=O LPGJZPGTRPOXLL-UHFFFAOYSA-N 0.000 description 1
- NUAZXIMIJGAYFN-UHFFFAOYSA-N n-methyl-1h-benzimidazole-2-sulfonamide Chemical compound C1=CC=C2NC(S(=O)(=O)NC)=NC2=C1 NUAZXIMIJGAYFN-UHFFFAOYSA-N 0.000 description 1
- DQCYMMOOWJEHBY-UHFFFAOYSA-N n-pyridin-2-yl-1h-benzimidazole-2-sulfonamide Chemical compound N=1C2=CC=CC=C2NC=1S(=O)(=O)NC1=CC=CC=N1 DQCYMMOOWJEHBY-UHFFFAOYSA-N 0.000 description 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
- 125000006501 nitrophenyl group Chemical group 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 238000003359 percent control normalization Methods 0.000 description 1
- 230000002085 persistent effect Effects 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 238000004634 pharmacological analysis method Methods 0.000 description 1
- WVONOTFBACQFPO-UHFFFAOYSA-N phenyl-(2-sulfanylidene-1,3-dihydrobenzimidazol-5-yl)methanone Chemical compound C=1C=C2NC(=S)NC2=CC=1C(=O)C1=CC=CC=C1 WVONOTFBACQFPO-UHFFFAOYSA-N 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- OVARTBFNCCXQKS-UHFFFAOYSA-N propan-2-one;hydrate Chemical compound O.CC(C)=O OVARTBFNCCXQKS-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 229910052979 sodium sulfide Inorganic materials 0.000 description 1
- GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 239000007916 tablet composition Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 239000004246 zinc acetate Substances 0.000 description 1
Classifications
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles 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 in position 2
- C07D235/28—Sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains three hetero rings
- C07D513/14—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8605721A FR2597478B1 (fr) | 1986-04-21 | 1986-04-21 | Benzimidazoles et imidazopyridines sulfonamides, leur preparation et leur application en tant que medicaments. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DD297817A5 true DD297817A5 (de) | 1992-01-23 |
Family
ID=9334440
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD87301968A DD297817A5 (de) | 1986-04-21 | 1987-04-20 | Benzimidazol-2- und imidazopyridin-2-sulfonamid-derivate, ihre herstellung und verwendung als medikamente oder zwischenprodukte fuer diese |
Country Status (20)
| Country | Link |
|---|---|
| US (2) | US4933338A (pl) |
| EP (1) | EP0246126A1 (pl) |
| JP (1) | JPH0643404B2 (pl) |
| KR (1) | KR930003613B1 (pl) |
| CN (1) | CN87102916A (pl) |
| AU (1) | AU608511B2 (pl) |
| BR (1) | BR8701897A (pl) |
| CA (1) | CA1300133C (pl) |
| DD (1) | DD297817A5 (pl) |
| DK (1) | DK185487A (pl) |
| ES (1) | ES2005158A6 (pl) |
| FR (1) | FR2597478B1 (pl) |
| HU (1) | HUT63151A (pl) |
| IN (1) | IN167204B (pl) |
| NO (1) | NO871643L (pl) |
| PL (1) | PL156736B1 (pl) |
| PT (1) | PT84724B (pl) |
| RU (1) | RU1813087C (pl) |
| YU (1) | YU46193B (pl) |
| ZA (1) | ZA872739B (pl) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HU195220B (en) * | 1983-05-03 | 1988-04-28 | Byk Gulden Lomberg Chem Fqb | Process for production of new fluor-alkoxi-benzimidasole-derivatives and medical compositions containig them |
| KR950001015B1 (ko) * | 1986-01-10 | 1995-02-07 | 닛뽕 케미화 가부시끼가이샤 | 술폭시드 유도체의 제조방법 |
| WO1989010927A1 (en) * | 1988-05-12 | 1989-11-16 | Eisai Co., Ltd. | Pyridinium salt and pharmacological composition containing the same |
| IL113472A0 (en) | 1994-04-29 | 1995-07-31 | Lilly Co Eli | Non-peptidyl tachykinin receptor antogonists |
| CA2332928A1 (en) | 1998-05-23 | 1999-12-02 | Byk Gulden Lomberg Chemische Fabrik Gmbh | Quinoline-aminomethyl-pyridyl derivatives with anti-helicobacter activity |
| AU1708099A (en) | 1998-06-03 | 1999-12-20 | Amgen, Inc. | N-linked sulfonamides of n-heterocyclic carboxylic acids or carboxylic acid isosteres |
| AU2003282510A1 (en) * | 2002-10-11 | 2004-05-04 | Bristol-Myers Squibb Company | Hexahydro-benzimidazolone compounds useful as anti-inflammatory agents |
| CN101497616B (zh) * | 2008-01-30 | 2011-05-18 | 山东轩竹医药科技有限公司 | 含有氨基氧基取代的吡啶的咪唑并吡啶的化合物 |
| CN110551145B (zh) * | 2019-10-24 | 2022-08-05 | 江苏师范大学 | 一类呋喃并香豆素-Tröger’s Base衍生物及其合成方法与应用 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE502319A (pl) * | 1950-04-04 | |||
| US2603649A (en) * | 1950-04-04 | 1952-07-15 | American Cyanamid Co | Heterocyclic sulfonamides and method of preparing the same |
| GB833049A (en) * | 1957-04-04 | 1960-04-21 | Omikron Gagliardi Soc Di Fatto | Improvements in the preparation of heterocyclic sulfonamides |
| DE2726625A1 (de) * | 1976-06-25 | 1977-12-29 | Ciba Geigy Ag | Verfahren zum flammfestmachen von polyesterfasermaterialien |
| GB8316645D0 (en) * | 1983-06-18 | 1983-07-20 | Wyeth John & Brother Ltd | Heterocyclic compounds |
-
1986
- 1986-04-21 FR FR8605721A patent/FR2597478B1/fr not_active Expired
-
1987
- 1987-04-09 IN IN305/DEL/87A patent/IN167204B/en unknown
- 1987-04-10 DK DK185487A patent/DK185487A/da not_active Application Discontinuation
- 1987-04-13 AU AU71438/87A patent/AU608511B2/en not_active Ceased
- 1987-04-13 CA CA000534593A patent/CA1300133C/fr not_active Expired - Fee Related
- 1987-04-14 ES ES8701081A patent/ES2005158A6/es not_active Expired
- 1987-04-15 US US07/038,874 patent/US4933338A/en not_active Expired - Fee Related
- 1987-04-16 EP EP87400875A patent/EP0246126A1/fr not_active Withdrawn
- 1987-04-16 ZA ZA872739A patent/ZA872739B/xx unknown
- 1987-04-17 HU HU871716A patent/HUT63151A/hu unknown
- 1987-04-20 RU SU874202461A patent/RU1813087C/ru active
- 1987-04-20 PT PT84724A patent/PT84724B/pt not_active IP Right Cessation
- 1987-04-20 DD DD87301968A patent/DD297817A5/de not_active IP Right Cessation
- 1987-04-21 YU YU72387A patent/YU46193B/sh unknown
- 1987-04-21 KR KR1019870003936A patent/KR930003613B1/ko not_active IP Right Cessation
- 1987-04-21 NO NO871643A patent/NO871643L/no unknown
- 1987-04-21 JP JP62098483A patent/JPH0643404B2/ja not_active Expired - Lifetime
- 1987-04-21 BR BR8701897A patent/BR8701897A/pt unknown
- 1987-04-21 PL PL1987265299A patent/PL156736B1/pl unknown
- 1987-04-21 CN CN198787102916A patent/CN87102916A/zh active Pending
-
1989
- 1989-04-28 US US07/344,966 patent/US4943570A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| NO871643D0 (no) | 1987-04-21 |
| HUT63151A (en) | 1993-07-28 |
| JPS62289568A (ja) | 1987-12-16 |
| EP0246126A1 (fr) | 1987-11-19 |
| IN167204B (pl) | 1990-09-22 |
| DK185487A (da) | 1987-10-22 |
| US4943570A (en) | 1990-07-24 |
| KR870010050A (ko) | 1987-11-30 |
| FR2597478A1 (fr) | 1987-10-23 |
| YU46193B (sh) | 1993-05-28 |
| BR8701897A (pt) | 1988-02-02 |
| PT84724B (pt) | 1989-12-29 |
| KR930003613B1 (ko) | 1993-05-08 |
| NO871643L (no) | 1987-10-22 |
| PT84724A (fr) | 1987-05-01 |
| DK185487D0 (da) | 1987-04-10 |
| CN87102916A (zh) | 1988-04-27 |
| ZA872739B (en) | 1987-12-30 |
| RU1813087C (ru) | 1993-04-30 |
| JPH0643404B2 (ja) | 1994-06-08 |
| CA1300133C (fr) | 1992-05-05 |
| PL156736B1 (pl) | 1992-04-30 |
| US4933338A (en) | 1990-06-12 |
| AU7143887A (en) | 1987-10-22 |
| ES2005158A6 (es) | 1989-03-01 |
| FR2597478B1 (fr) | 1988-12-16 |
| YU72387A (en) | 1989-02-28 |
| AU608511B2 (en) | 1991-04-11 |
| PL265299A1 (en) | 1988-07-21 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| ENJ | Ceased due to non-payment of renewal fee |