DE1620564C - - Google Patents
Info
- Publication number
- DE1620564C DE1620564C DE1620564C DE 1620564 C DE1620564 C DE 1620564C DE 1620564 C DE1620564 C DE 1620564C
- Authority
- DE
- Germany
- Prior art keywords
- methane
- hydroxyphenyl
- bis
- quinolyl
- hydrogen
- 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.)
- Expired
Links
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 27
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 19
- CPELXLSAUQHCOX-UHFFFAOYSA-N hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 3
- SRSXLGNVWSONIS-UHFFFAOYSA-N Benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 claims description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 2
- 229910000042 hydrogen bromide Inorganic materials 0.000 claims description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 2
- FBBDOOHMGLLEGJ-UHFFFAOYSA-N methane;hydrochloride Chemical compound C.Cl FBBDOOHMGLLEGJ-UHFFFAOYSA-N 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 125000005493 quinolyl group Chemical group 0.000 claims description 2
- 229940092714 benzenesulfonic acid Drugs 0.000 claims 1
- MYHZZWBEVDHDBV-UHFFFAOYSA-N benzenesulfonic acid;methane Chemical compound C.OS(=O)(=O)C1=CC=CC=C1 MYHZZWBEVDHDBV-UHFFFAOYSA-N 0.000 claims 1
- RGFDUTPSNJTRCY-UHFFFAOYSA-N methane;4-methylbenzenesulfonic acid Chemical compound C.CC1=CC=C(S(O)(=O)=O)C=C1 RGFDUTPSNJTRCY-UHFFFAOYSA-N 0.000 claims 1
- PUBHCAQZIBCNLD-UHFFFAOYSA-N methane;hydrobromide Chemical compound C.C.Br PUBHCAQZIBCNLD-UHFFFAOYSA-N 0.000 claims 1
- DUDRFISLZJPLTJ-UHFFFAOYSA-N methane;phosphoric acid Chemical compound C.OP(O)(O)=O DUDRFISLZJPLTJ-UHFFFAOYSA-N 0.000 claims 1
- LRPCLTPZMUIPFK-UHFFFAOYSA-N methane;sulfuric acid Chemical compound C.OS(O)(=O)=O LRPCLTPZMUIPFK-UHFFFAOYSA-N 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- 150000003839 salts Chemical class 0.000 description 8
- 239000011780 sodium chloride Substances 0.000 description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- 150000007513 acids Chemical class 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 239000000825 pharmaceutical preparation Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- -1 (4-hydroxyphenyl) - Chemical class 0.000 description 2
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 2
- 229940077388 benzenesulfonate Drugs 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-M methanesulfonate Chemical compound CS([O-])(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-L phosphate Chemical compound OP([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-L 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N P-Toluenesulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- SMUQFGGVLNAIOZ-UHFFFAOYSA-N Quinaldine Chemical class C1=CC=CC2=NC(C)=CC=C21 SMUQFGGVLNAIOZ-UHFFFAOYSA-N 0.000 description 1
- 210000002784 Stomach Anatomy 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 230000002496 gastric Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 230000002475 laxative Effects 0.000 description 1
- 239000008141 laxative Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- XGZVLEAZGCUUPH-UHFFFAOYSA-N methylamino(methylimino)methanesulfonic acid Chemical compound CNC(=NC)S(O)(=O)=O XGZVLEAZGCUUPH-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 230000002035 prolonged Effects 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- SMWDFEZZVXVKRB-UHFFFAOYSA-N quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
Family
ID=
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE3853901T2 (de) | Kristalline 7-(2-(2-Aminothiazol-4-yl)-2-hydroxyiminoacetamido)-3-vinyl-3-cephem-4-carboxyl-Säure (syn Isomer). | |
| DE3010375A1 (de) | Flammschutzmittel, verfahren zu deren herstellung und flammhemmende kunstharzmassen | |
| DE1906527B2 (de) | Thioninderivate, Verfahren zu deren Herstellung und pharmazeutische Präparate, welche diese enthalten | |
| DE1620564C (US06262066-20010717-C00315.png) | ||
| DE1620564B (de) | Salze des Bis (4 hydroxyphenyl) (chi nolyl 2)-rnethans und ein Verfahren zu ihrer Herstellung Ausscheidung aus 1620495 | |
| DE489726C (de) | Verfahren zur Darstellung schwer loeslicher Salze von organischen Basen und von Alkaloiden | |
| DE2430550C2 (de) | Äthanol-Wasser-Solvate von Natriumhexametaphosphatkomplexen des α-6-Desoxy-5-hydroxy-tetracyclin und ein Verfahren zu deren Herstellung | |
| DE1795133C2 (de) | 5-Nitro-8-(5'-brom-alpha-furoyloxy)-chinaldin,ein Verfahren zu seiner Herstellung und Arzneimittel | |
| DE876538C (de) | Verfahren zur Herstellung aminogruppenhaltiger aromatischer Sulfonsaeureester | |
| DE2632115A1 (de) | Neue serotoninderivate, verfahren zu deren herstellung und diese enthaltende arzneimittel | |
| DE854952C (de) | Verfahren zur Herstellung von komplexen Aureomycin-Verbindungen | |
| DD154817A5 (de) | Verfahren zur darstellung der molekularen verbindung von beta-diaethylaminoaethylamid der p-chlorophenoxyessigsaeure mit 4-n-butyl-3,5-diketo-1,2-diphenylpyrazolidin | |
| AT207381B (de) | Verfahren zur Herstellung von neuer Pyrviniumsalze der Pamoinsäure | |
| DE3443270A1 (de) | Menadioncholinbisulfit-addukt und verfahren zu dessen herstellung | |
| DE2521905A1 (de) | Fumarsaeuresalz des 1-diaethylamino- aethyl-3-(p-methoxybenzyl)-1,2-dihydro- chinoxalin-2-ons, verfahren zu seiner herstellung und diese verbindung enthaltende arzneimittel | |
| DE444970C (de) | Verfahren zur Herstellung von Salzen der Aminobenzoesaeurealkylester mit aromatischen Sulfosaeuren | |
| DE949885C (de) | Verfahren zur Herstellung von Kondensationsprodukten des Sulfaguanidins | |
| DE1695759B1 (de) | 5-Methyl-7-nitro-8-hydroxychinolin-derivate und ein Verfahren zu ihrer Herstellung | |
| DE412171C (de) | Verfahren zur Darstellung von in Wasser loeslichen organischen Arsen- und Antimonverbindungen | |
| DE454698C (de) | Verfahren zur Darstellung von in Wasser leichtloeslichen Verbindungen der m-Aminobenzoesaeurealkylester | |
| DE2359256C3 (de) | N-Phenyl-N-benzyl-4-amino-l-methylpiperidin-citrat, Verfahren zu seiner Herstellung und seine Verwendung Knoll AG, 6700 Ludwigshafen | |
| DE1203781B (de) | Verfahren zur Herstellung von trypanocid wirksamen Phenanthridiniumderivaten | |
| DE2318043C3 (de) | Bis-eckige Klammer auf 4,7-dihydroxycumarinyl-(3) eckige Klammer zu- essigsäure und deren pharmakologisch verträgliche Salze sowie Verfahren zu deren Herstellung und diese Verbindungen enthaltende Arzneimittel | |
| DE484835C (de) | Verfahren zur Darstellung von Chlorjodverbindungen des 2-Aminopyridins und seiner Derivate | |
| DE825548C (de) | Verfahren zur Herstellung von neuen diquartaeren Salzen von Pyrimidylaminocinnolinen |
