DE735560C - Process for the preparation of water-soluble 4,4-diaminodiphenylsulfone compounds - Google Patents
Process for the preparation of water-soluble 4,4-diaminodiphenylsulfone compoundsInfo
- Publication number
- DE735560C DE735560C DESCH113623D DESC113623D DE735560C DE 735560 C DE735560 C DE 735560C DE SCH113623 D DESCH113623 D DE SCH113623D DE SC113623 D DESC113623 D DE SC113623D DE 735560 C DE735560 C DE 735560C
- Authority
- DE
- Germany
- Prior art keywords
- water
- diaminodiphenylsulfone
- soluble
- compounds
- preparation
- 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
- 238000000034 method Methods 0.000 title claims description 3
- 238000002360 preparation method Methods 0.000 title description 6
- MQJKPEGWNLWLTK-UHFFFAOYSA-N Dapsone Chemical class C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=C1 MQJKPEGWNLWLTK-UHFFFAOYSA-N 0.000 claims description 9
- 150000004676 glycans Chemical class 0.000 claims description 2
- 125000001976 hemiacetal group Chemical group 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 150000002772 monosaccharides Chemical class 0.000 claims description 2
- 229920001282 polysaccharide Polymers 0.000 claims description 2
- 239000005017 polysaccharide Substances 0.000 claims description 2
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 235000019270 ammonium chloride Nutrition 0.000 description 3
- OWEGMIWEEQEYGQ-UHFFFAOYSA-N 100676-05-9 Natural products OC1C(O)C(O)C(CO)OC1OCC1C(O)C(O)C(O)C(OC2C(OC(O)C(O)C2O)CO)O1 OWEGMIWEEQEYGQ-UHFFFAOYSA-N 0.000 description 2
- SHZGCJCMOBCMKK-UHFFFAOYSA-N D-mannomethylose Natural products CC1OC(O)C(O)C(O)C1O SHZGCJCMOBCMKK-UHFFFAOYSA-N 0.000 description 2
- GUBGYTABKSRVRQ-PICCSMPSSA-N Maltose Natural products O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@@H](CO)OC(O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-PICCSMPSSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000008103 glucose Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- SHZGCJCMOBCMKK-JFNONXLTSA-N L-rhamnopyranose Chemical compound C[C@@H]1OC(O)[C@H](O)[C@H](O)[C@H]1O SHZGCJCMOBCMKK-JFNONXLTSA-N 0.000 description 1
- PNNNRSAQSRJVSB-UHFFFAOYSA-N L-rhamnose Natural products CC(O)C(O)C(O)C(O)C=O PNNNRSAQSRJVSB-UHFFFAOYSA-N 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 201000007100 Pharyngitis Diseases 0.000 description 1
- 206010061372 Streptococcal infection Diseases 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- PYMYPHUHKUWMLA-WDCZJNDASA-N arabinose Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)C=O PYMYPHUHKUWMLA-WDCZJNDASA-N 0.000 description 1
- PYMYPHUHKUWMLA-UHFFFAOYSA-N arabinose Natural products OCC(O)C(O)C(O)C=O PYMYPHUHKUWMLA-UHFFFAOYSA-N 0.000 description 1
- SRBFZHDQGSBBOR-UHFFFAOYSA-N beta-D-Pyranose-Lyxose Natural products OC1COC(O)C(O)C1O SRBFZHDQGSBBOR-UHFFFAOYSA-N 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- -1 diacetyl compound Chemical class 0.000 description 1
- 229930182478 glucoside Natural products 0.000 description 1
- 150000008131 glucosides Chemical class 0.000 description 1
- 150000002402 hexoses Chemical class 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 150000002972 pentoses Chemical class 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000008265 rhamnosides Chemical class 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 231100000820 toxicity test Toxicity 0.000 description 1
Landscapes
- Saccharide Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
Verfahren zur Herstellung wasserlöslicher 4, 4'-Diaminodiphenylsulfonverbindungen Es ist bekannt, daß das ¢, 4'-Diaminodiphexiylsulfon, dessen Herstellung auf verschiedenen Wegen möglich ist, sowie seine Diacetylverbindung zwar Präparate von hoher Wirksamkeit gegen Kokkeninfektionen, wie sie durch Streptokokken, Pneumokokken usw. hervorgerufen werden, darstellen, daß aber ein großer Nachteil für ihre Verwendung in ihrer Wasserunlöslichkeit liegt.Process for the preparation of water-soluble 4,4'-diaminodiphenylsulfone compounds It is known that [, 4'-diaminodiphexiylsulfone, its preparation on various Because it is possible, as well as its diacetyl compound, preparations of high effectiveness against cocci infections such as those caused by streptococci, pneumococci, etc. are, but represent a major disadvantage for their use in their water insolubility lies.
Es wurde nun gefunden, daß man zu wasserlöslichen Verbindungen des 4, 4'-Diaminodiphenylsulfons gelangen kann, wenn man 4, 4'-Diaminodiphenylsulfon mit Mono-oder Polysacchariden, die eine Aldehyd- bzw. Halbacetalgruppe enthalten, insbesondere Pentosen und Hexosen, wie Rhamnose, Glucose, Axabinos,e, Maltose, kondensiert. Die Kondensation wird zweckmäßig in alkoholischer Lösung bei erhöhter Temperatur; gegebenenfalls unter Anwendung eines Kondensationsmittels, wie z. B. Ammoniumchlorid, ausgeführt. Die so erhaltenen Kondensationsprodukte weisen die therapeutische Wirksamkeit des Ausgangsstoffes in vielfach erhöhtem Maße auf; außerdem ist deren Applikationsart nicht nur auf die perorale, wie beim Ausgangsstoff, beschränkt.It has now been found that water-soluble compounds of the 4, 4'-Diaminodiphenylsulfons can get, if one 4, 4'-Diaminodiphenylsulfon with mono- or polysaccharides that contain an aldehyde or hemiacetal group, in particular pentoses and hexoses, such as rhamnose, glucose, axabinos, e, maltose, condensed. The condensation is expediently carried out in alcoholic solution at an elevated temperature; optionally using a condensing agent, such as. B. ammonium chloride, executed. The condensation products thus obtained show the therapeutic effectiveness of the starting material to a much greater extent; also its type of application not only limited to the oral, as with the starting material.
Nachstehend seien Beispiele für die Herstellung der neuen Verbindungen gegeben, ohne jedoch die Herstellungsmöglichkeiten auf diese zu beschränken.The following are examples of the preparation of the new compounds given, but without restricting the manufacturing options to this.
Beispiel i i Mol 4, 4'-Diaminodiphenylsulfon werden mit 6 Mol Rhamnosie in Alkohol 4 Stunden am Rückflußkühler gekocht und der Alkohol dann im Vakuum abdestilliert. Das als Rückstand hinterbleibende braune öl, welches allenfalls noch weiter gereinigt werden kann, stellt das 4, 4'-Diaminodiph.enylsulfonrhamnosid dar. Es ist in Wasser sehr leicht löslich und besitzt etwa zehnmal so starke Wir, kung auf die Streptokokkeninfektion wie das -wasserunlösliche 4., 4'-Diaminodiphenylsulfon. Beispiel 2 4- 4"1'-Diaminodiphenylsulfon werden mit 12- Glucose und r g Ammoniumchlorid in Zoo cmj Alkohol 3i,'2 Stunden auf dem Wasserbad erhitzt. Die Lösung wird im Vakuum eingeengt und das 4, 4'-Diaminodiphenylsulfonglucosid als in Wasser leicht lösliches öl erhalten. Es zeigt ungefähr die gleiche Wirkung auf die Streptakokheninfektion wie das Rhamnosid.Example i i moles of 4,4'-diaminodiphenyl sulfone are with 6 moles of rhamnosie Boiled in alcohol for 4 hours on a reflux condenser and the alcohol then distilled off in vacuo. The brown oil that remains as a residue, which at most which can be purified even further is the 4,4'-diaminodiph.enylsulfonrhamnosid It is very easily soluble in water and has about ten times as strong a we, effect on streptococcal infection such as the water-insoluble 4, 4'-diaminodiphenyl sulfone. Example 2 4- 4 "1'-diaminodiphenylsulfone are made with 12-glucose and r g ammonium chloride in zoo cmj alcohol 3i, 'heated on a water bath for 2 hours. The solution is in vacuo concentrated and the 4, 4'-diaminodiphenylsulfonglucoside as easily soluble in water get oil. It shows roughly the same effect on strep throat infection like the rhamnoside.
Beispiel 3 i Mol 4, 4'-Diaminodiphenylsulfon werden mit 6 Mol Arabinose in Alkohol 4. Stunden am Kühler gekocht und der Alkohol dann im Vakuum abdestilliiert. Das als Rückstand hinterbliebene hellbraun gefärbte Öl, welches allenfalls noch weiter gereinigt werdenkann, stellt das 4, 4'-Diaminodiphenylsulfonarabinosid dar. ES ist in Wasser leicht löslich und zeigt die gleichen physiologischen Eigenschaften wie das Glucosid.Example 3 i moles of 4,4'-diaminodiphenyl sulfone are mixed with 6 moles of arabinose Boiled in alcohol on a condenser for 4 hours and then distilled off the alcohol in vacuo. The light brown oil left behind as residue, which at most is still which can be further purified is the 4,4'-diaminodiphenylsulfonarabinoside. ES is easily soluble in water and shows the same physiological properties like the glucoside.
Beispiel q.Example q.
5 g 4, 4'-Diaminodiphenylsulfon werden mit 459 Maltose, o,5 g Ammoniumchlorid und 25o cm2 Methanol mehrere Stunden auf dem Wasserbade zum Sieden erhitzt. Danach werden 2o cma Wasser hinzugefügt und das Methanol auf dem Wasserbade abgetrieben. Es hinterbleibt das 4, 4'-Diaminodiphenylsulfonmaltosid als gelb gefärbter dicker Sirup, der sich leicht in Wasser auflöst.5 g of 4,4'-diaminodiphenyl sulfone are mixed with 459 maltose, 0.5 g of ammonium chloride and 250 cm2 of methanol are heated to boiling on the water bath for several hours. Thereafter 2o cma water are added and the methanol is driven off on the water bath. The 4,4'-diaminodiphenylsulfone maltoside remains behind as a thicker yellow color Syrup that dissolves easily in water.
Durch Toxizitätsversuche an Mäusen wurde festgestellt, daß 2omg dieser neuen Präparate von der Maus vertragen werden, während bereits 5 mg 4, 4'-Diaminodiphenylsulfon toxisch wirken.Toxicity tests on mice found that 2omg of this new preparations are tolerated by the mouse while already 5 mg of 4, 4'-diaminodiphenyl sulfone have a toxic effect.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DESCH113623D DE735560C (en) | 1937-08-21 | 1937-08-21 | Process for the preparation of water-soluble 4,4-diaminodiphenylsulfone compounds |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DESCH113623D DE735560C (en) | 1937-08-21 | 1937-08-21 | Process for the preparation of water-soluble 4,4-diaminodiphenylsulfone compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE735560C true DE735560C (en) | 1943-05-18 |
Family
ID=7449927
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DESCH113623D Expired DE735560C (en) | 1937-08-21 | 1937-08-21 | Process for the preparation of water-soluble 4,4-diaminodiphenylsulfone compounds |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE735560C (en) |
-
1937
- 1937-08-21 DE DESCH113623D patent/DE735560C/en not_active Expired
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2422254A1 (en) | AMINOGLYCOSIDE DERIVATIVES AND THEIR SALTS, PROCESS FOR THEIR PRODUCTION AND PHARMACEUTICAL PREPARATIONS | |
| DE735560C (en) | Process for the preparation of water-soluble 4,4-diaminodiphenylsulfone compounds | |
| DE3820588A1 (en) | 2 ', 3'-DIDESOXY-4-THIOURIDINE DERIVATIVES, METHOD FOR THE PRODUCTION THEREOF, AND ANTIVIRUS AGENTS CONTAINING THEM | |
| DE2942818A1 (en) | NEW ANTITUMORANTHRACYCLINE WITH A CONTENT OF BRANCHED CHAIN AMINODEOXY SUGARS AND METHOD FOR THE PRODUCTION THEREOF | |
| DE2357864A1 (en) | Anti-diabetic agents prepn. - from biguanidine (salt) and nicotinic acid (salt) | |
| DE1282852B (en) | Orally applicable medicinal product containing aescin | |
| DE1793694C3 (en) | Helveticoside derivatives | |
| DE665511C (en) | Process for the preparation of the active ingredient of calebasse curare in crystallized, pure form | |
| DE810027C (en) | Process for the production of a novel Abkoemmlings des ‡ -Phenylaethylalkohols | |
| DE545917C (en) | Process for the preparation of condensation products of amino-substituted arsenic compounds | |
| DE495336C (en) | Process for the preparation of basic oxime ethers and their salts | |
| DE752680C (en) | Anion exchange | |
| DE2307795C3 (en) | 11 beta 17alpha, 21 trihydroxy-6 | |
| AT113002B (en) | Process for the preparation of monoboric acid choline. | |
| DE2436479A1 (en) | METHOD OF CLEANING UP STEROID HETEROSIDES | |
| DE1793686C3 (en) | Helveticoside derivatives and medicinal products containing them | |
| DE646706C (en) | Process for the preparation of substituted 6, 7-dioxy-1, 2, 3, 4-tetrahydroisoquinoline-1-carboxylic acids | |
| DE2542708A1 (en) | N-SUBSTITUTED IMINODIC ACID, PROCESS FOR THEIR PREPARATION AND THEIR USE | |
| DE491573C (en) | Process for obtaining durable filicin solutions | |
| AT139605B (en) | Process for the partial degradation of digitalis glucosides. | |
| AT146635B (en) | Process for the preparation of compounds of dihydrocodeine, which are readily soluble in water, with alkylated barbituric acids. | |
| DE2015076C3 (en) | Antibiotic known as Tolypomycin RB (B-2847 RB) and the process for making it | |
| DE220267C (en) | ||
| DE87099C (en) | ||
| AT325783B (en) | PROCESS FOR SEPARATING THE GLYCOFRANGULIN COMPLEX FROM VEGETABLE RAW MATERIALS, IN PARTICULAR FROM THE DRIED BARK OF THE ROTARY TREE |