DE726739C - Process for the production of clumps of 4-aminobenzenesulfonamides - Google Patents
Process for the production of clumps of 4-aminobenzenesulfonamidesInfo
- Publication number
- DE726739C DE726739C DEH161688D DEH0161688D DE726739C DE 726739 C DE726739 C DE 726739C DE H161688 D DEH161688 D DE H161688D DE H0161688 D DEH0161688 D DE H0161688D DE 726739 C DE726739 C DE 726739C
- Authority
- DE
- Germany
- Prior art keywords
- aminobenzenesulfonamides
- acid
- parts
- production
- clumps
- 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
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical class NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 title claims description 10
- 238000000034 method Methods 0.000 title claims description 4
- 239000002253 acid Substances 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 7
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 claims description 4
- XJGFWWJLMVZSIG-UHFFFAOYSA-N 9-aminoacridine Chemical compound C1=CC=C2C(N)=C(C=CC=C3)C3=NC2=C1 XJGFWWJLMVZSIG-UHFFFAOYSA-N 0.000 claims 1
- 229960001441 aminoacridine Drugs 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 229940124530 sulfonamide Drugs 0.000 description 4
- 230000000844 anti-bacterial effect Effects 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- CIKWKGFPFXJVGW-UHFFFAOYSA-N ethacridine Chemical compound C1=C(N)C=CC2=C(N)C3=CC(OCC)=CC=C3N=C21 CIKWKGFPFXJVGW-UHFFFAOYSA-N 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- HVBSAKJJOYLTQU-UHFFFAOYSA-N 4-aminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 235000011007 phosphoric acid Nutrition 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-M Methanesulfonate Chemical compound CS([O-])(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 229950000244 sulfanilic acid Drugs 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/22—Amides of acids of phosphorus
- C07F9/224—Phosphorus triamides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
Verfahren zur Herstellung von Abkömmlingen der 4-Aminobenzolsulfonamide Nach dem Verfahren des Patents 713 079 werden durch Erhitzen von 4-Aminobenzolsulfonamiden der allgemeinen Formel worin R und R, Alkyl oder Wasserstoff, R2 Alky1, Aryl oder Wasserstoff bedeuten, oder deren Salzen mit Phosphoroxychlorid Phosphorsäuredichloride dieser 4-Aminobenzolsulfonamide erhalten, die sich durch Umsetzung mit Ammoniak, Alkylaminen oder Alkalien in stark bakterizid wirkende Phosphorsäuren bzw. Phosphamidsäuren umwandeln lassen.Process for the preparation of derivatives of the 4-aminobenzenesulfonamides According to the process of patent 713 079 , by heating 4-aminobenzenesulfonamides of the general formula where R and R, alkyl or hydrogen, R2 alkyl, aryl or hydrogen, or their salts with phosphorus oxychloride, phosphoric acid dichlorides of these 4-aminobenzenesulfonamides are obtained, which can be converted into strongly bactericidal phosphoric acids or phosphamic acids by reaction with ammonia, alkylamines or alkalis.
Es wurde nun gefunden, daß man aus diesen Phosphamidsäuren der 4-Aminobenzolsulfonamide besonders wertvolle bakterizide Verbindungen erhält, wenn man sie mit alkoxylierten Aminoacridinbasen umsetzt. Die Darstellung der neuen Verbindungen erfolgt durch Neutralisation der Base mit einer 4-Aminobenzolsulfonamidphosphamidsäure oder durch Umsetzung eines leicht löslichen Salzes einer geeigneten Base mit einem Salz einer 4-Aminobenzolsulfonamidphosphamidsäure. Diese Umsetzungen können in der Kälte oder Wärme vorgenommen werden. Die so erhaltenen Salze kristallisieren aus oder können durch Eindampfen in festem Zustand erhalten werden. Man kann auch die Lösung der neutral reagierenden Salze unmittelbar für Injektionszwecke in Ampullen abfüllen.It has now been found that these phosphamic acids can be converted into 4-aminobenzenesulfonamides particularly valuable bactericidal compounds are obtained when they are alkoxylated with Aminoacridinebasen converts. The new connections are displayed by Neutralization of the base with a 4-aminobenzenesulfonamide phosphamic acid or by Implementation of a readily soluble salt of a suitable base with a salt of a 4-aminobenzenesulfonamide phosphamic acid. These reactions can take place in the cold or Heat can be made. The salts obtained in this way crystallize out or can can be obtained by evaporation in the solid state. One can also solve the Fill neutrally reacting salts into ampoules immediately for injection purposes.
Die neuen Verbindungen weisen neuartige Wirkungen auf. Ihre bakterizide Wirkung ist viel größer als die Wirkung der Ausgangsbasen und des Sulfanilsäureamids zusammen. So ist z. B. das sulfanilamidphosphamidsaure 2-Methoxy-6-chlor-9-a-diäthylamino-8-pentylaminoacridin gegen Streptokokken dreimal so wirksam wie 4-Aminobenzolsulfonamid, während 2-Methoxy-6-chlor-9-a-diäthylamino-8-pentylaminoacridin in einer zehnmal so hohen Dosis unwirksam ist. Das sulfanilamidphosphamidsaure 2-Äthoxy-6, 9-diaminoacridin ist gegen Streptokokken in der Dosis von o,o66 g pro kg bei der Maus zu 8o bis ioo°/o wirksam, während 2-Äthoxy-6, 9-diaminoacridin in der Dosis von o,23 g pro kg vollständig unwirksam ist: Beispiel i g Teile 2-Methoxy-6-chlor-9-a-diäthylamino - 8 - pentylaminoacridindihydrochlorid werden in Wasser gelöst und die Acridinbase durch Sodazusatz gefällt. Die Base wird durch 9,8 Teile Sulfanilamidphosphamidsäure, suspendiert iniooTeilen Wasser, neutralisiert. Man erhält eine klare, gelbe, neutrale Lösung des sulfanilamidphosphamidsauren 2-Methoxy-6-chlor-9-a-diäthylamino- b-pentylaminoacridins, die direkt für Injektionen verwendet werden kann. Beispiel 2 .1 Teile 2-Äthoxy-6, 9-diaminoacridin werden in 4.o Teilen Wasser und 4.,5 Teilen Sulfanilamidphosphamidsäure neutralisiert. Das sulfanilamidphosphamid-saure 2-Äthoxy-6, 9-dia:minoacridin bildet ein gelbes Pulver, das abgesaugt, mit wenig Wasser gewaschen und getrocknet wird. Beispiel 3 Man löst 2-Methoxy-6-chlor-x-diäthylamino - 8-pentylaminoacridinmethylsulfonat, entsprechend q. Teilen Base, in 2o Teilen Wasser und gibt eine Lösung von 6,2 Teilen des Natriumsalzes der Sulfanilamidphosphamidsäure in 2o Teilen Wasser hinzu. Die entstehende gelbe Lösung des sulfanilatnidphosphamidsauren 2-Methoxy-6-chlor-9-a-diäthylamino-8-pentylaminoacridins kann unmittelbar für therapeutische Zwecke verwendet werden.The new compounds have novel effects. Your bactericidal The effect is much greater than the effect of the starting bases and the sulfanilic acid amide together. So is z. B. the sulfanilamidphosphamidsaure 2-methoxy-6-chloro-9-a-diethylamino-8-pentylaminoacridine against streptococci three times as effective as 4-aminobenzenesulfonamide, while 2-methoxy-6-chloro-9-a-diethylamino-8-pentylaminoacridine is ineffective at a dose ten times higher. The sulfanilamidophosphamidic acid 2-ethoxy-6, 9-diaminoacridine is against streptococci in the dose of o, o66 g per kg in the mouse to 80 to 100 per cent effective, while 2-ethoxy-6, 9-diaminoacridine in the dose of 0.23 g per kg is completely ineffective: Example i g parts of 2-methoxy-6-chloro-9-a-diethylamino - 8 - pentylaminoacridine dihydrochloride are dissolved in water and the acridine base precipitated by adding soda. The base is replaced by 9.8 parts of sulfanilamide phosphamic acid, suspended inioo parts of water, neutralized. A clear, yellow, neutral one is obtained Solution of the sulfanilamidophosphamide acid 2-methoxy-6-chloro-9-a-diethylamino-b-pentylaminoacridins, which can be used directly for injections. Example 2 .1 part of 2-ethoxy-6, 9-diaminoacridine in 4.o parts of water and 4., 5 parts of sulfanilamidophosphamic acid neutralized. The sulfanilamidophosphamidic acid 2-ethoxy-6, 9-dia: forms minoacridine a yellow powder that is filtered off with suction, washed with a little water and dried. Example 3 Dissolve 2-methoxy-6-chloro-x-diethylamino-8-pentylaminoacridine methylsulfonate, according to q. Parts of base in 2o parts of water and gives a solution of 6.2 parts of the sodium salt of sulfanilamidophosphamic acid in 2o parts of water. the resulting yellow solution of sulfanilatnidphosphamide acid 2-methoxy-6-chloro-9-a-diethylamino-8-pentylaminoacridins can be used immediately for therapeutic purposes.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEH161688D DE726739C (en) | 1938-07-30 | 1938-07-30 | Process for the production of clumps of 4-aminobenzenesulfonamides |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEH161688D DE726739C (en) | 1938-07-30 | 1938-07-30 | Process for the production of clumps of 4-aminobenzenesulfonamides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE726739C true DE726739C (en) | 1942-10-27 |
Family
ID=7183503
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEH161688D Expired DE726739C (en) | 1938-07-30 | 1938-07-30 | Process for the production of clumps of 4-aminobenzenesulfonamides |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE726739C (en) |
-
1938
- 1938-07-30 DE DEH161688D patent/DE726739C/en not_active Expired
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