CH265666A - Process for the preparation of a new condensation product of 6-sulfanilamido-3-methyl-pyridazine. - Google Patents
Process for the preparation of a new condensation product of 6-sulfanilamido-3-methyl-pyridazine.Info
- Publication number
- CH265666A CH265666A CH265666DA CH265666A CH 265666 A CH265666 A CH 265666A CH 265666D A CH265666D A CH 265666DA CH 265666 A CH265666 A CH 265666A
- Authority
- CH
- Switzerland
- Prior art keywords
- pyridazine
- sulfanilamido
- methyl
- condensation product
- preparation
- Prior art date
Links
- 239000007859 condensation product Substances 0.000 title claims description 7
- 238000000034 method Methods 0.000 title claims description 6
- 238000002360 preparation method Methods 0.000 title claims description 4
- INANRCZUSPEFOC-UHFFFAOYSA-N 2-amino-N-(3-methylpyridazin-4-yl)benzenesulfonamide Chemical compound S(=O)(C1=CC=CC=C1N)(=O)NC1=C(N=NC=C1)C INANRCZUSPEFOC-UHFFFAOYSA-N 0.000 title description 7
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 20
- 239000002253 acid Substances 0.000 claims description 6
- 150000007513 acids Chemical class 0.000 claims description 5
- 239000000843 powder Substances 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000008098 formaldehyde solution Substances 0.000 description 2
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000004312 hexamethylene tetramine Substances 0.000 description 1
- 235000010299 hexamethylene tetramine Nutrition 0.000 description 1
- 229960004011 methenamine Drugs 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
- C07D237/02—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings
- C07D237/06—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D237/10—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members 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 to ring carbon atoms
- C07D237/20—Nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
<B>Verfahren zur Herstellung eines neuen Kondensationsproduktes des</B> 6-Sulfanilamido- 3-methyl-pyridazins. Die vorliegende Erfindung betrifft ein Verfahren zur Herstellung eines -Kondensa tionsproduktes des Formaldehyds mit 6-Sulf- anilamido-3-methyl-pyridazin. Die neue Ver bindung zeigt gegenüber dem 6-Sulfanilamido- 3-methyl-pyridazin wertvollere therapeutische Eigenschaften.
Das neue Kondensationsprodukt des 6-Sulfanilamido-3-methyl-pyridazins wird er findungsgemäss dadurch erhalten, dass man 6-Sulfanilamido-3-methyl-pyridazin mit Form aldehyd umsetzt. Statt Formaldehyd selbst können auch Formaldehyd abgebende Mittel, wie Paraformaldeliyd oder Hexamethylen- tetramin, verwendet werden.
Die Umsetzung wird vorteilhaft in Gegenwart von Verdün- nungsmitteln, wie Wasser, verdünnten Säu ren oder organischen Lösungsmitteln, bei spielsweise Alkohol, durchgeführt.
Die Herstellbarkeit des neuen Kondensa- tionsproduktes sowie besonders die llög@ich- keit seiner Isolierung in einer für die thera peutische Verwendung geeigneten Form war durchaus nicht selbstverständlich. Gewisse Sulfanilamide der lieterocyclischen Reihe geben mit Formaldehyd nur schmierige Reak tionsprodukte.
Die verfahrensgemäss erhaltene Verbin dung bildet ein gelbliches Pulver, das in Säuren unlöslich ist. Sie soll als Heilmittel Verwendung finden.
<I>Beispiel:</I> 26,4 Gewichtsteile 6 - Sulfanilamido - 3 - methyl-pyridazin werden in 250 Volumteilen Nasser aufgeschwemmt und durch Zusatz von 25 V olumteilen konzentrierter Salzsäure in Lösung gebracht. Hierauf tropft man unter gutem Rühren 15 Volumteile 40%ige Formaldehydlösung allmählich ein. Das Reak tionsprodukt beginnt bald sieh in feiner Form abzuscheiden.
Nachdem alle Formaldehycl- lösung zugesetzt ist, lässt man 1 Stunde stehen, saugt ab, wäscht gründlich mit Wasser, schwemmt in Wasser auf, neu tralisiert die letzten Spuren Säure mit Sodalösung, saugt ab, trocknet bei 50 C und siebt durch ein feines Sieb. Man erhält so 26 Gewichtsteile eines gelblichen Pulvers, das in Säuren unlöslich ist. In Berührung mit Ätzalkalien verändert sich das Produkt in kurzer Zeit, und es tritt Auflösung ein.
<B> Process for the preparation of a new condensation product of </B> 6-sulfanilamido-3-methyl-pyridazine. The present invention relates to a process for the preparation of a condensation product of formaldehyde with 6-sulfanilamido-3-methyl-pyridazine. Compared to 6-sulfanilamido-3-methyl-pyridazine, the new compound shows more valuable therapeutic properties.
The new condensation product of 6-sulfanilamido-3-methyl-pyridazine is obtained according to the invention by reacting 6-sulfanilamido-3-methyl-pyridazine with formaldehyde. Instead of formaldehyde itself, formaldehyde-releasing agents, such as paraformaldelyde or hexamethylene tetramine, can also be used.
The reaction is advantageously carried out in the presence of diluents, such as water, dilute acids or organic solvents, for example alcohol.
The producibility of the new condensation product and especially the ability to isolate it in a form suitable for therapeutic use was by no means a given. Certain sulfanilamides of the lieterocyclic series give only greasy reaction products with formaldehyde.
The compound obtained according to the process forms a yellowish powder which is insoluble in acids. It is said to be used as a remedy.
<I> Example: </I> 26.4 parts by weight of 6 - sulfanilamido - 3 - methyl-pyridazine are suspended in 250 parts by volume of water and dissolved by adding 25 parts by volume of concentrated hydrochloric acid. 15 parts by volume of 40% formaldehyde solution are then gradually added dropwise with thorough stirring. The reaction product soon begins to separate out in fine form.
After all the formaldehyde solution has been added, the mixture is left to stand for 1 hour, suctioned off, washed thoroughly with water, washed up in water, the last traces of acid are neutralized with soda solution, suctioned off, dried at 50 C and sieved through a fine sieve. This gives 26 parts by weight of a yellowish powder which is insoluble in acids. In contact with caustic alkalis, the product changes in a short time and dissolution occurs.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH265666T | 1947-10-09 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH265666A true CH265666A (en) | 1949-12-15 |
Family
ID=4475813
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH265666D CH265666A (en) | 1947-10-09 | 1947-10-09 | Process for the preparation of a new condensation product of 6-sulfanilamido-3-methyl-pyridazine. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH265666A (en) |
-
1947
- 1947-10-09 CH CH265666D patent/CH265666A/en unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CH265666A (en) | Process for the preparation of a new condensation product of 6-sulfanilamido-3-methyl-pyridazine. | |
| DE542286C (en) | Process for the representation of high molecular substances | |
| AT163822B (en) | Process for the preparation of new condensation products of sulfanilamidopyrimidines | |
| CH261505A (en) | Process for the preparation of a new condensation product of 2-sulfanilamido-5-ethyl-thiodiazols- (1,3,4). | |
| DE855002C (en) | Process for the production of polyvinyl acetals in fine powder form | |
| DE851065C (en) | Process for the production of valuable condensation products | |
| DE960190C (en) | Process for the preparation of condensation products from 4-acylamino-benzene-1-sulfonamides and formaldehyde | |
| DE845939C (en) | Process for the production of water-soluble condensation products | |
| DE688821C (en) | Process for the preparation of synthetic resins from phenolic alcohols | |
| DE859148C (en) | Process for the aftertreatment of higher molecular weight condensation products from fatty acids and polyamines | |
| AT148984B (en) | Process for the preparation of aromatic compounds. | |
| CH267601A (en) | Process for the preparation of a biguanide derivative. | |
| CH216301A (en) | Process for the production of a new condensation product. | |
| CH217133A (en) | Process for the production of a water-soluble, higher molecular weight, α-substituted benzylamine derivative. | |
| CH240350A (en) | Process for the production of a condensation product. | |
| CH185343A (en) | Process for the preparation of a sulfenamide. | |
| CH280034A (en) | Process for the preparation of a derivative of p-amino-benzenesulfonyl-urea. | |
| CH217137A (en) | Process for the production of a water-soluble, higher molecular weight, α-substituted benzylamine derivative. | |
| CH210979A (en) | Process for the production of a new condensation product. | |
| CH208534A (en) | Process for the production of a new condensation product. | |
| CH298897A (en) | Process for the production of copolymers from acrylic acid amide with acrylic acid nitrile. | |
| CH267605A (en) | Process for the preparation of a biguanide derivative. | |
| CH252071A (en) | Process for the preparation of a new amide derivative. | |
| CH219929A (en) | Process for the preparation of a condensation product. | |
| CH212411A (en) | Process for the production of a betaine-like condensation product. |