CH366049A - Process for the production of new sulfonamides - Google Patents
Process for the production of new sulfonamidesInfo
- Publication number
- CH366049A CH366049A CH5600258A CH5600258A CH366049A CH 366049 A CH366049 A CH 366049A CH 5600258 A CH5600258 A CH 5600258A CH 5600258 A CH5600258 A CH 5600258A CH 366049 A CH366049 A CH 366049A
- Authority
- CH
- Switzerland
- Prior art keywords
- amino
- reaction
- sub
- agent
- carried out
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 12
- 229940124530 sulfonamide Drugs 0.000 title claims description 5
- 150000003456 sulfonamides Chemical class 0.000 title claims description 5
- 238000004519 manufacturing process Methods 0.000 title description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 12
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 6
- -1 p-Amino-benzenesulfonyl Chemical group 0.000 claims description 6
- 238000009833 condensation Methods 0.000 claims description 5
- 230000005494 condensation Effects 0.000 claims description 5
- 150000008065 acid anhydrides Chemical class 0.000 claims description 3
- 150000004820 halides Chemical class 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 3
- QWCJHSGMANYXCW-UHFFFAOYSA-N sulfaphenazole Chemical compound C1=CC(N)=CC=C1S(=O)(=O)NC1=CC=NN1C1=CC=CC=C1 QWCJHSGMANYXCW-UHFFFAOYSA-N 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- GGCZERPQGJTIQP-UHFFFAOYSA-N sodium;9,10-dioxoanthracene-2-sulfonic acid Chemical compound [Na+].C1=CC=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 GGCZERPQGJTIQP-UHFFFAOYSA-N 0.000 claims description 2
- 239000012345 acetylating agent Substances 0.000 claims 1
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- JFAVFYXYKVKSTM-UHFFFAOYSA-N Acetylsulfaphenazole Chemical compound C=1C=C(N)C=CC=1S(=O)(=O)N(C(=O)C)C1=CC=NN1C1=CC=CC=C1 JFAVFYXYKVKSTM-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 230000010933 acylation Effects 0.000 description 2
- 238000005917 acylation reaction Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 206010048960 Streptococcal sepsis Diseases 0.000 description 1
- TUCNEACPLKLKNU-UHFFFAOYSA-N acetyl Chemical compound C[C]=O TUCNEACPLKLKNU-UHFFFAOYSA-N 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 230000000973 chemotherapeutic effect Effects 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 210000000936 intestine Anatomy 0.000 description 1
- 230000005923 long-lasting effect Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or 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
- C07D231/38—Nitrogen atoms
- C07D231/42—Benzene-sulfonamido pyrazoles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Description
Verfahren zur Herstellung neuer Sulfonamide Gegenstand der Erfindung ist ein Verfahren zur Herstellung von 3-[N-(p-Amino-benzolsulfonyl)-N- acyl-amino]-2-phenyl-pyrazolen der Formel
EMI0001.0005
Der Acylrest ist dabei vorzugsweise ein niederer Alkanoylrest, besonders der Acetylrest.
Die neuen Verbindungen, in erster Linie das 3 - [N- (p-Amino-benzolsulfonyl)-N-acetyl-amino]-2- phenyl-pyrazol, besitzen wertvolle chemotherapeu tische Eigenschaften. Sie haben eine starke und lang dauernde Wirkung gegenüber der Streptokokkensepsis der Maus und zeigen weiter sehr gute Aktivität ge genüber Coli-Bakterien im Urin und im Darm. Ausserdem sind sie praktisch frei von unangenehmen Geschmacksqualitäten, wie sie oft den Sulfonamiden anhaften, und können deshalb mit Vorteil für die Herstellung von Tabletten und Sirups dienen.
Die neuen Verbindungen werden erfindungs gemäss erhalten, indem man 3-(p-Amino-benzolsul- fonamido)-2-phenyl-pyrazol mit acylierenden Mitteln behandelt. Als acylierende Mittel dienen vor allem Säureanhydride oder Halogenide. Die Reaktion wird zweckmässig in Anwesenheit von Kondensationsmit teln durchgeführt. Arbeitet man mit Säureanhydriden, wie Essigsäureanhydrid, so verwendet man als Kon densationsmittel insbesondere Basen, wie tertiäre Amine, z.
B. Pyridin, oder Trialkylamine, wie Tri- methylamin. Zur Umsetzung mit Säurehalogeniden, wie Acetylchlorid, verwendet man das Sulfonamid zweckmässig in Form eines Salzes, wie des Silber salzes, oder man arbeitet in Gegenwart von Salze bildenden Kondensationsmitteln. Die Acyherung wird zweckmässig in einem inerten organischen Lö sungsmittel, im wesentlichen unter wasserfreien Be dingungen, durchgeführt.
Besonders geeignet als Lö sungsmittel sind niedere aliphatische Ketone, wie Aceton. Zur Vermeidung einer weitergehenden Acy- lierung verwendet man zweckmässig ungefähr äqui- molekulare Mengen der Reaktionsteilnehmer sowie des Kondensationsmittels.
Im folgenden Beispiel sind die Temperaturen in Celsiusgraden angegeben.
<I>Beispiel</I> In einem mit Rührer und Thermometer ver- sehenen Kolben werden 32 g 3-(p-Amino-benzol- sulfonamido)-2-phenyl-pyrazol in 80 cm3 Aceton und 16 cm3 trockenem Pyridin bei 20-25 gelöst. Unter Rühren werden innerhalb 10 Minuten 11 g Essigsäureanhydrid zugegeben. Man rührt während 5 Stunden und lässt die Mischung während 10 Stun den stehen.
Es wird dann unter Rühren 100 cm3 3 1/aiges wässeriges Ammoniak und etwas frisches Eis zugegeben, wonach ein öliges Produkt ausfällt. Man versetzt es mit 500 cm3 Wasser und lässt wäh rend 10 Stunden bei Zimmertemperatur stehen, wo bei das gebildete Öl allmählich kristallisiert. Das so erhaltene 3 - [N - (p-Amino-benzolsulfonyl)-N-acetyl- amino]-2-phenyl-pyrazol wird aus Äthanol umkristal- lisiert und wird so in weissen Kristallen vom F. 178 bis 180 erhalten.
Process for the preparation of new sulfonamides The invention relates to a process for the preparation of 3- [N- (p-amino-benzenesulfonyl) -N-acyl-amino] -2-phenyl-pyrazoles of the formula
EMI0001.0005
The acyl radical is preferably a lower alkanoyl radical, especially the acetyl radical.
The new compounds, primarily 3 - [N- (p-Amino-benzenesulfonyl) -N-acetyl-amino] -2-phenyl-pyrazole, have valuable chemotherapeutic properties. They have a strong and long-lasting effect against streptococcal sepsis in mice and also show very good activity against coli bacteria in the urine and intestines. In addition, they are practically free of unpleasant taste qualities, such as those often associated with sulfonamides, and can therefore be used to advantage in the production of tablets and syrups.
The new compounds are obtained according to the invention by treating 3- (p-amino-benzenesulfonamido) -2-phenyl-pyrazole with acylating agents. Acylating agents in particular are acid anhydrides or halides. The reaction is expediently carried out in the presence of condensation agents. If you work with acid anhydrides, such as acetic anhydride, then used as a condensation agent in particular bases, such as tertiary amines, z.
B. pyridine, or trialkylamines such as trimethylamine. For reaction with acid halides, such as acetyl chloride, the sulfonamide is expediently used in the form of a salt, such as the silver salt, or one works in the presence of salt-forming condensation agents. The acylation is expediently carried out in an inert organic solvent, essentially under anhydrous conditions.
Lower aliphatic ketones, such as acetone, are particularly suitable as solvents. To avoid further acylation, it is expedient to use approximately equimolecular amounts of the reactants and of the condensing agent.
In the following example the temperatures are given in degrees Celsius.
<I> Example </I> In a flask equipped with a stirrer and thermometer, 32 g of 3- (p-amino-benzenesulfonamido) -2-phenyl-pyrazole are dissolved in 80 cm3 of acetone and 16 cm3 of dry pyridine at 20- 25 solved. 11 g of acetic anhydride are added with stirring over the course of 10 minutes. The mixture is stirred for 5 hours and the mixture is left to stand for 10 hours.
100 cm3 of 3 liter aqueous ammonia and some fresh ice are then added with stirring, after which an oily product precipitates. It is mixed with 500 cm3 of water and left to stand for 10 hours at room temperature, whereupon the oil formed gradually crystallizes. The 3 - [N - (p-amino-benzenesulfonyl) -N-acetyl-amino] -2-phenyl-pyrazole obtained in this way is recrystallized from ethanol and is thus obtained in white crystals with a melting point of 178 to 180.
Claims (1)
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH5600258A CH366049A (en) | 1958-02-18 | 1958-02-18 | Process for the production of new sulfonamides |
| ES0247096A ES247096A1 (en) | 1958-02-18 | 1959-02-07 | Procedure for the obtaining of new sulfonamides (Machine-translation by Google Translate, not legally binding) |
| SE152659A SE301316B (en) | 1958-02-18 | 1959-02-17 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH5600258A CH366049A (en) | 1958-02-18 | 1958-02-18 | Process for the production of new sulfonamides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH366049A true CH366049A (en) | 1962-12-15 |
Family
ID=4520224
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH5600258A CH366049A (en) | 1958-02-18 | 1958-02-18 | Process for the production of new sulfonamides |
Country Status (3)
| Country | Link |
|---|---|
| CH (1) | CH366049A (en) |
| ES (1) | ES247096A1 (en) |
| SE (1) | SE301316B (en) |
-
1958
- 1958-02-18 CH CH5600258A patent/CH366049A/en unknown
-
1959
- 1959-02-07 ES ES0247096A patent/ES247096A1/en not_active Expired
- 1959-02-17 SE SE152659A patent/SE301316B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ES247096A1 (en) | 1959-06-01 |
| SE301316B (en) | 1968-06-04 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CH366049A (en) | Process for the production of new sulfonamides | |
| DE2157708C3 (en) | 2 ', 6'-dichlorobenzaldehyde-1-alkyl-3-sulfonylsemicarbazones and processes for their preparation | |
| CH366545A (en) | Process for the preparation of new N-acyl-sulfonamides | |
| AT222271B (en) | Process for the preparation of new, therapeutically effective sulfonamide complex compounds | |
| DE2336526A1 (en) | Anthelmintic 2,6-diacyloxy-benzanilides - prepd. by acylation of 2,6-dihydroxy-3,5-dichloro-benzanilides | |
| DE733965C (en) | Process for the production of condensation products | |
| AT233586B (en) | Process for the preparation of new 4,4'-disubstituted diphenyl sulfones | |
| AT256818B (en) | Process for the preparation of new substituted o-phenoxyphenl esters | |
| DE824206C (en) | Process for the production of nucleosides by hydrolytic cleavage of nucleic acid | |
| AT226730B (en) | Process for the production of new sulfonylureas | |
| AT165068B (en) | Process for the preparation of acylated p-aminobenzenesulfonamides | |
| DE1255111B (en) | Process for the preparation of benzophenone derivatives | |
| DE820735C (en) | Process for the production of urea derivatives | |
| DE3876925T2 (en) | CONDENSATION PRODUCTS MADE FROM 2,2,4-TRIMETHYL-1,2-DIHYDRO-CHINOLINE AND OXO COMPOUNDS AND DERIVATIVES THEREOF. | |
| DE919469C (en) | Process for the preparation of the threo-1-phenyl-1,3-diacyloxy-2-aminopropane hydrochloride | |
| AT205023B (en) | Process for the preparation of new sulfonylamino compounds | |
| AT205022B (en) | Process for the preparation of new sulfonylamino compounds | |
| DE929191C (en) | Process for the production of aminocarboxylic acids | |
| AT158872B (en) | Process for the production of 5.5-disubstituted or 1.5.5-trisubstituted barbituric acids. | |
| AT214915B (en) | Process for the preparation of thiophene disulfochlorides | |
| DE2314676C3 (en) | Process for the preparation of 2-phenyl-5-benzothiazolylacetic acid and its salts | |
| CH252235A (en) | Process for the preparation of a, y-diphenoxypropane-4: 4'-bis (carbonamidine) -di-B-oxyethanesulfonate. | |
| CH156442A (en) | Process for the preparation of a derivative of 3-nitro-4-oxybenzamide. | |
| DE1197458B (en) | Process for the preparation of sulfenic acid derivatives | |
| DE2207723A1 (en) | New derivative of 6-aminopenicillanic acid and process for its preparation |