DE1119869B - Process for the preparation of N- (p-aminobenzenesulfonyl) -N-acetyl-5-amino-1-phenyl-pyrazole - Google Patents
Process for the preparation of N- (p-aminobenzenesulfonyl) -N-acetyl-5-amino-1-phenyl-pyrazoleInfo
- Publication number
- DE1119869B DE1119869B DEC18366A DEC0018366A DE1119869B DE 1119869 B DE1119869 B DE 1119869B DE C18366 A DEC18366 A DE C18366A DE C0018366 A DEC0018366 A DE C0018366A DE 1119869 B DE1119869 B DE 1119869B
- Authority
- DE
- Germany
- Prior art keywords
- carried out
- phenyl
- process according
- pyrazole
- amino group
- 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.)
- Pending
Links
- -1 p-aminobenzenesulfonyl Chemical group 0.000 title claims description 7
- 238000002360 preparation method Methods 0.000 title claims description 3
- 238000000034 method Methods 0.000 title claims 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 8
- 125000003277 amino group Chemical group 0.000 claims description 7
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 4
- 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 4
- 239000003960 organic solvent Substances 0.000 claims description 2
- 230000010933 acylation Effects 0.000 claims 2
- 238000005917 acylation reaction Methods 0.000 claims 2
- 101100119767 Caenorhabditis elegans fat-4 gene Proteins 0.000 claims 1
- 101100468762 Caenorhabditis elegans ric-3 gene Proteins 0.000 claims 1
- 125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 claims 1
- 230000003442 weekly effect Effects 0.000 claims 1
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 229940124530 sulfonamide Drugs 0.000 description 3
- 150000003456 sulfonamides Chemical class 0.000 description 3
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 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 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
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 1
- 206010048960 Streptococcal sepsis Diseases 0.000 description 1
- 239000012345 acetylating agent Substances 0.000 description 1
- 238000006640 acetylation reaction Methods 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 125000004442 acylamino group Chemical group 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- HOPRXXXSABQWAV-UHFFFAOYSA-N anhydrous collidine Natural products CC1=CC=NC(C)=C1C HOPRXXXSABQWAV-UHFFFAOYSA-N 0.000 description 1
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 230000000973 chemotherapeutic effect Effects 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- UTBIMNXEDGNJFE-UHFFFAOYSA-N collidine Natural products CC1=CC=C(C)C(C)=N1 UTBIMNXEDGNJFE-UHFFFAOYSA-N 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- HPYNZHMRTTWQTB-UHFFFAOYSA-N dimethylpyridine Natural products CC1=CC=CN=C1C HPYNZHMRTTWQTB-UHFFFAOYSA-N 0.000 description 1
- 210000005069 ears Anatomy 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 238000007327 hydrogenolysis reaction Methods 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 210000000936 intestine Anatomy 0.000 description 1
- 230000005923 long-lasting effect Effects 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- TXXWBTOATXBWDR-UHFFFAOYSA-N n,n,n',n'-tetramethylhexane-1,6-diamine Chemical compound CN(C)CCCCCCN(C)C TXXWBTOATXBWDR-UHFFFAOYSA-N 0.000 description 1
- GCRYKXLRCQDDAD-UHFFFAOYSA-N n-(2-phenylpyrazol-3-yl)benzenesulfonamide Chemical compound C=1C=CC=CC=1S(=O)(=O)NC1=CC=NN1C1=CC=CC=C1 GCRYKXLRCQDDAD-UHFFFAOYSA-N 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- JVXZJEUVAOVXIX-UHFFFAOYSA-N propan-2-one;pyridine Chemical compound CC(C)=O.C1=CC=NC=C1 JVXZJEUVAOVXIX-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 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
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 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)
- Plural Heterocyclic Compounds (AREA)
Description
DEUTSCHESGERMAN
PATENTAMTPATENT OFFICE
C18366IVd/12pC18366IVd / 12p
9. FEBRUAR 1959FEBRUARY 9, 1959
BEKANNTMACHUNG DER ANMELDUNG UND AUSGABE DER AUSLEGESCHRIFT: 21. DEZEMBBR 1961NOTICE THE REGISTRATION AND ISSUE OF THE EDITORIAL: DECEMBBR 21, 1961
Gegenstand der Erfindung ist die Herstellung des N-(p-Aminobenzolsulfonyl)-N-acetyl-5-amino-l-phenyl-pyrazols der FormelThe invention relates to the preparation of N- (p-aminobenzenesulfonyl) -N-acetyl-5-amino-1-phenyl-pyrazole the formula
HC CHHC CH
4 34 3
CH3 CH 3
C8H5 C 8 H 5
Die neue Verbindung wird erhalten, wenn man ein 5 - (Benzolsulf onamido) -1 -phenyl - pyrazol der allgemeinen FormelThe new compound is obtained if you have a 5 - (Benzolsulfonamido) -1 -phenyl - pyrazole of the general formula
HC CHHC CH
C6H5 C 6 H 5
worin R die Aminogruppe oder einen durch Reduktion in diese überführbaren Rest bedeutet, in an sich bekannter Weise Ni-acetyliert und anschließend in Verbindungen mit einem in die Aminogruppe überführbaren Rest R diesen in die freie Aminogruppe umwandelt.in which R denotes the amino group or a radical which can be converted into this by reduction, in a manner known per se Way Ni-acetylated and then in Compounds with a radical R which can be converted into the amino group and these into the free amino group converts.
Ein in die Aminogruppe durch Reduktion umwandelbarer Rest ist z. B. die Nitro- oder Azogruppe oder eine durch Hydrogenolyse spaltbare Acylaminogruppe, wie die Carbobenzoxyaminogruppe. Die Reduktion wird in an sich bekannter Weise durchgeführt, zweckmäßig unter Vermeidung von hydrolysierenden Bedingungen und höheren Temperaturen, um Abspaltung oder Umlagerung des Nj-Acetylrestes an das N4-Stickstoffatom zu vermeiden. Besonders geeignet ist die Reduktion mit Wasserstoff in Gegenwart von Katalysatoren, wie Edelmetallkatalysatoren, z. B. Palladium auf Kohle.A radical which can be converted into the amino group by reduction is e.g. B. the nitro or azo group or an acylamino group which can be cleaved by hydrogenolysis, such as the carbobenzoxyamino group. The reduction is carried out in a manner known per se, expediently avoiding hydrolyzing conditions and higher temperatures, in order to avoid cleavage or rearrangement of the Nj -acetyl radical to the N 4 nitrogen atom. Reduction with hydrogen in the presence of catalysts such as noble metal catalysts, e.g. B. Palladium on charcoal.
Die Nj-Acetylierung wird in üblicher Weise unter Verwendung Nj-acetylierender Mittel durchgeführt. Solche sind vor allem die Säureanhydride oder -halogenide, wie -chloride. Die Reaktion wird zweckmäßig in Gegenwart basischer Mittel, wie anorganischer oder organischer Basen, z. B. Alkalicarbonaten, oder tertiären Aminen, wie Pyridin, Picolin, Lutidin, Collidin, Trimethylamine Triäthylamin, Tributylamin oder 1,6-Bis-dimethylamino-hexan, und in Gegenwart inerter Verdünnungsmittel, insbesondere organischer Lösungsmittel, wie Dioxan, Benzol, Toluol, halo-Verf ahren zur HerstellungThe Nj-acetylation is carried out in the usual way Use of Nj-acetylating agents carried out. Such are especially the acid anhydrides or -halides, such as -chloride. The reaction is expedient in the presence of basic agents, such as inorganic ones or organic bases, e.g. B. alkali carbonates, or tertiary amines such as pyridine, picoline, lutidine, Collidine, trimethylamine, triethylamine, tributylamine or 1,6-bis-dimethylamino-hexane, and in the presence inert diluents, especially organic solvents such as dioxane, benzene, toluene, halo-Verf ears for production
des N-(p-Aminobenzolsulfonyl)-des N- (p-aminobenzenesulfonyl) -
N-acetyl-5-amino- 1-phenyl-pyrazolsN-acetyl-5-amino-1-phenyl-pyrazoles
Anmelder:Applicant:
CIBA Aktiengesellschaft, Basel (Schweiz)CIBA Aktiengesellschaft, Basel (Switzerland)
Vertreter: Dipl.-Ing. E. Splanemann, Patentanwalt, Hamburg 36, Neuer WaU 10Representative: Dipl.-Ing. E. Splanemann, patent attorney, Hamburg 36, Neuer WaU 10
Beanspruchte Priorität:
Schweiz vom 18. Februar 1958 (Nr. 56 002)Claimed priority:
Switzerland of February 18, 1958 (No. 56 002)
Dr. Jean Druey, Riehen,Dr. Jean Druey, Riehen,
und Dr. Paul Schmidt, Therwil (Schweiz),and Dr. Paul Schmidt, Therwil (Switzerland),
sind als Erfinder genannt wordenhave been named as inventors
genierte Kohlenwasserstoffe, z. B. Methylenchlorid oder Chloroform, Dimethylformamid, niederen aliphatischen Ketonen, wie Aceton oder Methyläthylketon, oder gegebenenfalls den basischen Mitteln selbst, z. B. Pyridin oder Mischungen davon, wie besonders Pyridin—Aceton, durchgeführt. Vorteilhaft arbeitet man in möglichst wasserfreiem Medium. Wird ein Säurehalogenid verwendet, so kann man auch ein Metallsalz des Sulfonamids, z. B. ein Alkalisalz oder, besser, das Silbersalz, verwenden, wodurch sich die oben empfohlene Beifügung basischer Mittel erübrigt. Ihrer zusätzlichen Verwendung, z. B. als Verdünnungsmittel, steht aber nichts im Weg.gened hydrocarbons, e.g. B. methylene chloride or chloroform, dimethylformamide, lower aliphatic Ketones, such as acetone or methyl ethyl ketone, or optionally the basic agents itself, e.g. B. pyridine or mixtures thereof, such as especially pyridine-acetone carried out. Advantageous one works in a medium that is as water-free as possible. If an acid halide is used, one can also a metal salt of sulfonamide, e.g. B. an alkali salt or, better, the silver salt, use, whereby the addition of basic agents recommended above is unnecessary. Your additional use, e.g. B. as Thinner, but nothing gets in the way.
Bei Verwendung des 5-(p-Aminobenzolsulfonamido)-1-phenyl-pyrazols ist darauf zu achten, daß die Reaktion unter milden Bedingungen und unter Verwendung etwa äquimolekularer Mengen der Reaktionsteilnehmer durchgeführt wird, um zu vermeiden, daß die Nx,N4-Bis-acetylverbindung oder durch Acylwanderung die N4-Acetylverbindung entsteht. Vorteilhaft arbeitet man deshalb bei niederer Temperatur, z. B. unter 400C, wie zwischen 10 und 30° C, und in wasserfreiem Medium. Bei Verwendung der Säurehalogenide empfiehlt es sich, von den Metallsalzen des Sulfonamids, wie dem Silbersalz, auszugehen.When using 5- (p-aminobenzenesulfonamido) -1-phenyl-pyrazole, care must be taken that the reaction is carried out under mild conditions and using approximately equimolecular amounts of the reactants in order to avoid that the N x , N 4 - Bis-acetyl compound or the N 4 -acetyl compound is formed by acyl migration. It is therefore advantageous to work at a low temperature, e.g. B. below 40 0 C, such as between 10 and 30 ° C, and in an anhydrous medium. When using the acid halides, it is advisable to start from the metal salts of the sulfonamide, such as the silver salt.
Die neue Verbindung besitzt wertvolle chemotherapeutische Eigenschaften. Sie hat eine starke und lang dauernde Wirkung gegenüber der StreptokokkensepsisThe new compound has valuable chemotherapeutic properties. She has a strong and long lasting effect against streptococcal sepsis
109 750/549109 750/549
der Maus und zeigt weiter" sehr gute Aktivität gegenüber Coli-Bakterien im Urin und im Darm. Außerdem ist sie praktisch frei von unangenehmen Geschmäcksqualitäten, wie sie oft den Sulfonamiden anhaften, und kann deshalb mit Vorteil für die Herstellung von Tabletten und Sirups dienen.of the mouse and also shows "very good activity against Coli bacteria in the urine and in the intestine. In addition it is practically free of unpleasant taste qualities, as often attached to sulfonamides, and can therefore be used to advantage in the manufacture of tablets and syrups.
Die Erfindung wird im folgenden Beispiel beschrieben. Die Temperaturen sind in Celsiusgraden angegeben. The invention is described in the following example. The temperatures are given in degrees Celsius.
IOIO
In einem mit Rührer und Thermometer versehenen Kolben werden 32 g 5-(p-Amino-benzolsulfonamido)-1-phenyl-pyrazol in 80 cm3 Aceton und 16 cm3 trockenem Pyridin bei 20 bis 25° gelöst. Unter Rühren werden innerhalb 10 Minuten 11g Essigsäureanhydrid zugegeben. Man rührt während 5 Stunden und läßt die Mischung während 10 Stunden stehen. Es wird dann unter Rühren 100 cm3 3 %iges wäßriges Ammoniak und etwas frisches Eis zugegeben, wonach ein öliges Produkt ausfällt. Man versetzt es mit 500 cm3 Wasser und läßt während 10 Stunden bei Zimmertemperatur stehen, wobei das gebildete Öl allmählich kristallisiert. Das so erhaltene N-(p-Aminobenzolsulfonyty-N-acetyl-S-amino-1 -phenyl-pyrazol wird aus Äthanol umkristallisiert und wird so in weißen Kristallen vom F. 178 bis 180° erhalten.In a flask equipped with a stirrer and thermometer, 32 g of 5- (p-amino-benzenesulfonamido) -1-phenyl-pyrazole are dissolved in 80 cm 3 of acetone and 16 cm 3 of dry pyridine at 20 to 25 °. While stirring, 11 g of acetic anhydride are added over the course of 10 minutes. The mixture is stirred for 5 hours and the mixture is left to stand for 10 hours. It is cm ig it added under stirring 100 3 3% aqueous ammonia and some fresh ice, after which an oily product precipitates. It is mixed with 500 cm 3 of water and left to stand for 10 hours at room temperature, the oil formed gradually crystallizing. The N- (p-aminobenzene-sulfonyty-N-acetyl-S-amino-1-phenyl-pyrazole thus obtained is recrystallized from ethanol and is thus obtained in white crystals with a melting point of 178 ° to 180 °.
Claims (7)
Formel45 sulfonamido) -l-phenyl-pyrazole the general
formula
Deutsche Patentschrift Nr. 952 809;
britische Patentschrift Nr. 788 140;
HeIv. chim. Acta, 41 [1958], S. 306 bis 309;
Schweizerische medizinische Wochenschrift,
[1958], S. 835 bis 839 und 858 bis 863.Considered publications:
German Patent No. 952 809;
British Patent No. 788 140;
HeIv. chim. Acta, 41 [1958], pp. 306-309;
Swiss medical weekly,
[1958], pp. 835 to 839 and 858 to 863.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1119869X | 1958-02-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1119869B true DE1119869B (en) | 1961-12-21 |
Family
ID=4558585
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEC18366A Pending DE1119869B (en) | 1958-02-18 | 1959-02-09 | Process for the preparation of N- (p-aminobenzenesulfonyl) -N-acetyl-5-amino-1-phenyl-pyrazole |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE1119869B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3374227A (en) * | 1963-01-10 | 1968-03-19 | Ciba Geigy Corp | Sulfonamides |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE952809C (en) * | 1939-05-24 | 1956-11-22 | Dehydag Gmbh | Process for the production of pellets of aromatic sulfonamides |
| GB788140A (en) * | 1955-04-07 | 1957-12-23 | Hoffmann La Roche | Novel 4-substituted-pyrazole derivatives and a process for the manufacture and conversion thereof |
-
1959
- 1959-02-09 DE DEC18366A patent/DE1119869B/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE952809C (en) * | 1939-05-24 | 1956-11-22 | Dehydag Gmbh | Process for the production of pellets of aromatic sulfonamides |
| GB788140A (en) * | 1955-04-07 | 1957-12-23 | Hoffmann La Roche | Novel 4-substituted-pyrazole derivatives and a process for the manufacture and conversion thereof |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3374227A (en) * | 1963-01-10 | 1968-03-19 | Ciba Geigy Corp | Sulfonamides |
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