DE1079064B - Process for the production of new sulfonamides - Google Patents
Process for the production of new sulfonamidesInfo
- Publication number
- DE1079064B DE1079064B DEC17158A DEC0017158A DE1079064B DE 1079064 B DE1079064 B DE 1079064B DE C17158 A DEC17158 A DE C17158A DE C0017158 A DEC0017158 A DE C0017158A DE 1079064 B DE1079064 B DE 1079064B
- Authority
- DE
- Germany
- Prior art keywords
- group
- nitro
- azo
- acylamino
- salts
- 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
- 238000000034 method Methods 0.000 title claims description 7
- 150000003456 sulfonamides Chemical class 0.000 title claims description 6
- 229940124530 sulfonamide Drugs 0.000 title claims description 5
- 238000004519 manufacturing process Methods 0.000 title description 2
- -1 nitro, azo Chemical group 0.000 claims description 9
- 150000003839 salts Chemical class 0.000 claims description 8
- 125000004442 acylamino group Chemical group 0.000 claims description 7
- 125000003277 amino group Chemical group 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 5
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 11
- 229960000583 acetic acid Drugs 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 7
- 241001465754 Metazoa Species 0.000 description 4
- 239000003513 alkali Substances 0.000 description 4
- 239000003610 charcoal Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- LYPGDCWPTHTUDO-UHFFFAOYSA-M sodium;methanesulfinate Chemical compound [Na+].CS([O-])=O LYPGDCWPTHTUDO-UHFFFAOYSA-M 0.000 description 3
- XYMLBSKTNOUTLV-UHFFFAOYSA-N 4-amino-N-(6-methylsulfonylpyridazin-3-yl)benzenesulfonamide Chemical compound NC1=CC=C(C=C1)S(=O)(=O)NC=1N=NC(=CC=1)S(=O)(=O)C XYMLBSKTNOUTLV-UHFFFAOYSA-N 0.000 description 2
- 241000588724 Escherichia coli Species 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- BKPRCEQHUNKSBG-UHFFFAOYSA-N [N+](=O)([O-])C1=CC=C(C=C1)S(=O)(=O)NC=1N=NC(=CC1)Cl Chemical compound [N+](=O)([O-])C1=CC=C(C=C1)S(=O)(=O)NC=1N=NC(=CC1)Cl BKPRCEQHUNKSBG-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 2
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 208000015181 infectious disease Diseases 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- GAGIHZFTFKBBDR-UHFFFAOYSA-N 3-methylsulfonylpyridazine Chemical compound CS(=O)(=O)C1=CC=CN=N1 GAGIHZFTFKBBDR-UHFFFAOYSA-N 0.000 description 1
- JXRGUPLJCCDGKG-UHFFFAOYSA-N 4-nitrobenzenesulfonyl chloride Chemical compound [O-][N+](=O)C1=CC=C(S(Cl)(=O)=O)C=C1 JXRGUPLJCCDGKG-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- YZCKVEUIGOORGS-UHFFFAOYSA-N Hydrogen atom Chemical compound [H] YZCKVEUIGOORGS-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 206010022678 Intestinal infections Diseases 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- CZRSYHRJFOYNNE-UHFFFAOYSA-N N-(6-methylsulfonylpyridazin-3-yl)-4-nitrobenzenesulfonamide Chemical compound [N+](=O)([O-])C1=CC=C(C=C1)S(=O)(=O)NC=1N=NC(=CC=1)S(=O)(=O)C CZRSYHRJFOYNNE-UHFFFAOYSA-N 0.000 description 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000002512 chemotherapy Methods 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000000645 desinfectant Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 1
- XNEFVTBPCXGIRX-UHFFFAOYSA-N methanesulfinic acid Chemical compound CS(O)=O XNEFVTBPCXGIRX-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- DQGCGYHKEFSCGC-UHFFFAOYSA-N n-[4-[(6-chloropyridazin-3-yl)sulfamoyl]phenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1S(=O)(=O)NC1=CC=C(Cl)N=N1 DQGCGYHKEFSCGC-UHFFFAOYSA-N 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- VLYWMPOKSSWJAL-UHFFFAOYSA-N sulfamethoxypyridazine Chemical compound N1=NC(OC)=CC=C1NS(=O)(=O)C1=CC=C(N)C=C1 VLYWMPOKSSWJAL-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 210000002700 urine Anatomy 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)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Description
DEUTSCHESGERMAN
Gegenstand der vorliegenden Erfindung ist die Herstellung neuer Sulfonamide der FormelThe present invention relates to the preparation of new sulfonamides of the formula
-SO,—NH--SO, -NH-
-N=N--N = N-
-SO2-R-SO 2 -R
worin R einen Alkylrest mit 1 bis 3 Kohlenstoffatomen darstellt, sowie ihrer Salze, wie z. B. der Alkali- und Erdalkalisalze, besonders der Natrium-, Magnesium- und Aluminiumsalze. Als niedere Alkylreste R kommen dabei in Betracht: Äthyl, Propyl, besonders aber Methyl.wherein R is an alkyl radical having 1 to 3 carbon atoms, and their salts, such as. B. the Alkali and alkaline earth salts, especially the sodium, magnesium and aluminum salts. As lower alkyl radicals R are: ethyl, propyl, but especially methyl.
Die neuen Verbindungen besitzen wertvolle therapeutische Eigenschaften. Sie sind chemotherapeutisch wirksam, z. B. bei der experimentellen Kokken- oder E.coli-Infektion von Tieren, z. B. der Maus, und können als Heilmittel z.B. bei Kokkeninfektionen oder bei Darminfektionen Verwendung finden. Die neuen Sulfonamide besitzen besonders eine gute urindesinfizierende Wirkung. Gegenüber bekannten Sulfanilamido-pyridazinen, wie dem aus der deutschen Patentschrift 1 018 423 bekannten 3-(p-Aminobenzolsulfonamido)-6-methoxy-pyridazin, zeichnen sich insbesondere durch eine überlegene Wirkung gegenüber E. coli aus. ■ . : .The new compounds have valuable therapeutic properties. You are chemotherapy effective, e.g. B. in the experimental cocci or E. coli infection of animals, e.g. B. the mouse, and can be used as remedies e.g. for cocci infections or intestinal infections. The new Sulphonamides have a particularly good urine disinfectant effect. Compared to known sulfanilamido-pyridazines, such as the 3- (p-aminobenzenesulfonamido) -6-methoxypyridazine known from German patent specification 1 018 423, are characterized in particular by a superior effect compared to E. coli. ■. :.
Die neuen Verbindungen werden dadurch hergestellt, daß man in Verbindungen der FormelThe new compounds are prepared by converting into compounds of the formula
-SO9-NH--SO 9 -NH-
worin X für die Aminogruppe oder eine Nitro, Azo- oder Acylaminogruppe steht und Y eine reaktionsfähig veresterte Oxygruppe darstellt oder, wenn X eine Nitro-, Azo- oder Acylaminogruppe ist, auch die Gruppe —SO2—R selbst bedeutet, nach an sich bekannten Verfahrensweisen die Nitro-, Azo-, Acylamino- oder reaktionsfähig veresterte Oxygruppe in die freie Aminogruppe bzw. die Gruppierung — SO2—R und gegebenenfalls erhaltene freie Verbmdungen in ihre Salze überführt.where X is the amino group or a nitro, azo or acylamino group and Y is a reactive esterified oxy group or, if X is a nitro, azo or acylamino group, the group —SO 2 —R itself is known per se Procedures, the nitro, azo, acylamino or reactive esterified oxy group is converted into the free amino group or the grouping - SO 2 --R and any free compounds obtained are converted into their salts.
Die Überführung der durch Reduktion oder Hydrolyse in die Aminogruppe umwandelbaren Nitro-, Azo- oder Acylaminogruppen, besonders der Acetyl- oder Carbäthoxyaminogruppe, wird in an sich bekannter Weise durchgeführt, die Reduktion z. B. mit katalytisch erregtem oder mit naszierendem Wasserstoff, wie er z. B. durch die Einwirkung von Metallen auf Säuren erhalten wird, die Hydrolyse mit sauren, vorzugsweise jedoch alkalischen, hydrolysierenden Mitteln, wie wäßrigen Alkali- oder Erdalkalihydroxyden. The conversion of the nitro, azo, which can be converted into the amino group by reduction or hydrolysis or acylamino groups, especially the acetyl or carbethoxyamino group, is known per se Way carried out, the reduction z. B. with catalytically excited or with nascent hydrogen, how he z. B. obtained by the action of metals on acids, hydrolysis with acidic, but preferably alkaline, hydrolyzing agents, such as aqueous alkali or alkaline earth metal hydroxides.
Die in die Gruppierung —SO2—R überführbare,
reaktionsfähig veresterte Oxygruppe, besonders ein Verfahren zur Herstellung neuer
SulfonamideThe reactive esterified oxy group which can be converted into the —SO 2 —R group, especially a process for the production of new ones
Sulfonamides
Anmelder:Applicant:
CIBA Aktiengesellschaft,
Basel (Schweiz)CIBA Aktiengesellschaft,
Basel, Switzerland)
Vertreter: Dipl.-Ing. E. Splanemanii, Patentanwalt,
Hamburg 36, Neuer Wall 10Representative: Dipl.-Ing. E. Splanemanii, patent attorney,
Hamburg 36, Neuer Wall 10
Beanspruchte Priorität:
Schweiz vom 18. Juli 1957 und 29. April 1958Claimed priority:
Switzerland from July 18, 1957 and April 29, 1958
Dr. Jean Druey, Riehen, und Dr, Hans Isler,Dr. Jean Druey, Riehen, and Dr, Hans Isler,
Bottmingen (Schweiz)
sind als Erfinder genannt wordenBottmingen (Switzerland)
have been named as inventors
Halogenatom, namentlich Chlor oder Brom, wird durch Reaktion mit R-Sulfinsäuren, besonders Methansulfinsäure, in die R-Sulfonylgruppe übergeführt,. Für diese Reaktion wird die Alkansulfuisäure mit Vorteil in der Form eines Metall-, wie Alkali- oder Erdalkalisalzes verwendet.Halogen atom, namely chlorine or bromine, is produced by reaction with R-sulfinic acids, especially methanesulfinic acid, converted into the R-sulfonyl group. Alkanesulfuic acid is advantageous for this reaction used in the form of a metal such as alkali or alkaline earth salt.
Von den neuen Sulfonamides lassen sich in üblicher Weise Salze gewinnen, so z. B. durch Umsetzung mit Basen, wie Alkali- oder Erdalkalihydroxyden oder organischen Basen.Salts can be obtained from the new sulfonamides in the usual way, e.g. B. by implementing with Bases, such as alkali or alkaline earth metal hydroxides or organic bases.
Die Ausgangsstoffe sind bekannt oder können nach an sich bekannten Methoden gewonnen werden.The starting materials are known or can be obtained by methods known per se.
Die Erfindung wird in den nachfolgenden Beispielen beschrieben, ohne daß damit eine Einschränkung des Erfindungsgegenstandes beabsichtigt ist. Die Temperaturen sind in Celsiusgraden angegeben.The invention is described in the following examples, without thereby limiting the Subject of the invention is intended. The temperatures are given in degrees Celsius.
25,3g3-(p-Amino-benzoisulfonamidoi)-6-chlor-pyridazin, 10,8 g methansulfinsaures Natrium und 340 cm3 Methanol werden im verschlossenen Rohr während 6 Stunden auf 135 bis 140° erhitzt. Man filtriert dann von ungelösten Anteilen ab und verdampft das Methanol im Wasserstrahlvakuum. Der Rückstand wird in 300 cm3 1 η-Natronlauge aufgenommen, die Lösung über Tierkohle filtriert, das Filtrat mit 240 cm3 2 η-Essigsäure angesäuert und der Niederschlag abgenutscht. Er wird aus SOO cm3 2 n-Essigsäure kristallisiert.25.3 g of 3- (p-Amino-benzoisulfonamido i ) -6-chloropyridazine, 10.8 g of sodium methanesulfinate and 340 cm 3 of methanol are heated to 135 ° to 140 ° for 6 hours in a sealed tube. Undissolved components are then filtered off and the methanol is evaporated off in a water-jet vacuum. The residue is taken up in 300 cm 3 of 1 η-sodium hydroxide solution, the solution is filtered through animal charcoal, the filtrate is acidified with 240 cm 3 of 2 η-acetic acid and the precipitate is filtered off with suction. It is crystallized from 50 cm 3 2 of n-acetic acid.
:. -.-- 909· 769/549:. -.-- 909 769/549
Das so erhaltene 3-(p-Amino-benzoisulf onamido) 6-methylsulfonyl-pyridazin schmilzt bei 196 bis 199°.The 3- (p-Amino-benzoisulfonamido) 6-methylsulfonyl-pyridazine obtained in this way melts at 196 to 199 °.
29,7 g 3- (p-Acetylatnino-benzolsulfonamido) -6-chlorpyridazin, 10,8 g methansulfinsaures Natrium und 340 cm3 Methanol werden im verschlossenen Rohr während 6 Stunden auf 135 bis 140° erhitzt. Man filtriert-dann vom ungelösten Anteil ab und, verdampft das Methanol im Wasserstrahlvakuum. Der Rückstand wird in 250 cm3 2 η-Natronlauge aufgenommen, die Lösung über Tierkohle filtriert, das Filtrat während 2 Stunden gekocht und dann mit Salzsäure auf einen pH-Wert von 6 bis 7 gestellt, wonach das im Beispiel 1 beschriebene 3- (p-Amino-benzolsulf onamido) -6-methylsulfonyl-pyridazin ausfällt. Es kann, wie dort angegeben, aus 2 η-Essigsäure kristallisiert werden.29.7 g of 3- (p-Acetylatnino-benzenesulfonamido) -6-chloropyridazine, 10.8 g of sodium methanesulfinate and 340 cm 3 of methanol are heated in a sealed tube to 135 ° to 140 ° for 6 hours. The undissolved portion is then filtered off and the methanol is evaporated off in a water-jet vacuum. The residue is taken up in 250 cm 3 2 η-sodium hydroxide solution, the solution filtered over animal charcoal, the filtrate is boiled for 2 hours and then with hydrochloric acid to a p H value of 6 and 7, after which the 3- described in Example 1 ( p-Amino-benzenesulfonamido) -6-methylsulfonyl-pyridazine precipitates. As stated there, it can be crystallized from 2η-acetic acid.
28,5 g 3-(p-Nitro-benzolsulfonamido)-6-chlor-pyridazin, 10,8 g methansulfinsaures Natrium und 340 cm3 Methanol werden im verschlossenen Rohr während 6 Stunden auf 150 bis 140° erhitzt. Man dampft dann das Methanol im Vakuum ab, nimmt den Rückstand in 1 η-Natronlauge auf, filtriert die Lösung über Tierkohle und säuert mit 2 η-Essigsäure an. Das so erhaltene rohe 3-(p-Nitro-benzolsulfonamido)-6-methylsulfonyl-pyridazin wird in Eisessig gelöst und mit Palladium-Kohle als Katalysator bei Zimmertemperatur mit Wasserstoff reduziert. Innerhalb 5 Stunden wird die berechnete Menge aufgenommen. Man filtriert dann vom Katalysator ab, dampft im Vakuum den Eisessig ab und kristallisiert den Rückstand aus 2 η-Essigsäure. 3-(p-Amino-benzolsulfonamido)-6-methylsulfonyl-pyridazin wird so in Kristallen vom Schmelzpunkt 196 bis 199° erhalten.28.5 g of 3- (p-nitro-benzenesulfonamido) -6-chloropyridazine, 10.8 g of sodium methanesulfinate and 340 cm 3 of methanol are heated to 150 ° to 140 ° for 6 hours in a sealed tube. The methanol is then evaporated off in vacuo, the residue is taken up in 1η sodium hydroxide solution, the solution is filtered through animal charcoal and acidified with 2η acetic acid. The crude 3- (p-nitro-benzenesulfonamido) -6-methylsulfonyl-pyridazine obtained in this way is dissolved in glacial acetic acid and reduced with hydrogen at room temperature using palladium-carbon as a catalyst. The calculated amount will be absorbed within 5 hours. The catalyst is then filtered off, the glacial acetic acid is evaporated off in vacuo and the residue is crystallized from 2η-acetic acid. 3- (p-Amino-benzenesulfonamido) -6-methylsulfonyl-pyridazine is obtained in this way in crystals with a melting point of 196 ° to 199 °.
Das als Ausgangsstoff verwendete 3 - (p - Nitrobenzolsulfonamido)-6-chlor-pyridazin wird analog dem 3-(p-Acetaminobenzolsulf onamido)-6-chlor-pyridazin durch Umsetzung von p-Nitrobenzolsulfochlorid mit 3-Amino6-chlor^pyridazin erhalten; F.= 180° (Zersetzung).The 3 - (p - nitrobenzenesulfonamido) -6-chloro-pyridazine used as starting material is analogous to 3- (p-acetaminobenzene sulfonamido) -6-chloropyridazine by converting p-nitrobenzenesulfonyl chloride obtained with 3-amino6-chloro ^ pyridazine; F. = 180 ° (decomposition).
Claims (2)
USA.-Patentschrift Nr. 2 712 012;
Arzneimittelforschung, 1958, S. 197 ff.Considered publications:
U.S. Patent No. 2,712,012;
Pharmaceutical research, 1958, p. 197 ff.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1079064X | 1957-07-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1079064B true DE1079064B (en) | 1960-04-07 |
Family
ID=4556263
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEC17158A Pending DE1079064B (en) | 1957-07-18 | 1958-07-09 | Process for the production of new sulfonamides |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE1079064B (en) |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2712012A (en) * | 1954-11-10 | 1955-06-28 | American Cyanamid Co | 3-sulfanilamido-6-substituted pyridazines and method of preparing the same |
-
1958
- 1958-07-09 DE DEC17158A patent/DE1079064B/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2712012A (en) * | 1954-11-10 | 1955-06-28 | American Cyanamid Co | 3-sulfanilamido-6-substituted pyridazines and method of preparing the same |
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