CH351275A - Process for the preparation of a new aminobenzenesulfonamide - Google Patents
Process for the preparation of a new aminobenzenesulfonamideInfo
- Publication number
- CH351275A CH351275A CH351275DA CH351275A CH 351275 A CH351275 A CH 351275A CH 351275D A CH351275D A CH 351275DA CH 351275 A CH351275 A CH 351275A
- Authority
- CH
- Switzerland
- Prior art keywords
- phenyl
- amino
- pyrazole
- converted
- amino group
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 9
- 238000002360 preparation method Methods 0.000 title claims description 4
- YAZSBRQTAHVVGE-UHFFFAOYSA-N 2-aminobenzenesulfonamide Chemical compound NC1=CC=CC=C1S(N)(=O)=O YAZSBRQTAHVVGE-UHFFFAOYSA-N 0.000 title description 4
- 125000003277 amino group Chemical group 0.000 claims description 11
- 238000006243 chemical reaction Methods 0.000 claims description 8
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 6
- UAKMORCTNRFNMR-UHFFFAOYSA-N 2-phenyl-1,3-dihydropyrazol-3-amine Chemical compound NC1N(NC=C1)C1=CC=CC=C1 UAKMORCTNRFNMR-UHFFFAOYSA-N 0.000 claims description 5
- 125000001424 substituent group Chemical group 0.000 claims description 4
- -1 benzenesulfonic acid halide Chemical class 0.000 claims description 3
- 239000007859 condensation product Substances 0.000 claims description 3
- 150000003839 salts Chemical class 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
- 229940092714 benzenesulfonic acid Drugs 0.000 claims description 2
- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 2
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 2
- KEQTWHPMSVAFDA-UHFFFAOYSA-N 2,3-dihydro-1h-pyrazole Chemical group C1NNC=C1 KEQTWHPMSVAFDA-UHFFFAOYSA-N 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- 239000002244 precipitate Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 206010061372 Streptococcal infection Diseases 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 230000035876 healing Effects 0.000 description 2
- 239000007800 oxidant agent Substances 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 229940067157 phenylhydrazine Drugs 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 229940124530 sulfonamide Drugs 0.000 description 2
- 150000003456 sulfonamides Chemical class 0.000 description 2
- GRDXCFKBQWDAJH-UHFFFAOYSA-N 4-acetamidobenzenesulfonyl chloride Chemical compound CC(=O)NC1=CC=C(S(Cl)(=O)=O)C=C1 GRDXCFKBQWDAJH-UHFFFAOYSA-N 0.000 description 1
- MTERSQYMYBGZTP-UHFFFAOYSA-N 4-amino-n-(5-methyl-2-phenylpyrazol-3-yl)benzenesulfonamide Chemical compound C=1C=CC=CC=1N1N=C(C)C=C1NS(=O)(=O)C1=CC=C(N)C=C1 MTERSQYMYBGZTP-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 208000035473 Communicable disease Diseases 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- VTLYFUHAOXGGBS-UHFFFAOYSA-N Fe3+ Chemical class [Fe+3] VTLYFUHAOXGGBS-UHFFFAOYSA-N 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- ZNMQWFBOQXNGKR-UHFFFAOYSA-N N-[4-[[5-(4-acetamidophenyl)sulfonyl-3-amino-2-phenyl-1,3-dihydropyrazol-4-yl]sulfonyl]phenyl]acetamide Chemical compound C(C)(=O)NC1=CC=C(C=C1)S(=O)(=O)C1=C(C(N(N1)C1=CC=CC=C1)N)S(=O)(=O)C1=CC=C(C=C1)NC(C)=O ZNMQWFBOQXNGKR-UHFFFAOYSA-N 0.000 description 1
- PSFOMYYDCTXBHG-UHFFFAOYSA-N N4-Acetylsulfaphenazole Chemical compound C1=CC(NC(=O)C)=CC=C1S(=O)(=O)NC1=CC=NN1C1=CC=CC=C1 PSFOMYYDCTXBHG-UHFFFAOYSA-N 0.000 description 1
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 1
- 125000004442 acylamino group Chemical group 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000000973 chemotherapeutic effect Effects 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000006114 decarboxylation reaction Methods 0.000 description 1
- 230000000249 desinfective effect Effects 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 210000000936 intestine Anatomy 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
- 239000000203 mixture Substances 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 239000000725 suspension Substances 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 eines neuen Aminobenzolsulfonamids Gegenstand der vorliegenden Erfindung ist ein Verfahren zur Herstellung von 3-(p-Amino-benzol- sulfonamido)-2-phenyl-pyrazol der Formel
EMI0001.0005
Diese neue Verbindung besitzt bei experimen teller Infektion an Tieren, wie z. B. bei mit Strepto- kokken infizierten Mäusen, eine überraschend. gute Heilwirkung. Sie kann daher vorzugsweise als Heil mittel bei Infektionserkrankungen, z. B. Strepto- kokkeninfektionen, Verwendung finden.
Gegenüber bekannten, vergleichbaren Aminobenzolsulfonamiden besitzt die neue Verbindung überraschend bessere chemotherapeutische Eigenschaften. So tritt der Heil effekt auf die Streptokokkeninfektion an der Maus unter Behandlung mit der neuen Verbindung schon bei einer Blutkonzentration auf, die nur die Hälfte derjenigen des bekannten 3-(p-Amino-benzolsulfon- amido)-2-phenyl-5-methylpyrazols beträgt.
Weiterhin zeigt die neue Verbindung im Darm eine bessere antibakterielle Wirkung als die oben genannte 5-Me- thyl-Verbindung und ist dieser auch im Hinblick auf die Urindesinfizierende Wirkung überlegen.
Das erfindungsgemässe Verfahren ist dadurch ge kennzeichnet, dass man eine Verbindung der Formel
EMI0001.0019
mit einem gegebenenfalls in 4- oder 5-Stellung durch eine freie oder veresterte Carboxylgruppe substituierten 2-Phenyl-3-Y-dihydropyrazol umsetzt, wobei X und Y mit Ausnahme einer in einem von ihnen enthaltenen Iminogruppe, -NH-, sich bei der Reaktion abspaltende Reste und R die Amino- gruppe oder einen in die Aminogruppe überführbaren Substituenten bedeutet,
und in dem erhaltenen Kon densationsprodukt den Dihyd'ropyrazolring zum Pyr- azolring oxydiert, die gegebenenfalls vorhandene freie oder veresterte Carboxylgruppe abspaltet und, falls R einen in die Aminogruppe überführbaren Rest bedeutet, diesen in die Aminogruppe überführt, wo bei die drei letzteren Reaktionen in beliebiger Reihen folge durchgeführt werden können.
So kann man bei spielsweise ein Benzolsulfonsäurehalogenid, insbeson dere das Chlorid, das in p-Stellung einen in die Aminogruppe überführbaren Substituenten aufweist, mit einem 3-Amino-2-phenyl-dihydro-pyrazol, das unsubstituiert ist oder eine freie oder veresterte Carboxylgruppe besitzt, reagieren lassen.
Die ver fahrensgemässe Umsetzung wird vorteilhaft in An wesenheit von Verdünnungs- und Kondensations- mitteln durchgeführt. Ein in die Aminogruppe überführbarer Substituent ist z. B. ein solcher, der sich durch Hydrolyse, wie eine Acylaminogruppe, z. B. die Acetylamino- oder Carbäthoxyaminogruppe, durch Reduktion, wie eine Nitro- oder Azogruppe in die Aminogruppe umwandeln lässt.
Die Oxydation kann in üblicher Weise, z. B. unter Verwendung von Oxydationsmitteln, wie Eisen-III-salze, Wasserstoff peroxyd und dergleichen, vorgenommen werden. Läuft die Reaktion jedoch über ein durch Hydrolyse in das Endprodukt zu überführendes Zwischenpro dukt, wie das 3-(p-Acetylamino-benzolsulfonamido)- 2-phenyl-pyrazol, so tritt die Oxydation bei der üblichen Verseifung ohne besondere Zugabe von Oxydationsmitteln ein.
Die Abspaltung der freien oder veresterten Carboxylgruppe kann in üblicher Weise durch Decarboxylierung, gegebenenfalls nach Hydrolyse, erfolgen.
Von den neuen Aminobenzolsulfonamiden lassen sich in üblicher Weise Salze gewinnen, so z. B. durch Umsetzung mit Basen, wie Alkali- oder Erdalkali- hydroxyden, oder organischen Basen.
Das Natrium- salz des neuen Sulfonamids weist in 1% iger wässri- ger Lösung den sehr niedrigen pH-Wert von 8 auf.
Die Ausgangsstoffe sind bekannt oder lassen sich nach an sich bekannten Methoden gewinnen.
Das neue Sulfonamid und seine Salze können als Heilmittel Verwendung finden, und zwar zweckmässig in einer Menge von über 0,1 g pro Dosierungseinheit, zweckmässig zwischen 0,25 und 3 g.
Im nachstehenden Beispiel sind die Temperaturen in Celsiusgraden angegeben.
<I>Beispiel</I> Eine Lösung von 6,44 g 3-Amino-2-phenyl-di- hydro-pyrazol in 50 cm 3 Pyridin wird innerhalb zehn Minuten mit 23,8 g p-Acetylamino-benzolsulfon- säurechlorid versetzt. Die Temperatur steigt auf etwa 65 . Nach Abklingen der exothermen Reaktion er hitzt man während einer Stunde auf 95 (Innen temperatur) und bringt dann die Reaktionslösung auf 500 cm3 2n Salzsäure und etwas Eis. Es fällt ein Niederschlag aus, von dem abgenutscht wird.
Das Kondensationsprodukt enthält Bis-(p-acetylamino- benzolsulfonyl)-3-amino-2-phenyl-dihydro-pyrazol.
Das so erhaltene rohe Produkt wird direkt mit 360 cm3 2,5n Natronlauge versetzt, und die erhal tene Suspension wird während. zwei Stunden gekocht, mit Tierkohle versetzt und filtriert. Man stellt dann das Filtrat mit 5n Salzsäure auf PH 5-6, wonach ein kristalliner Niederschlag ausfällt, der abgenutscht und aus Alkohol umkristallisiert wird. Es wird so 3 - (p - Amino - benzolsulfonamido@- 2-phenyl-pyrazol vom F. 177-178 erhalten.
Das gewonnene 3-(p-Amino-benzolsulfonamido)- 2-phenyl-pyrazol lässt sich in üblicher Weise in sein Natriumsalz überführen.
Das als Ausgangsstoff verwendete 3-Amino-2- phenyl-dihydro-pyrazol wird auf folgende Weise be reitet: 16,1 g ss-Cyano-äthyl-phenylhydrazin (durch Kon densation von Phenylhydrazin mit Acrylnitril her gestellt) werden mit 200 cm3 8n alkoholischer Salz säure versetzt. Es fällt sofort ein weisser Niederschlag aus. Man rührt dann während einer Stunde bei Zim- mertemperatur und erhitzt noch zwei Stunden zum Sieden.
Nach dem Erkalten wird von dem ausgefal lenen, hygroskopischen Niederschlag abgenutscht. Das so erhaltene Hydrochlorid wird in 70 cm- Wasser gelöst, und die Lösung wird unter Eiskühlung stark alkalisch gestellt, wonach ein weisser Nieder schlag ausfällt, von dem abgenutscht wird. Das so erhaltene 3-Amino-2-phenyl-dihydro-pyrazol schmilzt nach dem Umkristallisieren aus Isopropyläther bei 106-107 .
Process for the preparation of a new aminobenzenesulfonamide The present invention relates to a process for the preparation of 3- (p-amino-benzenesulfonamido) -2-phenyl-pyrazole of the formula
EMI0001.0005
This new compound possesses experimental infection in animals such. B. in mice infected with streptococci, a surprising one. good healing properties. It can therefore preferably be used as a remedy for infectious diseases such. B. streptococcal infections find use.
Compared to known, comparable aminobenzenesulfonamides, the new compound has surprisingly better chemotherapeutic properties. Thus, the healing effect on streptococcal infection in the mouse occurs under treatment with the new compound at a blood concentration that is only half that of the known 3- (p-amino-benzenesulfonamido) -2-phenyl-5-methylpyrazole .
Furthermore, the new compound shows a better antibacterial effect in the intestine than the above-mentioned 5-methyl compound and is also superior to it with regard to the urine disinfecting effect.
The inventive method is characterized in that a compound of the formula
EMI0001.0019
with a 2-phenyl-3-Y-dihydropyrazole optionally substituted in the 4- or 5-position by a free or esterified carboxyl group, where X and Y, with the exception of an imino group contained in one of them, -NH-, differ in the reaction radicals which split off and R denotes the amino group or a substituent which can be converted into the amino group,
and in the condensation product obtained, the Dihyd'ropyrazolring oxidizes to the pyrazole ring, splits off any free or esterified carboxyl group present and, if R denotes a radical which can be converted into the amino group, converts this into the amino group, where the last three reactions in any Sequence can be carried out.
For example, a benzenesulfonic acid halide, in particular the chloride which has a substituent that can be converted into the amino group in the p-position, with a 3-amino-2-phenyl-dihydro-pyrazole which is unsubstituted or has a free or esterified carboxyl group let react.
The implementation according to the method is advantageously carried out in the presence of diluents and condensation agents. A substituent which can be converted into the amino group is e.g. B. one which is obtained by hydrolysis, such as an acylamino group, e.g. B. the acetylamino or carbethoxyamino group, can be converted into the amino group by reduction, such as a nitro or azo group.
The oxidation can be carried out in a conventional manner, e.g. B. using oxidizing agents such as iron (III) salts, hydrogen peroxide and the like. However, if the reaction takes place via an intermediate product to be converted into the end product by hydrolysis, such as 3- (p-acetylamino-benzenesulfonamido) -2-phenyl-pyrazole, the oxidation occurs during the usual saponification without special addition of oxidizing agents.
The cleavage of the free or esterified carboxyl group can be carried out in the customary manner by decarboxylation, if appropriate after hydrolysis.
Salts can be obtained from the new aminobenzenesulfonamides in the usual way, e.g. B. by reaction with bases, such as alkali or alkaline earth metal hydroxides, or organic bases.
The sodium salt of the new sulfonamide has a very low pH of 8 in a 1% aqueous solution.
The starting materials are known or can be obtained by methods known per se.
The new sulfonamide and its salts can be used as medicaments, expediently in an amount of over 0.1 g per dosage unit, expediently between 0.25 and 3 g.
In the example below, the temperatures are given in degrees Celsius.
<I> Example </I> A solution of 6.44 g of 3-amino-2-phenyl-dihydropyrazole in 50 cm 3 of pyridine is admixed with 23.8 g of p-acetylamino-benzenesulphonic acid chloride within ten minutes . The temperature rises to around 65. After the exothermic reaction has subsided, it is heated to 95 (internal temperature) for one hour and then the reaction solution is brought to 500 cm3 of 2N hydrochloric acid and a little ice. A precipitate separates out and is filtered off with suction.
The condensation product contains bis (p-acetylamino-benzenesulfonyl) -3-amino-2-phenyl-dihydro-pyrazole.
The crude product obtained in this way is mixed directly with 360 cm3 of 2.5N sodium hydroxide solution, and the suspension obtained is during. Boiled for two hours, mixed with animal charcoal and filtered. The filtrate is then adjusted to pH 5-6 with 5N hydrochloric acid, after which a crystalline precipitate separates out, which is filtered off with suction and recrystallized from alcohol. This gives 3 - (p - amino - benzenesulfonamido @ - 2-phenyl-pyrazole, melting point 177-178.
The 3- (p-amino-benzenesulfonamido) -2-phenyl-pyrazole obtained can be converted into its sodium salt in the usual way.
The 3-amino-2-phenyl-dihydro-pyrazole used as starting material is prepared in the following way: 16.1 g of ss-cyano-ethyl-phenylhydrazine (made by condensation of phenylhydrazine with acrylonitrile) are more alcoholic with 200 cm3 of 8n Hydrochloric acid added. A white precipitate falls out immediately. The mixture is then stirred for one hour at room temperature and heated to the boil for a further two hours.
After cooling, the hygroscopic precipitate which has precipitated is filtered off with suction. The hydrochloride obtained in this way is dissolved in 70 cm water, and the solution is made strongly alkaline while cooling with ice, after which a white precipitate separates out, from which it is suction filtered. The 3-amino-2-phenyl-dihydro-pyrazole obtained in this way melts at 106-107 after recrystallization from isopropyl ether.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH344413T | 1957-02-21 | ||
| CH351275T | 1957-02-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH351275A true CH351275A (en) | 1961-01-15 |
Family
ID=25736950
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH351275D CH351275A (en) | 1957-02-21 | 1957-02-21 | Process for the preparation of a new aminobenzenesulfonamide |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH351275A (en) |
-
1957
- 1957-02-21 CH CH351275D patent/CH351275A/en unknown
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