CH201119A - Method of making a therapeutically useful compound. - Google Patents
Method of making a therapeutically useful compound.Info
- Publication number
- CH201119A CH201119A CH201119DA CH201119A CH 201119 A CH201119 A CH 201119A CH 201119D A CH201119D A CH 201119DA CH 201119 A CH201119 A CH 201119A
- Authority
- CH
- Switzerland
- Prior art keywords
- making
- therapeutically useful
- useful compound
- compound
- compounds
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims description 13
- 238000004519 manufacturing process Methods 0.000 title description 2
- 238000000034 method Methods 0.000 claims description 5
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 claims description 5
- 229940124530 sulfonamide Drugs 0.000 claims description 4
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 claims description 3
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims description 3
- 229940014800 succinic anhydride Drugs 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 2
- JDVPQXZIJDEHAN-UHFFFAOYSA-N succinamic acid Chemical group NC(=O)CCC(O)=O JDVPQXZIJDEHAN-UHFFFAOYSA-N 0.000 claims description 2
- 239000001384 succinic acid Substances 0.000 claims description 2
- -1 succinic acid halide Chemical class 0.000 claims description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 238000001990 intravenous administration Methods 0.000 description 2
- 238000007920 subcutaneous administration Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 150000008043 acidic salts Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 150000008331 benzenesulfonamides Chemical class 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical compound OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung einer therapeutisch wertvollen Verbindung. Es wurde gefunden, dass Verbindungen der allgemeinen Formel
EMI0001.0004
therapeutisch wertvoll sind.
R bedeutet in dieser Formel einen organi schen Rest, welcher eine salzbildende Gruppe enthält oder eine Gruppe, die fähig ist, in eine solche überzugehen.
B' stellt einen durch mindestens eine Sul- fonsäureamidgruppe oder durch eine Gruppe, die sich in eine Sulfonsäureamidgruppe über führen lässt, substituierten organischen Rest oder auch Wasserstoff oder einen beliebigen Kohlenwasserstoffrest dar. R" bedeutet Was serstoff oder einen beliebigen Kohlenwasser stoffrest. Als besonders wertvoll haben sich Ver bindungen erwiesen, bei denen R und/oder R' aromatische Reste darstellen mit Substituen- ten, die in p-Stellung zueinander stehen.
R und R' können jedoch auch heterocyclischer oder aliphatischer Natur sein.
Die Herstellung dieser Verbindungen er folgt zum Beispiel nach an sich bekannten Verfahren. So kann man zum Beispiel geeig nete Säurechloride bezw. -anhydride mit ent sprechenden Aminoverbindungen umsetzen, so dass Verbindungen der Formel
EMI0001.0026
erhalten werden.
Die neuen Verbindungen eignen sich vor züglich zur intravenösen und subcutanen Darreichung, da ihre Salze, insbesondere ihre Alkalisalze mit neutraler Reaktion wasserlös lich sind, wohingegen die bereits bekannten Benzolsulfonamide, sowie ihre basischen Derivate, nur in Form ihrer stark sauer reagierenden Salze, z. B.
Chlorhydrate, in Wasser löslich sind, was ihre intravenöse oder subcutane Application ausschliesst. Die neuen Verbindungen besitzen durch ihre allgemeine Verwendungsmöglichkeit einen gegenüber den für dieses Anwendungsgebiet bislang bekannten Verbindungen besonderen thera peutischen Wert.
Gegenstand des vorliegenden Patentes ist ein Verfahren zur Herstellung einer neuen therapeutisch wertvollen Verbindung, da durch gekennzeichnet, dass man 4-Aminoben- zol-sulfonamid mit einer Verbindung um setzt, die den Rest -CO(CH,)z. COOH an das 4-Aminobenzol-sulfonamid abgibt, wie Bernsteinsäureanhydrid oder ein Halbhaloge- nid der Bernsteinsäure. <I>Beispiel:
</I> 17,2 g 4-Aminobenzolsulfonamid, erhal ten aus dem entsprechenden Sulfochlorid und Ammoniak, und 11,2g Bernsteinsäureanhy- drid werden, feinst pulverisiert, eine Stunde auf 170 bis 180 erhitzt. Das erhaltene Pro dukt wird in verdünntem Natriumcarbonat aufgenommen, die Lösung filtriert und das acylierte Produkt durch Säure gefällt.
Durch Umkristallisieren aus Wasser wird das N--(4 -Sulfamidobenzol)-bernsteinsäuremono- amid in farblosen Nadeln vom F. 211 in guter Ausbeute erhalten.
Method of making a therapeutically useful compound. It was found that compounds of the general formula
EMI0001.0004
are therapeutically valuable.
In this formula, R denotes an organic radical which contains a salt-forming group or a group which is capable of changing into one.
B 'represents an organic radical substituted by at least one sulfonic acid amide group or by a group which can be converted into a sulfonic acid amide group, or else hydrogen or any hydrocarbon radical. R "means hydrogen or any hydrocarbon radical. As particularly valuable Ver compounds have been found in which R and / or R 'represent aromatic radicals with substituents which are in the p-position to one another.
However, R and R 'can also be heterocyclic or aliphatic in nature.
These compounds are prepared, for example, by methods known per se. So you can, for example, appropriate acid chlorides BEZW. -react anhydrides with appropriate amino compounds, so that compounds of the formula
EMI0001.0026
can be obtained.
The new compounds are suitable for intravenous and subcutaneous administration because their salts, especially their alkali salts with a neutral reaction, are water-soluble, whereas the already known benzenesulfonamides and their basic derivatives, only in the form of their strongly acidic salts, e.g. B.
Chlorhydrates, are soluble in water, which precludes their intravenous or subcutaneous application. Due to their general use, the new compounds have a particular therapeutic value compared to the compounds previously known for this field of application.
The subject of the present patent is a process for the preparation of a new therapeutically valuable compound, characterized in that 4-aminobenzene-sulfonamide is reacted with a compound which contains the radical -CO (CH,) z. COOH releases to the 4-aminobenzenesulfonamide, such as succinic anhydride or a half-halide of succinic acid. <I> example:
17.2 g of 4-aminobenzenesulfonamide, obtained from the corresponding sulfochloride and ammonia, and 11.2 g of succinic anhydride, finely pulverized, heated to 170 to 180 for one hour. The product obtained is taken up in dilute sodium carbonate, the solution is filtered and the acylated product is precipitated with acid.
Recrystallization from water gives the N - (4-sulfamidobenzene) succinic acid monoamide in colorless needles with a melting point of 211 in good yield.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE201119X | 1936-06-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH201119A true CH201119A (en) | 1938-11-15 |
Family
ID=5764617
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH201119D CH201119A (en) | 1936-06-15 | 1937-06-09 | Method of making a therapeutically useful compound. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH201119A (en) |
-
1937
- 1937-06-09 CH CH201119D patent/CH201119A/en unknown
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