CH278408A - Process for the preparation of a derivative of p-amino-salicylic acid. - Google Patents
Process for the preparation of a derivative of p-amino-salicylic acid.Info
- Publication number
- CH278408A CH278408A CH278408DA CH278408A CH 278408 A CH278408 A CH 278408A CH 278408D A CH278408D A CH 278408DA CH 278408 A CH278408 A CH 278408A
- Authority
- CH
- Switzerland
- Prior art keywords
- amino
- preparation
- salicylic acid
- derivative
- acid
- Prior art date
Links
- WUBBRNOQWQTFEX-UHFFFAOYSA-N 4-aminosalicylic acid Chemical class NC1=CC=C(C(O)=O)C(O)=C1 WUBBRNOQWQTFEX-UHFFFAOYSA-N 0.000 title claims description 6
- 238000002360 preparation method Methods 0.000 title claims description 5
- 238000000034 method Methods 0.000 title claims description 4
- 229960004909 aminosalicylic acid Drugs 0.000 claims description 4
- 239000013078 crystal Substances 0.000 claims description 2
- 238000000354 decomposition reaction Methods 0.000 claims description 2
- 150000001875 compounds Chemical group 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
- 239000005711 Benzoic acid Substances 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000003385 bacteriostatic effect Effects 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 235000019441 ethanol Nutrition 0.000 description 1
- 229940126601 medicinal product Drugs 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- -1 pentenylacetyl halide Chemical class 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000001226 reprecipitation Methods 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/12—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by halogen atoms or by nitro or nitroso groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung eines Derivates der p-Amino-salicylsäure. Es wurde gefunden, dass man zu Substan zen mit wertvollen therapeutischen Eigen schaften gelangt, wenn man p-Amino-salicyl- säure oder deren Salze oder Ester mit acylie- renden Mitteln behandelt, die eine Cyclopen- tenyl-oder Cyclopentylgruppe enthalten.
Dieses Resultat war um so überraschender, als in der Literatur darauf hingewiesen wird, dass bei Substitution in der 4-Aminogruppe zttm Bei spiel durch aliphatische Säuren die bakterio- statische Wirkung vermindert wird (The Lan- eet 1946, Seite 15).
Gegenstand des vorliegenden Patentes ist ein Verfahren zur Herstellung von 4-d2',3'- Cy elopentenylacetylamino - 2 - oxy -1 - benzoe- säure, welches dadurch gekennzeichnet ist, dass man auf p-Ainino-salicylsäure ein 42,3-Cyclo- pentenylacetyllialogenid einwirken lässt. Das Produkt soll als Arzneimittel verwendet wer den.
Es entspricht der Formel:
EMI0001.0028
Beispiel: 121 g p-Amino-salicylsäure werden unter Zugabe von Dimethylanilin bei gewöhnlicher Temperatur mit 114,5 g 42,3-Cyclopentenyl- acet.ylchlorid vermischt, wobei die Tempera tur auf etwa 30 steigt.
Nach mehrstündigem Stehenlassen wird das Reaktionsprodukt in Sodalösung aufgenommen, diese durch Aus schütteln mit Äther gewaschen und aus der wässrigen Lösung durch Ansäuern mit Salz säure die 4-A 2',3'-Cyelopentenylacety lamino- 2-oxy-l-benzoesäure ausgefällt. Nach noch maligem Umfällen aus Natriumkarbonatlösung mit Hilfe von Salzsäure wird aus verdünntem Äthylalkohol umkristallisiert und die weisse Kristallmasse im Exsikkator zur Trockne ge bracht.
Das reine Präparat schmilzt bei 205 C unter Zersetzung.
Process for the preparation of a derivative of p-amino-salicylic acid. It has been found that substances with valuable therapeutic properties are obtained if p-aminosalicylic acid or its salts or esters are treated with acylating agents which contain a cyclopentyl or cyclopentyl group.
This result was all the more surprising as it is pointed out in the literature that substitution in the 4-amino group, for example by aliphatic acids, reduces the bacteriostatic effect (The Laneeet 1946, page 15).
The subject of the present patent is a process for the preparation of 4-d2 ', 3'-Cy elopentenylacetylamino - 2 - oxy -1 - benzoic acid, which is characterized in that a 42,3-Cyclo is added to p-amino-salicylic acid - lets pentenylacetyl halide act. The product is intended to be used as a medicinal product.
It corresponds to the formula:
EMI0001.0028
Example: 121 g of p-amino-salicylic acid are mixed with 114.5 g of 42,3-cyclopentenyl-acet.yl chloride at normal temperature with the addition of dimethylaniline, the temperature rising to about 30.
After standing for several hours, the reaction product is taken up in soda solution, washed by shaking it off with ether and the 4-A 2 ', 3'-Cyelopentenylacety lamino-2-oxy-1-benzoic acid is precipitated from the aqueous solution by acidification with hydrochloric acid. After repeated reprecipitation from sodium carbonate solution with the help of hydrochloric acid, it is recrystallized from dilute ethyl alcohol and the white crystal mass is brought to dryness in a desiccator.
The pure preparation melts at 205 ° C. with decomposition.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH278408T | 1949-07-06 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH278408A true CH278408A (en) | 1951-10-15 |
Family
ID=4481706
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH278408D CH278408A (en) | 1949-07-06 | 1949-07-06 | Process for the preparation of a derivative of p-amino-salicylic acid. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH278408A (en) |
-
1949
- 1949-07-06 CH CH278408D patent/CH278408A/en unknown
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