CH251025A - Process for the preparation of B-picolyl nicotinate. - Google Patents
Process for the preparation of B-picolyl nicotinate.Info
- Publication number
- CH251025A CH251025A CH251025DA CH251025A CH 251025 A CH251025 A CH 251025A CH 251025D A CH251025D A CH 251025DA CH 251025 A CH251025 A CH 251025A
- Authority
- CH
- Switzerland
- Prior art keywords
- pyridyl
- picolyl
- preparation
- carbinol
- nicotinate
- Prior art date
Links
Landscapes
- Pyridine Compounds (AREA)
Description
Verfahren zur Herstellung von Nicotinsäure-p-picolylester. Es wurde gefunden, dass Ester des Pyr- idyl,3-carbinols mit organischen Säuren. ga- pillarerweiterung bewirken. Diese blutdruck- senkenden Ester zeichnen sich durch Reiz losigkeit und gute Verträglichkeit aus.
Sie können sowohl oral a19 auch parenteral appli ziert werden.
Die Herstellung .der Ester des Pyridyl-3- .carbinols kann durch folgende Verfahren geschehen: Einwirken von Säuren auf das Pyridyl-3-carbinol, Veresterung mit Säure anhydriden, Umsetzung der Säurehalogenide mit dem freien Pyridyl-3-carbinoloder einem Salz desselben oder Behandeln des 3-Ghlor- methyl:
-pyridins mit einem Salz der zu ver- esternden Säure.
Das als Ausgangsverbindung dienende Pyri-dyl-3-,car'binol kann durch Einwirkung von Nitriten auf 3-Aminomethyl-pymidin bei tiefer Temperatur in Gegenwart von alipha.- tischen Carboneäuren gewonnen werden.
Gegenstand .des vorliegenden Patentes ist ein Verfahren zur Hentellung von Nicotin- säure-ss-picoly'lester, welches dadurch gekenn- zeichnet ist, dass Pyridyl-3,-carbinol mit Nico- tinsäureanhydrid erhitzt wird.
Der Nicotinsäure-ss-picolylester schmilzt bei 47 . Er ist leicht löslich in Wasser sowie in den üblichen, organischen Lösungsmitteln und schwer löslich in Ligroin und Petrol- äther. Die neue Verbindung soll als Arzneimittel verwendet werden.
<I>Beispiel:</I> 54,5 Gewichtsteile Pyridyl-3-carbinol und 113 Gewichtsteile Nicotinsäureanhydrid wer den in einer Stickstoffatmosphäre während 10 Stunden auf 150 erhitzt. Darauf wird der Ester in der gälte mit einer gesättigten. galiumcarbonatlösung in Freiheit gesetzt und der alkalischen Flüssigkeit mit Chloroform entzogen.
Die vereinigten Auszüge wenden mit gesättigter Kochsalzlösung alkalifrei ge waschen, die Lösung mit Pottasche getrock net und das Lösungsmittel im Teilvakuum verdampft. Nach einem Destillationsvorlauf von regeneriertem Pyridyl-3-car'binal destil liert der Nicotxi@nsäure-ss-picolylester im Hoch vakuum bei 134 unter einem Druck von 0,0,5 mm über.
Die Ausbeute an Nieotin6äure- ss-picolylesster, berechnet auf umgesetztes Pyridyl-3-carbinol, beträgt 80 % der Theorie.
Process for the preparation of p-picolyl nicotinate. It has been found that esters of pyridyl, 3-carbinol with organic acids. cause gap widening. These antihypertensive esters are characterized by their lack of irritation and good tolerance.
They can be applied either orally or parenterally.
The production of the esters of pyridyl-3-carbinol can be done by the following processes: action of acids on the pyridyl-3-carbinol, esterification with acid anhydrides, reaction of the acid halides with the free pyridyl-3-carbinol or a salt thereof or treatment of 3-chloromethyl:
-pyridins with a salt of the acid to be esterified.
The pyridyl-3-carbinol used as the starting compound can be obtained by the action of nitrites on 3-aminomethyl-pymidine at low temperature in the presence of aliphatic carbonic acids.
The subject of the present patent is a process for the preparation of nicotinic acid-β-picoly'l ester, which is characterized in that pyridyl-3-carbinol is heated with nicotinic anhydride.
The nicotinic acid ss-picolyl ester melts at 47. It is easily soluble in water as well as in the usual organic solvents and hardly soluble in ligroin and petroleum ether. The new compound is to be used as a medicament.
<I> Example: </I> 54.5 parts by weight of pyridyl-3-carbinol and 113 parts by weight of nicotinic anhydride are heated to 150 in a nitrogen atmosphere for 10 hours. Then the ester is in the cold with a saturated. Galium carbonate solution set free and removed from the alkaline liquid with chloroform.
The combined extracts are washed with saturated sodium chloride solution free of alkali, the solution is dried with potash and the solvent is evaporated in a partial vacuum. After a distillation forerun of regenerated pyridyl-3-carbinal distil the nicotxi @ nic acid-ss-picolyl ester in high vacuum at 134 under a pressure of 0.0.5 mm over.
The yield of nieotin6 acid ss-picolylesster, calculated on converted pyridyl-3-carbinol, is 80% of theory.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH251025T | 1946-06-04 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH251025A true CH251025A (en) | 1947-09-30 |
Family
ID=4468557
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH251025D CH251025A (en) | 1946-06-04 | 1946-06-04 | Process for the preparation of B-picolyl nicotinate. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH251025A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1106327B (en) * | 1955-12-14 | 1961-05-10 | Lannacher Heilmittel | Process for the preparation of 7-ª-oxyaethyltheophylline nicotinic acid ester |
| DE1109181B (en) * | 1955-12-14 | 1961-06-22 | Lannacher Heilmittel | Process for the preparation of the morphine-bis-nicotinic acid ester |
| US3265704A (en) * | 1966-08-09 | Picoline esters |
-
1946
- 1946-06-04 CH CH251025D patent/CH251025A/en unknown
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3265704A (en) * | 1966-08-09 | Picoline esters | ||
| DE1106327B (en) * | 1955-12-14 | 1961-05-10 | Lannacher Heilmittel | Process for the preparation of 7-ª-oxyaethyltheophylline nicotinic acid ester |
| DE1109181B (en) * | 1955-12-14 | 1961-06-22 | Lannacher Heilmittel | Process for the preparation of the morphine-bis-nicotinic acid ester |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CH251025A (en) | Process for the preparation of B-picolyl nicotinate. | |
| AT163742B (en) | Process for the preparation of esters of pyridyl-3-carbinol | |
| DE2436332A1 (en) | SUBSTITUTED TETRAHYDROFURANS AND PROCESS FOR THEIR PRODUCTION | |
| CH251023A (en) | Process for the preparation of B-picolyl nicotinate. | |
| DE322746C (en) | Process for the preparation of ethylidene diacetate | |
| DE1803911C3 (en) | Process for the preparation of 7-chloro-2-methylamino-5-phenyl-3H-1,4benzodiazepine-4-oxide | |
| CH258206A (en) | Process for the preparation of pyridyl-3-carbinol acetate. | |
| CH253657A (en) | Process for the preparation of a new derivative of a carboxylic acid. | |
| AT232658B (en) | Process for the preparation of new steroids unsaturated in the 1- and 4-positions | |
| AT233176B (en) | Process for the preparation of new 21-half esters of 3, 20-dioxo-21-hydroxypregnane compounds which are unsaturated in ring A | |
| CH258205A (en) | Process for the preparation of phenylacetic acid B-picolate. | |
| AT266109B (en) | Process for the preparation of the sodium salt of (1-p-chlorobenzoyl-2-methyl-5-methoxy-3-indolyl) -acetic acid, optionally mixed with the free acid | |
| DE842489C (en) | Process for the preparation of therapeutically active oxyhydrophenanthrene carboxylic acids from the corresponding inactive diastereomers | |
| DE957943C (en) | Process for the preparation of 3-methyl-3-carboxycyclohexanone- (l) -2 - /? - propionic acid and derivatives thereof | |
| CH251026A (en) | Process for the preparation of B-picolyl nicotinate. | |
| AT227256B (en) | Process for the production of new aminoindanes and their salts | |
| AT238886B (en) | Process for the preparation of 16β-methyl-1,4-pregnadiene-9α-fluoro-11β, 17α, 21-trihydroxy-3,20-dione and its 21-esters | |
| AT216499B (en) | Process for the preparation of β- (4-methoxybenzoyl) -β-haloacrylic acids | |
| CH251252A (en) | Process for the preparation of pyridyl-3-carbinol acetate. | |
| DE1118783B (en) | Process for the preparation of heterocyclic di- and / or tricarboxylic acids of aromatic character | |
| DE1030825B (en) | Process for the production of aromatic di- and polycarboxylic acids | |
| CH238688A (en) | Process for the preparation of a derivative of 3,4-dioxy-thiophane. | |
| DE1093793B (en) | Process for the preparation of water-soluble steroid compounds | |
| DE1076683B (en) | Process for the preparation of the formic acid esters of 1-alkynylcycloalkanols | |
| CH273602A (en) | Process for the production of |