DE1023768B - Process for the preparation of compounds of the carboline series - Google Patents
Process for the preparation of compounds of the carboline seriesInfo
- Publication number
- DE1023768B DE1023768B DEE11500A DEE0011500A DE1023768B DE 1023768 B DE1023768 B DE 1023768B DE E11500 A DEE11500 A DE E11500A DE E0011500 A DEE0011500 A DE E0011500A DE 1023768 B DE1023768 B DE 1023768B
- Authority
- DE
- Germany
- Prior art keywords
- compounds
- carboline
- preparation
- series
- oxy
- 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
Landscapes
- Nitrogen Condensed Heterocyclic Rings (AREA)
Description
Verfahren zur Herstellung von Verbindungen der Carbolinreihe Es sind Verbindungen der folgenden allgemeinen Formel bekannt: In dieser Formel bedeutet R' Wasserstoff oder Alkylradikale, R" Wasserstoff, Carboxyalkylradikale oder substituierte oder nicht substituierte Alkylradikale, R"' Wasserstoff, Oxyalkyl- oder Oxyacylradikale. Der Ring D kann geschlossen sein; in diesem Falle ist R" eine Carbonyl- oder Methylengruppe und der Stickstoff tertiär gebunden. Der Ring E kann aromatisch oder alicyclisch sein, mit oder ohne Heteroatome.Process for the preparation of compounds of the carboline series Compounds of the following general formula are known: In this formula, R 'denotes hydrogen or alkyl radicals, R "denotes hydrogen, carboxyalkyl radicals or substituted or unsubstituted alkyl radicals, R"' denotes hydrogen, oxyalkyl or oxyacyl radicals. The ring D can be closed; in this case R "is a carbonyl or methylene group and the nitrogen is tertiary bonded. The ring E can be aromatic or alicyclic, with or without heteroatoms.
Es wurde nun gefunden, daß Verbindungen der Formel in welcher R' H oder 0-Alkyl-Gruppen bedeutet, eine günstige therapeutische Wirkung besitzen. Sie sind z. B. Sympathikolytica und setzen den Blutdruck herab. Wenn man diese Carboline mit organischen Säuren verestert, dann erhält man Monoester, die eine ausgesprochen protrahierte pharmakologische Wirkung zeigen. Für die Veresterung kann man z. B. Trimethoxybenzoesäure verwenden, aber auch andere Säuren, z. B. Trimethoxyzimtsäure oder Propionsäure.It has now been found that compounds of the formula in which R 'denotes H or O-alkyl groups, have a beneficial therapeutic effect. You are e.g. B. Sympathikolytica and lower blood pressure. If these carbolines are esterified with organic acids, then monoesters are obtained which show a markedly protracted pharmacological effect. For the esterification you can, for. B. use trimethoxybenzoic acid, but also other acids, e.g. B. trimethoxycinnamic acid or propionic acid.
Beispiel 1 2 g 17-Methoxy-18-oxy-15,16,17,18,19,20-hexadehydroyohimbanchlorhydrat (hergestellt nach H ah n und H an s e 1, Ber. dtsch. Ges., 71, S. 2195 [1938]) werden in wasserfreiem Pyridin gelöst und mit 3 g 3,4,5-Trimethoxybenzoyl-chlorid versetzt. Man läßt bei Zimmertemperatur 4 Tage stehen und gießt dann in Eiswasser. Den so erhaltenen 3,4,5=rrimethoxy-benzoesäure-ester des 17-Methoxy-18-oxy-15,16,17,18,19,20-hexadehydro-y ohimbans kristallisiert man aus verdünntem Alkohol um. Schmp. 150 bis 151'. Beispiel 2 8,6 g 17-Methoxy-18-oxy-15,16,17,18,19,20-hexadehydroyohimban werden in 35 ccm wasserfreiem Pyridin gelöst und mit 9 ccm Propionsäureanhydrid versetzt. Man läßt bei Zimmertemperatur eine Nacht stehen und gießt dann auf viel Eis. Man filtriert den festen Niederschlag und kristallisiert den Propionsäureester aus verdünntem Äthylalkohol um. Schmelzpunkt 185 bis 186`. Example 1 2 g of 17-methoxy-18-oxy-15,16,17,18,19,20-hexadehydroyohimbane chlorohydrate (prepared according to H ah n and H an se 1, Ber. Dtsch. Ges., 71, p. 2195 [ 1938]) are dissolved in anhydrous pyridine and treated with 3 g of 3,4,5-trimethoxybenzoyl chloride. It is left to stand at room temperature for 4 days and then poured into ice water. The 3,4,5 = rrimethoxy-benzoic acid ester of 17-methoxy-18-oxy-15,16,17,18,19,20-hexadehydro-y ohimbans thus obtained is recrystallized from dilute alcohol. M.p. 150 to 151 '. Example 2 8.6 g of 17-methoxy-18-oxy-15,16,17,18,19,20-hexadehydroyohimbane are dissolved in 35 cc of anhydrous pyridine and 9 cc of propionic anhydride are added. It is left to stand at room temperature for one night and then poured onto a lot of ice. The solid precipitate is filtered off and the propionic acid ester is recrystallized from dilute ethyl alcohol. Melting point 185 to 186 '.
Claims (2)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
IT1023768X | 1954-11-03 |
Publications (1)
Publication Number | Publication Date |
---|---|
DE1023768B true DE1023768B (en) | 1958-02-06 |
Family
ID=11429328
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DEE11500A Pending DE1023768B (en) | 1954-11-03 | 1955-11-03 | Process for the preparation of compounds of the carboline series |
Country Status (1)
Country | Link |
---|---|
DE (1) | DE1023768B (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3096245A (en) * | 1959-10-29 | 1963-07-02 | Warner Lambert Pharmaceutical | 16alpha-methylyohimbone, process therefor and therapeutic compositions thereof |
-
1955
- 1955-11-03 DE DEE11500A patent/DE1023768B/en active Pending
Non-Patent Citations (1)
Title |
---|
None * |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3096245A (en) * | 1959-10-29 | 1963-07-02 | Warner Lambert Pharmaceutical | 16alpha-methylyohimbone, process therefor and therapeutic compositions thereof |
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