DE1023768B - Process for the preparation of compounds of the carboline series - Google Patents

Process for the preparation of compounds of the carboline series

Info

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
Application number
DEE11500A
Other languages
German (de)
Inventor
Dr Willy Logemann
Dr Luigi Almirante
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Pfizer Italia SRL
Original Assignee
Carlo Erba SpA
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Carlo Erba SpA filed Critical Carlo Erba SpA
Publication of DE1023768B publication Critical patent/DE1023768B/en
Pending legal-status Critical Current

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  • 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)

PATENTANSPRÜCHE: 1. Verfahren zur Herstellung von Verbindungen der Carbolinreihe, dadurch gekennzeichnet, daB man Verbindungen der Formel in welcher R' Wasserstoff oder 0-Alkyl-Gruppen bedeutet, mit organischen Säuren verestert. PATENT CLAIMS: 1. Process for the preparation of compounds of the carboline series, characterized in that compounds of the formula in which R 'denotes hydrogen or 0-alkyl groups, esterified with organic acids. 2. Verfahren nach Anspruch 1, dadurch gekennzeichnet, daß man 17-Methoxy-18-oxy-15,16,17, 18,19,20-hexadehydro-yohimban mit Propionsäureanhydrid umsetzt. In Betracht gezogene Druckschriften Berichte der deutschen chem. Ges., 71, S. 2192ff. (1938).2. The method according to claim 1, characterized in that 17-methoxy-18-oxy-15,16,17, 18,19,20-hexadehydro-yohimbane reacts with propionic anhydride. Considered Publications reports of the German chem. Ges., 71, pp. 2192ff. (1938).
DEE11500A 1954-11-03 1955-11-03 Process for the preparation of compounds of the carboline series Pending DE1023768B (en)

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)

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DE (1) DE1023768B (en)

Cited By (1)

* Cited by examiner, † Cited by third party
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

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
None *

Cited By (1)

* Cited by examiner, † Cited by third party
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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