GB889774A - Improvements in or relating to yohimbane derivatives - Google Patents

Improvements in or relating to yohimbane derivatives

Info

Publication number
GB889774A
GB889774A GB32451/58A GB3245158A GB889774A GB 889774 A GB889774 A GB 889774A GB 32451/58 A GB32451/58 A GB 32451/58A GB 3245158 A GB3245158 A GB 3245158A GB 889774 A GB889774 A GB 889774A
Authority
GB
United Kingdom
Prior art keywords
methoxy
benzo
methoxycarbonyl
acetoxy
yohimbane
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.)
Expired
Application number
GB32451/58A
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.)
Laboratoires Francais de Chimiotherapie SA
Original Assignee
Laboratoires Francais de Chimiotherapie SA
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 Laboratoires Francais de Chimiotherapie SA filed Critical Laboratoires Francais de Chimiotherapie SA
Publication of GB889774A publication Critical patent/GB889774A/en
Expired legal-status Critical Current

Links

Landscapes

  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)

Abstract

The invention comprises 9; 10-benzodeserpidine of the formula p <FORM:0889774/IV (b)/1> dextro - rotary 18b - acetoxy - 9, 10 - benzo - 17a - methoxy - 16b - methoxycarbonyl - D 3(14) - 20a - yohimbene, laevo - rotatory 18b - acetoxy - 9,10-benzo-17a - methoxy - 16b -methoxycarbonyl - 3b , 20a -yohimbane, its 3a -epimer and its 18b -hydroxy analogue, together with a process for their preparation by reacting the methyl ester of 1b - carboxymethyl - 2b - methoxycarbonyl - 3a - methoxy-4b -acetoxy-6b -formyl cyclohexane with 4,5-benzotryptamine in an inert solvent, reducing the resultant methyl ester of 18b -acetoxy-9,10-benzo - 17a - methoxy - 16b - methoxycarbonyl - 2 : 3,3 : 4-diseco-D 4(21)-20a -yohimbene-3-oic acid with a metal borohydride to yield dextro-rotary 9, 10 - benzo - 18b - hydroxy - 17a - methoxy - 16b - methoxycarbonyl - 3 - oxo - 2 : 3 - seco - 20a -yohimbane which is acetylated to the laevorotatory 18b -acetoxy derivative, cyclizing the latter by dehydration (e.g. with phosphorus oxychloride) to give dextro-rotary 18b -acetoxy-9, 10 - benzo - 17a - methoxy - 16b - methoxy - carbonyl-D 3(14)-20a -yohimbene (I), reducing the last mentioned compound with a metal/acid reducing system, preferably with zinc and formic acid, to laevo-rotary 18b -acetoxy-9,10-benzo-17a - methoxy - 16b - methoxycarbonyl - 3b , 20a - yohimbane, partially saponifying and then trimethoxybenzoylating the resulting laevo-rotatory 9, 10 - benzo - 18b - hydroxy - 17a - methoxy - 16b - methoxycarbonyl - 3b , 20a - yohimbane to give laevo-rotatory 9,10-benzo deserpidine. Reduction of I with sodium borohydride yields the epimeric 3a ,20a -yohimbane. Detailed examples are given. Specifications 862,611, 868,475 and 888,411 are referred to.
GB32451/58A 1957-10-15 1958-10-10 Improvements in or relating to yohimbane derivatives Expired GB889774A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR889774X 1957-10-15

Publications (1)

Publication Number Publication Date
GB889774A true GB889774A (en) 1962-02-21

Family

ID=9377286

Family Applications (1)

Application Number Title Priority Date Filing Date
GB32451/58A Expired GB889774A (en) 1957-10-15 1958-10-10 Improvements in or relating to yohimbane derivatives

Country Status (1)

Country Link
GB (1) GB889774A (en)

Similar Documents

Publication Publication Date Title
GB889774A (en) Improvements in or relating to yohimbane derivatives
US3113134A (en) Process for the production of reserpic acid diesters
NL7603461A (en) D-HOMOSTEROIDS AND METHOD FOR PREPARING THEM.
US3107250A (en) Process for the preparation of 6-aminopenicillanic acid and novel intermediates useful therein
FR1140070A (en) Process for the production of aryl fatty acid hydroxy derivatives
GB907802A (en) Improvements in or relating to yohimbane derivatives
UA6043A1 (en) Method for producing chloroambucyl derivatives (variants)
GB777754A (en) A method of preparing a new hydroxycoumarin derivative with anticoagulating properties
Weiss New Compounds. α-Auromercapto-acetanilide
GB844830A (en) Method for preparing succinaldehyde bisulphite compounds
GB748846A (en) A process for the manufacture of pregnan-3(-a)-ol-20-one and derivatives thereof
GB882844A (en) Glucuronic acid derivatives useful as intermediates in the production of antibacterials, and the production of said derivatives
GB868478A (en) Synthesis of deserpidine
GB837841A (en) Reserpic acid diesters and salts thereof and process for their manufacture
Burger et al. New Compounds. Di-(β-phenoxyehtyl) Oxalate
ES282859A1 (en) A procedure for the preparation of derivatives of 6-methyl and 1,6-dimethyl-ergoline ii (Machine-translation by Google Translate, not legally binding)
GB999091A (en) Benzo(a)quinolizine derivatives and method for making them
GB981460A (en) Hydrazine derivatives and process for making them
GB868476A (en) Improvements in or relating to reserpine derivatives
GB1024650A (en) Benzofuran derivatives and process for their production
GB788895A (en) New derivatives of androstadiene and their production
ES8303315A1 (en) 4-Methylmercapto-2-acetoxy-butyraldehyde
BE583595A (en) Process for the preparation of basic derivatives formed by esters of benzilic acid.
CA533483A (en) Process of preparing alkyl esters of 7:8-diamino nonoic acid
GB837949A (en) Reserpic acid diesters and salts thereof and process for their manufacture