ES269515A1 - Ethers of methyl 18-epi-reserpate and salts thereof and process for their manufacture - Google Patents

Ethers of methyl 18-epi-reserpate and salts thereof and process for their manufacture

Info

Publication number
ES269515A1
ES269515A1 ES0269515A ES269515A ES269515A1 ES 269515 A1 ES269515 A1 ES 269515A1 ES 0269515 A ES0269515 A ES 0269515A ES 269515 A ES269515 A ES 269515A ES 269515 A1 ES269515 A1 ES 269515A1
Authority
ES
Spain
Prior art keywords
methyl
salts
sulphonic acid
epi
reserpate
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
ES0269515A
Other languages
Spanish (es)
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.)
Novartis AG
Original Assignee
Ciba Geigy AG
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 Ciba Geigy AG filed Critical Ciba Geigy AG
Publication of ES269515A1 publication Critical patent/ES269515A1/en
Expired legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C303/00Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
    • C07C303/26Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of esters of sulfonic acids
    • C07C303/28Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of esters of sulfonic acids by reaction of hydroxy compounds with sulfonic acids or derivatives thereof

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Indole Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The invention comprises compounds of general formula <FORM:0999391/C2/1> in which R1 and R2 are alkyl (1-5 C), and X is hydroxy, chlorine, bromine, iodine or OR2 and their preparation by reacting a compound BrCR1(COOR2)2 with an alkali metal benzylate to form the diesters I (X = OR2), which are saponified with an alcoholic solution of an alkali metal hydroxide to the ester-acids I (X = ON), from which the halides are obtainable by known methods.ALSO:The invention comprises methyl 18-epi-OR-reserpates, in which R is methyl, ethyl, n-propyl or isopropyl, and their acid addition salts and the preparation of these compounds by subjecting a methyl reserpate, esterified in the 18 position with an organic sulphonic acid, to alcoholysis with an alcohol ROH and, if desired, converting the resulting bases into salts or the resulting salts into bases. A tertiary amine catalyst is usually used for the alcoholysis reaction. The organic radical of the sulphonic acid ester starting material may be lower alkyl, unsubstituted phenyl or a phenyl radical substituted with, for example, halogen atoms or nitro, carboxyl, carbalkoxy, carbamyl, cyano or methyl groups these sulphonic acid esters are prepared by reacting a methyl reserpate with the appropriate sulphonic acid halide in the presence of a base such as pyridine or collidine. Pharmaceutical preparations comprise the methyl 18-epi-OR-reserpates and their salts, which are sedatives, tranquillizers, antifibrillatory agents and local anaesthetics, together with a pharmaceutically suitable carrier. They may be in forms suitable for enteral or parenteral administration, e.g. tablets, dragees, capsules, solutions, suspensions or emulsions. Veterinary preparations, e.g. in the form of animal feedstuffs, are also mentioned. Salts specified include those with ascorbic, salicylic and p-aminosalicylic acids, methionine, tryptophan, lysine and arginine. Specifications 999,394 and 999,397 are referred to.
ES0269515A 1960-08-02 1961-08-02 Ethers of methyl 18-epi-reserpate and salts thereof and process for their manufacture Expired ES269515A1 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US4691160A 1960-08-02 1960-08-02
US7349060A 1960-12-05 1960-12-05
US11032061A 1961-05-16 1961-05-16

Publications (1)

Publication Number Publication Date
ES269515A1 true ES269515A1 (en) 1962-04-16

Family

ID=27367016

Family Applications (3)

Application Number Title Priority Date Filing Date
ES0269516A Expired ES269516A1 (en) 1960-08-02 1961-08-02 Ethers of methyl 18-epi-reserpate and salts thereof and process for their manufacture
ES0269515A Expired ES269515A1 (en) 1960-08-02 1961-08-02 Ethers of methyl 18-epi-reserpate and salts thereof and process for their manufacture
ES0269514A Expired ES269514A1 (en) 1960-08-02 1961-08-02 Ethers of methyl 18-epi-reserpate and salts thereof and process for their manufacture

Family Applications Before (1)

Application Number Title Priority Date Filing Date
ES0269516A Expired ES269516A1 (en) 1960-08-02 1961-08-02 Ethers of methyl 18-epi-reserpate and salts thereof and process for their manufacture

Family Applications After (1)

Application Number Title Priority Date Filing Date
ES0269514A Expired ES269514A1 (en) 1960-08-02 1961-08-02 Ethers of methyl 18-epi-reserpate and salts thereof and process for their manufacture

Country Status (6)

Country Link
AT (7) AT252461B (en)
CH (8) CH407146A (en)
ES (3) ES269516A1 (en)
GB (6) GB999391A (en)
NL (1) NL139529B (en)
SE (7) SE301478B (en)

Also Published As

Publication number Publication date
GB999392A (en) 1965-07-28
CH410969A (en) 1966-04-15
NL139529B (en) 1973-08-15
CH407145A (en) 1966-02-15
GB999391A (en) 1965-07-28
SE301486B (en) 1968-06-10
ES269514A1 (en) 1962-04-16
AT252462B (en) 1967-02-27
AT249274B (en) 1966-09-12
SE301484B (en) 1968-06-10
CH407146A (en) 1966-02-15
GB999397A (en) 1965-07-28
AT252463B (en) 1967-02-27
SE301321B (en) 1968-06-04
SE301485B (en) 1968-06-10
SE301478B (en) 1968-06-10
AT252461B (en) 1967-02-27
ES269516A1 (en) 1962-04-16
GB999398A (en) 1965-07-28
CH398627A (en) 1966-03-15
SE301650B (en) 1968-06-17
GB999399A (en) 1965-07-28
CH398628A (en) 1966-03-15
CH407144A (en) 1966-02-15
SE301487B (en) 1968-06-10
AT252459B (en) 1967-02-27
CH407143A (en) 1966-02-15
CH416658A (en) 1966-07-15
GB999393A (en) 1965-07-28
AT249273B (en) 1966-09-12
AT252460B (en) 1967-02-27

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