GB988001A - Improvements in or relating to lysergic acid derivatives - Google Patents

Improvements in or relating to lysergic acid derivatives

Info

Publication number
GB988001A
GB988001A GB2878561A GB2878561A GB988001A GB 988001 A GB988001 A GB 988001A GB 2878561 A GB2878561 A GB 2878561A GB 2878561 A GB2878561 A GB 2878561A GB 988001 A GB988001 A GB 988001A
Authority
GB
United Kingdom
Prior art keywords
acid
lysergic
alkali metal
amide
dissolving
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
GB2878561A
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.)
Sandoz Patent Ltd
Sandoz AG
Original Assignee
Sandoz Patent Ltd
Sandoz 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
Priority claimed from CH939760A external-priority patent/CH386440A/en
Priority claimed from CH96761A external-priority patent/CH390930A/en
Application filed by Sandoz Patent Ltd, Sandoz AG filed Critical Sandoz Patent Ltd
Publication of GB988001A publication Critical patent/GB988001A/en
Expired legal-status Critical Current

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  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Peptides Or Proteins (AREA)
  • Medicines Containing Plant Substances (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

The invention comprises compounds of the formula <FORM:0988001/C2/1> (wherein R1 is C1- 4 alkyl, C7- 10 monocyclic aralkyl or C2- 4 alkenyl and <FORM:0988001/C2/2> and their acid-addition salts; and their preparation (1) by hydrolysing a corresponding amide (wherein the nitrogen atom may be substituted by C1- 4 alkyl or hydroxyalkyl radicals or wherein the substituted amino portion of the amide radical is the tripeptide radical of a natural water insoluble ergot alkaloid) with an alkali metal hydroxide; or (2) by treating a corresponding N-unsubstituted compound, i.e. a lysergic or dihydrolysergic acid, with an alkali metal amide in liquid ammonia and reacting the resulting alkali metal salt with the appropriate halide R1-Hal. In process (1), when 9,10-dehydro-compounds are saponified the product is a mixture of lysergic and isolysergic acid derivatives and these are separated by dissolving in a suitable acid and precipitating with a base, by dissolving in a base and fractionally precipitating with an acid or by means of a combination of the two operations, or by fractional recrystallization, or by absorption analysis. In process (2), pure 1-methyl-D-lysergic acid may be isolated by bringing an aqueous solution to pH 4.5 to 5 with acetic acid, or by evaporating the solution to dryness, and pouring methanol over the residue to dissolve small quantities of 1-methyl-isolysergic acid and inorganic salts.
GB2878561A 1960-08-19 1961-08-09 Improvements in or relating to lysergic acid derivatives Expired GB988001A (en)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
CH939760A CH386440A (en) 1960-08-19 1960-08-19 Process for the production of new lysergic acids
CH1197460 1960-10-26
CH96761A CH390930A (en) 1961-01-27 1961-01-27 Process for the preparation of heterocyclic compounds
CH189161 1961-02-16

Publications (1)

Publication Number Publication Date
GB988001A true GB988001A (en) 1965-03-31

Family

ID=27428042

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2878561A Expired GB988001A (en) 1960-08-19 1961-08-09 Improvements in or relating to lysergic acid derivatives

Country Status (3)

Country Link
DE (1) DE1161566B (en)
ES (1) ES269962A1 (en)
GB (1) GB988001A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2005082902A1 (en) * 2004-02-20 2005-09-09 Ivax Pharmaceuticals S.R.O. Process for the manufacture of lysergic acid

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2005082902A1 (en) * 2004-02-20 2005-09-09 Ivax Pharmaceuticals S.R.O. Process for the manufacture of lysergic acid

Also Published As

Publication number Publication date
ES269962A1 (en) 1962-04-16
DE1161566B (en) 1964-01-23

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