GB736804A - Manufacture of mercury compounds of para-amino salicylic acid derivatives - Google Patents

Manufacture of mercury compounds of para-amino salicylic acid derivatives

Info

Publication number
GB736804A
GB736804A GB23380/52A GB2338052A GB736804A GB 736804 A GB736804 A GB 736804A GB 23380/52 A GB23380/52 A GB 23380/52A GB 2338052 A GB2338052 A GB 2338052A GB 736804 A GB736804 A GB 736804A
Authority
GB
United Kingdom
Prior art keywords
acetylamino
mercuri
carbamido
hydroxy
acid
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
GB23380/52A
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.)
Hoechst AG
Original Assignee
Hoechst AG
Farbwerke Hoechst 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 Hoechst AG, Farbwerke Hoechst AG filed Critical Hoechst AG
Publication of GB736804A publication Critical patent/GB736804A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/12—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by halogen atoms or by nitro or nitroso groups

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The invention comprises organo-mercury compounds of the general formula <FORM:0736804/IV (b)/1> wherein R represents hydrogen or an alkyl or hydroxyalkyl radical containing up to 6 carbon atoms, R1 represents an aliphatic acyl radical containing up to 6 carbon atoms and n is 1, 2 or 3, and a process for the preparation thereof wherein a p-amino-salicylic acid ester, acylated in the amino group by an aliphatic carboxylic acid containing up to 6 carbon atoms, is heated with allylamine, the allylamide thus obtained is condensed in an alkaline medium with an aliphatic halocarboxylic acid containing up to 6 carbon atoms and the condensation product is reacted with a mercuric salt of an organic carboxylic acid in the presence of water or an aliphatic mono- or poly-hydric alcohol containing up to 6 carbon atoms. The acyl radical attached to the nitrogen atom in the organomercury compound may be an acetyl, propionyl or butyryl radical. The ester radical in the salicylic acid ester reactant may be derived from an aliphatic or aromatic alcohol or a phenol-particularly from a lower aliphatic alcohol such as methanol, ethanol, propanol, isopropanol or butanol or amyl alcohol. Suitable aliphatic halocarboxylic acids are chloracetic, bromacetic, iodoacetic, chloropropionic, bromopropionic, iodopropionic, chlorobutyric, bromobutyric and iodobutyric acids. Suitable mono- and polyhydric alcohols are methanol, ethanol, propanol, isopropanol, butanol, amyl alcohol, ethylene glycol, 1,3-propylene glycol, 1,2-propylene glycol, 1,4-butanediol and glycerol. The alkali metal salts of the organo-mercury compounds are also referred to. In the examples the following compounds are prepared using 4-acetylamino - 1 - (N - allylcarbamido) - phenoxyacetic acid-2 for the reaction with the mercuric salt of a carboxylic acid and which has been obtained by heating 4 - acetylamino - 2 - hydroxybenzoic acid methyl ester with allylamine and reacting the resulting 4-acetylamino-2-hydroxybenzallylamide with chloracetic acid in the presence of sodium hydroxide; 4-acetylamino-1 - [N - (31 - hydroxy - mercuri - 21 - methoxypropyl - 11) - carbamido] - 2 - phenoxyacetic acid and the sodium salt thereof, 4-acetylamino-1 - [N - (31 - hydroxy - mercuri - 21 - hydroxypropyl - 11) - carbamido] - 2 - phenoxyacetic acid and the sodium salt thereof, 4-acetylamino-1 - [N - (31 - hydroxy - mercuri - 21 - b - hydroxyethoxy - propyl - 11) - carbamido] - 2 - phenoxyacetic acid and the sodium salt thereof, and 4-acetylamino - 1 - [N - (31 - hydroxy - mercuri - 21-b - hydroxypropoxy - propyl - 11) - carbamido]-2-phenoxyacetic acid and the sodium salt thereof.ALSO:Medicines containing organo-mercury compounds are obtained by dissolving in water an alkali metal salt of a compound of the general formula <FORM:0736804/VI/1> wherein R represents hydrogen or an alkyl or hydroxyalkyl radical containing up to 6 carbon atoms, R1 represents an aliphatic acyl radical containing up to 6 carbon atoms and n is 1, 2 or 3, and adding theophylline. In the examples compositions are prepared by forming aqueous solutions of each of the alkali metal salts of 4-acetylamino - 1 - [N - (31 - hydroxy - mercuri - 21 - methoxypropyl - 1) - carbamido] - 2 - phenoxyacetic acid, 4 - acetylamino - 1 - [N - (31-hydroxy - mercuri - 21 - hydroxypropyl - 11)-carbamido] - 2 - phenoxyacetic acid, 4 - acetylamino - 1 - [N - (31 - hydroxy - mercuri - 21 - b -hydroxyethoxy - propyl - 11) - carbamido] - 2-phenoxyacetic and 4 - acetylamino - 1 - [N - b 1-hydroxy - mercuri - 21 - b - hydroxypropoxypropyl - 11) - carbamido] - 2 - phenoxyacetic acid, and then adding theophylline.
GB23380/52A 1951-09-26 1952-09-17 Manufacture of mercury compounds of para-amino salicylic acid derivatives Expired GB736804A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE736804X 1951-09-26

Publications (1)

Publication Number Publication Date
GB736804A true GB736804A (en) 1955-09-14

Family

ID=6642409

Family Applications (1)

Application Number Title Priority Date Filing Date
GB23380/52A Expired GB736804A (en) 1951-09-26 1952-09-17 Manufacture of mercury compounds of para-amino salicylic acid derivatives

Country Status (1)

Country Link
GB (1) GB736804A (en)

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