GB726987A - Carboxylic acid derivatives - Google Patents

Carboxylic acid derivatives

Info

Publication number
GB726987A
GB726987A GB6850/53A GB685053A GB726987A GB 726987 A GB726987 A GB 726987A GB 6850/53 A GB6850/53 A GB 6850/53A GB 685053 A GB685053 A GB 685053A GB 726987 A GB726987 A GB 726987A
Authority
GB
United Kingdom
Prior art keywords
acid
hydroxyphenyl
propionic acid
ethyl
methyl
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
GB6850/53A
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.)
STWB Inc
Original Assignee
Sterling Drug Inc
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 Sterling Drug Inc filed Critical Sterling Drug Inc
Publication of GB726987A publication Critical patent/GB726987A/en
Expired legal-status Critical Current

Links

Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K49/00—Preparations for testing in vivo
    • A61K49/04—X-ray contrast preparations
    • A61K49/0433—X-ray contrast preparations containing an organic halogenated X-ray contrast-enhancing agent

Abstract

The invention comprises compounds of the formula <FORM:0726987/IV (b)/1> wherein R is hydrogen or a lower alkyl group having 1 or 2 carbon atoms, and non-toxic salts of such a compound. Such compounds are obtained by heating a compound having the formula <FORM:0726987/IV (b)/2> in acid solution with an excess of iodine monochloride. Salts mentioned are those of inorganic bases such as sodium, potassium or ammonium hydroxide and organic bases such as methylamine, ethylamine, and mono-, di-, and triethanolamines. Such bases neutralize the carboxylic group, and the strong inorganic bases, in sufficient quantity, also neutralize the phenolic group, giving a di-salt. The iodination may be effected in dilute acid medium, e.g. hydrochloric or acetic acid. The m-hydroxyphenylalkanoic acid can be prepared by condensing m-hydroxybenzaldehyde, an acid anhydride (RCH2CO)2O and a salt of the acid RCH2COOH to produce a substituted cinnamic acid, m-HOC6H4CH=C(R)COOH followed by reduction of the double bond catalytically or with sodium amalgam. The products are used as cholecystographic agents. In examples: (1) m-hydroxybenzaldehyde, sodium acetate and acetic anhydride are reacted to give m-hydroxycinnamic acid which is reduced with sodium amalgam to b -(m-hydroxyphenyl)-propionic acid and the latter on iodination is converted to b - (2,4,6 - triiodo - 3 - hydroxyphenyl)-propionic acid. Similarly prepared are (2) a -methyl - b - (2,4,6-triiodo - 3 - hydroxyphenyl)-propionic acid (a - methyl - m - hydroxycinnamic acid and a -methyl-b -(m-hydroxyphenyl)-propionic acid being intermediates), and (3) a -ethyl-b -(2,4,6-triido-3-hydroxyphenyl) propionic acid (a -ethyl-m-hydroxycinnamic acid and a - ethyl - a - (m - hydroxyphenyl) - propionic acid being intermediates).
GB6850/53A 1952-03-20 1953-03-12 Carboxylic acid derivatives Expired GB726987A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US726987XA 1952-03-20 1952-03-20

Publications (1)

Publication Number Publication Date
GB726987A true GB726987A (en) 1955-03-23

Family

ID=22109226

Family Applications (1)

Application Number Title Priority Date Filing Date
GB6850/53A Expired GB726987A (en) 1952-03-20 1953-03-12 Carboxylic acid derivatives

Country Status (1)

Country Link
GB (1) GB726987A (en)

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