Substituted oxiranecarboxylic acids, their preparation and their

Details Substituted oxiranecarboxylic acids, their preparation and their Substituted oxiranecarboxylic acids, their preparation and their

1982-04-06

1984-02-07

Milestone, Norma S.

Drug, bio-affecting and body treating compositions

Nonspecific immunoeffector, per se ; or nonspecific...

549549, C07D30348

Patent

active

044303394

DESCRIPTION:

BRIEF SUMMARY
The invention relates to epoxycycloalkylalkanecarboxylic acids, processes for their preparation, their use and medicaments containing them.
The compounds according to the invention are used in the pharmaceutical industry as intermediate products and for the preparation of medicaments.
The invention relates to epoxycycloalkylalkanecarboxylic acids of the general formula I ##STR2## wherein R denotes a hydrogen atom or a lower alkyl group, Y denotes an oxygen atom (--O--) or a methylene group (--CH.sub.2 --), m denotes an integer from 0 to 6, n denotes an integer from 0 to 6 and p denotes an integer from 2 to 11 (and m cannot be 0 or 1 if Y represents an oxygen atom, and the sum of the numbers m, n and p is an integer from 6 to 15), and to the salts of the carboxylic acids; or to epoxycycloalkylalkanecarboxylic acids of the general formula (Ia) ##STR3## wherein k is an integer from 1 to 5, inclusive, and p being an integer of from 7 to 16,
Suitable lower alkyl groups are straight-chain or branched alkyl radicals having 1 to 4 carbon atoms: straight-chain alkyl radicals are the methyl, ethyl, n-propyl and n-butyl radicals, of which the methyl radical and the ethyl radical are preferred. Examples of branched alkyl radicals are the isopropyl, isobutyl and sec.-butyl radical, of which the isopropyl radical is preferred.
Suitable salts are salts with inorganic and organic bases. Pharmacologically unacceptable salts are converted by methods which are in themselves known into pharmacologically, that is to say biologically, acceptable salts, which are preferred amongst the salts according to the invention. Cations which are used for the formation of salts are above all the cations of the alkali metals, alkaline earth metals or earth metals; however, the corresponding cations of organic nitrogen bases, such as amines, aminoalkanols, amino-sugars, basic aminoacids and the like, are also used.
Examples which may be mentioned are the salts with lithium, sodium, potassium, magnesium, calcium, aluminium, ethylenediamine, dimethylamine, diethylamine, morpholine, piperidine, piperazine, N-lower alkylpiperazines (for example N-methylpiperazine), methylcyclohexylamine, benzylamine, ethanolamine, diethanolamine, triethanolamine, tris-(hydroxymethyl)-aminomethane, 2-amino-2-methylpropanol, 2-amino-2-methyl-1,3-propanediol, glucamine, N-methylglucamine, glucosamine, N-methylglucosamine, lysine, ornithine, arginine and quinoline.
Epoxycycloalkylalkanecarboxylic acids of the general formula I* ##STR4## wherein R* denotes a hydrogen atom or a lower alkyl group, Y* denotes a methylene group (--CH.sub.2 --), m* denotes an integer from 1 to 6, n* denotes the number 1 and p* denotes an integer from 4 to 7 (and the sum of the numbers m*, n* and p* is an integer from 6 to 11), and also the salts of the carboxylic acids form an embodiment of the invention.
Epoxycycloalkylalkanecarboxylic acids of the general formula I** ##STR5## wherein R** denotes a hydrogen atom or a lower alkyl group, Y** denotes an oxygen atom (--O--), m** denotes an integer from 2 to 6, n** denotes an integer from 0 to 4 and p** denotes an integer from 4 to 7 (and the sum of the numbers m**, n** and p** is an integer from 6 to 11), and also the salts of the carboxylic acids form a further embodiment of the invention.
The following may be mentioned as examples of representatives of the compounds according to the invention: 2-(4-cyclohexylbutyl)-oxirane-2-carboxylic acid ethyl ester, 2-(5-cyclopropylpentyl)-oxirane-2-carboxylic acid methyl ester, 2-(3-cyclooctylpropyl)-oxirane-2-carboxylic acid ethyl ester, 2-(8-cyclopentyloctyl)-oxirane-2-carboxylic acid methyl ester, 2-(2-cycloundecylethyl)-oxirane-2-carboxylic acid n-propyl ester, 2-(3-cyclododecylpropyl)-oxirane-2-carboxylic acid ethyl ester, 2-(6-cyclohexylhexyl)-oxirane-2-carboxylic acid n-butyl ester, 2-(10-cyclopentyldecyl)-oxirane-2-carboxylic acid ethyl ester, 2-(2-cycloheptylethyl)-oxirane-2-carboxylic acid isopropyl ester, 2-(7-cyclobutylheptyl)-oxirane-2-carboxylic acid methyl ester, 2-cyclononylmethyl-oxir

REFERENCES:
patent: 4196300 (1980-04-01), Mohrbacher et al.

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