Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Nitrogen containing other than solely as a nitrogen in an...
Patent
1993-01-14
1995-03-21
Raymond, Richard L.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Nitrogen containing other than solely as a nitrogen in an...
514478, 514512, 514534, 514546, 514557, 514626, 558276, 560110, 560168, 560250, 562574, 564197, 564291, 564292, A61K 3114, C07C21163
Patent
active
053995902
DESCRIPTION:
BRIEF SUMMARY
The present invention relates to the field of organic chemistry and more particularly to that of therapeutic chemistry.
A more particular subject of the invention is new compounds of quaternary ammonium type having at least one halogenoalkyl radical with a nitrogen.
Specifically a subject of the invention is new quaternary ammonium salts corresponding to general formula (I): ##STR2## in which Hal is a halogen atom other than fluorine R and R.sub.1, identical or different, are linear or branched chain lower alkyl radicals, n is an integer varying from 2 to 16, Z is an alkenyl radical having up to 3 carbon atoms, a carboxyl, or the OR.sub.2 group where R.sub.2 is a hydrogen, an optionally substituted lower alkyl radical, an acyl remainder derived from a saturated carboxylic or carbonic mineral or organic acid having 1 to 20 carbon atoms, a tocol radical, a sterol radical or a carboxamide chain with the following form: ##STR3## in which n.sub.1 is an integer varying from 0 to 4, R.sub.3 and R.sub.4, identical or different, are either one a hydrogen and in this case the other substituent represents the alkylene chain of a heterocycle, optionally interrupted by one or more heteroatoms chosen from the group constituted by an oxygen or sulphur atom or the --NH-- group, or identical or different lower alkyl radicals, or form together the alkylene chain of a nitrogenous heterocycle being able to contain another heteroatom as well as one or more functional groups chosen from the group constituted by a halogen, an oxo group, an amino group or a glucoside radical, and A is a hydroxyl or an anion of a mineral or organic acid with the restriction that the acyl remainder cannot include a 1-hydroxy 1,1-diphenyl acetic acid remainder, that when Hal is an iodine, R.sub.2 is not an acetyl remainder and when Hal is a bromine and R.sub.2 is an acetyl remainder, n is different from 2.
Among these, the following compounds are currently preferred: ##STR4## in which R, R.sub.1 and Hal are as defined previously, n is and integer varying from 2 to 4, A is a hydroxyl or an anion of a mineral or organic acid, R.sub.5 is a hydrogen, an acyl remainder derived from a mineral or organic acid having 1 to 18 carbon atoms or a lower alkyl optionally substituted by a hydroxy, a lower alkoxy, an amino group or an alkyl- or dialkylamino radical, ##STR5## in which the substituents R, R.sub.1, Hal, n and A are as defined previously, R.sub.6 is a hydrogen, a halogen or a lower alkyl radical and R.sub.7 is hydrogen or a sugar molecule, ##STR6## in which the substituents R, R.sub.1, Hal, n, R.sub.7 and A have the meanings given previously, ##STR7## in which R.sub.1, R, Hal and A are as defined previously R.sub.8 is a hydrogen or a sugar molecule, the hydroxyls of which are free, blocked or phosphorylated, i.e. derivatives of guanine (2,9) or adenine (6,9), ##STR8## in which R, R.sub.1, Hal, n, A and R.sub.8 are as defined previously which are derivatives of cordycepin, ##STR9## in which B, C and D are hydrogens, a hydroxyl or methyl radical and E is a farnesyl or phytyl chain and R, R.sub.1 , n, Hal and A retain the previous meanings i.e. ethers of .alpha., .beta., .gamma. or .epsilon. tocopherol, ##STR10## i.e. ethers of sitosterol in which R, R.sub.1, Hal, n and A are as defined previously, ##STR11## in which R, R.sub.1, Hal and A are as defined previously n is an integer comprised between 6 and 16 n' is equal to 0 or 1, ##STR12## in which n" is equal to 1, 2 or 3 and R, R.sub.1, Hal and A are as defined previously.
In the last two groups, there can be more particularly mentioned:
The invention also relates to pharmaceutical compositions containing as active ingredient at least one compound of general formula (I'): ##STR13## in which Hal, R and R.sub.1 are as defined previously Z' is a hydrogen, the OR.sub.2 group as defined previously, an alkenyl radical or a carboxyl group n is an integer varying from 1 to 16 and A is a hydroxyl or an anion of a therapeutically-compatible mineral or organic acid in combination or in a mixture with an excipient o
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