Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Patent
1993-07-22
1996-01-02
Gupta, Yogendra N.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
514386, 514399, 544322, 544332, 5483181, 5483185, 5483315, 5483415, A61K 31505, A61K 31415, C07D23942, C07D23388
Patent
active
054808847
DESCRIPTION:
BRIEF SUMMARY
The present invention relates to new compounds of guanidine structure which promote the growth, repair and regeneration of the neuronal axon and capable of improving the condition of patients suffering from neuropathies and myopathies. More generally, these compounds may be useful in the domain of degenerative diseases of the nervous system.
Its subject is also preparation processes which make it possible to obtain the said compounds and the pharmaceutical compositions containing these compounds.
To the knowledge of the Applicant, no compounds are available in human therapy which act on the regeneration of the peripheral nerve and which are capable of having a beneficial effect on neuromuscular disorders.
A compound, isaxonine or 2-(isopropylamine)pyrimidine, having very advantageous pharmacological properties, has indeed already been described in "La Nouvelle Presse Medicale", Masson, 1982, 16 (11), 1193-1280: however, marketed under the name of Nerfactor, it had to be withdrawn from the market on the grounds of hepatotoxicity.
Moreover, in the journal "Therapie" (1968, XXIII, pp. 1221-1232), veratrylguanidine and the hemisulfate of this compound have been described as antihypertensives.
However, the properties of these compounds in neurotherapy have, to the knowledge of the Applicant, never been described.
The subject of the invention is therefore to provide new compounds (leaving aside veratrylguanidine and its hemisulfate salt), useful in the domain of neuronal regeneration, which are therefore intended to have beneficial effects in diseases relating thereto such as myopathy.
According to the invention, the compounds correspond to the formula: ##STR2## in which: R.sub.1 is an isopropyl radical, a benzyl radical which is optionally substituted by one or more (C.sub.1 -C.sub.4)alkoxy radicals or a radical: ##STR3## R.sub.2, R.sub.3 and R.sub.4 together with the nitrogen atoms to which they are attached and the carbon atom to which the said nitrogen atoms are attached form a pyrimidine ring of formula II or a pyrimidinium ring of formula IIa: ##STR4## in which: n=0, 1, 2, radical, a phenyl radical or a hydrogen atom, radical and in general COOR.sub.8 may be an amine-protecting group, amino radical which they are attached and the carbon atom to which the said nitrogen atoms are attached an imidazole ring of formula: ##STR5## or 1,6-dihydropyrimidine of formula: ##STR6## R.sub.6 having one of the meanings of R.sub.5, or R.sub.2, R.sub.3 together form with the nitrogen atoms to which they are attached and the carbon atom to which the said nitrogen atoms are attached a ring of formula: ##STR7## R.sub.7 being a (C.sub.1 -C.sub.4)alkoxy radical or a 1-glyceryl radical with in this latter case R.sub.1 which may correspond to a hydrogen atom, exception of veratrylguanidine and the hemisulfate thereof.
The invention also relates to the pharmacologically acceptable salts of these compounds, especially the lactate, fumarate, hydrochloride, maleate, malate, ketoglutarate, glutarate, phenoxyacetate, sulfonate, picrate, tartrate and methanesulfonate.
According to a preferred variant of the invention, R.sub.1 is an isopropyl radical or a di- or trimethoxybenzyl radical or the radical: ##STR8##
According to a second preferred variant of the invention, taken or otherwise in combination with the one above, R.sub.4 is a methyl, ethyl, n-propyl or benzyl radical.
According to a third preferred variant, the invention relates to the lactate, fumarate, hydrochloride, maleate, malate, ketoglutarate, glutarate, phenoxyacetate, sulfonate, picrate, tartrate, methanesulfonate of veratrylguanidine.
The invention also relates to the medicinal products consisting of one of the compounds according to the invention, as has just been described above, and the pharmaceutical compositions containing at least one of these medicinal products and an acceptable carrier. These medicinal products and compositions are useful in the medical treatment in man or animals of certain disorders linked to the functioning of the nervous system.
The medicina
REFERENCES:
patent: 2145011 (1939-01-01), Albertlandolt et al.
Christopher et al. J. Am. Chem. Soc. 90(1), 113-120, 1968.
Vincent et al. J. Org. Chem. 28, 123-129, 1963.
E. Boschetti et al., "Synthesis and Pharmacologic Classification of New Hypotensive Agents", Chemical Abstracts, vol. 70, 1969.
C. M. Gupta, "Novel Glass of Hypoglecemic Agents", Chemical Abstracts, vol. 75, p. 450, col. 1, 1971.
Y.-K. Kim et al., "Synthesis and Curing Study of 5-5 Ring Fused Polyimide Based on Imidazole", Macromolecules, vol. 24, No. 23, pp. 6357-6360, 1991.
Koenig Herbert
Koenig Janine
Portier Marie-Madeleine
Potier Pierre
Quirosa-Guillou Catherine
Centre National de la Recherche Scientifique
Gupta Yogendra N.
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