Derivatives of lysine and aspartic acid

BACKGROUND OF INVENTION

There has for a long time been a need for a means of counteracting the effects of muscular fatigue and of temporary and involuntary muscular contractions, particularly in connection with sporting activities, wherein such physiological phenomena result from prolonged efforts.

OBJECT OF THE INVENTION

It is an object of the invention to satisfy the aforesaid need.

SUMMARY OF THE INVENTION

We have found that certain derivatives of lysine and aspartic acid have biological properties which counteract the effects of muscular fatigue and of temporary and involuntary muscular contractions. These derivatives, which form our invention, have the formula ##STR2## in which R represents a hydrogen atom and n is 1 or R represents a acyl group having from 6 to 26 carbon atoms and n is 2.

Lysine aspartate (R=H, n=1) may be prepared by the simple reaction of lysine with aspartic acid in an aqueous solution to a pH value of approximately 7. The lysine acyl aspartates (R=acyl, n=2) may be prepared by the total salination of the active amine function of lysine by a lipoamino acid, namely aspartic acid the amine function of which has been acylated by a compound containing an acyl group having from 6 to 26 carbon atoms.

In the lysine acyl aspartates, the acyl group may be saturated or unsaturated and may have a straight or branched chain. The acyl group is preferably selected from the group consisting of caproyl, capryl, lauryl, palmityl, undecenyl, oleyl and linoleyl groups.

The compounds of the invention are useful as the active ingredient of pharmaceutical compositions for topical application to men and animals and in methods of treating muscular fatigue and muscular contraction in men and animals by topical application. The compositions preferably contain from 0.5 to 10% by weight of the active ingredient.

We have further and surprisingly found that the compounds of the invention are of horitcultural use in stimulating the development of vegetation, particularly in the germination of seeds and in the treatment of leaves, the latter evidenced by a change in the intensity of the green colouration of the leaves upon such treatment. Our invention therefore emcompasses the new compounds, pharmaceutical and horticultural compositions containing them, and methods of treating men and animals against muscular fatigue and muscular contraction and of treating vegetation to stimulate its development.

DETAILED DESCRIPTION OF THE INVENTION

TABLE 1 ______________________________________ Type of Molecular Acid Theoretical Actual Derivative weight index Nitrogen Nitrogen ______________________________________ Lysine 279 0 15% 14.7% aspartate Lysine 551 0 12.7% 12.4% capryl aspartate Lysine 663 0 10.5% 10.1% Palmitic aspartate Lysine 607 0 11.5% 11.3% Lauric aspartate ______________________________________

Table 2 shows the results obtained in the treatment of muscular fatigue and the muscular decontraction effects obtained using lysine aspartate. Comparison is made with other aspartates.

TABLE 2 ______________________________________ Physiological Lysine Arginine Ornithine Guanidine Reaction aspartate aspartate aspartate aspartate ______________________________________ Relaxing very slight slight none effect marked Muscular very none none none decontraction marked effect, involuntary very rapid or after effort ______________________________________

As can be seen, the effectiveness is due to the association of the aspartic acid with the lysine. The aspartates of the two other basic amino acids, arginine and ornithine, and of quanidine have little or no effect. Table 3 shows the results obtained with various lysine acyl aspartates.

TABLE 3 ______________________________________ Effects Nature of the acyl chain obtained Acetyl Butyl Capryl Lauryl Palmityl ______________________________________ Relaxation of None none very very very lower limbs marked marked marked Effect on None none rapid rapid rapid muscular decontraction ______________________________________

It can be seen that lysine lower acyl aspartates are ineffective, whereas the lysine higher acyl aspartates according to the invention are notably effective.

The following formulations are examples of suitable pharmaceutical compositions according to the invention.

______________________________________ 1. Stearic acid 5 Cetyl polyoxyethylene alcohol 10 Isopropyl palmitate 10 Glycerol 10 Lysine aspartate 1 to 10 Water to make up to 100 2. Glycerol stearate 5 Beeswax 10 Vaseline oil 10 Sorbitol polyoxyethylene oleate 5 Glycerol 10 Lysine capryl aspartate 1 to 10 Water to make up to 100 3. Stearic acid 5 Cetyl polyethylene alcohol 10 Ethyl stearate 10 Glycerol 10 Lysine palmityl aspartate 1 to 10 Water to make up to 100 ______________________________________

The following formulations are examples of suitable horticultural compositions according to the invention.

______________________________________ (a) for the treatment of leaves 1 Lysine aspartate 1 to 5 Water to make up to 100 2. Lysine capryl aspartate 1 to 5 Water to make up to 100 3. Lysine lauryl aspartate 1 to 5 Water to make up to 100 4. Unidecenyl aspartate 1 to 5 Water to make up to 100 (b) for the treatment of seeds 1. Lysine aspartate 0.5 to 10 Bentonite (Fullers earth) to make up to 100 2. Lysine capryl aspartate 0.5 to 10 Sodium lauryl collagenate 5 Water to make up to 100 3. Lysine capryl aspartate 0.5 to 10 Bentonite (Fullers earth) to make up to 100 ______________________________________