# Patent

## Title
Phosphonoformaldehyde, a process for its preparation and its use as an

## Abstract

The compounds are claimed per se and in pharmaceutical and horticultural compositions. Methods of treatment of men, animals and vegetation are also claimed.

## Background
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.

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

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. ______________________________________ 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. ______________________________________ 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. ______________________________________ 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 ______________________________________

## Claims

1. A derivative of lysine and aspartic acid having the general formula ##STR3## in which R represents an acyl group having from 6 to 26 carbon atoms and n is 2 and in which the acyl group is derived from an aliphatic moncarboxylic acid.

2. A derivative of lysine and aspartic acid having the general formula ##STR4## in which R represents an acyl group having from 6 to 26 carbon atoms and n is 2 and wherein the acyl group is selected from the group consisting of caproyl, capryl, lauryl, palmityl, undecenyl, oleyl and linoleyl groups.