Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Patent
1996-04-22
1998-02-17
Davis, Zinna Northington
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
514352, 514618, 546309, 546333, 564162, C07D21356, C07C31744, A61K 3116, A61K 3144
Patent
active
057191689
DESCRIPTION:
BRIEF SUMMARY
This application is a 371 of PCT/FR94/0083 filed Jun. 30, 1994.
The present invention relates to acetamide derivatives which may be used therapeutically as feeding behaviour modifiers.
Various acetamide derivatives which may be used therapeutically are already known for their stimulatory effect on the central nervous system. Mention may be made in particular of adrafinil or benzhydrylsulphinyl acetohydroxamic acid (described in FR-A-2,326,181) and modafinil (described in FR-A-2,385,693) and other compounds described in FR-A-2,528,038, FR-A-2,601,673, FR-A-2,602,768 and FR-A-2,606,815.
The present invention aims to provide novel acetamide derivatives which are characterized by a modificatory or regulatory effect on feeding behaviour in man and animals.
The subject of the present invention is thus compounds of formula: ##STR2## in which: R.sub.1 is chosen from H and 3-chloro, methyl, pyridylmethyl group or both represent an ethyl group, when R.sub.2 =phenyl, pharmaceutically acceptable acids.
The compounds of formula I may generally be obtained according to known methods. Thus, the compounds of formula I in which n=1 may be obtained by oxidation, in particular by H.sub.2 O.sub.2, of a compound of formula I in which n=0, that is to say a thioacetamide of formula: ##STR3##
The thioacetamides of formula II may be obtained in particular by reaction of a reactive derivative of an acid of formula: ##STR4## in which Z is a reactive group, in particular Cl or OCH.sub.3, with an amine of formula:
As a variant, certain compounds may be obtained by reaction of an acid of formula: ##STR5## or one of the reactive derivatives thereof, with an amine of formula III.
The compounds according to the invention may be used therapeutically as feeding behaviour modifiers or regulators in man and animals.
Another subject of the present invention is thus therapeutic compositions comprising an effective amount of a compound of formula I or salts of compounds of formula I containing a pyridine group with pharmaceutically acceptable acids.
The therapeutic compositions according to the invention may be administered in particular via the oral route.
They may be in the form of solid or semi-solid preparations. Tablets, gelatin capsules and delayed-action forms may be mentioned as examples.
In these compositions, the active principal is generally mixed with one or more usual pharmaceutically acceptable excipients well known to those skilled in the art.
These compositions make it possible in particular to delay feeding and may thus constitute a valuable aid to weight control, in particular for individuals who are on a diet.
The effects on feeding behaviour have been demonstrated using a test in mice, according to a method described by Ladurelle et al. (Fundam. Clin. Pharmacol., 5, 481).
The examples which follow illustrate the preparation of the compounds of formula I.
EXAMPLE 1
Preparation of m-chlorobenzhydrylsulphinylacetamide (CRL 41096).
a) Preparation of m-chlorobenzhydrol
The following are placed in a three-necked flask: 4.86 g (0.2 g.at.) of magnesium covered with a small amount of anhydrous ether, a crystal of iodine and a few drops of bromobenzene are added in order to initiate the reaction; a solution of 32 g (0.204 mol) of bromobenzene in 200 ml of ether is then added dropwise. The mixture is then maintained at reflux on a water bath for about 1 hour, followed by cooling and dropwise addition, when cold, of a solution of 28.1 g (0.2 mol) of m-chlorobenzaldehyde in a small amount of ether. The complex thus obtained is filtered and then taken up in ether and hydrolysed with a water+HCl solution. The ether phase is then washed with water, dried over Na.sub.2 SO.sub.4 and evaporated.
28.14 g of a yellow oil are collected: m-chlorobenzhydrol (yield=65%).
b) Preparation of m-chlorobenzhydrylthioacetic acid
The following are placed in a three-necked flask: 12.86 g (0.156 mol) of thiourea in 65 ml of 48% HBr and 13 ml of water; the mixture is brought to 60.degree. C. and 28.4 g (0.13 mol) of m-chlorobenzhydrol are added in a single p
REFERENCES:
Copy of PCT International Search Report, 1994.
Davis Zinna Northington
Laboratoire L. Lafon
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