Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Reexamination Certificate
2000-10-12
2001-07-24
Powers, Fiona T. (Department: 1626)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
C514S576000, C514S578000, C556S120000, C562S044000, C562S105000
Reexamination Certificate
active
06265437
ABSTRACT:
The present invention relates to sulphonic, phosphonic and phosphinic acid derivatives intended for the treatment of dependency on alcohol and on other substances.
Japanese Patent JP 7612093 discloses compounds of formula:
as hypocholesterolaemics
Japanese Patent JP 63201643 discloses the use of potassium 4-palmitylsulphonate as adjuvant in photographic substrates.
FR-A-2,457,281 has disclosed acetylhomotaurine salts as membrane stabilizers. The calcium salt of acethylhomotaurine is used in the treatment of alcoholism (under the name of acamprosate).
A subject-matter of the present invention is novel sulphonic, phosphonic and phosphinic acid derivatives represented by the formula (I):
in which
X is
R
1
, R
2
and R
3
are selected from hydrogen and a C
1
-C
7
alkyl radical,
A is a group of formula
with v and w=0, 1 or 2
or a group of formula
R
5
and R
6
being selected, independently of one another, from hydrogen, a C
1
-C
7
alkyl radical, an aryl radical having from 6 to 14 carbon atoms and a heteroaryl radical selected from furyl, thienyl and thiazolyl, it being possible for the aryl and heteroaryl radicals to carry 1 to 3 substituents selected from a C
1
-C
7
alkyl group, a halogen or a trifluoromethyl group, and t=1-3,
R
4
is selected from hydrogen, a C
1
-C
7
alkyl radical, a CF
3
radical, an aryl radical having from 6 to 14 carbon atoms and a heteroaryl radical selected from furyl, thienyl and thiazolyl, it being possible for the aryl and heteroaryl radicals to carry 1 to 3 substituents selected from a C
1
-C
7
alkyl group, a halogen or a trifluoromethyl group,
M is a monovalent metal (Na, K, Li) or a divalent metal (Ca, Mg, Sr, Zn),
m=1 or 2,
p=1-2 and q=1-2, p and q being such that the electrical neutrality of the salt is ensured,
R
4
not being a methyl radical when R
1
, R
2
and R
3
are hydrogen.
The compounds of the invention can comprise chiral centres. The optical isomers, the racemates, the enantiomers and the diastereoisomers form part of the invention.
The Applicant company has shown that this family of products make it possible to decrease the consumption of alcohol in rats exhibiting alcohol dependency. Their therapeutic applications relate, inter alia, to the field of dependency on alcohol and on other substances capable of leading to habituation, such as, for example, opiates, nicotine derivatives, caffeine derivatives, amphetamines, cannabinoids or tranquillizers.
The present invention also applies to pharmaceutical compositions comprising, as active principle, one of the compounds of formula (I), optionally in combination with one or more pharmaceutically acceptable excipients or vehicles.
Mention may be made, among the compositions according to the invention, by way of example and without implied limitation, of tablets, capsules, including hard gelatin capsules, or solutions to be taken orally.
The compounds of the invention can be administered at doses of between 0.01 g and 1 g from one to three times daily.
Mention may be made, among the preferred compounds of the formula 1, of, for example:
calcium 3-(2-(methyl)propanoylamino)propanesulphonate
magnesium 3-(2-(methyl)propanoylamino)propanesulphonate
calcium 3-(butanoylamino)propanesulphonate
magnesium 3-(butanoylamino)propanesulphonate
calcium 3-(pentanoylamino)propanesulphonate
calcium 3-(benzoylamino)propanesulphonate
magnesium 3-(benzoylamino)propanesulphonate
zinc 3-(2-(methyl)propanoylamino)propanesulphonate
strontium 3-(2-(methyl)propanoylamino)propanesulphonate
calcium 3-(3-(methyl)butanoylamino)propanesulphonate
magnesium 3-(3-(methyl)butanoylamino)propanesulphonate
calcium 3-(2-2-(dimethyl)propanoylamino)propanesulphonate
magnesium 3-(2-2-(dimethyl)propanoylamino)propanesulphonate
calcium 3-(acetylamino)-2-methylpropanesulphonate
calcium 3-(acetylamino)-3-methylpropanesulphonate
magnesium 3-(acetylamino)-3-methylpropanesulphonate
calcium 3-(acetylamino)-1-methylpropanesulphonate
calcium 3-(acetylamino)-2-phenylpropanesulphonate
calcium 2-(2-acetylaminomethyl)phenylmethanesulphonate
calcium N-methyl-3-(acetylamino)propanesulphonate
calcium 3-(acetylamino)-2-2-dimethylpropanesulphonate
calcium 3-(trifluoromethylcarbonyl)propanesulphonate
Preference is very particularly given to the compounds of formula I in which R
4
is a C
2
-C
7
alkyl radical and in particular a branched radical.
The following compounds also form part of the invention:
3-((2-methyl)propanoylamino)propanesulphonic acid
3-(butanoylamino)propanesulphonic acid
3-(pentanoylamino)propanesulphonic acid
3-(benzoylamino)propanesulphonic acid
3-(acetylamino)propanephosphonic acid
N-methyl-3-(acetylamino)propanesulphonic acid
3-((3-methyl)butanoylamino)propanesulphonic acid
3-((2-2-dimethyl)propanoylamino)propanesulphonic acid
3-(acetylamino)-2-methylpropanesulphonic acid
3-(acetylamino)-3-methylpropanesulphonic acid
3-(acetylamino)-1-methylpropanesulphonic acid
3-(acetylamino)-2-phenylpropanesulphonic acid
2-(2-acetylaminomethyl)phenylmethanesulphonic acid
3-(acetylamino)-2-2-dimethylpropanesulphonic acid
3-(trifluoromethylcarbonoyl)propanesulphonic acid
The invention is also targeted at a process for the preparation of the compounds of the invention. The latter is summarized in Scheme 1.
The reaction can be carried out by reacting the compound of formula (II) with the base M(OH)
z
, where z is the valency of M, and then, while maintaining at a temperature of between 15° C. and 20° C., the anhydride of formula (IV) is added. Reaction is allowed to take place overnight and, after treatment, the compound of formula (I) is obtained.
The list of the following examples illustrating the invention is not limiting. In the proton nuclear magnetic resonance (
1
H NMR) data, the following abbreviations were employed:
ppm for parts per million
s for singlet
d for doublet
t for triplet
q for quartet
m for complex unresolved peak
j for the couplings, expressed in Hertz
dd for double doublet
REFERENCES:
patent: 4199601 (1980-04-01), Durlach
patent: 4355043 (1982-10-01), Durlach
patent: 2457281 (1980-12-01), None
Berthelon Jean-Jacques
Durbin Philippe
LIPHA
Powers Fiona T.
Young & Thompson
LandOfFree
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