Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Patent
1985-12-20
1987-12-15
Ford, John M.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
548308, 514390, C07D23530, A61K 31415
Patent
active
047133902
DESCRIPTION:
BRIEF SUMMARY
The object of the present invention is new sulfurated hydantoin derivatives used for the basic treatment of rheumatoid arthritis or evolutive chronic polyarthritis. These substances seek to correct the chronic inflammatory response which is characterized by this infection and are very clearly distinguished from non-steroid anti-inflammatories, which reduce the acute inflammatory reaction during episodes of exacerbation without however stopping the progress of this disease.
For the treatment of such diseases it is known to clinically use antimalarial compounds, gold complexes and D-penicillamine.
This latter molecule has a well-established activity but is responsible for numerous secondary effects which limit its use and are the cause of abandonment during treatment.
The object of the present invention is new pharmaceutical products based on sulfurated derivatives of hydantoin and their uses in pharmaceutical compositions. Such compounds possess structural characteristics such that they provide a different development from that of D-penicillamine whilst maintaining comparable activity, thus providing the possibility of achieving lower toxicity and a better therapeutic index.
The new sulfurated derivatives of hydantoin in accordance with the invention are composed of a structure of general formula (I): ##STR1## in which R represents a hydrogen atom, a lower alkyl group containing from 1 to 6 carbon atoms, a lower cycloalkyl group containing from 3 to 7 carbon atoms, or an aryl group with 6 carbon atoms. The new sulfurated derivatives of hydantoin also comprise their physiologically acceptable salts, their optical isomers, their mixtures and their racemic compounds. By physiologically acceptable salts are meant the salts obtained by the action of alkali or alkaline earth compounds in accordance with known methods or any other method described in the literature.
The claimed sulfurated derivatives of hydantoin have an asymmetric carbon at the 5 position, which gives them an optical activity. The optical isomers (enantiomers) which cover the compounds of the invention are conventionally designated by the symbols (R) and (S), or even by L and D, 1 and d, (+) or (-) or by combinations of said symbols.
When a specific designation has not been attributed to the compounds of the invention, these compounds designate both the individual enantiomers, their mixtures or their racemic compounds.
The pharmaceutical compositions of the present invention can comprise a single active hydantoin derivative or mixtures of several of said derivatives, taken in the broadest sense, and in particular comprising their salts and their optical isomers, their mixtures and their racemic compounds. The pharmaceutical compositions result from being placed in an appropriate form of administration, possibly with solid or liquid, inert, non-toxic vehicles and/or excipients which are used in galenic pharmaceutics. The choice of presentation of the compositions is carried out depending on whether it is to be administered orally, parenterally or by any other means. Thus, the galenic preparation may be in the form of tablets, pills, capsules, coated pills, drinkable or injectable solutions, or suppositories.
The unit dose used corresponds to a pharmacologically active dose established in accordance with methods which are well-known to one skilled in the art.
Among the new sulfurated derivatives of hydantoin used as active compounds in pharmaceutical compositions, the simplest derivative is obtained in the case of R=H, in general formula (I). In this case the compound is 5-(2-methyl 2-thiol ethyl) hydantoin.
The R substituent can be a lower alkyl group with 1 to 6 carbon atoms (methyl, ethyl, n-propyl, isopropyl, n-butyl, n-pentyl, n-hexyl). Preferably the methyl or ethyl group is selected. In such cases, the hydantoin derivatives are 3-methyl 5-(2-methyl 2-thiol) hydantoin and 3-ethyl 5-(2-methyl 2-thiol ethyl) hydantoin. The R substituent can be a lower cycloalkyl group containing from 3 to 7 carbon atoms selected from cyclopropyl, cyclobutyl, cy
REFERENCES:
patent: 4230709 (1980-10-01), Jamieson et al.
Poupaert et al., Eur. J. Med. Chem., Nov.-Dec., 1980-15, No. 6., pp. 511-514.
DuMont Pierre
Poupaert Jacques
Ford John M.
Region Wallonne
Whittenbaugh Robert C.
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