Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Radical -xh acid – or anhydride – acid halide or salt thereof...
Patent
1984-08-23
1987-06-16
Reamer, James H.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Radical -xh acid, or anhydride, acid halide or salt thereof...
562426, 562440, 562444, 562449, 562429, 562450, 514492, 514562, A61K 31195
Patent
active
046736905
DESCRIPTION:
BRIEF SUMMARY
The present invention relates to acylated enamide compounds consisting of acylated enamides as well as their salts, their complexes and their acylated and alkylated derivatives. The invention also relates to pharmaceutical compositions which contain these compounds and which can in particular be used for the prevention or treatment of cancers, the use of these compounds for the prevention of cancers and a process for the preparation of these compounds.
The acylated enamide compounds according to the invention are compounds corresponding to the general formula: ##STR3## in which Z represents an electron donor group, compounds.
The salts of these compounds can for example be ammonium salts, alkali metal salts such as the sodium or potassium salt, alkaline earth metal salts such as the magnesium and calcium salts, and salts of organic bases. The complexes of these compounds can be those formed with, for example, any metal salts. By acylated derivatives of these compounds, there are understood derivatives such as the esters and the amides of these compounds; preferably, the aromatic nucleus carrying the group Z does not contain acylated substituents.
Usually, the donor group is a halogen or a group selected from amongst the groups OR.sup.2, SR.sup.2, SeR.sup.2, N.dbd.R.sup.2 or NR.sup.2 R.sup.3, in which the oxygen, sulphur, selenium and nitrogen can form part of a ring and R.sup.2 and R.sup.3 can be identical or different and represent hydrogen or a saturated or unsaturated aliphatic or cyclic organic group containing from 1 to 20 carbon atoms. Most commonly, R.sup.2 and R.sup.3 represent a substituted or unsubstituted alkyl group containing from 1 to 6 carbon atoms. Preferably, the donor group is an OR.sup.2 group, where R.sup.2 represents hydrogen or a substituted or unsubstituted alkyl group containing from 1 to 6 carbon atoms. A very particularly preferred donor group is a methoxy group --OCH.sub.3.
Usually, R.sup.1 represents hydrogen, a halogen or any organic group. Preferably, R.sup.1 represents hydrogen or a substituted or unsubstituted aliphatic group containing from 1 to 4 carbon atoms, or an aromatic group containing from 5 to 8 carbon atoms. A particularly preferred meaning of R.sup.1 is hydrogen.
The preferred acylated enamide compounds according to the invention are the (methoxyphenylacetyl)dehydroalanines of the formula ##STR4## Amongst these, the preferred acylated enamide compound is that in which the methoxy substituent is in the paraposition.
A process for the preparation of acylated enamide compounds according to the invention consists of reacting an amide of the formula ##STR5## where R.sup.1, Z and n are as defined above, with pyruvic acid. The reaction can be carried out by bringing 1 mol of amide together with 1.2 mols of freshly distilled pyruvic acid and heating these, in benzene, to the reflux temperature in an apparatus equipped with a water separator. Refluxing is stopped when water ceases to separate out. The mixture is left until a precipitate forms and is then filtered, and the precipitate is treated with a saturated NaHCO.sub.3 solution. The fraction which is insoluble in a basic medium and which consists of unreacted amide is separated off and concentrated hydrochloric acid is then added gradually to the filtrate until a pH of about 3.5 and a precipitate result. After filtration and recrystallisation from ethanol, yields of between 30% and 95% are obtained. It can happen that a precipitate is not obtained after refluxing in benzene solution; in that case, the benzene is evaporated and the residue is treated in the same manner as described above.
The acylated enamide compounds according to the invention can also be prepared by any other appropriate organic synthesis. For example, the process described in French Pat. No. B-2,349,567 (SUMITOMO CHEMICAL COMPANY) can be employed.
The acylated enamide compounds according to the invention can be used as medicaments and especially for the treatment, in human or veterinary medicine, of all malignant tumoral proliferations such as canc
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Hervens Francoise M.
Roberfroid Marcel B.
Viehe Heinz G.
Biotec
Reamer James H.
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