Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Patent
1997-04-30
1998-12-29
Henley, III, Raymond
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
546196, A61K 31445, C07D40100
Patent
active
058542604
DESCRIPTION:
BRIEF SUMMARY
CROSS-REFERENCE TO RELATED APPLICATIONS
This application is the national stage of application No. PCT/EP 95/04519, filed on Nov. 16, 1995, which application claims priority from EP 94.203.421.6, filed on Nov. 23, 1994.
The present invention is concerned with a novel benzamide derivative and the pharmaceutically acceptable acid addition salts thereof, pharmaceutical compositions comprising said novel compound, processes for preparing said compounds and compositions, and the use thereof as a medicine, in particular in the treatment of conditions involving an impaired motility of the intestine, especially of the colon.
In our EP-0,389,037-A, published on Sep. 26, 1990, N-(3-hydroxy-4-piperidinyl) (dihydrobenzofuran or dihydro-2H-benzopyran)carboxamide derivatives are disclosed as having gastrointestinal motility stimulating properties. In our EP-0,445,862-A, published on Sep. 11, 1991, N-(4-piperidinyl) (dihydrobenzofuran or dihydro-2H-benzopyran)carboxamide derivatives are disclosed also having gastrointestinal motility stimulating properties.
The compound subject to the present application differs therefrom by showing superior enterokinetic properties.
The present invention concerns a compound of formula ##STR2## and the pharmaceutically acceptable acid addition salts thereof.
The chemical name of the compound of formula (I) is furancarboxamide.
The pharmaceutically acceptable acid addition salts as mentioned hereinabove are meant to comprise the therapeutically active non-toxic acid addition salt forms which the compounds of formula (I) are able to form. The latter can conveniently be obtained by treating the base form with such appropriate acid. Appropriate acids comprise, for example, inorganic acids such as hydrohalic acids, e.g. hydrochloric or hydrobromic acid; sulfuric; nitric; phosphoric and the like acids; or organic acids such as, for example, acetic, propanoic, hydroxyacetic, lactic, pyruvic, oxalic, malonic, succinic (i.e. butanedioic acid), maleic, fumaric, malic, tartaric, citric, methanesulfonic, ethanesulfonic, benzenesulfonic, p-toluenesulfonic, cyclamic, salicylic, p-aminosalicylic, pamoic and the like acids. The term addition salt as used hereinabove also comprises the solvates which the compounds of formula (I) as well as the salts thereof are able to form. Such solvates are, for example, hydrates, alcoholates and the like. Conversely the salt form can be converted by treatment with alkali into the free base form. Hereinafter the term "compounds of formula (I)" means the compound of formula (I) as well as the pharmaceutically acceptable acid addition salts thereof, unless otherwise mentioned.
Interesting compounds of formula (I) are the acid addition salts which are formed by treating the base form of the compound of formula (I) with hydrohalic acids or butanedioic acid.
Preferred compounds of formula (I) are furancarboxamide monohydrochloride and furancarboxamide butanedioate (1:1).
The compounds of formula (I) may be prepared according to procedures which are disclosed in EP-0,389,037-A and EP-0,445,862-A. A number of preparation alternatives are shown hereinunder.
In the following preparations, the reaction products may be isolated from the reaction mixture and, if necessary, further purified according to methodologies generally known in the art such as, for example, extraction, distillation, crystallization, trituration and chromatography.
The compounds of formula (I) can be prepared by N-alkylating an intermediate of formula (II) with an alkylating reagent of formula (III), wherein W is an appropriate leaving group such as a halo, e.g. chloro; or a sulfonyloxy leaving group, e.g. methanesulfonyloxy (mesylate) or a p-toluenesulfonyloxy (tosylate) in a reaction inert solvent such as a dipolar aprotic solvent, e.g. dimethyl formamide, in the presence of an appropriate base such as, for instance, triethylamine. A suitable catalyst such as potassium iodide may also be added to enhance the reaction rate. ##STR3##
The compound of formula (I) may also be prepared by an N-acylation reaction
REFERENCES:
patent: 5185335 (1993-02-01), Van Daele et al.
patent: 5374637 (1994-12-01), Van Daele et al.
Bosmans Jean-Paul Rene Marie Andre
Schuurkes Joannes Adrianus Jacobus
Van Daele, deceased Georges H. P.
Ciambrone Coletti Ellen
Henley III Raymond
Janssen Pharmaceutica N.V.
LandOfFree
Enterokinetic benzamide does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Enterokinetic benzamide, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Enterokinetic benzamide will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-1425146