Drug – bio-affecting and body treating compositions – Antigen – epitope – or other immunospecific immunoeffector – Bacterium or component thereof or substance produced by said...
Patent
1981-07-16
1983-11-29
Raymond, Richard
Drug, bio-affecting and body treating compositions
Antigen, epitope, or other immunospecific immunoeffector
Bacterium or component thereof or substance produced by said...
546333, A61K 3144, C07D21338
Patent
active
044180659
DESCRIPTION:
BRIEF SUMMARY
DESCRIPTION
1. Technical Field
The present invention relates to new compounds having therapeutic activity and to methods for their preparation. The invention also relates to the preparation of pharmaceutical preparations containing at least one of the compounds and to methods for their pharmacological use.
2. Background Art
It is known from the literature that certain 1,1-diphenyl-3-aminoprop-1-enes, such as the compound having the formula ##STR2## have an antidepressive effect, of J. Med. Chem. 14, 161-4 (1971). Compounds having the formula ##STR3## wherein X is chlorine or bromine and R is hydrogen or methyl, are described to have antidepressive effect, cf. U.S. Pat. No. 3,423,510. From the literature it is also known that compounds having the formula ##STR4## have antidepressive activity in animal models, cf. Belgian Patent Specifications No. 781,105 and No. 835,802.
DISCLOSURE OF INVENTION
(a) General outline
A main object of the present invention is to obtain new compounds having a good antidepressive effect. A further object of the invention is to obtain compounds having an antidepressive effect, and giving rise to only minor side-effects, in particular arrhythmogenic effects and anticholinergic effects. A further object is to provide antidepressive compounds useful for treatment of various kinds of depressions e.g. depressions connected with insufficient synaptic amounts of 5-hydroxytryptamine, noradrenaline or both. Further objects of the invention will be evident from the following description.
The compounds of the invention are characterized by the formula ##STR5## wherein R is H or CH.sub.3, n is 1 or 2, and X is a halogen selected from F, Cl, Br I and CF.sub.3 bound in an optional position to the phenyl group provided that when X is Br it is bound in a position other than the 4 position.
Pharmaceutically acceptable salts of these compounds are included within this invention.
Due to the lack of free rotation in the double bond the compounds of this invention may exist in different stereoisomeric forms, that is in cis-trans isomers or, according to the IUPAC nomenclature (J. Org. Chem. 35, 2849-2867, September 1970), in an E-form and a Z-form. The compound may be used therapeutically as a mixture of geometrical isomers or in pure E or Z form. The pure geometrical isomers may be prepared from an isomer mixture, from an isomer-pure starting material or directly by a stereoselective synthesis.
The compounds of this invention may be administered in the form of free bases or their salts with non-toxic acids. Some typical examples of these salts are the hydrobromide, hydrochloride, phosphate, sulphate, citrate, tartrate, malate and maleate.
(b) Pharmaceutical preparations
In clinical practice the compounds of the present invention will be normally administered orally, rectally or by injection, in the form of pharmaceutical preparations comprising the active ingredient either as a free base or as a pharmaceutically acceptable, non-toxic acid addition salt, e.g. as the hydrochloride, hydrobromide, lactate, acetate, sulphate or sulphamate in association with a pharmacetically acceptable carrier. Accordingly, terms relating to the novel compounds of this invention whether generical or specifical are intended to include both the free amine base and the acid addition salts of the free base, unless the context in which such terms are used, e.g. in the specific examples would be inconsistent with the broad concept. The carrier may be a solid, semisolid or liquid diluent, or a capsule. These pharmaceutical preparations constitute a further aspect of this invention.
Usually the active substance will constitute from 0.1 to 99% by weight of the preparation, more specifically from 0.5 to 20% by weight for preparations intended for injection and from 2 to 50% by weight for preparations suitable for oral administration.
To produce pharmaceutical preparations containing a compound of the invention in the form of dosage units for oral application, the selected compound may be mixed with a solid pulverulent carrier,
REFERENCES:
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Gordon, "Psychopharmacological Agents" vol. 1, pp. 54-55 (1964).
Hoffsommer et al., "Synthesis of Amitriptyline and Related Substances" Journal of Org. Chem. 28(7) pp. 1751-1753 (1963).
Chem. Abstracts 46:2055; 58:9031; 76:59467; 86:139786; 87:133285.
De Paulis Tomas
Hogberg Thomas
Ross Svante B.
Ulff Carl B. J.
Astra Lakemedel Aktiebolag
Raymond Richard
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