Substituted oxazolidines

Details Substituted oxazolidines Substituted oxazolidines

1996-06-10

1997-06-03

McKane, Joseph

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Having -c-, wherein x is chalcogen, bonded directly to...

548215, A61K 3147, C07D26302

Patent

active

056355246

DESCRIPTION:

BRIEF SUMMARY
This is a 371 of PCT/EP94/03937, filed Nov. 28, 1994.
The present invention relates to novel substituted oxazolidines of formula I ##STR2## wherein R.sub.1 and R.sub.2 are simultaneously hydrogen or both together are the identical alkyl radical of up to seven carbon atoms, and to the salts thereof in racemic and chiral form, to a process for the preparation of said compounds, to pharmaceutical compositions containing them, and to the use thereof as medicaments.
EP-A-0 422 889 and FR-A-2 545 482 describe amino-alcohols with stimulant activity on beta-adrenergic receptors.
U.S. Pat. No. 4,407,819 (American Cyanmide Co.) discloses oxazolidines which differ in the orientation of the substituents at the phenyl ring and in the substituents at the oxygen atom in the oxazolidine ring, and which are used as additives for animal feeds.
Throughout this specification, radicals and compounds qualified by the term "lower" will be understood as meaning those that carry up to 7, preferably up to 4, carbon atoms inclusive.
Lower alkyl is typically C.sub.1 -C.sub.4 alkyl such as methyl, ethyl, propyl or butyl. The novel compounds thus comprise all enantiomers, diastereoisomers and mixtures thereof, including racemates
Compounds of formula I within the scope of the invention are preferably obtained in the form of racemates of stereoisomers (R and S), most preferably in chiral R and S form.
Salts of compounds of formula I are preferably pharmaceutically acceptable salts, typically acid addition salts, which are formed, inter alia, with strong inorganic acids such as mineral acids, e.g. sulfuric acid, a phosphoric acid or a hydrohalic acid, with strong organic carboxylic acids such as lower alkanecarboxylic acids, typically acetic acid, or with dicarboxylic acids or unsaturated dicarboxylic acids such as malonic acid, maleic acid or furmaric acid, or with hydroxycarboxylic acids such as tartaric or citric acid, or with sulfonic acids such as lower alkanesulfonic acids or benzenesulfonic acids or substituted benzenesulfonic acids such as methane or p-toluenesulfonic acid, or salts with bases, typically alkali metal or alkaline earth metal salts, e.g. sodium, potassium or magnesium salts, pharmaceutically acceptable transition metal salts such as zinc or copper salts, or salts with ammonia or organic amines, including cyclic amines such as mono-, di- or tri-lower alkylamines, typically hydroxy-lower alkylamines, e.g. mono-, di- or trihydroxy-lower alkylamines, hydroxy-lower alkyl-lower alkylamines or polyhydroxy-lower alkylamines. Cyclic amines are typically morpholine, thiomorpholine, piperidine or pyrrolidine. Suitable mono-lower alkylamines typically include ethyl- and tert-butylamine, and suitable di-lower alkylamines are typically diethyl- and diisopropylamine, and suitable tri-lower alkylamines are typically trimethyl- and triethylamine. Corresponding hydroxy-lower alkylamines are typically mono-, di- and triethanolamine; hydroxy-lower alkyl-lower alkylamines are typically N,N-dimethylaminoethanol and N,N-diethylaminoethanol; a suitable polyhydroxy-lower alkylamine is glucosamine. Unsuitable salts are also included for pharmaceutical usages, as these may be used, inter alia, for the isolation and/or purification of free compounds of formula I and their pharmaceutically acceptable salts.
The compounds of formula I and their pharmaceutically acceptable salts have valuable pharmacological properties.
The novel compounds of formula I have a prolonged stimulating action on beta-adrenergic receptors or they induce relaxation of sensitive unstriated muscles.
Owing to this effective relaxation of unstriated muscles, the compounds of formula I can be used for the prevention or treatment of bronchial spasm and dispnoe in diseases such as bronchial asthma, chronic bronchitis and chronic obstructive pulmonary diseases, anaphylactic bronchial spasm and cystic fibrosis as well as for the prevention or alleviation of premature labour pains in a stage of pregnancy.
The compounds of formula I are also useful for the prevention or treatment

REFERENCES:
patent: 4064257 (1977-12-01), Berkoz et al.
patent: 4992474 (1991-02-01), Skidmore et al.
Johansen et al, Journal of Pharmaceutical Sciences vol. 72, No. 11, Nov. 1983, pp. 1294-1298.

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