Phenylethanolamines, their use as pharmaceuticals and as perform

Details Phenylethanolamines, their use as pharmaceuticals and as perform Phenylethanolamines, their use as pharmaceuticals and as perform

1990-08-20

1993-08-03

Waddell, Frederick E.

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Ester doai

514512, 514522, 514564, 514567, 514622, 514651, 514652, 514653, A61K 3122, A61K 31265, A61K 31275, A61K 31195

Patent

active

052329461

DESCRIPTION:

BRIEF SUMMARY
This invention relates to new phenylethanolamines of formula ##STR2## the optical isomers, diastereoisomers and acid addition salts thereof, particularly for pharmaceutical use the physiologically acceptable acid addition salts, which have valuable pharmacological properties, namely an effect on the metabolism, particularly the effect of lowering blood sugar, reducing body fat and increasing energy consumption, and lowering the atherogenic lipoproteins VLDL and LDL.
The new compounds may also be used as performance enhancers in animals, particularly in order to achieve higher daily weight increases and improved food utilisation in animal feeding, preferably in the fattening of animals, which is a further object of the invention.
In general formula I above carbon atoms, or hydroxymethylene group, group, carboxy, alkoxycarbonyl, aminocarbonyl, alkylaminocarbonyl or dialkylaminocarbonyl group, an alkoxy group with 1 to 3 carbon atoms substituted in the end position by a carboxy, alkoxycarbonyl, aminocarbonyl, alkylaminocarbonyl or dialkylaminocarbonyl group, or an alkoxy group with 2 or 3 carbon atoms substituted in the end position by a hydroxy, alkoxy, amino, alkylamino, dialkylamino, pyrrolidino, piperidino or hexamethyleneimino group, whilst all the above-mentioned alkyl or alkoxy groups may contain from 1 to 3 carbon atoms, unless otherwise stated.
As examples of the definitions of the groups given hereinbefore:
A may represent a methylene, 1-ethylidene, 1-n-propylidene, 1-n-butylidene, ethylene, 1-methylethylene, 2-methyl-ethylene, 1-ethyl-ethylene, 2-ethyl-ethylene, 1,2-dimethyl-ethylene, 1,1-dimethylethylene, 1-ethyl-1-methylethylene, 2,2-dimethyl-ethylene, 2-ethyl-2-methyl-ethylene, n-propylene, 1-methyl-n-propylene, 2-methyl-n-propylene, 3-methyl-n-propylene, 1-ethyl-n-propylene, 2-ethyl-n-propylene, 3-ethyl-n-propylene, 1,1-dimethyl-n-propylene, 2,3-dimethyl-n-propylene, 3,3-dimethyl-n-propylene, n-butylene or n-pentylene group,
B represents a bond, a methylene, ethylene, 1-ethylidene, carbonyl or hydroxymethylene group,
R.sub.1 represents a hydrogen, fluorine, chlorine or bromine atom or a trifluoromethyl group,
R.sub.2 represents a hydrogen atom or an amino group,
R.sub.3 represents a hydrogen, chlorine or bromine atom or a cyano group and
R.sub.4 represents a hydrogen, fluorine, chlorine or bromine atom, a methyl, ethyl, n-propyl, isopropyl, hydroxy, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, carboxy, methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, aminocarbonyl, methylaminocarbonyl, ethylaminocarbonyl, isopropylaminocarbonyl, dimethylaminocarbonyl, diethylaminocarbonyl, di-n-propylaminocarbonyl, N-ethyl-methylaminocarbonyl, N-ethyl-isopropylaminocarbonyl, 2-hydroxy-ethoxy, 3-hydroxy-n-propoxy, 2-methoxy-ethoxy, 2-ethoxy-ethoxy, 2-n-propoxyethoxy, 3-ethoxy-n-propoxy, 2-amino-ethoxy, 2-methylamino-ethoxy, 2-dimethylamino-ethoxy, 2-isopropylaminoethoxy, 2-di-n-propylamino-ethoxy, 2-(1-pyrrolidino)-ethoxy, 2-(1-piperidino)ethoxy, 2-(1-hexamethyleneimino)-ethoxy, 3-amino-n-propoxy, 3-diethylamino-n-propoxy, 3-(1-piperidino)-n-propoxy, carboxymethoxy, 2-carboxy-ethoxy, 3-carboxy-n-propoxy, methoxycarbonyl-methoxy, 2-methoxycarbonyl-ethoxy, ethoxycarbonylmethoxy, 2-ethoxycarbonyl-ethoxy, 3-ethoxycarbonyl-n-propoxy, n-propoxycarbonylmethoxy, 2-isopropoxycarbonyl-ethoxy, aminocarbonylmethoxy, 2-aminocarbonyl-ethoxy, ethoxy, dimethylaminocarbonylmethoxy, 2-dimethylamino-carbonyl-ethoxy, diethylaminocarbonylmethoxy, 2-diethylaminocarbonylethoxy, or 2-di-n-propylaminocarbonyl-ethoxy group.
By way of example, in addition to the compounds mentioned in the Examples, mention should also be made of the following compounds which are covered by general formula I given hereinbefore: fluoro-phenyl)-2-hydroxy-ethyl)-amino]propyl]diphenylmethane-2-carboxylate 4'-[2-[N-(2-(4-amino-3-cyano-5-fluoro-phenyl)-2-hydroxy-ethyl)-amino]propy l]biphenylyl-4-carboxylate, 4'-[2-[N-(2-(4-amino-3-cyano-5-fluoro-phenyl)-2-hydroxy-ethyl)-amino]propy l]biphenylyl-4-oxyacetate 4'-[2-[N-(2-(4-amino-3-cyano-5-fluoro-phenyl)-2

REFERENCES:
Chemical Abstracts (108: 111962h) 1987.

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