Substituted ethanolamine esters

Details Substituted ethanolamine esters Substituted ethanolamine esters

1995-04-17

1997-02-04

Conrad, Joseph

Organic compounds -- part of the class 532-570 series

Organic compounds

Nitriles

546335, 548504, 549 77, 549491, 560 12, 560 39, 560 61, 560100, 560105, C07C25549, C07C22908, C07D21355, C07D20916

Patent

active

055999662

DESCRIPTION:

BRIEF SUMMARY
FIELD OF USE OF THE INVENTION

The invention relates to novel compounds, processes for their preparation and their use as active compounds in medicaments.


KNOWN TECHNICAL BACKGROUND

German Patent Applications DE 37 04 223 and DE 40 28 398 and European Patent Applications EP 278 727, EP 278 728, EP 286 242, EP 303 464, EP 303 465, EP 303 466 and EP 422 889 describe variously substituted ethanolamine derivatives which, because of their .beta..sub.2 adrenoceptor-agonistic properties, are said to be particularly suitable for the treatment of diseases of the respiratory passages. British Patent 893,088 describes substituted amines which are said to have antihypertensive and in some cases also spasmolytic properties. The compounds disclosed in this patent are phenylethylamines substituted in a particular manner, which are substituted on the nitrogen atom by an alkyleneoxycarbonylphenyl radical, where this phenyl radical bonded directly to the carbonyl group must be substituted by three hydroxyl or alkoxy groups. German Auslegeschrift 11 26 889 likewise describes substituted amines (derived from reserpine) having an antihypertensive and spasmolytic action, in which the phenyl radical bonded directly to the carbonyl group must be substituted by at least one hydroxyl or alkoxy radical and if appropriate also by a further hydroxyl or alkoxy radical.


DESCRIPTION OF THE INVENTION

A novel group of substituted ethanolamine derivatives which differ structurally from the compounds of the prior art by a hydrolyzable ester group or by a longer chain length or a quite specific substitution has now been found. In a first aspect, the invention thus relates to compounds of formula I --E--(CH.sub.2).sub.n --Y--Ar.sub.2 (I) 1-4C-alkyl, phenyl or hydroxyl, or the group --CR'.sub.2 -- or --CHR'--CH.sub.2 O--, in which R' is 1-4C-alkyl, and in which Y is not oxygen if n is the number 0, (--NH--CO--NH.sub.2), formylamino (--NH--COH), 1-4C-alkylcarbonylamino (--NH--CO-1-4C-alkyl), di-1-4C-alkyl-carbamoyloxy [--O--CO--N(1-4C-alkyl).sub.2 ], toluyloxy (--O--CO--C.sub.6 H.sub.4 --CH.sub.3), hydroxymethyl (--CH.sub.2 OH), 1-4C-alkylcarbonyloxy (--O--CO-1-4C-alkyl), 1-4C-alkyl, 1-4C-alkoxy, 1-4C-alkylsulfonylamino (--NH--SO.sub.2 -1-4C-alkyl), 1-4C-alkylsulfonylmethyl (--CH.sub.2 --SO.sub.2 -1-4C-alkyl) or 1-4C-alkoxy-1-4C-alkyl, (--CF.sub.3), toluyloxy (--O--CO--C.sub.6 H.sub.4 --CH.sub.3), hydroxymethyl (--CH.sub.2 OH) or 1-4C-alkylcarbonyloxy (--O--CO-1-4C-alkyl) and radical, a pyridyl radical, a naphthyl radical, an indolyl radical, an indanyl radical or a benzo-1,4-dioxanyl radical, in which 1-4C-alkoxy, benzyloxy, nitro (--NO.sub.2), trifluoromethyl (--CF.sub.3), 1-4C-alkoxycarbonyl (--CO--O-1-4C-alkyl),carbamoyl (--CO--NH.sub.2), di-1-4C-alkylcarbamoyl [--CO--N(1-4C-alkyl).sub.2 ], amino (--NH.sub.2), 1-4C-alkylsulfonyl, phenyl or phenylcarbonylamino and (--O--CO--), n is the number 0 and Y is a bond, and in which R1 and R2 are not simultaneously hydroxyl if X is 1-4C-alkylene and E is carbonyloxy (--CO--O--),
1-12C-alkylene is straight-chain or branched alkylene radicals having 1 to 12 carbon atoms. Examples which may be mentioned are the radicals methylene (--CH.sub.2 --), ethylene (--CH.sub.2 CH.sub.2 --), trimethylene (--CH.sub.2 CH.sub.2 CH.sub.2 --), tetramethylene (--CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 --), pentamethylene (--CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 --), hexamethylene (--CH.sub.2 --(CH.sub.2).sub.4 --CH.sub.2 --), octamethylene (--CH.sub.2 --(CH.sub.2).sub.6 --CH.sub.2 --), decamethylene (--CH.sub.2 --(CH.sub.2).sub.8 --CH.sub.2 --), dodecamethylene (--CH.sub.2 --(CH.sub.2).sub.10 --CH.sub.2 --), 1,2-dimethylethylene [--CH(CH.sub.3)--CH(CH.sub.3)--], 1,1-dimethylethylene [--C(CH.sub.3).sub.2 --CH.sub.2 --], isopropylidene [--C(CH.sub.3).sub.2 --], 2,2-dimethylpropylene [--CH.sub.2 --C(CH.sub.3).sub.2 --CH.sub.2 --], 2-methylpropylene [--CH.sub.2 --CH(CH.sub.3)--CH.sub.2 --] and 2 -methylethylene [--CH.sub.2 --CH(CH.sub.3)--].
1-6C-alkyleneoxy-1-6C-alkylene is straight-chain or branched alkylene radic

REFERENCES:
patent: 4337207 (1982-06-01), Goodman

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