Biologically active catecholamine derivatives

Chemistry of carbon compounds – Miscellaneous organic carbon compounds – C-metal

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260404, 562444, 564165, 424309, 424324, C07C10329

Patent

active

043372074

ABSTRACT:
Biologically active derivatives of norepinephrine are disclosed. Such derivatives are catecholamines wherein isoproterenol is modified by extending the isopropyl functional grouping to an alkyl, aryl, or alkyl-aryl chain of variable length where said chain terminates in a carboxylic acid functional group, or in a substituted amide functional group. Such derivatives are .beta.-adrenergic and a number of such derivatives e.g., 6-(.beta.-3,4-dihydroxyphenyl-.beta.-hydroxy)-ethylamino heptanoic acid p-toluide, 6-(.beta.-3,4-dihydroxyphenyl-.beta.-hydroxy)-ethylamino heptanoic acid para-n-butyl anilide; 6-(.beta.,3,4-dihydroxyphenyl-.beta.-hydroxy)-ethylamino heptanoic acid para-methoxy anilide; 6-(.beta.-3,4-dihydroxyphenyl-.beta.-hydroxy)-ethylamino heptanoic acid paratrifluoromethyl anilide; and 6-(.beta.-3,4-dihydroxyphenyl-.beta.-hydroxy)-ethylamino heptanoic acid N-methyl para-toluide display a .beta.-adrenergic activity at least several orders of magnitude greater than isoproterenol itself. Several methods of producing such active derivatives are also disclosed.

REFERENCES:
patent: 3732300 (1973-05-01), Lunts et al.
patent: 4146638 (1979-03-01), Renth et al.
Wagner et al., Synthetic Organic Chemistry, John Wiley & Sons, N.Y., N.Y., 1955, pp. 660-661.

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