Biologically active catecholamine derivatives

US4337207A · kind A · utility

Assignee

• The Regents of the University of California · US

Inventors

• Murray Goodman · Village of La Jolla, US
• Michael S. Verlander · Del Mar, US
• Kenneth A. Jacobson · Silver Spring, US
• Kenneth L. Melmon · Woodside, US
• Neal Castagnoli · San Rafael, US

Key dates

• Filing date: Sep 4, 1980
• Grant date: Jun 29, 1982
• Expiry date: Sep 4, 2000

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07C233/00
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

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.