Pharmaceutically efficacious pteridine derivatives

• US 5,124,326 A
• Filed: 04/20/1990
• Issued: 06/23/1992
• Est. Priority Date: 04/21/1989
• Status: Expired due to Term

• Current Assignee: Roehm GmbH Chemische Fabrik
• Original Assignee: Roehm GmbH Chemische Fabrik
• Inventors: Mutschler, Ernst, Christner, Angelika, Hofmann, Ingrid
• Primary Examiner(s): Daus, Donald G.
• Application Number:
  US07/513,001
• Time in Patent Office: 795 Days
• Field of Search: 544/260, 544/118, 514/249, 514/234.2
• US Class Current: 514/234.2
• CPC Class Codes: A61P 7/10 Antioedematous agents; Diuretics
• CPC Class Codes: A61P 9/00 Drugs for disorders of the cardiovascular system
• CPC Class Codes: A61P 9/06 Antiarrhythmics
• CPC Class Codes: C07D 475/08 with a nitrogen atom directly attached in position 2

Abstract

A pharmaceutically efficacious pteridine compound of formula I: ##STR1## wherein A denote a bridging hydrocarbon group containing 1 to 8 carbon atoms and containing a ##STR2## group directly bonded to the phenyl group and one of the methylene radicals of the bridging A group is optionally replaced by --O--; R₁ is hydrogen, a cycloalkyl group with up to 7 carbon ring atoms, or an alkyl group having 1 to 6 carbon atoms, benzyl, or aryl; R₂ is hydrogen or an alkyl group having 1 to 6 carbon atoms, or wherein R₁ and R₂ together form a five- or six-membered heterocyclic group which optionally contains additional hetero atoms selected from the group consisting of nitrogen, oxygen, and sulfur; R₃ is hydrogen or an alkyl group having 1 to 3 carbon atoms; R₃ '"'"' is hydrogen, an optionally substituted alkyl group having 1 to 3 carbon atoms, carboxyl, hydroxyl or R₃ and R₃ '"'"' together with the carbon atom to which they are attached form a cycloalkyl group and the pharmaceutically acceptable acid addition salts thereof.

Claims

1. A pharmaceutically efficacious pteridine compound of formula I ##STR15## wherein A is cycloalkyl or --CR₃ R'"'"'₃ --(CR₃ R₄)_n --, said --CR₃ R'"'"'₃ -- moiety of said group A being directly bonded to the phenyl group of pteridine nucleus;

R₁ is hydrogen, a cycloalkyl group of up to 7 carbon ring atoms, an alkyl group of 1 to 6 carbon atoms or benzyl,

R₂ is hydrogen or an alkyl group of 1 to 6 carbon atoms, or

R₁ and R₂, together with the nitrogen atom to which they are attached, form ##STR16## wherein Y is >

CHR₇, --O-- or >

NR₈

R₆ is hydrogen or alkyl of 1 to 4 carbon atoms, R₇ and R₈ are hydrogen, alkyl of 1 to 6 carbon atoms or benzyl;

R₃ is hydrogen or an alkyl group of 1 to 3 carbon atoms;

R₃ '"'"' is hydrogen, an alkyl group of 1 to 3 carbon atoms, an alkyl group of 1 to 3 carbon atoms substituted with an OH group or an amino group, a carboxyl group or a hydroxyl group; and

R₄ is hydrogen, C_1-4 alkyl, OH or C_1-4 alkoxy;

n is 0 or 1 to 7;

or

a pharmaceutically acceptable acid addition salt thereof.

2. The compound of claim 1, wherein said salt is an acetate, hydrochloride, hydrobromide, sulfate, citrate, tartrate, succiinate, maleinate, fumarate, lactate or benzoate.

3. The compound of claim 1, wherein A is --CH₂ --, --CH(OH)--(CH₂)_n -- or --C(CH₃)₂ --(CH₂)_n --, wherein n is 0 or 1 to 7.

4. A pharmaceutical composition comprising a pharmaceutically effective amount of the compound of claim 1 in combination with a pharmaceutically effective carrier.

5. A method of achieving an anti-arrhythmic, cardioprotective, antihypertensive, anti-potassium uretic or diuretic efficacy effect, comprising:

administering a therapeutically effective amount of the composition of claim 4 to a subject in need of such effect.

6. The method of claim 5, wherein the dose of active agent ranges from 1 to 100 mg/kg of body weight.