US 5,332,737 A · Amino-1,3,5-triazines and their anhydrobase derivatives as agents for cardiovascular system

Abstract

This invention concerns novel compounds of the formula I: ##STR1## in which P is a group of formula II or a group of formula III; R.sup.1 is alkyl, cycloalkyl, cycloalkylalkyl, phenyl or phenylalkyl; R.sup.2 is hydrogen, alkyl, amino or alkylamino; R.sup.3 and R.sup.4 are independently hydrogen, alkyl, phenyl or benzyl; R.sup.6 is alkyl amino or alkylamino; C and D are independently ethylene or trimethylene; Z is a direct bond between C and D, or an oxy, thio, carbonyl, methylene, ethylenedioxymethylene, ethylidene, or isopropylidene link, or Z is a group of the formula .dbd.N.R.sup.5 in which R.sup.5 is alkyl, phenyl or benzyl; R8 is hydrogen, cycloalkylalkyl, alkyl, alkenyl, alkynyl or phenylalkyl; or R8 is a alkylene or alkenylene linked to the nitrogen atom of the group Q.A.N--, either of which linking groups may optionally bear a alkyl, phenyl or phenylalkyl substituent and either of which linking groups thereby completes a ring including two adjacent carbon atoms of ring Q, any carbon atoms in A and the adjacent nitrogen atom of the group --A.N--; A is a direct bond to the the group --N(R8)-- or is alkylene; Q is a phenyl or pyridyl moiety; Y is a physiologically acceptable anion; and wherein any one or more of said phenyl, benzene or pyridyl moieties may optionally be unsubstituted or bear one or more selected substituents. The invention also includes certain closely related anhydo-base derivatives which, like the compounds of formula I, possess beneficial effects on the cardiovascular system (and in particular beneficial effects modulated via the sino-atrial node). Also included are pharmaceutical compositions containing compounds of formula I (or a related anhydro-base) as active ingrdient, and processes for the manufacture of the various novel compounds.

Claims10

Dependent claims

A compound of the formula I

wherein:
P is a group of formula ##STR27## R.sup.1 is (1-10C)alkyl, (3-8C)cycloalkyl, (3-8C)cycloalkyl-(1-4C)alkyl, phenyl or phenyl(1-4C)alkyl;
R.sup.2 is hydrogen, (1-4C)alkyl, amino or (1-4C)alkylamino;
R.sup.6 is (1-4C)alkyl, amino or (1-6C) alkylamino;
R.sup.8 is hydrogen, (3-6C)cycloalkyl-(1-4C)alkyl, (1-6C)alkyl, (3-6C)alkenyl, (3-6C)alkynyl or phenyl(1-4C)alkyl;
or R.sup.8 is a (1-4C)alkylene or (2-4C)alkenylene linked to the nitrogen atom of the group Q.A.N--, either of which linking groups may optionally bear a (1-4C)alkyl, phenyl or phenyl(1-4C)alkyl substituent and either of which linking groups thereby completes a ring including two adjacent carbon atoms of ring Q, any carbon atoms in A and the adjacent nitrogen atom of the group --A.N--;
A is a direct bond to the group --N(R.sup.8)-- or is (1-6C)alkylene;
Q is a phenyl or pyridyl moiety;
Y is a physiologically acceptable anion;
and wherein any one or more of said phenyl, benzene or pyridyl moieties in R.sup.1, R.sup.8 and Q may optionally be unsubstituted or bear one or more substituents independently selected from halogeno, (1-4C)alkyl, (3-6C)alkenyl, (1-4C)alkoxy, cyano, trifluoromethyl, nitro, amino, hydroxy, (1-4C)alkylamino, dialkylamino of up to six carbon atoms, (1-4C)alkylthio, (1-4C)alkylsulphinyl, (1-4C)alkylsulphonyl and (1-4C)alkylenedioxy;
but excluding compounds in which Q is phenyl, A is a direct bond, R.sup.1 is phenyl, R.sup.8 is hydrogen, R.sup.2 and R.sup.6 are both amino, and Y is a physiologically acceptable anion.

8 more elements

A compound selected from formula Xa or X1a (or a tautomeric form thereof) ##STR30## wherein P is a group of formula ##STR31## R.sup.8 is hydrogen, (3-6C)cycloalkyl-(1-4C)alkyl, (1-6C)alkyl, (3-6C)alkenyl, (3-6C)alkynyl or phenyl(1-4C)alkyl;

or R.sup.8 is a (1-4C)alkylene or (2-4C)alkenylene linked to the nitrogen atom of the group Q.A.N--, either of which linking groups may optionally bear a (1-4C)alkyl, phenyl or phenyl(1-4C)alkyl substituent and either of which linking groups thereby completes a ring including two adjacent carbon atoms of ring Q, any carbon atoms in A and the adjacent nitrogen atom of the group --A.N--;
A is a direct bond to the group --N(R.sup.8)-- or is (1-6C)alkylene;
Q is a phenyl or pyridyl moiety;
Ra is (1-4C)alkyl;
Rb is (1-4C)alkyl;
Rc is (1-6C)alkyl, (3-6C)alkenyl, (3-6C)alkynyl or phenyl(1-4C)alkyl;
or Rc is (1-4C)alkylene or (2-4C)alkenylene linked to the nitrogen atom of the group Qa.Aa.N--, either of which linking groups may optionally bear a (1-4C)alkyl substituent and either of which linking groups thereby completes a ring including two adjacent carbon atoms of Q and the nitrogen of group --Aa.N--;
Rd is (1-4C)alkyl;
Qa is phenyl;
Aa is a direct bond to the group --NRc--.

7 more elements

Dependencies are inferred from the claim text.

Amino-1,3,5-triazines and their anhydrobase derivatives as agents for cardiovascular system

Life of this patent

Amino-1,3,5-triazines and their anhydrobase derivatives as agents for cardiovascular system

Life of this patent

Abstract

Claims10