US 3,946,004 A · Phenothiazines, phenoxazines and acridan bis-pyrrolinyl derivatives

Abstract

Novel amidine compounds selected from the group consisting of bis-pyrrolinyl derivatives of phenothiazines, phenoxazines and acridans are obtained by reacting a phenothiazine, phenoxazine or acridan with a pyrrolidinone in the presence of phosphorus oxychloride. The phenothiazine, phenoxazine, or acridan can also be alkylated with 2-chloro-1-(1-pyrrolin-2-yl)-2-pyrroline to provide compounds of the invention. Typical examples of bis-pyrrolinyl derivatives are 2-methoxy-10-[5-methyl-1-(5-methyl-1-pyrrolin-2-yl)-2-pyrrolin-2-yl]-pheno thiazine, 10-[1-(1-pyrrolin-2-yl)-2-pyrrolin-2-yl]phenoxazine, and 9,9-dimethyl-10-[5-methyl-1-(5-methyl-1-pyrrolin-2-yl)-2-pyrrolin-2-yl]acr idan. The amidine compounds are useful as diuretics, smooth muscle relaxants and antithrombogenic agents.

Claims7

Dependent claims

A compound selected from the group consisting of 10-(bis-pyrrolinyl)phenothiazines[, 10-bis-pyrrolinyl)acridans and 10-(bis-pyrrolinyl)phenoxazines]represented by [Formula 1] ##SPC4##

and non-toxic pharmaceutically acceptable acid addition salts thereof wherein
X is sulfur
Y represents hydrogen, trifluoromethyl, halogen, lower alkyl of from 1 to 4 carbon atoms inclusive or lower alkoxy of 1 to 4 carbon atoms inclusive;
and
R represents hydrogen or straight chain lower alkyl of 1 to 4 carbon atoms inclusive.

2 more elements

Dependencies are inferred from the claim text.

Facts

Application

05/521,618Filed 6 Nov 1974 · continuation in part

Priority

27 May 1971

Granted

23 Mar 1976

Term ends

Not estimatedThe source records don’t support an estimate.

Classification5 codes

C07D 417/04
Containing two hetero rings: directly linked by a ring-member-to-ring-member bond
C07D 401/14
Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a…:…
C07D 413/14
Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms:…
C07D 417/14
Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms,…

Phenothiazines, phenoxazines and acridan bis-pyrrolinyl derivatives

Life of this patent

Phenothiazines, phenoxazines and acridan bis-pyrrolinyl derivatives

Life of this patent

Abstract

Claims7