Tetrahydropyrimidine derivatives

• Main Authors: SWAIN GEOFFREY, HULL ROY
• Format: Patent
• Language: English
• Published: 22.05.1962
• Subjects: CHEMISTRY; HETEROCYCLIC COMPOUNDS; METALLURGY; ORGANIC CHEMISTRY

The invention comprises compounds of the general formula: <FORM:0868030/IV (b)/1> wherein R represents an amino group and R1 an hydroxy group or R represents as C1-5 alkyl radical optionally substituted by halogen or by a morpholino radical and R1 represents a C1-5 alkoxy, a C1-5 alkyl or an anilino radical and the preparation (a) of those compounds wherein R represents an amino group, or a C1-5 alkyl radical by interaction of urea, 5-nitro-2-furaldehyde o or a functional derivative thereof and a compound R1CH2COR2 wherein R1 represents a cyano radical and R2 an hydroxy group, or R1 represents the radical R3CO wherein R3 represents a C1-5 alkyl radical and R2 a C1-5 alkoxy or an anilino radical, under acidic conditions; (b) of those compounds wherein R represents a C1-5 alkyl optionally substituted by halogen or by a morpholino radical by halogenating a compound of the general formula: <FORM:0868030/IV (b)/2> wherein R4 represents a C1-5 alkyl radical followed, if necessary, by reaction of the halogeno compound with morpholine; and (c) of those compounds wherein R and R1 represent methyl radicals by heating 5-nitro-2-furaldehyde diureide with acetylacetone in the presence of a mineral acid. The Provisional Specification discloses compounds of the general formula of the products above wherein additionally R represents a hydrocarbon radical and R1 a hydrocarbon, a hydrocarbonoxy or an amino radical, optionally substituted. 5-Nitro-2-furaldehyde diureide is obtained from 5-nitro-2-furaldehyde and urea.ALSO:Pharmaceutical compositions comprise in addition to an inert diluent or carrier one or more of the compounds of the general formula <FORM:0868030/VI/1> wherein R represents an amino group and R1 an hydroxy group or R represents a C1-5 alkyl group optionally substituted by halogen or by a morpholino radical and R1 a C1-5 alkyl, a C1-5 alkoxy or an anilino group. Compositions include ointments, creams, jellies and lotions suitable for application to the eye.