Patent GB-971166-A (GB)
Title: Substituted triazino-pyrimidines
IPC: C07D239/42
Filed: 1961-01-31
Abstract: 971,166. Substituted triazino [5,4-d]-pyrimidines. KARL THOMAE G.m.b.H. Jan. 31, 1961 [Feb. 2, 1960], No. 3697/61. Heading C2C. The invention comprises V-triazino [5,4-d]- pyrimidines of the general formula wherein R<SP>1</SP> and R<SP>2</SP> are the same or different and each represent a hydrogen or halogen atom, a substituted or unsubstituted amino group, a hydroxy or ether group or the corresponding thio group, or a nitrogen atom forming part of a heterocyclic ring which may contain a further hetero atom, and R<SP>3</SP> represents a hydroxy or ether group or the corresponding thio group, a substituted or unsubstituted amino group or a nitrogen atom forming a part of a heterocyclic ring which may contain a further hetero atom; and salts thereof; and tautomers thereof and their salts in which at least one of R<SP>1</SP>, R<SP>2</SP> and R<SP>3</SP> represent hydroxy groups, said tautomers being compounds in which at least one of R<SP>1</SP>, R<SP>2</SP> and R<SP>3</SP> represent oxo groups, and N-alkyl, N-alkenyl, N-hydroxyalkyl, N-aralkyl and N- aryl derivatives of said tautomers; and the preparation of the above V-triazino [5,4-d]- pyrimidines of the above general formula wherein R<SP>3</SP> represents a hydroxy, mercapto or amino group or a tautomer of such a compound in which R<SP>3</SP> represents a hydroxy group by reacting a substituted pyrimidine of the general formula wherein R<SP>1</SP> represents a hydrogen or halogen atom, a mono- or di-substituted amino group, a hydroxy or ether group or the corresponding thio group or a nitrogen atom forming part of a heterocyclic ring which may contain a further hetero atom, R<SP>2</SP> represents any of the groups which may be represented by R<SP>1</SP> except a monosubstituted amino group, and X represents a mono-substituted or unsubstituted amido, thioamido or amidino group, with a diazotising agent such as an organic or inorganic nitrite under conditions forming nitrous acid therefrom; a process for the preparation of the above N- alkylated, N-alkenylated or N-aralkylated tautomers by treating a compound of the first general formula above, wherein at least one of R<SP>1</SP>, R<SP>2</SP> and R 3 represent a hydroxy group, with an alkylating, alkenylating or aralkylating agent such as the required halide or sulphate; a process for the preparation of compounds of the first general formula above wherein one or more of the symbols R<SP>1</SP>, R<SP>2</SP> and R<SP>3</SP> represent a substituted or unsubstituted amino group, by reacting compounds of the first general formula above, wherein one or more of the symbols R<SP>1</SP>, R<SP>2</SP> and R<SP>3</SP> represent a hydroxy group and R<SP>2</SP> is other than an unsubstituted or monosubstituted amino group with ammonia or the required amine; a process for the preparation of compounds of the first general formula above, wherein at least one of the symbols R<SP>1</SP> and R<SP>2</SP> represents a halogen atom or a mercapto group, by treating a compound of the first general formula above wherein at least one of the symbols R<SP>1</SP> and R<SP>2</SP> represents a hydroxy group, with a phosphorus halide or phosphorus pentasulphide; a process for the preparation of compounds of the first general formula above, wherein at least one of the groups R<SP>1</SP> and R<SP>2</SP> represents a substituted or unsubstituted amino group, a mercapto group or an ether or thioether group, or a nitrogen atom forming part of a heterocyclic ring which may contain a further hetero atom, by reacting a compound of the first general formula above in which at least one of the symbols R<SP>1</SP> and R<SP>2</SP> represents a halogen atom with ammonia, an amine, or a sulphide, a substituted sulphide, or a substituted hydroxide such as an alkali metal sulphide or alkyl-, aralkyl- or aryl-sulphide or an alkali metal alkoxide, aralkoxide or aryloxide, or a heterocyclic compound containing an imino nitrogen atom and, if desired, a further hetero atom; and a process for the preparation of compounds of the first general formula above wherein R<SP>3</SP> represents a substituted or unsubstituted amino group, a mercapto group or an ether or thioether group, or a nitrogen atom forming part of a heterocyclic ring which may contain a further hetero atom, by reacting a compound of the first general formula above, wherein the symbol R<SP>3</SP> is replaced by a halogen atom, with ammonia, an amine, a heterocyclic compound containing an imino nitrogen atom and, if desired, a further hetero atom, a sulphide, a substituted sulphide or substituted hydroxide. Therapeutic compositions contain one or more V-triazino-[5,4-d]-pyrimidines of the first general formula above and a pharmaceutical carrier. The compositions may be in the form of tablets, dragees, capsules, lozenges, ampoules, suppositories, syrups, elixirs, or injectable preparations.