Patent GB-873223-A (GB)
Title: Heterocyclic compounds
Inventor: MILLER GEORGE WILLIAM
IPC: C07D487/04
Filed: 1959-04-13
Abstract: The invention comprises mono-acyl derivatives of amines of the formula <FORM:0873223/IV (b)/1> (wherein R1, R2 and R3, which may be the same or different, are alkyl radicals which may be substituted by alkoxy radicals or halogen atoms, alkenyl, cycloalkyl or alkylthio radicals or halogen atoms, or R2 and R3 may be joined to form a polymethylene chain, or R3 is a hydrogen atom), the mono-acyl radical having the formula -COR4 wherein R4 is hydrogen, an alkyl radical which may be substituted by halogen atoms or a phenoxy radical, an aryl radical which may be substituted by nitro or methoxy radicals, an alkenyl radical which may be substituted by a carboxy radical, an aralkenyl radical or an alkoxy radical; and salts thereof; and their preparation by acylation of amines of the above formula. Suitable acylating agents include the acid R4COOH, the acid halide or the acid anhydride.  Examples are given and salts with alkali metal hydroxides and strong organic bases are referred to. An acetate salt also is described. In the Provisional Specification R1, R2 and R3 are defined as hydrogen or halogen atoms or hydrocarbon or alkylthio radicals and R4 is defined as an alkyl, substituted alkyl, aryl, substituted aryl or alkoxy group.  Specification 859,287 is referred to.ALSO:Pharmaceutical compositions comprise one or more mono-acyl derivatives of amines of the formula <FORM:0873223/VI/1> (wherein R1, R2 and R3, which may be the same or different, are alkyl radicals which may be substituted by alkoxy radicals or halogen atoms, alkenyl, cycloalkyl or alkylthio radicals or halogen atoms, or R2 and R3 may be joined to form a polymethylene chain, or R3 is a hydrogen atom), the mono-acyl radical having the formula -COR4, wherein R4 is hydrogen, an alkyl radical which may be substituted by halogen atoms or a phenoxy radical, an aryl radical which may be substituted by nitro or methoxy radicals, an alkenyl radical which may be substituted by a carboxy radical, an aralkenyl radical or an alkoxy radical, or a salt thereof, in admixture with a non-toxic pharmaceutical carrier or diluent.  Compositions for oral use may take the form of tablets, pills, capsules, syrups, solutions, suspensions or dispersible powders; for parenteral administration they may take the form of an injectable solution or suspension in an aqueous or oily medium or a sterile powder or dispersible powder from which an injectable solution or suspension can be prepared; and for topical application they may take the form of powders for insufflation, sprays for inhalation or aerosol preparations.  The compositions, in which the amount of active ingredient per dosage unit is desirably between 1 mg. and 750 mg., may also contain an antihistamine or other anti-inflammatory agent, e.g. 9-(2-methylaminopropyl)-10-thia - 1,9 - diaza - anthracene, prednisolone or hydrocortisone, or a sedative, e.g. phenobarbitone, or an antibacterial agent, e.g. sulphadimidine or penicillin V. Compositions containing 2-acetamido-7-methyl-5-n-propyl-s-triazolo-[2,3-c]-pyrimidine as the active ingredient, in the form of a syrup for paediatric use, which may also contain a flavouring agent, an oral preparation for use as a throat spray, a powdered preparation for insufflation, tablets, an aerosol formulation, soft capsules, enteric coated tablets and sugar coated tablets, are described in examples. Salts with alkali metal hydroxides and strong organic bases are also referred to, and an acetate salt also is described.  In the Provisional Specification R1, R2 and R3 are defined as hydrogen or halogen atoms or hydrocarbon or alkylthio radicals and R4 is defined as an alkyl, substituted alkyl, aryl, substituted aryl or alkoxy group.  Specification 859,287 is referred to.