Patent GB-1009809-A (GB)
Title: New oxazine derivatives and processes for their preparation
IPC: C07D213/81
Filed: 1962-11-06
Abstract: The invention comprises compounds of the general formula <FORM:1009809/C2/1> wherein R1 is a hydrogen atom or an alkyl radical having at most 4 carbon atoms and R2 is a hydrogen atom; a monovalent aliphatic or cyclo-aliphatic radical having at most 12 carbon atoms which may also contain halogen atoms, hydroxyl, ether carbonyl, carboxyl or carbalkoxy, alkylthio, nitrile, amido, or tertiary amino groups; phenyl; phenylalkyl; phenoxyalkyl; phenylalkenyl; heterocyclylalkyl having at most 12 carbon atoms and, if desired, the aromatic homocyclic and heterocyclic rings may be substituted by at most 3 substituents from the series: alkyl, alkoxy, trifluoromethyl, hydroxyl, nitro, amino groups and halogen atoms, and, in the aliphatic radical of these substituents, a methylene group may be replaced by a carbonyl group; an N-alkyl-N-phenyl-carbamoyl or a piperidino carbonylalkyl group having in all 12 carbon atoms, at most, and the preparation thereof by reacting a compound of the general formula <FORM:1009809/C2/2> under condensation reactions with a reactive carbonic acid derivative, especially with a derivative X-CO-Y, where X and Y independently of each other are hydrocarbon radicals each bound by way of an oxygen atom, a halogen atom, an NHR2 or 1-imidazole residue, and where the carbonic acid derivative is ClCOY1, where Y1 is chlorine methoxy, ethoxy or phenoxy, if desired, reacting a metal salt, preferably an alkali metal salt, of I, so obtained, wherein R2 is hydrogen, with a reactive ester of R21OH, where R21 is as defined under R2 with the exception of a phenyl radical which may be substituted; or, in a modification of the foregoing process, separating the compounds <FORM:1009809/C2/3> where R is an alkyl radical or a benzyl radical and Rx is an alkyl radical or a phenyl radical (the alkyl radicals having at most 6 carbon atoms) and heating the intermediates in an inert solvent; or by reacting a compound of the general formula <FORM:1009809/C2/4> wherein R1 is an alkyl group of at most 6 carbon atoms, in the presence of a base, with an isocyanate R2NCO or, if desired, converting the intermediate product formed in this reaction, i.e. compounds of the formula <FORM:1009809/C2/5> into I by heating; or by reacting a compound I where R2 is hydrogen with a compound H2C=CH-R11 where R11 is a cyano-, alkoxycarbonyl, acetyl, benzoyl, 2- or 4-pyridyl residue; or by reacting a compound I, wherein R2 is hydrogen with formaldehyde and a secondary amine HNR3R4 wherein each R3 and R4 are either an alkyl radical having at most 3 carbon atoms or together they represent a saturated heterocycle. Compound of formula I, wherein R2 contains an alkenylene residue may be hydrogenated to the corresponding alkylene residue; radicals containing nitro groups may be reduced to those containing amino groups and amino groups may in turn be converted into hydroxyl groups.  Pharmaceutical compositions having analgesic, antipyretic, antiphlogistic, muscle relaxing, baterostatic, fungistatic and monoamine-oxidase inhibitory activity comprise the oxazines of the invention together with a pharmaceutically acceptable carrier.