Method of preparing n-oxo-tetrahydro-.beta.-carbolines

Details Method of preparing n-oxo-tetrahydro-.beta.-carbolines Method of preparing n-oxo-tetrahydro-.beta.-carbolines

C - Chemistry, Metallurgy

07

D

167/208, 260/238

C07D 498/14 (2006.01) A61K 31/535 (2006.01) A61K 31/55 (2006.01) C07D 515/14 (2006.01)

Patent

CA 2018253

DIR 0443 Abstract The invention relates to a method of preparing N-oxo- tetrahydro-.beta.-carbolines having formula 1. Image (1) wherein - R1 is lower alkyl or alkoxy, halogen, tri- fluoromethyl, lower alkylthio, hydroxy, amino, lower mono- or dialkyl- or acylamino, - n has the value 0, 1 or 2, - R2 is hydrogen, lower alkyl or acyl, - R3 is hydrogen, lower alkyl or alkoxycarbonyl, or a phenyl group optionally substituted with a group R1, and - A together with the group -C-N-O-, forms a saturated heterocyclic ring system consisting of 6-8 ring atoms, wherein, in addition to the already present oxygen atom and nitrogen atom, an extra hetero atom Prom the group O, S and N may be present, which ring system may be substituted with one or more of the sub- stituents alkyl, alkoxycarbonyl, alkanoyl, alkoxy, hydroxy, oxo, amino, mono- or dialkylamino, alkanoyl- or alkoxycarbonylamino, which ring system may be annelated with a saturated carbocyclic group of 5 or 6 ring atoms, by an intramolecular ringclosure reaction DIR 0443 of compounds of formula 2 Image (2) wherein Z is an aldehyde function or acetal function, or is a functional group which can be converted into such a function during the ringclosure reaction. The eudistomin derivatives within the group of compounds having formula 1 have strong antiviral and antitumour activity.

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