GB1228737A - - Google Patents

Abstract

1,228,737. Tetracycline derivatives. SOC. BOULONNAISE DE RECHERCHES ET DE DIFFUSION PHARMACEUTIQUES " SOBORE." 6 Feb., 1969 [7 Feb., 1968; 19 June, 1968], No. 6480/69. Heading C2A. Novel tetracycline derivatives of Formula (A) wherein R 1 is H or Cl; R 2 is H or methyl; and R 6 is H or OH with the proviso that when R 1 is Cl, R 6 is H; R 3 is H, or an alkyl, aryl or aralkyl group which may be substituted, R 4 is an alkyl, aryl or aralkyl group which may be substituted and each of R 5 is a chloromethyl or bromomethyl group, or both of R 5 together constitute a single bond to form an ethyleneimino ring on the terminal N atom, are prepared by a Mannich reaction of one mole of the appropriate tetracycline with one mole of an aldehyde other than formaldehyde, or a ketone or a compound capable of producing such an aldehyde or ketone in situ, and a secondary alkylamine or halo-substituted secondary alkylamine. The reaction may be carried out in a single step, or in two stages by reacting either the tetracycline or the alkylamine with the aldehyde or ketone and then reacting the product with the other reaction component. As aldehyde reactants there may be used an aldehyde, or hemiacetal, or polymer or hydrate of an aldehyde; e.g. acetaldehyde, glyceraldehyde, ortho-, meta- or para - N,N - bis - # - chloroethylaminobenzaldehyde or ethyleneiminobenzaldehyde. Pharmaceutical compositions having antitumour, immunosuppressive and antibiotic activity comprise the tetracycline derivatives of Formula A above together with a pharmaceutically acceptable diluent or carrier.