2,3-diamino-2,3-didesoxyhexose derivatives and their use

Details 2,3-diamino-2,3-didesoxyhexose derivatives and their use 2,3-diamino-2,3-didesoxyhexose derivatives and their use

1985-12-18

1987-10-06

Brown, Johnnie R.

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Carbohydrate doai

514 23, 536 172, 536 179, 536 187, A61K 3170, C07H 506

Patent

active

046983317

DESCRIPTION:

BRIEF SUMMARY
The present invention concerns 2,3-diamino-2,3-didesoxyhexose derivatives, processes for their preparation, pharmaceutical compositions containing them and their use as pharmaceuticals especially as immunostimulants.
More particularly the invention concerns compounds of formula I ##STR2## wherein R.sub.2 and R.sub.3 are the same or different and each represent unsubstituted or substituted acyl, pyrophosphate, phosphorylethanolamine or pyrophosphorylethanolamine group, R.sub.4 represents the phosphate, pyrophosphate, phosphorylethanolamine or pyrophosphorylethanolamine group and one of R.sub.1 and R.sub.4 may additionally represent hydrogen and R.sub.5 represents hydrogen or a glycosyl radical R.sub.5 represent hydrogen.
The compounds of formula I may be obtained according to the invention by (a), to prepare compounds of formula Ia, ##STR3## acylating the corresponding compound of formula II ##STR4## whereby R.sub.2 and R.sub.3 are the same and are as defined above and R.sub.1.sup.I stands for hydrogen, lower alkyl or aralkyl,
(b), to prepare a compound of formula Ia wherein R.sub.2 and R.sub.3 are different acylating a compound of formula IIa, ##STR5## wherein R.sub.1.sup.I and R.sub.3 are as defined above or
(c), to prepare a compound of formula Ib, ##STR6## wherein R.sub.2 to R.sub.5 are as defined above and pyrophosphate, phosphorylethanolamine or pyrophosphorylethanolamine group whereby R.sub.1.sup.II and R.sub.4 are not simultaneously hydrogen, reacting a compound of formula Ic, ##STR7## wherein R.sub.2 and R.sub.3 are as defined for formula I, group and R.sub.1.sup.III and R.sub.4.sup.I are not simultaneously protecting groups, and R.sub.5.sup.I represents a protecting group or a glycosyl radical with a corresponding phosphorous compound obtained.
Processes (a) and (b) can be carried out for example by dissolving the compound of formula II or IIa together with the acylating agent in a solvent inert under the reaction conditions e.g. in a di-(lower)alkylcarboxylic acid amide such as dimethylformamide and allowing them to react at room temperature.
Process (c) can be carried out for example by dissolving a compound of formula Ic in a solvent inert under the reaction conditions e.g. in a cyclic ether such as tetrahydrofuran reacting same at low temperature e.g. -70.degree. with butyllithium in an aliphatic hydrocarbon e.g. in hexane and then adding phosphorochloridate. The free OH groups of the phosphate radical may also be protected e.g. by benzyl and these protecting groups can be removed after reaction e.g. hydrogenolytically.
Other protecting groups may also be removed in conventional manner. Thus, for example, protecting groups as R.sub.1.sup.III or R.sub.4.sup.I are usually removed acidically e.g. with an aqueous acid (ion exchanger).
End products can be isolated and purified in conventional manner.
The compounds of formula II are also new and form part of the invention. They can be prepared e.g. according to the following reaction scheme ##STR8## R.sub.1.sup.IV =lower alkyl or aralkyl, Ac=acetyl. The compounds of formulae IVa and IVb may be directly reduced to compounds of formula II.
By controlling the reaction conditions (e.g. time, quantity of catalyst) it is possible, to prepare the compounds of formula IIa, by in a first step reducing only the azido group. Following protection of the resulting amino group the nitro group can be reduced. In this manner starting materials of formula IIa may be obtained from which end-products wherein R.sub.2 and R.sub.3 are different may be prepared. ##STR9##
The compounds of formula Ic can be prepared from compounds of formula Ia or Ib wherein R.sub.2 and R.sub.3 are the same or different e.g. according to the following reaction scheme ##STR10##
The compounds, Id, Ie, If may be protected as appropriate in conventional manner.
The remaining starting materials are either known or may be prepared analogously to known compounds.
R.sub.2 and R.sub.3 are the same or different preferably the same and represent an acyl group such as an alkylcarbonyl group having for

REFERENCES:
patent: 4384998 (1983-05-01), Durette
patent: 4481196 (1984-11-01), Teraji et al.

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