2,3-didehydrosialic acid substituted with fluorine at 7-position and synthetic intermediate thereof
AssigneeDaikin Industries, Ltd.
InventorsTakao Iida, Yutaka Ohira
Life of this patent
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Abstract
The invention pertains to 2,7-Deoxy-7-fluoro-2,3-didehydrosialic acid and an intermediate thereof which are useful for developing practical drugs, such as an antiviral agent, a preventing agent for viral diseases, etc. and for a clinical application. In addition, they are also useful as a carcinostatic agent and an immunomodulation agent.
Claims11
A compound represented by the formula (I):
- ##STR16## wherein R is an aliphatic acyl group;
- R.sup.1 is a hydrogen atom or a lower alkyl group;
- each R.sup.2 is selected from the group consisting of a hydrogen atom, an aliphatic acyl group and an aromatic acyl group, and each R.sup.2 may be the same or different, provided that (i) when R.sup.1 is a hydrogen atom then each R.sup.2 is a hydrogen atom, and (ii) when R.sup.1 is a lower alkyl group then each R.sup.2 is the same or different and is selected from the group consisting of an aliphatic acyl group and an aromatic acyl group.
A compound represented by the formula (II):
- ##STR17## wherein R is an aliphatic acyl group;
- R.sup.1 is a lower alkyl group;
- each R.sup.2 is selected from the group consisting of an aliphatic acyl group and an aromatic acyl group, wherein each R.sup.2 may be the same or different;
- and R.sup.3 is a halogen atom.
A compound represented by the formula (III):
- ##STR18## wherein R is an aliphatic group;
- R.sup.1 is a lower alkyl group;
- each R.sup.2 is selected from the group consisting of a hydrogen atom, an aliphatic acyl group and an aromatic acyl group, wherein each R.sup.2 may be the same or different;
- and R.sup.4 is a thioacyl group, a thioalkyl group or a thioaryl group.
A 2,3-didehydrosialic acid derivative represented by the formula (IV):
- ##STR19## wherein Ac is an acetyl group.
A N-acetyl-7-deoxy-7-fluoro-neuraminic acid derivative represented by the formula (X):
- ##STR20## wherein R is a hydrogen atom or an alkyl group having 1 to 20 carbon atoms;
- and Ac is an acetyl group.
1,3-Di-O-acetyl-2-acetamide-2,4-dideoxy-4-fluoro-6-O- trityl-.alpha.-D-glucopyranose represented by the formula:
- ##STR21## wherein Tr is (C.sub.6 H.sub.5).sub.3 C--.
4-Deoxy-4-fluoro-D-glucosamine hydrochloride represented by the formula:
- ##STR22##
A process for producing N-acetyl-7-deoxy-7-fluoro-neuraminic acid, which comprises subjecting N-acetyl-4-deoxy-4-fluoro-D-glucosamine and sodium pyruvate to a condensation reaction in the presence of N-acetyl-neuraminic acid aldolase.
A process for producing N-acetyl-7-deoxy-7-fluoro-neuraminic acid alkyl ester, which comprises esterifying N-acetyl-7-deoxy-7-fluoro-neuramic acid by reacting with an alcohol having a C.sub.1 -C.sub.20 alkyl group.
A process for producing N-acetyl-4-deoxy-4-fluoro-D-glucosamine, which comprises subjecting 1,3-di-O-acetyl-N-acetyl-D-galactosamine to a tritylation, a fluorination, a detritylation and a hydrolysis with hydrochloric acid, and then subjecting the resulting 4-deoxy-4-fluoro-D-glucosamine hydrochloride to a N-acetylation.
Dependencies are inferred from the claim text.