Glycosidase inhibiting 1,4-dideoxy-4-fluoronojirimycin

Claim 2

A compound represented by the formula: ##STR18## wherein R represents hydrogen, alkyl radicals having from 1 to about 10 carbon atoms, alkenyl radicals having from 2 to about 10 carbon atoms, aryl, alkaryl and aralkyl radicals having from about 6 to about 16 carbon atoms, acyl having from about 1 to about 10 carbon atoms and carbobenzoxy; R 1 and R 2 independently represent hydrogen and hydroxy protecting groups; R 3 represents hydroxy, hydrogen and fluorine; R 4 represents hydrogen and hydroxy; or R 3 and R 4 together represent keto; and R 5 represents hydroxy, provided that when R 3 is fluorine, R 4 is hydrogen, when R 4 is hydroxy, R 3 is hydrogen and when R 3 is hydroxy, R 4 is hydrogen.

Claim 3

Compounds of claim 1 represented by the formula: ##STR19## wherein R represents hydrogen, alkyl radicals having from 2 to about 10 carbon atoms, alkenyl radicals having from 1 to about 10 carbon atoms, aryl, alkaryl and aralkyl radicals having from about 6 to about 16 carbon atoms, acyl having from about 1 to about 10 carbon atoms and carbobenzoxy.

Claim 4

A compound of claim 2 wherein R represents hydrogen.

Claim 5

A compound of claim 2 wherein R represents an alkyl radical having from 1 to about 10 carbon atoms.

Claim 6

A compound of claim 2 wherein R represents an alkyl radical having from 1 to about 6 carbon atoms.

Claim 7

A compound of claim 2 wherein R represents an alkyl radical having 4 carbon atoms.

Claim 8

A compound of claim 2 wherein R is n-butyl.

Claim 9

A compound of claim 1 represented by the formula: ##STR20## wherein R represents hydrogen, alkyl radicals having from 1 to about 10 carbon atoms, alkenyl radicals having from 2 to about 10 carbon atoms, aryl, aralkyl and alkaryl radicals having from about 6 to about 16 carbon atoms, acyl having from 1 to about 10 carbon atoms and carbobenzoxy; and R 1 and R 2 independently represent hydrogen, and hydroxy protecting groups; and R 5 represents hydroxy.

Claim 10

A compound of claim 8 wherein R represents hydrogen.

Claim 11

A compound of claim 8 wherein R represents an alkyl radical having from 1 to about 10 carbon atoms.

Claim 12

A compound of claim 8 wherein R represents an alkyl radical having from 1 to about 6 carbon atoms.

Claim 13

A compound of claim 8 wherein R represents an alkyl radical having 4 carbon atoms.

Claim 14

A compound of claim 8 wherein R is nbutyl.

Claim 15

A compound of claim 8 wherein R represents a carbobenzoxy radical.

Claim 16

A compound of claim 8 wherein R represents a butyryl radical.

Claim 17

1,4-dideoxy-4-fluoronojirimycin.

Claim 18

1,4-dideoxy-4-fluoronojirimycin.

Claim 19

N-butyl-1,4-dideoxy-4-fluoronojirimycin.

Claim 20

N-butyl-1,4-dideoxy-4-fluoronojirimycin.

Claim 21

Method of making the compound of claim 16 comprising the steps of: a) protecting the 4-hydroxy and 6-hydroxy groups of an N-protected-1-deoxynojirimycin compound; b) reacting the resulting N-protected-4,6-O-protected-1-deoxynojirimycin with a suitable hydroxy protecting group to protect the 2- and the 3-hydroxy groups; c) deprotecting the 4-hydroxy and 6-hydroxy groups; d) reacting the resulting N-protected-2,3-O-substituted-1-deoxynojirimycin with a suitable base under conditions which produce the corresponding N,6-O-carbamoyl-2,3-O-protected-1-deoxynojirimycin; e) reacting the resulting product of step d) with a suitable agent to produce the corresponding N,6-O-carbamoyl,2,3-O-protected-1, 5-dideoxy-1,5-imino-D-galactitol; f) reacting the resulting product of step e) with a suitable fluorine source to produce the corresponding N,6-O-carbamoyl-2,3-O-protected-1, 4-dideoxy-4-fluoronojirimycin; g) hydrolyzing the cyclic carbamate of the product produced in Step f); and h) deprotecting the 2-hydroxy and 3-hydroxy groups.

Claim 22

A glycosidase inhibiting composition comprising a compound of claim 1 and a pharmaceutically acceptable diluent and/or carrier.

Claim 23

A glycosidase inhibiting composition comprising a compound of claim 2 and a pharmaceutically acceptable diluent and/or carrier.

Claim 24

A glycosidase inhibiting composition comprising a compound of claim 8 and a pharmaceutically acceptable diluent and/or carrier.