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 N-substituted pseudo-aminosugars, their production and use

Details
Inventors: Horii, Satoshi; Kameda, Yukihiko; Fukase, Hiroshi;
Assignee: Takeda Chemical Industries, Inc. (Osaka, JP)
Primary Examiner: Hines; Robert V.
Assistant Examiner:
Attorney, Agent or Firm: Wegner & Bretschneider

A compound of the formula: ##STR1## wherein A is a chain hydrocarbon group having 1 to 10 carbon atoms optionally substituted by hydroxyl, phenoxy, thienyl, furyl, pyridyl, cyclohexyl or an optionally substituted phenyl group, or a cyclic hydrocarbon group having 3 to 7 carbon atoms optionally substituted by hydroxyl, B is hydrogen or hydroxyl, and their production and use. These compounds exhibit excellent inhibitory activity against .alpha.-glucoside hydrolase, thus are useful for hyperglycemic symptoms and various disorders caused by hyperglycemia.

DETAILED DESCRIPTION What is claimed is: 1.
A compound of the formula: ##STR35## wherein A is a chain hydrocarbon group having 1 to 10 carbon atoms which may be substituted by hydroxyl, phenoxy, thienyl, furyl, pyridyl, cyclohexyl or a phenyl which may be substituted by hydroxyl, lower alkoxy, lower alkyl or halogen group.
2.
A compound of the formula ##STR36## wherein A is a chain hydrocarbon group having 1 to 10 carbon atoms which may be substituted by hydroxyl, phenoxy, cyclohexyl or phenyl which may be substituted with hydroxyl, lower alkoxy, lower alkyl or halogen.
3.
A compound as claimed in claim 1, wherein A is a chain hydrocarbon of 1 to 6 carbon atoms which may be substituted by hydroxyl or phenyl group optionally substituted by halogen.
4.
A compound as claimed in claim 3, namely N-(1,3-dihydroxy-2-propyl)valiolamine.
5.
A compound as claimed in claim 1 or 3, namely N-(.
beta.
-hydroxyphenethyl)valiolamine.




Description:
The present invention relates to N-substituted Pseudo-aminosugars having an inhibitory activity against glucoside hydrolase, to processes for producing the same, and to .
alpha.
-glucosidase inhibitors containing the above-mentioned derivatives.
The present inventors previously isolated as a constituent of validamycin, an antibiotic, the compound of the formula ##STR2## , which was named "valienamine" (Y.
Kameda and S.
Horii; Journal of the Chemical Society; Chemical Communications, 1972, 746 to 747), and reported that valienamine possesses an action of suppressing the function of .
alpha.
-glucoside hydrolase (Y.
Kameda et al.
, Journal of Antibiotics 33, 1575 to 1576 (1980)).
In recent years, various compounds having valienamine moiety, which exhibit .
alpha.
-glycosidase inhibitory activity, are reported e.
g.
"Acarbose" in U.
S.
Pat.
No.
4,062,950, "Trestatin A, B and C" in German laid open patent application No.
2,905,649 but their actions to suppress the function of .
alpha.
-glucoside hydrolase are unsatisfactory.
The present inventors investigated an



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