US20040147591A1
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Azasugar compound
Assignee: Mitsubishi Chemical Corp
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Filing: 2003-12-04
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Granted: —
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Expires: 2023-12-04
Abstract
Abstract The present invention provides a compound represented by the formula (I) or a salt thereof: wherein R 1 represents a hydrogen atom, a C 1-10 alkyl group optionally having a substituent, or a protecting group of N; R 2 represents a C 1-10 alkyl group optionally having a substituent or a C 2-10 alkenyl group optionally having a substituent; R 3 and R 4 independently represent a hydrogen atom or a protecting group of hydroxyl group; X represents —N(R 5 )R 6 or a residue of amino acid or of an amino group of a peptide wherein R 5 and R 6 independently represent a hydrogen atom, a C 1-10 alkyl group optionally having a substituent, or a C 3-12 cycloalkyl group optionally having a substituent; and Y represents a hydrogen atom, —CH 2 NH 2 , —CONH 2 , or —COOH. The compound of the present invention is useful as a specific inhibitor of sugar chain related enzymes such as glycosyltransferase and glycosidase, and is useful as, for example, a medicine for treating or preventing diseases associated with sugar chain related enzymes.
Inventors
- 👤 Osamu Kanie
- 👤 Chikako Saotome
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-09 14:10
CPC Classifications
C; C07; C07D; C07D207/00; C07D207/02; C07D207/04; C07D207/10; C07D207/12; A; A61; A61P; A61P31/00; A61P31/12; A61P35/00; A61P37/00; A61P37/02; A61P37/04; A61P43/00; Y; Y02; Y02P; Y02P20/00; Y02P20/50; Y02P20/55
Claims Analysis
Total Claims: 12
Claim 1
Independent Claim
140 words
1 . A compound represented by the formula (I) or a salt thereof: wherein R 1 represents a hydrogen atom, a C 1-10 alkyl group optionally having a substituent, or a protecting group of N; R 2 represents a C 1-10 alkyl group optionally having a substituent or a C 2-10 alkenyl group optionally having a substituent; R 3 and R 4 independently represent a hydrogen atom or a protecting group of hydroxyl group; X represents —N(R 5 )R 6 or a residue of amino acid or of an amino group of a peptide wherein R 5 and R 6 independently represent a hydrogen atom, a C 1-10 alkyl group optionally having a substituent, or a C 3-12 cycloalkyl group optionally having a substituent; and Y represents a hydrogen atom, —CH 2 NH 2 , —CONH 2 , or —COOH.
Claim 2
Dependent Claim
140 words
1 . A compound represented by the formula (I) or a salt thereof: wherein R 1 represents a hydrogen atom, a C 1-10 alkyl group optionally having a substituent, or a protecting group of N; R 2 represents a C 1-10 alkyl group optionally having a substituent or a C 2-10 alkenyl group optionally having a substituent; R 3 and R 4 independently represent a hydrogen atom or a protecting group of hydroxyl group; X represents —N(R 5 )R 6 or a residue of amino acid or of an amino group of a peptide wherein R 5 and R 6 independently represent a hydrogen atom, a C 1-10 alkyl group optionally having a substituent, or a C 3-12 cycloalkyl group optionally having a substituent; and Y represents a hydrogen atom, —CH 2 NH 2 , —CONH 2 , or —COOH.
Claim 3
Dependent Claim
49 words
2 . The compound according to claim 1 or a salt thereof, wherein the configuration of the formula (I) is represented by the following formula (Ia): wherein R 1 , R 2 , R 3 , R 4 , x, and y are as defined in claim 1 .
Claim 4
Dependent Claim
49 words
3 . The compound according to claim 1 or a salt thereof, wherein the configuration of the formula (I) is represented by the following formula (Ib): wherein R 1 , R 2 , R 3 , R 4 , X, and Y are as defined in claim 1 .
Claim 5
Dependent Claim
49 words
4 . The compound according to claim 1 or a salt thereof, wherein the configuration of the formula (I) is represented by the following formula (Ic): wherein R 1 , R 2 , R 3 , R 4 , X, and Y are as defined in claim 1 .
Claim 6
Dependent Claim
39 words
5 . The compound according to any one of claims 1 to 4 or a salt thereof, wherein R 2 represents —CH 2 OR 12 wherein R 12 represents a hydrogen atom or a protecting group of hydroxyl group.
Claim 7
Dependent Claim
24 words
6 . An inhibitor of sugar chain related enzymes which comprises the compound of any of claims 1 to 5 or a salt thereof.
Claim 8
Dependent Claim
23 words
7 . A medicine which comprises, as an active ingredient, the compound of any of claims 1 to 5 or a salt thereof.
Claim 9
Dependent Claim
25 words
8 . The medicine according to claim 7 which is a medicine for the therapy or prevention of diseases associated with sugar chain related enzymes.
Claim 10
Dependent Claim
24 words
9 . The medicine according to claim 7 or 8 which is used as an antiviral agent, an anticancer agent, or an immunostimulant agent.
Claim 11
Dependent Claim
184 words
10 . A method for producing a compound represented by the formula (I) according to claim 1 which comprises a step of reacting a compound represented by the formula (II): wherein R 1 represents a hydrogen atom, a C 1-10 alkyl group optionally having a substituent, or a protecting group of N; R 2 represents a C 1-10 alkyl group optionally having a substituent or a C 2-10 alkenyl optionally having a substituent; and R 3 and R 4 independently represent a hydrogen atom or a protecting group of hydroxyl group; with a compound represented by the formula X—H: wherein X represents —N(R 5 )R 6 or a residue of amino acid or of an amino group of a peptide, and R 5 and R 6 independently represent a hydrogen atom, a C 1-10 alkyl group optionally having a substituent, or a C 3-12 cycloalkyl group optionally having a substituent; in the presence of a reducing agent, to produce a compound represented by the formula (III): wherein R 1 , R 2 , R 3 , R 4 and X are as defined above.
Claim 12
Dependent Claim
187 words
11 . A method for producing a compound represented by the formula (I) according to claim 1 which comprises a step of reacting a compound represented by the formula (II): wherein R 1 represents a hydrogen atom, a C 1-10 alkyl group optionally having a substituent, or a protecting group of N; R 2 represents a C 1-10 alkyl group optionally having a substituent or a C 2-10 alkenyl optionally having a substituent; and R 3 and R 4 independently represent a hydrogen atom or a protecting group of hydroxyl group; with a compound represented by the formula X—H: wherein X represents —N(R 5 )R 6 or a residue of amino acid or of an amino group of a peptide, and R 5 and R 6 independently represent a hydrogen atom, a C 1-10 alkyl group optionally having a substituent, or a C 3-12 cycloalkyl group optionally having a substituent; and a cyanation agent in the presence of Lewis acid, to produce a compound represented by the formula (IV): wherein R 1 , R 2 , R 3 , R 4 and X are as defined above.
References Cited (Backward Citations)
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