EP0098252A2
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EP
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New and novel glycosides, glycoconjugates and processes for their preparation
Assignee: Biocarb AB
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Filing: 1983-06-21
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Granted: —
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Expires: 2003-06-21
Abstract
Abstract An O-glycoside having the general formula:wherein Hal is chlorine, bromine or iodine, m is an integer of 2-20 inclusive and n is an integer of 1 to 10, inclusive, with the proviso that when n = 1 and m = 2, the aldose is different from glucose;An O-glycoside having the general formula:wherein n is an integer of from 1-10, inclusive, m is an integer of from 2-20, inclusive, R is selected from the group consisting of alkyl having at most 25 carbon atoms and aryl and R' is selected from the group consisting of H, CHO, CH(OR")<sub>2</sub>, NO2, NH<sub>2</sub>, OH, SH, COOH, COOCH<sub>3</sub>, COOCH<sub>2</sub>CH<sub>3</sub>, CONHNH<sub>2</sub> and CON<sub>3</sub>, wherein R" is C<sub>1-4</sub>-alkyl;A glycoconjugate having the general formula:wherein n is an integer of from 1-10, inclusive, m is an integer of from 2-20, inclusive, R is selected from the group consisting of alkyl having at most 25 carbon atoms and aryl and R" constitutes a carrier;A bi-dentate 0-glycoside having the general formula:wherein m, n and R have the above meaning; and processes for their preparation.
Inventors
- 👤 Jan Dahmén
- 👤 Torbjörn Frejd
- 👤 Göran Magnusson
- 👤 Ghazi Noori
Bibliographic Details
Application Number
—
Jurisdiction
EP
Data Source
google_patents
Last Synchronized
2026-11-07 11:11
CPC Classifications
C; C07; C07H; C07H3/00; C07H3/06; A; A61; A61K; A61K39/00; A61K39/385; A61K2039/60; A61K2039/6031; A61K2039/6087
Claims Analysis
Total Claims: 17
Claim 1
Independent Claim
81 words
An 0-glycoside having the general formula: wherein n is an integer of from 1-10, inclusive, m is an integer of from 2-20, inclusive, R is selected from the group consisting of alkyl having at most 25 carbon atoms and aryl and R' is selected from the group consisting of H, CHO, CH(OR'') 2 , N0 2 , NH 2 , OH, SH, COOH, COOCH 3 , COOCH 2 CH 3 , CONHNH 2 and CON3, wherein R" is C 1-4 -alkyl.
Claim 2
Dependent Claim
81 words
An 0-glycoside having the general formula: wherein n is an integer of from 1-10, inclusive, m is an integer of from 2-20, inclusive, R is selected from the group consisting of alkyl having at most 25 carbon atoms and aryl and R' is selected from the group consisting of H, CHO, CH(OR'') 2 , N0 2 , NH 2 , OH, SH, COOH, COOCH 3 , COOCH 2 CH 3 , CONHNH 2 and CON3, wherein R" is C 1-4 -alkyl.
Claim 3
Dependent Claim
37 words
Glycoside according to claim 1, wherein the sugar is an aldose selected from the group consisting of D-glucose, D-galactose, D-mannose, D-xylose, L-fucose, 2-acetamido-2-deoxy-D-glucose, 2-deoxy-2-phthalimido-glucose, 2-acetamido-2-deoxy-D-galactose, 2-azido-2-deoxy-D--glucose, 2-azido-2-deoxy-D-galactose, D-glucuronic acid and D-galacturonic acid, 2-deoxy-2-phthalimido glucose and 2-deoxy-2-phthalimido galactose.
Claim 4
Dependent Claim
20 words
An 0-glycoside according to claim 1 including a spacer arm, wherein R is alkyl and R' is COOCH 3 .
Claim 5
Dependent Claim
14 words
An 0-glycoside according to claim 3, wherein R is CH 2 -CH 2 .
Claim 6
Dependent Claim
12 words
An 0-glycoside according to claim 3 or 4, wherein m is 2.
Claim 7
Dependent Claim
30 words
An 0-glycoside according to claim 1, wherein m is 2, R is (CH 2 ) 1 , where 1 is an integer of up to 24, and R' is methyl.
Claim 8
Dependent Claim
26 words
An 0-glycoside according to claim 6 in the form of a glycolipid selected from the group: and wherein 1 is < 24, e.g. 7 or 17.
Claim 9
Dependent Claim
136 words
A process for preparing an 0-glycoside having the general formula: wherein n is an integer of from 1-10, inclusive, m is an integer of from 2-20, inclusive, R is selected from the group consisting of alkyl having at most 25 carbon atoms and aryl and R' 'is selected from the group consisting of H, CHO, CH(OR") 2 , N0 2 , NH 2 , OH, SH, COOH, COOCH 3 , COOCH 2 CH 3 , CONHNH 2 and CON 3 , wherein R" is C 1-4 -alkyl, comprising: reacting an Halo alkyl 0-glycoside having the general formula: wherein Hal is chlorine, bromine or iodine, m is an integer of 2-20 inclusive and n is an integer of 1 to 10, inclusive, with a thiol of the general formula: wherein R and R' have the above meaning.
Claim 10
Dependent Claim
136 words
A process for preparing an 0-glycoside having the general formula: wherein n is an integer of from 1-10, inclusive, m is an integer of from 2-20, inclusive, R is selected from the group consisting of alkyl having at most 25 carbon atoms and aryl and R' 'is selected from the group consisting of H, CHO, CH(OR") 2 , N0 2 , NH 2 , OH, SH, COOH, COOCH 3 , COOCH 2 CH 3 , CONHNH 2 and CON 3 , wherein R" is C 1-4 -alkyl, comprising: reacting an Halo alkyl 0-glycoside having the general formula: wherein Hal is chlorine, bromine or iodine, m is an integer of 2-20 inclusive and n is an integer of 1 to 10, inclusive, with a thiol of the general formula: wherein R and R' have the above meaning.
Claim 11
Dependent Claim
45 words
A glycoconjugate having the general formula: wherein n is an integer of from 1-10, inclusive, m is an integer of from 2-20, inclusive, R is selected from the group consisting of alkyl having at most 25 carbon atoms and aryl and R" constitutes a carrier.
Claim 12
Dependent Claim
45 words
A glycoconjugate having the general formula: wherein n is an integer of from 1-10, inclusive, m is an integer of from 2-20, inclusive, R is selected from the group consisting of alkyl having at most 25 carbon atoms and aryl and R" constitutes a carrier.
Claim 13
Dependent Claim
28 words
A glycoconjugate according to claim 7 having the formulae: and wherein R"' is selected from the group consisting of residues of proteins, polysaccharides, plastic materials and inorganic materials.
Claim 14
Dependent Claim
19 words
A bi-dentate 0-glycoside having the general formula: wherein m, n and R have the meaning given in claim 9.
Claim 15
Dependent Claim
17 words
An alkyl 0-glycoside having the formula: wherein n and m have the meaning given in claim 1.
Claim 16
Dependent Claim
12 words
An alkyl 0-glycoside according to claim 12 selected from the group: and
Claim 17
Dependent Claim
24 words
A process for preparing alkyl 0-glycosides comprising: dehalogenating a Haloalkyl 0-glycoside according to claim 8 using gaseous hydrogen, and recovering the alkyl 0-glycoside formed.
References Cited (Backward Citations)
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