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US 2010/0143980 A1Published application

Synthesis of novel xylosides and potential uses thereof

OwnerKuberan Balagurunathan, Ethirajan Manivannan +3inventors

InventorsKuberan Balagurunathan, Ethirajan Manivannan, V. Victor Xylophone, Vy My Tran, Khiem Nguyen

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Abstract Drawings Claims Description

Abstract

The present invention includes a xyloside for use in inducing synthesis of a glycosaminoglycan in a cell, the xyloside having a chemical structure of one of Formula (1), Formula (2), Formula (3), Formula (4), Formula (5), Formula (6), Formula (7), Formula (8), Formula (9), or Formula (10) as shown herein. Also, the present invention includes a method of making a xyloside for use in inducing synthesis of a glycosaminoglycan in a cell, wherein the method is performed with “Click” chemistry. Additionally, the present invention includes a method of administering a xyloside so as to induce synthesis of a glycosaminoglycan in a cell.

Claims14

Dependent claims

Claim 1A xyloside for use in inducing synthesis of a glycosaminoglycan in a cell · 273 words6 dependent Claim 2A xyloside for use in inducing synthesis of a glycosaminoglycan in a cell · 258 words6 dependent Claim 3A xyloside for use in inducing synthesis of a glycosaminoglycan in a cell · 112 words6 dependent Claim 4A xyloside for use in inducing synthesis of a glycosaminoglycan in a cell · 239 words6 dependent Claim 5A xyloside for use in inducing synthesis of a glycosaminoglycan in a cell · 257 words6 dependent Claim 6A method of making a xyloside for use in inducing synthesis of a glycosaminoglycan in a cell · 373 words6 dependent Claim 7A method of making a xyloside for use in inducing synthesis of a glycosaminoglycan in a cell · 361 words6 dependent Claim 8A method of using a xyloside for inducing synthesis of a glycosaminoglycan in a cell · 308 words6 dependent

A xyloside for use in inducing synthesis of a glycosaminoglycan in a cell, the xyloside comprising:

a chemical structure of one of Formula 1, Formula 2, Formula 3, Formula 4, Formula 5, Formula 6, Formula 7, Formula 8, Formula 9, or Formula 10;
n is from 0 to 10;
m is from 0 to 10;
X is one of a bond, S, SO2, O, N, or C;
R is one of H, CH2OH, halogen, COOH, acetyl-oxy, monosaccharide, disaccharide, oligosaccharide, or OH;
R′ is one of H, CH2OH, halogen, COOH, acetyl-oxy, monosaccharide, disaccharide, oligosaccharide, or OH;
R″ is one of H, CH2OH, halogen, COOH, acetyl-oxy, monosaccharide, disaccharide, oligosaccharide, or OH;
R″′ is one of H, CH2OH, halogen, COOH, acetyl-oxy, monosaccharide, disaccharide, oligosaccharide, or OH;
R″″ is one of H, CH2OH, halogen, COOH, acetyl-oxy, monosaccharide, disaccharide, oligosaccharide, or OH;
R″″′ is one of H, CH2OH, halogen, COOH, acetyl-oxy, monosaccharide, disaccharide, oligosaccharide, or OH;
and
R* is selected from the group consisting of H, OH, CH2OH, an unsubstituted aliphatic group, a substituted aliphatic group, a halo substituted aliphatic group, a straight chain aliphatic group, a branched chain aliphatic group, alkoxy, a cyclic aliphatic group, an aliphatic group having at least one hetero chain atom, a cyclic aliphatic group having at least one hetero ring atom, an unsubstituted aromatic group, a substituted aromatic group, a halo substituted aromatic group, a polyaromatic group, a substituted polyaromatic group, an aromatic group having at least one hetero ring atom, a polyaromatic group having at least one hetero ring atom, a nucleoside, a nucleotide, a carbohydrate, monosaccharide, disaccharide, oligosaccharide, a polysaccharide;
an amino acid, a polypeptide, combinations thereof, and derivatives thereof.

10 more elements

A xyloside for use in inducing synthesis of a glycosaminoglycan in a cell, the xyloside comprising:

a chemical structure of one of Formula 1, Formula 2, Formula 3, or Formula 4;
n is from 0 to 10;
m is from 0 to 10;
X is one of S, O, N, or C;
R is one of H, CH2OH, halogen, COOH, acetyl-oxy, monosaccharide, disaccharide, oligosaccharide, or OH;
R′ is one of H, CH2OH, halogen, COOH, acetyl-oxy, monosaccharide, disaccharide, oligosaccharide, or OH;
R″ is one of H, CH2OH, halogen, COOH, acetyl-oxy, monosaccharide, disaccharide, oligosaccharide, or OH;
R″′ is one of H, CH2OH, halogen, COOH, acetyl-oxy, monosaccharide, disaccharide, oligosaccharide, or OH;
R″″ is one of H, CH2OH, halogen, COOH, acetyl-oxy, monosaccharide, disaccharide, oligosaccharide, or OH;
R″″′ is one of H, CH2OH, halogen, COOH, acetyl-oxy, monosaccharide, disaccharide, oligosaccharide, or OH;
and
R* is selected from the group consisting of H, OH, CH2OH, an unsubstituted aliphatic group, a substituted aliphatic group, a halo substituted aliphatic group, a straight chain aliphatic group, a branched chain aliphatic group, alkoxy, a cyclic aliphatic group, an aliphatic group having at least one hetero chain atom, a cyclic aliphatic group having at least one hetero ring atom, an unsubstituted aromatic group, a substituted aromatic group, a halo substituted aromatic group, a polyaromatic group, a substituted polyaromatic group, an aromatic group having at least one hetero ring atom, a polyaromatic group having at least one hetero ring atom, a nucleoside, a nucleotide, a carbohydrate, monosaccharide, disaccharide, oligosaccharide, a polysaccharide;
an amino acid, a polypeptide, combinations thereof, and derivatives thereof.

10 more elements

A xyloside for use in inducing synthesis of a glycosaminoglycan in a cell, the xyloside comprising:

a chemical structure of one of Formula 5 or Formula 6;
R is one of H, CH2OH, halogen, COOH, acetyl-oxy, monosaccharide, disaccharide, oligosaccharide, or OH;
R′ is one of H, CH2OH, halogen, COOH, acetyl-oxy, monosaccharide, disaccharide, oligosaccharide, or OH;
R″ is one of H, CH2OH, halogen, COOH, acetyl-oxy, monosaccharide, disaccharide, oligosaccharide, or OH;
R″′ is one of H, CH2OH, halogen, COOH, acetyl-oxy, monosaccharide, disaccharide, oligosaccharide, or OH;
R″″ is one of H, CH2OH, halogen, COOH, acetyl-oxy, monosaccharide, disaccharide, oligosaccharide, or OH;
and
R″″′ is one of H, CH2OH, halogen, COOH, acetyl-oxy, monosaccharide, disaccharide, oligosaccharide, or OH.

5 more elements

A xyloside for use in inducing synthesis of a glycosaminoglycan in a cell, the xyloside comprising:

a chemical structure of one of Formula 7 or Formula 8;
n is from 0 to 10;
R is one of H, CH2OH, halogen, COOH, acetyl-oxy, monosaccharide, disaccharide, oligosaccharide, or OH;
R′ is one of H, CH2OH, halogen, COOH, acetyl-oxy, monosaccharide, disaccharide, oligosaccharide, or OH;
R″ is one of H, CH2OH, halogen, COOH, acetyl-oxy, monosaccharide, disaccharide, oligosaccharide, or OH;
R″′ is one of H, CH2OH, halogen, COOH, acetyl-oxy, monosaccharide, disaccharide, oligosaccharide, or OH;
R″″ is one of H, CH2OH, halogen, COOH, acetyl-oxy, monosaccharide, disaccharide, oligosaccharide, or OH;
R″″′ is one of H, CH2OH, halogen, COOH, acetyl-oxy, monosaccharide, disaccharide, oligosaccharide, or OH;
and
R* is selected from the group consisting of H, OH, CH2OH, an unsubstituted aliphatic group, a substituted aliphatic group, a halo substituted aliphatic group, a straight chain aliphatic group, a branched chain aliphatic group, alkoxy, a cyclic aliphatic group, an aliphatic group having at least one hetero chain atom, a cyclic aliphatic group having at least one hetero ring atom, an unsubstituted aromatic group, a substituted aromatic group, a halo substituted aromatic group, a polyaromatic group, a substituted polyaromatic group, an aromatic group having at least one hetero ring atom, a polyaromatic group having at least one hetero ring atom, a nucleoside, a nucleotide, a carbohydrate, monosaccharide, disaccharide, oligosaccharide, a polysaccharide;
an amino acid, a polypeptide, combinations thereof, and derivatives thereof.

8 more elements

A xyloside for use in inducing synthesis of a glycosaminoglycan in a cell, the xyloside comprising:

a chemical structure of one of Formula 9 or Formula 10;
n is from 0 to 10;
m is from 0 to 10;
X is one of a bond, S, SO2, O, N, or C;
R is one of H, CH2OH, halogen, COOH, acetyl-oxy, monosaccharide, disaccharide, oligosaccharide, or OH;
R′ is one of H, CH2OH, halogen, COOH, acetyl-oxy, monosaccharide, disaccharide, oligosaccharide, or OH;
R″ is one of H, CH2OH, halogen, COOH, acetyl-oxy, monosaccharide, disaccharide, oligosaccharide, or OH;
R′″ is one of H, CH2OH, halogen, COOH, acetyl-oxy, monosaccharide, disaccharide, oligosaccharide, or OH;
R″″ is one of H, CH2OH, halogen, COOH, acetyl-oxy, monosaccharide, disaccharide, oligosaccharide, or OH;
R″″′ is one of H, CH2OH, halogen, COOH, acetyl-oxy, monosaccharide, disaccharide, oligosaccharide, or OH;
and
R* is selected from the group consisting of H, OH, CH2OH, an unsubstituted aliphatic group, a substituted aliphatic group, a halo substituted aliphatic group, a straight chain aliphatic group, a branched chain aliphatic group, alkoxy, a cyclic aliphatic group, an aliphatic group having at least one hetero chain atom, a cyclic aliphatic group having at least one hetero ring atom, an unsubstituted aromatic group, a substituted aromatic group, a halo substituted aromatic group, a polyaromatic group, a substituted polyaromatic group, an aromatic group having at least one hetero ring atom, a polyaromatic group having at least one hetero ring atom, a nucleoside, a nucleotide, a carbohydrate, monosaccharide, disaccharide, oligosaccharide, a polysaccharide;
an amino acid, a polypeptide, combinations thereof, and derivatives thereof.

10 more elements

A method of making a xyloside for use in inducing synthesis of a glycosaminoglycan in a cell, the method comprising:

obtaining an N3-containing reagent having a chemical structure as in one of Reagent 1A, Reagent 1B, Reagent 1C, or Reagent 1D, wherein at least one of R, R′, R″, R″′, R″″, or R″″′ is protected by a protecting group that is capable of being deprotected without degrading the xyloside;
obtaining an alkynyl-containing reagent having a chemical structure as in one of Reagent 2A, Reagent 2B, or Reagent 2C;
reacting one of Reagents 1A-1D with one of Reagents 2A-2C;
and
deprotecting the at least one of R, R′, R″, R″′, R″″, or R″″′ that is protected by the protecting group so as to arrive at the at least one of R, R′, R″, R″′, R″″, or R″″′ so as to obtain the xyloside, wherein
n is from 0 to 10;
m is from 0 to 10;
X is one of a bond, S, SO2, O, N, or C;
R is one of H, CH2OH, halogen, COOH, acetyl-oxy, monosaccharide, disaccharide, oligosaccharide, or OH;
R′ is one of H, CH2OH, halogen, COOH, acetyl-oxy, monosaccharide, disaccharide, oligosaccharide, or OH;
R″ is one of H, CH2OH, halogen, COOH, acetyl-oxy, monosaccharide, disaccharide, oligosaccharide, or OH;
R″′ is one of H, CH2OH, halogen, COOH, acetyl-oxy, monosaccharide, disaccharide, oligosaccharide, or OH;
R″″ is one of H, CH2OH, halogen, COOH, acetyl-oxy, monosaccharide, disaccharide, oligosaccharide, or OH;
R″″′ is one of H, CH2OH, halogen, COOH, acetyl-oxy, monosaccharide, disaccharide, oligosaccharide, or OH;
and
R* is selected from the group consisting of H, OH, CH2OH, an unsubstituted aliphatic group, a substituted aliphatic group, a halo substituted aliphatic group, a straight chain aliphatic group, a branched chain aliphatic group, alkoxy, a cyclic aliphatic group, an aliphatic group having at least one hetero chain atom, a cyclic aliphatic group having at least one hetero ring atom, an unsubstituted aromatic group, a substituted aromatic group, a halo substituted aromatic group, a polyaromatic group, a substituted polyaromatic group, an aromatic group having at least one hetero ring atom, a polyaromatic group having at least one hetero ring atom, a nucleoside, a nucleotide, a carbohydrate, monosaccharide, disaccharide, oligosaccharide, a polysaccharide;
an amino acid, a polypeptide, combinations thereof, and derivatives thereof.

14 more elements

A method of making a xyloside for use in inducing synthesis of a glycosaminoglycan in a cell, the method comprising:

obtaining an alkynyl-containing reagent having a chemical structure as in one of Reagent 3A or Reagent 3B, wherein at least one of R, R′, R″, R″′, R″″, or R″″′ is protected by a protecting group that can be deprotected without degrading the xyloside;
obtaining an N3-containing reagent having a chemical structure as in Reagent 4A;
N3—R* Reagent 4A
reacting one of Reagent 3A-3B with Reagent 4A;
and
deprotecting the at least one of R, R′, R″, R″′, R″″, or R′″″ that is protected by the protecting group so as to arrive at the at least one of R, R′, R″, R′″, R″″, or R″″′ so as to obtain the xyloside, wherein
n is from 0 to 10;
m is from 0 to 10;
X is one of a bond, S, SO2, O, N, or C;
R is one of H, CH2OH, halogen, COOH, acetyl-oxy, monosaccharide, disaccharide, oligosaccharide, or OH;
R′ is one of H, CH2OH, halogen, COOH, acetyl-oxy, monosaccharide, disaccharide, oligosaccharide, or OH;
R″ is one of H, CH2OH, halogen, COOH, acetyl-oxy, monosaccharide, disaccharide, oligosaccharide, or OH;
R″′ is one of H, CH2OH, halogen, COOH, acetyl-oxy, monosaccharide, disaccharide, oligosaccharide, or OH;
R″″ is one of H, CH2OH, halogen, COOH, acetyl-oxy, monosaccharide, disaccharide, oligosaccharide, or OH;
R″″′ is one of H, CH2OH, halogen, COOH, acetyl-oxy, monosaccharide, disaccharide, oligosaccharide, or OH;
and
R* is selected from the group consisting of H, OH, CH2OH, an unsubstituted aliphatic group, a substituted aliphatic group, a halo substituted aliphatic group, a straight chain aliphatic group, a branched chain aliphatic group, alkoxy, a cyclic aliphatic group, an aliphatic group having at least one hetero chain atom, a cyclic aliphatic group having at least one hetero ring atom, an unsubstituted aromatic group, a substituted aromatic group, a halo substituted aromatic group, a polyaromatic group, a substituted polyaromatic group, an aromatic group having at least one hetero ring atom, a polyaromatic group having at least one hetero ring atom, a nucleoside, a nucleotide, a carbohydrate, monosaccharide, disaccharide, oligosaccharide, a polysaccharide;
an amino acid, a polypeptide, combinations thereof, and derivatives thereof.

15 more elements

A method of using a xyloside for inducing synthesis of a glycosaminoglycan in a cell, the method comprising:

providing a xyloside;
introducing the xyloside into the cell;
and
maintaining the cell under conditions in which the xyloside is capable of inducing the cell to synthesize the glycosaminoglycan,
wherein the xyloside has a chemical structure of one of Formula 1, Formula 2, Formula 3, Formula 4, Formula 5, Formula 6, Formula 7, Formula 8, Formula 9, or Formula 10;
n is from 0 to 10;
m is from 0 to 10;
X is one of a bond, S, SO2, O, N, or C;
R is one of H, CH2OH, halogen, COOH, acetyl-oxy, monosaccharide, disaccharide, oligosaccharide, or OH;
R′ is one of H, CH2OH, halogen, COOH, acetyl-oxy, monosaccharide, disaccharide, oligosaccharide, or OH;
R″ is one of H, CH2OH, halogen, COOH, acetyl-oxy, monosaccharide, disaccharide, oligosaccharide, or OH;
R″′ is one of H, CH2OH, halogen, COOH, acetyl-oxy, monosaccharide, disaccharide, oligosaccharide, or OH;
R″″ is one of H, CH2OH, halogen, COOH, acetyl-oxy, monosaccharide, disaccharide, oligosaccharide, or OH;
R″″′ is one of H, CH2OH, halogen, COOH, acetyl-oxy, monosaccharide, disaccharide, oligosaccharide, or OH;
and
R* is selected from the group consisting of H, OH, CH2OH, an unsubstituted aliphatic group, a substituted aliphatic group, a halo substituted aliphatic group, a straight chain aliphatic group, a branched chain aliphatic group, alkoxy, a cyclic aliphatic group, an aliphatic group having at least one hetero chain atom, a cyclic aliphatic group having at least one hetero ring atom, an unsubstituted aromatic group, a substituted aromatic group, a halo substituted aromatic group, a polyaromatic group, a substituted polyaromatic group, an aromatic group having at least one hetero ring atom, a polyaromatic group having at least one hetero ring atom, a nucleoside, a nucleotide, a carbohydrate, monosaccharide, disaccharide, oligosaccharide, a polysaccharide;
an amino acid, a polypeptide, combinations thereof, and derivatives thereof.

14 more elements

Dependencies are inferred from the claim text.

Facts

Application: 12/528,172Filed 15 Feb 2008
Priority: 22 Feb 2007
Published: 10 Jun 2010
Term ends: Not estimatedThe source records don’t support an estimate.

Classification5 codes

C07H 1/00
Processes for the preparation of sugar derivatives
A61K 31/70
Medicinal preparations containing organic active ingredients: carbohydrates; Sugars; Derivatives thereof
C07H 19/056
Heterocyclic radicals containing only nitrogen atoms as ring hetero atom: triazole or tetrazole radicals
C07H
Sugars

Family

Application60/891,168Us provisional application · filed 22 Feb 2007
Application60/896,230Us provisional application · filed 21 Mar 2007
US 2010/0143980 A1This patent

From the US filing history. Foreign family members aren’t listed.

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