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Biocompatible polymers, process for their preparation and compositions containing them

Inactive Publication Date: 2009-01-08
BARRITAULT DENIS +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

[0294]The model employed for evaluating the cicatrizing properties of the RGTA is the method already known in the prior art and described by Blanquaert F, et al., Bone, 1995; 17(6): 499-506.
[0295]This model comprises performing a circular trepanation of 5 millimeters in diameter in the calvaria of an adult rat. The defect is filled with a collagen buffer that has been cut to the same dimensions and impregnated with or not impregnated with a solution containing the RGTA. In the example presented here, the polymers studied are the type CMS polymers (RGTA 1005 and 1012) and the β-malic acid copolymers (RGTA 2011). Table III below presents the percentages of osseous filling established by image analysis of

Problems solved by technology

However, these CMDBS dextran derivatives are compounds which are difficult to synthesize and present the risk of salting out residues that are known for their toxic effects such as benzylamine.
Furthermore, the applications of the HBGFPP and thus of the CMDBS proposed in the prior art are limited solely to the repair and cicatrization of certain tissues.

Method used

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  • Biocompatible polymers, process for their preparation and compositions containing them
  • Biocompatible polymers, process for their preparation and compositions containing them
  • Biocompatible polymers, process for their preparation and compositions containing them

Examples

Experimental program
Comparison scheme
Effect test

example 1

Synthesis of Poly(β-Malic Acid) Derivatives from a Non-Polysaccharide Skeleton

[0129]In this example, the polymer of the invention is a copolymer of β-malic acids of general formula (II), the components A of which, substituted by X and / or Y and / or Z, are represented in FIG. 1. In FIG. 1:

[0130]A is —(O—CH2—CH2—CO)—

[0131]X is —COOH or —COO−Na+

[0132]Y is —CO—CH2—CHOH—CH2—SO3H or —CO—CH2—CHOH—CH2—SO3−Na+

[0133]Z is —CO—OCH3—CH(CH2—CH3)—CH3

[0134]x, y and z correspond to: the percentages of the X, Y and Z groups shown in Table I below in relation to the different polymers synthesized.

TABLE IType ofCarboxylicSulfonateHydrophobicReferencepolymergroups = Xgroups = Ygroups = ZRGTA 2010Pcoo−100%0%0%RGTA 2011P1S60%10%10%RGTA 2012P2S75%11%12%

[0135]Pcoo− corresponds to a polymer composed exclusively of carboxylic or carboxylate groups X. P1S and P2S correspond to polymers composed of sulfonate groups Y and hydrophobic butyl groups Z in addition to the groups X.

[0136]The synthesis of this polymer p...

example 2

Synthesis of Polysaccharide Polymers Constituted by Substituted Glucose Motif

I—Synthesis of Carboxymethyl Dextran Sulfates Designated CMDS

[0175]In this example, the polymer of the invention is constituted of substituted dextran in which the glucose A motifs substituted by X and / or Y and in which Z is nothing are represented in FIG. 5. The different types of grafting are shown in FIG. 5 in which:

[0176]A is a glucose monomer on which X, Y and Z are grafted by the intermediary of the hydroxyl functions in position 2 and / or position 3 and / or position 4 and / or by the intermediary of the Y groups for Z,

[0177]X is —CH2COOH or —CH2COO−Na+

[0178]Y is —SO3H or SO3−Na+

[0179]Z is a variable group of which several examples are presented below.

[0180]The polymers of type CMDS in which Z=nothing contain multiple types of monomers. The first types of substituted monomers are the carboxymethyl glucose of type A-X substituted in position 2 and / or 3 and / or 4 (motifs presented in FIG. 5). The addition of...

example 3

Measurement of the Anticoagulant Activities of the Polymers of Examples 1 and 2

[0276]The coagulation tests were performed using the Activated Cephalin Time technique or A.C.T. (Biggs, 1972, In: Human Blood Coagulation, Oxford Blackwell Scientific Publications). One hundred microliters of a polymer solution at different concentrations in Owen Koller buffer are incubated for 5 minutes at 37° C. with 100 microliters of plasma poor in platelets and 100 microliters of a solution of rabbit brain cephalin. 100 microliters of 0.25 M calcium chloride are added and the time until appearance of the coagulum is referenced by chronometry.

[0277]As shown in FIG. 11, the polymers of Examples 1 and 2 do not present anticoagulant activities greater than 50 IU / milligram, especially with respect to heparin which was used as a; positive control. It should be noted that all of the values for the anticoagulant activities of the products presented here as examples are lower than 10 IU / milligram of product....

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Abstract

A process for treating fibroses including administering a therapeutically effective amount of a pharmaceutical composition which includes at least one biocompatible polymer of the following general formula (I): AaXxYy wherein: A represents a monomer selected from the group consisting of a sugar or —(O—CH2—CH2—CO)—, X represents a carboxyl group bonded to monomer A and is contained within a group according to the following formula: —R—COO—R′, in which R is a bond or an aliphatic hydrocarbon chain, optionally branched and / or unsaturated, and which can contain one or more aromatic rings except for benzylamine and benzylamine sulfonate, and R′ represents a hydrogen atom or a cation, Y represents a sulfate or sulfonate group bonded to monomer A and is contained within a group according to one of the following formulas: —R—O—SO3—R′, —R—N—SO3—R′, —R—SO3—R′, in which R is a bond or an aliphatic hydrocarbon chain, optionally branched and / or unsaturated, and which can contain one or more aromatic rings except for benzylamine and benzylamine sulfonate, and R′ represents a hydrogen atom or a cation, a represents the number of monomers A such that the mass of the polymers of formula (I) is greater than approximately 5,000 da, x represents a substitution rate of the monomers A by the groups X, which is between approximately 20 and 150%, and y represents a substitution rate of the monomers A by the groups Y, which is between approximately 30 and 150%.

Description

RELATED APPLICATION[0001]This is a continuation of International Application No. PCT / FR99 / 01774, with an international filing date of Jul. 20, 1999, which is based on French Patent Application No. 98 / 09309, filed Jul. 21, 1998.FIELD OF THE INVENTION[0002]This invention pertains to new biocompatible polymers, a process for their preparation and compositions containing them.BACKGROUND[0003]Known in the prior art are polymer derivatives of dextrans obtained by substitution by carboxymethyl, carboxymethyl-benzylamide and carboxymethyl-benzylamide-sulfonate residues. These polymers, the process for their preparation and their properties, are described in French Patent No. 2,461,724 as well as in U.S. Pat. No. 4,740,594. Among these polymers, certain of them imitate the properties of heparin and can be used as plasma substitution products because of their anticoagulant and anticomplement properties. Others imitate a different property of heparin which consists of a stabilization, protecti...

Claims

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Application Information

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IPC IPC(8): A61K31/715A61K31/194A61K9/08A61K47/48A61P1/00A61P3/00A61P9/10A61P9/12A61P17/02A61P17/16A61P21/00A61P25/00A61P29/00A61P31/00A61P31/08A61P39/00A61P39/06A61P43/00C08B37/02C08G63/688C08G85/00
CPCC08B37/0021C08G63/6882A61K31/795A61K31/765A61K31/721A61P1/00A61P3/00A61P9/00A61P9/10A61P9/12A61P17/00A61P17/02A61P17/16A61P21/00A61P25/00A61P29/00A61P31/00A61P31/08A61P39/00A61P39/06A61P43/00
Inventor BARRITAULT, DENISCARUELLE, JEAN-PIERRE
Owner BARRITAULT DENIS
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