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Polymer-carbohydrate conjugates for drug delivery technology

A compound and chemical technology, applied in the direction of active ingredients of hydroxyl compounds, drug delivery, organic chemistry, etc., can solve problems such as increasing the boiling temperature and melting point of compounds, and decreasing

Inactive Publication Date: 2016-07-20
UKRAINIAN INDEPENDENT INFORMATION AGENCY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

A permanent dipole can lead to an increased boiling temperature and a decrease in the melting point of the compound

Method used

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  • Polymer-carbohydrate conjugates for drug delivery technology
  • Polymer-carbohydrate conjugates for drug delivery technology
  • Polymer-carbohydrate conjugates for drug delivery technology

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0132] Example 1. Preparation of amino groups protected by tert-butylcarbamate (Boc)

[0133] A high-yield and efficient synthetic method under catalyst-free and room temperature conditions has been reported before [Chankeshwara, SV and Chakraborti, AK. Org. Lett. , (2006); 8, 3259], and was used with some modifications. To the MeOH solution of the anthranilate-containing starting compound, di-tert-butyldicarbonate was added in a molar ratio of 1:1. The resulting mixture was stirred overnight at room temperature. When the reaction was complete, the solvent was removed under vacuum, the residue was dissolved in ethyl acetate and washed once with saturated aqueous ammonium chloride solution, then washed with Na 2 SO 4 Drying and concentration afforded the expected product (>90%). An example of this reaction is illustrated in Reaction Scheme 5, where R is the main structure of the central backbone. This method produces N-t-Boc derivatives chemoselectively without any by-pro...

Embodiment 2

[0136] Example 2. Deprotection of Boc-protected amino groups

[0137] Useful reagents for the deprotection of tert-butyl carbamate or tert-butyl ester include phosphoric acid and trifluoroacetic acid. The reaction yield is high, and it is very convenient [Li, B. Berliner, M. etc, J. Org. Chem., 2006; 71, 9045]. In Boc-carbamate (10% crude product) in CH 2 Cl 2 An equal volume of trifluoroacetic acid was added to the solution. The resulting solution was stirred overnight at room temperature, then the solvent was removed by evaporation and the residue was redissolved in CH 2 Cl 2 , then saturated NaHCO 3 washed with MgSO 4 dry. The solvent was evaporated and used directly in the next step without further purification.

Embodiment 3

[0138] Example 3. Preparation of N-Boc-cholesterol serine ester

[0139] Dissolve 0.03 mol of N-Boc-serine in 100 mL of chloroform with constant stirring under nitrogen. 0.03 mol of cholesterol chloroformate dissolved in 100 mL of chloroform was added to this heterogeneous mixture of N-Boc-serine, followed by 10 mL of anhydrous pyridine. The reaction was stirred continuously at room temperature for 30 minutes, the mixture became homogeneous and the reaction was complete when no detectable cholesterol chloroformate was present in the mixture. The solvent was removed under vacuum and the crude product was used in the next step without further purification. The resulting product (70-80% yield) is shown in Chemical Structure 2:

[0140]

[0141] Chemical structure 2

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Abstract

The invention comprises compounds, methods of making, and methods of using. The compounds may have a linear or cylic backbone and three or four appended functional groups: one or two lipohilic compounds including sterols or "fat soluble" vitamins, one or two hydrophilic polymer, and one or two carbohydrate. A group of polymer-carbohydrate conjugates having a central backbone and three appended functional groups are disclosed whereinone lipophilic compound is void of both steroid acids. The conjugate may have fatty acids as the primary lipophilic carrier, one hydrophilic polymer, and one carbohydrate. Specific functional groups may be selected for specific applications in formulating pharmaceuticals, cosmetics, nutriceuticals, and the like. Typical coupling reaction of the conjugates may involve one or more or combinations or in series of alkylation including N-alkylation or O-alkylation, etherification, esterification and amidation chemical processes. A variety of linkers between the backbone and functional groups may also be selected to modify the carriers or center backbones for the coupling reactions and optimize performance of the conjugates.

Description

[0001] This application claims the U.S. Provisional Patent Application No. 61 / 912, No. 228 and Priority enjoyed by US Patent Application No. 14 / 561,219, filed by Wu Nian on December 5, 2014, entitled Polymer-Carbohydrate Conjugates for Drug Delivery Technology (polymer, carbohydrate and lipid conjugate drug delivery technology). technical field [0002] The present invention relates to polymer-carbohydrate conjugates, and specifically discloses the synthesis of polyethylene glycol-carbohydrate conjugates with sterols or known as "fat-soluble" vitamins (lipid vitamins) as lipophilic carriers, Free of both steroid and fatty acid as the main lipophilic component of the conjugate, preferably has substantially monodisperse PEG chains if used for intravenous drug administration. More specifically, the present invention relates to a class of polymer-carbohydrate conjugates containing sterols or sterols or lipophilic vitamin structural components to increase the lipophilic properties ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K47/30C07H15/00C08G81/00
CPCA61K9/0014A61K9/0019A61K9/0048A61K9/0095A61K9/08A61K31/05A61K31/337A61K31/506C08L71/02C08L2203/02C08G2650/26A61K47/26A61K47/28
Inventor 念·吴
Owner UKRAINIAN INDEPENDENT INFORMATION AGENCY
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