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Water soluble, randomly substituted partial N-, partial O-acetylated chitosan, preserving compositions containing chitosan, and processes for making thereof

A technology of water-soluble chitosan and chitosan derivatives, applied in the field of water-soluble randomly substituted part N-, part O-acetylated chitosan, antiseptic composition containing chitosan and its preparation field, capable of Solve problems such as preventing full utilization of reaction sites

Inactive Publication Date: 2004-06-23
ADJUVANT PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In particular, Kurita’s chitosan reactant was insoluble in the reaction mixture but dispersed as a swollen gel, which prevented full utilization of the reaction sites.

Method used

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  • Water soluble, randomly substituted partial N-, partial O-acetylated chitosan, preserving compositions containing chitosan, and processes for making thereof
  • Water soluble, randomly substituted partial N-, partial O-acetylated chitosan, preserving compositions containing chitosan, and processes for making thereof
  • Water soluble, randomly substituted partial N-, partial O-acetylated chitosan, preserving compositions containing chitosan, and processes for making thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0126] The in vitro biocompatibility study of Example 1 was based on the agar diffusion test described in USP / NF 22(87) Biological Reactivity Tests In-Vitro. In this test, on a replica agarose surface directly covered with a confluent monolayer of L-929 mouse fibroblasts, a filter plate with a 0.1 ml aliquot of Example 1 and the appropriate negative and positive control filter plates are placed . at 37°C, 5% CO 2 After culturing in medium for 24-26 hours, the culture was tested, and the results showed that Example 1 did not cause cell lysis or toxicity, thus meeting the biocompatibility requirements of USP (see Table 1-c).

[0127] The in vitro biocompatibility test result of table 1-c embodiment 1

[0128] Test / Control Item 1 Sample number Dissolution zone level 2 reactivity 1

[0129] (mm)

[0130] Example 1 1 0.0 0 None

[0131] 2 0.0 0 None

[0132] Filter Plate Control 1 0.0 0 None

[0133] 2 0.0 0 None ...

Embodiment 2

[0147] This example reveals the activity of different hydroxyalkyl chitosan solutions against E. coli in the 28 day US Preservative Efficacy Test (PET). Solutions 2a-e were prepared according to the method described in Example 1 using the following recipes.

[0148] Example formulations #2a-e:

[0149] 0.05% EDTA

[0150] 1.00% boric acid

[0151] Ultrapure water (q.s. adjusted to 100.00ml)

[0152] 0.5M sodium hydroxide (q.s. adjust pH=6.9)

[0153] Sodium chloride (q.s. adjust mOsm=300)

[0154]a: control; b=0.25% ethylene glycol chitosan (SIGMA Chemical Co.); c=0.25% hydroxypropyl chitosan (Austin Chemical Co.); d=0.25% hydroxybutyl chitosan (Austin Chemical Co. Co.); e = 0.25% di-hydroxypropyl chitosan (Technology Resource International Corporation).

[0155] The conditions for PET were the same as in Example 1, except that no reseeding was introduced on day 14. Only E. coli was selected as the screening microorganism in the test because earlier tests showed that E....

Embodiment 3

[0168] This example illustrates the effect of pH on the antimicrobial activity of ethylene glycol. The test microorganism used in Example 3 was Pseudomonas aeruginosa (ATCC No. 9027), which is a microorganism requiring attention in common contact lens-associated eye infections and infectious keratitis.

[0169] Embodiment 3 formula

[0170] Ethylene glycol chitosan (Sigma Chemical) 0.5%

[0171] Pluronic TM F68 (BASF Corporation) 0.05%

[0172] EDTA0.05%

[0173] Sodium borate decahydrate 0.08%

[0174] Boric acid 0.72%

[0175] Ultrapure water q.s adjusted to 100.00ml

[0176] Sodium hydroxide solution (0.5M) q.s adjusted to pH=6.6, 7.2 or 7.8

[0177] Sodium chloride q.s adjusted to mOsm=300±10

[0178] Table 3: Comparison of the antimicrobial activity of Example 3 against Pseudomonas aeruginosa

[0179] Pseudomonas aeruginosa Cfu after 24 hours 1，2

[0180] PH=6.6 PH=7.2 PH=7.8

[0181] 2 184 >1000

[0182] Note: 1 The inoculum concentration was 10...

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PUM

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Abstract

The present invention is directed to a water soluble, randomly substituted partial N-, partial O- acetylated chitosans or chitosan derivatives and methods of preparing water soluble, randomly substituted partial N-, partial O-acetylated chitosans or chitosan derivatives comprising the steps of dissolving the chitosan or chitosan derivative into an aqueous acidic solution and reacting the chitosan or chitosan derivative with an acetylating agent in the presence of a phase transfer reagent. The composition comprising: (a) at least one chitosan or chitosan derivative and (b) at least one buffer solution, as well as methods of preserving contact lens solutions and disinfecting contact lens using such composition.

Description

[0001] Cross References to Related Applications [0002] This application is a continuation-in-part of U.S. Application Serial No. 09 / 838,528, filed April 19, 2001, which is in turn Application Serial No. 09 / 611,160, application A continuation-in-part of U.S. application dated July 6, 2000, which claims priority from application serial number 60 / 199,406, filed April 21, 2000, and application serial number 60 / 202,548, filed on US provisional application dated May 10, 2000, which are incorporated herein by reference in their entirety. technical field [0003] The present invention relates to a kind of novel water-soluble randomly substituted part N-, part O-acetylated chitosan or its derivatives, and including water-soluble randomly substituted part N-, part O-acetylated chitosan, The antiseptic composition of chitosan or its derivatives also relates to a novel preparation method of water-soluble arbitrarily substituted partially N-, partially O-acetylated chitosan, and chitosa...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K9/00A61K47/36A61L12/14C08L5/08
CPCA61L12/14C08L5/08
Inventor 威廉·M·亨卡特里娜·L·贝格鲍尔开·C·苏王桂贵
Owner ADJUVANT PHARMA
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