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Use of alpha-hydroxy carbonyl compounds as reducing agents

A technology for compounds and organic compounds, applied in the direction of active ingredients of hydroxy compounds, active ingredients of nitro compounds, organic reduction, etc., can solve the problems of non-disclosure and the like

Active Publication Date: 2009-03-18
GORDIAN PHARMA LIMITED
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] In addition, the above-mentioned documents do not disclose (relating to the reduction with α-hydroxycarbonyl compounds) the use of solvent systems containing more than 10% by weight of organic solvents

Method used

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  • Use of alpha-hydroxy carbonyl compounds as reducing agents
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  • Use of alpha-hydroxy carbonyl compounds as reducing agents

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0374] Example 1: Chemical Activation of Tretazicar

[0375] Reported chemistries for the manufacture of active 4-hydroxyamino derivatives from tretazicar use harsh reducing conditions in organic solvents to achieve yields below 30% (Knox et al., 1993; Knox et al., 1988). The inventors have found that dihydroxyacetone (DHA) is capable of reducing tretazicar to the desired hydroxylamine in aqueous solution under mildly basic conditions. At pH 9, the yield was >85%, and the only other product detected by tretazicar reduction was 5-(aziridin-1-yl)-2-hydroxyamino-4-nitrobenzamide.

[0376] Dihydroxyacetone (DHA; 1,3-dihydroxy-2-propanone; CAS No: 62147-49-3, Beil.8, 266, Merck Index 13, 3166; image 3 ) is the active ingredient in sunscreen or self-tanning lotions and is FDA-approved. DHA is a colorless sugar that darkens the color of the skin by staining. It interacts with dead surface cells in the epidermis to produce a color shift. Generally within 5 to 7 days after applica...

Embodiment 2

[0387] Example 2: Activation of tretazicar in emulsion for topical administration

[0388] Two emulsions designated A and B were prepared. To use, mix them in equal amounts. Emulsion A consisted of E45 base (white soft paraffin BP 14.5% w / w, light liquid paraffin Ph Eur 12.6% w / w, hypoallergenic anhydrous lanolin (Medilan) 1.0% w / w, Crookes Healthcare Ltd, Nottingham, UK ) composition), each gram contains 10mg tretazicar, 10mg NaHCO 3 and 90mg Na 2 CO 3 . Emulsion B contained E45 and contained 100 mg DHA dimer per gram. Components A and B were mixed to obtain a pale yellow emulsion. Turns brown after a few hours and continues to deepen over 24 hours. A suspension of 200 μg of the emulsion in 1 mL of water yielded a solution of approximately pH 10 as indicated by pH paper under vigorous stirring. Preliminary experiments with emulsions containing 10% of the above amounts of buffer salts gave solutions of the same initial pH. However, after 4 hours, the solution prepared...

Embodiment 3

[0393] Embodiment 3: External use of tretazicar emulsion

[0394] The above-prepared emulsion was mixed, and about 0.1 g was applied to the warts (growing, slope height 1.5 mm) on the fingers of healthy human volunteers, and covered with a plaster. The initial temperature (warmth) at which the emulsion was applied was recorded. After approximately 4 hours, the plaster was removed and the wart was observed to have fallen off, leaving a ~1 mm deep pit. The surrounding tissue turns yellow. After a few days, it gradually turned white, and no regrowth of the wart was observed after 6 weeks. There were also no reports of significant side effects.

[0395] Each gram contains 10mg tretazicar, 10mg NaHCO 3 and 90mg Na 2 CO 3 Emulsion A (composed of E45 base (white soft paraffin BP 14.5% w / w, light liquid paraffin Ph Eur 12.6% w / w, hypoallergenic anhydrous lanolin (Medilan) 1.0% w / w, Crookes Healthcare Ltd, Nottingham , composed of UK) mixed with lotion B (containing E45, contain...

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Abstract

There is provided the use as reducing agents of alpha-hydroxycarbonyl compounds capable of forming cyclic dimers. There is also provided corresponding methods of reducing reducible compounds, particularly reduction-activated prodrugs. Examples of the alpha-hydroxycarbonyl compounds used are dihydroxyacetone, glycolaldehyde, glyceraldehyde, erythrose, xylulose, erythrulose or 3-hydroxy-2-butanone.

Description

technical field [0001] The present invention relates to the use of certain compounds as reducing agents. In particular, the invention relates to the use of the compounds for the reduction-activated prodrugs which generate active substances for the inhibition of diseases. The active substance is in particular a DNA cross-linking agent, which can be used to inhibit the growth or proliferation of unwanted cells. Background technique [0002] The listing and discussion of published literature in this specification should not be taken as an acknowledgment of part of the state of the art or common general knowledge. [0003] α-Hydroxycarbonyl compounds (although their molecules can be oxidized) are not effective reducing agents in a low alkaline (pH<11) environment. [0004] Certain alpha-hydroxycarbonyl compounds (azoins) described in US 5,831,097 and EP 0 364 752 are effective reducing agents in the dye industry. However, the conditions described in EP 0 364 752 require a ...

Claims

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Application Information

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IPC IPC(8): A61K31/045A61K31/12
CPCA61K31/04A61K31/045A61K45/06A61K31/396C07B31/00C07D203/14A61K31/12A61M11/006A61K9/0014A61K9/0019A61K9/0031A61K9/0075A61K9/06A61K9/141A61P17/00A61P17/06A61P17/12A61P35/00A61P43/00A61K2300/00A21D2/06C07C49/24A61M11/02A61M15/009A61M2202/064
Inventor 理查德·约翰·诺克斯
Owner GORDIAN PHARMA LIMITED
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