Artemisinin Derivatives with Natural Amino Acids, Peptides, and Amino Sugars for Skin Imperfections and Infection in Mammals

a technology of artemisinin and amino acids, which is applied in the field of artemisinin derivatives, can solve the problems of affecting the function of the cellular membrane, reducing the activity of the hepatic cytochrome oxidase enzyme system, and and achieving the effect of reducing the toxicity of these compounds and generally reducing the reticulocyte coun

Inactive Publication Date: 2012-07-26
BIODERM RES
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Further, it affects cellular membrane functions and decreases hepatic cytochrome oxidase enzyme system activity.
The first manifestation of toxicity of these compounds is generally a decreased reticulocyte count.
Its low solubility in water and oil limited its widespread clinical ...

Method used

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  • Artemisinin Derivatives with Natural Amino Acids, Peptides, and Amino Sugars for Skin Imperfections and Infection in Mammals
  • Artemisinin Derivatives with Natural Amino Acids, Peptides, and Amino Sugars for Skin Imperfections and Infection in Mammals
  • Artemisinin Derivatives with Natural Amino Acids, Peptides, and Amino Sugars for Skin Imperfections and Infection in Mammals

Examples

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example 1

Preparation of N-(10-Deoxyartemisinylideneamino)acetic acid and Isomers (Formula VIII) in water solution

[0220]Ingredients. (1) Water 96.2 (2) Artemisinine 2.8 (3) Glycine 1.0. Procedure. The mixture of all ingredients is heated at 90 to 95 C for 2 hours. A solution of formula (VIII) in water is obtained.

example 2

Preparation of N-(10-Deoxyartemisinylideneamino)acetic acid Sodium in water solution

[0221]Ingredients. (1) Water 95.3 (2) Sodium Bicarbonate 0.9 (3) Glycine 1.0 (4) Artemisinin 2.8. Procedure. Mix (1) to (3). A clear solution is obtained. Heat to 80 to 90 C. Add (4). An instantaneous reaction occurs and a clear yellow solution is obtained. The mixing and heating is continued for 1 hour. A solution of Formula (VIII) Sodium salt in water is thus obtained.

example 3

Preparation of N-(10-Deoxyartemisinylideneamino)acetic acid from N-(10-Deoxyartemisinylideneamino)acetic acid Sodium in water solution

[0222]Ingredients. (1) Water 95.3 (2) Sodium Bicarbonate 0.9 (3) Glycine 1.0 (4) Artemisinin 2.8. Procedure. Mix (1) to (3). Heat to 70 to 80 C. Add (4). An instantaneous reaction occurs and a clear solution is obtained. The mixing and heating is continued for 1 hour. A solution of (VIII) Sodium in water is thus obtained. Water is evaporated to ⅓ in volume and the solution allowed to cool. The pH is adjusted to 6.5 with citric acid (2.0 grams of 50% solution). Compound (VIII) is obtained.

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Abstract

The present invention discloses certain derivatives of artemisinin and the active principles contained in Artemisia annua extracts with amino acids, peptides, and amino sugars and salts thereof (formula I). The compounds of the present invention possess wide-spectrum antibacterial and antifungal biological activity suitable for topical or oral application for the treatment of infections and topical ailments in mammals, including acne, rosacea, topical wounds, infections, dandruff, skin disfigurements caused by infection, skin discoloration, age spots, wrinkles, excess facial oil, and veterinary problems including canine infections;

Description

[0001]This invention is a continuation-in-part of U.S. patent application Ser. No. 12 / 957,598 (filed Dec. 1, 2010).BACKGROUND OF THE INVENTION[0002]This invention relates to certain Artemisinin derivatives that are classified as sesquiterpenes with an endo-peroxide group. The compounds of the present invention possess wide-spectrum antibacterial and antifungal biological activity, which are suitable for topical or oral application for the treatment of infections and topical ailments in mammals, including acne, rosacea, topical wounds, infections, dandruff, skin disfigurements, age spots, wrinkles, excess facial oil, and veterinary problems. The compounds of the present invention are of formula (I):[0003]Wherein,[0004]R1=H, alkyl, aryl, aralkyl, hydroxyalkyl, polyhydroxyalkyl, hydroxyaryl, polyhydroxyaryl, heterocyclic-alkyl, mercapto-alkyl, dithio-alkyl, carboxyalkyl, amidoalkyl, and guanidinoalkyl; and[0005]R2=OR3, NR3R4, and peptide; and[0006]R3, R4=H, alkyl, and aryl; and[0007]n=...

Claims

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Application Information

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IPC IPC(8): A61K31/357A61K31/4178A61K31/404A61P17/00A61Q19/08A61P17/10A61P17/18A61P17/12A61K8/49A61Q19/02A61P17/06A61P29/00A61P17/04A61P33/00A61P31/00C07D493/18
CPCA61K8/49A61K8/498C07D493/18A61Q19/02A61Q19/008A61Q5/006A61K2800/28A61K31/728A61K31/7008A61K31/205A61K31/357A61K31/404A61K31/4178A61K31/60A61K2300/00A61P17/00A61P17/04A61P17/06A61P17/10A61P17/12A61P17/18A61P29/00A61P31/00A61P33/00
Inventor GUPTA, SHYAM K
Owner BIODERM RES
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