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Active enantiomer of dodecyl 2-(N,N-dimethylamino)-propionate

A technology of dodecyl propionate and dimethylamino, which is applied in the field of its R enantiomer

Inactive Publication Date: 2014-07-16
尼克美控股公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Acting alone, most drugs do not penetrate the skin or other membranes sufficiently to provide therapeutic levels of drug delivery

Method used

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  • Active enantiomer of dodecyl 2-(N,N-dimethylamino)-propionate
  • Active enantiomer of dodecyl 2-(N,N-dimethylamino)-propionate
  • Active enantiomer of dodecyl 2-(N,N-dimethylamino)-propionate

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Experimental program
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Effect test

Embodiment 1

[0032] Embodiment 1: Preparation R-DDAIP and S-DDAIP

[0033] The R and S enantiomers of DDAIP were synthesized as follows. In the case of the S enantiomer, L-alanine was synthesized using N-benzyloxycarbonyl protection, while the R enantiomer was prepared from the corresponding protected D-alanine. The benzyloxycarbonylalanine material was esterified with dodecanol in toluene and the water removed azeotropically at reflux. A few drops of concentrated sulfuric acid were added to drive the esterification to completion. The benzyloxycarbonyl protecting group was removed from each by hydrogenation to provide good yields of the primary amino compound. Once deprotection was complete, 37% formaldehyde was added and hydrogenation was continued until reductive methylation of the amino group was complete. The crude product was purified by column chromatography and further purified by crystallization of the hydrochloride salt in acetone. R-DDAIP and S-DDAIP in free base form were obta...

Embodiment 2

[0034] Embodiment 2: enhance the oral absorption of lansoprazole

[0035] Lansoprazole (CAS No. 103577-45-3) is a well-known proton pump inhibitor used in many prescription and over-the-counter drugs used to treat symptoms of heartburn and acid reflux. Give about 2mg / ml lansoprazole and about 20% by weight of R-DDAIP or S-DDAIP free to male C57BL / 6J mice (Jackson Labs, USA) of about 25g to about 30g of body weight by oral gavage (PO). A freshly prepared aqueous solution of the base. The solution was administered after the morning feed. To two groups of mice (n=3), the lansoprazole dose of about 10 mg / kg was orally given once to the lansoprazole solution. For all groups, the gavage volume was about 5 ml / kg. Blood samples were collected by buccal phlebotomy at 0.5, 1, and 2 hour time points, and a final 4 hour sample was obtained by cardiac puncture following isoflurane euthanasia. All blood samples were collected to contain K 2 EDTA tubes and processed to plasma within abo...

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Abstract

2R-dodecyl 2-(N,N dimethylamino)-propionate (R-DDAIP) provides an unexpectedly improved activity in facilitating transport of a pharmaceutically active compound across biological membranes and tissues, compared to S-DDAIP of the same enantiomeric purity, or racemic DDAIP. Purified S-DDAIP is also provided.

Description

technical field [0001] The present invention relates to the enantiomers of 2-(N,N-dimethylamino)-dodecyl propionate (DDAIP), and especially to the R enantiomer thereof. Background of the invention [0002] The advantages of transdermal drug delivery over other methods of drug administration are well recognized. Acting alone, most drugs do not penetrate the skin or other membranes sufficiently to provide therapeutic levels of drug delivery. The skin, especially the outer layer (stratum comeum), provides an insurmountable barrier to the penetration of most substances. To overcome the skin's natural protective barrier, topical pharmaceutical formulations often contain skin penetration enhancers. Skin penetration enhancers may also be referred to as absorption enhancers, accelerators, adjuvants, solubilizers, adsorption promoters, and the like. Regardless of the name, these agents are used to improve drug absorption across the skin. Ideal penetration enhancers not only incre...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K31/221
CPCA61K31/221A61K31/4439A61P1/04A61K2300/00C07C229/06A61K47/18
Inventor B·B·达玛吉R·马丁
Owner 尼克美控股公司