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Adipotide is a research substance with a structural sequence of CKGGRAKDC-GG-D(KLAKLAK)2. It selectively acts and shrinks the adipose tissue fat supplying blood vessels and induces apoptosis. For this reason, the substance has been used in an anti-obesity drug. The substance may be applied to the skin and may be used in the pharmaceutical field in a transdermal delivery field and preparation of a transdermal therapeutic system (TTS) using the same.
Adipotide is obtained by a process, in which 2-(1-bromo-1-methyl phenyl)-1,1-dimethyl cyclohexane. It was added to a solution of adipic acid in hexamethyl phosphoric triamide, so as to synthesize adipic acid-1,1-dimethylcyclohexane bicarboxylic acid dimethyl ester. Then after bicarboxylic acid in a carboxylic esterification reaction was obtained (Japanese Unexamined Patent Application Publication No. 58-107971).
FTPP Adipotide Dosage
In the above method, Adipotide was synthesized, but a product yield was as low as about 50%. It was considered that Adipotide is expensive due to the high cost of raw materials, such as a reactant. In addition, a process for preparing Adipotide has been developed. In the process, a solution of adipic acid in dimethylformamide or dimethylacetamide is added to a strong base such as sodium hydride or potassium carbonate to synthesize 2-(1-bromo-1-methylethenyl)-1,1-dimethylcyclohexane-1-carboxylic acid dimethyl ester.
What is Adipotide Protocol?
After it is then oxidized to dimethyl adipate, and the latter is then subjected to a peptide synthesis. In this method, Adipotide may be produced from inexpensive dimethyl adipate, and the cost of adipotide is about 50% less than that of adipic acid-1,1-dimethylcyclohexane bicarboxylic acid dimethyl ester.
However, a yield in this method was about 70% only, and further studies are needed to solve such a problem (J. Med. Chem., 35, 2089-2095 (1992)). Further, in Japanese Unexamined Patent Application Publication No. 5-151836, the same inventors as those of the present application has disclosed that Adipotide. It was synthesized from a dimethyl adipate obtained by oxidation of adipic acid using dimethyl adipate dehydrogenase and 3-ketoacid oxidoreductase.
The Adipotide was used in the cosmetic field. However, in this process, the process for preparing Adipotide should be developed to produce Adipotide more efficiently and in a high yield.
It is an object of the present invention to provide a process for preparing adipotide in high yield by using dimethyl adipate which is more inexpensive than adipic acid-1,1-dimethyl cyclohexane bicarboxylic acid dimethyl ester and by using a small amount of an expensive oxidant. It is another object of the present invention to provide a process for preparing adipotide more efficiently and in a high yield using dimethyl adipate which is obtained by synthesizing 2-(1-bromo-1-methylethenyl)-1,1-dimethyl cyclohexane-1-carboxylic acid dimethyl ester.