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SHA-68

Chemical compound

SHA-68

Chemical compound

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SHA-68 is a drug which acts as a selective, non-peptide antagonist at the neuropeptide S receptor NPSR. In animal studies it reduced motor stereotypes, and blocks the stimulant action of neuropeptide S.

Synthesis

The synthesis of SHA-68 was shown in a patent (ref example 1, Ex 1, Ex 2, Ex 16).

The Grignard reaction between Methyl 2-piperazine carboxylate [2758-98-7] (1) and phenylmagnesium bromide [100-58-3] (2) occurs to give alpha,alpha-Diphenyl-2-piperazinemethanol [17532-20-6] (3). {This compound is called Azapipradrol}. Protection of the sterically more accessible piperazine nitrogen with Boc anhydride occurs to give PC23122074 (4). Treatment with ethyl chloroformate [541-41-3] (5) gives the cyclic urethane and hence, PC68420957 (6). Deprotection of the Boc group in the presence of trifluoroacetic acid gave 1,1-Diphenyltetrahydro-1H-oxazolo[3,4-a]pyrazin-3(5H)-one [847555-93-5] [847556-28-9] (7). Lastly, treatment with 4-fluorophenyl isocyanate [1195-45-5] (8) gave the substituted urea, thus completing the synthesis of SHA-68 (9).

SAR reveals similarity to RTI-118 and contains the same precursor.

References

References

  1. Fukatsu K, Nakayama Y, Tarui N, Mori M, Matsumoto H, Kurasawa O, Banno H. Bicyclic Piperazine Compound and Use Thereof. PCT Patent WO 2005/021555 A1. Published 26.08.2004
  2. (June 2008). "Synthesis and pharmacological in vitro and in vivo profile of 3-oxo-1,1-diphenyl-tetrahydro-oxazolo[3,4-a]pyrazine-7-carboxylic acid 4-fluoro-benzylamide (SHA 68), a selective antagonist of the neuropeptide S receptor". The Journal of Pharmacology and Experimental Therapeutics.
  3. Kohji Fukatsu, et al. WO2005021555 (to Takeda Pharmaceutical Co Ltd).
Info: Wikipedia Source

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4-fluorophenyl-compounds ureas oxazoles pyrazines
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