Piprozolin

Piprozolin

File:Piprozolin.png
Systematic (IUPAC) name
Ethyl (2Z)-2-(3-ethyl-4-oxo-5-piperidin-1-yl-1,3-thiazolidin-2-ylidene)acetate
Identifiers
CAS Number	17243-64-0
ATC code	A05AX01 (WHO)
PubChem	CID: 5911905
ChemSpider	4744588 Y
UNII	7786W0VV8M Y
ChEMBL	CHEMBL2105231
Chemical data
Formula	C14H22N2O3S
Molecular mass	298.40 g/mol
InChI InChI=1S/C14H22N2O3S/c1-3-16-11(10-12(17)19-4-2)20-14(13(16)18)15-8-6-5-7-9-15/h10,14H,3-9H2,1-2H3/b11-10- Y Key:UAXYBJSAPFTPNB-KHPPLWFESA-N Y
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Piprozolin (or piprozoline) is a medication for bile therapy.

Synthesis

Compared to fenclozic acid, piprozolin shows choleretic rather than antiinflammatory activity. That is, the compound is useful in those conditions where the flow of bile is to be increased.

File:Piprozolin synthesis.svg

Piprozolin synthesis: G. Satzinger et al., DE 2414345  (1975 to Goedecke), corresp to U.S. Patent 3,971,794 (1976 to Warner-Lambert).

Condensation of ethyl mercaptoacetate with ethyl cyanoacetate leads to thiazolinone (4); an intermediate such as 3, involving addition of the mercaptide to the nitrile function can reasonably be invoked. M/ethylation with di(m)ethyl sulfate proceeds on nitrogen with the comcomitant shift of the enamine to afford olefin (5). Bromination of the active methylene (6) followed by displacement of halogen by piperidine affords the choleretic piprozolin (7).