Piprozolin

Chemical compound

A05AX01 (WHO)

Identifiers

IUPAC name

Ethyl (2Z)-2-(3-ethyl-4-oxo-5-piperidin-1-yl-1,3-thiazolidin-2-ylidene)acetate

CAS Number

17243-64-0

PubChem CID

5911905

ChemSpider

4744588^Y

UNII

7786W0VV8M

ChEMBL

ChEMBL2105231

CompTox Dashboard (EPA)

DTXSID70864757

ECHA InfoCard100.037.512

Chemical and physical dataFormulaC₁₄H₂₂N₂O₃SMolar mass298.40 g·mol⁻¹

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

(verify)

Piprozolin (or piprozoline) is a medication for bile therapy.^[1]^[2]

Synthesis

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

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 concomitant 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).

References

^ Koss FW, Vollmer KO, Herrmann M (August 1972). "[Research with experimental animals on the mechanism of action of the new choleretic, 3-ethyl-4-oxo-5-piperidino-delta 2, alpha-thiazolidine-acetic acid ethyl ester (Piprozolin)]". Archives Internationales de Pharmacodynamie et de Therapie. 198 (2): 333–46. PMID 5074733.
^ "Piprozolin". Drugs-about.com.
^ Satzinger (1975). "Substituierte 2-Methylen-thiazolidone-(4)". Justus Liebigs Annalen der Chemie. 665: 150–165. doi:10.1002/jlac.19636650118.
^ DE 2414345, Satzinger G, Herrmann M, Vollmer K, issued 1975, assigned to Goeecke
^ US 3971794, Satzinger G, Herrmann M, Vollmer K, issued 1976, assigned to Warner-Lambert