Talipexole (B-HT920, Domnin) is a dopamine agonist that is marketed as a treatment for Parkinson's Disease in Japan by Boehringer Ingelheim; it was introduced in 1996.[1] As of December 2014 it was not approved for marketing in the US nor in Europe.[2]

Talipexole is a D2 dopamine receptor agonist and interacts with both pre- and post-synaptic receptors. It also is an α2-adrenergic agonist.[3]

The main side effects are drowsiness, dizziness, hallucinations and minor gastrointestinal complaints.[3] In Japan, Ministry of Health, Labour and Welfare mandated in 2008 that Boehringer add a warning to the label concerning the risk of sudden onset of sleep.[4]: 15 

Synthesis

Synthesis:[5] Patents:[6][7] Sino:[8]

The N-alkylation of azepan-4-one [105416-56-6] (1) with allyl bromide in the presence of potassium carbonate gives 1-allyl-azepan-4-one (2). This is halogenated with molecular bromine in acetic acid to give 1-allyl-5-bromohexahydro-4-azepinone (3). The last step involves cyclization with thiourea (4) in refluxing ethanol, completing the synthesis of talipexole (5).

See also

References

  1. ^ PharmaLetter 22 July 1996 First Launch In Japan For Talipexole
  2. ^ EvaluatePharma Database. Page accessed 9 December 2014
  3. ^ a b Benkert O, Müller-Siecheneder F, Wetzel H (1995). "Dopamine agonists in schizophrenia: a review". European Neuropsychopharmacology. 5 Suppl: 43–53. doi:10.1016/0924-977x(95)00022-h. PMID 8775758. S2CID 1600286.
  4. ^ Japanese Ministry of Health, Labour and Welfare March 2008 Pharmaceuticals and Medical Devices Safety Information No. 245
  5. ^ Serradell, M.N.; Blancafort, P.; Castaner, J.; Thorpe, P.J. Drugs Fut 1980,5(10),481.
  6. ^ Gerhart Dipl-Chem Dr Griss, 3 More » idem, DE 2040510  (1972 to Thomae Gmbh Dr K).
  7. ^ G Griss, M Kleemann, W Grell, H Ballhause, U.S. patent 3,804,849 (1974 to Boehringer Sohn Ingelheim
  8. ^ Deng Xianglin, et al. CN 104031072  (2014 to Chongqing Zen Pharmaceutical Co Ltd.).
Allikas: https://en.wikipedia.org/wiki/Talipexole
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