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Talipexole

From Wikipedia, the free encyclopedia
Chemical compound
Pharmaceutical compound
Talipexole
Clinical data
Trade namesDomin
Other namesAlefexole
AHFS/Drugs.comInternational Drug Names
Routes of
administration
Oral
ATC code
  • none
Legal status
Legal status
  • In general: ℞ (Prescription only)
Identifiers
  • 6-allyl-5,6,7,8-tetrahydro-4H-[1,3]thiazolo[4,5-d]azepin-2-amine
CAS Number
PubChemCID
IUPHAR/BPS
ChemSpider
UNII
ChEMBL
CompTox Dashboard(EPA)
Chemical and physical data
FormulaC10H15N3S
Molar mass209.31 g·mol−1
3D model (JSmol)
  • n1c2c(sc1N)CCN(CC2)C\C=C

  • DIHYDROCHLORIDE: C=CCN1CCC2=C(CC1)SC(=N2)N
  • InChI=1S/C10H15N3S/c1-2-5-13-6-3-8-9(4-7-13)14-10(11)12-8/h2H,1,3-7H2,(H2,11,12) ☒N
  • Key:DHSSDEDRBUKTQY-UHFFFAOYSA-N ☒N
 ☒NcheckY (what is this?)  (verify)

Talipexole (B-HT920,Domnin) is adopamine agonist that is marketed as atreatment for Parkinson's Disease in Japan byBoehringer 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 D2dopamine receptor agonist and interacts with both pre- and post-synaptic receptors. It also is anα2-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

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

The N-alkylation of azepan-4-one [105416-56-6] (1) withallyl 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 withthiourea (4) in refluxing ethanol, completing the synthesis of talipexole (5).

See also

[edit]

References

[edit]
  1. ^PharmaLetter 22 July 1996First Launch In Japan For Talipexole
  2. ^EvaluatePharma Database[permanent dead link]. Page accessed 9 December 2014
  3. ^abBenkert 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 2008Pharmaceuticals and Medical Devices Safety Information No. 245Archived 2014-12-10 at theWayback Machine
  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.).
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