Talipexole
Chemical compound
- none
- In general: ℞ (Prescription only)
- 6-allyl-5,6,7,8-tetrahydro-4H-[1,3]thiazolo[4,5-d]azepin-2-amine
- 101626-70-4
N - DIHYDROCHLORIDE: 36085-73-1 36085-73-1
Y
- 5374
- 5442
- 5181 N
- 7AM2J46Z1Y
- DIHYDROCHLORIDE: 9R6E1D8H1O Y
- ChEMBL1289023 N
- DTXSID8046321
- Interactive image
- DIHYDROCHLORIDE: Interactive image
- n1c2c(sc1N)CCN(CC2)C\C=C
- DIHYDROCHLORIDE: C=CCN1CCC2=C(CC1)SC(=N2)N
InChI
- 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-NN
N
Y (what is this?) (verify)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
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
- B-HT-958 [83718-64-3]
- Azepexole [36067-73-9]
- Pramipexole
References
- ^ PharmaLetter 22 July 1996 First Launch In Japan For Talipexole
- ^ EvaluatePharma Database. Page accessed 9 December 2014
- ^ 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.
- ^ Japanese Ministry of Health, Labour and Welfare March 2008 Pharmaceuticals and Medical Devices Safety Information No. 245
- ^ Serradell, M.N.; Blancafort, P.; Castaner, J.; Thorpe, P.J. Drugs Fut 1980,5(10),481.
- ^ Gerhart Dipl-Chem Dr Griss, 3 More » idem, DE 2040510 (1972 to Thomae Gmbh Dr K).
- ^ G Griss, M Kleemann, W Grell, H Ballhause, U.S. patent 3,804,849 (1974 to Boehringer Sohn Ingelheim
- ^ Deng Xianglin, et al. CN 104031072 (2014 to Chongqing Zen Pharmaceutical Co Ltd.).
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- ‡Withdrawn from market
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- §Never to phase III
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