Talipexole

Talipexole
Clinical data
Trade names	Domin
Other names	Alefexole
AHFS/Drugs.com	International Drug Names
Routes of; administration	Oral
ATC code	none;
Legal status
Legal status	In general: ℞ (Prescription only);
Identifiers
	IUPAC name 6-allyl-5,6,7,8-tetrahydro-4H-[1,3]thiazolo[4,5-d]azepin-2-amine;
CAS Number	101626-70-4 ; DIHYDROCHLORIDE: 36085-73-1 36085-73-1 ;
PubChem CID	5374;
IUPHAR/BPS	5442;
ChemSpider	5181 ;
UNII	7AM2J46Z1Y; DIHYDROCHLORIDE: 9R6E1D8H1O ;
ChEMBL	ChEMBL1289023 ;
CompTox Dashboard (EPA)	DTXSID8046321 ;
Chemical and physical data
Formula	C10H15N3S
Molar mass	209.31 g·mol−1
3D model (JSmol)	Interactive image; DIHYDROCHLORIDE: Interactive image;
	SMILES 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) ; Key:DHSSDEDRBUKTQY-UHFFFAOYSA-N ;
	(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).

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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[1] PharmaLetter 22 July 1996 First Launch In Japan For Talipexole

[2] EvaluatePharma Database. Page accessed 9 December 2014

[Talipexole-3] 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.).

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Synthesis

See also

References