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Azapirone
Umespirone
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    Umespirone

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    Umespirone
    Umespirone skeletal.svg
    Clinical data
    Routes of
    administration    		 By mouth
    ATC code
    • none
    Legal status
    Legal status
    • In general: uncontrolled
    Pharmacokinetic data
    Elimination half-life Unknown but effects last much longer than other azapirones, up to 23 hours after a single dose in human clinical studies.
    Identifiers
    • 3-butyl-7-[4-[4-(2-methoxyphenyl)piperazin-1-yl]butyl]-9,9-dimethyl-3,7-diazabicyclo[3.3.1]nonane-2,4,6,8-tetrone
    CAS Number
    PubChem CID
    ChemSpider
    UNII
    Chemical and physical data
    Formula C28H40N4O5
    Molar mass 512.651 g·mol−1
    3D model (JSmol)
    • O=C1N(C(=O)C2C(=O)N(C(=O)C1C2(C)C)CCCCN4CCN(c3ccccc3OC)CC4)CCCC

    Umespirone (KC-9172) is a drug of the azapirone class which possesses anxiolytic and antipsychotic properties. It behaves as a 5-HT1A receptor partial agonist (Ki = 15 nM), D2 receptor partial agonist (Ki = 23 nM), and α1-adrenoceptor receptor antagonist (Ki = 14 nM), and also has weak affinity for the sigma receptor (Ki = 558 nM). Unlike many other anxiolytics and antipsychotics, umespirone produces minimal sedation, cognitive/memory impairment, catalepsy, and extrapyramidal symptoms.

    Synthesis

    Synthesis: Patent:</ref>DE3529872 idem Uwe Schoen, Wolfgang Kehrbach, Werner Benson, Andreas Fuchs, Michael Ruhland, U.S. Patent 4,771,044 (1988 to Kali-Chemie Pharma Gmbh).</ref>

    The condensation between ethyl cyanoacetate (1) and acetone gives ethylisopropylidenecyanoacetate [759-58-0] (2). This product is reacted with N-butylcyanoacetamide [39581-21-0] (3) in sodium methoxide solution to give N-butyl-2,4-dicyano-3,3-dimethylglutarimide, CID:10681941 (4). The glutarimide is cyclized with phosphoric acid to yield 3-butyl-9,9-dimethyl-3,7-diazabicyclo[3.3.1]nonane-2,4,6,8-tetraone, https://pubchem.ncbi.nlm.nih.gov/compound/10825633 CID:10825633 (5).

    The reaction between 1-(o-anisyl)piperazine [35386-24-4] (6) and 1,4-dibromobutane [110-52-1] (7) gives the Quat salt CID:15895413(8).

    Convergent synthesis (in the presence of potassium carbonate) affords Umespirone (KC-9172) (9).

    See also



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