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BMY-14802

From Wikipedia, the free encyclopedia
Chemical compound
Pharmaceutical compound
BMY-14802
Clinical data
Other namesBMS-181100; MJ-14802
ATC code
  • None
Identifiers
  • 1-(4-fluorophenyl)-4-[4-(5-fluoropyrimidin-2-yl)piperazin-1-yl]butan-1-ol
CAS Number
PubChemCID
IUPHAR/BPS
ChemSpider
UNII
ChEMBL
CompTox Dashboard(EPA)
Chemical and physical data
FormulaC18H22F2N4O
Molar mass348.398 g·mol−1
3D model (JSmol)
  • c1cc(F)ccc1C(O)CCCN2CCN(CC2)c3ncc(F)cn3
  • InChI=1S/C18H22F2N4O/c19-15-5-3-14(4-6-15)17(25)2-1-7-23-8-10-24(11-9-23)18-21-12-16(20)13-22-18/h3-6,12-13,17,25H,1-2,7-11H2 ☒N
  • Key:ZXUYYZPJUGQHLQ-UHFFFAOYSA-N ☒N
 ☒NcheckY (what is this?)  (verify)

BMY-14802, also known asBMS-181100, is a drug withantipsychotic effects which acts as both asigma receptorantagonist and a5-HT1A receptoragonist.[1][2][3][4] It also hasaffinity for the5-HT2 andD4 receptors.[5] The drug reachedphase IIIclinical trials for the treatment ofpsychosis but was never marketed.[6]

Synthesis

[edit]

Patent (Ex1/2/5/6/7):[7]

The reaction of 4-chloro-4'-fluorobutyrophenone [3874-54-2] (1) withethylene glycol gives theketal, 2-(3-chloropropyl)-2-(4-fluorophenyl)-1,3-dioxolane [3308-94-9] (2). The reaction of 2-chloro-5-fluoro-4-methylthiopyrimidine [87789-51-3] (3) with N-carboethoxypiperazine [120-43-4] (4) gives ethyl-4-(5-fluoro-4-methylthio-2-pyrimidinyl)-1-piperazine carboxylate,PC10470079 (5). Catalytic hydrogenation removes the thiomethyl group giving ethyl-4-(5-fluoro-2-pyrimidinyl)-1-piperazine carboxylate [87789-52-4] (6). Acid hydrolysis of the carbamate protecting group gives a secondary amine and hence 5-fluoro-2-(piperazin-1-yl)pyrimidine [87789-49-9] (7). Alkylation of2 with7 and subsequent hydrolysis of theketal protecting group afforded 1-(4-fluorophenyl)-4-(4-(5-fluoro-2-pyrimidinyl)-1-piperazinyl)butan-1-one [133982-66-8] (8). Lastly, reduction of the benzoyl ketone with sodium borohydride gave the alcohol, completing the synthesis of BMY-14802 (9).

See also

[edit]

References

[edit]
  1. ^Taylor DP, Eison MS, Moon SL, Schlemmer RF, Shukla UA, VanderMaelen CP, et al. (1993). "A role for sigma binding in the antipsychotic profile of BMY 14802?".NIDA Research Monograph.133:125–157.PMID 8232511.
  2. ^Vanecek SA, Essman WD, Taylor DP, Woods JH (January 1998). "Discriminative stimulus characteristics of BMY 14802 in the pigeon".The Journal of Pharmacology and Experimental Therapeutics.284 (1):1–9.PMID 9435153.
  3. ^Kitanaka J, Kitanaka N, Tatsuta T, Hall FS, Uhl GR, Tanaka K, et al. (May 2009)."Sigma1 receptor antagonists determine the behavioral pattern of the methamphetamine-induced stereotypy in mice".Psychopharmacology.203 (4):781–792.doi:10.1007/s00213-008-1425-z.PMC 3157915.PMID 19052726.
  4. ^Paquette MA, Foley K, Brudney EG, Meshul CK, Johnson SW, Berger SP (July 2009)."The sigma-1 antagonist BMY-14802 inhibits L-DOPA-induced abnormal involuntary movements by a WAY-100635-sensitive mechanism".Psychopharmacology.204 (4):743–754.doi:10.1007/s00213-009-1505-8.PMC 2845289.PMID 19283364.
  5. ^Zamanillo D, Portillo-Salido E, Vela JM, Romero L (20 April 2012)."Sigma 1 Receptor Chaperone: Pharmacology and Therapeutic Perspectives". In Botana LM, Loza M (eds.).Therapeutic Targets: Modulation, Inhibition, and Activation. John Wiley & Sons. pp. 248–.ISBN 978-1-118-18552-0.
  6. ^"BMS 181100".AdisInsight. Springer Nature Switzerland AG.
  7. ^Joseph P. Yevich & Walter G. Lobeck, Jr.,U.S. patent 4,605,655 (1986 to Bristol Myers Co).
D1-like
Agonists
PAMs
Antagonists
D2-like
Agonists
Antagonists
5-HT1
5-HT1A
5-HT1B
5-HT1D
5-HT1E
5-HT1F
5-HT2
5-HT2A
5-HT2B
5-HT2C
5-HT3–7
5-HT3
5-HT4
5-HT5A
5-HT6
5-HT7
σ1
σ2
Unsorted
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