N-{2-[7-(Cyclohexylmethyl)-1,6-dihydro-2H-indeno[5,4-b]furan-8-yl]ethyl}acetamide

N-{2-[7-(Cyclohexylmethyl)-1,6-dihydro-2H-indeno[5,4-b]furan-8-yl]ethyl}acetamide

N-[2-(7-Benzyl-1,6-dihydro-2H-indeno[5,4-b]furan-8-yl)ethyl]acetamide

N-{2-[7-(Cyclohexylmethyl)-1,6-dihydro-2H-indeno[5,4-b]furan-8-yl]ethyl}acetamide

Acetamide, N-​[2-​[7-​(cyclohexylmethyl)​-​1,​6-​dihydro-​2H-​indeno[5,​4-​b]​furan-​8-​yl]​ethyl]​-

339.47, C22 H29 N O2

cas 1287785-08-3

Melatonin MT2 Agonists

Takeda……..innovator

Treatment of Sleep Disorders,

• Melatonin (N-acetyl-5-methoxytryptamine), which is a hormone synthesized and secreted principally in the pineal gland, increases in dark circumstances and decreases in light circumstances. Melatonin exerts suppressively on pigment cells and the female gonads, and acts as a synchronous factor of biological clock while taking part in transmittance of photoperiodic code. Therefore, melatonin is expected to be used for the therapy of diseases related with melatonin activity, such as reproduction and endocrinic disorders, sleep-awake rhythm disorders, jet-lag syndrome and various disorders related to aging, etc.
• Recently, it has been reported that the production of melatonin melatonin could reset the body’s aging clock (see Ann. N. Y. Acad. Sci., Vol. 719, pp. 456-460 (1994)). As previously reported, however, melatonin is easily metabolized by metabolic enzymes in vivo (see Clinical Examinations, Vol. 38, No. 11, pp. 282-284 (1994)). Therefore, it cannot be said that melatonin is suitable as a pharmaceutical substance.
• Various melatonin agonists and antagonists such as those mentioned below are known.

  • (1) EP-A-578620 discloses compounds of:

  
  

  • • 
    • (2) EP-A-420064 discloses a compound of:
      
    • (3) EP-A-447285 discloses a compound of:
      
    • (4) EP-A-662471 discloses a compound of:
      
    • (5) EP-A-591057 discloses a compound of:
      
    • (6) EP-A-527687 discloses compounds of:
      
      X=S, 0, Y=CH
      X=0, NH, Y=N
    • (7) EP-A-506539 discloses compounds of:
      
  • Tricyclic or more poly-cyclic compounds with a cyclic ether moiety, such as those mentioned below, are known.

    • (1) Compounds of:
      
      are disclosed in Tetrahedron Lett., Vol. 36, p. 7019 (1995).
    • (2) Compounds of:
      
      
      are disclosed in J. Med. Chem., Vol. 35, p. 3625 (1992).
    • (3) Compounds of:
      
      are disclosed in Tetrahedron, Vol. 48, p. 1039 (1992).
    • (4) Compounds of:
      
      are disclosed in Tetrahedron Lett., Vol. 32, p. 3345 (1991).
    • (5) A compound of:
      
      is disclosed in Bioorg. Chem., Vol. 18, p. 291 (1990).
    • (6) A compound of:
      
      is disclosed in J. Electroanal. Chem. Interfacial Electrochem., Vol. 278, p. 249 (1990).

    
    

    see

http://www.google.co.in/patents/EP0885210B1?cl=en

Highly Potent MT2-Selective Agonists

J. Med. Chem., 2011, 54 (9), pp 3436–3444

DOI: 10.1021/jm200221q

http://pubs.acs.org/doi/full/10.1021/jm200221q

N-{2-[7-(Cyclohexylmethyl)-1,6-dihydro-2H-indeno[5,4-b]furan-8-yl]ethyl}acetamide (15)

By a similar procedure that described for 8, 15 (79%) was obtained as a white solid; mp 133−134 °C (EtOAc/hexane).

1H NMR (CDCl3) δ 0.82−1.03 (2H, m), 1.06−1.32 (3H, m), 1.42−1.78 (6H, m), 1.96 (3H, s), 2.32 (2H, d, J = 7.2 Hz), 2.74 (2H, t, J = 7.2 Hz), 3.26 (2H, s), 3.32−3.52 (4H, m), 4.59 (2H, t, J= 8.6 Hz), 5.60 (1H, s), 6.59 (1H, d, J = 7.9 Hz), 7.11 (1H, d, J= 7.9 Hz).

MS (ESI) m/z 340 (M + H)+. Anal. (C22H29NO2) C, H, N.

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