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

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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:

     

      • Figure 00020001
      • (2) EP-A-420064 discloses a compound of:
        Figure 00020002
      • (3) EP-A-447285 discloses a compound of:
        Figure 00020003
      • (4) EP-A-662471 discloses a compound of:
        Figure 00020004
      • (5) EP-A-591057 discloses a compound of:
        Figure 00020005
      • (6) EP-A-527687 discloses compounds of:
        Figure 00030001

        X=S, 0, Y=CH
        X=0, NH, Y=N

      • (7) EP-A-506539 discloses compounds of:
        Figure 00030002
    • Tricyclic or more poly-cyclic compounds with a cyclic ether moiety, such as those mentioned below, are known.

      • (1) Compounds of:
        Figure 00030003

        are disclosed in Tetrahedron Lett., Vol. 36, p. 7019 (1995).

      • (2) Compounds of:
        Figure 00040001
        Figure 00040002

        are disclosed in J. Med. Chem., Vol. 35, p. 3625 (1992).

      • (3) Compounds of:
        Figure 00040003

        are disclosed in Tetrahedron, Vol. 48, p. 1039 (1992).

      • (4) Compounds of:
        Figure 00040004

        are disclosed in Tetrahedron Lett., Vol. 32, p. 3345 (1991).

      • (5) A compound of:
        Figure 00050001

        is disclosed in Bioorg. Chem., Vol. 18, p. 291 (1990).

      • (6) A compound of:
        Figure 00050002

        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

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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DR ANTHONY MELVIN CRASTO Ph.D

DR ANTHONY MELVIN CRASTO, Born in Mumbai in 1964 and graduated from Mumbai University, Completed his Ph.D from ICT, 1991,Matunga, Mumbai, India, in Organic Chemistry, The thesis topic was Synthesis of Novel Pyrethroid Analogues, Currently he is working with AFRICURE PHARMA, ROW2TECH, NIPER-G, Department of Pharmaceuticals, Ministry of Chemicals and Fertilizers, Govt. of India as ADVISOR, earlier assignment was with GLENMARK LIFE SCIENCES LTD, as CONSUlTANT, Retired from GLENMARK in Jan2022 Research Centre as Principal Scientist, Process Research (bulk actives) at Mahape, Navi Mumbai, India. Total Industry exp 32 plus yrs, Prior to joining Glenmark, he has worked with major multinationals like Hoechst Marion Roussel, now Sanofi, Searle India Ltd, now RPG lifesciences, etc. He has worked with notable scientists like Dr K Nagarajan, Dr Ralph Stapel, Prof S Seshadri, etc, He did custom synthesis for major multinationals in his career like BASF, Novartis, Sanofi, etc., He has worked in Discovery, Natural products, Bulk drugs, Generics, Intermediates, Fine chemicals, Neutraceuticals, GMP, Scaleups, etc, he is now helping millions, has 9 million plus hits on Google on all Organic chemistry websites. His friends call him Open superstar worlddrugtracker. His New Drug Approvals, Green Chemistry International, All about drugs, Eurekamoments, Organic spectroscopy international, etc in organic chemistry are some most read blogs He has hands on experience in initiation and developing novel routes for drug molecules and implementation them on commercial scale over a 32 PLUS year tenure till date Feb 2023, Around 35 plus products in his career. He has good knowledge of IPM, GMP, Regulatory aspects, he has several International patents published worldwide . He has good proficiency in Technology transfer, Spectroscopy, Stereochemistry, Synthesis, Polymorphism etc., He suffered a paralytic stroke/ Acute Transverse mylitis in Dec 2007 and is 90 %Paralysed, He is bound to a wheelchair, this seems to have injected feul in him to help chemists all around the world, he is more active than before and is pushing boundaries, He has 100 million plus hits on Google, 2.5 lakh plus connections on all networking sites, 100 Lakh plus views on dozen plus blogs, 227 countries, 7 continents, He makes himself available to all, contact him on +91 9323115463, email amcrasto@gmail.com, Twitter, @amcrasto , He lives and will die for his family, 90% paralysis cannot kill his soul., Notably he has 38 lakh plus views on New Drug Approvals Blog in 227 countries......https://newdrugapprovals.wordpress.com/ , He appreciates the help he gets from one and all, Friends, Family, Glenmark, Readers, Wellwishers, Doctors, Drug authorities, His Contacts, Physiotherapist, etc He has total of 32 International and Indian awards

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