Opiate analogs selective for the δ-opioid receptor

Details Opiate analogs selective for the δ-opioid receptor Opiate analogs selective for the δ-opioid receptor

2007-01-16

2007-01-16

Seaman, D. Margaret (Department: 1625)

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C546S045000, C546S046000

Reexamination Certificate

active

10665377

ABSTRACT:
Novel compounds which selectively bind to the δ-opioid receptor have been designed. These compounds have greater selectivity, improved water (blood) solubility, and enhanced therapeutic value as analgesics. Because agonists with selectivity for the δ-opioid receptor have shown promise in providing enhanced analgesis without the addictive properties, the compounds of the present invention are better than morphine, naltrindole (NTI), spiroindanyloxymorphone (SIOM), and other known μ-opioid receptor selectors as analgesics.

REFERENCES:
patent: 4816586 (1989-03-01), Portoghese
patent: 5298622 (1994-03-01), Portoghese et al.
patent: 5436249 (1995-07-01), Dappen et al.
patent: 5457208 (1995-10-01), Portoghese et al.
patent: 5578725 (1996-11-01), Portoghese et al.
patent: 5852030 (1998-12-01), Nagase et al.
patent: 5922887 (1999-07-01), Dondio et al.
patent: 6177438 (2001-01-01), Nagase et al.
patent: 6359111 (2002-03-01), Meyer et al.
patent: 0663401 (2000-06-01), None
patent: WO 99/67206 (1999-12-01), None
Kotick, J Med Chem, vol. 24, pp. 1445-1450, 1981.
Portoghese, J Med Chem, vol. 37, pp. 579-585, 1994.
Anathan, J Med Chem, vol. 42, 3527-3538, 1999.
Abdelhamid et al., “Selective blockage of Delta opiod receptors prevents the development of morphine tolerance and dependence in mice,”J. Pharmacol. Exp. Ther., 258(1):299-303, 1991.
Akil et al., “Endogenous opioids: biology and function,”Annual Rev. Neurosci., 7:223-255, 1984.
Ananthan et al., “Synthesis, opioid receptor binding, and bioassay of naltrindole analogues substituted in the indolic benzene moiety,”J. Med. Chem., 41(15):2872-2881, 1998.
Ananthan et al., “Synthesis, opioid receptor binding, and biological activities of naltrexone-derived pyrido- and pyrimidomorphinans,”J. Med. Chem., 42(18):3527-3538, 1999.
Bertolucci et al., “Microdialysis of opioid peptide release from the nucleus accumbens and ventrical pallidum of the freely moving rat,”Neurosci. Abstr., 18L1368, 1992.
Blisky et al., “SNC 80, a selective, nonpeptidic and systemically active opioid delta agonist,”J. Pharmacol. Exp. Ther., 273(1):359-366, 1995.
Bradbury et al., “Biosynthetic origin and receptor conformation of methionine enkephalin,”Nature, 260:165-166, 1976.
Conn et al., “An unusual fischer indole synthesis with 4-keto acids: an indole incorporating the terminal hydrazine nitrogen,”J. Org. Chem., 55(90):2908-2913, 1990.
Coombs et al., “Intrathecal morphine tolerance: use of intrathecal clonidine, DADLE, and intraventricular morphine,”Anesthesiology, 62(3):358-363, 1985.
Cramer III et al., “Comparative moleculer field analysis (CoMFA). 1. Effect of shape on binding of steroids to carrier proteins,”J. of the Am. Chem. Soc., 110(18):5959-5967, 1988.
Dressman and Lennėrnas, In:Oral Drug Absorption: Prediction and Assessment(Drugs and the Pharmaceutical Sciences), vol. 106, 2000.
Foley, In:Handbook of Experimental Pharmacology, Herz (ed.), vol. 104/II: Opioids II, Springer-Verlag, Berlin, 693-743, 1993.
Gomes-Flores and Weber, “Differential effects of buprenorphine and morphine on immune and neuroendocrine functions following acute administration in the rat mesencephalon periaqueductal gray,”Immunopharm., 48:145-156, 2000.
Hardman and Limbird, In:Goodman&Gilman's The Pharmacological Basis of Therapeutics, 10thed., McGraw-Hill Professional Publishing, 2001.
House et al., “Suppression of immune function by non-peptidic delta opioid receptor antagonists,”Neurosci. Lett., 198:119, 1995.
Hughes et al., “Identification of two related pentapeptides from the brain with potent opiate agonist activity,”Nature, 258:577-579, 1975.
Kaliszan et al., “Gradient HPLC in the determination of drug lipophilicity and acidity,”Pure Appl. Chem., 73:1465-1475, 2001.
Knapp et al., “Properties of TAN-67, a nonpeptidic δ-opioid receptor agonist, at cloned human δ- and μ-opioid receptors,”Eur. J. Pharmacol., 291(2):129-134, 1995.
Knapp et al., “Structure-activity relationships for SNC80 and related compounds at cloned human delta and mu opioid receptors,”J. Pharmacol. Exp. Ther., 277(3):1284-1291, 1996.
Koob et al., “Neural substrates of opiate withdrawal,”TINS, 15(5):186-191, 1992.
Liao et al., “De novo design, synthesis, and biological activities of high-affinity and selective non-peptide agonists of the δ-opioid receptor,”J. Med. Chem., 41(24):4767-4776, 1998.
Loh et al., “Molecular characterization of opioid receptors,”Annu. Rev. Pharmacol. Toxicol., 30:123-147, 1990.
Lutz and Pfister, “Opioid receptors and their pharmacological profiles,”J. Receptor Res., 12(3):267-286, 1992.
Martin, “Pharmacology of opioids,”Pharmacol. Rev., 35(4):283-323, 1983.
Okawa et al., “7-arylindenenaltrexones as selective δ1 opioid receptor antagonists,”J. Med. Chem., 41:4177-4180, 1998.
Olson et al., “Endogenous opiates: 1988,”Peptides, 10:1253-1280, 1989.
Pert and Snyder, “Opiate receptor: demonstration in nervous tissue,”Science, 179(4077):1011-1014, 1973.
Pfeiffer et al., “Psychotomimesis mediated by $/kappa $ opiate receptors,”Science, 233(4765):774-776, 1986.
Plobeck et al., “New diarylmethylpiperazines as potent and selective nonpeptidic δ opioid receptor agonists with increased in vitro metabolic stability,”J. Med. Chem., 43(21):3887-3894, 2000.
Olmsted et al., “A remarkable change of opioid receptor selectivity on the attachment of a peptidomimetic κ address element to the δ antagonist, natrindole: 5′[(N2-alkylamindino)methyl]naltrindole derivatives as a novel class of κ opioid receptor antagonists,”J. Med. Chem., 36:179-180, 1993.
Portoghese et al., “7-arylidenenaltrexones as selective δ1 opioid receptor antagonists,”J. Med. Chem., 41:4177-4180, 1998.
Raynor et al., “Pharmacological characterization of the cloned κ-, δ-, and μ- opioid receptors,”Molecular Pharmacol., 45:330-334, 1994.
Reid et al., “Naltrindole, and opioid delta receptor antagonist, blocks cocaine-induced facilitation of responding for rewarding brain stimulation,”Life Sci., 52:PL67-71, 1993.
Saltzman, In:Drug Delivery: Engineering Principles for Drug Therapy(Topics in Chemical Engineering), Oxford University Press, 2001.
Schiller et al., “The opioid μ agonist/δ antagonist DIPP-NH2[Ψ] produces a potent analgesic effect, no physical dependence, and less tolerance than morphine in rats,”J. Med. Chem., 42(18):3520, 1999.
Sharp and Yaksh, “Pain killers of the immune system,”Nat. Med., 3(8):831-832, 1997.
Simon, “Opioid receptors and endogenous opioid peptides,”Medicinal Res. Rev., 11(4):357-374, 1991.
Stevens et al., “Potent and selective indolomorphinan antagonists of the kappa-opioid receptor,”J. Med. Chem., 43(14):2759-2769, 2000.
Takemori and Portoghese, “Selective natrexone-derived opioid receptor antagonists,”Annu. Rev. Pharmacol. Toxicol., 32:239-269, 1992.
Wei et al., “N,N-diethyl-4-(phenylpiperidin-4-ylidenemethyl)benzamide: a novel exceptionally selective, potent δ opioid receptor agonist with oral bioavailability and its analogues,”J. Med. Chem., 43(21):3895-905, 2000.
Peng et al., “3D-QSAR comparative molecular field analysis on opioid receptor antagonists: pooling data from different studies,”Journal of Medicinal Chemistry, 48(5):1620-1629, 2005.
Peng et al., “3D-QSAR comparative molecular field analysis on opioid receptor agonists SNC80 and its analogs,”Journal of Molecular Graphics&Modeling, submitted Jan. 31, 2005.
Gao et al., “Synthesis of 7-arylmorphinans. Probing the address requirements for selectivity at opioid delta receptors,”J Med Ch

Affiliated with

Also associated with

Rating

Opiate analogs selective for the δ-opioid receptor does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Opiate analogs selective for the δ-opioid receptor, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Opiate analogs selective for the δ-opioid receptor will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-3810413