Substituted piperidine compounds and methods of their use

Details Substituted piperidine compounds and methods of their use Substituted piperidine compounds and methods of their use

2005-09-01

2010-10-26

Desai, Rita J (Department: 1625)

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C514S317000

Reexamination Certificate

active

07820827

ABSTRACT:
Novel 3,4-disubstituted-4-aryl-piperidine compounds are disclosed. Pharmaceutical compositions containing the 3,4-disubstituted-4-aryl-piperidine compounds and methods of their pharmaceutical uses are also disclosed. The compounds disclosed are useful, inter alia, as antagonists of opioid receptors.

REFERENCES:
patent: 4115400 (1978-09-01), Zimmerman
patent: 4176186 (1979-11-01), Goldberg et al.
patent: 4891379 (1990-01-01), Zimmerman et al.
patent: 4987126 (1991-01-01), Bargiotti et al.
patent: 5159081 (1992-10-01), Cantrell et al.
patent: 5250542 (1993-10-01), Cantrell et al.
patent: 5270328 (1993-12-01), Cantrell et al.
patent: 5434171 (1995-07-01), Frank et al.
patent: 5972954 (1999-10-01), Foss et al.
patent: 6451806 (2002-09-01), Farrar
patent: WO 02/30896 (2002-04-01), None
Bagnol, D., et al., “Cellular localization and distribution of the cloned MU and KAPPA opioid receptors in rat gastrointestinal tract,”Neuroscience, 1997, 81(2), 579-591.
Bagnol, D., et al., “Changes in enkephalin immunoreactivity of sympathetic ganglia and digestive tract of the cat after splanchnic nerve ligation,”Regul. Pept., 1993, 47, 259-273.
Bhargava, H.N., et al., “Effect of nitric oxide synthase inhibition on tolerance to the analgesic action of D-Pen2, D-Pen5enkephalin and morphine in the mouse,”Neuropeptides, 1996, 30(3), 219-223.
Bilsky, E.J., et al., “Effects of naloxone and D-Phe-Cys-Tyr-D-Trp-Arg-Thr-Pen-Thr-NH2and the protein kinase inhibitors H7 and H8 on acute morphine dependence and antinociceptive tolerance in mice,”J. Pharmacol. &Exp. Ther., 1996, 277(1), 484-490.
Bryan, W.M., et al., “Combinatorial chemistry. Preparation of phenoxypropanolamines,”Tetrahed. Let., 2000, 41. 6997-7000.
Burkett, B.A., et al., “N-Fmoc-dehydroalanine: a versatile molecular scaffold for the rapid solid-phase synthesis of cycloaliphatic amino acids,”Tetrahed. Let., 2000, 41, 6661-6664.
Cantrell, B.E., et al., “Preparation of ω- (4-phenylpiperidino)alkanoates as peripheral opioid receptor receptor antagonists,” CA 118:124401, 1993, 27 pages.
Cantrell, B.E., et al., “Preparation of phenylipiperidine derivatives as peripheral opioid antagonists” CA 119:139107, 1993, 29 pages.
Carpenter, R.L., “Methods using peripheral μ opioid antagonists for the treatment and prevention of dizziness and pruritus,” CA 135:29160, 2001, 6 pages.
Combs, A.P., et al., “N-Arylation of primary and secondary aliphatic amines on solid supports,”J. Comb. Chem., 2002, 4, 179-182.
DeHaven, R.N., et al., “Characterization of opioid receptors.,”Curr. Port. In Pharmac., Enna, S.J., et al. (Eds.), John Wiley & Sons, Inc., 1.4.1-1.4.12, 2000.
Dorland's Illustrated Medical Dictionary, 27thEd., W.B. Saunders Co., 1988, p. 816.
Dorland's Illustrated Medical Dictionary, 27thEd., W.B. Saunders Co., 1988, p. 375.
Dourish, C.T., et al., “Enhancement of morphine analgesia and prevention of morphine tolerance in the rat by the cholecystokinin antagonist L-364,718,”Eur. J. of Pharmacol., 1988, 147, 469-472.
Farrar, J.J., et al., “Methods using a peripheral μ opioid antagonist for the treatment and prevention of ileus,” CA 135:29144, 2001, 6 pages.
Farar, J.J., et al., “Compositions containing opioids and their antagonists,” 135:14336, 2001, 5 pages.
Frank, S.A., et al., “Preparation of 3,4,4,-trisubstituted piperidinyl N-alkylcarboxylates and intermediates, useful as opioid antagonists,” CA 123:313767, 1995, 5 pages.
Koch, T.R., et al., “Inhibitory neuropeptides and intrinsic inhibitory innervation of descending human colon,”Digestive Diseases&Sciences, 1991, 36(6), 712-718.
Kreek, M.J., et al., “Naloxone, a specific opioid antagonist, reverses chronic idiopathic constipation,”The Lancet, 1983, 261-262.
Livingston, E.H., et al., “Postoperative ileus,”Digestive Diseases and Sciences, 1990, 35(1), 121-132.
Mack, D.J., “Paralytic ileus: response to naloxone,”Br. J. Surg., 1989, 76(10), p. 1101.
Mao, M.J., et al., “Oral administration of dextromethorphan prevents the development of morphine tolerance and dependence in rats,”Pain, 1996, 67, 361-368.
Matthews, J., et al., “Based-promoted solid-phase synthesis of substituted hydantoins and thiohydantoins,”J. Org. Chem., 1997, 62, 6090-6092.
Mitch, C.H., et al., “Synthesis and absolute configuration of LY255582, a potent opioid antagonist,”J. of Org. Chem., 1991, 56, 1660-1663.
Nichols, M.L., et al., “Enhancement of the antiallodynic and antinociceptive efficacy of spinal morphine by antisera to dynorphin A (1-13) or MK-801 in a nerve-ligation model of a peripheral neuropathy,”Pain, 1997, 69, 317-322.
Okada, T., et al., “Preparation of 4-pyridyl or 4- (1-piperazinyl)-2,2-diphenylbutanamide derivatives as μ-opioid agonists and medicines containing the same,” 136:325561, 2002, 14 pages.
Orchin, et al.,The Vocabulary of Organic Chemistry,John Wiley&Sons, Inc., 1980, p. 126.
Piscopio, A.D., et al., “A second generation solid phase approach to Freidinger lactams: application of Fukuyama's amine synthesis and cyclative release via ring closing metathesis,”Tetrahed. Let., 1998, 39, 2667-2670.
Piscopio, A.D., et al., “Ring closing metathesis in organic synthesis: Evolution of a high speed, solid phase method for the preparation of β-turn mimetics,”Tetrahedron, 1999, 55, 8189-8198.
Raynor, K., et al., “Pharmacological characterization of the cloned κ-,δ-, and μ-opioid receptors,”Mol. Pharmacol., 1994, 45, 330-334.
Reisine, T., et al., “Opioid analgescis and antagonists,”Goodman&Gilman's The Pharmacological Basis of Therapeutics, 9thEd., 1996, 521-555.
Resnick, J., et al., “Delayed gastric emptying and postoperative ileus after nongastric abdominal surgery: Part I,”Am. J. of Gastroenterology, 1997, 92(5), 751-762.
Resnick, J., et al., “Delayed gastric emptying and postoperative ileus after nongastric abdominal surgery: Part II,”Am. J. of Gastroenterology, 1997, 92(6), 934-940.
Schang, J.C., et al., “Beneficial effects of naloxone in a patient with intestinal pseudoobstruction,”Am. J. Gastroenterology, 1985, 80(6), 407-411.
Schuller, A.G.P., et al., “M6G, but not morphine, inhibits GI transit in MU opioid receptor deficient mice,”Soc. For Neuroscience, 1998, 24, 210.7, p. 524 (abstract).
Smits, S.E., “antagonism by naloxone of morphine-induced single-dose dependence and antinociception in mice,”Res. Commun. In Chem. Pathology&Pharmacology, 1976, 15(4), 689-696.
Werner, J.A., et al., “Synthesis oftrans-3,4-dimethyl-4-(3-hydroxyphenyl)piperidine opioid antagonists: application of thecis-thermal elimination of carbonates to alkaloid synthesis,”J. Org. Chem., 1996, 61, 587-597.
Wittert, G., et al., “Tissue distribution of opioid receptor gene expression in the rat,”Biochem. &Biophys. Res. Commun., 1996, 218, 877-881.
Yang, L., et al., “Solid phase synthesis of Fmoc N-methyl amino acids: application of the Fukuyama amine synthesis,”Tetrahed. Let., 1997, 38(42), 7307-7310.
Zimmerman, D.M., et al., “Discovery of a potent, peripherally selective trans-3,4-dimethyl-4-(3-hydroxyphenyl)piperidine opioid antagonist for the treatment of gastrointestinal motility disorders,” CA 121:57300, 1994, 4 pages.

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