Organic compounds -- part of the class 532-570 series – Organic compounds – Carboxylic acids and salts thereof
Reexamination Certificate
2007-07-03
2007-07-03
Chang, Celia (Department: 1625)
Organic compounds -- part of the class 532-570 series
Organic compounds
Carboxylic acids and salts thereof
C546S239000, C546S240000, C560S008000, C560S115000, C560S159000, C560S160000, C562S450000, C562S555000, C564S156000, C564S157000, C564S158000, C564S159000
Reexamination Certificate
active
11250924
ABSTRACT:
The present invention relates to substantially pure piperidine derivative compounds of the formulae:whereinR1is hydrogen or hydroxy;R2is hydrogen;or R1and R2taken together form a second bond between the carbon atoms bearing R1and R2;R3is —COOH or —COOR4;R4has 1 to 6 carbon atoms;A, B, and D are the substituents of their respective rings each of which may be different or the same and are hydrogen, halogens, alkyl, hydroxy, alkoxy, or other substituents.A process of preparing such piperidine derivative compounds in substantially pure form is also disclosed.
REFERENCES:
patent: 3687956 (1972-08-01), Zivkovic
patent: 3806526 (1974-04-01), Carr et al.
patent: 3829433 (1974-08-01), Carr et al.
patent: 3839431 (1974-10-01), Sheehan et al.
patent: 3862173 (1975-01-01), Carr et al.
patent: 3878217 (1975-04-01), Carr et al.
patent: 3898271 (1975-08-01), Sheehan et al.
patent: 3922276 (1975-11-01), Duncan et al.
patent: 3931197 (1976-01-01), Carr et al.
patent: 3941795 (1976-03-01), Carr et al.
patent: 3946022 (1976-03-01), Carr et al.
patent: 3956296 (1976-05-01), Duncan et al.
patent: 3965257 (1976-06-01), Carr et al.
patent: 4028404 (1977-06-01), Bays et al.
patent: 4254129 (1981-03-01), Carr et al.
patent: 4254130 (1981-03-01), Carr et al.
patent: 4285957 (1981-08-01), Carr et al.
patent: 4285958 (1981-08-01), Carr et al.
patent: 4407823 (1983-10-01), Kirsch et al.
patent: 4550116 (1985-10-01), Soto et al.
patent: 4742175 (1988-05-01), Fawcett et al.
patent: 5375693 (1994-12-01), Woosley et al.
patent: 5578610 (1996-11-01), D'Ambra
patent: 5581011 (1996-12-01), D'Ambra
patent: 5589487 (1996-12-01), D'Ambra
patent: 5663412 (1997-09-01), D'Ambra
patent: 5750703 (1998-05-01), D'Ambra
patent: 6147216 (2000-11-01), Krauss et al.
patent: 6797826 (2004-09-01), D'Ambra
patent: 7022882 (2006-04-01), Tai et al.
patent: 84305268.9 (1985-03-01), None
patent: 1486058 (1986-09-01), None
patent: WO 93/21156 (1993-10-01), None
patent: WO 94/03170 (1994-02-01), None
patent: WO 95/00480 (1995-01-01), None
patent: WO 95/00482 (1995-01-01), None
Hackh's chemical dictionary p. 97 (1983).
Sheehan et al. “Antiinflammatory cyclopropyl . . . ” CA 76:140222 (1972).
K.Y. Chan, et al., “Direct enantiomeric separation of terfenadine and its major acid metabolite by high- performance liquid chromatography, and the lack of stereoselective terfenadine enantiomer biotransformation in man,”J. Chromatog., 271:291-97 (1991).
F.J. McCarty, et al., “Central Depressants. Phosphoramidates Derived from α,α-Disubstituted 4-Piperidinemethanols,”Department of Organic Research Scientific Laboratories, 26:4084-4088(1961).
Chemical Abstract, vol. 94, 1981, pp. 644, 94:156758e.
Chemical Abstract, vol. 110, 1989, pp. 762, 110:173097e.
Woosley, R.L., et al. “Mechanism of the Cardiotoxic Actions of Terfenadine,”JAMA269 (12):1532-36 (Mar. 1993).
Honig, P.K., et al. “Terfenadine-ketoconazole Interaction. Pharmacokinetic and Electrocardiographic Consequences,”JAMA, 269 (12):1513-18 (Mar. 1993).
Kuhlman, J.J., Jr., “Measurement of Azacyclonol in Urine and Serum of Humans Following Terfenadine (Seldane) Administration Using Gas Chromatography-mass Spectrometry,”J Chromatogr578 (2):207-13 (Jul. 1992).
Honig, P.K., et al., “Changes in the Pharmacokinetics and Electrocardiographic Pharmacodynamics of Terfenadine with Concomitant Administration of Erythromycin,”Clin Pharmacol Ther52(3): 231-8 (Sep. 1992).
Chen, T.M., et al., “Determination of the Metabolites of Terfenadine in Human Urine by Thermospray Liquid Chromatography-Mass Spectrometry,”J. Pharm. Biomed. Anal. 9(10-12):929-33, (1991).
Zamani, K., et al., “Enantiomeric Analysis of Terfenadine in Rat Plasma by HPLC,”Chirality, 3(6):467-70 (1991).
Eller, M.G., et al., “Absence of Food Effects on the Pharmacokinetics of Terfenadine,”Biopharm. Drug Dispos. 13(3):171-7 (Apr. 1992).
Chan, K.Y., “Direct Enantiomeric Separation of Terfenadine and its Major Acid Metabolite by High Performance Liquid Chromatography, and the Lack of Stereoselective Terfenadine Enantiomer Biotransformation in Man,”J. Chromatogr. 571(1-2) 291-7 (1991).
Eller, M.G., et al., “Pharmacokinetics of Terfenadine in Healthy Elderly Subjects,”J. Clin. Pharmacol. 32(3):267-71 (Mar. 1992).
Coutant, J.E., et al. “Determination of Terfenadine and Terfenadine Acid Metabolite in Plasma using Solid-Phase Extraction and High-Performance Liquid Chromatography with Fluorescence Detection,”J. Chromatogr. 570(1):139-48 (1991).
Luo, H., et al. “N(+)-glucuronidation of Aliphatic Tertiary Mines, A General Phenomenon in the Metabolism of H1-antihistamines in Humans,”Xenobiotca., 21(10):1281-8 (Oct. 1991).
Estelle, F., et al., “Pharmacokinetic Optimisation of Histamine H1-Receptor Antagonist Therapy,”Clin. Pharmacokinet., 21(5):372-93 (Nov. 1991).
Shall, L. et al., “Dose-Response Relationship Between Objective Measures of Histamine-Induced Weals and Dose of Terfenadine,”Acta. Derm. Venereol. 71(3):199-204 (1991).
Campoli-Richards, D.M., et al., “Cetirizine. A Review of its Pharmacological Properties and Clinical Potential in Allergic Rhinitis, Pollen-Induced Asthma, and Chronic Urticaria,”Drugs40(5)762-81 (Nov. 1990).
Snowman, A.M., et al., “Cetirizine: Actions on Neurotransmitter Receptors,”J. Allergy Clin. Immunol. 86(6-2)1025-8 (Dec. 1990).
Berman, B.D., “Perennial Allergic Rhinitis: Clinical Efficacy of a New Antihistamine,”J. Allergy Clin. Immunol. 86 (68-2)1004- (Dec. 1990).
Monahan, B.P., et al., “Torsades de Pointes Occurring in Association with Terfenadine Use,”JAMA, 264(21) 2788-90 (Dec. 1990).
Simons, K.J., et al., “Pharmacokinetics and Pharmacodynamics of Terfenadine and Chlorpheniramine In the Elderly,”J. Allergy Clin. Ummunol. 85(3)540-7 (Mar. 1990).
Sweeney, G.D., et al., “Anti-Allergy and Anti-Asthma Drugs. Disposition in Infancy and Childhood,”Clin. Pharmacokinet, 17 Suppl (1):156-68 (1989).
Coniglio, A.A., “Effect of Acute and Chronic Terfenadine on Free and Total Serum Phenytoin Concentrations in Epileptic Patients,”Epilepsia30(5):611-6 (Sep.-Oct. 1989).
Mann, K.V., et al., “Nonsedating Histamine H1-Receptor Antagonists,”Clin. Pharm. 8(5):331-44 (May 1898).
Barenhotz, H.A., “Loratadine: A Non Sedating Antihistamine with Once-Daily Dosing,”DICP23(6)44550 (Jun. 1989).
Brion, N., et al., “Lack of Effect of Terfenadine on Theophylline Pharmacokinetics and Metabolism in Normal Subjects,”Br J. Clin. Pharmacol., 27(3)391-5 (Mar. 1989).
Kaliner, M.A., “Non-sedating Antihistamines,”Allergy Proc. 9(6):649-63 (Nov.-Dec. 1988).
Maurer, H., et al., “Identification and Differentiation of Alkylamine Antihistamines and Their Metabolites I Urine by Computerized Gas Chromatography-Mass Spectrometry,”J. Chromatogr430(1):31-31 (Aug. 1988).
Simons, F.E., et al., “Lack of Subsensitivity to Terfenadine During Long-Term Terfenadine Treatment,”J. Allergy Clin Immunol82(6):1068-75 (Dec. 1988).
Shall, L., et al., “Assessment of the Duration of Action of Terfenadine on Histamine Induced Weals,”Br. J. Dermatol119(4):525-31 (Oct. 1988).
Akagi, M., “Antiallergic Effects of Terfenadine on Immediate Type Hypersensitivity Reactions,”Immunopharmacol Immunotoxicol9(2-3):257-79 (1987).
Snyder, S.H., et al., “Receptor Effects of Cetirizine,”Ann Allergy59(6-2):4-8 (Dec. 1987).
Simons, F.E., “The Pharmacokinetics and Pharmacodynamics of Terfenadine in Children,”J. Allergy Clin Immunol. (6):884-90 (1987).
Carter, C.A., et al., “Terfenadine, A Nonsedating Antihistamine,”Drug Intell Clin Pharm19(11):812-7 (Nov. 1985).
Paton, D.M., et al., Clinical Pharmacokinetics of H1-Receptor Antagonists (He Antihistamines)Clin Pharmacokinet. 10(6):477-97 (Nov.-Dec. 1985).
Woodward, J.K
AMR Technology , Inc.
Chang Celia
Heslin Rothenberg Farley & & Mesiti P.C.
LandOfFree
Piperidine derivatives and process for their production does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Piperidine derivatives and process for their production, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Piperidine derivatives and process for their production will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-3786797