Process for production of piperidine derivatives

Details Process for production of piperidine derivatives Process for production of piperidine derivatives

Filed on

2005-12-13

Date issued

2005-12-13

Examiner

Chang, Celia (Department: 1625)

Patent Class

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

SubClass

Organic compounds

SubSubClass

Heterocyclic carbon compounds containing a hetero ring...

Other Related Categories

C546S209000, C546S210000, C546S216000, C546S240000, C544S034000, C544S096000, C544S299000, C540S469000, C540S470000, C540S488000, C540S492000

Type

Reexamination Certificate

Status

active

Patent number

06974872

Description

ABSTRACT:
The present invention discloses processes for preparing piperidine derivative compounds of the formulae:whereinn is 0 or 1;R1is hydrogen or hydroxy;R2is hydrogen;or, when n is 0, R1and R2taken together form a second bond between the carbon atoms bearing R1and R2, provided that when n is 1, R1and R2are each hydrogen;R3is —COOH or —COOR4;R4is an alkyl or aryl moiety;A, B, and D are the substituents of their rings, each of which may be different or the same, and are selected from the group consisting of hydrogen, halogens, alkyl, hydroxy, alkoxy, and other substituents.

REFERENCES:
patent: 2919274 (1959-12-01), Faust et al.
patent: 3687956 (1972-08-01), Zivhovic
patent: 3806526 (1974-04-01), Carr et al.
patent: 3829433 (1974-08-01), Carr et al.
patent: 3839431 (1974-10-01), Sheeham
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: 4957927 (1990-09-01), Ferrand et al.
patent: 5204249 (1993-04-01), Schwartz et al.
patent: 5375693 (1994-12-01), Woosley et al.
patent: 5382600 (1995-01-01), Jönsson et al.
patent: 5578610 (1996-11-01), D'Ambra
patent: 5581011 (1996-12-01), D'Ambra
patent: 5589486 (1996-12-01), Harsanyi et al.
patent: 6201124 (2001-03-01), D'Ambra et al.
patent: 6242606 (2001-06-01), Krauss et al.
patent: 134124 (1985-03-01), 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
patent: WO 97 23213 (1997-07-01), None
Krauss et al. “Preparation of . . . ” CA 135:19556 (2001).
Greene “Protective groups in organic synthesis” Wiley interscience, p. 152-153, 185-186 (1982).
Meyers et al., “Oxazolines. IX. Synthesis of Homologated Acetic Acids and Esters,” J. Org. Chem., 39:2778-2783 (1974).
Meyers et al., “Oxazolines X. Synthesis of γ-Butyrolactones,”J. Org. Chem., 39:2783-2787 (1974).
Meyers et al., “Oxazolines. XI. Synthesis of Functionalized Aromatic and Aliphatic Acids. A Useful Protecting Group for Carboxylic Acids against Grignard and Hydride Reagents.” J. Org. Chem., 39:2787-2793 (1974).
Milstein et al., “A General, Selective, and Facile Method for Ketone Synthesis from Acid Chlorides and Organotin Compounds Catalyzed by Palladium,” Journal of the American Chemical Society, 100:3636-3638 (1978).
Milstein et al., “Mild, Selective, General Method of Ketone Synthesis from Acid Chlorides and Organotin Compounds Catalyzed by Palladium,” J. Org. Chem , 44:1613-1618 (1979).
March,Advanced Organic Chemistry: Reactions Mechanisms, and Structure, 4th Ed., New York: John Wiley & Sons, pp. 478-479 and 661-662 (1992).
Buchler et al., “Organic Syntheses,”Wiley Intersciencep. 789 (1970).
Fishwick et al., “An Efficient Route to S-N-(9 Fluorenylmethoxycarbonyl)-4′-(t-azi-2.2.2-tritjuoroethyl)phenylalanine,”Tetrahedron Letters, 35:4611-4614 (1994).
Neubold, “Cyclic Imido Acid Esters,” Ca 79:92196 (1973).
Boell et al., “2-Pyridinols,” CA 90:6252 (1978).
Caujolle et al., “Synthesis Amiparasitic and Antifungal Activities of Arylalkyl and Arylvinylthiazolines,” CA 119:139162 (1993).
Clarke et al., “A Facile One Stage Synthesis of Oxazolines Under Microwave Irradiation,” CA 124:317042 (1996).
Meyers et al., “Synthesis via Oxazolines. A Highly Stereoselective Synthesis of +/−)-cis-2-Methyl Cyclopentanecarboxylic Acid, Via a Kinetically Controlleed Cyclization,”J.C.S. Chem. Comm. pp. 768-770 (1974).
Swain et al., “Novel-HT3 Antagonists: Indol-3-yllspiro(azabicycloalkane-3.5′(4″H)oxazoles),” J. Med. Chem. 35(6):1019-31 (1992).
Kawai et al., “A Facile Synthesis of an Oxidation Product of Terfenadine,” J. Org. Chem. 59:2620-22 (1994).
Murugesan et al., “Preparation of N-isoxazolylbiphenylsulfonamides as Endothelin Antagonists,” CA 125:10795 (1996).
Busaeea et al., “A One Step Synthesis of Thiazolines from Esters,” CA 125:58380 (1996).
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,” Journal of Chromatography, 271:291-97 (1991).
F.J. McCarty, et al., “Central Depressants, Phosphoramidates Derived from α,α-Disubstituted 4-Piperidinemathanols,”Department of Organic Research, Scientific Laboratories, (1961).
Chemical Abstract, vol. 94, 1981, pp. 644, 94:156758e.
Chemical Abstract, vol. 110, 1989, pp. 762, 110:173097e.
Woosley, R.I. . , et al. “Mechanism of the Cardiotoxic Actions of Terfenadine,” JAMA 269 (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 Azacyclonal in Urine and Serum of Humans Following Terfenadine (Seklane) Administration Using Gas Chromatography-mass Spectrometry,” J. Chromatogr. 578 (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. Ther. 52(3): 231-8 (Sep. 1992).
Chen, T.M., et al., “Determination of the Metabolites of Terfenadine in Human Urine by Thermospray Liquid Chromatography-Mass Spectrometery,” J. Pharm. Biomed. Anal. 9(10-12):929-33, (1991).
Eller et al., “Pharmacokinetics of Terfenadine in Healthy Elderly Subjects,”J. Clin. Pharmacol. 32(3):267-71 (1992).
Coutant 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).
Lao, H., et al. “N( l )-glucuronidation of Aliphatic Tertiary Mines, A General Phenomenon in the Metabolism of III-antihistamines in Humans,” Xenobiotca.. 21(10):1281-8 (Oct. 1991).
Estelle, F., et al., “Pharmacokinetic Optimisation of Histamine III-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. Denn. 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. Immunol. 85(3)540-7 (Mar. 1990).
Sweeney, G.D., et al., “Anti-Allergy and Anti

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