Process for preparing 1,5-diaryl-3-substituted pyrazoles

Organic compounds -- part of the class 532-570 series – Organic compounds – Carboxylic acids and salts thereof

Reexamination Certificate

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Reexamination Certificate

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11215329

ABSTRACT:
A process for making a compound of formula I wherein the substituents are as described in the specification comprising reacting a ketone of formula II with succinic anhydride and an alkoxide base to form a compound of formula IIIwhich is reacted with a compound of formula IV to form a compound of Vand reacting with an alcohol to form the corresponding ester of formula VIand reacting the ester with N-methylhydroxylamine.

REFERENCES:
patent: 4808613 (1989-02-01), Kaneko et al.
patent: 4826868 (1989-05-01), Wachter et al.
patent: 4898952 (1990-02-01), Murray et al.
patent: 4944790 (1990-07-01), Moser et al.
patent: 5015763 (1991-05-01), Ono
patent: 5078780 (1992-01-01), Moser et al.
patent: 5114462 (1992-05-01), Moser et al.
patent: 5117054 (1992-05-01), Murray
patent: 5130421 (1992-07-01), Starrett et al.
patent: 5164381 (1992-11-01), Wachter et al.
patent: 5387602 (1995-02-01), Ferro
patent: 5624941 (1997-04-01), Barth et al.
patent: 5843958 (1998-12-01), Ferro et al.
patent: 6384233 (2002-05-01), Abdel-Magid et al.
patent: 6613914 (2003-09-01), Abdel-Magid et al.
patent: 0534800 (1993-03-01), None
patent: 218797 (1992-06-01), None
patent: 1597099 (1990-09-01), None
Murray, W. V. et al. Synthesis and Properties of Aryl 1,3-dioxo Carboxylic Acids, J. Org. Chem., 1990, vol. 55, pp. 3424-3426.
Murray, et al. (J. Org. Chem., vol. 55, pp. 3424-3426, (1990).
Yale, Harry L., The Hydroxamic Acids, Chem. Rev., 1943, 33, 209-257.
Nikishin, G.I, Troyansky, E.I, Svitanko, I.V. & Chizhov, O.S., N,O-Acylotropy in N-Methylpentanehydroxamic Acid, Tetrahedron Lett., 1984, 25, 97-88.
Murray, W.V. & Wachter, M.P., A Simple Regioselective Synthesis of Ethyl 1,5-Diarylpyrazole-3-carboxylates, Heterocyclic Chem., 1989, 26, 1389-1392.
Robinson, Tepoxalin, Drugs of the Future, 1990, 15, 9, 902-903.
Murray, W.V., Hadden, S.K., Wachter, M.P., Synthesis of 3-(1,5-Diphenyl-3-pyrazolyl)aryl Propanoates, J. Heterocyclic Chem., 1990, 27, 1933-1940.
Murray, W.V., Wachter, M.P., Synthesis and Properties of Aryl-1,3-dioxo Carboxylic Acids, J. of Org. Chem., 1990, 55, 3424-3426.
Murray, W., Wachter, M., Barton, D., Forero-Kelly, Y., The Regioselective Synthesis of Tepoxalin, 3-[5-(4-Chlorophenyl)-1-(4-methoxyphenyl)-3-pyrazolyl]-N-hydroxy-N-methylpropanamide and Related 1,5-Diarylpyrazole Anti-inflammatory Agents, Synthesis, 1991, 18-20.
Murray, W.V. & Hadden, S.K., A Facile Synthesis of Tepoxalin, 5-(4-Chlorophenyl)-N-hydroxy-1-(4-methoxyphenyl)-N-Methyl-1H-pyrazole-3-propanamide, J. of Org. Chem. 1992, 57, 6662-6663.
Murray, W.V., The Synthesis of 3-[3-(4-Chlorophenyl)-1-(4-methoxyphenyl)-5-pyrazolyl]-N-hydroxy-N-methylpropanamide, a Regioisomer of Tepoxalin, Tetrahedron Lett., 1993, 34, 1863-1866.
Burinsky, D.J., Armstrong, B.L., Oyler, A.R., & Dunphy, R., Characterization of Tepoxalin and its Related Compounds by High Performance Liquid Chromatoghaphy/Mass Spectrometry, pp. 159-164.
PCT Search Report of International Application No. PCT/US00/20917 mailed Feb. 14, 2001.
Turkish Search Report Application No. 2001/02194 dated Sep. 13, 2002.
Hungarian Search Report dated Jun. 11, 2002.

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