Rotamase enzyme activity inhibitors

Details Rotamase enzyme activity inhibitors Rotamase enzyme activity inhibitors

1996-05-13

1998-09-01

MacMillan, Keith

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Ester doai

514330, 514423, 514428, 514534, 514538, 514547, 514549, 514551, 514465, 514466, 549441, 560 39, 560 43, 560170, A61K 31445, A61K 3140, A61K 3122, A61K 3124

Patent

active

058011978

ABSTRACT:
This invention relates to the method of using specially formulated neurotrophic pipecolic acid derivative compounds having an affinity for FKBP-type immunophilins as inhibitors of the enzyme activity associated with immunophilin proteins, and particularly inhibitors of peptidyl-prolyl isomerase or rotamase enzyme activity to stimulate or promote neuronal growth or regeneration.

REFERENCES:
patent: 4310461 (1982-01-01), Krapcho et al.
patent: 4374829 (1983-02-01), Harris et al.
patent: 4390695 (1983-06-01), Krapcho et al.
patent: 4531964 (1985-07-01), Shimano et al.
patent: 4574079 (1986-03-01), Gavras et al.
patent: 4578474 (1986-03-01), Krapcho et al.
patent: 4593102 (1986-06-01), Shanklin, Jr.
patent: 4808573 (1989-02-01), Gold et al.
patent: 4818749 (1989-04-01), Gold et al.
patent: 5147877 (1992-09-01), Goulet
patent: 5156797 (1992-10-01), Armistead et al.
patent: 5252579 (1993-10-01), Skotnicki et al.
patent: 5294603 (1994-03-01), Rinehart
patent: 5319098 (1994-06-01), Burbaum et al.
patent: 5330993 (1994-07-01), Armistead et al.
patent: 5359138 (1994-10-01), Takeuchi et al.
patent: 5414083 (1995-05-01), Hackl et al.
patent: 5424454 (1995-06-01), Burbaum et al.
patent: 5447915 (1995-09-01), Schreiber et al.
patent: 5543423 (1996-08-01), Zelle et al.
Askin, D. et al., "Efficient Degradation of FK-506 to a versatile synthetic intermediate," J. Org. Chem., 1990, 55(20), 5451-4.
Goulet, Mark T., and Boger, Joshua, "Degradative studies on the tricarbonyl containing macrolide rapamycin," Tetrahedron Lett., 1990, 31(34), 4845-8.
Jones, T. et al., "Chemistry of tricarbonyl hemiketals and application of Evans technology to the total synthesis of the immunosuppressant (-)-FK-506," J. Am. Chem. Soc., 1990, 112(8), 2998-3017.
Jones, A. et al., "A formal synthesis of FK-506. Exploration of some alternatives to macrolactamization," J. Org. Chem., 1990, 55(9), 2786-97.
Rao, A.V., et al., "Studies directed towards the synthesis of immunosuppressive agent FK-506: construction of the tricarbonyl moiety," Tetrahedron Lett., 1990, 31(10), 1439-42.
Harding, M.W., et al., "A receptor for the immunosuppressant FK506 is a cis-trans peptidyl-prolyl isomerase," Nature Lett., 1989, 341, 758-60.
Finberg, Robert W. et al., "Prevention of HIV-1 Infection and Preservation of CD4 Function by the Binding of CPFs to gp120," Science, 1990, 249, 287-91.
Goodfellow, Val S. et al., "p-Nitrophenyl 3-diazopyruvate and diazopyruvamides, a New Family of Photoactivatable Cross-Linking Bioprobes," Biochemistry, 28(15), 6346-60, 1993.
Wasserman, H.H. et al., "Synthesis of the tricarbonyl region of FK-506 CA111(7):57366p!," J. Org. Chem., 1989, 54(22), 5406.
Wasserman, H.H. et al., "Synthesis of the tricarbonyl region of FK-506 through an amidosphere," J. Org. Chem., 1989, 54(12), 2785-6.
Askin, D. et al., "Chemistry of FK-506: benzilic acid rearrangement of the tricarbonyl system," Tetrahedron Lett., 1989, 30(6), 671-4.
Coleman, R., and Danishefsky, S., "Degradation and manipulations of the immunosuppressant FK506: preparation of potential synthetic intermediates," Heterocycles, 1989, 28(1), 157-61.
Faelth, Lars et al., "Interactions between C=S groups in 1,2-and 1,3-bis(thiocarbonyl) Compounds: A Study by Spectroscopy, X-Ray Crystallography, and CNDO/S Calculations," THEOCHEM, 1989, 55, 239-59.
Boulmedais, Ali et al., "Stererochemistry of Electrochemical Reduction of Optically Active .alpha.-ketoamides. II. Electroreduction of benzoylformamides derived from S-(-)-proline," Bull. Soc. Chim. Fr., 1989, (2), 185-91. (French).
Soai, Kenso et al., "Asymmetric Allylation of .alpha.-keto amides Derived from (S)-proline esters," Pept. Chem., 1986, 24, 327-330.
Munegumi, Toratane et al., "Asymmetric Catalytic Hydrogenations of N-pyruvoyl-(S)-proline esters," Bull. Chem. Soc. Jpn., 1987, 60(1), 243-53.
Egbertson, M. and Danishefsky, S., "A synthetic route to the tricarbonyl region of FK-506," J. Org. Chem., 1989, 54(1), 11-12.
Williams, D.R. and Benbow, J.W., "Synthesis of the .alpha.,.beta. diketo amide segment of the novel immunosuppressive FK506," J. Org. Chem., 1988, 53(191), 4643-4.
Kocienski, P. et al., "A synthesis of the C(1)-C(15) segment of tsukubaenolide (FK506)," Tetrahedron Lett., 1988, 29(35), 4481-4.
Tanaka, H. et al., "Structure of FK506, a novel imunosuppressant isolated from Streptomyces," J. Am. Chem. Soc., 1987, 109(16), 5031-3.
Soai, Kenso and Ishizaki, Miyuki, "Asymmetric Synthesis of Functionalized tertiary alcohols by diastereoselective allylation of chiral .alpha.-keto amides derived from (S)-proline esters: control of stereochemistry based on saturated coordination of Lewis acid," J. Org. Chem., 1986, 57(17) 3290-5. (English).
Soai, Kenso et al., "Asymmetric synthesis of both eaniomers of .alpha.-hydroxy acids by the diastereoselective reduction of chiral .alpha.-keto amides with complex metal hydrides in the presence of a metal salt," Chem. Lett., 1986, 11, 1897-900.
Soai, Kenso and Hasegawa, Hitoshi, "Diasteroselective reduction of chiral .alpha.-ketoamides derived from (S)-proline esters with sodium borohydride. Preparation of optically active .alpha.-hydroxy acids," J. Chem. Soc., 1985, 1(4), 769-72.
Soai, Kenso and Ishizaki, Miyuki, "Diastereoselective asymmetric allylation of chiral .alpha.-keto amides with allyltrimethylsilane. Preparation of protected homoallylic alcohols," J. Chem. Soc., 1984, 15, 1016-1017.
Soai, Kenso et al., "Sodium borohydride as diastereoselective reducing agent of chiral .alpha.-keto amides," Pept. Chem., 1982, 20, 81-4.
Bender, D., et al., "Periodate oxidation of .alpha.-keto .gamma.-lactams. Enol oxidation and .beta.-lactam formation. Mechanism of periodate hydroxylation reactions," J. Org. Chem., 1978, 43(17), 3354-62.
Colombo, L. et al., "Enantioselective synthesis of secondary alcohols in the presence of chiral ligands," Tetrahedron, 1982, 38(17), 2725-7.
Soai, Kenso et al., "Unusual effect of q mixed solvent on the asymmetric reduction of chiral .alpha.-keto amides with sodium borohydride," J. Chem. Soc., 1982, 21, 1282-3.
Steglich, Wolfgang et al., "Activated carboxylic acid derivatives. II. A simple synthesis of 2-oxycarboxylic acid amides, N-(2-oxoacyl)amino acid esters and 2-oxocarboxylic acid hydrazides," Synthesis, 1978, 8, 622-4. (German).
Cushman, D.W. et al., "Design of potent competitive inhibitors of angiotensin-converting enzyme. Carboxyalkanoyl and mercaptoalkanoyl amino acids," Biochemistry, 1977, 16(25), 5484-91.
Steglich, Wolfgang and Hinze, Sabine, "A rational synthesis of N-trifluroaceytylamino acids," Synthesis, 1976, 8, 399-401. (German).
Bycroft, Barrie W., and Lee, Grahame R., "Efficient asymmetric synthesis of .alpha.-amino from .alpha.-keto acids and ammonia with conservation of the chiral reagent," J. Chem. Soc., 1975, 24, 988-9.
Marshall, J.A. et al., Convenient synthesis of dioxopiperazines via aminolysis of .alpha.-(pyruvylamino) esters, Synth. Commun., 1975, 5(3), 237-44.
Haeusler, Johannes and Schmidt, Ulrich, "Amino acids and peptides. IX. Pyruvoyl amino acids," Chem. Ber., 1974, 107(1), 145-51. (German).
Hearn, Walter R., and Worthington, Robert E., "L-Proline-N-oxalic anhydride," J. Org. Chem., 1967, 32(12), 4072-4.
Chakaraborty, Tushar K., "Stuies towards the development of cyclic peptide-based analogs of macrolide immunosuppressants," Pure Appl. Chem., 1996, 68(3), 565-568.
Ponticelli, Claudio, "Treatment of the Nephrotic Syndrome with Cyclosporin A," J. of Autoimmunity, 1992, 5, 315-24.
Tindall, Richard S.A., "Immunointervention with Cyclosporin A in utoimmune Neurological Disorders," J. of Autoimmunity, 1992, 5, 301-13.
Tugwell, Peter, "Clyclosprin in the Treatment of Rheumatoid Arthritis," J. of Autoimmunity, 1992, 5, 231-40.
Fry, Lionel, "Psoriasis: Immunopathology and Long-term treatment with Cyclosporin," J. of Autoimmunity, 1992, 5, 277-83.
Feutren, Gilles, "The Optimal use of Cyclosporin A in Autoimmune Diseases," J. of Autoimmunity, 1992, 5, 183-95.
Slee, Deborah H. et al., Selectivity in the Inhibition of HIV and FIV Protease: Inhibitory and Mechanistic Studies of Pyrrolidine-Containing .alpha.-Keto Amide and Hydroxy

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