Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Patent
1997-08-01
1999-11-23
Kight, John
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
546226, 548533, 548540, 514422, 514423, A61K 31445, C07D21106
Patent
active
059901314
ABSTRACT:
This invention relates to neurotrophic low molecular weight, small molecule heterocyclic thioesters and ketones having an affinity for FKBP-type immunophilins, and their use as inhibitors of the enzyme activity associated with immunophilin proteins, particularly peptidyl-prolyl isomerase, or rotamase, enzyme activity.
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: 4766110 (1988-08-01), Ryan et al.
patent: 4808573 (1989-02-01), Gold et al.
patent: 4818749 (1989-04-01), Gold et al.
patent: 5147877 (1992-09-01), Goulet
patent: 5166317 (1992-11-01), Wallace et al.
patent: 5192773 (1993-03-01), Armistead et al.
patent: 5215969 (1993-06-01), Springer et al.
patent: 5232923 (1993-08-01), Fukazawa 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: 5385918 (1995-01-01), Connell 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: 5516797 (1996-05-01), Armistead et al.
patent: 5543423 (1996-08-01), Zelle et al.
patent: 5717092 (1998-02-01), Armistead et al.
Rao, A.V. Rama et al., "Studies directed towards the synthesis of immunosuppressive agent FK-506: synthesis of the entire bottom half," Tetrahedron Lett., 1991, 32(9), 1251-4.
Fisher, Matthew et al., "On the remarkable propensity for carbon-carbon bond cleavage reactions in the C(8)-C(10) region of FK-506," J. Org. Chem., 1991, 56(8), 2900-7.
Linde, Robert G. et al., "Straightforward synthesis if 1,2,3-tricarbonyl systems," J. Org. Chem., 1991, 56(7), 2534-8.
Hayward, C.M. et al., "An application of the Suarez reation to the regiospecific synthesis of the C.sub.28 -C.sub.42 segment of rapamycin,", 1993, 3989-92.
Waldmann, Herbert, "Proline benzyl ester as chiral auzilary in Barbier-type reactions in aqueous solution," 1990, Synlett, 10, 627-8.
Gold, Bruce G. et al., "Regulation of aberrant neurofilament phosophorylation in neuronal periokarya. IV. Evidence for the involvement of two signals," Brain Search, 626 (1993) 23-30.
Hauske, James R. et al., "Design and Synthesis of Novel FKBP Inhibitors," J. Med. Chem., 1992, 35, pp. 4284-4296.
Holt, Dennis A. et al., "Structure Acitivity Studies of Nonmacrocyclic Rapamycin Derivatives," Bioorganic & Medical Chemistry Letters, 1993, vol. 3, No. 10, pp. 1977-1980.
Yamashita, Dennis S. et al., "Design Synthesis and Evaluation of Dual Domain FKBP Ligands," Bioorganic & Medicinal Chemistry Letters, 1994, vol. 3, No. 2, pp. 325-328.
Teague, Simon J. et al., "Synthesis and Study of a Non Macrocyclic FK506 Derivative," Bioorganic & Medicinal Chemistry Letters, 1994, vol. 4, No. 13, pp. 1581-1584.
Luengo, Juan I. et al. "Synthesis and Structure-Activity Relationships of Macrocyclic FKBP Ligands," Bioorganic & Medicinal Chemistry Letters, 1994, vol. 4, No. 2, pp. 321-324.
Holt, Dennis A. et al., "Structure-Activity Studies of Synthetic FKBP Ligands as Prptidyl-Prolyl Isomerase Inhibitors," Bioorganic & Medicinal Chemistry Letters, 1994, vol. 4, No. 2, pp. 315-320.
Teague, Simon J. et al. "The Affinity of the Excised Binding Domain of the FK-506 for the Immunophilin FKBP12," Bioorganic & Medicinal Chemsitry Letters, 1993, vol. 3, No. 10, pp. 1947-1950.
Caffrey, Moya V. et al. "Synthesis and Evaluation of Dual Domain Macrocyclic FKBP12 Ligands," Bioorganic & Medicinal Chemsitry Letters, 1994, vol. 4, No. 21, pp. 2507-2510.
Birkenshaw, Timothy N. et al. "Synthesis FKBP12 Ligands. Design and Synthesis of Pyranose Replacements," Bioorganic & Medicinal Chemsitry Letters, 1994, vol. 4, No. 21, pp. 2501-2506.
Holt, Dennis A. et al. "Design, Synthesis, and Kinetic Evaluation of High-Affinity FKBP Ligands and the X-ray Crystal Structures of their Complexes with FKBP12", J. Am. Chem. Soc., 1993, 115, pp. 9925-9938.
Wang, Gary T. et al. "Synthesis and FKBP Binding of Small Molecule Mimics of the Tricarbonyl Region of FK506," Bioorganic & Medicinal Chemistry Letters, 1994, vol. 4, No. 9, pp. 1161-1166.
Snyder, Solomon H. and Sabatini, David M., "Immunophilins and the Nervous System," Nature Medicine, 1995, vol. 1, No. 1, pp. 32-37.
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 immunosuppresive FK506," J. Org. Chem., 1988, 53(191), 4643-4.
Kocienski, P. et al., "A synthesis of the C(1)-C(15) segemnt of tsukubaenolide (FK506)," Tetrahedron Lett., 1988, 29(35), 4481-4.
Tanaka, H. et al., "Structure of FK506, a novel immunosuppressant isolated from Streptomyces," J. Am. Chem. Soc., 1987, 109(16), 5031.3.
Marshall, J.A. et al., "Convenient synthesis of dioxopiperazines via aminolysis of .alpha.-(pyruvylamino) esters," Synth. Commun., 1975, 5(3), 237-44.
Stocks, Michael J. et al. "The Contricution to Binding of the Pyranoside Substituents in the Excised Binding Domain of FK-506," Bioorganic & Medicinal Chemistry Letters, 1994, vol. 4, No. 12, pp. 1457-1460.
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.
Steffan, Robert J. et al., "Base catalyzed degradation of rapamycin," Tetrahedron Lett., 1993, 34(23), 3699-702.
Nicolau, K.C. et al., "Total Synthesis of rapamycin," J. Am. Chem. Soc., 1993, 115(10), 4419-20.
Hayward, C.M. et al., "Total synthesis of rapamycin via a novel titanium-mediated aldol macrocyclization reaction," J. Am. Chem. Soc., 1993, 115(20), 9345-6.
Yohannes, Daniel et al. "Degradation of rapamycin: synthesis of a rapamycin-derived fragment containing the tricarbonyl and triene sectors," Tetrahedron Lett., 1993, 34(13), 2075-8.
Luengo, J. et al., "Studies on the chemistry of rapamycin: novel transformation under Lewis-acid catalysis," Tetrahedron Lett., 1993, 34(6), 991-4.
Yohannes, Daniel et al., "Degradation of rapamycin: retrieval of major intact subunits," Tetrahedron Lett., 1992, 33(49), 7469-72.
Hovarth, R. et al., "An application of the Evans-Prasad 1,3-Syn diol synthesis to a stereospecific synthesis of the C.sub.10 -C.sub.27 segment of rapamycin," Tetrahedron Lett., 1993, 34(25), 3993-3996.
Whitesell, J.K. et al., "Asymmetric Induction. Reduction, Nucleophilic Addition to, Ene Reactions of Chiral .alpha.-Ketoesters," J. Chem. Soc., Chem Commun., 1983, 802.
Ando, Takao et al., "Formation of Crossed Phenzine from the reaction between Tetra-p-anisyl- and Tetra-p-tolyl- hydrazines in Liquid Sulphur Dioxide," Chem. Comm., S. Chem. Comm., 1975, 989.
Kino, Toru et al., "FK-506, A novel immunosuppressant isolated from A Streptomyces," J. of Antibiotics, 1987, 40(9), 1249-55.
Goulet, Mark T. and Boger, Joshua, "Degradative studies on the tricarbonyl containing macrolide rapamycin," Tetrahedron Lett., 1991, 32(45), 6454.
Goulet, Mark T.et al., "Construction of the FK-506 analog from rapamycin-derived materials," Tetrahedron Lett., 1991, 32(36), 4627-30.
Armistead, D.M. et al., "Design, synthesis and structure of non-macrocyclic inhibitors of FKBP12, the major binding protein for the immunosuppressant FK506," Acta Crystallogr. 1995, D51(4), 522-8.
Luengo, J. et al., "Structure-activity studies of rapamycin analogs:evidence that the C-7 methodoxy group is part of the effector domain and positioned at the FKBP:12-FRAP interface," Chem. Biol., 1995, 2(7), 471-81.
Furber, Mark, "FKBP-12-ligand-calceineurin interactions: analogs of SBL506," J. Am. Chem. Soc., 1995, 117(27), 7267-8.
Wang CP et al., "A high performance liquid chromatographic method for the determination of
Hamilton Gregory S.
Li Jia-He
Aulakh Charanjit S.
GPI NIL Holdings Inc.
Heiman Lee C.
Kight John
Nath Gary M.
LandOfFree
Heterocyclic thioesters and ketones does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Heterocyclic thioesters and ketones, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Heterocyclic thioesters and ketones will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-1222290