Organic compounds -- part of the class 532-570 series – Organic compounds – Unsubstituted hydrocarbyl chain between the ring and the -c-...
Reissue Patent
2006-10-17
2006-10-17
Kifle, Bruck (Department: 1624)
Organic compounds -- part of the class 532-570 series
Organic compounds
Unsubstituted hydrocarbyl chain between the ring and the -c-...
C548S181000, C548S204000
Reissue Patent
active
RE039356
ABSTRACT:
The present invention relates to a process for the preparation of epothilone analogs by initially forming novel ring-opened epothilones and carrying out a macrolactamization reaction thereon. The subject process is amenable to being carried out in a single reaction vessel without isolation of the intermediate compound and provides at least about a three-fold increase in yield over prior processes for preparing the desired epothilone analogs.
REFERENCES:
patent: 6194181 (2001-02-01), Hofmann et al.
patent: 6204388 (2001-03-01), Danishefsky et al.
patent: 6211412 (2001-04-01), Georg et al.
patent: 6288237 (2001-09-01), Hoefle et al.
patent: 6320045 (2001-11-01), Kim et al.
patent: 6359140 (2002-03-01), Hofle et al.
patent: 6365749 (2002-04-01), Kim et al.
patent: 6593115 (2003-07-01), Vite et al.
patent: 6605599 (2003-08-01), Vite et al.
patent: 6982280 (2006-01-01), Hoefle et al.
patent: 2004/0132146 (2004-07-01), Benigni et al.
patent: 4138042.8 (1993-05-01), None
patent: 19542986.9 (1997-05-01), None
patent: 19639456.2 (1997-05-01), None
patent: 19636343.8 (1998-03-01), None
patent: 19645361.5 (1998-04-01), None
patent: 19645362.3 (1998-04-01), None
patent: 19647580.5 (1998-05-01), None
patent: 19701758 (1998-07-01), None
patent: 1970705.3 (1998-09-01), None
patent: 19707505.3 (1998-09-01), None
patent: 19713970 (1998-10-01), None
patent: 19720312 (1998-11-01), None
patent: 19821954 (1998-11-01), None
patent: 19726627 (1998-12-01), None
patent: 879 605 (1998-11-01), None
patent: 93/10121 (1993-05-01), None
patent: 97/19086 (1997-05-01), None
patent: 98/08849 (1998-03-01), None
patent: 98/22461 (1998-05-01), None
patent: 98/24427 (1998-06-01), None
patent: 98/25929 (1998-06-01), None
patent: 98/38192 (1998-09-01), None
patent: 98/47891 (1998-10-01), None
patent: 99/01124 (1999-01-01), None
patent: 99/02514 (1999-01-01), None
patent: 99/03848 (1999-01-01), None
patent: 99/07692 (1999-02-01), None
patent: 99/39694 (1999-08-01), None
patent: 99/42602 (1999-08-01), None
patent: 99/43320 (1999-09-01), None
patent: 99/43653 (1999-09-01), None
patent: 99/67252 (1999-12-01), None
patent: 00/00485 (2000-01-01), None
patent: 00/31247 (2000-06-01), None
patent: 00/37473 (2000-06-01), None
patent: 00/49021 (2000-08-01), None
patent: 00/66589 (2000-11-01), None
Altmann, K.H., et al., “Epothilones and Related Structures—A New Class of Microtubule Inhibitors With Patent in Vivo Antitumor Activity,” Biochim. Biophys Acta, 1470 (2000).
Nicolaou et al., “Total Synthesis of Epothilone E and Analogs with Modified Side Chains Through The Stille Coupling Reaction”, Angew. Chem. Int. Ed. 37, 84-87 (1998).
Nicolaou et al., “Total Synthesis of Oxazole- and Cyclopropane-Containing Epothilone B Analogues by the Macrolactonization Approach”, Chemistry, European Journal, vol. 3, No. 12, 1971-1986 (1997).
Nicolaou et al., “Chemical Biology of Epothilones”, Angew. Chem. Int. Ed., 37, 2014-2045 (1988).
Balog, A., et al., “Total Synthesis of (−)-Epothilone A”,Angew. Chem. Int. Ed. Engl.,vol. 35, No. 23/24, 2801-2803 (1996).
Bertini, F., et al., “Alkenes from Epoxides by Reductive Elimination with Magnesium Bromide-Magnesium Amalgam”,Chem. Commun. ,144 (1970).
Bollag, D.M., et al., “Epothilones, A New Class of Microtubule-stablizing Agents with a Taxol-like Mechanism of Action”,Cancer Res.55, No. 11, 2325-2333 (1995).
Fujisawa, T., et al., “Deoxygenation of Epoxides to Olefins with FeCl3—n-BuLi System”,Chem. Lett.,883-886 (1974).
Fujiwara, Y., et al., “Reductive Coupling of Carbonyl Compounds to Olefins by Tungsten Hexachloride-Lithium Aluminum Hydride and Some Tungsten and Molybdenum Carbonyls”,J. Org. Chem.,vol. 43, No. 12, 2477-2479 (1978).
Gladysz, J. A., et al., “Deoxygenation of Epoxides by Metal Atom Cocondensation”,J. Org. Chem.,vol. 41, No. 22, 3647-3648 (1976).
Hofle, G., et al., “Epothilone A and B—Novel 16-Memebered Macrolides with Cytotoxic Activity: Isolation, Crystal Structure, and Conformation in Solution”,Angew. Chem. Int. Ed. Engl.,vol. 35, No. 13/14, 1567-1569 (1996).
Hofle, G., et al., “N-Oxidation of Epothilone A-C and O-Acyl Rearrangement to C-19 and C-21—Substituted Epothilones”,Angew. Chem. Int. Ed.,vol. 38, No. 13/14, 1971-1974 (1999).
Inokuchi, T., et al., “Opening of Epoxides to Olefins or Halohydrins with Vanadium(II)-Tetrahydrofuran or Vanadium(III)-Tetrahydrofuran Complexes”,Synlett,No. 6, 510-512 (1992).
Kowalski, R. J., et al., “Activities of the Microtubule-stablizing Agents Epothilones A and B with Purified Tubulin and in Cells Resistant and in Cells Resistant to Paclitaxel (Taxol®)”J. Biol. Chem.,vol. 272, No. 4, 2534-2541 (1997).
Kupchan, S. M., et al., “Reductive Elimination of Epoxides to Olefins with Zinc-Copper Couple”,J. Org. Chem.,vol. 36, No. 9, 1187-1190 (1971).
Martin, M. G., et al., “Epoxides as Alkene Protecting Groups. A Mild and Efficient Deoxygenation”,Tetrahedron Letters, vol. 25, No. 3, 251-254 (1984).
McMurry, J. E., et al., “Reduction of Epoxides to Olefins with Low Valent Titanium”,J. Org. Chem.,vol. 40, No. 17, 2555-2556 (1975).
McMurry, J. E., et al., “Some Deoxygenation Reactions with Low-Valent Titanium (TiCl3/LiALH4)”,J. Org. Chem.,vol. 43, No. 17, 3249-3254 (1978).
Meng, D., et al., “Remote Effects in Macrolide Formation Through Ring-Forming Olefin Metathesis: An Application to the Synthesis of Fully Active Epothilone Congeners”,J. Am. Chem. Soc.,vol. 119, No. 11, 2733-2734 (1997).
Nicolaou, K. C., et al., “An Approach to Epothilones Based on Olefin Metathesis”,Angew. Chem. Int. Ed. Engl.,vol. 35, No. 20, 2399-2401 (1996).
Nicolaou, K. C., et al., “Total Synthesis of Epothilone A: The Macrolactonization Approach”,Angew. Chem. Int. Ed. Engl.,vol. 36, No. 5, 525-527 (1997).
Nicolaou, K. C., et al., “Designed Epothilones: Combinatorial Synthesis, Tubulin Assembly Properties, and Cytotoxic Action against Taxol-Resistant Tumor Cells”,Angew. Chem. Int. Ed. Engl.,vol. 36, No. 19, 2097-2103 (1997).
Nicolaou, K.C., et al., “The Olefin Metathesis Approach to Epothilone A and Its Analogues”,J. Am. Chem. Soc.,vol. 119, No. 34, 7960-7973 (1997).
Nicolaou, K. C., et al., “Total Syntheses of Epothilones A and B via a Macrolactonization-Based Strategy”,J. Am. Chem. Soc.,vol. 119, No. 34, 7974-7991 (1997).
Nicolaou, K. C., et al., “Synthesis of Epothilones A and B in Solid and Solution Phase”,Nature,vol. 387, 268-272 (1997).
Nicolaou, K. C., et al., “Synthesis of Epothilones A and B in Solid and Solution Phase” (Correction toNature387, 268-272 (1997)).Nature,390, 100 (1997).
Raucher, S., et al., “Total Synthesis of (+)-Dihydrocostunolide via Tandem Cope-Claisen Rearrangement”,J. Org. Chem.,vol. 51, No. 26, 5503-5505 (1986).
Sato, M, et al., “Reduction of Organic Compounds with Low-Valent Niobium (NbCl6/NaAlH4)”,Chem. Letters,157-160 (1982).
Schinzer, D., et al., “Total Synthesis of (−)-Epothilone A”,Angew, Chem. Int. Ed. Engl.,vol. 36, No. 5, 523-524 (1997).
Schobert, R., et al., “Reduction and Isomerization of Oxiranes and α-Diazoketones by Various Early Transition Metallocences”,Synlett,vol. 8, 465-466 (1990).
Sharpless, K. B., et al., “Lower Valent Tungsten Halides. A New Class of Reagents for Deoxygenation of Organic Molecules”,J. Amer. Chem. Soc.,vol. 94, No. 18, 6538-6540 (1972).
Su, D.-S., et al., “Total Synthesis of (−)-Epothilone B: An Extension of the Suzuki Coupling Method and Insights into Structure-Activity Relationships of the Epothilones”,Angew. Chem. Int. Ed. Engl.,vol. 36, No. 7, 757-759 (1997).
Su, D.-S., et al., “Structure-Activity Relationships of the Epothilones and the First in Vivo Comparison with Paclitaxel”;Angew. Chem. Int. Ed.
Borzilleri Robert M.
Favreau Denis
Guo Zhenrong
Kim Soong-Hoon
Li Wen Sen
Bristol-Myers Squibb Co.
Kifle Bruck
Winslow Anastasia P.
LandOfFree
Process for the preparation of epothilone analogs does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Process for the preparation of epothilone analogs, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Process for the preparation of epothilone analogs will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-3633755