Process of obtaining taxosteroids and precursors thereof

Details Process of obtaining taxosteroids and precursors thereof Process of obtaining taxosteroids and precursors thereof

2004-07-02

2009-11-17

Dentz, Bernard (Department: 1625)

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

N-c doai

C514S511000, C560S029000, C560S039000

Reexamination Certificate

active

07618999

ABSTRACT:
The present invention relates to a process of obtaining taxosteroids and precursors thereof from the hydrindane bicyclic ring system. The compounds have a tetracyclic system which combines the structural characteristics of taxanes, such as the bicyclo[5.3.1]undecane system (cycles A and B), fused to a six-membered ring (C), and of steroids, such as the CD bicycle, the A ring and the side chain (Sc). The process of preparing the compounds and their application as compositions with pharmacological properties of interest are described.

REFERENCES:
Garcia-Fandiñet al. “Tandem RCM of Dienynes for the Construction of Taxol-Type Carbocyclic Systems” Organic Letters, 2004, vol. 6, No. 2, pp. 193-196.
Liu et al. “Design, Synthesis, and Bioactivities of Steroid-Linked Taxol Analogues as Potential Targeted Drugs for Prostate and Breast Cancer” J. Nat. Prod., 2004, vol. 67, pp. 152-159.
Verdier-Pinard et al. “A Steroid Derivative with Paclitaxel-Like Effects on Tubulin Polymerization” Molecular Pharmacology, 2000, vol. 57, pp. 568-575.
Villalva-Servin et al. “A Direct Carbometallation-Stereoselective Cycloaddition-Ring Closing Metathesis Route to the Tricyclis ABC Core of Taxoids” SYNLETT, Nov. 7, 2003, vol. 9, pp. 1263-1266.
Wang et al. “Synthesis of B-Ring Homologated Estradiol Analogues that Modulate Tubulin Polymerization and Microtubule Stability” J. Med. Chem., 2000, vol. 43, No. 12, pp. 2419-2429.
Codesido et al. “Toward and Analogue of he Transition State of PreD3—D3Isomerization: Stereoselective Synthesis of Linearly Fused 6-8-6 Carbocyclic Systems” Org. Lett., 2002, vol. 4, No. 10, pp. 1651-1654.
Ojima et al. “Macrocycle Formation by Ring-Closing Metathesis. Application to the Syntheses of Novel Macrocyclic Taxoids” J. Am. Chem. Soc., 2000, vol. 122, No. 22, pp. 5343-5353.
Bourgeois et al. “Synthesis of BC Ring-Systems of Taxol by Ring-Closing Metathsis.”Synthesis. No. 6. 2000. pp. 869-882.
Codesido et al. “Access to [6.4.0]Carbocyclic Systems by Tandem Metathesis of Dienynes. A Step toward the Synthesis of a PreD-D Transition State Analogue.”Org. Lett. vol. 3. No. 10. 2001. pp. 1483-1486.
Danishefsky et al. “Total Synthesis of Baccatin III and Taxol.”J. Am. Chem. Soc. vol. 118. No. 12. 1996. pp. 2843-2859.
Deng et al. “A practical, highly enantioselective synthesis of the taxol side chain via asymmetric catalysis.”J. Org. Chem. vol. 57. No. 15. 1992. pp. 4320-4323.
Denis et al. “An efficient, enantioselectice synthesis of the taxol side chain.”J. Org. Chem. vol. 51. No. 1. 1986. pp. 46-50.
Denis et al. “An improved synthesis of the taxol side chain of RP 56976.”J. Org. Chem. vol. 55. No. 6. 1990. pp. 1957-1959.
Denis et al. “Direct, highly, efficient synthesis from (S)-(+)-phenylglycine of the taxol and ataxotere side chains.”J. Org. Chem. vol. 56. No. 24. 1991. pp. 6939-6942.
Furstner et al. “Coordinatively unsaturated ruthenium allenylidene complexes: highly effective, well defmed catlysts for the ring-closure metathesis of ci-w-dienes and dienynes.”Chem. Commun. 1999. pp. 601-602.
Georg et al. “Taxane Anticancer Agents: Basic Science and Current Status.”ACS Symposium Series 583. 1995. pp. ix-1.
Hamel et al. “The Coral-Dreived Natural Products Eleutherobin and Sarcodictyins A and B: Effects on the Assembly of Purified Tubulin with and without Microtubule-Associated Proteins and Binding at the Polymer Taxoid Site.”Biochemistry. vol. 38. No. 17. 1999. pp. 5490-5498.
Hofle et al. “Epothilone A and B-Novel 16-Membered Macrolides with Cytotoxic Activity: Isolation, Crystal Structure, and Conformation in Solution.”Angew. Chem. Int. Ed. Engl. vol. 35. No. 13/14. 1996. pp. 1567-1569.
Holton et al. “First total synthesis of taxol. 1. Functionalization of the B ring.”J. Am. Chem. Soc. vol. 116. No. 4. 1994. pp. 1597-1600.
Jordan. “Mechanism of Action of Antitumor Drugs that Interact with Microtubules and Tubulin.”Curr. Med. Chem. - Anti-Cancer Agents. vol. 2. 2002. pp. 1-17.
Kanazawa et al. “A short synthesis of the taxotere side chain through dilithiation of Boc-benzylamine.”J. Org. Chem. vol. 58. No. 1. 1993. pp. 255-257.
Davis et al. “Assymmetric synthesis of sulfmimines: applications to the synthesis of nonracemic.beta-amino acides and.alpha.-hydroxyl.beta.-amino acids.”J. of Organic Chemistry. vol. 57. No. 24. 1992. pp. 6387-6389.
Kim et al. “Catalytic Ring Closing Metathsis of Dienynes: Construction of Fused Bicyclic Rings.” J. Am. Chem. Soc . vol. 116. No. 23. 1994. pp. 10801-10802.
Kim et al. “Catalytic Ring Closing Metathsis of Dienynes: Construction of Fused Bicyclic [n. m.0] Rings.”J. Org. Chem. vol. 61. No. 3. 1996. pp. 1073-1081.
Kingston et al. “The Chemistry of Taxol and Related Taxoids.”Springer-Verlag Wein. New York. 2002. pp. 53-225.
Kingston. “Taxol, a molecule for all seasons.”Chem. Commun. 2001. pp. 867-880.
Long et al. “Eleutherobin, a Novel Cytotoxic Agent That Induces Tubulin Polymerizations, Is Similar to Paclitaxel (Taxole®)1”Cancer Research. vol. 58. 1998. pp. 1111-1115.
Mekhail et al. “Paclitaxel in cancer therapy.”Ashley Publications, London. 2002. pp. 755-766.
Miller et al. “Chemistry and Chemical Biology of Taxane Anticancer Agents.”The Chem. Record. vol. 1. 2001. pp. 195-211.
Nicolaou et al. “Total synthesis of taxol.”Nature. vol. 367. 1994. pp. 630-634.
Nicolaou et al. “Total syntheses of complex nature products.”Agnew. Chem. Int. Ed. Engl. vol. 34. No. 9. 1995. pp. 2069-2074.
Nicoletti et al. “IDN5109, a Taxane with Oral Bioavailability and Potent Antitumor Activity.”Cancer Research. vol. 60. 2000. pp. 842-846.
Ojima et al. “Efficient and practical asymmetric synthesis of the taxol C-13 side chain, N-benzoyl-(2R,35)-3-phenylisoserine, and its analogs via chiral 3-hydroxy-4-aryl-.beta.-lactams through chiral ester enolate-imine cyclocondensation.”J. Org. Chem. vol. 56. No. 5. 1991. pp. 1681-1683.
Rowinsky et al. “Taxol: A Novel Investigational Antimicrotubule Agent.”J. of National. Cancer Int. vol. 82. No. 15. 1990. pp. 1247-1259.
Scholl et al. “Synthesis and Activity of New Generation of Ruthenium-Based Olefin Metathesis Catalysts Coordinated with 1,3-Dimesity1-4-5-dihydroimidazol-2-ylidene Ligands.”Org. Letters. vol. 1. No. 6. 1999. pp. 953-956.
Suffness. “Taxol Science and Applications.”CRC Press, New York. 1995.
Wang et al. “Synthesis of B-Ring Homologated Estradiol Analogues that Modulated Tubulin Polymerization and Microtubule Stability.”J. Med. Chem. vol. 43. No. 12. 2000. pp. 2419-2429.
Winkler et al. “Stereoselective Synthesis of the Taxane Ring System via the Tandem Diels - Alder Cycloaddion.”J. Org. Chem. vol. 62. No. 9. 1997. pp. 2957-2962.
Wu et al. “Identification of a novel steroid derivative, NSC12983, as a paclitaxel-like tubulin assembly promoter by 3-D virtual screening.”Anti-Cancer Drug Design, vol. 16. 2001. pp. 129-133.
Zuercher et al. “Ruthenium-Catalyzed Polycyclization Reactions.”J. Org. Chem. vol. 63. No. 13. 1998. pp. 4291-4298.
Chabner et al. “Taxol.”Princ. Prac. Oncology, vol. 5. No. 9. 1991. pp. 1-10.

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