Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Reexamination Certificate
2006-10-03
2006-10-03
Aulakh, Charanjit S. (Department: 1625)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
C546S049000, C544S125000, C435S184000, C514S232800
Reexamination Certificate
active
07115619
ABSTRACT:
The present invention pertains to certain N8,N13-disubstituted quino[4,3,2-kl]acridinium salts of formula (Q−) which inhibit telomerase wherein: p is an integer from 0 to 4; q is an integer from 0 to 3; r is an integer from 0 to 4; each RAis —H or a ring substituent; each RBis —H or a ring substituent; each RCis —H or a ring substituent; RN8is a nitrogen substituent; RN13is a nitrogen substituent; and, Q is an anion. The present invention also pertains to pharmaceutical compositions comprising such compounds, and the use of such compounds and compositions, both in vitro and in vivo, to inhibit telomerase, to regulate cell proliferation, and in the treatment of proliferative conditions, such as cancer.
REFERENCES:
Stanslas et al; “Antitumor Polycyclic Acridines. 7. Synthesis and Biological Properties of DNA Affinic Tetra- and Pentacyclic Acridines”; Journal of Medicinal Chemistry, 2000, 43(8), 1563-1573, XP002201185.
Neidle, S., et al., 1999, “Telomerase as an Anti-Cancer Target: Current Status and Future Prospects,” Anti-Cancer Drug Design, vol. 14, pp. 341-347.
Oszczapowicz, J.; Jaroszewska-Manaj, J.; Ciszak E.; Gdaniec, M., 1988, “Formation of Qunioacridinium System. A Novel Reaction of Quinaldinium Salts,” Tetrahedron, vol. 44, No. 21, pp. 6645-6650.
Perry, P.J., et al., 1998, “1,4- and 2,6-Disubstituted Amidoanthracene-9, 10-dione Derivatives as Inhibitors of Human Telomerase,” J. Med. Chem., vol. 41, pp. 3253-3260.
Perry et al., 1998, “Telomeres and Telomerase: Targets for Cancer Chemotherapy!,” Exp. Opin. Ther. Patents, vol. 8, No. 12, pp. 1567-1586.
Reisch, J., et al., 1991, “Convenient Synthesis of Isoacronycine and Some Other New Acridone Derivatives,” Liebigs Ann. Chem., pp. 695-689.
Sharma, S., et al., 1997, “Preclinical and Clinical Strategies for Development of Telomerase and Telomere Inhibitors,” Annals of Oncology, vol. 8, pp. 1063-1074.
Song, Z., et al., 1993, “Improved Synthesis of Quinaldines by the Skraup Reaction,” J. Heterocyclic Chem., vol. 30, pp. 17-21.
Stanslas, J., et al., 2000, “Antitumor Polycyclic Acridines. 7. Synthesis and Biological Properties of DNA Affinic Tetra- and Pentacyclic Acridines,” J. Med. Chem., vol. 43, pp. 1563-1572.
Timari, G., et al., 1996, “Synthesis of Novel Ellipticine Analogues and Their Inhibition of Molony Leukemia Reverse Transcriptase,” Bioorganic & Medicinal Chemistry Letters, vol. 6, No. 23, p. 2831-2836.
Urquidi, V., et al., 1998, “Telomerase in Cancer: Clinical Applications,” Ann. Med., vol. 30, pp. 419-430.
Wolfe, J.P., et al., 2000, “Simple, efficient catalyst system for the palladium-catalyzed amination or aryl chlorides, bromides, and triflates,” J. Org. Chem., vol. 65, pp. 1158-1174.
Albert, A., 1966, The Acridines: Their Preparation, Physical, Chemical, and Biological Properties and Uses, 2ndEdition, Edward Arnold (Publishers) Ltd., London (table of contents).
Autexier, 1999, “Telomerase as a Possible Target for Anticancer Therapy,” Chemistry & Biology, Nov. 1999, vol. 6, pp. R299-R303.
Bostock-Smith, C.E., et al., 1999, “Molecular Recognition between a New Pentacyclic Acridinium Salt and DNA Sequences Investigated by Optical Spectroscopic Techniques, Proton Nuclear Magnetic Resonance Spectroscopy, and Molecular Modeling,” Biochemistry, vol. 38, No. 21, pp. 6723-6731.
Coulson, D.R., 1990, “Tetrakis(triphenylphoshine) palladium(0)”, Inorganic Synthesis, Chapter 28, pp. 107-109.
Gimenez-Arnau et al., 1998, “Antitumour Polycyclic Acridines. Part 4. Physico-chemical studies on the interactions between DNA and novel tetracyclic acridine derivatives,” Anti-Cancer Drug Design, vol. 13, pp. 431-451.
Gimenez-Arnau et al., 1998, “Antitumour Polycyclic Acridines. Part 2. Physicochemical Studies on the Interactions between DNA and Novel Polycyclic Acridine Derivatives,” Anti-Cancer Drug Design, vol. 13, pp. 125-143.
Gullier, F., et al., 1995, “Combined Metalation-Palladium-Catalyzed Cross Coupling Strategies. A Formal Synthesis of the Marine Alkaloid Amphimedine,” J. Org. Chem., vol. 60, pp. 292-296.
Hagan, D.J., et al., 1997, “Antitumour polycyclic acridines. Part 1. Synthesis of 7H-pyrido and 8H-quino-[4,3,2-kl]acridines by Graebe-Ullmann thermolysis of 9-(1,2,3-triazol-1-yl)acridines: application of differential scanning calorimetry to predict optimum cyclisation conditions,” J. Chem. Soc., Perkin Trans. I, pp. 2739-2746.
Hagan, D.J., et al., 1998, “Antitumour polycyclic acridines. Part 3. A two-step conversion of 9-azidoacridine to 7h-pyrido[4,3,2-kl]acridines by Graebe-Ullmann thermolysis of substituted 9-(1,2,3-triazol-1-yl) acridines,” J. Chem. Soc., Perkin Trans. I, pp. 915-923.
Hodgeman, D.K.C. and Prager, R.H., 1972, “Acridone Studies. VIII. Preparation and Properties of the Monobromo-, Nitro-, Amino-, and Piperadino-10-Methylacridones,” Aus.J. Chem., vol. 25, pp. 191-199.
Jaroszewaka-Manaj, J., et al., 2000, “1H, 13C and 15N NMR and GIAO CPHF Calculations on Two Quinoacridinium Salts,” Magnetic Resonance in Chemistry, vol. 38, No. 6, pp. 482-485.
Julino, M., et al., 1998, “Antitumour Polycyclic Acridines. Part 5. Synthesis of 7H-Pyrido[4,3,2-kl]acridines with exploitable functionality in the pyridine ring,” J. Chem. Soc., Perkin Trans. I, pp. 1677-1684.
Katritzky, A.R., et al., 1999, “Polycyclic Fused Phenanthridines: An Alternative Approach from Benzotriazoles,” J. Heterocyclic Chem., vol. 36, pp. 927-932.
Littke, A.F., et al., 1999, “Heck Reactions in the Presence of P(t-Bu)3: Expanded Scope and Milder Reaction Conditions for the Coupling of Aryl Chlorides,” J. Org. Chem., vol. 64, pp. 10-11.
Missailidis, S., et al., 1997, “Spectroscopic Studies of the Interactions Between DNA and Novel Polycyclic Acridine Derivatives,” in Spectroscopy of Biological Molecules: Modern Trends, (Euro. Conf.), 7th(editors: Carmona, P., et al.), pp. 391-392.
Mitchell, G., et al., 1987, Cyclo-octa[def]carbazole, a New Heterocyclic Paratropic Ring System, J. Chem. Soc., Perkin Trans. 1, vol. 2, pp. 403-412.
Heald Robert A
Kelland Lloyd R
Stevens Malcolm F. G.
Aulakh Charanjit S.
Cancer Research Technology Limited
Nixon & Vanderhye P.C.
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