Therapeutic acridone and acridine compounds

Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Heterocyclic carbon compounds containing a hetero ring...

Reexamination Certificate

Rate now

  [ 0.00 ] – not rated yet Voters 0   Comments 0

Details

C544S106000, C544S126000, C544S224000, C544S336000, C546S102000, C546S104000, C546S105000, C514S231200, C514S252110, C514S290000, C514S297000

Reexamination Certificate

active

11157977

ABSTRACT:
The present invention pertains to acridone and acridine compounds of formula (I), wherein either: (a) K is ═O, L is —H, alpha is a single bond, beta is a double bond, gamma is a single bond (acridones); or, (b) K is a 9-substituent, L is absent, alpha is a double bond, beta is a single bond, gamma is a double bond (acridines); and wherein: J1is a 2- or 3-substituent; J2is a 6- or 7-substituent; J1and J2are each independently a group of the formula —NHCO(CH2)nNR1R2, wherein: n is an integer from 1 to 5; and, R1and R2are independently hydrogen, C1-7alkyl, C3-20heterocyclyl, or C5-20aryl, or R1and R2, taken together with the nitrogen atom to which they are attached, form a heterocyclic ring having from 3 to 8 ring atoms; and wherein, when K is a 9-substituent, K is a group of the formula —N(RN)Q, wherein: RNis an amino substituent and is hydrogen, C1-7alkyl, C3-20heterocyclyl, or C5-20aryl; and, Q is C1-7alkyl, C3-20heterocyclyl, or C5-20aryl, and is optionally substituted; and pharmaceutically acceptable salts, esters, amides, solvates, hydrates and protected forms thereof. 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:
patent: 7160896 (2007-01-01), Neidle et al.
patent: 7205311 (2007-04-01), Neidle et al.
patent: 488 890 (1929-12-01), None
Autexier, C., 1999, “Telomerase as a Possible Target for Anticancer Therapy,”Chemistry&Biology, Nov. 1999, vol. 6, pp. R299-R303.
Bogert, M.T., et al., 1930, “Researches in the Acridine Series. The Synthesis of Isomers of Proflavine and of Neutral Acriflavine,”Collect. Czech. Chem. Comm., vol. 2, pp. 383-395.
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.
Cain, B.F., et al., 1974, “Potential Antitumor Agents. 14. Acridylmethanesulfonanilides,”J. Med. Chem.,vol. 17, No. 9, pp. 922-930.
Cain, B.F., et al., 1976, “Potential Antitumor Agents. 17. 9-Anilino-10-methylacridinium salts,”J. Med. Chem., vol. 19, No. 6, pp. 772-777.
Cain, B.F., et al., 1976, “Potential Antitumor Agents. 19. Multiply Substituted 4′-(9-Acridinylamino)methanesulfonanilides,”J. Med. Chem., vol. 19, No. 9, pp. 1124-1129.
Denny, W.A., et al., 1982, “Potential Antitumour Agents. 36. Quantitative Relationships between Experimental Antitumour Activity, Toxicity, and Structure for the General Class of 9-Anilinoacridine Antitumor Agents,”J. Med. Chem., vol. 25, pp. 276-315.
Gamage, S.A., et al., 1994, “Synthesis and in Vitro Evaluation of 9-Anilino-3,6-diaminoacridines Active Against a Multidrug Resistant Strain of the Malaria ParasitePlasmodium falciparum,” J. Med. Chem., vol. 37, No. 10, pp. 1486-1494.
Gimenez-Arnau, E. et al., 1998, “Antitumour Polycyclic Acridines, Part 2,”Anti-Cancer Drug Design, vol. 13, pp. 125-143.
Gimenez-Arnau, E., et al., 1998, “Antitumour Polycyclic Acridines, Part 4,”Anti-Cancer Drug Design, vol. 13, pp. 431-451.
Goldberg, A.A. and Kelly, W., 1946, “29. Synthesis of Diaminoacridines. Part 1,”J. Chem. Soc., p. 102-111.
Goldstein, H., and de Simo, M., 1927, “Quelques derives de l'acide phenyl-anthranilique III,”Helv. Chim. Acta., vol. 10, p. 603-606.
Hagan, D.H., et al., 1997, “Antitumour Polycyclic Acridines, Part 1,”J. Chem. Soc., Perkin Trans. 1, pp. 2739-2746.
Hagan, D.H., et al., 1998, “Antitumour Polycyclic Acridines, Part 3,”J. Chem. Soc., Perkin Trans. 1, pp. 915-923.
Harrison, R.J., et al., 1999, “Human Telomerase Inhibition by Substituted Acridine Derivatives,”Bioorganic&Medicinal Chemistry Letters, vol. 9, pp. 2463-2468.
Hoffmann, S., et al., 1986, “Synthese bisbasisch-substituierter Acridine als potentielle Nucleinsaureeffecktoren,”Zeitschrift fur Chemie, vol. 26, No. 9, pp. 331-332. (Partial English Translation Enclosed).
Julino, M., et al., 1998, “Antitumour Polycyclic Acridines, Part 5,”J. Chem. Soc., Perkin Trans. 1, pp. 1677-1684.
Klopman, G., et al., 1987, “Computer-Automated Structure Evaluation of Antiluekemic 9-Anilinoacridines,”Molecular Pharmacology, vol. 31, pp. 457-476.
Korolev, B.A., et al., 1976, “Preparation of 2-Aminoacridan by the Reduction of 2-Amino-9-Acridanone with Biborane,”J. Gen. Chem. USSR(Engl. Trans.), vol. 46, pp. 2250-2252.
Korolev, B.A., et al., 1977, “Acridines. II. Selective Reduction of Nitro Derivatives of 2-Amino-9-Acridanone with Diborane,”J. Gen. Chem. USSR(Engl. Trans.), vol. 47, pp. 2118-2122.
Matsumura, K., 1929, “The Synthesis of Certain Acridine Compounds,”J. Amer. Chem. Soc., vol. 51, pp. 816-820.
Moisan, M., et al., 1993, “New α,ω-Diamido and α,ω-Diamino Mono- and Di-Bridged Acridine Dimers,”Monatshefte fur Chemie, vol. 124, pp. 23-35.
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.
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, No. 17, pp. 3253-3260.
Perry, P.J., et al., 1998, “Human Telomerase Inhibition by Regioisomeric Disubstitued Amidoanthracene-9,10-diones,”J. Med. Chem., vol. 41, No. 24, pp. 4873-4884.
Perry, P.J. 1998, “Telomeres and Telomerase: Targets for Cancer Chemotherapy?,”Exp. Opin. Ther. Patents, vol. 8, No. 12, pp. 1567-1586.
Perry, P.J., et al., 1999, “2,7-Disubstituted Amidofluorenone Derivatives as Inhibitors of Human Telomerase,”J. Med. Chem., vol. 42, No. 14, pp. 2679-2684.
Perry, P.J., et al., 1999, “Design, Synthesis and Evaluation of Human Telomerase Inhibitors Based Upon a Tetracyclic Structural Motif,”Anti-Cancer Drug Design, vol. 14, pp. 373-382.
Read et al., Apr. 24, 2001, “Structure-based design of selective and potent G quadruplex-mediated telomerase inhibitors,”Proceedings of the National Academy of Science, vol. 98, No. 9, pp. 4844-4849.
Read, M.A., et al., 1999, “Molecular Modeling Studies on G-Quadruplex Complexes of Telomerase Inhibitors: Structure-Activity Relationships,”J. Med. Chem., vol. 42, pp. 4538-4546.
Sharma, S., et al., 1997, “Preclinical and Clinical Strategies for Development of Telomerase and Telomere Inhibitors,”Annals of Oncology, vol. 8, pp. 1063-1074.
Sun, D., et al., 1997, “Inhibition of Human Telomerase by a G-Quadruplex-Interactive Compound,”J. Med. Chem., vol. 40, pp. 2113-2116.
Urquidi, V., et al., 1998, “Telomerase in Cancer: Clinical Applications,”Ann. Med., vol. 30, pp. 419-430.
Lorente et al, Tetrahedron Letters, 1996, vol. 37, No. 25, pp. 4417-4420.
Perry et al, J. Med. Chem., 1998, vol. 41, pp. 3253-3260.
Read et al, PNAS, Apr. 24, 2001, 98(9), pp. 4844-4849.
Li et al, (2001): Biochemistry, vol. 40, pp. 15194-15202.

LandOfFree

Say what you really think

Search LandOfFree.com for the USA inventors and patents. Rate them and share your experience with other people.

Rating

Therapeutic acridone and acridine compounds does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Therapeutic acridone and acridine compounds, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Therapeutic acridone and acridine compounds will most certainly appreciate the feedback.

Rate now

     

Profile ID: LFUS-PAI-O-3877599

  Search
All data on this website is collected from public sources. Our data reflects the most accurate information available at the time of publication.