Monoacylated betulin and dihydrobetulin derivatives,...

Organic compounds -- part of the class 532-570 series – Organic compounds – Carboxylic acid esters

Reexamination Certificate

Rate now

  [ 0.00 ] – not rated yet Voters 0   Comments 0

Details

C514S169000, C552S511000

Reexamination Certificate

active

07365221

ABSTRACT:
Betulin and dihydrobetulin acyl derivatives according to the present invention have been found to have potent anti-HIV activity. The compounds of the present invention have Formula I as described herein, or pharmaceutically acceptable salts thereof; wherein R1is a C2-C20substituted or unsubstituted carboxyacyl or ester thereof; R2is hydrogen, halogen, hydroxyl or —OR3, R3is C2-C20substituted or unsubstituted carboxyacyl; and R4is hydrogen or C(C6H5)3; wherein the dashed line represents an optional double bond between C20 and C29.

REFERENCES:
patent: 5679828 (1997-10-01), Lee et al.
patent: 6172110 (2001-01-01), Lee et al.
patent: WO 96/39033 (1996-12-01), None
patent: WO 00/59492 (2000-10-01), None
patent: WO 01/59457 (2001-08-01), None
patent: WO 02/16395 (2002-02-01), None
patent: WO 02/26761 (2002-04-01), None
patent: WO 02/26762 (2002-04-01), None
Pokrovskii, A. G.; Plyasunvoa, O. A.; Il'icheva, T. N.; Borisova, O. A.; Fedyuk, N. V.; Petrenko, N. I.; Petukhova, V. Z.; Shul'ts, E. E.; Tolstikov, G. A. Synthesis of derivatives of plant triterpenes and study of their antiviral and immunostimulating activity. Khimiya v Interesakh Ustoichivogo Razvitiya (2001), 9(3), 485-491.
Pasich, Jan. Triterpenoid emulsifiers of plant origin. V. Emulsifying properties of betulin and certain of its esters. Farm. Polska (1965), 21(17-18), 661-5.
Fujioka, T., and Kashiwada, Y., “Anti-AIDS Agents. 11. Betulinic Acid and Platanic Acid as Anti-HIV Principles fromSyzigium claviflorum,and the Anti-HIV Activity of Structurally Related Triterpenoids,”J. Nat. Prod. 57:243-247, American Chemical Society and American Society of Pharmacognosy (1994).
Hashimoto, F., et al., “Anti-AIDS Agents-XXVII. Synthesis and Anti-HIV Activity of Betulinic Acid and Dihydrobetulinic Acid Derivatives,”Bioorg. Med. Chem. 5:2133-2143, Elsevier Science, Ltd. (1997).
Kanamoto, T., et al., “Anti-Human Immunodeficiency Virus Activity of YK-FH312 (a Betulinic Acid Derivative), a Novel Compound Blocking Viral Maturation,”Antimicrobial Agents Chemother. 45:1225-1230, American Society for Microbiology (Apr. 2001).
Kashiwada, Y., et al., “Betulinic Acid and Dihydrobetulinic Acid Derivatives as Potent Anti-HIV Agents,”J. Med. Chem. 39:1016-1017, American Chemical Society (1996).
Kashiwada, Y., et al., “Anti-AIDS Agents. 30. Anti-HIV Activity of Oleanolic Acid, Pomolic Acid, and Structurally Related Triterpenoids,”J. Nat. Prod. 61:1090-1095, American Chemical Society and American Society of Pharmacognosy (1998).
Kashiwada, Y., et al., “Synthesis and Anti-HIV Activity of 3-Alkylamido-3-deoxy-betulinic Acid Derivatives,”Chem. Pharm. Bull. 48:1387-1390, Pharmaceutical Society of Japan (2000).
Kashiwada, Y., et al., “Anti-AIDS Agents 38. Anti-HIV Activity of 3-O-Acyl Ursolic Acid Derivatives,”J. Nat. Prod. 63:1619-1622, American Chemical Society and American Society of Pharmacognosy (2000).
Ma, C., et al., “Inhibitory Effects of Ursolic Acid Derivatives fromCynomorium songaricum,and Related Triterpenes on Human Immunodeficiency Viral Protease,”Phytother. Res.(Supplement 1, 2ndIntl' Symposium on Natural Drugs)12:S138-S142, John Wiley & Sons, Ltd. (1998).
Ma, C., et al., “Inhibitory Effects of Constituents fromCynomorium songaricumand Related Triterpene Derivatives on HIV-1 Protease,”Chem. Pharm. Bull. 47:141-145, Pharmaceutical Society of Japan (1999).
Neamati, N., “A Small-molecule Antagonist of Virion Assembly,”Expert Opin. Investig. Drugs 10:1767-1770, Ashley Publications, Ltd. (Sep. 2001).
Pokrovskii, A.G., et al., “Synthesis of Derivatives of Plant Triterpenes and Study of Their Antiviral and Immunostimulating Activity,”Khimiya v Interesakh Ustoichivogo Razvitiya 9:485-491, Siberian Branch of the Russian Academy of Sciences (2001).
Sun, I-C., et al., “Anti-AIDS Agents. 34. Synthesis and Structure-Activity Relationships of Betulin Derivatives as Anti-HIV Agents,”J. Med. Chem. 41:4648-4657, American Chemical Society (1998).
Sun, I-C., et al., “Anti-AIDS Agents. 32. Synthesis and Anti-HIV Activity of Betulin Derivatives,”Bioorg. Med. Chem. Lett. 8:1267-1272, Elsevier Science, Ltd. (1998).
STNEasy, Accession No. 2001:541179, CAPLUS, ACS on STN (2003), English language abstract for Pokrovskii, A.G., et al., “Synthesis of Derivatives of Plant Triterpenes and Study of Their Antiviral and Immunostimulating Activity,”Khimiya v Interesakh Ustoichivogo Razvitiya 9:485-491 (2001).

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

Monoacylated betulin and dihydrobetulin derivatives,... does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Monoacylated betulin and dihydrobetulin derivatives,..., we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Monoacylated betulin and dihydrobetulin derivatives,... will most certainly appreciate the feedback.

Rate now

     

Profile ID: LFUS-PAI-O-2796361

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