Antiviral acyclic phosphonomethoxyalkylsubstituted alkenyl and a

Organic compounds -- part of the class 532-570 series – Organic compounds – Four or more ring nitrogens in the bicyclo ring system

Patent

Rate now

  [ 0.00 ] – not rated yet Voters 0   Comments 0

Details

544243, A61K 31675, C07F 96561, C07F 96506

Patent

active

056962630

ABSTRACT:
Compounds are provided that generally have the structure BCH.sub.2 CH(R)OCH.sub.2 P(O)(OH).sub.2, wherein B is a purinyl or pyrimidinyl base and R is C.sub.1-2 alkyl substituted with azido or amino, straight or branched alkenyl of 2-6 carbon atoms or alkynyl of 2-6 carbon atoms, together with the monester and diesters of such compounds with a C.sub.1-5 alkanol, and the corresponding salts, hydrates, solvates, the (R) or (S) isomers and the racemic (RS) mixtures thereof. The compounds have desirable antiviral activity.

REFERENCES:
patent: 4659825 (1987-04-01), Holy et al.
patent: 4724233 (1988-02-01), De Clercq et al.
patent: 5047533 (1991-09-01), Reist et al.
patent: 5142051 (1992-08-01), Holy et al.
Lal, JCS Perkins 1, p. 1993 (1992).
Holy et al, Coll. Czech. Chem. Comm. 54, 446 (1989).
Connolly, Antimicrobial Agents & Chemotherapy 36, pp. 245-254 (Feb. 1992).
Mansuri, Chem tech, Sep. 1992, p. 564.
Saari, J Med Chem 35, 3792-3802 (1992).
Merck Standby Statement of Sep. 14, 1993.
Anti viral Agents Bulletin 6, p162-163 (Jun. 1993).
Flexner, Anti microbial Agents & Chemotherapy 35, 2544 (Dec. 1991).
Antiviral Agents Bulletin 6, 231 (Aug. 1993).
Saunders, Drug Design and Discovery 8, 255 (1992).
Antiviral Agents Bulletin 6, 228 (Aug. 1993).
Staal, AIDS Research and Human Retroviruses 9, 299 (1993).
De Clerq, AIDS Research and Human Retroviruses 8, 119 (1992).
Jun. 19, 1990 Letter of Dr Eric Sandstrom.
Rosowsky et al., "Synthesis of 3'-O-Propargylthymidine as a Candidate Antiretroviral Agent," NUCLS & NUCLT 8(4):491-497 (1989).
Abstract for USSR 1,089,093 (Apr. 30, 1984).
Gao et al, J.A.C.S. 109,. 1275-1278 (1987).
Abstract for Gupta et al. Ind. J. Chem Soc (B) 20, 7, p534 (1981).
Abstract for Saxena, Ind. J. Chem Soc (B) 19, 4, p332 (1980).
Abstract for Kos, J. Organic Chem. 48(8), 1207 (1983).
Chu et al, "Chemistry and Antiviral Activities of Acyclonucleosides," J Het Chem 23:289-319 (1986).
De Clercq et al., "Efficacy of Phosphonylmethoxyalkyl Derivatives of Adenine in Experimental Herpes Simplex Virus and Vaccinia Virus Infections in Vivo," Antimicro AG & Chemo 33(2):185-191 (1989).
Holy et al., "Synthesis of (3-Hydroxy-2-Phosphonylmethoxypropyl) Derivatives of Heterocyclic Bases," Collect Czech Chem Commun 54:2470-2501 (1989).
Holy et al., "Synthesis of Isomeric and Enantiomeric O-Phosphonylmethyl Derivatives of 9-(2,3-Dihydroxypropyl) adenine," Collect Czech Chem Commun 54:2775-2791 (1987).
Joshi et al., "Ozonolysis of 6-N-Benzoyl-9-(5-deoxy-2,3-O-isopopylidene-beta-D-erythro-pent-4-enofurano syl)adenine and Related Compounds," Tet Lett 34(36):5807-5810 (1993).
Terry et al., "Broad-spectrum antiviral activity of the acyclic guanosine phosphonate (R,S)-HPMPG," Antiviral Res 10:235-252 (1988).
Translation of Czech application "PV 2047-90".
Prisbe, et al., J. Med. Chem., 29:671 (1986).
DeClercq, et al., Nature, 323:464-467 (1986).
DeClercq, E., Antiviral Res., 12:1 (1989).
Holy, et al., Nucl. Acids Res., Symposium Series 14, pp. 277-278 (1984).
Translation of Czech 263951.
Translation of Czech 263952.
De Clercq et al., "Antiviral activity of phosphonylmethoxyalkyl derivatives of purine and pyrimidines," Antiviral Res 8:261-272 (1987).
Harrison et al, "Compendium of Organic Synthetic Methods," pub. John Wiley & Sons pp. 86-87 (1971).
Holy et al., "Phosphonylmethyl Ethers of Nucleosides and Their Acyclic Analogues," Am Chem Soc 4:51-71 (1989).
House, Herbert O., "Modern Synthetic Reactions, 2nd ed.," The Benjamin/Cummings Publishing Company pp. 19, 49-57 (1972).
March, Jerry, "Advanced Organic Chemistry," pub. John Wiley & Sons p. 329 (1985).
Mazur et al., "Isosteres of Natural Phosphates. 11. Synthesis of a Phosphonic Acid Analogue of an Oligonucleotide," Tet. Lett. 40:3949-3956 (1984).
Pappo et al, "Osmium Tetroxide-Catalyzed Periodate Oxidation of Olefinic Bonds," J. Org. Chem. 21:478 (1956).
Uhlmann et al, "Antisense Oligonucleotides: A New Therapeutic Principle," Chem. Rev. 90:543-584 (1990).

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

Antiviral acyclic phosphonomethoxyalkylsubstituted alkenyl and a does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Antiviral acyclic phosphonomethoxyalkylsubstituted alkenyl and a, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Antiviral acyclic phosphonomethoxyalkylsubstituted alkenyl and a will most certainly appreciate the feedback.

Rate now

     

Profile ID: LFUS-PAI-O-1609042

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