Organic compounds -- part of the class 532-570 series – Organic compounds – Pteroyl per se or having -c- – wherein x is chalcogen – bonded...
Reexamination Certificate
2004-03-05
2008-12-23
Balasubramanian, Venkataraman (Department: 1624)
Organic compounds -- part of the class 532-570 series
Organic compounds
Pteroyl per se or having -c-, wherein x is chalcogen, bonded...
C544S317000, C549S310000, C536S026730, C536S028100
Reexamination Certificate
active
07468436
ABSTRACT:
A process for the resolution of a racemic mixture of nucleoside enantiomers that includes the step of exposing the racemic mixture to an enzyme that preferentially catalyzes a reaction in one of the enantiomers. The nucleoside enantiomer (−)-2-hydroxymethyl-5-(5-fluorocytosin-1-yl)-1,3-oxathiolane is an effective antiviral agent against HIV, HBV, and other viruses replicating in a similar manner.
REFERENCES:
patent: 4000137 (1976-12-01), Dvonch et al.
patent: 4336381 (1982-06-01), Nagata et al.
patent: 4861759 (1989-08-01), Mitsuya et al.
patent: 4879277 (1989-11-01), Mitsuya et al.
patent: 4900828 (1990-02-01), Belica et al.
patent: 4916122 (1990-04-01), Chu et al.
patent: 4963533 (1990-10-01), de Clercq et al.
patent: 5011774 (1991-04-01), Farina et al.
patent: 5041449 (1991-08-01), Belleau et al.
patent: 5047407 (1991-09-01), Belleau et al.
patent: 5059690 (1991-10-01), Zahler et al.
patent: 5071983 (1991-12-01), Koszalka et al.
patent: 5179104 (1993-01-01), Chu et al.
patent: 5185437 (1993-02-01), Koszalka et al.
patent: 5204466 (1993-04-01), Liotta et al.
patent: 5210085 (1993-05-01), Liotta et al.
patent: 5234913 (1993-08-01), Furman, Jr. et al.
patent: 5248776 (1993-09-01), Chu et al.
patent: 5270315 (1993-12-01), Belleau et al.
patent: 5276151 (1994-01-01), Liotta
patent: 5538975 (1996-07-01), Dionne
patent: 5539116 (1996-07-01), Liotta et al.
patent: 5618820 (1997-04-01), Dionne
patent: 5728575 (1998-03-01), Liotta et al.
patent: 5814639 (1998-09-01), Liotta et al.
patent: 5827727 (1998-10-01), Liotta et al.
patent: 5892025 (1999-04-01), Liotta
patent: 6069252 (2000-05-01), Liotta et al.
patent: 6346627 (2002-02-01), Liotta et al.
patent: 6703396 (2004-03-01), Liotta et al.
patent: 2002/0143194 (2002-10-01), Liotta et al.
patent: 2004/0038350 (2004-02-01), Liotta et al.
patent: 665187 (1995-12-01), None
patent: 0 217 580 (1987-04-01), None
patent: 0 337 713 (1989-10-01), None
patent: 0 350 811 (1990-01-01), None
patent: 0 357 009 (1990-03-01), None
patent: 0 361 831 (1990-04-01), None
patent: 0 375 329 (1990-06-01), None
patent: 0 421 636 (1991-04-01), None
patent: 0 433 898 (1991-06-01), None
patent: 0 494 119 (1992-07-01), None
patent: 0 515 144 (1992-11-01), None
patent: 0 515 156 (1992-11-01), None
patent: 0 515 157 (1992-11-01), None
patent: 0 526 253 (1993-02-01), None
patent: WO 88/07532 (1988-10-01), None
patent: WO 90/12023 (1990-10-01), None
patent: WO 91/11186 (1991-08-01), None
patent: WO 91/17159 (1991-11-01), None
patent: WO 92/08727 (1992-05-01), None
patent: WO 92/10496 (1992-06-01), None
patent: WO 92/10497 (1992-06-01), None
patent: WO 92/14729 (1992-09-01), None
patent: WO 92/14743 (1992-09-01), None
patent: WO 92/15308 (1992-09-01), None
patent: WO 92/18517 (1992-10-01), None
patent: WO 92/21676 (1992-12-01), None
patent: WO 93/03027 (1993-02-01), None
patent: WO 94/04154 (1994-03-01), None
Letter of Feb. 6, 1998, from the European patent representative acting for the patentee (Emory University) to the EPO regarding the opposed patent (European Patent Application No. 91904454.5).
Declaration of Dennis C. Liotta in relation to the Opposition by Emory University against Europan Patent No. 0382526.
Declaration of Dr. Irving Wainer in relation to the Opposition by Emory University against Europan Patent No. 0382526.
Declaration of Iam M. Mutton in relation to the Opposition by Emory University against Europan Patent No. 0382526.
Declaration of Michael John Dawson in relation to the Opposition by Emory University against Europan Patent No. 0382526.
1982-1986, gen subject list,Chemical Abstracts, 5654CS.
1987-1991, gen subject list,Chemical Abstracts, 6982GS, 7065GS-1067GS.
Allenmark, S.G. (eds.),Chromographic Enantioseparation: Methods and Applications, Wiley & Sons, Brisbane, 1988 [citation information only].
Alltech Associates, Inc., “The Separation of Optical Isomers,”Bulletin #87.
Armstrong, D.W.,Analytical Chemistry, 59(2):84-91 (1987).
Armstrong, D.W., “Chiral stationary phases for high performance liquid chromatography,”J. Liq. Chromatography, 7(S-2):353-376 (1984).
Armstrong, D.W.,Chromatographic Chiral Separation, 1986, vol. 40.
Asai, M., et al., “Studies on synthetic nucleotides. IV. Preparation of L-beta-ribonucleosides and L-beta-ribonucleotides,”J. Chem. Pharm. Bull, 15(12):1863-1870 (Dec. 1967).
Asseline, U., et al., “Synthesis and physicochemical properties of oligonucleotides built with either α-L or β-L nucleotides units and covalently linked to an acridine derivative,” Nucl. Acids Res., 19(15):4067-4074 (1991).
Balzarini, J., et al. “Synthesis and antiviral activity of the enantiomeric forms of carba-5-iodo-2′-deoxyuridine and carba-(E)-5-(2-bromovinyl)-2′-deoxyuridine”,J. Med. Chem, 32(8):1861-1865 (1989).
Balzarini, J., et al., “Potent and Selective Anti-HTLV-IIFLVA Activity of 2′,3′-Dideoxycytidinene, the 2′,3′-Unsaturated Derivative of 2′,3′-Dideoxycytidine,”Biochemical and Biophysical Research Communications, 140(2): 735-742 (1986).
Baum, R., et al.,Chemical&Engineering News, Jun. 26, 1989, p. 11.
Beach, J.W., et al., “Synthesis of Enantiomerically Pure (2′R,5′S)-(1)-1-[2-hydroxymethyl)-oxatiolan-5-yl] Cytosine as a Potent Antiviral Agent Against Hepatitis B Virus (HBV) and Human Immunodeficiency Virus (HIV),”J. Org. Chem., 57:2217-2219 (1992).
Belleau, B., et al.“Design and activity of a novel class of nucleoside analogs effective against HIV-1”,V. Intl. Conf on AIDS Abs., T.C.O.1. p. 515 (1989).
Belleau, B.,V. Intl. Conf on AIDS Abs., M.C.P.63 p. 552 (1989).
Belleau, B.,V. Intl. Conf. on AIDS(Jun. 6, 1989), copy of published abstract, with transcript of oral presentation and copies of the poster used in the presentation,V. International Conference on AIDS, Montreal, Quebec, Canada, Jun. 4-9, 1989.
Belleau, B., et al., “Design and Activity of a Novel Class of Nucleoside Analogs Effective Against HIV-I,” (Jun. 6, 1989) Specialty Session—No. 4576,V. International Conference on AIDS, Montreal, Quebec, Canada, Jun. 4-9, 1989.
Boehm,Anal. Chem., 1988, 522-528, 60.
Borthwick, A.D., et al., “Synthesis and Enzymatic Resolution of Carbocyclic 2′-Ara-Fluoro Guanosine: A Potent New Anti-Herpetic Agent,”J. Chem. Soc. Cornmun., 10:656-658 (1988).
Brown, “State of the art . . . ,”Advances in Chromatography, 1980:101-139.
Bzowska, A., et al., “Acyclonucleoside analogue inhibitors of mammalian purine nucleoside phosphory-lase,”Biochemical Pharmacology, 41(12):1791-1803, (Jun. 15, 1991).
Carruthers,Some Modern Methods Of Organic Synthesis, (1986).
Carter, S.D., et al., “Activities of(-)-Carbovir and 3′-Azido-3′-Deoxythymidine Against Human Immunodeficiency Virus In Vitro,”Antimicrobial Agents and Chemotherapy, 34(6):1297-1300 (Jun. 1990).
Chang, C.-N., et al, “Deoxycytidine Deaminase-resistant Steroisomer Is the Active Form of (±)-2′,3′-Dideoxy-3′-thiacytidine in the Inhibition of Hepatitis B Virus Replication,”The Journal of Biological Chemistry, 267(20): 13938-13942 (1992).
Chu, C.K., et al., “An Efficient Total Synthesis of 3′-Azido-3′-Deoxythiymidine (AZT) and 3′-Azido-2′,3′-Dideoxyuridine (AZDDU, CS-87) from D-Mannitol,”Tetrahedron Lett., 29(42):5349-5352 (1988).
Chu, C.K., et al., “Comparative Activity of 2′,3′-Saturated and Unsaturated Pyrimidine and Purine Nucleosides Against Human Immunodeficiency Virus Type 1 in Peripheral Blood Mononuclear Cells,”Biochem Pharm., 37(19):3543-3548 (1988).
Chu, C.K., et al., “Structure-Activity Relationships of Pyrimidine Nucleosides as Antiviral Agents for Human Immunodeficiency Virus Type 1 in Peripheral Blood Mononuclear Cells,”J. Med. Chem., 32:612 (1989).
Coates, J.A.V., et al., “The Separated Enantiomers of 2′-Deoxy-3′-thiacytidine(BCH-189) Both
Choi Woo-Baeg
Liotta Dennis C.
Schinazi Raymond F.
Balasubramanian Venkataraman
Emory University
King & Spalding
LandOfFree
Method of resolution and antiviral activity of... does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Method of resolution and antiviral activity of..., we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Method of resolution and antiviral activity of... will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-4021011