Mono- and disaccharide derivatives

Details Mono- and disaccharide derivatives Mono- and disaccharide derivatives

2009-04-20

2011-11-08

Peselev, Elli (Department: 1623)

Drug, bio-affecting and body treating compositions

Nonspecific immunoeffector, per se ; or nonspecific...

Reexamination Certificate

active

08052981

ABSTRACT:
The present invention includes a formulation comprising a physiological salt solution, or an oil-in-water emulsion, or a water immiscible solid phase, and an adjuvant comprising one or more disaccharide derivatives derived from cellobiose, gentiobiose, lactose, lactulose, maltose, melibiose, sucrose or turanose, wherein at least four of the free hydroxyl groups of the disaccharide molecule have been modified such that the disaccharide derivative has: (i) at least 3, but not more than N-1, fatty acid ester groups, wherein each of the fatty acid ester groups is represented by a general formula of —O—C(═O)—(CH2)xCH3wherein x is between 6 and 14, and (ii) at least one, but no more than N-1 anionic groups, wherein N is the number of hydroxyl groups of the disaccharide from which the derivative is derived and wherein the combined number of fatty acid esters and anionic groups does not exceed N.

REFERENCES:
patent: 4243663 (1981-01-01), Azuma et al.
patent: 4746742 (1988-05-01), Hasegawa et al.
patent: 5965603 (1999-10-01), Johnson et al.
patent: 2002/0120133 (2002-08-01), Obaje
patent: 3941061 (1991-06-01), None
patent: 0192296 (1986-08-01), None
patent: 0775494 (1997-05-01), None
patent: 0781559 (1997-07-01), None
patent: 0689454 (1997-09-01), None
patent: 1572368 (1980-07-01), None
patent: 2220211A (1990-01-01), None
patent: WO8404526 (1984-11-01), None
patent: WO9216231 (1992-10-01), None
patent: WO9620008 (1996-07-01), None
patent: WO9620222 (1996-07-01), None
Bazin et al., “Synthesis of Sucrose-Based Surfactants through Regioselective Sulfonation of Acylsucrose and the Nucleophilic Opening of a Sucrose Cyclic Sulfate”, Carbohydrate Research, vol. 309(2), pp. 189-205; May 1998.
Cox et al., “Adjuvants—A Classification and Review of their Modes of Action”, Vaccine, vol. 15. No. 3, pp. 248-256; 1997.
Gupta et al., “Adjuvants for Human Vaccines—Current Status, Problems and Future Prospects”, Vaccine, vol. 13, No. 14, pp. 1263-1276; 1995.
Hilgers et al., “Sufolipo-Cyclodextrin in Squalane-In-Water as a Novel and Safe Vaccine Adjuvant”, Vaccine, vol. 17, pp. 219-228; Feb. 1999.
Kotani et al., “Synthetic Lipid A with Endotoxic and Related Biological Activities Comparable to those of a Natural Lipid A from anEscherichia coliRe-Mutant”, Infection and Immunity, vol. 49, No. 1, pp. 225-237; Jul. 1985.
Kotani et al., “Immunobiologically Active Lipid A Analogs Synthesized According to a Revised Structural Model of Natural Lipid A”, Infection and Immunity, vol. 45, No. 1, pp. 293-296; Jul. 1984.
Kumazawa et al., “Importance of Fatty Acid Substituents of Chemically Synthesized Lipid A-Subunit Analogs in the Expression of Immunopharmacological Activity”, Infection and Immunity, vol. 56, No. 1, pp. 149-155; Jan. 1988.
Maeda et al., “Adjuvant Activities of Synthetic Lipid A Subunit Analogues and its Conjugates with Muramyl Dipeptide Derivatives”, Vaccine, vol. 7, pp. 275-281; Jun. 1989.
Nigam et al., “Effects of Structural Variations in Synthetic Glycolipids Upon Mitogenicity for Spleen Lymphocytes, Adjuvancy for Humoral Immune Response and on Anti-Tumour Potential”, Br. J. Cancer, vol. 46, pp. 782-793; 1982.
Nigam et al., “Maltose Tetrapalmitate, a Nontoxic Immunopotentiator with Antitumor Activity”, Cancer Research, vol. 38, pp. 3315-3321; Oct. 1978.
Takada et al., “Immunopharmacological Activities of a Synthetic Counterpart of a Biosynthetic Lipid A Precursor Molecule and of Its Analogs”, Infection and Immunity, vol. 48, No. 1, pp. 219-227; Apr. 1985.
Bazin et al., “Regiospecific Synthesis of New Methyl Sulfoglucopyranoside-Based Surfactants: Nucleophilic Displacement of a Cyclic Sulfate,” Synthesis, vol. 4, pp. 621-624; 1999.
Cao et al., “Lipase-Catalyzed Solid Phase Synthesis of Sugar Fatty Acid Esters,” Biocatalysis and Biotransformation, vol. 14, pp. 269-283; 1997.
Redmann et al., “Chemoenzymatic Synthesis of Glucose Fatty Esters,” Carbohydrate Research, vol. 300, pp. 103-108; 1997.
Akoh et al., “Emulsification Properties of Polyesters and Sucrose Ester Blends I: Carbohydrate Fatty Acid Polyesters,” Journal of the American Oil Chemists Society, vol. 69, pp. 9-13; 1992.
Nishikawa et al., “Chemical and Biochemical Studies on Carbohydrate Esters IX. Antitumor Effects of Selectively Fatty Acylated Products of Maltose”, Chem. Pharm. Bull. 29(2): 505-513 (1981).
Turkstra et al., “Chronic Toxicity and Testosterone Inhibitory Effects of Two Potential GnRH Human Prostate Cancer Vaccines in Young Male Pigs”, Chapter 8 in a dissertion published on Sep. 29, 2005, pp. 1-25.
Bodewes, et al., “A Single Immunization with CoVaccine HT-Adjuvanted H5N1 Influenza Virus Vaccine Induces Protective Cellular and Humoral Immune Responses in Ferrets”, Journal of Virology, pp. 7943-7952; Aug. 2010.
Opposition to EP1233969, Submissions of the Patentee, pp. 1-22; 2010.
Medical News Today, “Start of Phase 2a Clinical Study of Angiotensin Therapeutic Vaccine in Hypertension”, Jun. 26, 2008.
Opposition to EP1233969, Auxiliary Request.
Opposition to EP1233969, Table showing presence or absence of features of claim 1 of the Main Request in prior art documents D1-D20.
Opposition to EP1233969, Main Request.
Opposition to EP1233969, Authorsation.
Opposition to EP1233969, Patentee Letter to EPO dated Oct. 11, 2010.
Jones SD, Vaccines Europe-Informa Conference. Vaccine Scale-up and Manufacturing. Dec. 2-3, 2008, Brussels, Belgium.
“Efficacy and Safety Study of the Therapeutic Vaccine PEP223 in Prostrate Cancer Patients”, ClinicalTrials.gov., Oct. 11, 2010.
Health—Taking the Temperature of European Healthcare, FluVac—Increased Immunogenicity of Pandemic Influenza Vaccine, European Commission website on Oct. 11, 2010.
Opposition to EP1233969, Hilgers et al., “Synthetic Sulpholipopolysaccharides: Novel Adjuvants for Humoral Immune Responses”, Immunology, vol. 60, pp. 141-146; 1987.

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