Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Carbohydrate doai
Reexamination Certificate
2005-04-26
2005-04-26
Wilson, James O. (Department: 1623)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Carbohydrate doai
C536S001110, C536S004100, C536S055000, C536S055100, C536S055200, C536S055300, C536S123100, C536S124000
Reexamination Certificate
active
06884788
ABSTRACT:
The present invention relates to biscarbodiimides, thiourea derivatives, urea derivatives, and cross-linked hyaluronan derivatives having at least one intramolecular disulfide bond, and methods of preparation thereof. The invention also includes thiolated hyaluronan derivatives and salts thereof having at least one pendant thiol group or a modified pendant thiol group, and methods of preparation thereof. An example of a modified pendant thiol group is a sulfhydryl group linked to a small molecule such as a bioactive agent, for example a drug or pharmaceutically active moiety. A hyaluronan derivative having a sulfhydryl group linked to a pharmaceutically active moiety is useful as a sustained or controlled release drug delivery vehicle. Compositions containing the hyaluronan derivatives of the invention can reversibly viscosify in vivo or in vitro, in response to mild changes in condition, and are thus useful in ophthalmic surgery and in tissue engineering.
REFERENCES:
patent: 2832756 (1958-04-01), Melamed
patent: 4280954 (1981-07-01), Yannas et al.
patent: 4582865 (1986-04-01), Balazs et al.
patent: 4703108 (1987-10-01), Silver et al.
patent: 4713448 (1987-12-01), Balazs et al.
patent: 4937270 (1990-06-01), Hamilton et al.
patent: 4973493 (1990-11-01), Guire
patent: 5017229 (1991-05-01), Burns et al.
patent: 5099013 (1992-03-01), Balazs et al.
patent: 5118813 (1992-06-01), Reiner
patent: 5128326 (1992-07-01), Balazs et al.
patent: 5356883 (1994-10-01), Kuo et al.
patent: 5527893 (1996-06-01), Burns et al.
patent: 5616568 (1997-04-01), Pouyani et al.
patent: 5690961 (1997-11-01), Nguyen
patent: 6096727 (2000-08-01), Kuo et al.
patent: 6096728 (2000-08-01), Collins et al.
patent: 6174999 (2001-01-01), Miller et al.
patent: 6537979 (2003-03-01), Kuo et al.
patent: 0 416 250 (1991-03-01), None
patent: 57009759 (1982-01-01), None
patent: 2000-191538 (2000-07-01), None
patent: WO 8600912 (1986-02-01), None
patent: WO 8805436 (1988-07-01), None
patent: WO 8805436 (1988-07-01), None
patent: WO 8902445 (1989-03-01), None
patent: WO 9009401 (1990-08-01), None
patent: WO 9220349 (1992-11-01), None
patent: WO 9402517 (1994-02-01), None
patent: WO 0012146 (2000-03-01), None
patent: WO 0209792 (2002-02-01), None
patent: WO 02068383 (2002-09-01), None
Sparer, R.V., et al., “Controlled Release from Glycosaminoglycan Drug Complexes.” InControlled Release Delivery Systems, T.J. Roseman, et al., eds. (NY: Marcel Dekker, Inc.), pp. 107-119 (1983).
Beuvery, E.C., et al., “Analytical, Toxicological and Immunological Consequences of the Use of N-Ethyl-N′-(3-Dimethylaminopropyl) Carbodiimide as Coupling Reagent for the Preparation of Meningococcal Group C Polysaccharide-Tetanus Toxoid Conjugate as Vaccine for Human Use,”Develop. Biol. Standard., 63:117-128 (1986).
Kuo, J., et al., “Chemical Modification of Hyaluronic Acid by Carbodiimides,”Biconjugate Chem., 2(4): 232-241 (1991).
Sparer, Randal Vernon, “The Synthesis and Characterization of Crosslinked Chondroitin-4-Sulfate Hydrogels: Potential Biomaterials”. Masters Thesis, Case Western Reserve University, 1980.
Hermanson, G. T.,Bioconjugate Techniques(Academic Press), pp. 104-107 (1996).
Schwartz, W. E., et al., “N-(β-iodethyl)trifluoroacetamide: A new reagentfor the aminoethylation of thiol groups in proteins,”Anal. Biochem., 106:43-48 (1980).
Bernkop-Schnürch, A., et al., “Development of controlled drug release systems based on thiolated polymers,”Journal of Controlled Release, 66:39-44 (2000).
de Weers, O., et al., “Application of cystamine and N,N-Bis(glycyl)cystamine as Linkers in Polysaccharide-Protein Conjugation,”Bioconjugate Chem., 9:309-315 (1998).
Williams, A., and Ibrahim, I.T., “Carbodiimide Chemistry: Recent Advances,”Chem. Rev., 81(4):589-636 (1981).
March, J., “Eliminations: Reactions,”Advanced Organic Chemistry, Chapter 17: Reaction, Mechanisms, and Structure, (NY: John Wiley & Sons), p. 1043 (1992).
Schimmelschmidt, K., et al., “Darstellung und Umsetzungen der 2-Amino-äthythioschwefelsäure,”Chemische Berichte96(1):38-47 (1963).
Wojahn, H. and I. Lerch, “Aromatische Disulfid-Verbindungen mit tuberkulocider Wirkung,”Arzneimittel Forschung2:455-460 (1952).
Kjær, A. and B. Christensen, isoThyocyanates XXVI. Straight-Chain ω-Methylathioalkyl isoThyocyanates and some Derivatives,Acta Chem. Scand. 11(8): 1298-1307 (1957).
Kuo, Jing-wen, “Synthesis and Properties of Hyaluronic Acid Modified by Designed Carbodiimides”, Unpublished doctoral dissertation, State University of New York. (1989).
Kuo, Jing-wen, “Synthesis and Properties of Hyaluronic Acid Modified by Designed Carbodiimides”,DAI, 50(12): 5626-B (1990).
Pouyani, T., et al., “Solid-State NMR of N-Acylureas Derived from the Reaction of Hyaluronic Acid with Isotopically-Labeled Carbodiimides”,J. Am. Chem. Soc., 114: 5972-5976 (1992).
Bulpitt Paul C. A.
Sadozai Khalid K.
Sherwood Charles H.
Anika Therapeutics, Inc.
Hamilton Brook Smith & Reynolds P.C.
Krishnan Ganapathy
Wilson James O.
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