Water-soluble prodrugs

Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...

Reexamination Certificate

Rate now

  [ 0.00 ] – not rated yet Voters 0   Comments 0

Details

C544S245000, C546S051000, C514S283000

Reexamination Certificate

active

07910593

ABSTRACT:
An objective of the present invention is to provide water-soluble prodrugs that can be administered parenterally, and which show excellent water solubility and small interspecies or individual differences and are rapidly converted to the active form by chemical conversion. This invention provides water-soluble prodrugs represented by formula (1), or pharmaceutically acceptable salts, or hydrates or solvates thereof,(wherein,R1represents a hydrogen atom, or C1-C6 alkyl group;W represents a divalent group comprising a tertiary amino group or sulfonyl group; andY represents a residue of a compound represented by Y—OH comprising an alcoholic hydroxyl group).

REFERENCES:
patent: 4943579 (1990-07-01), Vishnuvajjala et al.
patent: 4975278 (1990-12-01), Senter et al.
patent: 6130039 (2000-10-01), Bandman et al.
patent: 6245750 (2001-06-01), Shepard
patent: 6265540 (2001-07-01), Isaacs et al.
patent: 6294344 (2001-09-01), O'Brien
patent: 6825194 (2004-11-01), Murata et al.
patent: 7109195 (2006-09-01), Murata et al.
patent: 7595400 (2009-09-01), Fukuda et al.
patent: 2001/0016329 (2001-08-01), Shepard
patent: 2002/0012663 (2002-01-01), Waksal
patent: 2003/0138864 (2003-07-01), Ishitsuka et al.
patent: 2009/0118271 (2009-05-01), Umeda et al.
patent: 2009/0149478 (2009-06-01), Endo et al.
patent: 2009/0312554 (2009-12-01), Fukuda et al.
patent: 2009/0326225 (2009-12-01), Fukuda et al.
patent: 199853264 (1998-07-01), None
patent: 1241192 (2000-01-01), None
patent: 1361700 (2002-07-01), None
patent: 1424912 (2003-06-01), None
patent: 0 074 256 (1983-03-01), None
patent: 0 220 601 (1987-05-01), None
patent: 0 296 597 (1988-12-01), None
patent: 0 471 358 (1992-02-01), None
patent: 0 495 432 (1992-07-01), None
patent: 0 506 478 (1992-09-01), None
patent: 0 667 165 (1995-08-01), None
patent: 0 897 924 (1999-02-01), None
patent: 1 757 609 (2007-02-01), None
patent: 1 854 792 (2007-11-01), None
patent: 2 334 256 (1999-08-01), None
patent: 2-71836 (1990-03-01), None
patent: 06-087746 (1994-03-01), None
patent: 9-241298 (1997-09-01), None
patent: 11-158080 (1999-06-01), None
patent: 2002-505672 (2002-02-01), None
patent: 2002-114710 (2002-04-01), None
patent: 2003-520195 (2003-07-01), None
patent: 2003-523980 (2003-08-01), None
patent: 2004-535363 (2004-11-01), None
patent: 2005-047934 (2005-02-01), None
patent: 2005-511643 (2005-04-01), None
patent: 2005-514359 (2005-05-01), None
patent: 2005-255643 (2005-09-01), None
patent: WO 90/03169 (1990-04-01), None
patent: WO 95/22549 (1995-08-01), None
patent: WO 96/38146 (1996-12-01), None
patent: WO 98/13059 (1998-04-01), None
patent: WO 98/28304 (1998-07-01), None
patent: WO 98/35940 (1998-08-01), None
patent: WO 98/51787 (1998-11-01), None
patent: WO 98/56807 (1998-12-01), None
patent: WO 98/57662 (1998-12-01), None
patent: WO 99/05103 (1999-02-01), None
patent: WO 00/51991 (2000-09-01), None
patent: WO 00/63418 (2000-10-01), None
patent: WO 01/20331 (2001-03-01), None
patent: WO 01/49291 (2001-07-01), None
patent: WO 01/62235 (2001-08-01), None
patent: WO 02/00168 (2002-01-01), None
patent: WO 02/10741 (2002-02-01), None
patent: WO 02/056885 (2002-07-01), None
patent: WO 02/070658 (2002-09-01), None
patent: WO 02/100172 (2002-12-01), None
patent: WO 03/043631 (2003-05-01), None
patent: WO 03/045942 (2003-06-01), None
patent: WO 03/045952 (2003-06-01), None
patent: WO 2004/012662 (2004-02-01), None
patent: WO 2004/014386 (2004-02-01), None
patent: WO 2004/073601 (2004-09-01), None
patent: WO 2005/097803 (2005-10-01), None
patent: WO 2006/028904 (2006-03-01), None
patent: WO 2006/090743 (2006-08-01), None
Smith, M. B. Organic Synthesis, McGraw-Hill, Inc. 1994, Chapter 1.
Del Poeta, et al., Comparison of In Vitro Activities of Camptothecin and Nitidine Derivatives against Fungal and Cancer Cells, Antimicrobial Agents and Chemotherapy, pp. 2862-2868, vol. 43, No. 12 (1999).
Shan et al., “Prodrug Strategies Based on Intramolecular Cyclization Reactions,” Journal of Pharmaceutical Sciences, Jul. 1997, 86(7), 765-767.
Albin et al., “Main Drug-metabolizing Enzyme Systems in Human Breast Tumors and Peritumoral Tissues,” Cancer Research, vol. 53, Aug. 1, 1993, pp. 3541-3546.
Alevizos et al., “Oral cancer in vivo gene expression profiling assisted by laser capture microdissection and microarray analysis,” Oncogene, vol. 20, Sep. 2001, pp. 6196-6204.
Batetta et al., “G6PD activity and gene expression in leukemic cells from G6PD-deficient subjects,” Cancer Letters, vol. 140, Jun. 1999, pp. 53-58.
Beall et al., “Mechanisms of action of quinone-containing alkylating agents I: NQ01-directed drug development,” Frontiers in Bioscience, vol. 5, Jul. 1, 2000, pp. 639-648.
Bielawska et al., “Prolidase as a prodrug converting enzyme II. Synthesis of praline analogue of anthraquinone-2-carboxylic acid and its susceptibility to the action of prolidase,” Rocz. Akad. Med. Bialymst., vol. 43, 1998, pp. 201-209.
Bielawska et al., “Prodilase as a prodrug converting enzyme III. Synthesis of praline analogues of melphalan and their susceptibility to the action of prolidase,” Rocz. Akad. Med. Bialymst., vol. 44, 1999, pp. 190-199.
Bielawska et al., “Prolidase-activated prodrug for cancer chemotherapy Cytotoxic activity of proline analogue of chlorambucil in breast cancer MCF-7 cells,” II Farmaco, vol. 55, Nov.-Dec. 2000, pp. 736-741.
Bielawska et al., “Cytotoxicity activity of L-proline analogues of anthraquinone-2-carboxylic acid in breast cancer MCF-7 cells,” Folia Histochemica et Cytobiologica, vol. 39, suppl. 2, May 2001, pp. 207-208.
Ciaccio et al., “Modulation of Detoxification Gene Expression in Human Colon HT29 Cells by Glutathione-S-Transferase Inhibitors,” Mol. Pharamcol., vol. 48, No. 4, Oct. 1995, pp. 639-647.
Gasa et al., “Elevated Activities and Properties of Arylsulfatases A and B and B-Variant in Human Lung Tumors,” Cancer Research, vol. 40, No. 10, Oct. 1980, pp. 3804-3809.
Greengard et al., “The Undifferentiated Enzymic Composition of Human Fetal Lung and Pulmonary Tumors,” Cancer Research, vol. 3, Mar. 1977, pp. 884-891.
Herzfeld et al., “Human Colon Tumors,” Cancer, vol. 42, No. 3, Sep. 1978, pp. 1280-1283.
Herzfeld et al., “Enzyme Activities in Human Fetal and Neoplastic Tissues,” Cancer, vol. 46, No. 9, Nov. 1980, pp. 2047-2054.
Hsu et al., “Overexpression of dihydrodiol Dehydrogenase as a Prognostic Marker of Non-Small Cell Lung Cancer,” Cancer Research, vol. 6, Mar. 15, 2001, pp. 2727-2731.
Kapitonov et al., “Cloning, Characterization, and Expression of Human Ceramide Galactosyltransferase cDNA,” Biochemical and Biophysical Research Communications, vol. 232, Mar. 1997, pp. 449-453.
Karna et al., “Collagen metabolism disturbances are accompanied by an increase in prolidase activity in lung carcinoma planoepitheliale,” Int. J. Exp. Path., vol. 81, No. 5, Oct. 2000, pp. 341-347.
Kashima et al., “Expression of Oligodendrocyte-associated Genes in Cell Lines Derived from Human Gliomas and Neuroblastomas,” Cancer Research, vol. 53, Jan. 1, 1993, pp. 170-175.
Kirschmann et al., “Differentially expressed genes associated with the metastatic phenotype in breast cancer,” Breast Cancer Research and Treatment, vol. 55, No. 2, May 1999, pp. 127-136.
Krovat et al., “Fingerprinting of cytochrome P450 and Microsomal Epoxide Hydrolase Gene Expression in Human Blood Cells,” Toxicological Sciences, vol. 55, No. 2, Jun. 2000, pp. 352-360.
Kuivaniemi et al., “Deficient production of lysyl oxidase in cultures of malignantly transformed human cells,” FEBS Lett, vol. 195, No. 1-2, Jan. 1986, pp. 261-264.
Kuo et al., “Human glucose-6-phosphate dehydrogenase (G6PD) gene transforms NIH 3T3 cells and induces tumors in nude mice,” Int. J. Cancer, vol. 85, No. 6, Mar. 2000, pp. 857-864.
Leenders et al., “Synthesis and evaluation of novel duanomycin-phosphate-sulfate-

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

Water-soluble prodrugs does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Water-soluble prodrugs, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Water-soluble prodrugs will most certainly appreciate the feedback.

Rate now

     

Profile ID: LFUS-PAI-O-2709913

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