Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Phosphorus containing other than solely as part of an...
Reexamination Certificate
2003-12-09
2008-12-09
Shiao, Rei-Tsang (Department: 1626)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Phosphorus containing other than solely as part of an...
C546S023000, C546S065000
Reexamination Certificate
active
07462609
ABSTRACT:
The present invention provides prodrugs derived from the sparingly soluble anticancer isocarbostyril narciclasine, a component of various Narcissus species, said prodrugs having potential for use against animal and human cancers. Also disclosed is an efficient procedure for the synthetic conversion of narciclasine to several more soluble cyclic phosphate compounds, including “narcistatin”.
REFERENCES:
patent: 4522811 (1985-06-01), Eppstein et al.
patent: 5529989 (1996-06-01), Pettit et al.
patent: 5830850 (1998-11-01), Gelb et al.
patent: 5985436 (1999-11-01), Hirokane et al.
patent: 7067480 (2006-06-01), Harnett et al.
patent: 11255650 (1999-09-01), None
patent: WO/2000/048606 (2000-08-01), None
International Search Report for International Application No. PCT/US03/39067 dated Mar. 25, 2004.
Pettit et al., “Antineoplastic Agents 500. Narcistatin”, J. Nat. Prod., 66:92-96, 2003.
Pettit et al., “Antineoplastic Agents. 450. Synthesis of (+)-Pancratistatin from (+)-Narcilasine as Relay1α”,J. Org. Chem., 66:2583-2587 (2001).
Khaldi et al., “A Short Route to Enantiomerically Pure Narciclasine Derivatives”,Tetrahedron Letters, 17:3003-3006 (1995).
Veronese et al., “Slow Release of Narciclasine from Matrices Obtained by Radiation-Induced Polymerization”,Journal of Controlled Release, 16:291-298 (1991).
Supplementary European Search Report for EP Application No. EP 03 81 2894 dated Jul. 25, 2007.
Ackerman et al., “Effects of Naproxen on Connective Tissue Changes in the Adjuvant Arthritic Rat”,Arthritis and Rheumatism, 22(12):1365-1374 (1979).
Afuwape et al., “The Role of the Angiogenic Molecule VEGF in the Pathogenesis of Rheumatoid Arthritis”,Histol. Histophathol, 17(6):961-972 (2002).
Afuwape et al., “Adenoviral Delivery of Soluble VEGF Receptor 1 (sFlt-1) Abrogrates Disease Activity in Murine Collagen-Induced Arthritis”,Gene Ther., 10:1950-1960 (2003).
Allen et al., “Suppression of Monocyte Function and Differential Regulation of IL-1 and IL-1ra by IL-4 Contribute to Resolution of Experimental Arthritis”,J. Immunol., 151(8):4344-4351 (1993).
Berge et al., “Pharmaceutical Salts”,J. Pharm. Sci., 66(1):1-19 (1997).
Borderie et al., “Nitric Oxide Synthase is Expressed in the Lymphomononuclear Cells of Synovial Fluid in Patients with Rheumatoid Arthritis”,The Journal of Rheumatology, 26(10):2083-2088 (1999).
Bresnihan et al., “Microscopic Measurement of Synovial Membrane Inflammation in Rheumatoid Arthritis: Proposals for the Evaluation of Tissue Samples by Quantitative Analysis”,Br J Rheumatol, 37:636-642 (1998).
Burmester et al., “Mononuclear Phagocytes and Rheumatoid Synovitus. Mastermind or Workhorse in Arthritis”,Arthritis Rheum.40(1):5-18 (1997).
Camilleri et al., “The Effect of Free and Lipsome-Encapsulated Clodronate on the Hepatic Mononuclear Phagocyte System in the Rat”,Clin. Exp. Immunol, 99:269-275 (1995).
Carol et al., “Immunohistochemical Study of Lymphoid Tissues in Adjuvant Arthritis (AA) by Image Analysis; Relationship with Synovial Lesions”,Clin. Exp. Immunol, 120:200-208 (2000).
Dijkstra et al., “Macrophages and Dendritic Cells in Antigeninduced Arthritis: An Immunohistochemical Study Using Cryostat Sections of the Whole Knee Joint of Rat”,Scand J. Immunol, 26:513-523 (1987).
Edmonds et al., “Antirheumatic Drugs: A Proposed New Classification”,Arthritis Rheum, 36(3):336-339 (1993).
Egeland, T., “Immunological Aspects of the Rheumatoid Synovium”,scand J. Rheumatol Suppl.66:27-33 (1987).
Feldmann et al., “Role of Cytokines in Rheumatoid Arthritis”,Annu. Rev. Immunol, 14:397-440 (1996).
Feldmann et al., “Anti-TNFα Therapy of Rhuematoid Arthritis: What Have We Learned?”,Ann. Rev. Immunol, 19:163-196 (2001).
Firestein et al., “Anticytokine Therapy in Rheumatoid Arthritis”,N. Engl. J. Med.337(3):195-197 (1997).
Fox, DA., “The Role of T Cells in the Immunopathogenesis of Rheumatoid Arthritis: New Perspectives”,Arthritis Rheum, 40(4):598-609 (1997).
Gabrielson et al., “Antivral (RNA) Activity of Selected Amaryllidaceae Isoquinoline Constituents and Sythesis of Related Substances”,J. Natural Products, 55(11):1569-1581 (1992).
Giatromanolaki et al., “The Angiogenic Pathway ‘Vascular Endothelial Growth Factor/FLK-I (KDR)- receptor’ in Rheumatoid Arthritis and Osteoarthritis”,J. of Pathology, 194(1):101-108 (2001).
Hudlicky et al., “Total Sythesis and Biological Evaluation of Amaryllidaceae Alkaloids: Narciclasine, ent-7-deoxypancratistatin Regioisomer of 7-Deoxypancratistatin, 10b-epi-deoxypancratistatin, and Truncated Derivatives”,J. Org. Chem., 67:8726-8743 (2002).
Idso et al., “Effects of Atomosperic CO2Enrichment on the Growth and Development ofHymenocallis Littoralis(Amaryllidaceae) and the Concentrations of Several Antineplastic and Antiviral Constituents of its Bulbs”,Am. J. Bot., 87(6):769-773 (2000).
Keffer et al., “Transgenic Mice Expressing Human Tumor Necrosis Factor: A Predictive Genetic Model of Arthritis”,EMBO J., 10(13):4025-4031.
Kinne et al., “Treatment of Rat Arthritides with Clodronate-Containing Liposomes”,Scand. J. Rheumatol Suppl., 24(101):91-97 (1995).
Kinne et al., “Long-Term Amelioration of Rat Adjuvant Arthritis Following Systemic Elimination of Macrophages by Clodronate-Containing Liposomes”,Arthritis Rheum, 38(12):1777-1790 (1995).
Kool et al, “Immunohistology of Joint Inflammation Induced in Rats by Cell Wall Fragments of Eubacterium Aerofaciens”,Scand J. Immunol, 36:497-506 (1992).
Lala et al., “Role of Nitric Oxide in Carcinogenesis and Tumour Progression”,Lancet Oncol., 2(3) 149-156 (2001).
Lavastre et al., “anti-Inflammatory Effect of Viscum Album Agglutinin-1 (VAA-1): Induction of Apoptosis in Activated Neutrophils and Inhibition of Lipopolysaccharide-Induced Neutrophilic Inflammation in Vivo”,Clin. Exp. Immunol, 137:272-278 (2004).
Lorton et al., “Norepinephrine Content in Primary and Secondary Lymphoid Organs is Altered in Rats with Adjuvant-Induced Arthritis”,Mech Ageing Dev., 94:145-163 (1997).
Lu et al., “Vascular Endothelial Growth Factor Expression and Regulation of Murine Collagen-Induced Arthristis”,J. Immunol, 164(11):5922-5927 (2000).
McNulty et al., “Studies Directed Towards the Refinement of the Pancratistatin Cytotoxic Pharmacophore”,BioOrganic & Medicinal Chemistry Letters, 11:169-172 (2001).
Mikami et al., “Suppressive Activity of Lycoricidinol (Narciclasine) Against Cytotoxicity of Neutrophil-Derived Calprotectin, and its Suppressive Effect on Rat Adjuvant Arthritis Model”,Biol Pharm Bull, 22(7):674-678 (1999).
Mulherin et al., “Synovial Tissue Macrophage Populations and Articular Damage in Rheumatoid Arthritis”,Arthritis Rheum, 39(1):115-124 (1996).
Mulherin et al., “Clinical Improvement and Radiological Deterioration in Rheumatoid Arthritis: Evidence that the Pathogenesis of Synovial Inflammation and Articular Erosion May Differ”,Br. J. Rheumatology, 35:1263-1268 (1996).
Nandakumar et al., “Collagen Type II-Specific Monoclonal Antibody-Induced Arthritis in Mice”,AJP, 163(5):1827-1837 (2003).
Ouarzane-Amara et al., “In Vitro Activities of two Antimitotic Compounds, Pancratistatin and 7-Deoxynarciclasine, AgainstEncephalitozoon Intestinals, a Microsporidium Causing Infections in Humans”,Antimicrob Agents Chemother, 45(12):3409-3415 (2001).
Paleolog et al., “Angiogenesis in Arthritis: Role in Disease Pathogenesis and as a Potential Therapeutic Target”,Angiogenesis, 2(4):295-307 (1998).
Paleolog et al., “Angiogenesis in Rheumatoid Arthritis”, Arthritis Res., 4(3):S81-90 (2002).
Pettit et al., “Synthesis of 10b-(R)-
Melody Noeleen
Pettit George R.
Arizona Board of Regents
Fennemore Craig P.C.
Shiao Rei-Tsang
LandOfFree
Narcistatin 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 Narcistatin prodrugs, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Narcistatin prodrugs will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-4041867