Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – 9,10-seco- cyclopentanohydrophenanthrene ring system doai
Reexamination Certificate
2011-05-17
2011-05-17
Qazi, Sabiha (Department: 1628)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
9,10-seco- cyclopentanohydrophenanthrene ring system doai
C552S653000
Reexamination Certificate
active
07943601
ABSTRACT:
This invention discloses 2-methylene-20-methyl-19,24,25,26,27-pentanor-vitamin D analogs, and specifically 2-methylene-20-methyl-1α-hydroxy-19,24,25,26,27-pentanor-vitamin D3, and pharmaceutical uses therefore. This compound exhibits activity in arresting the proliferation of undifferentiated cells and inducing their differentiation to the monocyte thus evidencing use as an anti-cancer agent and for the treatment of skin diseases such as psoriasis as well as skin conditions such as wrinkles, slack skin, dry skin and insufficient sebum secretion. This compound also has little, if any, calcemic activity and therefore may be used to treat autoimmune disorders or inflammatory diseases in humans as well as renal osteodystrophy. This compound may also be used for the treatment or prevention of obesity.
REFERENCES:
patent: 4666634 (1987-05-01), Miyamoto et al.
patent: 5086191 (1992-02-01), DeLuca et al.
patent: 5536713 (1996-07-01), Deluca et al.
patent: 5843928 (1998-12-01), Deluca et al.
patent: 5856536 (1999-01-01), Deluca et al.
patent: 5936133 (1999-08-01), Deluca et al.
patent: 5945410 (1999-08-01), DeLuca et al.
patent: 6566352 (2003-05-01), DeLuca et al.
patent: 6579861 (2003-06-01), DeLuca et al.
patent: 6627622 (2003-09-01), DeLuca et al.
patent: 6835723 (2004-12-01), DeLuca et al.
Arbour et al., “A Highly Sensitive Method for Large-Scale Measurements of 1,25-Dihydroxyvitamin D,” Analytical Biochemistry, vol. 255, pp. 148-154, (1998).
Baggiolini et al., “Stereocontrolled Total Synthesis of 1α,25-Dihydroxycholecalciferol and 1α,25-Dihydroxyergocalciferol,” Journal of Organic Chemistry, 51, pp. 3098-3108, (1986).
Collins et al, “Normal Functional Characteristics of Cultured Human Promyelocytic Leukemia Cells (HL-60) After Inducation of Differentiation by Dimethylsulfoxide,” The Journal of Experimental Medicine, vol. 149, pp. 969-974, (1979).
Darwish et al, “Identification of Transcription Factor That Binds to the Promoter Region of the Human Parathyroid Hormone Gene,” Archives of Biochemistry and Biophysics, vol. 365, No. 1, pp. 123-130, (1999).
Fall et al, “Vitamin D Heterocyclic Analogues. Part 1: A Stereoselective Route to CD Systems with Pyrazole Rings in their Side Chains,” Tetrahedron Letters 43, pp. 1433-1436, (2002).
Lythgoe et al, “Calciferol and its Relatives. Part22. A Direct Total Synthesis of Vitamin D2 and Vitamin D3,” J. Chem. Soc. Perkin Trans. 1, p. 590, (1978).
Lythgoe, “Synthetic Approaches to Vitamin D and its Relatives,” Chem. Soc. Rev. 9, p. 449, (1983).
Miyamoto et al, “Synthetic Studies of Vitamin D Analogues. XIV. Synthesis and Calcium Regulating Activity of Vitamin D3 Analogues Bearing a Hydroxyalkoxy Group at the 2β-Position,” Chem. Pharm. Bull., vol. 41 No. 6, pp. 1111-1113, (1993).
Nishii et al, “The Development of Vitamin D3 Analogues for the Treatment of Osteoporosis,” Osteoporosis Int., Suppl. 1, pp. S190-S193, (1993).
Okano et al, “Regulatory Activities of 2β-(3-Hydroxypropoxy)-1α,25-Dihydroxy-Vitamin D3, a Novel Synthetic Vitamin D3 Derivative, on Calcium Metabolism,” Biochemical and Biophysical Research Communications, vol. 163 No. 3, pp. 1444-1449, (1989).
Ostrem et al, “24- and 26-homo-1,25-dihydroxyvitamin D3: Preferential activity in inducing differentiation of human leukemia cells HL-60 in vitro,” Proc. Natl. Acad. Sci. USA, vol. 84, pp. 2610-2614, (1987).
Perlman et al, “1α,25-Dihydroxy-19-Nor-Vitamin D3. A Novel Vitamin D-Related Compound with Potential Therapeutic Activity,” Tetrahedron Letters, vol. 31 No. 13, pp. 1823-1824, (1990).
Perlman et al, “Novel Synthesis of 19-Nor-Vitamin D Compounds,” Tetrahedron Letters, vol. 32 No. 52, pp. 7663-7666, (1991).
Plum et al, “Biologically Active Noncalcemic Analogs of 1α,25-Dihydroxyvitamin D with an Abbreviated Side Chain Containing No Hydroxyl,” PNAS, vol. 101 No. 18, pp. 6900-6904, (2004).
Posner et al, “Stereocontrolled Total Synthesis of Calcitriol Derivatives: 1,25-Dihydroxy-2-(4′-hydroxybutyl)vitamin D3 Analogs of an Osteoporosis Drug,” Journal of Organic Chemistry, vol. 59 No. 25, pp. 7855-7861, (1994).
Posner et al, “2-Fluoroalkyl A-Ring Analogs of 1,25-Dihydroxyvitamin D3. Stereocontrolled Total Synthesis via Intramolecular and Intermolecular Diets—Alder Cycloadditions. Preliminary Biological Testing,” Journal of Organic Chemistry, vol. 60 No. 14, pp. 4617-4628, (1995).
Sardina et al, “Studies on the Synthesis of Side-Chain Hydroxylated Metabolites of Vitamin D. 2. Stereocontrolled Synthesis of 25-Hydroxyvitamin D2,” J. Org. Chem., 51, pp. 1264-1269, (1986).
Sicinski et al, “New 1α,25-Dihydroxy-19-Norvitamin D3 Compounds of High Biological Activity: Synthesis and Biological Evaluation of 2-Hydroxymethyl, 2-Methyl, and 2-Methylene Analogues,” Journal of Medical Chemistry, 41, pp. 4662-4674, (1998).
Sicinski et al, “New Highly Calcemic 1α,25-Dihydroxy-19-Norvitamin D3 Compounds with Modified Side Chain: 26,27-Dihomo- and 26,27-Dimethylene Analogs in 20S-Series,” Steroids, vol. 67, pp. 247-256, (2002).
Toh et al, “Studies on a Convergent Route to Side-Chain Analogues of Vitamin D: 25-Hydroxy-23-Oxavitamin D3,” J. Org. Chem., 48, 1414, (1983).
Clagett-Dame Margaret
DeLuca Hector F.
Glebocka Agnieszka
Plum Lori A.
Sicinski Rafal R.
Andrus Sceales Starke & Sawall LLP
Qazi Sabiha
Wisconsin Alumni Research Foundation
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