Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – 9,10-seco- cyclopentanohydrophenanthrene ring system doai
Reexamination Certificate
2006-09-26
2006-09-26
Qazi, Sabiha N. (Department: 1616)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
9,10-seco- cyclopentanohydrophenanthrene ring system doai
C552S653000
Reexamination Certificate
active
07112579
ABSTRACT:
This invention provides a novel class of vitamin D related compounds, namely, the 2-alkyl-19-nor-vitamin D derivatives, as well as a general method for their chemical synthesis. The compounds have the formula:where Y1and Y2, which may be the same or different, are each selected from the group consisting of hydrogen and a hydroxy-protecting group, R6is selected from the group consisting of alkyl, hydroxyalkyl and fluoroalkyl, and where the group R represents any of the typical side chains known for vitamin D type compounds. These 2-substituted compounds, especially the 2α-methyl and the 2α-methyl-20S derivatives, are characterized by relatively high intestinal calcium transport activity and relatively high bone calcium mobilization activity resulting in novel therapeutic agents for the treatment of diseases where bone formation is desired, particularly low bone turnover osteoporosis. These compounds also exhibit pronounced activity in arresting the proliferation of undifferentiated cells and inducing their differentiation to the monocyte thus evidencing use as anti-cancer agents and for the treatment of diseases such as psoriasis.
REFERENCES:
patent: 4666634 (1987-05-01), Miyamoto et al.
patent: 5086191 (1992-02-01), DeLuca et al.
patent: 5237110 (1993-08-01), DeLuca et al.
patent: 5246925 (1993-09-01), DeLuca et al.
patent: 5536713 (1996-07-01), DeLuca et al.
patent: 5587497 (1996-12-01), DeLuca et al.
patent: 5817648 (1998-10-01), Kutner et al.
patent: 5843928 (1998-12-01), Deluca et al.
patent: 5936133 (1999-08-01), Deluca et al.
patent: 5945410 (1999-08-01), DeLuca et al.
patent: 6277837 (2001-08-01), DeLuca et al.
patent: 6316642 (2001-11-01), DeLuca et al.
patent: 6369099 (2002-04-01), DeLuca et al.
patent: 6392071 (2002-05-01), DeLuca et al.
patent: 6440953 (2002-08-01), DeLuca et al.
patent: 6458827 (2002-10-01), DeLuca et al.
patent: 6482812 (2002-11-01), DeLuca et al.
patent: 6506912 (2003-01-01), DeLuca et al.
patent: 6537981 (2003-03-01), DeLuca et al.
patent: 6544969 (2003-04-01), DeLuca et al.
patent: 6566352 (2003-05-01), DeLuca et al.
patent: 6573256 (2003-06-01), Bishop et al.
patent: 6667298 (2003-12-01), DeLuca et al.
patent: 6680309 (2004-01-01), Bishop et al.
patent: 6696431 (2004-02-01), DeLuca et al.
patent: 2004/0152675 (2004-08-01), DeLuca et al.
patent: 0078704 (1987-04-01), None
patent: 0184206 (1989-04-01), None
patent: 0387077 (1994-01-01), None
patent: 0480572 (1995-06-01), None
patent: 0516410 (1998-07-01), None
patent: 0474517 (1998-11-01), None
patent: WO 90/09991 (1990-09-01), None
patent: WO 96/01811 (1996-01-01), None
Balasubramanian et al “Recent Developments in Cancer, Etc.” Annual Reports in Medicinal Chemistry, 33, 1998, Academic Press, San Deigo, pp. 151-159.
Draetta et al “Section V. Topics in Biology”, Annual Reports in Medicinal Chemistry, 31, 1996, Academic Press, San Diego, pp. 241-246.
Chemical Abstracts, XP-002066055, vol. 121, No. 21, Nov. 21, 1994.
Posner et al, “2-Fluoroalkyl A-Ring Analogs of 1,25-Dihydroxyvitamin D3-Stereocontrolled Total Synthesis via Intramolecular and Intermolecular Diels-Alder Cycloadditions. Preliminary Biological Testing”, Journal of Organic Chemistry, 60, pp. 4617-4628, 1995.
Slatopolsky et al, “A New Analog of Calcitriol, 19-Nor-1,25-(OH)2 D2 Suppresses Parathyroid Hormone Secretion in Uremic Rats in the Absence of Hypercalcemia”, American Journal of Kidney Disorders, 26(5), 832-60, 1995.
Posner et al, “Stereocontrolled Synthesis of a Trihydroxylated A Ring as an Immediate Precursor to 1Alpha,2Alpha,25-Trihydroxyvitamin D3”, Journal of Organic Chemistry, 56, pp. 4339-4341, Apr. 15, 1995.
Chemical Abstracts, “Chemistry of Synthetic High Polymers”, vol. 110, No. 10, Abstract 110: 82505v, Mar. 6, 1989.
Okano et al, “Regulatory Activities of 2beta-(3-Hydroxypropoxy)-1alpha,25-Dihydroxyvitamin D3. A Novel Synthetic Vitamin D3 Derivative on Calcium Metabolism”, Biochemical and Biophysical Research Communications, vol. 163, No. 3, pp. 1444-1449, Sep. 29, 1989.
Bouillon et al, “Biological Activity of Dihydroxylated 19-Nor-(Pre)Vitamin D3”, Bioactivity of 19-Nor-Pre D, vol. 8, No. 8, pp. 1009-1015, 1993.
Sarandeses et al, “Synthesis of 1alpha,25-Dihydroxy-19-Norprevitamin D3”, tetrahedron Letters, pp. 5445-5448, Apr. 1992.
Perlman et al, “1alpha,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, Feb. 1990.
Baggiolini et al, “Stereochemical Total Synthesis of 1a,25-Dihydroxycholecalciferol and 1beta,25-Dihydroxyerocalciferol”, Journal of Organic Chemistry, 51, pp. 3098-3108, 1986.
Kiegiel et al, “Chemical Conversion of Vitamin D3 to its 1,25-Dihydroxy Metabolite”, Tetrahedron Letters, vol. 31, No. 43, pp. 6057-60660, 1991.
DeLuca Hector F.
Sicinski Rafal R.
Andrus Sceales Starke & Sawall LLP
Qazi Sabiha N.
Wisconsin Alumni Research Foundation
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