2-propylidene-19-nor-vitamin D compounds

Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – 9,10-seco- cyclopentanohydrophenanthrene ring system doai

Reexamination Certificate

Rate now

  [ 0.00 ] – not rated yet Voters 0   Comments 0

Details

C552S653000

Reexamination Certificate

active

10821479

ABSTRACT:
2-propylidene-19-nor-vitamin D compounds are disclosed as well as pharmaceutical uses for these compounds and methods of synthesizing these compounds. These compounds are characterized by high bone calcium mobilization activity and high intestinal calcium transport activity. This results in novel therapeutic agents for the treatment and prophylaxis of diseases where bone formation is desired, particularly osteoporosis, as well as autoimmune diseases such as multiple sclerosis, diabetes mellitus and lupus. These compounds also exhibit pronounced 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. These compounds also increase both breaking strength and crushing strength of bones evidencing use in conjunction with bone replacement surgery such as hip and knee replacements.

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: 5843927 (1998-12-01), DeLuca
patent: 5843928 (1998-12-01), DeLuca et al.
patent: 5877168 (1999-03-01), Miyamoto et al.
patent: 5936133 (1999-08-01), DeLuca et al.
patent: 5945410 (1999-08-01), DeLuca et al.
patent: 6392071 (2002-05-01), DeLuca et al.
patent: 6806262 (2004-10-01), DeLuca et al.
patent: 6846811 (2005-01-01), DeLuca et al.
patent: 6992074 (2006-01-01), DeLuca et al.
patent: 2002/0087015 (2002-07-01), DeLuca et al.
patent: 0184206 (1985-12-01), None
patent: 0078704 (1987-04-01), None
patent: 0387077 (1990-09-01), None
patent: 0480572 (1992-04-01), None
patent: 0474517 (1992-11-01), None
patent: 0516410 (1992-12-01), None
patent: 1524264 (2005-04-01), None
patent: WO90/09991 (1990-09-01), None
patent: WO 01/02221 (2001-06-01), None
Baggiolini et al, “Stereochemical Total Synthesis of 1α,25-Dihydroxycholecalciferol and 1β,25-Dihydroxyerocalciferol”, Journal of Organic Chemistry, 51, pp. 3098-3108, 1986.
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.
Chemical Abstracts, “Chemistry of Synthetic High Polymers”, vol. 110, No. 10, Abstract 110: 82505v, Mar. 6, 1989.
Chemical Abstracts, XP-002066055, vol. 121, No. 21, Nov. 21, 1994.
Fujishima et al, “Synthesis and Biological Activity of 2-Methyl-20-EPI Analogues of 1α,25-Dihydroxyvitamin D3,” Bioorganic & Medicinal Chemistry Letters, 8, pp. 2145-2148, 1998.
Kiegiel et al, “Chemical Conversion of Vitamin D3to its 1,25-Dihydroxy Metabolite”, Tetrahedron Letters, vol. 31, No. 43, pp. 6057-60660, 1991.
Konno et al, “A Novel and Practical Route to A-Ring Enyne Synthon for 1α,25-Dihydroxyvitamin D3Analogs: Synthesis of A-ring Diastereomers of 1α,25-Dihydroxy-Vitamin D3and 2-Methyl-1,25-Dihydroxyvitamin D3,” Bioorganic & Medicinal Chemistry Letters, 8, pp. 151-156, 1998.
Okano et al, “Regulatory Activities of 2β-(3-Hydroxypropoxy)-1α,25-Dihydroxyvitamin D3. A Novel Synthetic Vitamin D3Derivative on Calcium Metabolism”, Biochemical and Biophysical Research Communications, vol. 163, No. 3, pp. 1444-1449, Sep. 29, 1989.
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, Feb. 1990.
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.
Posner et al, “Stereocontrolled Synthesis of a Trihydroxylated A Ring as an Immediate Precursor to 1α,2α,25-Trihydroxyvitamin D3”, Journal of Organic Chemistry, 56, pp. 4339-4341, Apr. 15, 1995.
Sarandeses et al, “Synthesis of 1α,25-Dihydroxy-19-Norprevitamin D3”, Tetrahedron Letters, pp. 5445-5448, Apr. 1992.
Sicinski et al, “New 1α,25-Dihydroxy-19-Norvitamin D3Compounds 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.
Slatopolsky et al, “A New Analog of Calcitriol, 19-Nor-1,25-(OH)2D2Suppresses Parathyroid Hormone Secretion in Uremic Rats in the Absence of Hypercalcemia”, American Journal of Kidney Disorders, 26(5), 832-60, 1995.
Suhara et al, “Synthesis and Biological Evaluation of Novel 2α-Substituted 1α,25-Dihydroxyvitamin D3Analogues,” Biolorganic & Medicinal Chemistry Letters, 10, pp. 1129-1132, Mar. 16, 2000.

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

2-propylidene-19-nor-vitamin D compounds does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with 2-propylidene-19-nor-vitamin D compounds, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and 2-propylidene-19-nor-vitamin D compounds will most certainly appreciate the feedback.

Rate now

     

Profile ID: LFUS-PAI-O-3788609

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