Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – 9,10-seco- cyclopentanohydrophenanthrene ring system doai
Reexamination Certificate
2006-08-22
2006-08-22
Pryor, Alton (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
07094776
ABSTRACT:
A method of modifying or altering the structure of a 1α-hydroxylated vitamin D compound to increase its biological activity by altering the conformational equilibrium of the A-ring to favor a chair conformation that presents the 1α-hydroxyl in the axial orientation. This is accomplished by either locking the A-ring chair conformation in a geometry having an axially orientated 1α-hydroxyl, or by the addition of one or more substituents to the A-ring which interact with other substituents in the molecule or on the A-ring to provide a driving force to the A-ring to adopt a chair conformation which presents the 1α-hydroxyl in the axial orientation.
REFERENCES:
patent: 4666634 (1987-05-01), Miyamoto et al.
patent: 5536713 (1996-07-01), Deluca et al.
patent: 5877168 (1999-03-01), Miyamoto et al.
patent: 5945410 (1999-08-01), DeLuca et al.
patent: 6369099 (2002-04-01), DeLuca et al.
patent: 0184206 (1986-06-01), None
patent: 0516410 (1992-12-01), None
patent: 0387077 (1994-01-01), None
patent: WO 9601811 (1996-01-01), None
Katsuhito et al, 6001 Chemical Abstracts, 2β-Substituted Vitamin D Derivatives, vol. 121, No. 21, 1994.
Fujishima et al, Synthesis and Biological Activity of 2-Methyl-20-EPI Analogues of 1α,25-Dihydroxyvitamin D3, Bioorganic & Medicinal Chemistry Letters, vol. 8, No. 16, pp. 2145-2148, Aug. 18, 1998.
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-Dihydroxyvitamin D3and 2-Methyl-1,25-Dihydroxyvitamin D3, Bioorganic & Medicinal Chemistry Letters, vol. 8, No. 2, pp. 151-156, Jan. 20, 1998.
Okamura et al, Vitamin D: Concerning the Relationship Between Molecular Topology and Biological Function, Proc. Nat. Acada, Sci., U.S.A., Oct. 1974, vol. 71, No. 10, pp. 4194-4197.
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.
Posner et al, 2-Fluroalkyl 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, vol. 60, No. 14, pp. 4617-4623, Jul. 14, 1995.
Posner et al, Stereocontrolled Synthesis of a Trihydroxylated A Ring as an Immediate Precursor to 1α,2α,25-Trihydroxyvitamin D3, J. Org. Chem. 56, pp. 4339-4341, Apr. 15, 1991.
Sincinski 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 or Medicinal Chemistry, vol. 41, pp. 4662-4674, Oct. 22, 1998.
Sincinski et al, Synthesis, Conformational Analysis and Biological Activity of the 1α,25-Dihydroxy-10,19-Dihydrovitamin D3Isomers, Bioorganic Chemistry, vol. 22, pp. 150-171, 1994.
Trinh et al, Crystal Structure of 25-Hydroxy-Vitamin D3Monohydrate: A Stereo-chemical Analysis of Vitamin D Molecules, J. Org. Chem., 1977, pp. 393-401.
Trinh et al, Solid-State Conformations of Vitamin D3, J. Org. Chem., vol. 41, No. 21, 1976, pp. 3476-3478.
DeLuca Hector F.
Sicinski Rafal R.
Andrus Sceales Starke & Sawall LLP
Pryor Alton
Wisconsin Alumni Research Foundation
LandOfFree
Method of locking 1α-OH of vitamin D compounds in... does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Method of locking 1α-OH of vitamin D compounds in..., we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Method of locking 1α-OH of vitamin D compounds in... will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-3713741