Organic compounds -- part of the class 532-570 series – Organic compounds – Azides
Patent
1998-10-20
2000-01-11
Shah, Mukund J.
Organic compounds -- part of the class 532-570 series
Organic compounds
Azides
552 4, 514 63, 514151, 5142362, 514319, 514359, 544132, 546 14, 546205, 548255, C07C40100, C07D24904, A61K 3141, A61K 31655
Patent
active
060138149
ABSTRACT:
The present invention relates to novel 1.alpha.-hydroxy vitamin D derivatives in which the 17-position side chain carries an azide or optionally substituted 1,2,3-triazole group, including compounds of general formula (I) where R.sup.1 represents a methyl group having .alpha.- or .beta.-configuration; W represents a valence bond or a C.sub.1-5 alkylene group; X represents azide or an optionally substituted triazole group; and A.dbd. represents a cyclohexylidene moiety characteristic of the A-ring of a 1.alpha.-hydroxylated vitamin D or analogue thereof. Active compounds of the invention exhibit cell modulating activity while exhibiting a substantial lack of calcaemic effect.
REFERENCES:
patent: 4772433 (1988-09-01), Hesse
patent: 5446635 (1995-08-01), Herf et al.
Rahul et al., Chemical Abstracts, vol. 103, No. 19, abstract No. 160 275s, Nov. 1985.
Perlman et al., 1-alpha-Hydroxy-19-Nor-Vitamin D C-22 Aldehyde. A Valuable Intermediate in the Synthesis of side Chain Modified 1-alpha,25-Dihydroxy-19-Nor-Vitamine D3, Tetrahedron Letters, vol. 33, No. 21, pp. 2937-2940, May 1992.
Calverley, Synthesis of MC 903, A Biologically Active Vitamin D Metabolite Analogue, Tetrahedron Letters, vol. 43, No. 17, pp. 4609-4619, 1987.
Cram and Hammond, "Organic Chemistry", McGraw-Hill Book Co., NY, 2nd Ed pp. 565-567, 1964.
Hesse Robert Henry
Ramgopal Malathi
Reddy Gaddam Subba
Setty Sundara Katugam Srinivasasetty
Coleman Brenda
Research Institute for Medicine and Chemistry, Inc.
Shah Mukund J.
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