[go: up one dir, main page]

Hatcher et al., 2005 - Google Patents

A-ring hydroxymethyl 19-nor analogs of the natural hormone 1α, 25-dihydroxyvitamin D3: Synthesis and preliminary biological evaluation

Hatcher et al., 2005

Document ID
3374724823145558792
Author
Hatcher M
Peleg S
Dolan P
Kensler T
Sarjeant A
Posner G
Publication year
Publication venue
Bioorganic & medicinal chemistry

External Links

Snippet

A series 5–8 of 1-and 3-CH2OH 19-nor analogs of the hormone calcitriol (1) has been prepared. Surprisingly, 19-nor 1α-CH2OH analog 5a is more antiproliferative at 100nM concentration than the corresponding regioisomeric analog 6a with the natural 1α-OH …
Continue reading at www.sciencedirect.com (other versions)

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J71/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton is condensed with a heterocyclic ring
    • C07J71/0036—Nitrogen-containing hetero ring
    • C07J71/0042—Nitrogen only
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C401/00—Irradiation products of cholesterol or its derivatives; Vitamin D derivatives, 9,10-seco cyclopenta[a]phenanthrene or analogues obtained by chemical preparation without irradiation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J71/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton is condensed with a heterocyclic ring
    • C07J71/0005—Oxygen-containing hetero ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic System
    • C07F9/02—Phosphorus compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2101/00—Systems containing only non-condensed rings
    • C07C2101/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2101/16—The ring being unsaturated
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2102/00—Systems containing two condensed rings
    • C07C2102/02—The rings having only two atoms in common
    • C07C2102/14—All rings being cycloaliphatic
    • C07C2102/24—The ring system contains nine carbon atoms (e.g. perhydroindane)
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J31/00—Normal steroids containing one or more sulfur atoms not belonging to a hetero ring
    • C07J31/006—Normal steroids containing one or more sulfur atoms not belonging to a hetero ring not covered by C07J31/003
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C35/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring
    • C07C35/21—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring polycyclic, at least one hydroxy group bound to a non-condensed ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J9/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of more than two carbon atoms, e.g. cholane, cholestane, coprostane
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J13/00—Normal steroids containing carbon, hydrogen, halogen or oxygen having a carbon-to-carbon double bond from or to position 17
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J1/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, not substituted in position 17 beta by a carbon atom, e.g. estrane, androstane
    • C07J1/0003—Androstane derivatives
    • C07J1/0018—Androstane derivatives substituted in position 17 beta, not substituted in position 17 alfa
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O-metal, -CHO, keto, ether, groups, groups, or groups
    • C07C59/40—Unsaturated compounds
    • C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides

Similar Documents

Publication Publication Date Title
US4851401A (en) Novel cyclopentano-vitamin D analogs
US5260290A (en) Homologated vitamin D2 compounds and the corresponding 1α-hydroxylated derivatives
EP1180035B1 (en) NON-CALCEMIC, ANTIPROLIFERATIVE, TRANSCRIPTIONALLY ACTIVE SULFUR-CONTAINING ANALOGS OF 1-alpha, 25-DIHYDROXY VITAMIN D3
HU215604B (en) Process for producing biologically effective 19-nor-d vitamin compounds and pharmaceutical compositions comprising such compounds
GB2127023A (en) Synthesis of 25-hydroxyvitamin d2 and related compounds
US4769181A (en) 1,25-dihydroxyvitamin D2 compounds
CZ284926B6 (en) Derivatives of 25-carboxylic acid in a series of d vitamin, pharmaceutical preparations in which the derivatives are comprised as well as their use in the preparation of medicaments
JP2731839B2 (en) Homogenized Vitamin D <2> compounds and corresponding 1α-hydroxylated derivatives
JPH10509715A (en) 18,19-dinor-vitamin D compounds
US5830885A (en) Antiproliferative vitamin D3 hybrids
US5403832A (en) Vitamin D3 analogues
US20040224930A1 (en) 25-SO2-Substituted analogs of 1mu,25-dihydroxyvitamin D3
AU629831B2 (en) Side chain unsaturated 1 alpha-hydroxyvitamin d homologs for the treatment of leukemia
Hatcher et al. A-ring hydroxymethyl 19-nor analogs of the natural hormone 1α, 25-dihydroxyvitamin D3: Synthesis and preliminary biological evaluation
US5354744A (en) Side chain unsaturated 1 alpha-hydroxyvitamin D analogs
AU4320999A (en) Method for making hydroxy-25-ene-vitamin d compounds
CA2619311A1 (en) Synthesis of 1.alpha.-fluoro-25-hydroxy-16-23e-diene-26,27-bishomo-20-epi-cholecalciferol
Grzywacz et al. Methyl substitution of the 25-hydroxy group on 2-methylene-19-nor-1α, 25-dihydroxyvitamin D3 (2MD) reduces potency but allows bone selectivity
Posner et al. Highly antiproliferative, low-calcemic, side-chain ketone analogs of the hormone 1α, 25-dihydroxyvitamin D3
NO972257L (en) 18-nor-vitamin D compounds
WO1996030338A1 (en) 1-substituted vitamin d3 analogues
Posner et al. Antiproliferative vitamin D 3 hybrids
EP0468037A1 (en) Process for preparing vitamin d2 compounds and the corresponding 1 alpha-hydroxylated derivatives.
Posner et al. Vitamin D 3 analogues
WO1985003299A1 (en) Side-chain unsaturated 1-hydroxyvitamin d compounds