FR2446278A2 - 1-alpha-hydroxy-vitamin=D deriv. preparation - by solvolysis of 1-alpha-hydroxy-cyclo-vitamin=D using carboxylic acid e.g. acetic to give 3 O-acyl cpd. which is hydrolysed or reduced - Google Patents

1-alpha-hydroxy-vitamin=D deriv. preparation - by solvolysis of 1-alpha-hydroxy-cyclo-vitamin=D using carboxylic acid e.g. acetic to give 3 O-acyl cpd. which is hydrolysed or reduced

Info

Publication number
FR2446278A2
FR2446278A2 FR7916805A FR7916805A FR2446278A2 FR 2446278 A2 FR2446278 A2 FR 2446278A2 FR 7916805 A FR7916805 A FR 7916805A FR 7916805 A FR7916805 A FR 7916805A FR 2446278 A2 FR2446278 A2 FR 2446278A2
Authority
FR
France
Prior art keywords
hydroxy
vitamin
1alpha
acyl
solvolysis
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
FR7916805A
Other languages
French (fr)
Other versions
FR2446278B2 (en
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Wisconsin Alumni Research Foundation
Original Assignee
Wisconsin Alumni Research Foundation
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from US05/914,796 external-priority patent/US4195027A/en
Priority claimed from US06/041,079 external-priority patent/US4260549A/en
Application filed by Wisconsin Alumni Research Foundation filed Critical Wisconsin Alumni Research Foundation
Publication of FR2446278A2 publication Critical patent/FR2446278A2/en
Application granted granted Critical
Publication of FR2446278B2 publication Critical patent/FR2446278B2/fr
Granted legal-status Critical Current

Links

Classifications

    • 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
    • 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
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14—The ring being saturated
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2602/00—Systems containing two condensed rings
    • C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
    • C07C2602/14—All rings being cycloaliphatic
    • C07C2602/18—All rings being cycloaliphatic the ring system containing six carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2602/00—Systems containing two condensed rings
    • C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
    • C07C2602/14—All rings being cycloaliphatic
    • C07C2602/24—All rings being cycloaliphatic the ring system containing nine carbon atoms, e.g. perhydroindane

Abstract

Prepn. of a 1alpha-hydroxy-vitamin D of formula (7) or 5,6-trans-1alpha-hydroxy-vitamin D of formula (8) by submitting a 1alpha-hydroxycyclovitamin D of formula (3) to solvolysis in the presence of a low mol.wt.organic carboxylic acid to give a 1alpha-hydroxy-3-0-acyl-vitamin D (5B) and/or 5,6-trans-1alpha-hydroxy-3-0-acylvitamin D (6B) which are hydrolysed to give the desired 3-hydroxycpds(7) and (8): R1,R2,R3 independently = H,F, hydroxy, lower alkyl, lower alkoxy, lower acyl or aromatic acyl, R4 = H or lower alkyl and Z = H, lower alkyl, lower acyl or aromatic acyl). The 1alpha-hydroxy vitamin D derivs. of formulae (7) and (8) have similar activity to the natural 1alpha-hydroxy vitamin D derivs. and are used to treat bone and calcium metabolism disorders such as osteodystrophy, osteomalacia and osteoporosis. Process allows direct solvolysis of (3) without protection of the 1-hydroxy gp. thus avoiding degradation due to protection and deprotection and avoids degradation caused by causing p-toluene sulphonic acid as solvolysis agent. The purer product simpler sepn. of the cis and trans isomers gives improved yields on an industrial scale.
FR7916805A 1978-01-16 1979-06-28 1-alpha-hydroxy-vitamin=D deriv. preparation - by solvolysis of 1-alpha-hydroxy-cyclo-vitamin=D using carboxylic acid e.g. acetic to give 3 O-acyl cpd. which is hydrolysed or reduced Granted FR2446278A2 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US86944878A 1978-01-16 1978-01-16
US05/914,796 US4195027A (en) 1978-01-16 1978-06-12 Process for preparing 1α-hydroxylated compounds
US06/041,079 US4260549A (en) 1979-05-21 1979-05-21 Process for preparing 1α-hydroxylated compounds

Publications (2)

Publication Number Publication Date
FR2446278A2 true FR2446278A2 (en) 1980-08-08
FR2446278B2 FR2446278B2 (en) 1984-04-27

Family

ID=27365843

Family Applications (1)

Application Number Title Priority Date Filing Date
FR7916805A Granted FR2446278A2 (en) 1978-01-16 1979-06-28 1-alpha-hydroxy-vitamin=D deriv. preparation - by solvolysis of 1-alpha-hydroxy-cyclo-vitamin=D using carboxylic acid e.g. acetic to give 3 O-acyl cpd. which is hydrolysed or reduced

Country Status (3)

Country Link
BE (1) BE877356R (en)
FR (1) FR2446278A2 (en)
NL (1) NL188286C (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2545824A1 (en) * 1983-05-09 1984-11-16 Wisconsin Alumni Res Found DERIVATIVE 1A, 25-DIHYDROXYLS OF VITAMIN D2 AND INTERMEDIATE PRODUCTS FOR THEIR PREPARATION AND PHARMACEUTICAL COMPOSITIONS COMPRISING THESE DERIVATIVES

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
PL170447B1 (en) * 1990-09-21 1996-12-31 Lunar Corp Method of obtaining novel 1 alpha-hydroxyvitamin d4 and novel transition and analog compounds
US5763429A (en) * 1993-09-10 1998-06-09 Bone Care International, Inc. Method of treating prostatic diseases using active vitamin D analogues
US6503893B2 (en) 1996-12-30 2003-01-07 Bone Care International, Inc. Method of treating hyperproliferative diseases using active vitamin D analogues
CN1254293A (en) 1997-02-13 2000-05-24 骨疗国际公司 Targeted therapeutic delivery of vitamin D compounds

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
CA1978 *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2545824A1 (en) * 1983-05-09 1984-11-16 Wisconsin Alumni Res Found DERIVATIVE 1A, 25-DIHYDROXYLS OF VITAMIN D2 AND INTERMEDIATE PRODUCTS FOR THEIR PREPARATION AND PHARMACEUTICAL COMPOSITIONS COMPRISING THESE DERIVATIVES

Also Published As

Publication number Publication date
NL7905040A (en) 1980-07-17
FR2446278B2 (en) 1984-04-27
NL188286C (en) 1992-05-18
NL188286B (en) 1991-12-16
BE877356R (en) 1979-10-15

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