WO2006074227A3 - HIGHLY ANTIPROLIFERATIVE, LOW-CALCEMIC, ANALOGS OF THE HORMONE 1α, 25-DIHYDROXYVITAMIN D3 WITH CARBONYL SIDE CHAINS - Google Patents

HIGHLY ANTIPROLIFERATIVE, LOW-CALCEMIC, ANALOGS OF THE HORMONE 1α, 25-DIHYDROXYVITAMIN D3 WITH CARBONYL SIDE CHAINS Download PDF

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Publication number
WO2006074227A3
WO2006074227A3 PCT/US2006/000183 US2006000183W WO2006074227A3 WO 2006074227 A3 WO2006074227 A3 WO 2006074227A3 US 2006000183 W US2006000183 W US 2006000183W WO 2006074227 A3 WO2006074227 A3 WO 2006074227A3
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WO
WIPO (PCT)
Prior art keywords
antiproliferative
hormone
calcitriol
calcemic
analogs
Prior art date
Application number
PCT/US2006/000183
Other languages
French (fr)
Other versions
WO2006074227A2 (en
Inventor
Gary H Posner
Sandra Sinishtaj
Byung Chul Suh
Hyung Jin Kim
S H Tony Lee
Zhiyu Zhang
Heung Bae Jeon
Mehmet Kahraman
Hongbin Li
Kimberly Petersen
Original Assignee
Univ Johns Hopkins
Gary H Posner
Sandra Sinishtaj
Byung Chul Suh
Hyung Jin Kim
S H Tony Lee
Zhiyu Zhang
Heung Bae Jeon
Mehmet Kahraman
Hongbin Li
Kimberly Petersen
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
Application filed by Univ Johns Hopkins, Gary H Posner, Sandra Sinishtaj, Byung Chul Suh, Hyung Jin Kim, S H Tony Lee, Zhiyu Zhang, Heung Bae Jeon, Mehmet Kahraman, Hongbin Li, Kimberly Petersen filed Critical Univ Johns Hopkins
Publication of WO2006074227A2 publication Critical patent/WO2006074227A2/en
Publication of WO2006074227A3 publication Critical patent/WO2006074227A3/en

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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

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The present invention discloses a series of new carbonyl side chain anlogs of calcitriol (I). Unexpectedly, several of these ketone analogs, such as the 24- and 25-tert-butyl ketones, amides, hydroxymate esters and a hetero atom ketones even though lacking the classical side-chain tertiary hydroxyl group, are considerably more antiproliferative in vitro than the hormone calcitriol (I) even at physiologically relevant low nanomolar concentrations and are less calcemic than calcitriol (I) in vivo.
PCT/US2006/000183 2005-01-04 2006-01-03 HIGHLY ANTIPROLIFERATIVE, LOW-CALCEMIC, ANALOGS OF THE HORMONE 1α, 25-DIHYDROXYVITAMIN D3 WITH CARBONYL SIDE CHAINS WO2006074227A2 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US64134005P 2005-01-04 2005-01-04
US60/641,340 2005-01-04

Publications (2)

Publication Number Publication Date
WO2006074227A2 WO2006074227A2 (en) 2006-07-13
WO2006074227A3 true WO2006074227A3 (en) 2006-09-28

Family

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Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2006/000183 WO2006074227A2 (en) 2005-01-04 2006-01-03 HIGHLY ANTIPROLIFERATIVE, LOW-CALCEMIC, ANALOGS OF THE HORMONE 1α, 25-DIHYDROXYVITAMIN D3 WITH CARBONYL SIDE CHAINS

Country Status (1)

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WO (1) WO2006074227A2 (en)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU2008242711A1 (en) 2007-04-18 2008-10-30 Johns Hopkins University Low calcemic, highly antiproliferative, analogs of calcitriol
ES2396524B2 (en) 2012-12-11 2013-08-01 Universidade De Santiago De Compostela Versatile and functionalized intermediates in the synthesis of vitamin D and new vitamin D derivatives
WO2022059684A1 (en) * 2020-09-15 2022-03-24 帝人ファーマ株式会社 Vitamin d derivative having cyclic amine in side chain
PT117825A (en) * 2022-02-28 2023-09-20 Univ Santiago Compostela SILA-ANALOGS OF VITAMIN D, METHOD OF PRODUCTION OF SAID COMPOUNDS, USES THEREOF AND PHARMACEUTICAL COMPOSITION COMPRISING THE COMPOUNDS
TW202400184A (en) * 2022-03-11 2024-01-01 日商帝人製藥股份有限公司 Medicine containing vitamin d derivative or pharmaceutically acceptable salt or solvate thereof, used in combination with immunomodulatory substance

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5403832A (en) * 1992-03-12 1995-04-04 The Johns Hopkins University Vitamin D3 analogues
US5830885A (en) * 1992-03-12 1998-11-03 The Johns Hopkins University Antiproliferative vitamin D3 hybrids
US6380408B1 (en) * 1999-04-01 2002-04-30 The Johns Hopkins University Non-calcemic, antiproliferative, transcriptionally active sulfur-containing analogs of 1α, 25-dihydroxy vitamin D3
US6982258B2 (en) * 2001-10-12 2006-01-03 Cytochroma Inc. Low-calcemic oxime analogs of 1α,25-dihydroxy vitamin D3

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5403832A (en) * 1992-03-12 1995-04-04 The Johns Hopkins University Vitamin D3 analogues
US5830885A (en) * 1992-03-12 1998-11-03 The Johns Hopkins University Antiproliferative vitamin D3 hybrids
US6380408B1 (en) * 1999-04-01 2002-04-30 The Johns Hopkins University Non-calcemic, antiproliferative, transcriptionally active sulfur-containing analogs of 1α, 25-dihydroxy vitamin D3
US6982258B2 (en) * 2001-10-12 2006-01-03 Cytochroma Inc. Low-calcemic oxime analogs of 1α,25-dihydroxy vitamin D3

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Publication number Publication date
WO2006074227A2 (en) 2006-07-13

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