US 2012/0258938 A1 · Enzymatic Production or Chemical Synthesis and Uses for 5,7-Dienes and UVB Conversion Products Thereof

Abstract

Provided herein are steroidal compounds that are androsta-5,7-dienes or pregna-5,7-dienes and ultraviolet B (UVB) conversion products thereof and cholecalciferol derivatives hydroxylated at one or more of C1, C17, C20, C23, C24, C25, and C26 which includes pharmaceutical, cosmeceutical or nutraceutical compositions of the steroidal compounds as shown in Tables 1A, 2A and 3. Also provided is a method for producing hydroxylated metabolites of cholecalciferol via CYP11A1, CYP24, CYP27A1, or CYP27B1 enzyme systems where the hydroxylase has an activity to hydroxylate position C1 or C20 or other position of the sidechain of a secosteroid or its 5,7-dieneal precursor and the hydroxylated metabolites so produced. Methods are provided for inhibiting proliferation of either a normally or abnormally proliferating cell, for modifying immune activity, or for treating a condition associated with the proliferating or quiescent cell or immune cells by contacting the cell with or administering any of the compounds described herein.

Claims30

Dependent claims

A hydroxylated derivative or analog of cholecalciferol having at least one carbon of a C17 sidechain thereof hydroxylated.

A derivative or analog compound of cholecalciferol that is:

(5Z,7E)-9,10-secocholesta-5,7,10(19)-triene-3β,20-diol,
(5Z,7E)-9,10-secocholesta-5,7,10(19)-triene-3β,20R-diol,
(5Z,7E)-9,10-secocholesta-5,7,10(19)-triene-3β,20S-diol,
(5Z,7E)-9,10-secocholesta-5,7,10(19)-triene-3β,20,23-triol,
(5Z,7E)-9,10-secocholesta-5,7,10(19)-triene-3β,20R,23-triol,
(5Z,7E)-9,10-secocholesta-5,7,10(19)-triene-3β,20S,23-triol,
(5Z,7E)-9,10-secocholesta-5,7,10(19)-triene-3β,20,24-triol,
(5Z,7E)-9,10-secocholesta-5,7,10(19)-triene-3β,20R,24-triol,
(5Z,7E)-9,10-secocholesta-5,7,10(19)-triene-3β,20S,24-triol,
(5Z,7E)-9,10-secocholesta-5,7,10(19)-triene-3β,20,25-triol,
(5Z,7E)-9,10-secocholesta-5,7,10(19)-triene-3β,20R,25-triol,
(5Z,7E)-9,10-secocholesta-5,7,10(19)-triene-3β,20S,25-triol,
(5Z,7E)-9,10-secocholesta-5,7,10(19)-triene-3β,20,26-triol,
(5Z,7E)-9,10-secocholesta-5,7,10(19)-triene-3β,20R,26-triol,
(5Z,7E)-9,10-secocholesta-5,7,10(19)-triene-3β,20S,26-triol,
5Z,7E)-9,10-secocholesta-5,7,10(19)-triene-3β,20,23,24-tetrol,
(5Z,7E)-9,10-secocholesta-5,7,10(19)-triene-3β,20R,23,24-tetrol,
(5Z,7E)-9,10-secocholesta-5,7,10(19)-triene-3β,20R,23,24-tetrol,
(5Z,7E)-9,10-secocholesta-5,7,10(19)-triene-3β,20,23,25-tetrol,
(5Z,7E)-9,10-secocholesta-5,7,10(19)-triene-3β,20R,23,25-tetrol,
(5Z,7E)-9,10-secocholesta-5,7,10(19)-triene-3β,20S,23,25-tetrol,
(5Z,7E)-9,10-secocholesta-5,7,10(19)-triene-3β,20,23,26-tetrol,
(5Z,7E)-9,10-secocholesta-5,7,10(19)-triene-3β,20R,23,26-tetrol,
(5Z,7E)-9,10-secocholesta-5,7,10(19)-triene-3β,20S,23,26-tetrol,
(5Z,7E)-9,10-secocholesta-5,7,10(19)-triene-1α,3β,20,23-tetrol,
(5Z,7E)-9,10-secocholesta-5,7,10(19)-triene-1α,3β,20R,23-tetrol,
(5Z,7E)-9,10-secocholesta-5,7,10(19)-triene-1α,3β,20S,23-tetrol,
(5Z,7E)-9,10-secocholesta-5,7,10(19)-triene-1α,3β,20,24-tetrol,
(5Z,7E)-9,10-secocholesta-5,7,10(19)-triene-1α,3β,20R,24-tetrol,
(5Z,7E)-9,10-secocholesta-5,7,10(19)-triene-1α,3β,20S,24-tetrol,
(5Z,7E)-9,10-secocholesta-5,7,10(19)-triene-1α,3β,20,26-tetrol,
(5Z,7E)-9,10-secocholesta-5,7,10(19)-triene-1α,3β,20R,26-tetrol,
(5Z,7E)-9,10-secocholesta-5,7,10(19)-triene-1α,3β,20S,26-tetrol,
(5Z,7E)-9,10-secocholesta-5,7,10(19)-triene-1α,3β,17α,20,23-tetrol,
5Z,7E)-9,10-secocholesta-5,7,10(19)-triene-1α,3β,17α,20R,23-tetrol,
(5Z,7E)-9,10-secocholesta-5,7,10(19)-triene-1α,3β,17α,20S,23-tetrol,
(5Z,7E)-9,10-secocholesta-5,7,10(19)-triene-1α,3β,17α,20,24-tetrol,
5Z,7E)-9,10-secocholesta-5,7,10(19)-triene-1α,3β,17α,20R,24-tetrol,
(5Z,7E)-9,10-secocholesta-5,7,10(19)-triene-1α,3β,17α,20S,24-tetrol,
(5Z,7E)-9,10-secocholesta-5,7,10(19)-triene-1α,3β,17α,20,25-tetrol,
5Z,7E)-9,10-secocholesta-5,7,10(19)-triene-1α,3β,17α,20R,25-tetrol,
(5Z,7E)-9,10-secocholesta-5,7,10(19)-triene-1α,3β,17α,20S,25-tetrol,
(5Z,7E)-9,10-secocholesta-5,7,10(19)-triene-1α,3β,17α,20,26-tetrol,
5Z,7E)-9,10-secocholesta-5,7,10(19)-triene-1α,3β,17α,20R,26-tetrol,
(5Z,7E)-9,10-secocholesta-5,7,10(19)-triene-1α,3β,17α,20S,26-tetrol, or
a tachysterol or a lumisterol analog thereof.

43 more elements

Dependencies are inferred from the claim text.

Facts

Application

13/460,375Filed 30 Apr 2012

Priority

28 Feb 2008

Published

11 Oct 2012

Term ends

Not estimatedThe source records don’t support an estimate.

Classification19 codes

C07J 3/00
Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17
A61P 1/00
Drugs for disorders of the alimentary tract or the digestive system
A61P 3/04
Drugs for disorders of the metabolism: anorexiants; Antiobesity agents
A61P 3/10
For glucose homeostasis: for hyperglycaemia, e.g. antidiabetics

Family

Application61/067,461Us provisional application · filed 28 Feb 2008

Application61/189,798Us provisional application · filed 22 Aug 2008

Application12/807,178Continuation in part · filed 30 Aug 2010

Application13/460,375Continuation in part

US 2011/0118228 A1Published application

US 2012/0258938 A1This patent

From the US filing history. Foreign family members aren’t listed.

Enzymatic Production or Chemical Synthesis and Uses for 5,7-Dienes and UVB Conversion Products Thereof

Life of this patent

Enzymatic Production or Chemical Synthesis and Uses for 5,7-Dienes and UVB Conversion Products Thereof

Life of this patent

Abstract

Claims30