Title:
SALVINORIN DERIVATIVES AS OPIOID RECEPTOR LIGANDS
Document Type and Number:
WIPO Patent Application WO2006031782
Kind Code:
A3
Abstract:
The invention provides compounds of formula (I), that are opioid receptor ligands. The invention also provides pharmaceutical compositions comprising such compounds as well as methods for treating diseases associated with opioid receptor function by administering such compounds to a mammal in need of treatment. The invention also provides a method for isolating intermediate materials useful for obtaining compounds of formula (I).
Inventors:
PRISINZANO THOMAS (US)
Application Number:
PCT/US2005/032505
Publication Date:
August 17, 2006
Filing Date:
September 12, 2005
Export Citation:
Assignee:
UNIV IOWA RES FOUND (US)
PRISINZANO THOMAS (US)
PRISINZANO THOMAS (US)
International Classes:
A61K31/352; A61P29/00; C07D405/14; C07D407/04; C07D413/04; C07D417/04
Domestic Patent References:
| WO2005089745A1 | 2005-09-29 |
Other References:
CHAVKIN, CHARLES ET AL: "Salvinorin A, an active component of the hallucinogenic sage Salvia divinorum is a highly efficacious .kappa.-opioid receptor agonist: Structural and functional considerations", JOURNAL OF PHARMACOLOGY AND EXPERIMENTAL THERAPEUTICS , 308(3), 1197-1203 CODEN: JPETAB; ISSN: 0022-3565, 2004, XP002363038
TIDGEWELL, KEVIN ET AL: "A facile method for the preparation of deuterium labeled salvinorin A: synthesis of [2,2,2-2H3]-salvinorin A", BIOORGANIC & MEDICINAL CHEMISTRY LETTERS , 14(20), 5099-5102 CODEN: BMCLE8; ISSN: 0960-894X, 2004, XP004565440
VALDES, LEANDER J., III ET AL: "Salvinorin C, a new neoclerodane diterpene from a bioactive fraction of the hallucinogenic Mexican mint Salvia divinorum", ORGANIC LETTERS , 3(24), 3935-3937 CODEN: ORLEF7; ISSN: 1523-7060, 2001, XP002363040
DATABASE CA [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; SARMA, A. S. ET AL: "Proton and carbon-13 NMR studies of trans-clerodane diterpenoids and congeners: stereochemical implications and certain correlations with cis-clerodanes", XP002363223, retrieved from STN Database accession no. 1987:50494
KOREEDA M ET AL: "The absolute stereochemistry of salvinorins", CHEMISTRY LETTERS, CHEMICAL SOCIETY OF JAPAN. TOKYO, JP, vol. 11, 1990, pages 2015 - 2018, XP002988061, ISSN: 0366-7022
VALDES J AND BUTLER M ET AL: "Divinorin A, a psychotropic terpenoid, and divinorin B from the hallucinogenic Mexican mint salvia divinorum", JOURNAL OF ORGANIC CHEMISTRY, AMERICAN CHEMICAL SOCIETY, WASHINGTON, DC, US, vol. 49, no. 24, 1984, pages 4716 - 4720, XP002988683, ISSN: 0022-3263
BEGUIN, CECILE ET AL: "Synthesis and in vitro pharmacological evaluation of salvinorin A analogues modified at C(2)", BIOORGANIC & MEDICINAL CHEMISTRY LETTERS , 15(11), 2761-2765 CODEN: BMCLE8; ISSN: 0960-894X, 2005, XP004906891
LEE, DAVID Y. W. ET AL: "Synthesis and in vitro pharmacological studies of new C(2) modified salvinorin A analogues", BIOORGANIC & MEDICINAL CHEMISTRY LETTERS , 15(16), 3744-3747 CODEN: BMCLE8; ISSN: 0960-894X, 2005, XP004985342
HARDING, WAYNE W. ET AL: "Neoclerodane Diterpenes as a Novel Scaffold for .mu. Opioid Receptor Ligands", JOURNAL OF MEDICINAL CHEMISTRY , 48(15), 4765-4771 CODEN: JMCMAR; ISSN: 0022-2623, 2005, XP002363043
HARDING, WAYNE W. ET AL: "Salvinicins A and B, new neoclerodane diterpenes from Salvia divinorum", ORGANIC LETTERS , 7(14), 3017-3020 CODEN: ORLEF7; ISSN: 1523-7060, 2005, XP002363044
MUNRO, THOMAS A. ET AL: "Studies toward the Pharmacophore of Salvinorin A, a Potent .kappa. Opioid Receptor Agonist", JOURNAL OF MEDICINAL CHEMISTRY , 48(2), 345-348 CODEN: JMCMAR; ISSN: 0022-2623, 2005, XP004684844
TIDGEWELL, KEVIN ET AL: "A facile method for the preparation of deuterium labeled salvinorin A: synthesis of [2,2,2-2H3]-salvinorin A", BIOORGANIC & MEDICINAL CHEMISTRY LETTERS , 14(20), 5099-5102 CODEN: BMCLE8; ISSN: 0960-894X, 2004, XP004565440
VALDES, LEANDER J., III ET AL: "Salvinorin C, a new neoclerodane diterpene from a bioactive fraction of the hallucinogenic Mexican mint Salvia divinorum", ORGANIC LETTERS , 3(24), 3935-3937 CODEN: ORLEF7; ISSN: 1523-7060, 2001, XP002363040
DATABASE CA [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; SARMA, A. S. ET AL: "Proton and carbon-13 NMR studies of trans-clerodane diterpenoids and congeners: stereochemical implications and certain correlations with cis-clerodanes", XP002363223, retrieved from STN Database accession no. 1987:50494
KOREEDA M ET AL: "The absolute stereochemistry of salvinorins", CHEMISTRY LETTERS, CHEMICAL SOCIETY OF JAPAN. TOKYO, JP, vol. 11, 1990, pages 2015 - 2018, XP002988061, ISSN: 0366-7022
VALDES J AND BUTLER M ET AL: "Divinorin A, a psychotropic terpenoid, and divinorin B from the hallucinogenic Mexican mint salvia divinorum", JOURNAL OF ORGANIC CHEMISTRY, AMERICAN CHEMICAL SOCIETY, WASHINGTON, DC, US, vol. 49, no. 24, 1984, pages 4716 - 4720, XP002988683, ISSN: 0022-3263
BEGUIN, CECILE ET AL: "Synthesis and in vitro pharmacological evaluation of salvinorin A analogues modified at C(2)", BIOORGANIC & MEDICINAL CHEMISTRY LETTERS , 15(11), 2761-2765 CODEN: BMCLE8; ISSN: 0960-894X, 2005, XP004906891
LEE, DAVID Y. W. ET AL: "Synthesis and in vitro pharmacological studies of new C(2) modified salvinorin A analogues", BIOORGANIC & MEDICINAL CHEMISTRY LETTERS , 15(16), 3744-3747 CODEN: BMCLE8; ISSN: 0960-894X, 2005, XP004985342
HARDING, WAYNE W. ET AL: "Neoclerodane Diterpenes as a Novel Scaffold for .mu. Opioid Receptor Ligands", JOURNAL OF MEDICINAL CHEMISTRY , 48(15), 4765-4771 CODEN: JMCMAR; ISSN: 0022-2623, 2005, XP002363043
HARDING, WAYNE W. ET AL: "Salvinicins A and B, new neoclerodane diterpenes from Salvia divinorum", ORGANIC LETTERS , 7(14), 3017-3020 CODEN: ORLEF7; ISSN: 1523-7060, 2005, XP002363044
MUNRO, THOMAS A. ET AL: "Studies toward the Pharmacophore of Salvinorin A, a Potent .kappa. Opioid Receptor Agonist", JOURNAL OF MEDICINAL CHEMISTRY , 48(2), 345-348 CODEN: JMCMAR; ISSN: 0022-2623, 2005, XP004684844
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