Title:
USE OF ANATABINE TO TREAT INFLAMMATION AND METHODS OF SYNTHESIZING ANATABINE
Document Type and Number:
WIPO Patent Application WO/2011/119722
Kind Code:
A3
Abstract:
Pharmaceutical compositions comprising an isolated form of anatabine or a salt thereof can be used to treat disorders comprising an inflammatory component, including chronic, low-level inflammation. In another aspect, methods for the synthetic preparation of anatabine involve reacting benzophenoneimine with 3-aminomethyl pyridine to form benzylhydrylidene-pyridin-3-yl-methyl-amine. The benzylhydrylidene-pyridin-3-yl-methyl-amine is treated with a non-nucleophilic base and a dielectrophile, such as cis-1,4-dichloro-2-butene, followed by acidification, then basification, to provide anatabine.
Inventors:
WILLIAMS JONNIE R (US)
PUTHIAPARAMPIL TOM THOMAS (IN)
DAVID THOMAS KANATHKUNN (IN)
RAJU MUPPALA SARVESWARA (US)
PUTHIAPARAMPIL TOM THOMAS (IN)
DAVID THOMAS KANATHKUNN (IN)
RAJU MUPPALA SARVESWARA (US)
Application Number:
PCT/US2011/029613
Publication Date:
December 29, 2011
Filing Date:
March 23, 2011
Export Citation:
Assignee:
ROCK CREEK PHARMACEUTICALS INC (US)
WILLIAMS JONNIE R (US)
PUTHIAPARAMPIL TOM THOMAS (IN)
DAVID THOMAS KANATHKUNN (IN)
RAJU MUPPALA SARVESWARA (US)
WILLIAMS JONNIE R (US)
PUTHIAPARAMPIL TOM THOMAS (IN)
DAVID THOMAS KANATHKUNN (IN)
RAJU MUPPALA SARVESWARA (US)
International Classes:
A61K31/4458; A61P29/00
Domestic Patent References:
| WO1999062531A1 | 1999-12-09 | |||
| WO2010030887A1 | 2010-03-18 | |||
| WO2002076434A2 | 2002-10-03 |
Foreign References:
| EP0567251A1 | 1993-10-27 |
Other References:
SHI FU-DONG ET AL: "Nicotinic attenuation of central nervous system inflammation and autoimmunity.", 1 February 2009, JOURNAL OF IMMUNOLOGY (BALTIMORE, MD. : 1950) 1 FEB 2009 LNKD- PUBMED:19155522, VOL. 182, NR. 3, PAGE(S) 1730 - 1739, ISSN: 1550-6606, XP002647118
DENTON TRAVIS T ET AL: "Nicotine-related alkaloids and metabolites as inhibitors of human cytochrome P-450 2A6.", 15 February 2004, BIOCHEMICAL PHARMACOLOGY 15 FEB 2004 LNKD- PUBMED:14757175, VOL. 67, NR. 4, PAGE(S) 751 - 756, ISSN: 0006-2952, XP002647119
BRASIER ALLAN R: "The NF-kappaB regulatory network.", 2006, CARDIOVASCULAR TOXICOLOGY 2006 LNKD- PUBMED:17303919, VOL. 6, NR. 2, PAGE(S) 111 - 130, ISSN: 1530-7905, XP002647120
FELPIN F -X ET AL: "Total synthesis of (S)-anabasine and (S)-anatabine", 2000, SYNLETT 2000 DE, NR. 11, PAGE(S) 1646 - 1648, ISSN: 0936-5214, XP002647121
FELPIN F X ET AL: "Efficient enantiomeric synthesis of pyrrolidine and piperidine alkaloids from tobacco.", 21 September 2001, THE JOURNAL OF ORGANIC CHEMISTRY 21 SEP 2001 LNKD- PUBMED:11559179, VOL. 66, NR. 19, PAGE(S) 6305 - 6312, ISSN: 0022-3263, XP002647122
AYERS JOSHUA T ET AL: "A general procedure for the enantioselective synthesis of the minor tobacco alkaloids nornicotine, anabasine, and anatabine.", 2005, THE AAPS JOURNAL 2005 LNKD- PUBMED:16353951, VOL. 7, NR. 3, PAGE(S) E752 - E758, ISSN: 1550-7416, XP002647123
DENTON TRAVIS T ET AL: "Nicotine-related alkaloids and metabolites as inhibitors of human cytochrome P-450 2A6.", 15 February 2004, BIOCHEMICAL PHARMACOLOGY 15 FEB 2004 LNKD- PUBMED:14757175, VOL. 67, NR. 4, PAGE(S) 751 - 756, ISSN: 0006-2952, XP002647119
BRASIER ALLAN R: "The NF-kappaB regulatory network.", 2006, CARDIOVASCULAR TOXICOLOGY 2006 LNKD- PUBMED:17303919, VOL. 6, NR. 2, PAGE(S) 111 - 130, ISSN: 1530-7905, XP002647120
FELPIN F -X ET AL: "Total synthesis of (S)-anabasine and (S)-anatabine", 2000, SYNLETT 2000 DE, NR. 11, PAGE(S) 1646 - 1648, ISSN: 0936-5214, XP002647121
FELPIN F X ET AL: "Efficient enantiomeric synthesis of pyrrolidine and piperidine alkaloids from tobacco.", 21 September 2001, THE JOURNAL OF ORGANIC CHEMISTRY 21 SEP 2001 LNKD- PUBMED:11559179, VOL. 66, NR. 19, PAGE(S) 6305 - 6312, ISSN: 0022-3263, XP002647122
AYERS JOSHUA T ET AL: "A general procedure for the enantioselective synthesis of the minor tobacco alkaloids nornicotine, anabasine, and anatabine.", 2005, THE AAPS JOURNAL 2005 LNKD- PUBMED:16353951, VOL. 7, NR. 3, PAGE(S) E752 - E758, ISSN: 1550-7416, XP002647123
Attorney, Agent or Firm:
RIVARD, Paul M. (1100 13th Street NW,Suite 120, Washington District of Columbia, US)
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