Title:
ANALOGS OF GERANYLGERANYLACETONE AND USES THEREOF
Document Type and Number:
WIPO Patent Application WO/2012/026813
Kind Code:
A3
Abstract:
The invention relates to novel therapeutic compounds, more in particular to biologically active analogs of geranylgeranylacetone (GGA), and various use thereof. Provided is a compound of the general formula (II) and uses thereof as medicament, for instance for the treatment of atrial fibrillation.
Inventors:
BRUNDEL BIANCA JOHANNA JOSEPHINA MARIA (NL)
STEEN HERMANNUS (NL)
HEERES ANDRE (NL)
BORST MARK (NL)
STEEN HERMANNUS (NL)
HEERES ANDRE (NL)
BORST MARK (NL)
Application Number:
PCT/NL2011/050576
Publication Date:
May 31, 2012
Filing Date:
August 25, 2011
Export Citation:
Assignee:
NYKEN HOLDING B V (NL)
BRUNDEL BIANCA JOHANNA JOSEPHINA MARIA (NL)
STEEN HERMANNUS (NL)
HEERES ANDRE (NL)
BORST MARK (NL)
BRUNDEL BIANCA JOHANNA JOSEPHINA MARIA (NL)
STEEN HERMANNUS (NL)
HEERES ANDRE (NL)
BORST MARK (NL)
International Classes:
C07C45/71; A61K31/10; A61K31/121; A61K31/15; C07C49/203; C07C49/217; C07C49/227; C07C251/36; C07C251/38; C07C317/08
Domestic Patent References:
| WO2006062402A2 | 2006-06-15 |
Foreign References:
| EP1609777A1 | 2005-12-28 | |||
| US4169157A | 1979-09-25 | |||
| EP2423177A1 | 2012-02-29 |
Other References:
DOLENCE J M ET AL: "Synthesis of Analogs of Farnesyl Diphosphate", TETRAHEDRON, ELSEVIER SCIENCE PUBLISHERS, AMSTERDAM, NL, vol. 52, no. 1, 1 January 1996 (1996-01-01), pages 119 - 130, XP004104589, ISSN: 0040-4020, DOI: DOI:10.1016/0040-4020(95)00909-R
CAMPS F ET AL: "Trifluoromethyl Analogs of Juvenile Hormones", TETRAHEDRON, ELSEVIER SCIENCE PUBLISHERS, AMSTERDAM, NL, vol. 34, 1 January 1978 (1978-01-01), pages 2179 - 2182, XP007916988, ISSN: 0040-4020
KEIJI MARUOKA ET AL: "Stabilization of Reactive Aldehydes by Complexation with Methylaluminum Bis( 2,6-diphenylphenoxide) and Their Synthetic Application", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, AMERICAN CHEMICAL SOCIETY, US, vol. 115, 1 January 1993 (1993-01-01), pages 3943 - 3949, XP007916989, ISSN: 0002-7863
PREPARATION OF: "Preparation of Modified Squalenes", JOURNAL OF THE CHEMICAL SOCIETY, CHEMICAL SOCIETY, LETCHWORTH; GB, vol. 77, 20 November 1955 (1955-11-20), pages 6073 - 6075, XP007916990, ISSN: 0368-1769
HUNT C ET AL: "The Photochemistry of 7,11-Dimethyldodeca-1,6,10-Trien-3-One", TETRAHEDRON, ELSEVIER SCIENCE PUBLISHERS, AMSTERDAM, NL, vol. 27, 1 January 1971 (1971-01-01), pages 1491 - 1497, XP007916991, ISSN: 0040-4020
GIANFRANCO PALA ET AL: "Terpene Compounds as Drugs. III. Terpenylketoximes", JOURNAL OF MEDICINAL CHEMISTRY, AMERICAN CHEMICAL SOCIETY, WASHINGTON, US, vol. 10, no. 5, 1 September 1967 (1967-09-01), pages 980, XP007916992, ISSN: 0022-2623, DOI: DOI:10.1021/JM00317A066
WEI-DONG Z. LI ET AL: "An Effective and Highly Stereoselective Julia Olefination of Cyclopropyl Carbinol Mediated by CeCl 3 .7H 2 O/NaI", ORGANIC LETTERS, vol. 7, no. 14, 1 July 2005 (2005-07-01), pages 3069 - 3072, XP055023251, ISSN: 1523-7060, DOI: 10.1021/ol051051+
SHIMIZU I ET AL: "FACILE SYNTHESIS OF TRIFLUOROMETHYL KETONES BY PALLADIUM-CATALYZED CARROLL TYPE REACTION", CHEMISTRY LETTERS, CHEMICAL SOCIETY OF JAPAN, JP, no. 7, 1 January 1989 (1989-01-01), XP000037360, ISSN: 0366-7022, DOI: 10.1246/CL.1989.1127
K MORI: "Synthesis of compounds with juvenile hormone activity-XII A stereoselective sunthesis of 6-ethyl-10-methyldodeca-5-trans, 9-cis-dien-2-one, a key intermediate in the synthesis of C18-Cecropia juvenile hormone", TETRAHEDRON, vol. 28, no. 14, 1 January 1972 (1972-01-01), pages 3747 - 3756, XP055023229, ISSN: 0040-4020, DOI: 10.1016/S0040-4020(01)93821-9
MASARU KOBAYASHI ET AL: "Stereochemical course of the transannular cyclization, in chloroform, of epoxycembranoids derived from the geometrical isomers of (14S)-14-hydroxy-1,3,7,11-cembratetraenes", THE JOURNAL OF ORGANIC CHEMISTRY, vol. 55, no. 6, 1 March 1990 (1990-03-01), pages 1947 - 1951, XP055023230, ISSN: 0022-3263, DOI: 10.1021/jo00293a049
OH S ET AL: "Synthesis of two marine farnesylacetones that dilate the basilar arteries of rabbits", BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, PERGAMON, ELSEVIER SCIENCE, GB, vol. 20, no. 14, 15 July 2010 (2010-07-15), pages 4206 - 4209, XP027104019, ISSN: 0960-894X, [retrieved on 20100519]
ITSUMARO KUMADAKI ET AL: "Synthesis of fluorine analogues of vitamin E.", CHEMICAL & PHARMACEUTICAL BULLETIN, vol. 36, no. 2, 1 January 1988 (1988-01-01), pages 515 - 520, XP055023351, ISSN: 0009-2363, DOI: 10.1248/cpb.36.515
MANABU MURAKAMI, KIYOSHI OKETANI, HIDEAKI FUJISAKI,TSUNEO WAKABAYASHI, YUICHI INAI, SHINYA ABE,ISAO YAMATSU AND TOSHIHARU OHGO: "EFFECT OF SYNTHETIC ACYCLIC POLYISOPRENOIDS ON THECOLD-RESTRAINT STRESS INDUCED GASTRIC ULCER IN RATS", JAPAN. J. PHARMACOL., vol. 33, 1 January 1983 (1983-01-01), pages 549 - 556, XP002672625
DATABASE Reaxys [online] Elsevier Properties SA; 28 March 2012 (2012-03-28), "6,10-dimethyl-undeca-5,9-dien-2-one O-methyl-oxime", XP002672465, retrieved from www.reaxys.com Database accession no. 6695244
BIANCA J J M BRUNDEL ET AL: "Induction of Heat Shock Response Protects the Heart Against Atrial Fibrillation", CIRCULATION RESEARCH, GRUNE AND STRATTON, BALTIMORE, US, vol. 99, 10 January 2006 (2006-01-10), pages 1394 - 1402, XP007916993, ISSN: 0009-7330, [retrieved on 20061116], DOI: DOI:10.1161/01.RES.0000252323.83137.FE
MASAO SAKABE1 ET AL: "Effects of a heat shock protein inducer on the atrial fibrillation substrate caused by acute atrial ischaemia", CARDIOVASCULAR RESEARCH, OXFORD UNIVERSITY PRESS, GB, vol. 78, 1 January 2008 (2008-01-01), pages 63 - 70, XP007916994, ISSN: 0008-6363, [retrieved on 20080131], DOI: DOI:10.1093/CVR/CVN019
CAMPS F ET AL: "Trifluoromethyl Analogs of Juvenile Hormones", TETRAHEDRON, ELSEVIER SCIENCE PUBLISHERS, AMSTERDAM, NL, vol. 34, 1 January 1978 (1978-01-01), pages 2179 - 2182, XP007916988, ISSN: 0040-4020
KEIJI MARUOKA ET AL: "Stabilization of Reactive Aldehydes by Complexation with Methylaluminum Bis( 2,6-diphenylphenoxide) and Their Synthetic Application", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, AMERICAN CHEMICAL SOCIETY, US, vol. 115, 1 January 1993 (1993-01-01), pages 3943 - 3949, XP007916989, ISSN: 0002-7863
PREPARATION OF: "Preparation of Modified Squalenes", JOURNAL OF THE CHEMICAL SOCIETY, CHEMICAL SOCIETY, LETCHWORTH; GB, vol. 77, 20 November 1955 (1955-11-20), pages 6073 - 6075, XP007916990, ISSN: 0368-1769
HUNT C ET AL: "The Photochemistry of 7,11-Dimethyldodeca-1,6,10-Trien-3-One", TETRAHEDRON, ELSEVIER SCIENCE PUBLISHERS, AMSTERDAM, NL, vol. 27, 1 January 1971 (1971-01-01), pages 1491 - 1497, XP007916991, ISSN: 0040-4020
GIANFRANCO PALA ET AL: "Terpene Compounds as Drugs. III. Terpenylketoximes", JOURNAL OF MEDICINAL CHEMISTRY, AMERICAN CHEMICAL SOCIETY, WASHINGTON, US, vol. 10, no. 5, 1 September 1967 (1967-09-01), pages 980, XP007916992, ISSN: 0022-2623, DOI: DOI:10.1021/JM00317A066
WEI-DONG Z. LI ET AL: "An Effective and Highly Stereoselective Julia Olefination of Cyclopropyl Carbinol Mediated by CeCl 3 .7H 2 O/NaI", ORGANIC LETTERS, vol. 7, no. 14, 1 July 2005 (2005-07-01), pages 3069 - 3072, XP055023251, ISSN: 1523-7060, DOI: 10.1021/ol051051+
SHIMIZU I ET AL: "FACILE SYNTHESIS OF TRIFLUOROMETHYL KETONES BY PALLADIUM-CATALYZED CARROLL TYPE REACTION", CHEMISTRY LETTERS, CHEMICAL SOCIETY OF JAPAN, JP, no. 7, 1 January 1989 (1989-01-01), XP000037360, ISSN: 0366-7022, DOI: 10.1246/CL.1989.1127
K MORI: "Synthesis of compounds with juvenile hormone activity-XII A stereoselective sunthesis of 6-ethyl-10-methyldodeca-5-trans, 9-cis-dien-2-one, a key intermediate in the synthesis of C18-Cecropia juvenile hormone", TETRAHEDRON, vol. 28, no. 14, 1 January 1972 (1972-01-01), pages 3747 - 3756, XP055023229, ISSN: 0040-4020, DOI: 10.1016/S0040-4020(01)93821-9
MASARU KOBAYASHI ET AL: "Stereochemical course of the transannular cyclization, in chloroform, of epoxycembranoids derived from the geometrical isomers of (14S)-14-hydroxy-1,3,7,11-cembratetraenes", THE JOURNAL OF ORGANIC CHEMISTRY, vol. 55, no. 6, 1 March 1990 (1990-03-01), pages 1947 - 1951, XP055023230, ISSN: 0022-3263, DOI: 10.1021/jo00293a049
OH S ET AL: "Synthesis of two marine farnesylacetones that dilate the basilar arteries of rabbits", BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, PERGAMON, ELSEVIER SCIENCE, GB, vol. 20, no. 14, 15 July 2010 (2010-07-15), pages 4206 - 4209, XP027104019, ISSN: 0960-894X, [retrieved on 20100519]
ITSUMARO KUMADAKI ET AL: "Synthesis of fluorine analogues of vitamin E.", CHEMICAL & PHARMACEUTICAL BULLETIN, vol. 36, no. 2, 1 January 1988 (1988-01-01), pages 515 - 520, XP055023351, ISSN: 0009-2363, DOI: 10.1248/cpb.36.515
MANABU MURAKAMI, KIYOSHI OKETANI, HIDEAKI FUJISAKI,TSUNEO WAKABAYASHI, YUICHI INAI, SHINYA ABE,ISAO YAMATSU AND TOSHIHARU OHGO: "EFFECT OF SYNTHETIC ACYCLIC POLYISOPRENOIDS ON THECOLD-RESTRAINT STRESS INDUCED GASTRIC ULCER IN RATS", JAPAN. J. PHARMACOL., vol. 33, 1 January 1983 (1983-01-01), pages 549 - 556, XP002672625
DATABASE Reaxys [online] Elsevier Properties SA; 28 March 2012 (2012-03-28), "6,10-dimethyl-undeca-5,9-dien-2-one O-methyl-oxime", XP002672465, retrieved from www.reaxys.com Database accession no. 6695244
BIANCA J J M BRUNDEL ET AL: "Induction of Heat Shock Response Protects the Heart Against Atrial Fibrillation", CIRCULATION RESEARCH, GRUNE AND STRATTON, BALTIMORE, US, vol. 99, 10 January 2006 (2006-01-10), pages 1394 - 1402, XP007916993, ISSN: 0009-7330, [retrieved on 20061116], DOI: DOI:10.1161/01.RES.0000252323.83137.FE
MASAO SAKABE1 ET AL: "Effects of a heat shock protein inducer on the atrial fibrillation substrate caused by acute atrial ischaemia", CARDIOVASCULAR RESEARCH, OXFORD UNIVERSITY PRESS, GB, vol. 78, 1 January 2008 (2008-01-01), pages 63 - 70, XP007916994, ISSN: 0008-6363, [retrieved on 20080131], DOI: DOI:10.1093/CVR/CVN019
Attorney, Agent or Firm:
Jansen, C.M. (Johan de Wittlaan 7, JR Den Haag, NL)
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