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Ep 1971588 B1 (19) & (11) EP 1 971 588 B1 (12) EUROPEAN PATENT SPECIFICATION (45) Date of publication and mention (51) Int Cl.: of the grant of the patent: C07D 303/48 (2006.01) C07D 303/14 (2006.01) 11.07.2012 Bulletin 2012/28 C07D 493/04 (2006.01) C07D 301/32 (2006.01) C07D 303/40 (2006.01) C07D 303/02 (2006.01) (2006.01) (2006.01) (21) Application number: 06840409.4 C07D 493/02 A61K 31/336 A61P 31/04 (2006.01) A61P 35/00 (2006.01) A01N 45/00 (2006.01) A61P 33/00 (2006.01) (22) Date of filing: 22.12.2006 A61P 35/02 (2006.01) A61P 31/00 (2006.01) A61P 33/02 (2006.01) C07D 303/32 (2006.01) (86) International application number: PCT/AU2006/002001 (87) International publication number: WO 2007/070985 (28.06.2007 Gazette 2007/26) (54) TIGLIEN-3-ONE DERIVATIVES TIGLIEN-3-ONDERIVATE DERIVES DE TIGLIEN-3-ONE (84) Designated Contracting States: (56) References cited: AT BE BG CH CY CZ DE DK EE ES FI FR GB GR • BROOKS G ET AL: "Daphnane diterpenes of HU IE IS IT LI LT LU LV MC NL PL PT RO SE SI Thymelaea hirsuta", PHYTOCHEMISTRY, SK TR PERGAMON PRESS, GB, vol. 29, no. 7, 1 January Designated Extension States: 1990 (1990-01-01), pages 2235-2237, AL BA HR MK RS XP026616241, ISSN: 0031-9422, DOI: DOI: 10.1016/0031-9422(90)83044-2 [retrieved on (30) Priority: 23.12.2005 AU 2005907278 1990-01-01] • DATABASE CA [Online] XP008118669 Database (43) Date of publication of application: accession no. (115:273076) 24.09.2008 Bulletin 2008/39 • TYLER M.I. ET AL.: ’Synthesis and structure- activity studies of potential antitumour agents (73) Proprietor: QBiotics Limited derived from esters of phorbol’ AUSTRALIAN Yungaburra, QLD 4884 (AU) JOURNAL OF CHEMISTRY vol. 40, no. 1, 1987, pages 193 - 200, XP008082434 (72) Inventors: • DATABASE CA [Online] XP008118671 Database • REDDELL, Paul Warren accession no. (101:147806) Yungaburra, Queensland 4884 (AU) • HAFEZ A. ET AL.: ’Active principles of the • GORDON, Victoria Anne Thymelaeaceae. III. Skin irritant and Yungaburra, Queensland 4884 (AU) cocarcinogenic factors from Pimelea simplex’ PLANTA MEDICA vol. 49, no. 1, 1983, pages 3 - 8, (74) Representative: McNab, Donald C. et al XP008082436 Marks & Clerk LLP • DATABASE CA [Online] XP008118672 Database Aurora accession no. (97:176609) 120 Bothwell Street • DATABASE CA [Online] XP008118670 Database Glasgow accession no. (93:232311) G2 7JS (GB) Note: Within nine months of the publication of the mention of the grant of the European patent in the European Patent Bulletin, any person may give notice to the European Patent Office of opposition to that patent, in accordance with the Implementing Regulations. Notice of opposition shall not be deemed to have been filed until the opposition fee has been paid. (Art. 99(1) European Patent Convention). EP 1 971 588 B1 Printed by Jouve, 75001 PARIS (FR) (Cont. next page) EP 1 971 588 B1 • BRYNES P.J. ET AL.: ’Plasminogen activator • DATABASE CA [Online] XP008118673 Database induction and platelet aggregation by phorbol accession no. (89:3208) and some of its derivatives: correlation with skin • DATABASE CA [Online] XP008118676 Database irritancy and tumor-promoting activity’ accession no. (88:37991) JOURNAL OF CANCER RESEARCH AND • DATABASE CA [Online] XP008118674 Database CLINICAL ONCOLOGY vol. 97, no. 3, 1980, pages accession no. (70:47662) 257 - 266, XP008127960 • DATABASE CA [Online] XP008118677 Database • DATABASE CA [Online] XP008118675 Database accession no. (69:10570) accession no. (92:141462) • DATABASE CA [Online] XP008118661 Database accession no. (89:192165) 2 EP 1 971 588 B1 Description FIELD OF THE INVENTION 5 [0001] This invention relates to bioactive molecules. More particularly, this invention relates to tiglien-3-one derivatives of potential therapeutic benefit and/or of use as a pharmaceutical and as an agrochenaical. BACKGROUND OF THE INVENTION 10 [0002] Bio-discovery is a growing field, which investigates and screens for bioactive natural products from natural environments, including plants, microorganisms, coral and other marine life. In the search for bioactive natural products, biological material is screened for molecules having properties that may be of therapeutic benefit for potential use in a range of treatments, for example treatments for cancer, antiprotozoal treatments, antiparasitic treatments, antibiotic treatments and anti-inflammatory treatments, or for pesticidal activity. 15 SUMMARY Of THE INVENTION [0003] The present invention arises from the discovery of new tiglien-3-one derivatives which have potentially new therapeutic uses as cytotoxic agents, antiprotozoal agents, antiparasitic agents and antibiotic agents or potential as 20 pesticidal agents for agricultural use. [0004] One aspect of the invention provides a compound of formula (II) 25 30 35 wherein: 40 X is selected from -O-, -S- and -NR25-; 1 2 R and R are independently selected from hydrogen, -OH, -OC1-C10 alkyl, -OC2-C)10 alkenyl, -OC2-C10 alkynyl, -Ocycloalkyl, -OC(O)C1-C10 alkyl, -OC(O)C1-C10 alkenyl, -OC(O)C2-C10 alkynyl, -OC(O)cycloalkyl, -OC(O)hetero- cyclyl, -OC(O)heteroaryl, -OC(O)NHC1-C10 alkyl, -OC(O)NHC2-C10 alkenyl, -OC(O)NHC2-C10 alkynyl, -OC(O)NH- cycloalkyl, -OC(O)NHaryl, -OC(O)NHheterocyclyl, -OC(O)NHheteroaryl, -OC(S)NHC1-C10 alkyl, -OC(S)NHC2-C10 45 alkenyl, -OC (S)NHC1-C10 alkynyl, -OC (S)NHcycloalkyl, -OC(S)NHaryl, -OC(S) NHheterocyclyl, -OC(S)NHheteroatyl 1 2 or R and R taken together are =O, =S, =NH or =N(C1-C6 alkyl); 3 R is hydrogen, -C1-C10 alkyl, -C2-C10 alkenyl or -C2-C10 alkynyl; 4 5 R and R are each hydrogen. -C 1-C10 alkyl, -C 1-C10 alkenyl, -C 2-C10 alkynyl, -OH, -OC 1-C10 alkyl -OC 2-C10 alkenyl, -OC2-C10 alkynyl, -Ocycloalkyl, -OC (O)C1C10 alkyl, -OC (O)C2-C10 alkenyl, -OC (O)C2-C10 alkynyl. -OC (O)cycloalkyl, 50 -OC(O)aryl, -OC(O)heterocyclyl, -OC(O)heteroaryl, -OC(O)NHC1-C10 alkyl, -OC(O)NHC2-C10 alkenyl, -OC(O) NHC2-C10 alkynyl. -OC(O)NHcycloalkyl, -OC(O)NHaryl, -OC(O)NHheterocyclyl, -OC(O)NHheteroaryl, -OC(S) NHC1-C10 alkyl, -OC(S)NHC2-C10 alkenyl, -OC(S)NHC2-C10 alkynyl, -OC(S)NHcycloalkyl, -OC(S)NHaryl,- OC(S) 25 4 5 NHheterocyclyl, -OC(S)NHheteroaryl, F, Cl, Br, I, -CN, -NO 2 or N(R )2, or R and R taken together form a double bond or are -O-, -S-, -NR25- or -CR26R27-; 55 6 R is selected from hydrogen, -C1-C10 alkyl, -C2-C10 alkenyl and -C2-C10 alkynyl; 8 R is selected from hydrogen, -C1-C10 alkyl, -C2-C10 alkenyl and -C2-C10 alkynyl; 10 R is selected from hydrogen, -C1-C10 alkyl, -C2-C10 alkenyl and -C1-C10 alkynyl; 11 R is selected from -OH, -OC1-C20 alkyl, -OC2-C20 alkenyl, -OC2-C20 alkynyl, -Ocycloalkyl, -OC(O)C1-C20 alkyl, 3 EP 1 971 588 B1 -OC(O)C2-C20 alkenyl, -OC(O)C1-C20 alkynyl, -OC(O)cycloalkyl, -OC(O)aryl, -OC(O)heterocyclyl, -OC(O)heteroar- yl, -OC(O)NHC1-C20 alkyl, -OC (O)NHC2-C20 alkenyl, -OC (O)NHC1-C20 alkynyl, -OC (O)NHeyrloalkyl, -OC(O)NHar- yl, -OC(O)NHheterocyclyl, -OC(O)NHheteroaryl, -OC(S)NHC1-C20 alkyl, -OC(S)NHC2-C20 alkenyl, -OC(S) 10 11 NHC2-C20 alkynyl, -OC (S)NHcycloalkyl, -OC(S)NHaryl, -OC(S)NHheterocyclyl, -OC(S)NHheteroaryl or R and R 5 taken together form a carbonyl group (=O); 12 R is selected from -OH, -OC1-C20 alkyl, -OC2C20 alkenyl, -OC2-C20 alkynyl, -Ocycloalkyl, -OC(O)C1-C20 alkyl, -OC(O)C2-C20 alkenyl, -OC(O)C2-C20 alkynyl, -OC(O)cycloalkyl, -OC(O)aryl, -OC(O)heterocyclyl, -OC(O)heteroar- yl, -OC(O)NHC1-C20 alkyl, -OC (O)NHC2-C10 alkenyl, -OC (O)NHC2-C20 alkynyl, -OC (O)NHcycloalkyl, -OC(O)NHar- yl, -OC(O)NHheterocyclyl, -OC(O)NHheteroaryl, -OC(S)NHC1-C20 alkyl, -OC(S)NHC2-C20 alkenyl, -OC(S) 10 NHC2-C20 alkynyl, -OC(S)NHcycloalkyl, -OC(S)NHaryl, -OC(S)NHheterocyclyl, -OC(S)NHheteroaryl; 13 14 R and R are independently selected from hydrogen and -C1-C10 alkyl; 18 R is selected from C 1-C20 alkyl, -C 2-C20 alkenyl, -C 2-C20 alkynyl, -OH, -OC 1-C10 alkyl, -OC 1-C10 alkenyl, -OC 2-C20 alkynyl, -Ocycloalkyl, -OC (O)C1-C20 alkyl, -OC(O)C2-C20 alkenyl, -OC (O)C2-C20 alkynyl, -OC (O)cycloalkyl, -OC(O) aryl, -OC(O)heterocyclyl, -OC(O)heteroaryl, -NHC 1-C20 alkyl, -NHC 1-C20 alkenyl,- NHC 2-C20 alkynyl, -NHcycloalkyl, 15 -NHaryl, -NHheterocyclyl, NHheteroaryl, -OC(O)NHC1-C20 alkyl, -OC(O)NHC2C20 alkenyl, -OC(O)NHC2-C20 alky- nyl,-OC (O)NHcycloalkyl, -OC(O)NHaryl, -OC(O)NHheterocyclyl, -OC(O)NHheteroacyl, -OC(S)NHC1-C10alkyl, -OC (S)NHC2-C20 alkenyl, -OC(S)NHC2-C20 alkynyl, -OC(S)NHycloallkyl, -OC(S)NHaryl, -OC(S)NHheterocyclyl, -OC (S)NHheteroaryl; 19 20 R and R are independently selected from hydrogen, -C 1-C6 alkyl, -C2-C6 alkenyl, -C2-C6 alkynyl, -OH, -OC 1-C6 20 alkyl, -OC2-C6 alkenyl, -OC 2-C6 alkynyl, -Ocycloalkyl, -OC (O)C1-C4 alkyl, -OC(O)C2-C6 alkenyl, -OC(O)C2-C6 alky- nyl, OC(O)cycloalkyl, -OC(O)aryl, -OC(O)heterocyclyl, -OC(O)heteroaryl or R19 and R20 taken together form a carbonyl or thiocarbonyl group; 11 R is selected from hydrogen, -C1-C10 alkyl, -C2-C10 alkenyl and -C2-C10 alkynyl; 22 R is selected from -OH, -OC1-C20 alkyl, -OC2-C20 alkenyl, -OC1-C20 alkynyl, -Ocycloalkyl, -OC(O)C1C20 alkyl, 25 -OC(O)C2-C20alkenyl, -OC (O)C2-C20alkynyl, -OC(O)cycloalkyl, -OC (O)aryl,-OC (O) heterocyclyl, -OC(O)heteroaryl, -OC(O)NHC1-C20 alkyl, -OC(O)NHC2-C20 alkenyl, -OC(O)NHC2-C20 alkynyl, -OC(O)NHcycloalkyl, -OC(O)NHaryl, -OC(O)NHheterocyclyl, -OC(O)NHheteroaryl, -OC(S)NHC1-C20 alkyl, -OC(S)NHC2-C20 alkenyl, -OC(S)NHC2-C20 alkynyl, -OC(S)NHcycloalkyl, -OC(S)NHaryl, -OC(S)NHheterocyclyl, -OC(S)NHheteroaryl or R21 and R22 taken together form a carbonyl group; 30 23 R is selected from hydrogen, -OH, -OC1-C20 alkyl, -OC2-C20 alkenyl, -OC2-C20 alkynyl, -Ocycloalkyl, -OC(O) C1-C20 alkyl, -OC (O)C2-C20 alkenyl, -OC (O)C2-C20 alkynyl, -OC (O)cycloalkyl, -OC(O)aryl,
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