WO2007013965A3 - Synthesis of scabronines and analogues thereof - Google Patents

Synthesis of scabronines and analogues thereof Download PDF

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Publication number
WO2007013965A3
WO2007013965A3 PCT/US2006/028155 US2006028155W WO2007013965A3 WO 2007013965 A3 WO2007013965 A3 WO 2007013965A3 US 2006028155 W US2006028155 W US 2006028155W WO 2007013965 A3 WO2007013965 A3 WO 2007013965A3
Authority
WO
WIPO (PCT)
Prior art keywords
scabronines
synthesis
analogs
disease
analogues
Prior art date
Application number
PCT/US2006/028155
Other languages
French (fr)
Other versions
WO2007013965A2 (en
Inventor
Samuel J Danishefsky
Stephen P Waters
Original Assignee
Sloan Kettering Inst Cancer
Univ Columbia
Samuel J Danishefsky
Stephen P Waters
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Sloan Kettering Inst Cancer, Univ Columbia, Samuel J Danishefsky, Stephen P Waters filed Critical Sloan Kettering Inst Cancer
Priority to CA002616028A priority Critical patent/CA2616028A1/en
Publication of WO2007013965A2 publication Critical patent/WO2007013965A2/en
Priority to US12/017,951 priority patent/US7910623B2/en
Publication of WO2007013965A3 publication Critical patent/WO2007013965A3/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C62/00—Compounds having carboxyl groups bound to carbon atoms of rings other than six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C62/30—Unsaturated compounds
    • C07C62/36—Unsaturated compounds containing —CHO groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/45—Carboxylic acid nitriles having cyano groups bound to carbon atoms of rings other than six-membered aromatic rings
    • C07C255/47—Carboxylic acid nitriles having cyano groups bound to carbon atoms of rings other than six-membered aromatic rings to carbon atoms of rings being part of condensed ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C62/00—Compounds having carboxyl groups bound to carbon atoms of rings other than six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C62/30—Unsaturated compounds
    • C07C62/32—Unsaturated compounds containing hydroxy or O-metal groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C62/00—Compounds having carboxyl groups bound to carbon atoms of rings other than six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C62/30—Unsaturated compounds
    • C07C62/38—Unsaturated compounds containing keto groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/74—Esters of carboxylic acids having an esterified carboxyl group bound to a carbon atom of a ring other than a six-membered aromatic ring
    • C07C69/757—Esters of carboxylic acids having an esterified carboxyl group bound to a carbon atom of a ring other than a six-membered aromatic ring having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C07C2603/02—Ortho- or ortho- and peri-condensed systems
    • C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
    • C07C2603/30—Ortho- or ortho- and peri-condensed systems containing three rings containing seven-membered rings

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

A novel synthesis of scabronines, which are related to a broader class of angularly fused tricyclic diterpenoids known as cyathanes, is provided. Scabronine G, its methyl ester derivative, and other analogs have been shown to have neurotrophic activity. Therefore, these compounds are particularly useful in treating neurodegenerative diseases such as Alzheimer's disease, Parkinson's disease, Huntington's diseases, etc. The invention provides for the synthesis of scabronines as well as analogs thereof. Pharmaceutical compositions and method of using the inventive compounds are also provided.
PCT/US2006/028155 2005-07-22 2006-07-21 Synthesis of scabronines and analogues thereof WO2007013965A2 (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
CA002616028A CA2616028A1 (en) 2005-07-22 2006-07-21 Synthesis of scabronines and analogues thereof
US12/017,951 US7910623B2 (en) 2005-07-22 2008-01-22 Synthesis of scabronines and analogues thereof

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US70169805P 2005-07-22 2005-07-22
US60/701,698 2005-07-22

Related Child Applications (1)

Application Number Title Priority Date Filing Date
US12/017,951 Continuation US7910623B2 (en) 2005-07-22 2008-01-22 Synthesis of scabronines and analogues thereof

Publications (2)

Publication Number Publication Date
WO2007013965A2 WO2007013965A2 (en) 2007-02-01
WO2007013965A3 true WO2007013965A3 (en) 2009-05-14

Family

ID=37683798

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2006/028155 WO2007013965A2 (en) 2005-07-22 2006-07-21 Synthesis of scabronines and analogues thereof

Country Status (2)

Country Link
CA (1) CA2616028A1 (en)
WO (1) WO2007013965A2 (en)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2011133651A1 (en) * 2010-04-20 2011-10-27 Chiral Quest , Inc. An enantioselective process for cycloalkenyl b-substituted alanines
CN109824686B (en) * 2019-02-22 2021-07-06 西北农林科技大学 Bird nest alkane type diterpenoid compound, preparation method and application thereof

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4629700A (en) * 1983-11-30 1986-12-16 Standard Oil Company (Indiana) Selective conversion of cyano compounds to amides and carboxylic acids
JPH0769961A (en) * 1993-08-31 1995-03-14 Kagome Co Ltd Cyathane derivative, and neuro growth factor production inducing agent and antimicrobial agent using the same as active component
JPH11269125A (en) * 1998-03-19 1999-10-05 Kagome Co Ltd Cyathane derivative and nerve growth factor production inducer containing the same as active ingredient
JP2002234896A (en) * 2001-02-09 2002-08-23 Kinokkusu:Kk Cyathane derivative
JP2003089670A (en) * 2001-09-18 2003-03-28 Nippon Tenganyaku Kenkyusho:Kk Cyathane derivative and composition including the same
US6683087B2 (en) * 2000-04-18 2004-01-27 Axon Biochemicals B.V. Phenylethylamines and condensed rings variants as prodrugs of catecholamines, and their use
US20050032802A1 (en) * 2002-12-05 2005-02-10 Gemin X Biotechnologies Inc. Diterpenoid compounds, compositions thereof and their use as anti-cancer or anti-fungal agents

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4629700A (en) * 1983-11-30 1986-12-16 Standard Oil Company (Indiana) Selective conversion of cyano compounds to amides and carboxylic acids
JPH0769961A (en) * 1993-08-31 1995-03-14 Kagome Co Ltd Cyathane derivative, and neuro growth factor production inducing agent and antimicrobial agent using the same as active component
JPH11269125A (en) * 1998-03-19 1999-10-05 Kagome Co Ltd Cyathane derivative and nerve growth factor production inducer containing the same as active ingredient
US6683087B2 (en) * 2000-04-18 2004-01-27 Axon Biochemicals B.V. Phenylethylamines and condensed rings variants as prodrugs of catecholamines, and their use
JP2002234896A (en) * 2001-02-09 2002-08-23 Kinokkusu:Kk Cyathane derivative
JP2003089670A (en) * 2001-09-18 2003-03-28 Nippon Tenganyaku Kenkyusho:Kk Cyathane derivative and composition including the same
US20050032802A1 (en) * 2002-12-05 2005-02-10 Gemin X Biotechnologies Inc. Diterpenoid compounds, compositions thereof and their use as anti-cancer or anti-fungal agents

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
OBARA, Y. ET AL.: "Scabronine G-Methylester Enhances Secretion of Neurotrophic Factors Mediated by an Activation of Protein Kinase C-.", MOLECULAR PHARMACOLOGY., vol. 59, no. 5, 2001, pages 1289, - 1296 *
WARD, D. ET AL.: "Synthetic Studies on Cyathin Diterpenes Total Synthesis of +/- -allocyathin B3.", CAN J CHEM. 2004., vol. 82, pages 254 - 258 *

Also Published As

Publication number Publication date
CA2616028A1 (en) 2007-02-01
WO2007013965A2 (en) 2007-02-01

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