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WO2008070934A1 - Inhibition d'invertébrés à l'aide de ligands qui modulent les récepteurs de l'ecdysone - Google Patents

Inhibition d'invertébrés à l'aide de ligands qui modulent les récepteurs de l'ecdysone Download PDF

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Publication number
WO2008070934A1
WO2008070934A1 PCT/AU2007/001944 AU2007001944W WO2008070934A1 WO 2008070934 A1 WO2008070934 A1 WO 2008070934A1 AU 2007001944 W AU2007001944 W AU 2007001944W WO 2008070934 A1 WO2008070934 A1 WO 2008070934A1
Authority
WO
WIPO (PCT)
Prior art keywords
group
phenyl
cycloalkyl
alkyl
alkenyl
Prior art date
Legal status (The legal status 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 status listed.)
Ceased
Application number
PCT/AU2007/001944
Other languages
English (en)
Inventor
Andris Juris Liepa
Wynona Marguerite Johnson
Kathleen Anne Turner
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Commonwealth Scientific and Industrial Research Organization CSIRO
Australian Wool Innovation Ltd
Original Assignee
Commonwealth Scientific and Industrial Research Organization CSIRO
Australian Wool Innovation Ltd
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 Commonwealth Scientific and Industrial Research Organization CSIRO, Australian Wool Innovation Ltd filed Critical Commonwealth Scientific and Industrial Research Organization CSIRO
Publication of WO2008070934A1 publication Critical patent/WO2008070934A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/36—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/44—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having three double bonds between ring members or between ring members and non-ring members
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D473/00—Heterocyclic compounds containing purine ring systems

Definitions

  • each R and R is independently selected from the group consisting of H, Cl- ClO alkyl, C3-C8 cycloalkyl, C4-C8 cycloalkenyl, C2-C10 alkenyl, C2-C10 alkynyl, phenyl, biphenyl, aralkyl, heterocyclyl and heterocyclylalkyl;
  • p is selected from 0-1 and q is selected from 0-2, provided that when p is 1, q is not 2;
  • R 1 and R 2 are joined together to form the group -C(O)-X-(CH 2 ) y - wherein the - C(O)- moiety is at the R 1 position and the -(CH 2 ) y - moiety is at the R 2 position;
  • X is selected from CH 2 , O, and NR;
  • R is selected from H and Cl-3alkyl; each CH 2 group is optionally substituted; and y is 1 to 3;
  • each R 6 , R 7 , R 9 , R 10 , R 13 , R 16 and R 17 is independently selected from the group consisting of Cl-ClO alkyl, C3-C8 cycloalkyl, C4-C8 cycloalkenyl, C2-C10 alkenyl, C2-C10 alkynyl, phenyl, biphenyl, aralkyl, heterocyclyl and heterocyclylalkyl;
  • alkynyl and “alkinyl” as used herein, refers to straight chain or branched hydrocarbon groups containing one or more triple bonds. Suitable alkynyl groups include, but are not limited to ethynyl, propynyl, butynyl, pentynyl and hexynyl.
  • the ligand binding regions from the EcR and USP proteins of the insect pest, Bovicola ovis, were co-expressed from a baculovirus vector, purified as a recombinant heterodimer (BOECR DEF /BOUSP DEF ) by immobilised metal affinity chromatography, and used in fluorescent polarisation assays (patent specifications PCT /AU2004/001701 and WO2005054271, which are hereby incorporated by cross-reference).

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

La présente invention concerne l'utilisation de γ-méthylène γ-lactames N-substituées en tant que ligands non stéroïdiens permettant de moduler les récepteurs de l'ecdysone en général (ce qui permet de contrôler la croissance des insectes), et en particulier les récepteurs de l'ecdysone de la calliphore australienne, Lucilia cuprina, et du pou du mouton, Bovicola ovis. L'invention a également trait à de nouvelles γ-méthylène γ-lactames N-substituées. Lesdits composés sont utiles en tant qu'insecticides ou en tant que têtes de série permettant l'élaboration d'insecticides. Les composés sont également utiles en tant qu'effecteurs pour les commutateurs de l'ecdysone.
PCT/AU2007/001944 2006-12-15 2007-12-17 Inhibition d'invertébrés à l'aide de ligands qui modulent les récepteurs de l'ecdysone Ceased WO2008070934A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
AUPCT/AU2006/001905 2006-12-15
PCT/AU2006/001905 WO2008070891A1 (fr) 2006-12-15 2006-12-15 Ligands permettant de moduler les récepteurs de l'ecdysone et de lutter contre la croissance des insectes

Publications (1)

Publication Number Publication Date
WO2008070934A1 true WO2008070934A1 (fr) 2008-06-19

Family

ID=39511130

Family Applications (2)

Application Number Title Priority Date Filing Date
PCT/AU2006/001905 Ceased WO2008070891A1 (fr) 2006-12-15 2006-12-15 Ligands permettant de moduler les récepteurs de l'ecdysone et de lutter contre la croissance des insectes
PCT/AU2007/001944 Ceased WO2008070934A1 (fr) 2006-12-15 2007-12-17 Inhibition d'invertébrés à l'aide de ligands qui modulent les récepteurs de l'ecdysone

Family Applications Before (1)

Application Number Title Priority Date Filing Date
PCT/AU2006/001905 Ceased WO2008070891A1 (fr) 2006-12-15 2006-12-15 Ligands permettant de moduler les récepteurs de l'ecdysone et de lutter contre la croissance des insectes

Country Status (1)

Country Link
WO (2) WO2008070891A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN113444039A (zh) * 2021-08-02 2021-09-28 河南省科学院高新技术研究中心 一种利用离子液体制备2,2,4-三甲基-1,2-二氢喹啉的方法

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN114907253B (zh) * 2021-02-09 2023-04-07 中国科学院化学研究所 一种多取代3-亚甲基异吲哚啉-1-酮的制备方法

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5045108A (en) * 1989-06-21 1991-09-03 Bayer Aktiengesellschaft Herbicidal and plant growth-regulating N-aryl-pyrrol-L-one and isoindol-2-one compounds

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5045108A (en) * 1989-06-21 1991-09-03 Bayer Aktiengesellschaft Herbicidal and plant growth-regulating N-aryl-pyrrol-L-one and isoindol-2-one compounds

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
ADHIKARI R. ET AL.: "Synthesis of N-Substituted gamma-Methylene gamma-Lactams", AUSTRALIAN JOURNAL OF CHEMISTRY, vol. 58, 2005, pages 882 - 890 *

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN113444039A (zh) * 2021-08-02 2021-09-28 河南省科学院高新技术研究中心 一种利用离子液体制备2,2,4-三甲基-1,2-二氢喹啉的方法
CN113444039B (zh) * 2021-08-02 2022-05-31 河南省科学院高新技术研究中心 一种利用离子液体制备2,2,4-三甲基-1,2-二氢喹啉的方法

Also Published As

Publication number Publication date
WO2008070891A1 (fr) 2008-06-19

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