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WO2011069995A1 - Nouveaux cyclooctadepsipeptides à 24 chaînons issus de souches fongiques et leur utilisation comme anthelminthiques ou endoparasiticides - Google Patents

Nouveaux cyclooctadepsipeptides à 24 chaînons issus de souches fongiques et leur utilisation comme anthelminthiques ou endoparasiticides Download PDF

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Publication number
WO2011069995A1
WO2011069995A1 PCT/EP2010/069040 EP2010069040W WO2011069995A1 WO 2011069995 A1 WO2011069995 A1 WO 2011069995A1 EP 2010069040 W EP2010069040 W EP 2010069040W WO 2011069995 A1 WO2011069995 A1 WO 2011069995A1
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WO
WIPO (PCT)
Prior art keywords
xrb
cyclooctadepsipeptides
fungal strains
novel
esi
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/EP2010/069040
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English (en)
Inventor
Achim Harder
Klemens Krieger
Thi Lam Huong Pham
Thanh Dam Huynh
Irmtraut Zaspel
Dietrich Ewald
Clemens Mügge
Hardy Weisshoff
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.)
Bayer Animal Health GmbH
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Bayer Animal Health GmbH
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 Bayer Animal Health GmbH filed Critical Bayer Animal Health GmbH
Priority to AU2010329998A priority Critical patent/AU2010329998B2/en
Priority to EP10790400.5A priority patent/EP2509967B1/fr
Priority to US13/514,538 priority patent/US20120302496A1/en
Priority to JP2012542507A priority patent/JP5779787B2/ja
Publication of WO2011069995A1 publication Critical patent/WO2011069995A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D273/00—Heterocyclic compounds containing rings having nitrogen and oxygen atoms as the only ring hetero atoms, not provided for by groups C07D261/00 - C07D271/00
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00—Antiparasitic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00—Antiparasitic agents
    • A61P33/10—Anthelmintics

Definitions

  • the present invention relates firstly to the discovery of the novel 24-membered cyclooctadepsipeptides (the previously unknown derivatives PF1022-V and PF1022-W of the known anthelmintic cyclooctadepsipeptide PF1022-A and the previously unknown derivatives XRB-C894, XRB-C942, XRB-C976, XRB-C1 01 0, XRB-C1 044, XRB-E922, XRB-E956, XRB-E990, XRB-E1024, XRB-S958, XRB-S992, XRB-S1026, XRB-S1060 of the known cyclooctadepsipeptide bassianolide) and the processes for the preparation of the abovementioned cyclooctadepsipeptides by means of the fungal strains from the family Xylariaceae, in particular the genera Rosellinia and Coniolariella,
  • Formula III Basic structure of the novel cyclooctadepsipeptides with 24 ring atoms (Raa: amino acid residues; Rfa: fatty acid residues; Raa and Rfa: see Table 1 )
  • Table 1 Amino acid residues (Raa) and fatty acid residues (Rfa) of the novel 24-membered cyclooctadepsipeptides (Nos. 3 to 17) comp. Narne Raa 1 Rfa 1 Raa 2 Rfa 2 Raa 3 Rfa J Raa 4 Rfa'
  • PF 1 022A (see formula I) is outstanding ly suitable for controlling endoparasites, especially in the field of human and veterinary medicine.
  • Such cyclooctadepsipeptides with 24 ring atoms and their use as endoparasiticides are already the subject matter of an earlier patent application (US005571793A).
  • Bassianolide (see formula II) has become known as an antibiotic with insecticidal activity (Kanaoka, M. ef a/., Bassianolide, a New Insecticidal Cyclodepsipeptide from Beauveria bassiana and Verticillium lecanii; Agric. Biol. Chem. 42 (1978), 629-635).
  • the present invention relates to the discovery of the previously unknown 24-membered cyclooctadepsipeptides (PF1022-V, P F 1 022-W , XR B-C894, XRB-C942 , XRB-C976, XRB-C 1010, XRB-C1 044, XRB-E922, XRB-E956, XRB-E990, XRB-E1024, XRB-S958, XRB-S992, XRB-S1026, XRB-S1060) in various isomeric forms (see formula I II, Table 1 and Figs.
  • the present invention relates to the preparation of novel 24-membered cyclooctadepsipeptides (PF1022-V, PF1022-W, XRB-C894, XRB-C942, XRB-C976, XRB-C1010, XRB-C 1 044, XRB-E922, XRB-E956, XRB-E990, XRB-E1 024, XRB-S958, XRB-S992, XRB-S1026, XRB-S1060) in various isomeric forms by means of the fungal strains from the family Xylariaceae, in particular the genera Rosellinia and Coniolariella, within which several fungal lines are capable of producing the cyclooctadepsipeptides.
  • the lines XR-909, XR-912, XR-91 3, XR-916 and XR-917 which differ in culture from the original strains by their growth habit and their capability for producing cyclooctadepsipeptides, were obtained from these CBS fungal strains after repeated selections on mSeed medium. The property of mycelial development is linked to the production of certain cyclooctadepsipeptides. Other fungal strains were isolated from natural sources.
  • the genus Rosellinia is a ubiquitous fungal genus of the family Xylariaceae, which belongs to the extensive order Xylariales (phylum Ascomycota).
  • the representatives of the genus Rosellinia are found on the bark of broad-leaved and coniferous trees in coolish locations of the moderate zones of the northern hemisphere. They live predominantly saprophytically on old or dead timber which is already in the process of degradation, or on herbaceous plants. They have characteristic spherical hard fruiting bodies, so-called perithecia with ostioles, in which asci with the species-typical spores develop. The asci are characterized by species-typical cubical or rectangular apical apparatuses which serve for ejecting the mature spores. The spores of the genus Rosellinia have species-typical germination slits.
  • the spores of R. abscondita are pale brown and between 16 to 24 x 5.5 to 8.5 ⁇ in size. Very frequently, the germination slit is arranged diagonally over the spore surface. The spore poles bear a mucous sheath. The spores of R. britannica are 22 to 27 x 7 to 9 ⁇ in size, brown and bear mucous sheaths. The spores of R. mammaeformis are 17 to 21 x 6 to 7 ⁇ in size, brown with darker ends. The species R. nectrioides is very similar to R. abscondita. The asco spores are likewise pale brown, but there are no appendages or mucous sheaths.
  • the perithecia of the species are usually embedded in a dark brown to black subiculum (thick layers of hyphae). The hyphae grow from the subiculum into the bark tissue and the layers therebelow.
  • the individual species make high demands on the environmental conditions which occur under natural conditions. Mature perithecia occur in mild winters and in the early months of the year. In general, the abovementioned Rosellinia species are rare.
  • the genus Coniolariella was renamed after various species, which had previously been classified under Rosellinia, had been classified as belonging to this genus (Checa et al. (2008) Mycol. Res. 1 12, 7, 795-801 ).
  • Pure cultures from fruiting bodies of Rosellinia, Coniiolariella and further Xylariaceaen in dead timber of broad-leaved and coniferous trees
  • Pure cultures were obtained from mature, intact perithecia which were as isolated as possible and which had been removed from dead timber. They were surface-disinfected with 0.05% strength AgN0 3 solution and rinsed repeatedly with sterile water. The perithecia were carefully crushed on a glass slide, and the asci and spores which were released were transferred into tubes containing sterile water.
  • the spore density was high, the spore suspension was diluted by a factor of ten, and 100 ⁇ of the respective dilution stage were plated onto malt extract agar (MEA). The plates were stored at 18 to 20°C, scored every day under the microscope, and germinating spores were transferred to fresh potato dextrose agar (PDA). The mycelium formed which grows on this medium is whitish, flat and delicate; no aerial mycelium develops.
  • Assaying the growth of fungal lines The growth of the fungal lines of the Xylariaceae in culture on malt extract agar (MEA), potato dextrose agar (PDA), cornmeal agar (CMA) or mSeed agar tends to be slow and to a high degree temperature-dependent. They develop a whitish flat delicate mycelium, in some cases also a filamentous mycelium, on these media.
  • MEA malt extract agar
  • PDA potato dextrose agar
  • CMA cornmeal agar
  • mSeed agar tends to be slow and to a high degree temperature-dependent. They develop a whitish flat delicate mycelium, in some cases also a filamentous mycelium, on these media.
  • Line XR-916 shows the highest growth rate at 15°C and, after 15 days, reaches a colony size of 85 mm on MEA and a colony size of 70 mm on PDA. Under these conditions, the growth of line XR-909 on MEA amounts to 62 mm and on PDA to 52 mm.
  • Line XR-913 shows a g rowth of 85 mm diameter on PDA and of 68 mm diameter on MEA.
  • Line XR-917 shows the same growth on both media and reaches colony sizes of in each case 85 mm.
  • line XR-916 reaches 46 mm on PDA and 51 mm on MEA.
  • line XR-909 reaches 45 mm on PDA and 50 mm on MEA.
  • Other lines have colony sizes of 85 mm on both media at 21 °C.
  • Fusarium and Verticillium isolates show good growth at temperatures between 22 and 25°C and Beauveria isolates at 20°C (on mSeed medium).
  • MEA malt extract 17 g/l, agar 15 g/l
  • PDA glucose 5 g/l, potato starch 20 g/l, agar 15 g/l
  • the methanolic mycelial extracts from the CBS fungal strains (CBS 1 1 1 .75, CBS 267.30, CBS 445.89, CBS 446.89, CBS 447.89, CBS 448.89, CBS 449.89, CBS 450.89, CBS 499.80) and from the newly obtained lines or isolates (XR-909, XR-91 3, XR-916, XR-91 7, XR-21 , etc.), and also from further fungal strains from the groups Fusarium, Beauveria and Verticillium were first analysed by means of LC-PDA-ESI-Q-TOF-MS.
  • the cell material was obtained from agar plates and extracted with methanol.
  • the methanolic extracts were concentrated in vacuo unti l free from methanol, and then extracted repeatedly with ethyl acetate.
  • HPLC condition isocratic (A / B : 33 / 67)
  • PDA detector 210 to 400 nm
  • Eluent A water (0.1 % HCOOH)
  • Eluent B acetonitrile (0.1 % HCOOH)
  • HPLC condition isocratic (A / B : 25 / 75)
  • PDA detector 210 to 400 nm
  • PDA detector 210 to 400 nm
  • PDA detector 210 to 400 nm
  • MS detector ESI-Q-TOF-MS (full-scan, m/z 130 to 1600)
  • Empirical formula C52H76N4O12 Accurate mass: 948.5460
  • Analytical data of bassianolide and of its novel derivatives (XRB-C894, XRB-C942, XRB-C976, XRB-C1010, XRB-C1044, XRB-D940, XRB-D974, XRB- E922, XRB-E956, XRB-E990, XRB-E1024, XRB-S958, XRB-S992, XRB-S1026, XRB-S1060) including their isomers
  • Empirical formula C49H86N4O12 Accurate mass: 922.6242
  • Empirical formula 0 5 8 ⁇ 8 ⁇ 4 ⁇ 2 Accurate mass: 1024.5773

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  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Public Health (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Tropical Medicine & Parasitology (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Peptides Or Proteins (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Micro-Organisms Or Cultivation Processes Thereof (AREA)

Abstract

La présente invention concerne la découverte des cyclooctadepsipeptides à 24 chaînons non encore identifiés PF1022-V, PF1022-W, XRB-C894, XRB-C942, XRB-C976, XRB-C1010, XRB-C1044, XRB-E922, XRB-E956, XRB-E990, XRB-E1024, XRB-S958, XRB-S992, XRB-S1026, XRB-S1060 (sous diverses formes isomères). L'invention concerne également des procédés de préparation des cyclooctadepsipeptides précédemment mentionnés, au moyen des souches fongiques appartenant à la famille Xylariaceae, en particulier les genres Rosellinia et Coniolariella, et au moyen des souches fongiques mitosporiques appartenant aux groupes Fusarium, Beauveria et Verticillium (ordres des Hypocreales et des Phyllachorales), et au moyen des préparations enzymatiques obtenues à partir de ces souches fongiques. En outre, l'invention concerne l'utilisation de ces souches pour préparer les nouveaux cyclooctadepsipeptides précédemment mentionnés et l'utilisation de bassianolide et desdits cyclooctadepsipeptides, individuellement ou en mélange, comme anthelminthiques ou endoparasiticides.
PCT/EP2010/069040 2009-12-11 2010-12-07 Nouveaux cyclooctadepsipeptides à 24 chaînons issus de souches fongiques et leur utilisation comme anthelminthiques ou endoparasiticides Ceased WO2011069995A1 (fr)

Priority Applications (4)

Application Number Priority Date Filing Date Title
AU2010329998A AU2010329998B2 (en) 2009-12-11 2010-12-07 Novel 24-membered cyclooctadepsipeptides from fungal strains and their use as anthelmintics or endoparasiticides
EP10790400.5A EP2509967B1 (fr) 2009-12-11 2010-12-07 Nouveaux cyclooctadepsipeptides à 24 chaînons issus de souches fongiques et leur utilisation comme anthelminthiques ou endoparasiticides
US13/514,538 US20120302496A1 (en) 2009-12-11 2010-12-07 Novel 24-membered cyclooctadepsipeptides from fungal strains and their use as anthelmintics or endoparasiticides
JP2012542507A JP5779787B2 (ja) 2009-12-11 2010-12-07 真菌株から由来の新規な２４員のシクロオクタデプシペプチドおよびその駆虫剤または内部寄生虫駆除剤としての使用

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EP09178799 2009-12-11
EP09178799.4 2009-12-11

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US (1) US20120302496A1 (fr)
EP (1) EP2509967B1 (fr)
JP (1) JP5779787B2 (fr)
AR (1) AR079341A1 (fr)
AU (1) AU2010329998B2 (fr)
TW (1) TW201138799A (fr)
UY (1) UY33095A (fr)
WO (1) WO2011069995A1 (fr)

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WO2013187480A1 (fr) 2012-06-13 2013-12-19 Ｍｅｉｊｉ Ｓｅｉｋａファルマ株式会社 Nouveau dérivé depsipeptidique cyclique et agent de lutte contre les organismes nuisibles comprenant ledit dérivé
CN106749569A (zh) * 2017-03-03 2017-05-31 重庆乾泰生物医药有限公司 一种pf1022a的分离纯化方法
CN106978353A (zh) * 2017-03-10 2017-07-25 广东省微生物研究所 特氏炭角菌及其栽培方法
WO2018093920A1 (fr) * 2016-11-16 2018-05-24 Merial, Inc. Composés depsipeptidiques anthelminthiques
CN108570016A (zh) * 2017-03-10 2018-09-25 上海医药工业研究院 一种pf1022a分离纯化的方法

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TW201609680A (zh) * 2013-12-18 2016-03-16 明治製菓藥業股份有限公司 環狀縮酚肽（ｃｙｃｌｉｃ ｄｅｐｓｉｐｅｐｔｉｄｅ）衍生物及含該衍生物所成之有害生物防治劑
ES2916216T3 (es) 2015-05-20 2022-06-29 Boehringer Ingelheim Animal Health Usa Inc Compuestos de depsipéptidos antihelmínticos
AU2016380868B2 (en) 2015-12-28 2019-11-28 Boehringer Ingelheim Animal Health USA Inc. Anthelmintic depsipeptide compounds
CN113943350B (zh) * 2021-11-02 2023-08-15 海南大学三亚南繁研究院 一种环肽化合物或其药学上可接受的盐及其制备方法和应用、药物及其应用
CN114875093B (zh) * 2022-05-20 2024-07-19 浙江海正药业股份有限公司 一种提高pf1022a发酵产量的方法
WO2025149943A1 (fr) * 2024-01-09 2025-07-17 Animol Discovery, Inc. Depsipeptides cycliques antiparasitaires

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EP0930304A1 (fr) 1996-08-07 1999-07-21 Meiji Seika Kabushiki Kaisha Procede de production de composes a base de cyclodepsipeptide et nouveau cyclodepsipeptide
WO2010107232A2 (fr) 2009-03-16 2010-09-23 Lg Electronics Inc. Procédé de retransmission permettant de prendre en charge des mimo dans une requête harq synchrone

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Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2013187480A1 (fr) 2012-06-13 2013-12-19 Ｍｅｉｊｉ Ｓｅｉｋａファルマ株式会社 Nouveau dérivé depsipeptidique cyclique et agent de lutte contre les organismes nuisibles comprenant ledit dérivé
JPWO2013187480A1 (ja) * 2012-06-13 2016-02-08 Ｍｅｉｊｉ Ｓｅｉｋａファルマ株式会社 新規環状デプシペプチド誘導体およびそれを含んでなる有害生物防除剤
TWI609860B (zh) * 2012-06-13 2018-01-01 Meiji Seika Pharma Co Ltd 新穎環狀酯肽（Ｄｅｐｓｉｐｅｐｔｉｄｅ）衍生物及含有其之有害生物防除劑
EP3441399A1 (fr) 2012-06-13 2019-02-13 Meiji Seika Pharma Co., Ltd. Nouveaux dérivés de depsipeptides cycliques et agents de lutte contre des organismes nuisibles les comprenant
WO2018093920A1 (fr) * 2016-11-16 2018-05-24 Merial, Inc. Composés depsipeptidiques anthelminthiques
CN110167921A (zh) * 2016-11-16 2019-08-23 勃林格殷格翰动物保健美国公司 驱蠕虫缩肽化合物
CN106749569A (zh) * 2017-03-03 2017-05-31 重庆乾泰生物医药有限公司 一种pf1022a的分离纯化方法
CN106749569B (zh) * 2017-03-03 2021-10-15 重庆乾泰生物医药有限公司 一种pf1022a的分离纯化方法
CN106978353A (zh) * 2017-03-10 2017-07-25 广东省微生物研究所 特氏炭角菌及其栽培方法
CN108570016A (zh) * 2017-03-10 2018-09-25 上海医药工业研究院 一种pf1022a分离纯化的方法
CN106978353B (zh) * 2017-03-10 2019-10-18 广东省微生物研究所 特氏炭角菌及其栽培方法
CN108570016B (zh) * 2017-03-10 2021-11-26 上海医药工业研究院 一种pf1022a分离纯化的方法

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AU2010329998A1 (en) 2012-07-05
UY33095A (es) 2011-07-29
TW201138799A (en) 2011-11-16
AR079341A1 (es) 2012-01-18
US20120302496A1 (en) 2012-11-29
AU2010329998B2 (en) 2015-05-21
EP2509967B1 (fr) 2016-02-17
EP2509967A1 (fr) 2012-10-17
JP5779787B2 (ja) 2015-09-16
JP2013513567A (ja) 2013-04-22

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