JPH06184126A - Cyclic depsipeptide and its production - Google Patents
Cyclic depsipeptide and its productionInfo
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- JPH06184126A JPH06184126A JP27909492A JP27909492A JPH06184126A JP H06184126 A JPH06184126 A JP H06184126A JP 27909492 A JP27909492 A JP 27909492A JP 27909492 A JP27909492 A JP 27909492A JP H06184126 A JPH06184126 A JP H06184126A
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- substance
- pf1022e
- culture
- cyclic depsipeptide
- production
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- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Abstract
Description
【０００１】[0001]
【産業上の利用分野】本発明は、新規な環状デプシペプ
チド並びにその製造法に関する。本発明の環状デプシペ
プチドPF1022E は駆虫作用を有しており医薬、動物薬等
の分野への応用が期待される。TECHNICAL FIELD The present invention relates to a novel cyclic depsipeptide and a method for producing the same. The cyclic depsipeptide PF1022E of the present invention has anthelmintic action and is expected to be applied to the fields of medicine, veterinary medicine and the like.
【０００２】[0002]
【従来の技術】駆虫活性を有する化合物は多数知られて
いるが、微生物の生産物で駆虫活性を有する物質として
はデストマイシンＡ、ハイグロマイシンＢ、アベルメク
チン等が挙げられるが、その数は少ない。本発明者らは
先にニワトリ回虫を用いる探索研究の結果、駆虫活性を
有する環状デプシペプチド物質（PF1022）を発見した
〔特開平3-35796〕。また、その類縁物質としては特願
平3-163085が知られている。その後、本物質生産菌の培
養物を精査したところ、新たに新規な環状デプシペプチ
ドを単離することができた。BACKGROUND OF THE INVENTION Many compounds having anthelmintic activity are known, and substances such as destomycin A, hygromycin B, avermectin and the like, which are microbial products and have anthelmintic activity, are small in number. The present inventors previously discovered a cyclic depsipeptide substance (PF1022) having anthelmintic activity as a result of exploratory research using Ascaris roundum [JP-A-3-35796]. Japanese Patent Application No. 3-163085 is known as a related substance. Then, when the culture of this substance-producing bacterium was scrutinized, a new cyclic depsipeptide could be newly isolated.
【０００３】[0003]
【発明が解決しようとする課題】寄生虫病と呼ばれる病
気は、人間および動物の健康ならびに農業に多大の被害
を及ぼす。そのような背景から新規にして有用な駆虫活
性物質の出現とその有利な製造法は常に求められる課題
である。本発明者らは以上のような点に着目し、その可
能性のある新規な物質を提供するとともに、その製造法
を確立することを目的とした。A disease called parasitic disease causes a great deal of damage to human and animal health and agriculture. From such a background, the emergence of new and useful anthelmintic active substances and their advantageous production methods are always demanded. The present inventors have paid attention to the above points, and have aimed to provide a novel substance having the possibility and to establish a manufacturing method thereof.
【０００４】[0004]
【課題を解決するための手段】本発明者らは上記の課題
を解決すべく新規な駆虫剤としての用途が期待される化
合物の探索を行って来たところ、上述の駆虫活性を有す
る環状デプシペプチド（PF1022物質）生産菌の培養物中
に、PF1022物質と類似の物理化学的性質を有する環状デ
プシペプチドPF1022E物質が存在することを見出し、こ
れを単離し、その物理化学的性質を明らかにすることに
より本発明を完成させた。本発明の目的は、新規環状デ
プシペプチドPF1022E物質ならびにその製造法を提供す
ることにある。第１の本発明の要旨とするところは、下
記の式（Ｉ）Means for Solving the Problems The present inventors have searched for compounds expected to be used as novel antiparasitic agents in order to solve the above problems. As a result, the cyclic depsipeptide having the above-mentioned anthelmintic activity is found. (PF1022 substance) By discovering that the cyclic depsipeptide PF1022E substance having physicochemical properties similar to that of the PF1022 substance exists in the culture of the producing bacterium, isolating it, and clarifying its physicochemical properties The present invention has been completed. An object of the present invention is to provide a novel cyclic depsipeptide PF1022E substance and a method for producing the same. The gist of the first aspect of the present invention lies in the following formula (I):
【０００５】[0005]
【化２】 （Ｉ） （Ｐｈはフェニル基を示し、Ｍｅはメチル基を示す。）[Chemical 2] (I) (Ph represents a phenyl group and Me represents a methyl group.)
【０００６】で表される環状デプシペプチドPF1022E 物
質を提供することである。さらに第２の発明は、糸状菌
に属するPF1022E物質生産菌を培養し、その培養物からP
F1022E物質を採取することを特徴とするPF1022E物質の
製造法にある。本発明に使用されるPF1022E物質生産菌
の一例としては、1988年、沖縄県与那国島のサトウキビ
葉から分離されたPF1022株がある。本菌株は工業技術院
微生物工業技術研究所に微工研菌寄第P-10504号として
寄託されていたが、現在は微工研条寄第2671号（FERM B
P-2671）として寄託されている。本菌株の性状は本発明
者らによる発明；「環状デプシペプチド物質およびその
製造法ならびにそれを含有する駆虫剤」（特開平3-3579
6) に述べられているものと同一である。A cyclic depsipeptide PF1022E substance represented by Furthermore, the second invention cultivates a PF1022E substance-producing bacterium belonging to the filamentous fungus,
The method for producing a PF1022E substance is characterized in that the F1022E substance is collected. An example of the PF1022E substance-producing bacterium used in the present invention is the PF1022 strain isolated in 1988 from sugar cane leaves on Yonaguni Island, Okinawa Prefecture. This strain had been deposited at the Institute of Microbial Science and Technology of the Institute of Industrial Science and Technology as Microconc.
It has been deposited as P-2671). The characteristics of this strain are the inventions of the present inventors; “Cyclic depsipeptide substance and its production method and anthelmintic agent containing the same” (JP-A-3-3579).
It is the same as described in 6).
【０００７】１．PF1022E物質生産菌の培養法 無胞子不完全菌目に属するPF1022E物質生産菌を通常の
微生物が利用しうる栄養物を含有する培地で培養する。
栄養源としては、従来カビの培養に利用されている公知
のものが使用できる。例えば、炭素源としては、グルコ
−ス、シュクロ−ス、水飴、デキストリン、澱粉、グリ
セロ−ル、糖密、動・植物油等を使用しうる。また、窒
素源としては、大豆粉、小麦胚芽、コ−ン・スティ−ブ
・リカ−、綿実粕、肉エキス、ペプトン、酵母エキス、
硫酸アンモニウム、硝酸ナトリウム、カリウム、カルシ
ウム、マグネシウム、コバルト、塩素、燐酸、硫酸およ
びその他のイオンを生成することができる無機塩類を添
加することは有効である。また、菌の発育を助け、PF10
22E物質の生産を促進するような有機および無機物を適
当に添加することができる。1. Cultivation method of PF1022E substance-producing bacterium The PF1022E substance-producing bacterium belonging to the incomplete Asporia order is cultured in a medium containing nutrients that can be used by ordinary microorganisms.
As the nutrient source, known ones conventionally used for culturing fungi can be used. For example, as the carbon source, glucose, sucrose, starch syrup, dextrin, starch, glycerol, sugar concentrate, animal / vegetable oil and the like can be used. As the nitrogen source, soybean flour, wheat germ, cone steve liquor, cottonseed meal, meat extract, peptone, yeast extract,
It is effective to add ammonium sulfate, sodium nitrate, potassium, calcium, magnesium, cobalt, chlorine, phosphoric acid, sulfuric acid and other inorganic salts capable of forming ions. It also helps the growth of the bacteria, PF10
Organic and inorganic substances which promote the production of 22E substance can be added appropriately.
【０００８】培養法としては、好気的条件での培養法、
特に深部培養法が最も適している。培養に適当な温度は
15〜30℃であるが、多くの場合26℃付近で培養する。PF
1022E物質の生産は培地や培養条件により異なるが、振
盪培養、タンク培養のいずれにおいても通常2〜10日間
でその蓄積が最高に達する。培養中のPF1022E物質の蓄
積量が最高になった時に培養を停止し、培養液から目的
物質を単離精製する。As the culture method, a culture method under aerobic conditions,
Particularly, the deep culture method is most suitable. Suitable temperature for culturing
The temperature is 15 to 30 ° C, but in most cases, the culture is performed at around 26 ° C. PF
The production of 1022E substance varies depending on the medium and culture conditions, but the maximum accumulation is usually reached in 2 to 10 days in both shaking culture and tank culture. When the accumulated amount of the PF1022E substance in the culture reaches the maximum, the culture is stopped, and the target substance is isolated and purified from the culture solution.
【０００９】２．PF1022E物質の精製法 本発明によって得られるPF1022E物質の培養液からの採
取に当たっては、その性状を利用した通常の分離手段、
例えば、溶剤抽出法、イオン交換樹脂法、吸着又は分配
カラムクロマト法、ゲルろ過法、透析法、沈澱法等を単
独でまたは適宜組合せて抽出精製することができる。例
えば、培養菌体中からはアセトン−水、メタノ−ル−水
または酢酸エチル等で抽出される。また培養液中に蓄積
されたPF1022E物質は、水と混ざらない有機溶剤、例え
ば、ブタノ−ル、酢酸エチル等で抽出すれば有機溶剤層
に抽出される。PF1022E物質を更に精製するには、シリ
カゲル（ワコ−ゲルC-200、和光純薬工業社製等) 、ア
ルミナ等の吸着剤やセファデックスLH-20（ファルマシ
ア社製）、トヨパ−ルHW-40（株式会社東ソ−社製）等
を用いるクロマグラフィ−を行うとよい。以上のような
方法により、あるいはこれらを適宜組合せることによ
り、高純度のPF1022E物質が得られる。得られたPF1022E
物質の物理化学的性状は次の通りである。2. Purification method of PF1022E substance In collecting from the culture solution of the PF1022E substance obtained by the present invention, a normal separation means utilizing its properties,
For example, a solvent extraction method, an ion exchange resin method, an adsorption or distribution column chromatography method, a gel filtration method, a dialysis method, a precipitation method and the like can be used alone or in combination and extracted and purified. For example, acetone-water, methanol-water, ethyl acetate or the like is extracted from the cultured cells. The PF1022E substance accumulated in the culture solution can be extracted into the organic solvent layer by extracting with an organic solvent immiscible with water, such as butanol or ethyl acetate. To further purify the PF1022E substance, silica gel (Wako-Gel C-200, manufactured by Wako Pure Chemical Industries, Ltd.), an adsorbent such as alumina, Sephadex LH-20 (manufactured by Pharmacia), Toyopar HW-40 Chromagraphy using (manufactured by Toso Co., Ltd.) or the like may be performed. The PF1022E substance with high purity can be obtained by the above method or by appropriately combining them. Obtained PF1022E
The physicochemical properties of the substance are as follows.
【００１０】１．PF1022E物質の物理化学的性状 （１）色および形状 ：無色粉末 （２）融点 ：142〜144℃ （３）分子式 ：Ｃ52Ｈ76Ｎ4Ｏ13
（４）マススペクトル (EI-MS) ：m/z 964 （Ｍ+） （５）比旋光度 ：〔α〕D25 ＝−100
。(c 1.0, MeOH) （６）紫外部吸収スペクトル ： λmax nm (MeOH,E1% 1cm)：278(6.5) （７）赤外部吸収スペクトル ： 図１ 3434,2959,2872,1744,1663,1518,1470,1416,1370,1331,
1271,1194,1128,1078,1028,835,750,702,511 （KBr cm
ー1） （８） 1Ｈ ＮＭＲスペクトル ： 図２ （９）溶解性 ：クロロホルム、アセトン、酢酸エチ
ル、メタノ−ル、ジメチルスルホキシドに可溶で、水に
不溶である。 （10）薄層クロマトグラフィ−（シリカゲルプレ−ト60
F254、0.25mm、西独メルク社製）：クロロホルム：酢酸
エチル＝１：１ Rf値 0.24 （11）塩基性、酸性、中性の区分：中性物質 さらに構造研究の結果、PF1022E物質の化学構造を、前
記の式（Ｉ）のごとく決定した。1. Physicochemical properties of PF1022E substance (1) Color and shape: colorless powder (2) Melting point: 142-144 ° C (3) Molecular formula: C 52 H 76 N 4 O 13
(4) Mass spectrum (EI-MS): m / z 964 (M + ) (5) Specific rotation: [α] D 25 = -100
. (c 1.0, MeOH) (6) Ultraviolet absorption spectrum: λ max nm (MeOH, E 1% 1cm ): 278 (6.5) (7) Infrared absorption spectrum: Fig. 1 3434,2959,2872,1744,1663, 1518,1470,1416,1370,1331,
1271,1194,1128,1078,1028,835,750,702,511 (KBr cm
-1 ) (8) 1 H NMR spectrum: Fig. 2 (9) Solubility: Soluble in chloroform, acetone, ethyl acetate, methanol and dimethyl sulfoxide, but insoluble in water. (10) Thin layer chromatography (silica gel plate 60
F 254 , 0.25mm, manufactured by Merck & Co., Ltd. of West Germany): Chloroform: Ethyl acetate = 1: 1 Rf value 0.24 (11) Basic, acidic, neutral classification: Neutral substance As a result of further structural studies, the chemical structure of PF1022E substance Was determined as in formula (I) above.
【００１１】以下に本発明の実施例を示すが、PF1022E
物質の性状が本発明によって明らかにされたので、それ
らの性状にもとづきPF1022E物質の製造法を種々考案す
ることができる。従って本発明は実施例に限定されるも
のではなく、実施例の修飾手段は勿論、本発明によって
明らかにされたPF1022E物質の性状にもとづいて公知の
手段を施してPF1022E物質を生産、濃縮、抽出、精製す
る方法をすべて包括する。An example of the present invention will be shown below. PF1022E
Since the properties of the substance have been clarified by the present invention, various methods for producing the PF1022E substance can be devised based on those properties. Therefore, the present invention is not limited to the examples, the modification means of the examples, of course, the known means based on the properties of the PF1022E substance revealed by the present invention to produce, concentrate and extract the PF1022E substance. , Including all methods of purification.
【００１２】[0012]
【実施例】種培地として、可溶性澱粉2.0%、グルコ−ス
1.0%、ポリペプトン0.5%、小麦胚芽0.6%、酵母エキス0.
3%、大豆粕0.2%、炭酸カルシウム0.2%の組成からなる培
地を用いた。また生産培地として、グルコ−ス2.0%、澱
粉1.0%、小麦胚芽0.8%、大豆粕1.3%、肉エキス0.38% 、
塩化ナトリウム0.13%、炭酸カルシウム0.15%の組成から
なる培地を用いた。なお、殺菌前pHはすべてpH7.0に調
整して使用した。[Example] As a seed medium, soluble starch 2.0%, glucose
1.0%, polypeptone 0.5%, wheat germ 0.6%, yeast extract 0.
A medium having a composition of 3%, soybean meal 0.2% and calcium carbonate 0.2% was used. As a production medium, glucose 2.0%, starch 1.0%, wheat germ 0.8%, soybean meal 1.3%, meat extract 0.38%,
A medium having a composition of 0.13% sodium chloride and 0.15% calcium carbonate was used. The pH before sterilization was adjusted to pH 7.0 before use.
【００１３】前記の種培地(40 ml)を分注した200 ml容
三角フラスコを120℃で15分間殺菌し、PF1022株の斜面
寒天培養の2〜3白金耳を接種し、26℃で48時間振盪培養
して種培養とした。次いで、前記の種培地50 Lを130 L
容醗酵槽に仕込み120 ℃で15分間殺菌し、これに前記フ
ラスコ種培養25本を接種して、26℃で48時間振盪培養
し、これをタンク種培養とした。次いで、前記の生産培
地１KLを２KL容醗酵槽に仕込み、120 ℃で25分間殺菌
し、これに前記タンク種培養より40L接種し、26℃で７
日間通気攪拌培養した。培養終了後、濾過助剤として珪
藻土を加えて濾過し、菌体約90gを得た。A 200 ml Erlenmeyer flask into which the seed medium (40 ml) was dispensed was sterilized at 120 ° C. for 15 minutes, inoculated with 2 to 3 platinum loops of a slope agar culture of PF1022 strain, and at 26 ° C. for 48 hours. Shaking culture was used as a seed culture. Then, 50 L of the above seed medium was added to 130 L.
It was charged into a fermenter and sterilized at 120 ° C for 15 minutes, 25 seed cultures of the above flask were inoculated into the fermenter, and the mixture was shake-cultured at 26 ° C for 48 hours to obtain a tank seed culture. Then, 1 KL of the above-mentioned production medium was charged into a 2 KL fermenter and sterilized at 120 ° C. for 25 minutes, and 40 L of the above-mentioned tank seed culture was inoculated into the fermenter at 26 ° C.
The culture was performed with aeration and stirring for one day. After the culture was completed, diatomaceous earth was added as a filter aid and the mixture was filtered to obtain about 90 g of bacterial cells.
【００１４】２バッチ分の菌体180Kgにメタノ−ル(710
L)を加え、２時間攪拌後菌体を濾別して菌体抽出液を得
た。菌体抽出液は、減圧下でメタノ−ルを留去して50 L
の濃縮液とした。この濃縮液を酢酸エチル(60 L)を加
え、活性成分を抽出し、酢酸エチル層を濃縮乾固し油状
物質を得た。この油状物質にヘキサン- アセトニトリル
の混合溶媒5 Lを加え攪拌後分配したアセトニトリル濃
縮乾固し、粉末(1.64 Kg)を得た。この粉末をメタノ−
ル−脱イオン水1.64 L（50:1）に溶解し氷冷して5時間
攪拌し、一夜冷却し結晶化した。結晶をNo.3のグラスフ
ィルタ−で濾過し、冷メタノ−ル(2.3 L)で洗う。結晶
母液を濃縮乾固し粉末260gを得た。この粉末260gのう
ち、40 gをシリカゲルのカラムクロマト（クロロホル
ム：酢酸エチル＝１：１、ワコ−ゲルＣ-200 400 g）で
精製を２回、（クロロホルム：酢酸エチル＝２：１、ワ
コ−ゲルＣ-200 400 g）で精製を１回行いPF1022E物質
1.77 gを得た。本物質は前記の物理化学的性状を有す
る。Two batches of bacterial cells (180 kg) were treated with methanol (710
L) was added and the mixture was stirred for 2 hours, and the bacterial cells were filtered off to obtain a bacterial cell extract. The bacterial cell extract was distilled under a reduced pressure to remove methanol to obtain 50 L.
The concentrated solution of Ethyl acetate (60 L) was added to this concentrated solution to extract the active ingredient, and the ethyl acetate layer was concentrated to dryness to obtain an oily substance. To this oily substance, 5 L of a mixed solvent of hexane-acetonitrile was added, and the mixture was stirred and distributed, and the acetonitrile was concentrated to dryness to obtain a powder (1.64 Kg). This powder was
Le-deionized water was dissolved in 1.64 L (50: 1), ice-cooled, stirred for 5 hours and cooled overnight for crystallization. The crystals are filtered through a No. 3 glass filter and washed with cold methanol (2.3 L). The crystal mother liquor was concentrated to dryness to obtain 260 g of powder. Of 260 g of this powder, 40 g was purified twice by silica gel column chromatography (chloroform: ethyl acetate = 1: 1, Waco-Gel C-200 400 g) (chloroform: ethyl acetate = 2: 1, Waco-gel). One purification with Gel C-200 400 g) and PF1022E substance
Got 1.77 g. This substance has the above-mentioned physicochemical properties.
【００１５】[0015]
【発明の効果】本発明のPF1022E物質は、新規な環状デ
プシペプチドでありPF1022物質と同様に駆虫剤としての
用途が期待される。The PF1022E substance of the present invention is a novel cyclic depsipeptide and is expected to be used as an anthelmintic agent like the PF1022 substance.
【００１６】[0016]
【図面の簡単な説明】[Brief description of drawings]
【図１】PF1022E物質のKBr中での赤外部吸収スペクトル[Figure 1] Infrared absorption spectrum of PF1022E substance in KBr
【図２】PF1022E物質の重メタノ−ル溶液中での500 MHz
1H NMRスペクトルFigure 2: 500 MHz of PF1022E substance in heavy methanol solution
1 H NMR spectrum
───────────────────────────────────────────────────── フロントページの続き (72)発明者 高木 誠之 神奈川県横浜市港北区師岡町760番地 明 治製菓株式会社薬品総合研究所内 (72)発明者 岡田 忠明 神奈川県横浜市港北区師岡町760番地 明 治製菓株式会社薬品総合研究所内 (72)発明者 村井 安 神奈川県小田原市栢山788 明治製菓株式 会社薬品技術研究所内 (72)発明者 米田 利夫 神奈川県小田原市栢山788 明治製菓株式 会社薬品技術研究所内 (72)発明者 飯沼 勝春 神奈川県小田原市栢山788 明治製菓株式 会社薬品技術研究所内 ─────────────────────────────────────────────────── ─── Continuation of the front page (72) Masayuki Takagi, 760, Shimooka-cho, Kohoku-ku, Yokohama-shi, Kanagawa Meiji Seika Co., Ltd., Pharmaceutical Research Laboratory (72) Tadaaki Okada, 760, Shimo-oka, Kohoku-ku, Yokohama-shi, Kanagawa Meiji Confectionery Co., Ltd., Pharmaceutical Research Laboratory (72) Inventor, Yasushi Murai, 788 Kajiyama, Odawara, Kanagawa Prefecture Meiji Seika Co., Ltd., Pharmaceutical Technology Research Institute (72) Inventor, Toshio Yoneda, 788, Kajiyama, Odawara, Kanagawa Prefecture Meiji Confectionary Co., Ltd. In-house (72) Inventor Katsuharu Iinuma 788 Kayayama, Odawara-shi, Kanagawa Meiji Seika Co., Ltd.
Claims (2)
で表される環状デプシペプチドPF1022E 物質。1. The following formula (I): (I) (Ph represents a phenyl group and Me represents a methyl group.)
A cyclic depsipeptide PF1022E substance represented by:
産菌を培養し、その培養物から請求項１で示されるPF10
22E物質を採取することを特徴とするPF1022E物質の製造
法。2. A PF1022E substance-producing bacterium belonging to a non-sporeless bacterium is cultured, and PF10 shown in claim 1 is obtained from the culture.
A method for producing a PF1022E substance, which comprises collecting 22E substance.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP27909492A JP2873894B2 (en) | 1992-10-19 | 1992-10-19 | Cyclic depsipeptide and method for producing the same |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP27909492A JP2873894B2 (en) | 1992-10-19 | 1992-10-19 | Cyclic depsipeptide and method for producing the same |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH06184126A true JPH06184126A (en) | 1994-07-05 |
| JP2873894B2 JP2873894B2 (en) | 1999-03-24 |
Family
ID=17606336
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| Application Number | Title | Priority Date | Filing Date |
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| JP27909492A Expired - Fee Related JP2873894B2 (en) | 1992-10-19 | 1992-10-19 | Cyclic depsipeptide and method for producing the same |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1997011064A1 (en) * | 1995-09-22 | 1997-03-27 | Meiji Seika Kaisha, Ltd. | Novel cyclic depsipeptide pf1022 derivatives |
| WO1997020945A1 (en) * | 1995-12-07 | 1997-06-12 | Bayer Aktiengesellschaft | Process for the preparation of substituted aryl lactic acid containing cyclodepsipeptides with 24 ring atoms |
| WO1998005655A1 (en) * | 1996-08-07 | 1998-02-12 | Meiji Seika Kaisha, Ltd. | Process for producing cyclodepsipeptide compounds and novel cyclodepsipeptide |
| JP2013513567A (en) * | 2009-12-11 | 2013-04-22 | バイエル・インテレクチュアル・プロパティ・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツング | Novel 24-membered cyclooctadepsipeptide derived from fungal strains and its use as an anthelmintic or endoparasite control agent |
-
1992
- 1992-10-19 JP JP27909492A patent/JP2873894B2/en not_active Expired - Fee Related
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1997011064A1 (en) * | 1995-09-22 | 1997-03-27 | Meiji Seika Kaisha, Ltd. | Novel cyclic depsipeptide pf1022 derivatives |
| US6329338B1 (en) * | 1995-09-22 | 2001-12-11 | Meiji Seika Kaisha, Ltd. | Derivatives of cyclodepsipeptide PF1022 substance |
| WO1997020945A1 (en) * | 1995-12-07 | 1997-06-12 | Bayer Aktiengesellschaft | Process for the preparation of substituted aryl lactic acid containing cyclodepsipeptides with 24 ring atoms |
| US6033879A (en) * | 1995-12-07 | 2000-03-07 | Bayer Aktiengesellschaft | Process for the preparation of substituted aryl lactic acid containing cyclodepsipeptides with 24 ring atoms |
| WO1998005655A1 (en) * | 1996-08-07 | 1998-02-12 | Meiji Seika Kaisha, Ltd. | Process for producing cyclodepsipeptide compounds and novel cyclodepsipeptide |
| CN1082052C (en) * | 1996-08-07 | 2002-04-03 | 明治制果株式会社 | Process for producing cyclodepsipeptide compounds and novel cyclodepsipeptide |
| JP2013513567A (en) * | 2009-12-11 | 2013-04-22 | バイエル・インテレクチュアル・プロパティ・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツング | Novel 24-membered cyclooctadepsipeptide derived from fungal strains and its use as an anthelmintic or endoparasite control agent |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2873894B2 (en) | 1999-03-24 |
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