WO1999067281A1 - Cyclooctadepsipeptides substitues - Google Patents

Cyclooctadepsipeptides substitues Download PDF

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Publication number
WO1999067281A1
WO1999067281A1 PCT/EP1999/004028 EP9904028W WO9967281A1 WO 1999067281 A1 WO1999067281 A1 WO 1999067281A1 EP 9904028 W EP9904028 W EP 9904028W WO 9967281 A1 WO9967281 A1 WO 9967281A1
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WO
WIPO (PCT)
Prior art keywords
spp
formula
substituted
stands
amino
Prior art date
Application number
PCT/EP1999/004028
Other languages
German (de)
English (en)
Inventor
Jürgen Scherkenbeck
Hubert Dyker
Andrew Plant
Achim Harder
Georg Von Samson Himmelstjerna
Original Assignee
Bayer Aktiengesellschaft
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 Aktiengesellschaft filed Critical Bayer Aktiengesellschaft
Priority to JP2000555932A priority Critical patent/JP2002518520A/ja
Priority to KR1020007013553A priority patent/KR20010043957A/ko
Priority to HU0102476A priority patent/HUP0102476A3/hu
Priority to PL99345866A priority patent/PL345866A1/xx
Priority to CA002332122A priority patent/CA2332122A1/fr
Priority to AU45114/99A priority patent/AU4511499A/en
Priority to EP99927953A priority patent/EP1090031A1/fr
Priority to BR9911574-3A priority patent/BR9911574A/pt
Publication of WO1999067281A1 publication Critical patent/WO1999067281A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K11/00—Depsipeptides having up to 20 amino acids in a fully defined sequence; Derivatives thereof
    • C07K11/02—Depsipeptides having up to 20 amino acids in a fully defined sequence; Derivatives thereof cyclic, e.g. valinomycins ; Derivatives thereof
    • 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
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K38/00—Medicinal preparations containing peptides

Definitions

  • the invention relates to new substituted cyclooctadepsipeptides, processes for their preparation and their use for controlling parasites, in particular helminths in veterinary and human medicine, and intermediates for their preparation.
  • a cyclooctadepsipeptide with the name PF1022 is known from EP 382 173 A2. From EP 626 376 AI, EP 634 408 AI and EP 718 293 AI further 24-membered cyclodepsipeptides are known. Their anthelmintic effect is not satisfactory in all cases.
  • a method for sulfonylating depsipeptides is known from WO 96/11 945. However, no unified connections are known from this.
  • Amino, mono- or dialkylamino with 1 to 4 carbon atoms per alkyl part Bis (hydroxyalkyl) amino with 1-4 C-atoms in the alkyl part, bis (alkoxyalkyl) - amino with 1 to 4 C-atoms per alkoxy or alkyl part, mono- or di-C ⁇ _4-alkylamino by phenyl, furyl, morpholinyl or pyridyl is substituted;
  • n 0, 1 or 2
  • m stands for 1 or 2.
  • C 1 -C 4 -alkyl may be mentioned as substituents for the optionally substituted radicals.
  • Acyl such as Cj. 4- alkylcarbonyl, benzoyl, C ] _ 4 -alkoxycarbonyl.
  • the compounds of the formula (I) according to the invention are outstandingly suitable for controlling helminths in veterinary and human medicine.
  • R 1 represents -SO 2 -A
  • n and m stand for 1,
  • R 2 represents hydrogen or - SO 2 -A
  • A preferably represents amino, mono- or dimethyl-, diethyl-, diisopropyl-amino, N-mono- or N, N-bis (ethoxymethyl) amino, - (hydroxyethyl) amino, - (ethoxyethyl) amino, - (methoxyethyl) amino, mono- or dibenzylamino.
  • R 1 and R 2 stand for the radical -SO 2 -A in the para position, where A stands for 1-piperazinyl, which is optionally simply substituted by C j ⁇ alkylcarbonyl or C j " 4 alkoxycarbonyl, furthermore amino, Mono- C ⁇ _ alkyl amino, the alkyl part is optionally simply substituted by morpholino, furyl or pyridyl, Di-Cj. 4 -alkylamino, furthermore 1-pyrrolidinyl or 1-piperidinyl.
  • A stands for 1-piperazinyl, which is optionally simply substituted by C j ⁇ alkylcarbonyl or C j " 4 alkoxycarbonyl, furthermore amino, Mono- C ⁇ _ alkyl amino, the alkyl part is optionally simply substituted by morpholino, furyl or pyridyl, Di-Cj. 4 -alkylamino, furthermore 1-pyrrolidinyl or 1-piperidinyl.
  • the new substituted cyclic depsipeptides of the formula (I) and their acid addition salts and metal salt complexes have very good anthelmintic properties and can preferably be used in the field of veterinary medicine. Surprisingly, they are more effective in combating worm diseases than constitutionally similar, known compounds of the same type
  • halosulfonic acids HalS0 3 H
  • chlorosulfonic acid or with sulfuryl chloride or sulfur dioxide / chlorine
  • Lewis acids optionally in one against the reaction genetically inert diluent and optionally in the presence of Lewis acids.
  • the reaction takes place at temperatures from 0 to 150 ° C., preferably at 0 to 80 ° C., particularly preferably at 0 to 60 ° C.
  • Suitable diluents are all organic solvents which are inert to the reagents. These include in particular aliphatic and aromatic, optionally halogenated hydrocarbons, such as pentane, hexane, heptane, cyclohexane. Petroleum ether, gasoline, ligroin, benzene, toluene, methylene chloride, ethylene chloride. Chloroform, carbon tetrachloride, chlorobenzene and o-dichlorobenzene, furthermore ethers such as diethyl and dibutyl ether, glycol dimethyl ether and diglycol dimethyl ether.
  • ketones such as acetone, methyl ether, methyl isopropyl and methyl isobutyl ketone, also esters, such as methyl acetate and ethyl acetate, and also nitriles, e.g. Acetonitrile and propionitrile,
  • Benzonitrile e.g. Dimethylformamide, dimethylacetamide and N-methylpyrrolidone, as well as dimethyl sulfoxide, tetramethylene sulfone and hexamethylphosphoric acid triamide.
  • amides e.g. Dimethylformamide, dimethylacetamide and N-methylpyrrolidone, as well as dimethyl sulfoxide, tetramethylene sulfone and hexamethylphosphoric acid triamide.
  • the depsipeptides are reacted with an excess of reagent (5 to 10 equivalents) and an excess of Lewis acid (15 to 20 equivalents).
  • halogen sulfones in particular chlorosulfones, obtainable in this stage are compounds of the formula (I) in which the radicals R 1 and / or R 2 represent the radical -S0 2 -halogen, in particular -SO 2 -Cl.
  • diluents mentioned above are suitable as diluents for the implementation of the halogen sulfones. Either the amine is used as the base
  • Forml A-H is used in excess or alkali metal hydroxides, alkali metal or alkaline earth metal carbonates or tertiary, aliphatic or aromatic amines are used.
  • the second stage of the reaction takes place either after the product of the first stage has been isolated and purified, or immediately after the first stage. It is carried out at temperatures from -10 to + 150 ° C, preferably between -5 ° C and + 20 ° C. It is operated at normal pressure.
  • the compound PF 1022 can also be reacted with sulfuric acid (oleum) to give the corresponding -SO OH substituted compound. This compound can then be reacted with a halogenating agent to give the corresponding halogen sulfone. The halogen sulfone is then reacted with amines to the corresponding sulfonamides as described above.
  • the diluent is distilled off and the compounds of the formula (I) are reacted in the customary manner, e.g. chromatographically, cleaned.
  • the active ingredients are suitable for combating pathogenic endoparasites, which occur in humans and in animal husbandry and animal breeding in useful, breeding, zoo, laboratory, experimental and hobby animals, with favorable warm-blooded toxicity. They are effective against all or individual stages of development of the pests and against resistant and normally sensitive species. By fighting the pathogenic endoparasites, disease. Deaths and reduced performance (for example in the production of meat, milk, wool, skins, eggs, honey, etc.) are reduced, so that the use of the active ingredients results in a more economical and more specialized animal husbandry is possible.
  • Pathogenic endoparsites include cesthodes, trematodes, nematodes, acantocephals in particular:
  • Cyclophyllidea for example: Mesocestoides spp., Anoplocephala spp., Paranoplocephala spp., Moniezia spp., Thysanosomsa spp., Thysaniezia spp., Avitelellina spp., Stilesia spp., Cittotaenia spp., Andyella spp., Bertella spp spp., Taenia spp., Echinococcus spp., Hydatigera spp., Davainea spp., Raillietina spp., Hymenolepis spp., Echinolepis spp., Echinocotyle spp., Diorchis spp., Dipylidium spp., Joyeuxiella spp., Diplop. .
  • Opisthorchis spp. Clonorchis spp. Metorchis spp., Heterophyes spp., Metagonimus spp ..
  • Stronylus spp. Triodontophorus spp., Oesophagodontus spp., Trichonema spp., Gyalocephalus spp., Cylindropharynx spp., Poteriostomum spp., Cyclococercus spp., Cylicostephanus sppum, spp., Oesophag.
  • Stephanurus spp. Ancylostoma spp., Uncinaria spp., Bunostomum spp., Globocephalus spp., Syngamus spp., Cyathostoma spp., Metastrongylus spp., Dictyocaulus spp., Muellerius spp., Protostrongylus spp., Neostr spp., Pneumostrongylus spp., Spicocaulus spp., Elaphostrongylus spp.
  • Parelaphostrongylus spp. Crenosoma spp., Paracrenosoma spp., Angiostrongylus spp., Aelurostrongylus spp., Filaroides spp., Parafilaroides spp., Trichostrongylus spp., Haemonchus spp., Ostertagia spp., Cooperemat. Spp., Marshallemat ., Hyostrongylus spp., Obeliscoides spp., Amidostomum spp., Ollulanus spp ..
  • Oxyuris spp. Enterobius spp., Passalurus spp., Syphacia spp., Aspiculuris spp., Heterakis spp ..
  • Ascaridia for example: Ascaris spp., Toxascaris spp., Toxocara spp., Parascaris spp., Anisakis spp., Ascaridia spp ..
  • the livestock and breeding animals include mammals such as cattle, horses, sheep, pigs, goats, camels, water buffalos, donkeys, rabbits, fallow deer, reindeer, fur animals such as mink, chinchilla, raccoon, birds such as chickens, geese, turkeys, Ducks, freshwater and saltwater fish such as trout, carp, eels, reptiles.
  • Insects such as Honey bee and silkworm.
  • Laboratory and experimental animals include mice, rats, guinea pigs, golden hamsters. Dogs and cats.
  • the pets include dogs and cats.
  • the application can be prophylactic as well as therapeutic.
  • the active ingredients are used directly or in the form of suitable preparations enterally, parenterally, dermally, nasally, by treating the environment or with the aid of shaped articles containing the active ingredient, e.g. Strips, plates, ribbons, collars. Ear tags, limb straps, marking devices.
  • enteral application of the active ingredients takes place e.g. orally in the form of powder. Tablets, capsules, pastes, drinkers, granules, orally applicable solutions.
  • Suspensions and emulsions, boluses, medicated feed or drinking water happens e.g. in the form of diving (dipping), spraying (spraying) or pouring on (pour-on and spot-on).
  • Parenteral use happens e.g. in the form of injection (intramuscular, subcutaneous, intravenous, intraperitoneal) or by implants.
  • Suitable preparations are:
  • Solutions such as solutions for injection, oral solutions, concentrates for oral administration after dilution, solutions for use on the skin or in body cavities.
  • Solid preparations such as powders, premixes or concentrates, granules, pellets, tablets, boluses, capsules; Aerosols and inhalants, molded articles containing active ingredients.
  • Solutions for injection are administered intravenously, intramuscularly and subcutaneously.
  • Injection solutions are prepared by dissolving the active ingredient in a suitable solvent and possibly adding additives such as solubilizers, acids, bases, buffer salts, antioxidants, preservatives.
  • additives such as solubilizers, acids, bases, buffer salts, antioxidants, preservatives.
  • Solutions are sterile filtered and filled.
  • solvents physiologically compatible solvents such as water, alcohols such as ethanol, butanol, benzyl alcohol, glycerol, propylene glycol, polyethylene glycols, N-methyl-pyrrolidone, and mixtures thereof.
  • the active compounds can also be dissolved in physiologically tolerable vegetable or synthetic oils which are suitable for injection.
  • solution mediators solvents which promote the dissolution of the active ingredient in the main solvent or prevent its precipitation.
  • solvents which promote the dissolution of the active ingredient in the main solvent or prevent its precipitation. Examples are polyvinyl pyrrolidone, polyoxyethylated castor oil, polyoxyethylated sorbitan esters.
  • Preservatives are: benzyl alcohol, trichlorobutanol, p-hydroxybenzoic acid ester. n-butanol.
  • Oral solutions are applied directly. Concentrates are used orally after previous dilution to the application concentration. Oral solutions and concentrates are prepared as described above for the injection solutions, whereby sterile work can be dispensed with.
  • Solutions for use on the skin are dripped on, spread on, rubbed in, sprayed on or sprayed on. These solutions are prepared as described above for the injection solutions.
  • Thickeners are: inorganic thickeners such as bentonites, colloidal silica, aluminum monostearate, organic thickeners such as cellulose derivatives, polyvinyl alcohols and their copolymers, acrylates and metacrylates.
  • Gels are applied to or spread on the skin or placed in body cavities. Gels are produced by adding sufficient thickening agent to solutions which have been prepared as described for the injection solutions to produce a clear mass with an ointment-like consistency.
  • the thickeners specified above are used as thickeners.
  • Pour-on formulations are poured or sprayed onto limited areas of the skin, the active ingredient penetrating the skin and acting systemically.
  • pour-on formulations are prepared by dissolving, suspending or emulsifying the active ingredient in suitable solvents or solvent mixtures that are compatible with the skin. If necessary, other auxiliaries such as dyes, absorption-promoting substances, antioxidants, light stabilizers and adhesives are added.
  • solvents water, alkanols, glycols, polyethylene glycols, polypropylene glycols, glycerol, aromatic alcohols such as benzyl alcohol, phenylethanol. Phenoxyethanol, esters such as ethyl acetate, butyl acetate, benzyl benzoate, ethers such as Alkylene glycol alkyl ethers such as dipropylene glycol monomethyl ether, diethylene glycol monobutyl ether, ketones such as acetone, methyl ethyl ketone, aromatic and / or aliphatic hydrocarbons, vegetable or synthetic oils, DMF, dimethyl acetamide, N-methyl pyrrolidone, 2,2-dimethyl-4-oxy-methylene 1,3-dioxolane.
  • solvents water, alkanols, glycols, polyethylene glycols, polypropylene glycols, glycerol, aromatic alcohols such as benzyl alcohol, phenylethanol
  • Dyes are all dyes approved for use on animals, which can be dissolved or suspended.
  • Absorbing substances are e.g. DMSO, spreading oils such as isopropyl myristate, dipropylene glycol pelargonate, silicone oils, fatty acid esters, triglycerides, fatty alcohols.
  • spreading oils such as isopropyl myristate, dipropylene glycol pelargonate, silicone oils, fatty acid esters, triglycerides, fatty alcohols.
  • Antioxidants are sulfites or metabisulfites such as potassium metabisulfite, ascorbic acid, butylated hydroxytoluene, butylated hydroxyanisole, tocopherol.
  • Light stabilizers are e.g. Novantisol acid.
  • Adhesives are e.g. Cellulose derivatives, starch derivatives, polyacrylates, natural polymers such as alginates, gelatin.
  • Emulsions can be used orally, dermally or as injections.
  • Emulsions are either water in oil or oil in water.
  • hydrophobic phase paraffin oils, silicone oils, natural ones
  • Vegetable oils such as sesame oil, almond oil, castor oil, synthetic triglycerides such as Capryl capric acid bigylceride, triglyceride mixture with vegetable fatty acids of chain length Cg_i 2 or other specially selected natural fatty acids, partial glyceride mixtures of saturated or unsaturated fatty acids, which may also contain hydroxyl groups, mono- and diglycerides of Cg / Ci Q fatty acids.
  • Fatty acid esters such as ethyl stearate, di-n-butyryl adipate, lauric acid hexyl ester, dipropylene glycol pelargonate, esters of a branched fatty acid of medium chain length with saturated fatty alcohols of chain length Ci ö-Cj, isopropyl myristate, isopropyl palmitate, caprylic / capric alcohol esters of the saturated fatty length C12-C18, isopropyl stearate, oleic acid oleyl ester, oleic acid decyl ester, ethyl oleate, lactic acid ethyl ester, waxy fatty acid esters such as artificial duck pancreas fat, dibutyl phthalate, adipic acid diisopropyl ester, the latter related ester mixtures and others
  • Fatty alcohols such as isotridecyl alcohol, 2-octyldodecanol, cetylstearyl alcohol, oleyl alcohol.
  • Fatty acids such as Oleic acid and its mixtures.
  • hydrophilic phase The following can be mentioned as the hydrophilic phase:
  • Alcohols such as e.g. Propylene glycol, glycerin, sorbitol and their mixtures.
  • nonionic surfactants e.g. polyoxyethylated castor oil, polyoxyethylated sorbitan monooleate, sorbitan monostearate, glycerol monostearate, polyoxyethyl stearate, alkylphenol polyglycol ether;
  • ampholytic surfactants such as di-Na-N-lauryl- ⁇ -iminodipropionate or lecithin;
  • anionic surfactants such as Na lauryl sulfate.
  • auxiliaries substances which increase viscosity and stabilize the emulsion, such as carboxymethyl cellulose, methyl cellulose and other cellulose and starch derivatives, polyacrylates, alginates, gelatin, gum arabic,
  • Polyvinylpyrrolidone polyvinyl alcohol, copolymers of methyl vinyl ether and maleic anhydride, polyethylene glycols, waxes, colloidal silica or mixtures of the substances listed.
  • Suspensions can be used orally, dermally or as an injection. They are produced by suspending the active ingredient in a carrier liquid, optionally with the addition of further auxiliaries such as wetting agents, dyes, absorption-promoting substances, preservatives, antioxidants, and light stabilizers.
  • the surfactants specified above may be mentioned as wetting agents (dispersants).
  • Semi-solid preparations can be administered orally or dermally. They differ from the suspensions and emulsions described above only in their higher viscosity.
  • the active ingredient is mixed with suitable carriers, if appropriate with the addition of auxiliaries, and brought into the desired shape.
  • Inorganic and organic substances serve as such.
  • Inorganic substances are, for example Table salt, carbonates such as calcium carbonate, hydrogen carbonates, aluminum oxides, silicas, clays, precipitated or colloidal silicon dioxide, phosphates.
  • Organic substances are e.g. Sugar, cellulose, food and animal feed such as milk powder, animal meal, cereal flour and meal, starches.
  • Excipients are preservatives, antioxidants, dyes, which have already been listed above.
  • auxiliaries are lubricants and lubricants such as Magnesium stearate, stearic acid, talc, bentonite, decay-promoting substances such as starch or cross-linked polyvinylpyrrolidone, binders such as e.g. Starch, gelatin or linear polyvinylpyrrolidone as well as dry binders such as microcrystalline cellulose.
  • lubricants and lubricants such as Magnesium stearate, stearic acid, talc, bentonite, decay-promoting substances such as starch or cross-linked polyvinylpyrrolidone, binders such as e.g. Starch, gelatin or linear polyvinylpyrrolidone as well as dry binders such as microcrystalline cellulose.
  • the active substances can also be present in the preparations as a mixture with synergists or with other active substances which act against pathogenic endoparasites.
  • Such agents are e.g. L-2,3,5,6-tetrahydro-6-phenyl-imidazothiazole, benzimidazole carbamate, praziquantel, pyrantel, febantel.
  • Ready-to-use preparations contain the active ingredient in concentrations of 10 ppm - 20 percent by weight, preferably 0.1-10 percent by weight.
  • Preparations which are diluted before use contain the active ingredient in concentrations of 0.5-90% by weight, preferably 5 to 50% by weight.

Abstract

Nouveaux cyclooctadepsipeptides substitués de formule (I) dans laquelle R1, R2, m et n sont tels que définis dans le descriptif, procédé de préparation et d'utilisation desdits peptides pour combattre les endoparasites et médicaments contenant ces principes actifs.
PCT/EP1999/004028 1998-06-24 1999-06-11 Cyclooctadepsipeptides substitues WO1999067281A1 (fr)

Priority Applications (8)

Application Number Priority Date Filing Date Title
JP2000555932A JP2002518520A (ja) 1998-06-24 1999-06-11 置換シクロオクタデプシペプチド類
KR1020007013553A KR20010043957A (ko) 1998-06-24 1999-06-11 치환된 시클로옥타뎁시펩타이드
HU0102476A HUP0102476A3 (en) 1998-06-24 1999-06-11 Substituted cyclooctadepsipeptides
PL99345866A PL345866A1 (en) 1998-06-24 1999-06-11 Substituted cyclooctadepsipeptides
CA002332122A CA2332122A1 (fr) 1998-06-24 1999-06-11 Cyclooctadepsipeptides substitues
AU45114/99A AU4511499A (en) 1998-06-24 1999-06-11 Substituted cyclooctadepsipeptides
EP99927953A EP1090031A1 (fr) 1998-06-24 1999-06-11 Cyclooctadepsipeptides substitues
BR9911574-3A BR9911574A (pt) 1998-06-24 1999-06-11 Ciclooctadepsipeptìdeos substituìdos

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19828047A DE19828047A1 (de) 1998-06-24 1998-06-24 Substituierte Cyclooctadepsipeptide
DE19828047.5 1998-06-24

Publications (1)

Publication Number Publication Date
WO1999067281A1 true WO1999067281A1 (fr) 1999-12-29

Family

ID=7871814

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP1999/004028 WO1999067281A1 (fr) 1998-06-24 1999-06-11 Cyclooctadepsipeptides substitues

Country Status (11)

Country Link
EP (1) EP1090031A1 (fr)
JP (1) JP2002518520A (fr)
KR (1) KR20010043957A (fr)
CN (1) CN1307586A (fr)
AU (1) AU4511499A (fr)
BR (1) BR9911574A (fr)
CA (1) CA2332122A1 (fr)
DE (1) DE19828047A1 (fr)
HU (1) HUP0102476A3 (fr)
PL (1) PL345866A1 (fr)
WO (1) WO1999067281A1 (fr)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102008030764A1 (de) 2008-06-28 2009-12-31 Bayer Animal Health Gmbh Kombination von Amidin-Derivaten mit cyclischen Depsipeptiden
WO2010102762A1 (fr) 2009-03-10 2010-09-16 Bayer Animal Health Gmbh Préparation à base d'huile contenant de la triazine antiprotozoaires et des cyclodepsipeptides anthélminthiques
WO2012028556A1 (fr) 2010-08-31 2012-03-08 Bayer Animal Health Gmbh Lactones macrocycliques et leur utilisation et leurs combinaisons avec d'autres substances actives
DE102010064245A1 (de) 2010-12-28 2012-06-28 Bayer Animal Health Gmbh Makrocylischen Lactone und deren Verwendung und deren Kombinationen mit anderen Wirkstoffen

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102008031284A1 (de) * 2008-07-02 2010-01-07 Bayer Schering Pharma Aktiengesellschaft Neue Bekämpfungsmöglichkeit der Giardiose

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0626375A1 (fr) * 1993-05-26 1994-11-30 Bayer Ag Octacyclodepsipeptides ayant une activité endoparasiticide
US5747448A (en) * 1993-02-19 1998-05-05 Meiji Seika Kaisha, Ltd. Derivatives of cyclodepsipeptide PF 1022
WO1998043965A1 (fr) * 1997-04-02 1998-10-08 Bayer Aktiengesellschaft Thiodepsipeptides pour lutter contre des endoparasites et procede simple permettant de les preparer

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5747448A (en) * 1993-02-19 1998-05-05 Meiji Seika Kaisha, Ltd. Derivatives of cyclodepsipeptide PF 1022
EP0626375A1 (fr) * 1993-05-26 1994-11-30 Bayer Ag Octacyclodepsipeptides ayant une activité endoparasiticide
WO1998043965A1 (fr) * 1997-04-02 1998-10-08 Bayer Aktiengesellschaft Thiodepsipeptides pour lutter contre des endoparasites et procede simple permettant de les preparer

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102008030764A1 (de) 2008-06-28 2009-12-31 Bayer Animal Health Gmbh Kombination von Amidin-Derivaten mit cyclischen Depsipeptiden
WO2010102762A1 (fr) 2009-03-10 2010-09-16 Bayer Animal Health Gmbh Préparation à base d'huile contenant de la triazine antiprotozoaires et des cyclodepsipeptides anthélminthiques
DE102009012423A1 (de) 2009-03-10 2010-09-16 Bayer Animal Health Gmbh Zubereitung auf Ölbasis
WO2012028556A1 (fr) 2010-08-31 2012-03-08 Bayer Animal Health Gmbh Lactones macrocycliques et leur utilisation et leurs combinaisons avec d'autres substances actives
DE102010064245A1 (de) 2010-12-28 2012-06-28 Bayer Animal Health Gmbh Makrocylischen Lactone und deren Verwendung und deren Kombinationen mit anderen Wirkstoffen

Also Published As

Publication number Publication date
AU4511499A (en) 2000-01-10
CN1307586A (zh) 2001-08-08
PL345866A1 (en) 2002-01-14
KR20010043957A (ko) 2001-05-25
DE19828047A1 (de) 1999-12-30
EP1090031A1 (fr) 2001-04-11
CA2332122A1 (fr) 1999-12-29
JP2002518520A (ja) 2002-06-25
BR9911574A (pt) 2001-03-20
HUP0102476A2 (hu) 2001-10-28
HUP0102476A3 (en) 2003-08-28

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