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WO1992008454A1 - Utilisation d'avermectines et de milbemycines pour le traitement d'infestations parasitiques chez les ruminants - Google Patents

Utilisation d'avermectines et de milbemycines pour le traitement d'infestations parasitiques chez les ruminants Download PDF

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Publication number
WO1992008454A1
WO1992008454A1 PCT/GB1991/001978 GB9101978W WO9208454A1 WO 1992008454 A1 WO1992008454 A1 WO 1992008454A1 GB 9101978 W GB9101978 W GB 9101978W WO 9208454 A1 WO9208454 A1 WO 9208454A1
Authority
WO
WIPO (PCT)
Prior art keywords
optionally
compound
formula
substituted
treatment
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/GB1991/001978
Other languages
English (en)
Inventor
Roderick John Dorgan
David Owen Morgan
Peter Robin Shelley
Simon Edward Blanchflower
Geoffrey Harold Baker
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.)
Beecham Group PLC
Original Assignee
Beecham Group PLC
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 Beecham Group PLC filed Critical Beecham Group PLC
Publication of WO1992008454A1 publication Critical patent/WO1992008454A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/70—Carbohydrates; Sugars; Derivatives thereof
    • 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
    • A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system

Definitions

  • This invention relates to a method of treating parasites in ruminant animals. 5
  • This invention is particularly concerned with the use of certain avermectins and milbemycins described in EP-A-0 421 568 (USSN 525,094) for the treatment or prophylaxis of endo- and ectoparasitic infestations of 10 ruminants, such as cattle and sheep.
  • the compounds used in this invention have parasiticidal properties, for example against nematodes, and are useful for the treatment of helminthiasis in ruminant animals.
  • helminthiasis encompasses diseases of animals caused by infestation with parasitic worms such as Strongyles, Ascarids, hookworms, lungworms, filarial worms and whipworms.
  • the compounds used in this invention are also active against Arthropods.
  • the phylum Arthropoda comprises insects - such as biting flies, lice, bugs, beetles and fleas - and arachnids - such as mites and ticks.
  • the present invention provides the use of a compound of general formula (I) as defined below for the manufacture of a medicament for the treatment or prophylaxis of endo and ectoparasitic infestations, especially helminthiasis and
  • the present invention also provides a method of treatment or prophylaxis of endo- and ectoparasitic infestations, 35 especially helminthiasis and anthropod or nematode infestations, which comprises administering an effective non-toxic amount of a compound of general formula (I) as defined below to a ruminant animal in need thereof.
  • This invention is particularly concerned with the use of a compound of general formula (I) to combat infestations in ruminants of lice, lungworm, Hypoderma (the larval stage of warble fly) and gastrointestinal worms (such as Cooperia, Trichostronqylus, Haemonchus) .
  • the present invention includes prophylatic treatment of healthy animals to prevent infestation, as well as treatment of infected animals.
  • the compounds of general formula (I) may be formulated for administration with carriers and adjuvants in any convenient way for use in veterinary medicine, by analogy with known anthelmintics.
  • the compounds of general formula (I) may be administered to animals orally (as a paste, drench, bolus, capsule or tablet) , parenterally, percutaneously, as a food additive (eg granules, pellets or powder) , topically (as a cream, wash or spray) , or transdermally (as a pour-on) .
  • a food additive eg granules, pellets or powder
  • topically as a cream, wash or spray
  • transdermally as a pour-on
  • the compounds of general formula (I) may be formulated as a mixture with each other and/or with other anthelmintics, insecticides, acaricides or other pharmacologically active substances.
  • the composition consists of sufficient material to provide a dose of from 0.001 to lOOmg of active ingredient per kg of animal body weight per dose, more suitably 0.01 to lOmg/kg per dose.
  • a composition for use in the invention may suitably contain from 0.1% by weight, preferably from 1.0 to 60% by weight, of the compound of general formula (I) (based on the total -3- weight of the composition) , depending on the method of administration.
  • the compound used in this invention is an avermectin or milbemycin selected from avermectins and milbemycins having the general formula (I) :
  • R 1 1 is hydrogen or optionally protected hydroxy
  • R . is alkoxy, optionally protected hydroxy, oxo or optionally 0-substituted oximmo
  • R° is hydrogen, optionally protected 30 hydroxy,or a group 4'- ( ⁇ -L-oleandrosyl)- ⁇ -L-oleandrosyloxy or ⁇ -L- oleandrosyloxy wherein the terminal hydroxy group is optionally protected
  • R , R , R° and R are the same or o different and each is hydrogen or an organic radical
  • R is an optionally substituted amino or imino group such as optionally O-substituted oxyimino, optionally N-substituted hydrazone, or optionally N-substituted semicarbazone; with the proviso that the compound of formula (I) is not a compound of formula (E) or (F)below or a compound disclosed in EP-A-0 307 220.
  • R 3 is in
  • EP-A-0 259 779, EP-A-0 293 549, EP-A-0 307 225 and GB-A-2192630 describe compounds of formula (E) :
  • R 1 is optionally protected hydroxy or methoxy
  • ⁇ is optionally protected hydroxy, oxo, or an imino group such as optionally O-substituted oxyimino, optionally N-substituted hydrazone, or optionally N-substituted semicarbazone
  • R n is methyl, ethyl or isopropyl
  • the dashed line is a double bond or an epoxide group.
  • R° is optionally protected hydroxy or methoxy
  • P is hydrogen or a sugar residue
  • R ⁇ is optionally protected hydroxy, oxo, or an imino group such as optionally O-substituted oxyimino or optionally N-substituted hydrazone
  • R r is isopropyl or sec-butyl.
  • the compound used in the present invention is VS 54396 or VS 55759 disclosed respectively in Example 6 (Z- and E-isomers) and in Example 36 (E-isomer) of EP-A-0 421 568 (U.S. Patent Application serial No. 525,094). 5
  • the preparation of these compounds is illustrated below as Examples 1 and 2.
  • This product (3.35g 5.7 mmol) was dissolved in methanol (25 ml) and a solution of mercuric oxide (56 mg, 0.26 mmol) water (3.5 ml) and concentrated sulphuric acid (0.75 ml, 14 mmol)was added dropwise at 20°C. The mixture was stirred at 20°C for 2 h., water was added and the mixture was extracted with dichloromethane (3 x 100 ml) . The combined organic layers were washed with sodium bicarbonate solution (100 ml), dried (MgS0 4 ) and evaporated to give the title ketone (3.2g)) pure by nmr + tic.
  • Efficacy was determined by monitoring the number of grubs in the animals back weekly. Grub determination were made by palpating the animal's backs weekly until no new grubs appeared. Charts were prepared at each observation period to show the location of each grub. Exiting grubs were observed, if possible, and a determination made as to their viability.
  • the compound under test was applied by sucutaneous injection.

Landscapes

  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Environmental Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • Pest Control & Pesticides (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Agronomy & Crop Science (AREA)
  • Molecular Biology (AREA)
  • Plant Pathology (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)

Abstract

Les avermectines et les milbémycines sont utiles au traitement ou à la prophylaxie d'infestations endo- et ectoparasitaires chez les ruminants.
PCT/GB1991/001978 1990-11-16 1991-11-11 Utilisation d'avermectines et de milbemycines pour le traitement d'infestations parasitiques chez les ruminants Ceased WO1992008454A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB909024926A GB9024926D0 (en) 1990-11-16 1990-11-16 Novel treatment
GB9024926.9 1990-11-16

Publications (1)

Publication Number Publication Date
WO1992008454A1 true WO1992008454A1 (fr) 1992-05-29

Family

ID=10685474

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/GB1991/001978 Ceased WO1992008454A1 (fr) 1990-11-16 1991-11-11 Utilisation d'avermectines et de milbemycines pour le traitement d'infestations parasitiques chez les ruminants

Country Status (5)

Country Link
AU (1) AU8875091A (fr)
GB (1) GB9024926D0 (fr)
IE (1) IE913970A1 (fr)
WO (1) WO1992008454A1 (fr)
ZA (1) ZA919022B (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1994027598A1 (fr) * 1993-05-26 1994-12-08 Commonwealth Scientific And Industrial Research Organisation Compositions anti-parasitaires

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0237339A1 (fr) * 1986-03-12 1987-09-16 American Cyanamid Company Composés macrolides
EP0259779A1 (fr) * 1986-09-12 1988-03-16 American Cyanamid Company Dérivés des composés LL-F28249 comportant en position 23 un groupement oxo(céto) ou imine
EP0260536A2 (fr) * 1986-09-12 1988-03-23 American Cyanamid Company Dérivés 23-imino de composés 23-céto et leurs utilisation comme pesticides.
EP0260537A1 (fr) * 1986-09-12 1988-03-23 American Cyanamid Company Dérivés 13-déoxy-23-oxo(céto) et 23-imino des composés de 13-déoxy-C-076-aglycone

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0237339A1 (fr) * 1986-03-12 1987-09-16 American Cyanamid Company Composés macrolides
EP0259779A1 (fr) * 1986-09-12 1988-03-16 American Cyanamid Company Dérivés des composés LL-F28249 comportant en position 23 un groupement oxo(céto) ou imine
EP0260536A2 (fr) * 1986-09-12 1988-03-23 American Cyanamid Company Dérivés 23-imino de composés 23-céto et leurs utilisation comme pesticides.
EP0260537A1 (fr) * 1986-09-12 1988-03-23 American Cyanamid Company Dérivés 13-déoxy-23-oxo(céto) et 23-imino des composés de 13-déoxy-C-076-aglycone

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1994027598A1 (fr) * 1993-05-26 1994-12-08 Commonwealth Scientific And Industrial Research Organisation Compositions anti-parasitaires
US5840324A (en) * 1993-05-26 1998-11-24 Commonwealth Scientific And Industrial Organisation Antiparasitic compositions

Also Published As

Publication number Publication date
GB9024926D0 (en) 1991-01-02
IE913970A1 (en) 1992-05-20
ZA919022B (en) 1992-09-30
AU8875091A (en) 1992-06-11

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