WO2002094288A1 - Compositions veterinaires comprenant des derives d'oxime avermectine et du praziquantel - Google Patents

Compositions veterinaires comprenant des derives d'oxime avermectine et du praziquantel Download PDF

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Publication number
WO2002094288A1
WO2002094288A1 PCT/IB2002/001025 IB0201025W WO02094288A1 WO 2002094288 A1 WO2002094288 A1 WO 2002094288A1 IB 0201025 W IB0201025 W IB 0201025W WO 02094288 A1 WO02094288 A1 WO 02094288A1
Authority
WO
WIPO (PCT)
Prior art keywords
praziquantel
selamectin
monosaccharide
formulation
treatment
Prior art date
Application number
PCT/IB2002/001025
Other languages
English (en)
Inventor
Bernard Frank Bishop
Original Assignee
Pfizer Limited
Pfizer Inc.
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 Pfizer Limited, Pfizer Inc. filed Critical Pfizer Limited
Priority to EP02716978A priority Critical patent/EP1381374A1/fr
Priority to CA002443068A priority patent/CA2443068A1/fr
Priority to JP2002591005A priority patent/JP2004526804A/ja
Priority to BR0208654-9A priority patent/BR0208654A/pt
Priority to MXPA03009023A priority patent/MXPA03009023A/es
Publication of WO2002094288A1 publication Critical patent/WO2002094288A1/fr

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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
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/496—Non-condensed piperazines containing further heterocyclic rings, e.g. rifampin, thiothixene or sparfloxacin
    • 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
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/4985—Pyrazines or piperazines ortho- or peri-condensed with heterocyclic ring systems
    • 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
    • A61K31/7042—Compounds having saccharide radicals and heterocyclic rings
    • A61K31/7048—Compounds having saccharide radicals and heterocyclic rings having oxygen as a ring hetero atom, e.g. leucoglucosan, hesperidin, erythromycin, nystatin, digitoxin or digoxin
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00—Antiparasitic agents
    • A61P33/14—Ectoparasiticides, e.g. scabicides
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00

Definitions

  • the invention described herein relates to the provision of a combination therapy in the field of treatment (including prophylaxis) of parasitic infestations and consequences thereof, particularly in veterinary medicine.
  • the invention relates to antiparasitic therapy using a combination of avermectin- like compounds, specifically 13-monosaccharide-5-oxime compounds, and praziquantel.
  • EP 0 717 993 describes a synergistic combination of avermectins/milbemycins with praziquantel, in particular for the treatment of cestode and nematode infestations in horses.
  • Particular species mentioned therein include Anoplocephala perfiolata, Strongylidae, Gasterophilus spp., and Parascari aquorum.
  • Particular avermectins mentioned therein include ivermectin, abamectin, moxidectin and doramectin.
  • Formulations of selamectin in di(C 2 -4 glycol) mono(C ⁇ -4 alkyl) ethers including dipropylene glycol monomethyl ether (DPGMME), and alcohols such as ethanol and isopropy alcohol (IPA) are disclosed in International Patent Application, publication no. WO00/30449, herein incorporated by reference.
  • DPGMME dipropylene glycol monomethyl ether
  • IPA isopropy alcohol
  • Selamectin is the active ingredient of the product marketed under the trade names RevolutionTM, StrongholdTM, etc. by Pfizer Inc. and associated companies, particularly for the treatment (including prophylaxis) of endo- and ecto-parasite infestations in companion animals such as cats and dogs.
  • Praziquantel is 2-(cyclohexylcarbonyl)-1 ,2,3,6,7-11b-hexahydro-4H- pyrazino[2,1-a]isoquinolin-4-one, also known as an active ingredient in EMBAY 8440TM, BiltricideTM, CesolTM, and DroncitTM. It is mentioned in the Merck Index, 11th edition, para.7714, and references therein, herein incorporated by reference.
  • Desirable attributes in particular for a topical application for administration to companion animals such as cats and dogs, and especially in relation to a treatment for the control of flea, heartworm and tapeworm infestation, include: efficacy; persistence of efficacy; low volume; cosmetically acceptable; convenient; need for small number of applications for broad spectrum parasite control; compliant treatment; safe; suitable pharmacokinetic profile; suitable transdermal flux profile; rapid rate of onset; low dose of active ingredient(s); cutaneous tolerability; and stability on storage.
  • Praziquantel has a widespread use in animals orally at higher doses than those which we have tested.
  • Dr. J.A. Shmidl in Shawnee, Kansas treated two cats orally with doses of 25 and 50 mg/kg. There were no signs of clinical toxicity or evidence of gross lesions in the gastrointestinal tract.
  • Dr. S.M. Kruckenberg reports on the oral treatment of seven cats (6 females and 1 male) with a 5 mg/kg dose during all critical periods of reproduction. Two groups of seven cats (6 females and 1 male) each were also treated subcutaneously and intramuscularly with a praziquantel injectable solution with a 5 mg/kg dose during all critical periods of reproduction. Dr. Kruckenberg further evaluated the oral use of praziquantel in one male and three female cats in a controlled study. Two groups of 4 cats (1 male and 3 females) each were also treated subcutaneously and intramuscularly with the praziquantel injectable solution. All treated cats received 3X the label rate. Four females and 1 male served as untreated controls.
  • the treated males received 7 treatments at 2-week intervals throughout the breeding season. Each treated female received a treatment prior to breeding, during the embryogenic period of pregnancy, during late pregnancy and again during lactation.
  • the study confirmed the lack of effects on fertility, conception, fetal development or pregnancy when praziquantel was administered at 3X dosage levels.
  • Dr. Shmidl further treated two kittens (4 1/2 to 7 1/2 weeks old) twice at a 14- day interval.
  • the dosage rate was 5X the label dose. Slight depression was observed in one kitten. No significant clinical toxicity signs or clinical pathology and histopathology changes were attributed to this dosage rate.
  • the safety index for the use of praziquantel tablets in cats has been derived from controlled studies using the final tablet formulation (vomiting was the only effect with dual treatments of 100 mg/kg at a 14-day interval). Vomiting at high dosage rates is the typical reaction which prevents significant clinical toxicity signs from occurring.
  • the safety factor is at least 5X the label rate when the product is administered at 14 day intervals to kittens 5 1/2 weeks of age and older.
  • CUTTER Tape-Tabs (praziquantel) Tapeworm Tablets will remove the common tapeworms, Dipylidium caninum and Taenia taeniaeformis , from cats and kittens.
  • CUTTER Tape-Tabs (praziquantel) Tapeworm Tablets for Cats and Kittens are sized for easy administration to either adult cats or kittens.
  • the tablets may be given directly in the mouth or crumbled and mixed with the food.
  • praziquantel tablets were 100% effective in the treatment of tapeworm infections of dogs and cats due to Taenia pisiformis , Taenia taeniaeformis and Dipylidium caninum. Additionally praziquantel effectively (100%) eliminated experimental T. taeniaeformis infections as young as seven (7) days from cats. Summary of Preclinical Effectiveness Data for Praziquantel Tablets in Cats
  • praziquantel has a solubility above 60 mg/g (6% w/w) even in the presence of selamectin at up to 120 mg/g (12% w/w). Above 50% IPA however, this solubility may be increased to over 90 mg/g (9% w/w) in the supersaturated state.
  • a series of IPA / DPGMME mixtures were prepared in duplicate as outlined in Table 1. To these were added a fixed amount of selamectin to provide a constant concentration of 120 mg per ml i.e. the maximum selamectin concentration found in StrongholdTM.
  • Praziquantel was analysed using an gradient HPLC method modified from that developed for selamectin. This method was validated with respect to praziquantel linearity over the range 10 to 200 mg per ml of praziquantel (in the solubility test solutions) and in the presence of 120 mg per ml of selamectin. This same method was also used to check on the selamectin content in these same solutions.
  • compositions containing selamectin and praziquantel are shown below, wherein the composition within the formulation is expressed % weight by volume:
  • An aspect of the invention is the provision of a combination therapy using a formulation comprising a 13-monosaccharide 5-oxime avermectin such as selamectin at around 6-12% w/v, and praziquantel at around 3-9% w/v (preferably around 6% w/v), in a veterinarily acceptable carrier, diluent or adjuvant.
  • a formulation comprising a 13-monosaccharide 5-oxime avermectin such as selamectin at around 6-12% w/v, and praziquantel at around 3-9% w/v (preferably around 6% w/v), in a veterinarily acceptable carrier, diluent or adjuvant.
  • the (13-monosaccharide 5-oxime avermectin such as selamectin)- containing formulation comprises a di(C 2 - 4 glycol) mono(C 1 ⁇ alkyl) ether and an optional skin-acceptable solvent.
  • the (13-monosaccharide 5-oxime avermectin such as selamectin)- containing formulation is suitable for topical, preferably spot-on, application.
  • Another aspect of the invention is the provision of an antiparasitic combination therapy whereby a 13-monosaccharide 5-oxime avermectin such as selamectin is provided at around 6-12mg/kg (re. host animal) and praziquantel is provided at up to 18mg/kg (re. host animal).
  • a 13-monosaccharide 5-oxime avermectin such as selamectin is provided at around 6-12mg/kg (re. host animal) and praziquantel is provided at up to 18mg/kg (re. host animal).
  • the selamectin is present in the formulation at about 1 % to about 16% (w/v), more preferably about 4% to about 12% w/v, and most preferably about 6% to about 12% w/v.
  • Specific preferred formulations contain selamectin at about 6% w/v and about 12% w/v.
  • the praziquantel is present in the formulation at about 0.5 to about 10% w/v, more preferably about 3 to about 9% w/v , most preferably about 6% w/v.
  • the di(C 2-4 glycol) mono(C ⁇ - alkyl) ether is diethylene glycol monomethyl ether (DEGMME) or dipropylene glycol monomethyl ether (DPGMME), more preferably DPGMME.
  • DEGMME diethylene glycol monomethyl ether
  • DPGMME dipropylene glycol monomethyl ether
  • the skin-acceptable solvent is present and is ethanol or isopropanol, more preferably isopropanol.
  • the formulation containing the avermectin 13-monosaccharide oxime has a w/v to v/v ratio of avermectin 13-monosaccharide oxime to the glycol monomethyl ether is in the range (0.5 to 2) to 1 , more preferably (0.7 to 1.4) to 1 , yet more preferably (0.9 to 1.1 ) to 1 , most preferably about 1 :1.
  • a preferred formulation according to the invention also contains antioxidant, preferably selected from propylgallate, BHA (2-t-butyl-4-methoxyphenol), and BHT (2,6-di-f-butyl-4-methylphenol), more preferably BHT.
  • antioxidant preferably selected from propylgallate, BHA (2-t-butyl-4-methoxyphenol), and BHT (2,6-di-f-butyl-4-methylphenol), more preferably BHT.
  • a preferred formulation according to the invention consists of:
  • DEGMME or DPGMME at 1 to 16% w/v, and at a w/v or v/v ratio of active compound to DEGMME/DPGMME of about 1 :1 ;
  • a more preferred formulation consists of (a) selamectin at a level of 6% to 12% w/v;
  • a pharmaceutical or veterinary composition which comprises a 13- monosaccharide 5-oxime avermectin such as selamectin and praziquantel and a pharmaceutical or veterinary carrier;
  • kits useful in the treatment of a parasitic infestation of flea and/or heartworm and tapeworm in a mammal which comprises a 13- monosaccharide 5-oxime avermectin, such as selamectin, and praziquantel and a pharmaceutical or veterinary carrier, and instructions for the treatment of a parasitic infestation of flea and/or heartworm and tapeworm in a mammal.

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  • Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Chemical & Material Sciences (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Tropical Medicine & Parasitology (AREA)
  • Epidemiology (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Molecular Biology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicinal Preparation (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)

Abstract

La présente invention concerne une polythérapie antiparasitaire faisant appel à une combinaison d'un 5-oxime avermectine monosaccharide 13, tel que de la sélamectine, et du praziquantel.
PCT/IB2002/001025 2001-04-04 2002-03-28 Compositions veterinaires comprenant des derives d'oxime avermectine et du praziquantel WO2002094288A1 (fr)

Priority Applications (5)

Application Number Priority Date Filing Date Title
EP02716978A EP1381374A1 (fr) 2001-04-04 2002-03-28 Compositions veterinaires comprenant des derives d'oxime avermectine et du praziquantel
CA002443068A CA2443068A1 (fr) 2001-04-04 2002-03-28 Compositions veterinaires comprenant des derives d'oxime avermectine et du praziquantel
JP2002591005A JP2004526804A (ja) 2001-04-04 2002-03-28 アベルメクチンオキシム誘導体およびプラジクアンテルを含む獣医学的組成物
BR0208654-9A BR0208654A (pt) 2001-04-04 2002-03-28 Composições veterinárias compreendendo derivados de avermectina-oxima e praziquantel
MXPA03009023A MXPA03009023A (es) 2001-04-04 2002-03-28 Composiciones veterinarias que comprenden derivados de oximaavermectina y praziquantel.

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB0108485.4 2001-04-04
GBGB0108485.4A GB0108485D0 (en) 2001-04-04 2001-04-04 Combination therapy

Publications (1)

Publication Number Publication Date
WO2002094288A1 true WO2002094288A1 (fr) 2002-11-28

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PCT/IB2002/001025 WO2002094288A1 (fr) 2001-04-04 2002-03-28 Compositions veterinaires comprenant des derives d'oxime avermectine et du praziquantel

Country Status (7)

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EP (1) EP1381374A1 (fr)
JP (1) JP2004526804A (fr)
BR (1) BR0208654A (fr)
CA (1) CA2443068A1 (fr)
GB (1) GB0108485D0 (fr)
MX (1) MXPA03009023A (fr)
WO (1) WO2002094288A1 (fr)

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1610613A2 (fr) * 2003-04-04 2006-01-04 Merial Ltd. Formulations veterinaires anthelminthiques topiques
US7763583B2 (en) 2003-12-13 2010-07-27 Bayer Animal Health Gmbh Endoparasiticidal compositions for topical application
WO2010107791A2 (fr) 2009-03-17 2010-09-23 Concert Pharmaceuticals, Inc. Composés de pyrazinoisoquinoline
US9233100B2 (en) 2012-02-06 2016-01-12 Merial, Inc. Parasiticidal oral veterinary compositions comprising systemically-acting active agents, methods and uses thereof
US9237751B2 (en) 2009-03-27 2016-01-19 Norbrook Laboratories Limited Topical parasiticide composition
US9770449B2 (en) 2010-04-02 2017-09-26 Merial Inc. Parasiticidal compositions comprising multiple active agents, methods and uses thereof
US11285101B2 (en) 2012-04-04 2022-03-29 Intervet Inc. Soft chewable pharmaceutical products

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2936710B1 (fr) * 2008-10-07 2011-01-07 Ceva Sante Animale Composition veterinaire antiprolactinique destinee aux ruminants
JP5723567B2 (ja) * 2010-08-06 2015-05-27 丸石製薬株式会社 含窒素複素環式化合物の定量方法

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1994015944A1 (fr) * 1993-01-18 1994-07-21 Pfizer Limited Nouveaux agents antiparasitaires apparentes aux milbemycines et aux avermectines
WO1995005181A2 (fr) * 1993-08-12 1995-02-23 Biovet-Joint Stock Company Agent anti-parasitaire destine aux animaux
EP0717993A2 (fr) * 1994-11-28 1996-06-26 Virbac S.A. Compositions antihelmintiques pour équidés
WO1998006407A1 (fr) * 1996-07-30 1998-02-19 Ashmont Holdings Limited Formulations anti-helminthes
WO2000030449A1 (fr) * 1998-11-19 2000-06-02 Pfizer Limited Formulations antiparasitaires

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1994015944A1 (fr) * 1993-01-18 1994-07-21 Pfizer Limited Nouveaux agents antiparasitaires apparentes aux milbemycines et aux avermectines
WO1995005181A2 (fr) * 1993-08-12 1995-02-23 Biovet-Joint Stock Company Agent anti-parasitaire destine aux animaux
EP0717993A2 (fr) * 1994-11-28 1996-06-26 Virbac S.A. Compositions antihelmintiques pour équidés
WO1998006407A1 (fr) * 1996-07-30 1998-02-19 Ashmont Holdings Limited Formulations anti-helminthes
WO2000030449A1 (fr) * 1998-11-19 2000-06-02 Pfizer Limited Formulations antiparasitaires

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
BENCHAOUI H A ET AL: "Efficacy and safety of selamectin against fleas on dogs and cats presented as veterinary patients in Europe.", VETERINARY PARASITOLOGY, vol. 91, no. 3-4, 2000, pages 223 - 232, XP002202199, ISSN: 0304-4017 *
BISHOP B F ET AL: "PREFACE; Selamectin: A novel broad-spectrum endectocide for dogs and cats.", VETERINARY PARASITOLOGY, vol. 91, no. 3-4, 2000, pages 161 - 162, XP002202197, ISSN: 0304-4017 *
BISHOP B F ET AL: "Selamectin: A novel broad-spectrum endectocide for dogs and cats.", VETERINARY PARASITOLOGY, vol. 91, no. 3-4, 2000, pages 163 - 176, XP002202198, ISSN: 0304-4017 *

Cited By (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1610613A2 (fr) * 2003-04-04 2006-01-04 Merial Ltd. Formulations veterinaires anthelminthiques topiques
JP2006522154A (ja) * 2003-04-04 2006-09-28 メリアル リミテッド 動物用駆虫局所製剤
EP1610613A4 (fr) * 2003-04-04 2012-05-02 Merial Ltd Formulations veterinaires anthelminthiques topiques
US7763583B2 (en) 2003-12-13 2010-07-27 Bayer Animal Health Gmbh Endoparasiticidal compositions for topical application
WO2010107791A2 (fr) 2009-03-17 2010-09-23 Concert Pharmaceuticals, Inc. Composés de pyrazinoisoquinoline
US9237751B2 (en) 2009-03-27 2016-01-19 Norbrook Laboratories Limited Topical parasiticide composition
US9770449B2 (en) 2010-04-02 2017-09-26 Merial Inc. Parasiticidal compositions comprising multiple active agents, methods and uses thereof
US9233100B2 (en) 2012-02-06 2016-01-12 Merial, Inc. Parasiticidal oral veterinary compositions comprising systemically-acting active agents, methods and uses thereof
US9259417B2 (en) 2012-02-06 2016-02-16 Merial, Inc. Parasiticidal oral veterinary compositions comprising systemically-acting active agents, methods and uses thereof
US9931320B2 (en) 2012-02-06 2018-04-03 Merial Inc. Parasiticidal oral veterinary compositions comprising systemically-acting active agents, methods and uses thereof
US10596156B2 (en) 2012-02-06 2020-03-24 Boehringer Ingelheim Animal Health USA Inc. Parasiticidal oral veterinary compositions comprising systemically-acting active agents, methods and uses thereof
US11285101B2 (en) 2012-04-04 2022-03-29 Intervet Inc. Soft chewable pharmaceutical products
US11337917B2 (en) 2012-04-04 2022-05-24 Intervet Inc. Soft chewable pharmaceutical products

Also Published As

Publication number Publication date
EP1381374A1 (fr) 2004-01-21
BR0208654A (pt) 2004-03-09
CA2443068A1 (fr) 2002-11-28
MXPA03009023A (es) 2004-02-12
GB0108485D0 (en) 2001-05-23
JP2004526804A (ja) 2004-09-02

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