WO2000030449A1 - Antiparasitic formulations - Google Patents
Antiparasitic formulations Download PDFInfo
- Publication number
- WO2000030449A1 WO2000030449A1 PCT/IB1999/001715 IB9901715W WO0030449A1 WO 2000030449 A1 WO2000030449 A1 WO 2000030449A1 IB 9901715 W IB9901715 W IB 9901715W WO 0030449 A1 WO0030449 A1 WO 0030449A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- formulation according
- formulation
- dpgmme
- monomethyl ether
- glycol monomethyl
- Prior art date
Links
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
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/365—Lactones
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0014—Skin, i.e. galenical aspects of topical compositions
- A61K9/0017—Non-human animal skin, e.g. pour-on, spot-on
-
- 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
-
- 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
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
- A61K47/10—Alcohols; Phenols; Salts thereof, e.g. glycerol; Polyethylene glycols [PEG]; Poloxamers; PEG/POE alkyl ethers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0014—Skin, i.e. galenical aspects of topical compositions
-
- 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
- A61P33/14—Ectoparasiticides, e.g. scabicides
Definitions
- This invention relates to antiparasitic formulations, particularly antiparasitic formulations containing avermectins or milbemycins, including derivatives thereof, suitable for topical application to mammals, including humans and domestic animals such as cats and dogs, and which are useful in the treatment of conditions caused by endo- and/or ectoparasites.
- formulations of substances active against fleas and/or heartworms are especially of interest.
- Antiparasitic avermectins, milbemycins and their derivatives have been described in numerous publications, see for example European Patent Applications publication nos. 0 214 731, 0 284 176, 0 317 148, 0 308 145, 0 340 832, 0 335 541, 0 350 187, 0 170 006, 0 254 583, 0 334 484, 0 410 615, British Patent Application numbers 1 573 955, 1 390 336, International Patent Applications publication nos.
- ivermectin IvomecTM
- doramectin DectomaxTM
- moxidectin moxidectin
- abamectin AvomecTM
- a long-acting antiparasitic formulation suitable for topical application including:
- the formulations of the invention have a good cosmetic profile. For instance when applied topically to the fur of a domestic animal such as a cat or dog, they spread well giving good skin contact across a wide range of temperatures. They do not leave an unsightly oily patch, of the type associated with some commercial avermectin or milbemycin formulations in fatty excipients.
- formulations according to the invention are effective enough to enable long periods, e.g. a several weeks or a month, between treatments.
- the active compound has activity against both endo- and ectoparasites.
- the active compound is selected from ivermectin, doramectin, abamectin, moxidectin, and the avermectin 13-monosaccharide 5-oximes generically and specifically disclosed in International Patent Application publication no. WO 94/15944.
- the active compound is 5-oximino-22,23-dihydro-25- cyclohexylavermectin B 1 monosaccharide (selamectin).
- the di(C,_, glycol) mono(C alkyl) ether is diethylene glycol monomethyl ether (DEGMME) or dipropylene glycol monomethyl ether (DPGMME). More preferably the glycol monomethyl ether is DPGMME.
- any source of phamaceutical/veterinary quality di(C 2 _ 4 glycol) mono(C, .4 alkyl) ethers may be used.
- an acceptable commercial source of DPGMME is Dow Corning, whose product "Dowanol DPMTM" has the following characteristics: B.pt. 74.6°C at 13mbar; freezing point -83°C, density 0.948g/cm 3 at 25°C, viscosity 3.72 Pas at 25°C and refractive index of 1.421 at 25°C.
- the di(C 2 . 4 glycol) mono(C,_ 4 alkyl) ether is present in the formulation at a level of up to about 20% v/v, yet more preferably in the range about 2-16% v/v, further more preferably in the range about 4-12% v/v, and most preferably in the range about 6- 12% v/v.
- the skin acceptable volatile solvent is present and is ethanol or isopropanol (IPA). More preferably the skin acceptable solvent is IPA.
- the w/v to v/v ratio of active compound to the glycol monomethyl ether is in the range about (0.5 to 2) to 1.
- the w/v to v/v ratio of active compound to the glycol monomethyl ether is about (0.7 to 1.4) to 1.
- the w/v to v/v ratio of active compound to the glycol monomethyl ether is about (0.9 to 1.1) to 1.
- the w/v to v/v ratio of active compound to the glycol monomethyl ether is about 1:1.
- the level of active avermectin or milbemycin in the total formulation is in the range about 1% to about 16% w/v, more preferably about 4% to about 12% w/v, yet more preferably about 6 to about 12% w/v.
- the formulation can further include an antioxidant, such as propylgallate,
- BHA (2-t-butyl-4-methoxyphenol), or BHT (2,6-di-t-butyl-4-methylphenol).
- the antioxidant if present, is BHT.
- the antioxidant if present, is at a level of less than 0.2% w/v, more preferably less than 0.1% w/v.
- the formulation consists of: (a) 5-oximino-22,23-dihydro-25-cyclohexylavermectin Bl monosaccharide (selamectin, at a level of 1% to 16% w/v);
- the formulation consists of:
- a preferred group of formulations consists of the formulations mentioned in the Examples below.
- Another aspect of the invention is a method of treatment of a condition caused by an endo- or ectoparasite by administration of an effective amount of a formulation according to the invention.
- Another aspect of the invention is a formulation according to the invention for use in medicine.
- Formulations according to the invention can be made by standard methods, for example by dissolution of the avermectin and/or milbemycin and optional antioxidant in the solvent or solvents, in accordance with standard pharmaceutical or veterinary practice, e.g. by agitation of a mixture of the ingredients, if necessary with concurrent warming.
- the invention is illustrated by the following examples, in which (i) the BHT antioxidant (if present) was dissolved in a mixture of DPGMME or DEGMME and IPA, (ii) the drug substance was added, and the mixture stirred until dissolution took place, (iii) any residue was filtered off prior to filling into appropriate containers.
- a formulation consisting of (a) 5-oximino-22,23-dihydro-25-cyclohexylavermectin Bl monosaccharide at 6% w/v
- a formulation consisting of (a) 5-oximino-22,23-dihydro-25-cyclohexylavermectin Bl monosaccharide at 8% w/v (b) DPGMME at 16% v/v (c) BHA 0.1 % w/v (d) IPA q.s. 100% v/v.
- Example 8 A formulation consisting of
- the amount of antiparasitic avermectin / milbemycin material in a unit dose of the formulation can of course vary depending on the efficacy of the avermectin / milbemycin in treating the condition of interest, the desired frequency of application, etc., according to standard veterinary and pharmaceutical practice.
- formulations of the invention can be administered in a way appropriate to the specific use envisaged, the particular species and weight of host animal being treated, the parasite or parasites involved, degree of infestation, etc., according to standard medical and veterinary practice.
- a dose of 5-oximino-22,23-dihydro-25- cyclohexylavermectin B 1 monosaccharide (selamectin) of between 4 mg/kg and 12 mg/kg, preferably about 9 mg/kg body weight of the host animal as a single dose once per month will be satisfactory for flea control and heartworm prophylaxis, but of course there will be instances where higher or lower dosage ranges are indicated and such are within the scope of this invention.
- a typical dosage regime for a 6mg/kg dose, to a domestic animal such as a typical domestic cat or dog, would be 0.25ml to 2ml of the formulation of Example 1 per dose per month.
- formulations according to the invention are especially suitable to be administered topically.
- dip, spray, pour-on, spot-on, jetting fluid, shampoos, collar, tag or harness may be used.
- Particularly preferred is a spot-on formulation.
- reference to treatment includes prevention, alleviation and cure of the condition or conditions caused by the parasite or parasites.
- the efficacy of the formulations according to the invention is illustrated by the following.
- Three formulations of selamectin were administered as a single topical dose of 8 mg/kg, and evaluated over time against induced infestations of the flea (Ctenocephalides felis) on dogs.
- the three formulations each contained 160 mg/mL of selamectin and, respectively, 16% w/v diethylene glycol monomethyl ether
- Efficacy was assessed by comb counts of viable fleas present on each dog. Each dog was infested with approximately 100 unfed viable adult C. felis on days 1, 4, 11, 18, 23, 27, 32, and 39, and comb counts were conducted approximately 72 hours after each infestation, on days 4, 7, 14, 21, 26, 30, 35 and 42. There were no adverse drug reactions and no mortalities during the study. Geometric mean flea comb counts for each of the three selamectin formulations were significantly lower (P ⁇ 0.05) than those of the saline control on each post-treatment flea counting day. Efficacies (percentage reductions in geometric mean flea comb counts) on day 30 were 98.6%, 98.2% and 99.4% for T2, T3 and T4, respectively.
- the efficacy of a selamectin formulation was evaluated against induced infestations of Ctenocephalides felis on dogs for the determination of an appropriate dose.
- the formulation contained 12% (120 mg/mL) of selamectin and 11.26% w/v dipropylene glycol monomethyl ether (DPGMME) in isopropanol.
- Forty-eight dogs 24 males and 24 females were allocated randomly by flea counts within sex to one of four groups: placebo (negative control, Tl) or selamectin at 3 mg/kg (T2), 6 mg/kg (T3) or 9 mg/kg (T4).
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- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Epidemiology (AREA)
- General Chemical & Material Sciences (AREA)
- Zoology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Dermatology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Dentistry (AREA)
- Tropical Medicine & Parasitology (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Organic Chemistry (AREA)
- Wood Science & Technology (AREA)
- Environmental Sciences (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Saccharide Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Abstract
Description
Claims
Priority Applications (23)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
HU0104235A HU229493B1 (en) | 1998-11-19 | 1999-10-20 | Antiparasitic formulations |
AU59959/99A AU5995999C1 (en) | 1998-11-19 | 1999-10-20 | Antiparasitic formulations |
CNB998134554A CN1147232C (en) | 1998-11-19 | 1999-10-20 | Antiparasitic formulations |
NZ510678A NZ510678A (en) | 1998-11-19 | 1999-10-20 | Antiparasitic formulations containing avermectin and di-glycol monomethyl ether |
SK662-2001A SK287540B6 (en) | 1998-11-19 | 1999-10-20 | Antiparasitic formulation |
IL14210499A IL142104A0 (en) | 1998-11-19 | 1999-10-20 | Antiparasitic formulations |
PL348638A PL204763B1 (en) | 1998-11-19 | 1999-10-20 | Antiparasitic formulations |
SI9930759T SI1130966T2 (en) | 1998-11-19 | 1999-10-20 | Antiparasitic formulations |
BRPI9915458-7A BR9915458B1 (en) | 1998-11-19 | 1999-10-20 | topical antiparasitic formulation. |
AT99972494T ATE288201T1 (en) | 1998-11-19 | 1999-10-20 | ANTIPARASITIC FORMULATIONS |
EA200100458A EA003959B1 (en) | 1998-11-19 | 1999-10-20 | Antiparasitic formulations |
EP99972494A EP1130966B2 (en) | 1998-11-19 | 1999-10-20 | Antiparasitic formulations |
DK99972494T DK1130966T4 (en) | 1998-11-19 | 1999-10-20 | Antiparasitic formulations |
DE69923583T DE69923583T3 (en) | 1998-11-19 | 1999-10-20 | Antiparasitic formulations |
CA002351730A CA2351730C (en) | 1998-11-19 | 1999-10-20 | Antiparasitic formulations containing avermectin 13-monosaccharide 5-oxime |
JP2000583347A JP3507799B2 (en) | 1998-11-19 | 1999-10-20 | Antiparasitic formulation |
IL142104A IL142104A (en) | 1998-11-19 | 2001-03-19 | Antiparasitic formulations |
IS5907A IS5907A (en) | 1998-11-19 | 2001-03-23 | Combinations against parasites |
NO20012389A NO20012389L (en) | 1998-11-19 | 2001-05-15 | Antiparasitic formulations |
HR20010368A HRP20010368B1 (en) | 1998-11-19 | 2001-05-17 | Antiparasitic formulations |
BG105601A BG65440B1 (en) | 1998-11-19 | 2001-06-14 | Antiparasitic formulations |
HK02102583.7A HK1040593B (en) | 1998-11-19 | 2002-04-08 | Antiparasitic formulations |
IL173567A IL173567A0 (en) | 1998-11-19 | 2006-02-06 | Antiparasitic formulations |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB9825402.2 | 1998-11-19 | ||
GBGB9825402.2A GB9825402D0 (en) | 1998-11-19 | 1998-11-19 | Antiparasitic formulations |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2000030449A1 true WO2000030449A1 (en) | 2000-06-02 |
Family
ID=10842728
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/IB1999/001715 WO2000030449A1 (en) | 1998-11-19 | 1999-10-20 | Antiparasitic formulations |
Country Status (43)
Cited By (16)
Publication number | Priority date | Publication date | Assignee | Title |
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WO2001020994A1 (en) * | 1999-09-22 | 2001-03-29 | Ashmont Holdings Limited | Sheep pour-on |
WO2001040446A1 (en) * | 1999-12-02 | 2001-06-07 | Lilly Co Eli | Pour-on formulations |
US6426333B1 (en) | 1996-09-19 | 2002-07-30 | Merial | Spot-on formulations for combating parasites |
US6482425B1 (en) | 1996-09-19 | 2002-11-19 | Merial | Parasiticidal combination |
WO2002094288A1 (en) * | 2001-04-04 | 2002-11-28 | Pfizer Limited | Veterinary compositions comprising avermectin-oxime derivatives and praziquantel |
US6998131B2 (en) | 1996-09-19 | 2006-02-14 | Merial Limited | Spot-on formulations for combating parasites |
KR100600402B1 (en) * | 2002-05-22 | 2006-07-14 | 주식회사 엘지생명과학 | Formulation for using Pour-on Skin Application of ivermectin and manufacturing method thereof |
GB2444572A (en) * | 2006-12-05 | 2008-06-11 | Michael Hilary Burke | Process for the preparation of a stable anhydrous ivermectin formulation |
US7772194B2 (en) | 2001-09-17 | 2010-08-10 | Eli Lilly And Company | Pesticidal formulations |
WO2011157101A1 (en) * | 2010-06-17 | 2011-12-22 | Rotam Agrochem International Co., Ltd | Pesticidal composition |
WO2013026117A1 (en) * | 2011-08-25 | 2013-02-28 | Eurofarma Laboratórios S.A. | Non-residual, pour-on veterinary compositions, use, kit, and method for treating parasitic diseases |
WO2014189837A1 (en) * | 2013-05-20 | 2014-11-27 | Zoetis Llc | Long-acting spiro-isoxazoline antiparasitic compositions |
AP3472A (en) * | 2011-01-14 | 2015-11-30 | Gsi Geosyntec Invest Bv | Method and device for laying down and tensioning an impermeable cover for hydraulic works in loose material |
WO2018167271A1 (en) | 2017-03-17 | 2018-09-20 | Krka, D.D., Novo Mesto | Stable topical veterinary composition |
WO2019101961A1 (en) * | 2017-11-23 | 2019-05-31 | Ceva Sante Animale | Composition containing moxidectin for treating parasites infestations |
EP2608660B1 (en) * | 2010-07-30 | 2020-04-01 | Ceva Sante Animale | Compositions for treating heartworm infestation |
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GB9825402D0 (en) * | 1998-11-19 | 1999-01-13 | Pfizer Ltd | Antiparasitic formulations |
US20030064941A1 (en) * | 2001-05-21 | 2003-04-03 | Pfizer Inc. | Avermectin and praziquantel combination therapy |
US20040037869A1 (en) * | 2002-08-16 | 2004-02-26 | Douglas Cleverly | Non-animal product containing veterinary formulations |
US20040151759A1 (en) * | 2002-08-16 | 2004-08-05 | Douglas Cleverly | Non-animal product containing veterinary formulations |
US7666444B2 (en) * | 2004-02-02 | 2010-02-23 | Wyeth | Antiparasitic composition |
DE102004053964A1 (en) * | 2004-11-09 | 2006-05-11 | Bayer Healthcare Ag | Remedy for demodicosis |
PL2396006T3 (en) * | 2009-02-16 | 2013-06-28 | Zoetis Llc | High dosage doramectin formulation |
AU2010224685A1 (en) | 2009-03-18 | 2011-11-03 | Fidopharm, Inc. | Parasiticidal formulation |
UA108641C2 (en) | 2010-04-02 | 2015-05-25 | PARASITICID COMPOSITION CONTAINING FOUR ACTIVE AGENTS AND METHOD OF APPLICATION | |
WO2012054331A1 (en) * | 2010-10-20 | 2012-04-26 | Galderma S.A. | Method of treating otitis externa using macrocyclic lactone compound |
BG1461U1 (en) * | 2011-03-18 | 2011-07-29 | "Ендектовет" Еоод | Compositions of an antiparasitic remedy |
EP2768513B8 (en) * | 2011-10-18 | 2020-05-20 | Institut national de recherche pour l'agriculture, l'alimentation et l'environnement | Use of avermectin derivative for increasing bioavailability and efficacy of macrocylic lactones |
DK2785719T3 (en) | 2011-12-02 | 2017-12-04 | Merial Inc | LONG-EFFECTIVE INJECTABLE MOXIDECTIN FORMULATIONS AND HIS UNKNOWN MOXIDECTIN CRYSTAL FORMS |
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AR094882A1 (en) | 2013-02-26 | 2015-09-02 | Zoetis Llc | SELAMECTINE FOR THE TREATMENT OF INFESTATIONS BY SEA LIPES, COMPOSITION |
RU2020122841A (en) | 2017-12-15 | 2022-01-18 | Тарсус Фармасьютикалс, Инк. | ISOXAZOLINE PARASITICIDAL COMPOSITIONS AND METHODS FOR THE TREATMENT OF BLEPHARITIS |
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EP0879229B1 (en) | 1996-01-30 | 2002-11-06 | Takeda Chemical Industries, Ltd. | Arylpyrazole insecticides |
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1998
- 1998-11-19 GB GBGB9825402.2A patent/GB9825402D0/en not_active Ceased
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1999
- 1999-10-20 SK SK662-2001A patent/SK287540B6/en not_active IP Right Cessation
- 1999-10-20 KR KR10-2001-7006309A patent/KR100458406B1/en active IP Right Grant
- 1999-10-20 PL PL348638A patent/PL204763B1/en unknown
- 1999-10-20 AT AT05000644T patent/ATE469550T1/en active
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- 1999-10-20 DE DE69923583T patent/DE69923583T3/en not_active Expired - Lifetime
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- 1999-10-20 EP EP05000644A patent/EP1522219B1/en not_active Revoked
- 1999-10-20 DK DK05000644.4T patent/DK1522219T3/en active
- 1999-10-20 JP JP2000583347A patent/JP3507799B2/en not_active Expired - Lifetime
- 1999-10-20 PT PT99972494T patent/PT1130966E/en unknown
- 1999-10-20 ES ES05000644T patent/ES2344505T3/en not_active Expired - Lifetime
- 1999-10-20 DE DE69942465T patent/DE69942465D1/en not_active Expired - Lifetime
- 1999-10-20 HU HU0104235A patent/HU229493B1/en unknown
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- 1999-10-20 SI SI9931046T patent/SI1522219T1/en unknown
- 1999-10-20 ES ES99972494T patent/ES2237213T3/en not_active Expired - Lifetime
- 1999-10-20 WO PCT/IB1999/001715 patent/WO2000030449A1/en active Application Filing
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- 1999-10-20 CN CNB998134554A patent/CN1147232C/en not_active Expired - Lifetime
- 1999-10-20 IL IL14210499A patent/IL142104A0/en active IP Right Grant
- 1999-10-20 CZ CZ2001-1734A patent/CZ304345B6/en not_active IP Right Cessation
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- 1999-11-17 MA MA25851A patent/MA25029A1/en unknown
- 1999-11-17 DZ DZ990245A patent/DZ2945A1/en active
- 1999-11-17 PE PE1999001163A patent/PE20001319A1/en not_active Application Discontinuation
- 1999-11-18 ZA ZA9907174A patent/ZA997174B/en unknown
- 1999-11-18 CO CO99072702A patent/CO5150175A1/en unknown
- 1999-11-18 AP APAP/P/1999/001697A patent/AP1210A/en active
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2001
- 2001-03-19 IL IL142104A patent/IL142104A/en not_active IP Right Cessation
- 2001-03-23 IS IS5907A patent/IS5907A/en unknown
- 2001-05-15 NO NO20012389A patent/NO20012389L/en not_active Application Discontinuation
- 2001-05-17 HR HR20010368A patent/HRP20010368B1/en not_active IP Right Cessation
- 2001-06-14 BG BG105601A patent/BG65440B1/en unknown
- 2001-10-16 US US09/978,936 patent/US6797701B2/en not_active Expired - Lifetime
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2002
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US6426333B1 (en) | 1996-09-19 | 2002-07-30 | Merial | Spot-on formulations for combating parasites |
US6482425B1 (en) | 1996-09-19 | 2002-11-19 | Merial | Parasiticidal combination |
US6962713B2 (en) | 1996-09-19 | 2005-11-08 | Merial | Spot-on formulations for combating parasites |
US6998131B2 (en) | 1996-09-19 | 2006-02-14 | Merial Limited | Spot-on formulations for combating parasites |
WO2001020994A1 (en) * | 1999-09-22 | 2001-03-29 | Ashmont Holdings Limited | Sheep pour-on |
WO2001040446A1 (en) * | 1999-12-02 | 2001-06-07 | Lilly Co Eli | Pour-on formulations |
WO2001040446A3 (en) * | 1999-12-02 | 2002-01-17 | Lilly Co Eli | Pour-on formulations |
US6955818B1 (en) | 1999-12-02 | 2005-10-18 | Eli Lilly And Company | Pour-on formulations |
WO2002094288A1 (en) * | 2001-04-04 | 2002-11-28 | Pfizer Limited | Veterinary compositions comprising avermectin-oxime derivatives and praziquantel |
US8048861B2 (en) | 2001-09-17 | 2011-11-01 | Eli Lilly And Company | Pesticidal formulations |
US7772194B2 (en) | 2001-09-17 | 2010-08-10 | Eli Lilly And Company | Pesticidal formulations |
KR100600402B1 (en) * | 2002-05-22 | 2006-07-14 | 주식회사 엘지생명과학 | Formulation for using Pour-on Skin Application of ivermectin and manufacturing method thereof |
GB2444572B (en) * | 2006-12-05 | 2011-10-19 | Michael Hilary Burke | A process for the preparation of a stable anhydrous anthelmintic formulation |
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GB2495659B (en) * | 2010-06-17 | 2017-10-04 | Jiangsu Rotam Chemistry Co Ltd | Pesticidal composition |
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WO2013026117A1 (en) * | 2011-08-25 | 2013-02-28 | Eurofarma Laboratórios S.A. | Non-residual, pour-on veterinary compositions, use, kit, and method for treating parasitic diseases |
WO2014189837A1 (en) * | 2013-05-20 | 2014-11-27 | Zoetis Llc | Long-acting spiro-isoxazoline antiparasitic compositions |
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WO2018167271A1 (en) | 2017-03-17 | 2018-09-20 | Krka, D.D., Novo Mesto | Stable topical veterinary composition |
WO2019101961A1 (en) * | 2017-11-23 | 2019-05-31 | Ceva Sante Animale | Composition containing moxidectin for treating parasites infestations |
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