NZ733600B2 - Topical Delivery Formulation - Google Patents
Topical Delivery Formulation Download PDFInfo
- Publication number
- NZ733600B2 NZ733600B2 NZ733600A NZ73360015A NZ733600B2 NZ 733600 B2 NZ733600 B2 NZ 733600B2 NZ 733600 A NZ733600 A NZ 733600A NZ 73360015 A NZ73360015 A NZ 73360015A NZ 733600 B2 NZ733600 B2 NZ 733600B2
- Authority
- NZ
- New Zealand
- Prior art keywords
- formulation
- polymer
- solvent
- add
- hcl
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 168
- 238000009472 formulation Methods 0.000 title claims abstract description 65
- 230000000699 topical Effects 0.000 title claims description 16
- 239000002904 solvent Substances 0.000 claims abstract description 79
- 229920000642 polymer Polymers 0.000 claims abstract description 77
- KFZMGEQAYNKOFK-UHFFFAOYSA-N iso-propanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims abstract description 42
- 239000004014 plasticizer Substances 0.000 claims abstract description 32
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 31
- 239000004480 active ingredient Substances 0.000 claims abstract description 14
- 239000011159 matrix material Substances 0.000 claims abstract description 6
- -1 aliphatic ester Chemical class 0.000 claims description 59
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 claims description 48
- 229920002689 polyvinyl acetate Polymers 0.000 claims description 24
- 238000001704 evaporation Methods 0.000 claims description 23
- 239000011118 polyvinyl acetate Substances 0.000 claims description 23
- QZCLKYGREBVARF-UHFFFAOYSA-N tributyl 2-acetyloxypropane-1,2,3-tricarboxylate Chemical group CCCCOC(=O)CC(C(=O)OCCCC)(OC(C)=O)CC(=O)OCCCC QZCLKYGREBVARF-UHFFFAOYSA-N 0.000 claims description 21
- 150000001875 compounds Chemical class 0.000 claims description 17
- 244000078703 ectoparasites Species 0.000 claims description 16
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims description 10
- 229920003176 water-insoluble polymer Polymers 0.000 claims description 8
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinylpyrrolidone Chemical group C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 claims description 7
- 230000001225 therapeutic Effects 0.000 claims description 7
- 239000003814 drug Substances 0.000 claims description 6
- 150000002500 ions Chemical class 0.000 claims description 6
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- 229920002451 polyvinyl alcohol Polymers 0.000 claims description 5
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- 235000013855 polyvinylpyrrolidone Nutrition 0.000 claims description 5
- ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical group CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 claims description 4
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- XTXRWKRVRITETP-UHFFFAOYSA-N vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 claims description 4
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- 230000000052 comparative effect Effects 0.000 claims 4
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- 238000000034 method Methods 0.000 description 22
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- 229940083542 Sodium Drugs 0.000 description 11
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
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- RLLPVAHGXHCWKJ-HKUYNNGSSA-N (3-phenoxyphenyl)methyl (1R,3R)-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate Chemical compound CC1(C)[C@@H](C=C(Cl)Cl)[C@H]1C(=O)OCC1=CC=CC(OC=2C=CC=CC=2)=C1 RLLPVAHGXHCWKJ-HKUYNNGSSA-N 0.000 description 6
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- 239000012049 topical pharmaceutical composition Substances 0.000 description 5
- HBXWUCXDUUJDRB-UHFFFAOYSA-N 1-octadecoxyoctadecane Chemical compound CCCCCCCCCCCCCCCCCCOCCCCCCCCCCCCCCCCCC HBXWUCXDUUJDRB-UHFFFAOYSA-N 0.000 description 4
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- RRZXIRBKKLTSOM-XPNPUAGNSA-N avermectin B1a Chemical compound C1=C[C@H](C)[C@@H]([C@@H](C)CC)O[C@]11O[C@H](C\C=C(C)\[C@@H](O[C@@H]2O[C@@H](C)[C@H](O[C@@H]3O[C@@H](C)[C@H](O)[C@@H](OC)C3)[C@@H](OC)C2)[C@@H](C)\C=C\C=C/2[C@]3([C@H](C(=O)O4)C=C(C)[C@@H](O)[C@H]3OC\2)O)C[C@H]4C1 RRZXIRBKKLTSOM-XPNPUAGNSA-N 0.000 description 4
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Classifications
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- 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
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/08—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing solids as carriers or diluents
- A01N25/10—Macromolecular compounds
-
- 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
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
-
- 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
- A01N53/00—Biocides, pest repellants or attractants, or plant growth regulators containing cyclopropane carboxylic acids or derivatives thereof
-
- 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
- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
- A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
-
- 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
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/415—1,2-Diazoles
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- 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
- A61P33/10—Anthelmintics
Abstract
The invention is a pour-on antiparasitic formulation having superior water resistant properties. The pour-on formulation utilizes one or more polymers (water insoluble with or without water soluble) in the range of about 5 to about 40% w/w, one or more solvents in the range of about 50 to about 94% w/w, with or without additive (e.g., isopropanol or ethanol) in the range of about 5 to about 30% w/w, and optionally a plasticizer in the range of about 0.5 to about 25% w/w. The pour-on antiparasitic formulation features limited spreading when applied to animals (cattle, sheep, dogs and the like). The pour-on antiparasitic formulation further partially evaporates, leaving a water resistant polymer matrix that diffuses at least one active ingredient to the animal’s skin. w/w, with or without additive (e.g., isopropanol or ethanol) in the range of about 5 to about 30% w/w, and optionally a plasticizer in the range of about 0.5 to about 25% w/w. The pour-on antiparasitic formulation features limited spreading when applied to animals (cattle, sheep, dogs and the like). The pour-on antiparasitic formulation further partially evaporates, leaving a water resistant polymer matrix that diffuses at least one active ingredient to the animal’s skin.
Description
TITLE OF THE INVENTION
Topical Delivery Formulation
CROSS-REFERENCE TO D APPLICATIONS
This application is a Divisional of New Zealand Patent Application 722669, the entire
contents of which are orated herein by reference. This ation claims priority to U.S.
Provisional Patent Application No. 61/929,371, filed January 20, 2014.
FIELD OF THE INVENTION
The present disclosure relates generally to topical delivery systems and their manufacture.
More specifically, the disclosure relates to topical antiparasitic delivery systems for animals.
BACKGROUND
Animals such as mammals are often susceptible to te ations. These
parasites may be ectoparasites, such as insects, and endoparasites such as filariae and worms.
icated animals, such as cats and dogs, are often infested with one or more of the
following ectoparasites:
- fleas (Ctenocephalides felis, Ctenocephalides sp. and the like),
- ticks (Rhipicephalus sp., Ixodes sp., entor sp., Amblyomma sp. and the like),
- mites (Demodex sp., tes sp., Otodectes sp. and the like), - lice (Trichodectes sp.,
Cheyletielfa sp., Linognathus sp., and the like), and
- flies (Hematobia sp., Musca sp., Stomoxys sp., Dermatobia sp., Cochliomyia sp.,
mosquitoes (family Culicidae) and the like).
Fleas are a particular problem because not only do they adversely affect the health of the
animal or human, but they also cause a great deal of logical stress. Moreover, fleas are
also vectors of pathogenic agents in animals, such as dog tapeworm (Dipylidium caninum) and
may also transmit pathogens to humans.
Similarly, ticks are also l to the physical and psychological health of the animal or
human. However, the most serious problem associated with ticks is that they are the vector of
pathogenic agents, which cause diseases in both humans and animals. Major diseases which are
caused by ticks include borreliosis (Lyme disease caused by Borrelia burgdorfen), babesiosis (or
piroplasmosis caused by Babesia sp.) and rickettsiosis (also known as Rocky Mountain spotted
fever). Ticks also release toxins which cause inflammation or paralysis in the host. Occasionally,
these toxins are fatal to the host, such as in the case of the Australian paralysis tick, Ixodes
holocyclus.
Moreover, mites and lice are particularly difficult to combat since there are very few
active substances which act on these parasites and they require frequent ent.
se, farm animals are also susceptible to parasite infestations. For example, cattle are
affected by a large number of parasites (e.g, arthropod pests, such as fleas, lice and ticks, and
mites). A parasite that is very prevalent among farm animals is the tick genus Boophl'lus.
especially those of the species micropJus (cattle tick), decoloratus and anulatus. Ticks. such as
Boophz'lus microplus, are particularly difficult to control because they live in the e where
the farm animals graze. Other important parasites of cattle and sheep are listed below:
(a) myiases such as Dermatobz'a hominis (known as Beme in Brazil), Hypoderma, and
Cochlyomz'a hominivorax (greenbottle); sheep myiases such as Lucilz’a sericata, Lucilz’a cuprz’na
(known as blowfly strike in Australia, New Zealand and South Africa). These are flies whose
larva constitutes the animal parasite;
(b) flies proper, namely those whose adult constitutes the parasite, such as obz'a irritans
(i.e., horn fly);
(c} lice such as Linognathus vituz’ etc.; and
(d) mites such as Sarcoptes scabiez’ and Psoroptes ovis.
The above list is not exhaustive and other ectoparasites are well known in the art to be harmful to
animals.
Protection of animals against parasites is essential to insure a healthy and safe
nment for s and their owners. Pour-on and spot-on topical formulations are widely
used to deliver treatment agaist variety of al and internal parasiticids, such as ticks, fleas,
flies, mites, worms, etc. These formulations are solutions that are applied onto the back of an
animal and allowed to spread or penetrate. To be effective, these ations need to retain an
active in upper layers of skin or drive an active into the skin for systemic absorbtion, and to be
able to withstand eVironmental stress (e.g., rain), to prevent removal of the drug. Depending on
the intended use, topical formulations typically consist of a solvent with or without a ation
enhancer (for systemically delivered drugs), or a solvent or co-solvents with addition of
spreading agent, and various performance ves for delivery into upper layers of the skin.
This is a traditional approach to formulating a topical pour-on or n solution. Currently
marketed l pour-ons for production animals for protection from external parasites do not
have good water resistance and need to be re-applied ntly.
For example, the cial products for control of horn fly on cows provide limited
protection lasting from several days to two weeks and require re-application after rain throughout
the fly . This creates unnecessary stress for animals resulting in significant productivity
losses and onal labor efforts for farmers.
Current commercially ble topical solutions to control horn fly population on cows
provide limited duration of protection lasting from several days to about two weeks. Current
treatments fiarther e frequent re-application due to a wash-off after exposure to
environmental conditions such as rain.
Extension of efficacy to one month or longer will provide continuous protection against
the horn fly with less frequent applications. Fewer applications will be less stressfill for the
animals and less time and labor consuming for the farmers.
There are several problems that contribute to the short duration of the active ient(s)
in the current pour-on nonsystemic formulations. First, the conventional solvent system (organic
solvents) applied topically is expected to spread the active ingredient and retain it on the skin for
the duration of the desired treatment period. Second, a complete dose intended to last for the
duration of the treatment period is applied at one time. Third, conventional solvent systems are
not well formulated to resist some weather nges. The active ingredient is completely
exposed to nmental conditions. The solvent carrying the active ingredient is washed off
during rain, rendering it non-efficacious. Fourth, the solvent system may not stay on the animal
during the treatment process resulting in a non-efficacious ent.
Compounds that t a degree of activity against a wide range of ectoparasites
including arthopods and insects are known in the art. One such class of nds is the
arylpyrazoles which are referred to, for example, in US. Patent Nos. 5,122,530; 5,246,255;
,576,429; 5,885,607; 6,010,710; 6,083,519; 6,096,329; 6,685,954; EP 0 234 119 and EP 0 295
117 (US. Patent Nos. 5,232,940; 5,547,974; 5,608,077; 5,714,191; 5,916,618 and 6,372,774); EP
0 352 944 (US. Patent No. 4,963,575); EP 8 (US. Patent No. 5.817,688; 5,922,885;
,994,386; 6.124,339; 6,180,798 and 6,395,906); EP 0846686 (US. Patent No. 6,069,157); WO
98/28278, WO 08/05489, US. 381 and US. 8,445,519. All ofthe aforementioned patents
and patent publications are herein incorporated by reference.
The arylpyrazoles are known to possess excellent activity against insects, such as fleas
and ticks. Fipronil is a specific type of l-N-arylpyrazole that is particularly effective against fleas
and ticks and is the active ingredient in Frontline® and Frontline Plus®. Another arylpyrazole, l-
(2-chlorofluorotrifluoromethylphenyl)dichlorofluoro-methylsulf1nylmethylpyrazole-
3-carbonitrile, has structure and properties similar to f1pronil.
Other classes of compounds are also known in the art to be effective parasiticides.
Examples include macrocyclic lactones (e.g., avermectins and their tives ivermectin,
eprinomectin, selamectin, doramectin and abamectin), benzimidazoles (e.g., triclabendazole),
levamisole, closantel and pment inhibitors such as S-methoprene.
There is a need for a ation that can be applied as a pour-on or a spot-on
formulation but offers higher water resistance and extended duration of efficacy. This will
decrease stress to the animals and avoid the labor and costs associated with le pour-on
applications. It will further avoid labor and costs ated with attaching and retrieving ear tags.
SUMMARY OF THE INVENTION
The topical solution of the invention es at least one active ient and a volatile
solvent system that contains at least one dissolved polymer. The t system is not designed to
maximize spreading, but instead, to have some spreading and to evaporate shortly after dosing,
leaving a water-resistant film ofpolymer on the skin and hair. This could consist of a contiguous
film or a conglomerate of polymer particles adhering to hair and skin of an animal. After
evaporation of the volatile solvent(s), the active(s), ped into the polymer will diffuse out at
a specified rate and will be d by skin lipids of an animal. The active(s) need to be able to
dissolve not only in the volatile solvent system, but also in the polymer. The rate of diffusion can
be impacted by selection of ts, their ratios, selection of polymers, addition of a
plasticizer(s) and its chemical composition, or by the skin lipids naturally occurring on skin. The
selection of excipients also will impact such formulation properties as water resistance, run-off
during dosing, and duration of efficacy.
The invention es for an increased duration of efficacy of a topical formulation
through the use of a r dissolved in the formulation. As the formulation dries on the
surface r hair or skin), the active ingredient is entrapped in the resulting polymer matrix.
The rate of release of the active can be controlled by incorporating and adjusting the amount of a
“plasticizer” (i.e., a solvent that is fluid in the solidified polymer). The resultant polymer matrix
will then perform similarly to the ional transdermal patch or ear tag.
In one aspect, the invention is a topical delivery formulation with one or more solvents to
include saturated aliphatic ketones, esters and alcohols. The invention further includes a water
insoluble polymer alone or in combination with a water soluble polymer, and, optionally a
plasticizer.
Examples of solvents include, but are not limited to, methyl isobutyl ketone, butyl acetate,
ethyl lactate, isopropyl alcohol or ethanol. Examples of water insoluble polymers include, but are
not limited to, vinyl acetate, polyisobutene, methacrylates, polyurethanes, styrenes and polyolefin
elastomers. Non-limiting examples of water e polymers include povidone, polyvinyl
alcohol, polyacrylic acid and ethyl cellulose. The al plasticizer may be, for e, an
aliphatic ester such as acetyl tributyl citrate. Other esters may function as plasticizers, for
example, triethyl citrate, tributyl citrate, acetyl triethyl citrate, cetearyl ate and lanolin.
Further, polymers (e.g., polybutene), oils (e.g., castor oil), and propylene glycol and propylene
glycol esters may function as plasticizers. Oily actives, such as pyrethroids (e.g., permethrin) and
growth regulators (e.g., (s)-methoprene) can also act as plasticizers.
In r , the invention is a method of making a topical delivery formulation
using the solvents, polymers and optional plasticizers described .
In yet another aspect, the invention is a use of a topical delivery formulation in the
manufacture of a medicament for the therapeutic and/or prophylactic treatment of an animal
against an ectoparasite and/or an endoparasite.
In yet another aspect, there is provided a method for the therapeutic and/or prophylactic
treatment of an animal t an endoparasite sing stering to an animal in need
thereof a topical ry formulation, comprising:
at least one veterinary active ingredient having endoparasiticidal activity;
one or more solvent(s) selected from the group consisting of saturated aliphatic
ketones, esters and alcohols;
a water insoluble polymer alone or in ation with a water e polymer; and
optionally a plasticizer.
DETAILED PTION OF THE INVENTION
In one aspect, the invention is a topical delivery formulation with one or more solvents
to include saturated aliphatic ketones, esters and alcohols. The invention further includes a
water insoluble polymer alone or in combination with a water soluble polymer, and, optionally
a plasticizer.
Examples of solvents include, but are not limited to, methyl isobutyl ketone, butyl acetate,
ethyl lactate, isopropyl l or ethanol. A non-limiting example of a water insoluble
polymer
5a followed by page 6
is vinyl e. Non-limiting examples of water soluble polymers e povidone, polyvinyl
alcohol or ethyl cellulose. The optional plasticizer may be an aliphatic ester such as acetyl
tributyl citrate.
Veterinarily active ingredients, which include, but are not limited to, ides,
anthelmintics, antiparasitics, insecticides and insect repellants, may also be added to the
compositions of the invention. Antiparasitic agents can include both ectoparasiticidal and
endoparasiticidal agents. These agents are well-known in the art (see e.g. Plamb' Veterinary Drag
Handbook, 5th Edition, ed. Donald C. Plumb, Blackwell Publishing, (2005) or The Merck
Veterinary Manual, 9th Edition, (January 2005) and include but are not limited to acarbose,
acepromazine maleate, acetaminophen, acetazolamide, acetazolamide sodium, acetic acid,
acetohydroxamic acid, acetyl cysteine, acitretin, acyclovir, albendazole, albuterol sulfate,
alfentanil HCl, allopurinol, alprazolam, altrenogest, amantadine HCl, amikacin sulfate,
aminocaproic acid, aminopentamide hydrogen e, aminophylline/theophylline, amiodarone
HCl, amitraz, amitriptyline HCl, pine besylate, ammonium chloride, ammonium
molybdenate, amoxicillin, amoxicillin, clavulanate potassium, amphotericin B desoxycholate,
amphotericin B lipid-based, ampicillin, ium HCl, antacids (oral), nin, apomorphione
HCl, apramycin sulfate, ascorbic acid, asparaginase, aspiring, atenolol, atipamezole HCl,
atracurium besylate, atropine e, aumofin, ioglucose, one, oprine,
omycin, baclofen, barbituates, benazepril HCl, betamethasone, bethanechol chloride,
dyl, bismuth subsalicylate, bleomycin sulfate, boldenone undecylenate, es,
bromocriptine mesylate, budenoside, buprenorphine HCl, buspirone HCl, an, butorphanol
tartrate, cabergoline, calcitonin salmon, calcitrol, calcium saits, captopril, carbenicillin indanyl
sodium, carbimazole, carboplatin, camitine, carprofen, carvedilol, cefadroxil, cefazolin sodium,
cefixime, cefoperazone sodium, cefotaxime sodium, cefotetan um, cefoxitin sodium,
cefpodoxime proxetil, idime, ceftiofur sodium, ceftiofur HCI, ceftiaxone sodium,
cephalexin, cephalosporins, cephapirin, charcoal (activated), mbucil, chloramphenicol,
chlordiazepoxide, chlordiazepoxide +/- clidinium bromide, chlorothiazide, chlorpheniramine
maleate, chlorpromazine HCl, chlorpropamide, etracycline, chorionic gonadotropin (HCG),
chromium, cimetidine, ciprofloxacin, cisapride, cisplatin, citrate salts, clarithromycin, clemastine
fumarate, clenbuterol HCl, clindamycin, clofazimine, clomipramine HCl, claonazepam,
clonidine, cloprostenol sodium, clorazepate dipotassium, lon, cloxacillin, codeine
phosphate, colchicine, corticotropin (ACTH), cosyntropin, cyclophosphamide, cyclosporine,
cyproheptadine HCl, cytarabine, dacarbazine, dactinomycin/actinomycin D, dalteparin sodium,
danazol, dantrolene sodium, dapsone, decoquinate, deferoxamine mesylate, deracoxib, deslorelin
acetate, desmopressin acetate, desoxycorticosterone pivalate, detomidine HCl, dexamethasone,
thenol, dexraazoxane, dextran, diazepam, diazoxide (oral), dichlorphenamide, rvos,
diclofenac , dicloxacillin, diethylcarbamazine citrate, diethylstilbestrol (DES), difloxacin
HCl, digoxin, dihydrotachysterol (DHT), diltiazem HCl, ydrinate, dimercaprol/BAL,
dimethyl sulfoxide, dinoprost tromethamine, diphenylhydramine HCl, ramide phosphate,
dobutamine HCl, docusate, dolasetron mesylate, domperidone, ne HCl, doramectin,
doxapram HCl, doxepin HCl, doxorubicin HCl, doxycycline, edetate calcium disodium, calcium
EDTA, edrophonium chloride, ril, enoxaparin , enrofloxacin, ephedrine sulfate,
epinephrine, epoetin/erythropoietin, eprinomectin, epsiprantel, erythromycin, esmolol HCl,
estradiol ate, ethacrynic acid/ethacrynate sodium, ethanol (alcohol), etidronate sodium,
etodolac, etomidate, euthanasia agents obarbital, famotidine, fatly acids (essential/omega),
felbamate, fenbendazole, fentanyl, ferrous sulfate, filgrastim, f1nasteride, f1pronil, florfenicol,
fluconazole, flucytosine, fludrocortisone acetate, flumazenil, flumethasone, flunixin
meglumine, fluorouracil (S-FU), fluoxetine, fluticasone nate, fluvoxamine maleate,
zole (4-MP), filrazolidone, furosemide, gabapentin, gemcitabine HCl, gentamicin sulfate,
glimepiride, glipizide, on, glucocorticoid agents, glucosamine/chondroitin sulfate,
glutamine, glyburide, glycerine (oral), glycopyrrolate, relin, grisseofulVin, guaifenesin,
halothane, hemoglobin glutamer—200 (oxyglobln®), heparin, hetastarch, hyaluronate sodium,
hydrazaline HCl, hydrochlorothiazide, hydrocodone bitartrate, hydrocortisone, hydromorphone,
hydroxyurea, hydroxyzine, ifosfamide, imidacloprid, imidocarb dipropinate, impenem-cilast?ltin
sodium, imipramine, inamrinone e, insulin, interferon alfa-2a (human inant), Iodide
(sodium/potassium), ipecac (syrup), ipodate sodium, iron dextran, isoflurane, terenol HCl,
isotretinoin, isoxsuprine HCl, itraconazole, ivermectin, kaolin/pectin, ketamine HCl,
ketoconazole, ketoprofen, ketorolac tromethamine, ose, leuprolide, levamisole,
levetiracetam, levothyroxine , lidocaine HCl, lincomycin HCl, liothyronine sodium,
prll, lomustine (CCNU), lufenuron, lysine, magnesium, mannitol, oxacin,
mechlorethamine HCl, meclizine HCl, meclofenamic acid, medetomidine HCl, medium chain
cerides, medroxyprogesterone acetate, megestrol acetate, melarsomine, melatonin,
meloxican, melphalan, meperidine HCl, mercaptopurine, meropenem, metformin HCl,
methadone HCl, methazolamide, methenamine mandelate/hippurate, methimazole, methionine,
methocarbamol, methohexital sodium, methotrexate, methoxyflurane, methylene blue,
methylphenidate, methylprednisolone, metoclopramide Hel, olol, metronidaxole,
mexiletine HCl, mibolerlone, midazolam HCl, milbemycin oxime, mineral oil, minocycline HCl,
misoprostol, ne, mitoxantrone Hel, el tartrate, morphine sulfate, moxidectin,
naloxone HCl, lone decanoate, naproxen, narcotic (opiate) agonist analgesics, neomycin
sulfate, neostigmine, niacinamide, xanide, nitenpyram, nitrofurantoin, nitroglycerin,
nitroprusside sodium, dine, novobiocin sodium, nystatin, octreotide acetate, olsalazine
sodium, omeprozole, ondansetron, opiate antidiarrheals, orbifJoxacin, oxacillin sodium,
oxazepam, oxfendazole, oxybutynin chloride, oxymorphone HCl, oxytretracycline, oxytocin,
pamidronate disodium, pancreptipase, pancuronium bromide, paromomycin sulfate, parozetine
HCl, pencillamine, general ation penicillins, penicillin G, penicillin V, ium,
pentazocine, pentobarbital sodium, pentosan polysulfate sodium. pentoxifyiline, pergolide
mesylate, phenobarbital, phenoxybenzamine HCl, pheylbutazone, phenylephrine HCl,
phenypropanolamine HCl, oin sodium, ones, parenteral phosphate,
phytonadione/Vitamin K-l, ndan, zine, pirlimycin HCl, cam, polysulfated
glycosaminogiycan, ponazuril, potassium chloride, pralidoxime chloride, praziquantel,
prazosin HCl, prednisolone/prednisone, primidone, procainamide HCl, procarbazine HCl,
prochlorperazlne, propantheline bromide, propofol, propranolol HCl, protamine sulfate,
pseudoephedrine HCl, psyllium hilic mucilloid, pyrantel pamoate, pyridostlgmine
bromide, pyrilamine maleate, pyrimethamine, quinacrine HCl, quinidine, ranltidine HCl,
rifampin, s-adenosyl-methionine (SAMe), saline/hyperosmotic laxative, selamectin, selegiline
HCl, deprenyl, sertraline HCl, mer HCl, sevoflurane, rin/milk thistle, sodium
bicarbonate, sodium poiystyrene sulfonate, sodium stibogluconate, sodium e, sodum
thiosulfate, somatotropin, sotalol HCl, spectinomycin HCl, spironolactone, olol,
streptokinase, streptozocin, succimer, succinylcholine chloride, sucralfate, sufentanil citrate,
sulfachlorpyridazine sodium, sulfadiazine/trimethroprim, sulfamethoxazole/trimethoprim,
sulfadimentoxine, sulfadimethoxine/ormetoprlm, sulfasalazine, taurine, tepoxaline, terbinafline
HCl, terbutaline sulfate, terone, tetracycline HCl, thiabendazole, thiacetarsamide sodium,
thiamine HCl, thioguanine, thiopental sodium, ropin, tiamulin, ilin disodium,
tiletamine HCl, zolazepam HCl, tilmocsin, tiopronin, tobramycin sulfate, tocainide HCl,
tolazoline HCl, amic acid, topiramate, tramadol HCl, trimcinolone acetonide, trientine HCl,
trilostane, trimepraxine tartrate w/prednisolone, tripelennamine HCl, n, urdosiol, valproic
acid, vanadium, vancomycin HCl, vasopressin, vecuronium bromide, verapamil HCl, vinblastine
sulfate, vincristine sulfate, vitamin E/selenium, warfarin , xylazine HCl, yohimbine HCl,
zidovudine (AZT), zinc acetate/zinc sulfate, zonisamide and mixtures thereof.
In one embodiment of the invention, pyrazole compounds such as phenylpyrazoles, as
described above (e.g., flpronil), are known in the art and are suitable actives alone or in
combination with other active compounds of the invention. Examples of such pyrazole
compounds include but are not limited to those described in US. Patent Nos. 6,001,384;
6,010,710; 6,083,519; 6,096,329; 6,174,540; 6,685,954 6,998,131; 7,759,381 and 8,445,519.
Each is assigned to Merial, Ltd., (Duluth, GA, USA) and incorporated by reference herein. (RS)-
-amino [2,6-dichloro(trifluoromethyl)phenyl](trifluoromethylsulf1nyl)- 1 zole-3 -
itrile (i.e., il), 1H—pyrazolecarbonitrile, 1-[2,6-dichlorotrifluoromethyl)phenyl]-
-methyl[(trifluoromethyl)sulf1nyl] (i.e., ML465), and 1-(2-chlorofluoro
trifluoromethylphenyl)dichlorofluoro-methylsulfinylmethylpyrazolecarbonitrile (i. e.,
ML198) are specifically referenced.
In another embodiment of the invention, nodulisporic acid and its derivatives (a class of
known acaricidal, minitic, anti-parasitic and insecticidal ) can be added to the
compositions of the invention. These compounds are used to treat or prevent infections in humans
and s and are described, for example, in US. Patent No. 5,399,582 and 5,962,499. The
composition can include one or more of the known nodulisporic acid derivatives in the art,
including all stereoisomers, such as those described in the literature cited above.
In another embodiment of the invention, one or more macrocyclic lactones, which act as
an ide, anthelmintic agent and insecticide, can be added to the compositions of the
ion. The macrolides are well-known in the art. See e.g., Macrolides - Chemistry,
pharmacology and clinical uses - edited by Bryskier et al., published by Amette ell,
(1993). Macrolides include, but are not d to, 12-membered ring macrolides (e. g.
methymycin, neomethymycin, YC-17, litorin); 14-membered ring macrolides (e.g., erythromycin
A-F, oleandomycin, sporeamicin, roxithromycin, dirithromycin, f1urithromycin, clarithromycin,
davercin); 15-membered ring macrolides (e.g., azithromycin); 16-membered ring macrolides
(e.g., josamycin, kitasamycin, spiramycin, midecamycin, mycin, miokamicin) and 17-
membered ring macrolides (e.g., lankadicin).
The macrocyclic lactones also include, but are not limited to, avermectins, such as
abamectin, ctin, doramectin, emamectin, eprinomectin, ivermectin, latidectin, lepimectin,
selamectin and milbemycins, such as milbemectin, milbemycin D, moxidectin and nemadectin.
Also included are the 5-oxo and 5-oxime derivatives of said ctins and milbemycins.
Examples of combinations of razole compounds with macrocyclic lactones include but are
not limited to those described in US. Patent Nos. 6,426,333; 6,482,425; 6,962,713 and 6,998,131
- each assigned to Merial, Ltd. (Duluth, GA, USA).
The macrocyclic lactone compounds are known in the art and can easily be obtained
commercially or through synthesis techniques known in the art. Reference is made to the widely
available technical and commercial literature. For avermectins, ivermectin and abamectin,
reference may be made, for example, to the work "Ivermectin and Abamectin", 1989, by M.H.
Fischer and H. Mrazik, William C. Campbell, published by Springer Verlag., or Albers-
Schonberg et al. (1981), “Avermectins ure Determination”, J. Am. Chem. Soc., 103, 4216-
4221. For doramectin, "Veterinary Parasitology", vol. 49, No.1, July 1993, 5-15 may be
consulted. For milbemycins, reference may be made, inter alia, to Davies H.G. et al., 1986,
"Avermectins and ycins", Nat. Prod. Rep., 3, 87-121, Mrozik H. et al., 1983, Synthesis of
Milbemycins from Avermectins, Tetrahedron Lett., 24, 5333-5336, US. Patent No. 4,134,973
and EP 0 677 054.
Macrocyclic lactones are either natural ts or are semi-synthetic derivatives thereof.
The structure of the ctins and milbemycins are closely related, e. g., by sharing a x
16-membered macrocyclic lactone ring; milbemycins lack the glycosidic moiety of the
avermectins. The natural t avermectins are disclosed in US. Patent No. 4,310,519 to
Albers-Schonberg et al., and the dihydro avermectin compounds are disclosed in a
et al., US. Patent No. 4,199,569. Mention is also made of Kitano, US. Patent No. 4,468,390,
Beuvry et al., US. Patent No. 5,824,653, EP 0 007 812 A1, U.K. Patent Specification 1 390 336,
EP 0 002 916, and Ancare New Zealand Patent No. 237 086, inter alia. Naturally occurring
ycins are described in Aoki et al., US. Patent No. 3,950,360 as well as in the various
references cited in "The Merck Index" 12th ed., S. Budavari, Ed., Merck & Co., Inc. Whitehouse
Station, New Jersey (1996). Latidectin is described in the "International Nonproprietary Names
for Pharmaceutical Substances (INN)", WHO Drug Information, vol. 17, no. 4, pp. 263-286,
(2003). Semisynthetic derivatives of these classes of compounds are well known in the art and
are described, for example, in US. Patent No. 5,077,308, US. Patent No. 4.859,657, US. Patent
No. 4.963,582, US. Patent No. 317, US. Patent No. 719, US. Patent No. 4.874,749,
US. Patent No. 4,427,663, US. Patent No. 4,310,519, US. Patent No. 4,199,569, US. Patent
No. 5,055,596, US. Patent No. 4,973,711, US. Patent No. 677, US. Patent No. 4,920,148
and EP 0 667 054.
In another embodiment of the invention, the class of acaricides or insecticides known as
insect growth regulators (IGRs) can also be added to the compositions of the invention.
Compounds belonging to this group are well known to the tioner and represent a wide range
of different chemical classes. These compounds all act by interfering with the development or
growth of the insect pests. Insect growth regulators are bed, for example, in US. Patent No.
3,748.356; US. Patent No. 3,818,047; US. Patent No. 4,225,598; US. Patent No. 4,798,837;
US. Patent No. 4,751,225, EP 0179022 or UK. 2 140 010 as well as US. Patent Nos. 6,096,329
and 6,685,954 (both assigned to Merial Ltd., Duluth, GA). Examples of IGRs suitable for use
include but are not d to methoprene, oxyfen, hydroprene, cyromazine, f1uazuron,
lufenuron, novaluron, pyrethroids, formamidines and 1-(2, 6-difluorobenzoyl)—3-(2-fluoro(trifl
uoromethyl)phenylurea. An anthelmintic agent that can be combined with the compound of the
invention to form a ition can be a benzene disulfonamide compound, which includes but
is not limited to clorsulon; or a cestodal agent, which includes but is not limited to praziquantel,
pyrantel or morantel.
An antiparasitic agent that can be combined with the nd of the ion to form a
composition can be a ically active peptide or protein including, but not limited to,
depsipeptides, which act at the neuromuscular junction by stimulating presynaptic receptors
belonging to the secretin receptor family resulting in the paralysis and death of parasites. In one
embodiment of the depsipeptide, the depsipeptide is emodepside.
An insecticidal agent that can be combined with the compound of the invention to form a
composition can be a spinosyn (e.g. spinosad) or a substituted pyridylmethyl derivative
compound such as imidacloprid. Agents of this class are described above and for example, in
US. Patent No. 4,742,060 or in EP 0 892 060. It would be well within the skill level of the
practitioner to decide which individual compound can be used in the ive ation to
treat a particular infestation of an insect.
Insect repellants, alone or in combination with the above, may also be considered actives
in the present invention. Examples include pyrethroids such as allethrin, alphamethrin,
methrin, byfenthrin, cycloprothrin, cyfluthirin, decamethrin, cyhalothrin, cypermethrin,
deJtamethrin, cyanophenylmethylbenzyl 2,2-dimethyl(2-chlorotrifluoro-
methylvinyl)cyclopropane-carboxylate, fenpropathrin, fenfluthrin, fenvalerate, flucythrinate,
flumethrin, fluvalinate, hrin, resmethrin and tralomethrin.
In general, the pesticidal agent or repellant is included in a dose of between about 0.1 ug
and about 10 mg. In one embodiment of the invention, the pesticidal agent or repellant is
ed in a dose of between about 1 ug and about 10 mg. In another embodiment of the
invention, the pesticidal agent or repellant is ed in a dose of about 5 to about 200 ug/kg of
weight of animal. In yet another embodiment of the invention, the pesticidal agent or repellant is
included in a dose between about 0.1 to about 10 mg/kg of weight of . In still another
embodiment of the invention, the pesticidal agent or repellant is included in a dose between about
0.5 to 50 mg/kg.
The proportions, by weight, of the 1-arylalkyl pyrazole compound and any additional
pesticidal agent are, for example, between about 5/1 and about 10,000/ 1. However, one of
ordinary skill in the art would be able to select the appropriate ratio of 1-arylalkyl pyrazole
compound and the onal pesticidal agent for the intended host and use thereof.
In another embodiment of the invention, the formulation can be in ready-to-use on
form as is described in US. Patent No. 6,395,765, incorporated herein by reference. In addition
to the active(s) nd, the solution can n a crystallization inhibitor. The crystallization
inhibitor can be present in a proportion of about 1 to about 20% (w/v). Alternatively, the
crystallization inhibitor can be present in a proportion of about 5 to about 15%. In another
embodiment of the amount of crystallization inhibitor, the amount corresponds to the test in
which 0.3 ml of a solution comprising 10% (w/v) of 1-arylalkyl pyrazole compound in the
liquid carrier and 10% of the inhibitor are deposited on a glass slide at 20°C and allowed to stand
for 24 hours. The slide is then observed with the naked eye. Acceptable inhibitors are those
whose on provides for few (e.g., less than ten crystals) or no crystal.
Crystallization inhibitors which are useful for the ion include but are not limited to:
(a) polyvinylpyrrolidone, polyvinyl alcohols, copolymers of Vinyl acetate and of
Vinylpyrrolidone, polyethylene glycols, benzyl alcohol, mannitol, ol, sorbitol or
polyoxyethylenated esters of sorbitan; lecithin or sodium carboxymethylcellulose; or acrylic
derivatives, such as methacrylates;
(b) anionic surfactants, such as alkaline stearates (e.g., sodium, potassium or ammonium
stearate); calcium stearate or triethanolamine stearate; sodium abietate; alkyl sulphates, which
include but are not limited to sodium lauryl sulphate and sodium cetyl sulphate; sodium
dodecylbenzenesulphonate or sodium dioctyl sulphosuccinate; or fatty acids (e.g., coconut oil);
(c) ic surfactants, such as water-soluble ary ammonium salts of formula
N+R'R"R'"R""Y-, in which the R radicals are identical or different optionally hydroxylated
hydrocarbon radicals and Y- is an anion of a strong acid, such as halide, sulphate and sulphonate
anions; cetyltrimethylammonium bromide is one ofthe cationic surfactants which can be used;
(d) amine salts of formula N+R'R"R"', in which the R radicals are identical or different optionally
ylated arbon radicals; octadecylamine hydrochloride is one of the cationic
surfactants which can be used;
(e) non-ionic surfactants, such as optionally polyoxyethylenated esters of sorbitan, e.g.,
rbate 80, or polyoxyethylenated alkyl ethers; polyethylene glycol stearate,
polyoxyethylenated derivatives of castor oil, polyglycerol esters, polyoxyethylenated fatty
alcohols, yethylenated fatty acids or mers of ethylene oxide and of propylene oxide;
(f) amphoteric surfactants, such as substituted lauryl compounds of betaine; or
(g) a mixture of at least two of the compounds listed in ) above.
In another embodiment of the ion, the formulation can also comprise an
antioxidizing agent intended to inhibit oxidation in air. This agent may be present in a proportion
of about 0.005 to about 1 % (w/v) Alternatively, the antioxidizing agent may be present in a
tion of about 0.01 to about 0.05%. Antioxidizing agents include, but are not limited to,
butylated yanisole, butylated hydroxy toluene, ic acid, sodium metabisulphite,
propyl gallate, sodium thiosulphate or a mixture of not more than two of the above.
Embodiments of the invention may also include colorants, fragrances and pH stabilizers
known in the art. Examples of colorants include, but are not limited to, titanium dioxide and iron
oxide. A comprehensive list of acceptable nts may be found at 37 CFR, Title 21, Part 74.
Colorants and pH stabilizers are conventional and known in the art.
The invention is also ed toward a method of treating an animal (e.g., a mammal),
against ectoparasitic infection by administering an ectoparasiticidally effective amount of the
composition of the invention. s which can be treated include, but are not d to,
humans, cats, dogs, cattle, chickens, cows, deer, goats, horses, llamas, pigs, sheep and yaks. In
one embodiment of the invention, the mammals treated are humans, cats or dogs.
In another embodiment for treatment against ectoparasites, the ectoparasite is one or more
insect or arachnid including those of the genera Ctenocephalides, ha’pz’cephalus, Dermacentor,
Ixodes, Boophz'lus, Ambylomma, Haemaphysall's, Hyalomma, Sarcoptes, Psoroptes, OtOdectes,
Chorioptes, Hypoderma. Damalz'm'a, Linognathus, Haematopinus, Solenoptes, Trichodectes, and
Felicola.
In r embodiment for the treatment against ectoparasites, the ectoparasite is from the
genera Ctenocephalides, cephalus, entor, Ixodes and/or Boophl'lus. The
ectoparasites treated include but are not d to fleas, ticks, mites mosquitoes, flies, lice,
blowfly and ations thereof. Specific examples include but are not d to cat and dog
fleas cephalz’desfelz’s, Ctenocephalz’des sp. and the like), ticks (Rhipicephalus sp., Ixodes
sp., Dermacentor sp., Amblyoma sp. and the like), and mites (Demodex sp., Sarcoptes sp.,
0t0dectes sp. and the like), lice (Trichodectes sp., Cheyletz'ella sp., athus sp., and the like),
mosquitoes (Aedes sp., Culex sp., Anopheles sp., and the like) and flies (Hematobz'a sp., Musca
sp., Stomoxys sp., Dematobz'a sp., Cochlz'omyz'a sp., and the like). In yet another embodiment for
the treatment against ectoparasites, the ectoparasite is a flea and/or tick.
onal examples of ectoparasites include but are not limited to the tick genus
Boophz'lus, especially those of the s lus (cattle tick), decoloratus and annulatus;
myiases such as Dermatobz'a hominis (known as Beme in Brazil) and Cochlz'omyz'a hominivorax
(greenbottle); sheep myiases such as Lucilz’a sericata, Lucilz’a cuprz’na (known as blowfly strike in
Australia, New Zealand and South Africa). Flies proper, namely those whose adult constitutes the
paraSite, such as Haematobz'a irritans (horn fly): lice such as Linognathus vitulorum, etc.; and
mites such as Sarcoptes scabicz' and Psoroptes ovis. The above list is not exhaustive and other
ectoparasites are well known in the art to be harmful to animals and humans. These include, for
example migrating dipterous larvae.
When an anthelmintic agent is added to the composition of the invention, the composition
can also be used to treat against endoparasites such as those helminths selected from the group
consisting ofAnaplocephala, Ancylostoma, Anecator, Ascarz's, Capillaria, Cooperl'a, z'dz'um,
Dirofilarz'a, Echinococcus, bius, FaSCz'ola, chus, Oesophagostumum, Osterz'agz'a,
Toxocara, Strongyloz'des, aris, Trichz'nella, Trichurz's, and Trichostrongylus.
In another embodiment, the compounds of the invention are administered in spot-on
formulations. While not wishing to be bound by theory, it is believed that these ations
work by l diffusion of active(s) encapsulated into the r or blend of polymers that
adhere to hair and skin after evaporation of solvent(s), and dissolution of the dose in the natural
oils of the host's skin or fur. Thus, the polymer becomes is a reservoir that stores and protects
active(s) from environmental stress, such as rain, for the duration of the treatment period, and
active(s) continues to gradually diffuse from the polymer and replenish the therapeutic amounts
of active(s) washed off during rain or removed by other means (e.g., licking, rubbing).
From there, the active agent(s) distribute around the host's body through the sebaceous glands of
the skin. The therapeutic agent also remains in the sebaceous glands.
In one embodiment of the location of administration, a single formulation containing the
active agent in a substantially liquid carrier and in a form which makes possible a single
application, (e. g., as a pour-on or can be applied as a spot-on at one or multiple locations of the
animal’s body) will be administered to the animal over a localized region of the , e.g.,
between the two ers or along the spine. The invention is further described by the following
non-limiting examples which fiarther illustrate the invention, and are not intended, nor should
they be interpreted to, limit the scope of the invention.
In one ation of the invention, Haematobia irritans (L., z'.e., horn fly), is a pest of
cattle that causes significant economic losses estimated at more than $1 billion in the United
States annually. Horn fly infestation leads to decreased milk tion, decreased g
s of calves, and decreased weight gains on growing cattle. (Domingues, L.N., et al.,
Discovery of the Rdl mutation in association with a cyclodiene resistant population of horn flies,
Haematobia irritans (Diptera: Musidae). Vet. Parasitol. (2013)).
Current commercially available topical ons to l horn fly population on cows
provide limited on of protection lasting from several days to about two weeks. Current
treatments fiarther require frequent re-application due to a wash-off after exposure to
environmental conditions such as rain. Extension of efficacy to one month or longer will provide
continuous tion against the horn fly with less frequent ations. Fewer applications will
be less stressful for the animals and less time and labor consuming for the farmers. This may be
accomplished by using active ingredients of superior efficacy, by using an ed delivery
mechanism, or both.
Although many different actives may work with the formulation of the invention, 1H-
pyrazolecarbonitrile, l-[2,6-dichloro(trifiuoromethyl)phenyl]methyl
[(trifiuoromethyl)sulfinyl] (i.e., ML465) is the compound used to test topical formulations for
control of horn fly on cows for a duration of one month or longer.
Water Resistance
In-vz’vo and in-vz’tro studies were conducted to compare wash-off resistance of formulations
prepared with lipophilic solvents and with polymers. Results indicate that a wash-off resistance is
higher for formulations with polymers. Water resistance ofknown solvent s used in
clinical in-vivo studies A and B was evaluated and results are summarized in Table 1 Table 1
below shows water resistance of conventional n formulations used in clinical studies A and
Table l.
o % ML465 in Solvent System Duration of
Efficacy Solutions, w/v above 90%
study efficacy (days)
% Tributyl acetyl citrate
A 3 .0 l 7
l 840
% yl acetyl citrate
% Polypropylene Glycol (15) stearyl ether
Soybean Oil
% Tributyl acetyl citrate
3% opylene Glycol (15) stearyl ether
8.5% Isopropyl palmitate
7% Isobutene H25
Soybean Oil
% Tributyl acetyl citrate
3% Polypropylene Glycol (15) stearyl ether
% Isopropyl palmitate
7% cetearyl octanoate
% butyl stearate
Soybean Oil
Trials A and B with traditional formulations containing ML465 did not result in a d
duration of cy due to the impact of water exposure during rains which occur randomly and
have highly variable intensity. It can be seen that the amount of ML465 washed off is at, or
below, 10% of the applied dose, indicating a sharp decrease upon exposure to water. This was not
sufficient to support thirty days efficacy duration. Thus, cy may depend on resistance of the
solvent system to water exposure.
The in-vz'vo studies of Table 1 were followed with in-vz'tro studies conducted to assess
water resistance of “conventional” solvent systems. Conventional pour-on solvent ations
described below were tested using ML465 as the active under exposure to water for 20 and 40
minutes.
Table 2
In-lab Water ance (% ML465 Removed after Water
Exosure n=2
% Tributyl acetyl citrate 2.4% 5.2%
Mil 01840
% Tributyl acetyl citrate 7.5% 10.1%
So bean oil
% yl acetyl citrate 5.2% 7.3%
6% Isobutene H25
So bean Oil
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% Tributyl acetyl citrate
% PPG-lS stearyl ether
% Isopropyl palmitate
% ceteary octanote
% butyl stearate
So bean Oil
Laboratory data indicate that ML465 is washed off after repeated exposure to water for all
ations tested. It means that with each rainfall, of random duration and intensity, the
concentration of ML465 on the skin will gradually decrease.
Next, the water resistance of the inventive solvent systems was tested in vitro. Table 3
shows the percentage of ML465 active lost upon exposure to water for 40 minutes. The
formulation of the invention lowered (i.e., improved) the tage of ML465 removed after
exposure to water compared with the conventional solvent systems in Tables 1 and 2.
Table 3.
In-lab Water Resistance
Solvent systems with 1% w/w ML465
Sample (% ML 465 Removed after 40
ID min. water exposure (n=2))
Methyl isobutyl ketone + 10% Polyvinyl
36 2.3%
Acetate + panol
The entrapment of an active into the polymer and continuous diffilsion of an active out of
the r will ensure protection from nmental conditions such as rain, and continuous
replenishment and presence of an active on skin to provide treatment for the duration of the
desired treatment period. Lipids present on animal skin will act as a carrier and will also be
continuously replenished by the animal.
The rate of diffusion can be controlled h the composition of the polymer part of the
formulation, such as use of a single polymer, blends of various polymers, or polymers of various
molecular weights. Furthermore, the rate of diffusion can also be controlled by addition of a
plasticizer in varying compositions and amounts. The plasticizer can be an external agent or the
sebacious lipids naturally present on the skin.
This formulation for topical delivery of a pharmaceutical active ingredient is through the
ation of a liquid formulation with a solvent system consisting of a single volatile solvent or
a combination of volatile ts, a r or a combination of polymers, one or several
actives, and optionally a plasticiser or a combination of cisers. The examples of solvent
systems tested are presented below. It should be possible for one skilled in the art to create
additional examples that would broaden the classes of als that could be utilized. Solvents
enVisioned by the present invention include a saturated aliphatic ketone (e.g., methyl isobutyl
ketone) or an ester (e.g, butyl acetate or ethyl lactate). These solvents could fiarther be combined
with, for example, isopropyl l or ethanol. Polymers enVisioned by the present invention
include at least a water insoluble polymer (e.g., a polyvinyl acetate of varying molecular weights)
that may be combined with water e rs (e.g., povidones, polyvinyl alcohol or ethyl
cellulose).
Optionally, the formulation of the present invention may include an al aliphatic
ester plasticizer (e.g., acetyl tributyl citrate), fragrances and coloring agents.
It should be noted that isopropanol may be a solvent or a plasticizer. r polymer nor
ML465 dissolve in isopropanol. It was added initially to reduce the strong odor of methyl
isobutyl ketone. Surprisingly, it was observed that on of isopropanol impacts the rate of
release of ML465 from the , thus making isopropanol a plasticizer in this case. For other
actives that either can be miscible with or dissolve in isopropanol, it can be a t.
After dosing, the liquid formulation does not have to spread to cover a body of an animal
like a conventional topical formulation. A volatile solvent(s) evaporates faster, leaVing a polymer
matrix patch that may not be evenly distributed around an application spot. The polymer will
adhere to hair or skin carrying an active that is entrapped in the polymer. The theraputic effect is
achieved by diffiJsion of the active(s) out of the polymer and blending with the lipids t on
an ’s skin that will carry it to cover the animal’s body. The degree of spreading of the
ation can be controlled through the selection of solvents and spreading agents.
Surprisingly, the addition of isopropanol to methyl yl ketone during solution preparation
resulted in an equal or even greater rate of API diffusion out of the API/polymer mixture
compared to API/polymer mixture with addition of a plasticizer Isopropanol is not considered to
be a traditional plasticizer for the polymer. It is postulated that its effect may be on the physical
structure of the polymer film (such as creating additional porosity). The concentration of
isopropanol can be below, equal or greater than concentration of polymer, with the upper limit
being a solubility of polymer/polymer combination in a solvent system. Polyvinyl acetate does
not dissolve in panol, ore panol cannot replace methyl isobutyl ketone
completely as there should be a sufficient amount of methyl isobutyl ketone for polymer to
This approach can be utilized to lly deliver various actives to production animals
such as cows, sheep, swine, horses, or ion animals, such as dogs and cats, and others to
protect against external parasites (e.g., fleas, ticks, mites, flies, etc.) or internal parasites.
Several embodiments of the invention are given in the following examples.
Example 1
methyl isobutyl ketone QS to 100%
Process: add methyl isobutyl ketone, in the amount of about 40% of the weight to be
prepared, into the container that can be tightly closed during preparation of formulation; add
polymer and mix until it dissolves, about 2 — 3 hours; add ML465, mix until dissolved;
QSlOO% with methyl isobutyl ketone, mix. Make sure the container is tightly closed to
prevent evaporation of solvent.
Example 2
Ingredients Function % w/w
ML465
Polyvinyl acetate MW 100000
Polyvinyl acetate MW 50000
methyl isobutyl ketone Solvent QS to 100%
Process: add methyl isobutyl ketone, in the amount of about 40% of the weight to be
prepared, into the container that can be tightly closed during preparation of formulation; add
polymers and mix until it dissolves, about 2 — 3 hours; add ML465, mix until ved;
QSlOO% with methyl isobutyl , mix. Make sure the container is tightly closed to
prevent evaporation of solvent.
Ingredients Function % w/w
Polyvinyl acetate MW 100000 Polymer 14.4
Isopropanol Additive 25 .0
methyl isobutyl ketone t QS to 100%
Process: add methyl isobutyl ketone, in the amount of about 40% of the weight to be
prepared, into the container that can be tightly closed during preparation of formulation; add
polymer and mix until it dissolves, about 2 — 3 hours; add ML465, mix until dissolved;
solwly add isopropanol — whilte flakes will be formed, continue to mix until flakes dissolve
and solution is clear, can add remaining methyl isopropyl ketone and mix until solution is
clear. Make sure the ner is tightly closed to prevent evaporation of solvent.
Example 4
methyl isobutyl ketone QS to 100%
Process: add methyl isobutyl ketone, in the amount of about 55% of the weight to be
prepared, into the container that can be tightly closed during preparation of formulation; add
polymer and mix until it dissolves, about 2 — 3 hours; add ML465, mix until dissolved;
QSlOO% with methyl yl ketone, mix. Make sure the container is tightly closed to
WO 09312
prevent evaporation of solvent.
Example 5
Polyvinyl e MW 100000 Polymer 20.0
Isopropanol Additive 8.5
methyl isobutyl ketone Solvent QS to 100%
Process: add methyl isobutyl , in the amount of about 55% of the weight to be
prepared, into the container that can be tightly closed during preparation of ation; add
polymer and mix until it dissolves, about 2 — 3 hours; add ML465, mix until dissolved;
slowly add isopropanol — whilte flakes will be formed, continue to mix until flakes dissolve
and solution is clear, can add remaining methyl isopropyl ketone at the same time as
isopropanol and mix until solution is clear. Make sure the container is tightly closed to
prevent evaporation of solvent.
Example 6
Polyvinyl acetate MW 100000 Polymer
Isopropanol Additive
Acetyl tributyl e Plasticizer
methyl isobutyl ketone Solvent QS to 100%
Process: add methyl isobutyl ketone, in the amount of about 55% of the weight to be
prepared, into the container that can be tightly closed during preparation of formulation; add
polymer and mix until it dissolves, about 2 — 3 hours; add ML465, mix until dissolved; add
acetyl tributyl citrate; slowly add panol — whilte flakes will be formed, the remaining
methyl isopropyl ketone can be added at the same time as addition of isopropanol, continue
to mix until flakes ve and solution is clear, can add remaining methyl isopropyl
ketone at the time of and mix until solution is clear. Make sure the container is tightly
closed to prevent evaporation of solvent.
Example 7
Ingredients Function % w/w
ML465 Active 4.0
Polyvinyl acetate MW 100000 Polymer 20.0
Isopropanol Additive 25
methyl isobutyl ketone Solvent QS to 100%
Process: add methyl isobutyl ketone, in the amount of about 50% of the weight to be prepared,
into the container that can be tightly closed during preparation of formulation; add polymer and
mix until it dissolves, about 2-3 hours; add ML465, mix until ved; slowly add isopropanol —
white flakes will be formed, continue to mix until flakes ve and solution is clear, the
remaining methyl isopropyl ketone can be added at the same time as on of isopropanol, and
mix until solution is clear. Make sure the container is tightly closed to prevent evaporation of
solvent.
Example 8
Ingredients Function % w/w
ML465 Active 4.0
Polyvinyl acetate MW 100000 Polymer
Acetyl tributyl e Plasticizer 3.0
methyl yl ketone Solvent QS to 100%
WO 09312
Process: add methyl isobutyl ketone, in the amount of about 50% of the weight to be prepared,
into the container that can be tightly closed during preparation of formulation; add polymer and
mix until it dissolves, about 2—3 hours; add ML465, mix until dissolved; add acetyl tributyl citrate
and the remaining methyl isopropyl ketone and mix. Make sure the container is tightly closed to
t evaporation of solvent.
Example 9
methyl isobutyl ketone QS to 100%
s: add methyl isobutyl ketone, in the amount of about 65% of the weight to be prepared,
into the container that can be tightly closed during preparation of formulation; add polymer and
mix until it dissolves, about 2 — 3 hours; add permethrin and mix; QSlOO% with methyl isobutyl
ketone, mix. Make sure the container is y closed to prevent evaporation of solvent.
Example 10
Ingredients Function % w/w
Polyvinyl acetate MW 100000 Polymer 20.0
Isopropanol Additive l 5 .0
methyl yl ketone Solvent QS to 100%
Process: add methyl isobutyl ketone, in the amount of about 50% of the weight to be prepared,
into the container that can be tightly closed during preparation of formulation; add polymer and
mix until it dissolves, about 2—3 hours; add permethrin, mix; slowly add isopropanol — white
2015/012031
flakes will be formed, continue to mix until flakes dissolve and solution is clear, the remaining
methyl isopropyl ketone can be added at the same time as addition of isopropanol, and mix until
solution is clear. Make sure the container is tightly closed to prevent evaporation of solvent.
Example 11.
Ingredients Function % w/w
Polyvinyl acetate MW 100000 Polymer
Isopropanol Additive
methyl isobutyl ketone Solvent QS to 100%
Process: add methyl isobutyl ketone, in the amount of about 50% of the weight to be prepared,
into the container that can be tightly closed during ation of formulation; add polymer and
mix until it dissolves, about 2—3 hours; add hrin, mix; slowly add isopropanol — white
flakes will be , continue to mix until flakes dissolve and solution is clear, the remaining
methyl isopropyl ketone can be added at the same time as addition of isopropanol, and mix until
solution is clear. Make sure the container is tightly closed to prevent evaporation of solvent.
Example 12.
Ingredients Function % w/w
Polyvinyl acetate MW 100000 r
Tributyl acetyl e Plasticizer 3.0
methyl isobutyl ketone Solvent QS to 100%
Process: add methyl isobutyl ketone, in the amount of about 50% of the weight to be prepared,
into the container that can be y closed during preparation of formulation; add polymer and
mix until it dissolves, about 2—3 hours; add permethrin, mix; add tributyl acetyl citrate and the
remaining methyl isopropyl ketone and mix. Make sure the container is tightly closed to prevent
evaporation of solvent.
Example 13.
ients Function
Permethrin Active
nyl acetate MW 100000 Polymer
Tributyl acetyl citrate Plasticizer 1.5
methyl isobutyl ketone Solvent QS to 100%
Process: add methyl isobutyl ketone, in the amount of about 50% of the weight to be prepared,
into the container that can be tightly closed during preparation of ation; add r and
mix until it dissolves, about 2—3 hours; add permethrin, mix; add tributyl acetyl citrate and the
remaining methyl isopropyl ketone and mix. Make sure the ner is tightly closed to prevent
evaporation of solvent.
Example 14 [did not prepare with active, but prepared t active]
Ingredients Function % w/w
ML465 Active 4.0
Polyvinyl acetate MW 100000 Polymer 43.0
methyl isobutyl ketone Solvent QS to 100%
Process: add methyl isobutyl ketone, in the amount of about 50% of the weight to be prepared,
into the container that can be tightly closed during preparation of formulation; add polymer and
mix until it dissolves, about 2—3 hours; add ML465, mix until dissolved; add the remaining
methyl isopropyl ketone and mix. Make sure the ner is tightly closed to prevent
evaporation of solvent.
Example 15
Ingredients Function
ML465 Active
Polyvinyl acetate MW 50000 Polymer
Acetyl tributyl citrate Plasticizer 3.0
methyl isobutyl ketone t QS to 100%
Process: add methyl isobutyl ketone, in the amount of about 50% of the weight to be prepared,
into the container that can be tightly closed during preparation of formulation; add polymer and
mix until it dissolves, about 2—3 hours; add ML465, mix until dissolved; add acetyl tributyl citrate
and the remaining methyl isopropyl ketone and mix. Make sure the container is tightly closed to
prevent evaporation of solvent.
Example 16 (did not prepared exactly with PVAc MW 50000, but prepared with MW100000)
ients on % w/w
ML465 Active 4.0
Polyvinyl acetate MW 50000 Polymer
Acetyl tributyl citrate Plasticizer 3.0
methyl isobutyl ketone Solvent QS to 100%
Process: add methyl yl ketone, in the amount of about 50% of the weight to be prepared,
into the container that can be tightly closed during preparation of formulation; add polymer and
mix until it dissolves, about 2—3 hours; add ML465, mix until ved; add acetyl tributyl citrate
and the remaining methyl isopropyl ketone and mix. Make sure the container is tightly closed to
prevent evaporation of t.
Example 17
2015/012031
Ingredients Function
ML465 Active
Polyvinyl acetate MW 50000 Polymer
Isopropanol Additive 25 .0
methyl isobutyl ketone Solvent QS to 100%
Process: add methyl yl ketone, in the amount of about 50% of the weight to be prepared,
into the container that can be y closed during preparation of formulation; add polymer and
mix until it dissolves, about 2-3 hours; add ML465, mix until dissolved; slowly add isopropanol —
white flakes will be formed, continue to mix until flakes dissolve and solution is clear, the
remaining methyl isopropyl ketone can be added at the same time as addition of panol,
mix until on is clear. Make sure the container is tightly closed to prevent evaporation of
solvent.
Example 18
Ingredients Function % w/w
ML465 Active 4.0
Polyvinyl acetate MW 50000 Polymer 7.2
Polyvinyl acetate MW 100000 Polymer 7.2
Isopropanol Additive 25 .0
methyl isobutyl ketone Solvent QS to 100%
Process: add methyl isobutyl ketone, in the amount of about 50% of the weight to be prepared,
into the ner that can be tightly closed during preparation of formulation; add polymers and
mix until it dissolves, about 2-3 hours; add ML465, mix until dissolved; slowly add isopropanol —
white flakes will be formed, continue to mix until flakes dissolve and solution is clear, the
remaining methyl isopropyl ketone can be added at the same time as addition of isopropanol,
mix until solution is clear. Make sure the container is tightly closed to prevent evaporation of
solvent.
Example 19
Polyvinyl acetate MW 100000 r
Kollidon SR Polymer
Isopropanol Additive
methyl isobutyl ketone Solvent QS to 100%
Process: add methyl isobutyl ketone, in the amount of about 50% of the weight to be prepared,
into the ner that can be y closed during preparation of formulation; add polyvinyl
acetate MW 100000 and mix until it dissolves, about 2-3 hours; add ML465, mix until dissolved;
slowly add isopropanol — white flakes will be formed, continue to mix until flakes dissolve and
solution is clear; add Kollidon SR and mix until dissolved; the remaining methyl isopropyl
ketone can be added at the same time as addition of Kollidon SR, mix until solution is clear.
Make sure the ner is tightly closed to prevent evaporation of solvent.
Example 20 film made from this solution crystallized
nyl acetate MW 100000 Polymer 20.0
Isopropanol Additive 8.0
Acetyl tributyl citrate Plasticizer 12.5
methyl isobutyl ketone Solvent QS to 100%
Process: add methyl isobutyl ketone, in the amount of about 50% of the weight to be prepared,
into the container that can be tightly closed during preparation of formulation; add r and
mix until it dissolves, about 2—3 hours; add ML465, mix until dissolved; add acetyl yl citrate
and mix; slowly add isopropanol — white flakes will be formed, continue to mix until flakes
dissolve and solution is clear; the remaining methyl isopropyl ketone can be added at the same
time as addition of isopropanol. Make sure the container is tightly closed to prevent ation
of solvent.
Example 21 film made from this solution crystallized
Polyvinyl acetate MW 100000 Polymer
Isopropanol Additive
Acetyl tributyl citrate Plasticizer
methyl isobutyl ketone Solvent QS to 100%
Process: add methyl isobutyl ketone, in the amount of about 50% of the weight to be prepared,
into the container that can be tightly closed during preparation of formulation; add r and
mix until it dissolves, about 2—3 hours; add ML465, mix until dissolved; add acetyl yl citrate
and mix; slowly add isopropanol — white flakes will be formed, continue to mix until flakes
dissolve and solution is clear; the ing methyl isopropyl ketone can be added at the same
time as addition of isopropanol. Make sure the container is tightly closed to prevent evaporation
of solvent.
Claims (21)
1. A topical delivery formulation in the form of a solution, which comprises: at least one active ingredient; a le solvent system containing at least one dissolved polymer, wherein said volatile solvent system consists of one or more solvent(s) selected from the group consisting of methyl isobutyl ketone, butyl acetate, ethyl lactate, l, and isopropanol, and wherein the volatile solvent represents from about 50 to about 94 % w/w of the composition; wherein said polymer comprises a water insoluble polymer that is polyvinyl acetate, alone or in combination with a water soluble polymer; and ally a plasticizer; wherein after , evaporation of the volatile t provides a water ant polymer matrix in which the active ingredient is entrapped; with the proviso that the active ingredient is not an arylpyrazole compound.
2. The formulation of claim 1, wherein the solvent is methyl isobutyl ketone.
3. The formulation of claim 1, wherein the solvent is butyl acetate.
4. The formulation of claim 1, wherein the t is ethyl lactate.
5. The formulation of any one of claims 1 to 4, wherein the vinyl acetate is polyvinyl acetate MW 100,000.
6. The formulation of any one of claims 1 to 4, wherein the vinyl acetate is polyvinyl acetate MW 50,000.
7. The formulation of any one of claims 1 to 6, wherein the water e polymer is a povidone.
8. The formulation of any one of claims 1 to 6, wherein the water e polymer is polyvinyl alcohol.
9. The formulation of any one of claims 1 to 6, wherein the water soluble polymer is ethyl cellulose.
10. The formulation of any one of claims 1 to 9, wherein the optional plasticizer is an aliphatic ester.
11. The formulation of claim 10, wherein the aliphatic ester is acetyl tributyl citrate.
12. The formulation of any one of claims 1 to 11, wherein the water insoluble polymer is from about 5% to about 40% w/w of the composition.
13. The formulation of any one of claims 1 to 12, wherein the water soluble polymer is from about 5% to about 40% w/w of the composition.
14. The formulation of any one of claims 1 to 13, wherein the plasticizer is from about 0.5% to about 5% w/w of the composition.
15. Use of a topical delivery formulation according to any one of claims 1 to 14 in the manufacture of a medicament for the therapeutic and/or prophylactic treatment of an animal against an ectoparasite.
16. A topical delivery formulation according to any one of claims 1 to 14 when used for the therapeutic and/or lactic treatment of an ectoparasite ion in a non-human animal.
17. A method for the therapeutic and/or lactic treatment of an rasite infection in a non-human animal comprising administering to the animal a l delivery formulation according to any one of claims 1 to 14.
18. The formulation of any one of claims 1 to 14, substantially as hereinbefore described with reference to any one of the Examples, excluding comparative examples.
19. The use of claim 15, substantially as hereinbefore bed with reference to any one of the es, excluding comparative examples.
20. The formulation of claim 16, substantially as hereinbefore described with reference to any one of the Examples, excluding comparative examples.
21. The method of claim 17, substantially as hereinbefore described with nce to any one of the Examples, excluding comparative examples.
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US201461929371P | 2014-01-20 | 2014-01-20 | |
US61/929,371 | 2014-01-20 | ||
NZ722669A NZ722669A (en) | 2014-01-20 | 2015-01-20 | Topical antiparasitic delivery systems for animals |
Publications (2)
Publication Number | Publication Date |
---|---|
NZ733600A NZ733600A (en) | 2020-12-18 |
NZ733600B2 true NZ733600B2 (en) | 2021-03-19 |
Family
ID=
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