USRE39592E1 - Extended release growth promoting two component composition - Google Patents
Extended release growth promoting two component composition Download PDFInfo
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- USRE39592E1 USRE39592E1 US11/023,337 US2333704A USRE39592E US RE39592 E1 USRE39592 E1 US RE39592E1 US 2333704 A US2333704 A US 2333704A US RE39592 E USRE39592 E US RE39592E
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- 0 *C12C=CC3=C4CCC(=O)C=C4CCC3C1CCC2O Chemical compound *C12C=CC3=C4CCC(=O)C=C4CCC3C1CCC2O 0.000 description 33
Classifications
-
- 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
- A61K9/0019—Injectable compositions; Intramuscular, intravenous, arterial, subcutaneous administration; Compositions to be administered through the skin in an invasive manner
- A61K9/0024—Solid, semi-solid or solidifying implants, which are implanted or injected in body tissue
-
- 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
-
- 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
- A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
-
- 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
- A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
- A61K31/565—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids not substituted in position 17 beta by a carbon atom, e.g. estrane, estradiol
-
- 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
- A61K9/20—Pills, tablets, discs, rods
- A61K9/28—Dragees; Coated pills or tablets, e.g. with film or compression coating
- A61K9/2806—Coating materials
- A61K9/2833—Organic macromolecular compounds
- A61K9/2853—Organic macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyethylene glycol, polyethylene oxide, poloxamers, poly(lactide-co-glycolide)
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J1/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, not substituted in position 17 beta by a carbon atom, e.g. estrane, androstane
-
- 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
- A61K9/20—Pills, tablets, discs, rods
- A61K9/2004—Excipients; Inactive ingredients
- A61K9/2013—Organic compounds, e.g. phospholipids, fats
-
- 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
- A61K9/20—Pills, tablets, discs, rods
- A61K9/2004—Excipients; Inactive ingredients
- A61K9/2022—Organic macromolecular compounds
- A61K9/2031—Organic macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyethylene glycol, polyethylene oxide, poloxamers
- A61K9/204—Polyesters, e.g. poly(lactide-co-glycolide)
-
- 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
- A61K9/20—Pills, tablets, discs, rods
- A61K9/2004—Excipients; Inactive ingredients
- A61K9/2022—Organic macromolecular compounds
- A61K9/205—Polysaccharides, e.g. alginate, gums; Cyclodextrin
- A61K9/2054—Cellulose; Cellulose derivatives, e.g. hydroxypropyl methylcellulose
Definitions
- compositions of growth promoters are those wherein R, R 1 , R 2 , R 3 , and R4, R 5 and R 6 are methyl and the aroyl or alkanoyl ester derivatives thereof, where applicable.
- Preferred biodegradable polymers are homopolymers and copolymers of glycolide, DL-lactide, L-lactide, glycolic acid, DL-lactic acid and L-lactic acid and combinations thereof.
- alkyl refers to a straight or branched chain hydrocarbon radical containing no unsaturation and having 1 to 5 carbon atoms. Examples of alkyl groups are methyl, ethyl, 1-propyl, 2-propyl, 1-butyl, 2-butyl, 1-pentyl, 3-pentyl, and the like; the term “alkanoic acid” refers to a compound formed by combination of a carboxyl group and a hydrogen atom or alkyl group.
- alkanoic acid examples include formic acid, acetic acid, propanoic acid, 1-methylpropanoic acid, 2,2-dimethylacetic acid, pentanoic acid, and the like; the term “alkanoyl” refers to the radical formed by removal of the hydroxyl group from an alkanoic acid. Examples of alkanoyl groups are formyl, acetyl, propanoyl, 2-methylpropanoyl, 2,2-dimethylacetyl, pentanoyl, and the like.
- aryl refers to an unsubstituted or a substituted phenyl group.
- aryl groups are benzene, 2-methylbenzene, 3-chlorobenzene, 4-hydroxybenzene, 3-methoxybenzene, methoxybenzene, 3-nitrobenzene, 2-trifluorobenzene, and the like.
- aroic acid refers to a compound formed by combination of an carboxyl group with an aryl group.
- aroic acids are benzoic acid, 2-methylbenzoic acid, 3-chlorobenzoic acid, 4-hydroxybenzoic acid, 3-methoxybenzoic acid, 3-nitrobenzoic acid, 2-trifluorobenzoic acid, and the like.
- aroyl refers to the radical formed by removal of the hydroxyl group from an aroic acid.
- aroyl examples include benzoyl, 2-methylbenzoyl, 3-chlorobenzoyl, 4-hydroxybenzoyl, 3-methoxybenzyol, 2-nitrobenzoyl, 2-trifluoromethylbenzoyl, and the like.
- the term “lower” as applied to any of the aforementioned groups or compounds refers to a group or compound having a carbon skeleton containing up to and including 5 carbon atoms.
- esteer derivatives refers to esters of the hydroxy group or groups of compounds of the present invention and an alkanoyl or aroyl group.
- ester derivatives are esters of formic acid, acetic acid, propanoic acid, 1-methylpropanoic acid, 2,2-dimethylacetic acid, pentanoic acid, benzoic acid, 2-methylbenzoic acid, 3-chlorobenzoic acid, 4-hydroxybenzoic acid, 3-methoxybenzoic acid, 2-nitrobenzoic acid and 2-trifluoromethylbenzoic acid and the like.
- optical antipodes exist as optical antipodes and as the racemic forms thereof.
- the optical antipodes may be prepared from the corresponding racemic forms by standard optical resolution techniques or by synthesis from optically active precursors.
- food animal refers to an animal raised for the purpose of providing a source of protein in the diet of humans or other animals.
- Examples of food animals are bovine animals, such as cows, cattle, steers, calves, and the like, ovine animals such as sheep; porcine animals such as pigs, and the like and avians such as chickens, turkeys and the like.
- conventional drug delivery refers to the temporally uncontrolled release of a drug into the blood of an animal resulting in a short duration of action, the blood levels of the drug being either initially high (intravenous administration) and falling off rapidly, or initially low (extramuscular administration), rapidly rising and falling off rapidly.
- steroid refers to a compound characterized by the presence of a perhydrocyclopentenophenanthrene ring system.
- biodegradable polymer refers to those synthetic and naturally occurring water-insoluble polymers that degrade by hydrolysis or enzymatic processes.
- useful biodegradable polymers include, but are not limited to the aliphatic polyesters of hydroxy acids (i.e. the “polylactides”) such as the homopolymers and copolymers prepared by ring-opening polymerization of glycolide, DL-lactide, L-lactide, ⁇ -butyrolactone, ⁇ -valerolactone, ⁇ -caprolactone, as well as blends of these polymers.
- the growth promoters of the compositions of the present invention are described in the art.
- the steroids of the formulas 1 and 3 are described in U.S. Pat. No. 3,939,265 issued to J. A. Grandadam on Feb. 17, 1996; the steroids in formula 2 are described in U.S. Pat. No. 2,236,574 issued to H. Koester, et al., on Apr. 11, 1941; the steroid of formula 3 is described in U.S. Pat. No. 2,232,438 issued to A. Butendant on Feb. 18, 1941; and the macrocycles of formula 5 are described in U.S. Pat. No. 3,239,345 issued to E. B. Hodge, et al., on Mar. 8, 1966.
- polylactides as defined herein are described in U.S. Pat. No. 5,366,734 issued Nov. 22, 1994 to F. G. Hutchinson and are prepared by polymerization of lactic acid or glycolic acid, alone, or the corresponding lactides or glycolides, or copolymerization of lactic acid and glycolic acid, or the corresponding lactides and glycolides, as described therein, or are available from commercial sources, for example, Birmingham Polymers, Inc., Birmingham, Ala.
- the homopolymers and copolymers of glycolide, DL-lactide and L-lactide, glycolic acid, DL-lactic acid and L-lactic acid, and combinations thereof, are characterized by their composition and molecular weight.
- Composition can be conveniently determined by nuclear magnetic resonance spectrometry.
- the composition is described as the molar composition based on the cyclic monomers from which the polymer was prepared.
- the composition is described as the molar composition of the hydroxyacid residues present.
- the compositions of the polylactides that are useful in preparing the formulations described herein include all homopolymers and copolymers that exhibit glass transition or crystalline melting transition temperatures greater than about 40° C.
- the inherent viscosities of the polylactides may fall within the range of about 0.1 dL/g to about 3.5 dL/g; that of the preferred polymers being in the range of about 0.3 dL/g to about 1.5 dL/g.
- the biodegradable polymer, preferably, a polylactide, of the second composition of the formulation serves as a coating of a core of the formulation and may be present as a minor component of the core in an amount within the range of from about 0 to about 10%.
- the timing of the initial release of the growth promoters from the second composition formulation, the coated composition is determined by the relative amounts of the promoters to the biodegradable polymeric coating, as well as the characteristics of the coating. Generally, the greater the proportion of biodegradable polymer to the growth promoters, the greater the retardation of the initial release of the growth promoters, i.e., the longer delayed release period. For example, in table 1, the uncoated pellet began releasing immediately while the 10.8 wt. % coasted pellet did not begin to release until approximately 45 days and the 19.8 wt. % of coated pellet did not begin to release until approximately 55 days.
- the in vitro rates of release of the growth promoters of the present invention are determined by conventional methods known in the art, for example, by the methods described by J. W. Gibson in Intrauterine Contraception: Advances and Future Prospects, G. I. Zatuchni, et al. Editors, Harper and Row, Philadelphia, Pa., 1984, pages 218 and 219.
- the second composition formulation containing growth promoters of formula 1 and 4 in the form of a coated pellet was added to an aqueous solution of a dissolution medium of sodium dodecyl sulfate (5 wt. %) and incubated at 37° C. Samples of the dissolution medium were removed periodically and analyzed by high performance liquid chromatography for the presence of the growth promoters.
- the second composition of the extended release composition is formulated by mixing the growth promoters, excipients, if any, such as a binder and an adhesive, and a solution of a biodegradable polymer, evaporating the solution, screening and drying the granulate, adding a lubricant, and tableting the granulate.
- the tablets, so obtained, containing the biodegradable polymer in the core, are then coated with a solution of a biodegradable polymer to provide the coated delayed release pellets.
- a solution of a biodegradable polymer e.g. a polylactide, preferably a copolymer of DL-lactide and glycolide, characterized by its inherent viscosity, and having a ratio of lactide units to glycolide units, preferably in the range of from about 50:50 to 90:10, most preferably in the range from about 60:40 to about 75:25, is added to a granulation of growth promoters, such as, for example, 17 ⁇ -acetoxyestra-4,9,11-trien-3-one, and estra-1,3,5(10)-trien-3,17 ⁇ -diol, an adhesive, preferably, cholesterol, a binder, preferably, ethylcellulose, in a planetary mixer, and the solvent is evaporated.
- a biodegradable polymer e.g. a polylactide, preferably a copolymer of DL-lactide and glycolide, characterized by its inherent viscosity
- the dried granules are mixed with a lubricant, preferably magnesium stearate, then tableted with a press optimally equipped with tools having a beveled edge, the fill weight being from about 25 mg to about 50 mg, a fill weight of about 33 mg being preferred, to provide core tablets.
- a lubricant preferably magnesium stearate
- a solution of a biodegradable polymer, preferably a copolymer having a ratio of DL-lactide to glycolide units of about 50:50 to about 90:10, most preferably in the range of from about 60:40 to about 75:25 in an organic solvent such as acetone is sprayed onto the core tablets in an air suspension coater-drier to provide delayed release pellets having the desired release rate properties.
- the pellets of the first composition granulation, the uncoated sustained release pellets containing growth promoters and excipients, if any, and the second composition granulation, the delayed release pellets, containing growth promoters, a biodegradable polymer, preferably a polylactide and excipients, if any, coated with a biodegradable polymer, preferably a polylactide, are administered to food animals in the feedlot to afford extended release of the growth promoters over the feedlot period.
- the extended release of the growth promoters is a composite of the sustained release and delayed release characteristics of the uncoated first and coated second compositions, respectively.
- the rate of release of the sustained release first composition initially increases, reaches a maximum and then rapidly decreases.
- the release of the growth promoters from the coated delayed release formulation is initially delayed over the period that the sustained release formulation releases the growth promoters and until the release reaches the maximum and begins to decline. At about that point in time, the coated formulation, without a burst release of promoters, releases the promoters to provide a composite release of the promoters over the extended period the food animal is in the feedlot.
- the composite rate of release of the growth promoters of the composition of the present invention is determined by the release rates of the first, the sustained, and the second, the delayed formulations.
- the sustained, first composition releases the growth promoters upon administration into the food animal. The rate of release of promoters increases sharply, reaches a maximum and then declines.
- the release of the growth promoters of the second composition is delayed from the time of administration.
- the composite release is extended over time, the time the food animal is in the feedlot.
- a composite release extended over about 1 day to about 180 days after administration may be obtained.
- An extended release of about 200 days after administering the feedlot period for bovines is attainable by appropriate adjustment of the release characteristics of the sustained and delayed compositions, the uncoated and coated compositions of the growth promoters.
- the growth promoting compositions of the present invention are administered to food animals by one of various methods known in the art.
- the growth promoting compositions are administered parenterally, typically, subcutaneously as pellets to an inedible member of the animal, by means of a syringe (of sufficient size to accommodate the pellets) or a conventional implant gun, the cartridge thereof being loaded with the pellets containing the sustained and delayed compositions.
- Administration of the pellets of the growth promoting first and second compositions by simultaneous implantation from the cartridge gun is preferred.
- the pellets of the first and second growth promoting compositions may be prepared in various shapes.
- a cylindrical shape is preferred.
- the length of the cylindrical pellet may vary from about 3 mm to about 6 mm, a length of about 4 mm to about 5 mm being more preferred, a length of about 4.3 mm being most preferred.
- the diameter of the pellet may vary from about 2 mm to about 4 mm, a diameter of about 2.5 mm to about 3.5 mm also being more preferred.
- the cylindrical pellets may have a beveled edge.
- the pellets may contain various amounts of growth promoters and coating levels.
- the pellets may contain about 16 mg to 24 mg of 17 ⁇ -acetoxyestra-4,9,11-trien-3-one, preferably about 19 to 21 mg of 17 ⁇ -acetoxyestra-4,9,11-trien-3-one, more preferably about 20 mg of 17 ⁇ -acetoxyestra-4,9,11-trien-3-one, and about 2.0 mg to about 6.0 mg of estra-1,3,5(10)-trien-3,17 ⁇ -diol, preferably about 3.0 mg to about 5.0 mg of estra-1,3,5(10)-trien-3,17 ⁇ -diol, more preferably either about 2.0 or 4.0 mg of estra-1,3,5(10)-trien-3,17 ⁇ -diol.
- the pellets may contain various amounts of growth promoters and coating levels. Typically, for example, the pellets may contain about 13 to about 25 weight percent of 17 ⁇ -acetoxyestra-4,9,11-trien-3-one and about 11.5 to 23.0 weight percent of estra-1,3,5(10)-trien-3,17 ⁇ -diol.
- the desired growth promotion is achieved when the present composition comprising an uncoated composition of growth promoters, the first composition, and a coated composition of growth promoters, the second composition, are administered simultaneously to a food animal at a dose of about 0.75 mg/day/animal to about 1.2 mg/day/animal, a dose of about 0.95 mg/day/animal being preferred to attain the desired weight gain for the period the animal is in the feedlot.
- doses are attained when about 8 to about 10 pellets of each composition are administered to the food animal.
- the release rates of the growth promoters from the first (uncoated) and second (coated) compositions of the present invention are determined by methods known in the art.
- release rates dissolution rates
- individual pellets of growth promoters 17 ⁇ -acetoxyestra-4,9,11-trien-3-one and estra-1,3,5(10)-trien-3,17 ⁇ -diol, uncoated and coated with 75:25-DL-lactide-glycolide copolymer were added to 50 ml of aqueous sodium dodecyl sulfate (5 wt. %) and incubated at 37° C., without agitation.
- Tablets 40 g as prepared in example 2 and placebo tablets prepared from Avicel PH-101 were charged into the coating chamber of 4/6-in. fluid bed coater (Coating Place, Inc., Verona, Wis.) equipped with a Wurster insert.
- the tablets were coated with 1.0 wt. % of DL-Lactide-glycolide acid copolymer in acetone solution using the following coating conditions: fluidization air—25-35 SCFM; atomization air—14 psig, 35 SCFH; liquid feed—0.8 mL/min; inlet air temperature—100-107° F.; outlet air temperature—90° F.
- Coating level was monitored by periodically interrupting the coating process, removing a sample, and measuring weight gain.
Abstract
Description
wherein R is loweralkyl; the ester derivatives, geometric isomers, stereoisomers, or optical isomers thereof, a compound of formula 2
wherein R1, and R2 are loweralkyl; the ester derivatives, geometric isomers, stereoisomers, or optical isomers thereof, a compound of formula 3
wherein R3 and R4 are loweralkyl; the geometric isomers, stereoisomers, or optical isomers thereof, a compound of formula 4
wherein R5 is loweralkyl; the ester derivatives, geometric isomers, stereoisomers, or optical isomers thereof; or a compound of formula 5
wherein R6 is loweralkyl; the ester derivatives, geometric isomers, stereoisomers, or optical isomers thereof; and a second composition comprising a compound of formula 1
wherein R is loweralky; the ester derivatives, geometric isomers, stereoisomers, or optical isomers thereof, a compound of formula 2
wherein R1 and R2 are loweralkyl; the ester derivatives, geometric isomers, stereoisomers, or optical isomers thereof, a compound of formula 3
wherein R5 is loweralkyl; the ester derivatives, geometric isomers, stereoisomers, or optical isomer thereof, a compound of formula 4
wherein R3 and R4 are loweralkyl; the geometric isomers, stereoisomers, or optical isomers thereof, and a compound of formula 5
wherein R6 is loweralkyl; the ester derivatives, geometric isomers, stereoisomers, or optical isomers thereof; and a biodegradable polymer selected from the group consisting of homopolymers and copolymers of γ-butyrolactone, δ-valerolactone, ε-caprolactone, glycolide, DL-lactide, L-lactide, glycolic acid, DL-lactic acid, L-lactic acid, and combinations thereof, polydioxanones, polyorthesters, polyanhydrides, polycarbonates, polyesteramides, and polyphosphazines, useful for the promotion of weight gain in food animals. The present invention also relates to a pharmaceutical dosage form containing the composition, a method of preparing the dosage form utilizing the composition, as well as pellets of the composition for implantation in food animals.
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- (a) 17β-acetoxyestra-4,9,11-trien-3-one;
- (b) 17β-benzoyloxyestra-4,9,11-trien-3-one;
- (c) 17β-propionyloxy-4-androsten-3-one;
- (d) pregn-4-en-3,20-dione;
- (e) estra-1,3,5(10)-trien-3,17β-diol;
- (f) 17β-benzoyloxyestra-1,3,5(10)-trien-3-ol;
- (g) 3,4,5,6,9,10,11,12-decahydro-7,14,16-trihydroxy-3-methyl-1H(2)-benzoxacyclotetradecin 1-one.
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- (a) 17β-acetoxyestra-4,9,11-trien-3-one;
- (b) 17β-benzoyloxyestra-4,9,11-trien-3-one;
- (c) 17β-propionyloxy-4-androsten-3-one;
- (d) pregn-4-en-3,20-dione;
- (e) estra-1,3,5(10)-trien-3,17β-diol;
- (f) 17β-benzoyloxyestra-1,3,5(10)-trien-3-ol; and
- (g) 3,4,5,6,9,10,11,12-decahydro-7,14,16-trihydroxy-3-methyl-1H(2)-benzoxacyclotetradecin-1-one.
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- (a) 17β-acetoxyestra-4,9,11-trien-3-one;
- (b) 17β-benzoyloxyestra-4,9,11-trien-3-one;
- (c) 17β-propionyloxy-4-androsten-3-one;
- (d) pregn-4-en-3,20-dione;
- (e) estra-1,3,5,(10)-trien-3,17β-diol;
- (f) 17β-benzoyloxyestra-1,3,5(10)-trien-3-ol;
- (g) 3,4,5,6,9,10,11,12-decahydro-7,14,16-trihydroxy-3-methyl-1H(2)-benzoxacyclotetradecin-1-one, and
- a biodegradable polymer, preferably, homopolymers and copolymers of glycolide, DL-lactide, L-lactide, glycolic acid, DL-lactic acid and L-lactic acid, and combinations thereof, more preferably copolymers of DL-lactide and glycolide and copolymers of L-lactide and glycolide.
- The formulation may contain, in addition to the growth promoters, the active ingredients, excipients, e.g., pharmaceutical binders and fillers, such as starch, ethylcellulose, cellulose acetate, sucrose, and polyvinylpyrrolidone. Ethylcellulose is preferred. The formulation may also contain an adhesive, for example, cholesterol, and a lubricant, for example, magnesium stearate.
TABLE 1 | |||
% Released | |||
Cores Coated | % Released Cores Coated | ||
Elapsed | % Released | with 75:25 | with 75:25 |
Time | Uncoated | DL-PLG | DL-PLG |
days | Core | 10.8 wt. % Coating | 19.8 wt. % Coating |
1 | 11.58 | 0.00 | 0.00 |
3 | 28.20 | 0.00 | 0.00 |
4 | 36.64 | 0.00 | 0.00 |
8 | 55.45 | 0.00 | 0.00 |
9 | 58.70 | 0.01 | 0.00 |
14 | 72.72 | 0.04 | 0.00 |
21 | 87.35 | 0.04 | ND |
28 | 96.73 | ND | 0.00 |
35 | 99.80 | 0.12 | 0.00 |
43 | 0.85 | 0.04 | |
50 | 5.04 | 0.94 | |
57 | 25.41 | 3.42 | |
64 | 42.01 | 10.84 | |
71 | 53.07 | ND | |
ND—Not determined | |||
DL-PLG refers to the copolymer of DL-lactide-glycolide |
17β-acetoxy-4,9,11-trien-3-one | 59.3 | ||
1,3,5(10)-estra-3,17β-diol | 11.9 | ||
Cholesterol | 18.6 | ||
Ethyl cellulose | 3.7 | ||
Magnesium Stearate | 1.5 | ||
75:25 DL-lactide-glycolide copolymer | 5.0 | ||
TABLE 2 |
Properties of TBA and E2 Uncoated Pellets |
and Pellets Coated with Lactide-Glycolide |
65:35 | 65:35 | 75:25 | 75:25 | ||
Uncoated | DL-lactide-glycolide | DL-lactide-glycolide | DL-lactide-glycolide | DL-lactide-glycolide | |
Property | Pellets | copolymer coating | copolymer coating | copolymer coating | copolymer coating |
Nominal Coating wt. | 10% | 20% | 10% | 20% | |
Pellet Wt, mg | 31.2 | 35.3 | 40.2 | 35.5 | 39.9 |
Pellet Length, mm | 3.96 | 4.22 | 4.35 | 4.17 | 4.26 |
Pellet Diameter, mm | 2.97 | 3.09 | 3.24 | 3.12 | 3.23 |
Harness, N | 69.0 | 120.3 | 163.4 | 116.6 | 156.1 |
TBA Content, mg | 17.2 | 16.9 | 17.4 | 16.7 | 16.8 |
TBA Content, wt % | 56.0 | 48.3 | 43.2 | 48.8 | 42.5 |
E2 Content, mg | 3.54 | 3.54 | 3.63 | 3.46 | 3.51 |
E2 Content, wt % | 11.5 | 10.1 | 9.0 | 10.1 | 8.9 |
TBA/E Ratio | 4.86 | 4.77 | 4.79 | 4.83 | 4.79 |
Coating Level (TBA | NA | 13.7 | 22.8 | 12.8 | 24.3 |
basis), wt % | |||||
Coating Level (E2 | NA | 12.2 | 21.7 | 12.2 | 22.6 |
basis), wt % | |||||
Coating Level (Wt | NA | 11.6 | 22.4 | 12.1 | 21.8 |
basis) wt % | |||||
Pellet weight, n = 50; Length, diameter, and hardness, n = 10; TBA and E2 contents, n = 5. | |||||
Weight percentage of TBA and E2 were calculated from the individual pellet weights used in the content assay. | |||||
TBA refers to 17β-acetoxyestra-4,9,11-trien-3-one | |||||
E2 refers to estra-1,3,5(10)-trien-3,17β-diol |
Claims (53)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US11/023,337 USRE39592E1 (en) | 1998-12-31 | 2004-12-22 | Extended release growth promoting two component composition |
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR9816707 | 1998-12-31 | ||
US09/273,862 US6498153B1 (en) | 1998-12-31 | 1999-03-22 | Extended release growth promoting two component composition |
US11/023,337 USRE39592E1 (en) | 1998-12-31 | 2004-12-22 | Extended release growth promoting two component composition |
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US09/273,862 Reissue US6498153B1 (en) | 1998-12-31 | 1999-03-22 | Extended release growth promoting two component composition |
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Publication Number | Publication Date |
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USRE39592E1 true USRE39592E1 (en) | 2007-04-24 |
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US09/273,862 Ceased US6498153B1 (en) | 1998-12-31 | 1999-03-22 | Extended release growth promoting two component composition |
US11/023,337 Expired - Lifetime USRE39592E1 (en) | 1998-12-31 | 2004-12-22 | Extended release growth promoting two component composition |
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US09/273,862 Ceased US6498153B1 (en) | 1998-12-31 | 1999-03-22 | Extended release growth promoting two component composition |
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US11648238B2 (en) | 2017-12-12 | 2023-05-16 | Intervet Inc. | Implantable isoxazoline pharmaceutical compositions and uses thereof |
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