CA2433679A1 - Polymer coated microparticles for sustained release - Google Patents

Polymer coated microparticles for sustained release Download PDF

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Publication number
CA2433679A1
CA2433679A1 CA002433679A CA2433679A CA2433679A1 CA 2433679 A1 CA2433679 A1 CA 2433679A1 CA 002433679 A CA002433679 A CA 002433679A CA 2433679 A CA2433679 A CA 2433679A CA 2433679 A1 CA2433679 A1 CA 2433679A1
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CA
Canada
Prior art keywords
glycerol
acid
microparticles
polymeric wax
derivative
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
CA002433679A
Other languages
French (fr)
Other versions
CA2433679C (en
Inventor
Joel Rosenblatt
Han Cui
Ram L. Kataria
Chuanbin Wu
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Ethicon Inc
Original Assignee
Ethicon Inc
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Ethicon Inc filed Critical Ethicon Inc
Publication of CA2433679A1 publication Critical patent/CA2433679A1/en
Application granted granted Critical
Publication of CA2433679C publication Critical patent/CA2433679C/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
    • A61K9/16—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction
    • 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
    • A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
    • A61K9/50—Microcapsules having a gas, liquid or semi-solid filling; Solid microparticles or pellets surrounded by a distinct coating layer, e.g. coated microspheres, coated drug crystals
    • A61K9/5005—Wall or coating material
    • A61K9/5021—Organic macromolecular compounds
    • A61K9/5031—Organic macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyethylene glycol, poly(lactide-co-glycolide)
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
    • A61K47/34—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyesters, polyamino acids, polysiloxanes, polyphosphazines, copolymers of polyalkylene glycol or poloxamers

Abstract

The present invention is directed to sustained release microparticle formulation for parenteral administration of biologically active substances, especially drugs. More specifically it relates to coated drug containing microparticles, wherein the coating is a synthetic, bioabsorbable, biocompatible polymeric wax that is the reaction product of a polybasic acid or derivative thereof, a polyol and a fatty acid, the polymeric wax having a melting point less than about 70°C, as determined by differential scanning calorimetry.

Claims (26)

1. Sustained release microparticles for parenteral administration of a therapeutic agent comprising:
a core comprising a biodegradable polymer and said therapeutic agent, and a coating comprising a synthetic, bioabsorbable, biocompatible polymeric wax comprising the reaction product of a polybasic acid or derivative thereof, a fatty acid; and a polyol, said polymeric wax having a melting point less than about 70°C, as determined by differential scanning calorimetry.
2. The microparticles of claim 1 wherein said polymeric wax comprises the reaction product of said polybasic acid or derivative thereof and a monoglyceride, said monoglyceride comprising the reaction product of said fatty acid and said polyol.
3. The microparticles of claim 2 wherein said polybasic acid or derivative thereof is selected from the group consisting of succinic acid, succinic anhydride, malic acid, tartaric acid, citric acid, diglycolic acid, diglycolic anhydride, glutaric acid, glutaric anhydride, adipic acid, pimelic acid, suberic acid, sebacic acid, fumaric acid, maleic acid, maleic anhydride, mixed anhydrides, esters, activated esters and acid halides.
4. The microparticles of claim 2 wherein said monoglyceride is selected from the group consisting of monostearoyl glycerol, monopalmitoyl glycerol, monomyrisitoyl glycerol, monocaproyl glycerol, monodecanoyl glycerol, monolauroyl glycerol, monolinoleoyl glycerol and monooleoyl glycerol.
5. The microparticles of claim 4 wherein said polybasic acid derivative is succinic anhydride.
6. The microparticles of claim 4 wherein said polybasic acid is succinic acid.
7. The microparticles of claim 1 wherein said polymeric wax has a number average molecular weight between about 1,000 g/mole and about 100,000 g/mole, as measured by gel permeation chromatography using polystyrene standards.
8. The microparticles of claim 1 wherein said polymeric wax is branched.
9. The microparticles of claim 1 wherein said polymeric wax comprises a copolymer.
10. The microparticles of claim 9 wherein said polymeric wax copolymer comprises the reaction product of said fatty acid, said polyol, and at least two of said polybasic acids or derivatives thereof selected from the group consisting of succinic acid, succinic anhydride, malic acid, tartaric acid, citric acid, diglycolic acid and diglycolic anhydride.
11. The microparticles of claim 9 wherein said polymeric wax copolymer comprises the reaction product of said polybasic acid or derivative thereof, and at least two monoglycerides selected from the group consisting of monostearoyl glycerol, monopalmitoyl glycerol, monomyrisitoyl glycerol, monocaproyl glycerol, monodecanoyl glycerol, monolauroyl glycerol, monolinoleoyl glycerol and monooleoyl glycerol.
12. The microparticles of claim 9 wherein said wax copolymer comprises the reaction product of said polybasic acid or derivative thereof, a monoglyceride selected from the group consisting of monostearoyl glycerol, monopalmitoyl glycerol, monomyrisitoyl glycerol, monocaproyl glycerol, monodecanoyl glycerol, monolauroyl glycerol, monolinoleoyl glycerol and monooleoyl glycerol, and at least one additional polyol selected from the group consisting of ethylene glycol, 1,2-propylene glycol, 1,3-propanediol, bis-2-hydroxyethyl ether, 1,4-butanediol, 1,5-pentanediol, 1,6- hexanediol, 1,8-octanediol, 1,10-decanediol, 1, 12-dodecanediol, other diols, linear poly(ethylene glycol), branched polyethylene glycol), linear poly(propylene glycol), branched polypropylene glycol), linear polyethylene-co-propylene glycol)s and branched polyethylene-co-propylene glycol)s.
13. The microparticles of claim 1 wherein said bioactive agent is selected from the group consisting of antiinfectives, analgesics, anorexics, antihelmintics, antiarthritics, antiasthmatics, anticonvulsants, antidepressants, antidiuretics, antidiarrheals, antihistamines, antiinflammatory agents, antimigraine preparations, antinauseants, antineoplastics, antiparkinsonism drugs, antipruritics, antipsychotics, antipyretics, antispasmodics, anticholinergics, sympathomimetics, xanthine derivatives, calcium channel blockers, beta-blockers, antiarrhythmics, antihypertensives, diuretics, vasodilators, central nervous system stimulants,decongestants, hormones, steroids, hypnotics, immunosuppressives, muscle relaxants, parasympatholytics, psychostimulants, sedatives, tranquilizers, naturally derived or genetically engineered proteins, polysaccharides, glycoproteins, or lipoproteins, oligonucleotides, antibodies, antigens, cholinergics, chemotherapeutics, hemostatics, clot dissolving agents, radioactive agents and cystostatics.
14. The microparticles of claim 1 wherein said polymeric wax has a melting point between about 25°C and about 70°C.
15. The microparticles of claim 1 wherein said biodegradable polymer of said core comprises a second synthetic, bioabsorbable, biocompatible polymeric wax comprising the reaction product of a polybasic acid or derivative thereof, a fatty acid; and a polyol, said polymeric wax having a melting point less than about 70°C, as determined by differential scanning calorimetry.
16. The microparticles of claim 15 wherein said second polymeric wax comprises the reaction product of said polybasic acid or derivative thereof and a monoglyceride, said monoglyceride comprising the reaction product of said fatty acid and said polyol.
17. The microparticles of claim 16 wherein said polybasic acid or derivative thereof is selected from fhe group consisting of succiinic acid, succinic anhydride, malic acid, tartaric acid, citric acid, diglycolic acid, diglycolic anhydride, glutaric acid, glutaric anhydride, adipic acid, pimelic acid, suberic acid, sebacic acid, fumaric acid, maleic acid, maleic anhydride, mixed anhydrides, esters, activated esters and acid halides.
18. The microparticles of claim 16 wherein said monoglyceride is selected from the group consisting of monostearoyl glycerol, monopalmitoyl glycerol, monomyrisitoyl glycerol, monocaproyl glycerol, monodecanoyl glycerol, monolauroyl glycerol, monolinoleoyl glycerol and monooleoyl glycerol.
19. The microparticles of claim 18 wherein said polybasic acid derivative is succinic anhydride.
20. The microparticles of claim 18 wherein said polybasic acid is succinic acid
21. The microparticles of claim 15 wherein said second polymeric wax has a number average molecular weight between about 1,000 g/mole and about 100,000 g/mole, as measured by gel permeation chromatography using polystyrene standards.
22. The microparticles of claim 15 wherein said second polymeric wax is branched.
23. The microparticles of claim 15 wherein said second polymeric wax comprises a copolymer.
24. The microparticles of claim 23 wherein said polymeric wax copolymer comprises the reaction product of said fatty acid, said polyol, and at least two of said polybasic acids or derivatives thereof selected from the group consisting of succinic acid, succinic anhydride, malic acid, tartaric acid, citric acid, diglycolic acid and diglycolic anhydride.
25. The microparticles of claim 23 wherein said polymeric wax copolymer comprises the reaction product of said polybasic acid or derivative thereof, and at least two monoglycerides selected from the group consisting of monostearoyl glycerol, monopalmitoyl glycerol, monomyrisitoyl glycerol, monocaproyl glycerol, monodecanoyl glycerol, monolauroyl glycerol, monolinoleoyl glycerol and monooleoyl glycerol.
26. The microparticles of claim 23 wherein said wax copolymer comprises the reaction product of said polybasic acid or derivative thereof, a monoglyceride selected from the group consisting of monostearoyl glycerol, monopalmitoyl glycerol, monomyrisitoyl glycerol, monocaproyl glycerol, monodecanoyl glycerol, monolauroyl glycerol, monolinoleoyl glycerol and monooleoyl glycerol, and at least one additional polyol selected from the group consisting of ethylene glycol, 1,2-propylene glycol, 1,3-propanediol, bis-2-hydroxyethyl ether, 1,4-butanediol, 1,5-pentanediol, 1,6-hexanediol, 1,8-octanediol, 1,10-decanediol, 1,12-dodecanediol, other diols, linear poly(ethylene glycol), branched poly(ethylene glycol), linear poly(propylene glycol), branched poly(propylene glycol), linear poly(ethylene-co-propylene glycol)s and branched poly(ethylene-co-propylene glycol)s.
CA2433679A 2002-06-28 2003-06-26 Polymer coated microparticles for sustained release Expired - Fee Related CA2433679C (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US10/183,260 US7101566B2 (en) 2002-06-28 2002-06-28 Polymer coated microparticles for sustained release
US10/183,260 2002-06-28

Publications (2)

Publication Number Publication Date
CA2433679A1 true CA2433679A1 (en) 2003-12-28
CA2433679C CA2433679C (en) 2012-05-15

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Country Status (9)

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US (1) US7101566B2 (en)
EP (1) EP1374860B1 (en)
KR (1) KR101054234B1 (en)
CN (1) CN100502949C (en)
AU (2) AU2003204626B2 (en)
CA (1) CA2433679C (en)
DE (1) DE60301301T2 (en)
ES (1) ES2247492T3 (en)
TW (1) TWI302838B (en)

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CN100502949C (en) 2009-06-24
AU2003204626A1 (en) 2004-01-15
KR20040002749A (en) 2004-01-07
AU2009200562A8 (en) 2009-04-02
TWI302838B (en) 2008-11-11
US20040001890A1 (en) 2004-01-01
EP1374860B1 (en) 2005-08-17
US7101566B2 (en) 2006-09-05
KR101054234B1 (en) 2011-08-08
AU2003204626B2 (en) 2008-12-18
AU2009200562B2 (en) 2011-08-25
CN1471907A (en) 2004-02-04
AU2009200562A1 (en) 2009-03-05
ES2247492T3 (en) 2006-03-01
DE60301301D1 (en) 2005-09-22
DE60301301T2 (en) 2006-07-06
CA2433679C (en) 2012-05-15
EP1374860A1 (en) 2004-01-02
TW200407176A (en) 2004-05-16

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