CA2909303C - Sustained release microspheres and method of producing the same - Google Patents
Sustained release microspheres and method of producing the same Download PDFInfo
- Publication number
- CA2909303C CA2909303C CA2909303A CA2909303A CA2909303C CA 2909303 C CA2909303 C CA 2909303C CA 2909303 A CA2909303 A CA 2909303A CA 2909303 A CA2909303 A CA 2909303A CA 2909303 C CA2909303 C CA 2909303C
- Authority
- CA
- Canada
- Prior art keywords
- dispersed phase
- solvent
- filtering
- betamethasone
- mixtures
- 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.)
- Active
Links
- 239000004005 microsphere Substances 0.000 title claims abstract description 54
- 238000013268 sustained release Methods 0.000 title claims abstract description 14
- 239000012730 sustained-release form Substances 0.000 title claims abstract description 14
- 238000000034 method Methods 0.000 title claims description 31
- 239000000203 mixture Substances 0.000 claims abstract description 48
- 238000009472 formulation Methods 0.000 claims abstract description 33
- 229920000642 polymer Polymers 0.000 claims abstract description 32
- 238000001914 filtration Methods 0.000 claims abstract description 30
- 239000002904 solvent Substances 0.000 claims abstract description 21
- 239000004480 active ingredient Substances 0.000 claims abstract description 18
- 230000002209 hydrophobic effect Effects 0.000 claims abstract description 17
- 230000000975 bioactive effect Effects 0.000 claims abstract description 14
- 239000004615 ingredient Substances 0.000 claims abstract description 14
- 238000004519 manufacturing process Methods 0.000 claims abstract description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 42
- 229960002537 betamethasone Drugs 0.000 claims description 34
- UREBDLICKHMUKA-DVTGEIKXSA-N betamethasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@H](C)[C@@](C(=O)CO)(O)[C@@]1(C)C[C@@H]2O UREBDLICKHMUKA-DVTGEIKXSA-N 0.000 claims description 34
- 229920000747 poly(lactic acid) Polymers 0.000 claims description 11
- 230000001954 sterilising effect Effects 0.000 claims description 11
- 238000004659 sterilization and disinfection Methods 0.000 claims description 7
- 239000004372 Polyvinyl alcohol Substances 0.000 claims description 6
- 229920002451 polyvinyl alcohol Polymers 0.000 claims description 6
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 claims 5
- 239000011877 solvent mixture Substances 0.000 claims 1
- 229940079593 drug Drugs 0.000 description 28
- 239000003814 drug Substances 0.000 description 28
- 239000000243 solution Substances 0.000 description 26
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 18
- 239000002033 PVDF binder Substances 0.000 description 6
- 235000019445 benzyl alcohol Nutrition 0.000 description 6
- 229920002981 polyvinylidene fluoride Polymers 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 238000002347 injection Methods 0.000 description 5
- 239000007924 injection Substances 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 238000005406 washing Methods 0.000 description 5
- 239000006069 physical mixture Substances 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- 230000007774 longterm Effects 0.000 description 3
- 238000012384 transportation and delivery Methods 0.000 description 3
- 208000003251 Pruritus Diseases 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000003246 corticosteroid Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000005538 encapsulation Methods 0.000 description 2
- 238000010255 intramuscular injection Methods 0.000 description 2
- 239000007927 intramuscular injection Substances 0.000 description 2
- 230000007803 itching Effects 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 230000004962 physiological condition Effects 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 230000002459 sustained effect Effects 0.000 description 2
- 241000196324 Embryophyta Species 0.000 description 1
- 206010020751 Hypersensitivity Diseases 0.000 description 1
- 208000020550 Joint related disease Diseases 0.000 description 1
- 241000159243 Toxicodendron radicans Species 0.000 description 1
- 238000002441 X-ray diffraction Methods 0.000 description 1
- 239000008186 active pharmaceutical agent Substances 0.000 description 1
- 230000000947 anti-immunosuppressive effect Effects 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 206010003246 arthritis Diseases 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 229960005354 betamethasone sodium phosphate Drugs 0.000 description 1
- PLCQGRYPOISRTQ-LWCNAHDDSA-L betamethasone sodium phosphate Chemical compound [Na+].[Na+].C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@H](C)[C@@](C(=O)COP([O-])([O-])=O)(O)[C@@]1(C)C[C@@H]2O PLCQGRYPOISRTQ-LWCNAHDDSA-L 0.000 description 1
- 239000012867 bioactive agent Substances 0.000 description 1
- 229920002988 biodegradable polymer Polymers 0.000 description 1
- 239000004621 biodegradable polymer Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000001186 cumulative effect Effects 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000004945 emulsification Methods 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000012510 hollow fiber Substances 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 238000011146 sterile filtration Methods 0.000 description 1
- 150000003431 steroids Chemical class 0.000 description 1
- 210000001258 synovial membrane Anatomy 0.000 description 1
- 238000012385 systemic delivery Methods 0.000 description 1
- 229940126585 therapeutic drug Drugs 0.000 description 1
- 229940100611 topical cream Drugs 0.000 description 1
- 229940042130 topical foam Drugs 0.000 description 1
- 229940042129 topical gel Drugs 0.000 description 1
- 229940100617 topical lotion Drugs 0.000 description 1
- 229940100615 topical ointment Drugs 0.000 description 1
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
- A61K9/1682—Processes
- A61K9/1694—Processes resulting in granules or microspheres of the matrix type containing more than 5% of excipient
-
- 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
- A61K31/57—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane or progesterone
- A61K31/573—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane or progesterone substituted in position 21, e.g. cortisone, dexamethasone, prednisone or aldosterone
-
- 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
- A61K9/1605—Excipients; Inactive ingredients
- A61K9/1629—Organic macromolecular compounds
- A61K9/1641—Organic macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyethylene glycol, poloxamers
- A61K9/1647—Polyesters, e.g. poly(lactide-co-glycolide)
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
Landscapes
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Immunology (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pulmonology (AREA)
- Transplantation (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Manufacturing Of Micro-Capsules (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201361790554P | 2013-03-15 | 2013-03-15 | |
| US61/790,554 | 2013-03-15 | ||
| PCT/US2014/028657 WO2014144309A1 (en) | 2013-03-15 | 2014-03-14 | Sustained release microspheres and method of producing the same |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2909303A1 CA2909303A1 (en) | 2014-09-18 |
| CA2909303C true CA2909303C (en) | 2021-10-19 |
Family
ID=51537672
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2909303A Active CA2909303C (en) | 2013-03-15 | 2014-03-14 | Sustained release microspheres and method of producing the same |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US9956177B2 (enExample) |
| EP (1) | EP2968184B1 (enExample) |
| JP (2) | JP2016515517A (enExample) |
| CN (1) | CN105705141B (enExample) |
| CA (1) | CA2909303C (enExample) |
| ES (1) | ES2697696T3 (enExample) |
| MX (1) | MX362187B (enExample) |
| WO (1) | WO2014144309A1 (enExample) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9956177B2 (en) | 2013-03-15 | 2018-05-01 | Oakwood Laboratories LLC | Sustained release microspheres and method of producing same |
| JP7576334B2 (ja) * | 2019-03-29 | 2024-10-31 | 国立研究開発法人量子科学技術研究開発機構 | 放射性医薬の製造方法及び放射性医薬 |
| WO2022114876A1 (ko) * | 2020-11-30 | 2022-06-02 | 주식회사 엘지화학 | 캐스파제 저해제를 함유하는 주사용 조성물 및 이의 제조 방법 |
| EP4297753A4 (en) | 2021-02-24 | 2025-01-01 | Oakwood Laboratories, Llc | Microsphere formulations comprising lurasidone and methods for making and using the same |
| US20240148662A1 (en) * | 2021-03-11 | 2024-05-09 | Oakwood Laboratories, Llc | Methods and systems for making polymer microspheres |
| CN116999412A (zh) * | 2023-08-03 | 2023-11-07 | 四川迈可隆生物科技有限公司 | 一种含有倍他米松药物的缓释微球制剂及其制备方法 |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5945125A (en) | 1995-02-28 | 1999-08-31 | Temple University | Controlled release tablet |
| US6046187A (en) * | 1996-09-16 | 2000-04-04 | Children's Medical Center Corporation | Formulations and methods for providing prolonged local anesthesia |
| SE9704186D0 (sv) * | 1997-11-14 | 1997-11-14 | Astra Ab | New composition of matter |
| US6270802B1 (en) | 1998-10-28 | 2001-08-07 | Oakwood Laboratories L.L.C. | Method and apparatus for formulating microspheres and microcapsules |
| WO2002078673A1 (fr) * | 2001-03-29 | 2002-10-10 | Takeda Chemical Industries, Ltd. | Procede de production d'un medicament sous forme de granules fins |
| JP2002356419A (ja) * | 2001-03-29 | 2002-12-13 | Takeda Chem Ind Ltd | 微粒薬物の製造法 |
| WO2005107714A2 (en) * | 2004-05-05 | 2005-11-17 | Alkermes Controlled Therapeutics, Inc. | Method of forming microparticles that include a bisphosphonate and a polymer |
| GB2461186B (en) | 2008-04-21 | 2010-09-01 | Otonomy Inc | Controlled release corticosteroid compositions and methods for the treatment of otic disorders |
| US20100086596A1 (en) * | 2008-10-06 | 2010-04-08 | Oakwood Laboratories LLC | Microspheres for releasing an octreotide compound without an initial time lag |
| US8343498B2 (en) * | 2008-10-12 | 2013-01-01 | Massachusetts Institute Of Technology | Adjuvant incorporation in immunonanotherapeutics |
| UA111162C2 (uk) * | 2010-08-04 | 2016-04-11 | Флекшен Терап'Ютікс, Інк. | Ін'єкційна композиція ацетоніду триамцинолону для лікування болю |
| US8708159B2 (en) * | 2011-02-16 | 2014-04-29 | Oakwood Laboratories, Llc | Manufacture of microspheres using a hydrocyclone |
| US9956177B2 (en) | 2013-03-15 | 2018-05-01 | Oakwood Laboratories LLC | Sustained release microspheres and method of producing same |
-
2014
- 2014-03-14 US US14/774,851 patent/US9956177B2/en active Active
- 2014-03-14 CA CA2909303A patent/CA2909303C/en active Active
- 2014-03-14 ES ES14762738T patent/ES2697696T3/es active Active
- 2014-03-14 EP EP14762738.4A patent/EP2968184B1/en active Active
- 2014-03-14 CN CN201480016260.6A patent/CN105705141B/zh active Active
- 2014-03-14 JP JP2016502862A patent/JP2016515517A/ja active Pending
- 2014-03-14 MX MX2015012231A patent/MX362187B/es active IP Right Grant
- 2014-03-14 WO PCT/US2014/028657 patent/WO2014144309A1/en not_active Ceased
-
2019
- 2019-04-19 JP JP2019080106A patent/JP6808777B2/ja active Active
Also Published As
| Publication number | Publication date |
|---|---|
| JP6808777B2 (ja) | 2021-01-06 |
| CN105705141A (zh) | 2016-06-22 |
| CN105705141B (zh) | 2018-12-28 |
| JP2016515517A (ja) | 2016-05-30 |
| MX362187B (es) | 2019-01-08 |
| ES2697696T3 (es) | 2019-01-25 |
| US20160030351A1 (en) | 2016-02-04 |
| EP2968184A1 (en) | 2016-01-20 |
| MX2015012231A (es) | 2016-05-05 |
| EP2968184B1 (en) | 2018-10-24 |
| JP2019112471A (ja) | 2019-07-11 |
| WO2014144309A1 (en) | 2014-09-18 |
| BR112015022524A2 (pt) | 2017-08-22 |
| CA2909303A1 (en) | 2014-09-18 |
| EP2968184A4 (en) | 2016-09-07 |
| US9956177B2 (en) | 2018-05-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request |
Effective date: 20190226 |