JP5913367B2 - バンコマイシンの噴霧乾燥 - Google Patents
バンコマイシンの噴霧乾燥 Download PDFInfo
- Publication number
- JP5913367B2 JP5913367B2 JP2013548475A JP2013548475A JP5913367B2 JP 5913367 B2 JP5913367 B2 JP 5913367B2 JP 2013548475 A JP2013548475 A JP 2013548475A JP 2013548475 A JP2013548475 A JP 2013548475A JP 5913367 B2 JP5913367 B2 JP 5913367B2
- Authority
- JP
- Japan
- Prior art keywords
- vancomycin
- peg
- solution
- powder
- mannitol
- 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.)
- Expired - Fee Related
Links
- 108010059993 Vancomycin Proteins 0.000 title claims description 51
- 238000001694 spray drying Methods 0.000 title claims description 31
- 229960003165 vancomycin Drugs 0.000 title claims description 17
- MYPYJXKWCTUITO-LYRMYLQWSA-N vancomycin Chemical compound O([C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=C2C=C3C=C1OC1=CC=C(C=C1Cl)[C@@H](O)[C@H](C(N[C@@H](CC(N)=O)C(=O)N[C@H]3C(=O)N[C@H]1C(=O)N[C@H](C(N[C@@H](C3=CC(O)=CC(O)=C3C=3C(O)=CC=C1C=3)C(O)=O)=O)[C@H](O)C1=CC=C(C(=C1)Cl)O2)=O)NC(=O)[C@@H](CC(C)C)NC)[C@H]1C[C@](C)(N)[C@H](O)[C@H](C)O1 MYPYJXKWCTUITO-LYRMYLQWSA-N 0.000 title claims description 17
- MYPYJXKWCTUITO-UHFFFAOYSA-N vancomycin Natural products O1C(C(=C2)Cl)=CC=C2C(O)C(C(NC(C2=CC(O)=CC(O)=C2C=2C(O)=CC=C3C=2)C(O)=O)=O)NC(=O)C3NC(=O)C2NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(CC(C)C)NC)C(O)C(C=C3Cl)=CC=C3OC3=CC2=CC1=C3OC1OC(CO)C(O)C(O)C1OC1CC(C)(N)C(O)C(C)O1 MYPYJXKWCTUITO-UHFFFAOYSA-N 0.000 title claims description 17
- 238000000034 method Methods 0.000 claims description 54
- 239000000843 powder Substances 0.000 claims description 47
- 229960001572 vancomycin hydrochloride Drugs 0.000 claims description 34
- LCTORFDMHNKUSG-XTTLPDOESA-N vancomycin monohydrochloride Chemical compound Cl.O([C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=C2C=C3C=C1OC1=CC=C(C=C1Cl)[C@@H](O)[C@H](C(N[C@@H](CC(N)=O)C(=O)N[C@H]3C(=O)N[C@H]1C(=O)N[C@H](C(N[C@@H](C3=CC(O)=CC(O)=C3C=3C(O)=CC=C1C=3)C(O)=O)=O)[C@H](O)C1=CC=C(C(=C1)Cl)O2)=O)NC(=O)[C@@H](CC(C)C)NC)[C@H]1C[C@](C)(N)[C@H](O)[C@H](C)O1 LCTORFDMHNKUSG-XTTLPDOESA-N 0.000 claims description 34
- 239000000243 solution Substances 0.000 claims description 33
- 239000007921 spray Substances 0.000 claims description 30
- 239000002202 Polyethylene glycol Substances 0.000 claims description 25
- 229920001223 polyethylene glycol Polymers 0.000 claims description 25
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 claims description 21
- 229930195725 Mannitol Natural products 0.000 claims description 21
- 239000000594 mannitol Substances 0.000 claims description 21
- 235000010355 mannitol Nutrition 0.000 claims description 21
- 229920002565 Polyethylene Glycol 400 Polymers 0.000 claims description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
- 239000007979 citrate buffer Substances 0.000 claims description 7
- 238000010253 intravenous injection Methods 0.000 claims description 6
- 238000002156 mixing Methods 0.000 claims description 5
- MYPYJXKWCTUITO-KIIOPKALSA-N chembl3301825 Chemical compound O([C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=C2C=C3C=C1OC1=CC=C(C=C1Cl)[C@@H](O)[C@H](C(N[C@@H](CC(N)=O)C(=O)N[C@H]3C(=O)N[C@H]1C(=O)N[C@H](C(N[C@H](C3=CC(O)=CC(O)=C3C=3C(O)=CC=C1C=3)C(O)=O)=O)[C@H](O)C1=CC=C(C(=C1)Cl)O2)=O)NC(=O)[C@@H](CC(C)C)NC)[C@H]1C[C@](C)(N)C(O)[C@H](C)O1 MYPYJXKWCTUITO-KIIOPKALSA-N 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- 239000007864 aqueous solution Substances 0.000 claims description 3
- 238000002347 injection Methods 0.000 claims description 3
- 239000007924 injection Substances 0.000 claims description 3
- 238000005507 spraying Methods 0.000 claims description 3
- 239000000203 mixture Substances 0.000 description 44
- 238000009472 formulation Methods 0.000 description 37
- 239000007789 gas Substances 0.000 description 27
- 238000001035 drying Methods 0.000 description 16
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- 239000008215 water for injection Substances 0.000 description 12
- 238000012546 transfer Methods 0.000 description 10
- 239000008186 active pharmaceutical agent Substances 0.000 description 9
- 238000011049 filling Methods 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 238000004108 freeze drying Methods 0.000 description 6
- 229910001873 dinitrogen Inorganic materials 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 238000001914 filtration Methods 0.000 description 4
- 239000002245 particle Substances 0.000 description 4
- 238000012545 processing Methods 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 239000000546 pharmaceutical excipient Substances 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 238000011084 recovery Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 108010032807 vancomycin B Proteins 0.000 description 3
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 238000013461 design Methods 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000003032 molecular docking Methods 0.000 description 2
- 238000005070 sampling Methods 0.000 description 2
- 230000001954 sterilising effect Effects 0.000 description 2
- 238000004659 sterilization and disinfection Methods 0.000 description 2
- 241000894006 Bacteria Species 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- 239000004471 Glycine Substances 0.000 description 1
- RVGRUAULSDPKGF-UHFFFAOYSA-N Poloxamer Chemical compound C1CO1.CC1CO1 RVGRUAULSDPKGF-UHFFFAOYSA-N 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 238000012865 aseptic processing Methods 0.000 description 1
- 238000000889 atomisation Methods 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004891 communication Methods 0.000 description 1
- 238000002788 crimping Methods 0.000 description 1
- 230000006837 decompression Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 238000007599 discharging Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000012061 filter integrity test Methods 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hcl hcl Chemical compound Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 230000036512 infertility Effects 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000012669 liquid formulation Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000010327 methods by industry Methods 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229960000502 poloxamer Drugs 0.000 description 1
- 229920001983 poloxamer Polymers 0.000 description 1
- 238000011045 prefiltration Methods 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- 238000012430 stability testing Methods 0.000 description 1
- 239000003381 stabilizer Substances 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
- 238000003860 storage Methods 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
Images
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
- A61K38/04—Peptides having up to 20 amino acids in a fully defined sequence; Derivatives thereof
- A61K38/14—Peptides containing saccharide radicals; Derivatives thereof, e.g. bleomycin, phleomycin, muramylpeptides or vancomycin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
- A61K38/04—Peptides having up to 20 amino acids in a fully defined sequence; Derivatives thereof
- A61K38/12—Cyclic peptides, e.g. bacitracins; Polymyxins; Gramicidins S, C; Tyrocidins A, B or C
-
- 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
-
- 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
- A61K9/1617—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
- A61K9/14—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
- A61K9/1617—Organic compounds, e.g. phospholipids, fats
- A61K9/1623—Sugars or sugar alcohols, e.g. lactose; Derivatives thereof; Homeopathic globules
-
- 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
-
- 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
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Gastroenterology & Hepatology (AREA)
- Immunology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Molecular Biology (AREA)
- Biophysics (AREA)
- Dermatology (AREA)
- Medicinal Preparation (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201161429844P | 2011-01-05 | 2011-01-05 | |
| US61/429,844 | 2011-01-05 | ||
| PCT/US2012/020160 WO2012094381A2 (en) | 2011-01-05 | 2012-01-04 | Spray drying vancomycin |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2014501781A JP2014501781A (ja) | 2014-01-23 |
| JP2014501781A5 JP2014501781A5 (OSRAM) | 2015-09-24 |
| JP5913367B2 true JP5913367B2 (ja) | 2016-04-27 |
Family
ID=46457949
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2013548475A Expired - Fee Related JP5913367B2 (ja) | 2011-01-05 | 2012-01-04 | バンコマイシンの噴霧乾燥 |
Country Status (10)
| Country | Link |
|---|---|
| US (3) | US8709310B2 (OSRAM) |
| EP (1) | EP2661254B1 (OSRAM) |
| JP (1) | JP5913367B2 (OSRAM) |
| CN (1) | CN103429228B (OSRAM) |
| AU (1) | AU2012204462A1 (OSRAM) |
| CA (1) | CA2823628A1 (OSRAM) |
| DK (1) | DK2661254T3 (OSRAM) |
| ES (1) | ES2645769T3 (OSRAM) |
| TW (1) | TW201309346A (OSRAM) |
| WO (1) | WO2012094381A2 (OSRAM) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ITLO20110001A1 (it) * | 2011-05-03 | 2012-11-04 | Fisiopharma Srl | Flaconi di vancomicina cloroidrata con stabilità migliorata |
| US8952105B2 (en) | 2012-05-23 | 2015-02-10 | Baker Hughes Incorporated | Variable TG article, method of making, and use of same |
| CN104043104B (zh) | 2013-03-15 | 2018-07-10 | 浙江创新生物有限公司 | 含盐酸万古霉素的喷雾干粉及其工业化制备方法 |
| JP6480866B2 (ja) * | 2013-09-30 | 2019-03-13 | 第一三共株式会社 | スプレードライ法を用いたＤ−マンニトールα型結晶の選択的製造方法 |
| WO2015138983A1 (en) | 2014-03-14 | 2015-09-17 | Cutispharma, Inc. | Composition and method for vancomycin oral liquid |
| PT107568B (pt) * | 2014-03-31 | 2018-11-05 | Hovione Farm S A | Processo de secagem por atomização para a produção de pós com propriedades melhoradas. |
| CA3132923A1 (en) * | 2019-03-08 | 2020-09-17 | Emphascience, Inc. | Stable pharmaceutical formulations of peptide and protein drugs |
| CN114432339B (zh) * | 2022-02-18 | 2023-05-26 | 重庆希尔安药业有限公司 | 一种聚乙二醇钠钾散及其制备方法 |
| CN119745821B (zh) * | 2024-11-28 | 2025-10-03 | 时森海(杭州)医药科技有限公司 | 一种盐酸万古霉素固体胶囊及其制备方法 |
Family Cites Families (83)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2911036A (en) | 1955-01-03 | 1959-11-03 | Melvin E Lazar | Spray-drying apparatus |
| DE3013839A1 (de) | 1979-04-13 | 1980-10-30 | Freunt Ind Co Ltd | Verfahren zur herstellung einer aktivierten pharmazeutischen zusammensetzung |
| US4831015A (en) | 1987-08-13 | 1989-05-16 | American Cyanamid Company | High potency biomass-free avoparcin and a method for its preparation |
| IL93618A0 (en) | 1989-03-06 | 1990-12-23 | Lilly Co Eli | Improved diluent formulation for daptomycin |
| JPH03193735A (ja) * | 1989-12-22 | 1991-08-23 | Shionogi & Co Ltd | グリコペプチド系抗生物質の安定化組成物 |
| JPH04142149A (ja) | 1990-10-02 | 1992-05-15 | Canon Inc | ファクシミリ装置 |
| ES2141108T3 (es) | 1991-07-02 | 2000-03-16 | Inhale Inc | Metodo y dispositivo para proporcionar medicamentos en aerosol. |
| US6673335B1 (en) | 1992-07-08 | 2004-01-06 | Nektar Therapeutics | Compositions and methods for the pulmonary delivery of aerosolized medicaments |
| US6582728B1 (en) | 1992-07-08 | 2003-06-24 | Inhale Therapeutic Systems, Inc. | Spray drying of macromolecules to produce inhaleable dry powders |
| US5785049A (en) | 1994-09-21 | 1998-07-28 | Inhale Therapeutic Systems | Method and apparatus for dispersion of dry powder medicaments |
| ES2179831T3 (es) | 1992-09-29 | 2003-02-01 | Inhale Therapeutic Syst | Liberacion en los pulmones de fragmentos activos de hormona paratiroidiana. |
| US6051256A (en) | 1994-03-07 | 2000-04-18 | Inhale Therapeutic Systems | Dispersible macromolecule compositions and methods for their preparation and use |
| GB9406769D0 (en) | 1994-04-06 | 1994-05-25 | Btr Plc | Valve system |
| PL179910B1 (pl) | 1994-05-06 | 2000-11-30 | Pfizer | Postac dawkowania o kontrolowanym uwalnianiu zawierajaca azytromycyne PL PL PL PL PL PL PL PL |
| EP0759939B1 (en) | 1994-05-18 | 2005-07-20 | Nektar Therapeutics | Methods and compositions for the dry powder formulation of interferons |
| WO1996011672A1 (en) | 1994-10-13 | 1996-04-25 | Wakamoto Pharmaceutical Co., Ltd. | Lyophilized preparation providing reversibly thermogelling water-base medicinal composition |
| IL116085A (en) | 1994-12-16 | 1999-12-31 | Ortho Pharma Corp | Spray dried erythropoietin |
| SI9500039B (sl) * | 1995-02-07 | 2002-02-28 | Lek, | Nov kombiniran postopek čiščenja Vankomicin hidroklorida |
| US7038219B2 (en) | 1996-05-22 | 2006-05-02 | Purepulse Technologies, Inc. | Sterilization of packages and their contents using light |
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- 2012-01-04 CA CA2823628A patent/CA2823628A1/en not_active Abandoned
- 2012-01-04 TW TW101100376A patent/TW201309346A/zh unknown
- 2012-01-04 ES ES12732323.6T patent/ES2645769T3/es active Active
- 2012-01-04 CN CN201280011863.8A patent/CN103429228B/zh not_active Expired - Fee Related
- 2012-01-04 JP JP2013548475A patent/JP5913367B2/ja not_active Expired - Fee Related
- 2012-01-04 US US13/343,297 patent/US8709310B2/en active Active
- 2012-01-04 EP EP12732323.6A patent/EP2661254B1/en active Active
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Also Published As
| Publication number | Publication date |
|---|---|
| CN103429228B (zh) | 2016-10-26 |
| US20130009330A1 (en) | 2013-01-10 |
| CN103429228A (zh) | 2013-12-04 |
| AU2012204462A1 (en) | 2013-07-11 |
| WO2012094381A2 (en) | 2012-07-12 |
| ES2645769T3 (es) | 2017-12-07 |
| US9763997B2 (en) | 2017-09-19 |
| US8709310B2 (en) | 2014-04-29 |
| EP2661254A4 (en) | 2015-01-28 |
| JP2014501781A (ja) | 2014-01-23 |
| DK2661254T3 (da) | 2017-11-06 |
| EP2661254B1 (en) | 2017-08-02 |
| US9023258B2 (en) | 2015-05-05 |
| TW201309346A (zh) | 2013-03-01 |
| CA2823628A1 (en) | 2012-07-12 |
| WO2012094381A3 (en) | 2013-06-20 |
| US20150231197A1 (en) | 2015-08-20 |
| US20140235530A1 (en) | 2014-08-21 |
| EP2661254A2 (en) | 2013-11-13 |
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