WO2001015664A2 - Coformulation methods and their products - Google Patents
Coformulation methods and their products Download PDFInfo
- Publication number
- WO2001015664A2 WO2001015664A2 PCT/GB2000/003328 GB0003328W WO0115664A2 WO 2001015664 A2 WO2001015664 A2 WO 2001015664A2 GB 0003328 W GB0003328 W GB 0003328W WO 0115664 A2 WO0115664 A2 WO 0115664A2
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- coformulation
- active substance
- oligomeric
- polymeric material
- paracetamol
- Prior art date
Links
- RZVAJINKPMORJF-UHFFFAOYSA-N CC(Nc(cc1)ccc1O)=O Chemical compound CC(Nc(cc1)ccc1O)=O RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
- KOWIZHDULJSRPT-WUKNDPDISA-N CS(c(cc1)ccc1/C(/c(cc1)ccc1Br)=C(\CCO1)/C1=O)(=O)=O Chemical compound CS(c(cc1)ccc1/C(/c(cc1)ccc1Br)=C(\CCO1)/C1=O)(=O)=O KOWIZHDULJSRPT-WUKNDPDISA-N 0.000 description 1
- OFOFOZKUGISWRT-WUKNDPDISA-N CS(c(cc1)ccc1/C(/c(cc1)ccc1Cl)=C(\CCO1)/C1=O)(=O)=O Chemical compound CS(c(cc1)ccc1/C(/c(cc1)ccc1Cl)=C(\CCO1)/C1=O)(=O)=O OFOFOZKUGISWRT-WUKNDPDISA-N 0.000 description 1
- CGIGDMFJXJATDK-UHFFFAOYSA-N Cc1c(CC(O)=O)c2cc(OC)ccc2[n]1C(c(cc1)ccc1Cl)=O Chemical compound Cc1c(CC(O)=O)c2cc(OC)ccc2[n]1C(c(cc1)ccc1Cl)=O CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 description 1
- FFGPTBGBLSHEPO-UHFFFAOYSA-N NC(N1c(cccc2)c2C=Cc2c1cccc2)=O Chemical compound NC(N1c(cccc2)c2C=Cc2c1cccc2)=O FFGPTBGBLSHEPO-UHFFFAOYSA-N 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
- A61K9/00—Medicinal preparations characterised by special physical form
-
- 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
- A61K9/1635—Organic macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyvinyl pyrrolidone, poly(meth)acrylates
-
- 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
- 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
- A61K9/1652—Polysaccharides, e.g. alginate, cellulose derivatives; Cyclodextrin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/06—Antiabortive agents; Labour repressants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D11/00—Solvent extraction
- B01D11/04—Solvent extraction of solutions which are liquid
- B01D11/0403—Solvent extraction of solutions which are liquid with a supercritical fluid
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D11/00—Solvent extraction
- B01D11/04—Solvent extraction of solutions which are liquid
- B01D11/0403—Solvent extraction of solutions which are liquid with a supercritical fluid
- B01D11/0407—Solvent extraction of solutions which are liquid with a supercritical fluid the supercritical fluid acting as solvent for the solute
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D11/00—Solvent extraction
- B01D11/04—Solvent extraction of solutions which are liquid
- B01D11/0403—Solvent extraction of solutions which are liquid with a supercritical fluid
- B01D11/0411—Solvent extraction of solutions which are liquid with a supercritical fluid the supercritical fluid acting as solvent for the solvent and as anti-solvent for the solute, e.g. formation of particles from solutions
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D11/00—Solvent extraction
- B01D11/04—Solvent extraction of solutions which are liquid
- B01D11/0488—Flow sheets
Definitions
- SEDSTM may be used to prepare such coformulations is surprising in view of earlier literature on the process.
- WO-95/01221 there are examples of drug/polymer coformulations (salmeterol xinafoate and hydroxypropyl cellulose), but although these apparently demonstrate "disturbance" of crystallinity, it is clear from the appended DSC/XRD data that significant amounts of the crystalline drug are still present.
- the anti-solvent used in the SEDSTM process is preferably supercritical carbon dioxide, although others (eg, as mentioned in the earlier SEDSTM literature) may be used instead or in addition.
- the oligomeric (which includes dimeric) or polymeric material may be any suitable excipient for the active substance, of whatever molecular weight and whether hydrophilic - such as a polyethylene glycol, hydroxypropyl methyl cellulose (HPMC) or polyvinyl pyrrolidone (PVP) - or hydrophobic - such as an ethyl cellulose (EC). It may be a biodegradable oligomer or polymer such as a polylactide or glycolide or a polylactide/glycolide. It may be crystalline, semi-crystalline or amorphous. It may be a homo- or co-oligomer/polymer, synthetic or naturally occurring.
- the active substance may be a single active substance or a mixture of two or more active substances. It may be monomeric or polymeric, organic (including organometallic) or inorganic, hydrophilic or hydrophobic. It may be a small molecule, for instance a synthetic drug like paracetamol, or a larger molecule such as a (poly)peptide, an enzyme, an antigen or other biological material. It preferably comprises a pharmaceutically active substance, although many other active substances, whatever their intended function (for instance, herbicides, pesticides, foodstuffs, nutriceuticals, etc.), may be coformulated with oligomers or polymers in accordance with the invention.
- a coformulation according to the invention preferably between 80 and 100%, more preferably between 90 and 100% or between 95 and 100%, most preferably 100%, of the active substance is present in an amorphous as opposed to crystalline form.
- the active substance preferably represents at least 1%, more preferably at least 2% or 5% or 10% or 20% or 25% or 30% or 35% or 40% or 50% or 60% or 70% or 80% or 90% of the system.
- products according to the invention can contain high loadings of the active substance, of which all or substantially all is present as a single amorphous phase.
- 4-[4-(methylsulfonyl)phe ⁇ yl]-3-phenyl-2(5H)-f ⁇ ranone is a COX-2 selective inhibitor approved for the treatment of osteoarthritis, treatment of primary dysmenorrhea and management of acute pain and is marketed in the U.S. under the tradename VIOXX ® (rofecoxib). See e.g., U.S. 5,474, 995, incorporated by reference herein.
- Figure 1 is a schematic illustration of apparatus usable to carry out methods, and obtain products, according to the invention
- Figures 2-5 are SEM (scanning electron microscope) photographs of some of the starting materials and products of Example I below;
- Figures 27 and 28 are SEM photographs of some of the products of Example II.
- Example IV the drug glibenclamide was coformulated with 75/25 DL-lactide- c ⁇ -caprolactone.
- a suitable solvent depended on the properties of both drug and polymer, but particularly on the latter because of the potential difficulties of processing polymeric solutions and dispersions.
- Polymeric dispersions can exhibit very high viscosities, even when dilute, whereas in "good” solvents the polymer matrix will relax and loosen, allowing both a greater degree of interaction and a lower viscosity, important respectively for the production of intimate drug/polymer mixtures and for the processing requirements of SEDSTM [8].
- R is H, CH 3 or [CH j CHtOHjCHJ
- the principal operating conditions were manipulated and optimised for each drug/polymer system. Different drug:polymer concentration ratios were also tested. It was found that temperatures in the range 34-50°C and pressures between 80 and 100 bar were preferable for processing these polymers.
- Anti-solven target solution flow rate ratios (into the particle formation vessel) were between 66: 1 and 200: 1, ie, an anti-solvent flow rate of 20 ml/min was used with target solution flow rates of between 0.1 and 0.3 ml min.
Abstract
Description
Claims
Priority Applications (6)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CA002382556A CA2382556A1 (en) | 1999-08-31 | 2000-08-31 | Coformulation methods and their products |
JP2001519878A JP2003508419A (en) | 1999-08-31 | 2000-08-31 | Co-compounding methods and their products |
EP00956682A EP1207856A2 (en) | 1999-08-31 | 2000-08-31 | Coformulation methods and their products |
KR1020027002715A KR20020047137A (en) | 1999-08-31 | 2000-08-31 | Coformulation methods and their products |
AU68550/00A AU783570B2 (en) | 1999-08-31 | 2000-08-31 | Coformulation methods and their products |
MXPA02001803A MXPA02001803A (en) | 1999-08-31 | 2000-08-31 | Coformulation methods and their products. |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB9920558.5 | 1999-08-31 | ||
GBGB9920558.5A GB9920558D0 (en) | 1999-08-31 | 1999-08-31 | Methods for particle formation and their products |
Publications (2)
Publication Number | Publication Date |
---|---|
WO2001015664A2 true WO2001015664A2 (en) | 2001-03-08 |
WO2001015664A3 WO2001015664A3 (en) | 2001-09-20 |
Family
ID=10860085
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/GB2000/003328 WO2001015664A2 (en) | 1999-08-31 | 2000-08-31 | Coformulation methods and their products |
Country Status (8)
Country | Link |
---|---|
EP (1) | EP1207856A2 (en) |
JP (1) | JP2003508419A (en) |
KR (1) | KR20020047137A (en) |
AU (1) | AU783570B2 (en) |
CA (1) | CA2382556A1 (en) |
GB (2) | GB9920558D0 (en) |
MX (1) | MXPA02001803A (en) |
WO (1) | WO2001015664A2 (en) |
Cited By (23)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB2371501A (en) * | 2000-11-09 | 2002-07-31 | Bradford Particle Design Ltd | Particle formation methods and their products |
FR2825292A1 (en) * | 2001-05-30 | 2002-12-06 | Csir | New process for coating an active substance with an inter polymeric complex in a supercritical liquid |
EP1263412A1 (en) | 2000-03-04 | 2002-12-11 | Eco2 SA | Micronized pharmaceuticals |
WO2003035673A1 (en) | 2001-10-22 | 2003-05-01 | Dompe S.P.A. | Supercritical fluids processing: preparation of protein microparticles and their stabilisation |
US6964978B2 (en) | 1999-12-08 | 2005-11-15 | Pharmacia Corporation | Solid-state form of celecoxib having enhanced bioavailability |
US7108867B2 (en) | 2001-01-26 | 2006-09-19 | Astrazeneca Ab | Process for preparing particles |
WO2007018953A1 (en) * | 2005-07-25 | 2007-02-15 | Hewlett-Packard Development Company, L.P. | Preparation of nanoparticles |
WO2007018954A2 (en) * | 2005-07-25 | 2007-02-15 | Hewlett-Packard Development Company, L.P. | Application of a bioactive agent in a solvent composition to produce a target particle morphology |
WO2007018887A2 (en) * | 2005-07-25 | 2007-02-15 | Hewlett-Packard Development Company, L.P. | Application of a bioactive agent to a substrate |
US7354601B2 (en) | 2003-05-08 | 2008-04-08 | Walker Stephen E | Particulate materials |
WO2008096144A1 (en) * | 2007-02-08 | 2008-08-14 | Thar Pharmaceuticals Inc. | Method of creating crystalline substances |
US7507823B2 (en) | 2004-05-06 | 2009-03-24 | Bristol-Myers Squibb Company | Process of making aripiprazole particles |
EP1330266B2 (en) † | 2000-10-19 | 2009-08-26 | Separex | Method for making very fine particles consisting of a principle inserted in a host molecule |
US7744923B2 (en) | 2006-10-11 | 2010-06-29 | Crititech, Inc. | Method for precipitation of small medicament particles into use containers |
EP2612703A2 (en) | 2002-04-17 | 2013-07-10 | Nektar Therapeutics | Particulate materials |
US8585942B2 (en) | 2007-12-07 | 2013-11-19 | Xspray Microparticles Ab | Process and arrangement for producing particles utilizing subcritical fluids |
US9023393B2 (en) | 2003-08-04 | 2015-05-05 | Bend Research, Inc. | Pharmaceutical compositions of adsorbates of amorphous drugs and lipophilic microphase-forming materials |
US9226900B2 (en) | 2008-07-11 | 2016-01-05 | Critical Pharmaceuticals Limited | Process for preparing microparticles |
US9468604B2 (en) | 2001-06-22 | 2016-10-18 | Bend Research, Inc. | Pharmaceutical compositions of dispersions of drug and neutral polymers |
US9486410B2 (en) | 2002-02-01 | 2016-11-08 | Bend Research, Inc. | Pharmaceutical compositions of amorphous dispersions of drugs and lipophilic microphase-forming materials |
US9700529B2 (en) | 2002-05-03 | 2017-07-11 | Nektar Therapeutics | Particulate materials |
US9808030B2 (en) | 2011-02-11 | 2017-11-07 | Grain Processing Corporation | Salt composition |
US9833451B2 (en) | 2007-02-11 | 2017-12-05 | Map Pharmaceuticals, Inc. | Method of therapeutic administration of DHE to enable rapid relief of migraine while minimizing side effect profile |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
AU2002342241B2 (en) | 2001-11-01 | 2007-07-19 | Novartis Ag | Spray drying methods and compositions thereof |
DK2802314T3 (en) * | 2012-01-13 | 2021-01-25 | Xspray Microparticles Ab | METHOD OF MANUFACTURE OF STABLE, AMORPHEY HYBRID NANOPARTICLES WHICH INCLUDE AT LEAST ONE PROTEIN CHINESE INHIBITOR AND AT LEAST ONE POLYMER STABILIZING AND MATRIX-FORMING COMPONENT |
ES2946549T3 (en) * | 2012-01-13 | 2023-07-20 | Xspray Pharma Ab Publ | Pharmaceutical composition of nilotinib |
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WO1998013136A1 (en) * | 1996-09-25 | 1998-04-02 | Mainelab | Method for preparing microcapsules of active substances coated with a polymer and novel microcapsules in particular resulting from the method |
EP0852140A1 (en) * | 1995-08-11 | 1998-07-08 | Nissan Chemical Industries, Limited | Methods for making hardly soluble medicine amorphous |
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US5980942A (en) * | 1997-01-23 | 1999-11-09 | Yissum Research Development Company Of The Hebrew University Of Jerusalem | Zero-order sustained release matrix tablet formulations of carbamazepine |
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1999
- 1999-08-31 GB GBGB9920558.5A patent/GB9920558D0/en not_active Ceased
-
2000
- 2000-08-31 KR KR1020027002715A patent/KR20020047137A/en not_active Application Discontinuation
- 2000-08-31 AU AU68550/00A patent/AU783570B2/en not_active Ceased
- 2000-08-31 WO PCT/GB2000/003328 patent/WO2001015664A2/en not_active Application Discontinuation
- 2000-08-31 MX MXPA02001803A patent/MXPA02001803A/en active IP Right Grant
- 2000-08-31 EP EP00956682A patent/EP1207856A2/en not_active Withdrawn
- 2000-08-31 JP JP2001519878A patent/JP2003508419A/en active Pending
- 2000-08-31 CA CA002382556A patent/CA2382556A1/en not_active Abandoned
- 2000-08-31 GB GB0021227A patent/GB2355194B/en not_active Expired - Fee Related
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Cited By (45)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6964978B2 (en) | 1999-12-08 | 2005-11-15 | Pharmacia Corporation | Solid-state form of celecoxib having enhanced bioavailability |
EP1263412A1 (en) | 2000-03-04 | 2002-12-11 | Eco2 SA | Micronized pharmaceuticals |
EP1330266B2 (en) † | 2000-10-19 | 2009-08-26 | Separex | Method for making very fine particles consisting of a principle inserted in a host molecule |
GB2371501B (en) * | 2000-11-09 | 2003-05-14 | Bradford Particle Design Ltd | Particle formation methods and their products |
GB2371501A (en) * | 2000-11-09 | 2002-07-31 | Bradford Particle Design Ltd | Particle formation methods and their products |
US10798955B2 (en) | 2000-11-09 | 2020-10-13 | Nektar Therapeutics | Compositions of particulate coformulation |
US7115280B2 (en) | 2000-11-09 | 2006-10-03 | Nektar Therapeutics Uk, Ltd. | Particle formation methods and their products |
US7108867B2 (en) | 2001-01-26 | 2006-09-19 | Astrazeneca Ab | Process for preparing particles |
US7829123B2 (en) | 2001-01-26 | 2010-11-09 | Astrazeneca Ab | Process |
GB2392619B (en) * | 2001-05-30 | 2004-10-20 | Csir | Method of encapsulating an active substance |
FR2825292A1 (en) * | 2001-05-30 | 2002-12-06 | Csir | New process for coating an active substance with an inter polymeric complex in a supercritical liquid |
GB2392619A (en) * | 2001-05-30 | 2004-03-10 | Csir | Method of encapsulating an active substance |
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Also Published As
Publication number | Publication date |
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EP1207856A2 (en) | 2002-05-29 |
KR20020047137A (en) | 2002-06-21 |
GB2355194A (en) | 2001-04-18 |
GB2355194B (en) | 2003-01-08 |
GB0021227D0 (en) | 2000-10-18 |
AU783570B2 (en) | 2005-11-10 |
AU6855000A (en) | 2001-03-26 |
GB9920558D0 (en) | 1999-11-03 |
WO2001015664A3 (en) | 2001-09-20 |
JP2003508419A (en) | 2003-03-04 |
MXPA02001803A (en) | 2004-02-26 |
CA2382556A1 (en) | 2001-03-08 |
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