WO2004096284A1 - Procede de preparation de complexes moleculaires - Google Patents
Procede de preparation de complexes moleculaires Download PDFInfo
- Publication number
- WO2004096284A1 WO2004096284A1 PCT/FR2004/000995 FR2004000995W WO2004096284A1 WO 2004096284 A1 WO2004096284 A1 WO 2004096284A1 FR 2004000995 W FR2004000995 W FR 2004000995W WO 2004096284 A1 WO2004096284 A1 WO 2004096284A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- active substance
- diffusion
- molecular
- agent
- soluble
- Prior art date
Links
Classifications
-
- 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
- A61K47/50—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 the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B82—NANOTECHNOLOGY
- B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
- B82Y5/00—Nanobiotechnology or nanomedicine, e.g. protein engineering or drug delivery
-
- 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
- A61K47/50—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 the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
- A61K47/69—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 the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit
- A61K47/6949—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 the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit inclusion complexes, e.g. clathrates, cavitates or fullerenes
- A61K47/6951—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 the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit inclusion complexes, e.g. clathrates, cavitates or fullerenes using cyclodextrin
-
- 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
-
- 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
- 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
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
Definitions
- the present invention relates to a process for the preparation of soluble molecular complexes comprising one or more poorly soluble active substances in an aqueous medium included in one or more host molecules, characterized in that it is limited by the following steps: ) contacting one or more active substances with one or more host molecules, (b). implementing a molecular diffusion step by contacting, in static mode, a dense fluid under pressure with the mixture obtained in step (a) in the presence of one or more diffusion agents, (c) ) recovery of the molecular complex thus formed.
- the term "dense fluid under pressure” is intended to mean any fluid used at a temperature or a pressure greater than their critical value.
- the term "active substance which is poorly soluble in an aqueous medium” means any active substance which has little or no solubility in an aqueous medium and in particular has a solubility of less than 20 ⁇ g / ml.
- it may be a pharmaceutical active agent (for example, analgesics, antipyretics, aspirin and its derivatives, antibiotics, anti-inflammatories, antiulcerers, antihypertensives, neuroleptics, antidepressants, oligonucleotides with therapeutic activity, peptides with therapeutic activity and proteins with therapeutic, cosmetic or nutraceutical activity.
- host molecule in the sense of the present invention any substance capable of capturing active substances.
- the host molecule is chosen from the group consisting of polyoses and monosaccharides, in particular cyclodextrins and their mixture.
- it is ⁇ -cyclodextrin, methyl- ⁇ -cyclodextrin, ⁇ -cyclodextrin or hydroxypropyl- ⁇ -cyclodextrin.
- diffusion agent in the sense of the present invention any solvent promoting interaction of the active substance with the host molecule.
- this diffusion agent is chosen from the group consisting of alcohols, ketones, ethers, esters and water with or without surfactant and their mixtures. Even more advantageously, it is water.
- the molecular diffusion step (b) of the process according to the present invention is carried out with stirring.
- the diffusion agent may be added continuously or discontinuously in an amount of between 1 and 50% by weight, preferably between 20 and 25% by weight.
- the time required for the molecular diffusion of step (b) is determined by any suitable method. This step (b) can be repeated as many times as desired to obtain a satisfactory dissolution rate.
- step (b) lasts between about 2 and 16 hours.
- step (b) The pressure and temperature conditions of step (b) are chosen so as to promote molecular diffusion.
- the pressure of the supercritical fluid is between 5 MPa and 40 MPa and the temperature between 0 and 120 ° C.
- step (b) of the process according to the present invention is carried out in a closed reactor, in particular an autoclave.
- the process can be carried out batchwise or continuously.
- the process according to the present invention is carried out batchwise.
- the present invention also relates to soluble molecular complexes comprising one or more substance (s) active (s) slightly soluble (s) in an aqueous medium included in one or more host molecules, characterized in that they are likely to be obtained by the method according to the present invention.
- the implementation of the molecular diffusion step in a dense medium under pressure in the presence of a diffusion agent allows a strong interaction of the particles of active substance with the host molecule, which favors the dissolution in an aqueous medium, which is multiplied by about 100 by the method according to the present invention.
- the inclusion rate of the active substance in the host molecule is evaluated by differential thermal analysis Differential Scanning Calorimetry). A temperature ramp under a stream of nitrogen is applied to the product to be tested, using a Perkin Elmer DSC 7 apparatus.
- the complexation yield is evaluated by measuring the reduction (or disappearance) of the thermal peak relative to the active ingredient remained free.
- One mole of minoxidil and two moles of ⁇ -cyclodextrin are introduced into a reactor.
- the carbon dioxide is subsequently introduced into the reactor under a pressure of 15 MPa and a temperature of 80 ° C.
- the whole is maintained under these operating conditions for a period of two hours.
- the inclusion rate is measured on the collected powder and is equal to 0%. No inclusion of the active substance is observable in the host molecule.
- One mole of piroxicam and two moles of ⁇ -cyclodextrin are introduced into a reactor.
- the carbon dioxide is subsequently introduced into the reactor under a pressure of 15 MPa and a temperature of 150 ° C.
- the whole is maintained under these operating conditions for a period of two hours.
- the inclusion rate is measured on the collected powder and is equal to 0%. No inclusion of the active substance is observable in the host molecule.
- the inclusion rate is measured on the collected powder and is equal to 50%.
- the inclusion rate is measured on the collected powder and is equal to 92%.
- Example 4 Piroxicam (active substance) and ⁇ -cyclodextrin (host molecule) 4.1. Without adding a broadcast agent
- One mole of piroxicam and two moles of ⁇ -cyclodextrin are introduced into a reactor.
- the carbon dioxide is subsequently introduced into the reactor under a pressure of 15 MPa and a temperature of 150 ° C.
- the whole is maintained under these operating conditions for a period of two hours.
- the inclusion rate is measured on the collected powder and is equal to 0%. No inclusion of the active substance is observable in the host molecule.
- the inclusion rate is measured on the collected powder and is equal to 28%.
- Example 5 tiaprofenic acid (active substance) and ⁇ -cyclodextrin (host molecule)
- One mole of tiaprofenic acid and two moles of ⁇ -cyclodextrin are introduced into a reactor.
- the carbon dioxide is subsequently introduced into the reactor under a pressure of 15 MPa and a temperature of 50 ° C. The whole is maintained under these operating conditions for a period of two hours.
- the inclusion rate is measured on the collected powder and is equal to 19%.
- One mole of tiaprofenic acid and two moles of ⁇ -cyclodextrin are introduced into a reactor, as well as 20.5% by weight of diffusion agent (water).
- the carbon dioxide is subsequently introduced into the reactor under a pressure of 15 MPa and a temperature of 50 ° C. The whole is maintained under these operating conditions for a period of two hours.
- the inclusion level is measured on the powder collected and is found to be equal to 100%.
- the inclusion of the active substance in the host molecule seems complete in this case.
- Example 6 Omeprazole (active substance) and ⁇ -cyclodextrin (host molecule)
- omeprazole One mole of omeprazole and two moles of ⁇ -cyclodextrin are introduced into a reactor.
- the carbon dioxide is subsequently introduced into the reactor under a pressure of 15 MPa and a temperature of 100 ° C. The whole is maintained under these operating conditions for a period of two hours. After relaxation of the medium, the inclusion rate is measured on the collected powder and is equal to 2%. Without addition of diffusion agent, the inclusion of the active substance in the host molecule seems very weak.
- omeprazole and ⁇ -cyclodextrin are introduced into a reactor, as well as 20.7% by weight of diffusion agent.
- the carbon dioxide is subsequently introduced into the reactor under a pressure of 15 MPa and a temperature of 100 ° C. The whole is maintained under these operating conditions for a period of two hours.
- the inclusion rate is measured on the collected powder and is equal to 66%.
- Example 7 Eflucimibe (active substance) and ⁇ -cyclodextrin (host molecule) 7.1. Without adding a broadcast agent
- One mole of eflucimibe and two moles of ⁇ -cyclodextrin are introduced into a reactor.
- the carbon dioxide is subsequently introduced into the reactor under a pressure of 30 MPa and a temperature of 100 ° C.
- the whole is maintained under these operating conditions for a period of sixteen hours.
- the inclusion rate is measured on the collected powder and is equal to 0%. Without addition of diffusion agent, the inclusion of the active substance in the host molecule is zero.
- Dissolution test A dissolution test was carried out on the products obtained in Examples 7.1 and 7.2.
- the amount of eflucimibe solubilized from the powder collected in Example 7.1 is 24 ⁇ g / ml instead of 22 ⁇ g / ml for the initial mixture.
- the amount of eflucimibe solubilized from the powder collected in Example 7. 2 is 160 ⁇ g / ml instead of 22 ⁇ g / ml for the mixture. initial.
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- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Nanotechnology (AREA)
- General Chemical & Material Sciences (AREA)
- General Engineering & Computer Science (AREA)
- Medical Informatics (AREA)
- Molecular Biology (AREA)
- Crystallography & Structural Chemistry (AREA)
- Biophysics (AREA)
- Biotechnology (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Diabetes (AREA)
- Obesity (AREA)
- Hematology (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
- Compounds Of Unknown Constitution (AREA)
- Steroid Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Cosmetics (AREA)
- Extraction Or Liquid Replacement (AREA)
- Peptides Or Proteins (AREA)
Abstract
Description
Claims
Priority Applications (18)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP04742568A EP1638609B1 (fr) | 2003-04-25 | 2004-04-23 | Procede de preparation de complexes moleculaires |
AT04742568T ATE555811T1 (de) | 2003-04-25 | 2004-04-23 | Verfahren zur herstellung von molekularkomplexen |
BRPI0409741A BRPI0409741B1 (pt) | 2003-04-25 | 2004-04-23 | método para a preparação de complexos moleculares |
US10/554,058 US8741346B2 (en) | 2003-04-25 | 2004-04-23 | Method for the preparation of molecular complexes |
CA2523342A CA2523342C (fr) | 2003-04-25 | 2004-04-23 | Procede de preparation de complexes moleculaires |
DK04742568.1T DK1638609T3 (da) | 2003-04-25 | 2004-04-23 | Fremgangsmåde til fremstilling af molekylekomplekser |
JP2006505810A JP5037936B2 (ja) | 2003-04-25 | 2004-04-23 | 分子複合体の調製のための方法 |
PL04742568T PL1638609T3 (pl) | 2003-04-25 | 2004-04-23 | Sposób wytwarzania kompleksów cząsteczkowych |
NZ543209A NZ543209A (en) | 2003-04-25 | 2004-04-23 | Method for the preparation of molecular complexes |
MXPA05011505A MXPA05011505A (es) | 2003-04-25 | 2004-04-23 | Metodo de preparacion de complejos moleculares. |
AU2004233621A AU2004233621B2 (en) | 2003-04-25 | 2004-04-23 | Method for the preparation of molecular complexes |
ES04742568T ES2386437T3 (es) | 2003-04-25 | 2004-04-23 | Procedimiento de preparación de complejos moleculares |
SI200431896T SI1638609T1 (sl) | 2003-04-25 | 2004-04-23 | Postopek za pripravo molekulskih kompleksov |
CN200480014408A CN100594941C (zh) | 2003-04-25 | 2004-04-23 | 分子络合物的制备方法 |
IL171520A IL171520A (en) | 2003-04-25 | 2005-10-20 | Method for the preparation of molecular complexes |
KR1020057020310A KR101208256B1 (ko) | 2003-04-25 | 2005-10-25 | 분자 복합체의 제조 방법 |
NO20055467A NO335160B1 (no) | 2003-04-25 | 2005-11-18 | Fremgangsmåte til fremstilling av molekylære komplekser |
HK06104203.9A HK1082430A1 (en) | 2003-04-25 | 2006-04-06 | Method for the preparation of molecular complexes |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR0305140A FR2854079B1 (fr) | 2003-04-25 | 2003-04-25 | Procede de preparation de complexes moleculaires |
FR03/05140 | 2003-04-25 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2004096284A1 true WO2004096284A1 (fr) | 2004-11-11 |
Family
ID=33104420
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/FR2004/000995 WO2004096284A1 (fr) | 2003-04-25 | 2004-04-23 | Procede de preparation de complexes moleculaires |
Country Status (23)
Country | Link |
---|---|
US (1) | US8741346B2 (fr) |
EP (2) | EP1638609B1 (fr) |
JP (1) | JP5037936B2 (fr) |
KR (1) | KR101208256B1 (fr) |
CN (1) | CN100594941C (fr) |
AT (1) | ATE555811T1 (fr) |
AU (1) | AU2004233621B2 (fr) |
BR (1) | BRPI0409741B1 (fr) |
CA (1) | CA2523342C (fr) |
DK (1) | DK1638609T3 (fr) |
ES (1) | ES2386437T3 (fr) |
FR (1) | FR2854079B1 (fr) |
HK (1) | HK1082430A1 (fr) |
IL (1) | IL171520A (fr) |
MX (1) | MXPA05011505A (fr) |
NO (1) | NO335160B1 (fr) |
NZ (1) | NZ543209A (fr) |
PL (1) | PL1638609T3 (fr) |
PT (1) | PT1638609E (fr) |
RU (2) | RU2353392C2 (fr) |
SI (1) | SI1638609T1 (fr) |
WO (1) | WO2004096284A1 (fr) |
ZA (1) | ZA200508469B (fr) |
Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2005097201A2 (fr) * | 2004-04-01 | 2005-10-20 | Pierre Fabre Medicament | Complexes d’inclusions comprenant du piroxicam, une cyclodextrine et l’arginine |
FR2876911A1 (fr) * | 2004-10-21 | 2006-04-28 | Pierre Fabre Medicament Sa | Complexe comprenant du piroxicam, une cyclodextrine et de l'arginine |
US7749982B2 (en) | 2004-10-21 | 2010-07-06 | Pierre Fabre Medicament | Complex containing mequitazine, a cyclodextrin and an interaction agent |
WO2010116097A1 (fr) * | 2009-04-09 | 2010-10-14 | Pierre Fabre Medicament | Procede de preparation de complexes moleculaires entre un agent retinoïde et des cyclodextrines |
WO2010116099A1 (fr) * | 2009-04-09 | 2010-10-14 | Galderma Research & Development | Procede de preparation de complexes moleculaires entre adapalene et des cyclodextrines |
US8614199B2 (en) | 2009-04-09 | 2013-12-24 | Galderma Research & Development | Compositions comprising at least one complex composed of a derivative of naphthoic acid and of at least one cyclodextrin and uses thereof |
US10532102B2 (en) | 2016-08-19 | 2020-01-14 | Foresee Pharmaceuticals Co., Ltd. | Pharmaceutical composition and methods of uses |
Families Citing this family (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2876914A1 (fr) * | 2004-10-21 | 2006-04-28 | Pierre Fabre Medicament Sa | Complexe comprenant un antibiotique, une cyclodextrine et un agent d'interaction |
JP5622187B2 (ja) * | 2009-09-08 | 2014-11-12 | 群泰生物科技股▲ふん▼有限公司 | 水溶性ミノキシジル組成物 |
US10328152B2 (en) | 2011-06-16 | 2019-06-25 | Nayan Patel | Method for stabilization and delivery of therapeutic molecules |
GB201609222D0 (en) | 2016-05-25 | 2016-07-06 | F2G Ltd | Pharmaceutical formulation |
US11819503B2 (en) | 2019-04-23 | 2023-11-21 | F2G Ltd | Method of treating coccidioides infection |
JP2022554420A (ja) * | 2019-10-21 | 2022-12-28 | エソレイト・リミテッド | 超微粒化合物を含む組成物およびその製造 |
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WO2002032462A1 (fr) * | 2000-10-19 | 2002-04-25 | Separex | Procede de fabrication de tres fines particules constituees d'un principe insere dans une molecule hôte |
WO2002083632A1 (fr) * | 2001-04-10 | 2002-10-24 | Pierre Fabre Medicament | Complexes d'anilides et de cyclodextrines, leur preparation et leur application en tant que medicament en particulier pour le traitement des dislipidemies |
WO2003030867A2 (fr) * | 2001-10-12 | 2003-04-17 | Pierre Fabre Medicament | Procede de preparation d'un compose d'interaction d'un derive anilide avec un support poreux par fluide supercritique |
FR2830760A1 (fr) * | 2001-10-12 | 2003-04-18 | Pf Medicament | Procede de preparation d'un compose d'interaction de substances actives avec un support poreux par fluide supercritique |
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JPH0677511B2 (ja) | 1986-12-05 | 1994-10-05 | 金印わさび株式会社 | 香辛成分の包接化合物の製造方法 |
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DE3744329A1 (de) * | 1987-12-28 | 1989-07-06 | Schwarz Pharma Gmbh | Verfahren zur herstellung einer mindestens einen wirkstoff und einen traeger umfassenden zubereitung |
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2003
- 2003-04-25 FR FR0305140A patent/FR2854079B1/fr not_active Expired - Fee Related
-
2004
- 2004-04-23 EP EP04742568A patent/EP1638609B1/fr not_active Expired - Lifetime
- 2004-04-23 EP EP10179575A patent/EP2289561A1/fr not_active Withdrawn
- 2004-04-23 PT PT04742568T patent/PT1638609E/pt unknown
- 2004-04-23 DK DK04742568.1T patent/DK1638609T3/da active
- 2004-04-23 PL PL04742568T patent/PL1638609T3/pl unknown
- 2004-04-23 CA CA2523342A patent/CA2523342C/fr not_active Expired - Fee Related
- 2004-04-23 CN CN200480014408A patent/CN100594941C/zh not_active Expired - Fee Related
- 2004-04-23 US US10/554,058 patent/US8741346B2/en not_active Expired - Fee Related
- 2004-04-23 JP JP2006505810A patent/JP5037936B2/ja not_active Expired - Fee Related
- 2004-04-23 NZ NZ543209A patent/NZ543209A/en not_active IP Right Cessation
- 2004-04-23 RU RU2005136664/15A patent/RU2353392C2/ru not_active IP Right Cessation
- 2004-04-23 AT AT04742568T patent/ATE555811T1/de active
- 2004-04-23 MX MXPA05011505A patent/MXPA05011505A/es active IP Right Grant
- 2004-04-23 WO PCT/FR2004/000995 patent/WO2004096284A1/fr active Search and Examination
- 2004-04-23 AU AU2004233621A patent/AU2004233621B2/en not_active Ceased
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WO2005097201A3 (fr) * | 2004-04-01 | 2006-08-17 | Pf Medicament | Complexes d’inclusions comprenant du piroxicam, une cyclodextrine et l’arginine |
US9243076B2 (en) | 2004-04-01 | 2016-01-26 | Pierre Fabre Medicament | Inclusion complexes containing piroxicam, a cyclodextrin and arginine |
US8461133B2 (en) | 2004-04-01 | 2013-06-11 | Pierre Fabre Medicament | Inclusion complexes containing an active substance, a cyclodextrin and an agent for interaction |
FR2876911A1 (fr) * | 2004-10-21 | 2006-04-28 | Pierre Fabre Medicament Sa | Complexe comprenant du piroxicam, une cyclodextrine et de l'arginine |
US7749982B2 (en) | 2004-10-21 | 2010-07-06 | Pierre Fabre Medicament | Complex containing mequitazine, a cyclodextrin and an interaction agent |
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FR2944280A1 (fr) * | 2009-04-09 | 2010-10-15 | Galderma Res & Dev | Procede de preparation de complexes moleculaires entre adapalene et des cyclodextrines |
WO2010116099A1 (fr) * | 2009-04-09 | 2010-10-14 | Galderma Research & Development | Procede de preparation de complexes moleculaires entre adapalene et des cyclodextrines |
US8614199B2 (en) | 2009-04-09 | 2013-12-24 | Galderma Research & Development | Compositions comprising at least one complex composed of a derivative of naphthoic acid and of at least one cyclodextrin and uses thereof |
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WO2010116097A1 (fr) * | 2009-04-09 | 2010-10-14 | Pierre Fabre Medicament | Procede de preparation de complexes moleculaires entre un agent retinoïde et des cyclodextrines |
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