WO1996037232A1 - Estabilizacion de sistemas coloidales mediante formacion de complejos ionicos lipido-polisacarido - Google Patents
Estabilizacion de sistemas coloidales mediante formacion de complejos ionicos lipido-polisacarido Download PDFInfo
- Publication number
- WO1996037232A1 WO1996037232A1 PCT/ES1996/000116 ES9600116W WO9637232A1 WO 1996037232 A1 WO1996037232 A1 WO 1996037232A1 ES 9600116 W ES9600116 W ES 9600116W WO 9637232 A1 WO9637232 A1 WO 9637232A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- suspension
- process according
- aqueous phase
- colloidal
- nanocapsules
- Prior art date
Links
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
- A61K9/48—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
- A61K9/51—Nanocapsules; Nanoparticles
- A61K9/5107—Excipients; Inactive ingredients
- A61K9/513—Organic macromolecular compounds; Dendrimers
- A61K9/5146—Organic macromolecular compounds; Dendrimers obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyethylene glycol, polyamines, polyanhydrides
- A61K9/5153—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
- A61K9/10—Dispersions; Emulsions
-
- 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
- A61K9/10—Dispersions; Emulsions
- A61K9/107—Emulsions ; Emulsion preconcentrates; Micelles
- A61K9/1075—Microemulsions or submicron emulsions; Preconcentrates or solids thereof; Micelles, e.g. made of phospholipids or block copolymers
-
- 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
- A61K9/51—Nanocapsules; Nanoparticles
- A61K9/5107—Excipients; Inactive ingredients
- A61K9/513—Organic macromolecular compounds; Dendrimers
- A61K9/5161—Polysaccharides, e.g. alginate, chitosan, cellulose derivatives; 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
- A61K9/48—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
- A61K9/51—Nanocapsules; Nanoparticles
- A61K9/5192—Processes
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S977/00—Nanotechnology
- Y10S977/70—Nanostructure
- Y10S977/788—Of specified organic or carbon-based composition
- Y10S977/797—Lipid particle
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S977/00—Nanotechnology
- Y10S977/70—Nanostructure
- Y10S977/788—Of specified organic or carbon-based composition
- Y10S977/797—Lipid particle
- Y10S977/798—Lipid particle having internalized material
- Y10S977/799—Containing biological material
- Y10S977/801—Drug
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S977/00—Nanotechnology
- Y10S977/902—Specified use of nanostructure
- Y10S977/904—Specified use of nanostructure for medical, immunological, body treatment, or diagnosis
- Y10S977/906—Drug delivery
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S977/00—Nanotechnology
- Y10S977/902—Specified use of nanostructure
- Y10S977/904—Specified use of nanostructure for medical, immunological, body treatment, or diagnosis
- Y10S977/906—Drug delivery
- Y10S977/907—Liposome
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S977/00—Nanotechnology
- Y10S977/902—Specified use of nanostructure
- Y10S977/904—Specified use of nanostructure for medical, immunological, body treatment, or diagnosis
- Y10S977/915—Therapeutic or pharmaceutical composition
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S977/00—Nanotechnology
- Y10S977/902—Specified use of nanostructure
- Y10S977/904—Specified use of nanostructure for medical, immunological, body treatment, or diagnosis
- Y10S977/926—Topical chemical, e.g. cosmetic or sunscreen
Definitions
- Lecithin is a naturally occurring substance whose main component is phosphatidylcholine (a neutral phospholipid) and whose secondary components are phosphatidylethanolamine, phosphatidylserine and phosphatidic acid (negatively charged phospholipids).
- phosphatidylcholine a neutral phospholipid
- secondary components are phosphatidylethanolamine, phosphatidylserine and phosphatidic acid (negatively charged phospholipids).
- lecithin available that differ in origin (soy, egg, organic tissues) and phosphatidylcholine content.
- Chitosan is a polymer of natural origin that is obtained through a process of deacetylation of chitin (a molecule that is extracted from the shell of crustaceans); It has a cationic aminopolysaccharide structure.
- chitosan a polymer of natural origin that is obtained through a process of deacetylation of chitin (a molecule that is extracted from the shell of crustaceans); It has a cationic aminopolysaccharide structure.
- chitosan are available on the market, including chitosans of different molecular weights and different degrees of deacetylation; it can also be presented in the form of chitosan base or salt (chitosan hydrochloride or glutamate).
- the proposed colloidal systems have lecithin and chitosan as distinctive components, giving them a positive surface charge and improving their stability.
- the rest of the components will depend on the type of system and will be an oil in the case of nanoemulsions, an oil and a hydrophobic polymer in the case of nanocapsules, and a hydrophobic polymer in the case of nanoparticles.
- These systems can include drugs, proteins and other biological components of possible interest in medicine or cosmetics. Consequently, its application as new forms of administration in humans extends to the field of medicine and cosmetology.
- Lecithins have phosphatidylcholine as their main component and various negatively charged phospholipids as secondary components, as a consequence, any colloidal system whose composition includes lecithins has a negative surface charge.
- emulsions with a positive net charge have been designed and recently patented. These emulsions are based on the use of cationic lipophilic surfactants, which is why they are introduced into the internal phase of the emulsion (S. Benita, Oil-in water emulsions of positively charged particles WO 93/18852)
- the present invention focuses on the use of a hydrophilic polysaccharide of cationic character, more specifically chitosan, which dissolves in the dispersing aqueous phase and an anionic lipid, more specifically lecithin , which dissolves in the disperse phase.
- a hydrophilic polysaccharide of cationic character more specifically chitosan
- an anionic lipid more specifically lecithin
- the systems included in this invention present numerous advantages over others previously described, the distinctive characteristic being the formation of an ionic complex at the interface of the system.
- Said advantages include: (1) they allow the obtaining of emulsions and suspensions of nanocapsules and nanoparticles that are stable during their storage at room temperature for several months, (2) the suspensions of nanocapsules described here are lyophilizable, achieving their perfect reconstitution after rehydration of the lyophilized product, (3) the suspensions of nanocapsules described here, coated with chitosan, are more stable in the presence of biological cations than conventional nano-casules not coated with chitosan (4), the particles or globules in suspension have a positive electrical charge, which facilitates their interaction with biological surfaces (eg epithelia) with negative surface charge.
- the present invention describes new systems of interest in therapeutics and cosmetics. These systems can be presented in a liquid form of variable viscosity, semi-solid (cream type) or solid, that is to say as a redispersible lyophilized powder.
- the internal phase or dispersed phase of the system can be formed by an oil or a polymer or both simultaneously and as a characteristic component it has an ammonium phospholipid. Said phase can contain varying proportions of an active ingredient.
- the oils can be of a vegetable type eg. peanuts, cotton, olive, castor, etc., or of semi-synthetic origin such as polyoxyethylene derivatives of natural oils (Migliol®, Labrafil®, Labrafac® ...) and endowed with H.L.B. (hydrophilic-lipophilic balance) highly variable.
- the polymer can be any hydrophobic polymer for pharmaceutical or cosmetic application. This hydrophobic polymer can be found in variable proportions with respect to oil from 0% to 100%.
- the dispersed phase When the polymer proportion is 0%, the dispersed phase will be made up of oil globules, thus constituting a submicroscopic emulsion (nanoemulsion) while when said proportion is 100%, the dispersed phase will be made up of solid particles (nanoparticles or nanospheres) .
- the oily phase will be dispersed or enveloped by the polymer constituting small capsules or reservoirs, the whole system forming a suspension of nanocapsules.
- the external phase is of the aqueous type and its specific component is chitosan. If it is desired to lyophilize the colloidal suspension, cryoprotective agents such as dextran and glucose must be incorporated into the external aqueous phase. Finally, any hydrophilic excipient capable of supplying a certain density or viscosity to the preparation can be included in said phase, as well as bacteriostatic agents to prevent the contamination of the preparation, odorous substances as well as active ingredients of a hydrophilic nature.
- composition of these systems can be formulated such that they contain one or more active ingredients that can be lipophilic or hydrophilic in character. If the active ingredient is lipophilic, it will be dissolved in the oil or in the polymer. Active ingredient is understood to be that for which the formulation is designed, that is, that which has to perform a certain function after administration to a living organism. The function can be to combat, alleviate or prevent a disease (eg vaccines, vitamins, ..,), improve the physical and aesthetic appearance (eg hydration of the skin, prevention or facilitation of hair loss) and the like. .
- a disease eg vaccines, vitamins, ..,
- improve the physical and aesthetic appearance eg hydration of the skin, prevention or facilitation of hair loss
- Cyclosporin A an in unomodulatory peptide and indomethacin (anti-inflammatory) and metipranolol (beta-blocker), have been examples of drugs tested in this invention.
- Tables 1 and 2 show the particle size of nanocapsules, nanoemulsions (table 1) and nanoparticles (table 2), containing Miglio ⁇ * 840 oil and made with different proportions of polyepsiloncaprolactone, soy lecithin and dextran.
- one of the advantages of the new systems included in the present invention lies in their positive charge, an aspect that gives these systems greater stability in contact with aqueous media containing cations, as well as a facilitated interaction with epithelial surfaces.
- ammonia As shown in Table 3, the Z potential values obtained for these formulations are between +30 and +60 mV, the value of said potential being in relation to the molecular weight of the chitosan.
- the process described in this invention makes it possible to prepare a new pharmaceutical, dermatological or cosmetic composition that can be used for its administration by different routes including topical, oral, nasal, pulmonary, vaginal and subcutaneous.
- the specific ingredients of this new composition provide the system with a positive surface charge and improved stability not only during storage but also after lyophilization and subsequent rehydration.
- PECL polyepsiloncaprolactone
- Table 3 Z potential of polyepsiloncaprolactone (PECL) nanocapsules and nanoemulsions containing Migliol ® 840 and prepared with a chitosan concentration (Seacure ® 320) of 0.2% (w / v).
- PECL polyepsiloncaprolactone
- Final concentration of PECL and lecithin in the suspension 1% and 0.5% (p / v) respectively.
- Example 2 A formulation similar to that described in Example 1 was prepared but containing a lower quantity of lecithin and a higher quantity of oil. The procedure was identical to that described above.
- Example 3 The particle size and Z potential results were 433 nm and + 32 mV before lyophilization and 582 nm and + 43 mV after the lyophilization process.
- Example 3 The particle size and Z potential results were 433 nm and + 32 mV before lyophilization and 582 nm and + 43 mV after the lyophilization process.
- the particle size and Z potential results were 463 nm and + 42 mV.
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Nanotechnology (AREA)
- Optics & Photonics (AREA)
- Physics & Mathematics (AREA)
- Biomedical Technology (AREA)
- Dispersion Chemistry (AREA)
- Biophysics (AREA)
- Molecular Biology (AREA)
- Medicinal Preparation (AREA)
- Cosmetics (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Abstract
Description
Claims
Priority Applications (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US08/776,507 US5843509A (en) | 1995-05-26 | 1996-05-24 | Stabilization of colloidal systems through the formation of lipid-polyssacharide complexes |
DE69634927T DE69634927T2 (de) | 1995-05-26 | 1996-05-24 | Stabilisation von kolloidalen systemen durch die bildung von ionischen lipid-polysaccharid-komplexen |
EP96914215A EP0771566B1 (en) | 1995-05-26 | 1996-05-24 | Stabilization of colloidal systems by the formation of ionic lipid-polysaccharide complexes |
AT96914215T ATE330636T1 (de) | 1995-05-26 | 1996-05-24 | Stabilisation von kolloidalen systemen durch die bildung von ionischen lipid-polysaccharid- komplexen |
CA002195881A CA2195881C (en) | 1995-05-26 | 1996-05-24 | Stabilization of colloidal systems through the formation of lipid-polysaccharide complexes |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
ESP9501035 | 1995-05-26 | ||
ES09501035A ES2093562B1 (es) | 1995-05-26 | 1995-05-26 | Estabilizacion de sistemas coloidales mediante formacion de complejos ionicos lipido-polisacarido. |
Publications (1)
Publication Number | Publication Date |
---|---|
WO1996037232A1 true WO1996037232A1 (es) | 1996-11-28 |
Family
ID=8290513
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/ES1996/000116 WO1996037232A1 (es) | 1995-05-26 | 1996-05-24 | Estabilizacion de sistemas coloidales mediante formacion de complejos ionicos lipido-polisacarido |
Country Status (9)
Country | Link |
---|---|
US (1) | US5843509A (es) |
EP (1) | EP0771566B1 (es) |
AT (1) | ATE330636T1 (es) |
CA (1) | CA2195881C (es) |
DE (1) | DE69634927T2 (es) |
DK (1) | DK0771566T3 (es) |
ES (1) | ES2093562B1 (es) |
PT (1) | PT771566E (es) |
WO (1) | WO1996037232A1 (es) |
Cited By (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1998032422A1 (en) * | 1997-01-24 | 1998-07-30 | Femmepharma | Pharmaceutical preparations and methods for their regional administration |
US6416778B1 (en) | 1997-01-24 | 2002-07-09 | Femmepharma | Pharmaceutical preparations and methods for their regional administration |
US7812010B2 (en) | 2003-01-02 | 2010-10-12 | Femmepharma, Inc. | Pharmaceutical preparations for treatments of diseases and disorders of the breast |
EP2266546A1 (en) | 2009-06-08 | 2010-12-29 | Advancell Advanced in Vitro Cell Technologies,S.A. | Process for the preparation of colloidal systems for the delivery of active compounds |
US8226972B2 (en) | 2001-12-20 | 2012-07-24 | Femmepharma Holding Company, Inc. | Vaginal delivery of drugs |
US8936786B2 (en) | 2008-01-08 | 2015-01-20 | Oshadi Drug Administration Ltd. | Methods and compositions for oral administration of protein and peptide therapeutic agents |
US9060932B2 (en) | 2009-07-09 | 2015-06-23 | Oshadi Drug Administration Ltd. | Matrix carrier compositions, methods and uses |
US9173836B2 (en) | 2003-01-02 | 2015-11-03 | FemmeParma Holding Company, Inc. | Pharmaceutical preparations for treatments of diseases and disorders of the breast |
WO2017014655A1 (en) | 2015-07-17 | 2017-01-26 | Uniwersytet Jagiellonski | Nanocapsule for delivery of lipophilic compound and process of preparation thereof |
Families Citing this family (70)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5766629A (en) | 1995-08-25 | 1998-06-16 | Sangstat Medical Corporation | Oral cyclosporin formulations |
FR2760641B1 (fr) * | 1997-03-13 | 2000-08-18 | Oreal | Emulsion huile-dans-eau stable, son procede de fabrication et son utilisation dans les domaines cosmetique et dermatologique |
DE19733625A1 (de) * | 1997-07-28 | 1999-02-04 | Lancaster Group Gmbh | Dekorative kosmetische O/W-Emulsion |
KR19990058599A (ko) * | 1997-12-30 | 1999-07-15 | 손경식 | 이중 캡슐을 함유하는 화장료 조성물 |
DE19826503A1 (de) * | 1998-06-13 | 1999-12-16 | Beiersdorf Ag | Kosmetische und dermatologische Zubereitungen mit einem Gehalt an Chitosan und Phospholipiden |
AU1275401A (en) * | 1999-10-29 | 2001-05-14 | Hunza Di Maria Carmela Marazzita S.A.S. | Fibrous-liponutritional complexes and compositions containing them |
FR2801811B1 (fr) * | 1999-12-06 | 2002-05-03 | Gerard Habar | Procede de fabrication de microcapsules portant des charges cationiques |
AU2001246459A1 (en) * | 2000-02-23 | 2001-09-03 | Henkel Kommanditgesellschaft Auf Aktien | Microcapsules and/or nanocapsules |
US6761901B1 (en) | 2000-05-02 | 2004-07-13 | Enzrel Inc. | Liposome drug delivery |
US6455073B1 (en) | 2000-07-10 | 2002-09-24 | Enzrel, Inc. | Covalent microparticle-drug conjugates for biological targeting |
US6689760B1 (en) | 2000-07-10 | 2004-02-10 | Enzrel Inc. | Anti-mycobacterial compositions |
AU2001296480A1 (en) | 2000-10-02 | 2002-04-15 | Kimberly-Clark Worldwide, Inc. | Recording medium with nanoparticles and methods of making the same |
US20030133972A1 (en) * | 2000-10-11 | 2003-07-17 | Targesome, Inc. | Targeted multivalent macromolecules |
US20030129223A1 (en) * | 2000-10-11 | 2003-07-10 | Targesome, Inc. | Targeted multivalent macromolecules |
WO2002072011A2 (en) * | 2001-03-08 | 2002-09-19 | Targesome, Inc. | Stabilized therapeutic and imaging agents |
US6673263B2 (en) | 2001-07-26 | 2004-01-06 | Ppg Industries Ohio, Inc. | Compositions incorporating chitosan for paint detackification |
US20040000329A1 (en) * | 2001-07-26 | 2004-01-01 | Albu Michael L. | Compositions and methods for paint overspray removal processes |
EP1443905A4 (en) * | 2001-10-03 | 2010-06-23 | Univ Johns Hopkins | COMPOSITIONS FOR ORAL GENE THERAPY AND METHOD OF USE THEREOF |
WO2003059288A2 (en) * | 2002-01-09 | 2003-07-24 | Enzrel, Inc. | Liposome drug delivery of polycyclic, aromatic, antioxidant or anti-inflammatory compounds |
US20030176310A1 (en) * | 2002-03-15 | 2003-09-18 | Huang Robert Y.M. | Chitosan/anionic surfactant complex membrane |
ES2197836B1 (es) * | 2002-06-28 | 2005-05-01 | Consejo Sup. Investig. Cientificas | Procedimiento para la preparacion de nano-emulsiones de tipo agua en aceite (w/o) por metodos de emulsificacion de condensacion. |
US6780896B2 (en) * | 2002-12-20 | 2004-08-24 | Kimberly-Clark Worldwide, Inc. | Stabilized photoinitiators and applications thereof |
US8409618B2 (en) | 2002-12-20 | 2013-04-02 | Kimberly-Clark Worldwide, Inc. | Odor-reducing quinone compounds |
US7666410B2 (en) | 2002-12-20 | 2010-02-23 | Kimberly-Clark Worldwide, Inc. | Delivery system for functional compounds |
WO2005018773A1 (en) * | 2003-08-20 | 2005-03-03 | Merck Patent Gmbh | Methods for extraction and concentration of hydrophilic compounds from hydrophobic liquid matrices |
US7794737B2 (en) | 2003-10-16 | 2010-09-14 | Kimberly-Clark Worldwide, Inc. | Odor absorbing extrudates |
US7678367B2 (en) | 2003-10-16 | 2010-03-16 | Kimberly-Clark Worldwide, Inc. | Method for reducing odor using metal-modified particles |
US7879350B2 (en) | 2003-10-16 | 2011-02-01 | Kimberly-Clark Worldwide, Inc. | Method for reducing odor using colloidal nanoparticles |
US7837663B2 (en) | 2003-10-16 | 2010-11-23 | Kimberly-Clark Worldwide, Inc. | Odor controlling article including a visual indicating device for monitoring odor absorption |
US7488520B2 (en) | 2003-10-16 | 2009-02-10 | Kimberly-Clark Worldwide, Inc. | High surface area material blends for odor reduction, articles utilizing such blends and methods of using same |
US7413550B2 (en) | 2003-10-16 | 2008-08-19 | Kimberly-Clark Worldwide, Inc. | Visual indicating device for bad breath |
US7754197B2 (en) | 2003-10-16 | 2010-07-13 | Kimberly-Clark Worldwide, Inc. | Method for reducing odor using coordinated polydentate compounds |
KR20060097020A (ko) * | 2003-10-31 | 2006-09-13 | 테바 파마슈티컬 인더스트리즈 리미티드 | 약물 전달용 나노입자 |
KR100638041B1 (ko) * | 2003-12-24 | 2006-10-23 | 주식회사 삼양사 | 수용성 약물의 경구투여용 나노입자 조성물 및 그의제조방법 |
US7846201B2 (en) * | 2004-02-20 | 2010-12-07 | The Children's Hospital Of Philadelphia | Magnetically-driven biodegradable gene delivery nanoparticles formulated with surface-attached polycationic complex |
US8562505B2 (en) * | 2004-02-20 | 2013-10-22 | The Children's Hospital Of Philadelphia | Uniform field magnetization and targeting of therapeutic formulations |
US9028829B2 (en) * | 2004-02-20 | 2015-05-12 | The Children's Hospital Of Philadelphia | Uniform field magnetization and targeting of therapeutic formulations |
US20060003956A1 (en) * | 2004-03-03 | 2006-01-05 | Casadome David O | Materials and methods for the derepression of the E-cadherin promoter |
WO2005087221A1 (en) * | 2004-03-15 | 2005-09-22 | Christine Allen | Biodegradable biocompatible implant and method of manufacturing same |
CN1311867C (zh) * | 2004-09-27 | 2007-04-25 | 侯新朴 | 一种用于鼻腔给药的神经生长因子制剂 |
ES2259914B1 (es) * | 2005-03-14 | 2007-06-16 | Advanced In Vitro Cell Technologies, S.L. | Nanoparticulas de quitosano y polietilenglicol como sistema de administracion de moleculas biologicamente activas. |
ATE515260T1 (de) * | 2006-03-13 | 2011-07-15 | Advanced In Vitro Cell Technologies S L | Stabile nanokapselsysteme für die verabreichung von wirkstoffen |
US7977103B2 (en) | 2006-04-20 | 2011-07-12 | Kimberly-Clark Worldwide, Inc. | Method for detecting the onset of ovulation |
US20080153789A1 (en) * | 2006-12-26 | 2008-06-26 | Femmepharma Holding Company, Inc. | Topical administration of danazol |
WO2008135828A2 (en) | 2007-05-03 | 2008-11-13 | Pfizer Products Inc. | Nanoparticles comprising a drug, ethylcellulose, and a bile salt |
WO2008135855A2 (en) | 2007-05-03 | 2008-11-13 | Pfizer Products Inc. | Nanoparticles comprising a cholesteryl ester transfer protein inhibitor and a nonionizable polymer |
EP2162120B1 (en) | 2007-06-04 | 2016-05-04 | Bend Research, Inc | Nanoparticles comprising a non-ionizable cellulosic polymer and an amphiphilic non-ionizable block copolymer |
US9545384B2 (en) | 2007-06-04 | 2017-01-17 | Bend Research, Inc. | Nanoparticles comprising drug, a non-ionizable cellulosic polymer and tocopheryl polyethylene glocol succinate |
EP2231169B1 (en) | 2007-12-06 | 2016-05-04 | Bend Research, Inc. | Pharmaceutical compositions comprising nanoparticles and a resuspending material |
US9233078B2 (en) | 2007-12-06 | 2016-01-12 | Bend Research, Inc. | Nanoparticles comprising a non-ionizable polymer and an Amine-functionalized methacrylate copolymer |
US8778400B2 (en) * | 2008-04-21 | 2014-07-15 | University Of South Australia | Nanoparticle-stabilized capsule formulation for treatment of inflammation |
US9207242B2 (en) | 2008-10-09 | 2015-12-08 | The University Of Hong Kong | Cadherin-17 as diagnostic marker and therapeutic target for liver cancer |
US20110003000A1 (en) * | 2009-07-06 | 2011-01-06 | Femmepharma Holding Company, Inc. | Transvaginal Delivery of Drugs |
EP2361509A1 (en) | 2010-02-15 | 2011-08-31 | Nestec S.A. | Liquid-filled protein-phosphatidic acid capsule dispersions |
EP2364600A1 (en) | 2010-02-18 | 2011-09-14 | Nestec S.A. | Liquid-filled chitosan-anionic liposoluble capsule dispsersions |
BRPI1002601E2 (pt) * | 2010-06-01 | 2020-06-30 | Embrapa Pesquisa Agropecuaria | composição nanoestruturada de uso veterinário para administração de fármacos |
US9326980B2 (en) * | 2013-07-21 | 2016-05-03 | Kimia Zist Parsian (Kzp) | Method and system for synthesizing nanocarrier based long acting drug delivery system for buprenorphine |
US9351932B2 (en) * | 2014-07-21 | 2016-05-31 | Kimia Zist Parsian (Kzp) | Method and system for synthesizing nanocarrier based long acting drug delivery system for methadone |
GB201522186D0 (en) | 2015-12-16 | 2016-01-27 | Singapore Health Services Pte Ltd And Nat University Of Singapore The | Treatment of fibrosis |
US20200129575A1 (en) | 2017-02-09 | 2020-04-30 | Universidade De Santiago De Compostela | Purified pollen particles and use thereof for administering nanosystems |
US11883401B2 (en) | 2019-01-08 | 2024-01-30 | Duke University | Compositions for the treatment of pathogenic- and/or chemical-induced lung injury and for the treatment of cancer and methods of using same |
CN113677706A (zh) | 2019-01-21 | 2021-11-19 | 新加坡保健服务私人有限公司 | 肝毒性的治疗 |
GB201902419D0 (en) | 2019-02-22 | 2019-04-10 | Singapore Health Serv Pte Ltd | Treatment of kidney injury |
CA3146344A1 (en) | 2019-05-03 | 2020-11-12 | Singapore Health Services Pte. Ltd. | Treatment and prevention of metabolic diseases |
GB201906291D0 (en) | 2019-05-03 | 2019-06-19 | Singapore Health Serv Pte Ltd | Treatment and prevention of metabolic diseases |
GB202009292D0 (en) | 2020-06-18 | 2020-08-05 | Singapore Health Serv Pte Ltd | Treatment and prevention of disease caused by type IV collagen dysfunction |
GB202017244D0 (en) | 2020-10-30 | 2020-12-16 | Nat Univ Singapore | Methods to extend health-span and treat age-related diseases |
EP4376948A1 (en) | 2021-07-26 | 2024-06-05 | Boehringer Ingelheim International GmbH | Treatment and prevention of alcoholic liver disease |
WO2023111196A1 (en) | 2021-12-16 | 2023-06-22 | Singapore Health Services Pte. Ltd. | Treatment and prevention of glomerular disease |
GB202212077D0 (en) | 2022-08-18 | 2022-10-05 | Tribune Therapeutics Ab | Agents that inhibit ccn ligand-induced signalling for treating disease |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0486959A1 (en) * | 1990-11-22 | 1992-05-27 | Vectorpharma International S.P.A. | Pharmaceutical composition of microparticles with controlled release and process of preparing it |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
IL101241A (en) * | 1992-03-16 | 1997-11-20 | Yissum Res Dev Co | Pharmaceutical or cosmetic composition comprising stabilized oil-in-water type emulsion as carrier |
-
1995
- 1995-05-26 ES ES09501035A patent/ES2093562B1/es not_active Expired - Fee Related
-
1996
- 1996-05-24 WO PCT/ES1996/000116 patent/WO1996037232A1/es active IP Right Grant
- 1996-05-24 PT PT96914215T patent/PT771566E/pt unknown
- 1996-05-24 DE DE69634927T patent/DE69634927T2/de not_active Expired - Lifetime
- 1996-05-24 DK DK96914215T patent/DK0771566T3/da active
- 1996-05-24 US US08/776,507 patent/US5843509A/en not_active Expired - Lifetime
- 1996-05-24 EP EP96914215A patent/EP0771566B1/en not_active Expired - Lifetime
- 1996-05-24 CA CA002195881A patent/CA2195881C/en not_active Expired - Fee Related
- 1996-05-24 AT AT96914215T patent/ATE330636T1/de not_active IP Right Cessation
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0486959A1 (en) * | 1990-11-22 | 1992-05-27 | Vectorpharma International S.P.A. | Pharmaceutical composition of microparticles with controlled release and process of preparing it |
Non-Patent Citations (1)
Title |
---|
FALDT, P.; ET AL.: "Stabilization by chitosan of soybean oil emulsions coated with phospholipid and glycocholic acid", COLLOIDS AND SURFACES A: PHYSICOCHEMICAL AND ENGINEERING ASPECTS, vol. 71, 1993, pages 187 - 195, XP002010333 * |
Cited By (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1998032422A1 (en) * | 1997-01-24 | 1998-07-30 | Femmepharma | Pharmaceutical preparations and methods for their regional administration |
US5993856A (en) * | 1997-01-24 | 1999-11-30 | Femmepharma | Pharmaceutical preparations and methods for their administration |
US6416778B1 (en) | 1997-01-24 | 2002-07-09 | Femmepharma | Pharmaceutical preparations and methods for their regional administration |
US6652874B2 (en) | 1997-01-24 | 2003-11-25 | Femmepharma | Pharmaceutical preparations and methods for their regional administration |
US8226972B2 (en) | 2001-12-20 | 2012-07-24 | Femmepharma Holding Company, Inc. | Vaginal delivery of drugs |
US7812010B2 (en) | 2003-01-02 | 2010-10-12 | Femmepharma, Inc. | Pharmaceutical preparations for treatments of diseases and disorders of the breast |
US9173836B2 (en) | 2003-01-02 | 2015-11-03 | FemmeParma Holding Company, Inc. | Pharmaceutical preparations for treatments of diseases and disorders of the breast |
US8936786B2 (en) | 2008-01-08 | 2015-01-20 | Oshadi Drug Administration Ltd. | Methods and compositions for oral administration of protein and peptide therapeutic agents |
US9949924B2 (en) | 2008-01-08 | 2018-04-24 | Oshadi Drug Administration Ltd. | Methods and compositions for oral administration of protein and peptide therapeutic agents |
EP2266546A1 (en) | 2009-06-08 | 2010-12-29 | Advancell Advanced in Vitro Cell Technologies,S.A. | Process for the preparation of colloidal systems for the delivery of active compounds |
US9060932B2 (en) | 2009-07-09 | 2015-06-23 | Oshadi Drug Administration Ltd. | Matrix carrier compositions, methods and uses |
US9504648B2 (en) | 2009-07-09 | 2016-11-29 | Oshadi Drug Administration Ltd. | Matrix carrier compositions, methods and uses |
WO2017014655A1 (en) | 2015-07-17 | 2017-01-26 | Uniwersytet Jagiellonski | Nanocapsule for delivery of lipophilic compound and process of preparation thereof |
Also Published As
Publication number | Publication date |
---|---|
DE69634927T2 (de) | 2008-05-15 |
ATE330636T1 (de) | 2006-07-15 |
DK0771566T3 (da) | 2006-10-23 |
ES2093562A1 (es) | 1996-12-16 |
CA2195881A1 (en) | 1996-11-28 |
ES2093562B1 (es) | 1997-07-01 |
US5843509A (en) | 1998-12-01 |
DE69634927D1 (de) | 2005-08-18 |
EP0771566A1 (en) | 1997-05-07 |
EP0771566B1 (en) | 2006-06-21 |
CA2195881C (en) | 2006-09-12 |
PT771566E (pt) | 2006-08-31 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
WO1996037232A1 (es) | Estabilizacion de sistemas coloidales mediante formacion de complejos ionicos lipido-polisacarido | |
CA1339008C (en) | Amphotericin b liposome preparation | |
Salimi | Liposomes as a novel drug delivery system: fundamental and pharmaceutical application | |
US5665379A (en) | Lipid particle forming matrix, preparation and use thereof | |
JP4786105B2 (ja) | リポソーム | |
US5962015A (en) | Stabilized liposomes | |
JP3695754B2 (ja) | 医薬組成物に関する改良 | |
CA2442539C (en) | Method and composition for solubilising a biologically active compound with low water solubility | |
KR20080102303A (ko) | 활성인 분자들의 투여를 위한 안정한 나노캡슐레이트 시스템 | |
WO2020203961A1 (ja) | 脂質膜構造体及びその製造方法 | |
JP2855594B2 (ja) | 脂質粒子形成マトリックス及びその製造方法 | |
WO1998004244A1 (es) | Aplicacion de nanoparticulas a base de polimeros hidrofilicos como formas farmaceuticas | |
CN111867562B (zh) | 不溶性药物的水性制剂 | |
TW201711677A (zh) | 磷脂-膽固醇酯奈米調配物及其相關方法 | |
ES2481940B1 (es) | Nanocápsulas de protamina | |
WO2010122204A1 (es) | Nanocapsulas de poliarginina | |
Katiyar et al. | Microemulsions: A novel drug carrier system | |
JPH035426A (ja) | 安定な電解質含有レシチン分散液 | |
JP2758297B2 (ja) | リポソーム調製物 | |
CN107530235B (zh) | 用于生产超小型脂质结构的一步法 | |
Bahrololoumi et al. | Niosomes as a promising nanovesicular drug delivery | |
JP3249583B2 (ja) | リポソーム製剤 | |
Desai et al. | An overview on niosomes as novel drug delivery systems | |
ES2596558B1 (es) | Liposomas recubiertos con albúmina | |
BR102023004857B1 (pt) | Nanocarreadores lipídicos carregados com nitrosilo complexo de rutênio para o tratamento de leishmaniose |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
AK | Designated states |
Kind code of ref document: A1 Designated state(s): CA JP US |
|
AL | Designated countries for regional patents |
Kind code of ref document: A1 Designated state(s): AT BE CH DE DK ES FI FR GB GR IE IT LU MC NL PT SE |
|
WWE | Wipo information: entry into national phase |
Ref document number: 1996914215 Country of ref document: EP |
|
WWE | Wipo information: entry into national phase |
Ref document number: 2195881 Country of ref document: CA |
|
WWE | Wipo information: entry into national phase |
Ref document number: 08776507 Country of ref document: US |
|
121 | Ep: the epo has been informed by wipo that ep was designated in this application | ||
WWP | Wipo information: published in national office |
Ref document number: 1996914215 Country of ref document: EP |
|
WWG | Wipo information: grant in national office |
Ref document number: 1996914215 Country of ref document: EP |