ES2581212T3 - Administración mejorada de tetahidrocannabinol - Google Patents
Administración mejorada de tetahidrocannabinol Download PDFInfo
- Publication number
- ES2581212T3 ES2581212T3 ES06827524.7T ES06827524T ES2581212T3 ES 2581212 T3 ES2581212 T3 ES 2581212T3 ES 06827524 T ES06827524 T ES 06827524T ES 2581212 T3 ES2581212 T3 ES 2581212T3
- Authority
- ES
- Spain
- Prior art keywords
- tetrahydrocannabinol
- sedds
- weight
- cannabidiol
- amg
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
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
- A61K9/10—Dispersions; Emulsions
- A61K9/107—Emulsions ; Emulsion preconcentrates; Micelles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/35—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom
- A61K31/352—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom condensed with carbocyclic rings, e.g. methantheline
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/35—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom
- A61K31/352—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom condensed with carbocyclic rings, e.g. methantheline
- A61K31/353—3,4-Dihydrobenzopyrans, e.g. chroman, catechin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/655—Azo (—N=N—), diazo (=N2), azoxy (>N—O—N< or N(=O)—N<), azido (—N3) or diazoamino (—N=N—N<) compounds
-
- 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
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
- A61K47/10—Alcohols; Phenols; Salts thereof, e.g. glycerol; Polyethylene glycols [PEG]; Poloxamers; PEG/POE alkyl ethers
-
- 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
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
- A61K47/12—Carboxylic acids; Salts or anhydrides thereof
-
- 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
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
- A61K47/14—Esters of carboxylic acids, e.g. fatty acid monoglycerides, medium-chain triglycerides, parabens or PEG fatty acid esters
-
- 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
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/22—Heterocyclic compounds, e.g. ascorbic acid, tocopherol or pyrrolidones
-
- 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
- A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
- A61K47/34—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyesters, polyamino acids, polysiloxanes, polyphosphazines, copolymers of polyalkylene glycol or poloxamers
-
- 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
- A61K47/44—Oils, fats or waxes according to two or more groups of A61K47/02-A61K47/42; Natural or modified natural oils, fats or waxes, e.g. castor oil, polyethoxylated castor oil, montan wax, lignite, shellac, rosin, beeswax or lanolin
-
- 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
- A61K9/4841—Filling excipients; Inactive ingredients
- A61K9/4858—Organic compounds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/08—Drugs for disorders of the alimentary tract or the digestive system for nausea, cinetosis or vertigo; Antiemetics
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Inorganic Chemistry (AREA)
- Organic Chemistry (AREA)
- Dispersion Chemistry (AREA)
- Biomedical Technology (AREA)
- Hospice & Palliative Care (AREA)
- Otolaryngology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pain & Pain Management (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Forma de dosificación oral de cannabinoides que comprende del 1 al 60% en peso de una forma farmacológicamente activa de cannabinoides en un sistema autoemulsionante que comprende del 20 al 80% en peso de medio oleoso, del 10 al 60% en peso de tensioactivo, seleccionándose el cannabinoide farmacológicamente activo del grupo que consiste en tetrahidrocannabinol, D9-tetrahidrocannabinol, D8-tetrahidrocannabinol, D8- tetrahidrocannabinol-DMH, análogo propílico del D9-tetrahidrocannabinol, 11-hidroxi-tetrahidrocannabinol, 11-nor-9- carboxi-tetrahidrocannabinol, 5'-azido-D8-tetrahidrocannabinol, AMG-1, AMG-3, AM411, AM708, AM836, AM855, AM919, AM926, AM938, cannabidiol, análogo propílico del cannabidiol, cannabinol, cannabicromeno, análogo propílico del cannabicromeno, cannabigerol, CP 47497, CP 55940, CP 55244, CP 50556, CT-3, dimetilheptil HHC, HU-210, HU-211, HU-308, WIN 55212-2, desacetil-L-nantradol, dexanabinol, JWH-051, levonantradol, L-759633, nabilona, O-1184, y mezclas de los mismos; y el medio oleoso se selecciona del grupo que consiste en triglicéridos y/o glicéridos mixtos y/o ácidos grasos libres que tienen de C6 a C32 átomos de carbono.
Description
25
30
35
40
45
50
55
TABLA 1
- Composición
- mg de ingrediente por formulación (% por cápsula)
- (i)
- (ii) (iii) (iv) (v) (vi) 5(vii)
- Δ9-THC (en forma de resina)
- 10 (3,85) 10 (3,85) 10 (3,85) 10 (3,85) 10 (3,65) 10 (3,71) 10 (4,1)
- Ácido oleico
- - 125 (48,1) 125 (48,1) 62 (24) - 235 (95,95)
- Capmul MCM (L)
- 250 (96,15) - - - - 10 -
- Labrasol
- - 125 (48,1) - - - 131,5 (48,88) -
- Labrafil M 1944CS
- - - 125 (48,1) 188 (72,16) 139 (50,70) 15 -
- Aceite de sésamo
- - - - - 125 (45,65) -
- Aceite de soja
- - - - - - 127,5 (47,41) -
- Total
- 260 (100) 260 (100) 260 (100) 260 (100) 274 (100) 269 (100) 20 245 (100)
[0088] La Figura 1 muestra que las formulaciones ensayadas demostraron ser más óptimas que las formulaciones comerciales. Estos estudios de disolución se llevaron a cabo utilizando SLS al 2% en medios acuosos (aparato de paleta, 75 rpm). Estas pruebas también establecieron que era posible mejorar la disolución de THC utilizando sistemas de administración de fármacos autoemulsionantes.
Ejemplo 2
[0089] La formulación preparada anteriormente vii (Tabla 1), que se clasificó como sistema SEDDS de tipo I, se evaluó en varios medios de disolución a 37ºC (paleta, 75 rpm) con el fin de determinar las condiciones de ensayo más adecuadas. El porcentaje de liberación obtenido en cada uno de los medio de disolución ensayados se expone en la Tabla 2.
TABLA 2
- Medio de disolución
- Porcentaje de liberación (min)
- 15
- 30 60 120 240
- Agua
- 0 0 0 0,3 1,1
- SLS al 2% en Agua
- ≥100,0 ≥100,0 ≥100,0 ≥100,0 ≥100,0
- Triton X-100 al 5%
- 67,5 ≥100,0 ≥100,0 ≥100,0 ≥100,0
- Tampón de acetato, pH 4,5
- 0,0 0,0 0,0 0,0, 0,0,
- Tampón de borato, pH 9,5
- 39,8 67,3 ≥100,0 ≥100,0 ≥100,0
- HCl 0,1N
- 0,0 0,0 0,0, 0,0, 0,0,
Es evidente a partir de los resultados anteriores en la tabla 2 que SLS al 2% o Triton X-100 al 5% es una elección ideal para evaluar formulaciones SEDDS de THC. Pueden ser necesarios medios adicionales, tales como medios gástricos e intestinales simulados para una evaluación adicional. En particular, se utilizan preferiblemente medios intestinales simulados de estado de ayuno (FaSSIF) y medios intestinales simulados de estado de alimentación (FeSSIF).
[0090] Los datos en la Tabla 2 también establece que los sistemas SEDDS tienen un efecto protector para Δ-9 THC frente a la degradación catalizada por ácido en el medio del estómago. Esto es debido al hecho de que el fármaco es retenido dentro de la matriz SEDDS tras la dilución inicial en medios acuosos y no está disponible para su liberación en el medio circundante. Tras realizar las pruebas de dilución acuosa para formulaciones de placebo descritas a continuación (Ejemplos 3 y 4), la formación de dispersiones sólidas de partícula gruesa o dispersiones turbias muestran además que los sistemas SEDDS protegen los cannabinoides activos frente a la degradación catalizada por ácido en el estómago (Ejemplo 5).
Ejemplo 3
[0091] Los sistemas SEDDS Tipo I, Tipo II y Tipo III preferidos son de naturaleza isotrópica con un comportamiento de fase uniforme antes de la dilución en medio acuoso. Las fórmulas de SEDDS separadas en fases no son de naturaleza isotrópica y muestran agrietamiento o mala uniformidad de matriz en el caso de semisólidos.
[0092] La Tabla 3 a continuación muestra los resultados de los exámenes de comportamiento de fase para seleccionar SEDDS, formulaciones de placebo que utilizan combinaciones de un medio portador oleoso con Cremophor EL. Los exámenes fueron macroscópicos (es decir, visuales), así como microscópicos (Olympus®
12
Stereomicroscope).
TABLA 3
- Ingrediente
- (a) mg (%) (b) mg (%) (c) mg (%) (d) mg (%)
- ESTADO FÍSICO
- Líquido Líquido Semisólido fluido Semisólido
- Agente activo
- 0 (3,85) 0 (3,85) 0 (3,85) 0 (3,85)
- Componente de Aceite/ Portador de Ácido Graso (por ejemplo Ácido Oleico)
- 120,0 (46,15) 121,75 (46,8) 158,0 (60,8) 112,5 (43,1)
- Componente de Tensioactivo (por ejemplo Cremóforo EL)
- 120,0 (46,15) 121,75 (46,8) 79,0 (30,4) 112,5 (43,1)
- Vitamina E, FCC
- 5,0 (1,925) - - -
- Palmitato de ascorbilo
- 5,0 (1,925) 6,5 (2,5) 13,0 (5,0) 26,0 (10,0)
- Total*
- 250 (100) 250 (100) 250 (100) 251 (100)
- *Porcentajes en “()”se basan en el peso de llenado de ∼260 mg para todas las formulaciones cargadas de fármaco
5
[0093] La Tabla 3 muestra que con el aumento de las concentraciones de palmitato de ascorbilo, la matriz SEDDS cambia de estado líquido a un estado semisólido o estado semisólido fluido. Por lo tanto, el palmitato de ascorbilo, un soluto anfifílico, sirve como un inductor de semisólido cuando está presente en concentraciones en exceso en la matriz de formulación SEDDS.
10 [0094] En el presente ejemplo, el medio portador oleoso se sustituye por varios "aceites". El componente tensioactivo se sustituye por diversos ingredientes. Los ingredientes adicionales en la matriz SEDDS incluyen modificadores de la viscosidad, antioxidantes, e inhibidores metabólicos/PGP. Cuando las matrices SEDDS se administran con o sin una cubierta de cápsula a un sistema gastrointestinal de mamíferos (véase el Ejemplo 5), se
15 aplica lo siguiente:
- (i)
- La dispersión acuosa inicial de los sistemas SEDDS en los contenidos ácidos del estómago da lugar a una dispersión de partícula gruesa o dispersión sólida para la protección frente al medio ácido.
- (ii)
- Con la presencia de sales biliares en el duodeno superior, la forma de dosificación SEDDS se incorpora en las vías de absorción de los lípidos de mamíferos, evitando así el metabolismo hepático de primer paso.
20 (iii) Cuando se comparan las composiciones SEDDS líquidas frente a las composiciones SEDDS semisólidas debido a una mayor concentración de anfifílico/no anfifilico, el primer sistema proporciona perfiles de disolución del fármaco más rápidos, mientras que el segundo sistema proporciona perfiles de disolución más prolongados, respectivamente.
(iv) Los sistemas SEDDS líquidos de liberan de forma inmediata las formas de dosificación, mientras que los 25 sistemas SEDDS semisólidos liberan de forma sostenida las formas de dosificación.
Ejemplo 4
[0095] Los sistemas SEDDS Tipo I, Tipo II y Tipo III preferidos son de naturaleza isotrópica con un comportamiento
30 de fase uniforme antes de la dilución en medio acuoso. Las fórmulas de SEDDS separadas en fases, que no son de naturaleza isotrópica, muestran agrietamiento o mala uniformidad de matriz en el caso de semisólidos. La Tabla 4 a continuación muestra los resultados de los exámenes de comportamiento de fase para seleccionar SEDDS, formulaciones de placebo que utilizan combinaciones de un medio portador oleoso con Labrasol. Los exámenes fueron macroscópicos (es decir, visuales), así como microscópicos (Olympus® Stereomicroscope).
35 TABLA 4
- Ingrediente
- (e) mg (%) (f) mg (%) (g) mg (%)
- ESTADO FÍSICO
- Líquido Semisólido fluido Semisólido
- Agente activo
- 0 (3,85) 0 (3,85) 0 (3,85)
- Componente de Aceite/ Portador de Ácido Graso (por ejemplo Ácido Oleico)
- 121,75 (46,8) 158,0 (60,8) 112,5 (43,1)
- Componente de Tensioactivo (por ejemplo, Labrasol)
- 121,75 (46,8) 79,0 (30,4) 112,5 (43,1)
- Palmitato de ascorbilo
- 6,5 (2,5) 13,0 (5,0) 26,0 (10,0)
13
Claims (1)
-
imagen1 imagen2
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US73416005P | 2005-11-07 | 2005-11-07 | |
US734160P | 2005-11-07 | ||
PCT/US2006/043126 WO2007056242A1 (en) | 2005-11-07 | 2006-11-03 | Improved delivery of tetrahydrocannabinol |
Publications (1)
Publication Number | Publication Date |
---|---|
ES2581212T3 true ES2581212T3 (es) | 2016-09-02 |
Family
ID=38023589
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
ES06827524.7T Active ES2581212T3 (es) | 2005-11-07 | 2006-11-03 | Administración mejorada de tetahidrocannabinol |
Country Status (9)
Country | Link |
---|---|
US (1) | US20070104741A1 (es) |
EP (1) | EP1903866B1 (es) |
JP (1) | JP2009514890A (es) |
AU (1) | AU2006311818B9 (es) |
CA (1) | CA2618705C (es) |
DK (1) | DK1903866T3 (es) |
ES (1) | ES2581212T3 (es) |
PT (1) | PT1903866E (es) |
WO (1) | WO2007056242A1 (es) |
Families Citing this family (104)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
MXPA06011871A (es) * | 2004-04-15 | 2007-10-08 | Chiasma Inc | Composiciones capaces de facilitar la penetracion a traves de una barrera biologica. |
US20070219131A1 (en) * | 2004-04-15 | 2007-09-20 | Ben-Sasson Shmuel A | Compositions capable of facilitating penetration across a biological barrier |
CN101132781A (zh) * | 2004-12-09 | 2008-02-27 | 茵西斯医疗公司 | 在室温下稳定的屈大麻酚剂型 |
US8497258B2 (en) | 2005-11-12 | 2013-07-30 | The Regents Of The University Of California | Viscous budesonide for the treatment of inflammatory diseases of the gastrointestinal tract |
EP2046290A4 (en) * | 2006-08-04 | 2011-08-17 | Insys Therapeutics Inc | AQUEOUS DRONABINOL FORMULATIONS |
IL181217A0 (en) * | 2007-02-08 | 2007-07-04 | Haim Levy | Pharmaceuticalcompositions based on a microemulsion |
US8222292B2 (en) | 2007-08-06 | 2012-07-17 | Insys Therapeutics, Inc. | Liquid cannabinoid formulations |
JP2010535774A (ja) * | 2007-08-06 | 2010-11-25 | インシス セラピューティクス インコーポレイテッド | 経口カンナビノイド液体製剤および治療方法 |
WO2009024590A2 (en) * | 2007-08-21 | 2009-02-26 | Basilea Pharmaceutica Ag | Antifungal composition |
EP2268274B1 (en) | 2008-03-20 | 2012-05-16 | Virun, Inc. | Vitamin e derivatives and their uses |
EP2548456B1 (en) | 2008-03-20 | 2015-07-08 | Virun, Inc. | Emulsions including a PEG-derivative of tocopherol |
US8003672B2 (en) * | 2008-04-21 | 2011-08-23 | Merck Sharp & Dohme Corp. | CB-1 receptor modulator formulations |
WO2010032140A2 (en) | 2008-09-17 | 2010-03-25 | Chiasma Inc. | Pharmaceutical compositions and related methods of delivery |
GB0818473D0 (en) | 2008-10-08 | 2008-11-12 | Probio Nutraceuticals As | Composition |
CA2765033C (en) | 2009-06-12 | 2020-07-14 | Meritage Pharma, Inc. | Methods for treating gastrointestinal disorders |
CN101632650B (zh) * | 2009-07-07 | 2013-11-27 | 沈阳药科大学 | 一种黄豆苷元自微乳化半固体骨架胶囊及其制备方法 |
US8735374B2 (en) * | 2009-07-31 | 2014-05-27 | Intelgenx Corp. | Oral mucoadhesive dosage form |
AU2009352678B2 (en) | 2009-09-15 | 2015-05-21 | Eluminex Biosciences (Suzhou) Limited | Pharmaceutical formulations comprising 9-cis-retinyl esters in a lipid vehicle |
AT509000B1 (de) * | 2009-10-23 | 2012-12-15 | Rausch Peter | Wasserlösliche zubereitungen von cannabinoiden und cannabispräparaten und deren anwendungen |
US10610528B2 (en) | 2009-12-08 | 2020-04-07 | Intelgenx Corp. | Solid oral film dosage forms and methods for making same |
US20110136815A1 (en) | 2009-12-08 | 2011-06-09 | Horst Zerbe | Solid oral film dosage forms and methods for making same |
WO2011119228A1 (en) | 2010-03-23 | 2011-09-29 | Virun, Inc. | Nanoemulsion including sucrose fatty acid ester |
GB201006200D0 (en) * | 2010-04-14 | 2010-06-02 | Ayanda As | Composition |
EP2563350B1 (en) | 2010-04-19 | 2020-10-14 | Retinagenix Therapeutics, Inc. | Therapeutic regimen and method for treating or ameliorating visual disorders associated with an endogenous retinoid deficiency |
WO2011162802A1 (en) | 2010-06-21 | 2011-12-29 | Virun, Inc. | Compositions containing non-polar compounds |
ES2553742T3 (es) * | 2010-08-04 | 2015-12-11 | Grünenthal GmbH | Forma de dosificación farmacéutica que comprende 6'-fluor-(N-metil- o N,N-dimetil)-4-fenil-4',9'-dihidro-3'H-espiro[ciclohexano-1,1'-pirano[3,4,b]indol]-4-amina |
US11730709B2 (en) | 2010-10-29 | 2023-08-22 | Infirst Healthcare Limited | Compositions and methods for treating severe pain |
US11202831B2 (en) | 2010-10-29 | 2021-12-21 | Infirst Healthcare Limited | Solid solution compositions and use in cardiovascular disease |
US9308213B2 (en) | 2010-10-29 | 2016-04-12 | Infirst Healthcare Limited | Solid solution compositions and use in chronic inflammation |
US9504664B2 (en) | 2010-10-29 | 2016-11-29 | Infirst Healthcare Limited | Compositions and methods for treating severe pain |
US9744132B2 (en) | 2010-10-29 | 2017-08-29 | Infirst Healthcare Limited | Solid solution compositions and use in chronic inflammation |
US9271950B2 (en) | 2010-10-29 | 2016-03-01 | Infirst Healthcare Limited | Compositions for treating chronic inflammation and inflammatory diseases |
US10695432B2 (en) | 2010-10-29 | 2020-06-30 | Infirst Healthcare Limited | Solid solution compositions and use in severe pain |
US11224659B2 (en) | 2010-10-29 | 2022-01-18 | Infirst Healthcare Limited | Solid solution compositions and use in severe pain |
US8895536B2 (en) | 2010-10-29 | 2014-11-25 | Infirst Healthcare Ltd. | Compositions and methods for treating chronic inflammation and inflammatory diseases |
US10695431B2 (en) | 2010-10-29 | 2020-06-30 | Infirst Healthcare Limited | Solid solution compositions and use in cardiovascular disease |
US9737500B2 (en) | 2010-10-29 | 2017-08-22 | Infirst Healthcare Limited | Compositions and methods for treating severe pain |
US8183227B1 (en) | 2011-07-07 | 2012-05-22 | Chemo S. A. France | Compositions, kits and methods for nutrition supplementation |
US8168611B1 (en) | 2011-09-29 | 2012-05-01 | Chemo S.A. France | Compositions, kits and methods for nutrition supplementation |
WO2013120025A1 (en) | 2012-02-10 | 2013-08-15 | Virun, Inc. | Beverage compositions containing non-polar compounds |
BR112014021602A2 (pt) | 2012-03-01 | 2021-06-08 | Quadra Logic Tech Inc | uso, kit e derivado de retinal sintético para melhorar a função visual em distúrbios visuais associados com a deficiência de produção endógena de retinóide |
US20150051299A1 (en) * | 2012-03-19 | 2015-02-19 | Ariel-University Research And Development Company, Ltd. | Treatment of schizophrenia using beta-caryophyllene and cb2 receptor agonists |
DE102012105063C5 (de) * | 2012-06-12 | 2023-09-14 | Thc Pharm Gmbh The Health Concept | Stabilisierung von Cannabinoiden und deren pharmazeutischen Zubereitungen |
US11253472B2 (en) | 2012-10-04 | 2022-02-22 | Benuvia Therapeutics Llc | Oral cannabinoid formulations |
US9345771B2 (en) | 2012-10-04 | 2016-05-24 | Insys Development Company, Inc. | Oral cannabinoid formulations |
US10265293B2 (en) | 2012-10-04 | 2019-04-23 | Insys Development Company, Inc. | Oral cannabinoid formulations |
EP3851101A1 (en) | 2013-02-12 | 2021-07-21 | Corbus Pharmaceuticals, Inc. | Ultrapure tetrahydrocannabinol-11-oic acids |
JP6581509B2 (ja) | 2013-02-28 | 2019-09-25 | ティーウィノット テクノロジーズ リミテッド | 化合物を合成する化学工学プロセス及び装置 |
US9351517B2 (en) | 2013-03-15 | 2016-05-31 | Virun, Inc. | Formulations of water-soluble derivatives of vitamin E and compositions containing same |
US11911361B2 (en) | 2014-05-29 | 2024-02-27 | Radius Pharmaceuticals, Inc. | Stable cannabinoid formulations |
US11331279B2 (en) | 2014-05-29 | 2022-05-17 | Radius Pharmaceuticals, Inc. | Stable cannabinoid formulations |
EP3160445B1 (en) * | 2014-06-26 | 2021-10-20 | Island Breeze Systems Ca, LLC | Mdi related products and methods of use |
BR112017003966A2 (pt) * | 2014-08-25 | 2018-10-23 | Full Spectrum Laboratories Ltd | aparelhos e métodos para a produção simultânea de compostos canabinoides |
MA41462A (fr) | 2015-02-03 | 2021-05-12 | Chiasma Inc | Méthode de traitement de maladies |
AU2016231788A1 (en) * | 2015-03-19 | 2017-10-12 | One World Cannabis Ltd | Preparations of cannabis emulsions and methods thereof |
US20170021029A1 (en) * | 2015-04-15 | 2017-01-26 | Jeffrey Charles Raber | Topical formulations and uses |
CA2985332C (en) | 2015-05-18 | 2023-01-03 | 5071, Inc. | Homogenous cannabis compositions and methods of making the same |
ES2938560T3 (es) | 2015-05-28 | 2023-04-12 | Radius Pharmaceuticals Inc | Formulaciones de cannabinoides estables |
GB2539472A (en) * | 2015-06-17 | 2016-12-21 | Gw Res Ltd | Use of cannabinoids in the treatment of epilepsy |
BR102015024165A2 (pt) * | 2015-09-18 | 2017-03-28 | Prati Donaduzzi & Cia Ltda | composição farmacêutica oral compreendendo canabinóide, processo para sua preparação e seu uso |
AU2016347651A1 (en) | 2015-10-26 | 2018-05-17 | Yissum Research Development Company Of The Hebrew University Of Jerusalem Ltd | Novel cannabinoid formulations |
US10376586B2 (en) | 2016-02-16 | 2019-08-13 | Entourage Bioscience, LLC | Method and compositions for solubilizing non-polar constituents |
JP2019511580A (ja) | 2016-04-15 | 2019-04-25 | エスアールイー ウェルネス インク.Sre Wellness Inc. | 乳化剤を使用して大麻油を親水性にする方法及び関連するカンナビノイド組成物 |
JP7053054B2 (ja) | 2016-04-15 | 2022-04-12 | エスアールイー ウェルネス,インク. | 大麻注入甘味料及び他の組成物 |
AU2017252575B2 (en) * | 2016-04-22 | 2021-11-18 | Spoke Sciences, Inc. | Fast-acting plant-based medicinal compounds and nutritional supplements |
CN109715152A (zh) * | 2016-04-29 | 2019-05-03 | 柯巴斯医药有限公司 | 医治感染的方法 |
GB2551985B (en) * | 2016-07-01 | 2019-01-30 | Gw Res Ltd | Novel formulation |
RU2019103297A (ru) | 2016-07-11 | 2020-08-11 | Интек Фарма Лтд. | Гастроретентивные составы для перорального введения и пути их применения |
IL246790A0 (en) * | 2016-07-14 | 2016-09-29 | Friedman Doron | Self-dissolving compounds of cannabinoids |
US20180263954A1 (en) * | 2016-09-27 | 2018-09-20 | CannTab Therapeutics, Limited | Sustained Release Cannabinoid Formulations |
WO2018058235A1 (en) * | 2016-09-27 | 2018-04-05 | CannTab Therapeutics Limited | Sustained release cannabinoid formulations |
IL248150B (en) | 2016-09-29 | 2018-05-31 | Garti Nissim | A method for selective extraction of cannabinoid from plant origin |
IL248148B (en) | 2016-09-29 | 2021-09-30 | Yissum Res Dev Co Of Hebrew Univ Jerusalem Ltd | A method for extracting a compound from plant origin |
IL248149B (en) | 2016-09-29 | 2020-03-31 | Garti Nissim | Formulations of dilutable cannabinoids and processes for their preparation |
US10188628B1 (en) | 2016-10-27 | 2019-01-29 | Alvin Kershman | Release composition for derivatives of Cannabaceae |
EA201892396A1 (ru) * | 2016-12-02 | 2019-04-30 | Ресептор Лайф Сайенсиз, Инк. | Быстродействующие растительные лекарственные соединения и биологически активные добавки |
CN110636834A (zh) * | 2017-02-15 | 2019-12-31 | 分子浸剂有限公司 | 制剂 |
US10231948B2 (en) | 2017-02-27 | 2019-03-19 | Jason Ty Nguyen | Metered dose inhaler compositions, systems, and methods |
FR3064469B1 (fr) * | 2017-03-30 | 2020-10-09 | Capsum | Particules colorees a teneur elevee en pigment |
CN111163806A (zh) | 2017-07-11 | 2020-05-15 | 阿奎诺瓦股份公司 | 含有姜黄素,乳香和黄腐酚的增溶物 |
EP3651738B1 (en) * | 2017-07-14 | 2024-04-03 | 5071, Inc. | Cannabinoid compositions and methods of preparation thereof |
US20190015346A1 (en) * | 2017-07-14 | 2019-01-17 | Pharmacannis Labs Llc | Self-emulsifying drug delivery system |
US20190022028A1 (en) * | 2017-07-21 | 2019-01-24 | Annabelle Manalo | Cannabidiol-enriched caprylic acid |
GB2572125B (en) * | 2018-01-03 | 2021-01-13 | Gw Res Ltd | Pharmaceutical |
GB2572126B (en) * | 2018-01-03 | 2021-01-13 | Gw Res Ltd | Pharmaceutical |
GB2569961B (en) * | 2018-01-03 | 2021-12-22 | Gw Res Ltd | Pharmaceutical |
SI25373A (sl) * | 2018-05-08 | 2018-08-31 | Danijela Marković | Naravna orodisperzibilna tableta |
CN110742861A (zh) * | 2018-07-04 | 2020-02-04 | 汉义生物科技(北京)有限公司 | 一种大麻二酚自乳化给药系统、固体自乳化制剂及其制备方法 |
AU2019300877A1 (en) * | 2018-07-09 | 2021-03-04 | New Age Nanotech Llc | Stabilized formulations of cannabinoid compositions |
FI3820529T3 (en) * | 2018-07-11 | 2023-09-29 | Aquanova Ag | CELL BILISAATE CONTAINING CURCUMIN AND AT LEAST THE CANNABINOID THC AS ANOTHER ACTIVE SUBSTANCE |
ES2960685T3 (es) | 2018-07-11 | 2024-03-06 | Aquanova Ag | Solubilizado de xantohumol |
EP3937915A4 (en) * | 2019-03-13 | 2022-12-21 | Milane, Michael | NOVEL NANOFORMULATION OF CANNABIDIOL (CBD) AND OTHER CANNABINOIDS FOR THE TREATMENT OF SKIN DISEASES |
CN113966213A (zh) * | 2019-04-18 | 2022-01-21 | 耶路撒冷希伯来大学伊森姆研究发展有限公司 | 用于亲脂性化合物的递送的自乳化药物递送系统 |
US11806645B1 (en) | 2019-05-07 | 2023-11-07 | Cannaceutical Extractions LLC | Methods of producing CBD/THC oils |
CN110269843A (zh) * | 2019-06-15 | 2019-09-24 | 云南飞久逍科技有限公司 | 一种大麻二酚cbd纳米乳冻干粉及其制备方法 |
US11542226B2 (en) * | 2020-04-23 | 2023-01-03 | Axim Biotechnologies, Inc. | Polyfunctional cannabinoids |
FR3110427B1 (fr) * | 2020-05-20 | 2023-07-14 | Laboratoires Eriger | Conjugué terpenique de couplage |
IL276051B (en) * | 2020-07-14 | 2021-04-29 | Cannassure Ltd | Oral cannabinoid compositions |
US11141457B1 (en) | 2020-12-28 | 2021-10-12 | Amryt Endo, Inc. | Oral octreotide therapy and contraceptive methods |
US11242328B1 (en) | 2021-02-25 | 2022-02-08 | Acid Neutral Alkaline Laboratory | Heterogeneous catalyst and method for preparation of aromatic tricyclic pyrans |
US11242330B1 (en) | 2021-02-25 | 2022-02-08 | Acid Neutral Alkaline Laboratory | Organic catalyst and method for preparation of aromatic tricyclic pyrans |
US12029720B2 (en) | 2021-04-29 | 2024-07-09 | Tilray Brands, Inc. | Cannabidiol-dominant formulations, methods of manufacturing, and uses thereof |
WO2023159277A1 (en) * | 2022-02-28 | 2023-08-31 | Emyria | Cannabinoid dosage form |
WO2024047529A1 (en) * | 2022-08-30 | 2024-03-07 | 2682130 Ontario Limited | Water-dispersible cannabinoid emulsion formulations, methods of making and applications |
Family Cites Families (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1995025504A1 (en) * | 1994-03-18 | 1995-09-28 | Pharmavene, Inc. | Emulsified drug delivery systems |
GB9726916D0 (en) * | 1997-12-19 | 1998-02-18 | Danbiosyst Uk | Nasal formulation |
GB9823246D0 (en) * | 1998-10-24 | 1998-12-16 | Danbiosyst Uk | A nasal drug delivery composition |
US6294192B1 (en) * | 1999-02-26 | 2001-09-25 | Lipocine, Inc. | Triglyceride-free compositions and methods for improved delivery of hydrophobic therapeutic agents |
US6383471B1 (en) * | 1999-04-06 | 2002-05-07 | Lipocine, Inc. | Compositions and methods for improved delivery of ionizable hydrophobic therapeutic agents |
IL151603A0 (en) * | 2000-03-09 | 2003-04-10 | Gw Pharma Ltd | A pharmaceutical composition containing cannabis and devices for delivering the same |
US6730330B2 (en) * | 2001-02-14 | 2004-05-04 | Gw Pharma Limited | Pharmaceutical formulations |
CH695661A5 (de) * | 2001-03-06 | 2006-07-31 | Forsch Hiscia Ver Fuer Krebsfo | Pharmazeutische Zusammensetzung. |
IL148736A0 (en) * | 2002-03-18 | 2002-09-12 | Pharmos Corp | Dexanabinol and dexanabinol analogs which regulate inflammation related genes |
US6946150B2 (en) * | 2002-08-14 | 2005-09-20 | Gw Pharma Limited | Pharmaceutical formulation |
-
2006
- 2006-11-03 JP JP2008539101A patent/JP2009514890A/ja not_active Withdrawn
- 2006-11-03 WO PCT/US2006/043126 patent/WO2007056242A1/en active Application Filing
- 2006-11-03 PT PT06827524T patent/PT1903866E/pt unknown
- 2006-11-03 ES ES06827524.7T patent/ES2581212T3/es active Active
- 2006-11-03 DK DK06827524.7T patent/DK1903866T3/en active
- 2006-11-03 EP EP06827524.7A patent/EP1903866B1/en active Active
- 2006-11-03 AU AU2006311818A patent/AU2006311818B9/en not_active Ceased
- 2006-11-03 CA CA2618705A patent/CA2618705C/en active Active
- 2006-11-03 US US11/592,393 patent/US20070104741A1/en not_active Abandoned
Also Published As
Publication number | Publication date |
---|---|
DK1903866T3 (en) | 2016-07-25 |
CA2618705A1 (en) | 2007-05-18 |
EP1903866A4 (en) | 2010-12-22 |
EP1903866A1 (en) | 2008-04-02 |
JP2009514890A (ja) | 2009-04-09 |
US20070104741A1 (en) | 2007-05-10 |
PT1903866E (pt) | 2016-06-09 |
AU2006311818A1 (en) | 2007-05-18 |
WO2007056242A1 (en) | 2007-05-18 |
AU2006311818B2 (en) | 2013-05-09 |
CA2618705C (en) | 2014-04-22 |
EP1903866B1 (en) | 2016-04-06 |
AU2006311818B9 (en) | 2013-05-16 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
ES2581212T3 (es) | Administración mejorada de tetahidrocannabinol | |
CA3028580C (en) | Cannabinoid formulations | |
JP7378402B2 (ja) | カンナビノイドを含む放出調節組成物 | |
JP7404242B2 (ja) | カンナビノイドを含む放出調節組成物 | |
Qian et al. | Self-nanoemulsifying drug delivery systems of myricetin: Formulation development, characterization, and in vitro and in vivo evaluation | |
US9265724B2 (en) | Oral dosage form of tetrahydrocannabinol and a method of avoiding and/or suppressing hepatic first pass metabolism via targeted chylomicron/lipoprotein delivery | |
US20160184258A1 (en) | Oral gastrointestinal dosage form delivery system of cannabinoids and/or standardized marijuana extracts | |
WO2016022936A1 (en) | An improved oral gastrointestinal dosage form delivery system of cannabinoids and/or standardized marijuana extracts | |
US20140357708A1 (en) | Oral dosage form of tetrahydrocannabinol and a method of avoiding and/or suppressing hepatic first pass metabolism via targeted chylomicron/lipoprotein delivery | |
WO2012033478A1 (en) | An improved oral dosage form of tetrahydrocannabinol and a method of avoiding and/or suppressing hepatic first pass metabolism via targeted chylomicron/lipoprotein delivery | |
AU2019205118B2 (en) | Modified release composition comprising a cannabinoid | |
KR102685325B1 (ko) | 칸나비노이드를 포함하는 변형 방출형 조성물 |