ES2581212T3 - Administración mejorada de tetahidrocannabinol - Google Patents

Administración mejorada de tetahidrocannabinol Download PDF

Info

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
Application number
ES06827524.7T
Other languages
English (en)
Inventor
Ram B. Murty
Santos B. Murty
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Murty Pharmaceuticals Inc
Original Assignee
Murty Pharmaceuticals Inc
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Murty Pharmaceuticals Inc filed Critical Murty Pharmaceuticals Inc
Application granted granted Critical
Publication of ES2581212T3 publication Critical patent/ES2581212T3/es
Active legal-status Critical Current
Anticipated expiration legal-status Critical

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)
  • Dispersion Chemistry (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Organic Chemistry (AREA)
  • Inorganic 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

imagen1
imagen2
imagen3
imagen4
imagen5
imagen6
imagen7
imagen8
imagen9
imagen10
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
imagen11
imagen12
imagen13
imagen14
imagen15
imagen16
imagen17

Claims (1)

  1. imagen1
    imagen2
ES06827524.7T 2005-11-07 2006-11-03 Administración mejorada de tetahidrocannabinol Active ES2581212T3 (es)

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 (102)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20050232981A1 (en) * 2004-04-15 2005-10-20 Ben-Sasson Shmuel A Compositions capable of facilitating penetration across a biological barrier
US20070219131A1 (en) * 2004-04-15 2007-09-20 Ben-Sasson Shmuel A Compositions capable of facilitating penetration across a biological barrier
MX2007007038A (es) * 2004-12-09 2008-03-07 Insys Therapeutics Inc Formulacion de dronabinol en temperatura ambiente.
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
AU2007281918A1 (en) * 2006-08-04 2008-02-14 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
EP2184983A1 (en) * 2007-08-06 2010-05-19 Insys Therapeutics Inc. Oral cannabinoid liquid formulations and methods of treatment
CN101784259B (zh) * 2007-08-21 2013-03-27 巴斯利尔药物股份公司 抗真菌组合物
DK2268160T3 (da) 2008-03-20 2013-01-07 Virun Inc Emulsioner omfattende et PEG-derivat af tokoferol
CA2715018C (en) * 2008-03-20 2012-11-13 Virun, Inc. Vitamin e derivatives and their uses
US8003672B2 (en) * 2008-04-21 2011-08-23 Merck Sharp & Dohme Corp. CB-1 receptor modulator formulations
EP2343982B1 (en) 2008-09-17 2017-03-22 Chiasma Inc. Pharmaceutical compositions and related methods of delivery
GB0818473D0 (en) 2008-10-08 2008-11-12 Probio Nutraceuticals As Composition
WO2010144865A2 (en) 2009-06-12 2010-12-16 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
JP5663025B2 (ja) 2009-09-15 2015-02-04 キューエルティー インコーポレイテッド ９−ｃｉｓ−レチニルエステルを脂質ビヒクル中に含む医薬製剤
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
CN103037708B (zh) 2010-03-23 2015-05-20 维尔恩公司 含有蔗糖脂肪酸酯的纳米乳液
GB201006200D0 (en) * 2010-04-14 2010-06-02 Ayanda As Composition
WO2011132084A2 (en) 2010-04-19 2011-10-27 Qlt 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
NZ604662A (en) * 2010-08-04 2014-08-29 Gruenenthal Gmbh Pharmaceutical dosage form comprising 6’-fluoro-(n-methyl- or n,n-dimethyl-)-4-phenyl-4’,9’-dihydro-3’h-spiro[cyclohexane-1,1’-pyrano[3,4,b]indol]-4-amine
US9271950B2 (en) 2010-10-29 2016-03-01 Infirst Healthcare Limited Compositions for treating chronic inflammation and inflammatory diseases
US9744132B2 (en) 2010-10-29 2017-08-29 Infirst Healthcare Limited Solid solution compositions and use in chronic inflammation
US11730709B2 (en) 2010-10-29 2023-08-22 Infirst Healthcare Limited Compositions and methods for treating severe pain
US9737500B2 (en) 2010-10-29 2017-08-22 Infirst Healthcare Limited Compositions and methods for treating severe pain
US11224659B2 (en) 2010-10-29 2022-01-18 Infirst Healthcare Limited Solid solution compositions and use in severe pain
US10695432B2 (en) 2010-10-29 2020-06-30 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
US11202831B2 (en) 2010-10-29 2021-12-21 Infirst Healthcare Limited Solid solution compositions and use in cardiovascular disease
US9504664B2 (en) 2010-10-29 2016-11-29 Infirst Healthcare Limited Compositions and methods for treating severe pain
US10695431B2 (en) 2010-10-29 2020-06-30 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
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
US10874122B2 (en) 2012-02-10 2020-12-29 Virun, Inc. Beverage compositions containing non-polar compounds
CA2865935C (en) 2012-03-01 2021-12-14 Qlt Inc. Therapeutic regimens and methods for improving visual function in visual disorders associated with an endogenous retinoid deficiency
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
WO2014134281A1 (en) 2013-02-28 2014-09-04 Full Spectrum Laboratories Limited Biosynthesis of cannabinoids
US9351517B2 (en) 2013-03-15 2016-05-31 Virun, Inc. Formulations of water-soluble derivatives of vitamin E and compositions containing same
US11331279B2 (en) 2014-05-29 2022-05-17 Radius Pharmaceuticals, Inc. Stable cannabinoid formulations
US11911361B2 (en) 2014-05-29 2024-02-27 Radius Pharmaceuticals, Inc. Stable cannabinoid formulations
US10610512B2 (en) 2014-06-26 2020-04-07 Island Breeze Systems Ca, Llc MDI related products and methods of use
CN106922153B (zh) * 2014-08-25 2018-11-02 蒂威诺特科技有限公司 用于大麻素化合物的同时生产的设备和方法
CA2975599A1 (en) 2015-02-03 2016-08-11 Chiasma Inc. Method of treating diseases
CA2982250A1 (en) * 2015-03-19 2016-09-22 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
WO2016186735A1 (en) 2015-05-18 2016-11-24 5071, Inc. Homogenous cannabis compositions and methods of making the same
WO2016191651A1 (en) 2015-05-28 2016-12-01 Insys Development Company, Inc. Stable cannabinoid formulations
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
EP3442522A4 (en) * 2016-04-15 2020-01-01 SRE Wellness, Inc. PROCESS FOR PRODUCING HYDROPHILIZED CANNABIS OIL USING EMULSIFIERS, AND COMPOSITIONS OF CANNABINOIDS THEREOF
WO2017180953A1 (en) * 2016-04-15 2017-10-19 Ronald Silver Cannabis infused sweeteners and elixirs
JP6983868B2 (ja) 2016-04-22 2021-12-17 レセプター・ホールディングス・インコーポレイテッド 即効性の植物由来医薬化合物及び栄養補給剤
WO2017190070A1 (en) * 2016-04-29 2017-11-02 Corbus Pharmaceuticals, Inc. Methods for the treatment of infection
GB2551985B (en) * 2016-07-01 2019-01-30 Gw Res Ltd Novel formulation
CN109414403A (zh) 2016-07-11 2019-03-01 因泰克制药有限公司 口服胃滞留制剂及其用途
IL246790A0 (en) * 2016-07-14 2016-09-29 Friedman Doron Self-dissolving compounds of cannabinoids
WO2018058235A1 (en) * 2016-09-27 2018-04-05 CannTab Therapeutics Limited Sustained release cannabinoid formulations
US20180263954A1 (en) * 2016-09-27 2018-09-20 CannTab Therapeutics, Limited Sustained Release Cannabinoid Formulations
IL248149B (en) 2016-09-29 2020-03-31 Garti Nissim Formulations of dilutable cannabinoids and processes for their preparation
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
IL248150B (en) * 2016-09-29 2018-05-31 Garti Nissim A method for selective extraction of cannabinoid from plant origin
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
JP2020509081A (ja) * 2017-02-15 2020-03-26 モレキュラー インフュージョンズ、エルエルシー 製剤
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
CN111201041A (zh) 2017-07-11 2020-05-26 阿奎诺瓦股份公司 具有姜黄素和任选至少另一种活性物质的增溶物
US20190015346A1 (en) * 2017-07-14 2019-01-17 Pharmacannis Labs Llc Self-emulsifying drug delivery system
US20190015383A1 (en) * 2017-07-14 2019-01-17 5071, Inc. Cannabinoid compositions and methods of preparation thereof
WO2019018705A1 (en) * 2017-07-21 2019-01-24 Masaya World, Llc CAPRYLIC ACID ENRICHED IN CANNABIDIOL
GB2572126B (en) * 2018-01-03 2021-01-13 Gw Res Ltd Pharmaceutical
GB2572125B (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
US20200138772A1 (en) * 2018-07-09 2020-05-07 Volker Berl Stabilized formulations of cannabinoid compositions
HRP20231146T1 (hr) 2018-07-11 2024-01-05 Aquanova Ag Solubilizat ksantohumola
CN112533638A (zh) * 2018-07-11 2021-03-19 阿奎诺瓦股份公司 具有姜黄素和至少一种大麻素作为其他活性物质的增溶物
EP3937915A4 (en) * 2019-03-13 2022-12-21 Milane, Michael NOVEL NANOFORMULATION OF CANNABIDIOL (CBD) AND OTHER CANNABINOIDS FOR THE TREATMENT OF SKIN DISEASES
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
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)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA2185803C (en) * 1994-03-18 2006-07-11 Edward M. Rudnic 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
SI1280515T1 (sl) * 2000-03-09 2007-06-30 Gw Pharma Ltd Farmacevtski sestavki, ki vsebujejo kanabis
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

Also Published As

Publication number Publication date
US20070104741A1 (en) 2007-05-10
WO2007056242A1 (en) 2007-05-18
AU2006311818B9 (en) 2013-05-16
CA2618705A1 (en) 2007-05-18
EP1903866B1 (en) 2016-04-06
PT1903866E (pt) 2016-06-09
AU2006311818B2 (en) 2013-05-09
CA2618705C (en) 2014-04-22
JP2009514890A (ja) 2009-04-09
EP1903866A4 (en) 2010-12-22
DK1903866T3 (en) 2016-07-25
EP1903866A1 (en) 2008-04-02
AU2006311818A1 (en) 2007-05-18

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
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
AU2016203127A1 (en) An improved oral gastrointestinal dosage form delivery system of cannabinoids and/or standardized marijuana extracts
AU2013213706A1 (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
Natesh et al. Development of a self-nanoemulsifying drug delivery system of diindolylmethane for enhanced bioaccessibility, bioavailability and anti-breast cancer efficacy