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)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (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

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 (104)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20070219131A1 (en) * 2004-04-15 2007-09-20 Ben-Sasson Shmuel A Compositions capable of facilitating penetration across a biological barrier
CN101084016A (zh) * 2004-04-15 2007-12-05 克艾思马有限公司 能够容易穿透生物学障碍的组合物
KR20070118069A (ko) * 2004-12-09 2007-12-13 인시스 테라퓨틱스, 인코포레이티드 실온에서 안정한 드로나비놀 제형
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
BRPI0715328A2 (pt) * 2006-08-04 2013-07-09 Insys Therapeutics Inc formulaÇço, e, dispositivo de dose unitÁria ou de dose méltipla para a administraÇço sublingual de uma droga
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
WO2009020666A1 (en) * 2007-08-06 2009-02-12 Insys Therapeutics Inc. Oral cannabinoid liquid formulations and methods of treatment
EP2192893B1 (en) * 2007-08-21 2015-08-19 Basilea Pharmaceutica AG Antifungal composition
EP2268160B1 (en) * 2008-03-20 2012-12-05 Virun, Inc. Emulsions including a peg-derivative of tocopherol
EP2268274B1 (en) * 2008-03-20 2012-05-16 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
GB2482810A (en) 2008-09-17 2012-02-15 Chiasma Inc Enhanced delivery of exenatide using a medium chain fatty acid and salt thereof
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
US20120178806A1 (en) * 2009-09-15 2012-07-12 Qlt Inc. 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
US20110136815A1 (en) * 2009-12-08 2011-06-09 Horst Zerbe Solid oral film dosage forms and methods for making same
US10610528B2 (en) 2009-12-08 2020-04-07 Intelgenx Corp. Solid oral film dosage forms and methods for making same
CA2792330C (en) 2010-03-23 2017-01-03 Virun, Inc Nanoemulsion including a peg-derivative of vitamin e and a sucrose fatty acid ester
GB201006200D0 (en) * 2010-04-14 2010-06-02 Ayanda As Composition
BR112012026939A2 (pt) 2010-04-19 2016-07-12 Quadra Logic Tech Inc método para tratamento de um paciente sofrendo da perda ou debilitação da visão
US8741373B2 (en) 2010-06-21 2014-06-03 Virun, Inc. Compositions containing non-polar compounds
SI2600838T1 (sl) * 2010-08-04 2015-12-31 Gruenenthal Gmbh Farmacevtska odmerna oblika, ki obsega 6'-fluoro-(N-metil- ali N,N-dimetil-)-4-fenil-4',9'-dihidro-3'H-spiro(cikloheksan-1,1'-pirano (3,4,b)indol)-4-amin
US9737500B2 (en) 2010-10-29 2017-08-22 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
US8895537B2 (en) 2010-10-29 2014-11-25 Infirst Healthcare Ltd. Compositions and methods for treating cardiovascular diseases
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
US11730709B2 (en) 2010-10-29 2023-08-22 Infirst Healthcare Limited Compositions and methods for treating severe pain
US10695432B2 (en) 2010-10-29 2020-06-30 Infirst Healthcare Limited Solid solution compositions and use in severe pain
US9271950B2 (en) 2010-10-29 2016-03-01 Infirst Healthcare Limited Compositions for treating chronic inflammation and inflammatory diseases
US9308213B2 (en) 2010-10-29 2016-04-12 Infirst Healthcare Limited Solid solution compositions and use in chronic inflammation
US11224659B2 (en) 2010-10-29 2022-01-18 Infirst Healthcare Limited Solid solution compositions and use in severe pain
US10695431B2 (en) 2010-10-29 2020-06-30 Infirst Healthcare Limited Solid solution compositions and use in cardiovascular disease
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
MX370928B (es) 2012-03-01 2020-01-08 Retinagenix LLC El uso de 9-cis-retinil acetato para mejorar la función visual de un sujeto que padece de pérdida de la función visual originada por una deficiencia retinoide endógena de 11-cis retinal.
JP6326563B2 (ja) * 2012-03-19 2018-05-23 アリエル−ユニバーシティー リサーチ アンド デベロップメント カンパニー リミテッド β−カリオフィレンとＣＢ２受容体アゴニストを用いた精神病の治療
DE102012105063C5 (de) * 2012-06-12 2023-09-14 Thc Pharm Gmbh The Health Concept Stabilisierung von Cannabinoiden und deren pharmazeutischen Zubereitungen
US10265293B2 (en) 2012-10-04 2019-04-23 Insys Development Company, Inc. Oral cannabinoid formulations
US9345771B2 (en) 2012-10-04 2016-05-24 Insys Development Company, Inc. Oral cannabinoid formulations
US11253472B2 (en) 2012-10-04 2022-02-22 Benuvia Therapeutics Llc Oral cannabinoid formulations
EP3851101A1 (en) 2013-02-12 2021-07-21 Corbus Pharmaceuticals, Inc. Ultrapure tetrahydrocannabinol-11-oic acids
EP2961402A4 (en) 2013-02-28 2016-11-23 Full Spectrum Lab Ltd 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
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
AU2015280412B2 (en) * 2014-06-26 2018-07-26 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
WO2016126830A1 (en) 2015-02-03 2016-08-11 Chiasma Inc. Method of treating diseases
WO2016147186A1 (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
DK3302437T3 (da) * 2015-05-28 2023-01-09 Radius Pharmaceuticals Inc Stabile cannabinoidformuleringer
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
PL3368014T3 (pl) 2015-10-26 2024-03-11 Yissum Research Development Company Of The Hebrew University Of Jerusalem Ltd Nowe preparaty kannabinoidów
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
EP3442521A4 (en) * 2016-04-15 2020-01-01 SRE Wellness, Inc. SWEETENERS AND ELIXIRS INFused WITH CANNABIS
MX2018012913A (es) 2016-04-22 2019-01-30 Receptor Life Sciences Inc Compuestos medicinales y suplementos nutricionales de base vegetal de rapida accion.
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
EP3481371A1 (en) * 2016-07-11 2019-05-15 Intec Pharma Ltd. Oral gastroretentive formulations and uses thereof
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
CA3036585A1 (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
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
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
EP3582755A4 (en) * 2017-02-15 2020-12-23 Molecular Infusions, LLC FORMULATIONS
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
CA3148455A1 (en) 2017-07-11 2019-01-17 Aquanova Ag Solubilizate with curcumin and optionally at least one other active substance
US20190015346A1 (en) * 2017-07-14 2019-01-17 Pharmacannis Labs Llc Self-emulsifying drug delivery system
CA3069694A1 (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
GB2569961B (en) * 2018-01-03 2021-12-22 Gw Res Ltd Pharmaceutical
GB2572126B (en) * 2018-01-03 2021-01-13 Gw Res Ltd Pharmaceutical
GB2572125B (en) * 2018-01-03 2021-01-13 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***二酚自乳化给药***、固体自乳化制剂及其制备方法
EP3820452A1 (en) * 2018-07-09 2021-05-19 Volker Berl Stabilized formulations of cannabinoid compositions
BR112020026393A2 (pt) * 2018-07-11 2021-03-23 Aquanova Ag solubilizado com curcumina e pelo menos o canabinoide thc como uma outra substância ativa
US11786484B2 (en) 2018-07-11 2023-10-17 Aquanova Ag Xanthohumol solubilizate
WO2020186212A1 (en) * 2019-03-13 2020-09-17 Milane Michael Novel nano-formulation of cannabidiol (cbd) and other cannabinoids for treatment of skin diseases
CA3137225A1 (en) * 2019-04-18 2020-10-22 Simon Benita Self-emulsifying drug delivery systems for delivery of lipophilic compounds
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***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
US11242330B1 (en) 2021-02-25 2022-02-08 Acid Neutral Alkaline Laboratory Organic catalyst and method for preparation of aromatic tricyclic pyrans
US11242328B1 (en) 2021-02-25 2022-02-08 Acid Neutral Alkaline Laboratory Heterogeneous 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)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0788346B9 (en) * 1994-03-18 2007-02-14 Supernus Pharmaceuticals, 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
AU782991B2 (en) * 2000-03-09 2005-09-15 GW Research Limited Pharmaceutical compositions
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
EP1903866A1 (en) 2008-04-02
AU2006311818B9 (en) 2013-05-16
AU2006311818B2 (en) 2013-05-09
EP1903866A4 (en) 2010-12-22
CA2618705A1 (en) 2007-05-18
JP2009514890A (ja) 2009-04-09
CA2618705C (en) 2014-04-22
PT1903866E (pt) 2016-06-09
EP1903866B1 (en) 2016-04-06
US20070104741A1 (en) 2007-05-10
WO2007056242A1 (en) 2007-05-18
AU2006311818A1 (en) 2007-05-18
DK1903866T3 (en) 2016-07-25

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
AU2016203127A1 (en) An improved oral gastrointestinal dosage form delivery system of cannabinoids and/or standardized marijuana extracts
AU2019205118B2 (en) Modified release composition comprising a cannabinoid
KR102685325B1 (ko) 칸나비노이드를 포함하는 변형 방출형 조성물
Natesh et al. Development of a self-nanoemulsifying drug delivery system of diindolylmethane for enhanced bioaccessibility, bioavailability and anti-breast cancer efficacy