WO2019067667A1 - Compositions pharmaceutiques à perméation améliorée - Google Patents

Compositions pharmaceutiques à perméation améliorée Download PDF

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Publication number
WO2019067667A1
WO2019067667A1 PCT/US2018/053026 US2018053026W WO2019067667A1 WO 2019067667 A1 WO2019067667 A1 WO 2019067667A1 US 2018053026 W US2018053026 W US 2018053026W WO 2019067667 A1 WO2019067667 A1 WO 2019067667A1
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WIPO (PCT)
Prior art keywords
pharmaceutical composition
composition according
polymeric matrix
less
film
Prior art date
Application number
PCT/US2018/053026
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English (en)
Inventor
Alexander Mark Schobel
Stephanie Marie VARJAN
Stephen Paul WARGACKI
Original Assignee
Aquestive Therapeutics, 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
Priority claimed from US15/724,234 external-priority patent/US11273131B2/en
Application filed by Aquestive Therapeutics, Inc. filed Critical Aquestive Therapeutics, Inc.
Priority to KR1020207012033A priority Critical patent/KR20200060457A/ko
Priority to JP2020517586A priority patent/JP7431724B2/ja
Priority to EP18786591.0A priority patent/EP3687509A1/fr
Priority to BR112020005967-6A priority patent/BR112020005967A2/pt
Priority to CA3076815A priority patent/CA3076815A1/fr
Priority to CN201880062717.5A priority patent/CN111132670A/zh
Publication of WO2019067667A1 publication Critical patent/WO2019067667A1/fr
Priority to IL273479A priority patent/IL273479A/en
Priority to JP2023188095A priority patent/JP2024012484A/ja

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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
    • A61K9/0012—Galenical forms characterised by the site of application
    • A61K9/0053—Mouth and digestive tract, i.e. intraoral and peroral administration
    • A61K9/006—Oral mucosa, e.g. mucoadhesive forms, sublingual droplets; Buccal patches or films; Buccal sprays
    • 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
    • A61K31/045—Hydroxy compounds, e.g. alcohols; Salts thereof, e.g. alcoholates
    • A61K31/05—Phenols
    • 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
    • A61K31/075—Ethers or acetals
    • A61K31/085—Ethers or acetals having an ether linkage to aromatic ring nuclear carbon
    • 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
    • A61K31/11—Aldehydes
    • 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
    • A61K31/13—Amines
    • A61K31/135—Amines having aromatic rings, e.g. ketamine, nortriptyline
    • A61K31/137—Arylalkylamines, e.g. amphetamine, epinephrine, salbutamol, ephedrine or methadone
    • 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
    • A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
    • A61K31/19—Carboxylic acids, e.g. valproic acid
    • A61K31/192—Carboxylic acids, e.g. valproic acid having aromatic groups, e.g. sulindac, 2-aryl-propionic acids, ethacrynic acid 
    • 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
    • A61K31/357—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having two or more oxygen atoms in the same ring, e.g. crown ethers, guanadrel
    • 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
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
    • A61K31/551—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole having two nitrogen atoms, e.g. dilazep
    • A61K31/5513—1,4-Benzodiazepines, e.g. diazepam or clozapine
    • 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
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
    • A61K31/551—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole having two nitrogen atoms, e.g. dilazep
    • A61K31/5513—1,4-Benzodiazepines, e.g. diazepam or clozapine
    • A61K31/5517—1,4-Benzodiazepines, e.g. diazepam or clozapine condensed with five-membered rings having nitrogen as a ring hetero atom, e.g. imidazobenzodiazepines, triazolam
    • 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
    • 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
    • A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
    • A61K47/36—Polysaccharides; Derivatives thereof, e.g. gums, starch, alginate, dextrin, hyaluronic acid, chitosan, inulin, agar or pectin
    • A61K47/38—Cellulose; Derivatives 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
    • A61K47/44—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
    • 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
    • A61K47/46—Ingredients of undetermined constitution or reaction products thereof, e.g. skin, bone, milk, cotton fibre, eggshell, oxgall or plant extracts
    • 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
    • A61K9/70—Web, sheet or filament bases ; Films; Fibres of the matrix type containing drug
    • A61K9/7007—Drug-containing films, membranes or sheets
    • 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
    • A61P25/08—Antiepileptics; Anticonvulsants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2300/00—Mixtures or combinations of active ingredients, wherein at least one active ingredient is fully defined in groups A61K31/00 - A61K41/00

Definitions

  • the pharmaceutical composition can be a film further comprising a polymeric matrix, the pharmaceutically active component being contained in the polymeric matrix.
  • the permeation enhancer can be a phytoextract.
  • the graphs show the permeation of an active material from a composition.
  • this graph shows average amount of active material permeated vs. time, with 8.00 mg/mL epinephrine bitartrate and 4.4 mg/mL epinephrine base solubilized.
  • this graph shows the impact of Enhancer L (clove oil) and film dimension (10-1-1 thinner, bigger film and 11-1-1 thicker, smaller film) on the concentration profiles of 40 mg Epinephrine films vs. a 0.3 mg Epipen.
  • this graph shows the alprazolam plasma concentration as a function of time following sublingual administration of alprazolam pharmaceutical composition films.
  • first double bond is between the sixth and seventh carbon atom, they are called co-6 fatty acids.
  • PUFAs are further metabolized in the body by the addition of carbon atoms and by desaturation (extraction of hydrogen).
  • Linoleic acid which is a co-6 fatty acid, is metabolized to ⁇ -linolenic acid, dihomo- ⁇ - linolinic acid, arachidonic acid, adrenic acid, tetracosatetraenoic acid, tetracosapentaenoic acid and docosapentaenoic acid
  • a-linolenic acid which is a co-3 fatty acid is metabolized to octadecatetraenoic acid, eicosatetraenoic acid, eicosapentaenoic acid (EPA), docosapentaenoic acid, tetracosapentaenoic acid, tetracosahexaen
  • a receptors are less sensitive to epinephrine, when activated, they override the vasodilation mediated by ⁇ -adrenoceptors because there are more peripheral al receptors than ⁇ -adrenoceptors.
  • the result is that high levels of circulating epinephrine cause vasoconstriction.
  • ⁇ - adrenoceptor stimulation dominates, producing vasodilation followed by decrease of peripheral vascular resistance.
  • the C3-C22 alcohol or acid can be an alcohol or acid having a straight C3-C22 hydrocarbon chain, for example a C3-C22 hydrocarbon chain optionally containing at least one double bond, at least one triple bond, or at least one double bond and one triple bond; said hydrocarbon chain being optionally substituted with C 1-4 alkyl, C 2- 4 alkenyl, C 2-4 alkynyl, C 1-4 alkoxy, hydroxyl, halo, amino, nitro, cyano, C 3-5 cycloalkyl, 3-5 membered heterocycloalkyl, monocyclic aryl, 5-6 membered heteroaryl, C 1-4 alkylcarbonyloxy, C 1-4 alkyloxycarbonyl, C 1-4 alkylcarbonyl, or formyl; and further being optionally interrupted by -0-, -N(R a )-, -N(R a )-C(0)- 0-, -0-C(0)-N(R a )-,
  • an interacter can also be a vasodilator or a therapeutic vasodilator.
  • useful water-soluble polymers include, but are not limited to, polyethylene oxide, pullulan, hydroxypropylmethyl cellulose, hydroxyethyl cellulose, hydroxypropyl cellulose, polyvinyl pyrrolidone, carboxymethyl cellulose, polyvinyl alcohol, sodium alginate, polyethylene glycol, xanthan gum, tragancanth gum, guar gum, acacia gum, arabic gum, polyacrylic acid, methylmethacrylate copolymer, carboxyvinyl copolymers, starch, gelatin, and combinations thereof.
  • biodegradable polymers include materials that chemically degrade, as opposed to materials that physically break apart (i.e., bioerodable materials).
  • bioerodable materials include materials that chemically degrade, as opposed to materials that physically break apart (i.e., bioerodable materials).
  • the polymers incorporated in the films can also include a combination of biodegradable or bioerodable materials.
  • aldehydes and esters such as benzaldehyde (cherry, almond), citral i.e., alphacitral (lemon, lime), neral, i.e., beta-citral (lemon, lime), decanal (orange, lemon), aldehyde C-8 (citrus fruits), aldehyde C-9 (citrus fruits), aldehyde C-12 (citrus fruits), tolyl aldehyde (cherry, almond), 2,6-dimethyloctanol (green fruit), or 2-dodecenal (citrus, mandarin), combinations thereof and the like.
  • aldehydes and esters such as benzaldehyde (cherry, almond), citral i.e., alphacitral (lemon, lime), neral, i.e., beta-citral (lemon, lime), decanal (orange, lemon), aldehyde C-8 (citrus fruits), aldeh
  • the graphs show the permeation of an active material from a composition.
  • the graph shows that for the Epinephrine Base - solubilized in-situ vs. the inherently soluble Epinephrine Bitartrate, no meaningful differences were observed.
  • Epinephrine Bitartrate was selected for further development based on ease of processing. Flux is derived as slope of the amount permeated as a function of time. Steady state flux is taken from the plateau of flux vs time curve multiplied by the volume of receiver media and normalized for permeation area.
  • Porcine oral mucosal tissue has similar histological characteristics to human oral mucosal tissue (Heaney TG, Jones RS, Histological investigation of the influence of adult porcine alveolar mucosal connective tissues on epithelial differentiation. Arch Oral Biol 23 (1978) 713— 717; Squier CA, and Collins P, The relationship between soft tissue attachment, epithelial downgrowth and surface porosity. Journal of Periodontal Research 16 (1981) 434-440). Lesch et al.
  • Treatment A no patients spit or blew out DBSF following initial adherence to the buccal mucosa, while 3 (9.1%>) subjects spit or blew out the film during Treatment B following initial placement.
  • DBSF was generally safe and well tolerated.
  • the most common adverse event possibly related to drug was somnolence reported in two (5.7 %) of 35 of subjects. There were no serious adverse events related to study drug, and no subject withdrew because of an adverse event.

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Epidemiology (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Emergency Medicine (AREA)
  • Physiology (AREA)
  • Nutrition Science (AREA)
  • Botany (AREA)
  • Inorganic Chemistry (AREA)
  • Biomedical Technology (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Organic Chemistry (AREA)
  • Pain & Pain Management (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicinal Preparation (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Medicines Containing Plant Substances (AREA)

Abstract

L'invention concerne des compositions pharmaceutiques ayant des propriétés de perméation de principe actif améliorées.
PCT/US2018/053026 2017-09-27 2018-09-27 Compositions pharmaceutiques à perméation améliorée WO2019067667A1 (fr)

Priority Applications (8)

Application Number Priority Date Filing Date Title
KR1020207012033A KR20200060457A (ko) 2017-09-27 2018-09-27 강화된 투과를 가지는 약물학적 조성물
JP2020517586A JP7431724B2 (ja) 2017-09-27 2018-09-27 増強された透過を有する医薬組成物
EP18786591.0A EP3687509A1 (fr) 2017-09-27 2018-09-27 Compositions pharmaceutiques à perméation améliorée
BR112020005967-6A BR112020005967A2 (pt) 2017-09-27 2018-09-27 composições farmacêuticas com permeação realçada
CA3076815A CA3076815A1 (fr) 2017-09-27 2018-09-27 Compositions pharmaceutiques a permeation amelioree
CN201880062717.5A CN111132670A (zh) 2017-09-27 2018-09-27 具有增强的渗透的药物组合物
IL273479A IL273479A (en) 2017-09-27 2020-03-22 Pharmaceutical preparations with improved permeability
JP2023188095A JP2024012484A (ja) 2017-09-27 2023-11-02 増強された透過を有する医薬組成物

Applications Claiming Priority (6)

Application Number Priority Date Filing Date Title
US201715717856A 2017-09-27 2017-09-27
US15/717,856 2017-09-27
US15/724,234 2017-10-03
US15/724,234 US11273131B2 (en) 2016-05-05 2017-10-03 Pharmaceutical compositions with enhanced permeation
US201862735822P 2018-09-24 2018-09-24
US62/735,822 2018-09-24

Publications (1)

Publication Number Publication Date
WO2019067667A1 true WO2019067667A1 (fr) 2019-04-04

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Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2018/053026 WO2019067667A1 (fr) 2017-09-27 2018-09-27 Compositions pharmaceutiques à perméation améliorée

Country Status (8)

Country Link
EP (1) EP3687509A1 (fr)
JP (2) JP7431724B2 (fr)
KR (1) KR20200060457A (fr)
CN (1) CN111132670A (fr)
BR (1) BR112020005967A2 (fr)
CA (1) CA3076815A1 (fr)
IL (1) IL273479A (fr)
WO (1) WO2019067667A1 (fr)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2021087359A1 (fr) * 2019-11-01 2021-05-06 Aquestive Therapeutics, Inc. Compositions de promédicament et procédés de traitement
US11191737B2 (en) 2016-05-05 2021-12-07 Aquestive Therapeutics, Inc. Enhanced delivery epinephrine compositions
US11273131B2 (en) 2016-05-05 2022-03-15 Aquestive Therapeutics, Inc. Pharmaceutical compositions with enhanced permeation
US11839602B2 (en) 2020-11-25 2023-12-12 Nicoventures Trading Limited Oral cannabinoid product with lipid component
US11896711B2 (en) 2019-12-09 2024-02-13 Nicoventures Trading Limited Process of making nanoemulsion

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN114894675B (zh) * 2022-05-06 2024-04-19 江苏省农业科学院 一种农药助剂在植物叶片表面渗透行为的比较方法

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US20050037055A1 (en) 2002-04-11 2005-02-17 Monosolrx Llc. Polyethylene oxide-based films and drug delivery systems made therefrom
US20050042271A1 (en) * 1999-11-19 2005-02-24 Xel Herbaceuticals, Inc . Transdermal delivery system for alkaloids of aconitum species
US7357891B2 (en) 2001-10-12 2008-04-15 Monosol Rx, Llc Process for making an ingestible film
US7425292B2 (en) 2001-10-12 2008-09-16 Monosol Rx, Llc Thin film with non-self-aggregating uniform heterogeneity and drug delivery systems made therefrom
US8652378B1 (en) 2001-10-12 2014-02-18 Monosol Rx Llc Uniform films for rapid dissolve dosage form incorporating taste-masking compositions
US8765167B2 (en) 2001-10-12 2014-07-01 Monosol Rx, Llc Uniform films for rapid-dissolve dosage form incorporating anti-tacking compositions
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JP2004043450A (ja) 2002-05-16 2004-02-12 Kyukyu Yakuhin Kogyo Kk 速溶性フィルム状製剤
EP2161021B1 (fr) 2007-06-07 2017-03-08 Sato Pharmaceutical Co. Ltd. Préparation de film médicinal avec une propriété de dissolution rapide et une flexibilité
JP5435853B2 (ja) 2007-09-28 2014-03-05 興和株式会社 塩酸フェニレフリン含有速溶性フィルム製剤及びその製造方法

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US20050042271A1 (en) * 1999-11-19 2005-02-24 Xel Herbaceuticals, Inc . Transdermal delivery system for alkaloids of aconitum species
US7357891B2 (en) 2001-10-12 2008-04-15 Monosol Rx, Llc Process for making an ingestible film
US7425292B2 (en) 2001-10-12 2008-09-16 Monosol Rx, Llc Thin film with non-self-aggregating uniform heterogeneity and drug delivery systems made therefrom
US8652378B1 (en) 2001-10-12 2014-02-18 Monosol Rx Llc Uniform films for rapid dissolve dosage form incorporating taste-masking compositions
US8765167B2 (en) 2001-10-12 2014-07-01 Monosol Rx, Llc Uniform films for rapid-dissolve dosage form incorporating anti-tacking compositions
US20050037055A1 (en) 2002-04-11 2005-02-17 Monosolrx Llc. Polyethylene oxide-based films and drug delivery systems made therefrom
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