WO2014144895A1 - Microcrystalline diketopiperazine compositions and methods - Google Patents

Microcrystalline diketopiperazine compositions and methods Download PDF

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Publication number
WO2014144895A1
WO2014144895A1 PCT/US2014/029491 US2014029491W WO2014144895A1 WO 2014144895 A1 WO2014144895 A1 WO 2014144895A1 US 2014029491 W US2014029491 W US 2014029491W WO 2014144895 A1 WO2014144895 A1 WO 2014144895A1
Authority
WO
WIPO (PCT)
Prior art keywords
particles
diketopiperazine
suspension
μιη
microcrystalline
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.)
Ceased
Application number
PCT/US2014/029491
Other languages
English (en)
French (fr)
Inventor
Bryan R. Wilson
Joseph J. Guarneri
Marshall L. Grant
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.)
Mannkind Corp
Original Assignee
Mannkind Corp
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 to AU2014228415A priority Critical patent/AU2014228415B2/en
Priority to CA2906817A priority patent/CA2906817C/en
Priority to KR1020157028971A priority patent/KR102246914B1/ko
Priority to KR1020217012093A priority patent/KR102391750B1/ko
Priority to MX2015013017A priority patent/MX369136B/es
Priority to US14/774,311 priority patent/US10421729B2/en
Priority to EP19186542.7A priority patent/EP3587404B1/en
Priority to ES14721140T priority patent/ES2754388T3/es
Priority to BR112015023168-3A priority patent/BR112015023168B1/pt
Priority to SG11201507564PA priority patent/SG11201507564PA/en
Priority to EP14721140.3A priority patent/EP2970149B1/en
Priority to CN201480015837.1A priority patent/CN105102436B/zh
Priority to KR1020227013752A priority patent/KR102499439B1/ko
Priority to HK16107016.7A priority patent/HK1219097B/en
Priority to JP2016503112A priority patent/JP6523247B2/ja
Application filed by Mannkind Corp filed Critical Mannkind Corp
Priority to MX2019012752A priority patent/MX392016B/es
Publication of WO2014144895A1 publication Critical patent/WO2014144895A1/en
Priority to IL241490A priority patent/IL241490B/en
Anticipated expiration legal-status Critical
Priority to AU2018253545A priority patent/AU2018253545B2/en
Priority to US16/532,968 priority patent/US10745359B2/en
Priority to AU2020200744A priority patent/AU2020200744B2/en
Priority to US16/925,166 priority patent/US11192862B2/en
Priority to AU2021203201A priority patent/AU2021203201B2/en
Priority to US17/470,212 priority patent/US20220048868A1/en
Priority to AU2022235510A priority patent/AU2022235510B2/en
Priority to AU2023282272A priority patent/AU2023282272B2/en
Priority to AU2025204271A priority patent/AU2025204271A1/en
Ceased legal-status Critical Current

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
    • A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
    • A61K9/141—Intimate drug-carrier mixtures characterised by the carrier, e.g. ordered mixtures, adsorbates, solid solutions, eutectica, co-dried, co-solubilised, co-kneaded, co-milled, co-ground products, co-precipitates, co-evaporates, co-extrudates, co-melts; Drug nanoparticles with adsorbed surface modifiers
    • A61K9/145—Intimate drug-carrier mixtures characterised by the carrier, e.g. ordered mixtures, adsorbates, solid solutions, eutectica, co-dried, co-solubilised, co-kneaded, co-milled, co-ground products, co-precipitates, co-evaporates, co-extrudates, co-melts; Drug nanoparticles with adsorbed surface modifiers with organic compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
    • C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
    • C07D241/06—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having one or two double bonds between ring members or between ring members and non-ring members
    • C07D241/08—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having one or two double bonds between ring members or between ring members and non-ring members with oxygen atoms directly attached to ring carbon atoms
    • 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
    • A61K31/557—Eicosanoids, e.g. leukotrienes or prostaglandins
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K38/00—Medicinal preparations containing peptides
    • A61K38/16—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
    • A61K38/17—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans
    • A61K38/22—Hormones
    • A61K38/26—Glucagons
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K38/00—Medicinal preparations containing peptides
    • A61K38/16—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
    • A61K38/17—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans
    • A61K38/22—Hormones
    • A61K38/28—Insulins
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
    • A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
    • 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
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/0012—Galenical forms characterised by the site of application
    • A61K9/007—Pulmonary tract; Aromatherapy
    • A61K9/0073—Sprays or powders for inhalation; Aerolised or nebulised preparations generated by other means than thermal energy
    • A61K9/0075—Sprays or powders for inhalation; Aerolised or nebulised preparations generated by other means than thermal energy for inhalation via a dry powder inhaler [DPI], e.g. comprising micronized drug mixed with lactose carrier particles
    • 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
    • A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
    • A61K9/50—Microcapsules having a gas, liquid or semi-solid filling; Solid microparticles or pellets surrounded by a distinct coating layer, e.g. coated microspheres, coated drug crystals
    • A61K9/5005—Wall or coating material
    • A61K9/5015—Organic compounds, e.g. fats, sugars
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/04—Anorexiants; Antiobesity agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
    • A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D1/00—Evaporating
    • B01D1/16—Evaporating by spraying
    • B01D1/18—Evaporating by spraying to obtain dry solids

Definitions

  • Drug delivery to the lungs for agents having systemic effects can also be performed.
  • Advantages of the lungs for delivery of systemic agents include the large surface area and the ease of uptake by the lung's mucosal surface.
  • Pulmonary drug delivery systems present many difficulties, for example, the use of propellants, and aerosolization of biological agents such as proteins and peptides can lead to denaturation, and excessive loss of the agent to be delivered.
  • One other problem associated with all of these forms of pulmonary drug delivery is that it is difficult to deliver drugs into the lungs due to problems in getting the drugs past all of the natural barriers, such as the cilia lining the trachea, and in trying to administer a uniform volume and weight of drug.
  • the present disclosure provides improved microcrystalline particles, compositions, methods of making the particles, and methods that allow for improved delivery of drugs to the lungs for treating diseases and disorders in a subject.
  • Embodiments disclosed herein achieve improved delivery by providing crystalline diketopiperazine compositions comprising microcrystalline diketopiperazine particles having high capacity for drug adsorption yielding powders having high drug content of one or more active agents.
  • Powders made with the present microcrystalline particles can deliver increased drug content in lesser amounts of powder dose, which can facilitate drug delivery to a patient.
  • the powders can be made by various methods including, methods utilizing surfactant- free solutions or solutions comprising surfactants depending on the starting materials.
  • Certain embodiments disclosed herein can comprise powders comprising a plurality of substantially uniform, microcrystalline particles, wherein the particles have a substantially hollow spherical structure and comprise a shell which can be porous, and comprises crystallites of a diketopiperazine that do not self-assemble.
  • a diketopiperazine composition comprising a plurality of substantially uniformly formed, microcrystalline particles, wherein the particles have a substantially hollow spherical structure and comprise a shell comprising crystallites of a diketopiperazine that do not self-assemble, and the particles have a volumetric mean geometric diameter less than equal to 5 ⁇ ; wherein the particles are formed by a method comprising the step of combining diketopiperazine in a solution and a solution of acetic acid without the presence of a surfactant and without the presence of an active agent, and concurrently homogenizing in a high shear mixer at high pressures of up to 2,000 psi to form a precipitate; washing the precipitate in suspension with deionized water; concentrating the suspension and drying the suspension in a spray drying apparatus.
  • the composition can comprise microcrystalline particles comprising one or more active ingredients; wherein the active ingredients are peptides, proteins, nucleic acid molecules, small organic molecules, or combinations thereof.
  • the active ingredient is a peptide, oligopeptide, polypeptide or protein
  • the peptide, oligopeptide, polypeptide or protein can be an endocrine hormone, a neurotransmitter, a vasoactive peptide, a receptor peptide, a receptor agonist or antagonist, and the like.
  • the endocrine hormone is insulin, parathyroid hormone, calcitonin, glucagon, glucagon-like peptide 1 , oxyntomodulin, peptide YY, leptin, or an analog of said endocrine hormone.
  • excipients can be incorporated into the particles by addition to one, another, or all feedstocks used in the spray drying step.
  • the compositions can contain insulin in amount up to, for example, 9 units or 10 units per milligram of powder to be delivered to a patient.
  • the crystalline diketopiperazine composition comprises a diketopiperazine of the formula 2,5-diketo-3,6-bis(N-X-4- aminoalkyl)piperazine, wherein alkyl denotes an alkyl containing 3 to 20 carbon atoms, including propyl, butyl, pentyl, hexyl, heptyl and the like; and the formula is, for example, 2,5-diketo-3,6-bis(N-X-4-aminobutyl)piperazine, wherein X is selected from the group consisting of fumaryl, succinyl, maleyl, malonyl, and glutaryl, or a salt thereof.
  • the diketopiperazine is (bis— 3,6-(N- fumaryl-4-aminobutyl)-2,5-diketo-diketopiperazine having the formula:
  • the suspension has a bimodal distribution of crystallites having particle sizes ranging from about 0.05 ⁇ to about 10 ⁇ in diameter and comprising a trans isomer content ranging from about 45% to 65%;
  • the method can further comprise the step of adding a third solution to the diketopiperazine crystallite suspension prior to atomizing the suspension; wherein the solution contains a drug or a pharmaceutically active ingredient, and the atomizing step can be performed using an external mixing 2-fluid nozzle into a spray dryer fitted with a high efficiency cyclone separator under air or gas, including nitrogen gas.
  • microcrystalline particles can be made by a process comprising, preparing a first solution comprising a diketopiperazine in water, for example, 2,5-diketo-3,6-(N-fumaryl-4-aminobutyl)piperazine disodium salt and a surfactant such as polysorbate 80; preparing a second solution comprising acetic acid at a concentration about 10.5% (w/w) and a surfactant at a concentration of about 0.5% (w/w); mixing the first solution and the second solution in a high shear mixer to form a suspension; optionally testing the suspension to determine the particle size distribution so that the suspension comprises a bimodal particle size distribution, with particles ranging in size from about 0.2 ⁇ to about 10 ⁇ in diameter, wherein a first peak of particles have an average diameter of about 0.4 ⁇ and a second peak of particle have an mean diameter of about 2.4 ⁇ , and spray-drying the suspension to obtain a dry powder.
  • a diketopiperazine in water for
  • Certain embodiments can comprise a disruption step to reduce the size of the larger-sized population in the bimodal distribution, for example utilizing sonication, stirring, or homogenization.
  • the disruption step can be performed prior to atomizing the suspension.
  • the method for making the microcrystalline diketopiperazine particles can further include a wash step using deionized water.
  • the atomizing step can be performed, for example, using an external mixing 2-fluid nozzle into a spray dryer fitted with a high efficiency cyclone separator.
  • a composition comprising more than one active agent can be made using the present method.
  • the method of making such composition comprises the steps of making microcrystalline diketopiperazine particles comprising more than one active agent wherein each active agent/ingredient is processed separately in a solution and added to separate suspensions of diketopiperazine particles and solution conditions are changed to promote adsorption of the active agent onto the surfaces of the crystallites, then the two or more separate suspensions comprising the active agents are blended prior to dispersing and spray-drying the particles.
  • the blend includes a suspension containing diketopiperazine particles without active agent, for example in order to achieve a lower overall content of the active agent.
  • the one or more independent solutions containing a single active agent can be combined with a single suspension comprising the diketopiperazine particles prior to dispersing and spray-drying the particles.
  • the resultant dry powder comprises a composition comprising two or more active ingredients.
  • the amount of each ingredient in the composition can be controlled depending on the need of the patient population to be treated.
  • the dry powder comprises a composition comprising 2,5-diketo-3,6-bis(N-X-4-aminobutyl)piperazine, wherein X is fumaryl and the composition comprises substantially homogeneous microcrystalline particles comprising a drug; wherein the particles are substantially spherical in shape having a substantially hollow core and the crystallites form a shell of the sphere.
  • the particle size distribution of the combination powder was centered between those of the two individual suspensions and was significantly narrower.
  • the combination powder comprised particles having a diameter of from about 1 ⁇ to about 10 ⁇ .
  • the crystallites containing the insulin were smaller (from about 0.25 ⁇ to about 10 ⁇ ) than the GLP-1 containing crystallites which have a diameter ranging from about 0.5 ⁇ to about 50 ⁇ .
  • the atomization step in spray drying probably dissociates the original clusters of crystallites in suspension and re-forms the particles with a size distribution that depends on the conditions in the suspension and spray-drying conditions.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Animal Behavior & Ethology (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Epidemiology (AREA)
  • Diabetes (AREA)
  • Organic Chemistry (AREA)
  • Endocrinology (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Zoology (AREA)
  • Gastroenterology & Hepatology (AREA)
  • Immunology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Obesity (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Hematology (AREA)
  • Emergency Medicine (AREA)
  • Otolaryngology (AREA)
  • Pulmonology (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Child & Adolescent Psychology (AREA)
  • Medicinal Preparation (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
PCT/US2014/029491 2013-03-15 2014-03-14 Microcrystalline diketopiperazine compositions and methods Ceased WO2014144895A1 (en)

Priority Applications (26)

Application Number Priority Date Filing Date Title
JP2016503112A JP6523247B2 (ja) 2013-03-15 2014-03-14 微結晶性ジケトピペラジン粒子の製造方法および乾燥粉末組成物の製造方法
KR1020157028971A KR102246914B1 (ko) 2013-03-15 2014-03-14 미세결정성 디케토피페라진 조성물 및 방법
KR1020217012093A KR102391750B1 (ko) 2013-03-15 2014-03-14 미세결정성 디케토피페라진 조성물 및 방법
MX2015013017A MX369136B (es) 2013-03-15 2014-03-14 Composiciones de dicetopiperazina microcristalina y metodos.
US14/774,311 US10421729B2 (en) 2013-03-15 2014-03-14 Microcrystalline diketopiperazine compositions and methods
EP19186542.7A EP3587404B1 (en) 2013-03-15 2014-03-14 Microcrystalline diketopiperazine compositions, methods for preparation and use thereof
ES14721140T ES2754388T3 (es) 2013-03-15 2014-03-14 Composiciones y métodos de dicetopiperazina microcristalina
BR112015023168-3A BR112015023168B1 (pt) 2013-03-15 2014-03-14 Composição de 3,6-bis(n-fumaril-4-aminobutil)-2,5-dicetopiperazina cristalina, método de produção de partículas de 3,6-bis(n-fumaril-4-aminobutil)-2,5-dicetopiperazina e uso de uma composição de dicetopiperazina cristalina
SG11201507564PA SG11201507564PA (en) 2013-03-15 2014-03-14 Microcrystalline diketopiperazine compositions and methods
EP14721140.3A EP2970149B1 (en) 2013-03-15 2014-03-14 Microcrystalline diketopiperazine compositions and methods
CN201480015837.1A CN105102436B (zh) 2013-03-15 2014-03-14 微晶二酮哌嗪组合物以及方法
KR1020227013752A KR102499439B1 (ko) 2013-03-15 2014-03-14 미세결정성 디케토피페라진 조성물 및 방법
HK16107016.7A HK1219097B (en) 2013-03-15 2014-03-14 Microcrystalline diketopiperazine compositions and methods
AU2014228415A AU2014228415B2 (en) 2013-03-15 2014-03-14 Microcrystalline diketopiperazine compositions and methods
MX2019012752A MX392016B (es) 2013-03-15 2014-03-14 Composiciones de dicetopiperazina microcristalina y métodos.
CA2906817A CA2906817C (en) 2013-03-15 2014-03-14 Microcrystalline diketopiperazine compositions and methods
IL241490A IL241490B (en) 2013-03-15 2015-09-10 Preparations containing microcrystalline dicotpiperazines and their uses
AU2018253545A AU2018253545B2 (en) 2013-03-15 2018-10-24 Microcrystalline diketopiperazine compositions and methods
US16/532,968 US10745359B2 (en) 2013-03-15 2019-08-06 Microcrystalline diketopiperazine compositions and methods
AU2020200744A AU2020200744B2 (en) 2013-03-15 2020-01-31 Microcrystalline diketopiperazine compositions and methods
US16/925,166 US11192862B2 (en) 2013-03-15 2020-07-09 Microcrystalline diketopiperazine compositions and methods
AU2021203201A AU2021203201B2 (en) 2013-03-15 2021-05-18 Microcrystalline diketopiperazine compositions and methods
US17/470,212 US20220048868A1 (en) 2013-03-15 2021-09-09 Microcrystalline Diketopiperazine Compositions and Methods
AU2022235510A AU2022235510B2 (en) 2013-03-15 2022-09-19 Microcrystalline diketopiperazine compositions and methods
AU2023282272A AU2023282272B2 (en) 2013-03-15 2023-12-14 Microcrystalline diketopiperazine compositions and methods
AU2025204271A AU2025204271A1 (en) 2013-03-15 2025-06-08 Microcrystalline diketopiperazine compositions and methods

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US201361800520P 2013-03-15 2013-03-15
US61/800,520 2013-03-15

Related Child Applications (2)

Application Number Title Priority Date Filing Date
US14/774,311 A-371-Of-International US10421729B2 (en) 2013-03-15 2014-03-14 Microcrystalline diketopiperazine compositions and methods
US16/532,968 Division US10745359B2 (en) 2013-03-15 2019-08-06 Microcrystalline diketopiperazine compositions and methods

Publications (1)

Publication Number Publication Date
WO2014144895A1 true WO2014144895A1 (en) 2014-09-18

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Application Number Title Priority Date Filing Date
PCT/US2014/029491 Ceased WO2014144895A1 (en) 2013-03-15 2014-03-14 Microcrystalline diketopiperazine compositions and methods

Country Status (13)

Country Link
US (5) US10421729B2 (enExample)
EP (2) EP3587404B1 (enExample)
JP (6) JP6523247B2 (enExample)
KR (3) KR102499439B1 (enExample)
CN (2) CN105102436B (enExample)
AU (7) AU2014228415B2 (enExample)
BR (1) BR112015023168B1 (enExample)
CA (1) CA2906817C (enExample)
ES (2) ES2754388T3 (enExample)
IL (1) IL241490B (enExample)
MX (2) MX392016B (enExample)
SG (2) SG10201708090TA (enExample)
WO (1) WO2014144895A1 (enExample)

Cited By (31)

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US9339615B2 (en) 2008-06-13 2016-05-17 Mannkind Corporation Dry powder inhaler and system for drug delivery
US9346766B2 (en) 2004-08-20 2016-05-24 Mannkind Corporation Catalysis of diketopiperazine synthesis
US9364436B2 (en) 2011-06-17 2016-06-14 Mannkind Corporation High capacity diketopiperazine microparticles and methods
US9446001B2 (en) 2005-09-14 2016-09-20 Mannkind Corporation Increasing drug affinity for crystalline microparticle surfaces
US9610351B2 (en) 2011-10-24 2017-04-04 Mannkind Corporation Methods and compositions for treating pain
US9630930B2 (en) 2009-06-12 2017-04-25 Mannkind Corporation Diketopiperazine microparticles with defined specific surface areas
US9655850B2 (en) 2008-12-29 2017-05-23 Mannkind Corporation Substituted diketopiperazine analogs for use as drug delivery agents
US9662461B2 (en) 2008-06-13 2017-05-30 Mannkind Corporation Dry powder drug delivery system and methods
US9675674B2 (en) 2004-08-23 2017-06-13 Mannkind Corporation Diketopiperazine salts for drug delivery and related methods
US9700690B2 (en) 2002-03-20 2017-07-11 Mannkind Corporation Inhalation apparatus
US9706944B2 (en) 2009-11-03 2017-07-18 Mannkind Corporation Apparatus and method for simulating inhalation efforts
US9801925B2 (en) 1999-06-29 2017-10-31 Mannkind Corporation Potentiation of glucose elimination
US9802012B2 (en) 2012-07-12 2017-10-31 Mannkind Corporation Dry powder drug delivery system and methods
US9925144B2 (en) 2013-07-18 2018-03-27 Mannkind Corporation Heat-stable dry powder pharmaceutical compositions and methods
US9943571B2 (en) 2008-08-11 2018-04-17 Mannkind Corporation Use of ultrarapid acting insulin
US9983108B2 (en) 2009-03-11 2018-05-29 Mannkind Corporation Apparatus, system and method for measuring resistance of an inhaler
CN108430976A (zh) * 2015-12-16 2018-08-21 日本曹达株式会社 芳基唑化合物和有害生物防除剂
US10130581B2 (en) 2006-02-22 2018-11-20 Mannkind Corporation Method for improving the pharmaceutic properties of microparticles comprising diketopiperazine and an active agent
US10159644B2 (en) 2012-10-26 2018-12-25 Mannkind Corporation Inhalable vaccine compositions and methods
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