WO2015031198A2 - Bendamustine pharmaceutical compositions - Google Patents

Bendamustine pharmaceutical compositions Download PDF

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Publication number
WO2015031198A2
WO2015031198A2 PCT/US2014/052341 US2014052341W WO2015031198A2 WO 2015031198 A2 WO2015031198 A2 WO 2015031198A2 US 2014052341 W US2014052341 W US 2014052341W WO 2015031198 A2 WO2015031198 A2 WO 2015031198A2
Authority
WO
WIPO (PCT)
Prior art keywords
bendamustine
drying
excipient
solid dispersion
concentration
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/US2014/052341
Other languages
English (en)
French (fr)
Other versions
WO2015031198A3 (en
Inventor
Vasilios VOUDOURIS
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.)
Individual
Original Assignee
Individual
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 JP2016538988A priority Critical patent/JP6571657B2/ja
Priority to CA2922099A priority patent/CA2922099C/en
Priority to MX2016002502A priority patent/MX376522B/es
Priority to CN201480045199.8A priority patent/CN105491886B/zh
Priority to ES14840972T priority patent/ES2957541T3/es
Priority to AU2014311570A priority patent/AU2014311570C1/en
Priority to EP14840972.5A priority patent/EP3043648B1/en
Application filed by Individual filed Critical Individual
Publication of WO2015031198A2 publication Critical patent/WO2015031198A2/en
Publication of WO2015031198A3 publication Critical patent/WO2015031198A3/en
Priority to IL244133A priority patent/IL244133A0/en
Anticipated expiration legal-status Critical
Priority to ZA2016/01645A priority patent/ZA201601645B/en
Priority to AU2018206777A priority patent/AU2018206777A1/en
Priority to AU2020286183A priority patent/AU2020286183A1/en
Priority to AU2020286280A priority patent/AU2020286280A1/en
Priority to AU2022263496A priority patent/AU2022263496A1/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
    • 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
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/4164—1,3-Diazoles
    • A61K31/4184—1,3-Diazoles condensed with carbocyclic rings, e.g. benzimidazoles
    • 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
    • A61K9/0087—Galenical forms not covered by A61K9/02 - A61K9/7023
    • A61K9/0095—Drinks; Beverages; Syrups; Compositions for reconstitution thereof, e.g. powders or tablets to be dispersed in a glass of water; Veterinary drenches
    • 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
    • A61K9/16—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction
    • 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
    • A61K9/16—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction
    • A61K9/1605—Excipients; Inactive ingredients
    • A61K9/1617—Organic compounds, e.g. phospholipids, fats
    • 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
    • A61K9/16—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction
    • A61K9/1605—Excipients; Inactive ingredients
    • A61K9/1617—Organic compounds, e.g. phospholipids, fats
    • A61K9/1623—Sugars or sugar alcohols, e.g. lactose; Derivatives thereof; Homeopathic globules
    • 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
    • A61K9/16—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction
    • A61K9/1605—Excipients; Inactive ingredients
    • A61K9/1629—Organic macromolecular compounds
    • A61K9/1635—Organic macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyvinyl pyrrolidone, poly(meth)acrylates
    • 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
    • A61K9/16—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction
    • A61K9/1605—Excipients; Inactive ingredients
    • A61K9/1629—Organic macromolecular compounds
    • A61K9/1641—Organic macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyethylene glycol, poloxamers
    • 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
    • A61K9/16—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction
    • A61K9/1605—Excipients; Inactive ingredients
    • A61K9/1629—Organic macromolecular compounds
    • A61K9/1652—Polysaccharides, e.g. alginate, cellulose derivatives; Cyclodextrin
    • 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
    • A61K9/16—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction
    • A61K9/1682—Processes
    • 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
    • A61K9/16—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction
    • A61K9/1682—Processes
    • A61K9/1694—Processes resulting in granules or microspheres of the matrix type containing more than 5% of excipient
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A61P35/02—Antineoplastic agents specific for leukemia
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/02—Immunomodulators
    • A61P37/06—Immunosuppressants, e.g. drugs for graft rejection

Definitions

  • compositions comprise nitrogen mustards, particularly the nitrogen mustard bendamustine, e.g., bendamustine HCI.
  • compositions of nitrogen mustards in particular, dry- powder bendamustine and methods of their use in treatment of various disease states, for instance neoplastic diseases and autoimmune diseases.
  • FIG. 4 provides a detailed view of a 2-liquid-phase spray nozzle useful for producing bendamustine dry-powder.
  • stable dry-powder preparation any dry-powder preparation having sufficient stability, such characteristics as similarly defined herein for a stable pharmaceutical composition, to have utility as a pharmaceutical product.
  • compositions comprising the solid dispersions.
  • the compositions can show greater stability and fewer impurities.
  • the compositions comprise a limited amount of impurities.
  • the compositions provide a limited amount of impurities after storage. It is believed that the increased stability of the compositions provided herein results from the limited aqueous exposure of the active components during manufacture and storage as well as the thermodynamic properties of the solid dispersions and the differences in the drying and solid state formation mechanisms between lyophilization and alternative forms of drying.
  • the solid forms or pharmaceutical compositions comprise little or no water. In certain embodiments, the solid forms or pharmaceutical compositions comprise substantially no water. In certain embodiments, the solid forms or pharmaceutical compositions comprise less than 1%, less than 0.75%, less than 0.5%, less than 0.25%, or less than 0.1% by weight water.
  • a non-aqueous pre-drying solution or dispersion comprising bendamustine is first formulated in a pharmaceutically acceptable compounding vessel.
  • An aqueous pre-drying solution or dispersion containing an acceptable excipient is also formulated in a separate pharmaceutically acceptable compounding vessel. Both solutions are then aseptically filtered, mixed by means of an in-line static mixer and continuously fed into the spray drier.
  • the aqueous and non-aqueous solutions comprise the two liquid inputs in a two-liquid-phase nozzle of a spray drier (see FIGS. 3 and 4).
  • Useful organic solvents include one or more of methanol, ethanol, propanol, iso-propanol, butanol, acetone, acetonitrile, dimethyl sulfoxide, methylene chloride, N-methyl-2-pyrrolidone (NMP), dimethyl formamide (DMF), dimethyl acetamide (DMA) and tert butanol.
  • the organic solvent is selected from acetone, acetonitrile, dimethyl sulfoxide, methylene chloride, N-methyl-2-pyrrolidone (NMP), dimethyl formamide (DMF), dimethyl acetamide (DMA), teri-butanol, and mixtures thereof.
  • DACHP(Myr)2 diphenylspiromustine, diplatinum cytostatic, Erba distamycin derivatives, Chugai DWA-2114R, ITI E09, elmustine, Erbamont FCE-24517, estramustine phosphate sodium, fotemustine, Unimed G-6-M, Chinoin GYKI- 17230, hepsul-fam, ifosfamide, iprop latin, lomustine, mafosfamide, melphalan, mitolactol, Nippon Kayaku N -121, NCI NSC-264395, NCI NSC-342215, oxaliplatin, Upjohn PCNU, prednimustine, Proter PTT-119, ranimustine, semustine, SmithKline S &F-101772, Yakult Honsha SN-22, spiromustine, Tanabe Seiyaku TA-077, tauromustine, temozolomide, teroxi

Landscapes

  • Health & Medical Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Veterinary Medicine (AREA)
  • Animal Behavior & Ethology (AREA)
  • Epidemiology (AREA)
  • Molecular Biology (AREA)
  • Biophysics (AREA)
  • Organic Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Immunology (AREA)
  • Hematology (AREA)
  • Transplantation (AREA)
  • Oncology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicinal Preparation (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Inorganic Chemistry (AREA)
PCT/US2014/052341 2013-08-27 2014-08-22 Bendamustine pharmaceutical compositions Ceased WO2015031198A2 (en)

Priority Applications (13)

Application Number Priority Date Filing Date Title
JP2016538988A JP6571657B2 (ja) 2013-08-27 2014-08-22 ベンダムスチンの薬学的組成物
CA2922099A CA2922099C (en) 2013-08-27 2014-08-22 Bendamustine pharmaceutical compositions
MX2016002502A MX376522B (es) 2013-08-27 2014-08-22 Composiciones farmacéuticas de bendamustina.
CN201480045199.8A CN105491886B (zh) 2013-08-27 2014-08-22 苯达莫司汀医药组合物
ES14840972T ES2957541T3 (es) 2013-08-27 2014-08-22 Composiciones farmacéuticas de bendamustina
AU2014311570A AU2014311570C1 (en) 2013-08-27 2014-08-22 Bendamustine pharmaceutical compositions
EP14840972.5A EP3043648B1 (en) 2013-08-27 2014-08-22 Bendamustine pharmaceutical compositions
IL244133A IL244133A0 (en) 2013-08-27 2016-02-15 Pharmaceutical compositions containing bendamustine
ZA2016/01645A ZA201601645B (en) 2013-08-27 2016-03-09 Bendamustine pharmaceutical compositions
AU2018206777A AU2018206777A1 (en) 2013-08-27 2018-07-19 Bendamustine Pharmaceutical Compositions
AU2020286183A AU2020286183A1 (en) 2013-08-27 2020-12-08 Bendamustine Pharmaceutical Compositions
AU2020286280A AU2020286280A1 (en) 2013-08-27 2020-12-10 Bendamustine Pharmaceutical Compositions
AU2022263496A AU2022263496A1 (en) 2013-08-27 2022-11-02 Bendamustine Pharmaceutical Compositions

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US201361870609P 2013-08-27 2013-08-27
US61/870,609 2013-08-27

Publications (2)

Publication Number Publication Date
WO2015031198A2 true WO2015031198A2 (en) 2015-03-05
WO2015031198A3 WO2015031198A3 (en) 2015-04-23

Family

ID=52584085

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2014/052341 Ceased WO2015031198A2 (en) 2013-08-27 2014-08-22 Bendamustine pharmaceutical compositions

Country Status (11)

Country Link
US (7) US9849115B2 (cg-RX-API-DMAC7.html)
EP (1) EP3043648B1 (cg-RX-API-DMAC7.html)
JP (1) JP6571657B2 (cg-RX-API-DMAC7.html)
CN (2) CN109953954A (cg-RX-API-DMAC7.html)
AU (5) AU2014311570C1 (cg-RX-API-DMAC7.html)
CA (1) CA2922099C (cg-RX-API-DMAC7.html)
ES (1) ES2957541T3 (cg-RX-API-DMAC7.html)
IL (1) IL244133A0 (cg-RX-API-DMAC7.html)
MX (2) MX376522B (cg-RX-API-DMAC7.html)
WO (1) WO2015031198A2 (cg-RX-API-DMAC7.html)
ZA (1) ZA201601645B (cg-RX-API-DMAC7.html)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9061011B1 (en) 2013-08-27 2015-06-23 Vasilios Voudouris Bendamustine pharmaceutical compositions

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CN106102722A (zh) * 2014-03-13 2016-11-09 V·沃道里斯 苯达莫司汀固体分散体和连续输液
JP6937016B2 (ja) * 2017-09-06 2021-09-22 東京理化器械株式会社 噴霧乾燥装置

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9061011B1 (en) 2013-08-27 2015-06-23 Vasilios Voudouris Bendamustine pharmaceutical compositions

Also Published As

Publication number Publication date
ES2957541T3 (es) 2024-01-22
CA2922099A1 (en) 2015-03-05
WO2015031198A3 (en) 2015-04-23
CN105491886A (zh) 2016-04-13
CN105491886B (zh) 2019-01-29
EP3043648A4 (en) 2017-11-22
MX2020006075A (es) 2020-08-24
JP6571657B2 (ja) 2019-09-04
AU2014311570A1 (en) 2016-03-10
ZA201601645B (en) 2017-04-26
US9849115B2 (en) 2017-12-26
EP3043648C0 (en) 2023-09-20
CA2922099C (en) 2022-11-29
EP3043648B1 (en) 2023-09-20
CN109953954A (zh) 2019-07-02
US20230310381A1 (en) 2023-10-05
US11701344B2 (en) 2023-07-18
JP2016531138A (ja) 2016-10-06
MX376522B (es) 2025-03-07
US20180071263A1 (en) 2018-03-15
US9061011B1 (en) 2015-06-23
US20210008036A1 (en) 2021-01-14
MX2016002502A (es) 2017-02-28
US20240299363A1 (en) 2024-09-12
EP3043648A2 (en) 2016-07-20
AU2014311570C1 (en) 2018-08-02
AU2020286280A1 (en) 2021-01-14
IL244133A0 (en) 2016-04-21
US10786486B2 (en) 2020-09-29
AU2018206777A1 (en) 2018-08-09
AU2014311570B2 (en) 2018-04-19
AU2022263496A1 (en) 2022-12-08
AU2020286183A1 (en) 2021-01-07
US20220079923A1 (en) 2022-03-17
US20150065549A1 (en) 2015-03-05

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