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US20170065671A1 - Methods for producing an oralsuspension of teichoplanin or teichoplanin analogs - Google Patents

Methods for producing an oralsuspension of teichoplanin or teichoplanin analogs Download PDF

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Publication number
US20170065671A1
US20170065671A1 US14/957,810 US201514957810A US2017065671A1 US 20170065671 A1 US20170065671 A1 US 20170065671A1 US 201514957810 A US201514957810 A US 201514957810A US 2017065671 A1 US2017065671 A1 US 2017065671A1
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US
United States
Prior art keywords
suspension
teicoplanin
sodium
combinations
sorbitol
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.)
Abandoned
Application number
US14/957,810
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English (en)
Inventor
Illya Keith Maher
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Individual
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Individual
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Filing date
Publication date
Application filed by Individual filed Critical Individual
Priority to US14/957,810 priority Critical patent/US20170065671A1/en
Publication of US20170065671A1 publication Critical patent/US20170065671A1/en
Abandoned legal-status Critical Current

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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K38/00—Medicinal preparations containing peptides
    • A61K38/04—Peptides having up to 20 amino acids in a fully defined sequence; Derivatives thereof
    • A61K38/14—Peptides containing saccharide radicals; Derivatives thereof, e.g. bleomycin, phleomycin, muramylpeptides or vancomycin
    • 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
    • A61K9/10—Dispersions; Emulsions
    • 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

Definitions

  • teicoplanin contains 4-hydroxyphenylglycine and 3,5-dihydroxyphenylglycine residues, a chlorine atom attached on each of the tyrosine residues, and three sugar moieties, N-fatty acyl- ⁇ -D-glucosamine, N-acetyl- ⁇ -D-glucosamine, and D-mannose (id.)
  • Solubility directly impacts a drug's dissolution rate, potency and time to onset. Low solubility can be a hurdle for active substance to be properly formulated.
  • Targocid and other teicoplanin analogs and/or formulations are sold as lyophilized powders.
  • Targocid also contains sodium chloride and sodium hydroxide as excipients.
  • Another object of the invention is to provide a stable, taste-masked, suspension of teicoplanin, comprising a particle size such that d 90 is less than about 170 ⁇ .
  • FIG. 1 shows the chemical structures of teichoplanins A 2 1-5 that are major components of the teicoplanin composition in the present invention.
  • the present invention is an oral, stable, pharmaceutical suspension of teicoplanin.
  • the suspension dosage form is taste masked and uniformally dispersed and/or dissolved, improving patient compliance, especially for children, elderly and those unable to swallow pills or digest oral solid dosage forms.
  • teicoplanin as used is the invention is meant to cover crystalline teicoplanin in the form of freebase or its pharmaceutically acceptable salt(s), hydrate(s), solvate(s) and physiologically functional derivative(s) and precursors thereof.
  • the term also includes all isomers or polymorphic forms not limited to pure or mixtures thereof.
  • Teicoplanin may be used as a single active agent, or may be combined with other active agents, vitamins, minerals, dietary supplements, oils, including sunflower oil, coconut oil, etc.
  • teicoplanin is milled or micronized to a desired particle size.
  • the suspension may be milled by various techniques for example air-jet milling, impact milling, ball milling, dry milling, wet milling, or any other approved method to decrease particle size.
  • air-jet milling impact milling, ball milling, dry milling, wet milling, or any other approved method to decrease particle size.
  • Using the above techniques helps in obtaining the desired particle size with increased wettability, solubility, dissolution and dispersion of Teicoplanin.
  • the active surface area is increased along with the dissolution time. Small sized particles slow the rate of sedimentation, dissolve faster, and are usually less gritty.
  • d 90 less than about 170 ⁇
  • d 90 means that “90% particles is less than about 170 ⁇ ”. It is noted that the notation d x means that X % of particles have—a diameter less than the specified diameter d.
  • the d 90 of the teicoplanin dispersed or suspended in the suspension is less than about 170 ⁇ and more preferably of less than about 70 ⁇ .
  • the size of the particles may be measured using a light scattering device, sedimentation methods, or other methods known to a skilled person. For example, Matersizer 2000 manufactured by Malvern instruments Ltd., Malvern UK may be used to measure the teicoplanin particles measured for the purpose of this invention.
  • the taste-masked, suspension according to the invention has a suspension base with the active ingredient dispersed in the suspension base.
  • the pharmaceutically acceptable suspension base may be, for example, an aqueous solvent such as water, with the suspending/viscosity-enhancing agent dispersed throughout the medium or a non-aqueous suspension base, which includes but is not limited to, sunflower oil, coconut oil, castor oil and mixtures thereof.
  • the pharmaceutically acceptable suspension base may contain various additive(s), which are known to a person skilled in art.
  • flavoring agents may be for example, without limitation, menthol, cinnamon, wintergreen, clove, bay, anise, eucalyptus, thyme, cedar leave, nutmeg, sage, almonds, cassia, vanilla, artificial vanilla, chocolate, artificial chocolate, bubble gum, both natural and artificial fruit flavors, such as cherry flavor, grape flavor, orange flavor, banana flavor, strawberry flavor, lemon flavor, grapefruit flavor and “mint” flavors such as peppermint flavor and spearmint flavor, lime flavor, apple flavor, pear flavor, peach flavor, raspberry flavor, plum flavor, pineapple flavor, apricot flavor and so forth, including combinations of two or more thereof.
  • the amount of flavoring agent may depend on a number of factors, including the desired organoleptic effect.
  • sweetening and/or flavoring agent(s) depends on the properties of the agent(s) used, however generally in an amount that is sufficient to mask the unpleasant taste and/or odor associated with teicoplanin as determinable by one skilled in the art. However, flavoring agents generally present is in a pharmaceutically acceptable range.
  • Sweeteners or sweetening agents include any compound that provides a sweet taste to make the product more palatable.
  • Sweeteners suitable for inclusion in the present invention may be determined by one skilled in the art including, for example without limitation, natural, synthetic sugars, artificial sweeteners, natural extracts and any material that imitates a sweet sensation in a patient.
  • Representative sugars useful in the present invention include, without limitation, xylose, ribose, glucose, mannose, galactose, fructose, dextrose, sucrose, maltose, partially hydrolyzed starch or corn syrup, and sugar alcohols such as sorbitol, xylitol, mannitol, glycerin, etc. and combination thereof.
  • Sugar sweeteners may be replaced or augmented by water-soluble artificial sweeteners, such as the suitable artificial sweeteners previously listed and mixtures thereof.
  • the amount of artificial sweetener used in the composition may vary to provide an appropriate amount of sweetness as determinable by one skilled in the art. Mixtures of sweetening and/or flavoring agents are preferably used. By suitable combination of sweetener and flavoring agents the unpleasant taste of the teicoplanin can be improved.
  • the pharmaceutical composition may also comprise antioxidant(s), which are agents or mixtures of agents that are capable of slowing or preventing oxidation of molecules or substances.
  • antioxidant(s) are agents or mixtures of agents that are capable of slowing or preventing oxidation of molecules or substances.
  • Representative examples include, but are not limited to, ascorbic acid, butylated hydroxy anisole, butylated hydroxyl toluene, gallic acid, maleic acid, propyl gallate, sodium bisulphate, sodium metabisulphite, tocopherols and mixtures thereof.
  • Additional preservatives useful in the present invention include, but are not limited to, sodium benzoate, potassium sorbate, salts of edetate (also known as salts of ethylenediaminetetraacetic acid, or EDTA, such as disodium edetate) and antimicrobial agents including parabens (p-hydroxybenzoic acids esters) such as methyl paraben, ethylparaben, propylparaben, butylparaben and the like, and combinations thereof.
  • Preservative(s) as used in the composition are in a pharmaceutically acceptable range.
  • the pharmaceutical composition may also comprise a suspending or viscosity enhancing agent or mixture of agents.
  • Suspending/viscosity enhancing refers to agents or mixtures of agents that increases the viscosity or thickness of the liquid and slowing particle sedimentation. For example, in a suspension these agents help to keep the active substance suspended to allow accurate dosing.
  • the pH of the composition is in range of about 2.0 about 8.0. Most preferably the pH of composition is in range from about 4.5 to about 6.5.
  • the pharmaceutical composition may also comprise wetting agent(s), which refers to a surface active agent or mixture of agents that lowers the interfacial tension between a solid and liquid or liquid and liquid. They help to crate a homogenous dispersion of solid particles in a liquid vehicle and include, but are not limited to acacia, poloxamers, polysorbates such as sorbitan monolaurate, polysorbate 80, and sodium lauryl sulfate and mixtures thereof.
  • wetting agent(s) refers to a surface active agent or mixture of agents that lowers the interfacial tension between a solid and liquid or liquid and liquid. They help to crate a homogenous dispersion of solid particles in a liquid vehicle and include, but are not limited to acacia, poloxamers, polysorbates such as sorbitan monolaurate, polysorbate 80, and sodium lauryl sulfate and mixtures thereof.
  • the pharmaceutical composition may also comprise suitable coloring agent(s) both natural and synthetic to provide an appealing color to the pharmaceutical composition, which include, but are not limited to US Food and Drug Administration (FDA) approved coloring agents; FD&C Red No. 3, FD&C Red No. 40, FD&C Yellow No. 6, FD&C Blue No. 2, D&C Green No. 5, D&C Orange No. 5, D&C Yellow No. 10, titanium dioxide pigments, amaranth carmine, lake colors, iron oxide pigments and mixtures thereof.
  • suitable coloring agent(s) both natural and synthetic to provide an appealing color to the pharmaceutical composition, which include, but are not limited to US Food and Drug Administration (FDA) approved coloring agents; FD&C Red No. 3, FD&C Red No. 40, FD&C Yellow No. 6, FD&C Blue No. 2, D&C Green No. 5, D&C Orange No. 5, D&C Yellow No. 10, titanium dioxide pigments, amaranth carmine, lake colors, iron oxide pigments and mixtures thereof.
  • FDA US Food and Drug
  • the suspension of teicoplanin can be prepared by a process comprising the steps of (1) dispersing teicoplanin in an aqueous or non aqueous base comprising (a) at least one dispersing agent; (b) at least one buffering agent (in the case of an aqueous base) and (c) at least one suspension vehicle and (2) further milling the suspension to obtain a homogenously dispersed teicoplanin suspension.
  • the suspension may further comprise at least one additive selected from the group comprising sweetening agents, antioxidants, taste enhancing agents, antifoaming agents, coloring agents, wetting agents, thickening agents, preservative or mixtures thereof.
  • Teicoplanin 4000 mg 1. Sunflower oil 80 ml 3. Butyl Paraben 400 mg 4. Alpha Tocopherol 1000 mg 5. Colloidal silicon dioxide 1000 mg 6. Sodium saccharin 250 mg 7. Sodium chloride 5 mg 8. Flavor Raspberry 5 ml 9. Fractionated coconut oil up to 100 ml

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • General Health & Medical Sciences (AREA)
  • Epidemiology (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Immunology (AREA)
  • Gastroenterology & Hepatology (AREA)
  • Dispersion Chemistry (AREA)
  • Braking Arrangements (AREA)
  • Mechanical Engineering (AREA)
  • Transportation (AREA)
  • General Engineering & Computer Science (AREA)
  • Medicinal Preparation (AREA)
US14/957,810 2015-09-08 2015-12-03 Methods for producing an oralsuspension of teichoplanin or teichoplanin analogs Abandoned US20170065671A1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
US14/957,810 US20170065671A1 (en) 2015-09-08 2015-12-03 Methods for producing an oralsuspension of teichoplanin or teichoplanin analogs

Applications Claiming Priority (2)

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US201562215425P 2015-09-08 2015-09-08
US14/957,810 US20170065671A1 (en) 2015-09-08 2015-12-03 Methods for producing an oralsuspension of teichoplanin or teichoplanin analogs

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US15/250,298 Active 2036-11-10 US10231928B2 (en) 2015-09-08 2016-08-29 Disc brake arrangement

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CA (1) CA2941044A1 (es)
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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20190282500A1 (en) * 2016-09-09 2019-09-19 Cutispharma, Inc. Suspensions and diluents for metronidazole and baclofen
US10751333B1 (en) * 2019-07-16 2020-08-25 Cutispharma, Inc. Compositions and kits for omeprazole suspension
US11207307B2 (en) 2016-06-16 2021-12-28 Azurity Pharmaceuticals, Inc. Composition and method for proton pump inhibitor suspension
US11633478B2 (en) 2019-07-16 2023-04-25 Azurity Pharmaceuticals, Inc. Compositions and kits for Omeprazole suspension

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
USD801895S1 (en) * 2015-09-22 2017-11-07 Saf-Holland, Inc. Brake torque plate
WO2017156212A1 (en) * 2016-03-11 2017-09-14 Hendrickson Usa, L.L.C. Bracket for anti-lock braking system sensor
US11846333B2 (en) * 2020-11-13 2023-12-19 Hendrickson Usa, L.L.C. Radial mounting torque plate for heavy-duty vehicles

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
SE0200218D0 (sv) * 2002-01-28 2002-01-28 Haldex Brake Prod Ab Torque Plate
US20120247885A1 (en) * 2011-03-31 2012-10-04 Bendix Spicer Foundation Brake Llc Adaptive Torque Plates
US9879738B2 (en) * 2014-09-16 2018-01-30 Hendrickson Usa, L.L.C. Torque plate for heavy-duty vehicles
US20160356329A1 (en) * 2015-06-04 2016-12-08 Wabco Europe Bvba Integrated torque plate and brake carrier

Cited By (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US11813253B2 (en) 2016-06-16 2023-11-14 Azurity Pharmaceuticals, Inc. Composition and method for proton pump inhibitor suspension
US11207307B2 (en) 2016-06-16 2021-12-28 Azurity Pharmaceuticals, Inc. Composition and method for proton pump inhibitor suspension
US20190282500A1 (en) * 2016-09-09 2019-09-19 Cutispharma, Inc. Suspensions and diluents for metronidazole and baclofen
US12458593B2 (en) 2016-09-09 2025-11-04 Azurity Pharmaceuticals, Inc. Suspensions and diluents for metronidazole and baclofen
US11324696B2 (en) 2016-09-09 2022-05-10 Azurity Pharmaceuticals, Inc. Suspensions and diluents for metronidazole and baclofen
US11446246B2 (en) 2016-09-09 2022-09-20 Azurity Pharmaceuticals, Inc. Suspensions and diluents for metronidazole and baclofen
US11633478B2 (en) 2019-07-16 2023-04-25 Azurity Pharmaceuticals, Inc. Compositions and kits for Omeprazole suspension
US11771686B2 (en) 2019-07-16 2023-10-03 Azurity Pharmaceuticals, Inc. Compositions and kits for omeprazole suspension
US11103492B2 (en) 2019-07-16 2021-08-31 Azurity Pharmaceuticals, Inc. Compositions and kits for omeprazole suspension
US11911473B2 (en) 2019-07-16 2024-02-27 Azurity Pharmaceuticals, Inc. Compositions and kits for omeprazole suspension
US12042539B2 (en) 2019-07-16 2024-07-23 Azurity Pharmaceuticals, Inc. Compositions and kits for Omeprazole suspension
US12329752B2 (en) 2019-07-16 2025-06-17 Azurity Pharmaceuticals, Inc. Compositions and kits for omeprazole suspension
US12440566B2 (en) 2019-07-16 2025-10-14 Azurity Pharmaceuticals, Inc. Compositions and kits for omeprazole suspension
US10751333B1 (en) * 2019-07-16 2020-08-25 Cutispharma, Inc. Compositions and kits for omeprazole suspension

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Publication number Publication date
MX2016011642A (es) 2018-03-07
US20170066426A1 (en) 2017-03-09
US10231928B2 (en) 2019-03-19
MX385230B (es) 2025-03-14
CA2941044A1 (en) 2017-03-08

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