US20090087489A1 - Imatinib compositions - Google Patents

Imatinib compositions Download PDF

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Publication number
US20090087489A1
US20090087489A1 US12/238,314 US23831408A US2009087489A1 US 20090087489 A1 US20090087489 A1 US 20090087489A1 US 23831408 A US23831408 A US 23831408A US 2009087489 A1 US2009087489 A1 US 2009087489A1
Authority
US
United States
Prior art keywords
pharmaceutical composition
imatinib mesylate
tablet
imatinib
composition
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
US12/238,314
Other languages
English (en)
Inventor
Bella Gerber
Zvika Doani
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.)
Teva Pharmaceuticals USA Inc
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
Application filed by Individual filed Critical Individual
Priority to US12/238,314 priority Critical patent/US20090087489A1/en
Assigned to TEVA PHARMACEUTICALS USA, INC. reassignment TEVA PHARMACEUTICALS USA, INC. ASSIGNMENT OF RIGHS IN BARBADOS Assignors: TEVA PHARMACEUTICAL INDUSTRIES LTD.
Assigned to TEVA PHARMACEUTICAL INDUSTRIES LTD. reassignment TEVA PHARMACEUTICAL INDUSTRIES LTD. ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: DOANI, ZVIKA, GERBER, BELLA
Publication of US20090087489A1 publication Critical patent/US20090087489A1/en
Abandoned 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
    • A61K9/20—Pills, tablets, discs, rods
    • A61K9/28—Dragees; Coated pills or tablets, e.g. with film or compression coating
    • A61K9/2806—Coating materials
    • A61K9/2833—Organic macromolecular compounds
    • A61K9/286—Polysaccharides, e.g. gums; Cyclodextrin
    • A61K9/2866—Cellulose; Cellulose derivatives, e.g. hydroxypropyl methylcellulose
    • 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
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/496—Non-condensed piperazines containing further heterocyclic rings, e.g. rifampin, thiothixene or sparfloxacin
    • 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
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
    • A61K31/506—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim not condensed and containing further heterocyclic rings
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00—Drugs for disorders of the respiratory system
    • 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
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P7/00—Drugs for disorders of the blood or the extracellular fluid
    • A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
    • 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
    • A61K9/20—Pills, tablets, discs, rods
    • A61K9/2004—Excipients; Inactive ingredients
    • A61K9/2013—Organic compounds, e.g. phospholipids, fats
    • A61K9/2018—Sugars, or sugar alcohols, e.g. lactose, mannitol; Derivatives thereof, e.g. polysorbates
    • 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
    • A61K9/20—Pills, tablets, discs, rods
    • A61K9/2004—Excipients; Inactive ingredients
    • A61K9/2022—Organic macromolecular compounds
    • A61K9/205—Polysaccharides, e.g. alginate, gums; Cyclodextrin
    • A61K9/2054—Cellulose; Cellulose derivatives, e.g. hydroxypropyl methylcellulose

Definitions

  • Form X is characterized by data selected from the group consisting of: a powder XRD pattern with peaks at about 6.0, 8.6, 11.4, 14.2, 18.3 ⁇ 0.2 degrees two-theta; a powder XRD pattern having peaks at about: 6.0, 8.6, 10.2, 11.4, 14.2, 18.3 ⁇ 0.2 degrees two-theta; a powder XRD pattern having at least five peaks selected from the list consisting of peaks at about: 6.0, 8.6, 10.2, 11.4, 14.2, 17.8, 18.3, 21.6, 22.4, 23.6, 24.8 ⁇ 0.2 degrees two-theta; a solid-state 13 C NMR spectrum with signals at about 159.9, 158.2 and 153.4 ⁇ 0.2 ppm; a solid-state 13 C NMR spectrum having chemical shift differences between the signal exhibiting the lowest chemical shift and another in the chemical shift range of 100 to 180 ppm of about 51.5, 49.8, and 45.0 ⁇ 0.1 ppm.
  • the present invention also provides processes for preparing a pharmaceutical composition, preferably a tablet, containing imatinib or a pharmaceutical acceptable salt thereof, preferably imatinib mesylate in an amount of about 23-29% w/w, preferably of 25-29% w/w, more preferably of about 28-29% w/w.
  • EUDRAGIT® potassium chloride
  • powdered cellulose sodium chloride
  • sorbitol talc
  • diluents are selected from the group consisting of: Mannitol, calcium carbonate, Starlac, lactose, and di-basic calcium phosphate, most preferably the diluent is Starlac (82-88% Lactose monohydrate and 12-18% Maize starch).
  • Solid pharmaceutical compositions that are compacted into a dosage form like a tablet can include excipients whose functions include helping to bind the active ingredient and other excipients together after compression.
  • Binders for solid pharmaceutical compositions include at least one of acacia, alginic acid, carbomer (e.g. carbopol), carboxymethylcellulose sodium, dextrin, ethyl cellulose, gelatin, guar gum, hydrogenated vegetable oil, hydroxyethyl cellulose, hydroxypropyl cellulose (e.g. KLUCEL®), hydroxypropyl methyl cellulose (e.g.
  • METHOCEL® liquid glucose, magnesium aluminum silicate, maltodextrin, methylcellulose, polymethacrylates, povidone (e.g. KOLLIDON®, PLASDONE®), pregelatinized starch, sodium alginate, or starch. More preferably the binders are selected from hydroxypropylcellulose, povidone (e.g. KOLLIDON®, PLASDONE®), or starch, most preferably the binder is povidone (e.g. KOLLIDON®, PLASDONE®).
  • Glidants can be added to improve the flow properties of non-compacted solid composition and improve the accuracy of dosing.
  • Excipients that can function as glidants include colloidal silicon dioxide, magnesium trisilicate, powdered cellulose, starch, talc, and/or tribasic calcium phosphate. Most preferably the glidants are selected from talc, colloidal silicon dioxide, silicone dioxide NF most preferably the glidants is silicon dioxide NF.
  • a dosage form such as a tablet is made by compaction of a powdered composition
  • the composition is subjected to pressure from a punch and dye.
  • Some excipients and active ingredients have a tendency to adhere to the surfaces of the punch and dye, which can cause the product to have pitting and other surface irregularities.
  • a lubricant can be added to the composition to reduce adhesion and ease release of the product form the dye.
  • Lubricants include, but are not limited to, magnesium stearate, calcium stearate, glyceryl monostearate, glyceryl palmitostearate, hydrogenated castor oil, hydrogenated vegetable oil, mineral oil, polyethylene glycol, sodium benzoate, sodium lauryl sulfate, sodium stearyl fumarate, stearic acid, talc, and/or zinc stearate.
  • the lubricants are selected from the group consisting of: sodium stearyl fumarate, magnesium stearate and talc.
  • the lubricants are selected from the group consisting of magnesium stearate, sodium stearyl fumarate and a mixture thereof.
  • Flavoring agents and flavor enhancers make the dosage form more palatable to the patient.
  • Common flavoring agents and flavor enhancers for pharmaceutical products that can be included in the composition of the present invention include, but are not limited to, maltol, vanillin, ethyl vanillin, menthol, citric acid, fumaric acid, ethyl maltol, or tartaric acid.
  • Solid compositions can also be dyed using any pharmaceutically acceptable colorant to improve their appearance and/or facilitate patient identification of the product and unit dosage level.
  • the tablets in accordance with the present invention comprise; from about 23% to 29% w/w, more preferably from about 25% to about 29% w/w, imatinib mesylate; from 10 to 60% w/w, more preferably from about 25% to about 60% w/w, of a diluent, filler or bulking agent, preferably lactose, more preferably starlac (82-88% Lactose monohydrate and 12-18% Maize starch); from 4 to 30% w/w, more preferably from about 10% to about 25% w/w, of a disintegrant, preferably crospovidone; from 0.2 to 5% w/w of a glidant, preferably silicon dioxide; and from 0.1 to 4% w/w, more preferably from about 0.5% to about 2% w/w, of a lubricant, preferably selected from magnesium stearate or sodium stearyl fumurate or the mixture thereof.
  • a diluent, filler or bulking agent

Landscapes

  • Health & Medical Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Chemical & Material Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Epidemiology (AREA)
  • Cardiology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Hematology (AREA)
  • Vascular Medicine (AREA)
  • Urology & Nephrology (AREA)
  • Diabetes (AREA)
  • Pulmonology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicinal Preparation (AREA)
US12/238,314 2007-09-25 2008-09-25 Imatinib compositions Abandoned US20090087489A1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
US12/238,314 US20090087489A1 (en) 2007-09-25 2008-09-25 Imatinib compositions

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US99532107P 2007-09-25 2007-09-25
US99565107P 2007-09-26 2007-09-26
US12/238,314 US20090087489A1 (en) 2007-09-25 2008-09-25 Imatinib compositions

Publications (1)

Publication Number Publication Date
US20090087489A1 true US20090087489A1 (en) 2009-04-02

Family

ID=40070888

Family Applications (2)

Application Number Title Priority Date Filing Date
US12/238,314 Abandoned US20090087489A1 (en) 2007-09-25 2008-09-25 Imatinib compositions
US12/238,328 Active 2031-03-09 US8414918B2 (en) 2007-09-25 2008-09-25 Stable imatinib compositions

Family Applications After (1)

Application Number Title Priority Date Filing Date
US12/238,328 Active 2031-03-09 US8414918B2 (en) 2007-09-25 2008-09-25 Stable imatinib compositions

Country Status (9)

Country Link
US (2) US20090087489A1 (fr)
EP (2) EP2086520A1 (fr)
JP (2) JP2010540465A (fr)
KR (1) KR101041203B1 (fr)
BR (1) BRPI0817946A2 (fr)
CA (1) CA2700844A1 (fr)
MX (1) MX2010003200A (fr)
RU (1) RU2470641C2 (fr)
WO (2) WO2009042803A1 (fr)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2011160798A1 (fr) * 2010-06-21 2011-12-29 Zaklady Farmaceutyczne Polpharma Sa Compositions pharmaceutiques comprenant de l'imatinib ou un sel pharmaceutiquement acceptable de celui-ci et procédés pour la fabrication de celles-ci
WO2012087256A2 (fr) * 2010-12-20 2012-06-28 Mahmut Bilgic Formulations de capsules pharmaceutiques
WO2017078647A1 (fr) 2015-11-05 2017-05-11 Koçak Farma Ilaç Ve Kimya Sanayi Anonim Şirketi Compositions pharmaceutiques d'imatinib

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TWI505828B (zh) 2010-12-20 2015-11-01 葛蘭素史克智慧財產（第二）有限公司 新穎醫藥組成物
CN102552268A (zh) * 2010-12-23 2012-07-11 天津泰普药品科技发展有限公司 一种含有α晶型甲磺酸伊马替尼的药物制剂
PL394169A1 (pl) 2011-03-09 2012-09-10 Adamed Spółka Z Ograniczoną Odpowiedzialnością Kompozycja farmaceutyczna metanosulfonianu imatinibu do napełniania jednostkowych postaci dawkowania oraz sposób jej wytwarzania
EA017781B1 (ru) * 2011-05-24 2013-03-29 Тева Канада Лимитед Покрытая пленочной оболочкой таблетка, содержащая иматиниб мезилат, и способ ее получения
EA026665B1 (ru) 2011-11-24 2017-05-31 Имунекс Фарма Илак Санайи Ве Тикарет А.С. Твердые формы препаратов иматиниба, ресуспензируемые непосредственно перед применением
AU2013223749A1 (en) 2012-02-21 2014-09-11 Sun Pharmaceutical Industries Limited Stable dosage forms of imatinib mesylate
CN102600146B (zh) * 2012-04-11 2014-10-08 兆科药业（合肥）有限公司 一种盐酸乐卡地平和氯沙坦钾复方制剂及其制备方法
JP5928159B2 (ja) * 2012-05-28 2016-06-01 ニプロ株式会社 医薬組成物
KR101520792B1 (ko) * 2013-04-10 2015-05-15 보령제약 주식회사 고부하 이매티닙 정제
ES2683361T3 (es) * 2013-05-14 2018-09-26 Hetero Research Foundation Composiciones de Imatinib
US20160143850A1 (en) * 2013-07-09 2016-05-26 Shilpa Medicare Limited Oral Pharmaceutical Compositions Comprising Imatinib Mesylate
WO2019016673A2 (fr) * 2017-07-20 2019-01-24 Kashiv Pharma Llc Composition pharmaceutique stable d'imatinib à administration par voie orale
US20220175774A1 (en) * 2020-12-07 2022-06-09 Alembic Pharmaceuticals Limited Bioavailable Oral Dosage Form Of Tyrosine-Kinase Inhibitor

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US6894051B1 (en) * 1997-07-18 2005-05-17 Novartis Ag Crystal modification of a N-phenyl-2-pyrimidineamine derivative, processes for its manufacture and its use
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Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2011160798A1 (fr) * 2010-06-21 2011-12-29 Zaklady Farmaceutyczne Polpharma Sa Compositions pharmaceutiques comprenant de l'imatinib ou un sel pharmaceutiquement acceptable de celui-ci et procédés pour la fabrication de celles-ci
EA029416B1 (ru) * 2010-06-21 2018-03-30 Заклады Фармацеутицне Польфарма Са Таблетка, содержащая иматиниб или его фармацевтически приемлемую соль, и способ ее получения
WO2012087256A2 (fr) * 2010-12-20 2012-06-28 Mahmut Bilgic Formulations de capsules pharmaceutiques
WO2012087255A3 (fr) * 2010-12-20 2012-08-16 Mahmut Bilgic Formulations pharmaceutiques
WO2012087256A3 (fr) * 2010-12-20 2012-09-27 Mahmut Bilgic Formulations de capsules pharmaceutiques
WO2017078647A1 (fr) 2015-11-05 2017-05-11 Koçak Farma Ilaç Ve Kimya Sanayi Anonim Şirketi Compositions pharmaceutiques d'imatinib

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BRPI0817946A2 (pt) 2015-05-05
WO2009042803A1 (fr) 2009-04-02
KR101041203B1 (ko) 2011-06-13
EP2086520A1 (fr) 2009-08-12
CA2700844A1 (fr) 2009-04-02
EP2081556A1 (fr) 2009-07-29
RU2470641C2 (ru) 2012-12-27
US20090092669A1 (en) 2009-04-09
KR20100054843A (ko) 2010-05-25
US8414918B2 (en) 2013-04-09
JP2011140508A (ja) 2011-07-21
WO2009042809A1 (fr) 2009-04-02
WO2009042809A8 (fr) 2009-07-02
MX2010003200A (es) 2010-04-30
RU2010110982A (ru) 2011-09-27

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