US20080249104A1 - Salt Forms of 4- (4-Methylpiperazin-1-Ylmethyl) -N- [4-Methyl-3- (4-Pyridin-3-Yl) Pyrimidin-2-Ylamino) Phenyl]- Benzamide - Google Patents

Salt Forms of 4- (4-Methylpiperazin-1-Ylmethyl) -N- [4-Methyl-3- (4-Pyridin-3-Yl) Pyrimidin-2-Ylamino) Phenyl]- Benzamide Download PDF

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US20080249104A1
US20080249104A1 US10/597,287 US59728708A US2008249104A1 US 20080249104 A1 US20080249104 A1 US 20080249104A1 US 59728708 A US59728708 A US 59728708A US 2008249104 A1 US2008249104 A1 US 2008249104A1
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salt
methyl
imatinib
phenyl
benzamide
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US10/597,287
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Hans Michael Burger
Paul William Manley
Michael Mutz
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Priority to US10/597,287 priority Critical patent/US20080249104A1/en
Publication of US20080249104A1 publication Critical patent/US20080249104A1/en
Priority to US13/368,811 priority patent/US8513256B2/en
Priority to US13/946,000 priority patent/US20140051853A1/en
Priority to US16/230,676 priority patent/US11612598B2/en
Abandoned legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • 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
    • A61P35/00—Antineoplastic agents
    • A61P35/04—Antineoplastic agents specific for metastasis

Definitions

  • the present invention relates to salts forms of the pharmaceutically active compound 4-[(4-methyl-1-piperazinyl)methyl]-N-[4methyl-3- 4-(3-pyridinyl)2-pyrimidinyl]amino phenyl -benzamide.
  • the pharmaceutically active compound 4-[(4-methyl-1-piperazinyl)methyl]-N-[4-methyl-3-[[4-(3-pyridinyl)-2-pyrimidinyl]amino]phenyl]-benzamide is commonly known by its INN name imatinib. Imatinib and its preparation are described in U.S. Pat. No. 5,521,184.
  • Basic pharmaceutically active compounds are commonly formulated into pharmaceutical preparations as an acid addition salt form, particularly as a crystalline acid addition salt.
  • imatinib is marketed in many countries as its monomethanesulfonate salt (imatinib mesylate) under the brandname GLIVEC or GLEEVEC.
  • GLIVEC monomethanesulfonate salt
  • GLEEVEC GLEEVEC
  • Two crystal forms of imatinib mesylate are described in WO 99/03854.
  • the crystal form designated as the beta form is described as having physical properties that make it advantageous for the manufacture of solid oral pharmaceutical dosage forms, such as tablet and capsule dosage forms.
  • the present invention relates to salt forms of imatinib, other than imatinib mesylate, that are useful for the manufacture of solid or liquid pharmaceutical dosage forms, particularly solid oral dosage forms, such as tablets and capsules, and liquid oral dosage forms, such as orally administered solutions and suspensions, as well as suppositories and other pharmaceutical dosage forms.
  • Each of these salt forms possesses one or more properties that provides advantages when used as a pharmaceutical active ingredient, such as physical properties that make it easier to manufacture one or more dosage forms, improved stability, improved bioavailability and other such properties that are known to one of skill in the art.
  • the salt forms of imatinib are prepared by methods known in the art for making acid addition salts of amines, e.g., by treatment of imatinib with an acid or a suitable anion exchange reagent.
  • imatinib or a solution of imatinib is combined with a solution of an organic or mineral acid in, e.g., a lower alcohol, such as methanol or ethanol, with or without heating.
  • the salt is isolated by crystallization or by evaporation of the solvent and, if desired, purified by re-crystallization from an appropriate re-crystallization solvent by methods known to one of skill in the art.
  • salts for the purpose of administering a salt of 4-[(4methyl-1-piperazinyl)methyl]-N-[4-methyl-3-[[4-(3-pyridinyl)-2-pyrimidinyl]amino]phenyl]-benzamide by means of an oral solution, in general those salts are preferred having an increased water solubility compared to the free base. Salts having a lower water solubility compared to the free base, render them in general more suitable for the manufacture of sustained release formulations compared to the free base.
  • Important embodiments of this invention include salts of 4-[(4-methyl-1-piperazinyl)methyl]-N-[4-methyl-3[[4(3-pyridinyl)-2-pyrimidinyl]amino]phenyl]-benzamide selected from the group consisting of a tartrate salt, such as a (D)( ⁇ ) tartrate salt or a (L)(+) tartrate salt, a hydrochloride salt, a citrate salt, a malate salt, particularly a D-malate salt, a fumarate salt, a succinate salt, a benzoate salt, a benzenesulfonate salt, a pamoate salt, a formate salt, a malonate salt, a 1,5-naphthalenedisulfonate salt, a salicylate salt, a cyclohexanesulfamate salt, a lactate salt, particularly a (S)-lactate salt, a mandelate salt, particularly an (R)(
  • Further important embodiments of this invention include imatinib ascorbate, imatinib formate, imatinib malonate, imatinib oxaloacetate, imatinib squarate and imatinib vanillate.
  • the acid addition salt is selected from the group consisting of a tartrate salt, such as a (D)( ⁇ ) tartrate salt or a (L)(+) tartrate salt, a hydrochloride salt, a citrate salt, a malate salt, particularly a D-malate salt, a fumarate salt, a succinate salt, a benzoate salt, a benzenesulfonate salt, a pamoate salt, a hemiformate salt, a malonate salt, a salicylate salt, a cyclohexanesulfamate salt, a mandelate salt, particularly an (R)( ⁇ ) mandelate salt, a hemiglutarate salt, an adipate salt, a vanillate salt and a sulfate salt.
  • a tartrate salt such as a (D)( ⁇ ) tartrate salt or a (L)(+) tartrate salt
  • a hydrochloride salt such as a citrate salt,
  • the acid addition salt is selected from the group consisting of imatinib D-tartrate, imatinib D-malate, imatinib hemiformate, imatinib malonate, imatinib salicylate, imatinib hemiglutamate, imatinib cyclohexanesulfamate, imatinib mandelate, particularly imatinib (R)( ⁇ ) mandelate, imatinib adipate, imatinib vanillate and imatinib sulfate.
  • the present invention further relates to a pharmaceutical composition
  • a pharmaceutical composition comprising one of the above mentioned salts of imatinib and a pharmaceutically acceptable carrier.
  • the invention relates to a pharmaceutical composition which comprises a pharmaceutically acceptable carrier and an acid addition salt of 4-[(4-methyl-1-piperazinyl)methyl]-N-[4-methyl-3-[[4-(3pyridinyl)-2-pyrimidinyl]amino]phenyl]-benzamide selected from the group consisting of a tartrate salt, such as a (D)( ⁇ ) tartrate salt or a (L)(+) tartrate salt, a hydrochloride salt; a citrate salt, a malate salt, particularly a D-malate salt, a fumarate salt, a succinate salt, a benzoate salt, a benzenesulfonate salt, a pamoate salt, a formate salt, a malonate salt, a 1,5naphthalenedisulfonate salt, a salicylate salt, a cyclohexanesulfamate salt, a lactate salt, particularly a (S)-lac
  • the acid addition salt is selected from the group consisting of imatinib ascorbate, imatinib formate, imatinib malonate, imatinib oxaloacetate, imatinib squarate and imatinib vanillate.
  • the invention relates also to a process for the treatment of warm-blooded animals suffering from a tumour disease, wherein a quantity of one of acid addition salt of 4-[(4-methyl-1-piperazinyl)methyl]-N-[4-methyl-3-[[4-(3-pyridinyl)-2-pyrimidinyl]amino]phenyl]-benzamide disclosed herein which is effective against the disease concerned, especially a quantity with antiproliferative and especially tumour-inhibiting efficacy, is administered to warm-blooded animals in need of such treatment, especially the treatment of gliomas, ovarian tumours, prostate tumours, gastro-intestinal stromal tumors, colon tumours, and tumours of the lung, such as especially small cell lung carcinoma, and tumours of the breast or other gynaecological tumours and, in particular leukemia.
  • effective doses for example daily doses of about 10-2000 mg, preferably 25-1000 mg, especially 50-800 mg, are administered to warm-blooded animals of about 70 kg bodyweight.
  • the present invention relates to the use of an acid addition salt of 4-[(4-methyl-1-piperazinyl)methyl]-N-[4-methyl-3-[[4-(3-pyridinyl)-2-pyrimidinyl]amino]phenyl]-benzamide according to any one claims 1 to 4 for the manufacture of a pharmaceutical composition for the treatment of a tumour disease, especially the treatment of gliomas, ovarian tumours, prostate tumours, gastro-intestinal stromal tumors, colon tumours, and tumours of the lung, such as especially small cell lung carcinoma, and tumours of the breast or other gynaecological tumours and, in particular leukemia.
  • a tumour disease especially the treatment of gliomas, ovarian tumours, prostate tumours, gastro-intestinal stromal tumors, colon tumours, and tumours of the lung, such as especially small cell lung carcinoma, and tumours of the breast or other gynaecological tumours and, in particular leukemia.
  • Aqueous hydrochloric acid (0.99 g of 37%) is added to a solution of 4-[(4-methyl-1-piperazinyl)methyl]-N-[4-methyl-3-[[4-(3-pyridinyl)-2-pyrimidinyl]amino]phenyl]-benzamide (4.94 g, 10 mmol) in ethanol (20 mL).
  • the solution is evaporated to dryness under reduced pressure and the resulting residue is re-crystallized from ethanol ethylacetate.
  • a solution of 4-hydroxy-3-methoxybenzoic acid (vanillic acid; Fluka, Buchs, Switzerland; 694 mg, 4 mmol) in ethanol (50 mL) is added to a solution of 4-[(4-methyl-1-piperazinyl)methyl]-N-[4-methyl-3-[[4-(3-pyridinyl)-2-pyrimidinyl]amino]phenyl]-benzamide (1.975 g, 4 mmol) in hot ethanol (150 mL at 90° C.). The solution is evaporated to dryness under reduced pressure and the resulting residue is re-crystallized from ethanol acetone.
  • a solution of 1,6-hexanedioic acid (adipic acid; Fluka, Buchs, Switzerland; 1081 mg, 4 mmol) in ethanol (80 mL) is added to a solution of 4-[(4-methyl-1-piperazinyl)methyl]-N-[4-methyl-3-[[4-(3-pyridinyl)-2-pyrimidinyl]amino]phenyl]-benzamide (1.975 g, 4 mmol) in hot ethanol (150 mL at 90° C.).
  • the hot solution is reduced in volume to 80 mL by rotary evaporation at 90° C. and 400 mbar and then slowly cooled to 20° C.
  • Composition Salt 100 mg Avicel 200 mg PVPPXL 15 mg Aerosil 2 mg Magnesium stearate 1.5 mg 318.5 mg
  • the capsules are prepared by mixing the components and filling the mixture into hard gelatin capsules, size 1.
  • Solubility in water at room temperature of the 4-[(4-methyl-1-piperazinyl)methyl]-N-[4-methyl-3-[[ 4 -(3-pyridinyl)-2-pyrimidinyl]amino]phenyl]-benzamide salts is as listed in Table 1 below.
  • the solubility of the free base in water at room temperature is 0.44 mg/ml.

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  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Veterinary Medicine (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Oncology (AREA)
  • Hematology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Pyridine Compounds (AREA)
US10/597,287 2004-02-04 2005-02-03 Salt Forms of 4- (4-Methylpiperazin-1-Ylmethyl) -N- [4-Methyl-3- (4-Pyridin-3-Yl) Pyrimidin-2-Ylamino) Phenyl]- Benzamide Abandoned US20080249104A1 (en)

Priority Applications (4)

Application Number Priority Date Filing Date Title
US10/597,287 US20080249104A1 (en) 2004-02-04 2005-02-03 Salt Forms of 4- (4-Methylpiperazin-1-Ylmethyl) -N- [4-Methyl-3- (4-Pyridin-3-Yl) Pyrimidin-2-Ylamino) Phenyl]- Benzamide
US13/368,811 US8513256B2 (en) 2004-02-04 2012-02-08 Salt forms of 4-(4-methylpiperazin-1-ylmethyl)-N-[4-methyl-3-(4-pyridin-3-yl)pyrimidin-2-ylamino)phenyl]-benzamide
US13/946,000 US20140051853A1 (en) 2004-02-04 2013-07-19 Salt forms of 4-(4-Methylpiperazin-1-ylmethyl)-N-[4-methyl-3-(4-pyridin-3-yl)pyrimidin-2-ylamino)phenyl]-benzamide
US16/230,676 US11612598B2 (en) 2005-05-26 2018-12-21 Compounds and methods for the treatment of cancer

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US54181704P 2004-02-04 2004-02-04
PCT/EP2005/001077 WO2005075454A2 (en) 2004-02-04 2005-02-03 SALT FORMS OF 4-(4-METHYLPIPERAZIN-1-YLMETHYL)-n-[4-METHYL-3-(4-PYRIDIN-3-YL)PYRIMIDIN-2-YLAMINO)PHENYL]-BENZAMIDE
US10/597,287 US20080249104A1 (en) 2004-02-04 2005-02-03 Salt Forms of 4- (4-Methylpiperazin-1-Ylmethyl) -N- [4-Methyl-3- (4-Pyridin-3-Yl) Pyrimidin-2-Ylamino) Phenyl]- Benzamide

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PCT/EP2005/001077 A-371-Of-International WO2005075454A2 (en) 2004-02-04 2005-02-03 SALT FORMS OF 4-(4-METHYLPIPERAZIN-1-YLMETHYL)-n-[4-METHYL-3-(4-PYRIDIN-3-YL)PYRIMIDIN-2-YLAMINO)PHENYL]-BENZAMIDE
US11/420,425 Continuation-In-Part US20070049602A1 (en) 2005-05-26 2006-05-25 Selective Apoptotic Induction in Cancer Cells Including Activation of Procaspase-3
PCT/US2008/061510 A-371-Of-International WO2008134474A2 (en) 2005-05-26 2008-04-25 Compositions and methods including cell death inducers and procaspase activation

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US13/087,595 Continuation US8592584B2 (en) 2005-05-26 2011-04-15 Compositions and methods including cell death inducers and procaspase activation
US13/087,595 Continuation-In-Part US8592584B2 (en) 2005-05-26 2011-04-15 Compositions and methods including cell death inducers and procaspase activation
US13/368,811 Continuation US8513256B2 (en) 2004-02-04 2012-02-08 Salt forms of 4-(4-methylpiperazin-1-ylmethyl)-N-[4-methyl-3-(4-pyridin-3-yl)pyrimidin-2-ylamino)phenyl]-benzamide

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US10/597,287 Abandoned US20080249104A1 (en) 2004-02-04 2005-02-03 Salt Forms of 4- (4-Methylpiperazin-1-Ylmethyl) -N- [4-Methyl-3- (4-Pyridin-3-Yl) Pyrimidin-2-Ylamino) Phenyl]- Benzamide
US13/368,811 Expired - Fee Related US8513256B2 (en) 2004-02-04 2012-02-08 Salt forms of 4-(4-methylpiperazin-1-ylmethyl)-N-[4-methyl-3-(4-pyridin-3-yl)pyrimidin-2-ylamino)phenyl]-benzamide
US13/946,000 Abandoned US20140051853A1 (en) 2004-02-04 2013-07-19 Salt forms of 4-(4-Methylpiperazin-1-ylmethyl)-N-[4-methyl-3-(4-pyridin-3-yl)pyrimidin-2-ylamino)phenyl]-benzamide

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US13/946,000 Abandoned US20140051853A1 (en) 2004-02-04 2013-07-19 Salt forms of 4-(4-Methylpiperazin-1-ylmethyl)-N-[4-methyl-3-(4-pyridin-3-yl)pyrimidin-2-ylamino)phenyl]-benzamide

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US (3) US20080249104A1 (zh)
EP (1) EP1713792B1 (zh)
JP (1) JP4937760B2 (zh)
KR (2) KR20060135735A (zh)
CN (1) CN100558723C (zh)
AR (1) AR047530A1 (zh)
AU (1) AU2005211514B2 (zh)
BR (1) BRPI0507464A (zh)
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RU (1) RU2375355C2 (zh)
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TW (1) TWI347186B (zh)
WO (1) WO2005075454A2 (zh)
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DE202010017129U1 (de) 2009-01-23 2011-09-14 Teva Pharmaceutical Industries Ltd. Rasagilinformulierung mit verzögerter Freisetzung

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TW201920110A (zh) 2009-01-16 2019-06-01 美商艾克塞里克斯公司 包含n-(4-{[6,7-雙(甲氧基)喹啉-4-基]氧基}苯基)-n'-(4-氟苯基)環丙烷-1,1-二甲醯胺之蘋果酸鹽之醫藥組合物及其用途
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DK2445502T4 (da) 2009-06-25 2022-11-28 Alkermes Pharma Ireland Ltd Heterocycliske forbindelser til behandling af neurologiske og psykologiske lidelser
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WO2017129624A1 (en) 2016-01-25 2017-08-03 Krka, D.D., Novo Mesto Fast dispersible pharmaceutical composition comprising tyrosine-kinase inhibitor
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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20090054415A1 (en) * 2005-04-13 2009-02-26 Bristol-Myers Squibb Company Combinations, methods and compositions for treating cancer
DE202010017129U1 (de) 2009-01-23 2011-09-14 Teva Pharmaceutical Industries Ltd. Rasagilinformulierung mit verzögerter Freisetzung

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