EP1877395A2 - Sels de l'ethylester d'acide 3-[(2-{[4-(hexyloxycarbonylamino-imino-methyl)-phenylamino]-methyl}-1-methyl-1h-benzimidazol-5-carbonyl)-pyridin-2-yl-amino]-propionique physiologiquement compatibles - Google Patents

Sels de l'ethylester d'acide 3-[(2-{[4-(hexyloxycarbonylamino-imino-methyl)-phenylamino]-methyl}-1-methyl-1h-benzimidazol-5-carbonyl)-pyridin-2-yl-amino]-propionique physiologiquement compatibles

Info

Publication number
EP1877395A2
EP1877395A2 EP06754844A EP06754844A EP1877395A2 EP 1877395 A2 EP1877395 A2 EP 1877395A2 EP 06754844 A EP06754844 A EP 06754844A EP 06754844 A EP06754844 A EP 06754844A EP 1877395 A2 EP1877395 A2 EP 1877395A2
Authority
EP
European Patent Office
Prior art keywords
methyl
amino
benzimidazole
carbonyl
pyridin
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.)
Withdrawn
Application number
EP06754844A
Other languages
German (de)
English (en)
Inventor
Peter Sieger
Norbert Hauel
Rolf Schmid
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.)
Boehringer Ingelheim International GmbH
Boehringer Ingelheim Pharma GmbH and Co KG
Boehringer Ingelheim Pharmaceuticals Inc
Original Assignee
Boehringer Ingelheim International GmbH
Boehringer Ingelheim Pharma GmbH and Co KG
Boehringer Ingelheim Pharmaceuticals Inc
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
Family has litigation
First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=36952435&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=EP1877395(A2) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Application filed by Boehringer Ingelheim International GmbH, Boehringer Ingelheim Pharma GmbH and Co KG, Boehringer Ingelheim Pharmaceuticals Inc filed Critical Boehringer Ingelheim International GmbH
Publication of EP1877395A2 publication Critical patent/EP1877395A2/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • 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
    • C07D401/12—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 linked by a chain containing hetero atoms as chain links
    • 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

Definitions

  • the invention relates to novel, physiologically acceptable salts for the active ingredient 3 - [(2- ⁇ [4- (hexyloxycarbonylamino-imino-methyl) -phenylamino] -methyl ⁇ -1-methyl-1 / - / - benzimidazole-5 carbonyl) -pyridin-2-yl-amino] -propionic acid ethyl ester, their enantiomers, their mixtures and their hydrates.
  • the compound of Chemical Formula I is the postoperative prophylaxis of deep vein thrombosis and the prophylaxis of strokes.
  • the object of the invention is to provide novel salts of the compound of the formula I with advantageous properties for the pharmaceutical application.
  • an active ingredient In addition to the actual effectiveness for the desired indication, an active ingredient must meet even further requirements in order to be able to be used as a medicament. These parameters are to a large extent related to the physicochemical nature of the active substance.
  • examples of these parameters are the effective stability of the starting material under various environmental conditions, stability in the course of preparation of the pharmaceutical formulation, and stability in the final compositions of the drug.
  • the drug used for the preparation of the drug compositions should therefore have a high stability, which must be ensured even under different environmental conditions. This is absolutely necessary in order to prevent the use of pharmaceutical compositions in which, in addition to the actual active substance, for example, degradation products thereof are contained. In such a case, an active ingredient content found in pharmaceutical formulations could be lower than specified.
  • the absorption of moisture reduces the content of drug due to the increase in weight caused by the absorption of water.
  • Moisture-prone drugs must be protected from moisture during storage, for example by adding suitable drying agents or by storing the drug in a humidity protected environment.
  • the ingestion of moisture may reduce the level of drug during manufacture if the drug is exposed to the environment without any protection from moisture.
  • a drug should only be slightly hygroscopic. Since the crystal modification of an active ingredient is important for the reproducible active ingredient content of a dosage form, there is a need to elucidate possibly existing polymorphism of a crystalline active substance in the best possible way.
  • solubility of the active ingredient Another criterion which, depending on the choice of formulation or the choice of the preparation process of the formulation of possibly outstanding importance, is the solubility of the active ingredient. If, for example, drug solutions (for example for infusions) are provided, adequate solubility of the active substance in physiologically compatible solvents is indispensable. Also for orally administered drugs sufficient solubility of the drug is of great importance.
  • the invention therefore provides the salts of 3 - [(2 - ⁇ [4- (hexyloxycarbonylamino-imino-methyl) -phenylamino] -methyl ⁇ -1-methyl-1 / - / - benzimidazole-5-carbonyl) - pyridin-2-yl-amino] -propionic acid ethyl ester with hydrochloric acid, maleic acid, tartaric acid, salicylic acid, citric acid and malonic acid and their enantiomers, their mixtures and their hydrates.
  • a further subject of the invention are pharmaceutical compositions containing at least one of the abovementioned salts or hydrates and processes for the preparation of these medicaments suitable for the prevention of venous thrombosis and stroke.
  • the salts according to the invention as well as 3 - [(2 - ⁇ [4- (hexyloxycarbonylamino-iminomethyl) -phenyl-amino] -methyl ⁇ -1-methyl-1 / - / - benzimidazole-5-carbonyl) -pyridin-2-yl free amino acid amino ester -propionic acid esters and methanesulfonic acid salt are also useful in the treatment and prevention of deep venous thrombosis in patients with heparin-induced thrombocytopenia and prevention of thrombosis in patients with intra-arterial or intravenous lines or Catheters and AV shunts suitable.
  • the melting points were determined by means of DSC, a device from Mettler-Toledo (type: DSC 821) was used for this purpose.
  • the melting temperature used was the onset temperature of the corresponding melting peak in the DSC diagram.
  • the accuracy of the stated melting points is about ⁇ 3 0 C.
  • the starting compound 3 - [(2 - ⁇ [4- (aminohexyloxycarbonylimino-methyl) -phenyl-amino] -methyl ⁇ -1-methyl-7 / - / - benzimidazole-5-carbonyl) -pyridin-2-yl amino] propionic acid ethyl ester can be prepared, for example, as described in International Application WO 98/37075, Example 113.
  • Example 3 Tartaric acid salt of 3 - [(2 - ⁇ [4- (amino-hexyloxycarbonylimino-methyl) -phenylamino] -methyl ⁇ -1-methyl-7 / - / - benzimidazole-5-carbonyl) -pyridine-2 yl-amino] -propionic acid ethyl ester
  • Example 4 Malonic acid salt of 3 - [(2 - ⁇ [4- (amino-hexyloxycarbonyl-imino-methyl) -phenyl-amino] -methyl ⁇ -1-methyl-7 / - / - benzimidazole-5-carbonyl) -pyridine-2 yl-amino] -propionic acid ethyl ester
  • Active substance and mannitol are dissolved in water. After bottling is freeze-dried.
  • the solution to the ready-to-use solution is water for injections.
  • composition (1) Active ingredient 50.0 mg
  • (1), (2) and (3) are mixed and granulated with an aqueous solution of (4).
  • the dried granules are admixed with (5).
  • From this mixture tablets are pressed, biplan with double-sided facet and one-sided part score. Diameter of the tablets: 9 mm.
  • (1) is triturated with (3). This trituration is added to the mixture of (2) and (4) under intensive mixing. This powder mixture is filled in a capsule filling machine in hard gelatin capsule size 3.
  • (1) is triturated with (3). This trituration is added to the mixture of (2) and (4) under intensive mixing.
  • 1 suppository contains: active substance 100.0 mg
  • Polyethylene glycol (M.G. 1500) 600.0 mg Polyethylene glycol (M.G. 6000) 460.0 mg Polyethyl sorbitan monostearate 840.0 mg 2,000.0 mg

Landscapes

  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Veterinary Medicine (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Engineering & Computer Science (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Public Health (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Hematology (AREA)
  • Diabetes (AREA)
  • Cardiology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

L'invention concerne de nouveaux sels physiologiquement compatibles du principe actif d'éthylester d'acide 3- [(2-{[4-(hexyloxycarbonylamino-imino-méthyl)-phénylamino]-méthyl}-1-méthyl-1H-benzimidazol-5-carbonyl)-pyridin-2-yl-amino]-propionique.
EP06754844A 2005-04-27 2006-04-25 Sels de l'ethylester d'acide 3-[(2-{[4-(hexyloxycarbonylamino-imino-methyl)-phenylamino]-methyl}-1-methyl-1h-benzimidazol-5-carbonyl)-pyridin-2-yl-amino]-propionique physiologiquement compatibles Withdrawn EP1877395A2 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102005020002A DE102005020002A1 (de) 2005-04-27 2005-04-27 Physiologisch verträgliche Salze von 3-[(2-{[4-(Hexyloxycarbonylamino-imino-methyl)-phenylamino]-methyl}-1-methyl-1H-benzimidazol-5-carbonyl)-pyridin-2-yl-amino]-propionsäure-ethylester
PCT/EP2006/061820 WO2006114415A2 (fr) 2005-04-27 2006-04-25 Sels de l'ethylester d'acide 3-[(2-{[4-(hexyloxycarbonylamino-imino-methyl)-phenylamino]-methyl}-1-methyl-1h-benzimidazol-5-carbonyl)-pyridin-2-yl-amino]-propionique physiologiquement compatibles

Publications (1)

Publication Number Publication Date
EP1877395A2 true EP1877395A2 (fr) 2008-01-16

Family

ID=36952435

Family Applications (1)

Application Number Title Priority Date Filing Date
EP06754844A Withdrawn EP1877395A2 (fr) 2005-04-27 2006-04-25 Sels de l'ethylester d'acide 3-[(2-{[4-(hexyloxycarbonylamino-imino-methyl)-phenylamino]-methyl}-1-methyl-1h-benzimidazol-5-carbonyl)-pyridin-2-yl-amino]-propionique physiologiquement compatibles

Country Status (10)

Country Link
US (2) US20060247278A1 (fr)
EP (1) EP1877395A2 (fr)
JP (1) JP2008539199A (fr)
AR (1) AR054261A1 (fr)
CA (1) CA2606090A1 (fr)
DE (1) DE102005020002A1 (fr)
PE (1) PE20061321A1 (fr)
TW (1) TW200716610A (fr)
UY (1) UY29493A1 (fr)
WO (1) WO2006114415A2 (fr)

Cited By (11)

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EP2722034A1 (fr) 2012-10-19 2014-04-23 Sanovel Ilac Sanayi ve Ticaret A.S. Formulations pharmaceutiques orales comprenant du dabigatran
EP2722033A1 (fr) 2012-10-19 2014-04-23 Sanovel Ilac Sanayi ve Ticaret A.S. Compositions pharmaceutiques de Dabigatran sous forme de base libre
EP2929884A1 (fr) 2014-04-11 2015-10-14 Sanovel Ilac Sanayi ve Ticaret A.S. Combinaisons pharmaceutiques de dabigatran et antagonistes du récepteur de h2
EP2933002A1 (fr) 2014-04-11 2015-10-21 Sanovel Ilac Sanayi ve Ticaret A.S. Compositions pharmaceutiques comprenants de dabigratan et des inhibiteurs de la pompe à protons
WO2017013106A1 (fr) 2015-07-20 2017-01-26 Sanovel Ilac Sanayi Ve Ticaret A.S. Préparations pharmaceutiques de dabigatran sous forme de base libre
EP3246020A1 (fr) 2016-05-20 2017-11-22 Sanovel Ilac Sanayi ve Ticaret A.S. Nouvelles formulations pharmaceutiques orales de dabigatran
EP3332771A1 (fr) 2016-12-07 2018-06-13 Sanovel Ilac Sanayi ve Ticaret A.S. Compositions de comprimé multicouche de dabigatran
EP3332770A1 (fr) 2016-12-07 2018-06-13 Sanovel Ilac Sanayi ve Ticaret A.S. Compositions pharmaceutiques de dabigatran
WO2019132839A1 (fr) 2017-12-27 2019-07-04 Sanovel Ilac Sanayi Ve Ticaret Anonim Sirketi Compositions pharmaceutiques orales de dabigatran
WO2019132838A1 (fr) 2017-12-27 2019-07-04 Sanovel Ilac Sanayi Ve Ticaret Anonim Sirketi Compositions pharmaceutiques de dabigatran
WO2019151966A2 (fr) 2017-12-28 2019-08-08 Sanovel Ilac Sanayi Ve Ticaret Anonim Sirketi Compositions pharmaceutiques de dabigatran sous forme de comprimés

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US20030181488A1 (en) 2002-03-07 2003-09-25 Boehringer Ingelheim Pharma Gmbh & Co. Kg Administration form for the oral application of 3-[(2-{[4-(hexyloxycarbonylamino-imino-methyl)-phenylamino]-methyl}-1-methyl-1H-benzimidazol-5-carbonyl)-pyridin-2-yl-amino]-propionic acid ethyl ester and the salts thereof
DE10339862A1 (de) * 2003-08-29 2005-03-24 Boehringer Ingelheim Pharma Gmbh & Co. Kg 3-[(2-{[4-(Hexyloxycarbonylamino-imino-methyl)- phenylamino]-methyl}-1-methyl-1H-benzimidazol-5-carbonyl)-pyridin-2-yl-amino]-propionsäure-ethylester-Methansulfonat und dessen Verwendung als Arzneimittel
US20100087488A1 (en) * 2006-10-10 2010-04-08 Boehringer Ingelheim International Gmgh Physiologically Acceptable Salts of 3-[(2--1-methyl-1H-benzimidazol-5-carbonyl)-pyridin-2-yl-amino]-propionic acid ethyl ester
US20110129538A1 (en) * 2008-03-28 2011-06-02 Boehringer Ingelheim International Gmbh Process for preparing orally administered dabigatran formulations
JP2011527318A (ja) 2008-07-14 2011-10-27 ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング ダビガトランを含有する医薬組成物の製造方法
AU2009315729A1 (en) 2008-11-11 2010-05-20 Boehringer Ingelheim International Gmbh Method for treating or preventing thrombosis using dabigatran etexilate or a salt thereof with improved safety profile over conventional warfarin therapy
EP2391893B1 (fr) * 2009-02-02 2014-09-03 Boehringer Ingelheim International GmbH Dabigatran lyophilisé
HUP1000069A2 (en) * 2010-02-02 2012-05-02 Egis Gyogyszergyar Nyilvanosan M Kod Ruszvunytarsasag New salts for the preparation of pharmaceutical composition
JP2013521318A (ja) 2010-03-08 2013-06-10 ラティオファルム ゲー・エム・ベー・ハー ダビガトランエテキシラートを含有する医薬組成物
JP2013532164A (ja) 2010-07-09 2013-08-15 エステヴェ キミカ， エス．エー． トロンビン特異的インヒビターを調製する方法
US20130116441A1 (en) 2010-07-09 2013-05-09 Esteve Quimica, S.A. Intermediates and process for preparing a thrombin specific inhibitor
PL2603503T3 (pl) 2010-09-27 2015-12-31 Ratiopharm Gmbh Sól bismesylanowa eteksylanu dabigatranu, postacie stałe i sposób ich otrzymywania
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JP2015504903A (ja) * 2012-01-24 2015-02-16 ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング 新規の経口投与用ダビガトラン製剤
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WO2014049585A2 (fr) 2012-09-28 2014-04-03 Ranbaxy Laboratories Limited Procédé de préparation d'étéxilate de dabigatran ou d'un sel pharmaceutiquement acceptable de cette substance
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CN103864756B (zh) * 2012-12-11 2018-06-15 四川海思科制药有限公司 丁二磺酸达比加群酯及其制备方法和用途
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Cited By (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2722033A1 (fr) 2012-10-19 2014-04-23 Sanovel Ilac Sanayi ve Ticaret A.S. Compositions pharmaceutiques de Dabigatran sous forme de base libre
WO2014060545A1 (fr) 2012-10-19 2014-04-24 Sanovel Ilac Sanayi Ve Ticaret A.S. Compositions pharmaceutiques de dabigatran sous forme de base libre
WO2014060561A1 (fr) 2012-10-19 2014-04-24 Sanovel Ilac Sanayi Ve Ticaret A.S. Formulations pharmaceutiques orales contenant du dabigatran
EP2722034A1 (fr) 2012-10-19 2014-04-23 Sanovel Ilac Sanayi ve Ticaret A.S. Formulations pharmaceutiques orales comprenant du dabigatran
US10130618B2 (en) 2014-04-11 2018-11-20 Sanovel Ilac Sanayi Ve Ticaret Anonim Sirketi Pharmaceutical combinations of dabigatran and proton pump inhibitors
EP2929884A1 (fr) 2014-04-11 2015-10-14 Sanovel Ilac Sanayi ve Ticaret A.S. Combinaisons pharmaceutiques de dabigatran et antagonistes du récepteur de h2
WO2015155297A1 (fr) 2014-04-11 2015-10-15 Sanovel Ilac Sanayi Ve Ticaret A.S. Combinaisons pharmaceutiques de dabigatran et d'antagonistes du récepteur h2
EP2933002A1 (fr) 2014-04-11 2015-10-21 Sanovel Ilac Sanayi ve Ticaret A.S. Compositions pharmaceutiques comprenants de dabigratan et des inhibiteurs de la pompe à protons
WO2017013106A1 (fr) 2015-07-20 2017-01-26 Sanovel Ilac Sanayi Ve Ticaret A.S. Préparations pharmaceutiques de dabigatran sous forme de base libre
EP3246020A1 (fr) 2016-05-20 2017-11-22 Sanovel Ilac Sanayi ve Ticaret A.S. Nouvelles formulations pharmaceutiques orales de dabigatran
WO2017198783A1 (fr) 2016-05-20 2017-11-23 Sanovel Ilac Sanayi Ve Ticaret A.S. Nouvelles formulations pharmaceutiques orales de dabigatran
EP3332771A1 (fr) 2016-12-07 2018-06-13 Sanovel Ilac Sanayi ve Ticaret A.S. Compositions de comprimé multicouche de dabigatran
EP3332770A1 (fr) 2016-12-07 2018-06-13 Sanovel Ilac Sanayi ve Ticaret A.S. Compositions pharmaceutiques de dabigatran
WO2018104370A1 (fr) 2016-12-07 2018-06-14 Sanovel Ilac Sanayi Ve Ticaret A.S. Compositions pharmaceutiques de dabigatran
WO2018104387A1 (fr) 2016-12-07 2018-06-14 Sanovel Ilac Sanayi Ve Ticaret A.S. Compositions de comprimés multicouche de dabigatran
WO2019132839A1 (fr) 2017-12-27 2019-07-04 Sanovel Ilac Sanayi Ve Ticaret Anonim Sirketi Compositions pharmaceutiques orales de dabigatran
WO2019132838A1 (fr) 2017-12-27 2019-07-04 Sanovel Ilac Sanayi Ve Ticaret Anonim Sirketi Compositions pharmaceutiques de dabigatran
WO2019151966A2 (fr) 2017-12-28 2019-08-08 Sanovel Ilac Sanayi Ve Ticaret Anonim Sirketi Compositions pharmaceutiques de dabigatran sous forme de comprimés

Also Published As

Publication number Publication date
AR054261A1 (es) 2007-06-13
WO2006114415A2 (fr) 2006-11-02
UY29493A1 (es) 2006-11-30
WO2006114415A3 (fr) 2007-01-25
US20060247278A1 (en) 2006-11-02
CA2606090A1 (fr) 2006-11-02
JP2008539199A (ja) 2008-11-13
US20090042948A1 (en) 2009-02-12
DE102005020002A1 (de) 2006-11-02
PE20061321A1 (es) 2007-01-15
TW200716610A (en) 2007-05-01

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