WO2008028959A1 - Forme cristalline d'hydrochlorure de moxifloxacine - Google Patents

Forme cristalline d'hydrochlorure de moxifloxacine Download PDF

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Publication number
WO2008028959A1
WO2008028959A1 PCT/EP2007/059397 EP2007059397W WO2008028959A1 WO 2008028959 A1 WO2008028959 A1 WO 2008028959A1 EP 2007059397 W EP2007059397 W EP 2007059397W WO 2008028959 A1 WO2008028959 A1 WO 2008028959A1
Authority
WO
WIPO (PCT)
Prior art keywords
moxifloxacin hydrochloride
crystalline form
water
crude
methanol
Prior art date
Application number
PCT/EP2007/059397
Other languages
English (en)
Inventor
Francisco Palomo Nicolau
Javier Villasante Prieto
Original Assignee
Quimica Sintetica, S. A.
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 Quimica Sintetica, S. A. filed Critical Quimica Sintetica, S. A.
Publication of WO2008028959A1 publication Critical patent/WO2008028959A1/fr

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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
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/47—Quinolines; Isoquinolines
    • A61K31/4709—Non-condensed quinolines and containing further heterocyclic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/04—Antibacterial agents

Definitions

  • the present invention refers to a new stable crystalline form of moxifloxacin hydrochloride, to a process of its preparation and to its use in the preparation of pharmaceuticals compositions.
  • the moxifloxacin hydrochloride is the international non-proprietary name of l-cyclopropyl-6- fluoro-1, 4-dihydro-8-metoxy-7- [ (4aS, 7aS) -octahydro-6H- pyrrol [3, 4-b] pyridin-6-yl] -4-oxo-3-quinolincarboxylic acid hydrochloride of Formula (I), which can be applied in medicine and used as antibacterial agent.
  • the stability of a pharmaceutically active substance is important in the pharmaceutical compositions to determine the conservation time of the drug. For this reason, the pharmaceutically active substance used to prepare pharmaceutical substances must be the most stable as possible to guarantee its stability in long-life storage under different environmental conditions. It must be taken into account that any change relative to the solid state of a pharmaceutical composition, capable to enhance its physical stability provides a significant advantage with respect to less stable forms of the drug.
  • the objective of the invention is to provide a new crystalline form of the moxifloxacin hydrochloride compound having constant physical properties .
  • the object of the present invention is to provide a new polymorphic form of stable moxifloxacin hydrochloride .
  • Another object of the present invention is to provide a process for preparing said polymorphic form.
  • Fig. 1 shows the X-ray powder diffraction pattern for the new crystalline form object of the invention.
  • Fig. 2 shows the infrared spectrum of the new crystalline form object of the invention.
  • the new crystalline form of moxifloxacin hydrochloride, object of the invention is stabilized in form of sesquihydrate .
  • the new crystalline form of moxifloxacin hydrochloride, object of the invention is characterized by the X-ray powder diffraction pattern of Fig. 1, having characteristic peaks at the angles 2 ⁇ of 8.1 ⁇ 0.2, 9.8 ⁇ 0.2, 15.2 ⁇ 0.2, 17.7 ⁇ 0.2 and 22.6 ⁇ 0.2.
  • the new crystalline form of moxifloxacin hydrochloride presents an infrared spectrum containing the characteristic peaks shown in table 2.
  • a process for preparing the new crystalline form of moxifloxacin hydrochloride comprising the following steps: i) to dissolve crude moxifloxacin hydrochloride in a mixture of methanol/water by heating at the reflux temperature; ii) to add acetone and to heat the dissolution at a temperature comprised between 40 and 45 0 C; iii) to cool until a temperature comprised between 15 and 25 0 C; iv) to separate the crystals formed by filtration; v) to wash and dry the obtained product until a constant weight is obtained.
  • the crude moxifloxacin hydrochloride used as starting product is obtained by the process described in the preparation example 4 disclosed in the European Patent Application EP07103405.
  • the dissolution of crude moxifloxacin hydrochloride is carried out, preferably, in mixtures of methanol/water 1.5:1 (vol/vol) , preferably 1:1 (vol/vol) and it is prepared, preferably, using up to 10, preferably 7-8, volumes of the mixture methanol/water for each weight unit of moxifloxacin hydrochloride.
  • the obtained solid is divided by filtration and it is washed with a mixture of acetone/methanol/water . Then, the humid solid is dried with a vacuum stove, preferably, at 4O 0 C until a constant weight.
  • the new crystalline form of moxifloxacin hydrochloride obtained is a stable sesquihydrate form along a prolonged time, which is suitable for its distribution and storing. These features make the new polymorphic form suitable in the development of a pharmaceutical product.
  • Another object of the present invention is to provide a pharmaceutical composition
  • a pharmaceutical composition comprising the crystalline form of moxifloxacin hydrochloride according to the first object of the invention, with one or more excipients or other auxiliary agents pharmaceutically acceptable.
  • Copper tube at 40KV and 40 mA.
  • the infrared spectrum was obtained in KBr using a spectrometer Perkin Elmer Spectrum One FT-IR.
  • table 2 attached the infrared absorbencies for the crystalline form of the invention are provided.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Medicinal Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Epidemiology (AREA)
  • Oncology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Communicable Diseases (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

La présente invention concerne une nouvelle forme cristalline stable d'hydrochlorure de moxifloxacine, un procédé permettant de la préparer et son utilisation dans la préparation de compositions pharmaceutiques. Est proposé un procédé comprenant les opérations consistant à : dissoudre de l'hydrochlorure de moxifloxacine brut dans un mélange de méthanol/eau par chauffage à la température de reflux; ajouter de l'acétone et chauffer le produit de dissolution à une température comprise entre 40 et 45 °C; refroidir jusqu'à une température comprise entre 15 et 25 °C; séparer les cristaux formés par filtration; et laver et sécher le produit obtenu jusqu'à ce qu'un poids constant soit obtenu.
PCT/EP2007/059397 2006-09-08 2007-09-07 Forme cristalline d'hydrochlorure de moxifloxacine WO2008028959A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
ESP200602303 2006-09-08
ES200602303A ES2303768B1 (es) 2006-09-08 2006-09-08 Nueva forma cristalina de moxifloxacino clorhidrato.

Publications (1)

Publication Number Publication Date
WO2008028959A1 true WO2008028959A1 (fr) 2008-03-13

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ID=38963213

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2007/059397 WO2008028959A1 (fr) 2006-09-08 2007-09-07 Forme cristalline d'hydrochlorure de moxifloxacine

Country Status (2)

Country Link
ES (1) ES2303768B1 (fr)
WO (1) WO2008028959A1 (fr)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2009087151A1 (fr) * 2008-01-08 2009-07-16 Chemo Ibérica, S.A. Formes polymorphes de chlorhydrate de moxifloxacine et leurs procédés de préparation
WO2010052726A1 (fr) * 2008-11-06 2010-05-14 Hetero Research Foundation Polymorphe inédit de l'hydrochlorure de moxifloxacine
CN102603738A (zh) * 2012-02-24 2012-07-25 天津市汉康医药生物技术有限公司 一种稳定的盐酸莫西沙星化合物
CN102924449A (zh) * 2012-10-30 2013-02-13 重庆福安药业集团庆余堂制药有限公司 盐酸莫西沙星h晶型及其制备方法和药物组合物
CN103965189A (zh) * 2013-12-30 2014-08-06 西安万隆制药股份有限公司 一种新的盐酸莫西沙星化合物

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0780390A1 (fr) * 1995-12-12 1997-06-25 Bayer Ag Modification cristalline du CDCH, procédé pour sa préparation et compositions pharmaceutiques la contenant
WO2004091619A1 (fr) * 2003-04-09 2004-10-28 Dr. Reddy's Laboratories Limited Forme cristalline iii de chlorhydrate de moxifloxacine anhydre et procede de preparation de cette derniere
WO2005012285A1 (fr) * 2003-08-05 2005-02-10 Matrix Laboratories Ltd Procede ameliore permettant de preparer un hydrochlorure de moxifloxacine
WO2005054240A1 (fr) * 2003-11-20 2005-06-16 Chemi Spa Polymorphes d'hydrochlorure d'acide 1-cyclopropyl-7-((s,s)-2,8-diazadicyclo(4.3.0)non-8-yl)-6-fluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinoline carboxylique, et leurs methodes de preparation
WO2006134491A2 (fr) * 2005-06-14 2006-12-21 Aurobindo Pharma Limited Nouvelle forme cristalline d'hydrochlorure de moxifloxacine et procede de preparation de cette derniere
WO2007010555A2 (fr) * 2005-07-15 2007-01-25 Msn Laboratories Limited Nouvelles formes cristallines d'hydrochlorure de moxifloxacine et procede de preparation associe
WO2007148137A1 (fr) * 2006-06-23 2007-12-27 Generics [Uk] Limited Nouvelle forme hydrate du monochlorhydrate de moxifloxacine

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1562942A1 (fr) * 2002-10-31 2005-08-17 Ranbaxy Laboratories, Ltd. Hydrochlorure amorphe de moxifloxacine

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0780390A1 (fr) * 1995-12-12 1997-06-25 Bayer Ag Modification cristalline du CDCH, procédé pour sa préparation et compositions pharmaceutiques la contenant
WO2004091619A1 (fr) * 2003-04-09 2004-10-28 Dr. Reddy's Laboratories Limited Forme cristalline iii de chlorhydrate de moxifloxacine anhydre et procede de preparation de cette derniere
WO2005012285A1 (fr) * 2003-08-05 2005-02-10 Matrix Laboratories Ltd Procede ameliore permettant de preparer un hydrochlorure de moxifloxacine
WO2005054240A1 (fr) * 2003-11-20 2005-06-16 Chemi Spa Polymorphes d'hydrochlorure d'acide 1-cyclopropyl-7-((s,s)-2,8-diazadicyclo(4.3.0)non-8-yl)-6-fluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinoline carboxylique, et leurs methodes de preparation
WO2006134491A2 (fr) * 2005-06-14 2006-12-21 Aurobindo Pharma Limited Nouvelle forme cristalline d'hydrochlorure de moxifloxacine et procede de preparation de cette derniere
WO2007010555A2 (fr) * 2005-07-15 2007-01-25 Msn Laboratories Limited Nouvelles formes cristallines d'hydrochlorure de moxifloxacine et procede de preparation associe
WO2007148137A1 (fr) * 2006-06-23 2007-12-27 Generics [Uk] Limited Nouvelle forme hydrate du monochlorhydrate de moxifloxacine

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
RAVIKUMAR, KRISHNAN ET AL., ACTA CRYSTALLOGRAPHICA SECTION C, vol. 62, 2006, pages O478 - O482, XP002466687 *

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2009087151A1 (fr) * 2008-01-08 2009-07-16 Chemo Ibérica, S.A. Formes polymorphes de chlorhydrate de moxifloxacine et leurs procédés de préparation
EP2083010A1 (fr) * 2008-01-08 2009-07-29 Chemo Ibérica, S.A. Formes polymorphes d'hydrochlorure de moxifloxacine et leurs procédés de préparation
WO2010052726A1 (fr) * 2008-11-06 2010-05-14 Hetero Research Foundation Polymorphe inédit de l'hydrochlorure de moxifloxacine
CN102603738A (zh) * 2012-02-24 2012-07-25 天津市汉康医药生物技术有限公司 一种稳定的盐酸莫西沙星化合物
CN102603738B (zh) * 2012-02-24 2013-12-11 天津市汉康医药生物技术有限公司 一种稳定的盐酸莫西沙星化合物
CN102924449A (zh) * 2012-10-30 2013-02-13 重庆福安药业集团庆余堂制药有限公司 盐酸莫西沙星h晶型及其制备方法和药物组合物
CN102924449B (zh) * 2012-10-30 2015-08-12 重庆福安药业集团庆余堂制药有限公司 盐酸莫西沙星h晶型及其制备方法和药物组合物
CN103965189A (zh) * 2013-12-30 2014-08-06 西安万隆制药股份有限公司 一种新的盐酸莫西沙星化合物
CN103965189B (zh) * 2013-12-30 2015-09-09 西安万隆制药股份有限公司 一种新的盐酸莫西沙星化合物

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Publication number Publication date
ES2303768A1 (es) 2008-08-16
ES2303768B1 (es) 2009-06-05

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