WO2004099183A1 - Nouvelles formes polymorphes de pantoprazole sodium - Google Patents

Nouvelles formes polymorphes de pantoprazole sodium Download PDF

Info

Publication number
WO2004099183A1
WO2004099183A1 PCT/IN2003/000177 IN0300177W WO2004099183A1 WO 2004099183 A1 WO2004099183 A1 WO 2004099183A1 IN 0300177 W IN0300177 W IN 0300177W WO 2004099183 A1 WO2004099183 A1 WO 2004099183A1
Authority
WO
WIPO (PCT)
Prior art keywords
pantoprazole sodium
solvent
pantoprazole
sodium form
process according
Prior art date
Application number
PCT/IN2003/000177
Other languages
English (en)
Inventor
Bandi Parthasaradhi Reddy
Kura Rathnakar Reddy
Rapolu Raji Reddy
Dasari Muralidhara Reddy
Kesireddy Subash Chander Reddy
Original Assignee
Hetero Drugs Limited
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 Hetero Drugs Limited filed Critical Hetero Drugs Limited
Priority to PCT/IN2003/000177 priority Critical patent/WO2004099183A1/fr
Priority to AU2003241150A priority patent/AU2003241150A1/en
Publication of WO2004099183A1 publication Critical patent/WO2004099183A1/fr

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

Definitions

  • the present invention relates to novel polymorphs of pantoprazole sodium, to processes for their preparation and to pharmaceutical compositions containing them.
  • Pantoprazole sodium chemically 5-(Difluoromethoxy)-2-[[(3,4-dimethoxy-2- pyridinyl)methyl]sulfinyl]-1 H-benzimidazole sodium salt, is represented by the following structure:
  • Pantoprazole sodium is an antiulcerative, which is disclosed and claimed in US 4,758,579. A crystalline form of pantoprazole sodium is mentioned in Analytical Profiles of Drug Substances and Excipients - volueme 29, year 2002, page no. 213-259.
  • the object of the present invention is to provide stable polymorphs of pantoprazole sodium, processes for preparing these forms and pharmaceutical compositions containing them.
  • pantoprazole sodium designated as form I, characterized by an x-ray powder diffraction spectrum having peaks expressed as 2 ⁇ at about
  • Figure 1 shows typical form I x-ray powder diffraction spectrum.
  • pantoprazole sodium form I is prepared by dissolving pantoprazole sodium in a suitable solvent and isolating pantoprazole sodium form I from the solution by adding an anti-solvent. Pantoprazole sodium in any crystalline or amorphous form may be used in the process. The quantity of the anti-solvent should be at least sufficient to precipitate pantoprazole sodium from the solution. In accordance with the present invention, an another process is provided for preparation of pantoprazole sodium form I.
  • Pantoprazole sodium form I is prepared by dissolving pantoprazole in a suitable solvent, adding sodium hydroxide to the solution and then isolating pantoprazole sodium form I from the solution by adding an anti-solvent.
  • the quantity of sodium hydroxide to pantoprazole is not limiting, but 0.5 to 2.0 moles of sodium hydroxide per mole of pantoprazole is preferable.
  • the quantity of the anti-solvent should be at least sufficient to precipitate pantoprazole sodium from the solution.
  • pantoprazole sodium designated as form II, characterized by an x-ray powder diffraction spectrum having peaks expressed as 2 ⁇ at about
  • Figure 2 shows typical form II x-ray powder diffraction spectrum.
  • pantoprazole sodium form II prepared by dissolving pantoprazole sodium in acetonitrile and isolating pantoprazole sodium form II from the solution by adding an anti-solvent.
  • Pantoprazole sodium in any crystalline or amorphous form may be used in the process.
  • the quantity of the anti-solvent should be at least sufficient to . precipitate pantoprazole sodium from the solution.
  • Pantoprazole sodium form II is prepared by dissolving pantoprazole in acetonitrile, adding sodium hydroxide and isolating pantoprazole sodium form II from the solution by adding an anti- solvent.
  • the quantity of sodium hydroxide to pantoprazole is not limiting, but 0.5 to 2.0 moles of sodium hydroxide per mole of pantoprazole is preferable.
  • the quantity of the anti-solvent should be at least sufficient to precipitate pantoprazole sodium from the solution.
  • a novel amorphous form of pantoprazole sodium designated as amorphous pantoprazole sodium, characterized by having broad x-ray diffraction spectrum as in figure 3.
  • a process is provided for preparation of amorphous pantoprazole sodium.
  • Amorphous pantoprazole sodium is prepared by dissolving pantoprazole sodium in an alcohol or a mixture of alcohols and removing the solvents from the solution.
  • Pantoprazole sodium in any crystalline or amorphous form may be used in the process.
  • the alcohol is selected from the group consisting of methanol, ethanol and isopropyl alcohol.
  • the solvent may be removed from the solution by vacuum drying or spray drying.
  • the 'suitable solvents' used in the above processes are methanol, ethanol, isopropyl alcohol and acetone; and a mixture thereof.
  • Preferable 'anti-solvent' is diisopropyl ether or toluene; or a mixture thereof.
  • a pharmaceutical composition comprising pantoprazole sodium form I and a pharmaceutically acceptable carrier or diluent.
  • a pharmaceutical composition comprising pantoprazole sodium form II and a pharmaceutically acceptable carrier or diluent.
  • a pharmaceutical composition comprising amorphous pantoprazole sodium and a pharmaceutically acceptable carrier or diluent.
  • Figure 1 is a x-ray powder diffraction spectrum of pantoprazole sodium form I.
  • Figure 2 is a x-ray powder diffraction spectrum of pantoprazole sodium form II.
  • Figure 3 is a x-ray powder diffraction spectrum of amorphous pantoprazole sodium. x-Ray powder diffraction spectrum was measured on a Bruker axs D8 advance x-ray powder diffractometer having a copper-K ⁇ radiation.
  • Pantoprazole and pantoprazole sodium used in the following examples are obtained from the previously known methods.
  • Pantoprazole sodium (5.0 gm) is dissolved in methanol (15 ml) at 30°C and then diisopropyl ether (250 ml) is added. The contents are stirred for 24 hours at 25°C to 30°C and filtered to give 4.8 gm of pantoprazole sodium form I.
  • Pantoprazole (10.0 gm) is dissolved in methanol (30 ml), sodium hydroxide (1.1 gm) is added at 25°C and stirred for 2 hours at 25°C to 30°C. Then diisopropyl ether (250 ml) is added to the solution and stirred for 1 hour at 25°C to 28°C. The separated solid is filtered to give 9.0 gm of pantoprazole sodium form I.
  • Pantoprazole sodium (10.0 gm) is dissolved in acetonitrile (50 ml) at 30°C and then diisopropyl ether (300 ml) is added. The contents are stirred for 6 hours at 25°C to 30°C and filtered to give 4.5 gm of pantoprazole sodium form II.
  • Pantoprazole (10.0 gm) is dissolved in acetonitrile (50 ml), sodium hydroxide (1.1 gm) is added slowly at 25°C to the clear solution. The contents are stirred for 3 hours at 25°C to 30°C. Then diisopropyl ether (300 ml) is added to the solution and stirred for 2 hours at 25°C to 30°C. The separated solid is filtered to give 9.1 gm of pantoprazole sodium form II.
  • Pantoprazole sodium (5.0 gm) is mixed with toluene (100 ml), heated to 70°C and then acetonitirile (50 ml) is added to form a clear solution. The solution is cooled to 30°C, stirred for 20 hours at 25°C to 30°C and the separated solid is filtered to give 4.3 gm of pantoprazole sodium form II.
  • Example 6 Example 3 is repeated using pantoprazole sodium form I instead of pantoprazole sodium.
  • the yield of pantoprazole sodium form II is 4.1 gm.
  • Example 1 is repeated using pantoprazole sodium form II instead of pantoprazole sodium.
  • the yield of pantoprazole sodium form I is 4.6 gm.
  • Pantoprazole sodium (5.0 gm) is dissolved in methanol (50 ml) at 25°C. The solution is subjected to vacuum drying at about 50°C for 7 hours to give amorphous pantoprazole sodium in near quantitative yield.
  • Example 9 Example 8 is repeated by subjecting the solution to spray drying instead of vacuum drying to give amorphous pantoprazole sodium.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

La présente invention a trait à de nouvelles formes polymorphes de pantoprazole sodium, à des leurs procédés de préparation et à des compositions les contenant.
PCT/IN2003/000177 2003-05-06 2003-05-06 Nouvelles formes polymorphes de pantoprazole sodium WO2004099183A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
PCT/IN2003/000177 WO2004099183A1 (fr) 2003-05-06 2003-05-06 Nouvelles formes polymorphes de pantoprazole sodium
AU2003241150A AU2003241150A1 (en) 2003-05-06 2003-05-06 Novel polymorphs of pantoprazole sodium

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/IN2003/000177 WO2004099183A1 (fr) 2003-05-06 2003-05-06 Nouvelles formes polymorphes de pantoprazole sodium

Publications (1)

Publication Number Publication Date
WO2004099183A1 true WO2004099183A1 (fr) 2004-11-18

Family

ID=33428277

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/IN2003/000177 WO2004099183A1 (fr) 2003-05-06 2003-05-06 Nouvelles formes polymorphes de pantoprazole sodium

Country Status (2)

Country Link
AU (1) AU2003241150A1 (fr)
WO (1) WO2004099183A1 (fr)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7507829B2 (en) 2002-12-19 2009-03-24 Teva Pharmaceuticals Industries, Ltd Solid states of pantoprazole sodium, processes for preparing them and processes for preparing known pantoprazole sodium hydrates
US7683177B2 (en) 2003-06-10 2010-03-23 Teva Pharmaceutical Industries Ltd Process for preparing 2-[(pyridinyl)methyl]sulfinyl-substituted benzimidazoles and novel chlorinated derivatives of pantoprazole
CN103214459A (zh) * 2013-03-22 2013-07-24 海南中化联合制药工业股份有限公司 泮托拉唑钠结晶化合物、药物组合物及其制备方法
CN103709140A (zh) * 2013-10-11 2014-04-09 寿光富康制药有限公司 泮托拉唑钠的晶体及其制备方法
WO2016127684A1 (fr) * 2015-02-12 2016-08-18 天津大学 Nouvelle forme cristalline de composé de pantoprazole sodique et son procédé de préparation
CN112587486A (zh) * 2020-12-29 2021-04-02 南京健友生化制药股份有限公司 一种注射用泮托拉唑钠冻干粉针及其制备方法

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2002041919A1 (fr) * 2000-11-22 2002-05-30 Altana Pharma Ag Preparation lyophilisee de pantoprazole et injection de pantoprazole

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2002041919A1 (fr) * 2000-11-22 2002-05-30 Altana Pharma Ag Preparation lyophilisee de pantoprazole et injection de pantoprazole

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7507829B2 (en) 2002-12-19 2009-03-24 Teva Pharmaceuticals Industries, Ltd Solid states of pantoprazole sodium, processes for preparing them and processes for preparing known pantoprazole sodium hydrates
US7915423B2 (en) 2002-12-19 2011-03-29 Teva Pharmaceutical Industries, Ltd. Solid states of pantoprazole sodium, processes for preparing them and processes for preparing known pantoprazole sodium hydrates
US7683177B2 (en) 2003-06-10 2010-03-23 Teva Pharmaceutical Industries Ltd Process for preparing 2-[(pyridinyl)methyl]sulfinyl-substituted benzimidazoles and novel chlorinated derivatives of pantoprazole
CN103214459A (zh) * 2013-03-22 2013-07-24 海南中化联合制药工业股份有限公司 泮托拉唑钠结晶化合物、药物组合物及其制备方法
CN103709140A (zh) * 2013-10-11 2014-04-09 寿光富康制药有限公司 泮托拉唑钠的晶体及其制备方法
WO2016127684A1 (fr) * 2015-02-12 2016-08-18 天津大学 Nouvelle forme cristalline de composé de pantoprazole sodique et son procédé de préparation
CN112587486A (zh) * 2020-12-29 2021-04-02 南京健友生化制药股份有限公司 一种注射用泮托拉唑钠冻干粉针及其制备方法
CN112587486B (zh) * 2020-12-29 2022-05-13 南京健友生化制药股份有限公司 一种注射用泮托拉唑钠冻干粉针及其制备方法

Also Published As

Publication number Publication date
AU2003241150A1 (en) 2004-11-26

Similar Documents

Publication Publication Date Title
US7300938B2 (en) Polymorphs of imatinib mesylate
US7491726B2 (en) Crystalline forms of aripiprazole
US20040010151A1 (en) Lansoprazole polymorphs and processes for preparation thereof
US7456181B2 (en) Aripiprazole crystalline forms
US20050143396A1 (en) Novel crystalline forms of ziprasidone hydrochloride
WO2004099183A1 (fr) Nouvelles formes polymorphes de pantoprazole sodium
US20050119328A1 (en) Novel crysalline forms of tegaserod maleate
EP2718272A2 (fr) Procédé de préparation de fébuxostat
EP2970284B1 (fr) Forme crystalline du cis-(e)-4-(3-fluorophenyl)-2',3',4',9'-tetra-hydro-n,n-dimethyl-2'-(1-oxo-3-phenyl-2-propenyl)-spiro[cyclohexane-1,1'[1h]-pyrido[3,4-b]indol]-4-amine
WO2009099933A2 (fr) Préparation de magnésium d’ésoméprazole et de ses hydrates
US20090233932A1 (en) Novel crystalline forms of lamotrigine
EP1598347A1 (fr) Polymorphes du sel de sodium de pantoprazole et procédé de préparation
WO2014195977A2 (fr) Nouveaux polymorphes de vismodegib
US20180273490A1 (en) Process for the Preparation of Eltrombopag Olamine
US20050143445A1 (en) Novel crystalline forms of levetiracetam
US7393874B2 (en) Polymorphs of tolterodine tartrate
US20050165075A1 (en) Novel amorphous form of valsartan
US20100204478A1 (en) Improved process for amophous rabeprazole sodium
WO2010089753A2 (fr) Nouveaux polymorphes du lopinavir
US20050154052A1 (en) Novel crystalline forms of (s)-citalopram oxalate
WO2012123963A2 (fr) Procédé pour la préparation d'ilopéridone et de coprécipité amorphe d'ilopéridone avec un excipient pharmaceutiquement acceptable
US20050143431A1 (en) Novel crystalline forms of parecoxib sodium
CN116640129A (zh) 一种精制方法
WO2004099140A1 (fr) Nouvelles formes cristallines de succinate de sumatriptan
WO2004087688A1 (fr) Nouvelles formes cristallines de gatifloxacine

Legal Events

Date Code Title Description
WWE Wipo information: entry into national phase

Ref document number: 671/CHENP/2003

Country of ref document: IN

AK Designated states

Kind code of ref document: A1

Designated state(s): AE AG AL AM AT AU AZ BA BB BG BR BY BZ CA CH CN CO CR CU CZ DE DK DM DZ EC EE ES FI GB GD GE GH GM HR HU ID IL IN IS JP KE KG KP KR KZ LC LK LR LS LT LU LV MA MD MG MK MN MW MX MZ NI NO NZ OM PH PL PT RO RU SC SD SE SG SK SL TJ TM TN TR TT TZ UA UG US UZ VC VN YU ZA ZM ZW

AL Designated countries for regional patents

Kind code of ref document: A1

Designated state(s): GH GM KE LS MW MZ SD SL SZ TZ UG ZM ZW AM AZ BY KG KZ MD RU TJ TM AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HU IE IT LU MC NL PT RO SE SI SK TR BF BJ CF CG CI CM GA GN GQ GW ML MR NE SN TD TG

121 Ep: the epo has been informed by wipo that ep was designated in this application
122 Ep: pct application non-entry in european phase
NENP Non-entry into the national phase

Ref country code: JP