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WO2008065542A2 - Procédé perfectionné pour la fabrication de risédronate sodique - Google Patents

Procédé perfectionné pour la fabrication de risédronate sodique Download PDF

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Publication number
WO2008065542A2
WO2008065542A2 PCT/IB2007/004344 IB2007004344W WO2008065542A2 WO 2008065542 A2 WO2008065542 A2 WO 2008065542A2 IB 2007004344 W IB2007004344 W IB 2007004344W WO 2008065542 A2 WO2008065542 A2 WO 2008065542A2
Authority
WO
WIPO (PCT)
Prior art keywords
risedronate
hemipentahydrate
monohydrate
acid
sodium
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.)
Ceased
Application number
PCT/IB2007/004344
Other languages
English (en)
Other versions
WO2008065542A3 (fr
Inventor
Siripragada Mahender Rao
Thangavel Arulmoli
Venu Sanjeevi Lakshmipathi
Vasanthakumar Jagannath
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.)
Orchid Pharma Ltd
Original Assignee
Orchid Chemicals and Pharmaceuticals Ltd
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 Orchid Chemicals and Pharmaceuticals Ltd filed Critical Orchid Chemicals and Pharmaceuticals Ltd
Publication of WO2008065542A2 publication Critical patent/WO2008065542A2/fr
Publication of WO2008065542A3 publication Critical patent/WO2008065542A3/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
    • C07F9/576—Six-membered rings
    • C07F9/58—Pyridine rings

Definitions

  • the present invention relates to an improved process for the preparation of hydrates of Risedronate monosodium, which is used for the treatment of osteoporosis.
  • Risedronate monosodium of formula (I) is chemically known as l-Hydroxy-2-(3- pyridyl) ⁇ thane-l ,l-diphosphonic acid monosodium salt, which is a pyridinyl bisphosphonate that inhibits osteoclast-mediated bone resorption and modulates bone metabolism.
  • US Patent No. 6,410,520 discloses the existence of Risedronate monosodium in three hydration states: hemipentahydrate, monohydrate and anhydrous.
  • the '520 patent also discloses selective crystallization of mono- and hemipentahydrates by heating an aqueous solution of 3-pyridyl-l-hydroxyethylidine-l,l-bisphosphonic acid sodium from about 45 0 C to about 75 0 C and crystallization of product by the addition of isopropanol, and cooling with different cooling ramp. According to '520 patent, monohydrate crystals were converted to the hemipentahydrate form.
  • US Patent application No. 2003 / 0195170 Al teaches the preparation of form B (monohydrate) of Risedronate sodium by refluxing a mixture of Risedronic acid, a sodium base, and a liquid comprising about 40% to about 60% v/v lower alkanol in water.
  • the alkanol may be methanol, ethanol or isopropanol.
  • the '520 patent publication yields Risedronate sodium as a mixture of monohydrate and hemipentahydrate forms.
  • PCT Application No.WO 2005 / 044831 teaches the preparation of bisphosphonic acid by reacting a carboxylic acid and phosphorus compound in sulfolane. This patent does not provide enablement conditions for preparing Risedronate sodium monohydrate or Risedronate sodium hemipentahydrate.
  • US 7,002,014 discloses the preparation of Risedronate sodium hemipentahydrate by dissolving Risedronic acid in an admixture of isopropyl alcohol and water using sodium hydroxide in sufficient amount to provide a pH of 6 at high temperature, followed by acidification and cooling to isolate the desired hemipentahydrate.
  • Still another objective of the present invention is to provide an improved process by which the desired form of hemipentahydrate or monohydrate of compound of formula (I) can be obtained consistently.
  • the present invention provides a process for the preparation of desired form of Risedronate monosodium such as hemipentahydrate or monohydrate, comprising the steps of: a) dissolving Risedronic acid in water in the presence of a base containing sodium ion; b) optionally adjusting the pH to 4.5 to 5.0; c) optionally adding sulfolane solvent; d) optionally seeding with Risedronate monosodium hemipentahydrate or monohydrate; e) isolating Risedronate monosodium monohydrate or its hemipentahydrate.
  • the present invention provides a process for preparing Risedronate sodium hemipentahydrate or Risedronate sodium monohydrate in pure form.
  • the process reported in '520 patent yields Risedronate sodium in a mixture of hemipentahydrate or monohydrate forms, the present invention provides a process in which the individual forms are isolated in pure form without having contamination of another form.
  • the Risedronate sodium hemipentahydrate is prepared by a) dissolving Risedronic acid in water using a base containing sodium ion (b) adjusting the pH of the solution to 4.S-S.0 using an acid (c) optionally adding sulfolane to the reaction mass at a temperature in the range of 45 - 75°C (d) slowly cooling and isolating Risedronate sodium hemipentahydrate. Accordingly the present invention provides a simple and industrially viable process for the production of Risedronate sodium hemipentahydrate on commercial scales.
  • the Risedronate sodium monohydrate is prepared by a) dissolving Risedronic acid in water using a base containing sodium ion by adjusting the pH to 4.5 to 5.0; (b) adding preheated (45 - 75° C) sulfolane to step (a) mass; (c) optionally seeding with Risedronate monohydrate (d) slowly cooling and isolating Risedronate sodium monohydrate.
  • the present invention provides a simple and industrially viable process for the production of Risedronate monohydrate in pure form with having contamination of other forms.
  • the addition of preheated sulfolane yields the Risedronate monohydrate in pure form without having contamination of other forms.
  • the addition of sulfolane at room temperature results in anhydrous form, and the nature of the reaction mass becomes thick resulting in difficulty in the filtration.
  • the base used is selected from sodium hydroxide, sodium carbonate, sodium bicarbonate, most preferably sodium hydroxide.
  • the acid used is selected from hydrochloric acid, sulfuric acid and the like, most preferably hydrochloric acid.
  • the Risedronate sodium monohydrate or hemihydrate prepared according to the present invention is stable and does not convert back to another form.
  • the invention is further illustrated by the following examples, which should not be construed to limit the scope of the invention in anyway.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Biochemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Molecular Biology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

La présente invention porte sur un procédé perfectionné destiné à la fabrication de formes hydratées pures de Risédronate monosodique, qui est utilisé pour le traitement de l'ostéoporose.
PCT/IB2007/004344 2006-09-22 2007-09-24 Procédé perfectionné pour la fabrication de risédronate sodique Ceased WO2008065542A2 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
IN1737/CHE/2006 2006-09-22
IN1737CH2006 2006-09-22

Publications (2)

Publication Number Publication Date
WO2008065542A2 true WO2008065542A2 (fr) 2008-06-05
WO2008065542A3 WO2008065542A3 (fr) 2008-11-27

Family

ID=39468331

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/IB2007/004344 Ceased WO2008065542A2 (fr) 2006-09-22 2007-09-24 Procédé perfectionné pour la fabrication de risédronate sodique

Country Status (1)

Country Link
WO (1) WO2008065542A2 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8076483B2 (en) 2006-05-11 2011-12-13 M/S. Ind Swift Laboratories Limited Process for the preparation of pure risedronic acid or salts

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
PE20011061A1 (es) * 2000-02-01 2001-11-20 Procter & Gamble Cristalizacion selectiva del acido 3-piridil-1-hidroxi-etiliden-1,1-bisfosfonico sodio como el hemipentahidrato o el monohidrato

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8076483B2 (en) 2006-05-11 2011-12-13 M/S. Ind Swift Laboratories Limited Process for the preparation of pure risedronic acid or salts

Also Published As

Publication number Publication date
WO2008065542A3 (fr) 2008-11-27

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