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WO2004083230A1 - Nouvelles formes cristallines de finasteride - Google Patents

Nouvelles formes cristallines de finasteride Download PDF

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Publication number
WO2004083230A1
WO2004083230A1 PCT/IN2003/000060 IN0300060W WO2004083230A1 WO 2004083230 A1 WO2004083230 A1 WO 2004083230A1 IN 0300060 W IN0300060 W IN 0300060W WO 2004083230 A1 WO2004083230 A1 WO 2004083230A1
Authority
WO
WIPO (PCT)
Prior art keywords
finasteride
hours
ray powder
powder diffraction
diffraction pattern
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/IN2003/000060
Other languages
English (en)
Inventor
Reddy Bandi Parthasaradhi
Reddy Kura Rathnakar
Reddy Rapolu Raji
Reddy Dasari Muralidhara
Reddy Kesireddy Subash Chander
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.)
Hetero Drugs Ltd
Original Assignee
Hetero Drugs 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 Hetero Drugs Ltd filed Critical Hetero Drugs Ltd
Priority to PCT/IN2003/000060 priority Critical patent/WO2004083230A1/fr
Priority to AU2003217439A priority patent/AU2003217439A1/en
Publication of WO2004083230A1 publication Critical patent/WO2004083230A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J73/00—Steroids in which the cyclopenta[a]hydrophenanthrene skeleton has been modified by substitution of one or two carbon atoms by hetero atoms

Definitions

  • the present invention relates to novel crystalline forms of finasteride, to processes for their preparation and pharmaceutical compositions containing them.
  • novel forms of finasteride are, thus, suitable for pharmaceutical preparations.
  • object of the present invention is to provide stable novel crystalline forms of finasteride, processes for preparation of the novel crystalline forms and pharmaceutical compositions containing these novel crystalline forms.
  • Form H1 a novel crystalline form of finasteride, designated as Form H1 , characterized by an x-ray powder diffraction pattern having peaks expressed as 2 ⁇ at about 5.3, 5.8, 6.8, 7.3, 9.0, 9.4, 10.7, 13.9, 14.9, 15.9, 17.3, 18.2, 19.0, 20.1 degrees.
  • Figure 1 shows typical Form H1 x-ray powder diffraction pattern.
  • a process for preparation of the Form H1 of finasteride comprising the steps of: a) mixing finasteride and an alcohol; b) maintaining at about 4,0°C to 60°C for about 10 minutes to 1 hour; c) cooling slowly to about 0°C to 5°C; d) maintaining for about 1 hour to 3 hours at about 0°C to 5°C; e) filtering the solid separated.
  • the alcohol is methanol, ethanol or isopropyl alcohol; or mixture thereof.
  • a novel crystalline form of finasteride designated as Form H2 characterized by an x-ray powder diffraction pattern having peaks expressed as 2 ⁇ at about 5.4, 9.9, 12.1 , 14.5, 15.2, 16.2, 19.3, 29.0 degrees.
  • Figure 2 shows typical Form H2 x-ray powder diffraction pattern.
  • a process for preparation of the Form H2 of finasteride comprising the steps of. a) dissolving finasteride in dioxane; b) maintaining at about 70°C to 80°C for about 10 minutes to 30 minutes; c) cooling the solution slowly to about 20°C to 25°C; d) maintaining at about 20°C to 25°C for about 2 hours to 4 hours; e) filtering the solid separated.
  • the previously known forms or finasteride prepared by a known method may be used in the above processes.
  • a pharmaceutical composition comprising Form H1 or Form H2 of finasteride.
  • Figure 1 is a x-ray powder diffraction pattern of Form H1 finasteride.
  • Figure 2 is a x-ray powder diffraction pattern of Form H2 finasteride. x-Ray powder diffraction spectrum was measured on a Siemens diffractometer.
  • Form H1 a novel crystalline form of finasteride, designated as Form H1, characterized by an x-ray powder diffraction pattern having peaks expressed as 2 ⁇ at about 5.3, 5.8,
  • Figure 1 shows typical Form H1 x-ray powder diffraction pattern.
  • finasteride is mixed with an alcohol.
  • the suitable alcohol is methanol or ethanol or iso propyl alcohol; or mixture thereof.
  • the previously known forms or finasteride prepared by a known method may be used. The contents are maintained at about 40°C to
  • Form H2 a novel crystalline form of finasteride, designated as Form H2, characterized by an x-ray powder diffraction pattern having peaks expressed as 2 ⁇ at about 5.4, 9.9,
  • Figure 2 shows typical Form H2 x-ray powder diffraction pattern.
  • a process for preparation of the Form H2 of finasteride is provided.
  • finasteride is dissolved in dioxane, the solution is heated to about 70°C to 80°C and maintained at this temperature for about 10 minutes to 30 minutes.
  • the solution is cooled slowly, in about 3 hours, to about 20°C to 25°C and maintained at the same temperature for about 2 hours to 4 hours.
  • the separated crystals are filtered to give Form H2 of finasteride.
  • the previously known forms or finasteride prepared by a known method may be used in the process.
  • a pharmaceutical composition comprising Form H1 or Form H2 of finasteride.
  • the forms of finasteride may be formulated in a form suitable for oral administration or injection.
  • Example 1 Finasteride (10 gm) (obtained by a known method) is dissolved in methanol (25 ml), heated to 55°C and maintained at this temperature for 15 minutes. The solution is slowly cooled to 0°C in 3 hours and maintained at 0°C for 1.5 hours. The separated crystals are filtered at 0°C to give 8.5 gm of Form H1 of finasteride.
  • Example 2 Finasteride (10 gm) (obtained by a known method) is dissolved in isopropyl alcohol (40 ml), heated to 55°C and maintained at this temperature for 15 minutes. The solution is slowly cooled to 0°C in 3 hours and maintained at 0°C for 1.5 hours. The separated crystals are filtered at 0°C to give 8.5 gm of Form H1 of finasteride.
  • Example 3 Finasteride (10 gm) (obtained by a known method) is dissolved in isopropyl alcohol (40 ml), heated to 55°C and maintained at this temperature for 15 minutes. The solution is slowly cooled to 0°C in 3 hours and maintained at 0°C for 1.5 hours. The separated crystals are filtered at 0°C to give 8.5 gm of Form H1 of finasteride.
  • Example 3 Finasteride (10 gm) (obtained by a known method) is dissolved in isopropyl alcohol (40 ml), heated to 55
  • Finasteride (10 gm) (obtained by a known method) is dissolved in dioxane (50 ml), heated the solution to 80°C and maintained at 80°C for 15 minutes. The solution is slowly cooled to 25°C, maintained for 3 hours at 25°C and the solid separated is filtered to give 9 gm of Form H2 of finasteride.
  • Example 4 Example 1 is repeated using Form H2 of finasteride instead of finasteride to give Form H1 of finasteride.
  • Example 5 Example 3 is repeated using Form H1 of finasteride instead of finasteride Form H2 of finasteride.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Steroid Compounds (AREA)

Abstract

La présente invention concerne de nouvelles formes cristallines de finastéride, des procédés pour les préparer et des compositions pharmaceutiques qui les contiennent.
PCT/IN2003/000060 2003-03-19 2003-03-19 Nouvelles formes cristallines de finasteride Ceased WO2004083230A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
PCT/IN2003/000060 WO2004083230A1 (fr) 2003-03-19 2003-03-19 Nouvelles formes cristallines de finasteride
AU2003217439A AU2003217439A1 (en) 2003-03-19 2003-03-19 Novel crystalline forms of finasteride

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/IN2003/000060 WO2004083230A1 (fr) 2003-03-19 2003-03-19 Nouvelles formes cristallines de finasteride

Publications (1)

Publication Number Publication Date
WO2004083230A1 true WO2004083230A1 (fr) 2004-09-30

Family

ID=33017816

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/IN2003/000060 Ceased WO2004083230A1 (fr) 2003-03-19 2003-03-19 Nouvelles formes cristallines de finasteride

Country Status (2)

Country Link
AU (1) AU2003217439A1 (fr)
WO (1) WO2004083230A1 (fr)

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5468860A (en) * 1992-11-19 1995-11-21 Merck & Co., Inc. New finasteride processes
US5652363A (en) * 1995-10-05 1997-07-29 C.D. Searle & Co. Pyrido-1,4-oxazinylalkyl-benzamide derivatives

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5468860A (en) * 1992-11-19 1995-11-21 Merck & Co., Inc. New finasteride processes
US5652363A (en) * 1995-10-05 1997-07-29 C.D. Searle & Co. Pyrido-1,4-oxazinylalkyl-benzamide derivatives

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
WAWRZYCKA I., ET AL.: "Structural characterization of polymorphs and molecular complexes to finasteride", JOURNAL OF MOLUCULAR STRUCTURE, vol. 474, 1999, pages 157 - 166, XP000920855 *

Also Published As

Publication number Publication date
AU2003217439A1 (en) 2004-10-11

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