WO2007090949A1 - Le monohydrate de rimonabant, son procede de preparation et les compositions pharmaceutiques en contenant - Google Patents
Le monohydrate de rimonabant, son procede de preparation et les compositions pharmaceutiques en contenant Download PDFInfo
- Publication number
- WO2007090949A1 WO2007090949A1 PCT/FR2007/000201 FR2007000201W WO2007090949A1 WO 2007090949 A1 WO2007090949 A1 WO 2007090949A1 FR 2007000201 W FR2007000201 W FR 2007000201W WO 2007090949 A1 WO2007090949 A1 WO 2007090949A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- rimonabant
- monohydrate
- acetone
- crystalline form
- water
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
-
- 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
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/415—1,2-Diazoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
Definitions
- the subject of the present invention is rimonabant monohydrate, its process of preparation and the pharmaceutical compositions containing it.
- Rimonabant is the international non-proprietary name for N-piperidino-5- (4-chlorophenyl) -1- (2,4-dichlorophenyl) -4-methylpyrazole-3-carboxamide.
- rimonabant monohydrate is meant the chemical compound consisting of a rimonabant molecule and a molecule of water.
- Rimonabant monohydrate preferentially exists in crystallized form.
- the present invention relates to rimonabant monohydrate, and more particularly to a crystalline form of rimonabant monohydrate.
- Obtaining a solvate of rimonabant with a molecule of water is particularly advantageous because rimonabant monohydrate is an active ingredient that can be administered to humans.
- the crystalline form of rimonabant monohydrate constitutes a powder whose characteristics are improved compared with powders constituted either by the crystalline form I of rimonabant or by the crystalline form II of rimonabant.
- a better filterability is observed than when it comes to filtering crystals of Form I or form II crystals of rimonabant.
- the improved filterability makes it possible to shorten the filtration step and brings about a significant improvement in the texture of the filter cake, which is characterized by a low moisture content of the powder before drying and a low level of residual solvent before drying.
- the resulting powder after drying has improved physical properties, particularly in terms of flowability and therefore of handling.
- the flowability of the crystalline form of rimonabant monohydrate was measured and compared to that of crystalline form II of rimonabant.
- the flowability of the crystalline forms is measured by the flowability index or compressibility index or Carr index as described in R.L. Carr: Evaluation of Flow Properties of Solids, Chem. Eng., 1965, 163-168 as well as in the European Pharmacopoeia.
- the densities are determined experimentally by compacting the product in a graduated cylinder according to the procedure described in the European Pharmacopoeia. The densities are determined after 10, 500, 1250 and 2500 shots. The Carr index is determined from the data measured at 10 and 1250 counts.
- an index of Carr less than or equal to 20% is considered to correspond to a good flow of the powders, while a Carr index greater than 21% is considered as corresponding to a passable flow of powders, or difficult or very difficult.
- an index of rimonabant monohydrate is considered to correspond to a good flow of the powders, while a Carr index greater than 21% is considered as corresponding to a passable flow of powders, or difficult or very difficult.
- Carr equal to 20%, that is to say good, while for the crystalline form II of rimonabant, we measure a Carr index of the order of 38%, that is to say very difficult.
- the Carr index measured for the crystalline form I of rimonabant also corresponds to a very difficult flowability.
- the good flowability index of the crystalline form of rimonabant monohydrate indicates that this form can easily be mixed with excipients during the preparation of pharmaceutical compositions for the administration of rimonabant monohydrate.
- the flow of the powder is improved and the content of active ingredient is better controlled. Thanks to the better flowability, the tableting process can be simplified by eliminating certain steps such as wet granulation, drying and calibration, which increases the rates and reduces the cost of production.
- the present invention also relates to the process for obtaining rimonabant monohydrate.
- This process is characterized in that the rimonabant in an organic solvent and water is added. More particularly, this process is characterized in that: a) a mixture of rimonabant is prepared in a solvent chosen from:
- step a) is carried out at room temperature.
- the process for preparing rimonabant monohydrate according to the invention is characterized in that: a) a saturated solution of rimonabant is prepared in a solvent chosen from:
- step a it is filtered to obtain a clear saturated solution.
- the rimonabant monohydrate formed by the process according to the invention is isolated by filtration.
- a solution of rimonabant in acetone is prepared. More particularly, a solution containing between 150 and 200 g / l of rimonabant in acetone is prepared, and preferably a solution containing 200 g / l of rimonabant in acetone.
- water is added dropwise so as to obtain an acetone / water mixture containing between 10 and 30% water by volume; preferably, the mixture contains 20% water.
- a process for obtaining rimonabant monohydrate in crystalline form is characterized in that: a) a mixture of rimonabant is prepared in a solvent chosen from:
- the process for preparing rimonabant monohydrate in crystalline form is characterized in that: a) a saturated solution of rimonabant in a solvent chosen from:
- step a) a solvent chosen from:
- step a it is filtered to obtain a clear saturated solution.
- the rimonabant monohydrate can be prepared in crystalline form according to a process characterized in that: a) a mixture containing between 150 and 200 g / l of rimonabant in acetone is prepared at room temperature, preferably 200 g / l; b) is added dropwise between 10% and 30% water by volume, preferably 20% water by volume; c) is cooled to a temperature between 0 ° C and 15 ° C, preferably 5 ° C; d) the crystals formed are filtered.
- step a the formed mixture can be filtered to obtain a clear saturated solution.
- the product obtained is dried at a temperature between room temperature and 40 ° C., preferably at room temperature.
- the solvent used in step a) of the process according to the invention is acetone, which leads to isolating the rimonabant monohydrate from an acetone / water mixture, this mixture has conductive and its use makes it possible to avoid the accumulation of electrostatically dangerous charges on the industrial level.
- Rimonabant monohydrate is characterized by various elements of its physicochemical analysis.
- Rimonabant monohydrate is characterized by elemental analysis and analysis of the water content measured on a Karl Fisher apparatus.
- the water content indicates the presence of the equivalent of one molecule of water per molecule of product.
- thermogravimetric analysis was carried out for rimonabant monohydrate by a thermogravimetric analysis device TGA 2950, marketed by TA Instruments SARL (PARIS, France); it is operated under a nitrogen atmosphere, the initial temperature is 30 ° C, it increases at a rate of 10 ° C / minute until decomposition of the product.
- thermo gravimetric mass loss curve indicates that the water molecule present is a hydration molecule.
- the differential enthalpy analysis of the crystalline form of rimonabant monohydrate is carried out under the same conditions on an MDSC 2920 differential enthalpy analysis apparatus, marketed by TA Instruments SARL (PARIS, France); it operates under a nitrogen atmosphere, the initial temperature is 30 ° C., it increases at a rate of 10 ° C./minute.
- PARIS differential enthalpy analysis apparatus
- the melting peak and the enthalpy difference of the substance ( ⁇ H) are measured before and after melting, in Joule per gram of material.
- the crystalline form of the rimonabant monohydrate loses its water of crystallization molecule between 40 ° C. and 100 ° C. It simultaneously has a melting peak of between 95 ° C. ⁇ 5 ° C. and 115 ° C. 5 ° C.
- the water vapor sorption / desorption measurement analysis is carried out on the crystalline form of rimonabant monohydrate on an SGA100 analysis apparatus marketed by VTI (USA). It operates between 0% and 100% relative humidity at 25 0 C after degassing the monohydrate form at 80 ° C. for 3 hours. Rimonabant monohydrate loses its water of hydration molecule during drying at 80 ° C. During the water vapor sorption cycle, the conversion of rimonabant to rimonabant monohydrate occurs from 40% relative humidity. The sorption / desorption isotherm is shown in FIG.
- the crystalline form of rimonabant monohydrate is also characterized by its infra-red spectrum (LR.). This is compared with that of the crystalline form II of rimonabant previously described.
- the crystalline form of rimonabant monohydrate is also characterized by the characteristic lines of the X-ray powder diffractogram.
- the crystalline form of rimonabant monohydrate is also characterized by its crystalline structure for which the mesh parameters have been determined by single-crystal X-ray diffraction.
- the values () in the right column are the standard deviations observed for this measurement.
- calculation software makes it possible to draw projected views of the crystal lattice of the molecule concerned.
- this representation of the molecule in the crystalline mesh demonstrates the presence of the water molecule that participates well in the crystalline structure (water of crystallization).
- Example preparation of the crystalline form of rimonabant monohydrate.
- rimonabant form II 80 g are suspended in 400 ml of acetone at room temperature with stirring overnight. The suspension is filtered with 2 ⁇ in order to obtain a solution of rimonabant in saturated and clear acetone.
- the rimonabant titer of the compound obtained is 96.6%. Thus, it appears that no impurity is quantifiable in the compound obtained.
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Hematology (AREA)
- Diabetes (AREA)
- Obesity (AREA)
- Child & Adolescent Psychology (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
Description
Claims
Priority Applications (9)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
BRPI0707711-4A BRPI0707711A2 (pt) | 2006-02-08 | 2007-02-05 | monohidrato de rimonabanto o respectivo processo de preparaÇço e as composiÇÕes farmacÊuticas que o contÊm |
EP07730917A EP1984341A1 (fr) | 2006-02-08 | 2007-02-05 | Le monohydrate de rimonabant, son procede de preparation et les compositions pharmaceutiques en contenant |
EA200870236A EA200870236A1 (ru) | 2006-02-08 | 2007-02-05 | Моногидрат римонабанта, способ его получения и фармацевтические композиции на его основе |
JP2008553793A JP2009526025A (ja) | 2006-02-08 | 2007-02-05 | リモナバント1水和物、これの調製方法およびこれを含む医薬組成物 |
CA002641494A CA2641494A1 (fr) | 2006-02-08 | 2007-02-05 | Le monohydrate de rimonabant, son procede de preparation et les compositions pharmaceutiques en contenant |
AU2007213649A AU2007213649A1 (en) | 2006-02-08 | 2007-02-05 | Rimonabant monohydrate, process for the preparation thereof and pharmaceutical compositions containing same |
IL192963A IL192963A0 (en) | 2006-02-08 | 2008-07-22 | Rimonabant monohydrate, process for the preparation thereof and pharmaceutical compositions containing same |
US12/186,753 US20090048449A1 (en) | 2006-02-08 | 2008-08-06 | Rimonabant monohydrate, process for the preparation thereof and pharmaceutical compositions containing same |
NO20083521A NO20083521L (no) | 2006-02-08 | 2008-08-13 | Rimonabantmonohydrat, fremgangsmate for fremstilling derav og farmasoytiske sammensetninger inneholdende samme |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR0601253A FR2897060B1 (fr) | 2006-02-08 | 2006-02-08 | Le monohydrate de rimonabant, son procede de preparation et les compositions pharmaceutiques en contenant |
FR0601253 | 2006-02-08 |
Related Child Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US12/186,753 Continuation US20090048449A1 (en) | 2006-02-08 | 2008-08-06 | Rimonabant monohydrate, process for the preparation thereof and pharmaceutical compositions containing same |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2007090949A1 true WO2007090949A1 (fr) | 2007-08-16 |
Family
ID=37075667
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/FR2007/000201 WO2007090949A1 (fr) | 2006-02-08 | 2007-02-05 | Le monohydrate de rimonabant, son procede de preparation et les compositions pharmaceutiques en contenant |
Country Status (20)
Country | Link |
---|---|
US (1) | US20090048449A1 (fr) |
EP (1) | EP1984341A1 (fr) |
JP (1) | JP2009526025A (fr) |
KR (1) | KR20080093042A (fr) |
CN (1) | CN101405271A (fr) |
AR (1) | AR059327A1 (fr) |
AU (1) | AU2007213649A1 (fr) |
BR (1) | BRPI0707711A2 (fr) |
CA (1) | CA2641494A1 (fr) |
DO (1) | DOP2007000023A (fr) |
EA (1) | EA200870236A1 (fr) |
FR (1) | FR2897060B1 (fr) |
GT (1) | GT200700014A (fr) |
IL (1) | IL192963A0 (fr) |
MA (1) | MA30312B1 (fr) |
NO (1) | NO20083521L (fr) |
TW (1) | TW200804343A (fr) |
UY (1) | UY30137A1 (fr) |
WO (1) | WO2007090949A1 (fr) |
ZA (1) | ZA200806713B (fr) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2008056377A2 (fr) * | 2006-11-06 | 2008-05-15 | Cadila Healthcare Limited | Nouvelles formes du rimonabant |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2008026219A2 (fr) * | 2006-09-01 | 2008-03-06 | Hetero Drugs Limited | Nouveaux polymorphes de rimonabant |
SI3229799T1 (sl) * | 2014-12-08 | 2019-03-29 | Crystal Pharmatech Co., Ltd. | Kristalinične oblike trinatrijevega supramolekularnega kompleksa, ki obsega valsartan in AHU-377, ter njihovi postopki |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0656354A1 (fr) * | 1993-12-02 | 1995-06-07 | Sanofi | N-pipéridino-3-pyrazolecarboxamide substitué |
WO2003040105A1 (fr) * | 2001-11-08 | 2003-05-15 | Sanofi-Synthelabo | Forme polymorphe du rimonabant, son procede de preparation et les compositions pharmaceutiques en contenant |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP4746931B2 (ja) * | 2005-07-22 | 2011-08-10 | 株式会社日立製作所 | フラットディスプレイパネルモジュール及びフラットディスプレイ装置 |
WO2008026219A2 (fr) * | 2006-09-01 | 2008-03-06 | Hetero Drugs Limited | Nouveaux polymorphes de rimonabant |
WO2008035023A1 (fr) * | 2006-09-19 | 2008-03-27 | Cipla Limited | Formes polymorphes de rimonabant |
-
2006
- 2006-02-08 FR FR0601253A patent/FR2897060B1/fr not_active Expired - Fee Related
-
2007
- 2007-02-01 DO DO2007000023A patent/DOP2007000023A/es unknown
- 2007-02-05 WO PCT/FR2007/000201 patent/WO2007090949A1/fr active Application Filing
- 2007-02-05 EP EP07730917A patent/EP1984341A1/fr not_active Withdrawn
- 2007-02-05 JP JP2008553793A patent/JP2009526025A/ja active Pending
- 2007-02-05 AU AU2007213649A patent/AU2007213649A1/en not_active Abandoned
- 2007-02-05 ZA ZA200806713A patent/ZA200806713B/xx unknown
- 2007-02-05 KR KR1020087019391A patent/KR20080093042A/ko not_active Application Discontinuation
- 2007-02-05 CA CA002641494A patent/CA2641494A1/fr not_active Abandoned
- 2007-02-05 EA EA200870236A patent/EA200870236A1/ru unknown
- 2007-02-05 CN CNA200780004742XA patent/CN101405271A/zh active Pending
- 2007-02-05 BR BRPI0707711-4A patent/BRPI0707711A2/pt not_active IP Right Cessation
- 2007-02-06 AR ARP070100477A patent/AR059327A1/es unknown
- 2007-02-06 GT GT200700014A patent/GT200700014A/es unknown
- 2007-02-08 UY UY30137A patent/UY30137A1/es not_active Application Discontinuation
- 2007-02-08 TW TW096104722A patent/TW200804343A/zh unknown
-
2008
- 2008-07-22 IL IL192963A patent/IL192963A0/en unknown
- 2008-08-06 US US12/186,753 patent/US20090048449A1/en not_active Abandoned
- 2008-08-13 NO NO20083521A patent/NO20083521L/no not_active Application Discontinuation
- 2008-08-26 MA MA31195A patent/MA30312B1/fr unknown
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0656354A1 (fr) * | 1993-12-02 | 1995-06-07 | Sanofi | N-pipéridino-3-pyrazolecarboxamide substitué |
WO2003040105A1 (fr) * | 2001-11-08 | 2003-05-15 | Sanofi-Synthelabo | Forme polymorphe du rimonabant, son procede de preparation et les compositions pharmaceutiques en contenant |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2008056377A2 (fr) * | 2006-11-06 | 2008-05-15 | Cadila Healthcare Limited | Nouvelles formes du rimonabant |
WO2008056377A3 (fr) * | 2006-11-06 | 2008-10-30 | Cadila Healthcare Ltd | Nouvelles formes du rimonabant |
Also Published As
Publication number | Publication date |
---|---|
EA200870236A1 (ru) | 2009-02-27 |
MA30312B1 (fr) | 2009-04-01 |
TW200804343A (en) | 2008-01-16 |
CN101405271A (zh) | 2009-04-08 |
FR2897060B1 (fr) | 2008-07-25 |
NO20083521L (no) | 2008-10-24 |
AR059327A1 (es) | 2008-03-26 |
US20090048449A1 (en) | 2009-02-19 |
KR20080093042A (ko) | 2008-10-17 |
DOP2007000023A (es) | 2008-02-15 |
EP1984341A1 (fr) | 2008-10-29 |
BRPI0707711A2 (pt) | 2011-05-10 |
ZA200806713B (en) | 2009-10-28 |
IL192963A0 (en) | 2009-02-11 |
JP2009526025A (ja) | 2009-07-16 |
AU2007213649A1 (en) | 2007-08-16 |
CA2641494A1 (fr) | 2007-08-16 |
UY30137A1 (es) | 2007-09-28 |
GT200700014A (es) | 2007-09-19 |
FR2897060A1 (fr) | 2007-08-10 |
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