WO2007026379A2 - Novel crystalline forms of risedronate monosodium - Google Patents
Novel crystalline forms of risedronate monosodium Download PDFInfo
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- WO2007026379A2 WO2007026379A2 PCT/IN2006/000315 IN2006000315W WO2007026379A2 WO 2007026379 A2 WO2007026379 A2 WO 2007026379A2 IN 2006000315 W IN2006000315 W IN 2006000315W WO 2007026379 A2 WO2007026379 A2 WO 2007026379A2
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- WIPO (PCT)
- Prior art keywords
- risedronate monosodium
- risedronate
- monosodium
- crystals
- novel crystalline
- Prior art date
Links
- DRFDPXKCEWYIAW-UHFFFAOYSA-M Risedronate sodium Chemical compound [Na+].OP(=O)(O)C(P(O)([O-])=O)(O)CC1=CC=CN=C1 DRFDPXKCEWYIAW-UHFFFAOYSA-M 0.000 title claims abstract description 38
- 238000000034 method Methods 0.000 claims abstract description 12
- 238000002360 preparation method Methods 0.000 claims abstract description 12
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 6
- 239000013078 crystal Substances 0.000 claims description 20
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 11
- 238000000634 powder X-ray diffraction Methods 0.000 claims description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 8
- 238000001228 spectrum Methods 0.000 claims description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 4
- 238000007865 diluting Methods 0.000 claims 3
- 239000003937 drug carrier Substances 0.000 claims 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- IIDJRNMFWXDHID-UHFFFAOYSA-N Risedronic acid Chemical compound OP(=O)(O)C(P(O)(O)=O)(O)CC1=CC=CN=C1 IIDJRNMFWXDHID-UHFFFAOYSA-N 0.000 description 14
- 229960000759 risedronic acid Drugs 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 9
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical class [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
- 238000002329 infrared spectrum Methods 0.000 description 4
- 229940089617 risedronate Drugs 0.000 description 4
- 239000007787 solid Substances 0.000 description 3
- 238000001035 drying Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000000825 pharmaceutical preparation Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- WGNUNYPERJMVRM-UHFFFAOYSA-N 3-pyridylacetic acid Chemical compound OC(=O)CC1=CC=CN=C1 WGNUNYPERJMVRM-UHFFFAOYSA-N 0.000 description 1
- 229940078581 Bone resorption inhibitor Drugs 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 1
- DSTCRCARRBIKOU-UHFFFAOYSA-J tetrasodium;1,1-diphosphonato-2-pyridin-3-ylethanol Chemical group [Na+].[Na+].[Na+].[Na+].[O-]P(=O)([O-])C(P([O-])([O-])=O)(O)CC1=CC=CN=C1 DSTCRCARRBIKOU-UHFFFAOYSA-J 0.000 description 1
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
- Present invention relates to novel crystalline forms of risedronate monosodium, process for their preparation and. pharmaceutical compositions containing them.
- Patent EP Appl. 186,405 describes preparation of risedronic acid and its monosodium salt useful as bone resorption inhibitor.
- Risedronic acid monosodium is sodium [1- hydroxy-2-(3 -pyridinyl)ethylidene]bisphosphonate of the formula-I.
- the aforesaid European patent describes the preparation of risedronate by bisphosphonylation of 3-pyridinylacetic acid using phosphorous trichloride and phosphorous acid.
- the resultant risedronic acid is converted to its monosodium using sodium hydroxide.
- the main objective of the present invention is to provide three stable and novel crystalline forms of risedronate monosodium, process for the preparation of said novel crystalline forms and pharmaceutical compositions containing these novel crystalline forms.
- a novel crystalline form of risedronate monosodium designated as Form I, characterized by an X-ray powder diffraction pattern having peaks expressed as 29 (intensity in %) 9.06 (8.4), 12.35 (100), 13.00 (2.1), 23.73 (2.7), 24.03 (2.6), 24.72 (35.3), and 31.26 (3.2) degrees.
- IR (KBr) spectrum of Form I is having peaks at 3370, 3096, 1655, 1569, 1478, 1436, 1387, 1320, 1213, 1133, 1073, 1032, 935, 890, 800, 742, 687, 660, 629, 604, 535, and 472cm- 1 .
- risedronate monosodium there is provided a process for preparation of Form I of risedronate monosodium.
- risedronic acid of formula-II is suspended in water and added aqueous sodium hydroxide and heated to get a clear solution. Cooling of this solution to 5-10 0 C gave crude risederonate monosodium crystals.
- the crude risedronate monosodium was recrystallized from aqueous methanol and the product isolated at 5-10°C to get Form I crystals of risedronate monosodium.
- a novel crystalline form of risedronate monosodium designated as Form II, characterized by an X-ray powder diffraction pattern having peaks expressed as 2 ⁇ (intensity in %) 6.09 (93.8), 9.08 (100), 12.1 (14.2), 12.34 (45.2), 13.03 (9.4), 14.44 (9.1), 15.85 (10.8), 16.68 (8.3), 17.26 (8.5), 19.15 (5.0), 19.87 (13.6), 20.65 (5.2), 21.97 (6.6), 23.02 (14.6), 23.71 (28.8), 25.60 (7.4), 27.87 (14.6), 30.41 (10.8), 31.27 (15.5), 31.86 (9.7), 35.50 (7.4), 36.61 (14.4), and 37.88 (6.4) degrees.
- IR (KBr) spectrum of Form II is having peaks at 3569, 3373, 1654, 1569, 1478, 1436, 1388, 1320, 1210, 1135, 1081, 1048, 986, 935, 887, 859, 818, 798, 746, 691, 660, 627, 606, 542, and 465cm ⁇
- risedronic acid of formula-II is suspended in water and added aqueous sodium hydroxide solution and heated to 60-70 0 C to get a clear solution. Ethanol was added to the solution and allowed to crystallize. The crystals were filtered at room temperature, and dried to get Form II crystals of risedronate monosodium.
- a novel crystalline form of risedronate monosodium designated as Form III, characterized by an X-ray powder diffraction pattern having peaks expressed as 2 ⁇ (intensity in %) 8.97 (100), 12.22 (43.6), 12.92 (7.8), 15.73 (9.5), 19.81 (6.7), 22.92 (10.8), 23.60 (5.4), 23.92 (10.6), 24.58 (32.9), 26.00 (5.2), 27.85 (13.5), 31.16 (16.3), 32.77 (5.0), and 36.49 (10.5) degrees.
- IR (KBr) spectrum of Form III is having peaks at 3620, 3361, 3096, 1654, 1569, 1478, 1436, 1387, 1319, 1212, 1133, 1074, 1033, 935, 890, 818, 801, 745, 688, 660, 630, 604, 566, 537, and 472cm "1 .
- risedronic acid of formula-II is suspended in water and added aqueous sodium hydroxide solution to get a clear solution at 60-70°C.
- the resultant solution was diluted with tetrahydrofuran to get the crystals of risedronate monosodium which were filtered at room temperature and dried to give Form III risedronate
- X-ray powder diffraction spectra were measured on a Siemens D5000 x-ray powder diffractometer having a copper-K ⁇ radiation (1.5406A). IR spectra were recorded on a Perkin Elmer FT IR instrument Model Paragon 1000.
- Example 1 Risedronate sodium (2Og) and water (100ml) were taken into a flask and heated to 80- 85 0 C to get a clear solution. The solution was slowly allowed to reach 30 0 C. After ⁇ reaching 50 0 C crystallization began. Methanol (100ml) was added to the reaction mass and cooled the reaction mass to 5-1O 0 C. After stirring the mass at 5-10 0 C for 1.5h reaction mass was filtered and washed the wet material with 2 x 15ml of 50% aqueous methanol. The wet material was dried to get 19. Ig of risedronate monsodium Form-I crystals.
- Present invention provides three novel crystalline forms designated as Form I, Form II, and Form III of risedronate monosodium, which are stable, reproducible, and suitable for pharmaceutical preparations.
- Present invention provides processes for the novel crystalline forms, namely Form I, Form II, and Form III of risedronate monosodium, which are simple and easy to adopt on a commercial scale.
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- 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Present invention is related to three novel crystalline forms of risedronate monosodium of Formula (I) and processes for the preparation of same. These forms are stable and suitable for pharmaceutical formulations.
Description
NOVEL CRYSTALLINE FORMS OF RISEDRONATE INTRODUCTION:
Present invention relates to novel crystalline forms of risedronate monosodium, process for their preparation and. pharmaceutical compositions containing them.
Patent EP Appl. 186,405 describes preparation of risedronic acid and its monosodium salt useful as bone resorption inhibitor. Risedronic acid monosodium is sodium [1- hydroxy-2-(3 -pyridinyl)ethylidene]bisphosphonate of the formula-I.
The aforesaid European patent describes the preparation of risedronate by bisphosphonylation of 3-pyridinylacetic acid using phosphorous trichloride and phosphorous acid. The resultant risedronic acid is converted to its monosodium using sodium hydroxide.
BACKGROUND OF INVENTION:
In the PCT application WO 03/086355 a number of polymorphs and pseudopolymorphs are disclosed for risedronate sodium. These forms are named as Form A, B, BB, Bl, C5 D, E, F, G, H. Process for preparation of these forms and thermal stability, inter conversion of these forms are also discussed in this patent application.
During the risedronate monosodium salt formation we observed three novel crystalline forms which are different from all the previously known forms of risedronate monosodium. These novel forms are found to be stable, reproducible, and suitable for pharmaceutical preparations.
Accordingly the main objective of the present invention is to provide three stable and novel crystalline forms of risedronate monosodium, process for the preparation of said novel crystalline forms and pharmaceutical compositions containing these novel crystalline forms.
DESCRIPTION OF THE INVENTION:
According to one aspect of the present invention there is provided a novel crystalline form of risedronate monosodium, designated as Form I, characterized by an X-ray powder diffraction pattern having peaks expressed as 29 (intensity in %) 9.06 (8.4), 12.35 (100), 13.00 (2.1), 23.73 (2.7), 24.03 (2.6), 24.72 (35.3), and 31.26 (3.2) degrees. IR (KBr) spectrum of Form I is having peaks at 3370, 3096, 1655, 1569, 1478, 1436, 1387, 1320, 1213, 1133, 1073, 1032, 935, 890, 800, 742, 687, 660, 629, 604, 535, and 472cm-1.
According to another aspect of the present invention there is provided a process for preparation of Form I of risedronate monosodium. Thus, risedronic acid of formula-II is suspended in water and added aqueous sodium hydroxide and heated to get a clear solution. Cooling of this solution to 5-100C gave crude risederonate monosodium crystals. The crude risedronate monosodium was recrystallized from aqueous methanol and the product isolated at 5-10°C to get Form I crystals of risedronate monosodium.
According to another aspect of the present invention there is provided a novel crystalline form of risedronate monosodium, designated as Form II, characterized by an X-ray powder diffraction pattern having peaks expressed as 2Θ (intensity in %) 6.09 (93.8), 9.08 (100), 12.1 (14.2), 12.34 (45.2), 13.03 (9.4), 14.44 (9.1), 15.85 (10.8), 16.68 (8.3), 17.26 (8.5), 19.15 (5.0), 19.87 (13.6), 20.65 (5.2), 21.97 (6.6), 23.02 (14.6), 23.71 (28.8), 25.60 (7.4), 27.87 (14.6), 30.41 (10.8), 31.27 (15.5), 31.86 (9.7), 35.50 (7.4), 36.61 (14.4), and 37.88 (6.4) degrees. IR (KBr) spectrum of Form II is having peaks at 3569, 3373, 1654, 1569, 1478, 1436, 1388, 1320, 1210, 1135, 1081, 1048, 986, 935, 887, 859, 818, 798, 746, 691, 660, 627, 606, 542, and 465cmΛ
According to another aspect of the present invention there is provided a process for preparation of Form II of risedronate monosodium. Thus, risedronic acid of formula-II is suspended in water and added aqueous sodium hydroxide solution and heated to 60-700C to get a clear solution. Ethanol was added to the solution and allowed to crystallize. The crystals were filtered at room temperature, and dried to get Form II crystals of risedronate monosodium.
According to another aspect of the present invention there is provided a novel crystalline form of risedronate monosodium, designated as Form III, characterized by an X-ray powder diffraction pattern having peaks expressed as 2Θ (intensity in %) 8.97 (100), 12.22 (43.6), 12.92 (7.8), 15.73 (9.5), 19.81 (6.7), 22.92 (10.8), 23.60 (5.4), 23.92 (10.6), 24.58 (32.9), 26.00 (5.2), 27.85 (13.5), 31.16 (16.3), 32.77 (5.0), and 36.49 (10.5) degrees. IR (KBr) spectrum of Form III is having peaks at 3620, 3361, 3096, 1654, 1569, 1478, 1436, 1387, 1319, 1212, 1133, 1074, 1033, 935, 890, 818, 801, 745, 688, 660, 630, 604, 566, 537, and 472cm"1.
According to another aspect of the present invention there is provided a process for preparation of Form III of risedronate monosodium. Thus, risedronic acid of formula-II is suspended in water and added aqueous sodium hydroxide solution to get a clear solution at 60-70°C. The resultant solution was diluted with tetrahydrofuran to get the crystals of risedronate monosodium which were filtered at room temperature and dried to give Form III risedronate
X-ray powder diffraction spectra were measured on a Siemens D5000 x-ray powder diffractometer having a copper-Kα radiation (1.5406A). IR spectra were recorded on a Perkin Elmer FT IR instrument Model Paragon 1000.
Fig.l Powder XRD of Form-I crystals of risedronate monosodium Fig.2 IR spectrum of Form-I crystals of risedronate monosodium Fig.3 Powder XRD of Form-II crystals of risedronate monosodium Fig.4 IR spectrum of Form-II crystals of risedronate monosodium
Fig.5 Powder XRD of Form-Ill crystals of risedronate monosodium Fig.6 IR spectrum of Form-Ill crystals of risedronate monosodium The details of the process of the invention are provided in the Examples given below which are provided by way of illustration only and therefore should not be construed to limit the scope of the invention.
Examples
Example 1 Risedronate sodium (2Og) and water (100ml) were taken into a flask and heated to 80- 850C to get a clear solution. The solution was slowly allowed to reach 300C. After ■ reaching 500C crystallization began. Methanol (100ml) was added to the reaction mass and cooled the reaction mass to 5-1O0C. After stirring the mass at 5-100C for 1.5h reaction mass was filtered and washed the wet material with 2 x 15ml of 50% aqueous methanol. The wet material was dried to get 19. Ig of risedronate monsodium Form-I crystals.
Example 2
Risedronic acid (5g) and water (30ml) were charged into a flask and aqueous sodium hydroxide (0.7g in 7ml of water) was added at 3O0C. The reaction mass was heated to 700C to get a clear solution. The reaction mass was filtered and ethanol (25ml) was added to the filtrate at 40-450C. After allowing the mass to reach 300C it was maintained for lhr at 3O0C. The reaction mass was filtered and the the wet solid washed with 2 x 5ml of 50% aqueous ethanol. Drying of the solid gave 4.7g of risedronate monosodium Form-II crystals.
Example 3
Risedronic acid (5g) and water (30ml) were charged into a flask. Aqueous sodium hydroxide (0.7g in 7ml of water) was added to the reaction mass and heated to 700C. to the resultant clear solution tetrahydrofuran (25ml) was adeed at 40-450C. The reaction mass was allowed to reach 3O0C and maintained there for Ih before filtration. The wet
solid was washed with 2 x 5ml of 50% aqueous tetrahydrofuran. Drying of the product yielded 4.8g of Form-Ill crystals of risedronate monosodium.
Advantages of present invention: 1. Present invention provides three novel crystalline forms designated as Form I, Form II, and Form III of risedronate monosodium, which are stable, reproducible, and suitable for pharmaceutical preparations.
2. Present invention provides processes for the novel crystalline forms, namely Form I, Form II, and Form III of risedronate monosodium, which are simple and easy to adopt on a commercial scale.
Claims
1. A novel crystalline form of risedronate monosodium, designated as Form I characterized by an X-ray powder diffraction pattern having peaks expressed as 2Θ (intensity in %) at about 9.06 (8.4), 12.35 (100), 13.00 (2.1), 23.73 (2.7), 24.03 (2.6), 24.72 (35.3), and 31.26 (3.2) degrees and the IR (KBr) spectrum having peaks at 3370, 3096, 1655, 1569, 1478, 1436, 1387, 1320, 1213, 1133, 1073, 1032, 935, 890, 800, 742, 687, 660, 629, 604, 535, and 472cm'1.
2. A novel crystalline form of risedronate monosodium, designated as Form II, characterized by an X-ray powder diffraction pattern having peaks expressed as 2Θ
(intensity in %) at about 6.09 (93.8), 9.08 (100), 12.1 (14.2), 12.34 (45.2), 13.03 (9.4), 14.44 (9.1), 15.85 (10.8), 16.68 (8.3), 17.26 (8.5), 19.15 (5.0), 19.87 (13.6), 20.65 (5.2), 21.97 (6.6), 23.02 (14.6), 23.71 (28.8), 25.60 (7.4), 27.87 (14.6), 30.41 (10.8), 31.27 (15.5), 31.86 (9.7), 35.50 (7.4), 36.61 (14.4), and 37.88 (6.4) degrees and the IR (KBr) spectrum having peaks at 3569, 3373, 1654, 1569, 1478, 1436, 1388, 1320, 1210, 1135, 1081, 1048, 986, 935, 887, 859, 818, 798, 746, 691, 660, 627, 606, 542, and 465cm"1.
3. A novel crystalline form of risedronate monosodium, designated as Form III, characterized by an X-ray powder diffraction pattern having peaks expressed as 2Θ (intensity in %) at about 8.97 (100), 12.22 (43.6), 12.92 (7.8), 15.73 (9.5), 19.81 (6.7),
22.92 (10.8), 23.60 (5.4), 23.92 (10.6), 24.58 (32.9), 26.00 (5.2), 27.85 (13.5), 31.16
(16.3), 32.77 (5.0), and 36.49 (10.5) degrees and the IR (KBr) spectrum having peaks at
-3620, 3361, 3096, 1654, 1569, 1478, 1436, 1387, 1319, 1212, 1133, 1074, 1033, 935,
890, 818, 801, 745, 688, 660, 630, 604, 566, 537, and 472cm"1.
4. A process for the preparation of Form I crystals of risedronate monosodium as defined in claim 1 comprising of dissolving risedronate monosodium in water and diluting it with methanol and isolating the Form-I crystals at 5-10°C.
5. A process for the preparation of Form II crystals of risedronate monosodium as defined in claim 2 comprising of dissolving risedronate monosodium in water and diluting it with ethanol and isolating the Form-II crystals at 25-30°C.
6. A process for the preparation of Form III crystals of risedronate monosodium as defined in claim 3 comprising of dissolving risedronate monosodium in water and diluting it with tetrahydrofuran and isolating the Form-Ill crystals at 25-30°C.
7. A pharmaceutical composition comprising the crystalline Form I of risedronate monosodium as defined in claim 1 and a pharmaceutically acceptable carrier. '
8. A pharmaceutical composition comprising the crystalline Form II of risedronate monosodium as defined in claim 8 and a pharmaceutically acceptable carrier.
9. A pharmaceutical composition comprising the crystalline Form III of risedronate monosodium as defined in claim 15 and a pharmaceutically acceptable carrier.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IN1209CH2005 | 2005-08-30 | ||
| IN1209/CHE/2005 | 2005-08-30 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| WO2007026379A2 true WO2007026379A2 (en) | 2007-03-08 |
| WO2007026379A3 WO2007026379A3 (en) | 2007-07-12 |
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ID=37709614
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/IN2006/000315 WO2007026379A2 (en) | 2005-08-30 | 2006-08-30 | Novel crystalline forms of risedronate monosodium |
Country Status (1)
| Country | Link |
|---|---|
| WO (1) | WO2007026379A2 (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2007291033A (en) * | 2006-04-26 | 2007-11-08 | Permachem Asia Ltd | Method for producing type-a crystal of 3-pyridyl-1-hydroxyethylidene-1,1-bisphosphonic acid sodium salt |
| US8076483B2 (en) | 2006-05-11 | 2011-12-13 | M/S. Ind Swift Laboratories Limited | Process for the preparation of pure risedronic acid or salts |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0186405A2 (en) * | 1984-12-21 | 1986-07-02 | The Procter & Gamble Company | Pharmaceutical compositions containing geminal diphosphonates |
| WO2003086355A1 (en) * | 2002-04-11 | 2003-10-23 | Teva Pharmaceutical Indudstries, Ltd. | Novel polymorphs and pseudopolymorphs of risedronate sodium |
-
2006
- 2006-08-30 WO PCT/IN2006/000315 patent/WO2007026379A2/en active Application Filing
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0186405A2 (en) * | 1984-12-21 | 1986-07-02 | The Procter & Gamble Company | Pharmaceutical compositions containing geminal diphosphonates |
| WO2003086355A1 (en) * | 2002-04-11 | 2003-10-23 | Teva Pharmaceutical Indudstries, Ltd. | Novel polymorphs and pseudopolymorphs of risedronate sodium |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2007291033A (en) * | 2006-04-26 | 2007-11-08 | Permachem Asia Ltd | Method for producing type-a crystal of 3-pyridyl-1-hydroxyethylidene-1,1-bisphosphonic acid sodium salt |
| 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 |
|---|---|
| WO2007026379A3 (en) | 2007-07-12 |
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