CN102887894A - Crystal form of solifenacin succinate and preparation method thereof - Google Patents
Crystal form of solifenacin succinate and preparation method thereof Download PDFInfo
- Publication number
- CN102887894A CN102887894A CN201110199259XA CN201110199259A CN102887894A CN 102887894 A CN102887894 A CN 102887894A CN 201110199259X A CN201110199259X A CN 201110199259XA CN 201110199259 A CN201110199259 A CN 201110199259A CN 102887894 A CN102887894 A CN 102887894A
- Authority
- CN
- China
- Prior art keywords
- succsinic acid
- crystal formation
- consumption
- preparation
- certain amount
- 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.)
- Pending
Links
Images
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention provides a novel crystal form of (3R)-1-azabicyclo[2.2.2]octan-3-yl(1S)-1-phenyl-3,4-dihydroisoquinoline-2(1H)-carboxylate butanedioic acid (solifenacin succinate, YM905) which is characterized in that an X-ray powder diffraction spectrum represented in degree of 2[theta] has characteristic peaks at positions of 3.5 +/- 0.2, 7.1 +/- 0.2, 10.8 +/- 0.2, 18.3 +/- 0.2, 21.5 +/- 0.2, 22.1 +/- 0.2, 24.9 +/- 0.2 and 35.5 +/- 0.2. The invention further provides two preparation methods of the solifenacin succinate with such crystal form. A first method is characterized by comprising the following steps: heating and dissolving the solifenacin succinate in acetone, adding a certain amount of ethyl acetate, cooling and crystallizing to obtain the solifenacin succinate with such crystal form; and a second method is characterized by comprising the following steps: dissolving a certain amount of solifenacin in isopropanol under a certain temperature, adding a certain amount of succinic acid, stirring to react, cooling and crystallizing to obtain the solifenacin succinate with such crystal form.
Description
Technical field
The invention belongs to the pharmaceutical chemistry synthesis technical field, relate to new crystal of succsinic acid YM-905 and preparation method thereof, and the application of the succsinic acid YM-905 of this crystal formation aspect preparation treatment overactive bladder medicine.
Background technology
Succsinic acid YM-905 (Solifenacin succinate), trade(brand)name: Vesicare, open in US Patent No. 6017927 and US6174896.Vesicare by FDA approval be used for overactive bladder (OAB) patient with the urinary incontinence and/or the treatment of frequent micturition, symptoms of urgency, once a day, specification is the tablet of 5 mg and 10 mg.
The molecular formula of YM-905 is C
23H
26O
2, molecular weight 362.46, chemistry (3R)-1-azabicyclo [2.2.2] octane by name-3-base (1S)-1-phenyl-3, the 4-dihydro-isoquinoline-2(1H)-and manthanoate, the succsinic acid YM-905 is its succinate form, has following chemical structure:
US Patent No. 20080114028 is pointed out: publication IPCOM000147748D discloses a kind of crystal formation of succsinic acid YM-905, it is characterized in that, powder x-ray diffraction figure is 3.9,11.2,14.3 with 18.8 ° ± 0.2 ° 2 θ place characteristic peak is arranged, and possible further PXRD is characterized as 7.6,19.3,21.1 there is characteristic peak at 23.2 and 25.2 ° ± 0.2 ° 2 θ place.In addition, US20080114028 discloses the another kind of crystal formation of succsinic acid YM-905, it is characterized in that, powder x-ray diffraction figure is 4.3,11.7,14.7,16.2,18.3,19.9,22.3 there is characteristic peak at 23.7 and 25.6 ° ± 0.2 ° 2q place, this patent has also been put down in writing the synthetic route of succsinic acid YM-905.
As everyone knows, compound all can two or more crystalline states exist, and this is the instinct of material.The molecule that structure is identical crystallizes into different solid forms, is called the polytropism material.Different crystal formations has different lattice energies, and it shows different physicalies when solid-state thus.Adopt preparation method of the present invention, obtained a kind of new crystal of succsinic acid YM-905 that is different from existing bibliographical information, prove (seeing accompanying drawing 1) by X-ray powder diffraction spectrum, thereby finished the present invention.
Summary of the invention
One object of the present invention is to provide a kind of succsinic acid YM-905 ((3R)-1-azabicyclo [2.2.2] octane-3-base (1S)-1-phenyl-3, the 4-dihydro-isoquinoline-2(1H)-the manthanoate succinate) crystal formation, its powder x-ray diffraction digital proof is the another new crystal formation that is different from above-mentioned published two kinds of crystal formations, its superior in quality, favorable reproducibility, HPLC normalization method purity is more than 99%, clinical treatment for overactive bladder.
Another object of the present invention has provided the preparation method of succsinic acid YM-905 of the crystal formation of the present invention of suitable suitability for industrialized production.
A further object of the present invention has provided the succsinic acid YM-905 that contains the crystal formation of the present invention for the treatment of significant quantity and the composition of one or more pharmaceutical carriers; Wherein said composition is oral preparations.
For achieving the above object, the invention provides following technical scheme:
The new crystal of a kind of succsinic acid YM-905 ((3R)-1-azabicyclo [2.2.2] octane-3-base (1S)-1-phenyl-3,4-dihydro-isoquinoline-2(1H)-manthanoate succinate) is characterized in that using Cu-K
aRadiation, λ=1.5405, spending X-ray powder diffraction spectrum that 2 θ represent 3.5 ± 0.2,7.1 ± 0.2,10.8 ± 0.2,18.3 ± 0.2,21.5 ± 0.2,22.1 ± 0.2,24.9 ± 0.2, there is characteristic peak (as shown in Figure 1) at 35.5 ± 0.2 places; Its infrared absorption pattern is at 3016 ± 5cm
-1, 2943 ± 5cm
-1, 1719 ± 5cm
-1, 1690 ± 5cm
-1, 1581 ± 5cm
-1There is absorption peak (as shown in Figure 2) at the place; Being further characterized in that its DTA(differential thermal analysis) the endothermic transition temperature is in about 146 ℃ (as shown in Figure 3).
Succsinic acid YM-905 crystal formation of the present invention, its described X-ray powder diffraction 2 θ positions 10.8 ± 0.2 place's diffracted intensities are 100%.
The preparation method of the succsinic acid YM-905 of crystal formation of the present invention is characterized in that: the succsinic acid YM-905 after the heating for dissolving, is added a certain amount of ethyl acetate again in acetone, obtain the succsinic acid YM-905 of this crystal formation by cooling crystallization; The consumption of wherein said acetone is 3 ~ 50 times (mL/g) of succsinic acid YM-905, and the consumption of ethyl acetate is 3 ~ 60 times of succsinic acid YM-905s (mL/g); The consumption of preferred acetone is 30 ~ 40 times of succsinic acid YM-905s (mL/g), and the consumption of ethyl acetate is 50 ~ 60 times of succsinic acid YM-905s (mL/g).
The another kind of preparation method of the succsinic acid YM-905 of crystal formation of the present invention, it is characterized in that: under certain 40 ~ 60 ℃, a certain amount of YM-905 is dissolved in the Virahol, adds a certain amount of succsinic acid, stirring reaction, then cooling crystallization obtains the succsinic acid YM-905 of this crystal formation; The consumption of wherein said Virahol is 2 ~ 20 times of YM-905s (mL/g), preferred 10 ~ 15 times (mL/g).
Among typical embodiment of the present invention, succsinic acid YM-905 0.5 g is added acetone 15 mL, be heated to backflow, until completely dissolved, add again 10 mL ethyl acetate, room temperature cooling crystallize out, filter, heat drying obtains succsinic acid YM-905 0.37 g of crystal formation of the present invention to constant weight, and purity is greater than 99%.
Another typical embodiment of the present invention: under 50 ℃, 3 g YM-905s are dissolved in the 30 mL Virahols, obtain the solution of clear.Add 1.07 g succsinic acids, stir 20 min, obtain soup compound.After mixture was cooled to room temperature, stirring was spent the night.Vacuum filtration goes out product, with 10 mL washed with isopropyl alcohol, then places 55 ℃ vacuum drier dry, spends the night and places the rear succsinic acid YM-905 that obtains crystal formation of the present invention, and purity is greater than 99%.
The succsinic acid YM-905 of crystal formation of the present invention has following feature:
1.X-ray powder diffraction:
Instrument: Rigaku D/max2500 type X-ray diffractometer;
Target: Cu-K
аRadiation (λ=1.5405), 2 θ sweep limit: 0-50 °
Step angle: 0.04 ℃
Computing time: 0.5 second
Pipe is pressed: 40KV
Pipe stream: 100mA
Sweep velocity: 8 ℃/min
Filter disc: graphite monochromator
X-ray powder diffraction result such as the following table of the succsinic acid YM-905 of crystal formation of the present invention:
| 2θ | Spacing (d value) | I/I 0 |
| 3.54 | 24.9 | 67 |
| 7.14 | 12.3 | 43 |
| 10.84 | 8.1 | 100 |
| 14.02 | 6.3 | 15 |
| 14.56 | 6.0 | 14 |
| 18.30 | 4.8 | 65 |
| 19.08 | 4.6 | 14 |
| 20.76 | 4.2 | 14 |
| 21.56 | 4.1 | 37 |
| 22.10 | 4.0 | 30 |
| 22.44 | 3.9 | 17 |
| 22.64 | 3.9 | 17 |
| 23.02 | 3.8 | 13 |
| 24.92 | 3.5 | 23 |
| 35.50 | 2.5 | 23 |
2. infrared spectra (IR):
Instrument: PE-983G infrared spectrometer
Sample preparation: KBr compressing tablet
Infrared spectra wave number (the cm of the succsinic acid YM-905 of crystal formation of the present invention
– 1) be: 3016 ± 5cm
-1, 2943 ± 5cm
-1, 1719 ± 5cm
-1, 1690 ± 5cm
-1, 1581 ± 5cm
-1
3. differential thermal analysis (DTA):
Instrument: Rigaku standard type TG-DTA analyser
Temperature range: room temperature～400 ℃
Heat-up rate: 10 ℃/minute
The endothermic transition temperature of the succsinic acid YM-905 of crystal formation of the present invention is at about 146 ℃.
The present invention further discloses and contain the pharmaceutical composition that the succsinic acid YM-905 with crystal formation of the present invention for the treatment of significant quantity and one or more pharmaceutical carriers form.Wherein said composition is oral preparations, the preferred oral preparation.For example tablet, capsule, granule, oral liquid etc.
One or more pharmaceutical carriers of the present invention comprise: stablizer, thinner, disintegrating agent, solvent, tackiness agent and lubricant etc.For example starch, Microcrystalline Cellulose, N.F,USP MANNITOL, dextrin, sucrose, lactose etc. of thinner wherein.Described tackiness agent such as water, ethanol, starch slurry, Vltra tears, Xylo-Mucine, sodium alginate or polyvinylpyrrolidone etc.Described lubricant comprises stearic acid, boric acid etc.Described disintegrating agent comprises starch, sodium starch glycolate element, low-substituted hydroxypropyl cellulose, croscarmellose sodium etc.Described stablizer such as agar, acrylic resin, ether of cellulose and carboxymethyl cellulose etc.
The medicinal compositions that contains the succsinic acid YM-905 of crystal formation of the present invention can be treated the overactive bladder of urgent urination, frequent micturition symptom.
Stability test
The result: the succsinic acid YM-905 with crystal formation of the present invention under high light, high temperature, super-humid conditions 0-10 days, the accelerated test 0-6 month, outward appearance, X-ray powder diffraction all do not change, and stable crystal form is described, give birth to without turning trichite, still keep original crystal formation; Related substance, content do not change in addition, illustrate that this crystal formation chemical stability is good, are fit to manufacturing and the standing storage of pharmaceutical preparation.
Description of drawings:
Fig. 1 is the succsinic acid YM-905 X-ray powder diffraction collection of illustrative plates of crystal formation of the present invention;
Fig. 2 is the succsinic acid YM-905 infared spectrum of crystal formation of the present invention;
Fig. 3 is that the succsinic acid YM-905 TG-DTA of crystal formation of the present invention is analyzed (TG-DTA) figure.
Embodiment
Following examples are with helping understand the present invention, and are not used in and also should be interpreted as the by any way restriction to inventing in the listed claim.Wherein the mensuration of fusing point adopts the YRT-3 type melting point apparatus of Precision Instrument Factory, Tianjin Univ. to measure; The preparation of succsinic acid YM-905 compound crude product is referring to US Patent No. 20080114028.
Reference example 1
Get the reaction flask of a 500mL, (be called for short " IQL ", 46g), carbonyl dimidazoles (is called for short " CDI ", 39g) with 230 mL toluene, stirred two hours under the room temperature, add 2g CDI again to add (S)-IQL.After then stirring 45 minutes, mixture is filtered, filtrate decompression is steamed the toluene solution that obtains IQL-imidazoles (" IQL-Im ") except partial solvent.
Get the reaction flask of a 1L, 34 g(R be housed)-the 3-quinuclidinol, 15g sodium hydride (60%), and 46 mL DMF, stirring at room progressively was heated to 85 ℃ after 1 hour.The toluene solution of IQL-Im is dropwised in 30 min, and then at 85 ℃ of lower stirring reaction 4 h, ambient temperature overnight is placed afterwards.Wash reaction solution (4 * 300 mL) with water, isolate organic layer, remove the YM-905 that solvent obtains 73 g oilies under reduced pressure.
Under the room temperature oily matter is dissolved in the 350 mL ethanol, in solution, adds the 24g succsinic acid, Precipitation is arranged this moment.Leach precipitation, with washing with alcohol (3 * 50 mL), place 50 ℃ vacuum drier dry.Obtain 79 g YM-905 succinate crude products after one week.
Succsinic acid YM-905 crude product 0.5 g that makes with reference to embodiment 1 adds acetone 15 mL, be heated to backflow, until completely dissolved, add 10 mL ethyl acetate, room temperature cooling crystallize out filters again, heat drying is to constant weight, obtain succsinic acid YM-905 0.37 g of crystal formation of the present invention, HPLC measures purity 99.7%, and the X-ray powder diffraction collection of illustrative plates is seen Fig. 1.Optical purity is 99.5%, and fusing point is 146.8 ~ 149.2 ℃.
Embodiment 2
Succsinic acid YM-905 crude product 1 g that makes with reference to embodiment 1 adds acetone 30 mL, be heated to backflow, until completely dissolved, add again 20 mL ethyl acetate, room temperature cooling crystallize out, filter, heat drying obtains succsinic acid YM-905 0.77 g of crystal formation of the present invention to constant weight, and HPLC measures 99.8%, optical purity is 99.5%, and the X-ray powder diffraction collection of illustrative plates is seen Fig. 1.Fusing point is 146.8 ~ 148.8 ℃.
Under 50 ℃, YM-905 3 g that make with reference to embodiment 1 are dissolved in the 30 mL Virahols, obtain the solution of clear.Add 1.07 g succsinic acids, stir 20 min, obtain soup compound.After mixture was cooled to room temperature, stirring was spent the night.Vacuum filtration goes out product, with 10 mL washed with isopropyl alcohol, then places 55 ℃ vacuum drier dry, spends the night and places the rear succsinic acid YM-905 that obtains crystal formation of the present invention.The X-ray powder diffraction collection of illustrative plates is seen Fig. 1.
Embodiment 4
Succsinic acid YM-905 5 g with crystal formation of the present invention add lactose 43 g, and Microcrystalline Cellulose 16 g mix, add an amount of 10% HPMC solution and granulate, drying adds sodium starch glycolate 5.3g again, Magnesium Stearate 0.7g, mixing, compressing tablet, film coating is made 1000.
Embodiment 5
Succsinic acid YM-905 5 g of crystal formation of the present invention, add lactose 106g, starch,pregelatinized 25 g, hydroxypropylcellulose 4 g, croscarmellose sodium 2.5g, pure water is granulated, and drying adds Magnesium Stearate 1 g, croscarmellose sodium 1.3 g mix, compressing tablet, film coating is made 1000.
Embodiment 6
Succsinic acid YM-905 5 g of crystal formation of the present invention add dextrin 29 g, and lactose 164.5 g use 70% alcohol granulation, drying, and Magnesium Stearate 1.5 g mix, and are encapsulated, make 1000 seed lac wafers.
Owing to described the present invention with specific embodiment, the technician who is proficient in this technology can make amendment and the equivalence change to it, and this is understood to include within the scope of the present invention.
Claims (7)
1. the new crystal of a succsinic acid YM-905 ((3R)-1-azabicyclo [2.2.2] octane-3-base (1S)-1-phenyl-3,4-dihydro-isoquinoline-2(1H)-manthanoate succinate) is characterized in that using Cu-K
aRadiation, λ=1.5405, spending X-ray powder diffraction spectrum that 2 θ represent 3.5 ± 0.2,7.1 ± 0.2,10.8 ± 0.2,18.3 ± 0.2,21.5 ± 0.2,22.1 ± 0.2,24.9 ± 0.2, there is characteristic peak at 35.5 ± 0.2 places, as shown in Figure 1; Its infrared absorption pattern is at 3016 ± 5cm
-1, 2943 ± 5cm
-1, 1719 ± 5cm
-1, 1690 ± 5cm
-1, 1581 ± 5cm
-1There is absorption peak at the place, as shown in Figure 2; Its differential thermal analysis endothermic transition temperature is at about 146 ℃, as shown in Figure 3.
2. succsinic acid YM-905 crystal formation claimed in claim 1, its described X-ray powder diffraction 2 θ positions 10.8 ± 0.2 place's diffracted intensities are 100%.
3. the preparation method of the succsinic acid YM-905 of the described crystal formation of claim 1 is characterized in that: the succsinic acid YM-905 after the heating for dissolving, is added a certain amount of ethyl acetate again in acetone, obtain the succsinic acid YM-905 of crystal formation of the present invention by cooling crystallization; The consumption of wherein said acetone is 3 ~ 50 times (mL/g) of succsinic acid YM-905, and the consumption of ethyl acetate is 3 ~ 60 times of succsinic acid YM-905s (mL/g).
4. preparation method claimed in claim 4, wherein the consumption of acetone is preferably 30 ~ 40 times of succsinic acid YM-905s (mL/g); The consumption of ethyl acetate is preferably 50 ~ 60 times of succsinic acid YM-905s (mL/g).
5. the preparation method of the succsinic acid YM-905 of the described crystal formation of claim 1, another feature also is: under 40 ~ 60 ℃, a certain amount of YM-905 is dissolved in the Virahol, add a certain amount of succsinic acid, stirring reaction, then cooling crystallization obtains the succsinic acid YM-905 of the described crystal formation of claim 1; Wherein the consumption of Virahol is 2 ~ 20 times of YM-905s (mL/g), preferred 10 ~ 15 times (mL/g).
6. pharmaceutical composition, it contains succsinic acid YM-905 and one or more pharmaceutical carriers of the crystal formation that claim 1 defines for the treatment of significant quantity.
7. pharmaceutical composition claimed in claim 7, wherein said composition is oral preparations.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201110199259XA CN102887894A (en) | 2011-07-18 | 2011-07-18 | Crystal form of solifenacin succinate and preparation method thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201110199259XA CN102887894A (en) | 2011-07-18 | 2011-07-18 | Crystal form of solifenacin succinate and preparation method thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN102887894A true CN102887894A (en) | 2013-01-23 |
Family
ID=47531592
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201110199259XA Pending CN102887894A (en) | 2011-07-18 | 2011-07-18 | Crystal form of solifenacin succinate and preparation method thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN102887894A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105362245A (en) * | 2014-08-30 | 2016-03-02 | 山东中泰药业有限公司 | Tablet composition with solifenacin and preparation method of tablet composition |
Citations (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2007076116A2 (en) * | 2005-12-21 | 2007-07-05 | Teva Pharmaceutical Industries Ltd. | Intermediates for preparing solifenacin |
| US20070191425A1 (en) * | 2004-03-16 | 2007-08-16 | Masatoshi Inakoshi | Solifenacin-containing composition |
| WO2008011462A2 (en) * | 2006-07-19 | 2008-01-24 | Dr. Reddy's Laboratories Ltd. | Process for preparing solifenacin and its salts |
| WO2008013851A2 (en) * | 2006-07-24 | 2008-01-31 | Teva Pharmaceutical Industries Ltd. | Processes for preparing polymorphic forms of solifenacin succinate |
| WO2008062282A2 (en) * | 2006-11-22 | 2008-05-29 | Medichem S.A. | An improved process for the synthesis of solifenacin |
| WO2008077357A2 (en) * | 2006-12-22 | 2008-07-03 | Zentiva, A.S. | A method for the preparation of solifenacin |
| US20080287680A1 (en) * | 2004-02-09 | 2008-11-20 | Astellas Pharma Inc. | Solifenacin Succinate-Containing Composition |
| WO2009011844A1 (en) * | 2007-07-13 | 2009-01-22 | Teva Pharmaceutical Industries Ltd. | Processes for solifenacin preparation |
| US20090203915A1 (en) * | 2008-02-08 | 2009-08-13 | Dipharma Francis S.R.L. | Process for the preparation of solifenacin |
| WO2009139002A2 (en) * | 2008-05-12 | 2009-11-19 | Msn Laboratories Limited | An improved process for the preparation of solifenacin and its pharmaceutically acceptable salts thereof |
| WO2009142522A1 (en) * | 2008-05-23 | 2009-11-26 | Zaklady Farmaceutyczne Polpharma Sa | Process for preparation of solifenacin and/or the pharmaceutically acceptable salts thereof of high pharmaceutical purity |
| CN101711248A (en) * | 2007-03-30 | 2010-05-19 | 医药化学公司 | An improved process for the synthesis of solifenacin |
| WO2010103529A1 (en) * | 2009-03-09 | 2010-09-16 | Megafine Pharma(P) Ltd. | A new method for the preparation of solifenacin and new intermediate thereof |
| WO2011003624A1 (en) * | 2009-07-09 | 2011-01-13 | Krka, D.D., Novo Mesto | A process for the preparation and purification of solifenacin salts |
-
2011
- 2011-07-18 CN CN201110199259XA patent/CN102887894A/en active Pending
Patent Citations (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20080287680A1 (en) * | 2004-02-09 | 2008-11-20 | Astellas Pharma Inc. | Solifenacin Succinate-Containing Composition |
| US20070191425A1 (en) * | 2004-03-16 | 2007-08-16 | Masatoshi Inakoshi | Solifenacin-containing composition |
| WO2007076116A2 (en) * | 2005-12-21 | 2007-07-05 | Teva Pharmaceutical Industries Ltd. | Intermediates for preparing solifenacin |
| WO2008011462A2 (en) * | 2006-07-19 | 2008-01-24 | Dr. Reddy's Laboratories Ltd. | Process for preparing solifenacin and its salts |
| WO2008013851A2 (en) * | 2006-07-24 | 2008-01-31 | Teva Pharmaceutical Industries Ltd. | Processes for preparing polymorphic forms of solifenacin succinate |
| WO2008062282A2 (en) * | 2006-11-22 | 2008-05-29 | Medichem S.A. | An improved process for the synthesis of solifenacin |
| WO2008077357A2 (en) * | 2006-12-22 | 2008-07-03 | Zentiva, A.S. | A method for the preparation of solifenacin |
| CN101711248A (en) * | 2007-03-30 | 2010-05-19 | 医药化学公司 | An improved process for the synthesis of solifenacin |
| WO2009011844A1 (en) * | 2007-07-13 | 2009-01-22 | Teva Pharmaceutical Industries Ltd. | Processes for solifenacin preparation |
| US20090203915A1 (en) * | 2008-02-08 | 2009-08-13 | Dipharma Francis S.R.L. | Process for the preparation of solifenacin |
| WO2009139002A2 (en) * | 2008-05-12 | 2009-11-19 | Msn Laboratories Limited | An improved process for the preparation of solifenacin and its pharmaceutically acceptable salts thereof |
| WO2009142522A1 (en) * | 2008-05-23 | 2009-11-26 | Zaklady Farmaceutyczne Polpharma Sa | Process for preparation of solifenacin and/or the pharmaceutically acceptable salts thereof of high pharmaceutical purity |
| WO2010103529A1 (en) * | 2009-03-09 | 2010-09-16 | Megafine Pharma(P) Ltd. | A new method for the preparation of solifenacin and new intermediate thereof |
| WO2011003624A1 (en) * | 2009-07-09 | 2011-01-13 | Krka, D.D., Novo Mesto | A process for the preparation and purification of solifenacin salts |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105362245A (en) * | 2014-08-30 | 2016-03-02 | 山东中泰药业有限公司 | Tablet composition with solifenacin and preparation method of tablet composition |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN102256494A (en) | Polymorphs of (s)-3-aminomethyl-7-(3-hydroxy-propoxy)-3h-benzo[c][1,2] oxaborol-1-ol | |
| CN104603123A (en) | Solid forms of trelagliptin, preparation method and applications thereof | |
| CN111875530A (en) | Pramipexole hydrate crystal and preparation method thereof | |
| CN103073542A (en) | Preparation method and application of tropisetron citrate crystal form II | |
| CN102887894A (en) | Crystal form of solifenacin succinate and preparation method thereof | |
| CN115304608B (en) | Pyrazolopyrimidine ester compound crystal form and preparation method thereof | |
| CN103059013B (en) | Crystal formation of Dasatinib monohydrate and preparation method thereof | |
| CN106674321A (en) | Preparation method of sofosbuvir crystal form 6 | |
| CN115260210B (en) | Cepharanthine crystal form and preparation method thereof | |
| CN102659644B (en) | Crystal forms of 2-aminoethyl sulfonic acid and preparation processes for crystal forms | |
| CN114008023B (en) | Crystal form of Sofos-piramide and preparation method thereof | |
| CN105777651A (en) | Crystal form of poly adenosinediphosphate-ribose polymerase (PARP) inhibitor, preparation method for crystal form and medicinal use of crystal form | |
| CN115353456A (en) | Flurbiprofen axetil crystal and preparation method thereof | |
| KR19980064288A (en) | New Form of Polysiloxane Mesylate (Type III) | |
| CN116621828A (en) | Crystal forms of oxazolidinone derivative, preparation method and application thereof | |
| CN106478636A (en) | Ticagrelor crystal formation and preparation method | |
| CN111606816A (en) | Dezocine crystal form and preparation method thereof | |
| CN110804058B (en) | Novel ibrutinib crystal form and preparation method thereof | |
| CN108570045B (en) | Crystal form of anisodamine hydrobromide, preparation method and pharmaceutical composition thereof | |
| CN105859748B (en) | Polycyclic compound sodium salt and its polymorphic, preparation method and application | |
| CN118126112B (en) | Co-crystal of cytotoxin intermediate and preparation method thereof | |
| CN106317035A (en) | Empagliflozin monocrystalline and preparation method and purpose thereof | |
| WO2023131017A1 (en) | Crystal form of fused ring derivative, and preparation method therefor and use thereof | |
| CN117304188A (en) | Novel crystal form of avibactam monosodium salt | |
| CN117263938A (en) | Novel crystal form of avibactam monosodium salt |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| ASS | Succession or assignment of patent right |
Owner name: JIANGSU DEYUAN PHARMACEUTICAL CO., LTD. Effective date: 20121226 |
|
| C41 | Transfer of patent application or patent right or utility model | ||
| TA01 | Transfer of patent application right |
Effective date of registration: 20121226 Address after: 300193 Tianjin City, Nankai District Anshan West Road No. 308 six floor Applicant after: Tianjin Pharmaceutical Group Technology Development Co., Ltd. Applicant after: JIANGSU DEYUAN PHARMACEUTICAL CO., LTD. Address before: 300193 Tianjin City, Nankai District Anshan West Road No. 308 building six pharmaceutical research institute Applicant before: Tianjin Pharmaceutical Group Technology Development Co., Ltd. |
|
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C53 | Correction of patent of invention or patent application | ||
| CB02 | Change of applicant information |
Address after: 300193 Tianjin City, Nankai District Anshan West Road No. 308 six floor Applicant after: Tianjin Pharmaceutical Group Technology Development Co., Ltd. Applicant after: JIANGSU DEYUAN PHARMACEUTICAL CO., LTD. Address before: 300193 Tianjin City, Nankai District Anshan West Road No. 308 six floor Applicant before: Tianjin Pharmaceutical Group Technology Development Co., Ltd. Applicant before: JIANGSU DEYUAN PHARMACEUTICAL CO., LTD. |
|
| C12 | Rejection of a patent application after its publication | ||
| RJ01 | Rejection of invention patent application after publication |
Application publication date: 20130123 |