CN106632391A - Prasugrel hydrochloride compound, preparation method of prasugrel hydrochloride compound and pharmaceutical composition containing prasugrel hydrochloride - Google Patents
Prasugrel hydrochloride compound, preparation method of prasugrel hydrochloride compound and pharmaceutical composition containing prasugrel hydrochloride Download PDFInfo
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- CN106632391A CN106632391A CN201611202689.1A CN201611202689A CN106632391A CN 106632391 A CN106632391 A CN 106632391A CN 201611202689 A CN201611202689 A CN 201611202689A CN 106632391 A CN106632391 A CN 106632391A
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- Prior art keywords
- prasugrel
- prasugrel hydrochloride
- preparation
- hydrochloride compound
- compound
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- 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.)
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/13—Crystalline forms, e.g. polymorphs
Abstract
The invention provides a prasugrel hydrochloride compound. The compound has a crystal form Z1. The X-ray diffraction data are as follows: characteristic absorption peaks exist at the reflection angles 2 theta of 8.367 degrees, 13.796 degrees, 14.834 degrees, 22.363 degrees and 30.343 degrees. The prepared prasugrel hydrochloride compound with the crystal form Z1 can be used for treating atherosclerosis and acute coronary syndromes.
Description
Technical field
The invention belongs to pharmaceutical technology field, more particularly to a kind of prasugrel hydrochloride compound and preparation method thereof and
Pharmaceutical composition containing prasugrel hydrochloride.
Background technology
Prasugrel hydrochloride, chemical name 2- [2- (acetoxyl group) -6,7- dihydro-thiophenes simultaneously [3,2-c] pyridine -5 (4H) -
Base] -1- cyclopropyl -2- (2- fluorophenyls) acetophenone hydrochloride, opened jointly by Japanese Sankyo companies and EliLilly companies of the U.S.
Send out, and in 2 Yue23Huo European Union approval listing in 2009, be applied to treat atherosclerotic and acute coronary syndromes
Levy.
At present, there are various crystal formations known to prasugrel hydrochloride, patent WO2002004461 disclose crystal formation A B1 B2,
Patent WO2009062044 disclose crystal formation C D E it is unformed, WO2012175031 disclose crystal formation H1 H2 H3.And medicine
Crystal formation vital impact is suffered from the solubility of medicine, body absorption, distribution, improving the crystal formation of medicine contributes to carrying
The bioavilability of high medicine and the stability of preparation.
The content of the invention
In view of this, present invention aims to the deficiencies in the prior art, and a kind of salt with crystal formation Z1 is provided
Sour prasugrel compound, can treat atherosclerotic and acute coronary syndrome.
In order to realize foregoing invention purpose, the present invention provides technical scheme below：
A kind of prasugrel hydrochloride compound, with crystal formation Z1, X-ray diffraction data are as follows：It is in the θ of angle of reflection 2
There is characteristic absorption peak at 8.367 °, 13.796 °, 14.834 °, 22.363 ° and 30.343 °.
Present invention also offers the preparation method of the prasugrel hydrochloride compound described in such scheme, including following step
Suddenly：
1) after at 30～60 DEG C by the mixing of prasugrel, ketones solvent and alcohols solvent, prasugrel mixing is obtained molten
Liquid；
2) to the step 1) the prasugrel mixed solution and dripping chlorobenzoyl chloride that obtains, 20～40min is stirred, will
To solution system be down to 23～27 DEG C, growing the grain obtains the prasugrel hydrochloride compound with Z1 crystal formations.
Preferably, the ketones solvent is acetone, butanone or methyl iso-butyl ketone (MIBK), the ketones solvent and prasugrel matter
Amount is than being 5～20:1.
Preferably, the alcohols solvent is the mol ratio of methyl alcohol, ethanol or isopropanol, the alcohols solvent and prasugrel
For 1.5～8:1.
Preferably, the step 2) in the mol ratio of chlorobenzoyl chloride and prasugrel be 1～2.5:1.
Preferably, the time of the growing the grain is 5～48h.
The invention provides a kind of pharmaceutical composition, including described prasugrel hydrochloride compound and pharmaceutically acceptable
Auxiliary material.
Preferably, the formulation of described pharmaceutical composition includes tablet, capsule, supensoid agent, granule, coating agent, film
Garment piece or soft capsule.
Preferably, it is 5～20mg that the quality with crystal formation Z1 prasugrel hydrochloride compounds is contained in per unit preparation.
The invention provides a kind of prasugrel hydrochloride compound, the compound has crystal formation Z1, X-ray diffraction data
It is as follows：It is have characteristic absorption peak at 8.367 °, 13.796 °, 14.834 °, 22.363 ° and 30.343 ° in the θ of angle of reflection 2.The present invention
The prasugrel compound with crystal formation Z1 for preparing can treat atherosclerotic and acute coronary syndrome.
Description of the drawings
The X- powder diagrams of the prasugrel hydrochloride compound that Fig. 1 is obtained for the embodiment of the present invention, the compound has
Crystal formation Z1, X-ray diffraction data are as follows：It it is 8.367 °, 13.796 °, 14.834 °, 22.363 ° and 30.343 ° in the θ of angle of reflection 2
There is characteristic absorption peak at place.
The prasugrel hydrochloride compound TG-DSC collection of illustrative plates that Fig. 2 is obtained for the embodiment of the present invention.
The prasugrel hydrochloride compound infared spectrum that Fig. 3 is obtained for the embodiment of the present invention.
Specific embodiment
The invention provides a kind of prasugrel hydrochloride compound, with crystal formation Z1, X-ray diffraction data are as follows：Anti-
The θ of firing angle 2 is have characteristic absorption peak at 8.367 °, 13.796 °, 14.834 °, 22.363 ° and 30.343 °.
In the present invention, described is at 8.367 °, 13.796 °, 14.834 °, 22.363 ° and 30.343 ° in the θ of angle of reflection 2
Diffracted intensity be respectively 4238,2792,5578,6225 and 3190.
Present invention also offers the preparation method of the prasugrel hydrochloride compound described in such scheme, including following step
Suddenly：
1) after at 30～60 DEG C by the mixing of prasugrel, ketones solvent and alcohols solvent, prasugrel mixing is obtained molten
Liquid；
2) to the step 1) the prasugrel mixed solution and dripping chlorobenzoyl chloride that obtains, 20～40min is stirred, will
To solution system be cooled to 23～27 DEG C, growing the grain obtains the prasugrel hydrochloride compound with Z1 crystal formations.
The present invention is preferably suspended in prasugrel in ketones solvent, after being warmed up to 30～60 DEG C of dissolvings, obtains pula lattice
Thunder ketone solution；The prasugrel ketone solution is mixed with alcohols solvent again, obtains prasugrel mixed solution.
In the present invention, the ketones solvent is acetone, butanone or methyl iso-butyl ketone (MIBK).In the present invention, the ketone
Solvent is preferably 5～20 with the mass ratio of prasugrel:1, more preferably 8～18:1, most preferably 10～15:1.The present invention is right
The source of the ketone reagent is not particularly limited, using commercial goods.
In the present invention, the alcohol reagent is methyl alcohol, ethanol or isopropanol.In the present invention, the alcohol reagent with
The mol ratio of prasugrel is preferably 1.5～8:1, more preferably 2.0～6.5:1, most preferably 2.5～6.The present invention is to described
The source of alcohol reagent is not particularly limited, using commercial goods.
In the present invention, the prasugrel is suspended in ketones solvent, is warmed up to 30～60 DEG C of dissolvings, it is preferred to heat up
To 35～55 DEG C, more preferably 40～50 DEG C.In the present invention, the temperature after the alcohols solvent is added to keep constant.
After obtaining prasugrel mixed solution, the present invention is stirred to the prasugrel mixed solution and dripping chlorobenzoyl chloride
20～40min is mixed, the solution system for obtaining is down to into 23～27 DEG C, growing the grain obtains the prasugrel hydrochloride with Z1 crystal formations
Compound.
In the present invention, the chlorobenzoyl chloride is preferably 1～2.5 with the mol ratio of prasugrel:1, more preferably 1.2～
2.0:1, most preferably 1.5～1.8:1.The present invention is not particularly limited to the source of the chlorobenzoyl chloride, using commercial goods
.
In the present invention, the speed of the stirring be 10～200rpm, preferably 50～150rpm, more preferably 100～
145rpm.The time of the stirring is 20～40min, more preferably preferably 25～35min, 30min.
In the present invention, the solution system that obtains of chlorobenzoyl chloride is added dropwise and is cooled to 23～27 DEG C of growing the grains, it is preferably dropped to 24～
26 DEG C, more preferably it is down to 25 DEG C.The time of the growing the grain is 5～48h, most preferably preferably 8～40h, 12～35h.
The present invention is filtered, washed and dried the growing the grain product for obtaining preferably after growing the grain, obtains the salt with Z1 crystal formations
Sour prasugrel.In the present invention, the growing the grain product obtains filter cake after filtering；The filter cake is washed, the washing
Detergent is preferably acetone；The amount of the detergent of the washing is preferably 5～10 times of filter residue；The number of times of the washing
Preferably 1～2 time.
The present invention does not have special restriction to the mode of the drying, using the skill of drying well known to those skilled in the art
Art scheme, in the present invention, the drying is preferably vacuum dried；The vacuum drying vacuum is preferably 0.085
～0.095MPa；The vacuum drying temperature is preferably 40～45 DEG C；In the present invention, by the filtration cakes torrefaction after the washing
To constant weight.
Present invention also offers a kind of pharmaceutical composition, including the hydrochloric acid pula lattice with crystal formation Z1 described in such scheme
Thunder compound and pharmaceutically acceptable auxiliary material.The present invention does not have special restriction, ability to the species and consumption of the auxiliary material
Field technique personnel can be as needed the suitable auxiliary material of dosage form selection；In the present invention, the formulation of described pharmaceutical composition includes
Tablet, capsule, supensoid agent, granule, coating agent, Film coated tablets or soft capsule.
In the present invention, when the formulation of described pharmaceutical composition makes tablet, the auxiliary material of the tablet include mannitol,
HPMC, microcrystalline cellulose, Ac-Di-Sol and magnesium stearate.Source of the present invention to above-mentioned auxiliary material
It is not particularly limited, is routinely selected using those skilled in the art.
In the present invention, when described pharmaceutical composition makes capsule, the auxiliary material of the capsule includes hydroxypropyl methylcellulose
Element, microcrystalline cellulose, CMS that and magnesium stearate.The present invention is not particularly limited to the source of above-mentioned auxiliary material, adopts
Those skilled in the art routinely select.
In the present invention, when described pharmaceutical composition makes granule, the auxiliary material of the granule includes lactose, hydroxypropyl
Methylcellulose, Ac-Di-Sol and magnesium stearate.The present invention is not particularly limited to the source of above-mentioned auxiliary material, adopts
Routinely selected with those skilled in the art.
In the present invention, it is 5 that the quality with crystal formation Z1 prasugrel hydrochloride compounds is contained in the per unit preparation
～20mg, preferably 8～18mg, more preferably 10～15mg.
With reference to embodiment is to a kind of prasugrel hydrochloride compound for providing of the invention and preparation method thereof and contains
The pharmaceutical composition of prasugrel hydrochloride is described in detail, but they can not be interpreted as to the scope of the present invention
Limit.
Embodiment 1
The preparation method of the prasugrel hydrochloride compound with crystal formation Z1, comprises the following steps：
1) acetone 100ml is added in 200ml there-necked flasks, prasugrel 10.0g is added, makes prasugrel be suspended in third
In ketone, 35 DEG C are warming up to, are stirred to being completely dissolved, obtain prasugrel ketone solution；
2) in step 1) at a temperature of, isopropanol 3.5ml is added in prasugrel ketone solution, then to the solution for obtaining
Chlorobenzoyl chloride 4.5ml is added dropwise in system；
3) after completion of dropping, insulated and stirred 30 minutes；
4) 25 DEG C are cooled to, growing the grain 24 hours；
5) material filtering for obtaining growing the grain, the filter residue being filtrated to get is washed 2 times using 5 times of acetone, after washing
Filter residue is dried to obtain the prasugrel hydrochloride compound with crystal formation Z1 in the case where vacuum is 0.085MPa.
The present invention weighs the prasugrel hydrochloride compound for obtaining, and weight is 8.95g, is calculated yield for 81.4%；
Jing HPLC detect that purity is 99.5%.
The prasugrel hydrochloride compound for obtaining is carried out X-ray diffraction detection by the present invention, and the condition of detection is：Germany
Brooker D8Advance, LynxEye detector array, voltage 40KV, electric current 40MA, 0.02 ° of step-length, test speed 0.1sec/
Step, testing result is as shown in figure 1, show that the X-ray diffraction data of the compound are as follows in Fig. 1：It is in the θ of angle of reflection 2
There are characteristic absorption peak, as seen from Figure 1, the present embodiment at 8.367 °, 13.796 °, 14.834 °, 22.363 ° and 30.343 °
The prasugrel hydrochloride compound for preparing has crystal formation Z1.
The prasugrel hydrochloride compound for obtaining is carried out TG-DSC detections by the present invention, and the condition of detection is：U.S. TA is public
Department differential scanning calorimeter Q2000, detection range 0-400 DEG C, testing result is shown in Fig. 2, and 180 DEG C of the data display of TG-DSC has one
Highly endothermic peak.The prasugrel hydrochloride compound for obtaining is carried out infrared detection by the present invention, and infared spectrum is shown in Fig. 3.
Using X-ray diffraction detection method, prasugrel hydrochloride compound has the absworption peak of following characteristics, is shown in Table 1：
The absworption peak of the prasugrel hydrochloride compound of table 1
Embodiment 2
The preparation method of the prasugrel hydrochloride compound with crystal formation Z1, comprises the following steps：
1) butanone 100ml is added in 200ml there-necked flasks, prasugrel 10.0g is added, makes prasugrel be suspended in fourth
In ketone, 35 DEG C are warming up to, are stirred to being completely dissolved, obtain prasugrel ketone solution；
2) in step 1) at a temperature of, ethanol 3.5ml is added in prasugrel ketone solution, then to the solution body for obtaining
Chlorobenzoyl chloride 4.5ml is added dropwise in system；
3) after completion of dropping, insulated and stirred 30 minutes.
4) 24 DEG C are cooled to, growing the grain 24 hours；
5) material filtering for obtaining growing the grain, the filter residue being filtrated to get is washed 2 times using 10 times of butanone, after washing
Filter residue is dried to obtain the prasugrel hydrochloride compound with crystal formation Z1 in the case where vacuum is 0.090MPa.
The present invention weighs the prasugrel hydrochloride compound for obtaining, and weight is 6.25 grams, and it is 56.8% to be calculated yield,
Jing HPLC detect that purity is 99.6%.
The prasugrel hydrochloride compound for obtaining is carried out X-ray diffraction detection by the present invention, and the X-ray of the compound is spread out
Penetrate data as follows：It is have characteristic absorption peak at 8.367 °, 13.796 °, 14.834 °, 22.363 ° and 30.343 ° in the θ of angle of reflection 2,
It can be seen from the results that the prasugrel hydrochloride compound that the present embodiment is prepared has crystal formation Z1.
Embodiment 3
The preparation method of the prasugrel hydrochloride compound with crystal formation Z1, comprises the following steps：
1) butanone 120ml is added in 200ml there-necked flasks, prasugrel 10.0g is added, makes prasugrel be suspended in fourth
In ketone, 45 DEG C are warming up to, are stirred to being completely dissolved, obtain prasugrel ketone solution；
2) in step 1) at a temperature of, ethanol 4.5ml is added in prasugrel ketone solution, then to the solution body for obtaining
Chlorobenzoyl chloride 5.5ml is added dropwise in system；
3) after completion of dropping, insulated and stirred 30 minutes；
4) 27 DEG C are cooled to, growing the grain 48 hours；
5) material filtering for obtaining growing the grain, the filter residue being filtrated to get is washed 1 time using 8 times of butanone, after washing
Filter residue is dried to obtain the prasugrel hydrochloride compound with crystal formation Z1 in the case where vacuum is 0.095MPa.
The present invention weighs the prasugrel hydrochloride compound for obtaining, and weight is 9.25g, is calculated yield for 84.1%；
Jing HPLC detection purity is 99.6%.
The prasugrel hydrochloride compound for obtaining is carried out X-ray diffraction detection by the present invention, and the X-ray of the compound is spread out
Penetrate data as follows：It is have characteristic absorption peak at 8.367 °, 13.796 °, 14.834 °, 22.363 ° and 30.343 ° in the θ of angle of reflection 2,
It can be seen from the results that the prasugrel hydrochloride compound that the present embodiment is prepared has crystal formation Z1.
Embodiment 4
The preparation method of the prasugrel hydrochloride compound with crystal formation Z1, comprises the following steps：
1) acetone 100ml is added in 200ml there-necked flasks, prasugrel 10.0g is added, makes prasugrel be suspended in third
In ketone, 55 DEG C are warming up to, are stirred to being completely dissolved, obtain prasugrel ketone solution；
2) in step 1) at a temperature of, isopropanol 2.5ml is added in prasugrel ketone solution, then to the solution for obtaining
Chlorobenzoyl chloride 3.7ml is added dropwise in system；
3) after completion of dropping, insulated and stirred 30 minutes；
4) 25 DEG C are cooled to, growing the grain 5 hours；
5) material filtering for obtaining growing the grain, the filter residue being filtrated to get is washed 2 times using 6 times of acetone, after washing
Filter residue is dried to obtain the prasugrel hydrochloride compound with crystal formation Z1 in the case where vacuum is 0.085MPa.
The present invention weighs the prasugrel hydrochloride compound for obtaining, and weight is 7.95g, is calculated yield for 72.3%；
Jing HPLC detect that purity is 99.5%.
The prasugrel hydrochloride compound for obtaining is carried out X-ray diffraction detection by the present invention, and the X-ray of the compound is spread out
Penetrate data as follows：It is have characteristic absorption peak at 8.367 °, 13.796 °, 14.834 °, 22.363 ° and 30.343 ° in the θ of angle of reflection 2,
It can be seen from the results that the prasugrel hydrochloride compound that the present embodiment is prepared has crystal formation Z1.
Embodiment 5
By 75g mannitol, 10g HPMCs, 75g microcrystalline celluloses, 12g Ac-Di-Sols difference
80 mesh sieves are crossed, the prasugrel compound 12g of the crystal formation Z1 for then obtaining with embodiment 1 mixes, dry granulating machine granulation；Xiang get
To particle in add 1g magnesium stearates, mixing, be pressed into 1000, obtain the prasugrel hydrochloride tablet with Z1 crystal formations.
Embodiment 6
10g HPMCs, 120g microcrystalline celluloses are crossed respectively 80 mesh sieves, the crystalline substance for then obtaining with embodiment 2
The prasugrel compound 6g of type Z1 is well mixed, dry granulating machine granulation；10g CMSs are added in the particle for obtaining
Sodium and 1g magnesium stearates, are well mixed, filling into 1000 capsules, obtain the prasugrel hydrochloride capsule with Z1 crystal formations.
Embodiment 7
The component of granule：The prasugrel hydrochloride compound of crystal formation Z1, lactose, HPMC is crosslinked carboxylic first
Base sodium cellulosate, magnesium stearate g.
140g lactose, 10g HPMCs, 12g Ac-Di-Sols are crossed respectively 80 mesh sieves, Ran Houyu
The prasugrel compound 12g of the crystal formation Z1 that embodiment 3 is obtained is well mixed, dry granulating machine granulation；To in the particle for obtaining
1g magnesium stearates are added, is well mixed, it is filling into 1000 bags of particles, obtain the prasugrel hydrochloride granule with Z1 crystal formations.
As seen from the above embodiment, the prasugrel hydrochloride compound for obtaining is carried out X-ray diffraction detection by the present invention,
The compound is have characteristic absorption peak at 8.367 °, 13.796 °, 14.834 °, 22.363 ° and 30.343 ° in the θ of angle of reflection 2, is had
There are crystal formation Z1 structures, and the prasugrel compound with crystal formation Z1 can treat atherosclerotic and acute coronary
Syndrome.
The above is only the preferred embodiment of the present invention, it is noted that for the ordinary skill people of the art
For member, under the premise without departing from the principles of the invention, some improvements and modifications can also be made, these improvements and modifications also should
It is considered as protection scope of the present invention.
Claims (9)
1. a kind of prasugrel hydrochloride compound, it is characterised in that with crystal formation Z1, X-ray diffraction data are as follows：In reflection
The θ of angle 2 is have characteristic absorption peak at 8.367 °, 13.796 °, 14.834 °, 22.363 ° and 30.343 °.
2. the preparation method of the prasugrel hydrochloride compound described in claim 1, comprises the following steps：
1) after at 30～60 DEG C by the mixing of prasugrel, ketones solvent and alcohols solvent, prasugrel mixed solution is obtained；
2) to the step 1) the prasugrel mixed solution and dripping chlorobenzoyl chloride that obtains, stirs 20～40min, by what is obtained
Solution system is down to 23～27 DEG C, and growing the grain obtains the prasugrel hydrochloride compound with Z1 crystal formations.
3. preparation method according to claim 2, it is characterised in that the ketones solvent is that acetone, butanone or methyl are different
Butyl ketone, the ketones solvent is 5～20 with prasugrel mass ratio:1.
4. preparation method according to claim 2, it is characterised in that the alcohols solvent is methyl alcohol, ethanol or isopropanol, institute
It is 1.5～8 that alcohols solvent is stated with the mol ratio of prasugrel:1.
5. preparation method according to claim 2, it is characterised in that the step 2) in chlorobenzoyl chloride and prasugrel
Mol ratio is 1～2.5:1.
6. preparation method according to claim 2, it is characterised in that the time of the growing the grain is 5～48h.
7. a kind of pharmaceutical composition, including the prasugrel hydrochloride compound described in claim 1 and pharmaceutically acceptable auxiliary
Material.
8. pharmaceutical composition according to claim 7, it is characterised in that the formulation of described pharmaceutical composition include tablet,
Capsule, supensoid agent, granule, coating agent, Film coated tablets or soft capsule.
9. pharmaceutical composition according to claim 8, it is characterised in that containing having crystal formation Z1 hydrochloric acid in per unit preparation
The quality of prasugrel compound is 5～20mg.
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| CN201611202689.1A CN106632391A (en) | 2016-12-23 | 2016-12-23 | Prasugrel hydrochloride compound, preparation method of prasugrel hydrochloride compound and pharmaceutical composition containing prasugrel hydrochloride |
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| Application Number | Priority Date | Filing Date | Title |
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| CN201611202689.1A CN106632391A (en) | 2016-12-23 | 2016-12-23 | Prasugrel hydrochloride compound, preparation method of prasugrel hydrochloride compound and pharmaceutical composition containing prasugrel hydrochloride |
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1452624A (en) * | 2000-07-06 | 2003-10-29 | 三共株式会社 | Hydropyridine deriv. acid addition salts |
| WO2009062044A2 (en) * | 2007-11-09 | 2009-05-14 | Dr. Reddy's Laboratories Ltd. | Processes for the preparation of prasugrel, and its salts and polymorphs |
| WO2011057593A2 (en) * | 2009-11-16 | 2011-05-19 | Zentiva, K.S. | New salts of prasugrel and a method of their production |
| CN105601643A (en) * | 2015-12-23 | 2016-05-25 | 山东鲁抗医药股份有限公司 | Preparation method of high-purity prasugrel hydrochloride |
-
2016
- 2016-12-23 CN CN201611202689.1A patent/CN106632391A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1452624A (en) * | 2000-07-06 | 2003-10-29 | 三共株式会社 | Hydropyridine deriv. acid addition salts |
| WO2009062044A2 (en) * | 2007-11-09 | 2009-05-14 | Dr. Reddy's Laboratories Ltd. | Processes for the preparation of prasugrel, and its salts and polymorphs |
| WO2011057593A2 (en) * | 2009-11-16 | 2011-05-19 | Zentiva, K.S. | New salts of prasugrel and a method of their production |
| CN105601643A (en) * | 2015-12-23 | 2016-05-25 | 山东鲁抗医药股份有限公司 | Preparation method of high-purity prasugrel hydrochloride |
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Application publication date: 20170510 |