WO2012123858A1 - Amorphous lurasidone hydrochloride - Google Patents
Amorphous lurasidone hydrochloride Download PDFInfo
- Publication number
- WO2012123858A1 WO2012123858A1 PCT/IB2012/051073 IB2012051073W WO2012123858A1 WO 2012123858 A1 WO2012123858 A1 WO 2012123858A1 IB 2012051073 W IB2012051073 W IB 2012051073W WO 2012123858 A1 WO2012123858 A1 WO 2012123858A1
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- Prior art keywords
- lurasidone hydrochloride
- amorphous
- solvent
- process according
- lurasidone
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/496—Non-condensed piperazines containing further heterocyclic rings, e.g. rifampin, thiothixene or sparfloxacin
-
- 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
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
Definitions
- the present invention provides amorphous lurasidone hydrochloride, processes for its preparation, pharmaceutical composition comprising it and its use for the treatment of schizophrenia.
- Lurasidone hydrochloride is chemically (3aR,4S,7R,7aS)-2- ⁇ (lR,2R)-2-[4-(l,2- benzisothiazol-3-yl)piperazin-l-ylmethyl]cyclohexylmethyl ⁇ hexahydro-4,7-methano-2H- isoindole-l,3-dione hydrochloride, having the structure as represented by Formula I, and is known from U.S. Patent No. 5,532,372.
- the present invention provides amorphous lurasidone hydrochloride, a process for its preparation, pharmaceutical compositions comprising it and its use for the treatment of schizophrenia.
- Amorphous lurasidone hydrochloride of the present invention is a highly pure, easy to filter, free-flowing solid having small average particle size.
- Amorphous lurasidone hydrochloride of the present invention is stable in terms of polymorphic conversion, has reproducible dissolution profile and has good bioavailability.
- a first aspect of the present invention provides amorphous lurasidone
- a second aspect of the present invention provides a process for the preparation of amorphous lurasidone hydrochloride comprising subjecting a reaction mixture containing lurasidone hydrochloride to agitated thin film drying.
- a third aspect of the present invention provides a process for the preparation of amorphous lurasidone hydrochloride comprising concentrating a reaction mixture containing lurasidone hydrochloride in a solvent under reduced pressure.
- a fourth aspect of the present invention provides a process for the preparation of amorphous lurasidone hydrochloride comprising subjecting a solution of lurasidone hydrochloride in a solvent to spray drying.
- a fifth aspect of the present invention provides a process for the preparation of amorphous lurasidone hydrochloride comprising subjecting a solution of lurasidone hydrochloride in a solvent to lyophilization.
- a sixth aspect of the present invention provides a pharmaceutical composition
- a pharmaceutical composition comprising amorphous lurasidone hydrochloride and one or more pharmaceutically acceptable carriers, diluents or excipients.
- a seventh aspect of the present invention provides use of amorphous lurasidone hydrochloride for the treatment of schizophrenia.
- Figure 1 X-ray Diffraction (XRD) spectrum of amorphous lurasidone
- Figure 2 Infra-red (IR) spectrum of amorphous lurasidone hydrochloride.
- FIG. 3 Differential Scanning thermogram (DSC) of amorphous lurasidone hydrochloride.
- Amorphous lurasidone hydrochloride of the present invention may be
- Amorphous lurasidone hydrochloride of the present invention may be prepared by contacting lurasidone hydrochloride with a solvent at ambient temperature and subjecting the resulting solution to agitated thin-film drying technique.
- Amorphous lurasidone hydrochloride may also be prepared by concentrating a reaction mixture of lurasidone hydrochloride in a solvent under reduced pressure. It may also be prepared by spray drying, lyophilization or by solvent-antisolvent treatment.
- contacting refers to dissolving, slurrying, stirring, or a combination thereof.
- ambient temperature refers to a temperature in the range of about 20°C to 30°C.
- the solvent to be used for the preparation of amorphous lurasidone hydrochloride of the present invention may be selected from alcohols, ketones, chlorinated hydrocarbons or ethers.
- alcohols include methanol or ethanol.
- ketones include acetone, methyl ethyl ketone or methyl isobutyl ketone.
- chlorinated hydrocarbons include dichloromethane or chloroform.
- ethers include tetrahydrofuran or diethyl ether.
- chlorinated hydrocarbon is used as the solvent.
- amorphous lurasidone hydrochloride may be prepared by an agitated thin film drying process comprising feeding a solution of lurasidone hydrochloride in a chlorinated solvent to vacuum rotary evaporator followed by suction at ambient temperature to about 100°C under reduced pressure.
- amorphous lurasidone hydrochloride may be prepared by concentrating a solution of lurasidone hydrochloride in a chlorinated solvent under reduced pressure at ambient temperature to about 100°C.
- amorphous lurasidone hydrochloride may be prepared by spray drying a solution of lurasidone hydrochloride in a chlorinated solvent under reduced pressure at ambient temperature.
- the solution of lurasidone hydrochloride in chlorinated solvent may be charged to a spray dryer supplied with nitrogen gas at a feed pump rate of about 3 mL/minute.
- the inlet temperature may be maintained at about 70°C to 80°C and the outlet temperature may be maintained at about 65°C to 75°C.
- Amorphous lurasidone hydrochloride may be dried using any suitable method such as drying under reduced pressure, drying under atmospheric pressure, air drying or drying with aeration of inert gas such as nitrogen. Preferably, drying may be carried out at ambient temperature to about 80°C under reduced pressure.
- Amorphous lurasidone hydrochloride of the present invention has an HPLC purity greater than 98%.
- Amorphous lurasidone hydrochloride of the present invention may be administered as part of a pharmaceutical composition for the treatment of schizophrenia. Accordingly, in a further aspect, there is provided a pharmaceutical composition that comprises amorphous lurasidone hydrochloride and one or more pharmaceutically acceptable carriers, diluents or excipients and optionally other therapeutic ingredients.
- the amorphous lurasidone hydrochloride of the present invention may conventionally be formulated into tablets, capsules, suspensions, dispersions, injectables and other pharmaceutical forms. Any suitable route of administration may be employed, for example, peroral or parental.
- X-ray diffraction patterns were recorded using Panalytical Expert PRO with Xcelerator as detector, 3-40 as scan range, 0.02 as step size and 3-40° 2 ⁇ as range.
- IR spectrum was recorded using Perkin Elmer Spectrum one FT-IR spectrometer. HPLC purity was determined by using a YMC Pack ODS-AM(250x4.6)mm ⁇ m column with a flow rate: 1.5 mL/minute; column oven temperature: 45°C; Detector: UV at 230nm; Injection volume: 10 ⁇ ; Run time: 37 minutes using buffer and acetonitrile as diluent and lmL ortho-phosphoric acid + 100 mL water as buffer.
- Spray drying was carried out using a BUCHI mini spray dryer B-290 fitted with a fluid pressure nozzle of diameter: 0.7 mm using the parameters: Carrier gas: Nitrogen at 40 mmHg; Air inlet temperature: about 70°C to about 80°C; Outlet temperature: about 65°C to about 75°C; Aspiration: 70%.
- Lurasidone hydrochloride (1 g) was dissolved in dichloromethane (50 mL) at ambient temperature. The solution was fed into vacuum rotary evaporator and subjected to agitated thin-film drying technique at about 70°C to 80°C to obtain a solid. The solid was dried at about 45°C under reduced pressure to obtain amorphous lurasidone hydrochloride.
- Lurasidone hydrochloride (0.5 g) was dissolved in dichloromethane (20 mL) at ambient temperature. The solution was concentrated under reduced pressure at an oil bath temperature of about 70°C to 80°C. The solid material was dried at about 45°C under reduced pressure to obtain amorphous lurasidone hydrochloride.
- Lurasidone hydrochloride (3.5 g) was dissolved in dichloromethane (150 mL) at ambient temperature. The solution was charged to a spray dryer at feed pump rate of about 3 mL/minute. The solid was dried at about 45°C under reduced pressure to obtain amorphous lurasidone hydrochloride.
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- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
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- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Psychiatry (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The present invention provides amorphous lurasidone hydrochloride, processes for its preparation, pharmaceutical composition comprising it and its use for the treatment of schizophrenia.
Description
AMORPHOUS LURASIDONE HYDROCHLORIDE
Field of the Invention
The present invention provides amorphous lurasidone hydrochloride, processes for its preparation, pharmaceutical composition comprising it and its use for the treatment of schizophrenia.
Background of the Invention
Lurasidone hydrochloride is chemically (3aR,4S,7R,7aS)-2-{(lR,2R)-2-[4-(l,2- benzisothiazol-3-yl)piperazin-l-ylmethyl]cyclohexylmethyl}hexahydro-4,7-methano-2H- isoindole-l,3-dione hydrochloride, having the structure as represented by Formula I, and is known from U.S. Patent No. 5,532,372.
Formula I
U.S. Patent No. 7,605,260 describes the preparation of lurasidone hydrochloride.
Summary of the Invention
The present invention provides amorphous lurasidone hydrochloride, a process for its preparation, pharmaceutical compositions comprising it and its use for the treatment of schizophrenia. Amorphous lurasidone hydrochloride of the present invention is a highly pure, easy to filter, free-flowing solid having small average particle size. Amorphous lurasidone hydrochloride of the present invention is stable in terms of polymorphic conversion, has reproducible dissolution profile and has good bioavailability.
A first aspect of the present invention provides amorphous lurasidone
hydrochloride.
A second aspect of the present invention provides a process for the preparation of amorphous lurasidone hydrochloride comprising subjecting a reaction mixture containing lurasidone hydrochloride to agitated thin film drying.
A third aspect of the present invention provides a process for the preparation of amorphous lurasidone hydrochloride comprising concentrating a reaction mixture containing lurasidone hydrochloride in a solvent under reduced pressure.
A fourth aspect of the present invention provides a process for the preparation of amorphous lurasidone hydrochloride comprising subjecting a solution of lurasidone hydrochloride in a solvent to spray drying.
A fifth aspect of the present invention provides a process for the preparation of amorphous lurasidone hydrochloride comprising subjecting a solution of lurasidone hydrochloride in a solvent to lyophilization.
A sixth aspect of the present invention provides a pharmaceutical composition comprising amorphous lurasidone hydrochloride and one or more pharmaceutically acceptable carriers, diluents or excipients.
A seventh aspect of the present invention provides use of amorphous lurasidone hydrochloride for the treatment of schizophrenia.
Brief Description of the Figures
Figure 1 : X-ray Diffraction (XRD) spectrum of amorphous lurasidone
hydrochloride.
Figure 2: Infra-red (IR) spectrum of amorphous lurasidone hydrochloride.
Figure 3: Differential Scanning thermogram (DSC) of amorphous lurasidone hydrochloride.
Figure 4: Thermogravimetric Analysis (TGA) of amorphous lurasidone
hydrochloride.
Detailed Description of the Invention
Various embodiments and variants of the present invention are described below.
Amorphous lurasidone hydrochloride of the present invention may be
characterized by the X-ray diffraction pattern as depicted in Figure 1. It may also be characterized by Infra-red spectrum as depicted in Figure 2. It may also be characterized by differential scanning thermogram as depicted in Figure 3. It may also be characterized by thermogravimetric analysis as depicted in Figure 4.
Amorphous lurasidone hydrochloride of the present invention may be prepared by contacting lurasidone hydrochloride with a solvent at ambient temperature and subjecting the resulting solution to agitated thin-film drying technique. Amorphous lurasidone hydrochloride may also be prepared by concentrating a reaction mixture of lurasidone hydrochloride in a solvent under reduced pressure. It may also be prepared by spray drying, lyophilization or by solvent-antisolvent treatment.
The term "contacting" as used herein, refers to dissolving, slurrying, stirring, or a combination thereof.
The term "ambient temperature", refers to a temperature in the range of about 20°C to 30°C.
The solvent to be used for the preparation of amorphous lurasidone hydrochloride of the present invention may be selected from alcohols, ketones, chlorinated hydrocarbons or ethers. Examples of alcohols include methanol or ethanol. Examples of ketones include acetone, methyl ethyl ketone or methyl isobutyl ketone. Examples of chlorinated hydrocarbons include dichloromethane or chloroform. Examples of ethers include tetrahydrofuran or diethyl ether. In a preferred embodiment of the present invention, chlorinated hydrocarbon is used as the solvent.
In one embodiment of the present invention, amorphous lurasidone hydrochloride may be prepared by an agitated thin film drying process comprising feeding a solution of lurasidone hydrochloride in a chlorinated solvent to vacuum rotary evaporator followed by suction at ambient temperature to about 100°C under reduced pressure.
In another embodiment of the present invention, amorphous lurasidone hydrochloride may be prepared by concentrating a solution of lurasidone hydrochloride in a chlorinated solvent under reduced pressure at ambient temperature to about 100°C.
In yet another embodiment of the present invention, amorphous lurasidone hydrochloride may be prepared by spray drying a solution of lurasidone hydrochloride in a chlorinated solvent under reduced pressure at ambient temperature. The solution of lurasidone hydrochloride in chlorinated solvent may be charged to a spray dryer supplied with nitrogen gas at a feed pump rate of about 3 mL/minute. The inlet temperature may be maintained at about 70°C to 80°C and the outlet temperature may be maintained at about 65°C to 75°C.
Amorphous lurasidone hydrochloride may be dried using any suitable method such as drying under reduced pressure, drying under atmospheric pressure, air drying or drying with aeration of inert gas such as nitrogen. Preferably, drying may be carried out at ambient temperature to about 80°C under reduced pressure.
Amorphous lurasidone hydrochloride of the present invention has an HPLC purity greater than 98%.
Amorphous lurasidone hydrochloride of the present invention may be administered as part of a pharmaceutical composition for the treatment of schizophrenia. Accordingly, in a further aspect, there is provided a pharmaceutical composition that comprises amorphous lurasidone hydrochloride and one or more pharmaceutically acceptable carriers, diluents or excipients and optionally other therapeutic ingredients. The amorphous lurasidone hydrochloride of the present invention may conventionally be formulated into tablets, capsules, suspensions, dispersions, injectables and other pharmaceutical forms. Any suitable route of administration may be employed, for example, peroral or parental.
In the foregoing section, embodiments are described by way of examples to illustrate the processes of invention. However, these are not intended in any way to limit the scope of the present invention. Several variants of the examples would be evident to persons ordinarily skilled in the art which are within the scope of the present invention.
Methods
X-ray diffraction patterns were recorded using Panalytical Expert PRO with Xcelerator as detector, 3-40 as scan range, 0.02 as step size and 3-40° 2Θ as range.
IR spectrum was recorded using Perkin Elmer Spectrum one FT-IR spectrometer.
HPLC purity was determined by using a YMC Pack ODS-AM(250x4.6)mm^m column with a flow rate: 1.5 mL/minute; column oven temperature: 45°C; Detector: UV at 230nm; Injection volume: 10 μί; Run time: 37 minutes using buffer and acetonitrile as diluent and lmL ortho-phosphoric acid + 100 mL water as buffer.
Spray drying was carried out using a BUCHI mini spray dryer B-290 fitted with a fluid pressure nozzle of diameter: 0.7 mm using the parameters: Carrier gas: Nitrogen at 40 mmHg; Air inlet temperature: about 70°C to about 80°C; Outlet temperature: about 65°C to about 75°C; Aspiration: 70%.
EXAMPLES
Example 1 :
Lurasidone hydrochloride (1 g) was dissolved in dichloromethane (50 mL) at ambient temperature. The solution was fed into vacuum rotary evaporator and subjected to agitated thin-film drying technique at about 70°C to 80°C to obtain a solid. The solid was dried at about 45°C under reduced pressure to obtain amorphous lurasidone hydrochloride.
Yield: 70%
HPLC Purity: 98.62%
Example 2:
Lurasidone hydrochloride (0.5 g) was dissolved in dichloromethane (20 mL) at ambient temperature. The solution was concentrated under reduced pressure at an oil bath temperature of about 70°C to 80°C. The solid material was dried at about 45°C under reduced pressure to obtain amorphous lurasidone hydrochloride.
Yield: 80%
HPLC Purity: 98.66%
Example 3 :
Lurasidone hydrochloride (3.5 g) was dissolved in dichloromethane (150 mL) at ambient temperature. The solution was charged to a spray dryer at feed pump rate of
about 3 mL/minute. The solid was dried at about 45°C under reduced pressure to obtain amorphous lurasidone hydrochloride.
Yield: 42.85%
Claims
1. Amorphous lurasidone hydrochloride.
2. Amorphous lurasidone hydrochloride according to claim 1 characterized by X-ray diffraction pattern as depicted in Figure 1.
3. Amorphous lurasidone hydrochloride according to claim 1 characterized by Infra- red spectrum as depicted in Figure 2.
4. Amorphous lurasidone hydrochloride according to claim 1 characterized by differential scanning thermogram as depicted in Figure 3.
5. Amorphous lurasidone hydrochloride according to claim 1 characterized by thermogravimetric analysis as depicted in Figure 4.
6. A process for preparation of amorphous lurasidone hydrochloride comprising subjecting a reaction mixture containing lurasidone hydrochloride in a solvent to agitated thin film drying.
7. The process according to claim 6, wherein the solvent is selected from the group comprising of alcohols, ketones, chlorinated hydrocarbons and ethers.
8. The process according to claim 6, wherein the solvent is dichloromethane.
9. The process according to claim 6, wherein agitated thin-film drying is carried out at about 80°C.
10. A process for preparation of amorphous lurasidone hydrochloride comprising concentrating a reaction mixture of lurasidone hydrochloride in a solvent under reduced pressure.
11. The process according to claim 10, wherein the solvent is selected from the group comprising of alcohols, ketones, chlorinated hydrocarbons and ethers.
12. The process according to claim 10, wherein the solvent is dichloromethane.
13. The process according to claim 10, wherein the reaction mixture is concentrated at about 80°C under reduced pressure.
14. A process for preparation of amorphous lurasidone hydrochloride comprising subjecting a solution of lurasidone hydrochloride in a solvent to spray drying.
15. The process according to claim 14, wherein the solvent is selected from the group consisting of alcohols, ketones, chlorinated hydrocarbons and ethers.
16. The process according to claim 14, wherein the solvent is dichloromethane.
17. The process according to claim 14, wherein inlet temperature of the spray dryer is about 80°C and outlet temperature is about 75°C.
18. The process according to claim 14, wherein solution of lurasidone hydrochloride is charged to a spray dryer at feed pump rate of about 3 mL/minute.
19. A process for preparation of amorphous lurasidone hydrochloride comprising subjecting a solution of lurasidone hydrochloride in a solvent to lyophilization.
20. Pharmaceutical composition comprising amorphous lurasidone hydrochloride and one or more pharmaceutically acceptable carriers, diluents or excipients.
21. Use of amorphous lurasidone hydrochloride for treatment of schizophrenia.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IN699/DEL/2011 | 2011-03-14 | ||
| IN699DE2011 | 2011-03-14 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO2012123858A1 true WO2012123858A1 (en) | 2012-09-20 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/IB2012/051073 Ceased WO2012123858A1 (en) | 2011-03-14 | 2012-03-07 | Amorphous lurasidone hydrochloride |
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| WO (1) | WO2012123858A1 (en) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2013121440A1 (en) | 2012-02-13 | 2013-08-22 | Cadila Healthcare Limited | Process for preparing benzisothiazol-3-yl-peperazin-l-yl-methyl-cyclo hexyl-methanisoindol-1,3-dione and its intermediates |
| CN104059061A (en) * | 2014-07-04 | 2014-09-24 | 中国药科大学 | Co-amorphous substance of indissolvable drug |
| WO2014076712A3 (en) * | 2012-11-14 | 2015-03-12 | Hetero Research Foundation | Lurasidone hydrochloride solid dispersion |
| CN106512011A (en) * | 2016-11-04 | 2017-03-22 | 中国药科大学 | A method of slowly releasing a medicine |
| US9790237B2 (en) | 2014-06-16 | 2017-10-17 | Johnson Matthey Public Limited Company | Processes for making alkylated arylpiperazine and alkylated arylpiperidine compounds including novel intermediates |
| CN111978315A (en) * | 2020-09-02 | 2020-11-24 | 中国药科大学 | Lurasidone hydrochloride tryptophan/L-proline co-amorphous substance and preparation method and application thereof |
| CN113024535A (en) * | 2019-12-24 | 2021-06-25 | 上海科胜药物研发有限公司 | Preparation method of lurasidone hydrochloride |
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| US5532372A (en) | 1990-07-06 | 1996-07-02 | Sumitomo Pharmaceuticals Company, Ltd. | Imide derivatives, and their production and use |
| EP1652848A1 (en) * | 2003-07-29 | 2006-05-03 | Dainippon Sumitomo Pharma Co., Ltd. | Process for producing imide compound |
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2012
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| US5532372A (en) | 1990-07-06 | 1996-07-02 | Sumitomo Pharmaceuticals Company, Ltd. | Imide derivatives, and their production and use |
| EP1652848A1 (en) * | 2003-07-29 | 2006-05-03 | Dainippon Sumitomo Pharma Co., Ltd. | Process for producing imide compound |
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Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2013121440A1 (en) | 2012-02-13 | 2013-08-22 | Cadila Healthcare Limited | Process for preparing benzisothiazol-3-yl-peperazin-l-yl-methyl-cyclo hexyl-methanisoindol-1,3-dione and its intermediates |
| US9409899B2 (en) | 2012-02-13 | 2016-08-09 | Cadila Healthcare Limited | Process for preparing benzisothiazol-3-yl-piperazin-1-yl-methyl-cyclo hexylmethanisoindol-1,3-dione and its intermediates |
| WO2014076712A3 (en) * | 2012-11-14 | 2015-03-12 | Hetero Research Foundation | Lurasidone hydrochloride solid dispersion |
| US9790237B2 (en) | 2014-06-16 | 2017-10-17 | Johnson Matthey Public Limited Company | Processes for making alkylated arylpiperazine and alkylated arylpiperidine compounds including novel intermediates |
| US9957283B1 (en) | 2014-06-16 | 2018-05-01 | Johnson Matthey Public Limited Company | Processes for making alkylated arylpiperazine and alkylated arylpiperidine compounds including novel intermediates |
| CN104059061A (en) * | 2014-07-04 | 2014-09-24 | 中国药科大学 | Co-amorphous substance of indissolvable drug |
| CN106512011A (en) * | 2016-11-04 | 2017-03-22 | 中国药科大学 | A method of slowly releasing a medicine |
| CN113024535A (en) * | 2019-12-24 | 2021-06-25 | 上海科胜药物研发有限公司 | Preparation method of lurasidone hydrochloride |
| CN114728952A (en) * | 2019-12-24 | 2022-07-08 | 浙江华海药业股份有限公司 | A kind of preparation method of lurasidone hydrochloride |
| US12304906B2 (en) | 2019-12-24 | 2025-05-20 | Zhejiang Huahai Pharmaceutical Co., Ltd. | Method for preparing lurasidone hydrochloride |
| CN111978315A (en) * | 2020-09-02 | 2020-11-24 | 中国药科大学 | Lurasidone hydrochloride tryptophan/L-proline co-amorphous substance and preparation method and application thereof |
| CN111978315B (en) * | 2020-09-02 | 2023-03-24 | 中国药科大学 | Lurasidone hydrochloride tryptophan/L-proline co-amorphous substance and preparation method and application thereof |
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