WO2022044040A1 - Novel polymorphs of (s)-3-(1-(9h-purin-6-yl-amino)ethyl)-8-chloro-2-phenylisoquinolin-1(2h)-one - Google Patents

Novel polymorphs of (s)-3-(1-(9h-purin-6-yl-amino)ethyl)-8-chloro-2-phenylisoquinolin-1(2h)-one Download PDF

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WO2022044040A1
WO2022044040A1 PCT/IN2021/050816 IN2021050816W WO2022044040A1 WO 2022044040 A1 WO2022044040 A1 WO 2022044040A1 IN 2021050816 W IN2021050816 W IN 2021050816W WO 2022044040 A1 WO2022044040 A1 WO 2022044040A1
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duvelisib
crystalline form
formula
ethyl
chloro
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PCT/IN2021/050816
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French (fr)
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WO2022044040A8 (en
Inventor
Thirumalai Rajan Srinivasan
Eswaraiah Sajja
Vijayavitthal T MATHAD
Venkata Narasayya SALADI
Bal Raju Kammari
Pratap Reddy MANDAD
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Msn Laboratories Private Limited, R&D Center
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Publication of WO2022044040A1 publication Critical patent/WO2022044040A1/en
Publication of WO2022044040A8 publication Critical patent/WO2022044040A8/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D473/00—Heterocyclic compounds containing purine ring systems
    • C07D473/26—Heterocyclic compounds containing purine ring systems with an oxygen, sulphur, or nitrogen atom directly attached in position 2 or 6, but not in both
    • C07D473/32—Nitrogen atom
    • C07D473/34—Nitrogen atom attached in position 6, e.g. adenine

Definitions

  • the present invention relates novel crystalline forms of (S)-3-(l-(9H-purin-6-yl- amino)ethyl)-8-chloro-2-phenylisoquinolin-l(2H)-one compound of formula- 1 and its process for preparation thereof.
  • Duvelisib is chemically known as (S)-3-(l-(9H-purin-6-ylamino)ethyl)-8-chloro-2- phenylisoquinolin-l(2H)-one compound of formula- 1.
  • Duvelisib was developed by Intellikine and Infinity pharma. It is used to treat chronic lymphocytic leukemia (CLL) or small lymphocytic lymphoma (SLL) after other treatments have failed. It was approved by USFDA in September 2018.
  • CLL chronic lymphocytic leukemia
  • SLL small lymphocytic lymphoma
  • Polymorphism is the occurrence of different crystalline forms of a single compound and it is a property of some compounds and complexes. Thus, polymorphs are distinct solids sharing the same molecular formula, yet each polymorph may have distinct physical properties. Therefore, a single compound may give rise to a variety of polymorphic forms where each form has different and distinct physical properties, such as different solubility profiles, different melting point temperatures and/or different x-ray diffraction peaks. Since the solubility of each polymorph may vary, identifying the existence of pharmaceutical polymorphs is essential for providing pharmaceuticals with predicable solubility profiles. It is desirable to investigate all solid state forms of a drug, including all polymorphic forms, and to determine the stability, dissolution and flow properties of each polymorphic form.
  • Polymorphic forms of a compound can be distinguished in a laboratory by X-ray diffraction spectroscopy and by other methods such as, infrared spectrometry. Additionally, polymorphic forms of the same drug substance or active pharmaceutical ingredient, can be administered by itself or formulated as a drug product (also known as the final or finished dosage form), and are well known in the pharmaceutical art to affect, for example, the solubility, stability, flowability, tractability and compressibility of drug substances and the safety and efficacy of drug products.
  • the present invention provides novel crystalline form of Duvelisib of formula- 1, which is herein after designated as Form-M and process for the preparation thereof.
  • the present invention also provides novel crystalline form of Duvelisib of formula- 1, which is herein after designated as Form-S and process for the preparation thereof.
  • Figure-1 Illustrates the PXRD pattern of crystalline Form-M of Duvelisib.
  • Figure-2 Illustrates the PXRD pattern of crystalline Form-S of Duvelisib.
  • suitable solvent refers to “hydrocarbon solvents” such as n-hexane, n-heptane, cyclohexane, pet ether, toluene, pentane, cycloheptane, methyl cyclohexane, m-, o-, or p-xylene, nitro methane and the like; “ether solvents” such as dimethoxy methane, tetrahydrofuran, 1,3 -dioxane, 1,4-dioxane, furan, diethyl ether, ethylene glycol dimethyl ether, ethylene glycol diethyl ether, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, triethylene glycol dimethyl ether, anisole, methyl t-butyl ether, 1,2-dimethoxy ethane, anisole and the like; “ester solvents” such as methyl
  • Ambient condition refers to temperature at 25-30°C and atmospheric pressure.
  • the first embodiment of the present invention provides a novel crystalline Form-S of Duvelisib of formula- 1.
  • the first aspect of the first embodiment provides crystalline Form-S of Duvelisib of formula- 1, which characterized by its X-ray powder diffraction (XRD) pattern having peaks at about 10.7 and 21.5 ⁇ 0.2 degrees 2-theta.
  • XRD X-ray powder diffraction
  • the second aspect of the first embodiment provides crystalline Form-S of Duvelisib of formula- 1, is further characterized by its X-ray powder diffraction (XRD) pattern having peaks at about 8.7, 17.1, 17.5 and 13.9 ⁇ 0.2 degrees 2-theta.
  • XRD X-ray powder diffraction
  • the third aspect of the first embodiment provides crystalline Form-S of Duvelisib of formula- 1 characterized by its powder X-Ray diffraction (XRD) pattern as illustrated in figure-2.
  • XRD powder X-Ray diffraction
  • the fourth aspect of the first embodiment of the present invention provides a process for the preparation of crystalline Form-S of Duvelisib of formula-1, comprising: a) providing a solution of Duvelisib of formula- 1 in a solvent, b) adding the solution of step-a) to anti-solvent, c) filtering the compound obtained in step-b), and d) drying the compound obtained in step-c) to provide crystalline Form-S of Duvelisib of formula- 1.
  • the compound obtained in step-c) is crystalline form of Duvelisib which is hereinafter referred to as Form-M.
  • the fifth aspect of the first embodiment provides crystalline Form-M of Duvelisib of formula- 1 characterized by its powder X-Ray diffraction (XRD) pattern as illustrated in figure- 1.
  • XRD powder X-Ray diffraction
  • dissolving Duvelisib in a solvent comprising in a suitable solvent selected from alcohol solvents, ester solvents, polar aprotic solvents, ketone solvents, ether solvents, nitrile solvents and water or mixtures thereof.
  • the mixture in step-a) can be optionally heated to a temperature of about 30°C or about 40°C or about 50°C or about 60°C or about 80°C or about 100°C or any other suitable temperature to provide a solution.
  • the anti-solvent used in step-b) is xylene.
  • the crystalline Form-S of Duvelisib is stable for several months. For example, it is stable at least for 10 months when stored at ambient condition, therefore, the said crystalline Form-S of Duvelisib is storage stable.
  • the crystalline Form-S of Duvelisib produced according to the present invention may be dried in suitable drying equipment such as tray dryer, vacuum oven, rotatory cone dryer, air oven, fluidized bed dryer, spin flash dryer, flash dryer, or the like.
  • suitable drying equipment such as tray dryer, vacuum oven, rotatory cone dryer, air oven, fluidized bed dryer, spin flash dryer, flash dryer, or the like.
  • the drying may be carried out at atmospheric pressure or under reduced pressure at temperature of less than about 100°C, less than about 60°C, less than about 40°C, or any other suitable temperature.
  • the drying may be carried out for any time period required for obtaining a desired quality, such as from about 15 minutes to 10 hours or longer.
  • Crystalline Form-S of Duvelisib of formula- 1 produced by the process of the present invention can be further micronized or milled to get desired particle size to achieve desired solubility profile based on different forms of pharmaceutical composition requirements.
  • Techniques that can be used for particle size reduction include but not limited to single or multi-stage micronization using cutting mills, pin/cage mills, hammer mills, jet mills, fluidized bed jet mills, ball mills and roller mills. Milling or micronization can be performed before drying or after drying of the product.
  • Crystalline Form-S of Duvelisib obtained according to the present invention has particle sizes of less than about 250 pm or less than about 150 pm or less than about 100 pm or less than about 50 pm, or less than about 40 pm or less than about 30 pm or less than about 20 pm or less than about 10 pm or less than about 5 pm
  • the present invention provides pharmaceutical composition comprising crystalline Form-S of Duvelisib and one or more pharmaceutically acceptable excipients.
  • the excipient can be selected from Excipient Development for Pharmaceutical, Biotechnology, and Drug Delivery Systems 2006.
  • composition comprising crystalline Form- S of Duvelisib and one or more pharmaceutically acceptable excipients is formulated in a manner suitable for the route of administration to be used.
  • pharmaceutical compositions include tablets, pills, powders, liquids, suspensions, emulsions, granules, capsules, suppositories, or injection preparations.
  • the present invention provides crystalline Form-S of Duvelisib prepared according to the present invention having purity of about 99.9%; preferably about 99.95%; more preferably about 99.97% as measured by HPLC.
  • the starting material Duvelisib or its monohydrate used in the present invention can be prepared from any of the processes known in the art.
  • the invention also encompasses pharmaceutical compositions comprising crystalline Form-S of Duvelisib of formula- 1 of the present invention.
  • pharmaceutical compositions or “pharmaceutical formulations” include tablets, pills, powders, liquids, suspensions, emulsions, granules, capsules, suppositories, or injection preparations.
  • P-XRD Method of Analysis PXRD analysis of compound of formula- 1 is carried out by using BRUKER/D8 ADVANCE diffractometer using Cu Ka radiation of wavelength 1.5406 A 0 and continuous scan speed of 0.03°/min.
  • Example-1 Preparation of crystalline Form-M of Duvelisib
  • Dimethylformamide (0.2 ml) was added to Duvelisib (0.5 gms) at 25-30°C and stirred for 15 minutes at the same temperature.
  • the mixture was added to xylene (10 ml) at 25-30°C and stirred for 10 minutes at the same temperature. Filtered the solid, washed with xylene and suck dried.
  • Example-2 Preparation of crystalline Form-S of Duvelisib
  • Dimethylformamide (0.2 ml) was added to Duvelisib monohydrate (0.5 gms) at 25- 30°C and stirred for 15 minutes at the same temperature.
  • the mixture was added to xylene (10 ml) at 25-30°C and stirred for 10 minutes at the same temperature. Filtered the solid, washed with xylene and suck dried.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

The present invention relates novel crystalline forms of (S)-3-(1-(9H-purin-6-yl-amino)ethyl)-8-chloro-2-phenylisoquinolin-1(2H)-one compound of formula-1 and its process for preparation thereof. Formula-1 The present invention provides novel crystalline form of Duvelisib of formula-1, which is herein after designated as Form-M and process for the preparation thereof. The present invention also provides novel crystalline form of Duvelisib of formula-1, which is herein after designated as Form-S and process for the preparation thereof.

Description

Novel polymorphs of (S)-3-(l-(9H-purin-6-yl-amino)ethyl)-8-chloro-2-phenyl isoquinolin- l(2H)-one
Related Application:
This application claims the benefit of priority of our Indian patent application number 202041036475 filed on 25th August 2020 which is incorporated herein by reference.
Field of the invention:
The present invention relates novel crystalline forms of (S)-3-(l-(9H-purin-6-yl- amino)ethyl)-8-chloro-2-phenylisoquinolin-l(2H)-one compound of formula- 1 and its process for preparation thereof.
Figure imgf000003_0001
Formula- 1
Background of the invention:
Duvelisib is chemically known as (S)-3-(l-(9H-purin-6-ylamino)ethyl)-8-chloro-2- phenylisoquinolin-l(2H)-one compound of formula- 1.
Duvelisib was developed by Intellikine and Infinity pharma. It is used to treat chronic lymphocytic leukemia (CLL) or small lymphocytic lymphoma (SLL) after other treatments have failed. It was approved by USFDA in September 2018.
(S)-3-(l-(9H-purin-6-ylamino)ethyl)-8-chloro-2-phenylisoquinolin-l(2H)-one hydrate was first disclosed in US8193182 B2.
Polymorphism is the occurrence of different crystalline forms of a single compound and it is a property of some compounds and complexes. Thus, polymorphs are distinct solids sharing the same molecular formula, yet each polymorph may have distinct physical properties. Therefore, a single compound may give rise to a variety of polymorphic forms where each form has different and distinct physical properties, such as different solubility profiles, different melting point temperatures and/or different x-ray diffraction peaks. Since the solubility of each polymorph may vary, identifying the existence of pharmaceutical polymorphs is essential for providing pharmaceuticals with predicable solubility profiles. It is desirable to investigate all solid state forms of a drug, including all polymorphic forms, and to determine the stability, dissolution and flow properties of each polymorphic form.
Polymorphic forms of a compound can be distinguished in a laboratory by X-ray diffraction spectroscopy and by other methods such as, infrared spectrometry. Additionally, polymorphic forms of the same drug substance or active pharmaceutical ingredient, can be administered by itself or formulated as a drug product (also known as the final or finished dosage form), and are well known in the pharmaceutical art to affect, for example, the solubility, stability, flowability, tractability and compressibility of drug substances and the safety and efficacy of drug products.
Brief description of the invention:
The present invention provides novel crystalline form of Duvelisib of formula- 1, which is herein after designated as Form-M and process for the preparation thereof.
The present invention also provides novel crystalline form of Duvelisib of formula- 1, which is herein after designated as Form-S and process for the preparation thereof.
Brief description of the Drawings:
Figure-1: Illustrates the PXRD pattern of crystalline Form-M of Duvelisib.
Figure-2: Illustrates the PXRD pattern of crystalline Form-S of Duvelisib.
Detailed description of the invention:
As used herein the term “suitable solvent” used in the present invention refers to “hydrocarbon solvents” such as n-hexane, n-heptane, cyclohexane, pet ether, toluene, pentane, cycloheptane, methyl cyclohexane, m-, o-, or p-xylene, nitro methane and the like; “ether solvents” such as dimethoxy methane, tetrahydrofuran, 1,3 -dioxane, 1,4-dioxane, furan, diethyl ether, ethylene glycol dimethyl ether, ethylene glycol diethyl ether, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, triethylene glycol dimethyl ether, anisole, methyl t-butyl ether, 1,2-dimethoxy ethane, anisole and the like; “ester solvents” such as methyl formate, methyl acetate, ethyl acetate, isopropyl acetate, n-butyl acetate, isobutyl acetate, vinyl acetate and the like; “polar-aprotic solvents such as dimethyl acetamide (DMA), dimethylformamide (DMF), dimethylsulfoxide (DMSO), N-methyl pyrrolidone (NMP) and the like; “chloro solvents” such as dichloromethane, dichloroethane, chloroform, carbon tetrachloride and the like; “ketone solvents” such as acetone, methyl ethyl ketone, acetyl acetone, methyl isobutyl ketone and the like; “nitrile solvents” such as acetonitrile, propionitrile, isobutyronitrile and the like; “alcoholic solvents” such as methanol, ethanol, n-propanol, isopropanol, n-butanol, isobutanol, t-butanol, 2-nitroethanol, 2- fluoroethanol, 2,2,2-trifluoroethanol, ethylene glycol, polyethylene glycol, polyethylene glycol-400, 2-methoxyethanol, 1,2-ethoxyethanol, diethylene glycol, 1, 2, or 3-pentanol, neopentyl alcohol, t-pentyl alcohol, diethylene glycol monoethylether, cyclohexanol, benzyl alcohol, phenol, or glycerol and the like; “polar solvents” such as water and or mixtures thereof.
As used herein the term “Ambient condition” refers to temperature at 25-30°C and atmospheric pressure.
The first embodiment of the present invention provides a novel crystalline Form-S of Duvelisib of formula- 1.
The first aspect of the first embodiment provides crystalline Form-S of Duvelisib of formula- 1, which characterized by its X-ray powder diffraction (XRD) pattern having peaks at about 10.7 and 21.5 ± 0.2 degrees 2-theta.
The second aspect of the first embodiment provides crystalline Form-S of Duvelisib of formula- 1, is further characterized by its X-ray powder diffraction (XRD) pattern having peaks at about 8.7, 17.1, 17.5 and 13.9 ± 0.2 degrees 2-theta.
The third aspect of the first embodiment provides crystalline Form-S of Duvelisib of formula- 1 characterized by its powder X-Ray diffraction (XRD) pattern as illustrated in figure-2.
The fourth aspect of the first embodiment of the present invention provides a process for the preparation of crystalline Form-S of Duvelisib of formula-1, comprising: a) providing a solution of Duvelisib of formula- 1 in a solvent, b) adding the solution of step-a) to anti-solvent, c) filtering the compound obtained in step-b), and d) drying the compound obtained in step-c) to provide crystalline Form-S of Duvelisib of formula- 1.
The fourth aspect of the first embodiment, the compound obtained in step-c) is crystalline form of Duvelisib which is hereinafter referred to as Form-M.
The fifth aspect of the first embodiment provides crystalline Form-M of Duvelisib of formula- 1 characterized by its powder X-Ray diffraction (XRD) pattern as illustrated in figure- 1.
In an aspect providing a solution of Duvelisib by contacting Duvelisib with a suitable solvent, comprising dissolving Duvelisib in dimethylformamide or a mixture of dimethylformamide and xylene.
In an aspect dissolving Duvelisib in a solvent comprising in a suitable solvent selected from alcohol solvents, ester solvents, polar aprotic solvents, ketone solvents, ether solvents, nitrile solvents and water or mixtures thereof.
In an aspect, the mixture in step-a) can be optionally heated to a temperature of about 30°C or about 40°C or about 50°C or about 60°C or about 80°C or about 100°C or any other suitable temperature to provide a solution.
In an aspect, the anti-solvent used in step-b) is xylene.
In another aspect of first embodiment, the crystalline Form-S of Duvelisib is stable for several months. For example, it is stable at least for 10 months when stored at ambient condition, therefore, the said crystalline Form-S of Duvelisib is storage stable.
In the process of the present invention, the crystalline Form-S of Duvelisib produced according to the present invention may be dried in suitable drying equipment such as tray dryer, vacuum oven, rotatory cone dryer, air oven, fluidized bed dryer, spin flash dryer, flash dryer, or the like. The drying may be carried out at atmospheric pressure or under reduced pressure at temperature of less than about 100°C, less than about 60°C, less than about 40°C, or any other suitable temperature. The drying may be carried out for any time period required for obtaining a desired quality, such as from about 15 minutes to 10 hours or longer.
Crystalline Form-S of Duvelisib of formula- 1 produced by the process of the present invention can be further micronized or milled to get desired particle size to achieve desired solubility profile based on different forms of pharmaceutical composition requirements. Techniques that can be used for particle size reduction include but not limited to single or multi-stage micronization using cutting mills, pin/cage mills, hammer mills, jet mills, fluidized bed jet mills, ball mills and roller mills. Milling or micronization can be performed before drying or after drying of the product.
Crystalline Form-S of Duvelisib obtained according to the present invention has particle sizes of less than about 250 pm or less than about 150 pm or less than about 100 pm or less than about 50 pm, or less than about 40 pm or less than about 30 pm or less than about 20 pm or less than about 10 pm or less than about 5 pm
In another embodiment, the present invention provides pharmaceutical composition comprising crystalline Form-S of Duvelisib and one or more pharmaceutically acceptable excipients. wherein the excipient can be selected from Excipient Development for Pharmaceutical, Biotechnology, and Drug Delivery Systems 2006.
In yet another embodiment, pharmaceutical composition comprising crystalline Form- S of Duvelisib and one or more pharmaceutically acceptable excipients is formulated in a manner suitable for the route of administration to be used. As used herein, the term "pharmaceutical compositions" include tablets, pills, powders, liquids, suspensions, emulsions, granules, capsules, suppositories, or injection preparations.
In the second embodiment, the present invention provides crystalline Form-S of Duvelisib prepared according to the present invention having purity of about 99.9%; preferably about 99.95%; more preferably about 99.97% as measured by HPLC.
The starting material Duvelisib or its monohydrate used in the present invention can be prepared from any of the processes known in the art.
The invention also encompasses pharmaceutical compositions comprising crystalline Form-S of Duvelisib of formula- 1 of the present invention. As used herein, the term "Pharmaceutical compositions" or "pharmaceutical formulations" include tablets, pills, powders, liquids, suspensions, emulsions, granules, capsules, suppositories, or injection preparations.
P-XRD Method of Analysis: PXRD analysis of compound of formula- 1 is carried out by using BRUKER/D8 ADVANCE diffractometer using Cu Ka radiation of wavelength 1.5406 A0 and continuous scan speed of 0.03°/min.
The process described in the present invention is demonstrated in examples illustrated below. These examples are provided as illustration only and therefore should not be construed as limitation of the scope of the invention.
Examples:
Example-1: Preparation of crystalline Form-M of Duvelisib
Dimethylformamide (0.2 ml) was added to Duvelisib (0.5 gms) at 25-30°C and stirred for 15 minutes at the same temperature. The mixture was added to xylene (10 ml) at 25-30°C and stirred for 10 minutes at the same temperature. Filtered the solid, washed with xylene and suck dried.
The PXRD pattern of the obtained compound is illustrated in Figure- 1.
Example-2: Preparation of crystalline Form-S of Duvelisib
Dried the solid obtained in example- 1 at 60-65°C for 2-3 hrs.
Yield: 400 mg.
The PXRD pattern of the obtained compound is illustrated in Figure-2.
Example-3: Preparation of crystalline Form-M of Duvelisib
Dimethylformamide (0.2 ml) was added to Duvelisib monohydrate (0.5 gms) at 25- 30°C and stirred for 15 minutes at the same temperature. The mixture was added to xylene (10 ml) at 25-30°C and stirred for 10 minutes at the same temperature. Filtered the solid, washed with xylene and suck dried.
The PXRD pattern of the obtained compound is illustrated in Figure- 1.
Example-4: Preparation of crystalline Form-S of Duvelisib
Dried the solid obtained in example-3 at 60-65°C for 2-3 hrs.
Yield: 400 mg.
The PXRD pattern of the obtained compound is illustrated in Figure-2.

Claims

We Claim:
1. Crystalline Form-S of Duvelisib of formula- 1
Figure imgf000009_0001
Formula- 1 characterized by PXRD (powder X-Ray diffractogram) pattern having peaks at about 10.7 and 21.5 ± 0.2° 29.
2. Crystalline Form-S of Duvelisib as claimed in claim 1, is further characterized by its X-ray powder diffraction pattern having additional peaks at about 8.7, 17.1, 17.5 and 13.9 ± 0.2° of 26.
3. Crystalline Form-S of Duvelisib as claimed in claim 1, is further characterized by its PXRD (powder X-Ray diffractogram) pattern substantially in accordance with figure - 2.
4. A process for the preparation of crystalline Form-S of Duvelisib, comprising: a) providing a solution of Duvelisib of formula- 1 in a solvent, b) combining the solution of step-a) with an anti-solvent, and obtaining the crystalline Form-S of Duvelisib of formula- 1.
5. The process as claimed in claim 4, wherein filtering the compound obtained in step-b) to provide crystalline Form-M of Duvelisib.
6. The process as claimed in claim 4, wherein filtering and drying the compound obtained in step-b) to provide crystalline Form-S of Duvelisib.
7. Crystalline Form-M of Duvelisib as claimed in claim 5, further characterized by PXRD (powder X-Ray diffractogram) pattern substantially in accordance with figure- 1. The process as claimed in claim 4, wherein in step a) providing a solution of Duvelisib by dissolving Duvelisib in dimethylformamide or a mixture of dimethylformamide and xylene. The process as claimed in claim 4, wherein in step-a) providing a solution of Duvelisib by optionally heating to a temperature ranging from about 25 °C to reflux temperature of the solvent. The process as claimed in claim 4, wherein the anti-solvent used in step-b) is xylene. Crystalline Form-S of Duvelisib as claimed in claim 1, having purity of about 99.9% as measured by HPLC.
8
PCT/IN2021/050816 2020-08-25 2021-08-25 Novel polymorphs of (s)-3-(1-(9h-purin-6-yl-amino)ethyl)-8-chloro-2-phenylisoquinolin-1(2h)-one WO2022044040A1 (en)

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Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20090312319A1 (en) * 2008-01-04 2009-12-17 Intellikine Certain chemical entities, compositions and methods
WO2012097000A1 (en) * 2011-01-10 2012-07-19 Pingda Ren Processes for preparing isoquinolinones and solid forms of isoquinolinones
CN105712996A (en) * 2015-02-12 2016-06-29 苏州晶云药物科技有限公司 Novel crystal form of IPI-145 and preparation method of novel crystal form

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20090312319A1 (en) * 2008-01-04 2009-12-17 Intellikine Certain chemical entities, compositions and methods
WO2012097000A1 (en) * 2011-01-10 2012-07-19 Pingda Ren Processes for preparing isoquinolinones and solid forms of isoquinolinones
CN105712996A (en) * 2015-02-12 2016-06-29 苏州晶云药物科技有限公司 Novel crystal form of IPI-145 and preparation method of novel crystal form

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