DESC:FIELD OF THE INVENTION:
The present invention relates to the solid forms of Daprodustat.
The present invention also relates to a process for the preparation of solid forms of Daprodustat.

BACKGROUND OF THE INVENTION:
Daprodustat is chemically known as N-[(1,3-dicyclohexyl-6-hydroxy-2,4-dioxo-1,2,3,4-tetrahydro-5-pyrimidinyl)carbonyl]glycine, having the structure of Formula I,

[Formula I]
Daprodustat has been developed by GlaxoSmithKline (GSK) and approved by PMDA (Pharmaceuticals and Medical Devices Agency), Japan on Jun. 29, 2020, under the proprietary name Duvroq®. Daprodustat is used for the treatment of anemia in patients with chronic kidney disease.
U.S. patent number US8324208 first disclosed Daprodustat.
U.S. patent number US11117871 discloses two crystalline forms of a Daprodustat compound (Crystal forms CS1 and CS9).
U.S. patent application US20210387952 discloses 5 crystalline forms of Daprodustat namely Crystalline Forms 1, 2, 3, 4 and 5.
U.S. patent application US20220169619 discloses 2 crystalline forms of Daprodustat namely Crystalline Forms M and K.
Discovering new solid-state forms of a pharmaceutical product may yield materials having desirable processing properties, such as ease of handling, ease of processing, storage stability, and ease of purification or as desirable intermediate crystal forms that facilitate conversion to other polymorphic forms. New solid-state forms of a pharmaceutically useful compound can also provide an opportunity to improve the performance characteristics of a pharmaceutical product. It enlarges the repertoire of materials that a formulation scientist has available for formulation optimization, for example by providing a product with different properties, e.g., a different crystal habit, higher crystallinity, or polymorphic stability, which may offer better processing or handling characteristics, improved dissolution profile, or improved shelf - life (chemical physical stability). For at least these reasons, there is a need for additional solid-state forms of Daprodustat.
The inventors of the present invention have developed new crystalline forms of Daprodustat namely Crystalline forms AL1, AL2, and AL3. The inventor has also developed Daprodustat amorphous solid dispersion with at least one pharmaceutically acceptable excipient.
The amorphous solid dispersion as well as crystalline polymorphs of Daprodustat of the present invention have many advantageous properties including chemical purity, stability such as chemical stability as well as thermal and mechanical stability with respect to polymorphic conversion, stability towards dehydration and/or storage stability, low content of residual solvent, a lower degree of hygroscopicity, flowability, solubility, morphology or crystal habit, and advantageous processing and handling characteristics such as compressibility, and bulk density.

OBJECT OF THE INVENTION:
The main object of the present invention is to provide novel crystalline forms of Daprodustat namely Crystalline forms AL1, AL2, and AL3.
Another object of the present invention is to provide amorphous solid dispersion of Daprodustat with at least one pharmaceutically acceptable excipient.
Further object of the present invention is to provide a commercially viable process for the preparation of crystalline forms AL1, AL2, AL3, as well as process for the preparation of amorphous solid dispersion of Daprodustat with at least one pharmaceutically acceptable excipient.

SUMMARY OF INVENTION:
The main aspect of the present invention is to provide novel crystalline forms of Daprodustat designated as AL1, AL2, AL3 and their process for the preparation.
First aspect of the present invention is to provide novel crystalline form AL1 of Daprodustat characterized by X-ray powder diffraction (XRPD) pattern as shown in Figure-1.
Second aspect of the present invention is to provide novel crystalline form AL2 of Daprodustat characterized by X-ray powder diffraction (XRPD) pattern as shown in Figure-2.
Third aspect of the present invention is to provide novel crystalline form AL3 of Daprodustat characterized by X-ray powder diffraction (XRPD) pattern as shown in Figure-3.
Fourth aspect of the present invention is to provide commercially viable processes for the preparation of crystalline forms of Daprodustat namely AL1, AL2, and AL3.
Fifth aspect of the present invention is to provide amorphous solid dispersion of Daprodustat of Formula I with at least one pharmaceutically acceptable excipient.
BRIEF DESCRIPTION OF DRAWINGS:
Figure-1: X-ray powder diffractogram (XRPD) of crystalline form AL1 of Daprodustat obtained according to Example-1
Figure-2: X-ray powder diffractogram (XRPD) of crystalline form AL2 of Daprodustat obtained according to Example-2
Figure-3: X-ray powder diffractogram (XRPD) of crystalline form AL3 of Daprodustat obtained according to Example-3
Figure-4: X-ray powder diffractogram (XRPD) of amorphous solid dispersion of Daprodustat with PVPK-30 obtained according to Example-5
Figure-5: X-ray powder diffractogram (XRPD) of amorphous solid dispersion of Daprodustat with Copovidone obtained according to Example-6
DETAILED DESCRIPTION OF INVENTION:
In order to provide a clear and consistent understanding of the terms used in the present specification, a number of definitions are provided below. Moreover, unless defined otherwise, all technical and scientific terms as used herein have the same meaning as understood by the person skilled in the art.
The use of the word “a” or “an” when used in conjunction with the term “comprising” in the claims and/or the specification may not only mean “one”, but also encompasses the meaning of “one or more”, “at least one”, and “one or more than one”. Similarly, the word “another” may mean at least a second or more.
As used in this specification the words “comprising” (and any form of comprising, such as “comprise” and “comprises”), “consisting” (and any form of consisting, such as “consists”), “having” (and any form of having, such as “have” and “has”), “including” (and any form of including, such as “include” and “includes”) or “containing” (and any form of containing, such as “contain” and “contains”), are inclusive or open-ended and do not exclude additional, unrecited elements or process steps.
The invention will now be described in detail in connection with certain preferred embodiments, so that various aspects thereof may be fully understood and appreciated.
According to first embodiment, the present invention provides crystalline form AL1 of Daprodustat characterized by X-ray powder diffraction (XRPD) pattern as shown in Figure-1.
In the first embodiment, crystalline form AL1 can be characterized by X-ray powder diffraction (XRPD) pattern comprising peak at 8.17, 16.36, 24.47 and 26.69± 0.2° 2?.
In the first embodiment, crystalline form AL1 can be further characterized by X-ray powder diffraction (XRPD) pattern comprising peaks at 8.17, 16.36, 21.58, 24.47 and 26.69 ± 0.2° 2?.
According to second embodiment, the present invention provides a process for the preparation of crystalline form AL1 of Daprodustat, comprising the steps of:
a) dissolving Daprodustat and D-camphorsulfonic acid in solvent;
b) optionally filtering solution of step a),
c) cooling and isolating resulting solid to obtain crystalline form AL1 of Daprodustat.
In the second embodiment, solvent used in step a) can be selected from the group consisting of alcohol such as methanol, ethanol, n-propyl alcohol, isopropyl alcohol, n-butyl alcohol, isobutyl alcohol, secondary-butyl alcohol or tert-butyl alcohol; ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, ethyl isobutyl ketone; alkyl acetates such as methyl acetate, ethyl acetate, n-propyl acetate, isopropyl acetate, n-butyl acetate or isobutyl acetate; ethers such as diethyl ether, n-propyl ether, diisopropyl ether, methyl tertiary butyl ether, tetrahydrofuran, 2-methyl tetrahydrofuran or dimethoxyethane; nitriles such as acetonitrile, propionitrile, butyronitrile or isobutyronitrile; halogenated aliphatic hydrocarbons such as dichloromethane, dichloroethane, chloroform or carbon tetrachloride; aromatic hydrocarbons such as benzene, toluene or xylene; polar aprotic solvent such as dimethylsulfoxide, N,N-dimethylformamide or N-methylpyrrolidone; water; or mixture(s) thereof.
In the second embodiment, step a) can be carried out at a temperature of 45°C to reflux temperature of solvent used.
In the second embodiment, solution of Daprodustat and D-camphorsulfonic acid obtained after step a) can be filtered, cooled to room temperature, and stirred for 1 hour to 2 hours at 5°C to 30°C.
In the second embodiment, obtained solid can be isolated by filtration and can be dried under Vacuum Tray Drier at a temperature of about 25°C to about 40°C, for about 1 hour to 4 hours.
According to third embodiment, the present invention provides a crystalline form AL2 of Daprodustat characterized by X-ray powder diffraction (XRPD) pattern as shown in Figure-2.
In the third embodiment, crystalline form AL2 can be characterized by X-ray powder diffraction (XRPD) pattern comprising peaks at 3.36 and 18.79 ± 0.2° 2?.
In the third embodiment, crystalline form AL2 can be further characterized by X-ray powder diffraction (XRPD) pattern comprising peaks at 15.84, 19.66, and 20.01± 0.2° 2?.
According to fourth embodiment, the present invention provides a process for the preparation of crystalline form AL2 of Daprodustat, comprising the steps of:
a) dissolving the Daprodustat in non-polar solvent; and
b) removing solvent of step a) to obtain crystalline form AL2 of Daprodustat.
In the fourth embodiment, non-polar solvent used in step a) can be selected from solvents including but not limited to alkanes such as pentane, hexane, and heptane; aromatic hydrocarbon such as benzene, toluene, and xylene; ether such as diethyl ether, methyl tertiary butyl ether (MTBE).
In the fourth embodiment, step a) can be carried out at a temperature of 50°C to reflux temperature of solvent used.
In the fourth embodiment, solution obtained in step a) can be filtered to make it particle free prior to step b).
In the fourth embodiment, crystalline form AL2 can be obtained by subjecting the particle free solution obtained in step a) to distillation under vacuum at a temperature of 40°C to 60°C.
According to fifth embodiment, the present invention provides crystalline form AL3 of Daprodustat characterized by X-ray powder diffraction (XRPD) pattern as shown in Figure-3.
In the fifth embodiment, crystalline form AL3 can be characterized by X-ray powder diffraction (XRPD) pattern comprising peak at 6.62, 7.14, 16.09 and 20.89 ± 0.2° 2?.
According to sixth embodiment, the present invention provides a process for the preparation of crystalline form AL3 of Daprodustat, comprising the steps of:
a) dissolving the Daprodustat in a polar protic solvent; and
b) isolating crystalline form AL3 of Daprodustat.
In the sixth embodiment, polar protic solvent used in step a) can be selected from solvents including but not limited to water; alcohols such as methanol, ethanol, iso-propanol, butanol, 2-butanol; acids such as acetic acid.
In the sixth embodiment, step a) can be carried out at a temperature of 70°C to 90°C.
In the sixth embodiment, step b) can be carried out by filtering solution obtained after step a) to obtain a particle free solution and removing solvent from free solution to obtain crystalline form AL3 of Daprodustat. The solvent can be removed by distillation.
Alternatively, particle free solution can be cooled to 5°C to 30°C. Resulting mixture can be stirred for 1 hour to 3 hours. Resulting solid can be filtered and dried to obtain crystalline form AL3 of Daprodustat.

According to seventh embodiment, the present invention provides amorphous solid dispersion of Daprodustat with at least one pharmaceutically acceptable excipient.
In the seventh embodiment, pharmaceutically acceptable excipient can be selected from the group consisting of polyvinyl pyrrolidone, povidone K-30, povidone K-60, povidone K-90, polyvinylpyrrolidone vinylacetate, co-povidone NF, polyvinylacetal diethylaminoacetate (AEA®), polyvinyl acetate phthalate, polysorbate 80, polyoxyethylene– polyoxypropylene copolymers (Poloxamer® 188), polyoxyethylene (40) stearate, polyethyene glycol monomethyl ether, polyethyene glycol, poloxamer 188, pluronic F-68, methylcellulose, methacrylic acid copolymer (Eudragit or Eudragit-RLPO), hydroxypropylmethyl cellulose phthalate, hydroxypropylmethyl cellulose acetate succinate (HPMC-AS), hydroxypropylmethyl cellulose, hydroxypropyl cellulose SSL(HPC-SSL), hydroxypropyl cellulose SL(HPC-SL), hydroxypropyl cellulose L (HPC-L), hydroxyethyl cellulose, Soluplus® (polyvinyl caprolactam-polyvinyl acetatepolyethylene glycol graft copolymer (PCL-PVAc-PEG)), gelucire 44/14, ethyl cellulose, D-alpha-tocopheryl polyethylene glycol 1000 succinate, cellulose acetate phthalate, carboxymethylethylcelluloseand the like; cyclodextrins, gelatins, hypromellose phthalates, sugars, polyhydric alcohols, and the like; water soluble sugar excipients, preferably having low hygroscopicity, which include, but are not limited to, mannitol, lactose, fructose, sorbitol, xylitol, maltodextrin, dextrates, dextrins, lactitol and the like; polyethylene oxides, polyoxyethylene derivatives, polyvinyl alcohols, propylene glycol derivatives and the like; organic amines such as alkyl amines (primary, secondary, and tertiary), aromatic amines, alicyclic amines, cyclic amines, aralkyl amines, hydroxylamine or its derivatives, hydrazine or its derivatives, and guanidine or its derivatives, or mixtures thereof.
In the seventh embodiment, amorphous solid dispersion of Daprodustat with at least one pharmaceutically acceptable excipient can have weight ratio of 1:0.1 w/w to 1: 10 w/w.
In the seventh embodiment, present invention also provides a process for the preparation of amorphous solid dispersion of Daprodustat with at least one pharmaceutically acceptable excipient, comprising the step of:
a) providing a solution of Daprodustat and at least one pharmaceutically acceptable excipient in solvent;
b) removing the solvent from the solution obtained in step a);
c) isolating amorphous solid dispersion of Daprodustat;
d) optionally, combining amorphous solid dispersion of step c) with at least one additional pharmaceutically acceptable excipient.
In the seventh embodiment, solvent used in step a) can be selected from the group consisting of alcohol such as methanol, ethanol, n-propyl alcohol, isopropyl alcohol, n-butyl alcohol, isobutyl alcohol, secondary-butyl alcohol or tert-butyl alcohol; ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, ethyl isobutyl ketone; alkyl acetates such as methyl acetate, ethyl acetate, n-propyl acetate, isopropyl acetate, n-butyl acetate or isobutyl acetate; ethers such as diethyl ether, n-propyl ether, diisopropyl ether, methyl tertiary butyl ether, tetrahydrofuran, 2-methyl tetrahydrofuran or dimethoxyethane; nitriles such as acetonitrile, propionitrile, butyronitrile or isobutyronitrile; halogenated aliphatic hydrocarbons such as dichloromethane, dichloroethane, chloroform or carbon tetrachloride; aromatic hydrocarbons such as benzene, toluene or xylene; polar aprotic solvent such as dimethylsulfoxide, N,N-dimethylformamide or N-methylpyrrolidone; water; or mixture(s) thereof.
In the seventh embodiment, step a) can be carried out by dissolving Daprodustat and at least one pharmaceutically acceptable excipient in a solvent simultaneously or by dissolving components in solvent separately to form individual solutions and combining those solutions later.
In the seventh embodiment, a solution of Daprodustat and the excipient can be prepared at 10°C to about the reflux temperature of the solvent used. Generally, stirring and/or heating can be used to reduce the time required for the dissolution process.
In the seventh embodiment, a solution of Daprodustat and the excipient can be filtered to make it clear, free of unwanted particles. In embodiments, the obtained solution can be optionally treated with an adsorbent material, such as carbon and/or hydrose, to remove coloured components, etc., before filtration.
In the seventh embodiment, removal of solvent at step b) can be carried out by methods known in the art or any procedure disclosed in the present application. In preferred embodiments, removal of solvent may include, but not limited to solvent evaporation under atmospheric pressure or reduced pressure / vacuum such as a rotational distillation using Büchi® Rotavapor®, spray drying, freeze drying, agitated thin film drying and the like.
In the seventh embodiment, the amorphous solid dispersion of Daprodustat and excipient obtained from step b) can be optionally dried before or after isolating at step c).
In the seventh embodiment, amorphous solid dispersion of Daprodustat obtained at step c) can be optionally combined with at least one additional pharmaceutically acceptable excipient at step d).
In the seventh embodiment, amorphous solid dispersion of Daprodustat can be combined with additional excipient using a technique known in art or by the procedures disclosed in the present application.
In the seventh embodiment, present invention provides amorphous solid dispersion of Daprodustat with PVPK-30, characterized by X-ray powder diffraction (XRPD) pattern as shown in Figure-4 and amorphous solid dispersion of Daprodustat with Copovidone characterized by X-ray powder diffraction (XRPD) pattern as shown in Figure-5.
All PXRD data reported in present invention are obtained using a PANalytical X-ray Diffractometer, with copper Ka radiation.
XRPD Conditions:
Instrument Name X-ray diffractometer
Make & model Malvern PANalytical and Empyrean
Source CuLFF (Long fine focus)
Wavelength 1.5406 A?
While the present invention has been described in terms of its specific aspects and embodiments, certain modifications and equivalents will be apparent to those skilled in the art and are intended to be included within the scope of the present invention.

EXAMPLES:
Following examples are given by way of illustration. It may be understood for the person skilled in the art that these examples are only typical embodiments of the invention and are not therefore considered to be limiting the scope of the present invention.
Example 1: Preparation of Crystalline Form AL1 of Daprodustat
Daprodustat (5 gm) and D-camphorsulfonic acid (2.95 gm) were dissolved in tetrahydrofuran (50 mL) at 50°C to 55°C. The obtained solution was filtered to make it particle free. Resulting solution was cooled slowly to 25°C to 30°C and stirred for 1 hour. The precipitated solid was filtered, dried under vacuum tray drier at 25°C to 30°C for about 1.5 hours to obtain a title compound.
Yield: 80%

Example 2: Preparation of Crystalline Form AL2 of Daprodustat
Daprodustat (5gm) was dissolved in methyl tertiary butyl ether (250 mL) at 60°C. Resulting solution was filtered to make it particle free. The particle free solution was then distilled under vacuum at 50°C to 55°C to obtain a titled compound.
Yield: 85%

Example 3: Preparation of Crystalline Form AL3 of Daprodustat
Daprodustat (5gm) was dissolved in isopropyl alcohol (150 mL) at 70°C to 80°C. Resulting solution was filtered to obtain particle free solution. The particle free solution was then distilled under vacuum at 50°C to 55°C to obtain a titled compound.
Yield: 71%

Example 4: Preparation of Crystalline Form AL3 of Daprodustat
Daprodustat (3gm) was dissolved in 2-butanol (54 mL) at 70°C to 80°C. Resulting solution was filtered to obtain particle free solution. The particle free solution
was cooled slowly to 25°C to 30°C and stirred for 2 hours. The precipitated solid was filtered, dried under vacuum tray drier at 25°C to 30°C for 2 hours to obtain a title compound.
Yield: 75%

Example 5: Preparation of amorphous solid dispersion of Daprodustat with PVPK-30
Daprodustat (1 gm) and PVP K-30 (1 gm) were dissolved in tetrahydrofuran (15 mL) at 50°C to 55°C. Resulting solution was filtered to obtain a particle free solution. Resulting solution was distilled under reduced pressure at 50°C to 55°C to obtain a title compound.
Yield: 85%

Example 6: Preparation of amorphous solid dispersion of Daprodustat with copovidone
Daprodustat (1 gm) and copovidone (1 gm) were dissolved in tetrahydrofuran (15 mL) at 50°C to 55°C. Resulting solution was filtered to obtain a particle free solution. Resulting solution was distilled under reduced pressure at 50°C to 55°C to obtain a title compound.
Yield: 85%
,CLAIMS:I / We Claim:
1. A crystalline form AL1 of Daprodustat characterized by X-ray powder diffraction (XRPD) pattern comprising peak at 8.17, 16.36, 24.47 and 26.69± 0.2° 2?.
2. A crystalline form AL2 of Daprodustat characterized by X-ray powder diffraction (XRPD) pattern comprising peaks at 3.36 and 18.79 ± 0.2° 2?.
3. A crystalline form AL3 of Daprodustat characterized by X-ray powder diffraction (XRPD) pattern comprising peak at 6.62, 7.14, 16.09 and 20.89 ± 0.2° 2?.
4. An amorphous solid dispersion of Daprodustat with at least one pharmaceutically acceptable excipient.
5. The amorphous solid dispersion as claimed in claim 4, wherein pharmaceutically acceptable excipient is selected from the group consisting of polyvinyl pyrrolidone, povidone K-30, povidone K-60, povidone K-90, polyvinylpyrrolidone vinylacetate, co-povidone NF, polyvinylacetal diethylaminoacetate (AEA®), polyvinyl acetate phthalate, polysorbate 80, polyoxyethylene– polyoxypropylene copolymers (Poloxamer® 188), polyoxyethylene (40) stearate, polyethyene glycol monomethyl ether, polyethyene glycol, poloxamer 188, pluronic F-68, methylcellulose, methacrylic acid copolymer (Eudragit or Eudragit-RLPO), hydroxypropylmethyl cellulose phthalate, hydroxypropylmethyl cellulose acetate succinate (HPMC-AS), hydroxypropylmethyl cellulose, hydroxypropyl cellulose SSL(HPC-SSL), hydroxypropyl cellulose SL(HPC-SL), hydroxypropyl cellulose L (HPC-L), hydroxyethyl cellulose, Soluplus® (polyvinyl caprolactam-polyvinyl acetatepolyethylene glycol graft copolymer (PCL-PVAc-PEG)), gelucire 44/14, ethyl cellulose, D-alpha-tocopheryl polyethylene glycol 1000 succinate, cellulose acetate phthalate, carboxymethylethylcelluloseand the like; cyclodextrins, gelatins, hypromellose phthalates, sugars, polyhydric alcohols, and the like; water soluble sugar excipients, preferably having low hygroscopicity, which include, but are not limited to, mannitol, lactose, fructose, sorbitol, xylitol, maltodextrin, dextrates, dextrins, lactitol and the like; polyethylene oxides, polyoxyethylene derivatives, polyvinyl alcohols, propylene glycol derivatives and the like; organic amines such as alkyl amines (primary, secondary, and tertiary), aromatic amines, alicyclic amines, cyclic amines, aralkyl amines, hydroxylamine or its derivatives, hydrazine or its derivatives, and guanidine or its derivatives, or mixtures thereof.
6. A process for the preparation of amorphous solid dispersion of Daprodustat with at least one pharmaceutically acceptable excipient, comprising the step of:
a) providing a solution of Daprodustat and at least one pharmaceutically acceptable excipient in solvent;
b) removing the solvent from the solution obtained in step a);
c) isolating amorphous solid dispersion of Daprodustat;
d) optionally, combining amorphous solid dispersion of step c) with at least one additional pharmaceutically acceptable excipient.
7. The process as claimed in claim 6, wherein pharmaceutically acceptable excipient is selected from the group consisting of polyvinyl pyrrolidone, povidone K-30, povidone K-60, povidone K-90, polyvinylpyrrolidone vinylacetate, co-povidone NF, polyvinylacetal diethylaminoacetate (AEA®), polyvinyl acetate phthalate, polysorbate 80, polyoxyethylene– polyoxypropylene copolymers (Poloxamer® 188), polyoxyethylene (40) stearate, polyethyene glycol monomethyl ether, polyethyene glycol, poloxamer 188, pluronic F-68, methylcellulose, methacrylic acid copolymer (Eudragit or Eudragit-RLPO), hydroxypropylmethyl cellulose phthalate, hydroxypropylmethyl cellulose acetate succinate (HPMC-AS), hydroxypropylmethyl cellulose, hydroxypropyl cellulose SSL(HPC-SSL), hydroxypropyl cellulose SL(HPC-SL), hydroxypropyl cellulose L (HPC-L), hydroxyethyl cellulose, Soluplus® (polyvinyl caprolactam-polyvinyl acetatepolyethylene glycol graft copolymer (PCL-PVAc-PEG)), gelucire 44/14, ethyl cellulose, D-alpha-tocopheryl polyethylene glycol 1000 succinate, cellulose acetate phthalate, carboxymethylethylcelluloseand the like; cyclodextrins, gelatins, hypromellose phthalates, sugars, polyhydric alcohols, and the like; water soluble sugar excipients, preferably having low hygroscopicity, which include, but are not limited to, mannitol, lactose, fructose, sorbitol, xylitol, maltodextrin, dextrates, dextrins, lactitol and the like; polyethylene oxides, polyoxyethylene derivatives, polyvinyl alcohols, propylene glycol derivatives and the like; organic amines such as alkyl amines (primary, secondary, and tertiary), aromatic amines, alicyclic amines, cyclic amines, aralkyl amines, hydroxylamine or its derivatives, hydrazine or its derivatives, and guanidine or its derivatives, or mixtures thereof.
8. The process as claimed in claim 6, wherein solvent is selected from the group consisting of alcohol such as methanol, ethanol, n-propyl alcohol, isopropyl alcohol, n-butyl alcohol, isobutyl alcohol, secondary-butyl alcohol or tert-butyl alcohol; ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, ethyl isobutyl ketone; alkyl acetates such as methyl acetate, ethyl acetate, n-propyl acetate, isopropyl acetate, n-butyl acetate or isobutyl acetate; ethers such as diethyl ether, n-propyl ether, diisopropyl ether, methyl tertiary butyl ether, tetrahydrofuran, 2-methyl tetrahydrofuran or dimethoxyethane; nitriles such as acetonitrile, propionitrile, butyronitrile or isobutyronitrile; halogenated aliphatic hydrocarbons such as dichloromethane, dichloroethane, chloroform or carbon tetrachloride; aromatic hydrocarbons such as benzene, toluene or xylene; polar aprotic solvent such as dimethylsulfoxide, N,N-dimethylformamide or N-methylpyrrolidone; water; or mixture(s) thereof.
9. An amorphous solid dispersion of Daprodustat with PVPK-30.
10. An amorphous solid dispersion of Daprodustat with Copovidone.