NZ731963B2 - Anticancer compositions - Google Patents

Anticancer compositions Download PDF

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Publication number
NZ731963B2
NZ731963B2 NZ731963A NZ73196315A NZ731963B2 NZ 731963 B2 NZ731963 B2 NZ 731963B2 NZ 731963 A NZ731963 A NZ 731963A NZ 73196315 A NZ73196315 A NZ 73196315A NZ 731963 B2 NZ731963 B2 NZ 731963B2
Authority
NZ
New Zealand
Prior art keywords
solid dispersion
arn
hpmcas
formulation
prostate cancer
Prior art date
Application number
NZ731963A
Other versions
NZ731963A (en
Inventor
Dennis Martin Hester
Jason Michael Vaughn
Original Assignee
Aragon Pharmaceuticals Inc
Filing date
Publication date
Application filed by Aragon Pharmaceuticals Inc filed Critical Aragon Pharmaceuticals Inc
Priority to NZ770528A priority Critical patent/NZ770528A/en
Priority claimed from PCT/US2015/063661 external-priority patent/WO2016090098A1/en
Publication of NZ731963A publication Critical patent/NZ731963A/en
Publication of NZ731963B2 publication Critical patent/NZ731963B2/en

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Classifications

    • 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
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/4164—1,3-Diazoles
    • A61K31/4184—1,3-Diazoles condensed with carbocyclic rings, e.g. benzimidazoles
    • 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
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
    • A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
    • 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
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
    • A61K31/444—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a six-membered ring with nitrogen as a ring heteroatom, e.g. amrinone
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/0012—Galenical forms characterised by the site of application
    • A61K9/0053—Mouth and digestive tract, i.e. intraoral and peroral administration
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
    • A61K9/141—Intimate drug-carrier mixtures characterised by the carrier, e.g. ordered mixtures, adsorbates, solid solutions, eutectica, co-dried, co-solubilised, co-kneaded, co-milled, co-ground products, co-precipitates, co-evaporates, co-extrudates, co-melts; Drug nanoparticles with adsorbed surface modifiers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
    • A61K9/141—Intimate drug-carrier mixtures characterised by the carrier, e.g. ordered mixtures, adsorbates, solid solutions, eutectica, co-dried, co-solubilised, co-kneaded, co-milled, co-ground products, co-precipitates, co-evaporates, co-extrudates, co-melts; Drug nanoparticles with adsorbed surface modifiers
    • A61K9/146—Intimate drug-carrier mixtures characterised by the carrier, e.g. ordered mixtures, adsorbates, solid solutions, eutectica, co-dried, co-solubilised, co-kneaded, co-milled, co-ground products, co-precipitates, co-evaporates, co-extrudates, co-melts; Drug nanoparticles with adsorbed surface modifiers with organic macromolecular compounds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
    • A61K9/16—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
    • A61K9/16—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction
    • A61K9/1605—Excipients; Inactive ingredients
    • A61K9/1629—Organic macromolecular compounds
    • A61K9/1652—Polysaccharides, e.g. alginate, cellulose derivatives; Cyclodextrin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
    • A61K9/16—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction
    • A61K9/1682—Processes
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/20—Pills, tablets, discs, rods
    • A61K9/2004—Excipients; Inactive ingredients
    • A61K9/2022—Organic macromolecular compounds
    • A61K9/205—Polysaccharides, e.g. alginate, gums; Cyclodextrin
    • A61K9/2054—Cellulose; Cellulose derivatives, e.g. hydroxypropyl methylcellulose
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/20—Pills, tablets, discs, rods
    • A61K9/2072—Pills, tablets, discs, rods characterised by shape, structure or size; Tablets with holes, special break lines or identification marks; Partially coated tablets; Disintegrating flat shaped forms
    • A61K9/2077—Tablets comprising drug-containing microparticles in a substantial amount of supporting matrix; Multiparticulate tablets
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents

Abstract

The present invention concerns pharmaceutical formulations of ARN-509 (4-[7-(6-cyano-5-trifluoromethylpyridin-3-yl)-8-oxo-6-thioxo-5,7-diazaspiro[3.4]oct-5-yl]-2-fluoro-N-methylbenzamide), which can be administered to a mammal, in particular a human, suffering from an androgen receptor (AR)-related disease or condition, in particular cancer, more in particular prostate cancer, including but not limited to castration-resistant prostate cancer, metastatic castration resistant prostate cancer, chemotherapy-naive metastatic castration resistant prostate cancer, biochemically relapsed hormone sensitive prostate cancer, or high-risk, non-metastatic castration-resistant prostate cancer. In one aspect, these formulations comprise a solid dispersion of ARN-509 and HPMCAS. In one aspect, the solid dispersion of ARN-509 and HPMCAS is obtainable, in particular is obtained, by melt-extruding a mixture comprising ARN-509 and HPMCAS and optionally subsequently milling said melt-extruded mixture. In one aspect, the solid dispersion of ARN-509 and HPMCAS is obtainable, in particular is obtained, by spray drying a mixture comprising ARN-509 and HPMCAS in a suitable solvent.

Claims (30)

Claims
1. A solid dispersion comprising F F3C NC N N H O N O S N (ARN-509) and hydroxypropyl methylcellulose acetate succinate (HPMCAS); wherein the weightby-weight ratio of ARN-509 : HPMCAS in the solid dispersion is in the range from 1 : 5 1 to 1 : 5.
2. The solid dispersion according to claim 1 wherein the dispersion consists of ARN509 and HPMCAS. 10 3. The solid dispersion according to claim 1 or 2wherein the weight-by-weight ratio of
3. ARN-509 : HPMCAS in the solid dispersion is 1:3.
4. The solid dispersion according to claim 1 or 2 wherein the weight-by-weight ratio of ARN-509 : HPMCAS in the solid dispersion is 1:2. 15
5. The solid dispersion according to claim 1 or 2 wherein the weight-by-weight ratio of ARN-509 : HPMCAS in the solid dispersion is 1:1.
6. The solid dispersion according to any one of the preceding claims wherein ARN-509 20 is present in amorphous form.
7. The solid dispersion according to any one of the preceding claims wherein the dispersion is a solid solution. 25
8. The solid dispersion according to any one of the preceding claims wherein the HPMCAS is hydroxypropyl methylcellulose acetate succinate granular grade (HPMCAS LG).
9. The solid dispersion according to any one of the preceding claims obtainable by 30 spray drying.
10. The solid dispersion according to any one of claims 1 to 8 obtainable by hot melt extrusion. 51
11. A particle consisting of a solid dispersion as defined in any one of the preceding claims. 5
12. A particle comprising a solid dispersion as defined in any one of claims 1 to 10.
13. A pharmaceutical formulation comprising a pharmaceutically acceptable carrier and a solid dispersion according to any one of claims 1 to 10. 10
14. A pharmaceutical formulation comprising a pharmaceutically acceptable carrier and particles according to claim 11 or 12.
15. The formulation according to claim 13 or 14 wherein the formulation comprises 60 mg of ARN-509. 15
16. The formulation according to claim 13 or 14 wherein the formulation comprises 120 mg of ARN-509.
17. The formulation according to claim 13 or 14 wherein the formulation comprises 20 240 mg of ARN-509.
18. The formulation according to any one of claims 13 to 17 wherein the weight of the solid dispersion ranges from 20 to 40 % of the total weight of the formulation. 25
19. The formulation according to any one of claims 13 to 18 wherein the formulation is a tablet.
20. The formulation according to claim 19 which is suitable for oral administration. 30
21. A process for preparing the solid dispersion according to claim 9 comprising the steps of mixing ARN-509 and HPMCAS in a suitable solvent and spray drying said mixture.
22. The process according to claim 21 wherein the suitable solvent is a mixture of 35 dichloromethane and methanol. 52
23. The process according to claim 22 wherein the weight:weight ratio of dichloromethane to methanol in the mixture is 4 : 6.
24. Use of the pharmaceutical formulation according to any one of claims 13 to 20 for 5 the preparation of a medicament for the treatment of prostate cancer.
25. Use according to claim 24 wherein the medicament is for oral administration.
26. A solid dispersion as claimed in any one of claims 1-10 substantially as 10 described herein and with reference to any example thereof.
27. A particle as claimed in claim 11 or 12 substantially as described herein and with reference to any example thereof. 15
28. A pharmaceutical formulation as claimed in any one of claims 13-20 substantially as described herein and with reference to any example thereof.
29. A process as claimed in any one of claims 21-23 substantially as described herein and with reference to any example thereof. 20
30. A use as claimed in claims 24 or 25 substantially as described herein and with reference to any example thereof.
NZ731963A 2014-12-05 2015-12-03 Anticancer compositions NZ731963B2 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
NZ770528A NZ770528A (en) 2014-12-05 2015-12-03 Anticancer compositions

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP14196594 2014-12-05
PCT/US2015/063661 WO2016090098A1 (en) 2014-12-05 2015-12-03 Anticancer compositions

Publications (2)

Publication Number Publication Date
NZ731963A NZ731963A (en) 2024-03-22
NZ731963B2 true NZ731963B2 (en) 2024-06-25

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