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NZ739127B2 - Solid pharmaceutical compositions for treating hcv - Google Patents

Solid pharmaceutical compositions for treating hcv Download PDF

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Publication number
NZ739127B2
NZ739127B2 NZ739127A NZ73912716A NZ739127B2 NZ 739127 B2 NZ739127 B2 NZ 739127B2 NZ 739127 A NZ739127 A NZ 739127A NZ 73912716 A NZ73912716 A NZ 73912716A NZ 739127 B2 NZ739127 B2 NZ 739127B2
Authority
NZ
New Zealand
Prior art keywords
pharmaceutically acceptable
compound
composition
pharmaceutical dosage
oral pharmaceutical
Prior art date
Application number
NZ739127A
Other versions
NZ739127A (en
Inventor
Katharin Asmus
Yi Gao
Colleen Garrett
Harald Hach
Adivaraha Jayasankar
Samuel Kyeremateng
Ute Lander
Thomas Mueller
Marius Naris
Constanze Obermiller
Original Assignee
Abbvie Inc
Filing date
Publication date
Priority claimed from US15/192,211 external-priority patent/US20160375087A1/en
Application filed by Abbvie Inc filed Critical Abbvie Inc
Priority to NZ775565A priority Critical patent/NZ775565B2/en
Priority claimed from PCT/US2016/042806 external-priority patent/WO2017015211A1/en
Publication of NZ739127A publication Critical patent/NZ739127A/en
Publication of NZ739127B2 publication Critical patent/NZ739127B2/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
    • A61K31/435—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
    • A61K31/445—Non condensed piperidines, e.g. piperocaine
    • A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
    • A61K31/454—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. pimozide, domperidone
    • 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
    • A61K31/498—Pyrazines or piperazines ortho- and peri-condensed with carbocyclic ring systems, e.g. quinoxaline, phenazine
    • 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
    • A61K31/4985—Pyrazines or piperazines ortho- or peri-condensed with heterocyclic ring systems
    • 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
    • A61K9/20—Pills, tablets, discs, rods
    • A61K9/2004—Excipients; Inactive ingredients
    • A61K9/2022—Organic macromolecular compounds
    • A61K9/2027—Organic macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyvinyl pyrrolidone, poly(meth)acrylates
    • 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
    • A61K9/2086—Layered tablets, e.g. bilayer tablets; Tablets of the type inert core-active coat
    • A61K9/209—Layered tablets, e.g. bilayer tablets; Tablets of the type inert core-active coat containing drug in at least two layers or in the core and in at least one outer layer
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12—Antivirals
    • A61P31/14—Antivirals for RNA viruses
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12—Antivirals
    • A61P31/14—Antivirals for RNA viruses
    • A61P31/18—Antivirals for RNA viruses for HIV

Abstract

The present invention features solid pharmaceutical compositions comprising Compound 1 and Compound 2. In one embodiment, the solid pharmaceutical composition includes (1) a first layer which comprises 100 mg Compound 1, as well as a pharmaceutically acceptable hydrophilic polymer and a pharmaceutically acceptable surfactant, all of which are formulated in amorphous solid dispersion; and (2) a second layer which comprises 40 mg Compound 2, as well as a pharmaceutically acceptable hydrophilic polymer and a pharmaceutically acceptable surfactant, all of which are formulated in amorphous solid dispersion.

Claims (27)

WHAT IS CLAIMED IS:
1. A solid oral pharmaceutical dosage composition comprising: a first composition comprising: 50% to 80% by weight of one or more pharmaceutically acceptable polymers, and 100 mg Compound 1 ( ),wherein the weight percentage of the one or more pharmaceutically acceptable polymers is relative to the total weight of the first composition; and a second composition comprising: from more than 80% to 90% by weight of one or more pharmaceutically acceptable polymers, and 40 mg Compound 2 ( ), wherein the weight percentage of the one or more pharmaceutically acceptable polymers is relative to the total weight of the second composition; wherein the formulation is a tablet comprising a first layer and a second layer, the first layer comprising the first composition and the second layer comprising the second composition; and wherein administration of three of the tablets to a population of healthy, non-fasted adult humans results in a mean Cmax value between about 333 ng/mL and about 1113 ng/mL for Compound 1.
2. The solid oral pharmaceutical dosage formulation of claim 1, wherein the first composition comprises a first amorphous solid dispersion comprising Compound 1.
3. The solid oral pharmaceutical dosage formulation of claim 1, wherein the second composition comprises a second amorphous solid dispersion comprising Compound 2.
4. The solid oral pharmaceutical dosage formulation of claim 2, wherein the first amorphous solid dispersion comprises the one or more pharmaceutically acceptable polymers.
5. The solid oral pharmaceutical dosage formulation of claim 2, wherein the first amorphous solid dispersion further comprises one or more pharmaceutically acceptable surfactants.
6. The solid oral pharmaceutical dosage formulation of claim 4, wherein the first amorphous solid dispersion further comprises one or more pharmaceutically acceptable surfactants.
7. The solid oral pharmaceutical dosage formulation of claim 3, wherein the second amorphous solid dispersion comprises the one or more pharmaceutically acceptable polymers.
8. The solid oral pharmaceutical dosage formulation of claim 3, wherein the second amorphous solid dispersion further comprises one or more pharmaceutically acceptable surfactants.
9. The solid oral pharmaceutical dosage formulation of claim 7, wherein the second amorphous solid dispersion further comprises one or more pharmaceutically acceptable surfactants.
10. The solid oral pharmaceutical dosage formulation ofclaim 6, wherein the one or more pharmaceutically acceptable polymers comprise copovidone, and the one or more pharmaceutically acceptable surfactants comprise Vitamin E TPGS.
11. The solid oral pharmaceutical dosage formulation of claim 9, wherein the one or more pharmaceutically acceptable polymers comprise copovidone, and the one or more pharmaceutically acceptable surfactant comprises Vitamin E TPGS.
12. The solid oral pharmaceutical dosage formulation of claim 11, wherein the one or more pharmaceutically acceptable surfactants further comprise propylene glycol monocaprylate.
13. The solid oral pharmaceutical dosage formulation of claim 1, wherein the first composition comprises a first amorphous solid dispersion comprising Compound 1, one or more pharmaceutically acceptable polymers and one or more pharmaceutically acceptable surfactants; and the second composition comprises a second amorphous solid dispersion comprising Compound 2, one or more pharmaceutically acceptable polymers and one or more pharmaceutically acceptable surfactants.
14. The solid oral pharmaceutical dosage formulation of claim 13, wherein the one or more pharmaceutically acceptable polymers comprise copovidone, and the one or more pharmaceutically acceptable surfactants comprises Vitamin E TPGS.
15. The solid oral pharmaceutical dosage formulation of claim 13, wherein the first amorphous solid dispersion comprises Compound 1, one or more pharmaceutically acceptable polymers comprising copovidone, and one or more pharmaceutically acceptable surfactants comprises Vitamin E TPGS; and the second amorphous solid dispersion comprises Compound 2, one or more pharmaceutically acceptable polymers comprising copovidone, and one or more pharmaceutically acceptable surfactants comprising Vitamin E TPGS and Propylene glycol monocaprylate.
16. The solid oral pharmaceutical dosage formulation of any one of claims 13 to 15, wherein the first amorphous solid dispersion comprises 10% to 40% by weight of Compound 1, and the second amorphous solid dispersion comprises 5% to 20% by weight of Compound 2.
17. The solid oral pharmaceutical dosage formulation of any one of claims 13 to 16, wherein the first amorphous solid dispersion comprises 15% to 30% by weight of Compound 1, and the second amorphous solid dispersion comprises 5% to 15% by weight of Compound 2.
18. The solid oral pharmaceutical dosage formulation of claim 13, wherein the first amorphous solid dispersion comprises 15% to 30% by weight of Compound 1, and the second amorphous solid dispersion comprises 5% to 15% by weight of Compound 2.
19. The solid oral pharmaceutical dosage formulation of claim 15, wherein the first amorphous solid dispersion comprises 15% to 30% by weight of Compound 1, and the second amorphous solid dispersion comprises 5% to 15% by weight of Compound 2.
20. The solid oral pharmaceutical dosage formulation of claim 1, wherein the first layer further comprises a disintegrant.
21. The solid oral pharmaceutical dosage formulation of claim 20, wherein the disintegrant comprises Croscarmellose sodium.
22. The solid oral pharmaceutical dosage formulation of claim 1, wherein the first layer and the second layer further comprise a lubricant.
23. The solid oral pharmaceutical dosage formulation of claim 22, wherein the lubricant comprises sodium stearyl fumarate.
24. A solid oral pharmaceutical dosage formulation comprising: a first composition comprising: 50% to 80% by weight of one or more pharmaceutically acceptable polymers, and 100 mg Compound 1 wherein the weight percentage of the one or more pharmaceutically acceptable polymers is relative to the total weight of the first composition; and a second composition comprising: from more than 80% to 90% by weight of one or more pharmaceutically acceptable polymers, and 40 mg Compound 2 wherein the weight percentage of the one or more pharmaceutically acceptable polymers is relative to the total weight of the second composition; wherein the formulation is a tablet comprising a first layer and a second layer, the first layer comprising the first composition and the second layer comprising the second composition; and wherein administration of three of the tablets to a population of healthy, non-fasted adult humans results in a mean AUC value between about 1099 ng·h/mL and about 3680 ng/mL for Compound 1.
25. A solid oral pharmaceutical dosage formulation comprising: a first composition comprising: 50% to 80% by weight of one or more pharmaceutically acceptable polymers, and 100 mg Compound 1 wherein the weight percentage of the one or more pharmaceutically acceptable polymers is relative to the total weight of the first composition; and a second composition comprising: from more than 80% to 90% by weight of one or more pharmaceutically acceptable polymers, and 40 mg Compound 2 wherein the weight percentage of the one or more pharmaceutically acceptable polymers is relative to the total weight of the second composition; wherein the formulation is a tablet comprising a first layer and a second layer, the first layer comprising the first composition and the second layer comprising the second composition; and wherein administration of three of the tablets to a population of healthy, fasted adult humans results in a mean C value between about 85 ng/mL and about 684 ng/mL for Compound 1.
26. A solid oral pharmaceutical dosage formulation comprising: a first composition comprising: 50% to 80% by weight of one or more pharmaceutically acceptable polymers, and 100 mg Compound 1 wherein the weight percentage of the one or more pharmaceutically acceptable polymers is relative to the total weight of the first composition; and a second composition comprising: from more than 80% to 90% by weight of one or more pharmaceutically acceptable polymers, and 40 mg Compound 2 wherein the weight percentage of the one or more pharmaceutically acceptable polymers is relative to the total weight of the second composition; wherein the formulation is a tablet comprising a first layer and a second layer, the first layer comprising the first composition and the second layer comprising the second composition; and wherein administration of three of the tablets to a population of healthy, fasted adult humans results in a mean AUC value between about 429 ng·h/mL and about 2431 ng/mL for Compound 1.
27. A solid oral pharmaceutical dosage formulation that is a bilayer tablet and that is bioequivalent to a solid oral tablet pharmaceutical dosage formulation comprising a. 500 mg of Compound 1 20% extrusion granulation, comprising: i. 20% (100 mg) Compound 1 ii. 69% copovidone, iii. 10% vitamin E TPGS, and iv. 1% colloidal silicon dioxide; b. 400 mg of Compound 2 10% extrusion granulation, comprising i. 10% (40 mg) Compound 2 ii. 79% copovidone, iii. 8% vitamin E TPGS, iv. 2% propylene glycol monocaprylate, and v. 1% colloidal silicone dioxide; c. 26.3 mg croscarmellose sodium; d. 4.7 mg colloidal silicon dioxide; e. 4.7 mg sodium stearyl fumarate; and f. 28.1 mg HPMC coating.
NZ739127A 2016-07-18 Solid pharmaceutical compositions for treating hcv NZ739127B2 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
NZ775565A NZ775565B2 (en) 2016-07-18 Solid pharmaceutical compositions for treating HCV

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US201562193639P 2015-07-17 2015-07-17
US201662295309P 2016-02-15 2016-02-15
US15/192,211 US20160375087A1 (en) 2015-06-26 2016-06-24 Solid Pharmaceutical Compositions for Treating HCV
PCT/US2016/042806 WO2017015211A1 (en) 2015-07-17 2016-07-18 Solid pharmaceutical compositions for treating hcv

Publications (2)

Publication Number Publication Date
NZ739127A NZ739127A (en) 2024-05-31
NZ739127B2 true NZ739127B2 (en) 2024-09-03

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