Nova Patents
CA2802180C

Solid compositions

Abstract

The present invention features solid compositions comprising Compound IA, IB, IC or ID, or a pharmaceutically acceptable salt thereof, in an amorphous form. In one embodiment, Compound IA, IB, IC or ID, or a pharmaceutically acceptable salt thereof, is formulated in an amorphous solid dispersion which comprises a pharmaceutically acceptable hydrophilic polymer and preferably a pharmaceutically acceptable surfactant.

CA2802180C, drawing sheet 1
Sheet 1 of 1

Term

Projected expiry 9 June 2031.

  1. Priority
  2. Filed
  3. Granted
  4. Today
  5. Projected expiry

2 claims: 2 independent, 0 dependent

  1. 1
    A solid dosage form, comprising an amorphous solid dispersion which includes (1) dimethyl (25,2^)-1,1 ’-((2S,2’S)-2,2’-(4,4’-((2S^S)-l -(4-ter/- butylphenyl)pyrrolidine-2,5-diyl)bis(4,lphenylene))bis(azanediyl)bis(oxomethylene)bis(pyrrolidine-2,l-diyl))bis(3-mcthyll-oxobutane-2,l-diyl)dicarbamate or a pharmaceutically acceptable salt thereof;
  2. 2
    (2) a pharmaceutically acceptable hydrophilic polymer;and optionally (3) a pharmaceutically acceptable surfactant. 2. The solid dosage form of claim 1, wherein said polymer has a T8 of at least 50 °C. 3. The solid dosage form of claim 2, wherein said amorphous solid dispersion comprises said surfactant. 4. The solid dosage form of claim 3, wherein said surfactant has an HLB value of at least 10. 5. The solid dosage form according to any one of claims 1-4, wherein said polymer is a homopolymer or copolymer of N-vinyl pyrrolidone. 6. The solid dosage form according to any one of claims 1-4, wherein said polymer is copovidone. 7. The solid dosage form according to any one of claims 1-6, wherein said surfactant is Dalpha-tocopheryl polyethylene glycol 1000 succinate. 8. The solid dosage form according to any one of claims 1-7, where said amorphous solid dispersion is a solid solution. CA 2802180 2018-08-10 9. The solid dosage form according to any one of claims 1-8, further comprising an antiHepatitis C Virus (HCV) agent. 10. The solid dosage form of claim 9, wherein said anti-Hepatitis C Virus (HCV) agent is an HCV protease inhibitor. 11. The solid dosage form of claim 9, wherein said anti-Hepatitis C Virus (HCV) agent is an HCV polymerase inhibitor. 12. Use of the solid dosage form of any one of claims 1-11 for treatment of hepatitis C virus (HCV) infection in an HCV patient. 13. A process of making the solid dosage form of any one of claims 1-11, comprising dissolving dimethyl (2S,2'S)-1,1 ’-((2S,2’S)-2,2’-(4,4’-((2S^S>l-(4-/errbutylphenyl)pyrrolidine-2,5-diyl)bis(4,l- phenylene))bis(azanediyl)bis(oxomethylene)bis(pyrrolidine-2,l-diyl))bis(3-methyl-l-oxobutane2,l-diyl)dicarbamate or a pharmaceutically acceptable salt thereof in a solvent, and further comprising drying the solvent. 14. The process of claim 13, wherein said solvent is a pharmaceutically acceptable hydrophilic polymer. 15. A solid dosage form, comprising an amorphous solid dispersion which includes (1) dimethyl (2S,2'S)-1,1 ’-((2S,2’S)-2,2’-(4,4’-((2S,5S)-l-(4-tert- butylphenyl)pyrrolidine-2,5-diyl)bis(4,lphenylene))bis(azanediyl)bis(oxomethylene)bis(pyrrolidinc-2,l-diyl))bis(3-methyl-l-oxobutane2,l-diyl)dicarbamate or a pharmaceutically acceptable salt thereof;(2) a pharmaceutically acceptable hydrophilic polymer;and optionally (3) a pharmaceutically acceptable surfactant, wherein said polymer has a Tg of at least 50°C;and CA 2802180 2018-08-10 wherein said surfactant has an HLB value of at least 10. 16. A solid dosage form, comprising an amorphous solid dispersion which includes (1) dimethyl (25,25)-1,1 ’-((2S,2’S)-2,2’-(4,4’.((2S,5S)-l.(4-tert- butylphenyl)pyrrolidine-2,5-diyl)bis(4,1 phenylene))bis(azanediyl)bis(oxomethylene)bis(pyrrolidinc-2,l-diyl))bis(3-methyl-l-oxobutane2,l-diyl)dicarbamate or a pharmaceutically acceptable salt thereof;(2) a pharmaceutically acceptable hydrophilic polymer;and optionally (3) a pharmaceutically acceptable surfactant, wherein said polymer has a Tg of at least 50°C and said polymer is homopolymer or copolymer of N-vinyl pyrrolidone and wherein said surfactant has an HLB value of at least 10. 17. A solid dosage form, comprising an amorphous solid dispersion which includes (1) dimethyl (25,25)-1,1 ’-((2S,2’S)-2,2’-(4,4’-((2S,5S)-l-(4-tert- butylphenyl)pyrrolidine-2,5-diyl)bis(4,lphenylene))bis(azanediyl)bis(oxomethylene)bis(pyrrolidine-2,l-diyl))bis(3-methyl-1-oxobutane2,l-diyl)dicarbamate or a pharmaceutically acceptable salt thereof;(2) a pharmaceutically acceptable hydrophilic polymer;and (3) a pharmaceutically acceptable surfactant, wherein said polymer is copovidone;and wherein said surfactant is D-alpha-tocopheryl polyethylene glycol 1000 succinate.
Independent claims2