IP Library Granted Patent US 9,457,086
Granted Patent B2
US 9,457,086 · App. 14/197,405 · Granted Oct 4, 2016

Pharmaceuticals for oral delivery

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Quick Facts
Patent No.
US 9,457,086
App. No.
14/197,405
Granted
Oct 4, 2016
Kind
B2
Abstract

The present invention provides solid oral dosage forms and methods of treating subjects in need thereof. The solid oral dosage forms of the present invention provide a mixture including at least one compound classified as BCS Class II, BCS Class III or BCS Class IV, where the compound does not include a peptide bond in the compound's molecular structure; an absorption enhancer; and coated organic acid particles; an enteric coating; and a water soluble barrier positioned between the mixture and the enteric coating.

Claims (51)

1. A solid oral dosage form comprising:

a mixture comprising at least one active pharmaceutical compound classified as BCS Class III, wherein the compound does not include a peptide bond in the compound's molecular structure and functional excipients, wherein the functional excipients consist of:

an absorption enhancer; and

from 100 mg to 500 mg of coated citric acid particles, wherein the citric acid particles are coated with a water soluble coat that separates the citric acid from the active pharmaceutical compound, wherein, if the dosage form was added to ten milliliters of 0.1 M aqueous sodium bicarbonate solution, the pH of the solution would be lowered to no higher than 5.5;

an enteric coating; and

a water soluble barrier positioned between the mixture and the enteric coating, thereby separating the mixture from the enteric coating,

wherein, when the solid dosage form is administered orally, the solid dosage form provides for a synergistic increase in systemic bioavailability when compared to the systemic bioavailability provided by administration of a solid dosage form containing an equal dose of the active pharmaceutical compound without the functional excipients.

2. The solid oral dosage form of claim 1 , wherein the absorption enhancer comprises a surface acting agent.

3. The solid oral dosage form of claim 2 , wherein the surface acting agent is an acid soluble bile acid.

4. The solid oral dosage form of claim 1 , wherein the absorption enhancer comprises an acylcarnitine.

5. The solid oral dosage form of claim 4 , wherein the acylcarnitine is lauroyl carnitine.

6. The solid oral dosage form of claim 1 , wherein the at least one active pharmaceutical compound is an antibiotic or an antiviral compound.

7. The solid oral dosage form of claim 1 , wherein the at least one active pharmaceutical compound is selected from the group consisting of tigecycline, zanamivir, kanamycin, and tobramycin.

8. A solid oral dosage form comprising:

a mixture comprising at least one antibiotic or antiviral compound classified as BCS Class III, wherein the compound does not include a peptide bond in the compound's molecular structures and functional excipients, wherein the functional excipients consist of:

lauroyl-carnitine; and

from 100 mg to 500 mg of coated citric acid particles, wherein the citric acid particles are coated with a water soluble coat that separates the citric acid from the at least one antibiotic or antiviral compound, wherein, if the dosage form was added to ten milliliters of 0.1 M aqueous sodium bicarbonate solution, the pH of the solution would be lowered to no higher than 5.5;

an enteric coating; and

a water soluble barrier positioned between the mixture and the enteric coating, thereby separating the mixture from the enteric coating,

wherein, when the solid dosage form is administered orally, the solid dosage form provides for a synergistic increase in systemic bioavailability when compared to the systemic bioavailability provided by administration of a solid dosage form containing an equal dose of the antibiotic or antiviral compound without the functional excipients.

9. A method for enhancing the systemic bioavailability of a therapeutically effective amount of at least one active pharmaceutical compound classified as BCS Class III to a subject in need thereof comprising orally administering a solid oral dosage form comprising:

a mixture comprising the at least one active pharmaceutical compound, wherein the active pharmaceutical compound does not include a peptide bond in the compound's molecular structure and functional excipients, wherein the functional excipients consist of:

an absorption enhancer; and

from 100 mg to 500 mg of coated citric acid particles, wherein the citric acid particles are coated with a water soluble coat that separates the citric acid from the at least one active pharmaceutical compound, wherein, if the dosage form was added to ten milliliters of 0.1 M aqueous sodium bicarbonate solution, the pH of the solution would be lowered to no higher than 5.5;

an enteric coating; and

a water soluble barrier positioned between the mixture and the enteric coating,

thereby separating the mixture from the enteric coating,

wherein, oral administration results in a synergistic increase in systemic bioavailability of the active pharmaceutical compound when compared to the systemic bioavailability provided by administration of a solid dosage form containing an equal dose of the active pharmaceutical compound without the functional excipients.

10. A method of treating a bacterial or viral infection in a subject in need thereof comprising orally administering a solid oral dosage form comprising:

a mixture comprising at least one active pharmaceutical, antibacterial, or antiviral compound classified as BCS Class III, wherein the compound does not include a peptide bond in the compound's molecular structure and functional excipients, wherein the functional excipients consist of:

an absorption enhancer; and

from 100 mg to 500 mg of coated citric acid particles, wherein the citric acid particles are coated with a water soluble coat that separates the citric acid from the at least one active pharmaceutical compound, wherein, if the dosage form was added to ten milliliters of 0.1 M aqueous sodium bicarbonate solution, the pH of the solution would be lowered to no higher than 5.5;

an enteric coating; and

a water soluble barrier positioned between the mixture and the enteric coating, thereby separating the mixture from the enteric coating,

wherein oral administration results in a synergistic increase in systemic bioavailability of the active compound when compared to the systemic bioavailability provided by administration of a solid dosage form containing an equal dose of the active compound without functional excipients.

11. The solid oral dosage form of claim 1 , wherein the citric acid in the coated citric acid particles has a pKa lower than 4.2.

12. The solid oral dosage form of claim 8 , wherein the at least one antibiotic or antiviral compound is selected from the group consisting of tigecycline, zanamivir, kanamycin, and tobramycin.

13. The solid oral dosage form of claim 1 , wherein the absorption enhancer comprises from 50 mg to 100 mg lauroyl carnitine.

14. The solid oral dosage form of claim 8 , wherein the lauroyl carnitine is present in an amount from 50 mg to 100 mg.

15. The solid oral dosage form of claim 1 , wherein the absorption enhancer comprises one or more absorption enhancers.

16. The solid oral dosage form of claim 1 , wherein when orally administered the solid dosage form provides about a 4-fold to about a 7-fold increase of the mean systemic bioavailability of the active pharmaceutical compound in comparison to the mean systemic bioavailability provided by a solid dosage form containing an equal dose of active pharmaceutical compound without the functional excipients, as measured in a Beagle dog model.

17. A solid oral dosage form comprising:

a mixture comprising at least one active pharmaceutical compound classified as BCS Class III, wherein the compound does not include a peptide bond in the compound's molecular structure,

an absorption enhancer, and

from 100 mg to 500 mg of coated citric acid particles, wherein the citric acid particles are coated with a water soluble coat that separates the citric acid from the active compound, wherein, if the dosage form was added to ten milliliters of 0.1 M aqueous sodium bicarbonate solution, the pH of the solution would be lowered to no higher than 5.5;

an enteric coating; and

a water soluble barrier positioned between the mixture and the enteric coating, thereby separating the mixture from the enteric coating,

the solid dosage form providing, when orally administered, about a 4-fold to about a 7-fold increase of the mean systemic bioavailability of the active pharmaceutical compound in comparison to the mean systemic bioavailability provided by a solid dosage form containing an equal dose of active pharmaceutical compound without the absorption enhancer and the coated citric acid particles, as measured in a Beagle dog model.

18. The solid oral dosage form of claim 17 , wherein the absorption enhancer comprises one or more absorption enhancers.

19. The solid oral dosage form of claim 17 , wherein the absorption enhancer comprises from 50 mg to 100 mg lauroyl carnitine.

20. The solid oral dosage form of claim 17 , wherein the at least one active pharmaceutical compound is selected from the group consisting of tigecycline, zanamivir, kanamycin, and tobramycin.

Assignments (3)
RELEASE OF SECURITY INTEREST Recorded Jun 28, 2023
From: CADENCE BANK, A MISSISSIPPI BANK AND SUCCESSOR BY MERGER TO CADENCE BANK, N.A., A NATIONAL BANKING ASSOCIATION, AS AGENT
To: ENTERIS BIOPHARMA, INC.
Reel/Frame 064149/0741 →
SECURITY INTEREST Recorded Aug 26, 2019
From: ENTERIS BIOPHARMA, INC.
To: CADENCE BANK, N.A.
Reel/Frame 050174/0428 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 16, 2014
From: CARL, STEPHEN M; VRETTOS, JOHN STANLEY; STERN, WILLIAM
To: ENTERIS BIOPHARMA, INC.
Reel/Frame 032912/0271 →