IP Library Granted Patent US 8,361,488
Granted Patent B2
US 8,361,488 · App. 12/109,983 · Granted Jan 29, 2013

Methods and compositions for controlled release oral dosage of a vitamin D compound

Inventors: Charles W. Bishop (Mount Horeb, WI); Samir P. Tabash (Whitby, CA); Sammy Asiamah Agudoawu (Mississauga, CA); Jay A. White (Newmarket, CA); Keith H. Crawford (Highlands Ranch, CO); Eric J. Messner (Lake Forest, IL); P. Martin Petkovich (Kingston, CA)
Assignees: Cytochroma Inc.; Proventiv Therapeutics, LLC
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Quick Facts
Patent No.
US 8,361,488
App. No.
12/109,983
Granted
Jan 29, 2013
Kind
B2
Abstract

A stable, controlled release formulation for oral dosing of vitamin D compounds is disclosed. The formulation is prepared by incorporating one or more vitamin D compounds into a solid or semi-solid mixture of waxy materials. Oral dosage forms can be prepared by melt-blending the components described herein and filling gelatin capsules with the formulation.

Claims (29)

1. A formulation for controlled release of a vitamin D compound in the gastrointestinal tract of a subject which ingests the formulation, comprising a solid or semi-solid, waxy mixture comprising a waxy controlled release carrier agent, a lipoidic agent, an oily vehicle for the vitamin D compound, and a vitamin D compound, wherein the vitamin D compound comprises a compound selected from the group consisting of 25-hydroxyvitamin D 2 , 25-hydroxyvitamin D 3 , or a combination thereof.

2. The formulation according to claim 1 , wherein the mixture is solid or semi-solid at room temperature and semi-solid or liquid at body temperature.

3. The formulation according to claim 1 , wherein the waxy controlled release carrier agent comprises a non-digestible wax.

4. The formulation according to claim 3 , wherein the non-digestible wax comprises paraffin wax.

5. The formulation according to claim 1 , wherein the waxy controlled release carrier agent is present in an amount in a range of 5 wt % to 35 wt %.

6. The formulation according to claim 1 , wherein the lipoidic agent has a HLB in a range of about 13 to about 18.

7. The formulation according to claim 1 , wherein the lipoidic agent is an emulsifier having a HLB less than 7.

8. The formulation according to claim 1 , wherein the lipoidic agent comprises a polyglycolized glyceride.

9. The formulation according to claim 8 , wherein the polyglycolized glyceride is characterized by a melting point of about 44° C. and a HLB of about 14.

10. The formulation according to claim 1 , wherein the lipoidic agent includes a mixture of a lipophilic emulsifier which has an HLB of less than 7 and an absorption enhancer that preferably has an HLB value from 13 to 18.

11. The formulation according to claim 1 , wherein the oily vehicle comprises a non-digestible oil.

12. A controlled-release oral dosage formulation of a vitamin D compound, comprising a pharmacologically active amount of a vitamin D compound and a release-modifying agent in an amount effective to control the release rate of the vitamin D compound from the dosage form to reduce the maximum serum concentration of the vitamin D compound in a dose interval (Cmax) and/or reduce the maximum change in serum concentration of the vitamin D compound and/or increase the time for the plasma concentration of the vitamin D compound to reach its maximum in a dose interval following administration (Tmax) and/or decrease a ratio of the maximum serum concentration of the vitamin D compound within 24 hours after administration to the concentration 24 hours after administration (Cmax 24hr /C 24hr ), as compared to either or both of (a) an equivalent amount of the vitamin D compound administered by bolus IV injection and (b) the same dosage form omitting the effective amount of the release-modifying agent, wherein the vitamin D compound comprises a compound selected from the group consisting of 25-hydroxyvitamin D 2 , 25-hydroxyvitamin D 3 , or a combination thereof.

13. The formulation according to claim 12 , wherein the dosage form is characterized by both reduced Cmax and increased Tmax.

14. The formulation according to claim 12 , wherein the vitamin D compound comprises 25-hydroxyvitamin D 3 .

15. The formulation according to claim 1 , wherein the vitamin D compound comprises 25-hydroxyvitamin D 3 .

16. A formulation for controlled release of a vitamin D compound in the gastrointestinal tract of a subject which ingests the formulation, comprising a solid or semi-solid, waxy mixture comprising a waxy controlled release carrier agent, a lipoidic agent, an oily vehicle for the vitamin D compound, and a vitamin D compound, wherein the mixture is solid or semi-solid at room temperature and semi-solid or liquid at body temperature, and wherein the vitamin D compound comprises a compound selected from the group consisting of 25-hydroxyvitamin D 2 , 25-hydroxyvitamin D 3 , or a combination thereof.

17. A formulation for controlled release of a vitamin D compound in the gastrointestinal tract of a subject which ingests the formulation, comprising a solid or semi-solid, waxy mixture comprising a waxy controlled release carrier agent, a lipoidic agent, an oily vehicle for the vitamin D compound, and a vitamin D compound, wherein the oily vehicle comprises a non-digestible oil, and wherein the vitamin D compound comprises a compound selected from the group consisting of 25-hydroxyvitamin D 2 , 25-hydroxyvitamin D 3 , or a combination thereof.

18. A formulation for controlled release of a vitamin D compound in the gastrointestinal tract of a subject which ingests the formulation, comprising a solid or semi-solid, waxy mixture comprising paraffin wax, fatty acid mono- and di-glycerides, a mineral oil, a polyglycolized glyceride, and a vitamin D compound selected from the group consisting of 25-hydroxyvitamin D 2 , 25-hydroxyvitamin D 3 , or a combination thereof.

19. The formulation according to claim 12 , wherein the reduction in Cmax is of at least 20%.

20. The formulation according to claim 19 , wherein the reduction in Cmax is of at least 70%.

21. The formulation according to claim 19 , wherein the increase in Tmax is of at least 100%.

22. The formulation according to claim 12 , wherein the reduction of the maximum change in serum concentration of the vitamin D compound is of at least 20%.

23. The formulation according to claim 22 , wherein the reduction of the maximum change in serum concentration of the vitamin D compound is of at least 70%.

24. The formulation according to claim 22 , wherein the increase in Tmax is of at least 100%.

25. The formulation according to claim 12 , wherein the decrease in Cmax 24hr /C 24 hr is of at least 20%.

26. The formulation according to claim 25 , wherein the decrease in Cmax 24hr /C 24 hr is of at least 30%.

27. The formulation according to claim 25 , wherein the increase in Tmax is of at least 100%.

28. The formulation according to claim 12 , wherein the increase in Tmax is of at least 100%.

29. The formulation according to claim 28 , wherein the increase in Tmax is of at least 150%.

Assignments (17)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 30, 2021
From: OPKO IRELAND GLOBAL HOLDINGS, LTD.
To: EIRGEN PHARMA LTD.
Reel/Frame 055765/0953 →
NUNC PRO TUNC ASSIGNMENT Recorded Jul 31, 2015
From: CYTOCHROMA INC.
To: CYTOCHROMA CAYMAN ISLANDS LTD.
Reel/Frame 036238/0359 →
CONFIRMATORY PATENT RIGHTS AGREEMENT Recorded Jul 31, 2015
From: OPKO IP HOLDINGS II, INC.
To: OPKO IRELAND GLOBAL HOLDINGS, LTD.
Reel/Frame 036238/0486 →
NUNC PRO TUNC ASSIGNMENT Recorded Jul 31, 2015
From: OPKO HEALTH, INC.
To: OPKO RENAL, LLC
Reel/Frame 036243/0691 →
NUNC PRO TUNC ASSIGNMENT Recorded Jul 31, 2015
From: CYTOCHROMA CAYMAN ISLANDS LTD.
To: OPKO IP HOLDINGS II, INC.
Reel/Frame 036224/0163 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 31, 2015
From: PROVENTIV THERAPEUTICS, LLC
To: OPKO HEALTH, INC.
Reel/Frame 036225/0082 →
RELEASE OF SECURITY INTEREST Recorded Mar 4, 2013
From: COMERICA BANK, A TEXAS BANKING ASSOCIATION AND AUTHORIZED FOREIGN BANK UNDER THE BANK ACT (CANADA)
To: CYTOCHROMA INC.
Reel/Frame 029914/0404 →
RELEASE OF SECURITY INTEREST Recorded Mar 4, 2013
From: COMERICA BANK, A TEXAS BANKING ASSOCIATION AND AUTHORIZED FOREIGN BANK UNDER THE BANK ACT (CANADA)
To: PROVENTIV THERAPEUTICS , LLC
Reel/Frame 029914/0067 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 31, 2012
From: CRAWFORD, KEITH H.; MESSNER, ERIC J.
To: PROVENTIV THERAPEUTICS, LLC
Reel/Frame 029215/0807 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 31, 2012
From: PETKOVICH, P. MARTIN
To: CYTOCHROMA INC.
Reel/Frame 029215/0629 →
RELEASE OF SECURITY INTEREST Recorded Aug 31, 2012
From: GENERAL ELECTRIC CAPITAL CORPORATION
To: CYTOCHROMA, INC.; CYTOCHROMA HOLDINGS ULC; PROVENTIV THERAPEUTICS, LLC
Reel/Frame 028881/0338 →
SECURITY AGREEMENT Recorded Aug 16, 2012
From: PROVENTIV THERAPEUTICS, LLC
To: COMERICA BANK, A TEXAS BANKING ASSOCIATION AND AUTHORIZED FOREIGN BANK UNDER THE BANK ACT (CANADA)
Reel/Frame 028802/0035 →
SECURITY AGREEMENT Recorded Aug 16, 2012
From: CYTOCHROMA INC., A CORPORATION EXISTING UNDER THE LAWS OF ONTARIO
To: COMERICA BANK, A TEXAS BANKING ASSOCIATION AND AUTHORIZED FOREIGN BANK UNDER THE BANK ACT (CANADA)
Reel/Frame 028801/0539 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 21, 2012
From: TABASH, SAMIR P.; WHITE, JAY A.; AGUDOAWU, SAMMY
To: CYTOCHROMA INC.
Reel/Frame 028418/0540 →
SECURITY AGREEMENT Recorded Sep 28, 2010
From: CYTOCHROMA INC.; PROVENTIV THERAPEUTICS, LLC; CYTOCHROMA HOLDINGS ULC
To: GENERAL ELECTRIC CAPITAL CORPORATION
Reel/Frame 025051/0215 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 24, 2009
From: TABASH, SAMIR P.; WHITE, JAY A.; AGUDOAWU, SAMMY
To: CYTOCHROMA INC.
Reel/Frame 022443/0908 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 24, 2009
From: BISHOP, CHARLES W.
To: PROVENTIV THERAPEUTICS, LLC
Reel/Frame 022471/0929 →
Continuity (2)
Provisional Application 60913853 · Apr 25, 2007
Related Publication 20090176748A1 · Jul 9, 2009