Soft-gelatin capsule formulation

US 20070172523A1
Filed: 01/23/2007
Published: 07/26/2007
Est. Priority Date: 01/24/2006
Status: Active Grant

First Claim

Patent Images

1. A soft gelatin capsule formulation of a 15-keto-prostaglandin compound, which comprises:

a soft gelatin capsule shell comprising gelatin and an sugar alcohol as a plasticizer, anda mixture comprising a 15-keto-prostaglandin compound and a pharmaceutically acceptable vehicle, which is filled in the shell.

View all claims

10 Assignments

Timeline View

Assignment View

0 Petitions

Accused Products

Abstract

The present invention discloses a soft gelatin capsule formulation of a 15-keto-prostaglandin compound, which comprises: a soft gelatin capsule shell comprising gelatin and sugar alcohol as a plasticizer, and a mixture comprising a 15-keto-prostaglandin compound and a pharmaceutically acceptable vehicle which is filled in the shell. By encapsulating the 15-keto-prostaglandin compound in the specified soft gelatin capsule shell, stability of the compound is significantly improved.

Citations

15 Claims

1. A soft gelatin capsule formulation of a 15-keto-prostaglandin compound, which comprises:
- a soft gelatin capsule shell comprising gelatin and an sugar alcohol as a plasticizer, anda mixture comprising a 15-keto-prostaglandin compound and a pharmaceutically acceptable vehicle, which is filled in the shell.
- View Dependent Claims (2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14)
- - 2. The formulation of claim 1, wherein the 15-keto-prostaglandin compound is a compound of the formula (I):
    - wherein L, M and N are hydrogen, hydroxy, halogen, lower alkyl, hydroxy(lower)alkyl, lower alkanoyloxy or oxo, wherein at least one of L and M is a group other than hydrogen, and the five-membered ring may have at least one double bond;
      
      A is —
      
      CH₃, or —
      
      CH₂OH, —
      
      COCH₂OH, —
      
      COOH or a functional derivative thereof;
      
      B is —
      
      CH₂—
      
      CH₂—
      
      , —
      
      CH═
      
      CH—
      
      or —
      
      C≡
      
      C—
      
      ;
      
      R₁is a saturated or unsaturated bivalent lower or medium aliphatic hydrocarbon residue, which is unsubstituted or substituted with halogen, lower alkyl, hydroxy, oxo, aryl or heterocyclic group, and at least one of carbon atom in the aliphatic hydrocarbon is optionally substituted by oxygen, nitrogen or sulfur; and
      
      Ra is a saturated or unsaturated lower or medium aliphatic hydrocarbon residue, which is unsubstituted or substituted with halogen, oxo, hydroxy, lower alkyl, lower alkoxy, lower alkanoyloxy, cyclo(lower)alkyl, cyclo(lower)alkyloxy, aryl, aryloxy, heterocyclic group or heterocyclicoxy group;
      
      lower alkoxy;
      
      lower alkanoyloxy;
      
      cyclo(lower)alkyl;
      
      cyclo(lower)alkyloxy;
      
      aryl;
      
      aryloxy;
      
      heterocyclic group;
      
      heterocyclicoxy group.
  - 3. The formulation of claim 1, wherein the 15-keto-prostaglandin compound is a 13,14-dihydro-15-keto-prostaglandin compound.
  - 4. The formulation of claim 1, wherein the 15-keto-prostaglandin compound is a 15-keto-16-mono or 16,16-di-halogen-prostaglandin compound.
  - 5. The formulation of claim 1, wherein the 15-keto-prostaglandin compound is a 13,14-dihydro-15-keto-16-mono- or 16,16-di-halogen-prostaglandin compound.
  - 6. The formulation of claim 1, wherein the 15-keto-prostaglandin compound is a 15-keto-16-mono- or 16,16-di-fluoro-prostaglandin compound.
  - 7. The formulation of claim 1, wherein the 15-keto-prostaglandin compound is a 13,14-dihydro-15-keto-16-mono- or 16,16-di-fluoro-prostaglandin compound.
  - 8. The formulation of claim 1, wherein the 15-keto-prostaglandin compound is a 15-keto-prostaglandin E compound.
  - 9. The formulation of claim 1, wherein the 15-keto-prostaglandin compound is a 13,14-dihydro-15-keto-16,16-difluoro-prostaglandin E₁.
  - 10. The formulation of claim 1, wherein the 15-keto-prostaglandin compound is a 13,14-dihydro-15-keto-16,16-difluoro-18S-methyl-prostaglandin E₁.
  - 11. The formulation of claim 1, wherein the pharmaceutically acceptable vehicle is a fatty acid ester or a polyol.
  - 12. The formulation of claim 1, wherein the fatty acid ester is a glyceride.
  - 13. The formulation of claim 1, wherein the sugar alcohol is selected from the group consisting of sorbitol, maltitol, sugar alcohol solution derived from corn starch, hydrogenated maltose syrup and a mixture thereof.
  - 14. The formulation of claim 1, wherein the sugar alcohol comprises sorbitol and sorbitan as its major component.

15. A method for stabilizing a 15-keto-prostaglandin compound, which comprises:
- dissolving, dispersing or mixing the 15-keto-prostaglandin in a pharmaceutically acceptable vehicle to give a liquid mixture, and incorporating the liquid mixture in a soft gelatin capsule which comprises gelatin and a sugar alcohol as a plasticizer.

Specification

Resources

Litigation Campaign Assessment

Current Assignee
Sucampo GmbH (Mallinckrodt plc)
Original Assignee
R-Tech UENO Limited (Mallinckrodt plc)
Inventors
Harada, Yasuhiro, Hashitera, Yukiko, Hirata, Ryu

Granted Patent

US 8,026,393 B2
Time in Patent Office

Days
Field of Search
US Class Current

424/456
CPC Class Codes

A61K 31/352   condensed with carbocyclic ...

A61K 31/557   Eicosanoids, e.g. leukotrie...

A61K 31/5575   having a cyclopentane, e.g....

A61K 9/4816   Wall or shell material

A61K 9/4825   Proteins, e.g. gelatin gela...

A61K 9/4858   Organic compounds

A61P 1/00   Drugs for disorders of the ...

A61P 1/10   Laxatives

A61P 43/00   Drugs for specific purposes...

Soft-gelatin capsule formulation

First Claim

10 Assignments

0 Petitions

Accused Products

Abstract

Citations

15 Claims

Specification

Solutions

Use Cases

Quick Links

Soft-gelatin capsule formulation

First Claim

10 Assignments

Subscription Required

Subscription Required

0 Petitions

Subscription Required

Accused Products

Subscription Required

Abstract

Citations

15 Claims

Specification

Subscription Required

Solutions

Use Cases

Quick Links