CA2318008A1 - Solid oral pharmaceutical formulation of modified release that contains an acid labile benzimidazole compound - Google Patents

Solid oral pharmaceutical formulation of modified release that contains an acid labile benzimidazole compound Download PDF

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Publication number
CA2318008A1
CA2318008A1 CA002318008A CA2318008A CA2318008A1 CA 2318008 A1 CA2318008 A1 CA 2318008A1 CA 002318008 A CA002318008 A CA 002318008A CA 2318008 A CA2318008 A CA 2318008A CA 2318008 A1 CA2318008 A1 CA 2318008A1
Authority
CA
Canada
Prior art keywords
inert
water
alkaline
alkaline polymer
modified release
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
CA002318008A
Other languages
French (fr)
Other versions
CA2318008C (en
Inventor
Antonio Lopez Cabrera
Pedro Juan Solanas Ibarra
Vincent Mancinelli
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Esteve Pharmaceuticals SA
Original Assignee
Laboratorios Del Dr. Esteve, S.A.
Antonio Lopez Cabrera
Pedro Juan Solanas Ibarra
Vincent Mancinelli
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Laboratorios Del Dr. Esteve, S.A., Antonio Lopez Cabrera, Pedro Juan Solanas Ibarra, Vincent Mancinelli filed Critical Laboratorios Del Dr. Esteve, S.A.
Publication of CA2318008A1 publication Critical patent/CA2318008A1/en
Application granted granted Critical
Publication of CA2318008C publication Critical patent/CA2318008C/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

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Classifications

    • 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
    • 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
    • A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
    • A61K31/444—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a six-membered ring with nitrogen as a ring heteroatom, e.g. amrinone
    • 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
    • A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
    • A61K9/50—Microcapsules having a gas, liquid or semi-solid filling; Solid microparticles or pellets surrounded by a distinct coating layer, e.g. coated microspheres, coated drug crystals
    • A61K9/5073—Microcapsules having a gas, liquid or semi-solid filling; Solid microparticles or pellets surrounded by a distinct coating layer, e.g. coated microspheres, coated drug crystals having two or more different coatings optionally including drug-containing subcoatings
    • A61K9/5078—Microcapsules having a gas, liquid or semi-solid filling; Solid microparticles or pellets surrounded by a distinct coating layer, e.g. coated microspheres, coated drug crystals having two or more different coatings optionally including drug-containing subcoatings with drug-free core
    • 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
    • A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
    • 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
    • A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
    • A61K9/50—Microcapsules having a gas, liquid or semi-solid filling; Solid microparticles or pellets surrounded by a distinct coating layer, e.g. coated microspheres, coated drug crystals
    • A61K9/5005—Wall or coating material
    • A61K9/5021—Organic macromolecular compounds
    • A61K9/5026—Organic macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyvinyl pyrrolidone, poly(meth)acrylates

Abstract

The pharmaceutical formulation consists of a number of pellets that comprise a inert nucleus, a layer with the active ingredient, one or more intermediate layers that comprise at least a system of modified release, and an external layer of enteric coating.
These pellets can be obtained applying the different layers by means of fluid bed coating techniques using aqueous solutions or suspensions of the components of such layers. The pharmaceutical formulations can be hard gelatine capsules or tablets and are suitable for use in the prevention and treatment of disorders related to abnormal gastric acid secretion.

Claims (24)

1. A pellet comprising an acid labile benzimidazole compound, wherein the pellet comprises:
(a) an inert nucleus;
(b) a layer disposed over said inert nucleus (a), comprising an acid labile benzimidazole compound, an inert, non-alkaline polymer soluble in water and one or more pharmaceutically acceptable inert excipients;
(c) one or more intermediate layers that comprise:
(i) an inert, non-alkaline coating, formed of an inert, non-alkaline polymer soluble in water and one or more pharmaceutically acceptable inert excipients; and (ii) a system of modified release that comprises an inert, non-alkaline polymer soluble in water and an inert, non-alkaline polymer insoluble in water;
said intermediate layer(s) (c) disposed over said layer (b) that covers the inert nucleus; and (d) an external layer comprising an enteric coating disposed over said intermediate layers) (c).
2. A pellet according to claim 1, in which said intermediate layers (c) comprise one or more layers of an inert, non-alkaline coating and one or more layers of a system of modified release that comprises an inert, non-alkaline polymer soluble in water and an inert, non-alkaline polymer insoluble in water.
3. A pellet according to claim 1 wherein, the inert, non-alkaline coating, formed of an inert, non-alkaline polymer soluble in water and one or more pharmaceutically acceptable inert excipients, and the system of modified release that comprises an inert, non-alkaline polymer soluble in water and an inert, non-alkaline polymer insoluble in water, are mixed in a single layer.
4. A pellet according to claim 1, in which said intermediate layers (c) comprise a mixture of one or more layers of inert, non-alkaline coating, and one or more layers of said system of modified release that comprises an inert, non-alkaline polymer soluble in water and an inert, non-alkaline polymer insoluble in water, and one or more layers of a mixture of inert, non-alkaline coating, and said system of modified release that comprises an inert, non-alkaline polymer soluble in water and an inert, non-alkaline polymer insoluble in water.
5. A pellet according to claim 1 wherein the inert, non-alkaline coating, formed of an inert, non-alkaline polymer soluble in water and one or more pharmaceutically acceptable inert excipients is disposed over the layer (b); the layer comprising the system of modified release that comprises an inert, non-alkaline polymer soluble in water and an inert, non-alkaline polymer insoluble in water is disposed over the layer of the inert, non-alkaline coating; and the layer (d) is disposed over the layer formed by the system of modified release comprising an inert, non-alkaline polymer soluble in water and an inert, non-alkaline polymer insoluble in water.
6. A pellet according to claim 1 wherein said acid labile benzimidazole compound is a compound of formula (I) wherein R1 is hydrogen, methoxy or difluoromethoxy, R2 is methyl or methoxy, R3 is methoxy, 2,2,2-trifluoroethoxy or 3-methoxypropoxy, and R4 is hydrogen or methyl.
7. A pellet according to claim 1 wherein said acid labile benzimidazole compound is selected from the group consisting of omeprazole, lansoprazole and pantoprazole.
8. A pellet according to claim 1 wherein, said inert, non-alkaline polymer soluble in water, present in the layer (b) is selected from hydroxypropylmethylcellulose (HPMC) and hydroxypropylcellulose (HPC).
9. A pellet according to claim 1 wherein, said inert, non-alkaline polymer soluble in water of the inert, non-alkaline coating, present in the intermediate layer(s) (c) is hydroxypropylmethylcellulose (HMPC).
10. A pellet according to claim 1 wherein, said inert, non-alkaline polymer soluble in water of the system of modified release, present in the intermediate layer(s) (c) is hydroxypropylmethylcellulose (HMPC).
11. A pellet according to claim 1 wherein, said inert, non-alkaline polymer insoluble in water of the system of modified release, present in the intermediate layer(s) (c) is ethylcellulose or a copolymer of ammonium methacrylate.
12. A pellet according to claim 1 wherein, said external layer (d) comprises a gastro-resistant polymer, a plasticizer and one or more pharmaceutically acceptable inert excipients.
13. A method for obtaining a gastro-resistant pellet of modified release that contains as an active ingredient an acid labile benzimidazole compound, that comprises:
(i) applying an aqueous suspension of an acid labile benzimidazole compound, an inert, non-alkaline polymer soluble in water, and one or more pharmaceutically acceptable inert excipients to cover an inert nucleus;
(ii) applying one or more intermediate layers, separated or mixed among themselves that contain (i) an inert, non-alkaline coating, formed of an inert, non-alkaline polymer soluble in water and one or more pharmaceutically acceptable inert excipients;
and (ii) a system of modified release that comprises an inert, non-alkaline polymer soluble in water and an inert, non-alkaline polymer insoluble in water, separated or mixed; and (iii) covering said intermediate layer or layers with an aqueous suspension that comprises a gastro-resistant polymer, a plasticizer and one or more pharmaceutically acceptable inert excipients to create an external layer of enteric coating.
14. A method according to claim 13 wherein said acid labile benzimidazole compound is a compound of formula (I) wherein R1 is hydrogen, methoxy or difluoromethoxy, R2 is methyl or methoxy, R3 is methoxy, 2,2,2-trifluoroethoxy or 3-methoxypropoxy, and R4 is hydrogen or methyl.
15. A method according to claim 13 wherein said acid labile benzimidazole compound is selected from the group consisting of omeprazole, lansoprazole and pantoprazole.
16. A method according to claim 13 wherein, said inert, non-alkaline polymer soluble in water, present in the suspension applied in step (i) is selected from hydroxypropylmethylcellulose (HPMC) and hydroxypropylcellulose (HPC).
17. A method according to claim 13 wherein, said inert, non-alkaline polymer soluble in water, comprised in the inert, non-alkaline coating, present in the suspension applied in step (ii) is hydroxypropylmethylcellulose (HMPC).
18. A method according to claim 13 wherein, said inert, non-alkaline polymer soluble in water, comprised in the system of modified release, present in the suspension applied in step (ii) is hydroxypropylmethylcellulose (HMPC).
19. A method according to claim 13 wherein, said inert, non-alkaline polymer insoluble in water, comprised in the system of modified release, present in the suspension applied in step (ii) is ethylcellulose or a copolymer of ammonium methacrylate.
20. A composition of modified release that comprises one or more pellets of claim 1.
21. A composition according to claim 20, in which one or more of the pellets have the same release profile of the benzimidazole.
22. A composition according to claim 20, in which one or more of the pellets have a different release profile of the benzimidazole.
23. A composition according to claim 20, comprising a mixture of (i) pellets with a quick release profile and (ii) pellets with a slow release profile, in a ratio (i):(ii), by weight, lying between 10:90 and 90:10.
24. A composition according to claim 20, in the form of a capsule or a tablet.
CA2318008A 1999-09-13 2000-09-12 Solid oral pharmaceutical formulation of modified release that contains an acid labile benzimidazole compound Expired - Fee Related CA2318008C (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
ES009902027A ES2168043B1 (en) 1999-09-13 1999-09-13 PHARMACEUTICAL FORM ORAL SOLID MODIFIED RELEASE CONTAINING A COMPOSITE OF BENCIMIDAZOL LABIL IN THE MIDDLE ACID.
ES9902027 2000-09-13

Publications (2)

Publication Number Publication Date
CA2318008A1 true CA2318008A1 (en) 2001-03-13
CA2318008C CA2318008C (en) 2010-08-17

Family

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Family Applications (1)

Application Number Title Priority Date Filing Date
CA2318008A Expired - Fee Related CA2318008C (en) 1999-09-13 2000-09-12 Solid oral pharmaceutical formulation of modified release that contains an acid labile benzimidazole compound

Country Status (12)

Country Link
US (1) US6780436B1 (en)
EP (1) EP1086694B1 (en)
JP (1) JP4885347B2 (en)
KR (1) KR100724201B1 (en)
AT (1) ATE334679T1 (en)
AU (1) AU777322B2 (en)
CA (1) CA2318008C (en)
CY (1) CY1106219T1 (en)
DE (1) DE60029712T2 (en)
DK (1) DK1086694T3 (en)
ES (2) ES2168043B1 (en)
PT (1) PT1086694E (en)

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Also Published As

Publication number Publication date
ATE334679T1 (en) 2006-08-15
DK1086694T3 (en) 2006-12-04
EP1086694A3 (en) 2002-09-25
JP2001199878A (en) 2001-07-24
JP4885347B2 (en) 2012-02-29
AU5791900A (en) 2001-03-15
DE60029712T2 (en) 2007-08-02
CA2318008C (en) 2010-08-17
EP1086694A2 (en) 2001-03-28
PT1086694E (en) 2006-12-29
EP1086694B1 (en) 2006-08-02
US6780436B1 (en) 2004-08-24
AU777322B2 (en) 2004-10-14
ES2168043A1 (en) 2002-05-16
CY1106219T1 (en) 2011-06-08
KR100724201B1 (en) 2007-05-31
DE60029712D1 (en) 2006-09-14
ES2269088T3 (en) 2007-04-01
KR20020020974A (en) 2002-03-18
ES2168043B1 (en) 2003-04-01

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