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WO2015114656A2 - Mucoadhesive tablet of pregabalin - Google Patents

Mucoadhesive tablet of pregabalin Download PDF

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Publication number
WO2015114656A2
WO2015114656A2 PCT/IN2015/000033 IN2015000033W WO2015114656A2 WO 2015114656 A2 WO2015114656 A2 WO 2015114656A2 IN 2015000033 W IN2015000033 W IN 2015000033W WO 2015114656 A2 WO2015114656 A2 WO 2015114656A2
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WO
WIPO (PCT)
Prior art keywords
mucoadhesive
mucoadhesive tablet
pregabalin
tablet according
tablet
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.)
Ceased
Application number
PCT/IN2015/000033
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French (fr)
Other versions
WO2015114656A3 (en
Inventor
Nilesh Patel
Umesh Setty
Ashish Sehgal
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.)
Intas Pharmaceuticals Ltd
Original Assignee
Intas Pharmaceuticals Ltd
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
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Publication of WO2015114656A2 publication Critical patent/WO2015114656A2/en
Publication of WO2015114656A3 publication Critical patent/WO2015114656A3/en
Anticipated expiration legal-status Critical
Ceased 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
    • A61K9/0012—Galenical forms characterised by the site of application
    • A61K9/0053—Mouth and digestive tract, i.e. intraoral and peroral administration
    • A61K9/0065—Forms with gastric retention, e.g. floating on gastric juice, adhering to gastric mucosa, expanding to prevent passage through the pylorus
    • 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
    • A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
    • A61K31/19—Carboxylic acids, e.g. valproic acid
    • A61K31/195—Carboxylic acids, e.g. valproic acid having an amino group
    • A61K31/197—Carboxylic acids, e.g. valproic acid having an amino group the amino and the carboxyl groups being attached to the same acyclic carbon chain, e.g. gamma-aminobutyric acid [GABA], beta-alanine, epsilon-aminocaproic acid or pantothenic acid
    • 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
    • A61K9/20—Pills, tablets, discs, rods
    • A61K9/2004—Excipients; Inactive ingredients
    • A61K9/2022—Organic macromolecular compounds
    • A61K9/2031—Organic macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyethylene glycol, polyethylene oxide, poloxamers

Definitions

  • the present invention relates to a mucoadhesive tablet comprising pregabalin with pharmaceutically acceptable excipients, wherein the mucoadhesive tablet maintains gastric retention for the time period during which the drug is released into the stomach. Further it relates to a process for the preparation of the mucoadhesive tablet
  • Pregabalin is an analogue of the physiologically important endogenous neurotransmitter [gamma] -amino butyric acid (GABA), which is involved in the regulation of neural processes.
  • GABA physiologically important endogenous neurotransmitter
  • Pregabalin is disclosed in U.S. Patent Nos. 6,197,819 and 5,563,175, which describe its use in the treatment of seizure disorders.
  • U.S. Patent No. 6,117,906 discloses the use of pregabalin in treating anxiety, while U.S. Patent No. 6,001 ,876 discloses its use in treating pain.
  • pregabalin is available as conventional immediate-release capsules marketed by CP Pharms/Pfizer under the brand name Lyrica ® .
  • Lyrica ® Capsules requires two or three times a day dosing.
  • a once-daily tablet is desirable.
  • pregabalin cannot be absorbed in the entire gastrointestinal tract (GIT).
  • GIT gastrointestinal tract
  • Pregabalin is only absorbed in the upper sections of the gut. It is therefore desirable to have a dosage form which has a longer retention time in the upper GIT and which, during that time, releases the active agent continuously over a longer period of time.
  • the U.S. Publication Application No. 2007/0269511 discloses a pregabalin formulation containing matrix forming agent and a swelling agent, wherein the matrix forming agent is polyvinyl acetate and polyvinylpyrrolidone, and the swelling agent is cross-linked polyvinylpyrrolidone.
  • the U.S. Publication Application No. 2010/0255067 describes pharmaceutical compositions comprising pregabalin, a hydrophobic release controlling agent, and other pharmaceutically acceptable excipients.
  • the U.S. Publication Application No. 2013/149253 describes oral dosage form for the modified release of pregabalin, comprising pregabalin in a matrix comprising a swelling agent, a matrix former and a buoyancy agent or alternatively a sedimentation agent. Therefore, a mucoadhesive tablet that retains in the upper parts of the gastrointestinal tract would be an ideal dosage form for pregabalin.
  • the objective of the present invention is to develop a mucoadhesive tablet of pregabalin.
  • the primary object of the invention is to provide a mucoadhesive tablet comprising pregabalin with pharmaceutically acceptable excipients, wherein the mucoadhesive tablet maintains gastric retention for the time period during which the drug is released into the stomach.
  • Another object of the invention is to provide a mucoadhesive tablet comprising pregabalin with at least mucoadhesive excipient, at least one swelling agent and at least one gelling agent, wherein the mucoadhesive tablet maintains gastric retention for the time period during which the drug is released into the stomach.
  • Another object of the invention is to provide a process for the preparation of a mucoadhesive tablet of pregabalin.
  • the invention relates to a mucoadhesive tablet comprising pregabalin with pharmaceutically acceptable excipients, wherein the mucoadhesive tablet maintains gastric retention for the time period during which the drug is released into the stomach.
  • the invention in another embodiment, relates to a mucoadhesive tablet comprising pregabalin with at least mucoadhesive excipient, at least one swelling agent and at least One gelling agent, wherein the mucoadhesive tablet maintains gastric retention for the time period during which the drug is released into the stomach.
  • the invention relates to a mucoadhesive tablet comprising pregabalin with polyethylene oxide (PEO) as mucoadhesive excipient, cross-linked homopolymers of l-vinyl-pyrrolidin-2-one (Crospovidone) as swelling agent, and sodium alginate as gelling agent.
  • PEO polyethylene oxide
  • Cross-linked homopolymers of l-vinyl-pyrrolidin-2-one (Crospovidone) as swelling agent
  • sodium alginate sodium alginate
  • the invention relates to a mucoadhesive tablet comprising pregabalin with tragacanth as mucoadhesive excipient, sodium starch glycolate as swelling agent, and polymers of acrylic acid cross-linked with polyalkenyl ethers or divinyl glycol such as carbomers (carbopols) as gelling agent.
  • the invention relates to a process for the preparation of a mucoadhesive tablet of pregabalin, preferably direct compression method.
  • the present invention relates to a mucoadhesive tablet comprising pregabalin with pharmaceutically acceptable excipients, wherein the mucoadhesive tablet maintains gastric retention for the time period during which the drug is released into the stomach.
  • the "mucoadhesive tablet” remains in the patient's stomach following oral administration, which is substantially longer than the average residence time of a corresponding immediate release dosage form.
  • the present invention may employ any pharmaceutically acceptable form of pregabalin, including its free form (zwitter ion), and its pharmaceutically acceptable complexes, acid addition salts, base addition salts solvates, hydrates, and polymorphs.
  • the present invention relates to a mucoadhesive tablet comprising pregabalin with at least mucoadhesive excipient, at least one swelling agent and at least one gelling agent, wherein the mucoadhesive tablet maintains gastric retention for the time period during which the drug is released into the stomach.
  • the "mucoadhesive excipient" of the present invention includes polyethylene glycol (PEG 8000), Tragacanth, polymethacrylate derivatives (Eudragit), polyethylene oxide (PEO) or combinations or copolymers thereof.
  • the mucoadhesive excipient is generally used in an amount ranging from about 5% to about 20% by weight of the tablet composition .
  • the "swelling agent" of the present invention includes croscarmellose sodium, sodium starch glycolate (SSG), microcrystalline cellulose (MCC), starch, cross- linked homopolymers of 1 -vinyl-pyrrolidin-2-one (Crospovidone) or combinations or copolymers thereof.
  • the swelling agent absorbs water from the gastric fluid and thereby the tablet expands in size larger than the pylorus.
  • the swelling agent is generally used in an amount ranging from about 5% to about 30% by weight of the tablet composition.
  • the "gelling agent" of the present invention includes polyvinyl pyrrol idone (PVP), polymers of acrylic acid cross-linked with polyalkenyl ethers or divinyl glycol such as carbomers (carbopols), alginates, preferably sodium alginate, hydroxyalkyl cellulose, especially hydroxyethyl cellulose (HEC), xanthan gum or combinations or copolymers thereof.
  • PVP polyvinyl pyrrol idone
  • carbomers carbomers
  • alginates preferably sodium alginate
  • hydroxyalkyl cellulose especially hydroxyethyl cellulose (HEC)
  • HEC hydroxyethyl cellulose
  • xanthan gum xanthan gum or combinations or copolymers thereof.
  • the gelling agent includes excipient that forms a gel when in contact with gastric fluid and thereby modulates the drug release characteristics of the tablet.
  • the gelling agent is generally used in an amount ranging from about 0.5% to about 40% by weight
  • the mucoadhesive tablet may also comprise further pharmaceutically acceptable excipients such as diluents, binders, rate-controlling agents, lubricants, wetting agent, glidants and coating excipients.
  • excipients such as diluents, binders, rate-controlling agents, lubricants, wetting agent, glidants and coating excipients.
  • the mucoadhesive tablet of pregabalin is designed for once-daily administration and achieves bioequivalence with immediate release dosage form of pregabalin that is taken two- or three-times daily.
  • the invention in another embodiment, relates to a process for the preparation of a mucoadhesive tablet of pregabalin. It can be prepared by routine tableting method including direct compression, granulation and pelletization methods. Preferably, the process for the preparation is direct compression method.
  • Example 1 Mucoadhesive Tablet by Direct Compression approach
  • the mucoadhesive tablet of the present invention is prepared by Direct Compr method in the procedural steps as described below. Manufacturing Process:

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Nutrition Science (AREA)
  • Physiology (AREA)
  • Medicinal Preparation (AREA)

Abstract

The present invention relates to a mucoadhesive tablet comprising pregabalin with at least one mucoadhesive excipient, at least one swelling agent and at least one gelling agent, wherein the mucoadhesive tablet maintains gastric retention for the time period during which the drug is released into the stomach. Further it relates to a process for the preparation of the mucoadhesive tablet.

Description

FIELD OF THE INVENTION
The present invention relates to a mucoadhesive tablet comprising pregabalin with pharmaceutically acceptable excipients, wherein the mucoadhesive tablet maintains gastric retention for the time period during which the drug is released into the stomach. Further it relates to a process for the preparation of the mucoadhesive tablet
BACKGROUND OF THE INVENTION
Pregabalin is an analogue of the physiologically important endogenous neurotransmitter [gamma] -amino butyric acid (GABA), which is involved in the regulation of neural processes.
The IUPAC name of pregabalin [INN] is (S)-3-(aminomethyl)-5-methyl hexano acid. The chemical structure of regabalin is shown in formula below:
Figure imgf000002_0001
Pregabalin is disclosed in U.S. Patent Nos. 6,197,819 and 5,563,175, which describe its use in the treatment of seizure disorders. U.S. Patent No. 6,117,906 discloses the use of pregabalin in treating anxiety, while U.S. Patent No. 6,001 ,876 discloses its use in treating pain. Currently, pregabalin is available as conventional immediate-release capsules marketed by CP Pharms/Pfizer under the brand name Lyrica®. The marketed product Lyrica® Capsules requires two or three times a day dosing. In order to improve patient compliance and to reduce the severity and frequency of side effects by reducing peak blood levels along with an increase in drug efficacy by increasing minimum plasma concentration, a once-daily tablet is desirable.
The development of a suitable onee-daily formulation is rendered more difficult by the fact that pregabalin cannot be absorbed in the entire gastrointestinal tract (GIT). Pregabalin is only absorbed in the upper sections of the gut. It is therefore desirable to have a dosage form which has a longer retention time in the upper GIT and which, during that time, releases the active agent continuously over a longer period of time. The U.S. Publication Application No. 2007/0269511 discloses a pregabalin formulation containing matrix forming agent and a swelling agent, wherein the matrix forming agent is polyvinyl acetate and polyvinylpyrrolidone, and the swelling agent is cross-linked polyvinylpyrrolidone. The U.S. Publication Application No. 2010/0255067 describes pharmaceutical compositions comprising pregabalin, a hydrophobic release controlling agent, and other pharmaceutically acceptable excipients.
The U.S. Publication Application No. 2013/149253 describes oral dosage form for the modified release of pregabalin, comprising pregabalin in a matrix comprising a swelling agent, a matrix former and a buoyancy agent or alternatively a sedimentation agent. Therefore, a mucoadhesive tablet that retains in the upper parts of the gastrointestinal tract would be an ideal dosage form for pregabalin. The objective of the present invention is to develop a mucoadhesive tablet of pregabalin. OBJECTS OF THE INVENTION
The primary object of the invention is to provide a mucoadhesive tablet comprising pregabalin with pharmaceutically acceptable excipients, wherein the mucoadhesive tablet maintains gastric retention for the time period during which the drug is released into the stomach.
Another object of the invention is to provide a mucoadhesive tablet comprising pregabalin with at least mucoadhesive excipient, at least one swelling agent and at least one gelling agent, wherein the mucoadhesive tablet maintains gastric retention for the time period during which the drug is released into the stomach.
Another object of the invention is to provide a process for the preparation of a mucoadhesive tablet of pregabalin. SUMMARY OF THE INVENTION
In a first embodiment, the invention relates to a mucoadhesive tablet comprising pregabalin with pharmaceutically acceptable excipients, wherein the mucoadhesive tablet maintains gastric retention for the time period during which the drug is released into the stomach.
In another embodiment, the invention relates to a mucoadhesive tablet comprising pregabalin with at least mucoadhesive excipient, at least one swelling agent and at least One gelling agent, wherein the mucoadhesive tablet maintains gastric retention for the time period during which the drug is released into the stomach.
In a preferred embodiment, the invention relates to a mucoadhesive tablet comprising pregabalin with polyethylene oxide (PEO) as mucoadhesive excipient, cross-linked homopolymers of l-vinyl-pyrrolidin-2-one (Crospovidone) as swelling agent, and sodium alginate as gelling agent.
In a preferred embodiment, the invention relates to a mucoadhesive tablet comprising pregabalin with tragacanth as mucoadhesive excipient, sodium starch glycolate as swelling agent, and polymers of acrylic acid cross-linked with polyalkenyl ethers or divinyl glycol such as carbomers (carbopols) as gelling agent.
In another embodiment, the invention relates to a process for the preparation of a mucoadhesive tablet of pregabalin, preferably direct compression method.
DETAILED DESCRIPTION
The present invention relates to a mucoadhesive tablet comprising pregabalin with pharmaceutically acceptable excipients, wherein the mucoadhesive tablet maintains gastric retention for the time period during which the drug is released into the stomach.
The "mucoadhesive tablet" remains in the patient's stomach following oral administration, which is substantially longer than the average residence time of a corresponding immediate release dosage form. The present invention may employ any pharmaceutically acceptable form of pregabalin, including its free form (zwitter ion), and its pharmaceutically acceptable complexes, acid addition salts, base addition salts solvates, hydrates, and polymorphs.
The present invention relates to a mucoadhesive tablet comprising pregabalin with at least mucoadhesive excipient, at least one swelling agent and at least one gelling agent, wherein the mucoadhesive tablet maintains gastric retention for the time period during which the drug is released into the stomach.
The "mucoadhesive excipient" of the present invention includes polyethylene glycol (PEG 8000), Tragacanth, polymethacrylate derivatives (Eudragit), polyethylene oxide (PEO) or combinations or copolymers thereof. The mucoadhesive excipient is generally used in an amount ranging from about 5% to about 20% by weight of the tablet composition .
The "swelling agent" of the present invention includes croscarmellose sodium, sodium starch glycolate (SSG), microcrystalline cellulose (MCC), starch, cross- linked homopolymers of 1 -vinyl-pyrrolidin-2-one (Crospovidone) or combinations or copolymers thereof.
The swelling agent absorbs water from the gastric fluid and thereby the tablet expands in size larger than the pylorus. The swelling agent is generally used in an amount ranging from about 5% to about 30% by weight of the tablet composition.
The "gelling agent" of the present invention includes polyvinyl pyrrol idone (PVP), polymers of acrylic acid cross-linked with polyalkenyl ethers or divinyl glycol such as carbomers (carbopols), alginates, preferably sodium alginate, hydroxyalkyl cellulose, especially hydroxyethyl cellulose (HEC), xanthan gum or combinations or copolymers thereof. The gelling agent includes excipient that forms a gel when in contact with gastric fluid and thereby modulates the drug release characteristics of the tablet. The gelling agent is generally used in an amount ranging from about 0.5% to about 40% by weight of the tablet composition. In addition to the above-mentioned ingredients, the mucoadhesive tablet may also comprise further pharmaceutically acceptable excipients such as diluents, binders, rate-controlling agents, lubricants, wetting agent, glidants and coating excipients.
The mucoadhesive tablet of pregabalin is designed for once-daily administration and achieves bioequivalence with immediate release dosage form of pregabalin that is taken two- or three-times daily.
In another embodiment, the invention relates to a process for the preparation of a mucoadhesive tablet of pregabalin. It can be prepared by routine tableting method including direct compression, granulation and pelletization methods. Preferably, the process for the preparation is direct compression method.
In order to further illustrate the present invention, the following examples are provided for the purpose of clarity of understanding. However, it is not intended in any way to limit the scope of present invention and it is readily apparent to those of ordinary skill in the art in light of the teachings of this invention that certain changes and modifications may be made thereto without departing from the scope of the invention. Example 1: Mucoadhesive Tablet by Direct Compression approach
Figure imgf000008_0001
The mucoadhesive tablet of the present invention is prepared by Direct Compr method in the procedural steps as described below. Manufacturing Process:
(i) Sift all ingredients through appropriate sieves,
(ii) Blend the sifted ingredients for an appropriate time,
: (iii) Compressed the blend into tablets
(iv) Optionally film coat the compressed tablets.
Dissolution Studies of Mucoadhesive tablet formulation (F3) as representative example:
Figure imgf000009_0001

Claims

We claim:
1. A mucoadhesive tablet comprising pregabalin with pharmaceutically acceptable excipients, wherein the mucoadhesive tablet substantially maintains gastric retention for the time period during which the drug is released into the stomach.
2. The mucoadhesive tablet according to claim 1, wherein the mucoadhesive tablet comprises pregabalin with at least one mucoadhesive excipient, at least one swelling agent and at least one gelling agent.
3. The mucoadhesive tablet according to claim 2, wherein the mucoadhesive excipient is selected from the group of polyethylene glycol (PEG 8000), tragacanth, polymethacrylate derivatives (Eudragit), polyethylene oxide (PEO) or combinations or copolymers thereof.
4. The mucoadhesive tablet according to claim 2, wherein the swelling agent is selected from the group of croscarmellose sodium, sodium starch glycolate (SSG), microcrystalline cellulose (MCC), starch, cross-linked homopolymers of 1 -vinyl - pyrrolidin-2-one (Crospovidone) or combinations or copolymers thereof.
5. The mucoadhesive tablet according to claim 2, wherein the gelling agent is selected from the group of polyvinyl pyrrolidone (PVP), polymers of acrylic acid cross-linked with polyalkenyl ethers or divinyl glycol such as carbomers (carbopols), alginates, preferably sodium alginate, hydroxy alkyl cellulose, especially hydroxy ethyl cellulose (HEC), xanthan gum or combinations or copolymers thereof.
6. The mucoadhesive tablet according to claim 1, wherein the mucoadhesive tablet is a once-daily administration and achieves bioequivalence with immediate release dosage form of pregabalin that is taken two- or three-times daily.
7. The mucoadhesive tablet according to claim 1, wherein the mucoadhesive tablet is prepared by direct compression method.
8. The mucoadhesive tablet according to claim 1 , wherein the mucoadhesive tablet comprises pregabalin, polyethylene oxide (PEO), cross-linked homopolymers of 1- vinyl-pyrrolidin-2-one (Crospovidone), sodium alginate; and optionally other pharmaceutically acceptable excipients.
9. The mucoadhesive tablet according to claim 1 , wherein the mucoadhesive tablet comprises pregabalin, polyethylene oxide, Crospovidone, sodium alginate, and optionally other pharmaceutically acceptable excipients.
10. The mucoadhesive tablet according to claim 1 , wherein the mucoadhesive tablet comprises pregabalin, tragacanth, sodium starch glycolate, carbomers, and optionally other pharmaceutically acceptable excipients.
PCT/IN2015/000033 2014-01-22 2015-01-20 Mucoadhesive tablet of pregabalin Ceased WO2015114656A2 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
IN215/MUM/2014 2014-01-22
IN215MU2014 IN2014MU00215A (en) 2014-01-22 2015-01-20

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WO2015114656A2 true WO2015114656A2 (en) 2015-08-06
WO2015114656A3 WO2015114656A3 (en) 2015-12-17

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN108159011A (en) * 2018-03-16 2018-06-15 中国药科大学 A kind of Pregabalin stomach retention sustained-release piece of biphasic controlled release and preparation method thereof
JP2018118966A (en) * 2017-01-23 2018-08-02 日新製薬株式会社 A compressed solid pharmaceutical composition comprising a γ-aminobutyric acid derivative substituted at the 3-position.

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2765998A1 (en) * 2011-10-11 2014-08-20 Ranbaxy Laboratories Limited A gastroretentive dosage system and process of preparation thereof

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2018118966A (en) * 2017-01-23 2018-08-02 日新製薬株式会社 A compressed solid pharmaceutical composition comprising a γ-aminobutyric acid derivative substituted at the 3-position.
CN108159011A (en) * 2018-03-16 2018-06-15 中国药科大学 A kind of Pregabalin stomach retention sustained-release piece of biphasic controlled release and preparation method thereof

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Publication number Publication date
IN2014MU00215A (en) 2015-08-28
WO2015114656A3 (en) 2015-12-17

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