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WO2012070785A1 - Composition pharmaceutique à libération contrôlée comprenant du lévétiracétam ou un sel pharmaceutiquement acceptable de celui-ci présentant une stabilité de dissolution améliorée et procédé pour sa fabrication - Google Patents

Composition pharmaceutique à libération contrôlée comprenant du lévétiracétam ou un sel pharmaceutiquement acceptable de celui-ci présentant une stabilité de dissolution améliorée et procédé pour sa fabrication Download PDF

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Publication number
WO2012070785A1
WO2012070785A1 PCT/KR2011/008420 KR2011008420W WO2012070785A1 WO 2012070785 A1 WO2012070785 A1 WO 2012070785A1 KR 2011008420 W KR2011008420 W KR 2011008420W WO 2012070785 A1 WO2012070785 A1 WO 2012070785A1
Authority
WO
WIPO (PCT)
Prior art keywords
pharmaceutical composition
sustained
release pharmaceutical
levetiracetam
water
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/KR2011/008420
Other languages
English (en)
Inventor
Sang-Joon Lee
Kwan-Young Chang
Jae-Soon Ahn
Jae-Min Cho
Kyoung-Un Kang
Hyun-Joo Lee
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.)
BIO PHARMARTIS Co Ltd
Hyundai Pharm Co Ltd
Original Assignee
BIO PHARMARTIS Co Ltd
Hyundai Pharm Co 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
Application filed by BIO PHARMARTIS Co Ltd, Hyundai Pharm Co Ltd filed Critical BIO PHARMARTIS Co Ltd
Publication of WO2012070785A1 publication Critical patent/WO2012070785A1/fr
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
    • 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
    • A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
    • A61K31/4015—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil having oxo groups directly attached to the heterocyclic ring, e.g. piracetam, ethosuximide
    • 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
    • A61K9/2027—Organic macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyvinyl pyrrolidone, poly(meth)acrylates
    • 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
    • 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
    • A61K9/2036—Silicones; Polysiloxanes
    • 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
    • A61K9/205—Polysaccharides, e.g. alginate, gums; Cyclodextrin
    • 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
    • A61K9/205—Polysaccharides, e.g. alginate, gums; Cyclodextrin
    • A61K9/2054—Cellulose; Cellulose derivatives, e.g. hydroxypropyl methylcellulose
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/08—Antiepileptics; Anticonvulsants

Definitions

  • the present invention relates to a sustained-release pharmaceutical composition comprising a levetiracetam or a pharmaceutically acceptable salt thereof, and to a method of preparing the same. More specifically, the present invention relates to a sustained-release pharmaceutical composition comprising a levetiracetam or a pharmaceutically acceptable salt thereof with improved dissolution stability that is constant dissolution rate under various releasing conditions, and to a method of preparing the same in a simple and easy process.
  • Levetiracetam is S-enantiomer of (S)-(-)-ethyl-2-oxo-l-pyrolidine acetamide and has a chemical structure of C 8 Hi 4 N 2 0 2 and a molecular weight of 170.21.
  • Levetiracetam is used as a protecting agent for preventing or treating a hypoxic-ischemic attack in central nervous system, and particularly, as an assistant anti-epileptic drug used to treat various types of seizures in adults.
  • the exact mechanism of levetiracetam to take an antiepileptic effect has not been identified, and how the antiepileptic effect is derived from the interaction with the known mechanism of inhibition and excitation of neurotransmission has not been reported.
  • the pharmaceutical composition including the levetiracetam shows different releasing rate of active ingredient as time goes on, thereby causing the delay in drug release. Thus, it lo wass the stability of the pharmaceutical composition and shortens the storage time.
  • a food which is known as another factor affecting the releasing rate does not affect the absorption rate of levetiracetam, but reduces the Cmax by 20% and delays in Tmax by 1.5 hour.
  • the sustained-release pharmaceutical composition containing water-soluble active ingredients such as levetiracetam is difficult to prepare.
  • a large amount of an excipient to control the drug release is used for obtaining the dissolution stability of levetiracetam-containing pharmaceutical composition, it increases the dosage size and thus causes the patient's inconvenience in drug administration.
  • the levetiracetam in a wet granulation process used normally for preparing the pharmaceutical composition containing the levetiracetam as an active ingredient, the levetiracetam can be dissociated due to the contact with liquid phase.
  • the demand for an additional drying step makes the process be complex, requires more time and increases the production cost due to the heat supply for drying.
  • the present invention relates to a sustained-release pharmaceutical composition
  • a sustained-release pharmaceutical composition comprising a levetiracetam or a pharmaceutically acceptable salt thereof with an improved dissolution stability that is constant under various releasing conditions.
  • the present invention provides a sustained-release pharmaceutical composition
  • a sustained-release pharmaceutical composition comprising an active ingredient including a levetiracetam or a pharmaceutically acceptable salt thereof; a sustained-release base material containing a water-swellable polymer; and a pharmaceutically acceptable excipient.
  • the present invention provides a method of preparing the sustained-release pharmaceutical composition, comprising the steps of mixing the levetiracetam or pharmaceutically acceptable salt thereof, the water-swellable polymer, and the pharmaceutically acceptable excipient; and lubricating and directly compressing the mixture into a tablet.
  • a sustained-release pharmaceutical composition comprising an active ingredient including a levetiracetam or a pharmaceutically acceptable salt thereof; a sustained-release base material including a water-swellable polymer; and a pharmaceutically acceptable excipient is provided.
  • the amount of active ingredient may be determined at an amount being sufficiently proper for preventing and/or treating the disease depending upon the subject to be administered, and may be adjusted by various factors, for examples, age, body weight, general health condition and sex of the subject, diet, administering time interval, the kind and severity of disease, the kind and amount of the other components contained the composition, formulation type, administering route, releasing rate of the composition, the treatment period, and co-administered drug.
  • the pharmaceutical composition of the present invention can be administered one to several times daily for adult at a total effective amount of 500 to 3,000 mg.
  • the administering amount or dosage of the active ingredient is determined, so as not to cause the side-effect due to the excess active ingredient.
  • the pharmaceutical composition of the present invention can be provided as a proper formulation type to be administered once daily.
  • the present inventors researched to provide the pharmaceutical composition in a proper formulation type to be administered once daily.
  • the formulation of pharmaceutical composition is prepared to be released slowly by using the sustained-release base material including the water-swellable, it was possible to effectively control the release rate of the levetiracetam or pharmaceutically acceptable salt thereof and to achieve the desired release rate of active ingredient, such as preferably 20-40% in 1 hour, 40-60% in 2 hours, and 80% or more in 6 hours or longer, thereby increasing the subject's compliance and obtaining the improved prevention or treatment effect, and then completed the present invention.
  • the pharmaceutical composition of an embodiment of the present invention has the proper condition of testing the bioequivalence under the fed condition. When the pharmaceutical composition was stored even for 6 months, it showed the consistent dissolution rate after 6 months and thus had the improved dissolution stability in various dissolution conditions.
  • the levetiracetam or pharmaceutically acceptable salt thereof may include levetiracetam, a racemate, an enanthiomer, an isomer, a hydrate, solvate and the like.
  • the levetiracetam or pharmaceutically acceptable salt thereof may be contained at an amount of 50 to 90wt%, and more preferably 60 to 80 wt% with respect to total pharmaceutical composition.
  • the levetiracetam or pharmaceutically acceptable salt thereof is contained at less than the range, the increased weight of composition itself makes it difficult to be administered and useless for a pharmaceutical composition.
  • the amount is excessively high, the composition cannot be formulated as a sustained- release type.
  • the sustained-release base material including the water-swellable polymer is used.
  • the examples of the water-swellable polymer may be at least one selected from the group consisting of methylcellulose, hydroxymethylcellulose, hydroxyethyl cellulose, hydroxypropyl cellulose, hydroxypropylmethylcellulose, hydro xybutylcellulose, hydro yethylmethylcellulose, hypromellose, galactomannans, tragacanth, agar, guar gum, polyfructan, methacrylate copolymer, polyvinylalcohol, polyvinylpyrrolidone, polyvinylpyrrolidone-vinylacetate copolymer(PVP-PVA), a mixture of polyvinylalcohol and polyvinylpyrrolidone, polyethylene oxide, polypropylene oxide, ethylene oxide-propylene oxide copolymer, acrylate polymer, methacrylate copolymer, alginate, carrageenan, acasia, xanthan gum, chitin derivative, sodium carmellose,titium carmel
  • the release rate of active ingredient is based on the viscosity of water-swellable polymer, and the viscosity of water-swellable polymer may be 50 to 100,000mPa ⁇ s, or more preferably 2000 to 15,000mPa ⁇ s, when it is measured at 2wt% concentration in water at 20 ° C, according to the methods disclosed in United States Pharmacopeia, such as Ubbelohde method.
  • the hydroxypropyl cellulose among the water-swellable polymers can has various viscosities.
  • the viscosity of the water-swellable polymer can be about 50 to about 10,000mPa ⁇ s, or more preferably about 3,000 to about 8,000mPa ⁇ s.
  • the polyethylene oxide to be used can has a viscosity of about 400 to 2O,O0OmPa ⁇ s and preferably about 2,000 to 15,000 mPa ⁇ s.
  • the hydro xyethyl cellulose can have viscosity of about 150 to 10,000mPa ⁇ s and more preferably about 4,500 to 8,000 mPa ⁇ s.
  • the pharmaceutical composition of the present invention includes the water-swellable polymer at an amount of 5 to 50 wt% preferably, and more preferably 15 to 35 wt%, on the basis of total pharmaceutical composition.
  • the water-swellable polymer is less than the ranges, the drug release rate gets faster and causes the side-effects such as Dose Dumping.
  • the low release rate makes it impossible to reach the optimal blood concentration, thereby not achieving the sufficient efficacy.
  • composition of the present invention may further include pharmaceutically acceptable excipient.
  • the examples of pharmaceutically acceptable excipients are filling agents such as lactose, corn starch, microcrystalline cellulose, polyethylene glycol and dicalcium phosphate; binders such as micro crystalline cellulose, high dispersible silica, mannitol, sugar such as lactose, and polyethylene glycol; lubricants such as colloidal silica, talc, stearic acid, magnesium stearate, and sodium stearyl fumarate; coating agents such as ethylcellulose, hydroxypropyl methylcellulose and methacrylic acid-alkyl acrylate copolymer; a solubilizing agent, a coloring agent, a pH adjuster, a surfactant, a emulsifying agent and the like, but can be selected properly according to the conventional technology known to an ordinarily-skilled person in the art without limitation.
  • binders such as micro crystalline cellulose, high dispersible silica, mannitol, sugar such as lactos
  • the effective control of the release rate of pharmaceutical composition can increase the subject's compliance, and show the prevention or treatment of the disease of interest.
  • the pharmaceutical composition can be prepared according to the general preparation method known to ordinarily-skilled person in the art without limitation. But, in the wet granulation method used generally, the active ingredient can be dissociated by contacting with liquid phase, and has high cost and long production time due to the need to additional drying step. Thus, the direct compression method can be used preferably.
  • An embodiment of the present invention provides a method of preparing the sustained-release pharmaceutical composition comprising the steps of mixing a levetiracetam or a pharmaceutically acceptable salt thereof, a water-swellable polymer and a pharmaceutically acceptable excipient; and lubricating and directly compressing the mixture into a tablet.
  • the method of preparing the pharmaceutical composition may include a step of coating the tablet with a coating agent after making the tablet.
  • the method of preparing the pharmaceutical composition it is possible to make pharmaceutical composition simply and easily which is very economical due to saving of time, endeavor and cost, and to improve the effect of prevention or treatment of the disease of interest by preventing the active ingredient dissociating due to the contact with liquid phase .
  • the effective control of the release rate of pharmaceutical composition can increase the subject's compliance by reducing the number of administration and maintain the plasma concentration of active ingredient, thereby showing the prevention or treatment of the disease of interest.
  • the pharmaceutical composition satisfies the condition of testing the bio equivalence under the fed condition. When the pharmaceutical composition is stored even for 6 months, it shows the consistent dissolution rate after 6 months. Thus the composition has an improved dissolution stability in various releasing conditions.
  • the method of preparing the pharmaceutical composition it is possible to make pharmaceutical composition simply and easily which is very economical due to saving of time, endeavor and cost, and to improve the effect of prevention or treatment of the disease of interest by preventing the active ingredient dissociating due to the contact with liquid phase.
  • the sustained-release pharmaceutical composition including the levetiracetam was prepared in a table 1.
  • levetiracetam, Polyethylene oxide and polyethylene glycol were sieved with 30-mesh sieve and mixed, and then were lubricated with colloidal silica and magnesium stearate.
  • the lubricated product was directly compressed to produce tablet (KP200/13, Gisan, Korea).
  • the tablet was coated with Opadry (SFC-30F, Sejong Pharmatec, Korea) to obtain final tablet.
  • the viscosity of the Polyethylene oxide used in Table 1 were as follows:
  • the sustained-release pharmaceutical composition including the levetiracetam was prepared in a table 2.
  • levetiracetam and hydroxypropyl cellulose (Examples 5 to 7) or hydroxyethyl cellulose(Examples 8 and 9), and polyethyle glycol were sieved with 30 -mesh sieve and mixed, and then was lubiricated with colloidal silica and magnesium stearic acid.
  • the lubricated mixture was compressed directly into tablet (KP200/13, Gisan, Korea).
  • the tablet was coated with opadry (SFC-30F, Sejongpharmatech, Korea) to produce the final tablet.
  • the viscosity of hydro xypropyl cellulose used in Table 2 are as follows.
  • the sustained-release pharmaceutical composition including the levetiracetam was prepared in a table 3.
  • levetiracetam, carbomer (Examples 10 and 1 1) or sodium alginate (Example 12), and polyethylene glycol were sieved with 30 -mesh sieve and mixed, and then was lubiricated with colloidal silica and magnesium stearic acid.
  • the lubricated mixture was compressed directly into tablet (KP200/13, Gisan, Korea).
  • the tablet was coated with opadry (SFC-30F, Sejongpharmatech, Korea) to produce the final tablet.
  • the viscosity of carbomer used in Table 3 are as follows.
  • the sustained-release pharmaceutical composition including the levetiracetam was prepared in a table 4.
  • levetiracetam was sieved with 30-mesh sieve, granulated with aqueous polyvinyl pyrrolidone solution, and dried at 50 ° C .
  • the dried granules were classified with 20-mesh sieve, mixed with hydroxypropyl methylcellulose, lubricated with Magnesium stearate and colloidal silica, and then compressed into tablet.
  • the tablet was coated with aqueous dispersion solution including ethyl cellulose (Comparative Example 1), Opadry(Comparative Example 3), or aqueous dispersion solution including ethylecellulose and Opadry (Comparative Example 2).
  • the coated tablet was cured at 55 ° C for 1 hour.
  • Test Example 1 Test of dissolution rate at various time
  • the tablets of Examples 1 to 12 represented the effective control of levetiracetam release, and constant release rate of levetiracetam which was 20-40% in 1 hour, 40-60% in 2 hours, 80% or higher in 6 hours, unlike the tablets of Comparative Examples 1 to 3 levetiracetam.
  • the stable release rate of pharmaceutical composition can increase the subject's compliance and have an improved dissolution stability in various releasing conditions.
  • Test Example 2 Test of dissolution stability in long-term storage
  • the tablets prepared by the direct compressing method in Examples 3 and 1 1 represented nearly constant release rate even after 6 months, but the tablet prepared by wet granulating method in Comparative Example 3 showed largely-decreased release rate. Thus, the result confirmed that the tablet prepared by the method of present invention maintained still excellent dissolution stability after long-term storage.
  • the sustained-release tablet is required to test bioequivalence at fed condition.
  • Example 3 and Comparative Example 1 were tested for the dissolution degree of levetiracetam by using 900m# of pH 1.2 hydrochloric acid/sodium chloride solution as a dissolving medium, which is similar to the gastrointestinal condition, and by adding the compounds in Table 7 at 40-mesh basket (USP type 1) at 37 ° C and 100 rpm in 1, 2, 4, 6, 8 and 12 hour. The results were shown in Table 7.
  • composition prepared by the Examples of the present invention showed constant dissolution rate which was not affected by the food-feeding, and very excellent dissolution stability.

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Abstract

La présente invention concerne une composition pharmaceutique à libération contrôlée comprenant du lévétiracétam ou un sel pharmaceutiquement acceptable de celui-ci et un procédé de préparation de celui-ci. De manière plus spécifique, la présente invention concerne une composition pharmaceutique à libération contrôlée comprenant du lévétiracétam ou un sel pharmaceutiquement acceptable de celui-ci présentant une stabilité de dissolution améliorée, c'est-à-dire une vitesse de dissolution constante sous diverses conditions de libération, et un procédé de préparation de celui-ci de manière simple et facile.
PCT/KR2011/008420 2010-11-23 2011-11-07 Composition pharmaceutique à libération contrôlée comprenant du lévétiracétam ou un sel pharmaceutiquement acceptable de celui-ci présentant une stabilité de dissolution améliorée et procédé pour sa fabrication Ceased WO2012070785A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
KR1020100116988A KR20120055313A (ko) 2010-11-23 2010-11-23 레베티라세탐 또는 이의 약학적으로 허용되는 염을 포함하는 용출 안정성이 개선된 서방형 약학 조성물 및 이의 제조방법
KR10-2010-0116988 2010-11-23

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Cited By (7)

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Publication number Priority date Publication date Assignee Title
CN105030714A (zh) * 2015-07-06 2015-11-11 长春中医药大学 阿尼西坦缓释片及其制备方法
WO2016191288A1 (fr) * 2015-05-22 2016-12-01 Agenebio, Inc. Compositions pharmaceutiques de lévétiracétam à libération prolongée
US10154988B2 (en) 2012-11-14 2018-12-18 The Johns Hopkins University Methods and compositions for treating schizophrenia
EP3590506A1 (fr) * 2015-05-22 2020-01-08 Agenebio, Inc. Compositions pharmaceutiques à libération prolongée comportant du lévétiracétam
US10806717B2 (en) 2013-03-15 2020-10-20 The Johns Hopkins University Methods and compositions for improving cognitive function
US11160785B2 (en) 2013-03-15 2021-11-02 Agenebio Inc. Methods and compositions for improving cognitive function
CN114146062A (zh) * 2021-03-17 2022-03-08 长沙晶易医药科技有限公司 一种组合物及其制备方法和用途

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WO2006080029A1 (fr) * 2005-01-27 2006-08-03 Alembic Limited Formulation de lévétiracétam à libération prolongée
US20070298098A1 (en) * 2005-02-16 2007-12-27 Elan Pharma International Limited Controlled Release Compositions Comprising Levetiracetam
US20090099151A1 (en) * 2005-06-29 2009-04-16 Panacea Biotec Ltd. Modified Release Pharmaceutical Compositions and Processes Thereof
US20090099154A1 (en) * 2005-06-29 2009-04-16 Panacea Biotec Ltd. Pharmaceutical Sustained Release Compositions and Processes Thereof
US20100151018A1 (en) * 2007-02-05 2010-06-17 Rd- Pharmagal Sustained-release levetiracetam composition and preparation process

Patent Citations (5)

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Publication number Priority date Publication date Assignee Title
WO2006080029A1 (fr) * 2005-01-27 2006-08-03 Alembic Limited Formulation de lévétiracétam à libération prolongée
US20070298098A1 (en) * 2005-02-16 2007-12-27 Elan Pharma International Limited Controlled Release Compositions Comprising Levetiracetam
US20090099151A1 (en) * 2005-06-29 2009-04-16 Panacea Biotec Ltd. Modified Release Pharmaceutical Compositions and Processes Thereof
US20090099154A1 (en) * 2005-06-29 2009-04-16 Panacea Biotec Ltd. Pharmaceutical Sustained Release Compositions and Processes Thereof
US20100151018A1 (en) * 2007-02-05 2010-06-17 Rd- Pharmagal Sustained-release levetiracetam composition and preparation process

Cited By (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US10154988B2 (en) 2012-11-14 2018-12-18 The Johns Hopkins University Methods and compositions for treating schizophrenia
US10624875B2 (en) 2012-11-14 2020-04-21 The Johns Hopkins University Methods and compositions for treating schizophrenia
US11160785B2 (en) 2013-03-15 2021-11-02 Agenebio Inc. Methods and compositions for improving cognitive function
US10806717B2 (en) 2013-03-15 2020-10-20 The Johns Hopkins University Methods and compositions for improving cognitive function
CN107810002B (zh) * 2015-05-22 2021-01-05 艾吉因生物股份有限公司 左乙拉西坦的延时释放药物组合物
EP3590506A1 (fr) * 2015-05-22 2020-01-08 Agenebio, Inc. Compositions pharmaceutiques à libération prolongée comportant du lévétiracétam
EA034167B1 (ru) * 2015-05-22 2020-01-14 Эйджинбайо, Инк. Фармацевтические композиции леветирацетама пролонгированного высвобождения
WO2016191288A1 (fr) * 2015-05-22 2016-12-01 Agenebio, Inc. Compositions pharmaceutiques de lévétiracétam à libération prolongée
US10159648B2 (en) 2015-05-22 2018-12-25 Agenebio, Inc. Extended release pharmaceutical compositions of levetiracetam
CN107810002A (zh) * 2015-05-22 2018-03-16 艾吉因生物股份有限公司 左乙拉西坦的延时释放药物组合物
US10925834B2 (en) 2015-05-22 2021-02-23 Agenebio, Inc. Extended release pharmaceutical compositions of levetiracetam
CN112843005A (zh) * 2015-05-22 2021-05-28 艾吉因生物股份有限公司 左乙拉西坦的延时释放药物组合物
AU2021204465B2 (en) * 2015-05-22 2022-08-18 Agenebio, Inc. Extended release pharmaceutical compositions of levetiracetam
CN112843005B (zh) * 2015-05-22 2023-02-21 艾吉因生物股份有限公司 左乙拉西坦的延时释放药物组合物
CN105030714A (zh) * 2015-07-06 2015-11-11 长春中医药大学 阿尼西坦缓释片及其制备方法
CN114146062A (zh) * 2021-03-17 2022-03-08 长沙晶易医药科技有限公司 一种组合物及其制备方法和用途

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