WO2007074996A1 - Composition pharmaceutique stable contenant du s-omeprazole et son procede de fabrication - Google Patents

Composition pharmaceutique stable contenant du s-omeprazole et son procede de fabrication Download PDF

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Publication number
WO2007074996A1
WO2007074996A1 PCT/KR2006/005601 KR2006005601W WO2007074996A1 WO 2007074996 A1 WO2007074996 A1 WO 2007074996A1 KR 2006005601 W KR2006005601 W KR 2006005601W WO 2007074996 A1 WO2007074996 A1 WO 2007074996A1
Authority
WO
WIPO (PCT)
Prior art keywords
omeprazole
inclusion complex
cyclodextrin
complex according
soluble polymer
Prior art date
Application number
PCT/KR2006/005601
Other languages
English (en)
Inventor
Nam Ho Kim
Jin Young Lee
Jae-Sun Kim
Nam Kyu Lee
Yong Youn Hwang
Ho Chul Shin
Key An Um
Original Assignee
Sk Chemicals 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 Sk Chemicals Co., Ltd. filed Critical Sk Chemicals Co., Ltd.
Publication of WO2007074996A1 publication Critical patent/WO2007074996A1/fr

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Classifications

    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B82—NANOTECHNOLOGY
    • B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
    • B82Y5/00—Nanobiotechnology or nanomedicine, e.g. protein engineering or drug delivery
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
    • 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
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/415—1,2-Diazoles
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
    • A61K47/36—Polysaccharides; Derivatives thereof, e.g. gums, starch, alginate, dextrin, hyaluronic acid, chitosan, inulin, agar or pectin
    • A61K47/38—Cellulose; Derivatives thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
    • A61K47/36—Polysaccharides; Derivatives thereof, e.g. gums, starch, alginate, dextrin, hyaluronic acid, chitosan, inulin, agar or pectin
    • A61K47/40—Cyclodextrins; Derivatives thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
    • A61K47/69—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit
    • A61K47/6949—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit inclusion complexes, e.g. clathrates, cavitates or fullerenes
    • A61K47/6951—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit inclusion complexes, e.g. clathrates, cavitates or fullerenes using 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
    • 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
    • A61K9/4841—Filling excipients; Inactive ingredients
    • A61K9/4866—Organic macromolecular compounds

Definitions

  • the present invention relates to a stable inclusion complex of S-omeprazole
  • Omeprazole is present in two isomer forms, R-isomer and S-isomer. Optically
  • S-omeprazole has better pharmaceutical profiles, improved pharmacokinetics and
  • WO 94/27988 and WO 98/54171 disclose alkali metal salts or alkaline earth
  • U.S. Patent No. 5,399,700 discloses a method for preparing an inclusion complex
  • 2004/0147481 discloses a similar method for preparing an inclusion complex of
  • S-omeprazole disclosed in these patents are complex, for example, slowly adding
  • an object of the present invention is to provide a stable inclusion
  • the present invention relates to a stable inclusion complex containing
  • inclusion complex is formed from S-omeprazole and cyclodextrin, and a method of
  • the present invention further relates to a method of preparing a stable inclusion
  • complex containing S-omeprazole comprising: 1) mixing S-omeprazole, cyclodextrin
  • S-omeprazole is stabilized using cyclodextrin and the present invention is characterized in that S-omeprazole is reacted in an alkaline
  • step 1) S-omeprazole, cyclodextrin and a water-soluble polymer are
  • the S-omeprazole may be in free form
  • S-omeprazole contains R-omeprazole in the amount of less than 5 % .
  • cyclodextrins can host hydrophobic compounds in the openings and protect them
  • cyclodextrins are classified into ⁇ -cyclodextrin, ⁇ -cyclodextrin and ⁇ -cyclodextrin.
  • ⁇ -cyclodextrin having an opening diameter of
  • Cyclodextrin is preferably used
  • the water-soluble polymer used in the present invention may improve
  • the polymer may be at least one
  • PEG polyethylene glycol
  • PVP polyvinyl pyrrolidone
  • CMC carboxymethyl cellulose
  • HPC hydroxypropyl cellulose
  • HMC hydroxyethyl cellulose
  • HEC hydroxypropyl methylcellulose
  • HPMC hydroxypropyl ethylcellulose
  • HPEC hydroxypropyl ethylcellulose
  • the water-soluble polymer is contained in the amount 0.1-100 parts
  • reaction solution becomes too viscous
  • the alkaline solution used in the present invention may be an
  • metal hydroxide may be sodium hydroxide, potassium hydroxide, barium
  • the alkali salt of inorganic acid may be a sodium salt or potassium salt of boric acid, carbonic acid or phosphoric acid.
  • the alkali salt of organic acid may be sodium acetate or sodium citrate.
  • amine may be selected from diethylamine, triethylamine, butylamine, ethylene
  • diamine triethanolamine, propylamine, dipropylamine, diethanolamine
  • the buffer may be carbonate buffer, phosphate buffer, amine salt buffer or
  • step 2) the resultant mixed solution is heated and stirred to induce
  • the stirring is performed at 20-100 0 C, preferably at 40-80 0 C.
  • 2.0-10.0 is used to adjust the pH to 7.0-10.0. More preferably, at least one
  • boric acid selected from boric acid, acetic acid and ammonium chloride is used.
  • S-omeprazole may be decomposed.
  • the reaction product is cooled, filtered, washed and dried to
  • the cooling is performed at 0-30 0 C, more preferably at 0-10 0 C. If the cooling temperature is below 0 0 C, impurities
  • the resultant inclusion complex has excellent storage stability against
  • the content (%) is the relative value compared with that of the initial
  • the inclusion complex containing S-omeprazole in accordance with the present invention has outstanding storage stability against

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Public Health (AREA)
  • Animal Behavior & Ethology (AREA)
  • Veterinary Medicine (AREA)
  • Epidemiology (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Nanotechnology (AREA)
  • Inorganic Chemistry (AREA)
  • Biotechnology (AREA)
  • Medical Informatics (AREA)
  • Molecular Biology (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • General Engineering & Computer Science (AREA)
  • Biophysics (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicinal Preparation (AREA)

Abstract

La présente invention concerne un complexe d'inclusion stable à base de S-oméprazole possédant une excellente stabilité de conservation, ainsi qu'un procédé destiné à la préparation de ce complexe. L'invention concerne plus particulièrement un complexe d'inclusion stable à base de S-oméprazole possédant une stabilité de conservation supérieure à celle d'autres compositions pharmaceutiques conventionnelles, préparé par mélange et stabilisation de S-oméprazole labile en milieu acide avec de la cyclodextrine et un polymère hydrosoluble dans une solution basique aqueuse, ainsi qu'un procédé destiné à la préparation de ce complexe.
PCT/KR2006/005601 2005-12-28 2006-12-20 Composition pharmaceutique stable contenant du s-omeprazole et son procede de fabrication WO2007074996A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
KR10-2005-0131847 2005-12-28
KR1020050131847A KR20070069567A (ko) 2005-12-28 2005-12-28 저장안정성이 우수한 ｓ-오메프라졸 함유 포접 복합체 및이의 제조방법

Publications (1)

Publication Number Publication Date
WO2007074996A1 true WO2007074996A1 (fr) 2007-07-05

Family

ID=38218197

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/KR2006/005601 WO2007074996A1 (fr) 2005-12-28 2006-12-20 Composition pharmaceutique stable contenant du s-omeprazole et son procede de fabrication

Country Status (2)

Country Link
KR (1) KR20070069567A (fr)
WO (1) WO2007074996A1 (fr)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2205218A1 (fr) * 2007-09-28 2010-07-14 CTC Bio, Inc. Composition pharmaceutique contenant de l'ésoméprazole
CN103768028A (zh) * 2014-01-15 2014-05-07 山东新时代药业有限公司 一种注射用埃索美拉唑钠无菌冻干粉末及其制备工艺
CN113893223A (zh) * 2021-09-29 2022-01-07 北京悦康科创医药科技股份有限公司 一种注射用艾司奥美拉唑钠冻干制剂及其制备方法
IT202100020933A1 (it) * 2021-08-03 2023-02-03 Farmalabor S R L “Veicolo farmaceutico e composizione farmaceutica comprendente lo stesso”

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2002098423A1 (fr) * 2001-06-06 2002-12-12 Cipla Limited Compose d'inclusion de s-omeprazole (esomeprazole) avec des cyclodextrines
US6667321B2 (en) * 1999-08-26 2003-12-23 Robert R. Whittle Alkoxy substituted benzimidazole compounds, pharmaceutical preparations containing the same, and methods of using the same
KR20050105565A (ko) * 2004-04-30 2005-11-04 에스케이케미칼주식회사 저장안정성이 우수한 벤즈이미다졸 유도체 함유 포접복합체 및 이의 제조방법

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6667321B2 (en) * 1999-08-26 2003-12-23 Robert R. Whittle Alkoxy substituted benzimidazole compounds, pharmaceutical preparations containing the same, and methods of using the same
WO2002098423A1 (fr) * 2001-06-06 2002-12-12 Cipla Limited Compose d'inclusion de s-omeprazole (esomeprazole) avec des cyclodextrines
KR20050105565A (ko) * 2004-04-30 2005-11-04 에스케이케미칼주식회사 저장안정성이 우수한 벤즈이미다졸 유도체 함유 포접복합체 및 이의 제조방법

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2205218A1 (fr) * 2007-09-28 2010-07-14 CTC Bio, Inc. Composition pharmaceutique contenant de l'ésoméprazole
EP2205218A4 (fr) * 2007-09-28 2010-11-17 Ctc Bio Inc Composition pharmaceutique contenant de l'ésoméprazole
AU2008304033B2 (en) * 2007-09-28 2014-05-01 Ctc Bio, Inc. Pharmaceutical composition containing esomeprazole
CN103768028A (zh) * 2014-01-15 2014-05-07 山东新时代药业有限公司 一种注射用埃索美拉唑钠无菌冻干粉末及其制备工艺
IT202100020933A1 (it) * 2021-08-03 2023-02-03 Farmalabor S R L “Veicolo farmaceutico e composizione farmaceutica comprendente lo stesso”
CN113893223A (zh) * 2021-09-29 2022-01-07 北京悦康科创医药科技股份有限公司 一种注射用艾司奥美拉唑钠冻干制剂及其制备方法
CN113893223B (zh) * 2021-09-29 2022-12-09 北京悦康科创医药科技股份有限公司 一种注射用艾司奥美拉唑钠冻干制剂及其制备方法

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Publication number Publication date
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