CA2449002C - Enhancement of oral bioavailability of non-emulsified formulation of prodrug esters with lecithin - Google Patents
Enhancement of oral bioavailability of non-emulsified formulation of prodrug esters with lecithin Download PDFInfo
- Publication number
- CA2449002C CA2449002C CA2449002A CA2449002A CA2449002C CA 2449002 C CA2449002 C CA 2449002C CA 2449002 A CA2449002 A CA 2449002A CA 2449002 A CA2449002 A CA 2449002A CA 2449002 C CA2449002 C CA 2449002C
- Authority
- CA
- Canada
- Prior art keywords
- lecithin
- cefditoren pivoxil
- formulation
- additional component
- emulsified
- 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.)
- Expired - Fee Related
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- 229940068977 polysorbate 20 Drugs 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
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- 230000003389 potentiating effect Effects 0.000 description 1
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- 150000003141 primary amines Chemical class 0.000 description 1
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- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- AWUCVROLDVIAJX-GSVOUGTGSA-N sn-glycerol 3-phosphate Chemical compound OC[C@@H](O)COP(O)(O)=O AWUCVROLDVIAJX-GSVOUGTGSA-N 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- PPASLZSBLFJQEF-RKJRWTFHSA-M sodium ascorbate Substances [Na+].OC[C@@H](O)[C@H]1OC(=O)C(O)=C1[O-] PPASLZSBLFJQEF-RKJRWTFHSA-M 0.000 description 1
- 235000010378 sodium ascorbate Nutrition 0.000 description 1
- 229960005055 sodium ascorbate Drugs 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
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- 229940079832 sodium starch glycolate Drugs 0.000 description 1
- 229920003109 sodium starch glycolate Polymers 0.000 description 1
- PPASLZSBLFJQEF-RXSVEWSESA-M sodium-L-ascorbate Chemical compound [Na+].OC[C@H](O)[C@H]1OC(=O)C(O)=C1[O-] PPASLZSBLFJQEF-RXSVEWSESA-M 0.000 description 1
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- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
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- CBXCPBUEXACCNR-UHFFFAOYSA-N tetraethylammonium Chemical compound CC[N+](CC)(CC)CC CBXCPBUEXACCNR-UHFFFAOYSA-N 0.000 description 1
- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
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- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 230000008280 toxic mechanism Effects 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
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Classifications
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/65—Tetracyclines
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- 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
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/34—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having five-membered rings with one oxygen as the only ring hetero atom, e.g. isosorbide
- A61K31/343—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having five-membered rings with one oxygen as the only ring hetero atom, e.g. isosorbide condensed with a carbocyclic ring, e.g. coumaran, bufuralol, befunolol, clobenfurol, amiodarone
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- 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
- A61K31/4353—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 ortho- or peri-condensed with heterocyclic ring systems
- A61K31/4375—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 ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a six-membered ring having nitrogen as a ring heteroatom, e.g. quinolizines, naphthyridines, berberine, vincamine
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- 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
- A61K31/54—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame
- A61K31/542—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame ortho- or peri-condensed with heterocyclic ring systems
- A61K31/545—Compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins, cefaclor, or cephalexine
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- 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
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/7042—Compounds having saccharide radicals and heterocyclic rings
- A61K31/7048—Compounds having saccharide radicals and heterocyclic rings having oxygen as a ring hetero atom, e.g. leucoglucosan, hesperidin, erythromycin, nystatin, digitoxin or digoxin
-
- 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
- A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
- A61K9/16—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction
- A61K9/1605—Excipients; Inactive ingredients
- A61K9/1617—Organic compounds, e.g. phospholipids, fats
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- A—HUMAN NECESSITIES
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- 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
- A61K9/2013—Organic compounds, e.g. phospholipids, fats
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- 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
- A61K9/0087—Galenical forms not covered by A61K9/02 - A61K9/7023
- A61K9/0095—Drinks; Beverages; Syrups; Compositions for reconstitution thereof, e.g. powders or tablets to be dispersed in a glass of water; Veterinary drenches
-
- 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
- A61K9/2095—Tabletting processes; Dosage units made by direct compression of powders or specially processed granules, by eliminating solvents, by melt-extrusion, by injection molding, by 3D printing
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Molecular Biology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- Biophysics (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US29414101P | 2001-05-29 | 2001-05-29 | |
| US86735301A | 2001-05-29 | 2001-05-29 | |
| US60/294,141 | 2001-05-29 | ||
| US09/867,353 | 2001-05-29 | ||
| PCT/US2002/016428 WO2002096354A2 (en) | 2001-05-29 | 2002-05-28 | Enhancement of oral bioavailability of non-emulsified formulation of prodrug esters with lecithin |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2449002A1 CA2449002A1 (en) | 2002-12-05 |
| CA2449002C true CA2449002C (en) | 2011-08-16 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2449002A Expired - Fee Related CA2449002C (en) | 2001-05-29 | 2002-05-28 | Enhancement of oral bioavailability of non-emulsified formulation of prodrug esters with lecithin |
Country Status (5)
| Country | Link |
|---|---|
| EP (1) | EP1401402B1 (enExample) |
| JP (1) | JP5051865B2 (enExample) |
| CA (1) | CA2449002C (enExample) |
| MX (1) | MXPA03010945A (enExample) |
| WO (1) | WO2002096354A2 (enExample) |
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| AU2003235962A1 (en) | 2002-10-02 | 2004-04-23 | Meiji Seika Kaisha, Ltd. | Antibacterial medicinal composition of enhanced oral absorptivity |
| PE20061107A1 (es) | 2005-03-14 | 2006-12-08 | Wyeth Corp | Composiciones de tigeciclina y metodos para su preparacion |
| EP1954253A4 (en) * | 2005-06-08 | 2011-07-27 | Elan Pharma Int Ltd | NANOTEILIC AND CONTROLLED RELEASED COMPOSITIONS WITH CEFDITORS |
| JP2007106684A (ja) * | 2005-10-11 | 2007-04-26 | Sawai Pharmaceutical Co Ltd | 抗菌性医薬組成物 |
| EP1952803A1 (en) | 2007-01-23 | 2008-08-06 | KTB-Tumorforschungs GmbH | Solid pharmaceutical dosage form containing hydrogenated phospholipids |
| EP2373344B1 (en) * | 2008-12-08 | 2016-03-30 | F. Hoffmann-La Roche AG | Combined drug administration |
| WO2012174731A1 (en) * | 2011-06-24 | 2012-12-27 | Cheng Haiyung | Method and improved pharmaceutical composition for improving the absorption of an ester prodrug |
| KR101561963B1 (ko) * | 2013-05-23 | 2015-10-22 | 영진약품공업 주식회사 | 세프디토렌 피복실의 신규 결정 형태 및 이의 제조 방법 |
| WO2016114727A1 (en) * | 2015-01-16 | 2016-07-21 | Öğün Yusuf Toktamiş | Cefditoren pivoxil compositions with improved stability and production methods thereof |
| CN110143957B (zh) * | 2019-06-20 | 2020-12-25 | 重庆医药高等专科学校 | 头孢妥仑匹酯开环物的制备方法 |
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| IE58487B1 (en) | 1984-09-07 | 1993-09-22 | Kaisha Maiji Seika | New cephalosporin compounds and the production thereof |
| JPS6216431A (ja) * | 1985-07-15 | 1987-01-24 | Nakanishi Michio | 医薬組成物 |
| JPS62205088A (ja) | 1986-03-03 | 1987-09-09 | Meiji Seika Kaisha Ltd | 新規セフエム化合物 |
| US5651991A (en) | 1987-10-28 | 1997-07-29 | Nippon Shinyaku Co. Ltd. | Drug carriers |
| EP0477270A1 (en) * | 1989-06-15 | 1992-04-01 | Med-Tal, Inc. | Prevention and treatment of microbial infection by phosphoglycerides |
| JP2785981B2 (ja) | 1989-11-20 | 1998-08-13 | 株式会社資生堂 | 乳化組成物 |
| US5319116A (en) | 1992-02-12 | 1994-06-07 | Gary Viole | Lecithin fractions and dilutions, methods for their preparation and pharmacological uses thereof |
| US6113921A (en) | 1993-03-23 | 2000-09-05 | Pharmos Corp. | Topical and transdermal delivery system utilizing submicron oil spheres |
| JPH0717866A (ja) * | 1993-06-16 | 1995-01-20 | Meiji Seika Kaisha Ltd | 医薬組成物 |
| JPH0840907A (ja) | 1994-08-03 | 1996-02-13 | Meiji Seika Kaisha Ltd | セファロスポリン注射剤 |
| AR004014A1 (es) | 1995-10-13 | 1998-09-30 | Meiji Seika Kaisha | Una composicion antibacteriana de cefditoren pivoxilo para administracion oral y metodo para obtener dicha composicion |
| CA2266404A1 (en) | 1996-09-17 | 1998-03-26 | Amur Pharmaceuticals, Inc. | Phospholipid drug derivatives |
| US6165997A (en) * | 1997-11-20 | 2000-12-26 | Statens Serum Institut | Phospholipids having antimicrobial activity with or without the presence of antimicrobials |
| ES2153786B1 (es) * | 1999-06-10 | 2001-10-16 | S A L V A T Lab Sa | Composicion farmaceutica liquida para la administracion oral de principios activos amargos y susceptibles de hidrolisis. |
-
2002
- 2002-05-28 CA CA2449002A patent/CA2449002C/en not_active Expired - Fee Related
- 2002-05-28 MX MXPA03010945A patent/MXPA03010945A/es active IP Right Grant
- 2002-05-28 WO PCT/US2002/016428 patent/WO2002096354A2/en not_active Ceased
- 2002-05-28 JP JP2002592867A patent/JP5051865B2/ja not_active Expired - Fee Related
- 2002-05-28 EP EP02737142.6A patent/EP1401402B1/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| MXPA03010945A (es) | 2004-02-27 |
| WO2002096354A2 (en) | 2002-12-05 |
| JP2005515155A (ja) | 2005-05-26 |
| EP1401402B1 (en) | 2016-09-07 |
| WO2002096354A3 (en) | 2003-03-20 |
| EP1401402A2 (en) | 2004-03-31 |
| CA2449002A1 (en) | 2002-12-05 |
| EP1401402A4 (en) | 2006-12-06 |
| JP5051865B2 (ja) | 2012-10-17 |
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| EEER | Examination request | ||
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