WO1999040932A1 - Mixed micellar pharmaceutical delivery system and method of preparation - Google Patents

Mixed micellar pharmaceutical delivery system and method of preparation Download PDF

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Publication number
WO1999040932A1
WO1999040932A1 PCT/CA1999/000106 CA9900106W WO9940932A1 WO 1999040932 A1 WO1999040932 A1 WO 1999040932A1 CA 9900106 W CA9900106 W CA 9900106W WO 9940932 A1 WO9940932 A1 WO 9940932A1
Authority
WO
WIPO (PCT)
Prior art keywords
formulation
insulin
acid
absorption enhancing
sodium
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/CA1999/000106
Other languages
English (en)
French (fr)
Other versions
WO1999040932A9 (en
Inventor
Pankaj Modi
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.)
Generex Pharmaceuticals Inc
Original Assignee
Generex Pharmaceuticals Inc
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 Generex Pharmaceuticals Inc filed Critical Generex Pharmaceuticals Inc
Priority to AU25053/99A priority Critical patent/AU750197B2/en
Priority to DE69937546T priority patent/DE69937546T2/de
Priority to DK99904638T priority patent/DK1053011T3/da
Priority to JP2000531183A priority patent/JP4499282B2/ja
Priority to NZ506024A priority patent/NZ506024A/en
Priority to EP99904638A priority patent/EP1053011B1/en
Publication of WO1999040932A1 publication Critical patent/WO1999040932A1/en
Publication of WO1999040932A9 publication Critical patent/WO1999040932A9/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

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
    • A61K9/006—Oral mucosa, e.g. mucoadhesive forms, sublingual droplets; Buccal patches or films; Buccal sprays
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K38/00—Medicinal preparations containing peptides
    • A61K38/16—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
    • A61K38/17—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans
    • A61K38/22—Hormones
    • A61K38/28—Insulins
    • 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
    • A61K9/0043—Nose
    • 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
    • A61K9/0056—Mouth soluble or dispersible forms; Suckable, eatable, chewable coherent forms; Forms rapidly disintegrating in the mouth; Lozenges; Lollipops; Bite capsules; Baked products; Baits or other oral forms for animals
    • 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
    • A61K9/10—Dispersions; Emulsions
    • A61K9/107—Emulsions ; Emulsion preconcentrates; Micelles
    • A61K9/1075—Microemulsions or submicron emulsions; Preconcentrates or solids thereof; Micelles, e.g. made of phospholipids or block copolymers
    • 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
    • A61K9/10—Dispersions; Emulsions
    • A61K9/127—Synthetic bilayered vehicles, e.g. liposomes or liposomes with cholesterol as the only non-phosphatidyl surfactant
    • A61K9/1271—Non-conventional liposomes, e.g. PEGylated liposomes or liposomes coated or grafted with polymers
    • A61K9/1272—Non-conventional liposomes, e.g. PEGylated liposomes or liposomes coated or grafted with polymers comprising non-phosphatidyl surfactants as bilayer-forming substances, e.g. cationic lipids or non-phosphatidyl liposomes coated or grafted with polymers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P23/00—Anaesthetics
    • 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
    • A61P25/04—Centrally acting analgesics, e.g. opioids
    • 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
    • A61P25/20—Hypnotics; Sedatives
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
    • A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
    • 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
    • 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
    • A61P31/12—Antivirals
    • 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
    • A61P31/12—Antivirals
    • A61P31/14—Antivirals for RNA viruses
    • A61P31/16—Antivirals for RNA viruses for influenza or rhinoviruses
    • 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
    • A61P31/12—Antivirals
    • A61P31/14—Antivirals for RNA viruses
    • A61P31/18—Antivirals for RNA viruses for HIV
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P7/00—Drugs for disorders of the blood or the extracellular fluid
    • A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors

Definitions

  • mixed micellar pharmaceutical formulation is suitably diluted to avoid irritation of the nasal passages.
  • the mixed micellar formulation is formed by sonication of the aqueous micellar pharmaceutical agent composition in the presence of lecithin.
  • compositions of the present invention require that the pharmaceutical formulation be in mixed micellar form.
  • the first micellar solution may be made by adding a buffer solution to powdered insulin, and then stirring until the powder is dissolved and a clear solution is obtained.
  • a typical buffer solution is an aqueous solution of sodium salicylate and sodium lauryl sulphate and disodium edetate. Typical concentration of sodium salicylate and sodium lauryl sulphate in the aqueous solution are about 3 to 20 wt . /wt . % of each compound in the solution.
  • insulin is present in the micellar solution in an amount which will give a concentration of about 2 to 4 wt . /wt . % of the final formulation.
  • the volunteers received 10 units insulin by injection (regular fast acting insulin, available from Eli Lilly) .
  • the volunteers received 100 units (1 mL volume per drop, approximately 20 drops) of the above-prepared oral insulin (10 times the injection dose) .
  • blood glucose levels were monitored every 15 minutes by Bayer's Glucometer Elite.
  • Oral insulin (50 units) was formulated using only alkali metal lauryl sulphate (5% by wt) . Blood glucose levels were monitored every 15 minutes using Bayer's glucometer Elite for 3 hours and the average results for four volunteers are shown in Table VI .
  • micellar oral insulin 50 units was formulated using alkali metal lauryl sulphate and sodium salicylate (both 4.4% by wt . ) and alkali metal edetate (2.2% by wt) with Phospholipon-H (10 mg) and tested on healthy volunteers .
  • the method involved mixing the sodium lauryl sulphate, sodium salicylate and alkali metal edetate with water in a beaker with a magnetic stirrer at medium speed until the ingredients were dissolved, to form buffer solution. Insulin powder was placed in a beaker and to this powder was added the buffer solution.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Veterinary Medicine (AREA)
  • General Health & Medical Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Public Health (AREA)
  • Medicinal Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • Epidemiology (AREA)
  • Organic Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Molecular Biology (AREA)
  • Diabetes (AREA)
  • Virology (AREA)
  • Biophysics (AREA)
  • Oncology (AREA)
  • Communicable Diseases (AREA)
  • Zoology (AREA)
  • Dispersion Chemistry (AREA)
  • Physiology (AREA)
  • Nutrition Science (AREA)
  • Endocrinology (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Biomedical Technology (AREA)
  • Otolaryngology (AREA)
  • Anesthesiology (AREA)
  • Immunology (AREA)
  • Gastroenterology & Hepatology (AREA)
  • Pain & Pain Management (AREA)
  • Neurosurgery (AREA)
  • Neurology (AREA)
  • Hematology (AREA)
  • Pulmonology (AREA)
  • Emergency Medicine (AREA)
  • Tropical Medicine & Parasitology (AREA)
PCT/CA1999/000106 1998-02-10 1999-02-05 Mixed micellar pharmaceutical delivery system and method of preparation Ceased WO1999040932A1 (en)

Priority Applications (6)

Application Number Priority Date Filing Date Title
AU25053/99A AU750197B2 (en) 1998-02-10 1999-02-05 Mixed micellar pharmaceutical delivery system and method of preparation
DE69937546T DE69937546T2 (de) 1998-02-10 1999-02-05 Mischmizell-arzneistoffverabreichungssystem und verfahren zu dessen herstellung
DK99904638T DK1053011T3 (da) 1998-02-10 1999-02-05 System i form af blandede miceller til indgivelse af lægemiddelstoffer og fremgangsmåde til fremstilling heraf
JP2000531183A JP4499282B2 (ja) 1998-02-10 1999-02-05 混合ミセル状薬剤の移送システム及び調製方法
NZ506024A NZ506024A (en) 1998-02-10 1999-02-05 Mixed micellar pharmaceutical delivery system and method of preparation
EP99904638A EP1053011B1 (en) 1998-02-10 1999-02-05 Mixed micellar pharmaceutical delivery system and method of preparation

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US09/021,114 1998-02-10
US09/021,114 US6017545A (en) 1998-02-10 1998-02-10 Mixed micellar delivery system and method of preparation
US09/216,733 1998-12-21
US09/216,733 US6231882B1 (en) 1998-02-10 1998-12-21 Mixed micellar delivery system and method of preparation

Publications (2)

Publication Number Publication Date
WO1999040932A1 true WO1999040932A1 (en) 1999-08-19
WO1999040932A9 WO1999040932A9 (en) 2000-03-30

Family

ID=21802420

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/CA1999/000106 Ceased WO1999040932A1 (en) 1998-02-10 1999-02-05 Mixed micellar pharmaceutical delivery system and method of preparation

Country Status (12)

Country Link
US (2) US6017545A (https=)
EP (1) EP1053011B1 (https=)
JP (1) JP4499282B2 (https=)
AT (1) ATE378062T1 (https=)
AU (1) AU750197B2 (https=)
BR (1) BR9804295A (https=)
DE (1) DE69937546T2 (https=)
DK (1) DK1053011T3 (https=)
ES (1) ES2296380T3 (https=)
NZ (1) NZ506024A (https=)
PT (1) PT1053011E (https=)
WO (1) WO1999040932A1 (https=)

Cited By (20)

* Cited by examiner, † Cited by third party
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WO2000018371A1 (en) * 1998-09-27 2000-04-06 Generex Pharmaceuticals Inc. Proteinic drug delivery system using membrane mimetics
WO2000037053A1 (en) * 1998-12-21 2000-06-29 Generex Pharmaceuticals Inc. Large molecule drug delivery system using aerosolized membrane-mimetic amphiphiles
WO2000037051A1 (en) * 1998-12-21 2000-06-29 Generex Pharmaceuticals Inc. Aerosol formulations for buccal and pulmonary application
WO2000037052A1 (en) * 1998-12-21 2000-06-29 Generex Pharmaceuticals Inc. Pulmonary drug delivery
WO2000056291A1 (en) * 1999-03-19 2000-09-28 Generex Pharmaceuticals Inc. Pharmaceutical solubilized in aerosol propellant
WO2001015666A1 (en) * 1999-08-31 2001-03-08 Generex Pharmaceuticals Inc. Mixed micellar pharmaceutical delivery system and method of preparation
WO2001017506A1 (en) * 1999-09-07 2001-03-15 Generex Pharmaceuticals Inc. Proteinic drug delivery system using membrane mimetics
WO2001039794A1 (fr) * 1999-11-30 2001-06-07 Oao 'quantum Satis' Medicament a usage peroral contenant de l'insuline et procede de fabrication correspondant
WO2001087268A1 (en) * 2000-05-19 2001-11-22 Generex Pharmaceuticals Inc. Micellar pharmaceutical compositions for buccal and pulmonary application
WO2001066085A3 (en) * 2000-03-06 2002-04-11 Generex Pharm Inc Micellar pharmaceutical compositions for buccal and pulmonary application
WO2001072278A3 (en) * 2000-03-30 2002-04-11 Generex Pharm Inc Method for administering insulin to the buccal region
WO2002051380A1 (de) 2000-12-22 2002-07-04 Audit Institute For Medical Services And Quality Assurance Gmbh Neue pharmazeutische zusammensetzung von wasserlöslichen oder schwer wasserlöslichen wirkstoffen
EP1230917A1 (de) * 2001-02-08 2002-08-14 Vectron Therapeutics AG Invasomen zur Therapie von Erkrankungen, ihre Herstellung und Verwendung
AU763251B2 (en) * 1998-02-10 2003-07-17 Generex Pharmaceuticals Inc. Mixed micellar pharmaceutical delivery system and method for preparation
EP1338272A1 (en) * 1998-12-21 2003-08-27 Generex Pharmaceuticals Inc. Aerosol formulations for buccal and pulmonary application comprising chenodeoxycholate or deoxycholate
JP2006517190A (ja) * 2002-12-24 2006-07-20 イーゲー スプリューテクニーク ゲーエムベーハー ウント ツェーオー．カーゲー 界面活性物質としてレシチンを含む投与エーロゾル
US7087215B2 (en) 1998-12-21 2006-08-08 Generex Pharmaceuticals Incorporated Methods of administering and enhancing absorption of pharmaceutical agents
AU2006200276B2 (en) * 1998-12-21 2007-11-29 Generex Pharmaceuticals Inc. Micellar pharmaceutical compositions for buccal and pulmonary application
CN115154427A (zh) * 2022-08-15 2022-10-11 保定冀中药业有限公司 一种提高四黄止痢颗粒治疗湿热泻痢效果的制备方法
EP3893847A4 (en) * 2018-12-10 2022-11-02 Halo Science LLC STABLE FORMULATIONS OF ANESTHETICS AND RELATED DOSAGE FORMS

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FR2686899B1 (fr) * 1992-01-31 1995-09-01 Rhone Poulenc Rorer Sa Nouveaux polypeptides biologiquement actifs, leur preparation et compositions pharmaceutiques les contenant.
US6017545A (en) * 1998-02-10 2000-01-25 Modi; Pankaj Mixed micellar delivery system and method of preparation
US6350458B1 (en) 1998-02-10 2002-02-26 Generex Pharmaceuticals Incorporated Mixed micellar drug deliver system and method of preparation
US7070799B1 (en) * 1998-02-10 2006-07-04 Generex Pharmaceuticals, Inc. Method for administering insulin to the buccal region
US6635617B1 (en) * 1998-10-16 2003-10-21 Novo Nordisk A/S Insulin preparations for pulmonary delivery containing menthol
US6849263B2 (en) * 1998-12-21 2005-02-01 Generex Pharmaceutical Incorporated Pharmaceutical compositions for buccal delivery of pain relief medications
US6436367B1 (en) * 1998-12-21 2002-08-20 Generex Pharmaceuticals Inc. Aerosol formulations for buccal and pulmonary application
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JP4499282B2 (ja) 2010-07-07
PT1053011E (pt) 2008-02-14
DE69937546T2 (de) 2008-05-29
AU2505399A (en) 1999-08-30
NZ506024A (en) 2002-02-01
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DK1053011T3 (da) 2008-03-25
AU750197B2 (en) 2002-07-11
EP1053011A1 (en) 2000-11-22
JP2003522096A (ja) 2003-07-22
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ATE378062T1 (de) 2007-11-15
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