CA2440578A1 - Oral peptide pharmaceutical dosage form and method of production - Google Patents

Oral peptide pharmaceutical dosage form and method of production Download PDF

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Publication number
CA2440578A1
CA2440578A1 CA002440578A CA2440578A CA2440578A1 CA 2440578 A1 CA2440578 A1 CA 2440578A1 CA 002440578 A CA002440578 A CA 002440578A CA 2440578 A CA2440578 A CA 2440578A CA 2440578 A1 CA2440578 A1 CA 2440578A1
Authority
CA
Canada
Prior art keywords
peptide
lamination
dosage form
lowering agent
layer
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.)
Granted
Application number
CA002440578A
Other languages
French (fr)
Other versions
CA2440578C (en
Inventor
George Crotts
Isaac Ghebre-Sellassie
Ashlesh Sheth
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.)
Enteris Biopharma Inc
Original Assignee
Individual
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 Individual filed Critical Individual
Publication of CA2440578A1 publication Critical patent/CA2440578A1/en
Application granted granted Critical
Publication of CA2440578C publication Critical patent/CA2440578C/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • 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
    • A61K38/23—Calcitonins
    • 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
    • A61K9/2072—Pills, tablets, discs, rods characterised by shape, structure or size; Tablets with holes, special break lines or identification marks; Partially coated tablets; Disintegrating flat shaped forms
    • A61K9/2086—Layered tablets, e.g. bilayer tablets; Tablets of the type inert core-active coat
    • 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
    • A61K9/2013—Organic compounds, e.g. phospholipids, fats
    • 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
    • A61K9/28—Dragees; Coated pills or tablets, e.g. with film or compression coating
    • A61K9/2806—Coating materials
    • A61K9/2833—Organic macromolecular compounds
    • A61K9/284—Organic macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyvinyl pyrrolidone
    • A61K9/2846—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
    • A61K9/28—Dragees; Coated pills or tablets, e.g. with film or compression coating
    • A61K9/2886—Dragees; Coated pills or tablets, e.g. with film or compression coating having two or more different drug-free coatings; Tablets of the type inert core-drug layer-inactive layer

Abstract

A pharmaceutical composition for oral delivery of a peptide is in the form o f a lamination having at least two layers. The first layer of the lamination includes at least one pharmaceutically acceptable pH-lowering agent. The second layer includes a therapeutically effective amount of the peptide. The composition also includes at least one absorption enhancer effective to promote bioavailability of the peptide, which is preferably in the second layer, and an enteric coating surrounding the lamination. In a preferred dosage form of a tablet, a water-soluble coating is applied between the lamination and the enteric coating which substantially prevents contact between the pH-lowering agent and the enteric coating. In a preferred embodiment, the peptide is salmon calcitonin, the pH-lowering agent is citri c acid, and the absorption enhancer is lauroyl l-carnitine.
CA002440578A 2001-03-08 2002-03-08 Oral peptide pharmaceutical dosage form and method of production Expired - Lifetime CA2440578C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US27431701P 2001-03-08 2001-03-08
US60/274,317 2001-03-08
PCT/US2002/007197 WO2002072075A1 (en) 2001-03-08 2002-03-08 Oral peptide pharmaceutical dosage form and method of production

Publications (2)

Publication Number Publication Date
CA2440578A1 true CA2440578A1 (en) 2002-09-19
CA2440578C CA2440578C (en) 2009-05-26

Family

ID=23047692

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002440578A Expired - Lifetime CA2440578C (en) 2001-03-08 2002-03-08 Oral peptide pharmaceutical dosage form and method of production

Country Status (8)

Country Link
US (1) US7316819B2 (en)
EP (1) EP1365747A4 (en)
JP (2) JP2004525123A (en)
AU (1) AU2002306681B2 (en)
CA (1) CA2440578C (en)
MX (1) MXPA03008072A (en)
NZ (1) NZ527844A (en)
WO (1) WO2002072075A1 (en)

Families Citing this family (73)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20030091708A1 (en) * 1997-03-13 2003-05-15 Garwood Anthony J.M. Irradiation in low oxygen environment
US6844315B2 (en) * 1998-05-20 2005-01-18 Erasmus Universiteit Rotterdam Immunoregulator
US8680059B2 (en) * 1998-05-20 2014-03-25 Biotempt B.V. Oligopeptide acetate and formulations thereof
US20030220258A1 (en) 2001-12-21 2003-11-27 Robbert Benner Treatment of ischemic events
US20040202645A1 (en) * 2003-04-08 2004-10-14 Khan Nisar Ahmed Administration of gene-regulatory peptides
US7358330B2 (en) 2001-03-29 2008-04-15 Biotempt B.V. Immunoregulatory compositions
EP1300418A1 (en) * 2001-10-04 2003-04-09 Erasmus Universiteit Rotterdam Gene regulation by oligopeptides
US7560433B2 (en) 2001-12-21 2009-07-14 Biotempt B.V. Treatment of multiple sclerosis (MS)
US7786084B2 (en) * 2001-12-21 2010-08-31 Biotempt B.V. Treatment of burns
US20030220257A1 (en) * 2001-12-21 2003-11-27 Robbert Benner Treatment of trauma
US20080318871A1 (en) * 2001-12-21 2008-12-25 Khan Nisar A Treatment of neurological disorders
US20080242837A1 (en) * 2001-12-21 2008-10-02 Khan Nisar A Peptide compositions
US20030181488A1 (en) * 2002-03-07 2003-09-25 Boehringer Ingelheim Pharma Gmbh & Co. Kg Administration form for the oral application of 3-[(2-{[4-(hexyloxycarbonylamino-imino-methyl)-phenylamino]-methyl}-1-methyl-1H-benzimidazol-5-carbonyl)-pyridin-2-yl-amino]-propionic acid ethyl ester and the salts thereof
US7156652B2 (en) * 2003-10-03 2007-01-02 Daiwa Kasei Industry Co., Ltd. Motor-driven injection molding apparatus
CA2536401C (en) * 2003-11-04 2011-08-30 Shire Laboratories Inc. Compositions of quaternary ammonium compounds containing bioavailability enhancers
US20090227505A1 (en) * 2004-01-07 2009-09-10 Biotempt B.V. Methods and uses for protein breakdown products
PE20142101A1 (en) * 2004-03-17 2014-12-27 Novartis Ag PHARMACEUTICAL COMPOSITIONS OF ALISKIREN
US20050282756A1 (en) 2004-06-18 2005-12-22 Mehta Nozer M Oral delivery of peptide pharmaceutical compositions
US8268791B2 (en) * 2004-08-25 2012-09-18 Aegis Therapeutics, Llc. Alkylglycoside compositions for drug administration
US9895444B2 (en) 2004-08-25 2018-02-20 Aegis Therapeutics, Llc Compositions for drug administration
US20140162965A1 (en) 2004-08-25 2014-06-12 Aegis Therapeutics, Inc. Compositions for oral drug administration
US20060046962A1 (en) 2004-08-25 2006-03-02 Aegis Therapeutics Llc Absorption enhancers for drug administration
US20090047347A1 (en) * 2005-07-29 2009-02-19 Aegis Therapeutics, Inc. Compositions for Drug Administration
CA2578202C (en) * 2004-08-30 2013-12-17 Toray Industries, Inc. Fractionation apparatus
AU2006266609C1 (en) * 2005-07-05 2011-10-27 Biotempt B.V. Treatment of tumors
US8093207B2 (en) 2005-12-09 2012-01-10 Unigene Laboratories, Inc. Fast-acting oral peptide pharmaceutical products
EP1864692A1 (en) * 2006-06-07 2007-12-12 Biotempt B.V. Use of peptides for the control of radiation injury
AU2006236006B2 (en) * 2006-04-13 2012-09-06 The University Of Queensland Cyclised a-conotoxin peptides
US8226949B2 (en) 2006-06-23 2012-07-24 Aegis Therapeutics Llc Stabilizing alkylglycoside compositions and methods thereof
ES2456333T3 (en) * 2007-02-12 2014-04-22 Biotempt B.V. Traumatic hemorrhage treatment with short oligopeptides
US20080260820A1 (en) * 2007-04-19 2008-10-23 Gilles Borrelly Oral dosage formulations of protease-resistant polypeptides
WO2008132727A2 (en) * 2007-04-26 2008-11-06 Technion Research And Development Foundation Ltd Oral delivery of proteins and peptides
US8377863B2 (en) * 2007-05-29 2013-02-19 Unigene Laboratories Inc. Peptide pharmaceutical for oral delivery
CA2689479A1 (en) * 2007-06-04 2008-12-11 Bce Inc. Methods and systems for validating online transactions using location information
US8969514B2 (en) 2007-06-04 2015-03-03 Synergy Pharmaceuticals, Inc. Agonists of guanylate cyclase useful for the treatment of hypercholesterolemia, atherosclerosis, coronary heart disease, gallstone, obesity and other cardiovascular diseases
CN101772513B (en) 2007-06-04 2013-11-13 协同医药品公司 Agonists of guanylate cyclase useful for the treatment of gastrointestinal disorders, inflammation, cancer and other disorders
FR2925333B1 (en) * 2007-12-19 2012-04-13 Farid Bennis PHARMACEUTICAL COMPOSITIONS COMPRISING AT LEAST ONE PROTEIN ACTIVE INGREDIENT PROTECTS DIGESTIVE ENZYMES
CA2756690C (en) 2008-03-28 2016-08-16 Hale Biopharma Ventures, Llc Administration of benzodiazepine compositions
ES2522968T3 (en) 2008-06-04 2014-11-19 Synergy Pharmaceuticals Inc. Guanylate cyclase agonists useful for the treatment of gastrointestinal disorders, inflammation, cancer and other disorders
JP2011528375A (en) 2008-07-16 2011-11-17 シナジー ファーマシューティカルズ インコーポレイテッド Guanylate cyclase agonists useful for the treatment of gastrointestinal disorders, inflammation, cancer, and other disorders
US8440631B2 (en) 2008-12-22 2013-05-14 Aegis Therapeutics, Llc Compositions for drug administration
EP2255794A1 (en) * 2009-05-29 2010-12-01 H e x a l Aktiengesellschaft Enteric coating
CA2784120A1 (en) 2009-12-16 2011-07-14 Nod Pharmaceuticals, Inc. Compositions and methods for oral drug delivery
US20110142889A1 (en) * 2009-12-16 2011-06-16 Nod Pharmaceuticals, Inc. Compositions and methods for oral drug delivery
MX2013000314A (en) 2010-07-09 2013-01-29 Affibody Ab Polypeptides.
US9616097B2 (en) 2010-09-15 2017-04-11 Synergy Pharmaceuticals, Inc. Formulations of guanylate cyclase C agonists and methods of use
WO2012174158A2 (en) 2011-06-14 2012-12-20 Hale Biopharma Ventures, Llc Administration of benzodiazepine
CA2854175A1 (en) 2011-11-02 2013-05-10 Keybioscience Ag Peptide analogs for treating diseases and disorders
DK3095484T3 (en) 2011-11-02 2018-06-25 Keybioscience Ag CALCITONIN MIMETICS FOR THE TREATMENT OF DISEASES AND DISORDERS
US20150018271A1 (en) 2012-03-01 2015-01-15 Yeda Research And Development Co. Ltd. Hsp60 derived peptides and peptide analogs for suppression and treatment of non-autoimmune diabetes
EP2830665A1 (en) * 2012-03-28 2015-02-04 Affibody AB Oral administration
KR102123457B1 (en) 2012-09-25 2020-06-16 애피바디 에이비 Albumin binding polypeptide
AU2014218599C1 (en) 2013-02-25 2018-09-06 Bausch Health Ireland Limited Guanylate cyclase receptor agonists for use in colonic cleansing
JP6375314B2 (en) 2013-03-05 2018-08-15 エンテリス・バイオファーマ・インコーポレイテッドＥｎｔｅｒｉｓ Ｂｉｏｐｈａｒｍａ，Ｉｎｃ． Solid oral dosage form
US10031183B2 (en) 2013-03-07 2018-07-24 Rai Strategic Holdings, Inc. Spent cartridge detection method and system for an electronic smoking article
AU2014235209B2 (en) 2013-03-15 2018-06-14 Bausch Health Ireland Limited Guanylate cyclase receptor agonists combined with other drugs
JP2016514671A (en) 2013-03-15 2016-05-23 シナジー ファーマシューティカルズ インコーポレイテッド Guanylate cyclase agonists and uses thereof
CA2926691A1 (en) 2013-10-10 2015-04-16 Synergy Pharmaceuticals, Inc. Agonists of guanylate cyclase useful for the treatment of opioid induced dysfunctions
ES2713851T3 (en) 2013-11-14 2019-05-24 Keybioscience Ag Mimetics of calcitonin for the treatment of diseases and disorders
WO2015091957A1 (en) 2013-12-20 2015-06-25 Affibody Ab Engineered albumin binding polypeptide
CN103645665B (en) * 2013-12-24 2016-06-08 南京富士通南大软件技术有限公司 A kind of programmable signal generator and signal generating method thereof
US20170174764A1 (en) 2014-03-27 2017-06-22 Yeda Research And Development Co. Ltd. T-cell receptor cdr3 peptides and antibodies
GB201500263D0 (en) 2015-01-08 2015-02-25 Keybioscience Ag Calcitonin analogues for treating diseases and disorders
KR102294577B1 (en) * 2015-01-12 2021-08-26 엔터리스 바이오파마, 인크. solid oral dosage form
EP3402804A1 (en) 2016-01-11 2018-11-21 Synergy Pharmaceuticals Inc. Formulations and methods for treating ulcerative colitis
WO2018026993A1 (en) * 2016-08-05 2018-02-08 Tarsa Therapeutics, Inc. Room temperature stable oral calcitonin formulation
US20180055090A1 (en) * 2016-08-31 2018-03-01 Altria Client Services Llc Methods and systems for cartridge identification
GB201704429D0 (en) 2017-03-21 2017-05-03 Keybioscience Ag Calcitonin mimetics for treating diseases and disorders
GB201707955D0 (en) 2017-05-18 2017-07-05 Keybioscience Ag Dual amylin and calcitonin receptor agonists for treating diseases and disorders
GB201813677D0 (en) 2018-08-22 2018-10-03 Keybioscience Ag Calcitonin mimetics for treating diseases and disorders
GB201813678D0 (en) 2018-08-22 2018-10-03 Keybioscience Ag Acylated calcitonin mimetics
WO2021034629A1 (en) * 2019-08-16 2021-02-25 9 Meters Biopharma, Inc. Larazotide formulations
EP4226918A1 (en) 2022-02-15 2023-08-16 Filip Majewski Pharmaceutical single dosage form for oral delivery of peptides

Family Cites Families (23)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5944311A (en) * 1982-09-07 1984-03-12 Santen Pharmaceut Co Ltd Slow-releasing granule and its preparation
SG64368A1 (en) 1988-06-30 1999-04-27 Astra Ab Dermorphin analogs their methods of preparation pharmaceutical compositions and methods of therapeutic treatment using the same
US5602100A (en) 1988-06-30 1997-02-11 Astra Ab Dermorphin analogs having pharmacological activity
SG42865A1 (en) * 1991-07-24 1997-10-17 Enzacor Pty Ltd Therapeutic compositions and methods
US5614219A (en) * 1991-12-05 1997-03-25 Alfatec-Pharma Gmbh Oral administration form for peptide pharmaceutical substances, in particular insulin
JP3172749B2 (en) * 1992-02-17 2001-06-04 ライオン株式会社 Ibuprofen-containing preparation
GB9402203D0 (en) * 1994-02-04 1994-03-30 Smithkline Beecham Plc Pharmaceutical formulation
ES2283503T3 (en) * 1994-04-22 2007-11-01 Astellas Pharma Inc. COLON SPECIFIC FARMACO RELEASE SYSTEM.
US5807746A (en) 1994-06-13 1998-09-15 Vanderbilt University Method for importing biologically active molecules into cells
JPH08325145A (en) * 1995-05-26 1996-12-10 Sumitomo Pharmaceut Co Ltd Stable isopropylantipyrine-containing preparation
SG80553A1 (en) * 1995-07-20 2001-05-22 Tanabe Seiyaku Co Pharmaceutical preparation in form of coated capsule releasable at lower part of digestive tract
US6039975A (en) * 1995-10-17 2000-03-21 Hoffman-La Roche Inc. Colon targeted delivery system
AU1808897A (en) * 1995-12-13 1997-07-03 Dullatur Limited A calcitonin preparation
US5840332A (en) * 1996-01-18 1998-11-24 Perio Products Ltd. Gastrointestinal drug delivery system
US5912014A (en) * 1996-03-15 1999-06-15 Unigene Laboratories, Inc. Oral salmon calcitonin pharmaceutical products
DE19626045C2 (en) * 1996-06-28 1998-12-03 Klinge Co Chem Pharm Fab A stable dosage form for oral administration containing omeprazole as the active ingredient and methods of making the same
SE9704870D0 (en) * 1997-12-22 1997-12-22 Astra Ab New pharmaceutical formulation I
US6187330B1 (en) * 1998-01-30 2001-02-13 Scios Inc. Controlled release delivery of peptide or protein
EP1086126A1 (en) 1998-06-10 2001-03-28 The Queen's University of Belfast Cell-permeable peptide
GB9824604D0 (en) * 1998-11-11 1999-01-06 Hewlett Healthcare Limited Treatment of allergic conditions
JP3796562B2 (en) * 1999-05-26 2006-07-12 ライオン株式会社 Multilayer tablet, method for producing multilayer tablet, and method for inhibiting peeling of multilayer tablet
JP2001055322A (en) * 1999-08-18 2001-02-27 Tanabe Seiyaku Co Ltd Pulse release type preparation
DE60027030D1 (en) 1999-09-27 2006-05-18 Elan Corp MEMBRANE TRANSLLATING PEPTIDE AS AN ACTIVE TRANSPORT SYSTEM

Also Published As

Publication number Publication date
JP2010184945A (en) 2010-08-26
EP1365747A4 (en) 2009-12-02
NZ527844A (en) 2005-08-26
WO2002072075A1 (en) 2002-09-19
CA2440578C (en) 2009-05-26
AU2002306681B2 (en) 2006-02-02
US20030017203A1 (en) 2003-01-23
EP1365747A1 (en) 2003-12-03
MXPA03008072A (en) 2004-03-16
JP2004525123A (en) 2004-08-19
US7316819B2 (en) 2008-01-08

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