CA2446619C - Permeation enhancers - Google Patents

Permeation enhancers Download PDF

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Publication number
CA2446619C
CA2446619C CA2446619A CA2446619A CA2446619C CA 2446619 C CA2446619 C CA 2446619C CA 2446619 A CA2446619 A CA 2446619A CA 2446619 A CA2446619 A CA 2446619A CA 2446619 C CA2446619 C CA 2446619C
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CA
Canada
Prior art keywords
drug
group
enhancer
straight chain
pharmaceutical composition
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
Application number
CA2446619A
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English (en)
French (fr)
Other versions
CA2446619A1 (en
Inventor
Araz A. Raoof
Mangaraju Gudipati
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.)
Merrion Research Ill Ltd
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Merrion Research Ill 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 Merrion Research Ill Ltd filed Critical Merrion Research Ill Ltd
Publication of CA2446619A1 publication Critical patent/CA2446619A1/en
Application granted granted Critical
Publication of CA2446619C publication Critical patent/CA2446619C/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

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    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00Medicinal preparations characterised by special physical form
    • A61K9/0012Galenical forms characterised by the site of application
    • A61K9/0019Injectable compositions; Intramuscular, intravenous, arterial, subcutaneous administration; Compositions to be administered through the skin in an invasive manner
    • A61K9/0024Solid, semi-solid or solidifying implants, which are implanted or injected in body tissue
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/185Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
    • A61K31/19Carboxylic acids, e.g. valproic acid
    • A61K31/20Carboxylic acids, e.g. valproic acid having a carboxyl group bound to a chain of seven or more carbon atoms, e.g. stearic, palmitic, arachidic acids
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/70Carbohydrates; Sugars; Derivatives thereof
    • A61K31/7088Compounds having three or more nucleosides or nucleotides
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/08Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
    • A61K47/12Carboxylic acids; Salts or anhydrides thereof
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00Medicinal preparations characterised by special physical form
    • A61K9/20Pills, tablets, discs, rods
    • A61K9/2004Excipients; Inactive ingredients
    • A61K9/2013Organic compounds, e.g. phospholipids, fats
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00Medicinal preparations characterised by special physical form
    • A61K9/48Preparations in capsules, e.g. of gelatin, of chocolate
    • A61K9/4841Filling excipients; Inactive ingredients
    • A61K9/4858Organic compounds
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00Drugs for dermatological disorders
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P19/00Drugs for skeletal disorders
    • A61P19/02Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12Antivirals
    • A61P31/20Antivirals for DNA viruses
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00Antineoplastic agents
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P7/00Drugs for disorders of the blood or the extracellular fluid
    • A61P7/04Antihaemorrhagics; Procoagulants; Haemostatic agents; Antifibrinolytic agents
    • CCHEMISTRY; METALLURGY
    • C12BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12NMICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
    • C12N15/00Mutation or genetic engineering; DNA or RNA concerning genetic engineering, vectors, e.g. plasmids, or their isolation, preparation or purification; Use of hosts therefor
    • C12N15/09Recombinant DNA-technology
    • C12N15/11DNA or RNA fragments; Modified forms thereof; Non-coding nucleic acids having a biological activity
    • C12N15/113Non-coding nucleic acids modulating the expression of genes, e.g. antisense oligonucleotides; Antisense DNA or RNA; Triplex- forming oligonucleotides; Catalytic nucleic acids, e.g. ribozymes; Nucleic acids used in co-suppression or gene silencing
    • CCHEMISTRY; METALLURGY
    • C12BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12NMICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
    • C12N15/00Mutation or genetic engineering; DNA or RNA concerning genetic engineering, vectors, e.g. plasmids, or their isolation, preparation or purification; Use of hosts therefor
    • C12N15/09Recombinant DNA-technology
    • C12N15/11DNA or RNA fragments; Modified forms thereof; Non-coding nucleic acids having a biological activity
    • C12N15/113Non-coding nucleic acids modulating the expression of genes, e.g. antisense oligonucleotides; Antisense DNA or RNA; Triplex- forming oligonucleotides; Catalytic nucleic acids, e.g. ribozymes; Nucleic acids used in co-suppression or gene silencing
    • C12N15/1136Non-coding nucleic acids modulating the expression of genes, e.g. antisense oligonucleotides; Antisense DNA or RNA; Triplex- forming oligonucleotides; Catalytic nucleic acids, e.g. ribozymes; Nucleic acids used in co-suppression or gene silencing against growth factors, growth regulators, cytokines, lymphokines or hormones
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K38/00Medicinal preparations containing peptides
    • CCHEMISTRY; METALLURGY
    • C12BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12NMICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
    • C12N2310/00Structure or type of the nucleic acid
    • C12N2310/30Chemical structure
    • C12N2310/31Chemical structure of the backbone
    • C12N2310/315Phosphorothioates
    • CCHEMISTRY; METALLURGY
    • C12BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12NMICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
    • C12N2310/00Structure or type of the nucleic acid
    • C12N2310/30Chemical structure
    • C12N2310/32Chemical structure of the sugar
    • C12N2310/3212'-O-R Modification

Landscapes

  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • Public Health (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • Genetics & Genomics (AREA)
  • Biomedical Technology (AREA)
  • Organic Chemistry (AREA)
  • Molecular Biology (AREA)
  • Epidemiology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Biotechnology (AREA)
  • General Engineering & Computer Science (AREA)
  • General Chemical & Material Sciences (AREA)
  • Zoology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Wood Science & Technology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Biophysics (AREA)
  • Physics & Mathematics (AREA)
  • Biochemistry (AREA)
  • Microbiology (AREA)
  • Plant Pathology (AREA)
  • Dermatology (AREA)
  • Neurosurgery (AREA)
  • Rheumatology (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Endocrinology (AREA)
  • Virology (AREA)
  • Pain & Pain Management (AREA)
  • Orthopedic Medicine & Surgery (AREA)
  • Immunology (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Communicable Diseases (AREA)
  • Hematology (AREA)
CA2446619A 2001-05-11 2002-05-13 Permeation enhancers Expired - Fee Related CA2446619C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US29043601P 2001-05-11 2001-05-11
US60/290,436 2001-05-11
PCT/US2002/015210 WO2002092069A1 (en) 2001-05-11 2002-05-13 Permeation enhancers

Publications (2)

Publication Number Publication Date
CA2446619A1 CA2446619A1 (en) 2002-11-21
CA2446619C true CA2446619C (en) 2011-04-26

Family

ID=23115989

Family Applications (2)

Application Number Title Priority Date Filing Date
CA2446619A Expired - Fee Related CA2446619C (en) 2001-05-11 2002-05-13 Permeation enhancers
CA002447444A Abandoned CA2447444A1 (en) 2001-05-11 2002-05-13 Antisense permeation enhancers

Family Applications After (1)

Application Number Title Priority Date Filing Date
CA002447444A Abandoned CA2447444A1 (en) 2001-05-11 2002-05-13 Antisense permeation enhancers

Country Status (6)

Country Link
US (3) US7820722B2 (enExample)
EP (2) EP1390383B1 (enExample)
JP (2) JP4489356B2 (enExample)
AT (1) ATE547095T1 (enExample)
CA (2) CA2446619C (enExample)
WO (2) WO2002092069A1 (enExample)

Families Citing this family (31)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7098192B2 (en) * 1999-04-08 2006-08-29 Isis Pharmaceuticals, Inc. Antisense oligonucleotide modulation of STAT3 expression
JP2004529953A (ja) * 2001-05-11 2004-09-30 エラン コーポレーシヨン ピーエルシー 浸透促進剤としてのイソステアリン酸塩
US9308220B2 (en) 2001-12-11 2016-04-12 Cosmo Technologies Limited Pharmaceutical compositions for the oral administration of heparin or derivatives thereof
ITMI20012599A1 (it) * 2001-12-11 2003-06-11 Cosmo Spa Composizioni farmaceutiche per la somministrazione orale di eparina osuoi derivati, utili per la terapia di malattie infiammatorie dell'int
EP1718274A2 (en) * 2004-01-26 2006-11-08 Control Delivery Systems, Inc. Controlled and sustained delivery of nucleic acid-based therapeutic agents
KR20070044805A (ko) * 2004-04-15 2007-04-30 키아스마, 인코포레이티드 생물학적 장벽 투과를 촉진시킬 수 있는 조성물
US20070219131A1 (en) * 2004-04-15 2007-09-20 Ben-Sasson Shmuel A Compositions capable of facilitating penetration across a biological barrier
JP5671451B2 (ja) 2008-05-07 2015-02-18 メリオン・リサーチ・Iii・リミテッド GnRH関連化合物の組成物および調製プロセス
JP5623406B2 (ja) 2008-09-17 2014-11-12 キアズマ インコーポレイテッド 医薬組成物および関連する送達方法
US9169279B2 (en) 2009-07-31 2015-10-27 Thar Pharmaceuticals, Inc. Crystallization method and bioavailability
PT2459176T (pt) 2009-07-31 2017-12-11 Gruenenthal Gmbh Método de cristalização e biodisponibilidade
US20160016982A1 (en) 2009-07-31 2016-01-21 Thar Pharmaceuticals, Inc. Crystallization method and bioavailability
DK3252068T3 (da) 2009-10-12 2025-08-25 Larry J Smith Metoder og sammensætninger til modulering af genekspression ved anvendelse af oligonukleotidbaserede lægemidler administreret in vivo eller in vitro
US20110142889A1 (en) * 2009-12-16 2011-06-16 Nod Pharmaceuticals, Inc. Compositions and methods for oral drug delivery
US20110182985A1 (en) * 2010-01-28 2011-07-28 Coughlan David C Solid Pharmaceutical Composition with Enhancers and Methods of Preparing thereof
WO2011120033A1 (en) 2010-03-26 2011-09-29 Merrion Research Iii Limited Pharmaceutical compositions of selective factor xa inhibitors for oral administration
WO2012071517A2 (en) 2010-11-24 2012-05-31 Thar Pharmaceuticals, Inc. Novel crystalline forms
PE20142463A1 (es) 2011-04-01 2015-01-22 Isis Pharmaceuticals Inc Modulacion de la expresion del transductor de senales y activador de la transcripcion 3 (stat3)
EA035030B1 (ru) 2011-11-18 2020-04-20 Сарепта Терапьютикс, Инк. Модифицированные морфолиновые аналоги олигонуклеотидов
MX375442B (es) 2012-09-21 2025-03-06 Intensity Therapeutics Inc Un agente terapéutico y un agente mejorador de la permeación intracelular para usarse en el tratamiento de cáncer.
CN107205948B (zh) 2015-01-29 2021-12-14 诺和诺德股份有限公司 包含glp-1激动剂和肠溶衣的片剂
EP3253401B1 (en) 2015-02-03 2025-04-02 Amryt Endo, Inc. Treating acromegaly with oral octreotide
US11866700B2 (en) * 2016-05-06 2024-01-09 Exicure Operating Company Liposomal spherical nucleic acid (SNA) constructs presenting antisense oligonucleotides (ASO) for specific knockdown of interleukin 17 receptor mRNA
US10195218B2 (en) 2016-05-31 2019-02-05 Grunenthal Gmbh Crystallization method and bioavailability
WO2019055539A1 (en) * 2017-09-12 2019-03-21 Prudhomme Robert K CELLULOSIC POLYMER NANOPARTICLES AND METHODS OF FORMING THE SAME
WO2019090030A1 (en) 2017-11-03 2019-05-09 Prudhomme Robert K Hydrophobic ion pairing and flash nanoprecipitation for formation of controlled-release nanocarrier formulations
US12186436B2 (en) 2018-07-19 2025-01-07 The Trustees Of Princeton University Triblock copolymer stabilizers for the formation of nanoparticles encapsulating soluble biologics, therapeutics, and imaging agents
US20200147032A1 (en) 2018-11-14 2020-05-14 Robert K. Prud'homme Dihydromyricetin hot melt extrusion formulations and methods for forming them
WO2020252346A1 (en) * 2019-06-14 2020-12-17 POWELL, Brooks Formulations of dihydromyricetin and a permeabilizer
JP2023542136A (ja) * 2020-09-17 2023-10-05 アストラゼネカ・アクチエボラーグ 経口投与用のアンチセンスオリゴヌクレオチドを含む医薬組成物
US11141457B1 (en) 2020-12-28 2021-10-12 Amryt Endo, Inc. Oral octreotide therapy and contraceptive methods

Family Cites Families (102)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB953626A (en) 1961-04-25 1964-03-25 Meito Sangyo Kk Enteric-coated tablets of dextran sulphate ester and method of preparation thereof
JPS5131687A (en) 1974-09-11 1976-03-17 Shin Nippon Rika Kk Shitsujunzai
JPS5927900A (ja) 1982-08-09 1984-02-14 Wakunaga Seiyaku Kk 固定化オリゴヌクレオチド
US4525339A (en) * 1982-10-15 1985-06-25 Hoffmann-La Roche Inc. Enteric coated oral dosage form
JPS5973600A (ja) 1982-10-19 1984-04-25 Okayasu Shoten:Kk 排卵誘発剤
FR2540122B1 (fr) 1983-01-27 1985-11-29 Centre Nat Rech Scient Nouveaux composes comportant une sequence d'oligonucleotide liee a un agent d'intercalation, leur procede de synthese et leur application
US4605735A (en) 1983-02-14 1986-08-12 Wakunaga Seiyaku Kabushiki Kaisha Oligonucleotide derivatives
US4948882A (en) 1983-02-22 1990-08-14 Syngene, Inc. Single-stranded labelled oligonucleotides, reactive monomers and methods of synthesis
US4469671A (en) * 1983-02-22 1984-09-04 Eli Lilly And Company Contraceptive device
US4824941A (en) 1983-03-10 1989-04-25 Julian Gordon Specific antibody to the native form of 2'5'-oligonucleotides, the method of preparation and the use as reagents in immunoassays or for binding 2'5'-oligonucleotides in biological systems
EP0147437A4 (en) 1983-05-31 1987-03-05 Choong-Gook Jang DRY COMPOSITIONS WITH DIRECT COMPRESSION FOR DOSAGE FORMS WITH CONTROLLED ADMINISTRATION.
DE3331009A1 (de) * 1983-08-27 1985-03-14 Basf Ag, 6700 Ludwigshafen Verfahren zur erhoehung der enteralen resorbierbarkeit von heparin bzw. heparinoiden sowie das so erhaeltliche heparin- bzw. heparinoidpraeparat
US4587044A (en) 1983-09-01 1986-05-06 The Johns Hopkins University Linkage of proteins to nucleic acids
US5118802A (en) 1983-12-20 1992-06-02 California Institute Of Technology DNA-reporter conjugates linked via the 2' or 5'-primary amino group of the 5'-terminal nucleoside
US5258506A (en) 1984-10-16 1993-11-02 Chiron Corporation Photolabile reagents for incorporation into oligonucleotide chains
US5430136A (en) 1984-10-16 1995-07-04 Chiron Corporation Oligonucleotides having selectably cleavable and/or abasic sites
US4828979A (en) 1984-11-08 1989-05-09 Life Technologies, Inc. Nucleotide analogs for nucleic acid labeling and detection
US5034506A (en) 1985-03-15 1991-07-23 Anti-Gene Development Group Uncharged morpholino-based polymers having achiral intersubunit linkages
US5288497A (en) * 1985-05-01 1994-02-22 The University Of Utah Compositions of oral dissolvable medicaments
US4645502A (en) * 1985-05-03 1987-02-24 Alza Corporation Transdermal delivery of highly ionized fat insoluble drugs
EP0208417A3 (en) * 1985-06-12 1989-09-06 SPOFA Spojené Podniky Pro Zdravotnickou Vyrobu Use of 1-(8-alpha-ergolinyl)-3,3-diethyl urea derivatives in the treatment of endometritis
US4762779A (en) 1985-06-13 1988-08-09 Amgen Inc. Compositions and methods for functionalizing nucleic acids
JPS638396A (ja) 1986-06-30 1988-01-14 Wakunaga Pharmaceut Co Ltd ポリ標識化オリゴヌクレオチド誘導体
US4906463A (en) * 1986-12-22 1990-03-06 Cygnus Research Corporation Transdermal drug-delivery composition
AU607172B2 (en) * 1986-12-22 1991-02-28 Cygnus, Inc. Diffusion matrix for transdermal drug administration
US6051609A (en) * 1997-09-09 2000-04-18 Tristrata Technology, Inc. Additives enhancing the effect of therapeutic agents
US5091171B2 (en) * 1986-12-23 1997-07-15 Tristrata Inc Amphoteric compositions and polymeric forms of alpha hydroxyacids and their therapeutic use
US4904582A (en) 1987-06-11 1990-02-27 Synthetic Genetics Novel amphiphilic nucleic acid conjugates
US4789547A (en) 1987-06-17 1988-12-06 Warner-Lambert Company Transdermal matrix system
US5525465A (en) 1987-10-28 1996-06-11 Howard Florey Institute Of Experimental Physiology And Medicine Oligonucleotide-polyamide conjugates and methods of production and applications of the same
US4994273A (en) * 1987-11-02 1991-02-19 Merck & Co., Inc. Solubility modulated drug delivery device
DE3738460A1 (de) 1987-11-12 1989-05-24 Max Planck Gesellschaft Modifizierte oligonukleotide
US5082830A (en) 1988-02-26 1992-01-21 Enzo Biochem, Inc. End labeled nucleotide probe
US4910205A (en) * 1988-05-02 1990-03-20 Schering Corporation Transdermal delivery of loratadine
US5109124A (en) 1988-06-01 1992-04-28 Biogen, Inc. Nucleic acid probe linked to a label having a terminal cysteine
US5512439A (en) 1988-11-21 1996-04-30 Dynal As Oligonucleotide-linked magnetic particles and uses thereof
ZA898331B (en) 1988-11-22 1990-07-25 Hoffmann La Roche Pharmaceutical compositions
US5190748A (en) * 1988-11-22 1993-03-02 Hoffmann-La Roche Inc. Absorption enhancement of antibiotics
IL92537A (en) 1988-12-15 1994-04-12 Riker Laboratories Inc Topical preparations and dermal systems containing 1-isobutyl-H1-imidazo [C-4,5] quinoline-4-amine
JPH02207018A (ja) 1989-02-07 1990-08-16 Kao Corp 皮膚外用剤
US4958013A (en) 1989-06-06 1990-09-18 Northwestern University Cholesteryl modified oligonucleotides
US5254469A (en) 1989-09-12 1993-10-19 Eastman Kodak Company Oligonucleotide-enzyme conjugate that can be used as a probe in hybridization assays and polymerase chain reaction procedures
US5486603A (en) 1990-01-08 1996-01-23 Gilead Sciences, Inc. Oligonucleotide having enhanced binding affinity
US5578718A (en) 1990-01-11 1996-11-26 Isis Pharmaceuticals, Inc. Thiol-derivatized nucleosides
AU7579991A (en) 1990-02-20 1991-09-18 Gilead Sciences, Inc. Pseudonucleosides and pseudonucleotides and their polymers
US5214136A (en) 1990-02-20 1993-05-25 Gilead Sciences, Inc. Anthraquinone-derivatives oligonucleotides
JPH03275633A (ja) 1990-03-23 1991-12-06 Teikoku Seiyaku Co Ltd 生理活性ポリペプチドの吸収促進剤
US5087620A (en) * 1990-05-17 1992-02-11 Bristol-Myers Squibb Co. Controlled dermal penetration enhancement using imidazoles
US5602240A (en) 1990-07-27 1997-02-11 Ciba Geigy Ag. Backbone modified oligonucleotide analogs
US5138045A (en) 1990-07-27 1992-08-11 Isis Pharmaceuticals Polyamine conjugated oligonucleotides
US5218105A (en) 1990-07-27 1993-06-08 Isis Pharmaceuticals Polyamine conjugated oligonucleotides
US5608046A (en) 1990-07-27 1997-03-04 Isis Pharmaceuticals, Inc. Conjugated 4'-desmethyl nucleoside analog compounds
US5489677A (en) 1990-07-27 1996-02-06 Isis Pharmaceuticals, Inc. Oligonucleoside linkages containing adjacent oxygen and nitrogen atoms
US5541155A (en) * 1994-04-22 1996-07-30 Emisphere Technologies, Inc. Acids and acid salts and their use in delivery systems
US5245022A (en) 1990-08-03 1993-09-14 Sterling Drug, Inc. Exonuclease resistant terminally substituted oligonucleotides
US6582908B2 (en) 1990-12-06 2003-06-24 Affymetrix, Inc. Oligonucleotides
IT1245761B (it) 1991-01-30 1994-10-14 Alfa Wassermann Spa Formulazioni farmaceutiche contenenti glicosaminoglicani assorbibili per via orale.
DE4115849A1 (de) * 1991-05-15 1992-11-19 Lohmann Therapie Syst Lts Penetrationsfoerdernde substanz
DE4116912A1 (de) * 1991-05-18 1992-11-26 Schering Ag Mittel zur transdermalen applikation enthaltend ergolin-derivate
AU653026B2 (en) 1991-06-07 1994-09-15 Teikoku Seiyaku Kabushiki Kaisha Physiologically active polypeptide-containing pharmaceutical composition
JP3026030B2 (ja) * 1991-07-13 2000-03-27 株式会社リコー カメラの測距装置
US5229130A (en) * 1991-12-20 1993-07-20 Cygnus Therapeutics Systems Vegetable oil-based skin permeation enhancer compositions, and associated methods and systems
CA2075517C (en) * 1992-04-01 1997-03-11 John Wick Transdermal patch incorporating a polymer film incorporated with an active agent
SE501389C2 (sv) 1992-04-24 1995-01-30 Leiras Oy Farmaceutiskt preparat och förfarande för dess framställning
JP3190441B2 (ja) * 1992-07-20 2001-07-23 エーザイ株式会社 塩酸アゼラスチンを含有する安定な製剤
RU2068689C1 (ru) 1992-09-24 1996-11-10 Товарищество с ограниченной ответственностью "Лекрон" Способ получения таблеток парацетамола
SE9302135D0 (sv) * 1993-06-18 1993-06-18 Kabi Pharmacia Ab New pharmaceutical composition
US5801154A (en) 1993-10-18 1998-09-01 Isis Pharmaceuticals, Inc. Antisense oligonucleotide modulation of multidrug resistance-associated protein
DK0744941T3 (da) 1994-02-16 2003-09-29 Abbott Lab Fremgangsmåde til fremstilling af findelte farmaceutiske formuleringer
US5580574A (en) * 1994-04-28 1996-12-03 Hoffmann-La Roche Inc. Pharmaceutical composition for transdermal delivery
IL110024A (en) 1994-06-15 1998-04-05 Yissum Res Dev Co Controlled release oral drug delivery system containing hydrogel- forming polymer
US5580731A (en) 1994-08-25 1996-12-03 Chiron Corporation N-4 modified pyrimidine deoxynucleotides and oligonucleotide probes synthesized therewith
FI962869A7 (fi) 1994-11-17 1996-09-16 Toray Industries Ihon läpi absorboituvissa oleva preparaatti
JP3908795B2 (ja) * 1994-11-29 2007-04-25 久光製薬株式会社 ケトチフェン含有経皮投与製剤
FR2732223B1 (fr) * 1995-03-30 1997-06-13 Sanofi Sa Composition pharmaceutique pour administration transdermique
US5650386A (en) * 1995-03-31 1997-07-22 Emisphere Technologies, Inc. Compositions for oral delivery of active agents
US5601839A (en) * 1995-04-26 1997-02-11 Theratech, Inc. Triacetin as a penetration enhancer for transdermal delivery of a basic drug
CA2220451A1 (en) * 1995-05-17 1996-11-21 Cedars-Sinai Medical Center Methods and compositions for improving digestion and absorption in the small intestine
US6572879B1 (en) * 1995-06-07 2003-06-03 Alza Corporation Formulations for transdermal delivery of pergolide
GB9516268D0 (en) * 1995-08-08 1995-10-11 Danbiosyst Uk Compositiion for enhanced uptake of polar drugs from the colon
US5766620A (en) * 1995-10-23 1998-06-16 Theratech, Inc. Buccal delivery of glucagon-like insulinotropic peptides
US5837289A (en) * 1996-07-23 1998-11-17 Grasela; John C. Transdermal delivery of medications using a combination of penetration enhancers
EP0942697A1 (en) * 1996-10-30 1999-09-22 THERATECH, INC. (a Delaware Corporation) Fatty acid esters of lactic acid salts as permeation enhancers
US6203817B1 (en) * 1997-02-19 2001-03-20 Alza Corporation Reduction of skin reactions caused by transdermal drug delivery
PL335410A1 (en) * 1997-02-28 2000-04-25 Minnesota Mining & Mfg Medium for transcutaneous testosterone administration
JPH1112177A (ja) * 1997-06-25 1999-01-19 Teikoku Seiyaku Co Ltd 安定なアスピリン含有外用製剤
US6262161B1 (en) * 1997-06-26 2001-07-17 The Dow Chemical Company Compositions having improved ignition resistance
AU731909B2 (en) 1997-07-01 2001-04-05 Isis Pharmaceuticals, Inc. Compositions and methods for the delivery of oligonucleotides via the alimentary canal
IL121268A0 (en) * 1997-07-09 1998-01-04 Dpharm Ltd Branched chain fatty acids their derivatives and use in the treatment of central nervous system disorders
IL121269A0 (en) * 1997-07-09 1998-01-04 Dpharm Ltd Compositions and methods for reversibly increasing permeability of biomembranes
JP4181232B2 (ja) 1997-07-18 2008-11-12 帝國製薬株式会社 ジクロフェナクナトリウム含有油性外用貼付製剤
WO1999045934A1 (fr) * 1998-03-11 1999-09-16 Grelan Pharmaceutical Co., Ltd. Preparations entero-solubles effervescentes
US20030228597A1 (en) 1998-04-13 2003-12-11 Cowsert Lex M. Identification of genetic targets for modulation by oligonucleotides and generation of oligonucleotides for gene modulation
AU745880B2 (en) * 1998-05-21 2002-04-11 Isis Pharmaceuticals, Inc. Compositions and methods for non-parenteral delivery of oligonucleotides
AU1071200A (en) * 1998-10-19 2000-05-08 Biotech Australia Pty Limited Systems for oral delivery
ES2301477T3 (es) * 1999-02-22 2008-07-01 Merrion Research I Limited Forma de dosificacion oral solida que contiene un potenciador.
US6267985B1 (en) * 1999-06-30 2001-07-31 Lipocine Inc. Clear oil-containing pharmaceutical compositions
US6153209A (en) * 1999-09-28 2000-11-28 The Procter & Gamble Company Article having a transferable breathable skin care composition thereon
US6264981B1 (en) * 1999-10-27 2001-07-24 Anesta Corporation Oral transmucosal drug dosage using solid solution
US6379960B1 (en) * 2000-12-06 2002-04-30 Isis Pharmaceuticals, Inc. Antisense modulation of damage-specific DNA binding protein 2, p48 expression
JP2004529953A (ja) 2001-05-11 2004-09-30 エラン コーポレーシヨン ピーエルシー 浸透促進剤としてのイソステアリン酸塩
EP1560931B1 (en) 2002-11-14 2011-07-27 Dharmacon, Inc. Functional and hyperfunctional sirna

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CA2447444A1 (en) 2002-11-21
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EP1390383A1 (en) 2004-02-25
US7820722B2 (en) 2010-10-26
EP1390383B1 (en) 2012-02-29
US20070004668A1 (en) 2007-01-04
ATE547095T1 (de) 2012-03-15
EP1392272B1 (en) 2014-08-06
CA2446619A1 (en) 2002-11-21
WO2002092616A1 (en) 2002-11-21
US8039444B2 (en) 2011-10-18
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EP1390383A4 (en) 2008-07-09
US20030176379A1 (en) 2003-09-18

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