CA2489865C - Transdermal delivery rate control using amorphous pharmaceutical compositions - Google Patents
Transdermal delivery rate control using amorphous pharmaceutical compositions Download PDFInfo
- Publication number
- CA2489865C CA2489865C CA2489865A CA2489865A CA2489865C CA 2489865 C CA2489865 C CA 2489865C CA 2489865 A CA2489865 A CA 2489865A CA 2489865 A CA2489865 A CA 2489865A CA 2489865 C CA2489865 C CA 2489865C
- Authority
- CA
- Canada
- Prior art keywords
- physiologically active
- active agent
- pharmaceutical composition
- penetration enhancer
- dermal penetration
- 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
Links
- 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 40
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- 239000003961 penetration enhancing agent Substances 0.000 claims abstract description 65
- 231100000223 dermal penetration Toxicity 0.000 claims abstract description 62
- 239000003623 enhancer Substances 0.000 claims abstract description 48
- 239000002904 solvent Substances 0.000 claims abstract description 23
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- ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 claims description 2
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- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 claims description 2
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- AHOUBRCZNHFOSL-UHFFFAOYSA-N Paroxetine hydrochloride Natural products C1=CC(F)=CC=C1C1C(COC=2C=C3OCOC3=CC=2)CNCC1 AHOUBRCZNHFOSL-UHFFFAOYSA-N 0.000 claims description 2
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- XSVMFMHYUFZWBK-NSHDSACASA-N Rivastigmine Chemical compound CCN(C)C(=O)OC1=CC=CC([C@H](C)N(C)C)=C1 XSVMFMHYUFZWBK-NSHDSACASA-N 0.000 claims description 2
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 claims description 2
- GKQPCPXONLDCMU-CCEZHUSRSA-N lacidipine Chemical compound CCOC(=O)C1=C(C)NC(C)=C(C(=O)OCC)C1C1=CC=CC=C1\C=C\C(=O)OC(C)(C)C GKQPCPXONLDCMU-CCEZHUSRSA-N 0.000 claims description 2
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- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims description 2
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Landscapes
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| AUPN814496A0 (en) * | 1996-02-19 | 1996-03-14 | Monash University | Dermal penetration enhancer |
| DE19814084B4 (de) * | 1998-03-30 | 2005-12-22 | Lts Lohmann Therapie-Systeme Ag | D2-Agonist enthaltendes transdermales therapeutisches System zur Behandlung des Parkinson-Syndroms und Verfahren zu seiner Herstellung |
| DE10041478A1 (de) | 2000-08-24 | 2002-03-14 | Sanol Arznei Schwarz Gmbh | Neue pharmazeutische Zusammensetzung |
| US20050181032A1 (en) * | 2002-06-25 | 2005-08-18 | Acrux Dds Pty Ltd. | Metastable pharmaceutical compositions |
| EP1534235B1 (en) * | 2002-06-25 | 2016-07-27 | Acrux DDS Pty Ltd | Transdermal delivery rate control using amorphous pharmaceutical compositions |
| US20050186141A1 (en) * | 2002-06-25 | 2005-08-25 | Acrux Dds Pty Ltd. | Transdermal aerosol compositions |
| US8246980B2 (en) * | 2002-07-30 | 2012-08-21 | Ucb Pharma Gmbh | Transdermal delivery system |
| US8211462B2 (en) * | 2002-07-30 | 2012-07-03 | Ucb Pharma Gmbh | Hot-melt TTS for administering rotigotine |
| DE10234673B4 (de) * | 2002-07-30 | 2007-08-16 | Schwarz Pharma Ag | Heißschmelz-TTS zur Verabreichung von Rotigotin und Verfahren zu seiner Herstellung sowie Verwendung von Rotigotin bei der Herstellung eines TTS im Heißschmelzverfahren |
| US8246979B2 (en) | 2002-07-30 | 2012-08-21 | Ucb Pharma Gmbh | Transdermal delivery system for the administration of rotigotine |
| ES2239196T3 (es) * | 2002-12-02 | 2005-09-16 | Schwarz Pharma Ag | Suministro iontoforetico de rotigotina para el tratamiento de la enfermedad de parkinson. |
| DE10261696A1 (de) * | 2002-12-30 | 2004-07-15 | Schwarz Pharma Ag | Vorrichtung zur transdermalen Verabreichung von Rotigotin-Base |
| GB0306859D0 (en) * | 2003-03-25 | 2003-04-30 | Arachnova Therapeutics Ltd | Topical formulation and use of buspirone |
| GB0319874D0 (en) * | 2003-08-22 | 2003-09-24 | Glaxo Group Ltd | Novel formulation |
| US20060263421A1 (en) | 2005-05-18 | 2006-11-23 | Abeille Pharmaceuticals Inc | Transdermal Method and Patch for Nausea |
| WO2006128255A1 (en) * | 2005-06-03 | 2006-12-07 | Acrux Dds Pty Ltd | Method and composition for transdermal drug delivery |
| ES2607454T3 (es) | 2005-06-03 | 2017-03-31 | Acrux Dds Pty Ltd | Método y composición para el suministro transdérmico de testosterona |
| US20070065494A1 (en) * | 2005-08-03 | 2007-03-22 | Watson Laboratories, Inc. | Formulations and Methods for Enhancing the Transdermal Penetration of a Drug |
| CN101600730B (zh) | 2006-10-12 | 2014-01-29 | Bhi有限合资公司 | 递送3-氨基-1-丙磺酸的方法、化合物、组合物和载体 |
| JP5114496B2 (ja) | 2007-01-11 | 2013-01-09 | アクルックス・ディ・ディ・エス・プロプライエタリー・リミテッド | 拡散器具 |
| AR068409A1 (es) * | 2007-09-14 | 2009-11-18 | Drugtech Corp | Composiciones farmaceuticas, transdermicas sin alcohol |
| AR068408A1 (es) * | 2007-09-14 | 2009-11-18 | Drugtech Corp | Pulverizacion de hormonas transdermicas |
| JP2011502172A (ja) * | 2007-11-02 | 2011-01-20 | アクルックス・ディ・ディ・エス・プロプライエタリー・リミテッド | ホルモンおよびステロイド用の経皮送達システム |
| KR100929560B1 (ko) * | 2008-01-09 | 2009-12-03 | 에코 퍼시픽 엘티디 | 그라니세트론을 함유한 매트릭스 형태의 경피 흡수제 |
| US20100178307A1 (en) * | 2010-01-13 | 2010-07-15 | Jianye Wen | Transdermal anti-dementia active agent formulations and methods for using the same |
| KR101292768B1 (ko) * | 2010-04-23 | 2013-08-05 | 아이큐어 주식회사 | 경피 흡수 제제 |
| CN108186611A (zh) | 2010-04-30 | 2018-06-22 | 帝国制药美国公司 | 丙炔基氨基茚满透皮组合物 |
| SG10201803321TA (en) * | 2010-12-02 | 2018-06-28 | Ferring Int Center Sa | Active enantiomer of dodecyl 2-(n,n-dimethylamino)-propionate |
| CA2827435C (en) * | 2011-02-15 | 2018-11-27 | Eli Lilly And Company | Methods for controlling pain in canines using a transdermal solution of fentanyl |
| EP2675454B1 (en) * | 2011-02-15 | 2020-01-22 | Audevard | Methods for controlling pain in equines using a transdermal solution of fentanyl |
| KR101853082B1 (ko) | 2011-03-24 | 2018-04-27 | 테이코쿠 팔마 유에스에이, 인코포레이티드 | 활성제층 및 활성제 변환층을 포함하는 경피 조성물 |
| EP2776020B1 (en) | 2011-11-09 | 2019-09-11 | Teikoku Seiyaku Co., Ltd. | Methods for the treatment of skin neoplasms |
| AU2013338243B2 (en) | 2012-11-02 | 2016-09-29 | Teikoku Seiyaku Co., Ltd. | Propynylaminoindan transdermal compositions |
| EP2968248A4 (en) * | 2013-03-15 | 2016-08-31 | Nal Pharmaceutical Group Ltd | TRANSDERMAL ACTIVE COMPOSITION SYSTEM WITH RIVASTIGMIN |
| USD750788S1 (en) | 2013-11-26 | 2016-03-01 | Acrux Dds Pty Ltd | Topical spreading applicator |
| USD749225S1 (en) | 2013-11-26 | 2016-02-09 | Acrux Dds Pty Ltd | Topical spreading applicator |
| US8785426B1 (en) | 2013-12-13 | 2014-07-22 | Upsher-Smith Laboratories, Inc. | Testosterone gel compositions and related methods |
| BR112017020358A2 (pt) | 2015-03-23 | 2018-07-17 | Biopharmx Inc | composição farmacêutica de tetraciclina para uso dermatológico |
| JP2018177724A (ja) * | 2017-04-18 | 2018-11-15 | 花王株式会社 | 外用薬 |
| WO2019140087A1 (en) * | 2018-01-10 | 2019-07-18 | Celista Pharmaceuticals Llc | Testosterone transdermal spray with film |
| US12186326B2 (en) * | 2018-07-05 | 2025-01-07 | Celista Pharmaceuticals Llc | Testosterone and estradiol transdermal spray |
Family Cites Families (97)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE555319A (enExample) | 1956-03-21 | 1900-01-01 | ||
| GB1192003A (en) | 1966-05-25 | 1970-05-13 | Struthers Scientific Int Corp | Improvements in or relating to Hair Dressing Preparation |
| GB1258394A (enExample) | 1968-01-17 | 1971-12-30 | ||
| GB1560401A (en) | 1976-01-28 | 1980-02-06 | Unilever Ltd | Skin treatment composition |
| DE2920500A1 (de) | 1979-05-21 | 1980-11-27 | Boehringer Sohn Ingelheim | Pharmazeutische zubereitung in form eines polyacrylatfilmes |
| US4506803A (en) * | 1982-08-09 | 1985-03-26 | Hoffmann-La Roche Inc. | Metered aerosol dispenser and method of using the dispenser |
| DE3311700A1 (de) * | 1983-03-30 | 1984-10-04 | Bayer Ag | Antimykotische mittel mit hoher wirkstoff-freisetzung in form von loesung und spray |
| US4912124A (en) * | 1984-02-23 | 1990-03-27 | Ortho Pharmaceutical Corporation | Antifungal dermatological solution |
| US4824676A (en) | 1984-10-11 | 1989-04-25 | Schering Corporation | Physiological means of enhancing transdermal delivery of drugs |
| US5008111A (en) | 1984-10-11 | 1991-04-16 | Schering Corporation | Physiological means of enhancing transdermal delivery of drugs |
| US4820724A (en) | 1986-03-31 | 1989-04-11 | University Of Southern California | Dual phase solvent carrier system |
| US5114946A (en) | 1987-06-12 | 1992-05-19 | American Cyanamid Company | Transdermal delivery of pharmaceuticals |
| US5474783A (en) | 1988-03-04 | 1995-12-12 | Noven Pharmaceuticals, Inc. | Solubility parameter based drug delivery system and method for altering drug saturation concentration |
| US5656286A (en) | 1988-03-04 | 1997-08-12 | Noven Pharmaceuticals, Inc. | Solubility parameter based drug delivery system and method for altering drug saturation concentration |
| US5082866A (en) * | 1988-06-01 | 1992-01-21 | Odontex, Inc. | Biodegradable absorption enhancers |
| US5164406A (en) | 1988-06-02 | 1992-11-17 | Bristol-Myers Squibb Co. | Method for enhancing transdermal penetration and compositions useful therein |
| US5788983A (en) | 1989-04-03 | 1998-08-04 | Rutgers, The State University Of New Jersey | Transdermal controlled delivery of pharmaceuticals at variable dosage rates and processes |
| CA2020964A1 (en) | 1989-07-12 | 1991-01-13 | Emmett M. Partain, Iii | Pharmaceutical active derivative delivery systems |
| US5091186A (en) | 1989-08-15 | 1992-02-25 | Cygnus Therapeutic Systems | Biphasic transdermal drug delivery device |
| JPH0794378B2 (ja) | 1989-08-18 | 1995-10-11 | 久光製薬株式会社 | エアゾール剤 |
| JPH0383924A (ja) | 1989-08-28 | 1991-04-09 | Kanebo Ltd | 経皮投与用組成物 |
| IL95952A0 (en) | 1989-10-19 | 1991-07-18 | Sterling Drug Inc | Aerosol composition for topical medicament |
| JP3046346B2 (ja) | 1990-03-12 | 2000-05-29 | 昭和電工株式会社 | 外用剤基剤又は補助剤とそれを含有する人又は動物の外用剤 |
| US5118494A (en) | 1990-03-23 | 1992-06-02 | Minnesota Mining And Manufacturing Company | Use of soluble fluorosurfactants for the preparation of metered-dose aerosol formulations |
| JP2974081B2 (ja) | 1990-07-26 | 1999-11-08 | 小池化学株式会社 | 人体用エアゾール組成物 |
| DE69105212T2 (de) | 1990-10-18 | 1995-03-23 | Minnesota Mining And Mfg. Co., Saint Paul, Minn. | Aerosolzubereitung, die beclometason 17,21-dipropionat enthält. |
| US5122383A (en) | 1991-05-17 | 1992-06-16 | Theratech, Inc. | Sorbitan esters as skin permeation enhancers |
| DE69222182T2 (de) | 1991-12-18 | 1998-02-26 | Warner Lambert Co | Verfahren für die herstellung einer festen dispersion |
| EP0560014A1 (en) | 1992-03-12 | 1993-09-15 | Atrix Laboratories, Inc. | Biodegradable film dressing and method for its formation |
| HU221598B (hu) | 1992-06-11 | 2002-11-28 | Theratech Inc. | Glicerin alkalmazása bőrön keresztüli hatóanyag-bevitel szabályozására |
| EP0581587A3 (en) | 1992-07-31 | 1995-05-17 | Tanabe Seiyaku Co | Basis for percutaneous administration. |
| DE4230588C1 (de) | 1992-09-12 | 1993-10-07 | Lohmann Therapie Syst Lts | Dexpanthenol-haltiges Pflaster zur transdermalen Applikation von Steroidhormonen und Verfahren zu seiner Herstellung |
| US5613958A (en) | 1993-05-12 | 1997-03-25 | Pp Holdings Inc. | Transdermal delivery systems for the modulated administration of drugs |
| DE4334553C2 (de) * | 1993-10-11 | 1998-05-20 | Synopharm Gmbh Pharmazeutische | Flüssiges pharmazeutisches System zur perkutanen Applikation |
| DE4446600A1 (de) | 1994-12-24 | 1996-06-27 | Lohmann Therapie Syst Lts | Transdermale Resorption von Wirkstoffen aus unterkühlten Schmelzen |
| US6416760B2 (en) | 1995-01-26 | 2002-07-09 | Societe L'oreal | Therapeutic/cosmetic compositions comprising CGRP antagonists for treating sensitive human skin |
| GB9504265D0 (en) | 1995-03-03 | 1995-04-19 | Medeva Plc | Corticosteroid-containing pharmaceutical composition |
| FR2732223B1 (fr) | 1995-03-30 | 1997-06-13 | Sanofi Sa | Composition pharmaceutique pour administration transdermique |
| US5780050A (en) | 1995-07-20 | 1998-07-14 | Theratech, Inc. | Drug delivery compositions for improved stability of steroids |
| US6916487B2 (en) * | 1996-02-19 | 2005-07-12 | Acrux Dds Pty Ltd | Transdermal delivery of antiemetics |
| US6929801B2 (en) * | 1996-02-19 | 2005-08-16 | Acrux Dds Pty Ltd | Transdermal delivery of antiparkinson agents |
| AUPN814496A0 (en) * | 1996-02-19 | 1996-03-14 | Monash University | Dermal penetration enhancer |
| US6923983B2 (en) | 1996-02-19 | 2005-08-02 | Acrux Dds Pty Ltd | Transdermal delivery of hormones |
| US7094422B2 (en) | 1996-02-19 | 2006-08-22 | Acrux Dds Pty Ltd. | Topical delivery of antifungal agents |
| US6998138B2 (en) | 1996-02-19 | 2006-02-14 | Acrux Dds Pty. Ltd. | Topical delivery of anti-alopecia agents |
| US6916486B2 (en) * | 1996-02-19 | 2005-07-12 | Acrux Dds Pty Ltd | Transdermal delivery of analgesics |
| US6004969A (en) * | 1996-04-15 | 1999-12-21 | National Science Council | Transdermal delivery of buprenorphine preparations |
| DE19616539A1 (de) * | 1996-04-25 | 1997-11-06 | Luitpold Pharma Gmbh | Acetylsalicylsäure enthaltende alkoholische Lösungen zur perkutanen Anwendung, deren Verwendung zur antithrombotischen Therapie sowie Arzneimittel |
| US6638948B1 (en) | 1996-09-09 | 2003-10-28 | Pentech Pharmaceuticals, Inc. | Amorphous paroxetine composition |
| AUPO379596A0 (en) * | 1996-11-22 | 1996-12-19 | Soltec Research Pty Ltd | Percutaneous delivery system |
| DE19701949A1 (de) | 1997-01-13 | 1998-07-16 | Jenapharm Gmbh | Transdermales therapeutisches System |
| IT1294748B1 (it) | 1997-09-17 | 1999-04-12 | Permatec Tech Ag | Formulazione per un dispositivo transdermico |
| US5968919A (en) | 1997-10-16 | 1999-10-19 | Macrochem Corporation | Hormone replacement therapy drug formulations for topical application to the skin |
| DE69840426D1 (de) | 1997-11-10 | 2009-02-12 | Strakan Int Ltd | Penetrationsfördernde und irritationsvermindernde Systeme mit Testosteron |
| EP0919550A1 (en) | 1997-11-26 | 1999-06-02 | Ucb, S.A. | Pseudopolymorphic forms of 2-2-4-bis(4-fluorophenyl)methyl-1-piperazinyl-ethoxy acetic acid dihydrochloride |
| AU749697B2 (en) | 1998-08-04 | 2002-07-04 | Jagotec Ag | Medicinal aerosol formulations |
| US5962505A (en) | 1998-08-31 | 1999-10-05 | Bobrove; Arthur M. | Method for treating hot flashes in humans |
| DE19843027A1 (de) * | 1998-09-19 | 2000-03-23 | Labtec Gmbh | Neohesperidin DC als Kristallisationsinhibitor |
| US6663874B2 (en) * | 1998-11-02 | 2003-12-16 | Victor Stevens | Composition to alleviate pain and topical method of applying same |
| ES2209812T3 (es) * | 1999-02-05 | 2004-07-01 | Cipla Ltd. | Pulverizaciones topicas que contienen una composicion filmogena. |
| DE19906152B4 (de) | 1999-02-10 | 2005-02-10 | Jenapharm Gmbh & Co. Kg | Wirkstoffhaltige Laminate für Transdermalsysteme |
| US6399093B1 (en) * | 1999-05-19 | 2002-06-04 | Advanced Medical Instruments | Method and composition to treat musculoskeletal disorders |
| JP2001270826A (ja) | 1999-09-28 | 2001-10-02 | Shoei:Kk | 皮膚疾患治療・予防用外用剤 |
| WO2001032115A1 (en) | 1999-11-04 | 2001-05-10 | Xel Herbaceuticals | Transdermal administration of huperzine |
| US20010041716A1 (en) * | 1999-12-02 | 2001-11-15 | Laing Timothy J. | Compositions and methods for locally treating inflammatory diseases |
| US6432415B1 (en) | 1999-12-17 | 2002-08-13 | Axrix Laboratories, Inc. | Pharmaceutical gel and aerosol formulations and methods to administer the same to skin and mucosal surfaces |
| JP2004159666A (ja) * | 1999-12-21 | 2004-06-10 | Ya Man Ltd | レーザ脱毛器 |
| IN191512B (enExample) * | 2000-01-21 | 2003-12-06 | Panacea Biotech | |
| US6562790B2 (en) | 2000-02-05 | 2003-05-13 | Chein Edmund Y M | Hormone therapy methods and hormone products for abating coronary artery blockage |
| US6387383B1 (en) | 2000-08-03 | 2002-05-14 | Dow Pharmaceutical Sciences | Topical low-viscosity gel composition |
| IN191090B (enExample) * | 2000-08-29 | 2003-09-20 | Ranbanx Lab Ltd | |
| JP2004524267A (ja) | 2000-08-30 | 2004-08-12 | ユニメッド・ファーマシューティカルズ・インコーポレーテッド | 男性の勃起障害の治療方法、及び性衝動の増強方法 |
| NZ536633A (en) | 2000-08-30 | 2006-03-31 | Unimed Pharmaceuticals Inc | Percutaneous delivery of testosterone via a hydroalcoholic gel as a method of increasing testosterone and related steroid concentrations in women |
| US20030139384A1 (en) | 2000-08-30 | 2003-07-24 | Dudley Robert E. | Method for treating erectile dysfunction and increasing libido in men |
| US6503894B1 (en) | 2000-08-30 | 2003-01-07 | Unimed Pharmaceuticals, Inc. | Pharmaceutical composition and method for treating hypogonadism |
| US6682757B1 (en) | 2000-11-16 | 2004-01-27 | Euro-Celtique, S.A. | Titratable dosage transdermal delivery system |
| GB0029634D0 (en) * | 2000-12-05 | 2001-01-17 | Norway Medical Group Int As | Use |
| US6743448B2 (en) | 2000-12-11 | 2004-06-01 | Abraham H. Kryger | Topical testosterone formulations and associated methods |
| JP2005523252A (ja) | 2002-01-26 | 2005-08-04 | マイクロ サイエンス テック コーポレーション リミテッド | 牧丹皮抽出物を有効成分として含む組成物 |
| US20030199584A1 (en) | 2002-04-11 | 2003-10-23 | Ahluwalia Gurpreet S. | Reduction of hair growth |
| US20050186141A1 (en) | 2002-06-25 | 2005-08-25 | Acrux Dds Pty Ltd. | Transdermal aerosol compositions |
| US20050181032A1 (en) | 2002-06-25 | 2005-08-18 | Acrux Dds Pty Ltd. | Metastable pharmaceutical compositions |
| EP1534235B1 (en) | 2002-06-25 | 2016-07-27 | Acrux DDS Pty Ltd | Transdermal delivery rate control using amorphous pharmaceutical compositions |
| AUPS317102A0 (en) * | 2002-06-25 | 2002-07-18 | Drug Delivery Solutions Pty Ltd | Transdermal aerosol compositions |
| US8206696B2 (en) | 2002-12-30 | 2012-06-26 | Aplicare, Inc. | Antimicrobial skin preparation |
| GB0302662D0 (en) | 2003-02-05 | 2003-03-12 | Strakan Ltd | Transdermal granisetron |
| FR2851470B1 (fr) | 2003-02-20 | 2007-11-16 | Besins Int Belgique | Composition pharmaceutique pour administration transdermique ou transmuqueuse |
| CA2433101A1 (en) | 2003-06-23 | 2004-12-23 | Igor Gonda | Method of treatment of a female suffering from androgen insufficiency |
| US20050025833A1 (en) | 2003-07-16 | 2005-02-03 | Chaim Aschkenasy | Pharmaceutical composition and method for transdermal drug delivery |
| US20050042268A1 (en) | 2003-07-16 | 2005-02-24 | Chaim Aschkenasy | Pharmaceutical composition and method for transdermal drug delivery |
| US20050020552A1 (en) | 2003-07-16 | 2005-01-27 | Chaim Aschkenasy | Pharmaceutical composition and method for transdermal drug delivery |
| DK1670433T3 (da) | 2003-10-10 | 2012-03-12 | Ferring Bv | Transdermal farmaceutisk formulering til mindskelse af hudrester |
| MXPA06005743A (es) | 2003-11-19 | 2007-04-17 | Acrux Dds Pty Ltd | Metodo y composicion para el tratamiento o profilaxis de trastornos de amiloidosis. |
| US20050123576A1 (en) | 2003-12-03 | 2005-06-09 | Ilana Lavon | Mupirocin compositions for topical use, an improved process of making same and methods of using same |
| EP2656859B1 (en) | 2004-03-03 | 2015-10-21 | ReVance Therapeutics, Inc. | Topical application and transdermal delivery of botulinum toxins |
| EP1634583A1 (en) | 2004-09-09 | 2006-03-15 | Laboratoires Besins International | Testosterone gels comprising propylene glycol as penetration enhancer |
| ES2607454T3 (es) | 2005-06-03 | 2017-03-31 | Acrux Dds Pty Ltd | Método y composición para el suministro transdérmico de testosterona |
-
2003
- 2003-06-24 EP EP03729716.5A patent/EP1534235B1/en not_active Revoked
- 2003-06-24 KR KR1020107009520A patent/KR20100055542A/ko not_active Ceased
- 2003-06-24 KR KR1020047021362A patent/KR20050045946A/ko not_active Ceased
- 2003-06-24 JP JP2004514440A patent/JP5160018B2/ja not_active Expired - Fee Related
- 2003-06-24 WO PCT/AU2003/000787 patent/WO2004000263A1/en not_active Ceased
- 2003-06-24 CA CA2489865A patent/CA2489865C/en not_active Expired - Fee Related
- 2003-06-24 BR BRPI0312007-4A patent/BRPI0312007B1/pt not_active IP Right Cessation
- 2003-06-24 EA EA200500084A patent/EA009024B1/ru not_active IP Right Cessation
- 2003-06-24 NZ NZ537360A patent/NZ537360A/en not_active IP Right Cessation
- 2003-06-24 EP EP10010704A patent/EP2266533A3/en not_active Withdrawn
- 2003-06-24 ES ES03729716.5T patent/ES2589077T3/es not_active Expired - Lifetime
- 2003-06-24 AU AU2003240301A patent/AU2003240301B2/en not_active Ceased
-
2004
- 2004-12-07 US US11/004,926 patent/US8357393B2/en not_active Expired - Fee Related
-
2009
- 2009-12-18 US US12/642,301 patent/US20100166674A1/en not_active Abandoned
-
2012
- 2012-04-12 JP JP2012090664A patent/JP5568108B2/ja not_active Expired - Fee Related
- 2012-12-11 US US13/710,761 patent/US8784878B2/en not_active Expired - Fee Related
-
2014
- 2014-06-16 US US14/305,529 patent/US20150094290A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| JP5568108B2 (ja) | 2014-08-06 |
| JP5160018B2 (ja) | 2013-03-13 |
| KR20050045946A (ko) | 2005-05-17 |
| EP1534235B1 (en) | 2016-07-27 |
| HK1077192A1 (en) | 2006-02-10 |
| EP2266533A3 (en) | 2011-12-14 |
| EP1534235A4 (en) | 2008-06-18 |
| EA009024B1 (ru) | 2007-10-26 |
| JP2006501172A (ja) | 2006-01-12 |
| EA200500084A1 (ru) | 2005-06-30 |
| CA2489865A1 (en) | 2003-12-31 |
| AU2003240301A1 (en) | 2004-01-06 |
| EP2266533A2 (en) | 2010-12-29 |
| US20150094290A1 (en) | 2015-04-02 |
| NZ537360A (en) | 2006-09-29 |
| US20100166674A1 (en) | 2010-07-01 |
| BRPI0312007B1 (pt) | 2015-04-14 |
| US20130316996A1 (en) | 2013-11-28 |
| US8784878B2 (en) | 2014-07-22 |
| BR0312007A (pt) | 2005-04-12 |
| US20050175680A1 (en) | 2005-08-11 |
| AU2003240301B2 (en) | 2008-02-14 |
| US8357393B2 (en) | 2013-01-22 |
| WO2004000263A1 (en) | 2003-12-31 |
| ES2589077T3 (es) | 2016-11-10 |
| JP2012162557A (ja) | 2012-08-30 |
| EP1534235A1 (en) | 2005-06-01 |
| KR20100055542A (ko) | 2010-05-26 |
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