WO1996020699B1 - Composition and methods for transdermal delivery of acid-labile drugs - Google Patents
Composition and methods for transdermal delivery of acid-labile drugsInfo
- Publication number
- WO1996020699B1 WO1996020699B1 PCT/US1996/000015 US9600015W WO9620699B1 WO 1996020699 B1 WO1996020699 B1 WO 1996020699B1 US 9600015 W US9600015 W US 9600015W WO 9620699 B1 WO9620699 B1 WO 9620699B1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- acid
- composition
- epa
- drug
- penetration
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims abstract 13
- 239000003814 drug Substances 0.000 title claims abstract 8
- 229940079593 drugs Drugs 0.000 title claims abstract 8
- 230000037317 transdermal delivery Effects 0.000 title 1
- 239000002253 acid Substances 0.000 claims abstract 3
- 230000015556 catabolic process Effects 0.000 claims abstract 2
- 230000004059 degradation Effects 0.000 claims abstract 2
- 238000006731 degradation reaction Methods 0.000 claims abstract 2
- 239000003937 drug carrier Substances 0.000 claims abstract 2
- 235000020673 eicosapentaenoic acid Nutrition 0.000 claims 5
- IMONTRJLAWHYGT-ZCPXKWAGSA-N Norethindrone Acetate Chemical compound C1CC2=CC(=O)CC[C@@H]2[C@@H]2[C@@H]1[C@@H]1CC[C@](C#C)(OC(=O)C)[C@@]1(C)CC2 IMONTRJLAWHYGT-ZCPXKWAGSA-N 0.000 claims 2
- 239000000853 adhesive Substances 0.000 claims 2
- 230000001070 adhesive Effects 0.000 claims 2
- 230000002708 enhancing Effects 0.000 claims 2
- 229960001652 norethindrone acetate Drugs 0.000 claims 2
- 239000002904 solvent Substances 0.000 claims 2
- GCAONVVVMAVFDE-NADBREJJSA-N (Z)-N-[(E)-octadec-9-enyl]octadec-9-enamide Chemical compound CCCCCCCC\C=C\CCCCCCCCNC(=O)CCCCCCC\C=C/CCCCCCCC GCAONVVVMAVFDE-NADBREJJSA-N 0.000 claims 1
- ALSTYHKOOCGGFT-KTKRTIGZSA-N Oleyl alcohol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 claims 1
- 150000001733 carboxylic acid esters Chemical class 0.000 claims 1
- 239000000969 carrier Substances 0.000 claims 1
- 125000003827 glycol group Chemical group 0.000 claims 1
- 150000002466 imines Chemical class 0.000 claims 1
- 229940055577 oleyl alcohol Drugs 0.000 claims 1
- 230000035515 penetration Effects 0.000 claims 1
- 229920000058 polyacrylate Polymers 0.000 claims 1
- 229920000642 polymer Polymers 0.000 claims 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 claims 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 claims 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 claims 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N Oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 abstract 2
- 239000005642 Oleic acid Substances 0.000 abstract 1
- 235000014113 dietary fatty acids Nutrition 0.000 abstract 1
- 239000000194 fatty acid Substances 0.000 abstract 1
- 150000004665 fatty acids Chemical class 0.000 abstract 1
- 150000007524 organic acids Chemical class 0.000 abstract 1
- 239000003961 penetration enhancing agent Substances 0.000 abstract 1
Abstract
A transdermal penetration-enhancing, drug acid-lability reducing composition and related method are described. Specifically, the transdermal composition comprises: (a) a therapeutically effective amount of a pharmacologically active drug which is subject to acid catalyzed degradation; (b) a pharmaceutically acceptable carrier substantially free of a lower alkanol; and (c) a penetration-enhancing amount of a functional derivative of a fatty acid. Such compositions increase the usefulness of transdermal compositions that rely upon an organic acid such as oleic acid penetration enhancer.
Claims
24
AMENDED CLAIMS
[received by the International Bureau on 6 August 1996 (06.08.96); original claims 1, 4, 7 and 8 amended; original claims 2 and 3 cancelled; remaining claims unchanged (1 page)]
1. A transdermal drug penetration enhancing composition comprising a mixture of (a) a therapeutically effective amount of a pharmacologically active, acid-labile drug subject to acid catalyzed degradation; (b) a pharmaceutically acceptable carrier substantially free of a lower alkanol; and (c) a penetration- enhancing amount of oleyl alcohol or oleamide.
4. The composition of claim 1, wherein said acid-labile drug is an α,β-unsaturated ketosteroid, a 5-dehydrosteroid, an α- ketoamino acid, a carboxylic acid ester, or an imine.
5. The composition of claim 4, wherein said drug is norethindrone acetate.
6. The composition of claim 5, wherein said adhesive comprises a blend of at least two polymers and a soluble polyvinylpyrrolidone.
7. The composition of any one of claims 1, 4-6, which further comprises a solvent.
8. The composition of claim 7, wherein said carrier is a polyacrylate adhesive, said acid-labile drug is norethindrone acetate; and said solvent is a glycol.
STATEMENT UNDER ARTICLE 19
Applicants have reviewed the following references cited in the International Search Report dated 06 June 96:
(1) WO A 95 18603
(2) WO A 93 08795
(3) EPA 0 573 133
(4) EPA 0 483 105
(5) EPA 0 275-716
(6) EPA 0 196 769
(7) WO A 92 10154
(8) EPA 0 379 045
With regard to WO A 95 18603, applicants respectfully assert that Examples 31-33 first appeared in WO A 95 18603 (filed 09 January 1995) and were not in the U.S. Patent application Serial No. 08/178,558 (filed 07 January 1994) . Accordingly, applicants should be accorded the priority date of 06 January 1995 and WO A 95 18603 should not be considered prior art against the claims of the present application.
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE69634559T DE69634559T2 (en) | 1995-01-06 | 1996-01-11 | MEDICAMENT AND METHOD FOR TRANSDERMAL ADMINISTRATION OF ACID-ELASTIC DRUGS |
| EP96902047A EP0801561B1 (en) | 1995-01-06 | 1996-01-11 | Composition and methods for transdermal delivery of acid-labile drugs |
| CA002209669A CA2209669C (en) | 1995-01-06 | 1996-01-11 | Composition and methods for transdermal delivery of acid-labile drugs |
| JP52121296A JP4081139B2 (en) | 1995-01-06 | 1996-01-11 | Compositions and methods for transdermal delivery of acid labile drugs |
| AT96902047T ATE292457T1 (en) | 1995-01-06 | 1996-01-11 | MEANS AND METHOD FOR THE TRANSDERMAL ADMINISTRATION OF ACID-LABINE MEDICINAL SUBSTANCES |
| DK96902047T DK0801561T3 (en) | 1995-01-06 | 1996-01-11 | Preparation and method for transdermal administration of acid-labile drugs |
| AU46505/96A AU718530B2 (en) | 1995-01-06 | 1996-01-11 | Composition and methods for transdermal delivery of acid-labile drugs |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US36975695A | 1995-01-06 | 1995-01-06 | |
| US08/369,756 | 1995-01-06 |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US08/863,563 Continuation-In-Part US6024974A (en) | 1995-01-06 | 1997-05-27 | Composition and methods for transdermal delivery of acid labile drugs |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| WO1996020699A1 WO1996020699A1 (en) | 1996-07-11 |
| WO1996020699B1 true WO1996020699B1 (en) | 1996-09-12 |
Family
ID=23456790
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/US1996/000015 WO1996020699A1 (en) | 1995-01-06 | 1996-01-11 | Composition and methods for transdermal delivery of acid-labile drugs |
Country Status (16)
| Country | Link |
|---|---|
| EP (1) | EP0801561B1 (en) |
| JP (1) | JP4081139B2 (en) |
| KR (1) | KR100543351B1 (en) |
| AR (1) | AR002701A1 (en) |
| AT (1) | ATE292457T1 (en) |
| AU (1) | AU718530B2 (en) |
| CA (1) | CA2209669C (en) |
| DE (1) | DE69634559T2 (en) |
| DK (1) | DK0801561T3 (en) |
| ES (1) | ES2239767T3 (en) |
| IL (1) | IL116539A (en) |
| NZ (1) | NZ301153A (en) |
| PT (1) | PT801561E (en) |
| TW (1) | TW438598B (en) |
| WO (1) | WO1996020699A1 (en) |
| ZA (1) | ZA9670B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9125816B2 (en) | 2000-08-30 | 2015-09-08 | Besins Healthcare Inc. | Pharmaceutical composition and method for treating hypogonadism |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5780050A (en) * | 1995-07-20 | 1998-07-14 | Theratech, Inc. | Drug delivery compositions for improved stability of steroids |
| NZ504108A (en) * | 1997-09-26 | 2002-06-28 | Noven Pharma | Bioadhesive compositions comprising a polyvinylpyrrolidone polymer and methods for topical administration of active agents |
| DE19906152B4 (en) * | 1999-02-10 | 2005-02-10 | Jenapharm Gmbh & Co. Kg | Active substance-containing laminates for transdermal systems |
| CA2448689C (en) * | 2001-05-31 | 2009-09-01 | Hisamitsu Pharmaceutical Co., Inc. | Percutaneously absorbable patches |
| DE10220230A1 (en) * | 2002-05-06 | 2003-11-27 | Sanol Arznei Schwarz Gmbh | Use of Rotigotine to treat restless leg syndrome |
| FR2905601A1 (en) * | 2006-09-11 | 2008-03-14 | Innoderm Sarl | Use of oleic derivatives as a method and composition promoting dermal penetration of active agents present in cosmetic, pharmaceutical or dermatological compositions |
| HU227970B1 (en) | 2007-07-10 | 2012-07-30 | Egis Gyogyszergyar Nyrt | Pharmaceutical compositions containing silicones of high volatility |
| KR100963162B1 (en) * | 2008-12-15 | 2010-06-15 | 김유근 | Method for stabilize 5-aminolevulinic acid |
| US10213421B2 (en) | 2012-04-04 | 2019-02-26 | Alkahest, Inc. | Pharmaceutical formulations comprising CCR3 antagonists |
| US10045935B2 (en) | 2012-07-31 | 2018-08-14 | Egis Pharmaceuticals Plc | Transdermal formulation containing COX inhibitors |
| US11154535B2 (en) | 2012-07-31 | 2021-10-26 | Egis Pharmaceuticals Plc | Transdermal formulation containing COX inhibitors |
| CN109503692A (en) * | 2018-12-05 | 2019-03-22 | 华中药业股份有限公司 | A kind of synthetic method of -17 beta-hydroxy -3- ketone of -17 Alpha-Methyl of androstane |
| AU2020240797A1 (en) * | 2019-03-19 | 2021-10-21 | Nobelpharma Co., Ltd. | Pharmaceutical composition having excellent drug absorption into the living body and excellent chemical stability |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3685895T2 (en) * | 1985-02-25 | 1992-12-24 | Univ Rutgers | DOSING SYSTEM FOR TRANSDERMAL ABSORPTION OF DRUG ACTIVE SUBSTANCES. |
| AU601528B2 (en) * | 1986-12-22 | 1990-09-13 | Ortho-Mcneil Pharmaceutical, Inc. | Resilient transdermal drug-delivery device and compositions and devices employing fatty acid esters/ethers of alkanediols and percutaneous absorption enhancers |
| CN1021196C (en) * | 1986-12-29 | 1993-06-16 | 新泽西州州立大学(鲁杰斯) | Prepn. method of progestin unit and system |
| US4994267A (en) * | 1988-03-04 | 1991-02-19 | Noven Pharmaceuticals, Inc. | Transdermal acrylic multipolymer drug delivery system |
| US5656286A (en) * | 1988-03-04 | 1997-08-12 | Noven Pharmaceuticals, Inc. | Solubility parameter based drug delivery system and method for altering drug saturation concentration |
| ES2081823T3 (en) * | 1988-10-27 | 1996-03-16 | Schering Ag | AGENT FOR TRANSDERMIC APPLICATION, CONTAINING GESTODEN. |
| US5202125A (en) * | 1990-12-10 | 1993-04-13 | Theratech, Inc. | Method and systems for administering nitroglycerin transdermally at enhanced transdermal fluxes |
| DE4210711A1 (en) * | 1991-10-31 | 1993-05-06 | Schering Ag Berlin Und Bergkamen, 1000 Berlin, De | TRANSDERMAL THERAPEUTIC SYSTEMS WITH CRYSTALIZATION INHIBITORS |
-
1995
- 1995-12-25 IL IL11653995A patent/IL116539A/en not_active IP Right Cessation
-
1996
- 1996-01-05 ZA ZA9670A patent/ZA9670B/en unknown
- 1996-01-05 TW TW085100091A patent/TW438598B/en not_active IP Right Cessation
- 1996-01-05 AR ARP960100904A patent/AR002701A1/en active IP Right Grant
- 1996-01-11 AU AU46505/96A patent/AU718530B2/en not_active Expired
- 1996-01-11 JP JP52121296A patent/JP4081139B2/en not_active Expired - Lifetime
- 1996-01-11 NZ NZ301153A patent/NZ301153A/en not_active IP Right Cessation
- 1996-01-11 DE DE69634559T patent/DE69634559T2/en not_active Expired - Lifetime
- 1996-01-11 PT PT96902047T patent/PT801561E/en unknown
- 1996-01-11 DK DK96902047T patent/DK0801561T3/en active
- 1996-01-11 CA CA002209669A patent/CA2209669C/en not_active Expired - Lifetime
- 1996-01-11 EP EP96902047A patent/EP0801561B1/en not_active Expired - Lifetime
- 1996-01-11 WO PCT/US1996/000015 patent/WO1996020699A1/en active IP Right Grant
- 1996-01-11 AT AT96902047T patent/ATE292457T1/en active
- 1996-01-11 ES ES96902047T patent/ES2239767T3/en not_active Expired - Lifetime
- 1996-01-11 KR KR1019970704622A patent/KR100543351B1/en not_active IP Right Cessation
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9125816B2 (en) | 2000-08-30 | 2015-09-08 | Besins Healthcare Inc. | Pharmaceutical composition and method for treating hypogonadism |
| US9132089B2 (en) | 2000-08-30 | 2015-09-15 | Besins Healthcare Inc. | Pharmaceutical composition and method for treating hypogonadism |
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