DE69738200T2 - Verwendung eines emulgatorsystems zur erhöhung des penetrationsflusses pharmazeutischer wirkstoffe - Google Patents
Verwendung eines emulgatorsystems zur erhöhung des penetrationsflusses pharmazeutischer wirkstoffe Download PDFInfo
- Publication number
- DE69738200T2 DE69738200T2 DE69738200T DE69738200T DE69738200T2 DE 69738200 T2 DE69738200 T2 DE 69738200T2 DE 69738200 T DE69738200 T DE 69738200T DE 69738200 T DE69738200 T DE 69738200T DE 69738200 T2 DE69738200 T2 DE 69738200T2
- Authority
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- Germany
- Prior art keywords
- group
- carbon atoms
- alkyl
- emulsifier
- 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 - Lifetime
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- 239000003995 emulsifying agent Substances 0.000 title claims description 218
- 239000013543 active substance Substances 0.000 title claims description 18
- 230000001965 increasing effect Effects 0.000 title claims description 9
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- 125000004432 carbon atom Chemical group C* 0.000 claims description 117
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 81
- 125000000217 alkyl group Chemical group 0.000 claims description 73
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 47
- -1 Alkyl betaine Chemical compound 0.000 claims description 37
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- 125000003342 alkenyl group Chemical group 0.000 claims description 25
- 125000001165 hydrophobic group Chemical group 0.000 claims description 19
- 229910052760 oxygen Inorganic materials 0.000 claims description 19
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 18
- 239000001257 hydrogen Substances 0.000 claims description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims description 18
- 125000004434 sulfur atom Chemical group 0.000 claims description 17
- 150000001298 alcohols Chemical class 0.000 claims description 16
- 150000003839 salts Chemical class 0.000 claims description 16
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- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 13
- 230000037317 transdermal delivery Effects 0.000 claims description 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
- PEDCQBHIVMGVHV-UHFFFAOYSA-N glycerol group Chemical group OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 12
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- 229910052757 nitrogen Inorganic materials 0.000 claims description 9
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- 150000007513 acids Chemical class 0.000 claims description 8
- 125000005233 alkylalcohol group Chemical group 0.000 claims description 8
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- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 7
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- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 6
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- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 6
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical compound OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 claims description 5
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- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 5
- 239000011734 sodium Substances 0.000 claims description 5
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- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 4
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 4
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 4
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 4
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims description 4
- 239000008186 active pharmaceutical agent Substances 0.000 claims description 4
- 150000003973 alkyl amines Chemical group 0.000 claims description 4
- 229940035676 analgesics Drugs 0.000 claims description 4
- 239000000730 antalgic agent Substances 0.000 claims description 4
- 229910052791 calcium Inorganic materials 0.000 claims description 4
- 229910052744 lithium Inorganic materials 0.000 claims description 4
- 229910052749 magnesium Inorganic materials 0.000 claims description 4
- 239000010452 phosphate Substances 0.000 claims description 4
- 229920006395 saturated elastomer Polymers 0.000 claims description 4
- 229910052708 sodium Inorganic materials 0.000 claims description 4
- 150000003512 tertiary amines Chemical group 0.000 claims description 4
- 108090000790 Enzymes Proteins 0.000 claims description 3
- 102000004190 Enzymes Human genes 0.000 claims description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 3
- 125000003368 amide group Chemical group 0.000 claims description 3
- 125000002791 glucosyl group Chemical group C1([C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)* 0.000 claims description 3
- 150000002431 hydrogen Chemical class 0.000 claims description 3
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- 230000007935 neutral effect Effects 0.000 claims description 3
- 239000011591 potassium Substances 0.000 claims description 3
- 229910052700 potassium Inorganic materials 0.000 claims description 3
- SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 claims description 2
- 229940127291 Calcium channel antagonist Drugs 0.000 claims description 2
- 125000003158 alcohol group Chemical group 0.000 claims description 2
- 125000005599 alkyl carboxylate group Chemical group 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims description 2
- 230000003288 anthiarrhythmic effect Effects 0.000 claims description 2
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- 229940125684 antimigraine agent Drugs 0.000 claims description 2
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- 239000000168 bronchodilator agent Substances 0.000 claims description 2
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- 125000001033 ether group Chemical group 0.000 claims description 2
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- 230000003533 narcotic effect Effects 0.000 claims description 2
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- 229960002715 nicotine Drugs 0.000 claims description 2
- SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 claims description 2
- 239000000813 peptide hormone Substances 0.000 claims description 2
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- 125000000547 substituted alkyl group Chemical group 0.000 claims description 2
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- 239000003071 vasodilator agent Substances 0.000 claims description 2
- JNYAEWCLZODPBN-UHFFFAOYSA-N 2-(1,2-dihydroxyethyl)oxolane-3,4-diol Polymers OCC(O)C1OCC(O)C1O JNYAEWCLZODPBN-UHFFFAOYSA-N 0.000 claims 1
- KWIUHFFTVRNATP-UHFFFAOYSA-N Betaine Natural products C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 claims 1
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- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
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- 239000012875 nonionic emulsifier Substances 0.000 claims 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 claims 1
- JNYAEWCLZODPBN-CTQIIAAMSA-N sorbitan Polymers OCC(O)C1OCC(O)[C@@H]1O JNYAEWCLZODPBN-CTQIIAAMSA-N 0.000 claims 1
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- RMLUKZWYIKEASN-UHFFFAOYSA-M sodium;2-amino-9-(2-hydroxyethoxymethyl)purin-6-olate Chemical compound [Na+].O=C1[N-]C(N)=NC2=C1N=CN2COCCO RMLUKZWYIKEASN-UHFFFAOYSA-M 0.000 description 1
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- 229940098760 steareth-2 Drugs 0.000 description 1
- 150000003431 steroids Chemical class 0.000 description 1
- JNMRHUJNCSQMMB-UHFFFAOYSA-N sulfathiazole Chemical compound C1=CC(N)=CC=C1S(=O)(=O)NC1=NC=CS1 JNMRHUJNCSQMMB-UHFFFAOYSA-N 0.000 description 1
- 229960001544 sulfathiazole Drugs 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- KQKPFRSPSRPDEB-UHFFFAOYSA-N sumatriptan Chemical compound CNS(=O)(=O)CC1=CC=C2NC=C(CCN(C)C)C2=C1 KQKPFRSPSRPDEB-UHFFFAOYSA-N 0.000 description 1
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- JYKSTGLAIMQDRA-UHFFFAOYSA-N tetraglycerol Chemical compound OCC(O)CO.OCC(O)CO.OCC(O)CO.OCC(O)CO JYKSTGLAIMQDRA-UHFFFAOYSA-N 0.000 description 1
- BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 description 1
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- GFNANZIMVAIWHM-OBYCQNJPSA-N triamcinolone Chemical compound O=C1C=C[C@]2(C)[C@@]3(F)[C@@H](O)C[C@](C)([C@@]([C@H](O)C4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 GFNANZIMVAIWHM-OBYCQNJPSA-N 0.000 description 1
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Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
- A61K47/10—Alcohols; Phenols; Salts thereof, e.g. glycerol; Polyethylene glycols [PEG]; Poloxamers; PEG/POE alkyl ethers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
- A61K47/14—Esters of carboxylic acids, e.g. fatty acid monoglycerides, medium-chain triglycerides, parabens or PEG fatty acid esters
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/26—Carbohydrates, e.g. sugar alcohols, amino sugars, nucleic acids, mono-, di- or oligo-saccharides; Derivatives thereof, e.g. polysorbates, sorbitan fatty acid esters or glycyrrhizin
-
- 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
- A61K9/0014—Skin, i.e. galenical aspects of topical compositions
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Dermatology (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/781,097 US6019997A (en) | 1997-01-09 | 1997-01-09 | Hydroalcoholic compositions for transdermal penetration of pharmaceutical agents |
| US781097 | 1997-01-09 | ||
| PCT/US1997/023483 WO1998030244A1 (en) | 1997-01-09 | 1997-12-23 | Hydroalcoholic compositions for transdermal penetration of pharmaceutical agents |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE69738200D1 DE69738200D1 (de) | 2007-11-22 |
| DE69738200T2 true DE69738200T2 (de) | 2008-07-10 |
Family
ID=25121692
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69738200T Expired - Lifetime DE69738200T2 (de) | 1997-01-09 | 1997-12-23 | Verwendung eines emulgatorsystems zur erhöhung des penetrationsflusses pharmazeutischer wirkstoffe |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US6019997A (enExample) |
| EP (1) | EP0957939B1 (enExample) |
| JP (1) | JP2001508062A (enExample) |
| AU (1) | AU738444B2 (enExample) |
| CA (1) | CA2274565C (enExample) |
| DE (1) | DE69738200T2 (enExample) |
| ES (1) | ES2293667T3 (enExample) |
| WO (1) | WO1998030244A1 (enExample) |
Families Citing this family (80)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU715468B2 (en) * | 1995-06-22 | 2000-02-03 | Minnesota Mining And Manufacturing Company | Stable hydroalcoholic compositions |
| US7566460B2 (en) * | 1995-06-22 | 2009-07-28 | 3M Innovative Properties Company | Stable hydroalcoholic compositions |
| EP1374847A1 (en) * | 1995-06-22 | 2004-01-02 | Minnesota Mining And Manufacturing Company | Stable hydroalcoholic compositions |
| US6623744B2 (en) * | 1995-06-22 | 2003-09-23 | 3M Innovative Properties Company | Stable hydroalcoholic compositions |
| US6440980B1 (en) | 1996-09-17 | 2002-08-27 | Avanir Pharmaceuticals | Synergistic inhibition of viral replication by long-chain hydrocarbons and nucleoside analogs |
| US6582711B1 (en) | 1997-01-09 | 2003-06-24 | 3M Innovative Properties Company | Hydroalcoholic compositions thickened using polymers |
| US6979456B1 (en) | 1998-04-01 | 2005-12-27 | Jagotec Ag | Anticancer compositions |
| AU4972599A (en) * | 1998-07-07 | 2000-01-24 | Transdermal Technologies, Inc. | Compositions for rapid and non-irritating transdermal delivery of pharmaceutically active agents and methods for formulating such compositions and delivery thereof |
| EP1105096B1 (en) | 1998-08-19 | 2003-10-29 | Skyepharma Canada Inc. | Injectable aqueous dispersions of propofol |
| CA2360300C (en) * | 1999-02-09 | 2008-08-26 | Samyang Corporation | A transdermal composition of an antivomiting agent and a preparation containing the same |
| KR100390870B1 (ko) * | 1999-02-09 | 2003-07-10 | 주식회사 삼양사 | 경피투여용 항구토제 조성물 및 이를 포함하는 제제 |
| US6679870B1 (en) * | 1999-07-23 | 2004-01-20 | Vasca, Inc. | Methods and kits for locking and disinfecting implanted catheters |
| US20030104041A1 (en) * | 1999-12-16 | 2003-06-05 | Tsung-Min Hsu | Transdermal and topical administration of drugs using basic permeation enhancers |
| US6562369B2 (en) * | 1999-12-16 | 2003-05-13 | Dermatrends, Inc. | Transdermal administration of androgenic drugs hydroxide-releasing agents as permeation enhancers |
| US6565879B1 (en) | 1999-12-16 | 2003-05-20 | Dermatrends, Inc. | Topical and transdermal administration of peptidyl drugs with hydroxide-releasing agents as skin permeation enhancers |
| US6582724B2 (en) * | 1999-12-16 | 2003-06-24 | Dermatrends, Inc. | Dual enhancer composition for topical and transdermal drug delivery |
| US6645520B2 (en) * | 1999-12-16 | 2003-11-11 | Dermatrends, Inc. | Transdermal administration of nonsteroidal anti-inflammatory drugs using hydroxide-releasing agents as permeation enhancers |
| US6558695B2 (en) | 1999-12-16 | 2003-05-06 | Dermatrends, Inc. | Topical and transdermal administration of peptidyl drugs using hydroxide releasing agents as permeation enhancers |
| US6586000B2 (en) * | 1999-12-16 | 2003-07-01 | Dermatrends, Inc. | Hydroxide-releasing agents as skin permeation enhancers |
| US6562368B2 (en) | 1999-12-16 | 2003-05-13 | Dermatrends, Inc. | Transdermal administration of oxybutynin using hydroxide-releasing agents as permeation enhancers |
| US6719997B2 (en) | 2000-06-30 | 2004-04-13 | Dermatrends, Inc. | Transdermal administration of pharmacologically active amines using hydroxide-releasing agents as permeation enhancers |
| US6602912B2 (en) | 2000-06-30 | 2003-08-05 | Dermatrends, Inc. | Transdermal administration of phenylpropanolamine |
| US6562370B2 (en) | 1999-12-16 | 2003-05-13 | Dermatrends, Inc. | Transdermal administration of steroid drugs using hydroxide-releasing agents as permeation enhancers |
| US6673363B2 (en) | 1999-12-16 | 2004-01-06 | Dermatrends, Inc. | Transdermal and topical administration of local anesthetic agents using basic enhancers |
| US20060121103A1 (en) * | 2000-05-11 | 2006-06-08 | Kenneth Kirby | Transdermal delivery system |
| US20040002482A1 (en) * | 2000-08-30 | 2004-01-01 | Dudley Robert E. | Androgen pharmaceutical composition and method for treating depression |
| US6503894B1 (en) * | 2000-08-30 | 2003-01-07 | Unimed Pharmaceuticals, Inc. | Pharmaceutical composition and method for treating hypogonadism |
| US20040092494A9 (en) * | 2000-08-30 | 2004-05-13 | Dudley Robert E. | 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 |
| SE0004750D0 (sv) | 2000-12-19 | 2000-12-19 | Astrazeneca Ab | Novel formulation |
| US7247315B2 (en) * | 2001-08-17 | 2007-07-24 | Lavipharm Laboratories Inc. | Compositions and medical device for transdermal delivery of a drug and methods of making and using same |
| NO20014746D0 (no) * | 2001-09-28 | 2001-09-28 | Clas M Kjoelberg | Smertelindrende middel |
| WO2003032915A2 (en) * | 2001-10-16 | 2003-04-24 | Avanir Pharmacueticals | Viral inhibition by n-docosanol |
| DE10154324A1 (de) * | 2001-11-06 | 2003-08-07 | Merz Pharma Gmbh & Co Kgaa | Topisch applizierbare Zusammensetzungen mit externer Wirkstoffdepotbildung, deren Herstellung sowie deren Verwendung |
| OA12856A (en) * | 2002-03-15 | 2006-09-15 | Unimed Pharmaceuticals Inc | Androgen pharmaceutical composition and method for treating depression. |
| MY139721A (en) * | 2002-04-19 | 2009-10-30 | Cpex Pharmaceuticals Inc | Pharmaceutical composition |
| US20040018163A1 (en) * | 2002-04-29 | 2004-01-29 | Wei Yu | Cosmetic compositions comprising at least one dimethicone, at least one linear hydrocarbon wax and at least one compatibilizing agent |
| US7192599B2 (en) * | 2002-06-03 | 2007-03-20 | Mmp, Inc. | Mattifying oil-in-water emulsion |
| US20050036953A1 (en) * | 2003-08-13 | 2005-02-17 | Moshe Arkin | Topical compositions of ammonium lactate |
| US20050037040A1 (en) * | 2003-08-13 | 2005-02-17 | Moshe Arkin | Topical compositions of urea and ammonium lactate |
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-
1997
- 1997-01-09 US US08/781,097 patent/US6019997A/en not_active Expired - Lifetime
- 1997-12-23 AU AU57098/98A patent/AU738444B2/en not_active Ceased
- 1997-12-23 ES ES97953326T patent/ES2293667T3/es not_active Expired - Lifetime
- 1997-12-23 EP EP97953326A patent/EP0957939B1/en not_active Expired - Lifetime
- 1997-12-23 JP JP53090298A patent/JP2001508062A/ja not_active Ceased
- 1997-12-23 WO PCT/US1997/023483 patent/WO1998030244A1/en not_active Ceased
- 1997-12-23 CA CA002274565A patent/CA2274565C/en not_active Expired - Fee Related
- 1997-12-23 DE DE69738200T patent/DE69738200T2/de not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| ES2293667T3 (es) | 2008-03-16 |
| AU738444B2 (en) | 2001-09-20 |
| CA2274565C (en) | 2008-04-08 |
| JP2001508062A (ja) | 2001-06-19 |
| CA2274565A1 (en) | 1998-07-16 |
| AU5709898A (en) | 1998-08-03 |
| US6019997A (en) | 2000-02-01 |
| EP0957939B1 (en) | 2007-10-10 |
| WO1998030244A1 (en) | 1998-07-16 |
| EP0957939A1 (en) | 1999-11-24 |
| DE69738200D1 (de) | 2007-11-22 |
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