CA2483786A1 - Preparations for the topical application of anti-androgenically active substances - Google Patents
Preparations for the topical application of anti-androgenically active substances Download PDFInfo
- Publication number
- CA2483786A1 CA2483786A1 CA002483786A CA2483786A CA2483786A1 CA 2483786 A1 CA2483786 A1 CA 2483786A1 CA 002483786 A CA002483786 A CA 002483786A CA 2483786 A CA2483786 A CA 2483786A CA 2483786 A1 CA2483786 A1 CA 2483786A1
- Authority
- CA
- Canada
- Prior art keywords
- formula
- compound
- lipid
- preparation
- alkenyl
- 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
Links
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
- A61K8/494—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom
- A61K8/4946—Imidazoles or their condensed derivatives, e.g. benzimidazoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/08—Antiseborrheics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/10—Anti-acne agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/14—Drugs for dermatological disorders for baldness or alopecia
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/72—Two oxygen atoms, e.g. hydantoin
- C07D233/76—Two oxygen atoms, e.g. hydantoin with substituted hydrocarbon radicals attached to the third ring carbon atom
- C07D233/78—Radicals substituted by oxygen atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q7/00—Preparations for affecting hair growth
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q7/00—Preparations for affecting hair growth
- A61Q7/02—Preparations for inhibiting or slowing hair growth
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Dermatology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Medicinal Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Birds (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Cosmetics (AREA)
- Medicinal Preparation (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
Disclosed is a preparation containing at least one form of lipid nanoparticles or a nanoemulsion, containing at least one compound of formula I and/or a stereoisomeric form of the compound of formula I, in which R1 represents -(C5-C17) alkyl or -(C5-C17) alkenyl. Said preparation is suitable for treating androgenetic alopecia, hirsutism, i.e. the prevention of undesired hair growth, seborrhoea, and acne and can also be used in cosmetics.
Claims (14)
1. A compound of the formula I
and/or a stereoisomeric form of the compound of the formula I
and/or a physiologically tolerated salt of the compound of the formula I, in which R1 is -(C5-C17)-alkyl or -(C5-C17)-alkenyl.
and/or a stereoisomeric form of the compound of the formula I
and/or a physiologically tolerated salt of the compound of the formula I, in which R1 is -(C5-C17)-alkyl or -(C5-C17)-alkenyl.
2. A compound of the formula I as claimed in claim 1, wherein R1 is -(C11-C15)-alkyl or -(C11-C15)-alkenyl.
3. A compound of the formula I as claimed in claim 1 or 2, which is the compound of the formula II
4. A pharmaceutical preparation comprising at least one lipid nanoparticle and at least one compound of the formula I as claimed in claim 1 and/or one stereoisomeric form of the compound of the formula I
and/or one physiologically tolerated salt of the compound of the formula I, in which R1 is -(C5-C17)-alkyl or -(C5-C17)-alkenyl.
and/or one physiologically tolerated salt of the compound of the formula I, in which R1 is -(C5-C17)-alkyl or -(C5-C17)-alkenyl.
5. A pharmaceutical preparation as claimed in claim 4, which comprises a compound of the formula I in which R1 is -(C11-C15)-alkyl or -(C11-C15)-alkenyl.
6. A pharmaceutical preparation as claimed in claim 4 or 5, which comprises a compound of the formula II
7. A process for preparing the compound of the formula I as claimed in one or more of claims 1 to 3, which comprises a) reacting a compound of the formula III
with an activated fatty acid of the formula IV
in which R1 is as defined in formula I, and X is a halogen radical, to give a compound of the formula I, or b) fractionating a compound of the formula I which has been prepared by process a) and which, because of its chemical structure, occurs in enantiomeric forms, by salt formation with enantiopure acids or bases, chromatography on chiral stationary phases or derivatization using chiral compounds such as amino acids, separation of the diastereomers obtained in this way, and elimination of the chiral groups, into the pure enantiomers, or c) either isolating the compound of the formula I which has been prepared by process a) in free form or, in the cases where acidic or basic groups are present, converting it into physiologically tolerated salts.
with an activated fatty acid of the formula IV
in which R1 is as defined in formula I, and X is a halogen radical, to give a compound of the formula I, or b) fractionating a compound of the formula I which has been prepared by process a) and which, because of its chemical structure, occurs in enantiomeric forms, by salt formation with enantiopure acids or bases, chromatography on chiral stationary phases or derivatization using chiral compounds such as amino acids, separation of the diastereomers obtained in this way, and elimination of the chiral groups, into the pure enantiomers, or c) either isolating the compound of the formula I which has been prepared by process a) in free form or, in the cases where acidic or basic groups are present, converting it into physiologically tolerated salts.
8. A medicament having an effective content of at least one compound of the formula 1 as claimed in one or more of claims 1 to 3 together with a pharmaceutically suitable and physiologically tolerated carrier, additive and/or other active ingredients and excipients.
9. A process for producing the pharmaceutical preparation as claimed in one or more of claims 4 to 6, which comprises high-pressure homogenization of the compound of the formula I in a hot lipid/surfactant solution and subsequent cooling.
10. A process for producing the preparation as claimed in one or more of claims 4 to 6, which comprises high-pressure homogenization of the compound of the formula I with lipids which are liquid at room temperature.
11. The process for producing the preparation as claimed in claims 9 and 10, wherein a surfactant and water are weighed into one vessel, and the compound of the formula I and a lipid are weighed into another vessel, the contents of the two vessels are heated to a temperature which is about 10°C above the melting point of said lipid, and then the contents of the two vessels are combined and the mixture is homogenized using a high-pressure homogenizes and finally cooled, whereupon the lipid crystallizes out to form lipid nanoparticles.
12. The process as claimed in one or more of claims 9 to 11, wherein Precirol, Compritol, Monosteol, Imwitor, Softisan, phosphatidylethanolamine or a mixture of the lipids is employed as lipid, and poloxamer is employed as surfactant.
13. The use of the compound of the formula I as claimed in one or more of claims 1 to 3 for producing a medicament for the treatment of androgenic alopecia, of hirsutism, of seborrhea or acne.
14. The use of the compound of the formula I as claimed in one or more of claims 1 to 3 or of the preparation as claimed in one or more of claims 4 to 6 in cosmetics.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10218963A DE10218963A1 (en) | 2002-04-27 | 2002-04-27 | Preparations for the topical application of antiandrogen active substances |
| DE10218963.3 | 2002-04-27 | ||
| PCT/EP2003/003837 WO2003093243A1 (en) | 2002-04-27 | 2003-04-14 | Preparations for the topical application of anti-androgenically active substances |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2483786A1 true CA2483786A1 (en) | 2003-11-13 |
| CA2483786C CA2483786C (en) | 2011-08-09 |
Family
ID=29264882
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2483786A Expired - Lifetime CA2483786C (en) | 2002-04-27 | 2003-04-14 | Preparations for the topical application of anti-androgenically active substances |
Country Status (17)
| Country | Link |
|---|---|
| EP (1) | EP1501806B1 (en) |
| JP (1) | JP4633459B2 (en) |
| AR (1) | AR039662A1 (en) |
| AT (1) | ATE321756T1 (en) |
| AU (1) | AU2003229658B2 (en) |
| BR (1) | BRPI0309579B8 (en) |
| CA (1) | CA2483786C (en) |
| DE (2) | DE10218963A1 (en) |
| DK (1) | DK1501806T3 (en) |
| ES (1) | ES2256735T3 (en) |
| IL (1) | IL164814A0 (en) |
| MX (1) | MXPA04009571A (en) |
| MY (1) | MY129714A (en) |
| PE (1) | PE20031044A1 (en) |
| PT (1) | PT1501806E (en) |
| TW (1) | TWI285637B (en) |
| WO (1) | WO2003093243A1 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2014077712A1 (en) * | 2012-11-14 | 2014-05-22 | Gdański Unwersytet Medyczny | Solid lipid nanoparticles of roxithromycin for hair loss or acne |
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1634874A4 (en) | 2003-06-12 | 2008-04-02 | Chugai Pharmaceutical Co Ltd | Imidazolidine derivative |
| US8034548B2 (en) | 2003-12-19 | 2011-10-11 | The Regents Of The University Of California | Methods and materials for assessing prostate cancer therapies |
| KR100783255B1 (en) | 2004-02-13 | 2007-12-06 | 워너-램버트 캄파니 엘엘씨 | Androgen receptor modulators |
| CN100475781C (en) * | 2004-02-13 | 2009-04-08 | 沃尼尔·朗伯有限责任公司 | Androgen receptor modulators |
| AU2005232526B2 (en) | 2004-02-24 | 2011-06-23 | The Regents Of The University Of California | Methods and materials for assessing prostate cancer therapies and compounds |
| US7507860B2 (en) | 2004-04-13 | 2009-03-24 | Pfizer Inc. | Androgen modulators |
| BRPI0509980A (en) | 2004-04-22 | 2007-10-16 | Warner Lambert Co | androgen modulators |
| MXPA06015169A (en) | 2004-07-08 | 2007-08-21 | Warner Lambert Co | Androgen modulators. |
| ES2302229T3 (en) * | 2004-08-31 | 2008-07-01 | Warner-Lambert Company Llc | ANDROGEN MODULATORS. |
| TW200724139A (en) * | 2005-05-05 | 2007-07-01 | Warner Lambert Co | Androgen modulators |
| US7709517B2 (en) | 2005-05-13 | 2010-05-04 | The Regents Of The University Of California | Diarylhydantoin compounds |
| HUE032085T2 (en) | 2006-03-27 | 2017-09-28 | Univ California | Androgen receptor modulator for the treatment of prostate cancer and androgen receptor-associated diseases |
| JP5350217B2 (en) | 2006-03-29 | 2013-11-27 | ザ リージェンツ オブ ザ ユニバーシティ オブ カリフォルニア | Diarylthiohydantoin compounds |
| TW201716385A (en) | 2007-10-26 | 2017-05-16 | 加州大學董事會 | Diarylhydantoin compounds |
| EP3124481B1 (en) | 2010-02-16 | 2018-03-28 | Aragon Pharmaceuticals, Inc. | Androgen receptor modulators and uses thereof |
| RU2503446C2 (en) * | 2012-02-07 | 2014-01-10 | Алексей Валентинович Одинцов | Hair growth product (versions) and methods of treating alopecia |
| SI3305285T1 (en) | 2012-09-26 | 2021-03-31 | Aragon Pharmaceuticals, Inc. | Anti-androgens for the treatment of non-metastatic castrate-resistant prostate cancer |
| WO2014078929A1 (en) * | 2012-11-26 | 2014-05-30 | Universidade Federal De Minas Gerais - Ufmg | Topical formulation for the prevention and treatment of alopecia and for inhibiting hair growth |
| JOP20200097A1 (en) | 2013-01-15 | 2017-06-16 | Aragon Pharmaceuticals Inc | Androgen receptor modulator and uses thereof |
| CN103965112A (en) * | 2014-05-13 | 2014-08-06 | 上海孚一生物科技有限公司 | Compound with antiandrogen activity as well as preparation method and application of compound |
| TWI726969B (en) | 2016-01-11 | 2021-05-11 | 比利時商健生藥品公司 | Substituted thiohydantoin derivatives as androgen receptor antagonists |
| JOP20200076A1 (en) | 2017-10-16 | 2020-04-30 | Aragon Pharmaceuticals Inc | Anti-androgens for the treatment of non-metastatic castration-resistant prostate cancer |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2693461B1 (en) * | 1992-07-08 | 1994-09-02 | Roussel Uclaf | New substituted phenylimidazolidines, process for their preparation, their use as medicaments and the pharmaceutical compositions containing them. |
| US5411981A (en) * | 1991-01-09 | 1995-05-02 | Roussel Uclaf | Phenylimidazolidines having antiandrogenic activity |
| FR2716110B1 (en) * | 1994-02-16 | 1996-04-05 | Roussel Uclaf | Cosmetic or pharmaceutical compositions comprising liposomes. |
| AU726572B2 (en) * | 1994-02-16 | 2000-11-09 | Aventis Pharma S.A. | Cosmetics or pharmaceutical compositions consisting of liposomes |
-
2002
- 2002-04-27 DE DE10218963A patent/DE10218963A1/en not_active Ceased
-
2003
- 2003-04-14 PT PT03722464T patent/PT1501806E/en unknown
- 2003-04-14 BR BRPI0309579A patent/BRPI0309579B8/en not_active IP Right Cessation
- 2003-04-14 DK DK03722464T patent/DK1501806T3/en active
- 2003-04-14 MX MXPA04009571A patent/MXPA04009571A/en active IP Right Grant
- 2003-04-14 WO PCT/EP2003/003837 patent/WO2003093243A1/en active IP Right Grant
- 2003-04-14 JP JP2004501382A patent/JP4633459B2/en not_active Expired - Lifetime
- 2003-04-14 DE DE50302818T patent/DE50302818D1/en not_active Expired - Lifetime
- 2003-04-14 AU AU2003229658A patent/AU2003229658B2/en not_active Expired
- 2003-04-14 CA CA2483786A patent/CA2483786C/en not_active Expired - Lifetime
- 2003-04-14 EP EP03722464A patent/EP1501806B1/en not_active Expired - Lifetime
- 2003-04-14 ES ES03722464T patent/ES2256735T3/en not_active Expired - Lifetime
- 2003-04-14 AT AT03722464T patent/ATE321756T1/en active
- 2003-04-15 PE PE2003000383A patent/PE20031044A1/en active IP Right Grant
- 2003-04-24 TW TW092109533A patent/TWI285637B/en not_active IP Right Cessation
- 2003-04-24 AR ARP030101423A patent/AR039662A1/en active IP Right Grant
- 2003-04-25 MY MYPI20031577A patent/MY129714A/en unknown
-
2004
- 2004-10-25 IL IL16481404A patent/IL164814A0/en unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2014077712A1 (en) * | 2012-11-14 | 2014-05-22 | Gdański Unwersytet Medyczny | Solid lipid nanoparticles of roxithromycin for hair loss or acne |
Also Published As
| Publication number | Publication date |
|---|---|
| TW200407312A (en) | 2004-05-16 |
| DE50302818D1 (en) | 2006-05-18 |
| EP1501806A1 (en) | 2005-02-02 |
| AU2003229658B2 (en) | 2010-07-29 |
| WO2003093243A1 (en) | 2003-11-13 |
| JP4633459B2 (en) | 2011-02-16 |
| EP1501806B1 (en) | 2006-03-29 |
| DK1501806T3 (en) | 2006-05-29 |
| AU2003229658A1 (en) | 2003-11-17 |
| IL164814A0 (en) | 2005-12-18 |
| ATE321756T1 (en) | 2006-04-15 |
| PE20031044A1 (en) | 2004-02-09 |
| BR0309579A (en) | 2005-03-01 |
| PT1501806E (en) | 2006-06-30 |
| TWI285637B (en) | 2007-08-21 |
| MXPA04009571A (en) | 2005-01-11 |
| DE10218963A1 (en) | 2003-11-20 |
| CA2483786C (en) | 2011-08-09 |
| BR0309579B1 (en) | 2014-10-07 |
| ES2256735T3 (en) | 2006-07-16 |
| JP2005535584A (en) | 2005-11-24 |
| BRPI0309579B8 (en) | 2021-05-25 |
| MY129714A (en) | 2007-04-30 |
| AR039662A1 (en) | 2005-03-02 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKEX | Expiry |
Effective date: 20230414 |