EP0065974A1 - Antischuppenmittel - Google Patents
AntischuppenmittelInfo
- Publication number
- EP0065974A1 EP0065974A1 EP19820900018 EP82900018A EP0065974A1 EP 0065974 A1 EP0065974 A1 EP 0065974A1 EP 19820900018 EP19820900018 EP 19820900018 EP 82900018 A EP82900018 A EP 82900018A EP 0065974 A1 EP0065974 A1 EP 0065974A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- hydrochloride
- imidazolylmethyl
- sulfide
- chloro
- dichlorobenzyl
- 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.)
- Withdrawn
Links
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 36
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 21
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 claims abstract description 6
- -1 1-imidazolylmethyl Chemical group 0.000 claims description 24
- LTYMSROWYAPPGB-UHFFFAOYSA-N diphenyl sulfide Chemical compound C=1C=CC=CC=1SC1=CC=CC=C1 LTYMSROWYAPPGB-UHFFFAOYSA-N 0.000 claims description 17
- 208000001840 Dandruff Diseases 0.000 claims description 15
- 210000004761 scalp Anatomy 0.000 claims description 8
- 238000011282 treatment Methods 0.000 claims description 8
- ORXKFTZGLMZRCV-UHFFFAOYSA-N 2-[[2-[(3,4-dichlorophenyl)methylsulfanyl]phenyl]methyl]-1h-imidazole Chemical compound C1=C(Cl)C(Cl)=CC=C1CSC1=CC=CC=C1CC1=NC=CN1 ORXKFTZGLMZRCV-UHFFFAOYSA-N 0.000 claims description 7
- 230000002401 inhibitory effect Effects 0.000 claims description 4
- 230000000069 prophylactic effect Effects 0.000 claims description 4
- 230000001225 therapeutic effect Effects 0.000 claims description 4
- 239000012876 carrier material Substances 0.000 claims 2
- 239000013543 active substance Substances 0.000 abstract description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
- 239000002304 perfume Substances 0.000 description 8
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- 239000002453 shampoo Substances 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- RMJOCNKBMMATRW-UHFFFAOYSA-N 2-[[2-[(3,4-dichlorophenyl)methylsulfanyl]phenyl]methyl]-1h-imidazole;hydrochloride Chemical compound Cl.C1=C(Cl)C(Cl)=CC=C1CSC1=CC=CC=C1CC1=NC=CN1 RMJOCNKBMMATRW-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000000499 gel Substances 0.000 description 4
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical group C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000006210 lotion Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 2
- 239000005662 Paraffin oil Substances 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 2
- 239000012670 alkaline solution Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 229960000541 cetyl alcohol Drugs 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 210000002615 epidermis Anatomy 0.000 description 2
- 150000002191 fatty alcohols Chemical class 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- BXWNKGSJHAJOGX-UHFFFAOYSA-N n-hexadecyl alcohol Natural products CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- 239000012312 sodium hydride Substances 0.000 description 2
- GUQPDKHHVFLXHS-UHFFFAOYSA-M sodium;2-(2-dodecoxyethoxy)ethyl sulfate Chemical compound [Na+].CCCCCCCCCCCCOCCOCCOS([O-])(=O)=O GUQPDKHHVFLXHS-UHFFFAOYSA-M 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 230000001256 tonic effect Effects 0.000 description 2
- LOZCIVRJQZXLLA-UHFFFAOYSA-N 1,2-dichloro-4-[[2-(chloromethyl)phenyl]sulfanylmethyl]benzene Chemical compound ClCC1=CC=CC=C1SCC1=CC=C(Cl)C(Cl)=C1 LOZCIVRJQZXLLA-UHFFFAOYSA-N 0.000 description 1
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical class CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 1
- PWORCFXRIYSRBB-UHFFFAOYSA-N 2-[[2-[(3,4-dichlorophenyl)methyl]-6-[3-[(3,4-dichlorophenyl)methyl]-2-(1H-imidazol-2-ylmethyl)phenyl]sulfanylphenyl]methyl]-1H-imidazole hydrochloride Chemical compound Cl.C1=C(Cl)C(Cl)=CC=C1CC1=CC=CC(SC=2C(=C(CC=3C=C(Cl)C(Cl)=CC=3)C=CC=2)CC=2NC=CN=2)=C1CC1=NC=CN1 PWORCFXRIYSRBB-UHFFFAOYSA-N 0.000 description 1
- 125000006512 3,4-dichlorobenzyl group Chemical group [H]C1=C(Cl)C(Cl)=C([H])C(=C1[H])C([H])([H])* 0.000 description 1
- 239000004166 Lanolin Substances 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000002280 amphoteric surfactant Substances 0.000 description 1
- 230000000843 anti-fungal effect Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- HLKZFSVWBQSKKH-UHFFFAOYSA-N but-3-enoic acid;1-ethenylpyrrolidin-2-one Chemical compound OC(=O)CC=C.C=CN1CCCC1=O HLKZFSVWBQSKKH-UHFFFAOYSA-N 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 230000032823 cell division Effects 0.000 description 1
- 230000001055 chewing effect Effects 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 230000036758 dandruff formation Effects 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000000834 fixative Substances 0.000 description 1
- 230000001976 improved effect Effects 0.000 description 1
- 229940039717 lanolin Drugs 0.000 description 1
- 235000019388 lanolin Nutrition 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- MYGZZDOIMOSOGQ-UHFFFAOYSA-N magnesium;1h-pyridine-2-thione Chemical compound [Mg].S=C1C=CC=CN1 MYGZZDOIMOSOGQ-UHFFFAOYSA-N 0.000 description 1
- 230000010534 mechanism of action Effects 0.000 description 1
- 229940126601 medicinal product Drugs 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 239000000419 plant extract Substances 0.000 description 1
- 229920000233 poly(alkylene oxides) Polymers 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910000338 selenium disulfide Inorganic materials 0.000 description 1
- JNMWHTHYDQTDQZ-UHFFFAOYSA-N selenium sulfide Chemical compound S=[Se]=S JNMWHTHYDQTDQZ-UHFFFAOYSA-N 0.000 description 1
- 229960005265 selenium sulfide Drugs 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 150000003722 vitamin derivatives Chemical class 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/415—1,2-Diazoles
-
- 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
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/006—Antidandruff preparations
Definitions
- the present invention relates to agents with anti-dandruff action, which act as active ingredients (3,4-dichlorobenzyl) - [2- (1-imidazolylmethyl) phenyl] sulfide, hydrochloride and 4-chloro-2- (l-imidazolylmethyl) diphenyl sulfide, hydrochloride contain.
- anti-dandruff agents such as zinc or magnesium pyridine thione or selenium disulfide
- Their mechanism of action consists in normalizing the significantly increased cell division activity in the epidermis in dandruff [Plewig, Klig ⁇ an Areh. clin. exp. Derm. 256, 406 (1970)].
- Effective anti-dandruff agents also have an anti-camthogenic effect, i.e. they lead to thinning of the epidermis.
- a reduction in toxicity would also be important as a promotion that is constantly being placed on modern medicinal products.
- the effectiveness against dandruff in the individual compositions must not deteriorate under the usual storage conditions of a bathroom.
- the antidandruff agent should also be inert towards other constituents of the application agent. Other characteristics of the active ingredient, such as color and smell, must meet the requirements that are placed on a cosmetic product today.
- the invention relates to an agent for inhibiting scaling of the scalp, characterized in that it has an effective dose (3,4-dichlorobenzyl) - [2- (1-imidazolylmethyl) phenyl] sulfide, hydrochloride or 4-chloro-2- ( Contains 1-imidasolylmethyl) diphenyl sulfide, hydrochloride.
- the invention also relates to the use of (3,4-dichlorobenzyl) - [2- (1-imidazolylmethyl) phenyl] sulfide, hydrochloride or 4-chloro-2- (1-imidazolylmethyl) diphenyl sulfide, hydrochloride for prophylactic and therapeutic treatment of the scalp against dandruff.
- (3,4-dichlorobenzyl) - [2- (1-imidazolylmethyl) phenyl] sulfide, hydrochloride and 4-chloro-2- (1-imidasolylmethyl) diphenyl sulfide, hydrochloride are formulated in a manner known per se by being mixed with 0.1-5% by weight in ethanol / water or isopropanol / water for hair lotions or in 1-5% by weight for Sharapoos (hairdressing gels or inlay agents) and customary auxiliaries and carriers.
- hair treatment agents which contain fatty alcohol-folyalkylene oxide adducts in their preparations, preferably those of fatty alcohols of chain length with 10-20 carbon atoms with 5-40 mol ethylene oxide units.
- Possible hair treatment agents with an anti-dandruff effect are: hair shampoo, hair tonic, hair fixative, hairdressing cream, hair conditioner, hair treatment, hair lotion etc.
- the anti-dandruff active ingredients (3.4-dichlorobenzyl) - [2- (1-imidazolylmethyl) - phenyl] sulfide hydrochloride and 4-Chloro-2- (1-imidazolylmethyl) diphenyl sulfide, hydrochloride in shampoos, hair lotions, inlay agents and hairdressing gels.
- the agents mentioned contain other carriers and components customary in hair treatment compositions in the usual proportions.
- Surfactant components such as fatty alcohol sulfates and fatty alcohol ether sulfates are intended for this purpose.
- Amphoteric surfactants can also be used for this (eg miranols). The best preparations can be achieved with the above-mentioned surfactant component fatty alcohol polyalkylene oxide adduct.
- Other additives are emulsifiers (e.g. Na, K or alkanolamine salts of fatty acids), thickeners (e.g. NaCl, NH 4 Cl in combinations with alkyl ether sulfates), superfatting agents (e.g.
- polyoxyethylated lanolin derivatives such as lecithin derivatives or alkylolamides
- framework components such as paraffin, full-fat alcohols, Protein breakdown products, vitamin complexes, solubilizers such as vinyl pyrrolidone-vinyl acetate copolymeridates, plant extracts.
- the active substances should be used in amounts between 0.001 and 0.1 g per patient and per day.
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Birds (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Cosmetics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3046391 | 1980-12-05 | ||
| DE19803046391 DE3046391A1 (de) | 1980-12-05 | 1980-12-05 | Antischuppenmittel |
| DE3104430 | 1981-02-04 | ||
| DE19813104430 DE3104430A1 (de) | 1981-02-04 | 1981-02-04 | Antischuppenmittel |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| EP0065974A1 true EP0065974A1 (de) | 1982-12-08 |
Family
ID=25789617
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP19820900018 Withdrawn EP0065974A1 (de) | 1980-12-05 | 1981-12-04 | Antischuppenmittel |
Country Status (3)
| Country | Link |
|---|---|
| EP (1) | EP0065974A1 (is") |
| JP (1) | JPS57502126A (is") |
| WO (1) | WO1982001819A1 (is") |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2013000572A1 (de) | 2011-06-30 | 2013-01-03 | 2LUTION GmbH | Mittel zur bekämpfung von parasiten an tieren |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS571781B2 (is") * | 1973-01-18 | 1982-01-12 | ||
| JPS5426197B2 (is") * | 1973-06-25 | 1979-09-03 | ||
| IE40911B1 (en) * | 1974-04-11 | 1979-09-12 | Schering Ag | Imidazole derivatives and process for their manufacture |
| DE2430039C2 (de) * | 1974-06-22 | 1983-11-10 | Bayer Ag, 5090 Leverkusen | Climbazol in kosmetischen Mitteln |
| GB2068228B (en) * | 1980-01-24 | 1984-02-29 | Janssen Pharmaceutica Nv | Anti-microbial compositions for the topical treatment of acne vulgaris |
-
1981
- 1981-12-04 JP JP57500101A patent/JPS57502126A/ja active Pending
- 1981-12-04 WO PCT/DE1981/000216 patent/WO1982001819A1/en not_active Application Discontinuation
- 1981-12-04 EP EP19820900018 patent/EP0065974A1/de not_active Withdrawn
Non-Patent Citations (1)
| Title |
|---|
| See references of WO8201819A1 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2013000572A1 (de) | 2011-06-30 | 2013-01-03 | 2LUTION GmbH | Mittel zur bekämpfung von parasiten an tieren |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS57502126A (is") | 1982-12-02 |
| WO1982001819A1 (en) | 1982-06-10 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PUAI | Public reference made under article 153(3) epc to a published international application that has entered the european phase |
Free format text: ORIGINAL CODE: 0009012 |
|
| 17P | Request for examination filed |
Effective date: 19820701 |
|
| AK | Designated contracting states |
Designated state(s): AT CH DE FR GB LU NL SE |
|
| STAA | Information on the status of an ep patent application or granted ep patent |
Free format text: STATUS: THE APPLICATION HAS BEEN WITHDRAWN |
|
| 18W | Application withdrawn |
Withdrawal date: 19831202 |
|
| RIN1 | Information on inventor provided before grant (corrected) |
Inventor name: STREHLKE, PETER |