EP0229155A1 - Complexe pharmaceutique et composition pour empecher la chute descheveux - Google Patents
Complexe pharmaceutique et composition pour empecher la chute descheveuxInfo
- Publication number
- EP0229155A1 EP0229155A1 EP86904524A EP86904524A EP0229155A1 EP 0229155 A1 EP0229155 A1 EP 0229155A1 EP 86904524 A EP86904524 A EP 86904524A EP 86904524 A EP86904524 A EP 86904524A EP 0229155 A1 EP0229155 A1 EP 0229155A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- surfactant polymer
- polyoxyethylene glycol
- complex
- polymer
- glycol derivative
- 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- Withdrawn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
- 201000004384 Alopecia Diseases 0.000 title claims abstract description 15
- 230000003676 hair loss Effects 0.000 title claims abstract description 15
- 208000024963 hair loss Diseases 0.000 title claims abstract description 15
- 239000000203 mixture Substances 0.000 title description 27
- 150000002334 glycols Chemical class 0.000 claims abstract description 24
- ZOJBYZNEUISWFT-UHFFFAOYSA-N allyl isothiocyanate Chemical class C=CCN=C=S ZOJBYZNEUISWFT-UHFFFAOYSA-N 0.000 claims abstract description 16
- 229920000642 polymer Polymers 0.000 claims description 39
- 239000004094 surface-active agent Substances 0.000 claims description 28
- -1 polyoxyethylene Polymers 0.000 claims description 24
- 229920003171 Poly (ethylene oxide) Polymers 0.000 claims description 20
- 238000000034 method Methods 0.000 claims description 14
- 239000008194 pharmaceutical composition Substances 0.000 claims description 10
- 235000016720 allyl isothiocyanate Nutrition 0.000 claims description 8
- 210000004761 scalp Anatomy 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 125000002947 alkylene group Chemical group 0.000 claims description 5
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 4
- 150000002148 esters Chemical class 0.000 claims description 4
- 239000000194 fatty acid Substances 0.000 claims description 4
- 229930195729 fatty acid Natural products 0.000 claims description 4
- 150000004665 fatty acids Chemical class 0.000 claims description 4
- 229950006451 sorbitan laurate Drugs 0.000 claims description 4
- 235000011067 sorbitan monolaureate Nutrition 0.000 claims description 4
- 229950004959 sorbitan oleate Drugs 0.000 claims description 4
- 229950003429 sorbitan palmitate Drugs 0.000 claims description 4
- 229950011392 sorbitan stearate Drugs 0.000 claims description 4
- 229920001451 polypropylene glycol Polymers 0.000 claims description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims 12
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims 6
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 claims 3
- 239000000600 sorbitol Substances 0.000 claims 3
- 239000007795 chemical reaction product Substances 0.000 claims 2
- 239000003937 drug carrier Substances 0.000 claims 1
- 230000002401 inhibitory effect Effects 0.000 claims 1
- 230000005764 inhibitory process Effects 0.000 claims 1
- 150000002540 isothiocyanates Chemical class 0.000 description 21
- 229920000053 polysorbate 80 Polymers 0.000 description 8
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 7
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
- 238000009792 diffusion process Methods 0.000 description 5
- 239000006071 cream Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 229920000136 polysorbate Polymers 0.000 description 3
- 229920000298 Cellophane Polymers 0.000 description 2
- 230000003808 decrease of hair loss Effects 0.000 description 2
- 239000006210 lotion Substances 0.000 description 2
- 235000019271 petrolatum Nutrition 0.000 description 2
- 239000002453 shampoo Substances 0.000 description 2
- 239000011877 solvent mixture Substances 0.000 description 2
- 229940099259 vaseline Drugs 0.000 description 2
- 208000001840 Dandruff Diseases 0.000 description 1
- 206010067482 No adverse event Diseases 0.000 description 1
- 208000002193 Pain Diseases 0.000 description 1
- 239000004264 Petrolatum Substances 0.000 description 1
- 239000011149 active material Substances 0.000 description 1
- 230000000172 allergic effect Effects 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 230000002421 anti-septic effect Effects 0.000 description 1
- 229940064004 antiseptic throat preparations Drugs 0.000 description 1
- 208000010668 atopic eczema Diseases 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 238000000502 dialysis Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003974 emollient agent Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 230000002070 germicidal effect Effects 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- IPCSVZSSVZVIGE-UHFFFAOYSA-M hexadecanoate Chemical compound CCCCCCCCCCCCCCCC([O-])=O IPCSVZSSVZVIGE-UHFFFAOYSA-M 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000000386 microscopy Methods 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 229940066842 petrolatum Drugs 0.000 description 1
- 208000017983 photosensitivity disease Diseases 0.000 description 1
- 231100000434 photosensitization Toxicity 0.000 description 1
- 229920001983 poloxamer Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000003871 white petrolatum Substances 0.000 description 1
Classifications
-
- 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
- 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
- A61K47/50—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 the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
- A61K47/51—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 the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent
- A61K47/56—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 the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic macromolecular compound, e.g. an oligomeric, polymeric or dendrimeric molecule
- A61K47/59—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 the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic macromolecular compound, e.g. an oligomeric, polymeric or dendrimeric molecule obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyureas or polyurethanes
- A61K47/60—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 the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic macromolecular compound, e.g. an oligomeric, polymeric or dendrimeric molecule obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyureas or polyurethanes the organic macromolecular compound being a polyoxyalkylene oligomer, polymer or dendrimer, e.g. PEG, PPG, PEO or polyglycerol
-
- 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
- A61K8/46—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur
-
- 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
- A61K8/4993—Derivatives containing from 2 to 10 oxyalkylene groups
Definitions
- This application is concerned with a pharmaceutically active complex useful to inhibit hair loss from the human scalp. More particularly, it is concerned with the complexes formed by reaction between allyl isothiocyanate and certain polyoxyalkylene glycols, with pharmaceutical compositions containing such complexes and with the use of the complexes to protect against loss of human hair.
- Polyoxyalkylene glycols are a well known class of surfactant polymers. They are ethers formed by the polymerization of selected • glycols. They are available in a variety of forms. Often they will carry other functional groups.
- the surfactant polymers useful in the practice of this invention will have a molecular weight of from 500 to 10,000, and the alkylene group will have 2 or 3 carbon atoms.
- Specific surfactant polymers useful in the practice of the invention may include copolymers derived from glycols with two or three carbon atoms in the alkylene groups.
- One class of surfactant polymers useful in the invention is available under the trademark Pluronic from BASF-Wyandotte.
- the class includes polyoxypropylene glycols.
- Tweens are polyoxyethylene glycol derivatives of fatty acid partial esters of sorbiton anhydrides. Amongst the most useful of the Tweens for the practice of this invention are polyoxyethylene glycol derivatives of sorbitan laurate, stearate, palmitate and oleate having molecular weights from 500 to 10,000.
- Still another useful class of polyoxyalkylene glycol derivatives is available from Union Carbide Corp. under the trademark Carbowax.
- ITC allyl isothiocyanate
- polyoxyethylene glycols at a temperature of from about 20 C to 60 C for a period of from about 0.5 to 30 hours, a complex will form.
- the ratio of ITC to surfactant polymer will depend upon the amounts of reactants employed. For the practice of this invention, the ratio of ITC to surfactant polymer is from about 1:1 to 1:20.
- the preferred solvents for the reaction are water and alkanols containing up to three carbon atoms. Ethanol and isopropanol are the preferred alkanols. Mixtures of solvents can be employed.
- the complex wil be utilized in the solvent mixture in which it is prepared, or the solvent mixture can be combined or blended with other carriers to form creams, lotions and the like. It is also convenient to utilize the solvent mix containing the dissolved complex to form shampoos which, for the purpose of this description and claims can be regarded as pharmaceutical compositions.
- SUBSTITUTE SHEET The complex need not be isolated. Its presence in the solution can be readily determined by the change in the infrared pattern between the original and final mixtures.
- the formation of the complexes can also be established by the fact that the rate of diffusion of the ITC is different from the rate of diffusion of the complex through cellophane into the same solvent in which the complex is prepared.
- the diffusion constants for certain samples are as follows:
- the first listed diffusion constant is for ITC alone.
- the second is for the complex that is formed after reaction between Tween 80 and ITC.
- Tween 80 is polyoxyethylene sorbitan monooleate.
- the diffusion rates were determined by the Drobnica method [Drobnica, Kanppova: Chem. Zvesti, 27 799 (1973)].
- the test material as prepared in a solvent was placed in a cellophane dialysis cell and the cell suspended in 10 times its volume of the same solvent. Aliquots were removed at selected time intervals from the solvent outside the cell and reacted to form thioglycols as a measure of the amount diffused.
- the complexes can be used in any of a variety of compositions including liquids, creams, lotions, emollients or other compositions generally employed for topical application.
- Useful compositions will contain from about 0.01% to 10% by weight of active complex based on the total weight of the composition.
- the compositions may contain other ingredients such as antiseptics, germicides or anti- dandruff compounds.
- compositions containing the complex when applied directly to the human scalp will inhibit hair loss.
- the preparation made according to Example 7 was tested with 30 different human subjects with a hair loss problem.
- the carrier of Example 7 without the complex was tested on 32 additional human subjects also suffering hair loss.
- the mixtures were applied by vigorous rubbing morning and evening for 30 consecutive days. Determination of the product effect was carried out by measuring the newly grown hair length, diameter and cuticle by light microscopy. The results are shown in the following table.
- Example 2 To 100 ml. of a 1.8:1 ethanol-water solution containing 0.00897 M ITC is added a solution of 0.0089 M Carbowax-6000 and the procedure of Example 1 is followed.
- the ITC:polymer ratio is 1:1.
- the concentration of the complex in the composition is approximately 5.3% by weight.
- Example 1 To 100 ml. of a 1.8:1. ethanol-water solution containing 0.00897 M ITC is added a solution of 0.0045 M Tween-80 and the procedure of Example 1 is followed to prepare a complex in which the molar ratio of ITC to polymer is 2:1 and the concentration of the complex in the composition is about 0.7% by weight.
- Example 5 To 100 ml. of a 1.8:1 ethanol-water solution containing 0.00449 M ITC is added a solution of 0.0049 M Carbowax-6000 and the procedure of Example 5 is followed. The mole ratio of ITC to polymer ratio is 1:1. The concentration of the complex in the composition is about 5%.
- Example 5 To 100 ml. of alcohol-water solution containing 0.00897 M ITC is added a solution of 0.0179 M Tween-80 and then the procedure described in Example 5 is followed. The ITC to polymer mole ratio is 1:1.9. The concentration of the complex in the composition is about 4.6%.
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Birds (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Dermatology (AREA)
- Cosmetics (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
Complexes d'isothiocyanate allylique et glycoles de polyoxyalcènedestinés à empêcher la chute des cheveux.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US74696485A | 1985-06-20 | 1985-06-20 | |
| US746964 | 1985-06-20 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| EP0229155A1 true EP0229155A1 (fr) | 1987-07-22 |
| EP0229155A4 EP0229155A4 (en) | 1991-03-13 |
Family
ID=25003095
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP19860904524 Withdrawn EP0229155A4 (en) | 1985-06-20 | 1986-06-16 | Pharmaceutical complex and composition to inhibit hair loss |
Country Status (3)
| Country | Link |
|---|---|
| EP (1) | EP0229155A4 (fr) |
| JP (1) | JPS63500517A (fr) |
| WO (1) | WO1986007535A1 (fr) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1999008514A1 (fr) * | 1997-08-20 | 1999-02-25 | Lxr Biotechnology, Inc. | Compositions contenant du polyethylene glycol et leurs utilisations |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4479903A (en) * | 1982-08-23 | 1984-10-30 | American Cyanamid Company | Process for the preparation of N-allyl-O-alkyl thionocarbamates |
| US4482500A (en) * | 1982-08-23 | 1984-11-13 | American Cyanamid Company | Process for the preparation of N-allyl-O-alkyl thionocarbamates |
| US4440783A (en) * | 1983-02-24 | 1984-04-03 | Bernard Weiss | Composition for repelling animals from garbage and the like |
| US4524178A (en) * | 1983-06-09 | 1985-06-18 | The Dow Chemical Company | Compositions of unsaturated polyesters or polyesteramides and efficient flexibilizers therefor |
-
1986
- 1986-06-16 WO PCT/US1986/001304 patent/WO1986007535A1/fr not_active Ceased
- 1986-06-16 EP EP19860904524 patent/EP0229155A4/en not_active Withdrawn
- 1986-06-16 JP JP61503578A patent/JPS63500517A/ja active Pending
Non-Patent Citations (2)
| Title |
|---|
| No further relevant documents have been disclosed. * |
| See also references of WO8607535A1 * |
Also Published As
| Publication number | Publication date |
|---|---|
| EP0229155A4 (en) | 1991-03-13 |
| JPS63500517A (ja) | 1988-02-25 |
| WO1986007535A1 (fr) | 1986-12-31 |
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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 |
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| AK | Designated contracting states |
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| 17P | Request for examination filed |
Effective date: 19870821 |
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| A4 | Supplementary search report drawn up and despatched |
Effective date: 19910122 |
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| AK | Designated contracting states |
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| STAA | Information on the status of an ep patent application or granted ep patent |
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| 18D | Application deemed to be withdrawn |
Effective date: 19900703 |
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| RIN1 | Information on inventor provided before grant (corrected) |
Inventor name: DARKO, LASZLO, L. |