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WO1986007535A1 - Complexe pharmaceutique et composition pour empecher la chute descheveux - Google Patents

Complexe pharmaceutique et composition pour empecher la chute descheveux Download PDF

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Publication number
WO1986007535A1
WO1986007535A1 PCT/US1986/001304 US8601304W WO8607535A1 WO 1986007535 A1 WO1986007535 A1 WO 1986007535A1 US 8601304 W US8601304 W US 8601304W WO 8607535 A1 WO8607535 A1 WO 8607535A1
Authority
WO
WIPO (PCT)
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.)
Ceased
Application number
PCT/US1986/001304
Other languages
English (en)
Inventor
Laszlo L. Darko
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
FARMACON Inc
Original Assignee
FARMACON Inc
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by FARMACON Inc filed Critical FARMACON Inc
Publication of WO1986007535A1 publication Critical patent/WO1986007535A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

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.
PCT/US1986/001304 1985-06-20 1986-06-16 Complexe pharmaceutique et composition pour empecher la chute descheveux Ceased WO1986007535A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US74696485A 1985-06-20 1985-06-20
US746,964 1985-06-20

Publications (1)

Publication Number Publication Date
WO1986007535A1 true WO1986007535A1 (fr) 1986-12-31

Family

ID=25003095

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US1986/001304 Ceased WO1986007535A1 (fr) 1985-06-20 1986-06-16 Complexe pharmaceutique et composition pour empecher la chute descheveux

Country Status (3)

Country Link
EP (1) EP0229155A4 (fr)
JP (1) JPS63500517A (fr)
WO (1) WO1986007535A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
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

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4440783A (en) * 1983-02-24 1984-04-03 Bernard Weiss Composition for repelling animals from garbage and the like
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
US4524178A (en) * 1983-06-09 1985-06-18 The Dow Chemical Company Compositions of unsaturated polyesters or polyesteramides and efficient flexibilizers therefor

Patent Citations (4)

* Cited by examiner, † Cited by third party
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

Non-Patent Citations (5)

* Cited by examiner, † Cited by third party
Title
CHEMICAL ABSTRACT, (Columbus Ohio, USA) Volume 94, Abstract No. 180499s, 04 February 1981 (04.02.81) *
CHEMICAL ABSTRACTS, (Columbus Ohio, USA) Volume 102. Abstract No. 12197g, 12 September 1984 (12.9.84) *
CONN, Current Therapy, 1981 edition, page 662 (1981) *
See also references of EP0229155A4 *
The Merck Index, 9th edition, Abstract No. 289 (1976) *

Cited By (1)

* Cited by examiner, † Cited by third party
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

Also Published As

Publication number Publication date
JPS63500517A (ja) 1988-02-25
EP0229155A4 (en) 1991-03-13
EP0229155A1 (fr) 1987-07-22

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