WO1995019758A1 - Composition pour soin des cheveux - Google Patents

Composition pour soin des cheveux Download PDF

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Publication number
WO1995019758A1
WO1995019758A1 PCT/JP1995/000083 JP9500083W WO9519758A1 WO 1995019758 A1 WO1995019758 A1 WO 1995019758A1 JP 9500083 W JP9500083 W JP 9500083W WO 9519758 A1 WO9519758 A1 WO 9519758A1
Authority
WO
WIPO (PCT)
Prior art keywords
compound
same
integer
formula
equation
Prior art date
Application number
PCT/JP1995/000083
Other languages
English (en)
Japanese (ja)
Inventor
Hisayuki Komasaki
Masahiro Ohta
Okihiko Sakamoto
Chika Hanzawa
Yoshiharu Tuji
Tetsuya Sakai
Kazuhisa Kandori
Akira Sano
Original Assignee
Shiseido Company, Ltd.
Nippon Shinyaku Co., Ltd.
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 Shiseido Company, Ltd., Nippon Shinyaku Co., Ltd. filed Critical Shiseido Company, Ltd.
Publication of WO1995019758A1 publication Critical patent/WO1995019758A1/fr

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Classifications

    • 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
    • A61K8/4906—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom
    • A61K8/4913—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having five membered rings, e.g. pyrrolidone carboxylic acid
    • 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
    • A61K8/96—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution
    • A61K8/97—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution from algae, fungi, lichens or plants; from derivatives thereof
    • A61K8/9783—Angiosperms [Magnoliophyta]
    • A61K8/9789—Magnoliopsida [dicotyledons]
    • 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
    • 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

Definitions

  • the present invention relates to a head composition comprising a specific bis-tetrahydrofuran-type compound analog (also referred to as acetogenins) and having an excellent effect of preventing hair loss and promoting hair growth.
  • a specific bis-tetrahydrofuran-type compound analog also referred to as acetogenins
  • hair tonics containing various chemicals have been known.
  • vitamins such as vitamin E, amino acids such as methionine, vasodilators such as acetylcholine derivatives, anti-inflammatory agents such as purple root extract, female hormones such as estradiol, skin such as cepharanthin; function enhancers
  • sesame Sesamum orientale L.
  • rhizomes of gourd Alphainia galanga Swartz.
  • Acelaceae parsley 'J Pierisoselinura crispum Nym.
  • sesame oil may have a skin softening effect
  • seeds of ghetto and antelope may have an effective effect on skin diseases. It is mentioned.
  • Antelope seeds have been used as an abortive agent in old times and have also been reported to exhibit insecticidal activity (RN Chopra, et al., "Glossary of Indian Medicinal _Plants" C.S.I. _R., New De lhi, 1956, p. 20). Since then, considerable research has been carried out on substances derived from the seeds of Antelope. For example, according to Y. Fujimot 0 et al., Chem. Pharm. Bull., 36> (1988) 4802-4806, the formula
  • Japanese Patent Application Laid-Open No. 3-41076 discloses a general formula containing an extract of an anthracite seed oil with an organic solvent and a derivative thereof.
  • plant extracts of vanrain contain various bis-tetrahydrofuran-type compound analogs, and their various biological activities are also known. It is not known that it is effective for hair growth. Also, the above-mentioned West Doi Patent No. 3, 614, 448 teaches that roasted seeds of Banreishi are mixed with other plant components to be effective in promoting hair growth and the like. However, it does not teach that a specific ingredient derived from a non-roasted species alone exhibits the above efficacy. In the composition thus prepared, impurities other than the active ingredient are irritating and have a problem in terms of safety.
  • an object of the present invention is to provide a composition which can be used more safely and comfortably, and which is effective for strong hair loss prevention, hair growth and the like.
  • the present inventors have conducted extensive screening for the effect of preventing alopecia of components derived from medicinal plants, and found that a wide variety of bis-tetrahydrofuran-type compound analogs derived from plants belonging to the family Annonaceae Of the following formula (I)
  • RR 2 , R 3 , R 4 , R 5 and R 6 independently represent a hydrogen atom or a hydroxyl group, and R 4 is a carbonyl group together with the carbon atom to which it is bonded. May be
  • R represents a hydrogen atom or an acetyl group
  • P is an integer 7 or 9, or
  • the object of the present invention can be solved by providing a head composition comprising at least one compound represented by the formula (I) and its ester derivative as an active ingredient. Further, according to the present invention, as another aspect, hair loss of a mammal comprising administering to the scalp an effective amount of at least one compound of the formula (I) and its ester derivative as an active ingredient A method for preventing or promoting hair growth is provided.
  • HHHHHHH 7 (same as above)
  • 15 C represents the carbon at position 15 when the carbonyl carbon in the lactone ring of the substituent Z is at position 1, and th represents threo, er Represents erythro, t represents trans, and c represents cis.
  • ester derivatives thereof are preferred.
  • the compounds C-11, C-13, C-11, C-14, C-15 and C-19 listed in Table 1 above can be mentioned as preferred compounds.
  • all of the compounds are as follows: 15 C / 16 C th; 16 CZ19 C t; 19 C / 20 C th; 20 C / 23 C t; Those represented by C / 24 Cer are particularly preferred.
  • the ester derivative according to the present invention is a compound obtained by esterifying one or more hydroxyl groups of the compound of the formula (I.) by an esterification reaction known per se. include c particular, Asechiru derivatives.
  • the composition of the present invention contains a compound represented by the formula (I), in particular, at least one selected from the above compounds (C-1) to (C-23) or an ester derivative thereof.
  • a compound represented by the formula (I) in particular, at least one selected from the above compounds (C-1) to (C-23) or an ester derivative thereof.
  • other active compounds and additives can be included as long as they do not adversely affect the intended use.
  • the optimal amount of these compounds to be included in the composition is not limited as it may vary depending on the combination with the other active compounds and excipients, and the dosage form.c However, in general, It is convenient to include 5 to 0.000001% by weight, preferably 0.1 to 0.00001% by weight, based on the total composition weight. In a composition containing less than 0.00000001%, the amount of the composition itself needs to be significantly increased, which is inconvenient. On the other hand, if it exceeds 5%, it is disadvantageous in formulation and is not preferred.
  • a composition as described above or one or more of the compounds of formula (I) and their ester derivatives, in particular one of the compounds mentioned as being preferred
  • the effective amount of the compound is simply added to a mammal, especially a human, in the form of a solution dissolved in a lower alcohol such as ethanol, or if necessary, suspended in purified water in the presence of the above-mentioned surfactant.
  • a mammal especially a human
  • a lower alcohol such as ethanol
  • purified water in the presence of the above-mentioned surfactant.
  • hair loss prevention or hair growth promotion in mammals can be achieved.
  • it can be applied to alopecia areata in humans.
  • an effective amount of at least one of the compound represented by the formula (I) and its ester derivative is applied to a site where prevention of hair loss or promotion of hair growth in a mammal, particularly human scalp.
  • the present invention provides a method for preventing hair loss or promoting hair growth in a mammal, comprising administering.
  • a compound represented by the formula (I) for preparing a composition for preventing hair loss or promoting hair growth in mammals, and an ester derivative thereof, particularly, Use of those preferred is also provided.
  • composition for the head of the present invention thus prepared is not limited to a particular dosage form, and may be in any dosage form, for example, a tonic, a hair cream, a shampoo, a scalp treatment, and a rinse. They can be prepared according to methods known per se.
  • the present invention is more effective in preventing and improving hair growth and preventing hair loss, as will be more apparent from the following specific examples, and can be used more safely and comfortably than conventional head compositions and their use. That is, since the composition for the head of the present invention enables the use of only the active ingredient, clothes and pillows at bedtime can be stained with the pigment contained in the extract without pigments or irritants, It does not stick and does not cause unpleasant feeling. In addition, extra irritation and harm caused by impurities are also eliminated.
  • the composition for the head of the present invention can be used in various dosage forms, for example, for the treatment of prevention and improvement of hair growth promotion and hair loss, etc., as a pharmaceutical preparation, and as various cosmetics. Available in manufacturing.
  • the leaf lKg of Annona squamosa L. was subjected to reflux extraction with 10 L of methanol for 12 hours.
  • the extract was filtered and concentrated, and then subjected to silica gel chromatography to purify form, a liquid mixture of puroform and ethyl acetate, and then ethyl acetate.
  • the target component was separated using a mixture of toluene and methanol as an eluent to obtain 100 Omg of compound (C-1).
  • the Annona reticulata was. Seeds 1 K g at 10 L of petroleum ether, was 12 hours Soxhlet extraction with 6 0 e C. After filtering and concentrating the extract, the target component is separated by silica gel column chromatography using chlorophonolem, a mixture of chlorophosolem and ethyl acetate, and then a mixture of ethyl acetate and methanol as eluents.
  • the leaf l of Annona cherimolia Mill. L Kg was extracted by refluxing with 10 L of methanol for 12 hours, and the extract was filtered and concentrated, and then subjected to silica gel chromatography to form clomate, and a mixture of cloform form and ethyl acetate Then, the target component was separated using a mixture of ethyl acetate and methanol as an eluent to obtain 15 Omg of a compound (C-23).
  • the IR and 1 HN MR spectra of this compound were consistent with known literature values.
  • Example 7 Measurement of hair growth effect (measurement of hair growth effect in mouse)
  • mice Using male C3H mice (60 days after birth), experiments were performed according to the method of Ogawa et al. (Normal and Abnomal Epidermal Differentiation M. Seiji and I. A. Bernstein, edited by The University of Tokyo Press). The back of a mouse is shaved to a size of about 2 x 4 cm, and the sample is applied once a day from the next day, one sample at a time, and the change in the area of the part where hair regeneration has begun is determined. Was compared. The sample was prepared by stirring and dissolving the dried product in 75% ethanol. In the test, 75% ethanol was used as a control. For each sample, 10 mice were used, and the average value of the area was determined. 15 The results for the back hair regeneration area are summarized in percentages. The compounding amount of each compound in the preparation is represented by a weight ratio (that is, weight volume) when the total volume of the preparation is 100.
  • the compound (C-20) obtained in Example 5 showed 100% hair growth by application of 15 at a concentration of 0.005%.
  • Effective means that hair renewal is observed at 2Z3 or more of the hair loss part ⁇
  • Excellent effect means that hair has grown at the hair loss part.
  • Vitamin B 6 0.2%
  • Vitamin E 0.01%
  • Formulation Examples 15 to 20 were produced by a conventional method.
  • Ingredients (5 :) to (6) are dissolved in ingredients (1) and (4), heated to 80 ° C and uniformly dissolved, then cooled to 30 ° C and cooled to 30 ° C. ) And mixed with stirring.
  • Comparative Example 2 was manufactured for the purpose of positioning the feel of use in the use test, and the use tests were compared with Formulation Example 1 and Comparative Example 1.
  • Table 5 shows the test results of Formulation Example 1 and Comparative Example 2.
  • Formulation Example 1 had a much better feel to use than Comparative Example 2, and was a formulation with no practical problems.
  • Table 6 shows the test results of Formulation Example 1 and Comparative Example 1. In comparison, both preparations had a very good feel to use, and the preparations were the same in use and had no practical problems. Table 6 Comparison of use in Preparation 1 to Comparative Example 1 (10 panelists) Item Evaluation point + 2 + 1 0 1 1-2 Average score of evaluation points Stickiness 1 0 0

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  • 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)
  • Engineering & Computer Science (AREA)
  • Microbiology (AREA)
  • Biotechnology (AREA)
  • Dermatology (AREA)
  • Mycology (AREA)
  • Botany (AREA)
  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Organic Chemistry (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Cosmetics (AREA)
  • Furan Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicines Containing Plant Substances (AREA)

Abstract

Une composition pour le soin des cheveux contient, comme ingrédient actif, au moins un élément choisi parmi des analogues de bis-tétrahydrofurane et leurs esters provenant d'une plante de la famille Annonaceae; l'utilisation des composés de bis-tétrahydrofurane, en particulier, un procédé contre la chute des cheveux ou favorisant la croissance des cheveux par administration de ces composés sur le cuir chevelu, et l'utilisation des composés décrits ci-dessus dans la préparation de ladite composition pour le soin des cheveux sont également décrits.
PCT/JP1995/000083 1994-01-25 1995-01-25 Composition pour soin des cheveux WO1995019758A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP6/23042 1994-01-25
JP6023042A JPH1135426A (ja) 1994-01-25 1994-01-25 頭部用組成物

Publications (1)

Publication Number Publication Date
WO1995019758A1 true WO1995019758A1 (fr) 1995-07-27

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ID=12099410

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP1995/000083 WO1995019758A1 (fr) 1994-01-25 1995-01-25 Composition pour soin des cheveux

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JP (1) JPH1135426A (fr)
WO (1) WO1995019758A1 (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6991818B2 (en) 2001-03-30 2006-01-31 Council Of Scientific & Industrial Research Compound iso-squamocin obtained from seeds of annona squamosa and composition containing the same
FR2895906A1 (fr) * 2006-01-06 2007-07-13 Limousine D Applic Biolog Dite Principe actif issu d'annova squamosa, procede d'obtention et utilisation cosmetique a visee anti-age

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP5676837B2 (ja) * 2007-11-02 2015-02-25 丸善製薬株式会社 毛乳頭細胞増殖促進剤、線維芽細胞増殖因子−７（ｆｇｆ−７）産生促進剤、血管内皮増殖因子（ｖｅｇｆ）産生促進剤、抗男性ホルモン剤、育毛剤及び頭髪化粧料
JP7445727B1 (ja) 2022-11-07 2024-03-07 株式会社ソディック ワイヤ放電加工装置

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH02104582A (ja) * 1987-07-09 1990-04-17 Arizona Board Of Regents ロリニアスタチン１

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH02104582A (ja) * 1987-07-09 1990-04-17 Arizona Board Of Regents ロリニアスタチン１

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6991818B2 (en) 2001-03-30 2006-01-31 Council Of Scientific & Industrial Research Compound iso-squamocin obtained from seeds of annona squamosa and composition containing the same
FR2895906A1 (fr) * 2006-01-06 2007-07-13 Limousine D Applic Biolog Dite Principe actif issu d'annova squamosa, procede d'obtention et utilisation cosmetique a visee anti-age

Also Published As

Publication number Publication date
JPH1135426A (ja) 1999-02-09

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