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WO2007013581A1 - Composition sedative - Google Patents

Composition sedative Download PDF

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Publication number
WO2007013581A1
WO2007013581A1 PCT/JP2006/314958 JP2006314958W WO2007013581A1 WO 2007013581 A1 WO2007013581 A1 WO 2007013581A1 JP 2006314958 W JP2006314958 W JP 2006314958W WO 2007013581 A1 WO2007013581 A1 WO 2007013581A1
Authority
WO
WIPO (PCT)
Prior art keywords
composition
group
hydrogen atom
general formula
sleep
Prior art date
Application number
PCT/JP2006/314958
Other languages
English (en)
Japanese (ja)
Inventor
Yasuyuki Hasegawa
Original Assignee
Kobayashi Pharmaceutical 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
Priority claimed from JP2005219377A external-priority patent/JP4632895B2/ja
Priority claimed from JP2006035834A external-priority patent/JP2007031421A/ja
Application filed by Kobayashi Pharmaceutical Co., Ltd. filed Critical Kobayashi Pharmaceutical Co., Ltd.
Publication of WO2007013581A1 publication Critical patent/WO2007013581A1/fr

Links

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
    • A61K31/045—Hydroxy compounds, e.g. alcohols; Salts thereof, e.g. alcoholates
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/20—Hypnotics; Sedatives

Definitions

  • the present invention relates to a sedative composition. More specifically, the present invention relates to a sedative composition that excels in the action of calming the spirit of humans and animals.
  • sandalwood has been rapidly decreasing in number in recent years due to overcutting, and sandalwood oil produced from the plant moss has been steadily decreasing. With such a decrease in the production of sandalwood oil, the development of synthetic compounds exhibiting the same scent as sandalwood oil is being energetically promoted today.
  • the sedative effect of sandalwood oil has no direct causal relationship with the smell of smelled sandalwood oil, and it is a compound that exhibits the same or similar scent as sandalwood.
  • the current situation is Tatsuno.
  • Patent Document 1 Japanese Patent Laid-Open No. 7-316582
  • Patent Document 2 Japanese Patent Publication No. 7-57734
  • An object of the present invention is to provide a composition for sedation which is excellent in the action of sedating a human or animal spirit.
  • the present invention provides the following inventions:
  • R to R are the same or different and each represents a hydrogen atom, a hydroxyl group or a methyl group;
  • 9 is the same or different and represents a hydrogen atom or a methyl group
  • A represents an ethylene group or a beylene group, and n represents an integer of 0 to 10]
  • a sedative composition comprising: a sedative composition.
  • Item 2 The composition for sedation according to Item 1, wherein in General Formula (1), at least three of R to R are acetyl groups.
  • R to R are all methyl groups, and R to R are all hydrogen atoms.
  • Item 2 The sedative composition according to Item 1.
  • Item 2 A sedative composition according to Item 1.
  • Item 5 The sedative composition according to Item 1, wherein n is 0 to 2 in the general formula (1).
  • R to R are all methyl groups, and R to R are all hydrogen atoms.
  • Item 2 The sedation according to Item 1, wherein one or both of R and R are acetyl groups.
  • R ⁇ R cation group R ⁇ R is hydrogen atom, R force S methyl group, R is hydrogen atom, A is ethyl
  • R ⁇ R force S methyl group R ⁇ R is hydrogen atom, R and R force S methyl group, A is beylene group,
  • n 0
  • Item 2 The sedative composition according to Item 1.
  • Item 8 In the sedative composition, the ratio of the compound represented by the general formula (1) to the total amount of the compound represented by the general formula (1) and the fragrance component is 10% by weight or more. Item 8. A sedative composition according to any one of items 1 to 7,
  • Item 9 The sedative composition according to any one of Items 1 to 8, which is in the form of a fragrance, a cosmetic, an inhalation agent, a textile detergent, or a food.
  • R to R are the same or different and each represents a hydrogen atom, a hydroxyl group or a methyl group,
  • R and R are the same or different and each represents a hydrogen atom or a methyl group
  • A represents an ethylene group or a beylene group
  • n an integer of 0 to 10]
  • a composition for improving sleep comprising:
  • Item 11 The sleep improving composition according to Item 10, wherein, in General Formula (1), at least three of R to R are methyl groups.
  • R to R are all methyl groups, and R to R are all hydrogen atoms.
  • Item 11 The composition for improving sleep according to Item 10, which is a child.
  • Item 11 The composition for improving sleep according to Item 10.
  • Item 14 The composition for improving sleep according to Item 10, wherein n force ⁇ -2 in the general formula (1).
  • Item 15. In the general formula (1), R to R are all methyl groups, and R to R are all hydrogen atoms.
  • R ⁇ R cation group R ⁇ R is hydrogen atom, R force S methyl group, R is hydrogen atom, A is ethyl
  • R ⁇ R cation group R ⁇ R is hydrogen atom, R force S methyl group, R is hydrogen atom, A is beryl
  • R ⁇ R force S methyl group R ⁇ R is hydrogen atom, R and R force S methyl group, A is beylene group,
  • n 0
  • Item 11 The composition for improving sleep according to Item 10, wherein
  • Item 17 In the composition for improving sleep, the ratio of the compound represented by the general formula (1) to the total amount of the compound represented by the general formula (1) and the fragrance component is 10% by weight or more. Item 17. The composition for improving sleep according to any one of Items 10 to 16.
  • Item 18 The sleep improving composition according to any one of Items 10 to 17, which is in the form of a fragrance, a cosmetic, an inhalation agent, a textile detergent, or a food.
  • the “sedative composition” is used to relax or improve sleep by soothing the mind of a human or animal.
  • the “sleep improvement composition” refers to a good sleep state that induces sleep by improving sleepiness when waking up, smoothing sleep, reducing arousal during sleep, etc. Is used to guide
  • the sedative composition of the present invention is characterized by containing a compound of the following general formula (1).
  • I ⁇ to R 7 are the same or different and are a hydrogen atom, a hydroxyl group or a methyl group, preferably a hydrogen atom or a methyl group.
  • at least three of R to R are preferably acetyl groups, particularly R methyl group and R
  • All of ⁇ R are preferably hydrogen atoms.
  • R and R are the same or different and each represents a hydrogen atom or a methyl group.
  • either one or both of R and R are S methyl groups.
  • A represents an ethylene group (CH 2 —CH 2) or a beylene group (CH ⁇ CH).
  • n is an integer of 0 to 10. In the compound of the general formula (1), preferably n is
  • n 0 or 1
  • n is 0.
  • R ⁇ R cation group R ⁇ R is hydrogen atom, R force S methyl group, R is hydrogen atom, A is ethyl
  • n 0 (ie, 3-methyl-5- (2,2,3-trimethyl-3-cyclopenten-1-yl) -pentan-2-ol);
  • R ⁇ R cation group R ⁇ R is hydrogen atom, R force S methyl group, R is hydrogen atom, A is beryl
  • R ⁇ R force S methyl group R ⁇ R is hydrogen atom, R and R force S methyl group, A is beylene group, and
  • the compound represented by the general formula (1) is a known compound or a compound that is easily derived from a known compound power.
  • the compound represented by the general formula (1) is produced by various known synthetic methods depending on the basic skeleton, the type of substituents, and the like.
  • the compound represented by the general formula (1) is a compound represented by the following general formula (2) (wherein R
  • ⁇ R and n are the same as described above) and an appropriate aldehyde or ketone is subjected to aldol condensation under appropriate conditions, and further reduced under appropriate conditions.
  • the compound represented by the general formula (2) used as the raw material mixture of the compound represented by the general formula (1) is a known compound or a compound easily derived from the known compound. is there.
  • the compound represented by the general formula (2) is camphorolenal (campholenicaldehyde; a compound in which R to R force S methyl group, R to R is hydrogen atom, n force SO in general formula (2)) Even if camphorolenal (campholenicaldehyde; a compound in which R to R force S methyl group, R to R is hydrogen atom, n force SO in general formula (2)) Even if camphorolenal (campholenicaldehyde; a compound in which R to R force S methyl group, R to R is hydrogen atom, n force SO in general formula (2)) Even if camphorolenal (campholenicaldehyde; a compound in which R to R force S methyl group, R to R is hydrogen atom, n force SO in general formula (2)) Even if camphorolenal (campholen
  • a pinene ( ⁇ -pinene) can be epoxidized, and the resulting epoxide can be reacted in the presence of ZnBr under appropriate conditions.
  • one compound may be used alone, or two or more compounds may be used in any combination. You can do it.
  • the compound represented by the general formula (1) includes a compound that itself exhibits a sandalwood fragrance.
  • a component exhibiting aroma such as an essential oil component or a synthetic fragrance obtained from natural plants and animals by an existing extraction method (hereinafter referred to as a fragrance composition) , "Denoted as" perfume ingredient ").
  • the total amount of the compound represented by the general formula (1) and the fragrance component fragment components other than the compound represented by the general formula (1).
  • the compound represented by the general formula (1) is preferably 10% by weight or more, preferably 40% by weight or more, and more preferably 70% by weight or more.
  • the sedative composition of the present invention may be composed of only the compound represented by the general formula (1), but depending on the form of use, it may be a carrier, a substrate, an additive, or the like. Other components may be contained.
  • the ratio of the compound represented by the general formula (1) depends on the use form of the composition, the degree of expected effect, the gender and age of the user, etc. Although different, for example, the ratio of the compound represented by the general formula (1) to 0.01 to L00% by weight, preferably 0.05 to 80% by weight, with respect to the total weight of the composition.
  • the form of the sedative composition of the present invention is not particularly limited as long as the compound represented by the general formula (1) is prepared so as to be inhaled or absorbed.
  • Specific examples of the form of the sedative composition of the present invention include fragrances, cosmetics, inhalation administration agents, textile detergents, foods and the like. Preferred are fragrances, cosmetics, inhalation administration agents, and textile products, and more preferred are fragrances and cosmetics.
  • fragrances examples include those for which conventional power is also used as fragrances, such as for bedrooms, living rooms, toilets, entrances, bathrooms, closets, and chiffons.
  • the form of the fragrance is not limited, and various forms such as a solid form, a semi-solid form (jelly form, gel form, etc.), a liquid form, and an aerosol form are used.
  • the fragrance may be used by spontaneously evaporating the compound represented by the general formula (1), or the compound may be evaporated by heating. In particular, if the compound represented by the general formula (1) is poor in volatility, it is desirable to evaporate by heating.
  • the sedative composition of the present invention is conventionally used as a fragrance in addition to the compound represented by the general formula (1).
  • Ingredients such as the base, support, additive, etc., can be contained.
  • the base compounded in the fragrance include water, ethanol, solid or liquid anionic, cationic, nonionic active agent, polymer agent, fats and oils, guar gum, xanthan gum, gum arabic, and dielan gum.
  • the sedative composition of the present invention is in the form of a fragrance
  • a particularly suitable blending ratio of the compound represented by the general formula (1) is represented by the general formula (1) in the composition.
  • the proportion of the compound is 5 to 80% by weight, more preferably 40 to 60% by weight.
  • cosmetics include biological cleaning agents such as sarcophagus, bathing agents, and the like.
  • Specific examples of cosmetics include creams, milky lotions, cosmetic powders, body lotions, hair styling, hair shampoos, sarcophagus, body soaps, antiperspirants, shampoos, rinses, perfumes, lotions, toothpastes, liquid toothpastes, washing Examples include mouth preparations, mouse pets, sunscreens, kitchen detergents, massage oils, massage creams, skin care oils, and the like.
  • the sedative composition of the present invention is represented by the general formula (1).
  • components such as bases and additives conventionally used in cosmetics can be contained.
  • the base is not particularly limited, and examples thereof include water, ethanol, talc, gelatin, wax, petrolatum, and lanolin.
  • the additive is not particularly limited, and examples thereof include humectants, skin softeners, preservatives, solubilizers, and fragrances.
  • a particularly suitable blending ratio of the compound represented by the general formula (1) is represented by the general formula (1) in the composition.
  • the proportion of the compound is 0.01 to 50% by weight, more preferably 0.05 to 10% by weight, and still more preferably 0.1 to 1% by weight.
  • An inhalation administration agent is a preparation in which the compound represented by the above general formula (1) is volatilized in the vicinity of the nose or applied to the nasal cavity to intentionally inhale the compound. Examples include nasal sprays, sprays, inhalation solutions, and masks carrying the compounds.
  • the sedation composition of the present invention is in the form of an inhalation administration agent, the sedation composition of the present invention has been conventionally used for an inhalation administration agent in addition to the compound represented by the general formula (1). Ingredients such as bases and additives can be included.
  • an inhalation gas is used, the gas that has been used in conventional inhalation administration agents can be used. Administration of the inhalation agent
  • the inhalation administration agent is a compound power represented by the above general formula (1) in the inhaled gas at the time of use, usually 0.000001 ppm to 10 ppm, preferably O.OOOOlppm to 0.1 ppm, It is desirable to set appropriately so as to volatilize at a concentration of about 0.0001 ppm to 0.001 ppm.
  • textile detergents include anionic, cationic, nonionic or zwitterionic detergents, textile softeners, textile softeners, dryer textile softeners, and the like. Can be mentioned.
  • the sedative composition of the present invention is in the form of a detergent for textile products, the compound represented by the general formula (1) can be adhered to the textile product by washing the textile product, and the compound is adhered. Excellent sedation can be obtained through the use of textile products.
  • the sedation composition of the present invention is made into the form of a detergent for textile products, the sedation composition of the present invention includes a detergent for textile products in addition to the compound represented by the general formula (1). Other ingredients used in can be used.
  • a particularly suitable blending ratio of the compound represented by the general formula (1) is as follows: The proportion of the compound represented is 0.01 to 10% by weight, more preferably 0.05 to 5% by weight.
  • Examples of foods include health foods, foods for sick people, foods for specified health use, and dietary supplements.
  • the compound represented by the above general formula (1) is inhaled through the oral mucosa, staying in the mouth for a relatively long time, or tea. It is preferable that the compound represented by the general formula (1) volatilizes and is inhaled through the nasal mucosa before being put into the mouth, such as a flavoring agent.
  • Specific examples of such foods include gums, teas, beverages, rice cakes, flavorings, spices, gummi, yogurt, ice cream, edible films and the like.
  • the sedative composition of the present invention is selected from the compounds represented by the above general formula (1) that are acceptable for food hygiene. It is prepared by blending as a component of food.
  • the sedative composition of the present invention prepared in a food form is used as a sedative food or for sedation, to be used for promoting sleep, to be used for stress relief, Or it is useful as a food displayed to be used to improve sleep.
  • a particularly suitable blending ratio of the compound represented by the general formula (1) is represented by the general formula (1) in the composition.
  • the proportion of the compound is 0.01 to 10% by weight.
  • the sedative composition of the present invention includes, for example, bedding such as futons and pillows; clothing; curtains; doors; screen doors; interior materials; On the other hand, there are those used in a mode in which the compound represented by the general formula (1) is sprayed or applied.
  • the compound represented by the general formula (1) is volatilized from various articles to which the compound represented by the general formula (1) is adhered.
  • An excellent sedative effect can be obtained.
  • Preferred examples of such forms include spray preparations, aerosol preparations, liquid, jelly-like or cream-like preparations, and those obtained by impregnating them with a nonwoven fabric.
  • the invention's effect [0038]
  • the sedative composition of the present invention exhibits the same or similar scent as sandalwood and can exhibit an excellent mental sedative effect on humans and animals.
  • the sedative composition of the present invention also has an excellent sleep improving effect, fatigue recovery effect, stress relieving effect or relaxing effect. It is also useful as a fatigue recovery composition, a stress relaxation composition, or a relaxation composition. Among them, the sedative composition of the present invention is particularly useful as a sleep improving composition for inducing a good sleep state and inducing a good sleep state.
  • Example 1 and 3 and Comparative Examples 1 and 3 The compositions of Example 1-3 and Comparative Example 1-3 all have a sandalwood fragrance.
  • R 8 is methyl group
  • R 9 is hydrogen atom
  • A is
  • 1 ⁇ to 1 3 is methyl
  • R 8 is a methyl group
  • R 9 is a hydrogen atom
  • A is
  • Pentene-1-yl -4-penten-2-ol (general)
  • the subjects put a micromini R'R type actigraph (manufactured by AMI, USA; obtained from Christi Shoji Co., Ltd.) on their non-dominant arm at the time of going to bed, and measured and digitized the minute movements of the sleeping body. . Also, together with “Yuka Yamamoto et al., Development and standardization of OSA sleep questionnaire (MA version) for middle-aged and elderly, elderly people”, Brain and Psychiatry, 10th, 4th, 1999, In accordance with the method reported in Section 401-409, subjects were asked to make a judgment on each item of the OSA sleep schedule. Each factor of recovery and sleep time was evaluated.
  • FIGs. 1 to 3 show the results of the compositions of Examples 1 to 3, respectively;
  • Figures 4 to 6 show the results of the compositions of Comparative Examples 1 to 3, respectively.
  • A shows the amount of activity during sleep (average value of 5 subjects) (unit: actigraph count) measured by micromini R'R type actigraph; Shows the results of quantification of each factor of sleepiness at sleep, sleep onset and sleep maintenance, dream, recovery from fatigue, and sleep time based on the judgment results of each item of the OSA sleep questionnaire (average value of 5 subjects) Indicates.
  • a cosmetic product (cream) having the following composition was prepared according to a conventional method.
  • Carboxyvinyl polymer (trade name “Carbopol 980”, BF Goodrich) 0.20
  • 3-methyl-5- (2,2,3 A cosmetic (cream) was prepared with the same composition as in Example 4 except that -trimethyl-3-cyclopenten-1-yl) -pentane-2-ol was used.
  • 3-methyl-5- (2,2,3-trimethyl-3-cyclopenten-1-yl) -4-penten-2-ol 3-methyl-5- (2,2,3-trimethyl
  • a cosmetic (cream) was prepared with the same composition as in Example 4 except that -3-cyclopenten-1-yl) -pentane-2-ol was used.
  • Fig. 1 shows the results of evaluating the mental sedation effect and sleep improvement effect of the composition of Example 1 in Test Example 1.
  • A shows the amount of sleep activity (vertical axis; unit is the number of actigraph counts) measured by micromini R'R type actigraph;
  • B shows the judgment result of each item of the OSA sleep survey form Based on sleepiness, wakefulness, sleep and sleep maintenance, dream, fatigue The numerical results (vertical axis; judgment value) for each factor of recovery and sleep time are shown.
  • Test Example 1 the results of evaluating the mental sedation effect and sleep improvement effect of the composition of Example 2 are shown. Items displayed by A and B in the figure are the same as those in Figure 1.
  • Test Example 1 the results of evaluating the mental sedation effect and sleep improvement effect of the composition of Example 3 are shown. Items displayed by A and B in the figure are the same as those in Figure 1.

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  • Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Medicinal Chemistry (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Neurosurgery (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Anesthesiology (AREA)
  • Neurology (AREA)
  • Biomedical Technology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Epidemiology (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

L'invention concerne une composition sédative présentant un excellent effet sédatif sur une personne ou un animal, ainsi qu'une composition favorisant le sommeil permettant d'améliorer la qualité du sommeil. L'invention consiste en une composition sédative ou favorisant le sommeil comprenant un composé représenté par la formule générale (1) : (1) où R1 à R7 représentent indépendamment un atome d'hydrogène, un groupe hydroxyle ou un groupe méthyle ; R8 et R9 représentent indépendamment un atome d'hydrogène ou un groupe méthyle ; A représente un groupe éthylène ou vinylène ; et n représente un entier compris entre 0 et 10.
PCT/JP2006/314958 2005-07-28 2006-07-28 Composition sedative WO2007013581A1 (fr)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
JP2005219377A JP4632895B2 (ja) 2005-07-28 2005-07-28 睡眠改善用組成物
JP2005-219377 2005-07-28
JP2006-035834 2006-02-13
JP2006035834A JP2007031421A (ja) 2006-02-13 2006-02-13 鎮静用組成物

Publications (1)

Publication Number Publication Date
WO2007013581A1 true WO2007013581A1 (fr) 2007-02-01

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Application Number Title Priority Date Filing Date
PCT/JP2006/314958 WO2007013581A1 (fr) 2005-07-28 2006-07-28 Composition sedative

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Country Link
WO (1) WO2007013581A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2008146883A1 (fr) * 2007-05-29 2008-12-04 Osaka Bioscience Institute Agent d'amélioration du sommeil

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS63199292A (ja) * 1987-02-13 1988-08-17 高砂香料工業株式会社 香料組成物及び該香料組成物を含む香粧品
JPH0328300A (ja) * 1989-06-26 1991-02-06 Kanebo Ltd 精油及び該精油を含む香粧品
JPH07316582A (ja) * 1994-05-21 1995-12-05 Shiseido Co Ltd 誘眠香料組成物
JPH1025245A (ja) * 1996-07-11 1998-01-27 Kobayashi Pharmaceut Co Ltd 経口催眠剤、催眠性飲食物及び催眠性餌料
JP2000109457A (ja) * 1998-08-17 2000-04-18 Givaudan Roure Internatl Sa オキシムカルボン酸誘導体
WO2002049600A1 (fr) * 2000-12-20 2002-06-27 Quest International B.V. Compostions de parfums

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS63199292A (ja) * 1987-02-13 1988-08-17 高砂香料工業株式会社 香料組成物及び該香料組成物を含む香粧品
JPH0328300A (ja) * 1989-06-26 1991-02-06 Kanebo Ltd 精油及び該精油を含む香粧品
JPH07316582A (ja) * 1994-05-21 1995-12-05 Shiseido Co Ltd 誘眠香料組成物
JPH1025245A (ja) * 1996-07-11 1998-01-27 Kobayashi Pharmaceut Co Ltd 経口催眠剤、催眠性飲食物及び催眠性餌料
JP2000109457A (ja) * 1998-08-17 2000-04-18 Givaudan Roure Internatl Sa オキシムカルボン酸誘導体
WO2002049600A1 (fr) * 2000-12-20 2002-06-27 Quest International B.V. Compostions de parfums

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
DIMOGLO A.S. ET AL.: "Investigation of the relationship between sandalwood odor and chemical structure: electron-topological approach", NEW JOURNAL OF CHEMISTRY, vol. 19, no. 2, February 1995 (1995-02-01), pages 149 - 154, XP002067557 *

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2008146883A1 (fr) * 2007-05-29 2008-12-04 Osaka Bioscience Institute Agent d'amélioration du sommeil
JPWO2008146883A1 (ja) * 2007-05-29 2010-08-19 財団法人大阪バイオサイエンス研究所 睡眠改善剤

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