WO2014148136A1 - Composé ayant une activité anti-allergique et son utilisation - Google Patents

Composé ayant une activité anti-allergique et son utilisation Download PDF

Info

Publication number
WO2014148136A1
WO2014148136A1 PCT/JP2014/052754 JP2014052754W WO2014148136A1 WO 2014148136 A1 WO2014148136 A1 WO 2014148136A1 JP 2014052754 W JP2014052754 W JP 2014052754W WO 2014148136 A1 WO2014148136 A1 WO 2014148136A1
Authority
WO
WIPO (PCT)
Prior art keywords
tic
unsubstituted
substituted
group
antiallergic
Prior art date
Application number
PCT/JP2014/052754
Other languages
English (en)
Japanese (ja)
Inventor
田中　宏幸
飯沼　宗和
Original Assignee
岐阜市
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 岐阜市 filed Critical 岐阜市
Publication of WO2014148136A1 publication Critical patent/WO2014148136A1/fr

Links

Images

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
    • C07C57/02—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms with only carbon-to-carbon double bonds as unsaturation
    • C07C57/03—Monocarboxylic acids
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
    • A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
    • A23L33/115—Fatty acids or derivatives thereof; Fats or oils
    • A23L33/12—Fatty acids or derivatives thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/08—Antiallergic agents
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/02—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
    • C07C233/09—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with carbon atoms of carboxamide groups bound to carbon atoms of an acyclic unsaturated carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/34—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups
    • C07C233/35—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
    • C07C233/38—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom having the carbon atom of the carboxamide group bound to a carbon atom of an acyclic unsaturated carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/22—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with hetero atoms directly attached to ring nitrogen atoms
    • C07D295/28—Nitrogen atoms
    • C07D295/32—Nitrogen atoms acylated with carboxylic or carbonic acids, or their nitrogen or sulfur analogues

Definitions

  • the present invention relates to a compound exhibiting antiallergic activity and its use.
  • This application claims priority based on Japanese Patent Application No. 2013-056798 filed on Mar. 19, 2013, the entire contents of which are incorporated by reference.
  • Non-patent Document 1 Treatment guidelines for allergic diseases have been recently created (Non-patent Document 1), and the usage rate of inhaled steroids and the like has increased accordingly, but such as allergic rhinitis, food allergy, atopic dermatitis, etc. In patients with diseases, patient satisfaction with treatment is still low. In Europe and the United States, the relationship between these allergic diseases and decreased QOL and productivity has been pointed out, and the development of new therapeutic agents is desired.
  • IgE antibodies are known to play a central role not only in the activation of mast cells but also in the presentation of antigens and the activation of various inflammatory cells. Particularly, anti-IgE antibodies have recently been used. Its role has been regained attention since the previous treatment was applied to the treatment of patients with atopic refractory asthma. On the other hand, some of the components derived from natural products have an antiallergic action, but the medium chain fatty acids for which various actions have been reported so far are unclear. Accordingly, the present inventors have focused on medium-chain fatty acid derivatives and have conducted research aimed at creating compounds having antiallergic activity.
  • Antiallergic compound represented by the following chemical formula (A) or (B): Where R1 is a hydrogen atom, an unsubstituted or substituted methyl group, an unsubstituted or substituted ethyl group, an unsubstituted or substituted pentyl group, or an unsubstituted or substituted phenyl group, and R2 is unsubstituted or substituted A substituted ethyl group, an unsubstituted or substituted aminoethyl group, an unsubstituted or substituted pentyl group, an unsubstituted or substituted phenyl group, or an unsubstituted or substituted piperidinyl group.
  • TIC medium chain fatty acid derivative
  • ACA mouse active skin anaphylaxis
  • IPD suplatast tosylate
  • OVA ovalbumin
  • B shows the effect of various TIC compounds on serum OVA-specific IgE levels. Compared with some IPD. Comparison was made using the following formula.
  • Ratio inhibition rate by TIC compound (%) / inhibition rate by IPD (%).
  • DPH diphenhydramine
  • PCA passive skin anaphylaxis
  • PCA (-); group in which purified water was orally administered to non-sensitized mice, PCA (+); group in which purified water was orally administered to mouse-sensitized mice, Vehi; vehicle (0.2% EtOH / PBS diluted solution) )
  • #, ## p ⁇ 0.05, 0.005 (by vs Vehi: Dunnett ’s multiple comparison test)
  • ACA active skin anaphylaxis
  • PCA passive skin anaphylaxis
  • the first aspect of the present invention relates to an antiallergic active compound.
  • the antiallergic activity compound of the present invention is represented by the following chemical formula (A) or (B).
  • R1 is a hydrogen atom, an unsubstituted or substituted methyl group, an unsubstituted or substituted ethyl group, an unsubstituted or substituted pentyl group, or an unsubstituted or substituted phenyl group
  • R2 is unsubstituted or substituted A substituted ethyl group, an unsubstituted or substituted aminoethyl group, an unsubstituted or substituted pentyl group, an unsubstituted or substituted phenyl group, or an unsubstituted or substituted piperidinyl group.
  • the substitution position when R1 and / or R2 is substituted is not particularly limited. It may be substituted at two or more positions. Examples of the substituent include F, Cl, Br, I
  • the compound of the present invention comprises (1) a derivative of a medium chain fatty acid having 10 or 11 carbon atoms, (2) a double bond at the end of the medium chain fatty acid, and (3) an amino group in the carboxylic acid moiety It has the feature of being bonded (it is an amide).
  • TIC-11006 N-2- (diisopropylamino) ethyl) undecen-10-enamide
  • TIC-11014 N-2- (diethylamino) ethyl) decen-9-enamide: N-2- (diethylamino) ethyl) dec-9-enamide
  • TIC-11022 N- (2- (diethylamino) ethyl) -N-methylundecen-10-enamide: N- (2- (diethylamino) ethyl) -N-methylundec-10-enamide
  • TIC-11030 N- (piperidin-1-yl) undecen-10-enamide :: N- (piperidin-1-yl) undec-10-enamide)
  • TIC-11035 N- (piperidin-1-yl) undecen-10-enamide :: N- (piperidin-1-yl) undec-10-enamide)
  • TIC-11006, TIC-11014, TIC-11022, TIC-11030, and TIC-11035 are compounds that have strong IgE production-suppressing activity and also have type-I allergic reaction-suppressing activity, and are highly useful. Among them, the action of TIC-11030 and TIC-11035 is strong. In addition, the detail of the synthesis
  • Another aspect of the present invention provides an antiallergic composition containing the antiallergic activity compound of the present invention or a pharmacologically acceptable salt thereof as an active ingredient.
  • the active ingredient of the composition of the present invention is one or more selected from the group consisting of TIC-11006, TIC-11014, TIC-11022, TIC-11030, TIC-11035, 11039 and TIC-11043.
  • a compound or a salt thereof is used.
  • these compounds have been identified as having both IgE production inhibitory activity and type I allergic reaction inhibitory activity, so their use can suppress IgE production and type I allergic reaction. The effect can be exerted by two actions of suppressing the above. In other words, both the source and symptoms of an allergic reaction can be suppressed.
  • the compound having a strong IgE production inhibitory action and also having a type I allergic reaction inhibitory action that is, one or more selected from the group consisting of TIC-11006, TIC-11014, TIC-11022, TIC-11030, and TIC-11035
  • a compound having a strong action that is, TIC-11030 and / or TIC-11035 or a pharmaceutically acceptable salt thereof is used as an active ingredient.
  • the composition of the present invention is used for the purpose of treating or preventing allergy.
  • the form of the composition of this invention is not specifically limited, Preferably it is a pharmaceutical, a quasi-drug, cosmetics, or a foodstuff. That is, the present invention provides, as a preferred embodiment, a pharmaceutical composition, a quasi-drug composition, a cosmetic composition, and a food composition containing the anti-allergic activity compound of the present invention or a pharmacologically acceptable salt thereof as an active ingredient. Offer things. Two or more kinds of antiallergic active compounds may be used in combination.
  • Examples of “pharmacologically acceptable salts” in this specification include salts (inorganic acid salts) with hydrochloric acid, phosphoric acid, sulfuric acid, nitric acid, boric acid, etc., formic acid, acetic acid, lactic acid, fumaric acid, maleic acid And salts (organic acid salts) with tartaric acid, citric acid, succinic acid, malonic acid and the like.
  • These salts can be prepared by conventional means.
  • the above illustration should not be used because “pharmacologically acceptable salt” is limitedly interpreted. That is, “pharmacologically acceptable salt” is to be interpreted broadly and is a term that includes various salts.
  • Preparation of the pharmaceutical composition and quasi-drug composition of the present invention can be performed according to a conventional method.
  • other pharmaceutically acceptable ingredients for example, carriers, excipients, disintegrants, buffers, emulsifiers, suspending agents, soothing agents, stabilizers, preservatives, preservatives, physiological Saline solution and the like.
  • excipient lactose, starch, sorbitol, D-mannitol, sucrose and the like can be used.
  • disintegrant starch, carboxymethylcellulose, calcium carbonate and the like can be used. Phosphate, citrate, acetate, etc. can be used as the buffer.
  • emulsifier gum arabic, sodium alginate, tragacanth and the like can be used.
  • suspending agent glyceryl monostearate, aluminum monostearate, methyl cellulose, carboxymethyl cellulose, hydroxymethyl cellulose, sodium lauryl sulfate and the like can be used.
  • soothing agent benzyl alcohol, chlorobutanol, sorbitol and the like can be used.
  • stabilizer propylene glycol, ascorbic acid or the like can be used.
  • preservatives phenol, benzalkonium chloride, benzyl alcohol, chlorobutanol, methylparaben, and the like can be used.
  • preservatives benzalkonium chloride, paraoxybenzoic acid, chlorobutanol and the like can be used.
  • the dosage form in the case of formulation is not particularly limited, for example, as nasal drops, eye drops, tablets, powders, fine granules, granules, capsules, syrups, injections, external preparations, suppositories, etc.
  • the pharmaceutical composition or quasi-drug composition of the invention can be provided.
  • the pharmaceutical composition of the present invention contains an active ingredient in an amount necessary for obtaining an expected therapeutic effect or preventive effect (that is, a therapeutically effective amount).
  • the quasi-drug composition of the present invention contains an active ingredient in an amount necessary for obtaining the expected improvement effect, prevention effect and the like.
  • the amount of the active ingredient contained in the pharmaceutical composition or quasi-drug composition of the present invention generally varies depending on the dosage form and form, but the amount of the active ingredient is, for example, about 0.1% by weight to about 95% so that a desired dosage can be achieved. Set within the weight% range.
  • the pharmaceutical composition and quasi-drug composition of the present invention are oral or parenteral (intravenous, intraarterial, subcutaneous, intramuscular, or intraperitoneal injection, transdermal, nasal, transmucosal depending on the dosage form and form. , Application, etc.).
  • the “subject” here is not particularly limited, and includes humans and non-human mammals (including pet animals, domestic animals, laboratory animals. Specifically, for example, mice, rats, guinea pigs, hamsters, monkeys, cows, pigs, goats. , Sheep, dogs, cats, chickens, quails, etc.).
  • the application subject is a human.
  • the dosage and usage of the pharmaceutical composition and quasi-drug composition of the present invention are set so as to obtain the expected effect.
  • the symptom, age, sex, weight, etc. of the subject of application are generally considered.
  • a person skilled in the art can set an appropriate dose in consideration of these matters.
  • As the administration schedule for example, once to several times a day, once every two days, or once every three days can be adopted. In the preparation of the administration / use schedule, it is possible to consider the symptoms of the application target, the duration of effect of the active ingredient, and the like.
  • the present application also provides a method for treating and preventing allergic diseases, which comprises administering a therapeutically effective amount of the pharmaceutical composition of the present invention to patients with allergic diseases.
  • the cosmetic composition of the present invention comprises an antiallergic active compound or a pharmacologically acceptable salt thereof, and ingredients / bases usually used in cosmetics (for example, various oils and fats, mineral oil, petrolatum, squalane, lanolin, Beeswax, denatured alcohol, dextrin palmitate, glycerin, glycerin fatty acid ester, ethylene glycol, paraben, camphor, menthol, various vitamins, zinc oxide, titanium oxide, benzoic acid, edetic acid, chamomile oil, carrageenan, chitin powder, chitosan, fragrance , Coloring agents, etc.).
  • ingredients / bases usually used in cosmetics (for example, various oils and fats, mineral oil, petrolatum, squalane, lanolin, Beeswax, denatured alcohol, dextrin palmitate, glycerin, glycerin fatty acid ester, ethylene glycol, paraben, camphor, menthol, various
  • the cosmetic composition examples include emulsions for face or body, lotions, creams, lotions, essences, oils, packs, sheets, cleaning agents, and the like.
  • the addition amount of the active ingredient in the cosmetic composition is not particularly limited.
  • the active ingredient may be added so as to be 0.1 wt% to 60 wt%.
  • one embodiment of the present invention is a food composition.
  • the “food composition” in the present invention include general foods (cereals, vegetables, meat, various processed foods, confectionery (such as strawberries, gums), milk, soft drinks, alcoholic beverages, etc.), dietary supplements (supplements) , Nutritional drinks, etc.), food additives, foods for pets, nutritional supplements for pets.
  • a dietary supplement or food additive it can be provided in the form of powder, granule powder, tablet, paste, liquid or the like.
  • the food composition of the present invention preferably contains an active ingredient in an amount that can be expected to have a therapeutic or preventive effect.
  • the amount added can be determined in consideration of the medical condition, health status, age, sex, weight, etc. of the person to whom it is used.
  • test compound was intraperitoneally administered every day for 2 weeks from the day of the first immunization (500 ⁇ g / kg).
  • target drug suplatast tosylate (IPD)
  • IPD suplatast tosylate
  • TIC-11006, TIC-11014, TIC-11022, TIC-11030, and TIC-11035 have a strong IgE production inhibitory action and can be expected to have a high therapeutic or preventive effect.
  • TIC-11030 and TIC-11035 have the strong IgE production inhibitory action and are the most effective compounds.
  • strong antiallergic activity was also observed in the known compounds TIC-11044 and TIC-11045.
  • the novel compound of the present invention can suppress both IgE production and type I allergic reaction. Therefore, it can be used as a novel antiallergic agent that can suppress both the source and symptoms of an allergic reaction.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Immunology (AREA)
  • General Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Pulmonology (AREA)
  • Animal Behavior & Ethology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Mycology (AREA)
  • Nutrition Science (AREA)
  • Food Science & Technology (AREA)
  • Polymers & Plastics (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

L'objet de cette invention est de pourvoir à un nouveau composé capable de supprimer à la fois la production d'IgE et l'activation des mastocytes, et à son utilisation. La solution selon l'invention porte sur un nouveau composé qui (1) est un dérivé d'un acide gras à chaîne moyenne ayant 10 ou 11 atomes de carbone, (2) comporte une double liaison à une extrémité de l'acide gras à chaîne moyenne, et dans lequel (3) un groupe amino se lie à un fragment acide carboxylique.
PCT/JP2014/052754 2013-03-19 2014-02-06 Composé ayant une activité anti-allergique et son utilisation WO2014148136A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2013056798 2013-03-19
JP2013-056798 2013-03-19

Publications (1)

Publication Number Publication Date
WO2014148136A1 true WO2014148136A1 (fr) 2014-09-25

Family

ID=51579831

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2014/052754 WO2014148136A1 (fr) 2013-03-19 2014-02-06 Composé ayant une activité anti-allergique et son utilisation

Country Status (1)

Country Link
WO (1) WO2014148136A1 (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN112194594A (zh) * 2020-08-20 2021-01-08 广东省科学院动物研究所 N，n-二乙基10-十一烯酰胺及其制备方法和在驱蚊中的应用
CN112898176A (zh) * 2021-01-22 2021-06-04 广东省科学院动物研究所 10-十一烯酰氨基甲基丙酸乙酯及其制备方法和在驱蚊中的应用

Citations (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS51127002A (en) * 1975-04-08 1976-11-05 Bayer Ag Carboxylic amide preparation method thereof and pharmaceutical composition and medicine containing same
JPS5218822A (en) * 1976-07-15 1977-02-12 Ajinomoto Co Inc Germicides for agricultural and gardening use
JPS56123923A (en) * 1980-06-21 1981-09-29 Japan Synthetic Rubber Co Ltd Conversion of unsaturated compound having functional group
JPH07196671A (ja) * 1993-12-28 1995-08-01 Shin Etsu Chem Co Ltd アミド基変性含フッ素オルガノポリシロキサン
JP2000143730A (ja) * 1998-06-19 2000-05-26 Ciba Specialty Chem Holding Inc 不飽和ポリアルキルピペリジンを重合する方法
JP2003509499A (ja) * 1999-09-21 2003-03-11 アストラゼネカ アクチボラグ キナゾリン誘導体およびそれらの医薬品としての使用
JP2005506947A (ja) * 1999-01-12 2005-03-10 ケンブリッジ ユニバーシティ テクニカル サービシズ リミティド 炎症反応を阻害又は増強するための組成物及び方法
JP2007530481A (ja) * 2004-03-24 2007-11-01 ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング エピナスチン及び１又は２以上の追加のミネラル又は１又は２以上の生薬のコンビネーションを含む皮膚疾患の治療用医薬組成物
JP2008013486A (ja) * 2006-07-05 2008-01-24 Soda Aromatic Co Ltd アラキドン酸代謝抑制剤
KR20100039532A (ko) * 2008-10-08 2010-04-16 주식회사 제닉 아토피 치료용 하이드로겔 조성물 및 이를 매트릭스로 사용하는 아토피 치료용 매트릭스 패치
WO2012026886A1 (fr) * 2010-08-27 2012-03-01 National University Of Singapore Colorant fluorescent à structure chalcone pour sonde de cellules souches embryonnaires

Patent Citations (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS51127002A (en) * 1975-04-08 1976-11-05 Bayer Ag Carboxylic amide preparation method thereof and pharmaceutical composition and medicine containing same
JPS5218822A (en) * 1976-07-15 1977-02-12 Ajinomoto Co Inc Germicides for agricultural and gardening use
JPS56123923A (en) * 1980-06-21 1981-09-29 Japan Synthetic Rubber Co Ltd Conversion of unsaturated compound having functional group
JPH07196671A (ja) * 1993-12-28 1995-08-01 Shin Etsu Chem Co Ltd アミド基変性含フッ素オルガノポリシロキサン
JP2000143730A (ja) * 1998-06-19 2000-05-26 Ciba Specialty Chem Holding Inc 不飽和ポリアルキルピペリジンを重合する方法
JP2005506947A (ja) * 1999-01-12 2005-03-10 ケンブリッジ ユニバーシティ テクニカル サービシズ リミティド 炎症反応を阻害又は増強するための組成物及び方法
JP2003509499A (ja) * 1999-09-21 2003-03-11 アストラゼネカ アクチボラグ キナゾリン誘導体およびそれらの医薬品としての使用
JP2007530481A (ja) * 2004-03-24 2007-11-01 ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング エピナスチン及び１又は２以上の追加のミネラル又は１又は２以上の生薬のコンビネーションを含む皮膚疾患の治療用医薬組成物
JP2008013486A (ja) * 2006-07-05 2008-01-24 Soda Aromatic Co Ltd アラキドン酸代謝抑制剤
KR20100039532A (ko) * 2008-10-08 2010-04-16 주식회사 제닉 아토피 치료용 하이드로겔 조성물 및 이를 매트릭스로 사용하는 아토피 치료용 매트릭스 패치
WO2012026886A1 (fr) * 2010-08-27 2012-03-01 National University Of Singapore Colorant fluorescent à structure chalcone pour sonde de cellules souches embryonnaires

Non-Patent Citations (4)

* Cited by examiner, † Cited by third party
Title
HAKALA, KIMMO ET AL.: "Synthesis of nitrogen- functionalized polyolefins with metallocene/ methylaluminoxane catalysts", POLYMER BULLETIN, vol. 46, no. 2-3, 2001, BERLIN, GERMANY, pages 123 - 130, XP001017502, DOI: doi:10.1007/s002890170065 *
MUKHERJEE, P. ET AL.: "Possible antifungal agents", JOURNAL OF THE INDIAN CHEMICAL SOCIETY, vol. 50, no. 4, 1973, pages 290 - 292 *
VIG, O. P. ET AL.: "Insect juvenile hormone analogs. Part VII. Syntheses of long chain aromatic ethers and nitrogen analogues", INDIAN JOURNAL OF CHEMISTRY, SECTION B: ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, vol. 19B, no. 8, 1980, pages 688 - 691 *
VYAS, L. K. ET AL.: "Formulation and development of anti-blemish preparation using microsponge technology", JOURNAL OF CHEMICAL AND PHARMACEUTICAL RESEARCH, vol. 2, no. 5, 2010, pages 562 - 571 *

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN112194594A (zh) * 2020-08-20 2021-01-08 广东省科学院动物研究所 N，n-二乙基10-十一烯酰胺及其制备方法和在驱蚊中的应用
WO2021159691A1 (fr) * 2020-08-20 2021-08-19 广东省科学院动物研究所 N,n-diéthyl-10-undécénamide, son procédé de préparation et utilisation de celui-ci pour repousser les moustiques
CN112898176A (zh) * 2021-01-22 2021-06-04 广东省科学院动物研究所 10-十一烯酰氨基甲基丙酸乙酯及其制备方法和在驱蚊中的应用
WO2021258733A1 (fr) * 2021-01-22 2021-12-30 广东省科学院动物研究所 10-undécylénylamino-méthyl-éthyl-propionate, son procédé de préparation et son utilisation comme répulsif à moustiques

Similar Documents

Publication Publication Date Title
JP6636108B2 (ja) アスタキサンチン抗炎症性相乗的組み合わせ
ES2585066T3 (es) Composiciones para el tratamiento de trastornos neurológicos
US20110311478A1 (en) Combinatorial Methods For Treating Cellular Proliferative Disorders And Immune Deficiencies Using Salicinium
US11149014B2 (en) Method for treating pain or associated condition or symptom
KR101710474B1 (ko) 갈아마이드 유도체 및 이의 용도
JP2019182881A (ja) 末梢神経障害の予防又は改善用組成物
JP6343000B2 (ja) オイゲノールを有効成分として含有するアトピー性皮膚炎の予防又は治療用組成物
US20220273600A1 (en) Lithium salts of n-substituted glycine compounds and uses thereof
JP6930037B2 (ja) 脳卒中の予防又は治療用組成物
US20070244079A1 (en) Preventive/remedy for allergic diseases
JPWO2002055091A1 (ja) 抗アレルギー剤
WO2017111069A1 (fr) Agent antiprurigineux
WO2014148136A1 (fr) Composé ayant une activité anti-allergique et son utilisation
WO2020130146A1 (fr) Agent destiné à améliorer la qualité musculaire
JP2007031302A (ja) アディポネクチン産生促進剤、及び代謝異常症候群予防剤
US20160008388A1 (en) Compositions and methods for immunotherapy
AU2020283844B2 (en) Composition for preventing or treating asthma, rhinitis or conjunctivitis, comprising N-acyl amino acid as active ingredient
JP4253161B2 (ja) アレルギー性疾患治療用外用剤
JP2007145741A (ja) ＩｇＥ捕捉剤、並びに抗アレルギー性の医薬組成物、化粧料組成物、食料組成物、飲料組成物及び飼料組成物
CN104177318A (zh) L-抗坏血酸-6-（10-羟基-2-癸烯酸）酯或其衍生物以及它们的应用
CN104262302A (zh) L-抗坏血酸-6-(e-2-癸烯酸)酯或其衍生物以及它们的应用
EP3977990A1 (fr) Composition permettant la prévention ou le traitement de l'asthme, de la rhinite ou de la conjonctivite, comprenant un acide n-acylaminé en tant que principe actif
WO2023145735A1 (fr) Thérapie et prévention innovantes pour supprimer les troubles liés au vieillissement, notamment la sarcopénie
WO2021079987A1 (fr) Agent d'amélioration de la qualité musculaire
JP6981311B2 (ja) 不安様症状の改善用組成物

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 14769822

Country of ref document: EP

Kind code of ref document: A1

NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 14769822

Country of ref document: EP

Kind code of ref document: A1

NENP Non-entry into the national phase

Ref country code: JP