JPS6054943B2 - Novel cyclohexenecarboxylic acid derivative - Google Patents
Novel cyclohexenecarboxylic acid derivativeInfo
- Publication number
- JPS6054943B2 JPS6054943B2 JP53008587A JP858778A JPS6054943B2 JP S6054943 B2 JPS6054943 B2 JP S6054943B2 JP 53008587 A JP53008587 A JP 53008587A JP 858778 A JP858778 A JP 858778A JP S6054943 B2 JPS6054943 B2 JP S6054943B2
- Authority
- JP
- Japan
- Prior art keywords
- novel
- acid derivative
- cyclohexenecarboxylic acid
- compound
- present
- 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.)
- Expired
Links
- NMEZJSDUZQOPFE-UHFFFAOYSA-N Cyclohex-1-enecarboxylic acid Chemical class OC(=O)C1=CCCCC1 NMEZJSDUZQOPFE-UHFFFAOYSA-N 0.000 title claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 238000000034 method Methods 0.000 description 5
- 239000000243 solution Substances 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000003266 anti-allergic effect Effects 0.000 description 3
- 239000000043 antiallergic agent Substances 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 235000019441 ethanol Nutrition 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 2
- 241000700199 Cavia porcellus Species 0.000 description 2
- 206010012442 Dermatitis contact Diseases 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- 239000007868 Raney catalyst Substances 0.000 description 2
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 2
- 229910000564 Raney nickel Inorganic materials 0.000 description 2
- 210000001015 abdomen Anatomy 0.000 description 2
- UAHWPYUMFXYFJY-UHFFFAOYSA-N beta-myrcene Chemical compound CC(C)=CCCC(=C)C=C UAHWPYUMFXYFJY-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 208000010247 contact dermatitis Diseases 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 238000002386 leaching Methods 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 239000002504 physiological saline solution Substances 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 230000003637 steroidlike Effects 0.000 description 2
- HJRJRUMKQCMYDL-UHFFFAOYSA-N 1-chloro-2,4,6-trinitrobenzene Chemical compound [O-][N+](=O)C1=CC([N+]([O-])=O)=C(Cl)C([N+]([O-])=O)=C1 HJRJRUMKQCMYDL-UHFFFAOYSA-N 0.000 description 1
- 241000700198 Cavia Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 206010030113 Oedema Diseases 0.000 description 1
- 206010070834 Sensitisation Diseases 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000003470 adrenal cortex hormone Substances 0.000 description 1
- VYBREYKSZAROCT-UHFFFAOYSA-N alpha-myrcene Natural products CC(=C)CCCC(=C)C=C VYBREYKSZAROCT-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000010531 catalytic reduction reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 210000005069 ears Anatomy 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 231100000957 no side effect Toxicity 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 150000004986 phenylenediamines Chemical class 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000008313 sensitization Effects 0.000 description 1
- 150000003431 steroids Chemical class 0.000 description 1
- 229940034610 toothpaste Drugs 0.000 description 1
- 239000000606 toothpaste Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Detergent Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
Description
【発明の詳細な説明】
本発明は一般式 （Ｉ）
＞（
「゛］
゛ゝィ
／ ′ （Ｉ）
゛＼
）
／’
＜ＣＨ３
゛「
（式中、Ｒは低級アルキル基を意味する）で表わされる
新規なシクロヘキセンカルボン酸誘導体に関するもので
ある。[Detailed Description of the Invention] The present invention has the following formula: This invention relates to a novel cyclohexenecarboxylic acid derivative represented by
本発明の化合物は文献未載の新規化合物てあり、抗アレ
ルギー作用を有し医薬品として産業上有用な化合物であ
る。The compound of the present invention is a novel compound that has not been described in any literature, and has an antiallergic effect and is industrially useful as a pharmaceutical.
又、本発明の化合物は医薬品及び界面活性剤の中間原料
としても有用な化合物である。The compound of the present invention is also useful as an intermediate raw material for pharmaceuticals and surfactants.
従来、抗アレルギー剤、特に遅延型抗アレルギー剤とし
ては副腎皮質ホルモン剤が知られているにすぎない。So far, only adrenocortical hormone agents have been known as anti-allergic agents, especially delayed-type anti-allergic agents.
しかし、ステロイド製剤は長期連用すると重篤な副作用
を発現するために副作用の少ない非ステロイド系抗アレ
ルギー剤の開発が望まれている。そこで本発明者等は非
ステロイド性の新規化合物を求め種々検討を進めた結果
、一般式（１）で表わされる化合物を合成し、薬理作用
を検討した所、顕著な抗アレルギー作用を有し且つ副作
用が皆無に等しいことを見出した。又、本発明の化合物
は本発明者等が先に特許を受けるべく出願中（出願番号
５２−７２６３９）の新規化合物群の中間原料として有
用な化合物である。However, since steroid preparations exhibit serious side effects when used continuously for a long period of time, there is a desire for the development of non-steroidal anti-allergic agents with fewer side effects. Therefore, the present inventors conducted various studies in search of a new non-steroidal compound, and as a result, synthesized a compound represented by general formula (1), and examined its pharmacological effects, and found that it has a remarkable antiallergic effect and It was found that there were almost no side effects. Furthermore, the compound of the present invention is a compound useful as an intermediate raw material for a group of new compounds for which the present inventors are currently applying for a patent (Application No. 52-72639).
又、本発明の化合物は界面活性作用を有し、ハミガキ，
ジャンプーの添加剤、洗剤、分散剤、乳化剤、可溶化剤
、化粧品用の界面活性剤等に利用出来る他これらの中間
原料として有用である。以下に本発明のもつ抗アレルギ
ー作用を薬理実験によつて示す。モルモツトでのｐ−フ
ェニレンジアミン誘発接触皮膚炎に対する作用１０％ｐ
−フェニレンジアミンを３０％エチルアルコールー生理
食塩液に溶解して脱脂綿に浸し、１０×３０Ｗ１Ｒの電
極とモルモツト脱毛頚部の間におき陽極とし、一方、生
理食塩液をガーゼに浸し１０×３０顛の電極とモルモツ
ト脱毛腹部の間におき陰極とし、３ｍＡの電流を１５分
間隔日６回通電し、感作した。In addition, the compound of the present invention has surfactant action and is useful for toothpaste,
It can be used as an additive for jumpers, detergents, dispersants, emulsifiers, solubilizers, surfactants for cosmetics, and as an intermediate raw material for these products. The antiallergic effect of the present invention will be shown below through pharmacological experiments. Effect on p-phenylenediamine-induced contact dermatitis in guinea pigs 10%p
- Dissolve phenylene diamine in 30% ethyl alcohol-physiological saline solution, soak it in absorbent cotton, and place it between a 10 x 30 W1R electrode and the depilated neck of a guinea pig to serve as an anode. A cathode was placed between the electrode and the guinea pig's depilated abdomen, and a current of 3 mA was applied at 15 minute intervals six times a day to sensitize it.
３〜４週間後に２％ｐ−フェニレンジアミンー生理食塩
液を０．０５ｍ１剪毛背部に皮内注射し２２時間後に１
％エバンス・ブルー１．０ｍ１を静脈注射した。After 3 to 4 weeks, 0.05 ml of 2% p-phenylenediamine-physiological saline was intradermally injected into the back of the shaved hair, and 22 hours later, 1
1.0 ml of % Evans Blue was injected intravenously.
薬物は２％ｐ−フェニレンジアミン溶液０．０５ｍ１適
用時に経口投与し、１％エバンス・ブルー１．０ｍ１適
用後２時間に放血致死させて、皮膚を剥離し、色素浸出
面積と浸出色素量を測定した。マウスでの塩化ピクリル
誘発接触皮膚炎マウスの剪毛腹部（面積２．５×１５Ｔ
ｗｔ）に７％塩化ピクリルーエチルアルコール溶液０．
１ｍ１を塗布、惑作した。The drug was administered orally when applying 0.05ml of 2% p-phenylenediamine solution, and 2 hours after applying 1.0ml of 1% Evans Blue, the animals were bled to death, the skin was peeled off, and the area of pigment leaching and the amount of pigment leaching were measured. did. Picryl chloride-induced contact dermatitis in mice. Shaved abdomen of mice (area 2.5 x 15T
wt) to 7% picrylic chloride ethyl alcohol solution.
1ml was applied and planted.
１０日後に同様の二次感作を行ない更に７日後に片耳宛
０．０２ｍｔの１％塩化ピクリルーオリーブ油溶液を両
耳に塗布し、この際に薬物を経口投与し、その直前及び
２＠間後の耳の厚みを厚み計で測定し浮腫を求めた。After 10 days, the same secondary sensitization was performed, and after 7 days, 0.02 mt of 1% chlorinated olive oil solution was applied to each ear on both ears. At this time, the drug was orally administered, and immediately before and between 2 The thickness of the later ear was measured using a thickness gauge to determine edema.
次に製造法に就いて述べる。Next, we will discuss the manufacturing method.
本発明の化合物は下記の反応式で示す様にミルセンとア
クリル酸誘導体とを反応させて得られた化合物（■）を
ラネーニツケルで接触還元後、加水分解する方法（Ａ法
）及び式（■）においてＲ１が水素原子の場合は直接接
触還元する方法（Ｂ法）によつて製造される。The compound of the present invention is produced by a method (method A) in which a compound (■) obtained by reacting myrcene with an acrylic acid derivative is catalytically reduced with Raney nickel and then hydrolyzed as shown in the reaction formula below (Method A) When R1 is a hydrogen atom, it is produced by a direct catalytic reduction method (method B).
但し、Ｒは低級アルキル基を、Ｒ１は水素原子又は低級
アルキル基を意味する。However, R means a lower alkyl group, and R1 means a hydrogen atom or a lower alkyl group.
以下に実施例を示し、本発明を更に具体的に説明する。EXAMPLES The present invention will be explained in more detail with reference to Examples below.
実施例１１−メチルー４−（４−メチルー３−ペンテニ
ル）−３−シクロヘキセンー１−カルボン酸５ｆをエタ
ノール２０ｍ１に溶解後活性化したラネーニツケル約１
ｙを加え水添した。Example 11-Methyl-4-(4-methyl-3-pentenyl)-3-cyclohexene-1-carboxylic acid 5f was dissolved in 20 ml of ethanol and then activated to produce about 1 Raney nickel.
y was added and hydrogenated.
反応終了後、触媒を沖別し、淵液の溶媒を留去し残渣を
アセトニトリルより再結晶すると無色柱状晶の１−メチ
ルー４−イソヘキシルー３−シクロヘキセンー１−カル
ボン酸４．５ｙを得た。この物質の融点及び元素分析値
は次の通りであつた。After the reaction was completed, the catalyst was removed, the solvent in the aqueous solution was distilled off, and the residue was recrystallized from acetonitrile to obtain 4.5y of 1-methyl-4-isohexy-3-cyclohexene-1-carboxylic acid as colorless columnar crystals. The melting point and elemental analysis values of this substance were as follows.
実施例２
１−メチルー４−イソヘキシルー３−シクロヘキセンー
１−カルボン酸メチルエステル２．４ｙをエタノール２
０ｍＬに溶解した溶液に水酸化ナトリウム１．２ｙを少
量の水に溶かして加え、還流下３時間反応させた。Example 2 2.4y of 1-methyl-4-isohexy-3-cyclohexene-1-carboxylic acid methyl ester was dissolved in ethanol 2
1.2 y of sodium hydroxide dissolved in a small amount of water was added to the solution in 0 mL, and the mixture was reacted under reflux for 3 hours.
Claims (1)
新規なシクロヘキセンカルボン酸誘導体。[Claims] 1. A novel cyclohexenecarboxylic acid derivative represented by the general formula ▲ Numerical formula, chemical formula, table, etc. ▼ (In the formula, R means a lower alkyl group).
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP53008587A JPS6054943B2 (en) | 1978-01-27 | 1978-01-27 | Novel cyclohexenecarboxylic acid derivative |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP53008587A JPS6054943B2 (en) | 1978-01-27 | 1978-01-27 | Novel cyclohexenecarboxylic acid derivative |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS54103845A JPS54103845A (en) | 1979-08-15 |
| JPS6054943B2 true JPS6054943B2 (en) | 1985-12-03 |
Family
ID=11697118
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP53008587A Expired JPS6054943B2 (en) | 1978-01-27 | 1978-01-27 | Novel cyclohexenecarboxylic acid derivative |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6054943B2 (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PT1695956E (en) * | 2003-11-27 | 2012-08-27 | Chugoku Marine Paints | Cyclic carboxylic acid compound and use thereof |
-
1978
- 1978-01-27 JP JP53008587A patent/JPS6054943B2/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| JPS54103845A (en) | 1979-08-15 |
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