JPH0136454B2 - - Google Patents
Info
- Publication number
- JPH0136454B2 JPH0136454B2 JP3287181A JP3287181A JPH0136454B2 JP H0136454 B2 JPH0136454 B2 JP H0136454B2 JP 3287181 A JP3287181 A JP 3287181A JP 3287181 A JP3287181 A JP 3287181A JP H0136454 B2 JPH0136454 B2 JP H0136454B2
- Authority
- JP
- Japan
- Prior art keywords
- present
- alkyl group
- formula
- compound
- general formula
- 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
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 150000005379 cyclohexanecarboxylic acid derivatives Chemical class 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 description 9
- 238000004519 manufacturing process Methods 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000000259 anti-tumor effect Effects 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 230000000144 pharmacologic effect Effects 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 230000003266 anti-allergic effect Effects 0.000 description 2
- 230000003356 anti-rheumatic effect Effects 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- ZPVFWPFBNIEHGJ-UHFFFAOYSA-N 2-octanone Chemical compound CCCCCCC(C)=O ZPVFWPFBNIEHGJ-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- 229940100198 alkylating agent Drugs 0.000 description 1
- 230000000340 anti-metabolite Effects 0.000 description 1
- 229940100197 antimetabolite Drugs 0.000 description 1
- 239000002256 antimetabolite Substances 0.000 description 1
- 239000002246 antineoplastic agent Substances 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 230000003908 liver function Effects 0.000 description 1
- 231100000957 no side effect Toxicity 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
Description
【発明の詳細な説明】
本発明は一般式（）
（式中、ＲはC2〜C10の直鎖アルキル基又は分枝
アルキル基を意味する）で表わされる新規なシク
ロヘキサ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 relates to the general formula () The present invention relates to a novel cyclohexanecarboxylic acid derivative represented by the formula (wherein R means a C2 - C10 straight-chain alkyl group or a branched alkyl group).
本発明の化合物は文献未載の新規化合物であ
り、抗腫瘍作用、抗アレルギー作用、肝機能改善
作用、抗リウマチ作用等の薬理作用を有し医薬品
として非常に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 pharmacological effects such as antitumor activity, antiallergic effect, liver function improving effect, and antirheumatic effect, and is a very useful compound as a pharmaceutical.
従来、抗腫瘍剤としては一般にアルキル化剤、
代謝拮抗剤等が臨床上用いられているが、概して
副作用が強くその使用が制限されているのが現状
である。そこで本発明者等は副作用の弱い新規な
抗腫瘍活性化合物を求め鋭意研究を重ねた結果、
一般式（）で表わされる新規化合物の合成に成
功し、薬理作用について種々検討したところ、こ
れらの化合物が顕著な抗腫瘍作用、抗アレルギー
作用、肝機能改善作用、抗リウマチ作用等の薬理
作用を有し、且つ副作用が皆無に等しいことを見
出し本発明を完成したのである。 Conventionally, antitumor agents generally include alkylating agents,
Although antimetabolites and the like are used clinically, their use is currently limited due to their generally strong side effects. Therefore, the present inventors conducted extensive research in search of a new antitumor active compound with weak side effects, and as a result,
After successfully synthesizing new compounds represented by the general formula () and conducting various studies on their pharmacological effects, we found that these compounds have remarkable pharmacological effects such as anti-tumor, anti-allergic, liver function-improving, and anti-rheumatic effects. The present invention was completed based on the discovery that the present invention has no side effects.
次に本発明の製造法について説明するが、これ
は一例にすぎず勿論他の化学的類似方法によつて
も製造できるものである。 Next, the manufacturing method of the present invention will be explained, but this is only an example, and it goes without saying that it can also be manufactured by other chemically similar methods.
製造法
（式中、Ｒは前記と同じ意味を有する）
但し、式中ＲはC2〜C10の直鎖アルキル基又は
分枝アルキル基を意味する。Manufacturing method (In the formula, R has the same meaning as above.) However, in the formula, R means a C2 to C10 straight chain alkyl group or a branched alkyl group.
尚、前記製造法の出発物質である一般式（）
で表わされる化合物は本願出願人が特許を受ける
べく本願と並行して出願中の特許出願に記載の方
法により合成すればよい。 In addition, the general formula () which is the starting material of the above production method
The compound represented by can be synthesized by the method described in the patent application currently being filed in parallel with the present application by the applicant of the present application.
前記製造法によれば一般式（）で表わされる
化合物をアルカリ（例えば水酸化ナトリウム、水
酸化カリウム等）又は酸（例えば塩酸、硫酸等）
中、加水分解させればよい。 According to the above production method, a compound represented by the general formula (
In the middle, it can be hydrolyzed.
以下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 below with reference to Examples.
実施例 １
１−ｎ−ブチル−６−オキサピシクロ〔３，
２，１〕オクタン−７−オン20ｇと水酸化ナトリ
ウム５ｇを含水メタノール200mlに溶解し30分間
還流した。反応終了後、溶媒を留去し残渣に水を
加えて溶解したのち塩酸酸性とした。析出した結
晶を取し、水洗、乾燥後アセトニトリルより再
結晶すると無色プリズム晶のシス−１−ｎ−ブチ
ル−３−ヒドロキシシクロヘキサンカルボン酸
18.1ｇを得た。Example 1 1-n-butyl-6-oxapicyclo[3,
2,1] 20 g of octan-7-one and 5 g of sodium hydroxide were dissolved in 200 ml of water-containing methanol and refluxed for 30 minutes. After the reaction was completed, the solvent was distilled off, and the residue was dissolved in water and then acidified with hydrochloric acid. The precipitated crystals are collected, washed with water, dried, and recrystallized from acetonitrile to yield colorless prismatic crystals of cis-1-n-butyl-3-hydroxycyclohexanecarboxylic acid.
18.1g was obtained.
この物質の融点及び元素分析値は次の通りであ
つた。 The melting point and elemental analysis values of this substance were as follows.
融 点 107〜108℃
元素分析値 C11H20O3
理論値 Ｃ：65.97 Ｈ：10.07
実測値 Ｃ：66.08 Ｈ：10.12
以下実施例１の方法に準じて次の化合物を合成
した。Melting point: 107-108°C Elemental analysis value: C 11 H 20 O 3 Theoretical value: C: 65.97 H: 10.07 Actual value: C: 66.08 H: 10.12 The following compound was synthesized according to the method of Example 1.
シス−３−ヒドロキシ−１−イソペンチルシク
ロヘキサンカルボン酸
融 点 101〜102℃
シス−１−ｎ−ヘキシル−３−ヒドロキシシク
ロヘキサンカルボン酸
融 点 102.5〜103.5℃ Cis-3-hydroxy-1-isopentylcyclohexanecarboxylic acid Melting point 101~102℃ Cis-1-n-hexyl-3-hydroxycyclohexanecarboxylic acid Melting point 102.5~103.5℃
Claims (1)
アルキル基を意味する）で表わされる新規なシク
ロヘキサンカルボン酸誘導体。[Claims] 1. General formula A novel cyclohexanecarboxylic acid derivative represented by the formula (wherein R means a C2 - C10 straight-chain alkyl group or a branched alkyl group).
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3287181A JPS57181033A (en) | 1981-03-05 | 1981-03-05 | Novel cyclohexanecarboxylic acid derivative |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3287181A JPS57181033A (en) | 1981-03-05 | 1981-03-05 | Novel cyclohexanecarboxylic acid derivative |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS57181033A JPS57181033A (en) | 1982-11-08 |
| JPH0136454B2 true JPH0136454B2 (en) | 1989-07-31 |
Family
ID=12370921
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP3287181A Granted JPS57181033A (en) | 1981-03-05 | 1981-03-05 | Novel cyclohexanecarboxylic acid derivative |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS57181033A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR101102574B1 (en) * | 2009-09-30 | 2012-01-03 | 조양래 | A preparative method for 1,4-disubstituted cyclohexane derivatives |
-
1981
- 1981-03-05 JP JP3287181A patent/JPS57181033A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS57181033A (en) | 1982-11-08 |
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