JPS6412274B2 - - Google Patents
Info
- Publication number
- JPS6412274B2 JPS6412274B2 JP1861881A JP1861881A JPS6412274B2 JP S6412274 B2 JPS6412274 B2 JP S6412274B2 JP 1861881 A JP1861881 A JP 1861881A JP 1861881 A JP1861881 A JP 1861881A JP S6412274 B2 JPS6412274 B2 JP S6412274B2
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- oxabicyclo
- methylpentyl
- present
- group
- 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
- 125000003119 4-methyl-3-pentenyl group Chemical group [H]\C(=C(/C([H])([H])[H])C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- KKVBULDFFNFYHJ-UHFFFAOYSA-N 6-oxabicyclo[3.2.1]octan-7-one Chemical class C1C2C(=O)OC1CCC2 KKVBULDFFNFYHJ-UHFFFAOYSA-N 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 description 10
- 230000000694 effects Effects 0.000 description 6
- 230000000259 anti-tumor effect Effects 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 230000000144 pharmacologic effect Effects 0.000 description 3
- 230000003266 anti-allergic effect Effects 0.000 description 2
- 230000003356 anti-rheumatic effect Effects 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 2
- 230000003908 liver function Effects 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- TVEXGJYMHHTVKP-UHFFFAOYSA-N 6-oxabicyclo[3.2.1]oct-3-en-7-one Chemical compound C1C2C(=O)OC1C=CC2 TVEXGJYMHHTVKP-UHFFFAOYSA-N 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- 229940100198 alkylating agent Drugs 0.000 description 1
- 230000001315 anti-hyperlipaemic effect Effects 0.000 description 1
- 230000000340 anti-metabolite Effects 0.000 description 1
- 239000000043 antiallergic agent Substances 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
- 238000009835 boiling Methods 0.000 description 1
- 239000003246 corticosteroid Substances 0.000 description 1
- 229960001334 corticosteroids Drugs 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000003637 steroidlike Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
Description
【発明の詳細な説明】
本発明は一般式（）
（式中、R1は水素原子又はメチル基を、R2は４
−メチルペンチル基又は４−メチル−３−ペンテ
ニル基を意味する）で表わされる新規な６−オキ
サビシクロ〔3.2.1〕オクタン−７−オン誘導体
に関するものである。[Detailed Description of the Invention] The present invention relates to the general formula () (In the formula, R 1 is a hydrogen atom or a methyl group, R 2 is 4
The present invention relates to a novel 6-oxabicyclo[3.2.1]octan-7-one derivative represented by -methylpentyl or 4-methyl-3-pentenyl.
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、抗高脂血症作用、抗リウマチ作用等の薬理
作用を有し医薬品として有用な化合物である。 The compound of the present invention is a new compound that has not been described in any literature, and it is a compound that is useful as a pharmaceutical and has pharmacological effects such as antitumor activity, antiallergy effect, liver function improvement effect, antihyperlipidemia effect, and antirheumatic effect. be.
従来、抗アレルギー剤としては一般に副賢皮質
ホルモン剤、抗腫瘍剤としてはアルキル化剤、代
謝拮抗剤等が知られているが、いずれも重篤な副
作用が発現するため、その使用が制限されてい
る。そこで、本発明者等は副作用の少ない非ステ
ロイド系の新規化合物及び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６−オキサビシクロ〔3.2.1〕オクタン−７
−オン誘導体を合成し薬理作用について種々検討
したところ、本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、抗高脂血症作
用、抗リウマチ作用等の薬理作用を有し且つ副作
用が少ないことを見出し本発明を完成したのであ
る。 Conventionally, corticosteroids have been known as anti-allergic agents, and alkylating agents, antimetabolites, etc. have been known as anti-tumor agents, but their use has been limited due to serious side effects. ing. Therefore, the present inventors conducted extensive research in search of new non-steroidal compounds with fewer side effects and compounds with antitumor activity.
After synthesizing the -one derivative and conducting various studies on its pharmacological effects, we found that this compound has significant pharmacological effects such as antitumor, antiallergic, liver function improving, antihyperlipidemic, and antirheumatic effects. They found that there were fewer side effects and completed the present invention.
次に本発明の製造法について説明する。尚、下
記反応式において出発物質である一般式（）で
表わされる化合物は本発明者等が既に特許を受け
るべく先に出願中の方法によつて合成することが
できる。 Next, the manufacturing method of the present invention will be explained. In addition, the compound represented by the general formula (), which is a starting material in the following reaction formula, can be synthesized by a method for which the present inventors have already applied for a patent.
製造法
但し、式中R1は水素原子又はメチル基を、R2
は４−メチルペンチル基又は４−メチル−３−ペ
ンテニル基を意味する。Manufacturing method However, in the formula, R 1 is a hydrogen atom or a methyl group, R 2
means 4-methylpentyl group or 4-methyl-3-pentenyl group.
上記製造法を具体的に説明すると、一般式
（）で表わされる化合物をそれらの融点温度に
５〜30分間加熱することにより高収率で一般式
（）で表わされる目的化合物を得ることができ
る。 To specifically explain the above production method, the target compound represented by the general formula () can be obtained in high yield by heating the compound represented by the general formula () to their melting point temperature for 5 to 30 minutes. .
以下に実施例を示し本発明を具体的に説明す
る。 EXAMPLES The present invention will be specifically explained below with reference to Examples.
実施例 １
ｃ−３，ｔ−４−ジヒドロキシル−ｃ−４−
（４−メチルペンチル）−ｒ−１−シクロヘキサン
カルボン酸24.4ｇを120℃にて15分間加熱後、減
圧蒸留に付すと、沸点114〜117℃／0.4mmHg、無
色油状の4α−ヒドロキシ−4β−（４−メチルペン
チル）−６−オキサビシクロ〔3.2.1〕オクタン−
７−オン18.3ｇを得た。Example 1 c-3,t-4-dihydroxyl-c-4-
When 24.4 g of (4-methylpentyl)-r-1-cyclohexanecarboxylic acid was heated at 120°C for 15 minutes and then subjected to vacuum distillation, 4α-hydroxy-4β- (4-Methylpentyl)-6-oxabicyclo[3.2.1]octane-
18.3 g of 7-one was obtained.
この物質の元素分析値は次の通りであつた。 The elemental analysis values of this substance were as follows.
元素分析値 C13H22O3 理 論 値 Ｃ：68.99 Ｈ：9.80 実 測 値 Ｃ：69.20 Ｈ：9.77 前記実施例に準じて次の化合物を合成した。 Elemental analysis value C 13 H 22 O 3 Theoretical value C: 68.99 H: 9.80 Actual value C: 69.20 H: 9.77 The following compound was synthesized according to the above example.
4α−ヒドロキシル−１−メチル−4β−（４−メ
チルペンチル）−６−オキサビシクロ〔3.2.1〕オ
クタン−７−オン
融点 84〜85.5℃
4α−ヒドロキシル−4β−（４−メチル−３−ペ
ンテニル）−６−オキサビシクロ〔3.2.1〕オクタ
ン−７−オン
4α−ヒドロキシル−１−メチル−4β−（４−メ
チル−３−ペンテニル）−６−オキサビシクロ
〔3.2.1〕オクタン−７−オン
沸点 137〜141℃／0.8mmHg 4α-hydroxyl-1-methyl-4β-(4-methylpentyl)-6-oxabicyclo[3.2.1]octan-7-one Melting point 84-85.5℃ 4α-hydroxyl-4β-(4-methyl-3-pentenyl )-6-oxabicyclo[3.2.1]octan-7-one 4α-hydroxyl-1-methyl-4β-(4-methyl-3-pentenyl)-6-oxabicyclo[3.2.1]octan-7-one Boiling point 137-141℃/0.8mmHg
Claims (1)
−メチルペンチル基又は４−メチル−３−ペンテ
ニル基を意味する）で表わされる新規な６−オキ
サビシクロ〔3.2.1〕オクタン−７−オン誘導体。[Claims] 1. General formula (In the formula, R 1 is a hydrogen atom or a methyl group, R 2 is 4
A novel 6-oxabicyclo[3.2.1]octan-7-one derivative represented by -methylpentyl group or 4-methyl-3-pentenyl group.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1861881A JPS57131780A (en) | 1981-02-09 | 1981-02-09 | Novel 6-oxabicyclo(3.2.1)octan-7-one derivative |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1861881A JPS57131780A (en) | 1981-02-09 | 1981-02-09 | Novel 6-oxabicyclo(3.2.1)octan-7-one derivative |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS57131780A JPS57131780A (en) | 1982-08-14 |
| JPS6412274B2 true JPS6412274B2 (en) | 1989-02-28 |
Family
ID=11976603
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1861881A Granted JPS57131780A (en) | 1981-02-09 | 1981-02-09 | Novel 6-oxabicyclo(3.2.1)octan-7-one derivative |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS57131780A (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4131062B2 (en) * | 1998-09-25 | 2008-08-13 | 信越化学工業株式会社 | Novel lactone-containing compound, polymer compound, resist material, and pattern forming method |
| JP4358940B2 (en) * | 1999-08-26 | 2009-11-04 | 丸善石油化学株式会社 | Polymerizable compound and polymer having cyclohexanelactone structure |
-
1981
- 1981-02-09 JP JP1861881A patent/JPS57131780A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS57131780A (en) | 1982-08-14 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Conder et al. | The synthesis of group V substituted derivatives of iron pentacarbonyl in high yield | |
| JPS6412274B2 (en) | ||
| Roling et al. | Formation and characterization of 1, 2-diiodoferrocene and related derivatives | |
| JPS62108871A (en) | Production of oxazoles | |
| JPH0154341B2 (en) | ||
| JPS628420B2 (en) | ||
| DE1795695A1 (en) | ADENOSINE DERIVATIVES AND METHOD FOR THEIR PRODUCTION | |
| JP2894525B2 (en) | Crystalline tetrakis (triphenylphosphine) palladium and method for producing the same | |
| JPH04501861A (en) | Production method of progesterone derivatives | |
| SU566842A1 (en) | Method of preparing substituted imidazopyridines | |
| Adam et al. | XI.—Synthesis of arachidic acid and some long-chain compounds | |
| JPH0136454B2 (en) | ||
| JPH0378384B2 (en) | ||
| JPH0136477B2 (en) | ||
| JPS59219267A (en) | Phthalazine derivative and its preparation | |
| JPS6346736B2 (en) | ||
| SU487078A1 (en) | Method for producing vanadium cyclopentadienyl diacetate dimer | |
| DE851066C (en) | Process for the production of antihistaminic substances | |
| SU576926A3 (en) | Method of preparing 4-(diphenylmethoxy)-1-methylpiperidine-4-1-oxy-2-(methyl-3-phenylpropylamino)-propyl phenolate | |
| DE1445590C (en) | Succinimiddenvate | |
| SU504441A1 (en) | The method of obtaining meta-or para-iodo derivatives of benzene, labeled with radioisotopes of iodine | |
| Butler et al. | New Compounds. Tetraallylethylenediamine and Hexallylethylenediammonium Dibromide | |
| Cutler et al. | The Possible Influence of Steric Effects, Field Effects and Hydrogen Bonding on the Chemical Reactivity of Certain 4, 10-Disubstituted-1, 7-phenanthrolines1 | |
| JPS6412275B2 (en) | ||
| JPS633859B2 (en) |