JPS6021160B2 - imidazothiazolium compounds - Google Patents
imidazothiazolium compoundsInfo
- Publication number
- JPS6021160B2 JPS6021160B2 JP5647877A JP5647877A JPS6021160B2 JP S6021160 B2 JPS6021160 B2 JP S6021160B2 JP 5647877 A JP5647877 A JP 5647877A JP 5647877 A JP5647877 A JP 5647877A JP S6021160 B2 JPS6021160 B2 JP S6021160B2
- Authority
- JP
- Japan
- Prior art keywords
- imidazothiazolium
- compounds
- phenylimidazo
- formula
- compound
- 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
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Description
【発明の詳細な説明】
本発明は新規なィミダゾチアゾＩＪゥム化合物に関する
ものである。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to novel imidazothiazo IJum compounds.
本発明の化合物の母核である６−フェニルィミダゾ〔２
．１−ｂ〕チァゾール類はＪ．Ｍｅｄ．Ｃｈｅｍ．，９
，５４５（１９６６）にその合成法及び駆虫剤としての
活性が述べられている。6-phenylimidazo [2
．． 1-b] Thiazoles are described in J. Med. Chem. ,9
, 545 (1966) describes its synthesis method and activity as an anthelmintic.
これらの中で特に２，３，５，６ーテトラヒドロー６−
フエニルイミダゾ〔２．１一ｂ〕チアゾールは家畜、人
間の駆虫剤として一般名「Ｔｅｔｒａｍｉｓｏｌｅ」と
して当業者によく知られている。また、この左施性異性
体は制がん効果を持ち一般名「戊ｖａｍｉｓｏｌｅ」と
して知られている。本発明の目的は前記式（１）で表わ
される殺線虫剤、駆虫剤及び制がん剤として価値ある新
規なイミダゾチアゾリウム化合物を提供することである
。Among these, 2,3,5,6-tetrahydro6-
Phenylimidazo[2.11b]thiazole is well known to those skilled in the art under the generic name "Tetramisole" as an anthelmintic for livestock and humans. In addition, this left-handed isomer has an anticancer effect and is known by the common name "vamisole." An object of the present invention is to provide a novel imidazothiazolium compound represented by the formula (1) that is valuable as a nematocide, anthelmintic, and an anticancer agent.
本発明のィミダゾチアゾリウム化合物は
式
（式中Ｒ，は低級アルキル基、Ｘは酸素原子または硫黄
原子を表わし、・・・は二重結合を選択できる。The imidazothiazolium compound of the present invention has the formula (where R is a lower alkyl group, X represents an oxygen atom or a sulfur atom, and . . . can be selected from a double bond.
）で表わされるものである。).
本発明の化合物は殺線虫剤人間または家畜の駆虫剤、お
よび制がん剤として有用な化合物である。The compounds of this invention are useful as nematicides, human or livestock anthelmintics, and anticancer agents.
式（１）の化合物を製造するには式（０）（式中・・・
は２重結合を選択できる。To produce the compound of formula (1), the compound of formula (0) (in the formula...
can select double bonds.
）で表わされる化合物と式（ｍ）
（式中、Ｒ，は低級アルキル基、Ｘは酸素腺子または硫
黄原子を表わしＹはハロゲン原子を表わす。) and the compound represented by the formula (m) (wherein R represents a lower alkyl group, X represents an oxygen atom or a sulfur atom, and Y represents a halogen atom.
）で表わされるリン酸ハロゲン化物を適当な溶媒中で反
応させることによって得ることができる。) can be obtained by reacting a phosphoric acid halide represented by the following in an appropriate solvent.
反応温度は２０℃〜１５０ｏｏ、好ましくは３０午０〜
８０℃であり、反応時間は長くとも数時間である。溶媒
としては反応に関係しないもの、例えばアルコール、ベ
ンゼン、トルエン、アセトン、クロロホルム、テトラヒ
ドロフラン等が好ましく、特に、アセトン、アルコール
が適当である。反応生成物は常法により回収される。即
ち、生成物が反応終了時に溶液から析出していればこれ
を炉週により回収できる。あるいは生成物が反応終了時
に溶解している場合は減圧で溶媒を除去することによっ
て回収できる。なお、原料である化合物式（０）は前記
文献に従い合成した。以下、実施例により本発明を説明
する。The reaction temperature is 20℃~150oo, preferably 30:00~
The temperature is 80°C, and the reaction time is several hours at most. As the solvent, solvents unrelated to the reaction, such as alcohol, benzene, toluene, acetone, chloroform, and tetrahydrofuran, are preferred, with acetone and alcohol being particularly suitable. The reaction product is recovered by conventional methods. That is, if the product is precipitated from the solution at the end of the reaction, it can be recovered by heating. Alternatively, if the product is dissolved at the end of the reaction, it can be recovered by removing the solvent under reduced pressure. Note that compound formula (0), which is a raw material, was synthesized according to the above-mentioned literature. The present invention will be explained below with reference to Examples.
実施例 １
２，３，５，６ーテトラヒドロ−６−フエニルイミダゾ
〔２．１−ｂ〕チアゾリオー７−○ーエチルフオスホロ
チオエート２，３，５，６ーテトラヒドロ−６−フエニ
ルイミダゾ〔２．１一ｂ〕チアゾール６．０夕（０．０
３モル）をアセトン５０のとに溶かし、この溶液へ０．
０ージェチルチオリン酸クロラィド５．７夕（０．０３
モル）を滴下した。Example 1 2,3,5,6-tetrahydro-6-phenylimidazo[2.1-b]thiazolio 7-○-ethylphosphorothioate 2,3,5,6-tetrahydro-6-phenylimidazo[2.1-b] ] Thiazole 6.0 yen (0.0
3 mol) is dissolved in 50 mol of acetone, and 0.0 mol is added to this solution.
0-jethylthiophosphoric acid chloride 5.7 hours (0.03
mol) was added dropwise.
滴下後５０℃にて３時間燈拝したところ最初は透明であ
ったがやがて白色結晶が生成し始めた。冷却したのち結
晶を炉取し、エタノールにて再結晶することにより５．
０夕（収率５１％）の、融点１８２〜１８３ｑｏの白色
針状結晶がえられた。元素分析値 Ｃ，３日，７Ｎ２０
２ＰＳ２として計算値（％）Ｃ：４７．５４Ｈ：５．２
３Ｎ：８．５蛇：９．４＄１９．５２実験値（％）Ｃ：
４７．２７Ｈ：５．１鮒：８，２が：９．２＄：１９．
３３実施例 ２
５，６ージヒドロー６ーフエニルイミダゾ〔２．１一ｂ
〕チアゾリオー７−○−エチルフオスホロチオエート５
，６−ジヒドロー６ーフエニルイミダゾ〔２．１−ｂ〕
チアゾール６．０夕（０．０３モル）をアセトン５０の
‘に溶かし、この溶液へ０，０−ジェチルリン酸クロラ
ィド５．７夕（０．０３モル）を滴下した。After the dropwise addition, the mixture was heated at 50° C. for 3 hours, and although it was initially transparent, white crystals soon began to form. 5. After cooling, the crystals are taken in a furnace and recrystallized with ethanol.
White needle-like crystals with a melting point of 182-183 qo were obtained in a yield of 0.0 m (yield 51%). Elemental analysis value C, 3 days, 7N20
Calculated value (%) as 2PS2 C: 47.54H: 5.2
3N: 8.5 Snake: 9.4 $19.52 Experimental value (%) C:
47.27H: 5.1 Carp: 8, 2: 9.2 $: 19.
33 Example 2 5,6-dihydro-6-phenylimidazo [2.11b
] Thiazolio 7-○-ethylphosphorothioate 5
, 6-dihydro 6-phenylimidazo [2.1-b]
6.0 mmol (0.03 mole) of thiazole was dissolved in 50 mmol of acetone, and 5.7 mmol (0.03 mole) of 0,0-jethylphosphoric acid chloride was added dropwise to this solution.
滴下時発熱すると共に白色結晶が生じた。更に５０℃に
て３時間燈拝し、冷却後結晶を炉取し、エタノールにて
再結晶することにより６．２夕（収率６３％）の収量で
融点１９１．５〜１９〆０の白色結晶が得られた。Upon dropping, heat was generated and white crystals were formed. After further heating at 50°C for 3 hours, the crystals were collected in a furnace after cooling and recrystallized with ethanol to produce a white product with a yield of 6.2 hours (yield 63%) and a melting point of 191.5-19.0. Crystals were obtained.
元素分析値 Ｃ，８日，が２０２塔２として計算値（％
）Ｃ：４７．８４Ｈ：４．６４Ｎ：８．５卵：９．４＄
：１９．６５実験値（％）Ｃ：４７．７４日４．欧州：
８．４１Ｐ：９．３お：１９．４０次に本発明化合物の
用途の一である殺線虫剤としての効果を試験例として示
した。The elemental analysis value C, 8th, is calculated as 202 tower 2 (%
) C: 47.84H: 4.64N: 8.5 Egg: 9.4$
: 19.65 Experimental value (%) C: 47.74 days 4. Europe:
8.41P: 9.3O: 19.40Next, the effect as a nematocide, which is one of the uses of the compound of the present invention, was shown as a test example.
〔試験例〕試験方法
供試薬剤を所定濃度の水溶液とし、次にこの薬剤を直径
９．５弧×高さ１．５弧のシャーレに約２比ｃ程度移し
これにＰａＭｇｒｅｌ１雌ＳＰＰ（自活性線虫）約５０
０頭入った液を注入し、一定時間ごとの死虫数を測定し
た。[Test example] Test method The test drug is made into an aqueous solution with a predetermined concentration. Next, this drug is transferred to a Petri dish with a diameter of 9.5 arcs and a height of 1.5 arcs at a rate of about 2c. nematodes) approx. 50
A solution containing 0 insects was injected, and the number of dead insects was measured at regular intervals.
なお、対照薬剤としてテトラミゾール （Ｔｅｔｒａｍｉｓｏｌｅ）塩酸塩を用いた。In addition, tetramisole was used as a control drug. (Tetramisole) hydrochloride was used.
供試化合物Ｐａｎａｇｒｅｌｌｕｓ ＳＰＰの死虫率（
多）（０ｏｎｔｒｏｌは何れも死虫率 ０※）Mortality rate of test compound Panagrellus SPP (
(0ontrol has a mortality rate of 0*)
第１図は２，３，５，６−テトラヒドロー６ーフエニル
イミダゾ〔２．１−ｂ〕チアゾリオ−７一〇ーェチルホ
スホロチオヱートのＫＢｒ結晶法による赤外吸収スペク
トルであり、第２図は５，６−ジヒドロー６−フエニル
イミダゾ〔２．１一ｂ〕イミダゾ１」オー７−○−エチ
ルホスホロチオヱートのＫＢｒ結晶法による赤外吸収ス
ペクトルである。
多！図第２図Figure 1 is an infrared absorption spectrum of 2,3,5,6-tetrahydro-6-phenylimidazo[2.1-b]thiazolio-710-ethylphosphorothioate obtained by the KBr crystal method. , FIG. 2 is an infrared absorption spectrum of 5,6-dihydro-6-phenylimidazo[2.1-b]imidazo-1'o-7-○-ethylphosphorothioate obtained by the KBr crystal method. Many! Figure 2
Claims (1)
硫黄原子を表わし、…は二重結合を選択できる。 ）で表わされるイミダゾチアゾリウム化合物。[Claims] 1 Represented by the formula ▲ There are mathematical formulas, chemical formulas, tables, etc. Imidazothiazolium compounds.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5647877A JPS6021160B2 (en) | 1977-05-18 | 1977-05-18 | imidazothiazolium compounds |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5647877A JPS6021160B2 (en) | 1977-05-18 | 1977-05-18 | imidazothiazolium compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS53144595A JPS53144595A (en) | 1978-12-15 |
| JPS6021160B2 true JPS6021160B2 (en) | 1985-05-25 |
Family
ID=13028196
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP5647877A Expired JPS6021160B2 (en) | 1977-05-18 | 1977-05-18 | imidazothiazolium compounds |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6021160B2 (en) |
-
1977
- 1977-05-18 JP JP5647877A patent/JPS6021160B2/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| JPS53144595A (en) | 1978-12-15 |
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