JPS5943462B2 - α-isocyano fatty acid amide derivatives and their production method - Google Patents
α-isocyano fatty acid amide derivatives and their production methodInfo
- Publication number
- JPS5943462B2 JPS5943462B2 JP57055708A JP5570882A JPS5943462B2 JP S5943462 B2 JPS5943462 B2 JP S5943462B2 JP 57055708 A JP57055708 A JP 57055708A JP 5570882 A JP5570882 A JP 5570882A JP S5943462 B2 JPS5943462 B2 JP S5943462B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- lower alkyl
- isocyano
- fatty acid
- compound according
- 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
- 235000014113 dietary fatty acids Nutrition 0.000 title claims description 5
- 229930195729 fatty acid Natural products 0.000 title claims description 5
- 239000000194 fatty acid Substances 0.000 title claims description 5
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 20
- -1 piperazino group Chemical group 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- CFCNTIFLYGKEIO-UHFFFAOYSA-N 2-isocyanoacetic acid Chemical compound OC(=O)C[N+]#[C-] CFCNTIFLYGKEIO-UHFFFAOYSA-N 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 4
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 4
- 125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 claims description 2
- LCDCPQHFCOBUEF-UHFFFAOYSA-N pyrrolidine-1-carboxamide Chemical compound NC(=O)N1CCCC1 LCDCPQHFCOBUEF-UHFFFAOYSA-N 0.000 claims description 2
- ZKWFSTHEYLJLEL-UHFFFAOYSA-N morpholine-4-carboxamide Chemical compound NC(=O)N1CCOCC1 ZKWFSTHEYLJLEL-UHFFFAOYSA-N 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 6
- CRXFROMHHBMNAB-UHFFFAOYSA-N methyl 2-isocyanoacetate Chemical compound COC(=O)C[N+]#[C-] CRXFROMHHBMNAB-UHFFFAOYSA-N 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- SLUNEGLMXGHOLY-UHFFFAOYSA-N benzene;hexane Chemical compound CCCCCC.C1=CC=CC=C1 SLUNEGLMXGHOLY-UHFFFAOYSA-N 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- WFCSWCVEJLETKA-UHFFFAOYSA-N 2-piperazin-1-ylethanol Chemical compound OCCN1CCNCC1 WFCSWCVEJLETKA-UHFFFAOYSA-N 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 230000035784 germination Effects 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000002911 monocyclic heterocycle group Chemical group 0.000 description 1
- 230000001473 noxious effect Effects 0.000 description 1
- JSPCTNUQYWIIOT-UHFFFAOYSA-N piperidine-1-carboxamide Chemical compound NC(=O)N1CCCCC1 JSPCTNUQYWIIOT-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000011403 purification operation Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Description
【発明の詳細な説明】
本発明は一般式
ＣＮ−ＣＨ２−ＣＯＮこＡＣＩ〕
（但し、ＮＯＡ基はモルホリノ基、ピペリジノ基、ピペ
ラジノ基またはピロリジノ基であつて、前記ピペラジノ
基の４位窒素原子上に低級アルキル基もしくはヒドロキ
シ低級アルキル基を有しうることを表わす。Detailed Description of the Invention The present invention is based on the general formula CN-CH2-CONACI] (However, the NOA group is a morpholino group, a piperidino group, a piperazino group, or a pyrrolidino group, and This means that the compound may have a lower alkyl group or a hydroxy lower alkyl group.
）で示されるα−イソシアノ脂肪酸アミド誘導体および
その製法に関する。) and its production method.
上記本発明の目的化合物〔Ｉ〕は水田、畑地等の農耕地
やその他非農耕地に発生する有害雑草の発芽抑制作用を
有する有用な農薬化合物である。The object compound [I] of the present invention is a useful agrochemical compound having an effect of suppressing the germination of noxious weeds that occur in agricultural land such as paddy fields and fields, and other non-agricultural land.
また本目的化合物印のうちα−イソシアノ酢酸ピペラジ
ンアミドは消炎作用をも有する有用な医薬化合物である
。本発明の目的化合物〔Ｉ〕の例としては、前記一般式
〔Ｉ〕においてＮ’、Ａ基が例えばモルホリノ基、ピペ
リジノ基、ピペラジノ基またはピロリジノ基の如き複素
単環式基であつて、前記ピペラジノ基の４位窒素原子上
に例えばメチル基、エチル基の如き低級アルキル基、ヒ
ドロキシメチル基、ヒドロキシエチル基の如きヒドロキ
シ低級アルキル基等を有する場合もある化合物が挙げら
れ、これらはいずれも新規化合物である。Among the target compounds, α-isocyanoacetic acid piperazine amide is a useful pharmaceutical compound that also has anti-inflammatory effects. As an example of the object compound [I] of the present invention, in the general formula [I], N' and A groups are heteromonocyclic groups such as a morpholino group, a piperidino group, a piperazino group, or a pyrrolidino group, and Examples include compounds that may have a lower alkyl group such as a methyl group or an ethyl group, or a hydroxy lower alkyl group such as a hydroxymethyl group or a hydroxyethyl group on the 4-position nitrogen atom of the piperazino group, all of which are novel. It is a compound.
本発明によれば、当該目的化合物〔〕は一般式（但し、
Ｎ●Ａ基は前記と同一意味を表わす。According to the present invention, the target compound [ ] has the general formula (however,
The N●A group has the same meaning as above.
）で示されるアミンと一般式ν よ１ υ ふ▲乙
ＶＶν ＾ＶＶ７（但し、Ｒは低級アルキル基を
表わす。) and the general formula ν YO1 υ FU ▲ VVν ＾VV7 (However, R represents a lower alkyl group.
）で示されるα−イソシアノ脂肪酸エステルとを反応さ
せることにより製することが出来る。) It can be produced by reacting with an α-isocyano fatty acid ester represented by the following formula.
本発明において原料化合物（９）の好適な例としてはモ
ルホリン、ピペリジン、ピロリジン、Ｎ−メチルピペラ
ジン又はＮ−（２−ヒドロキシエチノりピペラジンなど
があげられる。In the present invention, preferable examples of the raw material compound (9) include morpholine, piperidine, pyrrolidine, N-methylpiperazine, and N-(2-hydroxyethynolypiperazine).
また他方の原料化合物の好適な例としてはＲが例えばメ
チル基、エチル基、プロピル基、イソプロピル基の如き
低級アルキル基である化合物があげられ、これらの化合
物は上記原料アミン叩と反応させることによりそれぞれ
対応する目的化合物〔１〕へ誘導することが出来る。本
発明の反応は適当な溶媒中上記原料化合物０に対して原
料化合物（９）を約１．５乃至３モル程度作用させて実
施するのが好ましい。Preferred examples of the other raw material compound include compounds in which R is a lower alkyl group such as a methyl group, ethyl group, propyl group, or isopropyl group, and these compounds can be prepared by reacting with the raw material amine. Each can be guided to the corresponding target compound [1]. The reaction of the present invention is preferably carried out by allowing about 1.5 to 3 mol of starting compound (9) to act on the above starting compound 0 in a suitable solvent.
反応溶媒としては例えばメタノール、エタノールの如き
アルカノール、テトラヒドロフラン等を適宜使用出来る
。反応温度は室温付近にあるのが好適であり、この場合
反応は２乃至４８時間程度で完了する。かくして生成し
た本目的化合物〔〕は、例えば濃縮、抽出、カラムクロ
マトグラフイ一、再結晶等の公知単離精製操作に適宜付
することにより容易に取得することが出来る。実施例
１
α−イソシアノ酢酸メチルエステル１２９（０．１２モ
ル）およびモルホリン３１．６９（０．３６モル）をメ
タノール８０ｍ２に溶解し、室温にて２４時間かくはん
する。As the reaction solvent, for example, alkanols such as methanol and ethanol, tetrahydrofuran, etc. can be used as appropriate. The reaction temperature is preferably around room temperature, in which case the reaction is completed in about 2 to 48 hours. The objective compound thus produced can be easily obtained by appropriately subjecting it to known isolation and purification operations such as concentration, extraction, column chromatography, and recrystallization. Example
1. 129 (0.12 mol) of α-isocyanoacetic acid methyl ester and 31.69 (0.36 mol) of morpholine are dissolved in 80 m2 of methanol and stirred at room temperature for 24 hours.
反応終了液を減圧下に濃縮し得られる残査をクロロホル
ムで抽出する。この抽出液を水洗し、乾燥したのら溶媒
を留去する。得られる結晶性残査をエーテルで洗浄し口
取することにより、α−イソシアノ酢酸・モルホリンア
ミド１５９を得る。収率８１％ｏ実施例 ２
α−イソシアノ酢酸メチルエステル１０９（０．１モル
）およびピペリジン１７９（０．２モノ０をメタノール
１００ｍ１に溶解し、室温にて２時間かくはんする。The reaction-completed solution is concentrated under reduced pressure, and the resulting residue is extracted with chloroform. This extract is washed with water, dried, and the solvent is distilled off. The resulting crystalline residue is washed with ether and collected to obtain α-isocyanoacetic acid morpholinamide 159. Yield 81% o Example 2 α-isocyanoacetic acid methyl ester 109 (0.1 mol) and piperidine 179 (0.2 mono 0) were dissolved in 100 ml of methanol and stirred at room temperature for 2 hours.
反応終了液を減圧下に濃縮し得られる結晶性残査をエー
テルで洗浄し口取する。この結晶をベンゼン一ｎ−ヘキ
サンより再結晶することにより、α−イソシアノ酢酸・
ピペリジンアミド１３。７９を得る。The reaction-completed solution is concentrated under reduced pressure, and the resulting crystalline residue is washed with ether and collected. By recrystallizing this crystal from benzene-n-hexane, α-isocyanoacetic acid and
Piperidinamide 13.79 is obtained.
収率９０％ｏ実施例 ３
α−イソシアノ酢酸メチルエステル４．３９（０．０４
３モＪレ）およびピロリジン４．６９（（０．０６５モ
ル）をメタノール３０ｍ１に溶解し、室温にて２時間か
くはんする。Yield 90% o Example 3 α-isocyanoacetic acid methyl ester 4.39 (0.04
3 mole) and pyrrolidine 4.69 (0.065 mole) were dissolved in 30 ml of methanol and stirred at room temperature for 2 hours.
反応終了液を減圧下に讃縮し得られた残査をクロロホル
ムで抽出する。この抽出液を水洗し、乾燥したのち溶媒
を留去する。得られる結晶性残査をエーテルで洗浄し口
取することにより、α−イソシアノ酢酸・ピロリジンア
ミド４．０ｇを得る。収率６９％。実施例 ４α−イソ
シアノ酢酸メチルエステル１５９（０．１５モル）およ
びＮ−メチルピペラジン４５．５９（０．４５モル）を
メタノール１００ＴＩ１１に溶解し、室温にて２４時間
かくはんする。The reaction-completed liquid is condensed under reduced pressure, and the resulting residue is extracted with chloroform. This extract is washed with water, dried, and then the solvent is distilled off. The resulting crystalline residue is washed with ether and collected to obtain 4.0 g of α-isocyanoacetic acid/pyrrolidine amide. Yield 69%. Example 4 α-isocyanoacetic acid methyl ester 159 (0.15 mol) and N-methylpiperazine 45.59 (0.45 mol) are dissolved in methanol 100TI11 and stirred at room temperature for 24 hours.
反応終了液を減圧下に濃縮し得られた結晶性残査をエー
テルで洗浄し口取する。この結晶をベンゼン一ｎヘキサ
ンより再結晶することにより、α−イソシアノ酢酸・Ｎ
−メチルピペラジンアミド２０９を得る。収率８０％ｏ
実施例 ５
α−イソシアノ酢酸メチルエステル４．０９（０．０４
モル）およびＮ−（２−ヒドロキシエチル）ピペラジン
７．８９（０．０６モル）をメタノール５０ｍ１に溶解
し、室温にて４８時間かくはんする。The reaction-completed liquid was concentrated under reduced pressure, and the resulting crystalline residue was washed with ether and collected. By recrystallizing this crystal from benzene-N hexane, α-isocyanoacetic acid/N
-Methylpiperazine amide 209 is obtained. Yield 80%o
Example 5 α-isocyanoacetic acid methyl ester 4.09 (0.04
7.89 (0.06 mol) of N-(2-hydroxyethyl)piperazine are dissolved in 50 ml of methanol and stirred at room temperature for 48 hours.
Claims (1)
ラジノ基またはピロリジノ基であつて、前記ピペラジノ
基の４位窒素原子上に低級アルキル基もしくはヒドロキ
シ低級アルキル基を有しうることを表わす。 ）で示されるα−イソシアノ脂肪酸アミド誘導体。 ２ α−イソシアノ酢酸・モルホリンアミドである特許
請求の範囲第１項記載の化合物。 ３ α−イソシアノ酢酸・ピペリジンアミドである特許
請求の範囲第１項記載の化合物。 ４ α−イソシアノ酢酸・ピロリジンアミドである特許
請求の範囲第１項記載の化合物。 ５ α−イソシアノ酢酸・Ｎ−メチルピペラジンアミド
である特許請求の範囲第１項記載の化合物。 ６ α−イソシアノ酢酸・Ｎ′−（２−ヒドロキシエチ
ル）ピペラジンアミドである特許請求の範囲第１項記載
の化合物。 ７ 一般式 ＨＮ■Ａ （但し、Ｎ■Ａ基はモルホリノ基、ピペリジノ基、ピペ
ラジノ基またはピロリジノ基であつて、前記ピペラジノ
基の４位窒素原子上に低級アルキル基もしくはヒドロキ
シ低級アルキル基を有しうることを表わす。 ）で示されるアミンと一般式 ＣＮ−ＣＨ＿２−ＣＯＯＲ （但し、Ｒは低級アルキル基を表わす。 ）で示されるα−イソシアノ脂肪酸エステルとを反応さ
せることを特徴とする一般式ＣＮ−ＣＨ＿２−ＣＯＮ■
Ａ （但し、Ｎ■Ａ基は前記と同一意味を有する。 ）で示されるα−イソシアノ脂肪酸アミド誘導体の製法
。[Scope of Claims] 1 General formula CN-CH_2-CON■A [I] (However, the N■A group is a morpholino group, a piperidino group, a piperazino group, or a pyrrolidino group, and the nitrogen atom at the 4-position of the piperazino group An α-isocyano fatty acid amide derivative represented by the following formula (indicates that it may have a lower alkyl group or a hydroxy lower alkyl group on the top thereof). 2. The compound according to claim 1, which is α-isocyanoacetic acid/morpholinamide. 3. The compound according to claim 1, which is α-isocyanoacetic acid/piperidinamide. 4. The compound according to claim 1, which is α-isocyanoacetic acid/pyrrolidine amide. 5. The compound according to claim 1, which is α-isocyanoacetic acid/N-methylpiperazine amide. 6. The compound according to claim 1, which is α-isocyanoacetic acid/N'-(2-hydroxyethyl)piperazine amide. 7 General formula HN■A (However, the N■A group is a morpholino group, a piperidino group, a piperazino group, or a pyrrolidino group, and has a lower alkyl group or a hydroxy lower alkyl group on the nitrogen atom at the 4-position of the piperazino group. ) is characterized by reacting an amine represented by the general formula CN-CH_2-COOR with an α-isocyano fatty acid ester represented by the general formula CN-CH_2-COOR (where R represents a lower alkyl group). -CH_2-CON■
A method for producing an α-isocyano fatty acid amide derivative represented by A (wherein the N and A groups have the same meanings as above).
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP57055708A JPS5943462B2 (en) | 1982-04-02 | 1982-04-02 | α-isocyano fatty acid amide derivatives and their production method |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP57055708A JPS5943462B2 (en) | 1982-04-02 | 1982-04-02 | α-isocyano fatty acid amide derivatives and their production method |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP12750576A Division JPS5353617A (en) | 1976-10-23 | 1976-10-23 | Alpha-isocyano fatty acid amide derivatives and process for preparation of thesame |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS58172386A JPS58172386A (en) | 1983-10-11 |
| JPS5943462B2 true JPS5943462B2 (en) | 1984-10-22 |
Family
ID=13006377
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP57055708A Expired JPS5943462B2 (en) | 1982-04-02 | 1982-04-02 | α-isocyano fatty acid amide derivatives and their production method |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5943462B2 (en) |
-
1982
- 1982-04-02 JP JP57055708A patent/JPS5943462B2/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| JPS58172386A (en) | 1983-10-11 |
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