JPH10175958A - Production of 2-formylimidazole derivative - Google Patents

Production of 2-formylimidazole derivative

Info

Publication number
JPH10175958A
JPH10175958A JP8354391A JP35439196A JPH10175958A JP H10175958 A JPH10175958 A JP H10175958A JP 8354391 A JP8354391 A JP 8354391A JP 35439196 A JP35439196 A JP 35439196A JP H10175958 A JPH10175958 A JP H10175958A
Authority
JP
Japan
Prior art keywords
derivative
solvent
persulfate
formylimidazole
methylimidazole
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.)
Pending
Application number
JP8354391A
Other languages
Japanese (ja)
Inventor
Shigetoshi Kawada
成利 川田
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Nippon Synthetic Chemical Industry Co Ltd
Original Assignee
Nippon Synthetic Chemical Industry Co Ltd
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Nippon Synthetic Chemical Industry Co Ltd filed Critical Nippon Synthetic Chemical Industry Co Ltd
Priority to JP8354391A priority Critical patent/JPH10175958A/en
Publication of JPH10175958A publication Critical patent/JPH10175958A/en
Pending legal-status Critical Current

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Classifications

    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts

Abstract

PROBLEM TO BE SOLVED: To efficiently produce the subject compound important as an intermediate for medicines, agrochemicals, etc., by oxidizing a 2-methylimidazole derivative with a persulfate in the presence of a salt of a transition metal element in a solvent. SOLUTION: (A) A 2-methylimidazole derivative of formula I (R<1> and R<2> are each H, a halogen or a substituent group in which H is not bonded to a carbon atom directly bonded to an imidazole ring, such as phenyl) is oxidized with (B) a persulfate such as sodium persulfate as an oxidizing agent in a solvent such as water or an alcohol having affinity for water especially preferably in the presence of a catalyst such as copper sulfate under an acidic condition. The reaction product is neutralized with an alkali and subjected to concentration to dryness, extraction with a solvent, recrystallization, distillation, etc., to give the objective compound of formula II. The amount of the oxidizing agent used is 0.5-5.0mol based on 1mol of the component A, that of the catalyst is 0.05-50mol% based on the component B and that of the solvent is 1-200 pts.wt. based on 1 pt.wt. of the component A. The reaction is carried out at 5-80 deg.C for 0.5-10 hours.

Description

【発明の詳細な説明】DETAILED DESCRIPTION OF THE INVENTION

【０００１】[0001]

【発明の属する技術分野】本発明は２−ホルミルイミダ
ゾール誘導体の製造法に関する。TECHNICAL FIELD The present invention relates to a method for producing a 2-formylimidazole derivative.

【０００２】[0002]

【従来の技術】２−ホルミルイミダゾール誘導体は、医
薬、農薬等の中間体として重要であり、その製造法とし
て、例えば、ブチルリチウムとイミダゾール化合物を反
応させ、これにジメチルホルムアルデヒドを反応させる
方法（特開平１−１３１１６３号公報、特開昭６２−１
３５４６１号公報）、ジクロルアセトニトリルをアミジ
ン化合物とし、更に環化させる方法が提案されている
（Ｊ．Ｏｒｇ．Ｃｈｅｍ．６０，１０９０（１９９
５））。2. Description of the Related Art A 2-formylimidazole derivative is important as an intermediate for pharmaceuticals, agricultural chemicals and the like. For example, a method for producing it is a method of reacting butyllithium with an imidazole compound and then reacting it with dimethylformaldehyde. JP-A-1-131163, JP-A-62-1
No. 35461), and a method for further cyclizing dichloroacetonitrile as an amidine compound has been proposed (J. Org. Chem. 60 , 1090 (199).
5)).

【０００３】[0003]

【発明が解決しようとする課題】しかしながら、特開平
１−１３１１６３号公報、特開昭６２−１３５４６１号
公報開示技術では、ブチルリチウムの工業的な取り扱い
が難しく、更に超低温（−３５℃以下）で反応させなけ
ればならず、また多段階の反応工程を必要とし、また
Ｊ．Ｏｒｇ．Ｃｈｅｍ．６０，１０９０（１９９５）開
示技術では、高価な原料のジクロルアセトニトリルを用
いなければならず、更に超低温（−７８℃）で反応させ
なければならず、また多段階の反応工程を必要とする欠
点があった。However, in the techniques disclosed in Japanese Patent Application Laid-Open Nos. 1-131163 and 62-135461, industrial handling of butyllithium is difficult, and furthermore, at extremely low temperatures (-35 ° C. or lower). The reaction must be carried out and requires a multi-step reaction process. Org. Chem. 60 , 1090 (1995) discloses the disadvantage that expensive raw material dichloroacetonitrile must be used, the reaction must be carried out at an ultra-low temperature (-78 ° C), and a multi-step reaction process is required. was there.

【０００４】[0004]

【課題を解決するための手段】本発明者は、かかる課題
を解決するため鋭意研究を重ねた結果、下記化３で表さ
れる２−メチルイミダゾール誘導体（I）を酸化させる
ことにより、効率よく下記化４で表される２−ホルミル
イミダゾール誘導体（II）を製造できることを見い出し
本発明を完成した。Means for Solving the Problems The inventors of the present invention have conducted intensive studies in order to solve the above-mentioned problems, and as a result, by oxidizing the 2-methylimidazole derivative (I) represented by the following chemical formula 3, it is possible to efficiently obtain the compound. The present inventors have found that a 2-formylimidazole derivative (II) represented by the following formula 4 can be produced and completed the present invention.

【化３】 ［式中Ｒ1、Ｒ2は水素原子、ハロゲン原子、及びイミダ
ゾール環に直接結合した炭素原子に水素原子が結合して
いない置換基を意味する。］Embedded image [Wherein R 1 and R 2 represent a hydrogen atom, a halogen atom, and a substituent in which a hydrogen atom is not bonded to a carbon atom directly bonded to an imidazole ring. ]

【化４】 ［式中Ｒ1、Ｒ2は前記と同様の意味を有する。］Embedded image Wherein R 1 and R 2 have the same meaning as described above. ]

【０００５】[0005]

【発明の実施の形態】以下本発明を詳細に説明する。本
発明で原料となる２−メチルイミダゾール誘導体（I）
は下記化５で表される。DESCRIPTION OF THE PREFERRED EMBODIMENTS The present invention will be described below in detail. 2-Methylimidazole derivative (I) used as a raw material in the present invention
Is represented by the following formula 5.

【化５】 式中Ｒ1、Ｒ2は水素原子、ハロゲン原子、及びイミダゾ
ール環に直接結合した炭素原子に水素原子が結合してい
ない置換基、例えばフェニル基、ビフェニル基等を意味
する。さらに具体的には、例えば下記化合物を挙げるこ
とができるが、本発明にかかる２−メチルイミダゾール
誘導体（I）はこれらに限定されない。Embedded image In the formula, R 1 and R 2 represent a hydrogen atom, a halogen atom, and a substituent in which a hydrogen atom is not bonded to a carbon atom directly bonded to an imidazole ring, for example, a phenyl group, a biphenyl group and the like. More specifically, for example, the following compounds may be mentioned, but the 2-methylimidazole derivative (I) according to the present invention is not limited thereto.

【０００６】 ２−メチル−イミダゾール ４（５）−クロロ−２−メチル−イミダゾール ４，５−ジクロロ−２−メチル−イミダゾール ４（５）−ブロモ−２−メチル−イミダゾール ４，５−ジブロモ−２−メチル−イミダゾール ４（５）−フェニル−２−メチル−イミダゾール ４，５−ジフェニル−２−メチル−イミダゾール ４（５）−ビフェニル−２−メチル−イミダゾール ４，５−ジ−ビフェニル−２−メチル−イミダゾー
ル[0006] 2-Methyl-imidazole 4 (5) -chloro-2-methyl-imidazole 4,5-dichloro-2-methyl-imidazole 4 (5) -bromo-2-methyl-imidazole 4,5-dibromo-2 -Methyl-imidazole 4 (5) -phenyl-2-methyl-imidazole 4,5-diphenyl-2-methyl-imidazole 4 (5) -biphenyl-2-methyl-imidazole 4,5-di-biphenyl-2-methyl -Imidazole

【０００７】本発明の酸化反応で使用される酸化剤とし
ては過硫酸ナトリウム、過硫酸カリウム等の過硫酸アル
カリ金属塩、過硫酸カルシウム、過硫酸マグネシウム等
の過硫酸アルカリ土類金属塩、過硫酸アンモニウム、過
硫酸トリエチルアンモニウム等の過硫酸アンモニウム塩
等の過硫酸塩、あるいはこれらの水和物が挙げられ、好
ましくは過硫酸塩アルカリ土類金属塩、あるいはこれら
の水和物が用いられる。又該過硫酸塩は併用しても使用
される。過硫酸塩を用いる場合、ｐＨ０．１〜１０で反
応は進行するが、酸性条件下で行うことが好ましく、そ
の場合、塩酸、硫酸等でｐＨを１．０〜６．９、好まし
くは１．０〜５．０にする。酸化剤の使用量として好ま
しくは２−メチルイミダゾール誘導体（I）１モルに対
して０．５〜５．０モル、更に好ましくは０．８〜２．
０モルである。０．５モル未満、あるいは無添加では原
料の２−メチルイミダゾール誘導体（I）が残存し、
５．０モルを越えても、収率は上がらず、酸化剤が無駄
になるので好ましくない。The oxidizing agent used in the oxidation reaction of the present invention includes alkali metal persulfates such as sodium persulfate and potassium persulfate; alkaline earth metal salts such as calcium persulfate and magnesium persulfate; and ammonium persulfate. And persulfates such as ammonium persulfate such as triethylammonium persulfate, and hydrates thereof. Preferably, persulfate alkaline earth metal salts and hydrates thereof are used. The persulfate is used in combination. When a persulfate is used, the reaction proceeds at a pH of 0.1 to 10, but is preferably performed under acidic conditions. In this case, the pH is adjusted to 1.0 to 6.9, preferably to 1. 0 to 5.0. The oxidizing agent is preferably used in an amount of 0.5 to 5.0 mol, more preferably 0.8 to 2.0 mol, per 1 mol of the 2-methylimidazole derivative (I).
0 mol. If less than 0.5 mol or no addition, the raw material 2-methylimidazole derivative (I) remains,
If it exceeds 5.0 moles, the yield will not increase and the oxidizing agent will be wasted, which is not preferable.

【０００８】本発明で製造される２−ホルミルイミダゾ
ール誘導体（II）は下記化６で表される。The 2-formylimidazole derivative (II) produced by the present invention is represented by the following formula (6).

【化６】 ［式中Ｒ1、Ｒ2は前記と同様の意味を有する。］Embedded image Wherein R 1 and R 2 have the same meaning as described above. ]

【０００９】具体的な代表例として例えば下記化合物を
挙げることができるが、本発明にかかる２−ホルミルイ
ミダゾール誘導体（II）はこれらに限定されない。尚下
記２−ホルミルイミダゾール誘導体（II）の〜のそ
れぞれは、上記２−メチルイミダゾール誘導体（I）の
同番号のものから製造されている。Specific representative examples include, for example, the following compounds, but the 2-formylimidazole derivative (II) according to the present invention is not limited thereto. Each of the following 2-formylimidazole derivatives (II) is manufactured from the same 2-methylimidazole derivative (I).

【００１０】 ２−ホルミルイミダゾール ４（５）−クロロ−２−ホルミルイミダゾール ４，５−ジクロロ−２−ホルミルイミダゾール ４（５）−ブロモ−２−ホルミルイミダゾール ４，５−ジブロモ−２−ホルミルイミダゾール ４（５）−フェニル−２−ホルミルイミダゾール ４，５−ジフェニル−２−ホルミルイミダゾール ４（５）−ビフェニル−２−ホルミルイミダゾール ４，５−ジ−ビフェニル−２−ホルミルイミダゾー
ル2-formylimidazole 4 (5) -chloro-2-formylimidazole 4,5-dichloro-2-formylimidazole 4 (5) -bromo-2-formylimidazole 4,5-dibromo-2-formylimidazole 4 (5) -Phenyl-2-formylimidazole 4,5-diphenyl-2-formylimidazole 4 (5) -biphenyl-2-formylimidazole 4,5-di-biphenyl-2-formylimidazole

【００１１】反応は２−メチルイミダゾール誘導体
（I）を通常の酸化剤で酸化すれば反応は進行するが、
過硫酸塩で酸化する場合、遷移金属元素の塩を触媒とし
て、２−メチルイミダゾール誘導体（I）を過硫酸塩で
酸化させることが必要で、該遷移金属元素とは、２１Ｓ
ｃから３０Ｚｎまで、３９Ｙから４８Ｃｄまで、５７Ｌ
ａから８０Ｈｇまで、８９Ａｃ以上の元素を意味する。
触媒として、好ましくは遷移金属元素の塩として、特に
好ましくは硫酸銅（の水和物）が用いられる。又該遷移
金属元素の塩は２種以上を併用して用いてもよい。The reaction proceeds when the 2-methylimidazole derivative (I) is oxidized with an ordinary oxidizing agent.
When oxidizing with a persulfate, it is necessary to oxidize the 2-methylimidazole derivative (I) with a persulfate using a salt of the transition metal element as a catalyst.
From c to 30Zn, from 39Y to 48Cd, 57L
It means an element of 89Ac or more from a to 80Hg.
As a catalyst, preferably a salt of a transition metal element, particularly preferably copper sulfate (hydrate) is used. Further, two or more kinds of the salts of the transition metal element may be used in combination.

【００１２】触媒の使用量としては、過硫酸塩に対して
０．０５〜５０モル％が必要で、好ましくは０．１〜１
０モル％である。０．０５モル％未満では反応速度が遅
くなり、５０モル％を越えても収率の向上は見られな
い。The catalyst is used in an amount of 0.05 to 50 mol%, preferably 0.1 to 1 mol%, based on the persulfate.
0 mol%. If it is less than 0.05 mol%, the reaction rate will be low, and if it exceeds 50 mol%, no improvement in yield will be observed.

【００１３】反応は、溶媒中で行うことが必要で、用い
られる溶媒としては、水や水と混和性のあるメタノー
ル、エタノール等のアルコール、酢酸、プロピオン酸等
の酸、Ｎ，Ｎ−ジメチルホルムアミド、Ｎ，Ｎ−ジメチ
ルアセトアミド、ヘキサメチルホスホルアミド、アセト
ニトリル、アセトン等が挙げられるが、好ましくは水が
用いられる。The reaction must be carried out in a solvent. Examples of the solvent used include water, water-miscible alcohols such as methanol and ethanol, acids such as acetic acid and propionic acid, and N, N-dimethylformamide. , N, N-dimethylacetamide, hexamethylphosphoramide, acetonitrile, acetone and the like, but preferably water is used.

【００１４】溶媒の使用量として好ましくは２−メチル
イミダゾール誘導体（I）１重量部に対して１〜２００
重量部、更に好ましくは１０〜５０重量部である。The solvent is preferably used in an amount of 1 to 200 parts by weight based on 1 part by weight of the 2-methylimidazole derivative (I).
Parts by weight, more preferably 10 to 50 parts by weight.

【００１５】本発明で使用されるそれぞれの薬剤の仕込
み手段（順序）は任意であり、一括仕込み、分割仕込
み、連続仕込み、滴下仕込み等いずれも実施可能である
が、ｐＨを酸性に調整する場合、２−メチルイミダゾー
ル誘導体（I）を溶媒中に溶解し、触媒を入れた後で、
酸でｐＨを調整し、その溶液に酸化剤を仕込んで反応さ
せるのが好ましく、以下かかる方法について具体的に説
明する。まず、２−メチルイミダゾール誘導体（I）に
４０〜５０倍重量の溶媒を加え、そこにあらかじめ加え
る酸化剤の重量の０．１〜１０重量％の触媒を加え、前
記の如く酸でｐＨを調整する。次に２−メチルイミダゾ
ール誘導体（I）１モルに対して０．８〜２．０モルの
酸化剤を５〜８０℃、好ましくは１０〜４０℃で混合し
０．５〜１０時間反応させる。The means (sequential order) of charging the respective drugs used in the present invention is arbitrary, and any of batch charging, divided charging, continuous charging, and dropping charging can be performed. After dissolving the 2-methylimidazole derivative (I) in a solvent and adding a catalyst,
It is preferable to adjust the pH with an acid, and to add an oxidizing agent to the solution to cause a reaction. Such a method will be specifically described below. First, a solvent of 40 to 50 times weight is added to the 2-methylimidazole derivative (I), a catalyst of 0.1 to 10% by weight of the weight of the oxidizing agent added in advance is added thereto, and the pH is adjusted with an acid as described above. I do. Next, 0.8 to 2.0 mol of the oxidizing agent is mixed at 5 to 80 ° C, preferably 10 to 40 ° C, and reacted for 0.5 to 10 hours based on 1 mol of the 2-methylimidazole derivative (I).

【００１６】反応終了後は、炭酸カリウム、炭酸ナトリ
ウム、水酸化ナトリウム、水酸化カリウム、炭酸水素ナ
トリウム、炭酸水素カリウム等のアルカリで中和後、濃
縮乾固、溶媒抽出、再結晶、蒸留等により精製を行い目
的物を得る。After completion of the reaction, the mixture is neutralized with an alkali such as potassium carbonate, sodium carbonate, sodium hydroxide, potassium hydroxide, sodium hydrogen carbonate, potassium hydrogen carbonate, etc., and then concentrated to dryness, extracted with a solvent, recrystallized, distilled or the like. Purify to obtain the desired product.

【００１７】かくして得られた２−ホルミルイミダゾー
ル誘導体（II）は、医薬、農薬等の中間体として大変有
用である。The 2-formylimidazole derivative (II) thus obtained is very useful as an intermediate for pharmaceuticals, agricultural chemicals and the like.

【００１８】[0018]

【実施例】以下、実施例を挙げて本発明を具体的に説明
する。 実施例１ ２−メチルイミダゾール４．２ｇ（５１．１ミリモル）
を２００ｍｌの水に溶解し、硫酸銅・５水和物０．１２
５ｇ（０．５０１ミリモル）を入れ、希硫酸でｐＨ２に
調整した。この溶液に過硫酸ナトリウム１３．１ｇ（５
５．０ミリモル）を５０ｍｌの水に溶解した液を一括で
添加し、６５℃で１０ｈｒ反応した。その後反応液を放
冷し、炭酸カリウムで中和後、酢酸エチル３００ｍｌを
加えて抽出した後、有機層を濃縮したところ、黄色粉末
を得た。該粉末を高速液体クロマトグラフィーで分析し
た所、２−ホルミルイミダゾールの標品と一致し、純度
は７１％であった。1Ｈ−ＮＭＲのデータ：９．６３
（ｓ）１Ｈ、７．４１（ｓ）２ＨThe present invention will be specifically described below with reference to examples. Example 1 4.2 g (51.1 mmol) of 2-methylimidazole
Was dissolved in 200 ml of water, and copper sulfate pentahydrate 0.12 was dissolved.
5 g (0.501 mmol) was added and adjusted to pH 2 with dilute sulfuric acid. To this solution was added 13.1 g of sodium persulfate (5.
(5.0 mmol) in 50 ml of water was added all at once, and reacted at 65 ° C. for 10 hours. Thereafter, the reaction solution was allowed to cool, neutralized with potassium carbonate, extracted with 300 ml of ethyl acetate, and then the organic layer was concentrated to give a yellow powder. The powder was analyzed by high performance liquid chromatography and found to be consistent with the standard for 2-formylimidazole, with a purity of 71%. 1 H-NMR data: 9.63
(S) 1H, 7.41 (s) 2H

【００１９】実施例２ ２−メチルイミダゾールの水溶液に、硫酸鉄・７水和物
０．１３５ｇ（０．４８６ミリモル）、硫酸銅・５水和
物０．１２５ｇ（０．５０１ミリモル）を一括に添加し
た後ｐＨ２に調整した以外は実施例１と同様に操作し、
黄色粉末を得た。該粉末を高速液体クロマトグラフィー
で分析した所、２−ホルミルイミダゾールの標品と一致
し、純度は８１％であった。1Ｈ−ＮＭＲのデータ：
９．６３（ｓ）１Ｈ、７．４１（ｓ）２ＨEXAMPLE 2 0.135 g (0.486 mmol) of iron sulfate heptahydrate and 0.125 g (0.501 mmol) of copper sulfate pentahydrate were added to an aqueous solution of 2-methylimidazole at once. The same operation as in Example 1 was carried out except that the pH was adjusted to 2 after the addition,
A yellow powder was obtained. The powder was analyzed by high performance liquid chromatography, and found to be consistent with the preparation of 2-formylimidazole, with a purity of 81%. 1 H-NMR data:
9.63 (s) 1H, 7.41 (s) 2H

【００２０】[0020]

【発明の効果】２−メチルイミダゾール誘導体（I）を
酸化させると温和な条件で効率よく、２−ホルミルイミ
ダゾール誘導体（II）が生成される。When the 2-methylimidazole derivative (I) is oxidized, the 2-formylimidazole derivative (II) is efficiently produced under mild conditions.

Claims (3)

【特許請求の範囲】[Claims] 【請求項１】 下記化１で表される２−メチルイミダゾ
ール誘導体（I）を酸化させることを特徴とする下記化
２で表される２−ホルミルイミダゾール誘導体（II）の
製造法。 【化１】 ［式中Ｒ1、Ｒ2は水素原子、ハロゲン原子、及びイミダ
ゾール環に直接結合した炭素原子に水素原子が結合して
いない置換基を意味する。］ 【化２】 ［式中Ｒ1、Ｒ2は前記と同様の意味を有する。］1. A method for producing a 2-formylimidazole derivative (II) represented by the following chemical formula 2, comprising oxidizing a 2-methylimidazole derivative (I) represented by the following chemical formula 1. Embedded image [Wherein R 1 and R 2 represent a hydrogen atom, a halogen atom, and a substituent in which a hydrogen atom is not bonded to a carbon atom directly bonded to an imidazole ring. ] Wherein R 1 and R 2 have the same meaning as described above. ] 【請求項２】 遷移金属元素の塩、溶媒の存在下、過硫
酸塩で酸化させることを特徴とする請求項１記載の２−
ホルミルイミダゾール誘導体（II）の製造法。2. The method according to claim 1, wherein the oxidation is performed with a persulfate in the presence of a salt of a transition metal element and a solvent.
A method for producing a formyl imidazole derivative (II). 【請求項３】 酸性条件下で酸化させることを特徴とす
る請求項２記載の２−ホルミルイミダゾール誘導体（I
I）の製造法。3. The 2-formylimidazole derivative (I) according to claim 2, which is oxidized under acidic conditions.
I) Manufacturing method.
JP8354391A 1996-12-18 1996-12-18 Production of 2-formylimidazole derivative Pending JPH10175958A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP8354391A JPH10175958A (en) 1996-12-18 1996-12-18 Production of 2-formylimidazole derivative

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP8354391A JPH10175958A (en) 1996-12-18 1996-12-18 Production of 2-formylimidazole derivative

Publications (1)

Publication Number Publication Date
JPH10175958A true JPH10175958A (en) 1998-06-30

Family

ID=18437251

Family Applications (1)

Application Number Title Priority Date Filing Date
JP8354391A Pending JPH10175958A (en) 1996-12-18 1996-12-18 Production of 2-formylimidazole derivative

Country Status (1)

Country Link
JP (1) JPH10175958A (en)

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