JP2002193915A - Benzenesulfonate compound - Google Patents
Benzenesulfonate compoundInfo
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- JP2002193915A JP2002193915A JP2000399828A JP2000399828A JP2002193915A JP 2002193915 A JP2002193915 A JP 2002193915A JP 2000399828 A JP2000399828 A JP 2000399828A JP 2000399828 A JP2000399828 A JP 2000399828A JP 2002193915 A JP2002193915 A JP 2002193915A
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Abstract
Description
【０００１】[0001]
【発明の属する技術分野】本発明は、新規なベンゼンス
ルフォナート化合物に関する。[0001] The present invention relates to a novel benzenesulfonate compound.
【０００２】[0002]
【課題を解決するための手段】本発明のベンゼンスルフ
ォナート化合物は、文献未記載の新規化合物であって、
下記一般式（１）で表される。Means for Solving the Problems The benzenesulfonate compound of the present invention is a novel compound not described in the literature,
It is represented by the following general formula (1).
【０００３】[0003]
【化２】 Embedded image
【０００４】［式中、Ｘはハロゲン原子を示す。］ 特開平２−１９１２５６号公報に記されているように、
７−｛４−［（２，３−ジクロロフェニル）−１−ピペ
ラジニル］ブトキシ｝−３，４−ジヒドロカルボスチリ
ル（アリピプラゾール）は、精神分裂病治療剤として有
用な化合物である。また、７−｛４−［（２，３−ジク
ロロフェニル）−１−ピペラジニル］ブトキシ｝−３，
４−ジヒドロカルボスチリルを合成するための原料は、
７−（４−ハロゲノブトキシ）−３，４−ジヒドロカル
ボスチリルであることも、公知である。[Wherein, X represents a halogen atom. As described in JP-A-2-191256,
7- {4-[(2,3-Dichlorophenyl) -1-piperazinyl] butoxy} -3,4-dihydrocarbostyril (aripiprazole) is a compound useful as a therapeutic agent for schizophrenia. 7- {4-[(2,3-dichlorophenyl) -1-piperazinyl] butoxy} -3;
The raw materials for synthesizing 4-dihydrocarbostyril are:
It is also known to be 7- (4-halogenobutoxy) -3,4-dihydrocarbostyril.
【０００５】本発明のベンゼンスルフォナート化合物
は、７−（４−ハロゲノブトキシ）−３，４−ジヒドロ
カルボスチリルを合成するための中間体として有用であ
る。The benzenesulfonate compound of the present invention is useful as an intermediate for synthesizing 7- (4-halogenobutoxy) -3,4-dihydrocarbostyril.
【０００６】本発明のベンゼンスルフォナート化合物を
使用すれば、７−（４−ハロゲノブトキシ）−３，４−
ジヒドロカルボスチリルを工業的規模にて、安価に、し
かも簡便な操作で、高収率且つ高純度で製造できる。By using the benzenesulfonate compound of the present invention, 7- (4-halogenobutoxy) -3,4-
Dihydrocarbostyril can be produced on an industrial scale at low cost and with simple operation in high yield and high purity.
【０００７】[0007]
【発明の実施の形態】本発明において、Ｘ及びＸ1で示
されるハロゲン原子は、具体的には弗素原子、塩素原
子、臭素原子、沃素原子等が挙げられる。BEST MODE FOR CARRYING OUT THE INVENTION In the present invention, specific examples of the halogen atom represented by X and X 1 include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.
【０００８】本発明の化合物は、種々の方法により製造
されるが、代表的な方法を示せば、例えば下記反応式−
１に示す方法を挙げることができる。The compound of the present invention can be produced by various methods. A typical method is as follows.
1 can be mentioned.
【０００９】[0009]
【化３】 Embedded image
【００１０】［式中、Ｘ1はハロゲン原子を示す。Ｘは
前記に同じ。］ 反応式−１によれば、本発明の一般式（１）のベンゼン
スルフォナート化合物は、一般式（２）で表される化合
物と一般式（３）で表される化合物とを、適当な溶媒
中、塩基性化合物の存在下に反応させることにより製造
される。[In the formula, X 1 represents a halogen atom. X is the same as above. According to Reaction Scheme-1, the benzenesulfonate compound of the general formula (1) of the present invention is obtained by appropriately converting the compound represented by the general formula (2) and the compound represented by the general formula (3). It is produced by reacting in a suitable solvent in the presence of a basic compound.
【００１１】用いられる溶媒としては、反応に悪影響を
及ぼさない限り、この種の反応に通常使用される溶媒を
広く使用でき、例えばジメチルエーテル、テトラヒドロ
フラン、ジオキサン、モノグライム、ジグライム等のエ
ーテル類、アセトン、メチルエチルケトン等のケトン
類、ベンゼン、ｏ−ジクロロベンゼン、トルエン、キシ
レン等の芳香族炭化水素類、酢酸メチル、酢酸エチル等
のエステル類、ジクロロメタン、ジクロロエタン、クロ
ロホルム、四塩化炭素等のハロゲン化炭化水素類、Ｎ，
Ｎ−ジメチルホルムアミド、ジメチルスルホキシド、ヘ
キサメチルリン酸トリアミド等の非プロトン性極性溶媒
等又は之等の混合溶媒等が挙げられる。As the solvent to be used, any solvent commonly used in this type of reaction can be used unless it adversely affects the reaction. Ketones such as, benzene, o-dichlorobenzene, toluene, aromatic hydrocarbons such as xylene, methyl acetate, esters such as ethyl acetate, dichloromethane, dichloroethane, chloroform, halogenated hydrocarbons such as carbon tetrachloride, N,
Non-protonic polar solvents such as N-dimethylformamide, dimethyl sulfoxide, hexamethylphosphoric acid triamide and the like, and mixed solvents thereof and the like.
【００１２】塩基性化合物としては、公知のものを広く
使用でき、例えば水酸化ナトリウム、水酸化カリウム、
水酸化セシウム、水酸化リチウム、炭酸ナトリウム、炭
酸カリウム、炭酸セシウム、炭酸リチウム、炭酸水素ナ
トリウム、炭酸水素カリウム、炭酸銀等の無機塩基、水
素化ナトリウム、ナトリウムアミド、カリウム、ナトリ
ウム等のアルカリ金属、ナトリウムメチラート、ナトリ
ウムエチラート、カリウムエチラート等のアルコラー
ト、酢酸ナトリウム等の有機酸金属塩、トリエチルアミ
ン、トリプロピルアミン、ジイソプロピルエチルアミ
ン、ピリジン、キノリン、Ｎ，Ｎ−ジメチルアニリン、
Ｎ−メチルモルホリン、４−ジメチルアミノピリジン、
１，５−ジアザビシクロ〔４．３．０〕ノネン−５（Ｄ
ＢＮ）、１，８−ジアザビシクロ〔５．４．０〕ウンデ
セン−７（ＤＢＵ）、１，４−ジアザビシクロ〔２．
２．２〕オクタン（ＤＡＢＣＯ）等の有機塩基等が挙げ
られる。As the basic compound, known compounds can be widely used, for example, sodium hydroxide, potassium hydroxide,
Inorganic bases such as cesium hydroxide, lithium hydroxide, sodium carbonate, potassium carbonate, cesium carbonate, lithium carbonate, sodium hydrogencarbonate, potassium hydrogencarbonate, silver carbonate; alkali metals such as sodium hydride, sodium amide, potassium, sodium; Alcoholates such as sodium methylate, sodium ethylate and potassium ethylate, organic acid metal salts such as sodium acetate, triethylamine, tripropylamine, diisopropylethylamine, pyridine, quinoline, N, N-dimethylaniline,
N-methylmorpholine, 4-dimethylaminopyridine,
1,5-diazabicyclo [4.3.0] nonene-5 (D
BN), 1,8-diazabicyclo [5.4.0] undecene-7 (DBU), 1,4-diazabicyclo [2.
2.2] Organic bases such as octane (DABCO).
【００１３】一般式（２）で表される化合物と一般式
（３）で表される化合物との使用割合は、限定されるも
のではないが、通常一般式（３）で表される化合物に対
して一般式（２）で表される化合物を少なくとも等モル
量、好ましくは等モル〜１．５倍モル量程度使用するの
がよい。The use ratio of the compound represented by the general formula (2) to the compound represented by the general formula (3) is not limited, but is usually limited to the compound represented by the general formula (3). On the other hand, the compound represented by the general formula (2) is used at least in an equimolar amount, preferably in an equimolar to 1.5-fold molar amount.
【００１４】一般式（２）で表される化合物と一般式
（３）で表される化合物との反応は、冷却下、室温下及
び加温下のいずれでも進行するが、通常０〜１００℃程
度、好ましくは０℃〜５０℃付近にて好適に進行し、一
般に０．５〜５時間程度で終了する。The reaction between the compound represented by the general formula (2) and the compound represented by the general formula (3) proceeds under cooling, at room temperature or under heating. Degree, preferably around 0 ° C. to 50 ° C., and generally completes in about 0.5 to 5 hours.
【００１５】[0015]
【化４】 Embedded image
【００１６】［式中、Ｘは前記に同じ。］ 反応式−２によれば、一般式（５）で表される７−（４
−ハロゲノブトキシ）−３，４−ジヒドロカルボスチリ
ルは、式（４）で表される７−ヒドロキシ−３，４−ジ
ヒドロ−２（１Ｈ）−キノリノンと一般式（１）のベン
ゼンスルフォナート化合物とを反応させることにより製
造される。また、式（７）で表される７−｛４−
［（２，３−ジクロロフェニル）−１−ピペラジニル］
ブトキシ｝−３，４−ジヒドロカルボスチリルは、一般
式（５）で表される７−（４−ハロゲノブトキシ）−
３，４−ジヒドロカルボスチリルと式（６）で表される
化合物とを反応させることにより製造される。Wherein X is as defined above. According to the reaction formula-2, 7- (4) represented by the general formula (5)
-Halogenobutoxy) -3,4-dihydrocarbostyril is a compound of 7-hydroxy-3,4-dihydro-2 (1H) -quinolinone represented by the formula (4) and a benzenesulfonate compound of the general formula (1) And is produced by reacting In addition, 7-７4-
[(2,3-dichlorophenyl) -1-piperazinyl]
Butoxy {-3,4-dihydrocarbostyril is a compound represented by the general formula (5): 7- (4-halogenobutoxy)-
It is produced by reacting 3,4-dihydrocarbostyril with a compound represented by the formula (6).
【００１７】一般式（４）で表される化合物と一般式
（１）で表される化合物との反応は、適当な溶媒中、塩
基性化合物の存在下に行われる。The reaction between the compound represented by the general formula (4) and the compound represented by the general formula (1) is carried out in a suitable solvent in the presence of a basic compound.
【００１８】用いられる溶媒としては、反応に悪影響を
及ぼさない限り、この種の反応に通常使用される溶媒を
広く使用でき、例えば水、メタノール、エタノール、プ
ロパノール、イソプロピルアルコール、ブタノール、エ
チレングリコール等のアルコール類、ジメチルエーテ
ル、テトラヒドロフラン、ジオキサン、モノグライム、
ジグライム等のエーテル類、アセトン、メチルエチルケ
トン等のケトン類、ベンゼン、ｏ−ジクロロベンゼン、
トルエン、キシレン等の芳香族炭化水素類、酢酸メチ
ル、酢酸エチル等のエステル類、Ｎ，Ｎ−ジメチルホル
ムアミド、ジメチルスルホキシド、ヘキサメチルリン酸
トリアミド等の非プロトン性極性溶媒等又は之等の混合
溶媒等が挙げられる。As the solvent to be used, any solvent commonly used in this type of reaction can be used unless it adversely affects the reaction. Examples of the solvent include water, methanol, ethanol, propanol, isopropyl alcohol, butanol and ethylene glycol. Alcohols, dimethyl ether, tetrahydrofuran, dioxane, monoglyme,
Ethers such as diglyme, ketones such as acetone and methyl ethyl ketone, benzene, o-dichlorobenzene,
Aromatic hydrocarbons such as toluene and xylene; esters such as methyl acetate and ethyl acetate; aprotic polar solvents such as N, N-dimethylformamide, dimethylsulfoxide and hexamethylphosphoric acid triamide; and mixtures thereof. And the like.
【００１９】塩基性化合物としては、公知のものを広く
使用でき、例えば水酸化ナトリウム、水酸化カリウム、
水酸化セシウム、水酸化リチウム、炭酸ナトリウム、炭
酸カリウム、炭酸セシウム、炭酸リチウム、炭酸水素ナ
トリウム、炭酸水素カリウム、炭酸銀等の無機塩基、水
素化ナトリウム、ナトリウムアミド、カリウム、ナトリ
ウム等のアルカリ金属、ナトリウムメチラート、ナトリ
ウムエチラート、カリウムエチラート等のアルコラー
ト、酢酸ナトリウム等の有機酸金属塩、トリエチルアミ
ン、トリプロピルアミン、ジイソプロピルエチルアミ
ン、ピリジン、キノリン、Ｎ，Ｎ−ジメチルアニリン、
Ｎ−メチルモルホリン、４−ジメチルアミノピリジン、
１，５−ジアザビシクロ〔４．３．０〕ノネン−５（Ｄ
ＢＮ）、１，８−ジアザビシクロ〔５．４．０〕ウンデ
セン−７（ＤＢＵ）、１，４−ジアザビシクロ〔２．
２．２〕オクタン（ＤＡＢＣＯ）等の有機塩基等が挙げ
られる。As the basic compound, known compounds can be widely used, for example, sodium hydroxide, potassium hydroxide,
Inorganic bases such as cesium hydroxide, lithium hydroxide, sodium carbonate, potassium carbonate, cesium carbonate, lithium carbonate, sodium hydrogencarbonate, potassium hydrogencarbonate, silver carbonate; alkali metals such as sodium hydride, sodium amide, potassium, sodium; Alcoholates such as sodium methylate, sodium ethylate and potassium ethylate, organic acid metal salts such as sodium acetate, triethylamine, tripropylamine, diisopropylethylamine, pyridine, quinoline, N, N-dimethylaniline,
N-methylmorpholine, 4-dimethylaminopyridine,
1,5-diazabicyclo [4.3.0] nonene-5 (D
BN), 1,8-diazabicyclo [5.4.0] undecene-7 (DBU), 1,4-diazabicyclo [2.
2.2] Organic bases such as octane (DABCO).
【００２０】式（４）で表される化合物と一般式（１）
で表される化合物との反応においては、反応促進剤とし
て沃化カリウム、沃化ナトリウム等の沃化アルカリ金属
化合物を反応系内に存在させることもできる。The compound represented by the formula (4) and the compound represented by the general formula (1)
In the reaction with the compound represented by the formula, an alkali metal iodide compound such as potassium iodide or sodium iodide may be present in the reaction system as a reaction accelerator.
【００２１】一般式（１）で表される化合物の使用量
は、一般式（４）で表される化合物に対して通常等モル
〜５倍モル量程度、好ましくは等モル〜１．５倍モル量
程度とするのがよい。The amount of the compound represented by the formula (1) is usually about equimolar to 5 times, preferably 1 to 1.5 times the amount of the compound represented by the formula (4). It is preferable to use a molar amount.
【００２２】式（４）で表される化合物と一般式（１）
で表される化合物との反応は、室温下及び加温下のいず
れでも進行するが、通常室温〜２００℃程度、好ましく
は室温〜１５０℃付近にて好適に進行し、一般に１〜１
５時間程度で終了する。The compound represented by the formula (4) and the compound represented by the general formula (1)
The reaction with the compound represented by the formula (I) proceeds at room temperature or under heating, but usually proceeds suitably at room temperature to about 200 ° C, preferably at room temperature to about 150 ° C, and generally from 1 to 1
It ends in about 5 hours.
【００２３】一般式（５）で表される７−（４−ハロゲ
ノブトキシ）−３，４−ジヒドロカルボスチリルと式
（６）で表される化合物との反応は、公知であり、例え
ば特開平２−１９１２５６号公報に記載されている反応
条件を適用すればよい。The reaction between 7- (4-halogenobutoxy) -3,4-dihydrocarbostyril represented by the general formula (5) and the compound represented by the formula (6) is known. What is necessary is just to apply the reaction conditions described in 2-191256.
【００２４】上記各反応式で得られる各々目的化合物
は、通常の単離、精製手段により反応混合物から容易に
単離、精製することができる。このような単離、精製手
段としては、例えば溶媒抽出法、希釈法、再結晶法、カ
ラムクロマトグラフィー、プレパラティブ薄層クロマト
グラフィー等を挙げることができる。Each of the target compounds obtained by each of the above reaction formulas can be easily isolated and purified from the reaction mixture by ordinary isolation and purification means. Examples of such isolation and purification means include a solvent extraction method, a dilution method, a recrystallization method, column chromatography, and preparative thin-layer chromatography.
【００２５】[0025]
【実施例】以下に実施例を掲げて、本発明をより一層明
らかにするが、本発明はこれに限定されるものではな
い。The present invention will be further clarified with reference to the following examples, but the present invention is not limited to these examples.
【００２６】実施例１ ４−クロロブチル ２−ニトロベンゼンスルフォナート
の製造 ４−クロロ−１−ブタノール５ｇを５０ｍｌの塩化メチ
レンに溶解し、氷冷下にトリエチルアミン１１．５ｍｌ
を加えた。これに１１．１ｇの２−ニトロベンゼンスル
ホニルクロライドを反応温度が５℃を超えないように注
意しながら分割して加えた。添加後、約２時間攪拌し、
次に５％塩酸２００ｍｌを加えて、有機層を分取した。
有機層を更に５％塩酸、飽和重曹水、水の順に洗浄した
後、溶媒を留去した。残渣をアセトン／イソプロパノー
ルから再結晶して、標記の目的化合物９．２５ｇを得
た。Example 1 Preparation of 4-chlorobutyl 2-nitrobenzenesulfonate 5 g of 4-chloro-1-butanol was dissolved in 50 ml of methylene chloride, and 11.5 ml of triethylamine was added under ice cooling.
Was added. To this was added 11.1 g of 2-nitrobenzenesulfonyl chloride in portions, taking care that the reaction temperature did not exceed 5 ° C. After addition, stir for about 2 hours,
Next, 200 ml of 5% hydrochloric acid was added, and the organic layer was separated.
The organic layer was further washed with 5% hydrochloric acid, saturated aqueous sodium hydrogen carbonate and water in that order, and then the solvent was distilled off. The residue was recrystallized from acetone / isopropanol to obtain 9.25 g of the title compound.
【００２７】収率：６２．９％ 融点：５１〜５２℃ プロトンＮＭＲ（ＣＤＣｌ3、δｐｐｍ）１．８−２．
０（ｍ，４Ｈ），３．６（ｍ，２Ｈ），４．４（ｍ，２
Ｈ），７．７−７．９（ｍ，３Ｈ），８．１（ｍ，１
Ｈ）。Yield: 62.9% Melting point: 51-52 ° C. Proton NMR (CDCl 3 , δ ppm) 1.8-2.
0 (m, 4H), 3.6 (m, 2H), 4.4 (m, 2
H), 7.7-7.9 (m, 3H), 8.1 (m, 1
H).
【００２８】参考例１ ７−（４−クロロブトキシ）−３，４−ジヒドロ−２
（１Ｈ）−キノリノンの製造 炭酸カリウム９３ｇを精製水８３ｍｌに攪拌溶解し、エ
タノール４１０ｍｌと７−ヒドロキシ−３，４−ジヒド
ロ−２（１Ｈ）−キノリノン５５ｇを加えて約４０℃で
約３０分間攪拌した。次に、４−クロロブチル ２−ニ
トロベンゼンスルフォナート１１０ｇ（１．１倍モル）
を加え、約４０℃で５時間反応させた。反応終了後、減
圧下に溶媒を留去し、得られた残渣に精製水１７００ｍ
ｌを加えて加温し、分散した析出晶を濾取した。得られ
た結晶を少量の精製水で洗浄した後、乾燥し、標記の目
的化合物７５．３ｇを得た。Reference Example 1 7- (4-chlorobutoxy) -3,4-dihydro-2
Production of (1H) -quinolinone 93 g of potassium carbonate was dissolved in 83 ml of purified water with stirring, and 410 ml of ethanol and 55 g of 7-hydroxy-3,4-dihydro-2 (1H) -quinolinone were added, followed by stirring at about 40 ° C. for about 30 minutes. did. Next, 110 g (1.1 times mol) of 4-chlorobutyl 2-nitrobenzenesulfonate
Was added and reacted at about 40 ° C. for 5 hours. After completion of the reaction, the solvent was distilled off under reduced pressure, and 1700 m of purified water was added to the obtained residue.
l, and the mixture was heated, and the dispersed precipitated crystals were collected by filtration. The obtained crystals were washed with a small amount of purified water and then dried to obtain 75.3 g of the title compound.
【００２９】収率：９６．８％ 微黄色結晶 融点：１０７℃ プロトンＮＭＲ（ＣＤＣｌ3、δｐｐｍ）１．８（ｍ，
４Ｈ），２．４（ｍ，２Ｈ），２．７（ｍ，２Ｈ），
３．７（ｔ，２Ｈ），３．９（ｔ，２Ｈ），６．４
（ｄ，１Ｈ），６．５（ｑ，１Ｈ），７．０（ｄ，１
Ｈ），１０．０（ｂｓ，１Ｈ）。Yield: 96.8% slightly yellow crystals Melting point: 107 ° C. Proton NMR (CDCl 3 , δ ppm) 1.8 (m,
4H), 2.4 (m, 2H), 2.7 (m, 2H),
3.7 (t, 2H), 3.9 (t, 2H), 6.4
(D, 1H), 6.5 (q, 1H), 7.0 (d, 1
H), 10.0 (bs, 1H).
───────────────────────────────────────────────────── フロントページの続き (72)発明者 南川 純一 徳島県鳴門市撫養町大桑島字蛭子山88−３ Ｆターム(参考） 4H006 AA01 AB84 ────────────────────────────────────────────────── ─── Continuing on the front page (72) Inventor Junichi Minamikawa 88-3 Hirukoyama, Okuwajima, Fuyo-cho, Naruto-shi, Tokushima F-term (reference) 4H006 AA01 AB84
Claims (1)
ンスルフォナート化合物。1. A compound of the general formula (1) [Wherein, X represents a halogen atom. ] The benzene sulfonate compound represented by these.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN100497325C (en) * | 2004-04-21 | 2009-06-10 | 齐鲁制药有限公司 | Piperazine derivatives and their use in the preparation of quinolone derivatives |
| CN103755632A (en) * | 2001-09-25 | 2014-04-30 | 大塚制药株式会社 | Low hygroscopic aripiprazole drug substance and processes for the preparation thereof |
-
2000
- 2000-12-28 JP JP2000399828A patent/JP2002193915A/en active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103755632A (en) * | 2001-09-25 | 2014-04-30 | 大塚制药株式会社 | Low hygroscopic aripiprazole drug substance and processes for the preparation thereof |
| CN100497325C (en) * | 2004-04-21 | 2009-06-10 | 齐鲁制药有限公司 | Piperazine derivatives and their use in the preparation of quinolone derivatives |
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