JPH0672976A - Optically active substance of new n-@(3754/24)4-ethoxyphenyl-3-hydroxybutanamide - Google Patents
Optically active substance of new n-@(3754/24)4-ethoxyphenyl-3-hydroxybutanamideInfo
- Publication number
- JPH0672976A JPH0672976A JP25410292A JP25410292A JPH0672976A JP H0672976 A JPH0672976 A JP H0672976A JP 25410292 A JP25410292 A JP 25410292A JP 25410292 A JP25410292 A JP 25410292A JP H0672976 A JPH0672976 A JP H0672976A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- chemical formula
- hydroxybutanamide
- ethoxyphenyl
- optically active
- 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.)
- Granted
Links
Abstract
Description
【０００１】[0001]
【産業上の利用分野】前記〔化１〕で表される新規な光
学活性であるＮ−（４−エトキシフエニル）−３−ヒド
ロキシブタナミドのラセミ化合物は中枢神経系用薬とし
て解熱、鎮痛、消炎作用を有し、医薬として現在も利用
されている。一般に医薬用ラセミ化合物は医薬的に有用
な立体配置を有する化合物と医薬的に無用か、薬効があ
つても非常に弱いもの、或は副作用を有する立体配置の
化合物の混合物からなる。本発明は後記の方法にる上記
ラセミ化合物を分割することによつて、製造される副作
用が無いか又はより軽減された従来より薬効の高い新規
な〔化１〕で示される光学活性体に関するものである。BACKGROUND OF THE INVENTION A racemic compound of N- (4-ethoxyphenyl) -3-hydroxybutanamide, which is a novel optically active compound represented by the above [Chemical formula 1], is an antipyretic and analgesic drug for central nervous system. It has an anti-inflammatory effect and is still used as a medicine. In general, a pharmaceutical racemic compound is a mixture of a compound having a pharmaceutically useful configuration and a compound having a pharmaceutically useful configuration, a compound which is very weak even if it has a medicinal effect, or a configuration which has a side effect. The present invention relates to a novel optically active substance represented by [Chemical Formula 1] which has no side effect or is produced by dividing the racemic compound according to the method described below and has a higher medicinal effect than before. Is.
【０００２】[0002]
【従来の技術】従来光学分割の一般的方法として優先晶
析法、ジアステレオマ−法等が使用されているが適用範
囲が狭いのが難点であつた。2. Description of the Related Art Prior art crystallization methods, diastereomer methods and the like have been used as general methods for optical resolution, but their application range is narrow.
【０００３】[0003]
【発明が解決しようとする課題】上記の如く優先晶析法
やジアステレオマ−法等が光学分割の一般的な方法とし
て広く利用されているが、適用範囲が狭いため分割でき
る化合物が限定されていた。従つて優秀な薬効を持つ医
薬品でもラセミ混合物或は化合物の状態で使用せざるを
得ない問題点があつた。そのためやむなく患者は必要以
上の量の投与や副作用を強いられていた。本発明はこう
した問題を解決して〔化１〕で示す新規な光学活性体を
提供することを目的とするものである。As described above, the preferential crystallization method, the diastereomer method and the like are widely used as general methods for optical resolution, but the applicable range is limited because the application range is narrow. . Therefore, there is a problem that even a drug having an excellent medicinal effect must be used in the form of a racemic mixture or a compound. Therefore, the patient was forced to administer an excessive amount of the drug and side effects. An object of the present invention is to solve these problems and provide a novel optically active substance represented by [Chemical Formula 1].
【０００４】[0004]
【課題を解決するための手段】本発明はＮ−（４−エト
キシフエニル）−３−ヒドロキシブタナミドのラセミ体
を下記〔化２〕で表されるセルロ−ストリス置換フエニ
ルカルバメ−ト誘導体又は下記〔化３〕で表されるアミ
ロ−ストリス置換フエニルカルバメ−トを使用して光学
分割することによつて初めて製造された下記〔化１〕で
表される新規な光学活性Ｎ−（４−エトキシフエニル）
−３−ヒドロキシブタナミドに関するものである。DISCLOSURE OF THE INVENTION In the present invention, a racemic N- (4-ethoxyphenyl) -3-hydroxybutanamide is represented by the following [Chemical Formula 2] and a cellulostris-substituted phenylcarbamate derivative or A novel optically active N- (4-ethoxyphenol) represented by the following [Chemical formula 1] which was first produced by optical resolution using the amylo-stris substituted phenyl carbamate represented by the [Chemical formula 3]. Enil)
It relates to -3-hydroxybutanamide.
【０００５】[0005]
【化１】[Chemical 1]
【０００６】[0006]
【化２】ここにＸは低級アルキル基又はＣl を表す。Wherein X represents a lower alkyl group or Cl.
【０００７】[0007]
【化３】ここにＸは低級アルキル基又はＣl を表す。Wherein X represents a lower alkyl group or Cl.
【０００８】更に詳細には本発明は、上記〔化２〕もし
くは〔化３〕で示された化合物を多孔質球状のシリカゲ
ルに担持せしめ、これをカラムに充填して高速液体クロ
マトグラフイ−用キラルな固定相として使用した。More specifically, in the present invention, the compound represented by the above [Chemical formula 2] or [Chemical formula 3] is supported on porous spherical silica gel, which is packed in a column for high performance liquid chromatography. Used as a chiral stationary phase.
【０００９】上記のようにして調製されたキラルな固定
相を高速液体クロマトグラフイ−用カラムとし、種々な
極性の異なる溶媒を使用し、極性を調製した溶媒系を使
用するとラセミ体のＮ−（４−エトキシフエニル）−３
−ヒドロキシブタナミドが、光学活性な異性体に分割さ
れて製造することができた。When the chiral stationary phase prepared as described above is used as a column for high performance liquid chromatography, various polar solvents are used, and a solvent system having polar properties is used, racemic N- (4-ethoxyphenyl) -3
-Hydroxybutanamide could be prepared by resolution into its optically active isomers.
【００１０】本発明に使用される〔化２〕の一般式で示
すセルロ−ストリス置換フエニルカルバメ−ト誘導体又
はアミロ−ストリス置換フエニルカルバメ−トは、置換
フエニルイソシアネ−トをセルロ−ス又はアミロ−スと
反応させることによつて合成される。本発明に使用され
るセルロ−ストリス置換フエニルカルバメ−ト誘導体と
しては、セルロ−ストリス（３，５−ジメチルフエニル
カルバメ−ト）、セルロ−ストリス（フエニルカルバメ
−ト）、セルロ−ストリス（４−クロロフエニルカルバ
メ−ト）があり、又〔化３〕で表されるアミロ−ストリ
ス置換フエニルカルバメ−トとしては、アミロ−ストリ
ス（３，５−ジメチルフエニルカルバメ−ト）がある。The cellulostris-substituted phenylcarbamate derivative represented by the general formula of [Chemical Formula 2] or the amylo-stris-substituted phenylcarbamate used in the present invention is a substituted phenylisocyanate which is a cellulose or an amylose. It is synthesized by reacting with sucrose. The cellulostris-substituted phenylcarbamate derivative used in the present invention includes cellulostris (3,5-dimethylphenylcarbamate), cellulostris (phenylcarbamate), and cellulostris (4-chlorophenyl). And the amylostris-substituted phenylcarbamate represented by [Chemical Formula 3] is amylostris (3,5-dimethylphenylcarbamate).
【００１１】本発明においては、上記のようにして前記
〔化２〕で表されるセルロ−ストリス置換フエニルカル
バメ−ト誘導体又は、〔化３〕で表されるアミロ−スト
リス置換フエニルカルバメ−トを使用して〔化１〕で表
されるＮ−（４−エトキシフエニル）−３−ヒドロキシ
ブタナミドの光学活性異性体を光学分割する方法は何等
制約されることなく、如何なる方法を使用してもよい。In the present invention, the cellulostris-substituted phenylcarbamate derivative represented by the above [Chemical formula 2] or the amylo-Stris substituted phenylcarbamate represented by the [Chemical formula 3] is used as described above. The method for optically resolving the optically active isomer of N- (4-ethoxyphenyl) -3-hydroxybutanamide represented by [Chemical Formula 1] is not particularly limited, and any method may be used. .
【００１２】[0012]
【実施例】以下にラセミ体のＮ−（４−エトキシフエニ
ル）−３−ヒドロキシブタナミドを前記〔化２〕又は
〔化３〕を使用する光学分割によつて製造された新規な
光学活性Ｎ−（４−エトキシフエニル）−３−ヒドロキ
シブタナミドの製造方法を実施例によつて説明する。EXAMPLE A novel optical activity of racemic N- (4-ethoxyphenyl) -3-hydroxybutanamide prepared by optical resolution using the above [Chemical Formula 2] or [Chemical Formula 3] is shown below. The method for producing N- (4-ethoxyphenyl) -3-hydroxybutanamide will be described with reference to Examples.
【００１３】〔実施例１〕 アミロ−ストリス（３，５
−ジメチルフエニルカルバメ−ト）を３−アミノプロピ
ルトリメトキシシランで処理した大孔径シリカゲル（粒
子径10μm 、孔径0.4 μm ）に25wt％に担持せしめ、ス
ラリ−充填法により長さ25cm、内径0.46cmのクロマト管
に充填しキラルカラムを作製した。ヘキサン−２−プロ
パノ−ル−ジエチルアミン（80：20：0.1 ）を溶離液と
してＮ−（４−エトキシフエニル）−３−ヒドロキシブ
タナミド（ラセミ体）0.05mgを25℃、流速0.5ml/min で
上記カラムを通した。クロマトグラフ用機器としては、
ポンプ（島津ＬＣ−６ＡＤ）、ＵＶ検出器（島津ＳＰＤ
−６Ａ）、旋光計（昭和電工ＯＲ−１）を使用した。得
られたクロマトグラムを〔図１〕に示す。〔図１〕から
明らかなように、（−）体が先に溶出し、次いで（＋）
体が溶出し、各々の光学活性体に完全に分割された。Example 1 Amylo-Stris (3, 5)
-Dimethylphenylcarbamate) was loaded on 25 wt% of large-pore silica gel (particle diameter 10 μm, pore diameter 0.4 μm) treated with 3-aminopropyltrimethoxysilane, and the length was 25 cm and the inner diameter was 0.46 by the slurry filling method. A chromatographic tube of cm was packed to prepare a chiral column. Hexane-2-propanol-diethylamine (80: 20: 0.1) was used as an eluent, and 0.05 mg of N- (4-ethoxyphenyl) -3-hydroxybutanamide (racemic body) was added at 25 ° C and a flow rate of 0.5 ml / min. Through the above column. As a chromatograph device,
Pump (Shimadzu LC-6AD), UV detector (Shimadzu SPD
-6A) and a polarimeter (Showa Denko OR-1) were used. The obtained chromatogram is shown in FIG. As is clear from [Fig. 1], the (-) form was eluted first, followed by the (+) form.
The body eluted and was completely resolved into each optically active form.
【００１４】[0014]
【図１】[Figure 1]
【００１５】〔実施例２〕 〔実施例１〕と同一のキラ
ル充填剤を長さ25cm、内径２cmのクロマト管に充填した
キラルカラムを用いて、ヘキサン−２−プロパノ−ル−
ジエチルアミン（80：20：0.1 ）を溶離液としてＮ−
（４−エトキシフエニル）−３−ヒドロキシブタナミド
（ラセミ体）40mgを25℃、流速10ml/minで上記カラムを
通した。得られたクロマトグラムを〔図２〕に示す。こ
の操作を10回繰返し行い、溶液を減圧下留去し、光学純
度100.0 ％e.e.の（−）体132mg と光学純度99.5％e.e.
の（＋）体144mg を単離した。セルロ−ストリス置換フ
エニルカルバメ−ト誘導体によつても同様な方法によつ
て同様に本発明のラセミ体を分割することができる。各
々の性状は以下の通りである。 １Ｒ（ＫＢｒ）３１００cm-1、１６５０cm-1、１５１０
ｃｍ-1 Example 2 Using a chiral column in which the same chiral packing as in [Example 1] was packed in a chromatographic tube having a length of 25 cm and an inner diameter of 2 cm, hexane-2-propanol- was used.
N- with diethylamine (80: 20: 0.1) as the eluent
40 mg of (4-ethoxyphenyl) -3-hydroxybutanamide (racemate) was passed through the above column at 25 ° C and a flow rate of 10 ml / min. The obtained chromatogram is shown in FIG. This operation was repeated 10 times, the solution was distilled off under reduced pressure, and 132 mg of (-) form with an optical purity of 100.0% ee and an optical purity of 99.5% ee were obtained.
144 mg of the (+) form of were isolated. The racemate of the present invention can be similarly resolved by the same method with the cellulostris-substituted phenylcarbamate derivative. The properties of each are as follows. 1R (KBr) 3100 cm -1 , 1650 cm -1 , 1510
cm -1
【００１６】[0016]
【図２】[Fig. 2]
【００１７】化学純度 ラセミ体 ９９．９％ （−）体 ９９．５％ （＋）体 ９９．９％ 融 点 ラセミ体 １５８．１〜１５９．４℃ （−）体 １３８．８〜１３９．９℃ （＋）体 １３８．７〜１３９．８℃ Ｍａｓｓ（Ｍ+ ） 計算値 ２２３．１２０９ （−）体 実測値 ２２３．１２１０ （＋）体 実測値 ２２３．１２０２ 元素分析 Ｈ（％） Ｃ（％） Ｎ（％） 計算値 ７．６７ ６４．５５ ６．２７ （−）体 実測値 ７．６８ ６４．３０ ６．３９ （＋）体 実測値 ７．６１ ６４．３９ ６．２５Chemical purity Racemic body 99.9% (-) body 99.5% (+) body 99.9% Melting point racemate 158.1 to 159.4 ° C (-) body 138.8 to 139.9 ℃ (+) body 138.7-139.8 ℃ Mass (M + ) Calculated value 223.1209 (-) body Measured value 223.1210 (+) body measured value 223.1202 Elemental analysis H (%) C (%) ) N (%) Calculated value 7.67 64.55 6.27 (-) body Actual value 7.68 64.30 6.39 (+) body Actual value 7.61 64.39 6.25
【００１８】1H−ＮＭＲ δ（６０ＭＨz ，ＤＭＳ
Ｏ） １．１３（３Ｈ，ｄ，−ＣＨＣＨ3)、 １．３０（３Ｈ，
ｔ，−ＯＣＨ2 ＣＨ3)、２．３５（２Ｈ，ｄ，−ＣＨＣ
Ｈ3)、 ３．９７（２Ｈ，ｑ，−ＯＣＨ2 ＣＨ3)、３．９
−４．４（１Ｈ，ｍ，−ＣＨＣＨ3 ）、４．６８（１
Ｈ，ｄ，ＯＨ）、６．８１（２Ｈ，ｄ，ＡｒＨ）、７．
４８（２Ｈ，ｄ，ＡｒＨ）、９．６３（１Ｈ，ｓ，Ｎ
Ｈ） 比旋光度（ｃ＝１．０，エタノ−ル） （−）体 〔α〕25 D ＝−１９．３° （＋）体 〔α〕25 D ＝＋１９．８°[0018] 1 H-NMR δ (60MH z , DMS
O) 1.13 (3H, d, -CHCH 3), 1.30 (3H,
t, -OCH 2 CH 3), 2.35 (2H, d, -CHC
H 3), 3.97 (2H, q, -OCH 2 CH 3), 3.9
-4.4 (1H, m, -CHCH 3 ), 4.68 (1
H, d, OH), 6.81 (2H, d, ArH), 7.
48 (2H, d, ArH), 9.63 (1H, s, N
H) Specific optical rotation (c = 1.0, ethanol) (-) body [α] 25 D = -19.3 ° (+) body [α] 25 D = + 19.8 °
【００１９】[0019]
【発明の効果】今までに知られた優秀な薬効を持つ医薬
品でも光学分割の方法がなくラセミ混合物或は化合物の
状態で使用せざるを得なかつた。そのためやむなく患者
は必要以上に量の投与や副作用を強いられていた。本発
明はこうした問題解決に成功したものである。EFFECTS OF THE INVENTION Even a drug having an excellent medicinal effect which has been known so far has no method of optical resolution, and it is inevitable to use it in the form of a racemic mixture or a compound. Therefore, patients were forced to administer more doses and side effects than necessary. The present invention has succeeded in solving these problems.
【図１】実施例１によつて得られた光学活性体のクロマ
トグラムを示す。FIG. 1 shows a chromatogram of an optically active substance obtained according to Example 1.
【図２】実施例２によつて得られた光学活性体のクロマ
トグラムと施光計による施光度を示す。FIG. 2 shows a chromatogram of an optically active substance obtained according to Example 2 and a degree of illuminance measured by a photometer.
─────────────────────────────────────────────────────
─────────────────────────────────────────────────── ───
【手続補正書】[Procedure amendment]
【提出日】平成４年１１月１２日[Submission date] November 12, 1992
【手続補正１】[Procedure Amendment 1]
【補正対象書類名】明細書[Document name to be amended] Statement
【補正対象項目名】図面の簡単な説明[Name of item to be corrected] Brief description of the drawing
【補正方法】変更[Correction method] Change
【補正内容】[Correction content]
【図面の簡単な説明】[Brief description of drawings]
【図１】実施例１によつて得られた光学活性体のクロマ
トグラムと旋光計による比旋性の正負を示す。1 shows the chromatogram of the optically active substance obtained according to Example 1 and the positive and negative signs of the specific rotation measured by a polarimeter.
【図２】実施例２によつて得られた光学活性体のクロマ
トグラムを示す。FIG. 2 shows a chromatogram of the optically active substance obtained according to Example 2.
【手続補正２】[Procedure Amendment 2]
【補正対象書類名】図面[Document name to be corrected] Drawing
【補正対象項目名】全図[Correction target item name] All drawings
【補正方法】変更[Correction method] Change
【補正内容】[Correction content]
【図１】 [Figure 1]
【図２】 ─────────────────────────────────────────────────────
[Fig. 2] ─────────────────────────────────────────────────── ───
【手続補正書】[Procedure amendment]
【提出日】平成５年４月９日[Submission date] April 9, 1993
【手続補正１】[Procedure Amendment 1]
【補正対象書類名】明細書[Document name to be amended] Statement
【補正対象項目名】図面の簡単な説明[Name of item to be corrected] Brief description of the drawing
【補正方法】変更[Correction method] Change
【補正内容】[Correction content]
【図面の簡単な説明】[Brief description of drawings]
【図１】実施例１によつて得られた光学活性体のクロマ
トグラムと旋光計による比旋性性の正負を示す。FIG. 1 shows a chromatogram of the optically active substance obtained according to Example 1 and the positive and negative polarities measured by a polarimeter .
【図２】実施例２によつて得られた光学活性体のクロマ
トグラムを示す。FIG. 2 shows a chromatogram of the optically active substance obtained according to Example 2.
【手続補正２】[Procedure Amendment 2]
【補正対象書類名】図面[Document name to be corrected] Drawing
【補正対象項目名】図１[Name of item to be corrected] Figure 1
【補正方法】変更[Correction method] Change
【補正内容】[Correction content]
【図１】 [Figure 1]
【手続補正３】[Procedure 3]
【補正対象書類名】図面[Document name to be corrected] Drawing
【補正対象項目名】図２[Name of item to be corrected] Figure 2
【補正方法】変更[Correction method] Change
【補正内容】[Correction content]
【図２】 [Fig. 2]
Claims (3)
トキシフエニル）−３−ヒドロキシブタナミドの光学活
性体。 【化１】 1. A novel optically active form of N- (4-ethoxyphenyl) -3-hydroxybutanamide represented by [Chemical formula 1]. [Chemical 1]
シフエニル）−３−ヒドロキシブタナミドのそれぞれの
光学活性異性体の当量混合物（ラセミ体）を一般式〔化
２〕で表されるセルロ−ストリス置換フエニルカルバメ
−ト誘導体又は一般式〔化３〕で表される構造を有する
アミロ−ストリス置換フエニルカルバメ−トを使用して
光学分割することによつて得られる新規な〔化１〕で表
されるＮ−（４−エトキシフエニル）−３−ヒドロキシ
ブタナミドの光学活性体。 【化１】ここにセルロ−ストリス置換フエニルカルバメ
−ト誘導体を〔化２〕に示す。 【化２】 〔化２〕においてＸは低級アルキル基又はＣl を表す。
またアミロ−ストリス置換フエニルカルバメ−トを〔化
３〕に示す。 【化３】 〔化３〕においてＸは低級アルキル基又はＣl を表す。2. An equivalent mixture (racemic form) of each optically active isomer of the novel N- (4-ethoxyphenyl) -3-hydroxybutanamide according to claim 1 is represented by the general formula [Chemical Formula 2]. A novel [Chemical formula 1] obtained by optical resolution using a cellulostris-substituted phenylcarbamate derivative or an amylo-Stris substituted phenylcarbamate having a structure represented by the general formula [Chemical formula 3] An optically active form of N- (4-ethoxyphenyl) -3-hydroxybutanamide represented by: [Chemical Formula 1] Here, a cellulostris-substituted phenylcarbamate derivative is shown in [Chemical Formula 2]. [Chemical 2] In Formula 2, X represents a lower alkyl group or Cl.
An amylo-Stris substituted phenyl carbamate is shown in [Chemical Formula 3]. [Chemical 3] In Formula 3, X represents a lower alkyl group or Cl.
ニル）−３−ヒドロキシブタナミドの光学分割に使用さ
れる〔化２〕で表されるセルロ−ストリス置換フエニル
カルバメ−トが、セルロ−ストリス（３，５−ジメチル
フエニルカルバメ−ト）、セルロ−ストリス（フエニル
カルバメ−ト）、セルロ−ストリス（４−クロロフエニ
ルカルバメ−ト）の何れかであり、又〔化３〕で表され
るアミロ−ストリス置換フエニルカルバメ−トが、アミ
ロ−ストリス（３，５−ジメチルフエニルカルバメ−
ト）である請求項２記載の〔化１〕で示される光学活性
を有する新規なＮ−（４−エトキシフエニル）−３−ヒ
ドロキシブタナミド。 【化１】 【化２】 【化３】3. The cellulostris-substituted phenylcarbamate represented by [Chemical Formula 2] used for optical resolution of N- (4-ethoxyphenyl) -3-hydroxybutanamide according to claim 2, -Stris (3,5-dimethylphenylcarbamate), cellulostris (phenylcarbamate), cellulostris (4-chlorophenylcarbamate), or The amylo-stris substituted phenyl carbamates represented are amylo-stris (3,5-dimethyl phenyl carbamates).
And a novel N- (4-ethoxyphenyl) -3-hydroxybutanamide having optical activity represented by [Chemical formula 1] according to claim 2. [Chemical formula 1] [Chemical formula 2] [Chemical formula 3]
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP25410292A JP3316234B2 (en) | 1992-08-28 | 1992-08-28 | New optically active N- (4-ethoxyphenyl) -3-hydroxybutanamide |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP25410292A JP3316234B2 (en) | 1992-08-28 | 1992-08-28 | New optically active N- (4-ethoxyphenyl) -3-hydroxybutanamide |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH0672976A true JPH0672976A (en) | 1994-03-15 |
| JP3316234B2 JP3316234B2 (en) | 2002-08-19 |
Family
ID=17260253
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP25410292A Expired - Fee Related JP3316234B2 (en) | 1992-08-28 | 1992-08-28 | New optically active N- (4-ethoxyphenyl) -3-hydroxybutanamide |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP3316234B2 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1997049733A1 (en) * | 1996-06-27 | 1997-12-31 | Novartis Ag | Thermally immobilized polysaccharide derivatives |
-
1992
- 1992-08-28 JP JP25410292A patent/JP3316234B2/en not_active Expired - Fee Related
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1997049733A1 (en) * | 1996-06-27 | 1997-12-31 | Novartis Ag | Thermally immobilized polysaccharide derivatives |
Also Published As
| Publication number | Publication date |
|---|---|
| JP3316234B2 (en) | 2002-08-19 |
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