JPS62108870A - Optically active 5-sulfonyloxymethyl-2-oxazolidinone derivative and production thereof - Google Patents
Optically active 5-sulfonyloxymethyl-2-oxazolidinone derivative and production thereofInfo
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- JPS62108870A JPS62108870A JP60248664A JP24866485A JPS62108870A JP S62108870 A JPS62108870 A JP S62108870A JP 60248664 A JP60248664 A JP 60248664A JP 24866485 A JP24866485 A JP 24866485A JP S62108870 A JPS62108870 A JP S62108870A
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- formula
- optically active
- oxazolidinone
- yield
- aromatic hydrocarbon
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- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
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Abstract
Description
【発明の詳細な説明】
3、発明の1斗、川な説明
〔産業上の利用分野〕
本発明は、一般式 よ
(式中、几は芳苗族炭化水素基)
で表わされる光学活性な5−スlレホニルオキシメチル
ー2−オキサゾリジノン秀導体及びそれらの製造方法に
関する。一般式 尤で表すされる化合物は文献未記載の
新規化合物であり、医薬品の原料として重要な中間体で
ある。例えば、(8)体の場合、皿々(8)−β−ブロ
ッカ−への利用が期待できる化合物である。[Detailed description of the invention] 3. First and foremost explanation of the invention [Industrial application field] The present invention provides an optically active 5 compound represented by the general formula (wherein, 几 is an aromatic hydrocarbon group). -Threphonyloxymethyl-2-oxazolidinone excellent conductors and methods for producing them. The compound represented by the general formula Y is a new compound that has not been described in any literature, and is an important intermediate as a raw material for pharmaceuticals. For example, the (8) form is a compound that can be expected to be used as a (8)-β-blocker.
本発明者らは、既に、(1)3位N14換へにアル該エ
ステルラセミ体からリパーゼの不斉氷解により得られる
こと(下記の合成経路人参照)、(旬−アルコール
(S)−アルコール
又、(2)得られた(S)−アルコールを用いて(S)
−β−ブロッカ−へ誘導できることを報告している(下
記の合戎屈賂]35!:(1)。The present inventors have already discovered that (1) the 3-alcohol (S)-alcohol can be obtained from the 3-position N14 substitution from the ester racemate by asymmetric deicing using lipase (see synthetic route description below); Also, (2) using the obtained (S)-alcohol, (S)
It has been reported that it can induce -β-blocker (see below) 35!: (1).
文厭
(1) 111口ら、アグリカルチュラル・バイオロ
ジカル・ケミストリー(Agric、 uiol、 C
hem、 ) 。Bunkei (1) 111 Kuchi et al., Agricultural Biological Chemistry (Agri, uiol, C
hem, ).
2331(1984)、 (2)t:rら、11店、
19゜207(1985)。2331 (1984), (2) t:r et al., 11 stores,
19°207 (1985).
しかし、最近になって、桑畑作用を拡大、或いは副作用
を低減する目的で、Nia換基模試ルキル基以外の置換
基が導入された光学活性なβ−ブロッカ−或いはα、β
−ブロッカ−の開発が進められるようになってきた。こ
れ1こ対処する為、N置換基が容易に置換可能な汎用性
の高い光学活性な中間体の開発が望まれるようになった
。However, recently, optically active β-blockers, α,
The development of -blockers- has begun to progress. In order to address this problem, it has become desirable to develop a highly versatile optically active intermediate that can be easily substituted with an N substituent.
本発明者らは、上記目的に適う中間体として3位N置換
基が水素基である光学活性5−ヒドロキシメチル−2−
オキサゾリジノン(2)該エステルラセミ体 (4)
記する反応式C1こ示すルートを経て、光学活性之が得
られることを見い出している〔演目ら、アグリカルチュ
ラル・バイオロジカル・ケミストリー(Agric、
Biol、 Chem、 ) 、 49. 1509
(1985))。The present inventors have developed an optically active 5-hydroxymethyl-2-in which the 3-position N substituent is a hydrogen group as an intermediate suitable for the above purpose.
Oxazolidinone (2) The ester racemate (4) It has been found that optical activity can be obtained through the route shown in the reaction formula C1 [Ken et al., Agricultural Biological Chemistry (Agric,
Biol, Chem, ), 49. 1509
(1985)).
しかし、化合物見は吸湿性であり、純度の高い芝は低収
率でしか得られなかった。なお、単離収率及び光学純度
は以下の通りであった。However, the compound was hygroscopic, and highly pure grass could only be obtained at a low yield. The isolation yield and optical purity were as follows.
(s)−、;l : (R,S ) −4からの収率2
1%。(s)-,;l: Yield 2 from (R,S)-4
1%.
光学純度 100%e、 e。Optical purity 100% e, e.
(→−之:(R,5)−4からの収率30%。(→-yield: 30% from (R,5)-4.
光学純度 97%ee。Optical purity: 97%ee.
(1°8)−4〜7.5に調節
〜 2)無機酸によりPH7に戻す
塩の7濾過、除去
5)−液濃縮
一ン
(8)−2(8)−走
〔問題点をr+′I決するための手段及び作用効果〕本
発明者らは、+i’d記欠点全欠点し、単離収率の向上
を図る目的で更に検討を行った。(1°8) Adjust to -4 to 7.5 ~ 2) Return to pH 7 with inorganic acid 7 filtration and removal of salt 5) - Concentrate the solution (8) - 2 (8) - Run [Resolve the problem [Means for Determination and Functions and Effects] The present inventors conducted further studies for the purpose of eliminating all the drawbacks mentioned above and improving the isolation yield.
先づ、(”+6)−エステル 4をリパーゼにより不斉
水解した後、有機溶媒で抽出すると(13) −4が1
0らGる。この(s)−4を更にアルカリ加水分解し、
生成する(8)−アルコール 之を単離することなく、
この(8) −、lの他に・1′a酸塩、無機酸塩それ
に少量の水分を含む純a″60〜85%の徂aiii6
物を用いて直接スルホン譚エステル化することにより、
結晶性が良く、簡tiJα度の光学活性(8)−1’r
−収率よく調製する方法を見いだした(反応式C参照)
。First, (''+6)-ester 4 is asymmetrically hydrolyzed with lipase and then extracted with an organic solvent to convert (13)-4 to 1.
0raGru. This (s)-4 is further alkali hydrolyzed,
without isolating the (8)-alcohol produced.
In addition to this (8) -, l, 1'a acid salt, inorganic acid salt, and a small amount of water are included in pure a''60 to 85% Soaiii6
By direct sulfonate esterification using
Good crystallinity, optical activity of simple tiJα degree (8)-1'r
- Found a method for preparing it with good yield (see reaction formula C)
.
尚、(8)−走は前述の目的に適う新規化合()である
。Note that (8)-run is a new compound () that meets the above-mentioned purpose.
又、リパーゼ不斉氷解の除土ずる水層側の(R) −9
も水をそのまま濃縮し、同じような操作法により単離せ
ずに(R)−1が高収率で優られた。In addition, (R) -9 on the water layer side through the removal of soil by lipase asymmetric ice thawing
(R)-1 was obtained in high yield without isolation by concentrating the water directly and using a similar procedure.
以下、本発明を具体的に22゛a明する。The present invention will be explained in detail below.
本発明の原料として用いられる有機酸塩、無し1塩及び
少輩の水分を含む(8)−アルコール 2又は(R)
−之のaW3物は、次のような操作をへて得られる。Organic acid salt used as a raw material of the present invention, no salt and (8)-alcohol 2 or (R) containing a small amount of water
- The aW3 product can be obtained through the following operations.
Agric、Biol、 Chem、49.1509(
1985)に示す如く、塙11T
3〜7のアルキル基)にシュードモナス・アエルギノサ
(pseudomonas aeruginosa )
起dfi (II)リパーゼを作用させて、不ぐ水1す
乍を行う。次いで、(8)−エステル 速と(n)−ア
ルコール媒、例えば塩化メチレン又は酢酸エチルを用い
て抽出分層し、水11側の(I′t)−アルコール 之
はそのまま。J稲乾固する。一方、汀機ノ14側の(8
)−エステル 4はaHae、N aOH’9(D y
ルカ’) HテP H10′−12に保持しながら加
水分1!p% L/て(S)−アルコール 之とし、J
rs<UlmでPIEを7に戻してからi1J縮乾固す
る。更に夫々のアルコール えはメタノール又はアセト
ンでで)るだけ塩を濾過により:示いた後、−液を再び
l々縮乾固したのち、次のスルホン酸エステル化反応に
供する。純度60〜85%程度の(8) −2又は(R
) −2を含む徂扮末が得られる。但し、l縮の際、エ
ステル化工程での収率を上げる観点から、できるだけ水
を除き、乾燥しておくことが望ましい。Agric, Biol, Chem, 49.1509 (
(1985), Pseudomonas aeruginosa (alkyl groups of Hanawa 11T 3 to 7)
(II) Apply lipase to remove water. Next, the (8)-ester and (n)-alcohol medium, such as methylene chloride or ethyl acetate, are used to extract and separate the layers, leaving the (I't)-alcohol on the water side as it is. J. Dry and harden the rice. On the other hand, (8
)-ester 4 is aHae, NaOH'9(D y
Luca') HteP Hydroidize 1 while maintaining H10'-12! p% L/te(S)-alcohol, J
When rs<Ulm, return the PIE to 7 and then reduce to dryness with i1J. After removing the salt by filtration with each alcohol (methanol or acetone), the solution was condensed to dryness again and then subjected to the next sulfonic acid esterification reaction. (8)-2 or (R
) −2 is obtained. However, at the time of condensation, it is desirable to remove water as much as possible and dry it from the viewpoint of increasing the yield in the esterification step.
次に試剤として用いるスルホニルクロライド物(几5O
301) としては、例えばり−トルエンスルホニル
クロライド、ベンゼンスルホニルクロライドの如き芳香
族炭化水素基からなるスルホニルクロライド物が使用で
きる。またRが低級アルキル基からなる、例えばメタン
スルホンaりロライドも使用できるが、生成物尤の純度
を高め、かつ収率向上を図る観点からは+]ff述の結
晶性に侵れている芳a族炭化水素表スルホニルクロライ
ド物の方が・Jましい。塩2:ン性配合物としては、ト
リエチルアミン、ピリジン等の3級アミンが使用できる
。Next, a sulfonyl chloride (几5O) is used as a reagent.
As 301), sulfonyl chlorides comprising an aromatic hydrocarbon group such as -toluenesulfonyl chloride and benzenesulfonyl chloride can be used. In addition, methanesulfonyl chloride in which R is a lower alkyl group, for example, can be used, but from the viewpoint of increasing the purity of the product and improving the yield, aroma Sulfonyl chlorides of group a hydrocarbons are more preferable. Salt 2: Tertiary amines such as triethylamine and pyridine can be used as salt formulations.
不活性有機俗媒としては、塩化メチレン、アセトン、酢
酸エチル等の一般fa溶媒が使用できる。As the inert organic solvent, common fa solvents such as methylene chloride, acetone, and ethyl acetate can be used.
反応は、室温から有機溶媒の還流温度の範囲で行い、2
〜10時間で反応は完結する。反応後、等数の水で水洗
を2M行い、有機層をNa2804で脱水処理段、濃縮
し、酢酸エチル−ヘキサン=1〜1.5:1の糸で晶析
を行うことにより目的物スルホン酸エステルよを瘍純度
、かつ扁収率で得ることができる。The reaction is carried out in the range from room temperature to the reflux temperature of the organic solvent.
The reaction is complete in ~10 hours. After the reaction, the organic layer was washed with an equal number of 2M water, the organic layer was dehydrated with Na2804, concentrated, and crystallized using a thread of ethyl acetate-hexane = 1 to 1.5:1 to obtain the target sulfonic acid. Ester can be obtained with high purity and high yield.
以下、実施例により本発明を具体的に説明するが、本発
明はこれらの実施例に限定されるものではない。EXAMPLES Hereinafter, the present invention will be specifically explained with reference to Examples, but the present invention is not limited to these Examples.
#4例1
0.1Mリンを淑な何故(Phi 7.0 ) 2.1
5 (Jにシュートモ?−スーアエルギノサ(pseu
domonasaeruginosa ) 18源のリ
パーゼ21.5fを懸濁し、0れに(R,S ) −5
−ヘキサノイロキシメチル−2−オキサゾリジノン
加え、40″G、 6時間反応を行い、PHは5NN
a (、)r■ で7.0に保持する。反応後、冷却
してから、塩化メチレン2.15gで2回抽出分に用を
行う。#4 Example 1 Why 0.1M phosphorus is good (Phi 7.0) 2.1
5 (J to shoot mo? - Suaeruginosa (pseu
domonasaeruginosa) 18 sources of lipase 21.5f was suspended at 0 and (R,S)-5
-Hexanoyloxymethyl-2-oxazolidinone was added and the reaction was carried out at 40″G for 6 hours, and the pH was 5NN.
a (,)r■ is held at 7.0. After the reaction, the mixture was cooled and extracted twice with 2.15 g of methylene chloride.
(8)−エステルは174 化メチレンj1ツに、一方
(It) −5−ヒドロキシメチル−2−オキサゾリジ
ノン定1歳的に1ζ事られる。The (8)-ester is reacted with methylene 174, while (It)-5-hydroxymethyl-2-oxazolidinone is reacted with 1ζ.
次いで、塩化メチレンツζ9を1減圧編1婿後、1.1
倍モル1.にの5 N Na0flケ添1jilじ、
40 ’c、 4 il、’j問アルカリ氷解を行う。Next, methylene chloride ζ9 was reduced to 1.1
double mole 1. 5 N Na0 fl kesoe 1 jilji,
40'c, 4il,'j Perform alkaline ice thawing.
氷解後、5N@酸でPHを7に戻してから減圧譲肩占す
る。濃縮液をメタノール500 mlで溶解し、カプロ
ンr波ソーダ、硫酸ソーダ等の不溶物をI濾過により除
去する。P液を再び減圧濃縮することにより、次の反応
に供する(8)−、tを含む白色粉末75.7fが得ら
れた。純度は68%、収率44%であった。After thawing the ice, return the pH to 7 with 5N acid and then reduce the pressure. The concentrated solution is dissolved in 500 ml of methanol, and insoluble substances such as Kapron R-wave soda and sodium sulfate are removed by I filtration. By concentrating the P solution again under reduced pressure, 75.7f of white powder containing (8)- and t to be used in the next reaction was obtained. The purity was 68% and the yield was 44%.
一方、(R)−之を含む水浴液を減圧濃縮して上記と同
様の操作を行い、(R) −、Jを含む白い粉末77、
4 &を得た。純度は65%、収率43%であった。On the other hand, the water bath solution containing (R)- was concentrated under reduced pressure and the same operation as above was performed to obtain a white powder 77 containing (R)-,J.
4 I got &. The purity was 65% and the yield was 43%.
参考例2
メタノールで不溶物を一過する代りに、アセトン500
g’を用いた以外は参考例1に準じて調製した。Reference example 2 Instead of passing the insoluble matter with methanol, acetone 500
It was prepared according to Reference Example 1 except that g' was used.
(8) −1を含む白い粉末51.21得た。純度80
%、収率35%であった。また(川−之を含む白い粉末
47.1 f l得た。純度82%、収率33%であっ
た。(8) 51.21 of a white powder containing -1 was obtained. Purity 80
%, yield was 35%. In addition, 47.1 fl of a white powder containing sulfuric acid was obtained. The purity was 82% and the yield was 33%.
実施例1
粗(S)−ヒドロキシメチル−2−オキサゾリジノン
(幻14.6y(純度80%)、トリエチルアミン11
y1塩化メチレン100+/にトシルクロライド2(
lを添加し、室温下で6時間反応を行った。Example 1 Crude (S)-hydroxymethyl-2-oxazolidinone
(Phantom 14.6y (purity 80%), triethylamine 11
y1 methylene chloride 100+/tosyl chloride 2 (
1 was added thereto, and the reaction was carried out at room temperature for 6 hours.
HPLC分析は、カラムFtncpak 81101B
(0,46X25CIII)、展開溶媒 水−アセトニ
トリル=3:2、流g 2.1 at / his、構
出UV215Hmの条件で行い、反応経時変化を追跡し
た。保持時間は4.2分であった。HPLC analysis was performed using column Ftncpak 81101B.
(0,46X25CIII), developing solvent water-acetonitrile = 3:2, flow rate g 2.1 at/his, and UV 215Hm, and the reaction change over time was monitored. The retention time was 4.2 minutes.
反応後、等量の水120g+/で2回水洗し、塩化メチ
レン層を硫酸ソーダで脱水処理してから濃縮した。この
a縮物を酢酸エチル501どでMかし、ヘキサンを加え
ていくと目面物(s)−5−p−)シルオキシメチル−
2−オキサゾリジノン20.39、収率75%で得た。After the reaction, the mixture was washed twice with an equal amount of 120 g of water, and the methylene chloride layer was dehydrated with sodium sulfate and then concentrated. This a-condensate was dissolved in 501 ethyl acetate, etc., and by adding hexane, the product (s)-5-p-)yloxymethyl-
20.39% of 2-oxazolidinone was obtained in a yield of 75%.
物性値は以下の曲りであった。The physical property values were as follows.
形 状:無色、扮末
融 点:117〜117.5°C
比旋光度:〔α〕譬+40.8°(C=1.0、メタノ
ール
IHNMIL (90Ml1z、 CD01B )
δ(ppm):2.45 (3L(、s、 0f1B
−Ar )、 8.30〜3.78 (2H,m。Shape: Colorless, melting point: 117-117.5°C Specific optical rotation: [α]+40.8° (C=1.0, methanol IHNMIL (90Ml1z, CD01B)
δ (ppm): 2.45 (3L(,s, 0f1B
-Ar), 8.30-3.78 (2H, m.
−CH2N−)、 4.15 (2f(、d、 J=5
.11(z、 −CH2() )。-CH2N-), 4.15 (2f(,d, J=5
.. 11(z, -CH2()).
4.59〜4.90(Hf、 m、 −(J(−)、
6.05(01,s。4.59-4.90 (Hf, m, -(J(-),
6.05 (01,s.
broad、−NI(−)、7.28,7.73(ea
ch 2Hd。broad, -NI(-), 7.28, 7.73(ea
ch 2Hd.
J=8.4Hz、Ar−H)。J=8.4Hz, Ar-H).
元素分析:組成式C11H28NO68(MW271.
29 >計41直0;48.70%、[(;4.83%
。Elemental analysis: Composition formula C11H28NO68 (MW271.
29 > Total 41 shifts 0; 48.70%, [(; 4.83%
.
N;5.16% 測定値0;48.58%、II:4.78%。N; 5.16% Measured value 0: 48.58%, II: 4.78%.
N ; 5.09%
実施例2
粗(8)−、j 17.2f(純度68%)、溶媒ト
シて酢酸エチル100g/を用いた以外は実靭例1に準
じて調製し、(8)−5−1)−1−シルオキシメチル
−2−オキサゾリジノン19.61収率72%で得tこ
。比旋光度は〔α席+40.7°(C=1.0、メタノ
ール)であった。N; 5.09% Example 2 Crude (8)-, j 17.2f (purity 68%), prepared according to Example 1 except that 100 g/ethyl acetate was used as the solvent, (8) -5-1) -1-Syloxymethyl-2-oxazolidinone 19.61 was obtained in a yield of 72%. The specific optical rotation was [α+40.7° (C=1.0, methanol).
実施例3
tfl(→−5−ヒドロキシメチルー2−オキサゾリジ
ノン (心14.3g(純度82%)を用い、他はすべ
て実施例1に準じて行い、(i−5−1−シルオキシメ
チル−2−オキサゾリジノン (la) e20.9
y1収率77%でry t=。(a)−1a の物性[
直は以下の通りであった。Example 3 tfl(→-5-hydroxymethyl-2-oxazolidinone (14.3 g (purity 82%)) was used, and everything else was carried out according to Example 1, and (i-5-1-siloxymethyl- 2-oxazolidinone (la) e20.9
ry t= with y1 yield of 77%. (a)-1a Physical properties [
The direct line was as follows.
形 状:無色、勿、k
比旋光度:〔α)20−40.7°(C=1.O,メタ
ノール)111NM]、L (90MLrZ、 CD(
E13) δppm:2.45 (3H,S、 0l
−13−Ar )、 130〜8.78 (2■■、
In。Shape: Colorless, of course, k Specific optical rotation: [α) 20-40.7° (C = 1.O, methanol) 111NM], L (90MLrZ, CD (
E13) δppm: 2.45 (3H,S, 0l
-13-Ar), 130-8.78 (2■■,
In.
−0H2N −) 、 4..15 (21(、d、
J =5.11Lz、 −0H20−)。-0H2N-), 4. .. 15 (21(,d,
J = 5.11Lz, -0H20-).
4.59〜4.90(IIT、 rn、 −CI(−)
、 6.05(IH,S。4.59-4.90 (IIT, rn, -CI(-)
, 6.05 (IH, S.
broad、 −Nf(−)、 7.28.7.73(
each 21[d。broad, -Nf(-), 7.28.7.73(
each 21[d.
J=8.4kiz、 Ar−に■)
元素分析二姐成式C11II28NO58(N〜V27
1.29)訂シγ値0;48.70%、11;4.83
%、N;5.16%
測定値0;48.49%、li;4.71%、N;5.
11%J=8.4kiz, Ar-■) Elemental analysis two-part formula C11II28NO58 (N~V27
1.29) Correction gamma value 0; 48.70%, 11; 4.83
%, N; 5.16% Measured value 0; 48.49%, li; 4.71%, N; 5.
11%
Claims (4)
記載の化合物。(2) The compound according to claim 1, wherein the R substituent is a tolyl group.
リジノン¥(2)¥ ▲数式、化学式、表等があります▼と、一般式 RSO_2X¥(3)¥ (式中、Rは芳香族炭化水素基、Xはハロ ゲンを示す) で表わされるスルホニル化合物を塩基性化合物存在下、
不活性有機溶媒中で反応させることを特徴とする一般式
¥1¥ ▲数式、化学式、表等があります▼¥(1)¥ (式中、Rは芳香族炭化水素基を示す) で表わされる光学活性な5−スルホニルオキシメチル−
2−オキサゾリジノン誘導体の製造方法。(3) Optically active 5-hydroxymethyl-2-oxazolidinone¥(2)¥ ▲There are mathematical formulas, chemical formulas, tables, etc.▼ and the general formula RSO_2X¥(3)¥ (where R is an aromatic hydrocarbon group , X represents a halogen) in the presence of a basic compound,
Represented by the general formula ¥1¥ ▲Mathematical formulas, chemical formulas, tables, etc.▼¥(1)¥ (In the formula, R represents an aromatic hydrocarbon group) characterized by the reaction in an inert organic solvent Optically active 5-sulfonyloxymethyl-
A method for producing a 2-oxazolidinone derivative.
記載の製造方法。(4) The manufacturing method according to claim 3, wherein the R substituent is a tolyl group.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP60248664A JPS62108870A (en) | 1985-11-06 | 1985-11-06 | Optically active 5-sulfonyloxymethyl-2-oxazolidinone derivative and production thereof |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP60248664A JPS62108870A (en) | 1985-11-06 | 1985-11-06 | Optically active 5-sulfonyloxymethyl-2-oxazolidinone derivative and production thereof |
Publications (1)
Publication Number | Publication Date |
---|---|
JPS62108870A true JPS62108870A (en) | 1987-05-20 |
Family
ID=17181500
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP60248664A Pending JPS62108870A (en) | 1985-11-06 | 1985-11-06 | Optically active 5-sulfonyloxymethyl-2-oxazolidinone derivative and production thereof |
Country Status (1)
Country | Link |
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JP (1) | JPS62108870A (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5034535A (en) * | 1988-04-22 | 1991-07-23 | Astra Pharmaceutical Production Aktiebolag | Process for S-metoprolol via oxazolidin-2-one |
JPH03218367A (en) * | 1989-10-26 | 1991-09-25 | Tanabe Seiyaku Co Ltd | Naphthyloxazolidone derivative, its production and intermediate for synthesizing the same |
-
1985
- 1985-11-06 JP JP60248664A patent/JPS62108870A/en active Pending
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5034535A (en) * | 1988-04-22 | 1991-07-23 | Astra Pharmaceutical Production Aktiebolag | Process for S-metoprolol via oxazolidin-2-one |
JPH03218367A (en) * | 1989-10-26 | 1991-09-25 | Tanabe Seiyaku Co Ltd | Naphthyloxazolidone derivative, its production and intermediate for synthesizing the same |
JP2601008B2 (en) * | 1989-10-26 | 1997-04-16 | 田辺製薬株式会社 | Naphthyl oxazolidone derivatives, their preparation and their synthetic intermediates |
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