JPS617238A - Method of optical resolution of dl-clorprenaline - Google Patents
Method of optical resolution of dl-clorprenalineInfo
- Publication number
- JPS617238A JPS617238A JP12817184A JP12817184A JPS617238A JP S617238 A JPS617238 A JP S617238A JP 12817184 A JP12817184 A JP 12817184A JP 12817184 A JP12817184 A JP 12817184A JP S617238 A JPS617238 A JP S617238A
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- JP
- Japan
- Prior art keywords
- acid
- chlorprenaline
- water
- optical resolution
- crystals
- 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.)
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
【発明の詳細な説明】
[産業上の利用分野]
本発明は、下記式■で示される
dl−クロルブレナリンの工業的に有利な光学分割法に
関するものである。DETAILED DESCRIPTION OF THE INVENTION [Industrial Field of Application] The present invention relates to an industrially advantageous optical resolution method for dl-chlorbrenaline represented by the following formula (2).
[従来の技術]
dl−クロルプレナリンは気管支傘縮物質の遊離抑制作
用を有し、気管支筋を特異的に緩解するので、気管支喘
急等の呼吸器系疾患に使用されている。光学活性体の1
−りロルプレナリンは、更に優れた薬理作用を有する事
が知られているにも拘わらず、その光学活性体の分離方
法についての報告は見当らない。[Prior Art] dl-Chlorprenaline has the effect of suppressing the release of bronchoconstrictor substances and specifically relaxes bronchial muscles, and is therefore used for respiratory diseases such as bronchial asthma. Optically active substance 1
-Although it is known that relolprenaline has superior pharmacological effects, no reports have been found on methods for separating its optically active form.
[発明が解決しようとする問題点1
本発明は、安価な原料を用いて容易な操作で効率良く光
学分割を行う事が出来、高品質の光学活性体を1qる事
が出来ると共に、これに使用する光学分割剤の回収率も
高くて、T業生産士有利な方法を児出そうとするもので
ある。[Problem to be solved by the invention 1] The present invention makes it possible to efficiently perform optical resolution using inexpensive raw materials and easy operations, and to produce 1 q of high-quality optically active substances. The recovery rate of the optical resolution agent used is also high, and we are trying to develop a method that is advantageous to T-industry producers.
1問題点を解決づるための手段]
本発明省は、反応溶媒として水、メタノール、エタノー
ル等を用い、光学分割剤どじ−Cは安価でしかも大吊入
丁が容易なd−酒石酸、1−−グルタミン酸、1−−−
アスパラギン酸等を)パび、史にこれらアミノ酸のアセ
デル、ベンゾイル、クロルベンゾイル、二1へ[]ベン
ゾイル等のアシル誘導体や、d−酒石酸のアシル誘1す
体やアミド或はアニリド誘導体等の比較的簡t41な化
合物を合成し、dl−り[]ルプレナリンとの塩の生成
について種々検Hした。[Means for Solving Problem 1] The Ministry of the Invention uses water, methanol, ethanol, etc. as the reaction solvent, and the optical resolution agent Doji-C is d-tartaric acid, 1- -glutamic acid, 1---
Comparison of acyl derivatives such as acedel, benzoyl, chlorobenzoyl, and 21 [benzoyl], acyl derivatives of d-tartaric acid, amide or anilide derivatives, etc. A simple compound was synthesized, and various tests were conducted on the formation of salts with dl-li[]luprenaline.
殆どの場合、ジアステレオマー塩の結晶が析出しないで
飴状となったり、ラセミ体のまま結晶化したりして光学
分割の目的を果づ一事が出来なかったが、これらの中で
ただニトロタルドラニル酸と!−クロルプレナリンとか
らなるジアステレオマー塩のみが特異的に水に殆ど溶け
ない結晶を生成し、d−クロルプレナリンの塩は結晶し
ない事を発見した。In most cases, the crystals of the diastereomeric salts did not precipitate and became candy-like, or they crystallized as a racemate, making it impossible to achieve the purpose of optical resolution. With doranilic acid! It was discovered that only diastereomeric salts consisting of chlorprenaline and d-chlorprenaline specifically form crystals that are hardly soluble in water, while salts of d-chlorprenaline do not crystallize.
更に本発明賃はこの事実に基き、水を溶媒どして用いて
、1モルのdi−クロルプレナリンに1/2モルのニト
ロタル[ヘラニル酸と 1/2モルの塩酸とを同時に作
用させ、!−クロルプレプリンとニトロタル1−ラニル
酸からなるジアステレオマーjnの三水和物を結晶とし
て析出させ、d−クロルブレナリンは水に易溶性の塩酸
塩にして両者を効率良く分離する事に成功し、本発明を
完成した。Furthermore, based on this fact, the present invention was developed by simultaneously reacting 1 mole of di-chlorprenaline with 1/2 mole of nitrotal [heranilic acid and 1/2 mole of hydrochloric acid] using water as a solvent. ! - The trihydrate of diastereomer jn consisting of chlorprepurine and nitrothal-1-ranilic acid was precipitated as crystals, and d-chlorbrenaline was converted into a hydrochloride salt that is easily soluble in water, and the two were successfully separated efficiently. , completed the invention.
すなわち本発明は、下記式■で示されるdi−クロルプ
レナリンに、
該d!−りロルブレナリンの1/2当損の下記一般式■
で示されるニトロタルドラニル酸ど無i酸或は有機酸と
を水中で反応させて水に難溶性の!−クロルプレナリン
・ニトロタルドラニル酸塩の結晶を生成し、該!−り【
二1ルプレナリン・ニトロタルドラニル酸塩の結晶と水
に溶けたd〜クロルプレナリンの無機酸又は有機酸との
塩を分離することを特徴とするdアーク「)ルプレナリ
ンの光学分割法にかかるものである。That is, the present invention provides di-chlorprenaline represented by the following formula (2), and the d! -The following general formula for 1/2 loss of Rolbrenaline■
By reacting nitrotaldranilic acid or anhydrous acid or organic acid shown in water, it is difficult to dissolve in water! -Crystals of chlorprenaline nitrotaldranilate are formed, and the! −ri [
21. A d-arc method characterized by separating crystals of luprenaline nitrotaldranilate and a salt of d~chlorprenaline with an inorganic acid or an organic acid dissolved in water. It is something.
ここで、光学分割用に使用する前記一般式■で示される
ニトロタルドラニル酸は、メタニ1〜口体及びパラニト
ロ体が使用出来る。これらはd−酒石酸に無水酢酸を反
応させて得られるジアセヂル酒石酸無水物を、クロロボ
ルム中でメタニトロアニリン或はバラニトロアニリンと
加温反応させ、冷接水酸化ナトリウム水溶液を加えてり
ロロ小ルム溶液から抽出すると同時に加水分解を行って
アセチル基を脱し、液を塩酸で酸性にすることにより容
易に結晶を得る事が出来る。このニトロタルドラニル酸
は塩酸酸性の水及びアンモニア水には比較的安定で、取
り扱いも容易であり、又水には溶は難いのでその回収率
も非常に良く、光学分割剤として優れている。Here, as the nitrotaldranilic acid represented by the general formula (2) used for optical resolution, metani-1 to para-nitro and para-nitro can be used. These are made by reacting diacedyltartaric anhydride, which is obtained by reacting d-tartaric acid with acetic anhydride, with metanitroaniline or valanitroaniline in chloroborum, and adding a cold aqueous sodium hydroxide solution. Crystals can be easily obtained by performing hydrolysis at the same time as extraction from the solution to remove the acetyl group, and acidifying the solution with hydrochloric acid. This nitrotaldranilic acid is relatively stable and easy to handle in hydrochloric acid acidic water and ammonia water, and is difficult to dissolve in water, so the recovery rate is very high, making it an excellent optical resolution agent. .
!−クロルプレナリン・ニトロタルドラニル酸塩を形成
させる際に使用する無R酸としては塩酸、硫酸、リン酸
等、又有機酸としては酢酸、マレイン酸等が挙げられる
が、d−り[1ルプレナリンを水に溶は易い塩にして1
体ジアステレオマー塩を分離可能とするものであれば使
用可能である。! -R-free acids used in forming chlorprenaline nitrotaldranilate include hydrochloric acid, sulfuric acid, phosphoric acid, etc.; organic acids include acetic acid, maleic acid, etc.; 1 luprenaline as a salt that is easily soluble in water
Any diastereomer salt can be used as long as it allows separation of diastereomer salts.
[作 用]
!−り[1ルプレナリンのニトロタルドラニル酸塩は、
新規なジアステレオマー塩で比較的安定な化合物であり
、その二水和物は非常に結晶化し易く水には殆ど溶1)
ないから、光学分割に際Iノ殆ど定量的に結晶となって
析出し、又d−クロルプレナリンはニトロタルドラニル
酸どは塩を形成せず、塩酸塩のままであり、この11−
クロルプレナリン塩酸塩は水に非常によく溶けるので、
)濾過する事により両者を容易に分離する事が出来る。[Effect]! -ri [1 Luprenaline nitrotaldranilate is
It is a new diastereomeric salt and a relatively stable compound, and its dihydrate crystallizes very easily and is almost soluble in water1)
Therefore, during optical resolution, I almost quantitatively precipitates as a crystal, and d-chlorprenaline does not form a salt such as nitrotaldranil acid, but remains as a hydrochloride, and this 11-
Chlorprenaline hydrochloride is very soluble in water, so
) The two can be easily separated by filtration.
結晶は水洗により1体を損失する事無く、1体を完全に
除去する事が出来る。One crystal can be completely removed by washing with water without losing any of the crystals.
ジアステレオマー塩結晶に斉塩酸を加えてかき混ぜれば
、簡単にニトロタルトテニル酸が脱れて結晶となって、
析出し、オーりロルプレナリンは塩酸塩となって水に溶
ける。この!−クロルプレナリン塩酸塩水溶液及び前記
d−クロルプロレナリン塩酸塩含有)片波をアルカリ性
にしてやれば、それぞれ1体と1体に分割された高品質
の光学活性クロルプレナリンを得る事が出来、その操作
も容易である。If you add hydrochloric acid to the diastereomer salt crystals and stir, the nitrotaltothenyl acid will easily be removed and form crystals.
After precipitation, aurolprenaline becomes hydrochloride and dissolves in water. this! - Chlorprenaline hydrochloride aqueous solution and the above-mentioned d-chlorprorenaline hydrochloride-containing) If one side is made alkaline, it is possible to obtain high quality optically active chlorprenaline divided into one body and one body, respectively. Its operation is also easy.
本発明の方法は、1体のみのジアステレオマー塩を生成
させればよいので、一般に行われているジアステレオマ
ー塩による光学分割法に比し、効果を損う事無く分割剤
の使用量を半分に減らす事が出来るので優れており、又
この為に分割剤の回収作業を一段と容易にしている。Since the method of the present invention only needs to generate one diastereomer salt, the amount of resolving agent used can be reduced without impairing the effect compared to the commonly used optical resolution method using diastereomer salts. It is excellent because it can reduce the amount by half, and it also makes the work of recovering the dividing agent much easier.
[実 施 例]
以下、実施例に基づき本発明を更に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 described in more detail based on Examples, but the present invention is not limited to these Examples.
実施例1
2、Ofの水に粉末状のパラニトロタルドラニル酸[(
α)、 −+ 106.2” (C= 0.3、ジメ
チルホルムアミド) 、m、p、 216.5℃]、
1350及び濃塩酸45νfを加え、40℃に加温し、
撹拌しながら市−クロルプレナリン213.5(lを加
えるど結晶形が変化し、!−クロルプレナリンのパラニ
トロタルドラニル酸塩の結晶が析出した。40℃で2時
間撹拌を続けた後、室温にし、濾過、水洗、乾燥し、!
−りロルプレナリン・パラニトロタルドラニル酸塩二水
和物の白色結晶259gを得た[含量100.3%(非
水滴定法、無水物換算)、〔α〕。−十24,0° (
C= 1.0、ジメチルホルムアミド) 、m、p、
101.0℃(分解)、水分6.9%(カールフィッシ
ャー法)]。収率はほぼ定量的であった。元素分析値は
次の通りであった。Example 1 Powdered para-nitrotaldranilic acid [(
α), −+ 106.2” (C=0.3, dimethylformamide), m, p, 216.5°C],
1350 and concentrated hydrochloric acid 45νf, heated to 40°C,
While stirring, chlorprenaline 213.5 (l) was added, and the crystal form changed, and crystals of paranitrotaldranilate of chlorprenaline were precipitated. Stirring was continued at 40°C for 2 hours. After that, let it come to room temperature, filter it, wash it with water, dry it, and!
- 259 g of white crystals of relolprenaline paranitrotaldranilate dihydrate were obtained [content 100.3% (non-aqueous titration method, calculated as anhydride), [α]]. -124,0° (
C=1.0, dimethylformamide), m, p,
101.0°C (decomposition), moisture 6.9% (Karl Fischer method)]. The yield was almost quantitative. The elemental analysis values were as follows.
元素分析 C211(26C!N308 ・21−1
2.0として
計算値(%);
C: 4g、51 、H: 5,82 、N :
8.0g実測値(%):
C: 48.21 、H: 5.84 、N :
8.03この結晶を水1.51に懸濁し、濃塩酸100
xRを加え、室温で撹拌し続【プると、結晶は一旦溶
解し、代ってパラニトロタルドラニル酸の白色針状結晶
が析出した。2時間撹拌した後、濾過、水洗、乾燥し、
パラニトロタルドラニル酸130gを回収した[含量1
00.1%(アルカリ滴定法)、〔α)D−−1−10
7,Oo (c = 0.3、ジメチルホルムアミド)
、m、p、 216.2℃コ。次いで炉液と洗浄水と
を合し、活性炭処理して得られた無色液にクロロホルム
を加え、更にアンモニア水を加えてアルカリ性となし、
分液した。クロロホルム溶液を水洗、乾燥、濃縮し、!
−クロルプレナリン塩基の白色結晶106gを得たE含
量100.1%(非水滴定法)、〔α〕20=−71.
3゜(c = 1.0、ジメチルホルムアミド) 、
n+、p。Elemental analysis C211 (26C!N308 ・21-1
Calculated value (%) assuming 2.0; C: 4g, 51, H: 5,82, N:
8.0g Actual value (%): C: 48.21, H: 5.84, N:
8.03 Suspend the crystals in 1.51 g of water and add 100 g of concentrated hydrochloric acid.
When xR was added and the mixture was continuously stirred at room temperature, the crystals were once dissolved and white needle-like crystals of para-nitrotaldranilic acid were precipitated instead. After stirring for 2 hours, filter, wash with water, dry,
130 g of paranitrotaldranilic acid was recovered [content 1
00.1% (alkali titration method), [α) D--1-10
7, Oo (c = 0.3, dimethylformamide)
, m, p, 216.2℃. Next, the furnace liquid and washing water were combined and treated with activated carbon. Chloroform was added to the colorless liquid obtained, and aqueous ammonia was added to make it alkaline.
The liquid was separated. Wash the chloroform solution with water, dry it, concentrate it, and!
- 106 g of white crystals of chlorprenaline base were obtained, E content 100.1% (non-aqueous titration method), [α]20=-71.
3° (c = 1.0, dimethylformamide),
n+, p.
90.2℃]。収率はほぼ定量的であった。90.2°C]. The yield was almost quantitative.
!−クロルプ1ノナリン・パラニトロタルドラニル酸塩
の結晶戸数後の)片波には、d−クロルプレナリン塩酸
塩が含まれている。!−クロルプレナリン塩基を得た時
と同様な処理を行い、d−クロルプレナリン塩基の白色
結晶104qを得た[収率97.4%、含量99.9%
(非水滴定法)、〔α〕。−+ 66.6° (c =
i、o、ジメチルボルムアミド)、…、p、90.
8°C]。! - One wave after the crystallization of chlorp 1 nonaline paranitrotaldranilate contains d-chlorprenaline hydrochloride. ! - Performing the same treatment as when obtaining chlorprenaline base, white crystals 104q of d-chlorprenaline base were obtained [yield 97.4%, content 99.9%
(Non-aqueous titration method), [α]. −+ 66.6° (c =
i, o, dimethylborumamide), ..., p, 90.
8°C].
前述の!−クロルプレナリン塩基に当量の塩化水素をア
ルコール中で反応させて得られた結晶をアルコールより
再結晶し、!−りロルプレナリン塩酸塩の白色砂状結晶
を得た[含量100.0%(非水滴定法)、〔α〕。−
−64,5゜(c = 1.0、ジメチルホルムアミ
ド) 、m、p。As mentioned above! -The crystals obtained by reacting chlorprenaline base with an equivalent amount of hydrogen chloride in alcohol are recrystallized from alcohol, and! -White sandy crystals of lorprenaline hydrochloride were obtained [content 100.0% (non-aqueous titration method), [α]]. −
-64,5° (c = 1.0, dimethylformamide), m, p.
198.2℃]。又、d−クロルプレナリン塩基も同様
に処理し、d−クロルプレナリン塩酸塩の白色砂状結晶
を得た[含量100.2%、〔α〕0= + 64.2
° (c = 1.0、ジメチルホルムアミド)、=1
0−
m、p、198.0 °C] 。198.2°C]. In addition, d-chlorprenaline base was treated in the same manner to obtain white sandy crystals of d-chlorprenaline hydrochloride [content 100.2%, [α] 0 = + 64.2
° (c = 1.0, dimethylformamide), = 1
0-m, p, 198.0 °C].
精製した!−及びd−クロルブレナリン塩酸塩より生成
した各塩基を更にノルマルヘキサンより再結晶して得た
白色剣状結晶の比旋光度は次の通りであった。Refined! The specific optical rotations of white sword-shaped crystals obtained by further recrystallizing each base produced from - and d-chlorbrenaline hydrochloride from n-hexane were as follows.
!−クロルプレナリン塩基:
〔α]D・−−72,2° (C= 1.0、ジメチ
ルホルムアミド〉
d−クロルブレナリン塩基:
(a )D= + 72,0° (C= 1.0、ジ
メチルホルムアミド)
実施例2
メタニド「1タル1〜ラニル酸[〔α) 20= 84
,9゜(c = 0.3、ジメチルホルムアミド) 、
m、p。! -Chlorprenaline base: [α]D・−72,2° (C= 1.0, dimethylformamide) d-Chlorprenaline base: (a) D= + 72,0° (C= 1.0, dimethyl Formamide) Example 2 Methanide "1 tal 1 ~ ranilic acid [[α) 20 = 84
, 9° (c = 0.3, dimethylformamide),
m, p.
203.0℃]を用い、実施例1ど同様な操作を行ない
、!−クロルプレナリン・メタニ1へロタルトラニル酸
塩三水和物の白色結晶258gを得た[含量100.2
%(非水滴定法、無水物換算)、ムアミド) 、m、p
、 103.8℃、水分7.0%(カールフィッシャー
法)1o収率はほぼ定量的であった。元素分析値は次の
通りであった。203.0°C], perform the same operation as in Example 1, and! - Obtained 258 g of white crystals of chlorprenaline metani-1 helotartranilate trihydrate [content 100.2
% (non-aqueous titration method, anhydrous equivalent), m, p
, 103.8°C, water content 7.0% (Karl Fischer method) 1o yield was almost quantitative. The elemental analysis values were as follows.
元素分析C)−I CアNo ・21−120とし
て
計算値(%):
C: 118.51 、l−1: 5,82 、N
: 8,08実測値(%):
C: 48.33 、l−1: 5,93 、N +
8.01この結晶及びp液を実施例1ど同様に処即
し、!−及びd−り目ルプレナリン塩基の白色結晶を夫
々1qた。!−塩基:含吊100,2%(非水滴定法)
、(α)、 =−71,9° (c = 1.0、ジメ
チル小ルノ\アミド) 、m、p、90.6℃: d−
塩基:含量100,4%(非水滴定法)、(α)o−+
−68,3° (c = 1.0.ジメチルホルムア
ミド)、m、p、90.7℃
又、メタニド[1タルドラニル酸もほぼ定量的に回収さ
れた。Elemental analysis C)-I CA No. Calculated value (%) as 21-120: C: 118.51, l-1: 5,82, N
: 8,08 Actual value (%): C: 48.33, l-1: 5,93, N +
8.01 Treat this crystal and p solution in the same manner as in Example 1, and! 1 q of white crystals of - and d-th luprenaline bases were each obtained. ! -Base: Contains 100.2% (non-aqueous titration method)
, (α), = -71,9° (c = 1.0, dimethyl small \amide), m, p, 90.6°C: d-
Base: Content 100.4% (non-aqueous titration method), (α) o-+
-68.3° (c = 1.0. dimethylformamide), m, p, 90.7°C.Methanide [1-taldranilic acid was also recovered almost quantitatively.
「発明の効果]
以上述べたように本発明のd!−クロルグレナリンの光
学分割法によれば、下記の如き種々の優れた効果を発揮
する。"Effects of the Invention" As described above, the optical resolution method of d!-chlorgrenaline of the present invention exhibits various excellent effects as described below.
(I) ニトロタルドラニル酸を光学分割剤どして使
用するので、!−クロルプレナリンはニトロタルドラニ
ル酸と水に不溶性のジアステレオマー塩を生成し結晶化
するが、d−り[1ルプレナリンはジアステレオマーj
福を形成せず、水に易溶性の無機又は有機酸塩のまま存
在するので、!一体とd一体の分前が容易であり、光学
分割を容易に行える。(I) Nitrotaldranilic acid is used as an optical resolving agent, so! -Chlorprenaline forms a water-insoluble diastereomeric salt with nitrotaldranilic acid and crystallizes, but d-li[1luprenaline has diastereomer
Because it does not form Fuku and exists as an inorganic or organic acid salt that is easily soluble in water! The division of integral and d-integral is easy, and optical division can be easily performed.
(II) f−り1]ルプレナリン・ニトロタルドラ
ニル酸塩を酸処理することにより簡単に!−クロルプレ
ナリン塩酸塩が得られ、薬理活↑(1の高い!−クロル
プレナリンが容易に得られる。(II) easily by treating f-ri1] luprenaline nitrotaldranilate with acid! - Chlorprenaline hydrochloride is obtained, with high pharmacological activity ↑ (1!) - Chlorprenaline is easily obtained.
@) ニド[]タルドラニル酸は比較的安定で取り扱い
も容易であり、水に溶は難いので、!−クロルブレナリ
ンとの分前が容易であり目つ回収率も高い。従って、光
学分割剤として優れている。@) Nido[]taldranilic acid is relatively stable and easy to handle, and it is difficult to dissolve in water, so! - It can be easily mixed with chlorbrenaline and has a high recovery rate. Therefore, it is excellent as an optical resolution agent.
の 光学分割剤ニトロタルドラニル酸は1−ク【]ルプ
レナリンとのみジアステレオマー塩を形成し結晶化する
ので、使用量が61−クロルプレナリンの1/2当量で
よいため、経洛的である。The optical resolving agent nitrotaldranilic acid forms a diastereomeric salt only with 1-chlorprenaline and crystallizes, so the amount used is only 1/2 equivalent of 61-chlorprenaline, so it is not suitable for clinical use. It is.
特 許 出 願 人Patent applicant
Claims (1)
Iで示されるニトロタルトラニル酸と▲数式、化学式、
表等があります▼II(−NO_2はメタ又はパラ位) 無機酸或は有機酸とを水中で反応させて水に難溶性のl
−クロルプレナリン・ニトロタルトラニル酸塩の結晶を
生成し、該l−クロルプレナリン・ニトロタルトラニル
酸塩の結晶と水に溶けたd−クロルプレナリンの無機酸
又は有機酸との塩を分離することを特徴とするdl−ク
ロルプレナリンの光学分割法。[Claims] 1) dl-chlorprenaline represented by the following formula I: ▲There are mathematical formulas, chemical formulas, tables, etc.▼... I The following general formula of 1/2 equivalent of the dl-chlorprenaline: I
Nitrotartoranilic acid represented by I and ▲mathematical formula, chemical formula,
There are tables, etc. ▼II (-NO_2 is meta or para position) By reacting with an inorganic or organic acid in water, it is possible to create l
- Produce crystals of chlorprenaline nitrotartranilate, and combine the crystals of l-chlorprenaline nitrotartranilate with an inorganic or organic acid of d-chlorprenaline dissolved in water. A method for optical resolution of dl-chlorprenaline, characterized by separating the salt.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP12817184A JPS617238A (en) | 1984-06-21 | 1984-06-21 | Method of optical resolution of dl-clorprenaline |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP12817184A JPS617238A (en) | 1984-06-21 | 1984-06-21 | Method of optical resolution of dl-clorprenaline |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS617238A true JPS617238A (en) | 1986-01-13 |
JPS6121939B2 JPS6121939B2 (en) | 1986-05-29 |
Family
ID=14978157
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP12817184A Granted JPS617238A (en) | 1984-06-21 | 1984-06-21 | Method of optical resolution of dl-clorprenaline |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPS617238A (en) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP1384711A1 (en) * | 1996-06-13 | 2004-01-28 | SUMIKA FINE CHEMICALS Co., Ltd. | Optical resolution of a piperidine derivative |
WO2008015689A1 (en) * | 2006-08-02 | 2008-02-07 | Aarti Healthcare Limited | A process for the preparation of optically pure r (-) salbutamol and its pharmaceutically acceptable salts |
CN106045865A (en) * | 2016-05-25 | 2016-10-26 | 陕西科技大学 | Method for preparing clorprenaline optical isomers based on chiral liquid chromatography |
-
1984
- 1984-06-21 JP JP12817184A patent/JPS617238A/en active Granted
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP1384711A1 (en) * | 1996-06-13 | 2004-01-28 | SUMIKA FINE CHEMICALS Co., Ltd. | Optical resolution of a piperidine derivative |
US6815548B2 (en) | 1996-06-13 | 2004-11-09 | Sumika Fine Chemicals Co., Ltd. | Process for preparing a piperidine derivative |
WO2008015689A1 (en) * | 2006-08-02 | 2008-02-07 | Aarti Healthcare Limited | A process for the preparation of optically pure r (-) salbutamol and its pharmaceutically acceptable salts |
CN106045865A (en) * | 2016-05-25 | 2016-10-26 | 陕西科技大学 | Method for preparing clorprenaline optical isomers based on chiral liquid chromatography |
CN106045865B (en) * | 2016-05-25 | 2018-11-27 | 陕西科技大学 | A method of Clorprenaline optical isomer is prepared based on Chiral liquid chromatography |
Also Published As
Publication number | Publication date |
---|---|
JPS6121939B2 (en) | 1986-05-29 |
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