JPH0215065A - Production of high-purity o-5,6,7,8-tetrahydronaphthyl-n-methyl-n-(6-methoxy-2-pyridyl)thiocarbamate - Google Patents
Production of high-purity o-5,6,7,8-tetrahydronaphthyl-n-methyl-n-(6-methoxy-2-pyridyl)thiocarbamateInfo
- Publication number
- JPH0215065A JPH0215065A JP16512388A JP16512388A JPH0215065A JP H0215065 A JPH0215065 A JP H0215065A JP 16512388 A JP16512388 A JP 16512388A JP 16512388 A JP16512388 A JP 16512388A JP H0215065 A JPH0215065 A JP H0215065A
- Authority
- JP
- Japan
- Prior art keywords
- purity
- methyl
- pyridyl
- tetrahydronaphthyl
- methoxy
- 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
Links
- GNVMUORYQLCPJZ-UHFFFAOYSA-M Thiocarbamate Chemical compound NC([S-])=O GNVMUORYQLCPJZ-UHFFFAOYSA-M 0.000 title claims abstract description 17
- 238000004519 manufacturing process Methods 0.000 title claims description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims abstract description 25
- 238000001953 recrystallisation Methods 0.000 claims abstract description 6
- -1 isopropyl alcohol Chemical compound 0.000 claims abstract description 5
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 4
- GXHQLRBOZRJHPZ-UHFFFAOYSA-N 6-methoxy-n-methylpyridin-2-amine Chemical compound CNC1=CC=CC(OC)=N1 GXHQLRBOZRJHPZ-UHFFFAOYSA-N 0.000 claims abstract 2
- 230000000382 dechlorinating effect Effects 0.000 claims abstract 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 6
- 239000000741 silica gel Substances 0.000 claims description 6
- 229910002027 silica gel Inorganic materials 0.000 claims description 6
- 150000001298 alcohols Chemical class 0.000 claims 1
- 238000004440 column chromatography Methods 0.000 claims 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 abstract description 18
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 abstract description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract description 7
- 150000001875 compounds Chemical class 0.000 abstract description 5
- 239000003480 eluent Substances 0.000 abstract description 5
- 238000010898 silica gel chromatography Methods 0.000 abstract description 5
- 239000003814 drug Substances 0.000 abstract description 2
- 239000002245 particle Substances 0.000 abstract description 2
- 239000002904 solvent Substances 0.000 abstract description 2
- 238000004587 chromatography analysis Methods 0.000 abstract 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 239000012046 mixed solvent Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical compound CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- KTRFZWJCHOQHMN-UHFFFAOYSA-N chloromethanethioic s-acid Chemical compound SC(Cl)=O KTRFZWJCHOQHMN-UHFFFAOYSA-N 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
Abstract
Description
【発明の詳細な説明】
３、発明の詳細な説明
（産業上の利用分野）
本発明は、高純度０−５．６，７．８−テトラヒドロナ
フチル−Ｎ−メチル−Ｎ−（６−メトキシ−２−ピリジ
ル）チオカーバメイトの製造方法に関する。本発明の製
造方法により製造することかできるＯ−５，６，７，８
−テトラヒドロナフチル−Ｎ−メチル−Ｎ−（６−メト
キシ−２−ピリジル）チオカーバメイトは、医薬として
’ｈ−用な化合物である。Detailed Description of the Invention 3. Detailed Description of the Invention (Field of Industrial Application) The present invention provides highly purified 0-5.6,7.8-tetrahydronaphthyl-N-methyl-N-(6-methoxy The present invention relates to a method for producing -2-pyridyl)thiocarbamate. O-5, 6, 7, 8 that can be produced by the production method of the present invention
-Tetrahydronaphthyl-N-methyl-N-(6-methoxy-2-pyridyl)thiocarbamate is a compound used as a medicine.
（従来の技術）
０−５．６，７．８−テトラヒドロナフチル−Ｎ−メチ
ル−Ｎ−（６−メトキシ−２−ピリジル）チオカーバメ
イトは、該クロロチオホルメイトと２−メチルアミノ−
６−メドキシピリジノンを脱ハロゲン化水素試剤存在下
で反応させることにより製造できることは、公知である
。又、粗製物は、エタノール、イソプロピルアルコール
等の０１〜Ｃ３のアルコールを用いて再結晶、精製する
ことができる。(Prior art) 0-5.6,7.8-tetrahydronaphthyl-N-methyl-N-(6-methoxy-2-pyridyl)thiocarbamate is a chlorothioformate and 2-methylamino-
It is known that 6-medoxypyridinone can be produced by reacting it in the presence of a dehydrohalogenating agent. Moreover, the crude product can be recrystallized and purified using 01-C3 alcohol such as ethanol and isopropyl alcohol.
しかし、この方法で得られた該カーバメイトは、通常、
純ｉｑ９．ｓ％程度の目的物しか得ることができない。However, the carbamate obtained by this method usually
pure iq9. Only about s% of the target product can be obtained.
従って、純度９９．９以上である高純度○−５．６，７
．８−テトラヒドロナフチル−Ｎ−メチル−Ｎ−（６−
メトキシ−２−ピリジル）チオカーバメイトの製造、精
製方法か望まれていた。Therefore, high purity ○-5.6,7 with purity of 99.9 or higher
．． 8-tetrahydronaphthyl-N-methyl-N-(6-
A method for producing and purifying methoxy-2-pyridyl)thiocarbamate has been desired.
（本発明が解決しようとする問題点）
本発明の１」的は、高純度のＯ−５，６，７，，８テト
ラヒドロナフチル−Ｎ−メチル−Ｎ−（６−メドキンー
２−ピリジル）チオカーバメイトを得ることである。(Problems to be Solved by the Present Invention) The object of the present invention is to obtain highly purified O-5,6,7,,8 tetrahydronaphthyl-N-methyl-N-(6-medquin-2-pyridyl)thiophyl It is to obtain carbamate.
（問題点を解決するための手段及び作用）本発明者は、
粗製０−５．６，７．８−テトラヒドロナフチル−Ｎ−
メチル−Ｎ−（６−メドキンー２−ピリジル）チオカー
バメイトから高純度の該チオカーバメイトを得る方法い
ついて鋭意検討した結果、該粗製チオカーバメイトを０
１〜Ｃ３のアルコールから再結晶後、更にｎ−へキサン
から再結晶を行いシリカゲルカラムクロマトグラフ（溶
離液：ｎ−ヘキサン／酢酸エチル）を用いて、精製する
ことにより高純度の該チオカーバメイＩ・を製造出来る
ことを見出だし、本発明を完成した。(Means and effects for solving the problem) The present inventor:
Crude 0-5.6,7.8-tetrahydronaphthyl-N-
As a result of extensive research into a method for obtaining highly purified thiocarbamate from methyl-N-(6-medquin-2-pyridyl)thiocarbamate, we found that the crude thiocarbamate was
After recrystallization from 1-C3 alcohol, further recrystallization from n-hexane and purification using silica gel column chromatography (eluent: n-hexane/ethyl acetate) to obtain highly pure thiocarbamay I. The present invention was completed based on the discovery that it is possible to produce the following.
即ち本発明はＯ−５，６，７，８−テトラヒドロナフチ
ル−Ｎ−メチル−Ｎ−（６−メトキシ＝２−ピリジル）
チオカーバメイトをＣ１〜Ｃ３のアルコールから再結晶
後さらにｎ−へキサンから再結晶し、シリカゲルカラム
クロマトグラフを用いて精製することを特徴とする高純
度該チオカーバメイトの製造方法を提供するものである
。That is, the present invention provides O-5,6,7,8-tetrahydronaphthyl-N-methyl-N-(6-methoxy=2-pyridyl)
The present invention provides a method for producing a highly pure thiocarbamate, which comprises recrystallizing the thiocarbamate from a C1-C3 alcohol, recrystallizing it from n-hexane, and purifying it using silica gel column chromatography. .
以下、本発明について詳しく述べる。The present invention will be described in detail below.
粗製０−５．６，７．８−テトラヒドロナフチル−Ｎ−
メチル−Ｎ−（６−メトキシ−２−ピリジル）チオカー
バメイトは、２− （５，６，７゜８−テトラヒドロナ
フトキシ）−クロロチオホルメイトと２−メチルアミノ
−６−メドキシピリジンとを炭酸ナトリウム、炭酸カリ
ウム等のアルカリ金属炭酸塩の脱ハロゲン化水素試剤存
在下、イソプロピルアルコールと水の混合溶媒系中、縮
合することにより得ることが出来る。この粗製〇−５６
７８−テトラヒドロナフチル−Ｎ−メチル−Ｎ−（６−
メトキシ−２−ピリジル）チオカーバメイトを０１〜Ｃ
３のアルコールを用いてｊ結晶し、純度９９．５９６程
度の目的物を得る。Crude 0-5.6,7.8-tetrahydronaphthyl-N-
Methyl-N-(6-methoxy-2-pyridyl)thiocarbamate is a combination of 2-(5,6,7°8-tetrahydronaphthoxy)-chlorothioformate and 2-methylamino-6-medoxypyridine. It can be obtained by condensing an alkali metal carbonate such as sodium carbonate or potassium carbonate in a mixed solvent system of isopropyl alcohol and water in the presence of a dehydrohalogenating agent. This crude 〇-56
78-Tetrahydronaphthyl-N-methyl-N-(6-
01-C methoxy-2-pyridyl) thiocarbamate
Crystallize using alcohol No. 3 to obtain the target product with a purity of about 99.596.
史にｎ−ヘキサンを用いて再結晶することにより、純度
を９９．７９６まで高めることが出来る。ｎ−へキサン
再結晶無しにシリカゲルカラムクロマトグラフを用い精
製を行っても、目的物の純度９９゜９％以上のものは１
１１られない。次いでシリカゲルカラムクロマトグラフ
を用い精製する。By recrystallizing using n-hexane, the purity can be increased to 99.796. Even if purification is performed using silica gel column chromatography without recrystallization with n-hexane, the purity of the target product is 99.9% or higher.
11 I can't. Then, it is purified using silica gel column chromatography.
本発明で用いられる充填剤のシリカゲルは、市販品を前
処理なしで使用゛することが出来、粒径が１００〜３０
０メツシユの範囲のものが適当であるが、更に好ましく
は、平均２００メツシユのものを用いることが適当であ
る。充填されるシリカゲルの口は、該粗製チオカーバメ
イトに対して好ましくは、５０〜１００倍量が、更に好
ましくは、６０倍程度が適当である。展開に用いられる
溶媒は、ｎ−へキサンに対し酢酸エチルを２〜５ｖ。The filler silica gel used in the present invention can be used as a commercially available product without pretreatment, and has a particle size of 100 to 30 mm.
It is appropriate to use a material with a mesh size of 0 meshes, and more preferably a material with an average mesh size of 200 meshes. The amount of silica gel to be filled is preferably 50 to 100 times, more preferably about 60 times the amount of the crude thiocarbamate. The solvent used for development is ethyl acetate in a ratio of 2 to 5 vol against n-hexane.
１％添加した混合溶媒が適当である。又、展開流速は、
７〜１２ｍ１／ｍｉｎが適当である。A mixed solvent containing 1% is suitable. In addition, the development flow rate is
7 to 12 m1/min is appropriate.
（実施例）
以下、本発明を実施例によりさらに説明するが、本発明
はこれらにのみ限定されるものではない。(Examples) Hereinafter, the present invention will be further explained with reference to Examples, but the present invention is not limited to these.
実施例１
２−メチルアミノ−６−メドキシビリジン５２゜７１
ｇ （０，３８ｍｏ ｌ）をイソプロピルアルコール６
５０ｍ１と水３３ｍ１の混合液に溶かし、炭酸ナトリウ
ム３８．０２ｇ（０，３６ｍｏｌ）を慝濁させて、室温
にて撹拌下２− （５，６，７゜８−テトラヒドロナフ
トキシ）−クロロチオホルメイト８２．３１ｇ （０，
３６ｍｏｌ）を滴下した。滴下終了後、１２時間、撹拌
を継続した。スラリー状の反応物を吸引ろ別し、イソプ
ロピルアルコール及び水で洗浄後、イソプロピルアルコ
ール８００ｍ１に加熱溶解し、活性炭を１０ｇ加えて煮
沸後、ろ別、冷却して、粗製０−５．６，７゜８−テト
ラヒドロナフチル−Ｎ−メチル−Ｎ−（６−メトキシ−
２−ピリジル）チオカーバメイ１・９４．５ｇ （０，
２９ｍｏｌ、りｏロチオホルメイトからの収率７９．３
％を得た。さらにｎ−ヘキサン１２００ｍ１を用いて再
結晶を繰返した。Example 1 2-methylamino-6-medoxyviridine 52°71
g (0.38 mol) with isopropyl alcohol 6
2-(5,6,7°8-tetrahydronaphthoxy)-chlorothioform was dissolved in a mixture of 50 ml and 33 ml of water, suspended with 38.02 g (0.36 mol) of sodium carbonate, and stirred at room temperature. Mate 82.31g (0,
36 mol) was added dropwise. After the dropwise addition was completed, stirring was continued for 12 hours. The slurry-like reaction product was separated by suction filtration, washed with isopropyl alcohol and water, heated and dissolved in 800 ml of isopropyl alcohol, added with 10 g of activated carbon, boiled, filtered, and cooled to obtain crude 0-5.6,7.゜8-Tetrahydronaphthyl-N-methyl-N-(6-methoxy-
2-pyridyl) thiocarbamay 1.94.5g (0,
29 mol, yield 79.3 from riorothioformate
I got %. Furthermore, recrystallization was repeated using 1200 ml of n-hexane.
次に、得られた粗製チオカーバメイトのうち約２ｇを取
り、ジクロロメタン４０ｍ１に溶かし、！［均２００メ
ツシュのシリカゲル２０ｇを加え撹拌後、８０℃で３０
分間乾燥した。それを直径約３．５ｃｍのガラス製カラ
ム中のすでにｎ−へキサン／酢酸エチル−９５１５の混
合液で充填しておいた平均２００メツシユのシリカゲル
上に同組成の溶離液を用いて湿式充填し、１０ ｍ ｌ
／ ｍ ｉｎの速度で展開後、目的の精製０−５．６
，７゜８−テ）・ラヒドロナフチルーＮ−メチル−Ｎ（
６−メトキシ−２−ピリジル）チオカーバメイ１−１．
１６ｇをｉりた。Next, about 2 g of the obtained crude thiocarbamate was taken and dissolved in 40 ml of dichloromethane. [After adding 20 g of silica gel with a uniform mesh size of 200 and stirring, it was heated to 80°C for 30
Dry for a minute. This was wet packed using an eluent of the same composition onto an average of 200 mesh of silica gel that had already been packed with a mixture of n-hexane/ethyl acetate-9515 in a glass column with a diameter of about 3.5 cm. , 10ml
After development at a speed of /min, the desired purification 0-5.6
,7゜8-te)・Lahydronaphthyl-N-methyl-N(
6-methoxy-2-pyridyl)thiocarbamay 1-1.
I took 16g.
また、精製物について液体クロマトグラフィー（検出器
：ＵＶ−８０００、カラム順相Ｔ Ｓ ＫＣＥＬＳｉ−
６０，４，６ｍｍｘ２５ｃｍ、溶離液：ｎ−ヘキサン／
酢酸エチル−９８／２）により分析を行った結果、純度
は１００．０％であった。さらにシリカゲル薄層クロマ
トグラフィ（溶離液：ｎ−ペンタン／酢酸メチル／酢酸
−８５／１０１５．２００μｇ塗布、１０ｃｍ展開）に
より観察したところ、単一スポットを示し、窒素定量値
（Ｃ１８Ｈ２ｏＮ２０□Ｓ）は、９９．５％以上であっ
た。In addition, the purified product was subjected to liquid chromatography (detector: UV-8000, column normal phase T S KCEL Si-
60.4.6mm x 25cm, eluent: n-hexane/
As a result of analysis using ethyl acetate (98/2), the purity was 100.0%. Furthermore, observation by silica gel thin layer chromatography (eluent: n-pentane/methyl acetate/acetic acid-85/1015.200 μg applied, 10 cm development) showed a single spot, and the nitrogen quantitative value (C18H2oN20□S) was 99 It was .5% or more.
実例２．３および比較例Example 2.3 and comparative example
Claims (1)
ロロチオホルメイトと２−メチルアミノ−６−メトキシ
ピリジンンとを脱塩素化剤存在下で縮合して得られた粗
製Ｏ−５，６，７，８−テトラヒドロナフチル−Ｎ−メ
チル−Ｎ−（６−メトキシ−２−ピリジル）チオカーバ
メイトを、Ｃ＿１〜Ｃ＿３のアルコール類、次いでｎ−
ヘキサンで再結晶後、シリカゲルを充填したカラムクロ
マトグラフにより精製することを特徴とするＯ−５，６
，７，８−テトラヒドロナフチル−Ｎ−メチル−Ｎ−（
６−メトキシ−２−ピリジル）チオカーバメイトの製造
方法。Crude O-5 obtained by condensing 2-(5,6,7,8-tetrahydronaphthoxy)-chlorothioformate and 2-methylamino-6-methoxypyridine in the presence of a dechlorinating agent , 6,7,8-tetrahydronaphthyl-N-methyl-N-(6-methoxy-2-pyridyl)thiocarbamate, C_1 to C_3 alcohols, and then n-
O-5,6 characterized in that it is purified by column chromatography packed with silica gel after recrystallization with hexane.
,7,8-tetrahydronaphthyl-N-methyl-N-(
A method for producing 6-methoxy-2-pyridyl)thiocarbamate.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP16512388A JPH0215065A (en) | 1988-07-04 | 1988-07-04 | Production of high-purity o-5,6,7,8-tetrahydronaphthyl-n-methyl-n-(6-methoxy-2-pyridyl)thiocarbamate |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP16512388A JPH0215065A (en) | 1988-07-04 | 1988-07-04 | Production of high-purity o-5,6,7,8-tetrahydronaphthyl-n-methyl-n-(6-methoxy-2-pyridyl)thiocarbamate |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH0215065A true JPH0215065A (en) | 1990-01-18 |
Family
ID=15806350
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP16512388A Pending JPH0215065A (en) | 1988-07-04 | 1988-07-04 | Production of high-purity o-5,6,7,8-tetrahydronaphthyl-n-methyl-n-(6-methoxy-2-pyridyl)thiocarbamate |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0215065A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2005350447A (en) * | 2004-05-12 | 2005-12-22 | Tosoh Corp | O-(5,6,7,8-tetrahydro-2-naphthyl)-n-(6-methoxy-2-pyridyl)-n-methylthiocarbamate and method for producing the same |
| JP2006298832A (en) * | 2005-04-21 | 2006-11-02 | Tosoh Corp | High-purity o-(5,6,7,8-tetrahydro-2-naphthyl)-n-(6-methoxy-2-pyridyl)-n-methylthiocarbamate and its preparation method |
-
1988
- 1988-07-04 JP JP16512388A patent/JPH0215065A/en active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2005350447A (en) * | 2004-05-12 | 2005-12-22 | Tosoh Corp | O-(5,6,7,8-tetrahydro-2-naphthyl)-n-(6-methoxy-2-pyridyl)-n-methylthiocarbamate and method for producing the same |
| JP2006298832A (en) * | 2005-04-21 | 2006-11-02 | Tosoh Corp | High-purity o-(5,6,7,8-tetrahydro-2-naphthyl)-n-(6-methoxy-2-pyridyl)-n-methylthiocarbamate and its preparation method |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| FR2517302A1 (en) | ESTERS AND AMIDES OF 13 14-BISDEHYDROPROSTAGLANDINS | |
| JPS5817474B2 (en) | Yuukikagoubutsuni Cansurukairiyou | |
| JPS62161778A (en) | Manufacture of substituted cyclopropane derivative | |
| JPS5839822B2 (en) | Method for producing PGA type compounds | |
| JPH0215065A (en) | Production of high-purity o-5,6,7,8-tetrahydronaphthyl-n-methyl-n-(6-methoxy-2-pyridyl)thiocarbamate | |
| JPS6025952A (en) | Production of optically active 2,2-dimethylcyclo-propane- 1-carboxylic acid derivative | |
| JPH023797B2 (en) | ||
| FR2486076A1 (en) | AMINOCYCLOPENTANONE AMIDES, THEIR PREPARATION AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM | |
| JP2909145B2 (en) | Preparation of β-lactamase inhibitors | |
| JPS606958B2 (en) | Antibiotic purification method | |
| EP0240338B1 (en) | Butenoic acid derivatives | |
| JP5613780B2 (en) | Lamivudine oxalate and method for producing the same | |
| JPH0359063B2 (en) | ||
| JPS5858345B2 (en) | Preparation of esters of PGE↓2 analogs | |
| JP2652027B2 (en) | Preparation and isolation of (R) -2-hydroxyphenylbutyric acid and esters | |
| JPH078853B2 (en) | Method for producing dopamine derivative | |
| JPH0532629A (en) | Production of highly pure methyl carbamate | |
| SU1082318A3 (en) | Process for isolating z-1,2-diphenyl-1/n-(2-dimethylamino-ethoxy/phenyl)butene-1 or its salts | |
| JPH0610164B2 (en) | Isoprenyl benzoate derivative and process for producing the same | |
| CN110746450A (en) | Synthetic method of beraprost sodium key intermediate | |
| JPS6034948B2 (en) | Production method of active vitamin D↓3 types | |
| JPS61271258A (en) | Production of optically active amino alcohol | |
| JPS6312860B2 (en) | ||
| JPH069523A (en) | Purification of 4-dedimethylaminotetracycline | |
| JPH02225462A (en) | N-acetyl-indoline-2-carboxylic acid ester and optical resolution |