JPS588096A - Production method of 19-norethisterone - Google Patents
Production method of 19-norethisteroneInfo
- Publication number
- JPS588096A JPS588096A JP10674381A JP10674381A JPS588096A JP S588096 A JPS588096 A JP S588096A JP 10674381 A JP10674381 A JP 10674381A JP 10674381 A JP10674381 A JP 10674381A JP S588096 A JPS588096 A JP S588096A
- Authority
- JP
- Japan
- Prior art keywords
- reaction
- acetylene
- nad
- alcohol
- present
- 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
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- VIKNJXKGJWUCNN-XGXHKTLJSA-N norethisterone Chemical compound O=C1CC[C@@H]2[C@H]3CC[C@](C)([C@](CC4)(O)C#C)[C@@H]4[C@@H]3CCC2=C1 VIKNJXKGJWUCNN-XGXHKTLJSA-N 0.000 title 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 21
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 13
- 238000006243 chemical reaction Methods 0.000 claims description 12
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 11
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 11
- 235000011118 potassium hydroxide Nutrition 0.000 claims description 7
- 239000003960 organic solvent Substances 0.000 claims description 6
- 239000011541 reaction mixture Substances 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 5
- 239000007795 chemical reaction product Substances 0.000 claims description 3
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims 1
- 229940095064 tartrate Drugs 0.000 claims 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- -1 aliphatic alcohols Chemical class 0.000 description 2
- 238000006555 catalytic reaction Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 230000003472 neutralizing effect Effects 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- YEYKMVJDLWJFOA-UHFFFAOYSA-N 2-propoxyethanol Chemical compound CCCOCCO YEYKMVJDLWJFOA-UHFFFAOYSA-N 0.000 description 1
- TVEXGJYMHHTVKP-UHFFFAOYSA-N 6-oxabicyclo[3.2.1]oct-3-en-7-one Chemical compound C1C2C(=O)OC1C=CC2 TVEXGJYMHHTVKP-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- RJKFOVLPORLFTN-LEKSSAKUSA-N Progesterone Chemical class C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)C)[C@@]1(C)CC2 RJKFOVLPORLFTN-LEKSSAKUSA-N 0.000 description 1
- 229930182558 Sterol Natural products 0.000 description 1
- DWCSNWXARWMZTG-UHFFFAOYSA-N Trigonegenin A Natural products CC1C(C2(CCC3C4(C)CCC(O)C=C4CCC3C2C2)C)C2OC11CCC(C)CO1 DWCSNWXARWMZTG-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- WQLVFSAGQJTQCK-VKROHFNGSA-N diosgenin Chemical compound O([C@@H]1[C@@H]([C@]2(CC[C@@H]3[C@@]4(C)CC[C@H](O)CC4=CC[C@H]3[C@@H]2C1)C)[C@@H]1C)[C@]11CC[C@@H](C)CO1 WQLVFSAGQJTQCK-VKROHFNGSA-N 0.000 description 1
- WQLVFSAGQJTQCK-UHFFFAOYSA-N diosgenin Natural products CC1C(C2(CCC3C4(C)CCC(O)CC4=CCC3C2C2)C)C2OC11CCC(C)CO1 WQLVFSAGQJTQCK-UHFFFAOYSA-N 0.000 description 1
- 238000000855 fermentation Methods 0.000 description 1
- 230000004151 fermentation Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- OSVMTWJCGUFAOD-KZQROQTASA-N formestane Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CCC2=C1O OSVMTWJCGUFAOD-KZQROQTASA-N 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000000583 progesterone congener Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 150000003432 sterols Chemical class 0.000 description 1
- 235000003702 sterols Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Landscapes
- Steroid Compounds (AREA)
Abstract
(57)【要約】本公報は電子出願前の出願データであるた
め要約のデータは記録されません。(57) [Summary] This bulletin contains application data before electronic filing, so abstract data is not recorded.
Description
【発明の詳細な説明】
本発明は／ターノルエチステロン（以下「ＮＥＴ」とい
う）の製法に関する。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a method for producing ternorethisterone (hereinafter referred to as "NET").
さらに詳しくはｌターツルーアンドロスト−≠−エンー
３，１７−ジオン（以下「ＮＡＤ」という）から黄体ホ
ルモン剤として有用なＮＥＴの製法に関する。More specifically, the present invention relates to a method for producing NET, which is useful as a progestin, from 1-tertu-androst-≠-en-3,17-dione (hereinafter referred to as "NAD").
ＮＡＤはジオスゲニンから誘導される３β−ヒトゝロキ
シアンドロストーｊ−エンー／７−オンを経由して合成
される方法の外にステロール類の醗酵によって製造され
るアンドロスー−／、弘−ジエン−３，／７−シオンカ
ラエストロンヲ経由しても合成される。NAD is synthesized via 3β-human oxyandrostene/7-one derived from diosgenin, and also by fermentation of sterols. , /7-Sionkaraestrone can also be synthesized.
ＮＥＴはＮＡＤのエチニル化を行なって合成されるが従
来は試薬としてｔθｒｔ−ブトキシカリウムがアセチレ
ンと共に使用されていた。NET is synthesized by ethynylation of NAD, but tθrt-butoxypotassium has conventionally been used together with acetylene as a reagent.
本発明者番は、より安価なカセイカリを使用しかつ特定
の後処理方法を用いるｉとはより高収率高純度のＮＥＴ
がＮＡＤから容易に得られることを見出し本発明に到達
した。すなわち、本発明は、非プロトン性有機溶媒中で
純度り０チ以上のカセイカリとアルコールを２０℃〜６
０℃で反応させた後、反応生成物にアセチレンを供給し
得られたアセチレン付加物とＮ、ＡＤを２０℃以下で反
応させ、ついで得られた反応混合物を、２！−ＡＯ℃に
保持した夜酸性として酸接触反応させ、さらに中和する
ことによりＮＩＣＴを製造することを特徴とするＮＥＴ
の製法にある。The inventors believe that using cheaper caustic potash and using specific post-treatment methods will result in higher yields and higher purity NETs.
The present invention was achieved by discovering that the compound can be easily obtained from NAD. That is, in the present invention, caustic potash with a purity of 0 or higher and alcohol are heated in an aprotic organic solvent at 20°C to 6°C.
After reacting at 0°C, acetylene is supplied to the reaction product, and the resulting acetylene adduct is reacted with N and AD at 20°C or lower, and then the resulting reaction mixture is heated to 2! - A NET characterized in that NICT is produced by carrying out an acid catalytic reaction in the form of night acidity maintained at AO°C and further neutralizing it.
It is in the manufacturing method.
以下本発明の詳細な説明する。The present invention will be explained in detail below.
本発明方法においては、まず非プロトン性有機溶媒中で
カセイカリとアルコールを反応させる。非プロトン性有
機溶剤としてはテトラヒドロフラン、ジオキサン、Ｎ−
メチルピロリドン、ジメチルフォルムアミド、等があげ
られるが工業的にはテトラヒドロフランが一般的である
。In the method of the present invention, caustic potash and alcohol are first reacted in an aprotic organic solvent. Examples of aprotic organic solvents include tetrahydrofuran, dioxane, N-
Examples include methylpyrrolidone, dimethylformamide, etc., but tetrahydrofuran is industrially common.
カセイカリとしてはり０％以上の純度特に望ましくはり
３チ以上のも、のが使用される。Caustic potash having a purity of 0% or more, preferably 3% or more, is used.
一方、アルコールとしては、メタノール、エタノール、
グロパノール、インプロパツール、ｎ−ブタノール、θ
θＣ−ブタノール、ｔθｒｔ−ブタノール等の低級脂肪
族アルコールおよびエチレングリコールモノメチルエー
テル、エテレ／クリコールモノエチルエーテル、エチレ
ンクリコールモノプロピルエーテル、エチレングリコー
ルモノブチルエーテル等のエチレングリコールモノアル
キルエーテル等が通常用いられる。On the other hand, alcohols include methanol, ethanol,
Gropanol, Impropatool, n-butanol, θ
Lower aliphatic alcohols such as θC-butanol and tθrt-butanol, and ethylene glycol monoalkyl ethers such as ethylene glycol monomethyl ether, etele/glycol monoethyl ether, ethylene glycol monopropyl ether, and ethylene glycol monobutyl ether are usually used. .
アルコールの選定は溶媒の回収精製を考えると、溶剤と
十分沸点の離れたアルコールを選択するのが好ましい。Considering the recovery and purification of the solvent, it is preferable to select an alcohol whose boiling point is sufficiently different from that of the solvent.
カセイカリとアルコールとの反応温度は、１０℃〜還流
温度程度、好ましくは−ｏ−ｓｏ℃である。反応時間は
、通常、数分〜数時間程度である。The reaction temperature of caustic potash and alcohol is about 10°C to reflux temperature, preferably -o-so°C. The reaction time is usually about several minutes to several hours.
次いで得られた反応生成物にアセチレンを供給して反応
させる。反応温度は通常−２０〜士、２０℃程度、好ま
しくは−ｊ〜十１０℃程度であり、反応時間は通常、数
分〜数時間程度である０
さらに、得られたアセチレン付加物とＮＡＤを反応させ
る。ＮＡＤは、上記の有機溶媒溶液として用いることも
できる。Next, acetylene is supplied to the obtained reaction product to cause the reaction to occur. The reaction temperature is usually about -20°C to 20°C, preferably about -110°C, and the reaction time is usually about several minutes to several hours. Furthermore, the obtained acetylene adduct and NAD are Make it react. NAD can also be used as a solution in the above organic solvent.
反応時間は通常、数分〜数時間程度である。The reaction time is usually about several minutes to several hours.
反応温度が２０℃を超えると、転化１．率の低下、さら
には生成物の着手を生じるおそれがあるので、本発明に
おいては、上記反応においては、２０℃以下の温度が採
用される。When the reaction temperature exceeds 20°C, conversion 1. In the present invention, a temperature of 20° C. or lower is employed in the above reaction, since this may cause a decrease in the reaction rate or even formation of the product.
上記の反応において、前記力セイカリ及びアルコールの
使用量はＮＡＤに対し、それぞれ７〜３０倍モル、コ〜
／ｊ倍モル程度から選択される。前記非プロトン性有機
溶媒は、ＮＡＤ／ｙに対し、ｊ−！Ｏｄ、程度が使用さ
れる。In the above reaction, the amount of the alcohol and alcohol used is 7 to 30 times the mole of NAD, respectively.
/j times the mole. The aprotic organic solvent has a ratio of j-! to NAD/y. Od, degree is used.
なお、上記ＮＡＤとアセチレン付加物の反応に際しては
、アセチレンを存在させておくと、反応収率が一層向上
するので、好ましい。In addition, it is preferable to have acetylene present in the reaction between NAD and the acetylene adduct, since this further improves the reaction yield.
次いで、得られる反応混合物は、Ｊｊ〜６０℃に昇温、
保持される。時間は通常、数分〜１０時間程度である。Then, the resulting reaction mixture was heated to Jj ~ 60°C,
Retained. The time usually ranges from several minutes to about 10 hours.
１
この保持によって、反応混合物中の副生物が、ＮＦＸＴ
に変換し得る物質に後続の中和処理後に転換され、この
結果、ＮｇＴの収率が向上する。1 This retention ensures that by-products in the reaction mixture are free from NFXT
After the subsequent neutralization treatment, the NgT yield is improved.
次いで、反応混合物は、塩酸、硫酸、硝酸等の鉱酸又は
有機酸又はその水溶液等によって酸性とされ、１０℃〜
ｔｏ℃好ましくは−ｊ℃〜’Ａ Ｏ″ｃ１での温度で数
分から数時間攪拌下に処理され、酸接触反応が行なわれ
る。Next, the reaction mixture is made acidic with a mineral acid or an organic acid such as hydrochloric acid, sulfuric acid, nitric acid, or an aqueous solution thereof, and heated at 10°C to
The acid catalytic reaction is carried out under stirring for several minutes to several hours at a temperature of to°C, preferably -j°C to 'A O'c1.
さらに、カセイソーダ等のアルカリ水溶液で中和される
。Furthermore, it is neutralized with an alkaline aqueous solution such as caustic soda.
反応終了後、反応混合物から、常法によりＮＥＴが分離
される。この分離方法としては、例えば、溶媒を留去し
、ろ過またば抽出した後晶析してｐ遇する方法が埜げら
れる。この様Ｖこして収率よ（ＮＥＴを製造することが
できる。After the reaction is completed, NET is separated from the reaction mixture by a conventional method. Examples of this separation method include distilling off the solvent, filtering or extracting, and then crystallizing and treating. In this way, NET can be produced with a high yield.
以下、実施例により本発明をさらに詳細に説明するが、
本発明はその要旨を超えない限りこれら実施例に限定さ
れない。Hereinafter, the present invention will be explained in more detail with reference to Examples.
The present invention is not limited to these examples unless it exceeds the gist thereof.
実施例／
テトラヒドロフ２ン、２！−に？ｊ’ｌＡのカセイカリ
７．ｊ９をカロえさらにエタノールＬｊｍｌを力］１え
て≠Ｏ℃３０分間攪拌した。フレーク状のカセイカリは
カニ状に変わったｏ、 ／ ０℃に冷却してアセチレン
を２０分間通人した。さらにアセチレンの通人を続行し
ながら純度９７ｇ％のＮ Ａ Ｄ ２．３ ｆ １９を
２ｊ−のＴＨＦに溶解した溶液をｊ分で滴下した０３時
間後に３０℃に昇温し３０分間攪拌をつづけた。ついで
／♂チ塩酸水溶液ｊＯ−を加えて３０℃で３０分攪拌し
た。Example/Tetrahydrofurine, 2! −to? j'lA caustic potash7. Add 1 ml of ethanol, add 1 ml of ethanol, and stir at ≠0°C for 30 minutes. The flaky caustic potash turned into a crab-like shape. It was cooled to /0°C and soaked in acetylene for 20 minutes. Furthermore, while continuing to add acetylene, a solution of NAD 2.3 f 19 with a purity of 97 g% dissolved in 2j- of THF was added dropwise over j minutes. After 3 hours, the temperature was raised to 30°C and stirring was continued for 30 minutes. Ta. Then, an aqueous solution of /♂thihydrochloric acid jO- was added and stirred at 30°C for 30 minutes.
コＱ−カセイソーダ水溶液で中和を行ないテトラヒドロ
フランを留去した後けんだく状態の結晶を戸数し乾燥し
た。粗結晶重量はコ、ｌＩｊｇＮＥＴ純度はりｊｔ、Ｊ
チであった。（収率タグ、７−）
出 願 人 三菱化成工業株式会社After neutralizing with an aqueous solution of Co-Q-caustic soda and distilling off tetrahydrofuran, the suspended crystals were dried. Crude crystal weight is ko, lIjgNET purity balance jt, J
It was Chi. (Yield tag, 7-) Applicant Mitsubishi Chemical Industries, Ltd.
Claims (1)
イカリとアルコールを２０℃〜６０℃で反応させた後、
反応生成物にアセチレンを供給し、得られたアセチレン
付加物とｌターツルーアンドロスト−グーエン−３，／
７−ジオンを、２０℃以下で反応させ、ついで、得られ
た反応混合物をｊ ｊ −１０℃に保持した後酸性とし
て酸接触反応させ、さらに中和することにより／ターノ
ルエチステロンを生成させることを特徴とする／ターノ
ルエチステロンの製法。(1) After reacting caustic potash with a purity of 0% or more and alcohol at 20°C to 60°C in an aprotic organic solvent,
Acetylene is supplied to the reaction product, and the resulting acetylene adduct and l tartrate androst-gouene-3,/
7-dione is reacted at 20°C or lower, the resulting reaction mixture is then maintained at -10°C, acidified and subjected to an acid contact reaction, and further neutralized to produce ternorethisterone. Features/Manufacturing method of ternorethisterone.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10674381A JPS588096A (en) | 1981-07-08 | 1981-07-08 | Production method of 19-norethisterone |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10674381A JPS588096A (en) | 1981-07-08 | 1981-07-08 | Production method of 19-norethisterone |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS588096A true JPS588096A (en) | 1983-01-18 |
| JPS6355517B2 JPS6355517B2 (en) | 1988-11-02 |
Family
ID=14441397
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP10674381A Granted JPS588096A (en) | 1981-07-08 | 1981-07-08 | Production method of 19-norethisterone |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS588096A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2018185783A1 (en) * | 2017-04-06 | 2018-10-11 | Coral Drugs Pvt. Ltd. | Novel process for preparation of 19-norsteroids |
-
1981
- 1981-07-08 JP JP10674381A patent/JPS588096A/en active Granted
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2018185783A1 (en) * | 2017-04-06 | 2018-10-11 | Coral Drugs Pvt. Ltd. | Novel process for preparation of 19-norsteroids |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6355517B2 (en) | 1988-11-02 |
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