JPH0142265B2 - - Google Patents
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- Publication number
- JPH0142265B2 JPH0142265B2 JP57035757A JP3575782A JPH0142265B2 JP H0142265 B2 JPH0142265 B2 JP H0142265B2 JP 57035757 A JP57035757 A JP 57035757A JP 3575782 A JP3575782 A JP 3575782A JP H0142265 B2 JPH0142265 B2 JP H0142265B2
- Authority
- JP
- Japan
- Prior art keywords
- compound
- solvent
- ethyl acetate
- group
- spectrum
- 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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Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
【発明の詳細な説明】
本発明は一般式（）で示されるビタミンD3
誘導体に関する。[Detailed Description of the Invention] The present invention provides vitamin D 3 represented by the general formula ().
Regarding derivatives.
（式中R1は水素原子又は水酸基を意味し、R2は
水素原子又は低級アルキル基を意味し、ｎは２乃
至４の整数を意味する。）
一般式（）で示されるビタミンD3誘導体は
それ自体ビタミンＤ様の生理活性を有し医薬とし
て有用であり、かつ血中のビタミンD3とりわけ
1α位に水酸基を有するビタミンD3誘導体、例え
ば1α，25−ジヒドロキシビタミンD3を抗原抗体
反応を用いて測定する際に必要な抗体を製造する
ためのハプテンとしても使用しうる。 (In the formula, R 1 means a hydrogen atom or a hydroxyl group, R 2 means a hydrogen atom or a lower alkyl group, and n means an integer from 2 to 4.) Vitamin D 3 derivative represented by the general formula () itself has a physiological activity similar to vitamin D and is useful as a medicine, and especially vitamin D3 in the blood.
It can also be used as a hapten for producing antibodies required when measuring vitamin D 3 derivatives having a hydroxyl group at the 1α position, such as 1α,25-dihydroxyvitamin D 3 , using an antigen-antibody reaction.
本発明の一般式（）で示される化合物は山田
等の方法（Chemistry Letters 583〜586、1979）
によつて得られる一般式（）で示される化合物
を出発物質として以下式示する方法で製造され
る。 The compound represented by the general formula () of the present invention can be prepared by the method of Yamada et al. (Chemistry Letters 583-586, 1979 ).
It is produced by the method shown below using the compound shown by the general formula () obtained by as a starting material.
（式中R″は水酸基の保護基を意味し、R′は水素
原子又は低級アルキル基を意味し、Ｒは水素原
子又は保護された水酸基を意味しＲは水酸基か又
は水素原子を意味し、ｎは２乃至４の整数を意味
し、Ｘはハロゲン原子を意味する。）
前記の反応式において水酸基の保護基としては
例えば一般式（）で示される化合物から化合物
（）を製造する際に不活性なものであれば特に
制限はないが、好ましくはエーテル系の保護基で
あり具体的には２−テトラヒドロピラニル基、β
−メトキシエトキシメチル基、メトキシメチル基
等である。 (In the formula, R'' means a protecting group for a hydroxyl group, R' means a hydrogen atom or a lower alkyl group, R means a hydrogen atom or a protected hydroxyl group, R means a hydroxyl group or a hydrogen atom, (n means an integer from 2 to 4, and X means a halogen atom.) In the above reaction formula, as a protecting group for a hydroxyl group, for example, when producing a compound () from a compound represented by the general formula (), There is no particular restriction as long as it is active, but ether-based protecting groups are preferred, specifically 2-tetrahydropyranyl group, β
-methoxyethoxymethyl group, methoxymethyl group, etc.
一般式（）においてR2で示される低級アル
キル基として、具体的にはメチル基、エチル基、
プロピル基、ブチル基、ｔ−ブチル基等である。 Specifically, the lower alkyl group represented by R2 in the general formula () is a methyl group, an ethyl group,
These include a propyl group, a butyl group, a t-butyl group, and the like.
参考例
（式中THPは２−テトラヒドロピラニル基を意
味する。）
化合物（ａ）21.33mgの乾燥塩化メチレン1.0
ml溶液にジヒドロピラン13μ、Amberlyst−15
（ローム・アンド・ハース社製）３mgを加え室温
下撹拌する。約１時間後、樹脂を除去しクロロホ
ルム層を濃縮する。残渣をシルカゲル４ｇを用い
たカラムクロマトグラフイー（溶媒：ｎ−ヘキサ
ン：酢酸エチル＝４：１）に付し精製し化合物
（a′）22.74mgを得る。Reference example (In the formula, THP means 2-tetrahydropyranyl group.) Compound (a) 21.33 mg dry methylene chloride 1.0
ml solution of dihydropyran 13μ, Amberlyst−15
(manufactured by Rohm & Haas) and stirred at room temperature. After about 1 hour, the resin is removed and the chloroform layer is concentrated. The residue was purified by column chromatography using 4 g of silica gel (solvent: n-hexane: ethyl acetate = 4:1) to obtain 22.74 mg of compound (a').
NMRスペクトル（CDCl3）δ：0.53（ｓ、18位
−Ｈ）、0.63（ｓ、18位−Ｈ）、1.22（ｓ、26位−Ｈ
および27位−Ｈ）
マススペクトルｍ／ｅ：568（M+−SO2）、484、
466、400
化合物（a′）19.9mgのテトラヒドロフラン
400μ、ヘキサメチルホスホリツクトリアミド
20μの混合溶液にｔ−ブチル−γ−ヨ−ドブチ
レート10μを加えアルゴン気流下撹拌しながら
ドライアイス−アセトンで−78℃に冷却する。こ
の溶液にリチウム−ビス（トリメチルシリル）ア
ミド16.16mgのテトラヒドロフラン200μ溶液を
−78℃に冷却して滴下する。約１時間後冷却した
まま酢酸エチル５mlを加え徐々に室温にもどす。
酢酸エチル層を飽和食塩水で２度洗浄し硫酸マグ
ネシウムで乾燥する。過した後溶媒を留去し、
残渣をシリカゲル10ｇを用いたカラムクロマトグ
ラフイー（溶媒：ｎ−ヘキサン：酢酸エチル＝
４：１）に付し化合物（ｄ）6.6mgを得る。 NMR spectrum (CDCl 3 ) δ: 0.53 (s, 18th-H), 0.63 (s, 18th-H), 1.22 (s, 26th-H)
and 27th position -H) Mass spectrum m/e: 568 (M + -SO 2 ), 484,
466, 400 Compound (a′) 19.9 mg of tetrahydrofuran
400μ, hexamethylphosphoric triamide
Add 10μ of t-butyl-γ-iodobutyrate to a 20μ mixed solution, and cool to -78°C with dry ice-acetone while stirring under an argon stream. A solution of 16.16 mg of lithium-bis(trimethylsilyl)amide in 200 µ of tetrahydrofuran is cooled to -78°C and added dropwise to this solution. After about 1 hour, add 5 ml of ethyl acetate while cooling and gradually return to room temperature.
The ethyl acetate layer was washed twice with saturated brine and dried over magnesium sulfate. After evaporation, the solvent was distilled off,
The residue was subjected to column chromatography using 10 g of silica gel (solvent: n-hexane: ethyl acetate =
4:1) to obtain 6.6 mg of compound (d).
NMRスペクトル（CDCl3）δ：0.56（ｓ、18位
−Ｈ）、0.66（ｓ、18位−Ｈ）、1.21（ｓ、26位−Ｈ
および27位−Ｈ）
マススペクトルｍ／ｅ：710（M+−SO2）、626、
608、542、524
実施例 １
化合物（ａ）17.38mgのエタノール5.0ml溶液
をアルゴン置換したボンベンロール中に入れ炭酸
水素ナトリウム52mgを加えて撹拌下約２時間90〜
100℃に加熱する。冷後酢酸エチルを加えて希塩
酸（１回）、水（５回）で洗浄後、硫酸マグネシ
ウムで乾燥する。溶媒留去後カラムクロマトグラ
フイー（セフアデツクスLH−20、10ｇ，ｎ−ヘ
キサン：クロロホルム：メタノール＝100：300：
６）に付し精製し化合物（ａ）9.55mgを得る。 NMR spectrum (CDCl 3 ) δ: 0.56 (s, 18th-H), 0.66 (s, 18th-H), 1.21 (s, 26th-H)
and 27th position -H) Mass spectrum m/e: 710 (M + -SO 2 ), 626,
608, 542, 524 Example 1 A solution of 17.38 mg of compound (a) in 5.0 ml of ethanol was placed in an argon-substituted bomben roll, and 52 mg of sodium hydrogen carbonate was added thereto, followed by stirring for about 2 hours.
Heat to 100℃. After cooling, add ethyl acetate, wash with dilute hydrochloric acid (once) and water (5 times), and dry over magnesium sulfate. After distilling off the solvent, column chromatography (Sephadex LH-20, 10 g, n-hexane:chloroform:methanol = 100:300:
6) to obtain 9.55 mg of compound (a).
IRスペクトル：1705cm-1
NMRスペクトル（CDCl3）δ：0.57（3H、ｓ）、
3.88（1H、ｍ）、5.20（1H、ｔ、Ｊ＝７Hz）、
5.89（1H、ｄ、Ｊ＝12Hz）、6.23（1H、ｄ、Ｊ＝
12Hz）
UVスペクトルλEtOH nax：268nｍ、
λmin：231nｍ
マススペクトルｍ／ｅ：470（M+）、452、222
実施例 ２
化合物（ｂ）35mgと炭酸水素ナトリウム80mg
のエタノール５ml溶液をアルゴン気流下90〜95℃
で4.5時間加熱する。冷後炭酸水素ナトリウムを
去し、エタノールを減圧留去し残渣をシリカゲ
ル９ｇを用いたカラムクロマトグラフイー（溶
媒：酢酸エチル：ｎ−ヘキサン＝１：４）に付し
精製し化合物（ｂ）20mgを得る。IR spectrum: 1705 cm -1 NMR spectrum (CDCl 3 ) δ: 0.57 (3H, s),
3.88 (1H, m), 5.20 (1H, t, J=7Hz),
5.89 (1H, d, J = 12Hz), 6.23 (1H, d, J =
12Hz) UV spectrum λ EtOH nax : 268nm, λmin: 231nm Mass spectrum m/e: 470 (M + ), 452, 222 Example 2 Compound (b) 35mg and sodium bicarbonate 80mg
Add 5 ml of ethanol solution to 90-95℃ under argon stream.
Heat for 4.5 hours. After cooling, sodium hydrogen carbonate was removed, ethanol was distilled off under reduced pressure, and the residue was purified by column chromatography using 9 g of silica gel (solvent: ethyl acetate: n-hexane = 1:4) to obtain 20 mg of compound (b). get.
NMRスペクトル（CDCl3）δ：0.54（3H、ｓ）、
1.45（9H、ｓ）、3.92（1H、ｍ）、5.29（1H、ｔ、
Ｊ＝７Hz）、5.94（1H、ｄ、Ｊ＝12Hz）、6.17
（1H、ｄ、Ｊ＝12Hz）
IRスペクトル：1710cm-1
マススペクトルｍ／ｅ：526（M+）、469、451、
278
UVスペクトルλEtOH nax：264nｍ
実施例 ３
化合物（b′）10mgを用い以下実施例２と同様
に処理し化合物（ｂ）８mgを得る。NMR spectrum (CDCl 3 ) δ: 0.54 (3H, s),
1.45 (9H, s), 3.92 (1H, m), 5.29 (1H, t,
J=7Hz), 5.94 (1H, d, J=12Hz), 6.17
(1H, d, J = 12Hz) IR spectrum: 1710cm -1 mass spectrum m/e: 526 (M + ), 469, 451,
278 UV spectrum λ EtOH nax : 264nm Example 3 10 mg of compound (b') was treated in the same manner as in Example 2 to obtain 8 mg of compound (b).
実施例 ４
（式中THPは２−テトラヒドロピラニル基を意
味する。）
化合物（ｃ）63mgを無水塩化メチレン10mlに
溶解し、氷点下トリフルオロ酢酸１mlを滴下、撹
拌する。室温下２時間撹拌後塩化メチレンを更に
加え、飽和食塩水で５回洗浄する。塩化メチレン
を硫酸マグネシウムで乾燥後塩化メチレンを減圧
留去しセフアデツクスLH−20、10ｇを用いたカ
ラムクロマトグラフイー（溶媒：ｎ−ヘキサン：
クロロホルム：メタノール＝100：300：６）に付
し精製し化合物（c′）25.9mgを得る。化合物
（c′）をそのまま５mlのエタノールに溶解し、
炭酸水素ナトリウム60mgを加えアルゴン気流下90
〜95℃で３時間加熱撹拌する。冷後酢酸エチルを
加え希塩酸（１回）、飽和食塩水（６回）で洗浄
し硫酸マグネシウムで乾燥する。酢酸エチルを減
圧留去した後残渣をセフアデツクスLH−20、10
ｇを用いたカラムクロマトグラフイー（溶媒：ｎ
−ヘキサン：クロロホルム：メタノール＝100：
300：６）に付し精製し化合物（ｃ）8.7mgを得
る。Example 4 (In the formula, THP means 2-tetrahydropyranyl group.) 63 mg of compound (c) is dissolved in 10 ml of anhydrous methylene chloride, and 1 ml of subzero trifluoroacetic acid is added dropwise and stirred. After stirring for 2 hours at room temperature, methylene chloride was further added and the mixture was washed 5 times with saturated brine. After drying the methylene chloride with magnesium sulfate, the methylene chloride was distilled off under reduced pressure and subjected to column chromatography using 10 g of Sephadex LH-20 (solvent: n-hexane:
Purification was performed using chloroform:methanol=100:300:6) to obtain 25.9 mg of compound (c'). Dissolve compound (c′) as it is in 5 ml of ethanol,
Add 60 mg of sodium bicarbonate and incubate for 90 minutes under an argon atmosphere.
Heat and stir at ~95°C for 3 hours. After cooling, add ethyl acetate, wash with dilute hydrochloric acid (once) and saturated brine (six times), and dry over magnesium sulfate. After ethyl acetate was distilled off under reduced pressure, the residue was purified by Sephadex LH-20, 10.
Column chromatography using g (solvent: n
-Hexane:Chloroform:Methanol=100:
300:6) to obtain 8.7 mg of compound (c).
NMRスペクトル（CDCl3）δ：0.58（3H、ｓ）、
3.81（1H、ｍ）、5.20（1H、ｔ、Ｊ＝７Hz）、
5.42（2H、bs）、5.91（1H、ｄ、Ｊ＝12Hz）、
6.27（1H、ｄ、Ｊ＝12Hz）
マススペクトルｍ／ｅ：484（M+）
UVスペクトルλEtOH nax：269nｍ、
λmin：232nｍ
実施例 ５
参考例で得られた化合物（ｄ）1.2mgの塩化
メチレン500μ溶液を室温で撹拌し、蒸留水50μ
とトリフルオロ酢酸100μを滴下する。約２
時間後塩化メチレンを加え飽和食塩水で４〜５回
洗浄後硫酸マグネシウムで乾燥し溶媒を留去す
る。残渣をセフアデツクスLH−20、５ｇを用い
たカラムクロマトグラフイー（溶媒：ｎ−ヘキサ
ン：クロロホルム：メタノール＝100：300：６）
に付し精製し化合物（d′）を得る。この化合物
（d′）のエタノール３ml溶液をアルゴン置換し
たボンベンロール中に入れ炭酸水素ナトリウム
2.0mgを加えて撹拌下90〜100℃で２時間加熱す
る。冷後酢酸エチルを加えて酢酸エチル層を希塩
酸（１回）、水（５回）で洗浄後硫酸マグネシウ
ムで乾燥する。溶媒を留去した後残渣をセフアデ
ツクスLH−20、５ｇを用いたカラムクロマトグ
ラフイー（溶媒：ｎ−ヘキサン：クロロホルム：
メタノール＝100：300：６）に付し精製し化合物
（ｄ）225μｇを得る。NMR spectrum (CDCl 3 ) δ: 0.58 (3H, s),
3.81 (1H, m), 5.20 (1H, t, J=7Hz),
5.42 (2H, bs), 5.91 (1H, d, J=12Hz),
6.27 (1H, d, J = 12Hz) Mass spectrum m/e: 484 (M + ) UV spectrum λ EtOH nax : 269 nm, λmin: 232 nm Example 5 A solution of 1.2 mg of compound (d) obtained in Reference Example in 500 μm of methylene chloride was stirred at room temperature, and mixed with 50 μm of distilled water.
and 100μ of trifluoroacetic acid. Approximately 2
After an hour, methylene chloride was added, and the mixture was washed 4 to 5 times with saturated brine, dried over magnesium sulfate, and the solvent was distilled off. The residue was subjected to column chromatography using 5 g of Sephadex LH-20 (solvent: n-hexane: chloroform: methanol = 100:300:6).
and purification to obtain compound (d'). A solution of 3 ml of ethanol of this compound (d') in argon-substituted Bombenroll was added to sodium hydrogen carbonate.
Add 2.0 mg and heat at 90 to 100°C for 2 hours while stirring. After cooling, ethyl acetate was added, and the ethyl acetate layer was washed with dilute hydrochloric acid (once) and water (5 times), and then dried over magnesium sulfate. After distilling off the solvent, the residue was subjected to column chromatography using 5 g of Sephadex LH-20 (solvent: n-hexane: chloroform:
The mixture was purified with methanol (100:300:6) to obtain 225 μg of compound (d).
UVスペクトルλEtOH nax：268nｍ
マススペクトルｍ／ｅ：486（M+）、468
実施例 ６
参考例で得られた化合物（ｄ）870μｇとAm
−berlyst−15、470μｇのエタノール溶液500μ
を40℃で２〜３時間加熱撹拌する。室温にもどし
樹脂を除去した後エタノールを留去した残渣をシ
リカゲル５ｇを用いたカラムクロマトグラフイー
（溶媒：ｎ−ヘキサン：酢酸エチル＝４：１〜
１：１）に付し精製し化合物（ｅ）を得る。こ
の化合物（ｅ）のエタノール3.0ml溶液をアル
ゴン置換したボンベンロール中に入れ炭酸水素ナ
トリウム1.7mgを加えて撹拌下約２時間90〜100℃
に加熱する。冷後酢酸エチルを加えて酢酸エチル
層を希塩酸（１回）、水（５回）で洗浄後硫酸マ
グネシウムで乾燥する。溶媒を留去した後残渣を
シリカゲル５ｇを用いたカラムクロマトグラフイ
ー（溶媒：ｎ−ヘキサン：酢酸エチル＝４：１）
に付し精製し化合物（ｅ）50μｇを得る。UV spectrum λ EtOH nax : 268 nm Mass spectrum m/e: 486 (M + ), 468 Example 6 870 μg of compound (d) obtained in the reference example and Am
-berlyst-15, 470μg ethanol solution 500μ
Heat and stir at 40°C for 2 to 3 hours. After returning to room temperature and removing the resin, ethanol was distilled off, and the residue was subjected to column chromatography using 5 g of silica gel (solvent: n-hexane: ethyl acetate = 4:1 ~
1:1) to obtain compound (e). A 3.0 ml solution of this compound (e) in ethanol was placed in a bomben roll purged with argon, and 1.7 mg of sodium bicarbonate was added thereto, and the mixture was heated at 90 to 100°C for about 2 hours with stirring.
Heat to. After cooling, ethyl acetate was added, and the ethyl acetate layer was washed with dilute hydrochloric acid (once) and water (5 times), and then dried over magnesium sulfate. After distilling off the solvent, the residue was subjected to column chromatography using 5 g of silica gel (solvent: n-hexane: ethyl acetate = 4:1).
Purification was performed to obtain 50 μg of compound (e).
UVスペクトルλEtOH nax：268nｍ マススペクトルｍ／ｅ：542（M+）、524UV spectrum λ EtOH nax : 268nm Mass spectrum m/e: 542 (M + ), 524
Claims (1)
は水素原子又は低級アルキル基を意味し、ｎは２
乃至４の整数を意味する。）で示されるビタミン
D3誘導体。[Claims] 1. General formula (In the formula, R 1 means a hydrogen atom or a hydroxyl group, and R 2
means a hydrogen atom or a lower alkyl group, and n is 2
means an integer between 4 and 4. ) Vitamins indicated by
D3 derivative.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP57035757A JPS58154556A (en) | 1982-03-09 | 1982-03-09 | Novel vitamin d3 derivative |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP57035757A JPS58154556A (en) | 1982-03-09 | 1982-03-09 | Novel vitamin d3 derivative |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS58154556A JPS58154556A (en) | 1983-09-14 |
| JPH0142265B2 true JPH0142265B2 (en) | 1989-09-11 |
Family
ID=12450706
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP57035757A Granted JPS58154556A (en) | 1982-03-09 | 1982-03-09 | Novel vitamin d3 derivative |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS58154556A (en) |
-
1982
- 1982-03-09 JP JP57035757A patent/JPS58154556A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS58154556A (en) | 1983-09-14 |
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