JPH053875B2 - - Google Patents
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- Publication number
- JPH053875B2 JPH053875B2 JP13330885A JP13330885A JPH053875B2 JP H053875 B2 JPH053875 B2 JP H053875B2 JP 13330885 A JP13330885 A JP 13330885A JP 13330885 A JP13330885 A JP 13330885A JP H053875 B2 JPH053875 B2 JP H053875B2
- Authority
- JP
- Japan
- Prior art keywords
- hexafluoro
- hydroxy
- vitamin
- spectrum
- 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.)
- Expired - Lifetime
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
【発明の詳細な説明】
本発明はビタミンＤ様生理活性を有する新規な
フツ素置換ビタミンD3誘導体に関する。更に詳
しくは本発明は次式で示される26，26，26，27，
27，27−ヘキサフルオロ−25−ヒドロキシ−24−
オキソビタミンD3に関する。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to novel fluorine-substituted vitamin D 3 derivatives having vitamin D-like physiological activity. More specifically, the present invention provides 26, 26, 26, 27,
27,27-hexafluoro-25-hydroxy-24-
Concerning oxovitamin D3 .
本発明のフツ素化ビタミンD3は新規化合物で
あり、例えば26，26，26，27，27，27−ヘキサフ
ルオロ−25−ヒドロキシ−24−オキソプロビタミ
ンD3（）に紫外線を照射し次いで異性化すると
いう一連の反応に付すことにより製造することが
できる。この一連の反応はビタミンＤ類を製造す
る際の常法であり、処理手段等は例えば特開昭51
−19752号公報に詳しく記載されている。なお出
発物質であるプロビタミンD3誘導体（）は、
例えば特開昭57−106699号公報に記載されている
22−ブロム−23，24−ビスノル−５，７−コラジ
エン−3β−オール ３−テトラヒドロピラニル
エーテル（）を用い、以下式示する方法により
製造される。 The fluorinated vitamin D 3 of the present invention is a new compound. It can be produced by subjecting it to a series of reactions called isomerization. This series of reactions is a conventional method for producing vitamin D, and the processing means, etc.
- It is described in detail in Publication No. 19752. The starting material, provitamin D 3 derivative (), is
For example, it is described in Japanese Patent Application Laid-Open No. 57-106699.
22-bromo-23,24-bisnor-5,7-coladien-3β-ol It is produced by the method shown below using 3-tetrahydropyranyl ether ().
（反応式中THPは２−テトラヒドロピラニル
基を、phはフエニル基を意味する。）
実施例
ａ 26，26，26，27，27，27−ヘキサフルオロ−
25−ヒドロキシ−24−オキソプロビタミンD3
1.8mg、エーテル200mlを氷冷攪拌しながら30分
間アルゴンを導通させた後、バイコールフイル
ター（Vycorfilter）と高圧水銀ランプ
（200V）を用いて２分間光照射する。溶媒を留
去後カラムクロマトグラフイー（LH−20：
25g、クロロホルム：ヘキサン＝３：２）で精
製し、26，26，26，27，27，27−ヘキサフルオ
ロ−25−ヒドロキシ−24−オキソプレビタミン
D3642μgを得る。［UVスペクトル（局方エタノ
ール）λmax：260nm）］
ｂ 前記ａ）で得たプレビタミンD3体642μgを室
温、遮光して20日間放置する。溶媒を留去後カ
ラムクロマトグラフイー（LH−20：25g、ク
ロロホルム：ヘキサン＝３：２）で精製し、
26，26，26，27，27，27−ヘキサフルオロ−25
−ヒドロキシ−24−オキソビタミンD3380μgを
得た。 (In the reaction formula, THP means 2-tetrahydropyranyl group, and ph means phenyl group.) Example a 26,26,26,27,27,27-hexafluoro-
25-Hydroxy-24-oxoprovitamin D 3
After passing argon through 1.8 mg and 200 ml of ether while stirring on ice for 30 minutes, the mixture was irradiated with light for 2 minutes using a Vycor filter and a high-pressure mercury lamp (200 V). After distilling off the solvent, column chromatography (LH-20:
25g, purified with chloroform:hexane=3:2), 26,26,26,27,27,27-hexafluoro-25-hydroxy-24-oxoprevitamin
Obtain 642 μg of D3 . [UV spectrum (pharmacopoeial ethanol) λmax: 260 nm)] b 642 μg of the three previtamin Ds obtained in a) above was left at room temperature, protected from light, for 20 days. After distilling off the solvent, it was purified by column chromatography (LH-20: 25 g, chloroform:hexane = 3:2),
26, 26, 26, 27, 27, 27-hexafluoro-25
-Hydroxy-24-oxovitamin D 3 380 μg was obtained.
1HNMRスペクトル（CDCl3）δ：0.56（3H，
ｓ）、0.95（3H，ｄ，Ｊ＝6Hz），2.84（2H，
ｍ），３，98（1H，ｍ），4.85（1H，ｄ，Ｊ＝
2Hz），5.08（1H，ｍ）6.06（1H，ｄ，Ｊ＝
12Hz），6.28（1H，ｄ，Ｊ＝12Hz）
マススペクトルｍ／ｅ：522（M+）、489，355，
271，253，136，118
UVスペクトル（局方エタノール）λmax：
265，λmin：228nm1H NMR spectrum (CDCl 3 ) δ: 0.56 (3H,
s), 0.95 (3H, d, J=6Hz), 2.84 (2H,
m), 3,98 (1H, m), 4.85 (1H, d, J=
2Hz), 5.08 (1H, m) 6.06 (1H, d, J=
12Hz), 6.28 (1H, d, J = 12Hz) Mass spectrum m/e: 522 (M + ), 489, 355,
271, 253, 136, 118 UV spectrum (pharmacopoeia ethanol) λmax:
265, λmin: 228nm
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP13330885A JPS61291562A (en) | 1985-06-19 | 1985-06-19 | Novel fluorinated vitamin d3 derivative |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP13330885A JPS61291562A (en) | 1985-06-19 | 1985-06-19 | Novel fluorinated vitamin d3 derivative |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS61291562A JPS61291562A (en) | 1986-12-22 |
| JPH053875B2 true JPH053875B2 (en) | 1993-01-18 |
Family
ID=15101630
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP13330885A Granted JPS61291562A (en) | 1985-06-19 | 1985-06-19 | Novel fluorinated vitamin d3 derivative |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS61291562A (en) |
-
1985
- 1985-06-19 JP JP13330885A patent/JPS61291562A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS61291562A (en) | 1986-12-22 |
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