JPS5844679B2 - 11,12,13,14- Tetrahydroacyl diyosamycin - Google Patents
11,12,13,14- Tetrahydroacyl diyosamycinInfo
- Publication number
- JPS5844679B2 JPS5844679B2 JP3470975A JP3470975A JPS5844679B2 JP S5844679 B2 JPS5844679 B2 JP S5844679B2 JP 3470975 A JP3470975 A JP 3470975A JP 3470975 A JP3470975 A JP 3470975A JP S5844679 B2 JPS5844679 B2 JP S5844679B2
- Authority
- JP
- Japan
- Prior art keywords
- tetrahydroacyl
- diyosamycin
- absorption spectrum
- acyljosamycin
- catalyst
- 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
Links
Landscapes
- Saccharide Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
【発明の詳細な説明】
本発明は、一般式
（式中Ｒ１はアシル基を、およびＲ２は水素原子または
アシル基を意味する。DETAILED DESCRIPTION OF THE INVENTION The present invention is based on the general formula (where R1 represents an acyl group, and R2 represents a hydrogen atom or an acyl group).
） ４壷で示されるアシルジョサマイシ
ンを水素化することを特徴とする一般式
（式中Ｒ１およびＲ２は前記と同じ。) General formula characterized by hydrogenation of the acyljosamycin shown in 4 bottles (wherein R1 and R2 are the same as above).
）で示される１１，１２，１３，１４−テトラヒドロア
シルジョサマイシンの製造法に関する。) The present invention relates to a method for producing 11,12,13,14-tetrahydroacyljosamycin.
アシルジョサマイシンは特公昭４５−２０６８１号又は
特公昭４５−２１６８２号の方法によりジョサマイシン
（％公昭４１−２１７５９号公報参照）の有する２個の
２級水酸基の内、少なくとも１個がアシル化されている
苦味のない、且つジョサマイシンの生物学的活性を保持
するジョサマイシンの１０−及び／又は２−アシル誘導
体である。Acyljosamycin is obtained by acylating at least one of the two secondary hydroxyl groups of josamycin (see Japanese Patent Publication No. 41-21759) by the method of Japanese Patent Publication No. 45-20681 or No. 45-21682. It is a 10- and/or 2-acyl derivative of josamycin that has no bitter taste and retains the biological activity of josamycin.
鼓にいうアシル誘導体としては、たとえばアセチル、プ
ロピオニル、ブチリル等の誘導体を挙げることができる
。Examples of acyl derivatives referred to in drums include derivatives of acetyl, propionyl, butyryl, and the like.
本発明において目的とする１１，１２，１３゜１４−テ
トラヒドロアシルジョサマイシンはこのアシルジョサマ
イシンを水素化することにより得ることができる。The 11,12,13°14-tetrahydroacyljosamycin targeted in the present invention can be obtained by hydrogenating this acyljosamycin.
本発明を実施するには１１−位および１３−位の共役二
重結合を有する炭素原子のみ水素化をうける条件で行う
のが望ましく、通常は常温常圧で触媒の存在下にアシル
ジョサマイシンを適当な溶媒中で接触還元することによ
り行なわれる。In carrying out the present invention, it is preferable to carry out hydrogenation under conditions in which only the carbon atoms having conjugated double bonds at the 11- and 13-positions undergo hydrogenation, and usually an acyljosamycin is hydrogenated in the presence of a catalyst at room temperature and normal pressure. It is carried out by catalytic reduction in a suitable solvent.
触媒としては通常接触還元に用いられるものであればよ
く、白金、パラジウム、ロジウム、ニッケル等が挙げら
れ、又溶媒としてはメタノール、エタノール、ベンゼン
、アセトン、メチルエチルケトン、メチルイソブチルケ
トン、酢酸エチル、酢酸ブチル等の有機溶媒が用いられ
る。The catalyst may be any catalyst normally used for catalytic reduction, and examples of the solvent include methanol, ethanol, benzene, acetone, methyl ethyl ketone, methyl isobutyl ketone, ethyl acetate, and butyl acetate. Organic solvents such as
反応により得られた１１，１２，１３，１４−テトラヒ
ドロアシルジョサマイシンは触媒の除去後、濃縮、析出
化溶媒による析出あるいはカラムクロマトグラフィー等
の操作により分離精製される。After removing the catalyst, the 11,12,13,14-tetrahydroacyljosamycin obtained by the reaction is separated and purified by operations such as concentration, precipitation with a precipitation solvent, or column chromatography.
本発明で得られた１１，１２，１３，１４テトラヒドロ
アシルジヨサマイシンはダラム陽性菌感染症に有効な医
薬である。The 11,12,13,14 tetrahydroacyl diyosamycin obtained in the present invention is an effective drug for Durum positive bacterial infections.
実施例 １
１０−アセチルジョサマイシン１．６ｇを溶解したエタ
ノ−／Ｌ１５０ｒｒＬｌに５％パラジウム炭素粉末０．
５ｇの存在下、水素を２５°Ｃで２時間（９２ｍｌ消費
するまで）接触還元する。Example 1 5% palladium on carbon powder was added to 150rrLl of ethanol/L in which 1.6g of 10-acetyljosamycin was dissolved.
Hydrogen is catalytically reduced in the presence of 5 g at 25° C. for 2 hours (until 92 ml is consumed).
触媒を１別し、１液を減圧濃縮すると１α〕２５−６１
．６（Ｃ＝１クロロホルム）を示す１〇−アセチル−１
１，１２，１３，１４−テトロヒドロジョサマイシン１
．５４．！９の白色粉末を得る。Separate the catalyst and concentrate the liquid under reduced pressure to obtain 1α]25-61
．． 10-acetyl-1 indicating 6 (C=1 chloroform)
1,12,13,14-tetrohydrjosamycin 1
．． 54. ! 9 white powder is obtained.
元素分析値〔Ｃ４４Ｈ７５０１６Ｎとして〕Ｃ％
Ｎ％ Ｎ％
実測値 ６０．４２ ８．９９ １．４４理論
値 ６０．４６ ８，６５ １．６０本品の紫
外部吸収スペクトルは第１図に示す通りであって、ジョ
サマイシンの有するα、β、γ。Elemental analysis value [as C44H75016N] C%
N% N% Actual value 60.42 8.99 1.44 Theoretical value 60.46 8,65 1.60 The ultraviolet absorption spectrum of this product is as shown in Figure 1, and the α and β of josamycin , γ.
δ−不飽和アルコールのアシル誘導体に由来する２３２
ｍμの強い吸収が消失する。232 derived from acyl derivatives of δ-unsaturated alcohols
The strong absorption of mμ disappears.
本旨の赤外線吸収スペクトルを第２図に示す。The main infrared absorption spectrum is shown in FIG.
本旨の核磁気共鳴スペクトルでは５．５〜６．６ ｐ
ｐｍに−ｃ−６−Ｈの存在が見られない。The main nuclear magnetic resonance spectrum is 5.5 to 6.6 p.
No presence of -c-6-H is observed in pm.
実施例 ２
１０−ツーピオニルジョサマイシン１．６９を溶解した
エタノール５０ｍ１に５％パラジウム炭素粉末０．５ｇ
の存在下、水素を２５８Ｃで２時間（９７ｒ／ｌｌ消費
するまで）接触還元する。Example 2 0.5 g of 5% palladium on carbon powder in 50 ml of ethanol in which 1.69 of 10-two-pionyljosamycin was dissolved
The hydrogen is catalytically reduced at 258 C for 2 hours (until 97 r/ll is consumed).
以下実施例１と同様に行うと１１．１２，１３゜１４−
テトラヒドロ−１０−プロピオニルジョサマイシンの白
色粉末１．５１を得る。Following the same procedure as in Example 1, 11.12, 13°14-
1.51 of a white powder of tetrahydro-10-propionyljosamycin is obtained.
元素分析値’−Ｃ４！５Ｈ７□０１６Ｎとして〕Ｃ％
Ｎ％ Ｎ％
実演１１（直 ６１．０５ ９．００
１．３９理論値 ６０．８６ ８，７４
１．５８本品の紫外部吸収スペクトルは第３図に示す通
りであって、１０−プロピオニルジョサマイシンの有す
る２３２ｍμの強い吸収は消失する。Elemental analysis value '-C4!5H7□016N〕C%
N% N% Demonstration 11 (direct 61.05 9.00
1.39 theoretical value 60.86 8,74
1.58 The ultraviolet absorption spectrum of this product is as shown in Figure 3, and the strong absorption at 232 mμ of 10-propionyljosamycin disappears.
本旨の赤外線吸収スペクトルを第４図に示す。The main infrared absorption spectrum is shown in FIG.
本旨の核磁気共鳴スペクトルでは５．５〜６．６ｐｐｍ
に−Ｃ＝Ｃ−Ｈの存在が見られない。In the main nuclear magnetic resonance spectrum, it is 5.5 to 6.6 ppm.
The presence of -C=C-H is not observed in.
第１図は１０−アセチル−１１，１２，１３゜１４−テ
トラヒドロジョサマイシンの紫外部吸収スヘクトル、第
２図は１０−アセチル−１１，１２１３，１４−テトラ
ヒドロジョサマイシンの赤外線吸収スペクトル、第３図
は１１，１２，１３゜１４−テトラヒドロ−１０−プロ
ピオニルジョサマイシンの紫外部吸収上ベクトル、第４
図は１１゜１２．１３，１４−テトラヒドロ−１０−プ
ロピオニルジョサマイシンの赤外線吸収スペクトルを示
す。Figure 1 shows the ultraviolet absorption spectrum of 10-acetyl-11,12,13°14-tetrahydrjosamycin, Figure 2 shows the infrared absorption spectrum of 10-acetyl-11,1213,14-tetrahydrjosamycin, and Figure 3 shows the 11 , 12, 13° Ultraviolet absorption vector of 14-tetrahydro-10-propionyljosamycin, 4th
The figure shows the infrared absorption spectrum of 11°12.13,14-tetrahydro-10-propionyljosamycin.
Claims (1)
アシル基を意味する。 ）で示されるアシルジョサマイシンを水素化することを
特徴とする特許 （式中、Ｒ１およびＲ２は前記と同じ。 ）で示される１１，１２．１３，１．４−テトラヒドロ
アシルジョサマイシンの製造法。 ＊[Claims] A patent characterized by hydrogenating an acyljosamycin represented by the general formula 1 (wherein R□ represents an acyl group, and R2 represents a hydrogen atom or an acyl group). , R1 and R2 are the same as above.) A method for producing 11,12.13,1.4-tetrahydroacyljosamycin. *
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3470975A JPS5844679B2 (en) | 1975-03-22 | 1975-03-22 | 11,12,13,14- Tetrahydroacyl diyosamycin |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3470975A JPS5844679B2 (en) | 1975-03-22 | 1975-03-22 | 11,12,13,14- Tetrahydroacyl diyosamycin |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS51110584A JPS51110584A (en) | 1976-09-30 |
| JPS5844679B2 true JPS5844679B2 (en) | 1983-10-04 |
Family
ID=12421866
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP3470975A Expired JPS5844679B2 (en) | 1975-03-22 | 1975-03-22 | 11,12,13,14- Tetrahydroacyl diyosamycin |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5844679B2 (en) |
-
1975
- 1975-03-22 JP JP3470975A patent/JPS5844679B2/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| JPS51110584A (en) | 1976-09-30 |
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