JPS634554B2 - - Google Patents
Info
- Publication number
- JPS634554B2 JPS634554B2 JP7651180A JP7651180A JPS634554B2 JP S634554 B2 JPS634554 B2 JP S634554B2 JP 7651180 A JP7651180 A JP 7651180A JP 7651180 A JP7651180 A JP 7651180A JP S634554 B2 JPS634554 B2 JP S634554B2
- Authority
- JP
- Japan
- Prior art keywords
- methanol
- acid
- dihydromycinamicin
- mycinamicin
- under reduced
- 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
- 150000003839 salts Chemical class 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 229930187734 mycinamicin Natural products 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 239000002904 solvent Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
- 230000000844 anti-bacterial effect Effects 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
- 238000000921 elemental analysis Methods 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 229910000033 sodium borohydride Inorganic materials 0.000 description 3
- 239000012279 sodium borohydride Substances 0.000 description 3
- 238000004809 thin layer chromatography Methods 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- ZYBWTEQKHIADDQ-UHFFFAOYSA-N ethanol;methanol Chemical compound OC.CCO ZYBWTEQKHIADDQ-UHFFFAOYSA-N 0.000 description 2
- 239000012046 mixed solvent Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- 241000192125 Firmicutes Species 0.000 description 1
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 1
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 1
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000187723 Micromonospora sp. Species 0.000 description 1
- 241000204031 Mycoplasma Species 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- 239000003463 adsorbent Substances 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 239000003674 animal food additive Substances 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 235000003704 aspartic acid Nutrition 0.000 description 1
- OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 230000007012 clinical effect Effects 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 235000013922 glutamic acid Nutrition 0.000 description 1
- 239000004220 glutamic acid Substances 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 239000003120 macrolide antibiotic agent Substances 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 230000003449 preventive effect Effects 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
Landscapes
- Saccharide Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
本発明は、新規なマイシナミシン誘導体に関す
る。さらに詳しくは、本発明は、式
（式中、Ｒは水素原子または水酸基を示す）で
表わされる化合物またはその塩に関する。
マイシナミシン（Mycinamicin）は、ミクロ
モノスポラ・スピーシーズＡ―11725の産生する
塩基性16員環マクロライド系抗生物質の各成分、
即ちマイシナミシン，，およびの総称と
して命名されたものであり、各成分の化学構造は
J.Chem.Soc.Chem.Comm.，1980，119〜121に記
載されていて、最初は各々抗生物質A11725，
，ａおよびａと名付けられた（特開昭54−
148701号、特願昭54−31316号）。
本発明の目的化合物〔１〕は９位の水酸基の配
位により２種のエピマーおよび混合物が包含され
る。
上記の塩としては、医薬上許容できる塩であ
り、例えば塩酸、硫酸、リン酸などの無機酸との
塩、酢酸、プロピオン酸、酒石酸、クエン酸、コ
ハク酸、リンゴ酸、アスパラギン酸、グルタミン
酸、各種のスルホン酸などの有機酸との塩であ
る。その他の非毒性塩も包含される。
上記の目的化合物〔１〕およびその塩はグラム
陽性菌、グラム陰性菌およびマイコプラズマに対
し抗菌活性を有し、臨床上優れた感染治療効果の
期待される抗菌性物質であるばかりでなく、動物
の疾病の予防および治療剤として有用であり、飼
料添加用薬剤としても有用である。
本発明の目的化合物〔１〕は、マイシナミシン
またはを不活性有機溶媒中水素化ホウ素ナト
リウムで還元することにより得られる。
不活性有機溶媒としては、メタノール、エタノ
ールなどの低級アルカノールが好ましい。反応は
通常室温で進行する。反応時間はシリカゲルなど
に薄層クロマトグラフイーにより反応経過を追跡
できるので、マイシナミシンまたはの消失を
待つて適宜反応を終了すればよい。
得られた化合物〔１〕を反応液から採取するに
は反応液を水中に注ぎ、非親水性有機溶媒で抽出
し、得られた抽出液を水洗後、減圧乾固し、残渣
をシリカゲル、活性アルミナ、吸着樹脂などの吸
着剤を用いるカラムクロマトグラフイーにより精
製することにより得られる。
次に、本発明の目的化合物〔１〕の抗菌スペク
トラムを測定した結果を第１表に示す。
The present invention relates to novel mycinamicin derivatives. More specifically, the present invention provides the formula (wherein R represents a hydrogen atom or a hydroxyl group) or a salt thereof. Mycinamicin is a basic 16-membered ring macrolide antibiotic produced by Micromonospora sp. A-11725.
In other words, it was named as a generic term for mycinamicin, and the chemical structure of each component is
J.Chem.Soc.Chem.Comm., 1980, 119-121, and initially the antibiotics A11725,
, a and a (Japanese Unexamined Patent Application Publication No. 1989-1999)
No. 148701, Patent Application No. 1983-31316). The object compound [1] of the present invention includes two types of epimers and mixtures depending on the coordination of the hydroxyl group at the 9-position. The above salts include pharmaceutically acceptable salts, such as salts with inorganic acids such as hydrochloric acid, sulfuric acid, phosphoric acid, acetic acid, propionic acid, tartaric acid, citric acid, succinic acid, malic acid, aspartic acid, glutamic acid, It is a salt with various organic acids such as sulfonic acids. Other non-toxic salts are also included. The above target compound [1] and its salts have antibacterial activity against Gram-positive bacteria, Gram-negative bacteria, and mycoplasma, and are not only antibacterial substances that are expected to have excellent clinical effects in treating infections, but also in animals. It is useful as a preventive and therapeutic agent for diseases, and is also useful as a feed additive. The object compound [1] of the present invention can be obtained by reducing mycinamicin with sodium borohydride in an inert organic solvent. As the inert organic solvent, lower alkanols such as methanol and ethanol are preferred. The reaction usually proceeds at room temperature. The reaction time can be monitored by thin layer chromatography on silica gel or the like, so the reaction can be appropriately terminated after waiting for the mycinamicin to disappear. To collect the obtained compound [1] from the reaction solution, the reaction solution was poured into water, extracted with a non-hydrophilic organic solvent, and the obtained extract was washed with water and dried under reduced pressure. It is obtained by purification by column chromatography using an adsorbent such as alumina or adsorption resin. Next, Table 1 shows the results of measuring the antibacterial spectrum of the object compound [1] of the present invention.
【表】【table】
【表】
次に、実施例を挙げて本発明の化合物〔１〕の
製造例を具体的に説明する。
尚、実施例中のRf値は、特記しない限り次の
担体および展開溶媒を用いる薄層クロマトグラフ
イー（TLC）により測定したものである。
担体；メルク社製シリカゲル60プレート
F254Art5715
展開溶媒；クロロホルム―メタノール―28％ア
ンモニア水（150：10：１）実施例 １
９―ジヒドロマイシナミシン
マイシナミシン（Rf0.74）505mgをエタノー
ル―メタノール（４：1V／Ｖ）の混合溶媒20ml
に溶かし、これに水素化ホウ素ナトリウム60mgを
加え、室温で20時間撹拌する。反応液に水40mlを
加え、減圧下溶媒を留去した後、酢酸エチル30ml
で３回抽出する。酢酸エチル層を水洗し、無水硫
酸マグネシウムで乾燥後、減圧乾固して残渣513
mgを得る。これをシリカゲル（25ｇ、メルク社
製）のカラムクロマトグラフイーにてクロロホル
ム―メタノール―28％アンモニア水（400：10：
１）で溶出することにより、Rf0.47の区分と
Rf0.39の区分に分離した。各区分を減圧乾固して
各々Rf0.47の９―ジヒドロマイシナミシン127
mgとRf0.39の９―ジヒドロマイシナミシン281
mgを得る。
Rf0.47の９―ジヒドロマイシナミシン
無定形白色粉末
MS；697（M+）
元素分析〔C37H63NO11として〕
Ｃ％ Ｈ％ Ｎ％
測定値 63.71 9.37 1.77
計算値 63.68 9.10 2.01
〔α〕23 D−38.9゜（Ｃ＝1.0、メタノール）
UV；λMeOH nax 218nm（ξ＝34300）
λMoOH sh 232nm（ξ＝24100）
IR；υKBr nax 3450（OH）、1710（CO）、1650（二重
結合）、1170、1070、980-1cm
NMR；δCDc13 ppn 0.86〜1.32（６×CH3）2.28〔Ｎ
（CH3）2〕、3.52（OCH3）、3.61（OCH3）、4.27（d.，
1′位Ｈ）、4.55（d.，1″位Ｈ）、4.90（m.，15位Ｈ）
、
5.3〜6.8（３×HC＝CH）
Rf0.39の９―ジヒドロマイシナミシン
白色結晶
MS；697（M+）
元素分析〔C37H63NO11として〕
Ｃ％ Ｈ％ Ｎ％
測定値 63.10 9.31 2.30
計算値 63.68 9.10 2.01
〔α〕23 D−28.5゜（Ｃ＝1.0、メタノール）
UV；λMeOH nax 217nm（ξ＝33900）
λMeOH sh 232.5nm（ξ＝23900）
IR；υKBr nax 3450（OH）、1710（CO）、1645（二重
結合）、1165、1070、985-1cm
NMR；δCDc13 ppn 0.86〜1.32（６×CH3）、2.28〔Ｎ
（CH3）2〕、3.52（OCH3）、3.61（OCH3）、4.27（d.，
1′位Ｈ）、4.55（d.，1″位Ｈ）、4.90（m.，15位Ｈ）
、
5.4〜6.9（３×HC＝CH）
実施例 ２
９―ジヒドロマイシナミシン
マイシナミシン（Rf0.59）501mgをエタノー
ル―メタノール（４：1V／Ｖ）の混合溶媒20ml
に溶かし、これに水素化ホウ素ナトリウム65mgを
加え、室温で20時間撹拌する。反応液に水40mlを
加え、減圧下溶媒を留去した後、酢酸エチル30ml
で３回抽出する。酢酸エチル層を水洗し、無水硫
酸マグネシウムで乾燥後、減圧乾固して残渣499
mgを得る。これをシリカゲル（25ｇ、メルク社
製）のカラムクロマトグラフイーにてクロロホル
ム―メタノール−28％アンモニア水（400：10：
１）で溶出することにより、Rf0.33の区分を分離
する。この区分を減圧乾固して９―ジヒドロマイ
シナミシン380mgを得る。
無定形白色粉末
MS；713（M+）
元素分析〔C37H63NO12として〕
Ｃ％ Ｈ％ Ｎ％
測定値 62.37 9.12 2.01
計算値 62.25 8.89 1.96
〔α〕23 D−19.5（Ｃ＝1.0、メタノール）
UV；λMoOH nax 218nm（ξ＝30700）
λMeOH sh 232nm（ξ＝22100）
IR；υKBr nax 3460（OH）、1715（CO）、1650（二重
結合）、1170、1080、985-1cm
NMR；δCDc13 ppn 0.86〜1.32（６×CH3）、2.28〔Ｎ
（CH3）2〕、3.51（OCH3）、3.62（OCH3）、4.27（d.，
1′位Ｈ）、4.59（d.，1″位Ｈ）、4.88（m.，15位Ｈ）
、
5.4〜6.9（３×CH＝CH）[Table] Next, production examples of the compound [1] of the present invention will be specifically explained with reference to Examples. Note that the Rf values in the examples were measured by thin layer chromatography (TLC) using the following carrier and developing solvent, unless otherwise specified. Carrier: Merck silica gel 60 plate
F254Art5715 Developing solvent: Chloroform-methanol-28% aqueous ammonia (150:10:1) Example 1 9-dihydromycinamicin 505 mg of mycinamicin (Rf0.74) and 20 ml of mixed solvent of ethanol-methanol (4:1 V/V)
60 mg of sodium borohydride is added to this, and the mixture is stirred at room temperature for 20 hours. Add 40 ml of water to the reaction solution, distill off the solvent under reduced pressure, and add 30 ml of ethyl acetate.
Extract 3 times. The ethyl acetate layer was washed with water, dried over anhydrous magnesium sulfate, and dried under reduced pressure to obtain a residue of 513
Get mg. This was subjected to column chromatography using silica gel (25 g, manufactured by Merck & Co., Ltd.) using chloroform-methanol-28% aqueous ammonia (400:10:
By eluting with 1), the classification of Rf0.47 and
Separated into Rf0.39 category. Each section was dried under reduced pressure and each 9-dihydromycinamicin 127 with Rf0.47 was prepared.
9-dihydromycinamicin 281 with mg and Rf0.39
Get mg. 9-Dihydromycinamicin with Rf0.47 Amorphous white powder MS; 697 (M + ) Elemental analysis [as C 37 H 63 NO 11 ] C% H% N% Measured value 63.71 9.37 1.77 Calculated value 63.68 9.10 2.01 [α ] 23 D −38.9゜ (C=1.0, methanol) UV; λ MeOH nax 218nm (ξ=34300) λ MoOH sh 232nm (ξ=24100) IR; υ KBr nax 3450 (OH), 1710 (CO), 1650 ( double bond), 1170, 1070, 980 -1 cm NMR; δ CDc13 ppn 0.86-1.32 (6×CH 3 ) 2.28 [N
(CH 3 ) 2 ], 3.52 (OCH 3 ), 3.61 (OCH 3 ), 4.27 (d.,
1′ position H), 4.55 (d., 1″ position H), 4.90 (m., 15th position H)
,
5.3-6.8 (3×HC=CH) 9-dihydromycinamicin with Rf0.39 White crystal MS; 697 (M + ) Elemental analysis [as C 37 H 63 NO 11 ] C% H% N% Measured value 63.10 9.31 2.30 Calculated value 63.68 9.10 2.01 [α] 23 D −28.5゜ (C = 1.0, methanol) UV; λ MeOH nax 217 nm (ξ = 33900) λ MeOH sh 232.5 nm (ξ = 23900) IR; υ KBr nax 3450 (OH ), 1710 (CO), 1645 (double bond), 1165, 1070, 985 -1 cm NMR; δ CDc13 ppn 0.86-1.32 (6×CH 3 ), 2.28 [N
(CH 3 ) 2 ], 3.52 (OCH 3 ), 3.61 (OCH 3 ), 4.27 (d.,
1′ position H), 4.55 (d., 1″ position H), 4.90 (m., 15th position H)
,
5.4-6.9 (3×HC=CH) Example 2 9-dihydromycinamicin 501 mg of mycinamicin (Rf0.59) was added to 20 ml of a mixed solvent of ethanol-methanol (4:1 V/V)
65 mg of sodium borohydride is added to this, and the mixture is stirred at room temperature for 20 hours. Add 40 ml of water to the reaction solution, distill off the solvent under reduced pressure, and add 30 ml of ethyl acetate.
Extract 3 times. The ethyl acetate layer was washed with water, dried over anhydrous magnesium sulfate, and dried under reduced pressure to obtain a residue of 499
Get mg. This was subjected to column chromatography using silica gel (25 g, manufactured by Merck & Co., Ltd.) using chloroform-methanol-28% aqueous ammonia (400:10:
By eluting in step 1), the Rf0.33 category is separated. This fraction was dried under reduced pressure to obtain 380 mg of 9-dihydromycinamicin. Amorphous white powder MS; 713 (M + ) Elemental analysis [as C 37 H 63 NO 12 ] C% H% N% Measured value 62.37 9.12 2.01 Calculated value 62.25 8.89 1.96 [α] 23 D −19.5 (C = 1.0, methanol) UV; λ MoOH nax 218nm (ξ=30700) λ MeOH sh 232nm (ξ=22100) IR; υ KBr nax 3460 (OH), 1715 (CO), 1650 (double bond), 1170, 1080, 985 - 1 cm NMR; δ CDc13 ppn 0.86-1.32 (6×CH 3 ), 2.28 [N
(CH 3 ) 2 ], 3.51 (OCH 3 ), 3.62 (OCH 3 ), 4.27 (d.,
1′ position H), 4.59 (d., 1″ position H), 4.88 (m., 15th position H)
,
5.4～6.9 (3×CH=CH)
Claims (1)
表わされる化合物またはその塩。[Claims] 1 formula (wherein R represents a hydrogen atom or a hydroxyl group) or a salt thereof.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP7651180A JPS5718694A (en) | 1980-06-05 | 1980-06-05 | 9-dihydromycinamicin |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP7651180A JPS5718694A (en) | 1980-06-05 | 1980-06-05 | 9-dihydromycinamicin |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5718694A JPS5718694A (en) | 1982-01-30 |
| JPS634554B2 true JPS634554B2 (en) | 1988-01-29 |
Family
ID=13607279
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP7651180A Granted JPS5718694A (en) | 1980-06-05 | 1980-06-05 | 9-dihydromycinamicin |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5718694A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5099162A (en) * | 1987-07-22 | 1992-03-24 | Canon Kabushiki Kaisha | Coil of superconducting material for electric appliance and motor utilizing said coil |
-
1980
- 1980-06-05 JP JP7651180A patent/JPS5718694A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5718694A (en) | 1982-01-30 |
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