JPH0587517B2 - - Google Patents
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- Publication number
- JPH0587517B2 JPH0587517B2 JP59009877A JP987784A JPH0587517B2 JP H0587517 B2 JPH0587517 B2 JP H0587517B2 JP 59009877 A JP59009877 A JP 59009877A JP 987784 A JP987784 A JP 987784A JP H0587517 B2 JPH0587517 B2 JP H0587517B2
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- formula
- cooch
- methylene chloride
- acrylic acid
- compound
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Description
【発明の詳細な説明】 本発明は、式[Detailed description of the invention] The present invention is based on the formula
【式】
で示される新規なβ−置換アクリル酸誘導体、該
誘導体を有効成分とする抗菌剤および抗マイコプ
ラズマ剤に関する。
本発明者らは先に、土壌から分離したペニシリ
ウム属に属する糸状菌である「No.2188生産菌」
（微工研条寄「第142号」の培養物から、新規な抗
生物質で下記式〔〕で表わされるβ−（６−イ
ソシアノ）−３，７−ジオキサトリシクロ〔４，
１，０，02,4〕ヘプタン−４−イル）アクリル酸
（以下、β−置換アクリル酸と略記する）を得た
（特願昭57−128693号及び特願昭57−135557号参
照）。The present invention relates to a novel β-substituted acrylic acid derivative represented by the formula: an antibacterial agent and an antimycoplasma agent containing the derivative as an active ingredient. The present inventors previously identified "No. 2188 producing fungus", which is a filamentous fungus belonging to the genus Penicillium, isolated from soil.
(From the culture of ``Feikoken Joyori No. 142'', a new antibiotic, β-(6-isocyano)-3,7-dioxatricyclo[4,
1,0,0 2,4 ]heptane-4-yl) acrylic acid (hereinafter abbreviated as β-substituted acrylic acid) was obtained (see Japanese Patent Application Nos. 128693-1983 and 135557-1987). .
【化】
本発明化合物は、前記β−置換アクリル酸を更
に化学反応させて得られた化合物であり、以下に
示す如く優れた抗菌性並びに抗マイコプラズマ活
性を有する。
本発明の目的は、式The compound of the present invention is a compound obtained by further chemically reacting the β-substituted acrylic acid, and has excellent antibacterial properties and antimycoplasma activity as shown below. The purpose of the invention is to obtain the formula
【化】 〔式中、Ａは[ka] [In the formula, A is
【式】【formula】
【式】【formula】
【式】【formula】
【化】[ka]
【化】[ka]
【化】[ka]
【化】 又は−NHR1 （式中、R1は、Ｈ，[Chemical formula] or -NHR 1 (wherein R 1 is H,
【式】置換または 未置換フエニル基、[Formula] Substitution or unsubstituted phenyl group,
【式】【formula】
【式】−CH2CH2 OH，[Formula] −CH 2 CH 2 OH,
【式】又は[Formula] or
【式】
（式中、R2は−CH3，−CH2C6H5を示し、R3は−
CH2CH2−COOCH3，−CH2COOCH3，−CH2CH2
COOCH2C6H5，−CH2COOCH2C6H5，
[Formula] (In the formula, R 2 represents −CH 3 , −CH 2 C 6 H 5 , and R 3 represents −
CH 2 CH 2 −COOCH 3 , −CH 2 COOCH 3 , −CH 2 CH 2
COOCH 2 C 6 H 5 , −CH 2 COOCH 2 C 6 H 5 ,
【式】又は−CH2C6H5を示す））を示
す〕で示されるβ−置換アクリル酸誘導体、該誘
導体を有効成分とする抗菌剤および抗マイコプラ
ズマ剤を提供することにある。
本発明のβ−置換アクリル酸誘導体は、β−置
換アクリル酸のカルボキシル基のOHを窒素原子
を有する種々の置換基で置換することにより製造
し得る。
本発明のβ−置換アクリル酸誘導体の具体的化
合物を構造式とともに融点、赤外線スペクトルお
よびN.M.R.スペクトルの図面番号を第１表に示
す。An object of the present invention is to provide a β-substituted acrylic acid derivative represented by the formula: or -CH 2 C 6 H 5 ), and an antibacterial agent and an antimycoplasma agent containing the derivative as an active ingredient. The β-substituted acrylic acid derivative of the present invention can be produced by substituting the OH of the carboxyl group of β-substituted acrylic acid with various substituents having a nitrogen atom. Specific compounds of the β-substituted acrylic acid derivatives of the present invention are shown in Table 1 along with structural formulas, melting points, infrared spectra, and drawing numbers of NMR spectra.
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】
本発明化合物の生物学的性質は下記に示す通り
である。
(1) 抗菌性
この抗菌スペクトルは肉汁寒天培地を用いる寒
天希釈法により決定したものである。測定結果を
第２表および第３表に示す。
尚、Candida albicansの場合はサブロー寒天
培地を用いて抗菌スペクトルを決定した。
(2) 抗マイコプラズマ活性
Mycoplasma pneumoniae IID817を試験菌と
して用い、本発明化合物の抗マイコプラスマ活性
をブドウ糖１％PPLOブロス培地を用い、37℃で
培養し、液体培地希釈法により決定した。
尚、効果の判定は、薬剤無添加のフエノールレ
ツドの色調変化のあつた時に判定を行つた。
測定結果を第２表に示す。[Table] The biological properties of the compounds of the present invention are shown below. (1) Antibacterial properties This antibacterial spectrum was determined by the agar dilution method using a meat juice agar medium. The measurement results are shown in Tables 2 and 3. In the case of Candida albicans, the antibacterial spectrum was determined using Sabouraud agar medium. (2) Anti-mycoplasma activity Using Mycoplasma pneumoniae IID817 as a test bacterium, the anti-mycoplasma activity of the compound of the present invention was determined by culturing at 37°C in a glucose 1% PPLO broth medium and by a liquid medium dilution method. The effectiveness was evaluated when there was a change in color of phenol red without any drug added. The measurement results are shown in Table 2.
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】
上記から明らかな通り、本発明化合物は種々の
グラム陽性及びグラム陰性菌に対して抗菌活性を
有し、またマイコプラズマに対しても活性を有す
る。従つて治療薬及び消毒薬として使用すること
ができる。
本発明化合物を薬剤として使用する場合、薬剤
中に本発明化合物が有効成分として一般に0.01乃
至100重量％含まれる。本発明化合物を単独で使
用しない場合、本発明化合物を製薬上許容し得る
担体との混合物として使用し得る。前記担体とし
ては、水、ゼラチン、アラビアゴム、ラクトー
ス、デン粉、ステアリン酸マグネシウム、タル
ク、植物油、ポリアルキレングリコール、黄色ワ
セリン等の有機又は無機の不活性な担体材料を使
用することができる。また、該薬剤に他の薬及
び／又は補助薬、例えば保存剤、安定剤、湿潤
剤、乳化剤、浸透圧調節剤、緩衝剤等を含有させ
ても良い。
本発明化合物は、経口的または非経口的に適用
され、従つて経口的または非経口的に投与するた
めの形態、例えば固体形態（散剤、顆粒剤、錠
剤、糖衣錠、カプセル剤、坐薬等）、半固体形態
（軟膏等）、液体形態（懸濁液、溶液、乳濁液、ア
ンプル、注射液等）を任意にとり得る。投与量
は、年令、個体差、病状などにより適宜変化する
が、人間を対象とする場合には、一般的に経口的
には体重60Kgの成人、１日当り100〜1000mg、好
ましくは250〜500mgであり、非経口的には体重60
Kgの成人、１日当り50〜500mg、好ましくは100〜
200mgを１〜４回に分けて投与する。
次に実施例により本発明をより詳細に説明す
る。尚、本発明化合物を合成するために、β−置
換アクリル酸の構造に悪影響を与えない
[Table] As is clear from the above, the compounds of the present invention have antibacterial activity against various Gram-positive and Gram-negative bacteria, and also have activity against Mycoplasma. It can therefore be used as a therapeutic agent and disinfectant. When the compound of the present invention is used as a drug, the compound of the present invention is generally contained in the drug in an amount of 0.01 to 100% by weight as an active ingredient. When a compound of the present invention is not used alone, it may be used in a mixture with a pharmaceutically acceptable carrier. As the carrier, organic or inorganic inert carrier materials such as water, gelatin, gum arabic, lactose, starch, magnesium stearate, talc, vegetable oil, polyalkylene glycol, yellow petrolatum, etc. can be used. The drug may also contain other drugs and/or adjuvants, such as preservatives, stabilizers, wetting agents, emulsifiers, osmotic pressure regulators, buffers, and the like. The compounds of the invention can be applied orally or parenterally, and therefore forms for oral or parenteral administration, such as solid forms (powders, granules, tablets, dragees, capsules, suppositories, etc.); Semi-solid forms (ointments, etc.) and liquid forms (suspensions, solutions, emulsions, ampoules, injections, etc.) can optionally be used. The dosage will vary depending on age, individual differences, medical conditions, etc., but when targeting humans, the general dosage is 100 to 1000 mg per day, preferably 250 to 500 mg per day for an adult weighing 60 kg. and parenterally, body weight 60
Kg adults, 50-500 mg per day, preferably 100-
Administer 200 mg in 1 to 4 divided doses. Next, the present invention will be explained in more detail with reference to Examples. In addition, in order to synthesize the compound of the present invention, the structure of β-substituted acrylic acid is not adversely affected.
【式】構造を生成するための公知法が適用
可能であることは当業者にとり明らかであろう。
実施例 １
本発明化合物No.1の合成：
β−置換アクリル酸196mg（1.01mmole）を30
mlの塩化メチレンに溶解し、当モルのトリエチル
アミン（147μ）を添加した。常法に従つて、
イソブチルクロロフオルメート（137μ）を加
えて混合酸無水物とした後、同温度（−12〜−15
℃）でアンモニアガスを反応液中に導入した。
TLC（シリカゲル；塩化メチレン）により混合酸
無水物の消失を確認後、減圧下溶媒を留去した。
残渣を少量塩化メチレン−メタノール混合溶媒
（Ｖ／Ｖ＝15／１）に溶解し、同混合溶媒を展開
溶媒とするシリカゲルカラムクロマトにより精製
した。（Rf 0.28）得られた粗精製アミドをアセト
ン−ｎ−ヘキサン混合溶媒より再結晶すると無色
針状晶（＞120℃、分解）の化合物No.1が159mg
（82％）得られた。
実施例 ２
DCC直接法による本発明化合物No.7および
No.18の合成：
β−置換アクリル酸（306mg；1.59mmole）を
16mlの塩化メチレンに溶解し、得られた塩化メチ
レン溶液に室温下ジシクロヘキシルカルボジイミ
ド（以下DCCと略称する）345mgの塩化メチレン
溶液（10ml）を滴下した。10〜20分反応させた
後、アニリン155mgの塩化メチレン溶液（10ml）
を室温下で30分かけて滴下した。反応終了後反応
混合物を濾過して濾液を集めた。得られた濾液を
濃縮後、塩化メチレン−酢酸エチル混合溶液
（Ｖ／Ｖ＝20／１）を展開溶媒とするシリカゲル
カラムクロマトにより分離精製するとRf値0.33に
対応するアミドとして化合物No.18が132mg（31
％）また、Rf値0.25に対応するものとしてDCC
付加体である化合物No.7が233mg（37％）得られ
た。
実施例 ３
混合酸無水物法による本発明化合物No.18の合
成；
β−置換アクリル酸（1159mg；6mmole）を80
mlの塩化メチレンに溶解し、これにトリエチルア
ミン（879μ）を添加した。次に、−10〜−15℃
でイソブチルクロロフオルメート（IBCF）817μ
を少量ずつ滴下し、同温度で20〜30分反応させ
た。さらにアニリン793μの塩化メチレン溶液
（20ml）を15分を要して加えた後室温にもどして
３〜12時間反応させた。反応終了後、減圧下で溶
媒を留去し、その残渣を塩化メチレン−酢酸エチ
ル混合溶媒（Ｖ／Ｖ＝20／１）を用いたシリカゲ
ルカラムクロマトにより精製した。得られた粗精
製物をヘキサン−塩化メチレン混合溶媒より再結
晶すると化合物No.18を細針状晶として1121.2mg
（収率70％）得た。
実施例 ４
本発明化合物No.6の合成：
β−置換アクリル酸193mgとＮ−ヒドロキシス
クシイミド115mgを40mlの塩化メチレンに溶解し、
これに氷冷下DCC207mgの塩化メチレン溶液（10
ml）を滴下により添加した。30分後氷浴を取り外
して室温で３〜12時間攪拌した。
析出したジシクロヘキシル尿素を濾別した後そ
の濾液にベンジルアミン（109μ）の塩化メチ
レン溶液（５ml）を室温で滴下添加した。
反応終了後、減圧下溶媒を留去して10mlまで濃
縮し、これに約倍量（20ml）のｎ−ヘキサンを加
え１時間静置した後に析出物を集めた。得られた
析出物を塩化メチレン−酢酸エチル混合溶媒
（Ｖ／Ｖ＝20／１）を展開溶媒とするシリカゲル
カラムクロマトにより精製、さらに塩化メチレン
−ヘキサン混合溶媒より再結晶すると目的とする
化合物No.6が針状晶として得られた。収率240mg
（85％）であり、針状晶160℃以上で分解（着色）
した。
実施例 ５
本発明化合物No.8，No.9，No.10およびNo.11
の合成：
β−置換アクリル酸193mg（1mmole）とＮ−
ヒドロキシスクシイミド115mg（1mmole）を15
mlの塩化メチレンに溶解しベンジルアミド合成の
際の条件に準じて活性エステルとした。得られた
溶液に対応するアミノ酸の塩酸又はｐ−トルエン
スルホン酸塩等と有機塩基（トリエチルアミン
等）より調製したフリーベースを室温で滴下添加
した。12〜24時間反応を行なつた後、35℃減圧下
で溶媒を留去して濃縮した。濃縮物を塩化メチレ
ン−酢酸エチル混合溶媒（Ｖ／Ｖ＝10／１）を用
いた短シリカゲルカラムクロマトにより予備精製
して後、その溶出液を５〜７mlに濃縮して倍量の
ｎ−ヘキサンを加えた。析出した不溶部を集めて
塩化メチレンほ酢酸エチル（Ｖ／Ｖ＝20／１）用
いたシリカゲルカラムクロマトにより精製し、さ
らにヘキサン−塩化メチレン混合溶媒より再結晶
すると目的とする化合物No.8を細かい針状晶と
して156.6mg（45％）得た。
同様にして、下記化合物を生成した。
収量 収率
本発明化合物No. 9 100mg 30％
〃 No.10 478mg 60％
〃 No.11 394mg 52％
実施例 ６
本発明化合物No.15，No.16およびNo.17の合
成：
β−置換アクリル酸47.5mg（0.25mmole）を２
mlの塩化メチレンに溶解し、これにDCC51.2mgの
塩化メチレン溶液（２ml）を室温で滴下した。１
時間後６−アミノペニシラン酸ｐ−ブロモフエナ
シルエステル（P.Brmberg etal，Acta Chem.
Scand.，21，2210（1967））103mgの塩化メチレン
溶液を滴下添加した。反応終了後析出したジシク
ロヘキシル尿素を濾別し、濾液に約1.5倍量のｎ
−ヘキサンを添加し、析出物を収集した。得られ
た析出物を塩化メチレン−酢酸エチル混合溶媒
（Ｖ／Ｖ＝20／１）を用いたシリカゲルカラムク
ロマトにより精製し、さらに塩化メチレン−ヘキ
サン混合溶媒より再結晶すると目的とする化合物
No.15を細針状晶として72.4mg（50％）得た。
同様にして、下記化合物を生成した。
収量 収率
本発明化合物No.16 4.2mg 2.9％
〃 No.17 53mg 35％It will be apparent to those skilled in the art that known methods for generating the structure are applicable. Example 1 Synthesis of Compound No. 1 of the Invention: 196 mg (1.01 mmole) of β-substituted acrylic acid was added to 30
ml methylene chloride and equimolar triethylamine (147μ) was added. According to common law,
After adding isobutyl chloroformate (137μ) to make a mixed acid anhydride, it was heated at the same temperature (-12 to -15
Ammonia gas was introduced into the reaction solution.
After confirming the disappearance of the mixed acid anhydride by TLC (silica gel; methylene chloride), the solvent was distilled off under reduced pressure.
The residue was dissolved in a small amount of methylene chloride-methanol mixed solvent (V/V=15/1), and purified by silica gel column chromatography using the same mixed solvent as a developing solvent. (Rf 0.28) When the obtained crude amide was recrystallized from acetone-n-hexane mixed solvent, 159 mg of compound No. 1 was obtained as colorless needle-shaped crystals (>120℃, decomposed).
(82%) obtained. Example 2 Invention compound No. 7 and
Synthesis of No.18: β-substituted acrylic acid (306 mg; 1.59 mmole)
The mixture was dissolved in 16 ml of methylene chloride, and a methylene chloride solution (10 ml) containing 345 mg of dicyclohexylcarbodiimide (hereinafter abbreviated as DCC) was added dropwise to the obtained methylene chloride solution at room temperature. After reacting for 10-20 minutes, add 155 mg of aniline in methylene chloride solution (10 ml).
was added dropwise over 30 minutes at room temperature. After the reaction was completed, the reaction mixture was filtered and the filtrate was collected. After concentrating the obtained filtrate, it was separated and purified by silica gel column chromatography using a mixed solution of methylene chloride and ethyl acetate (V/V=20/1) as a developing solvent, and 132 mg of compound No. 18 was obtained as an amide corresponding to an Rf value of 0.33. (31
%) Also, DCC as corresponding to Rf value 0.25
233 mg (37%) of compound No. 7, which is an adduct, was obtained. Example 3 Synthesis of compound No. 18 of the present invention by mixed acid anhydride method; β-substituted acrylic acid (1159 mg; 6 mmole) was added to 80
ml of methylene chloride and to this was added triethylamine (879μ). Next, −10 to −15℃
Isobutyl chloroformate (IBCF) 817μ
was added dropwise little by little and reacted at the same temperature for 20 to 30 minutes. Furthermore, a methylene chloride solution (20 ml) containing 793 μ of aniline was added over a period of 15 minutes, and then the mixture was returned to room temperature and reacted for 3 to 12 hours. After the reaction was completed, the solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography using a mixed solvent of methylene chloride and ethyl acetate (V/V=20/1). When the obtained crude product was recrystallized from a hexane-methylene chloride mixed solvent, 1121.2 mg of compound No. 18 was obtained as fine needle-shaped crystals.
(yield 70%). Example 4 Synthesis of Invention Compound No. 6: 193 mg of β-substituted acrylic acid and 115 mg of N-hydroxysuccinimide were dissolved in 40 ml of methylene chloride,
To this was added a methylene chloride solution of 207 mg of DCC (10
ml) was added dropwise. After 30 minutes, the ice bath was removed and the mixture was stirred at room temperature for 3 to 12 hours. After the precipitated dicyclohexylurea was filtered off, a methylene chloride solution (5 ml) of benzylamine (109μ) was added dropwise to the filtrate at room temperature. After the reaction was completed, the solvent was distilled off under reduced pressure and concentrated to 10 ml. About twice the amount (20 ml) of n-hexane was added thereto, and the mixture was allowed to stand for 1 hour, after which the precipitate was collected. The obtained precipitate is purified by silica gel column chromatography using a methylene chloride-ethyl acetate mixed solvent (V/V=20/1) as a developing solvent, and further recrystallized from a methylene chloride-hexane mixed solvent to obtain the target compound No. 6 was obtained as needle crystals. Yield 240mg
(85%) and decomposes (colors) at 160℃ or higher as needle-like crystals.
did. Example 5 Compounds of the present invention No. 8, No. 9, No. 10 and No. 11
Synthesis: 193 mg (1 mmole) of β-substituted acrylic acid and N-
Hydroxysuccinimide 115mg (1mmole) 15
ml of methylene chloride to obtain an active ester according to the conditions used for benzylamide synthesis. A free base prepared from hydrochloric acid or p-toluenesulfonate of the corresponding amino acid and an organic base (triethylamine, etc.) was added dropwise to the obtained solution at room temperature. After reacting for 12 to 24 hours, the solvent was distilled off under reduced pressure at 35° C. and concentrated. After prepurifying the concentrate by short silica gel column chromatography using a mixed solvent of methylene chloride and ethyl acetate (V/V=10/1), the eluate was concentrated to 5-7 ml and diluted with double the amount of n-hexane. added. The precipitated insoluble portion was collected and purified by silica gel column chromatography using methylene chloride and ethyl acetate (V/V = 20/1), and further recrystallized from a hexane-methylene chloride mixed solvent to obtain the target compound No. 8 in fine particles. 156.6 mg (45%) was obtained as needle crystals. Similarly, the following compounds were produced. Yield Yield Compound of the present invention No. 9 100 mg 30% 〃 No. 10 478 mg 60% 〃 No. 11 394 mg 52% Example 6 Synthesis of compounds of the present invention No. 15, No. 16 and No. 17: β-substituted acrylic 47.5 mg (0.25 mmole) of acid 2
ml of methylene chloride, and a solution of 51.2 mg of DCC in methylene chloride (2 ml) was added dropwise thereto at room temperature. 1
After 6-aminopenicillanic acid p-bromophenacyl ester (P.Brmberg etal, Acta Chem.
Scand., 21 , 2210 (1967)) 103 mg of methylene chloride solution was added dropwise. After the completion of the reaction, the precipitated dicyclohexyl urea was separated by filtration, and about 1.5 times the amount of n was added to the filtrate.
- Hexane was added and the precipitate was collected. The obtained precipitate is purified by silica gel column chromatography using a mixed solvent of methylene chloride and ethyl acetate (V/V=20/1), and then recrystallized from a mixed solvent of methylene chloride and hexane to obtain the desired compound.
72.4 mg (50%) of No. 15 was obtained as fine needle-like crystals. Similarly, the following compounds were produced. Yield Yield Compound of the present invention No. 16 4.2 mg 2.9% 〃 No. 17 53 mg 35%
第１〜９９図は、本発明化合物No.1〜No.51の
赤外線吸収スペクトルまたはN.M.R.スペクトル
を示す図である。尚、IR吸収スペクトルを示す
図の縦軸は透過パーセントを示し、横軸は波数を
示す。
Figures 1 to 99 are diagrams showing infrared absorption spectra or NMR spectra of compounds No. 1 to No. 51 of the present invention. In addition, the vertical axis of the figure showing the IR absorption spectrum shows the transmission percentage, and the horizontal axis shows the wave number.
Claims (1)
CH2CH2COOCH3，−CH2COOCH3，−CH2CH2
COOCH2C6H5，−CH2COOCH2C6H5，
【式】又は−CH2C6H5を示す））を示 す］で示されるβ−置換アクリル酸誘導体。 ２ 置換フエニル基が【式】 【式】【式】 【式】【式】 【式】【式】 【式】【式】 【化】 【式】【式】 【式】【式】 【式】【式】 【式】または 【式】であることを特徴とする特許 請求の範囲第１項に記載のβ−置換アクリル酸誘
導体。 ３ 式 【化】 ［式中、Ａは【式】 【式】【式】 【式】【式】 【化】 【化】 【化】 【化】 又は −NHR1（式中、R1は、Ｈ，【式】置 換または未置換フエニル基、【式】 【式】【式】−CH2CH2 OH，【式】又は【式】 （式中、R2は−CH3，−CH2C6H5を示し、R3は−
CH2CH2COOCH3，−CH2COOCH3，−CH2CH2
COOCH2C6H5，−CH2COOCH2C6H5，
【式】又は−CH2C6H5を示す））を示 す］で示されるβ−置換アクリル酸誘導体を有効
成分とする抗菌剤。 ４ 式 【化】 ［式中、Ａは【式】 【式】【式】 【式】【式】 【化】 【化】 【化】 【化】 又は −NHR1（式中、R1は、Ｈ，【式】置 換または未置換フエニル基、【式】 【式】【式】 【式】又は【式】（式中、 R2は−CH3，−CH2C6H5を示し、R3は−CH2CH2
COOCH3，−CH2COOCH3，−CH2CH2COOCH2
C6H5，−CH2COOCH2C6H5，【式】又は −CH2C6H5を示す））を示す］で示されるβ−置
換アクリル酸誘導体を有効成分とする抗マイコプ
ラズマ剤。[Claims] 1 Formula: [Formula] [Formula] [Formula] [Formula] [Formula] [Formula] [Formula] [Formula] [Formula] [Formula] [Formula] [Formula] [Formula] [Formula] [Formula] [Formula] [Formula] [Formula] [Formula] [Formula] [Formula] [ Formula ] where R 1 is H, [Formula] substituted or unsubstituted phenyl group, [Formula] [Formula] [Formula] -CH 2 CH 2 OH, [Formula] or [Formula] (wherein R 2 is -CH 3 , −CH 2 C 6 H 5 and R 3 is −
CH 2 CH 2 COOCH 3 , −CH 2 COOCH 3 , −CH 2 CH 2
COOCH 2 C 6 H 5 , −CH 2 COOCH 2 C 6 H 5 ,
A β-substituted acrylic acid derivative represented by [Formula] or -CH 2 C 6 H 5 )]. 2 The substituted phenyl group is [formula] [formula] [formula] [formula] [formula] [formula] [formula] [formula] [formula] [formula] [formula] [formula] [formula] [formula] [formula] [Formula] [Formula] or [Formula] The β-substituted acrylic acid derivative according to claim 1, characterized in that it is 3 Formula: [Formula] [Formula] [Formula] [Formula] [Formula] [Formula] [Formula] [Formula] [Formula] [Formula] [Formula] [Formula] [Formula] [Formula] [Formula] or -NHR 1 (In the formula, R 1 is H, [Formula] substituted or unsubstituted phenyl group, [Formula] [Formula] [Formula] -CH 2 CH 2 OH, [Formula] or [Formula] (wherein R 2 is -CH 3 , -CH 2 C 6 H 5 and R 3 is −
CH 2 CH 2 COOCH 3 , −CH 2 COOCH 3 , −CH 2 CH 2
COOCH 2 C 6 H 5 , −CH 2 COOCH 2 C 6 H 5 ,
An antibacterial agent containing a β-substituted acrylic acid derivative represented by the formula: or -CH 2 C 6 H 5 ) as an active ingredient. 4 Formula [C] [In the formula, A is [Formula] [Formula] [Formula] [Formula] [Formula] [C] [C] [C] [C] [C] or -NHR 1 (In the formula, R 1 is H, [Formula] substituted or unsubstituted phenyl group, [Formula] [Formula] [Formula] [Formula] or [Formula] (wherein R 2 represents -CH 3 , -CH 2 C 6 H 5 , R 3 is −CH 2 CH 2
COOCH 3 , −CH 2 COOCH 3 , −CH 2 CH 2 COOCH 2
An anti-mycoplasma agent containing a β-substituted acrylic acid derivative represented by C 6 H 5 , -CH 2 COOCH 2 C 6 H 5 , [Formula] or -CH 2 C 6 H 5 ) as an active ingredient .
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59009877A JPS60152489A (en) | 1984-01-23 | 1984-01-23 | Beta-substituted acrylic acid derivative |
| US06/692,104 US4684664A (en) | 1984-01-23 | 1985-01-16 | Derivatives of β-(4-isocyano-1,2,3,4-diepoxycyclopentyl) acrylic acid |
| GB08501543A GB2153353B (en) | 1984-01-23 | 1985-01-22 | Derivatives of b-(4-isocyano-1,2-3,4-diepoxycyclopenthyl)acrylic acid |
| FR8500856A FR2558468B1 (en) | 1984-01-23 | 1985-01-22 | B- (4-ISOCYANO-1,2,3,4- DIEPOXYCYCLOPENTYL) ACRYLIC ACID DERIVATIVES AND COMPOSITIONS, PARTICULARLY PHARMACEUTICALS, CONTAINING THEM |
| DE19853501961 DE3501961A1 (en) | 1984-01-23 | 1985-01-22 | DERIVATIVES OF (BETA) - (4-ISOCYANO-1,2-3,4-DIEPOXYCYCLOPENTYL) ACRYLIC ACID |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59009877A JPS60152489A (en) | 1984-01-23 | 1984-01-23 | Beta-substituted acrylic acid derivative |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS60152489A JPS60152489A (en) | 1985-08-10 |
| JPH0587517B2 true JPH0587517B2 (en) | 1993-12-16 |
Family
ID=11732380
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP59009877A Granted JPS60152489A (en) | 1984-01-23 | 1984-01-23 | Beta-substituted acrylic acid derivative |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS60152489A (en) |
-
1984
- 1984-01-23 JP JP59009877A patent/JPS60152489A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS60152489A (en) | 1985-08-10 |
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