氰乙酸乙酯 | 105-56-6

• 物质功能分类: 有机原料 - 羧酸类化合物及衍生物 - 羧酸酯及其衍生物
• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: 氰乙酸乙酯
• 中文别名: 氰乙酸乙脂；氰基乙酸乙酯；乙基氰乙酸酯；氰基乙酰乙酯
• 英文名称: ethyl 2-cyanoacetate
• 英文别名: ethyl cyanoacetate；cyanoacetic acid ethyl ester
• CAS: 105-56-6
• 化学式: C₅H₇NO₂
• mdl: MFCD00001940
• 分子量: 113.116
• InChiKey: ZIUSEGSNTOUIPT-UHFFFAOYSA-N

物化性质

• 熔点：
  -22 °C (lit.)
• 沸点：
  208-210 °C (lit.)
• 密度：
  1.063 g/mL at 25 °C (lit.)
• 蒸气密度：
  3.9 (vs air)
• 闪点：
  >230 °F
• 溶解度：
  20g/l
• 介电常数：
  26.9（20℃）
• LogP：
  -0.119-1.05 at 23-25℃ and pH6.1
• 表面张力：
  70.2mN/m at 1.034g/L and 23℃
• 物理描述：
  Ethyl cyanoacetate appears as a colorless liquid. Denser than water. Contact may irritate skin, eyes and mucous membranes. May be toxic by ingestion. Used to make other chemicals.
• 颜色/状态：
  Colorless liquid
• 气味：
  Slight, pleasant odor
• 蒸汽密度：
  3.9 (Air = 1)
• 蒸汽压力：
  3.88X10-2 mm Hg at 25 °C
• 分解：
  When heated to decomposition or on contact with acid or acid fumes, it emits highly toxic fumes of /cyanides/.
• 折光率：
  Index of refraction = 1.4175 at 20 °C/D
• 保留指数：
  959;960;962
• 稳定性/保质期：

  1. 化学性质：氰基乙酸乙酯含有活性亚甲基，与溴作用生成溴代氰基乙酸乙酯。它还能与氨反应生成氰基乙酰胺，与乙醇和硫酸作用生成丙二酸二乙酯。它的酸性比苯酚弱，在酸碱条件下会发生水解反应。此外，氰基乙酸乙酯还可以与甲醛、乙醛或其他醛酮类物质发生缩聚反应。

  2. 稳定性：该化合物相对稳定。

  3. 避免接触的危险品：强氧化剂、强还原剂、强酸和强碱。

  4. 应避免接触潮湿空气。

  5. 聚合危害：不会发生聚合。

  6. 分解产物：分解会产生氰化物。

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  8
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  50.1
• 氢给体数：
  0
• 氢受体数：
  3

ADMET

代谢

氰乙酸乙酯可能会被不同组织的非特异性酯酶代谢，特别是在肝脏中代谢为氰乙酸和乙醇。

Ethyl cyanoacetate is likely to be metabolized by unspecific esterases of different tissues, in particular in the liver to cyanoacetic acid and ethanol.

来源:Hazardous Substances Data Bank (HSDB)

代谢

有机腈类通过肝脏中的细胞色素P450酶的作用转化为氰化物离子。氰化物迅速被吸收并在全身分布。氰化物主要通过罗丹酶或3-巯基丙酸硫转移酶代谢成硫氰酸盐。氰化物的代谢物通过尿液排出。

Organic nitriles are converted into cyanide ions through the action of cytochrome P450 enzymes in the liver. Cyanide is rapidly absorbed and distributed throughout the body. Cyanide is mainly metabolized into thiocyanate by either rhodanese or 3-mercaptopyruvate sulfur transferase. Cyanide metabolites are excreted in the urine. (L96)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 毒性总结

氰乙酸乙酯是氰乙酸的乙酯。在中性和碱性条件下，氰乙酸乙酯迅速水解为氰乙酸和乙醇……，而在酸性pH条件下，半衰期显著更长。体内的非特异性酯酶也可能催化其水解为氰乙酸和乙醇……由于酸和酯因其化学性质不同而具有不同的物理化学性质，因此必须分别评估与酸的酸性相关的效应（例如。生态毒性数据，局部刺激作用）。然而，由于相似的极性、蒸汽压和log Kow，可以预期环境和毒代动力学的分布范围在相似的量级……人类健康。从氰乙酸和氰乙酸乙酯的物理化学性质可以预期，这两种物质将通过所有暴露途径适度吸收。在口服给予氰乙酸后，在大鼠的组织和胎鼠组织中观察到相对均匀的分布。可以预期氰乙酸乙酯会有类似的行为。氰乙酸乙酯很可能被不同组织的非特异性酯酶代谢，特别是在肝脏中代谢为氰乙酸和乙醇。在大鼠吸入饱和蒸汽的7小时实验中，没有观察到死亡和毒性迹象，而对于50%氰乙酸水的气溶胶，大鼠的4小时LC50为1900 mg/m³。最显著的症状是眼睛、口腔和呼吸道的严重刺激征象。在一项1小时吸入实验中，氰乙酸乙酯在最大可达气溶胶浓度7380 mg/m³下，唯一的与物质相关发现是眼睛和上呼吸道的可逆刺激征象。据报道，氰乙酸在兔身上的皮肤LD50> 2000 mg/kg bw。在这项有限文件的研究中，报告了皮肤局部刺激作用和一些系统性影响（呼吸困难，行为改变），这表明经皮暴露后可能存在系统性毒性。对于氰乙酸乙酯，兔子和大鼠的皮肤LD50分别报告为> 1000和> 2000 mg/kg bw……。除了一只兔子皮肤轻微局部刺激外，没有观察到与治疗相关的发现。大鼠口服LD50值为1010 mg/kg bw。在剂量为1000 mg/kg bw时观察到呼吸困难、费力呼吸、冷漠和蹒跚步态的症状，尸检发现胃部有局部影响。在大鼠限制剂量2000 mg/kg bw下，氰乙酸乙酯只观察到与氰乙酸相似的系统性影响。氰乙酸对兔皮肤……和眼睛……具有腐蚀性，而氰乙酸乙酯对兔皮肤不刺激……对兔眼睛有中等刺激作用……。根据吸入毒性研究的结果，氰乙酸可以被认为是高度刺激呼吸道的粘膜，而氰乙酸乙酯对呼吸道只有轻微的刺激作用。在豚鼠的Buehler测试中，这两种物质都不是皮肤致敏物……。对氰乙酸乙酯进行了为期90天的口服（灌胃）研究……，大鼠的剂量为0、100、300和1000 mg/kg bw/day。这项研究中雌性大鼠的无明显有害作用水平（NOAEL）为100 mg/kg bw/day，雄性大鼠为300 mg/kg bw/day。在雌性动物300和1000 mg/kg bw/day剂量水平观察到血红蛋白值的显著剂量相关降低。在雄性1000 mg/kg bw/day剂量组中观察到尿量增加和肝脏（慢性胆管周围炎症）和肾上腺（肾上腺束状带空泡化）的可逆病理变化。对高剂量雄性精液计数和精子活力的额外检查发现，附睾中的活动精子百分比和精子计数明显下降（变化在历史对照数据的2个标准差之内，在睾丸或附睾中没有显著的器官重量变化或病理发现）。没有观察到对雌性性器官和发情周期的影响。氰乙酸和氰乙酸乙酯在标准细菌Ames试验中无论是否进行代谢激活均不显示致突变性。在这些Ames测试中，没有检测到Salmonella typhimurium TA102或E. coli WP2，然而，这是一个可以接受的限制，因为可以假定氰乙酸和氰乙酸乙酯都没有可能被TA102或E. coli WP2检测到的氧化或交联潜力。氰乙酸乙酯在体外细胞遗传学分析中，在存在和不存在代谢激活系统的情况下，对V79中国仓鼠肺细胞均未表现出裂变活性。所有氰乙酸乙酯的测试都按照OECD或EC指南和良好实验室规范进行。对于这两种物质，没有基因毒性的结构警示。总之，从现有信息来看，没有迹象表明这些物质具有基因毒性潜力，无论是基因突变还是染色体畸变。没有关于致癌性的数据。没有关于氰乙酸或氰乙酸乙酯的生育能力的具体研究。在为期90天的口服灌胃研究中……包括了氰乙酸乙酯对性腺的病理学评估以及额外的精液活力和精液计数调查，这些生育相关终点的NOAEL为300 mg/kg bw/day。在1000 mg/m³（LOAEL）观察到的精子活力下降和附睾精子计数减少，并未伴随着睾丸、附睾、卵巢或子宫

Ethyl cyanoacetate is the ethyl ester of cyanoacetic acid. Ethyl cyanoacetate hydrolyzes rapidly under neutral and alkaline conditions to cyanoacetic acid and ethanol ... , while in acid pH the half life is considerably longer. It also is likely that unspecific esterases in the body catalyze the hydrolysis to cyanoacetic acid and ethanol ... As the acid and the ester have different physical chemical properties due to their chemical nature, effects that are related to the acidity of the acid (e.g. ecotoxicity data, local irritating effects) have to be assessed separately. The environmental and toxicokinetic distribution can however be expected to range in a similar order of magnitude due to the similar polarity, vapor pressure and log Kow. ... Human Health. From the physical chemical properties of both cyanoacetic acid and ethyl cyanoacetate it can be expected that both substances will be moderately absorbed by all exposure routes. A relatively even distribution between tissues and also to embryonic tissues of pregnant rats was observed after oral administration of cyanoacetic acid. A similar behavior can be expected for ethyl cyanoacetate. Ethyl cyanoacetate is likely to be metabolized by unspecific esterases of different tissues, in particular in the liver to cyanoacetic acid and ethanol. While no mortality and no signs of toxicity were observed in a 7-hour vapor inhalation study in rats with saturated vapors of cyanoacetic acid, the 4-hour LC50 in rats for an aerosol of 50% cyanoacetic acid in water was 1900 mg/cu m. The most prominent symptoms were signs of severe irritation of eyes, mouth and respiratory tract. In a 1-hour inhalation study with ethyl cyanoacetate at the maximum attainable aerosol concentration of 7380 mg/cu m the only substance related findings were reversible signs of irritation of the eyes and the upper respiratory tract. For cyanoacetic acid a dermal LD50 > 2000 mg/kg bw in rabbits was reported. In this study with limited documentation local irritant effects on the skin and some systemic effects (dyspnea, behavioral changes) were reported, indicating a possible systemic toxicity after dermal exposure. For ethyl cyanoacetate a dermal LD50 > 1000 and > 2000 mg/kg bw was reported in rabbits and rats, respectively ... . No treatment related findings except for slight local skin irritation in the study in rabbits were observed. An acute oral LD50 value in rats of 1010 mg/kg bw has been reported for cyanoacetic acid. Symptoms including dyspnea, labored breathing, apathy and staggered gait were observed from doses of 1000 mg/kg bw and necropsy revealed local effects in the stomach. Only systemic effects similar to those reported for cyanoacetic acid were observed with ethyl cyanoacetate at a limit dose of 2000 mg/kg bw in rats. Cyanoacetic acid was corrosive to rabbit skin ... and eyes ... while ethyl cyanoacetate was not irritating to rabbit skin ... and moderately irritating to rabbit eyes... . Based on the results of the inhalation toxicity studies, cyanoacetic acid can be regarded as highly irritating to the mucous membranes of the respiratory tract while ethyl cyanoacetate only had a slight irritant effect on the respiratory tract. Both substances were not skin sensitizing in a Buehler test in guinea pigs ... . One 90-day oral (gavage) study in rats ... has been conducted with ethyl cyanoacetate at doses of 0, 100, 300 and 1000 mg/kg bw/day. The NOAEL in this study was 100 mg/kg bw/day for female rats and 300 mg/kg bw/day for male rats. A significant dose related reduction in hemoglobin values was observed at dose levels of 300 and 1000 mg/kg bw/day in female animals. In males of the 1000 mg/kg bw/day dose group increased urine volume and reversible pathological changes in liver (chronic peribiliary inflammation) and adrenals (vacuolization in the zona fasciculata of the adrenals) were observed. An additional examination of sperm counts and sperm motility in high dosed males revealed an apparently treatment related decrease in the percentage of motile sperms and sperm counts in the epididymis (changes within 2 standard deviations of the historical control data, no significant changes in organ weights or pathological findings in testes or epididymis). No effects were observed on female sex organs and estrous cycle. Both cyanoacetic acid and ethyl cyanoacetate were not mutagenic in the standard Ames assay in bacteria with and without metabolic activation. Neither Salmonella typhimurium TA102 nor E. coli WP2 were tested in these Ames tests, however, this is an acceptable restriction, because it can be assumed that neither cyanoacetic acid nor ethyl cyanoacetate has oxidizing or cross-linking potential, which may be detected by TA102 or E. coli WP2. Ethyl cyanoacetate did not show any clastogenic activity in the in vitro cytogenetic assay with V79 Chinese Hamster lung cells in the presence and absence of a metabolic activation system. All tests with ethyl cyanoacetate were conducted according to OECD or EC guidelines and GLP. For both substances, there is no structural alert for genotoxicity. In conclusion, from the available information, there is no indication of a genotoxic potential of the substances, both for gene mutations and chromosomal aberrations. No data are available on carcinogenicity. No specific studies on fertility are available for cyanoacetic acid or ethyl cyanoacetate. In a 90-day oral gavage study ... with ethyl cyanoacetate that included a histopathological evaluation of the gonads as well as additional investigations on sperm motility and sperm counts a NOAEL for these fertility related endpoints of 300 mg/kg bw/day was derived. A decrease of sperm motility and epididymal sperm counts observed in this study at 1000 mg/cu m (LOAEL) were not accompanied by significant reductions in testicular, epididymal, ovary or uterus weights, or any histopathological findings in these organs. Moreover, these effects are observed together with systemic toxicity. In a developmental toxicity study with ethyl cyanoacetate ... the NOAEL for embryotoxic or fetotoxic effects was 100 mg/kg bw/day based on an increase in minor skeletal anomalies in litters of the 300 and 1000 mg/kg bw/day dose groups and a reduced mean fetal weight at 1000 mg/kg bw/day. The NOAEL for maternal toxicity in this study was 300 mg/kg bw/day. Maternal toxicity in this study was however, only defined based on clinical signs, body weight development and macroscopic organ changes. Therefore it can not be excluded that the observed developmental effects are due to maternal toxicity. Studies on repeated dose toxicity and developmental toxicity conducted with ethyl cyanoacetate are considered relevant for cyanoacetic acid as well, as the ester will be rapidly metabolized to cyanoacetic acid and ethanol and its toxicity is likely to be mediated predominantly by cyanoacetic acid. Furthermore the study of the ester represents a "worst case" assumption for the acid as it can be assumed that the slightly more lipophilic ethyl ester is more readily absorbed than the corresponding acid and the maximum applicable dose of the ester is not limited by local irritation to mucous membranes. Therefore the ester can be administered at higher dose levels and is assumed to have a better bioavailability than the acid.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 毒性总结

有机腈在体内和体外都会分解成氰化物离子。因此，有机腈的主要毒性机制是它们产生有毒的氰化物离子或氢氰酸。氰化物是电子传递链第四复合体（存在于真核细胞线粒体膜中）中的细胞色素c氧化酶的抑制剂。它与这种酶中的三价铁原子形成配合物。氰化物与这种细胞色素的结合阻止了电子从细胞色素c氧化酶传递到氧气。结果，电子传递链被中断，细胞不能再通过有氧呼吸产生ATP能量。主要依赖有氧呼吸的组织，如中枢神经系统和心脏，受到特别影响。氰化物也通过与过氧化氢酶、谷胱甘肽过氧化物酶、变性血红蛋白、羟钴胺素、磷酸酶、酪氨酸酶、抗坏血酸氧化酶、黄嘌呤氧化酶、琥珀酸脱氢酶和Cu/Zn超氧化物歧化酶结合，产生一些毒性效应。氰化物与变性血红蛋白中的三价铁离子结合形成无活性的氰化变性血红蛋白。

Organic nitriles decompose into cyanide ions both in vivo and in vitro. Consequently the primary mechanism of toxicity for organic nitriles is their production of toxic cyanide ions or hydrogen cyanide. Cyanide is an inhibitor of cytochrome c oxidase in the fourth complex of the electron transport chain (found in the membrane of the mitochondria of eukaryotic cells). It complexes with the ferric iron atom in this enzyme. The binding of cyanide to this cytochrome prevents transport of electrons from cytochrome c oxidase to oxygen. As a result, the electron transport chain is disrupted and the cell can no longer aerobically produce ATP for energy. Tissues that mainly depend on aerobic respiration, such as the central nervous system and the heart, are particularly affected. Cyanide is also known produce some of its toxic effects by binding to catalase, glutathione peroxidase, methemoglobin, hydroxocobalamin, phosphatase, tyrosinase, ascorbic acid oxidase, xanthine oxidase, succinic dehydrogenase, and Cu/Zn superoxide dismutase. Cyanide binds to the ferric ion of methemoglobin to form inactive cyanmethemoglobin. (L97)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 致癌物分类

对人类不具有致癌性（未被国际癌症研究机构IARC列名）。

No indication of carcinogenicity to humans (not listed by IARC).

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 健康影响

短时间内接触高浓度的氰化物会对大脑和心脏造成伤害，甚至可能导致昏迷、癫痫、呼吸暂停、心脏骤停和死亡。长期吸入氰化物会引起呼吸困难、胸痛、呕吐、血象改变、头痛和甲状腺肿大。皮肤接触氰化物盐可能会引起刺激并产生溃疡。

Exposure to high levels of cyanide for a short time harms the brain and heart and can even cause coma, seizures, apnea, cardiac arrest and death. Chronic inhalation of cyanide causes breathing difficulties, chest pain, vomiting, blood changes, headaches, and enlargement of the thyroid gland. Skin contact with cyanide salts can irritate and produce sores. (L96, L97)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 暴露途径

口服（L96）；吸入（L96）；皮肤给药（L96）

Oral (L96) ; inhalation (L96) ; dermal (L96)

来源:Toxin and Toxin Target Database (T3DB)

吸收、分配和排泄

从氰乙酸和氰乙酯的理化性质来看，可以预期这两种物质通过所有暴露途径都会被适度吸收。在大鼠口服氰乙酸后，观察到组织之间以及怀孕大鼠的胚胎组织之间有相对均匀的分布。可以预期氰乙酯会有类似的行为。

From the physical chemical properties of both cyanoacetic acid and ethyl cyanoacetate it can be expected that both substances will be moderately absorbed by all exposure routes. A relatively even distribution between tissues and also to embryonic tissues of pregnant rats was observed after oral administration of cyanoacetic acid. A similar behavior can be expected for ethyl cyanoacetate.

来源:Hazardous Substances Data Bank (HSDB)

安全信息

• TSCA：
  Yes
• 危险品标志：
  Xi
• 安全说明：
  S26,S36/37,S37/39
• 危险类别码：
  R36/38
• WGK Germany：
  1
• 海关编码：
  2926909090
• 危险品运输编号：
  3276
• RTECS号：
  AG4110000
• 包装等级：
  O53
• 储存条件：
  储存注意事项： - 储存在阴凉、通风的库房中。 - 远离火种和热源。 - 保持容器密封。 - 应与氧化剂、还原剂、酸类、碱类及食用化学品分开存放，切忌混储。 - 配备相应品种和数量的消防器材。 - 储区应备有泄漏应急处理设备和合适的收容材料。

SDS

第一部分：化学品名称

制备方法与用途

化学性质

氰乙酸乙酯是一种无色或微黄色液体，具有芳香气味。它不溶于水，但能与乙醇和乙醚混溶，并溶解于氨水及强碱水溶液中。

用途

1. 医药领域：作为医药中间体，用于制备咖啡因、维生素B等。
2. 化学制品：用作彩色胶片的油溶性成色剂和502胶粘剂的原料。
3. 农药制造：是制备丙二酸二乙酯的中间体，进一步可用于合成2-氨基-4,6-二甲氧基嘧啶（作为磺酰脲类除草剂的中间体），以及杀虫剂氟虫腈和维生素B的中间体。
4. 精细化工产品：用作医药、染料等产品的中间体。在日本，常用于氰基丙烯酸酯类快干胶的制备，广泛应用于汽车零件及家用电器组装件粘接，并在维生素B6、合成染料等领域也有应用。

生产方法

1. 氯乙酸酯化氰化法：将氯乙酸与乙醇反应生成氯乙酸乙酯，经过精制后与氰化钠进行氰化反应，通过过滤和蒸馏步骤得到成品。
2. 氯乙酸氰化酯化法：先用纯碱中和氯乙酸生成氯乙酸钠，再与氰化钠作用得到氰乙酸钠，然后利用盐酸酸化并酯化得到氰乙酸乙酯。经过滤、蒸馏后可得成品。
3. 直接酯化法：将氰乙酸与乙醇进行酯化反应而得。

化学方程式

[ \text{NCCH}_2\text{COOH} + \text{C}_2\text{H}_5\text{OH}[\text{H}_2\text{SO}_4] → \text{NCCH}_2\text{COOC}_2\text{H}_5 + \text{H}_2\text{O} ]

类别

有毒物品，高毒级别

• 急性毒性：口服-大鼠 LD₅₀: 400 毫克/公斤。
• 可燃性危险特性：遇明火或受热产生有毒氰化物气体；遇水会释放出易燃气体。

储运特性

库房需保持通风、低温和干燥环境，并且应与食品、氧化剂及酸类分开存放运输。

灭火方法

使用雾状水、泡沫、干粉、二氧化碳或砂土进行灭火。

反应信息

• 作为反应物：
  描述：

  氰乙酸乙酯 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 16.0h， 生成 3-羟基丙腈
  参考文献：
  名称：

  Reduction selective par le borohydrure de sodium d'un groupe ester ou nitrile dans les epoxydes gem disubstitues par deux croupes attracteurs d'electrons

  摘要：

  DOI：

  10.1016/s0040-4020(01)81701-4
• 作为产物：
  描述：

  3-乙氧基丙腈 在 cobalt(II) acetate N-羟基邻苯二甲酰亚胺 作用下， 以 乙腈 为溶剂， 190.0 ℃ 、900.01 kPa 条件下， 反应 7.0h， 生成 氰乙酸乙酯
  参考文献：
  名称：

  Method for producing cyanoacetic acid esters

  摘要：

  一种生产一般式（I）的氰乙酸酯的方法：其中R代表一个可选择取代的直链或支链C1-8烷基或芳基C1-4烷基。根据该方法，在存在基于铅或过渡金属之一的催化剂的情况下，将一般式（II）的烷氧基丙腈：其中R如上所定义，氧化以形成所需的产物，使用氧气或氧化剂。

  公开号：

  US06700010B1
• 作为试剂：
  描述：

  2-Methyl-N-(1-oxy-pyridin-4-ylmethyl)-benzamide 在 乙酸酐 、 氰乙酸乙酯 、 肼 作用下， 反应 2.0h， 生成 2-甲基苯甲酰胺
  参考文献：
  名称：

  Brana, Miguel F.; Rodriguez, Maria L. Lopez; Rodriguez, Concepcion, Journal of Heterocyclic Chemistry, 1986, vol. 23, p. 1019 - 1022

  摘要：

  DOI：

文献信息

• [EN] THIOPHENE DERIVATIVES FOR THE TREATMENT OF DISORDERS CAUSED BY IGE<br/>[FR] DÉRIVÉS DE THIOPHÈNE POUR LE TRAITEMENT DE TROUBLES PROVOQUÉS PAR IGE
  申请人：UCB BIOPHARMA SRL

  公开号：WO2019243550A1

  公开（公告）日：2019-12-26

  Thiophene derivatives of formula (I) and a pharmaceutically acceptable salt thereof are provided. These compounds have utility for the treatment or prevention of disorders caused by IgE, such as allergy, type 1 hypersensitivity or familiar sinus inflammation.

  提供了公式（I）的噻吩衍生物及其药用可接受的盐。这些化合物对于治疗或预防由IgE引起的疾病具有用途，如过敏、1型超敏反应或家族性鼻窦炎。
• [EN] INHIBITORS OF GLYCINAMIDE RIBONUCLEOTIDE TRANSFORMYLASE<br/>[FR] INHIBITEURS DE LA TRANSFORMYLASE DE LA GLYCINAMIDE RIBONUCLEOTIDE
  申请人：SCRIPPS RESEARCH INST

  公开号：WO2003087065A1

  公开（公告）日：2003-10-23

  Potent human inhibitors of human glycinamide ribonucleotide transformylase and of aminoimidazole carboxamide ribonucleotide transformylase are designed, synthesized, and characterized.

  设计、合成和表征了对人类甘氨酰核糖核苷转甲基酶和氨基咪唑甲酰核糖核苷转甲基酶具有强效抑制作用的人类抑制剂。
• [EN] NOVEL ANTIVIRAL COMPOUNDS<br/>[FR] NOUVEAUX COMPOSÉS ANTIVIRAUX
  申请人：UNIV LEUVEN KATH

  公开号：WO2014170368A1

  公开（公告）日：2014-10-23

  The present invention relates to a series of novel compounds and derivatives thereof, methods to prevent or treat viral infections by using the novel compounds, processes for their preparation, their use to treat or prevent viral infections and their use to manufacture a medicine to treat or prevent viral infections, preferably infections with viruses belonging to the family of the Togaviridae and more preferably infections with chikungunya virus (CHIKV).

  本发明涉及一系列新化合物及其衍生物，利用这些新化合物预防或治疗病毒感染的方法，以及它们的制备过程，用于治疗或预防病毒感染以及用于制造治疗或预防病毒感染的药物，最好是用于治疗属于Togaviridae家族的病毒，更好地是用于治疗寨卡病毒感染。
• [EN] BICYCLIC ARYL SPHINGOSINE 1-PHOSPHATE ANALOGS<br/>[FR] ANALOGUES D’ARYLSPHINGOSINE-1-PHOSPHATE BICYCLIQUES
  申请人：BIOGEN IDEC INC

  公开号：WO2011017561A1

  公开（公告）日：2011-02-10

  Compounds that have agonist activity at one or more of the SlP receptors are provided. The compounds are sphingosine analogs that, after phosphorylation, can behave as agonists at SlP receptors.

  提供具有在一个或多个SlP受体上拮抗活性的化合物。这些化合物是鞘氨醇类似物，在磷酸化后可以在SlP受体上表现为拮抗剂。
• [EN] THIENOPYRIDONE DERIVATIVES AS AMP-ACTIVATED PROTEIN KINASE (AMPK) ACTIVATORS<br/>[FR] DÉRIVÉS DE THÉNOPYRIDONE COMME ACTIVATEURS DE LA PROTÉINE KINASE DÉPENDANTE DE L'AMP (AMPK)
  申请人：MERCK PATENT GMBH

  公开号：WO2009124636A1

  公开（公告）日：2009-10-15

  The present invention relates to compounds of formula (I) wherein R1, R2 and R3 are as defined in claim 1, including pharmaceutical compositions thereof and for their use in the treatment and/or prevention of diseases and disorders modulated by AMP agonists. The invention is also directed to intermediates and to a method of preparation of compounds of formula (I).

  本发明涉及式(I)的化合物，其中R1、R2和R3如权利要求1所定义，包括其药物组合物以及用于治疗和/或预防由AMP激动剂调节的疾病和紊乱的用途。该发明还涉及中间体和式(I)化合物的制备方法。

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