robenidine | 25875-51-8

• 物质功能分类: 生物化工 - 生化试剂 - 激动剂抑制剂
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: robenidine
• 英文别名: NCL812；1,3-bis-[(p-chlorobenzylidene)-amino]-guanidine；1,2-bis[(E)-(4-chlorophenyl)methylideneamino]guanidine
• CAS: 25875-51-8
• 化学式: C₁₅H₁₃Cl₂N₅
• 分子量: 334.208
• InChiKey: MOOFYEJFXBSZGE-LQGKIZFRSA-N

物化性质

• 熔点：
  289.5°C
• 沸点：
  490.35°C (rough estimate)
• 密度：
  1.3042 (rough estimate)
• 碰撞截面：
  187.59 Ų [M-H]-; 189.05 Ų [M+H]+

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  75.1
• 氢给体数：
  2
• 氢受体数：
  3

制备方法与用途

用途

盐酸氯苯胍是一种白色或淡黄色的结晶性粉末，常用于抗原虫治疗。

反应信息

• 作为产物：
  描述：

  1,3-二氨基胍盐酸盐 、 4-氯苯甲醛 以 乙醇 为溶剂， 反应 0.17h， 以91%的产率得到robenidine
  参考文献：
  名称：

  不对称和单体罗布定类似物的革兰氏阳性和革兰氏阴性抗生素活性

  摘要：

  罗非替丁的去对称化（1：N '，2-二（（E）-4-氯苄叉）肼-1-羧酰亚胺肼）和亚胺烷基取代基的引入具有良好的抗生素活性。值得注意的是，两种类似物对耐万古霉素的肠球菌（VRE）的效力有所提高，其中一种的MIC为0.5μgmL -1。发现有五个类似物比铅1具有更强的效价。吲哚部分的引入导致针对甲氧西林抗性金黄色葡萄球菌（MRSA）的活性最强的robenidine类似物，MIC为1.0μgmL -1。亚胺C = NH等位基因（C = O / C = S）不活跃。单体类似物为16–64μgmL-1对MRSA和VRE有效。缺少末端酰肼NH部分的类似物在64μgmL -1下显示适度的革兰氏阴性活性。研究表明，在16–64μgmL -1下， 4-叔丁基类似物对革兰氏阳性和阴性菌株均具有活性。通常，除伴随引入亚胺C-烷基外，对芳香族基团的其他修饰耐受性差。这些类似物对MRSA和VRE的活性范围为8μgmL

  DOI：

  10.1002/cmdc.201800463

文献信息

• Antiprotozoal imidazopyridine compounds
  申请人：Biftu Tesfaye

  公开号：US20060293303A1

  公开（公告）日：2006-12-28

  Compounds described by the Formula (I) or (II): or pharmaceutically acceptable salts, or N-oxides thereof. The compounds are useful for the treatment and prevention of protozoal diseases in mammals and birds. A method for controlling coccidiosis in poultry comprises administering an effective amount of the compound alone, or in combination with one or more anticoccidieal agent(s). A composition for controlling coccidiosis in poultry comprises the compound alone, or in combination with one or more anticoccidial agent(s). Methods for the treatment and prevention of mammalian protozoal diseases, such as, for example, toxoplasmosis, malaria. African typanosomiasis, Chagas disease, and opportunistic infections comprise administering the compound alone, or in combination with one or more antiprotozoal agent(s).

  由Formula (I)或(II)描述的化合物：或其药学上可接受的盐，或其N-氧化物。这些化合物对哺乳动物和鸟类的原虫病的治疗和预防有用。控制家禽球虫病的方法包括单独或与一种或多种抗球虫药剂联合投与有效量的化合物。用于控制家禽球虫病的组合物包括单独使用该化合物或与一种或多种抗球虫药剂的组合。用于治疗和预防哺乳动物原虫病的方法，例如弓形虫病、疟疾、非洲锥虫病、充血性心脏病和机会性感染包括单独或与一种或多种抗原虫药剂的组合投与该化合物。
• Pharmaceutical preparation comprising an active dispersed on a matrix
  申请人：——

  公开号：US20040058896A1

  公开（公告）日：2004-03-25

  The present invention relates to the field of pharmaceutical technology and describes a novel advantageous preparation for an active ingredient. The novel preparation is suitable for producing a large number of pharmaceutical dosage forms. In the new preparation an active ingredient is present essentially uniformly dispersed in an excipient matrix composed of one or more excipients selected from the group of fatty alcohol, triglyceride, partial glyceride and fatty acid ester.

  本发明涉及制药技术领域，描述了一种新的有利的活性成分制备方法。这种新的制备方法适用于生产大量的药物剂型。在这种新的制备方法中，活性成分基本上均匀地分散在由脂肪醇、甘油三酯、部分甘油酯和脂肪酸酯等多种赋形剂中选择的一种或多种赋形剂组成的赋形剂基质中。
• Naphthoquinone derivatives for the treatment of parasitic infections
  申请人：THE WELLCOME FOUNDATION LIMITED

  公开号：EP0537947A1

  公开（公告）日：1993-04-21

  The present invention relates to novel naphthoquinones of formula (I): wherein R³ is a C₁₋₃₅ non-aromatic hydrocarbon residue optionally substituted by one or more substituents selected from halo, C₁₋₆ alkoxy, hydroxy, phenyl, phenyl-C₁₋₆alkoxy and phenyl-C₁₋₆alkyl, each such phenyl group or mainly being optionally substituted by one or more groups selected from C₁₋₆ alkoxy, C₁₋₆ alkyl, C₁₋₆alkoxy-C₁₋₆alkyl, hydroxy, halogen, halo-C₁₋₆alkyl, amine and mono- or di-C₁₋₄alkyl-amino; and    either the dotted line represents a double bond between the 2 and 3 positions of the naphthyl ring, R¹ and R⁴ each represent =O, and R² represents a phosphate group wherein R⁵ and R⁶ which may be the same or different, each represent a hydrogen atom or a C₁₋₆ alkyl group;    or the dotted line represents double bonds between the 1,2 and 3,4 positions of the naphthyl ring, and R¹, R² and R⁴ each represent a phosphate group         -OP(O)(OR⁵)(OR⁶) (wherein R⁵ and R⁶ are as hereinbefore described) and physiologically acceptable salts thereof. The compounds of formula (I) are useful in the treatment of parasitic infections.

  本发明涉及公式（I）的新萘醌： 其中R³是C₁₋₃₅非芳香烃碳氢残基，可选择性地被一个或多个取代基所取代，所述取代基选自卤素，C₁₋₆烷氧基，羟基，苯基，苯基-C₁₋₆烷氧基和苯基-C₁₋₆烷基，每个苯基或主要是可选择性地被一个或多个选自C₁₋₆烷氧基，C₁₋₆烷基，C₁₋₆烷氧基-C₁₋₆烷基，羟基，卤素，卤基-C₁₋₆烷基，胺和单或二-C₁₋₄烷基氨基的基团所取代；且点线表示萘环的2和3位置之间的双键，R¹和R⁴各自表示=O，R²表示磷酸酯基团，其中R⁵和R⁶可以相同或不同，分别表示氢原子或C₁₋₆烷基；或者点线表示萘环的1,2和3,4位置之间的双键，R¹，R²和R⁴各自表示磷酸酯基团-OP（O）（OR⁵）（OR⁶）（其中R⁵和R⁶如上所述），以及其生理上可接受的盐。 公式（I）的化合物在治疗寄生虫感染方面非常有用。
• Heterocyclic compounds
  申请人：THE WELLCOME FOUNDATION LIMITED

  公开号：EP0447164A1

  公开（公告）日：1991-09-18

  A compound of formula (I):- wherein R¹ represents a hydrogen or halogen atom, or a cyano group; R² represents an optionally substituted carbocyclic group having 6 to 10 ring atoms and containing at least one aromatic ring; an optionally substituted heterocyclic group having 5 to 10 ring atoms, including 1 to 4 heteroatoms selected from O,N and S, and containing at least one aromatic ring; or an optionally substituted C₃₋₆cycloalkyl, C₃₋₆cycloalkyl- C₁₋₆alkyl, or C₁₋₁₀alkyl group; R³ and R⁴, which may be the same or different, each represent    a hydrogen or halogen atom, or a C₁₋₆alkyl group optionally substituted by 1 to 3 halogen atoms; and R⁵ represents    a hydrogen atom, a hydroxyl group, or a C₁₋₆alkyl group, optionally substituted by hydroxy, carboxy, amino or mono- or di-(C₁₋₄)alkyl amino,    and salts and other physiologically functional derivative thereof. The compounds are useful in the treatment of parasitic infections eg. malaria, coccidiosis and Pneumocystis carinii pneumonia.

  化合物的化学式为（I）：其中R¹代表氢原子或卤素原子或氰基；R²代表可选取代的碳环基团，其有6至10个环原子并含有至少一个芳香环；可选取代的杂环基团，其有5至10个环原子，包括1至4个从O、N和S中选取的杂原子，并含有至少一个芳香环；或可选取代的C₃₋₆环烷基、C₃₋₆环烷基- C₁₋₆烷基，或C₁₋₁₀烷基；R³和R⁴，它们可以相同也可以不同，每个代表氢原子或卤素原子，或由1至3个卤素原子取代的C₁₋₆烷基；R⁵代表氢原子、羟基，或由羟基、羧基、氨基或单烷基或双烷基(C₁₋₄)氨基取代的C₁₋₆烷基，以及其盐和其他生理功能衍生物。这些化合物在治疗寄生虫感染，例如疟疾、球虫病和肺孢子虫肺炎中有用。
• Water-soluble composition comprising a robenidine salt
  申请人：ABIC Ltd.

  公开号：US03954996A1

  公开（公告）日：1976-05-04

  There are disclosed water-soluble compositions comprising a 1,3-bis-[(p-chlorobenzylidene)-amino]-guanidine (called Robenidine) salt, particularly the hydrochloride. Said compositions comprise also a suitable water-soluble organic solvent and a suitable water-soluble solubilizer; the solvent and the solubilizer being miscible with each other. There are also disclosed aqueous solutions comprising the above composition and a method for the treatment of animals being infected with Cocciodiosis with said aqueous solution.

  公开了一种水溶性组合物，包括1,3-双[(对氯苯甲亚啉)-氨基]-鸟氨酸盐（称为Robenidine）,特别是盐酸盐。该组合物还包括适当的水溶性有机溶剂和适当的水溶性增溶剂；所述溶剂和增溶剂与彼此相混。还公开了包含上述组合物的水溶性溶液以及使用该水溶液治疗感染鸟球虫病的动物的方法。