N-(4,5-Dihydro-1H-imidazol-2-yl)-1H-benzimidazol-6-amine | 177843-18-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: N-(4,5-Dihydro-1H-imidazol-2-yl)-1H-benzimidazol-6-amine
• 英文别名: N-(4,5-dihydro-1H-imidazol-2-yl)-3H-benzimidazol-5-amine
• CAS: 177843-18-4
• 化学式: C₁₀H₁₁N₅
• 分子量: 201.23
• InChiKey: DPXMAQCBFXYNLT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  65.1
• 氢给体数：
  3
• 氢受体数：
  2

文献信息

• Methods of making 6-[(4,5-Dihydro-1H-imidazol-2-yl)amino-]-7-methyl-1H-benzimidazole-4-carbonitrile and its preferred salt form
  申请人：——

  公开号：US20040167194A1

  公开（公告）日：2004-08-26

  6-[(4,5-Dihydro-1H-imidazol-2-yl)amino-]-7-methyl-1H-benzimidazole-4-carbonitrile substantially free of 2,3,7-triamino-4,6-dimethyl-1,9-phenazinedicarbonitrile, and the anhydrous monoacetate salt thereof, are useful in the treatment of alpha-2 mediated disorders such as ocular hypertension.

  6-[(4,5-二氢-1H-咪唑-2-基)氨基]-7-甲基-1H-苯并咪唑-4-羧腈在2,3,7-三氨基-4,6-二甲基-1,9-苝二羧腈和其无水单乙酸盐的情况下，可用于治疗α-2介导的疾病，如眼压高。
• [EN] 5-(2-IMIDAZOLINYLAMINO)-BENZIMIDAZOLE DERIVATIVES, THEIR PREPARATION AND THEIR USE AS .ALPHA.-ADRENOCEPTOR AGONISTS WITH IMPROVED METABOLIC STABILITY<br/>[FR] 5-(2-IMIDAZOLINYLAMINO)-BENZIMIDAZOLE, DERIVES ET PROCEDES DE PREPARATION ET D'UTILISATION DE CES DERNIERS EN TANT QU'AGONISTES DU RECEPTEUR ALPHA-ADRENERGIQUE AYANT UNE MEILLEURE STABILITE METABOLIQUE
  申请人：PROCTER & GAMBLE

  公开号：WO1999026942A1

  公开（公告）日：1999-06-03

  The present invention is directed to compounds having a structure according formula (I), wherein: (a) R1 is alkyl; (b) R2 is selected from the group consisting of: hydrogen, alkyl, methoxy, cyano, and halo; (c) R3 is selected from the group consisting of: hydrogen, methyl, hydroxy, cyano and halo; (d) R4 is selected from the group consisting of: hydrogen, methyl, ethyl and isopropyl; (e) R5 is selected from the group consisting of: hydrogen, methyl, amino, methoxy, hydroxy, cyano and halo; (f) provided that at least one of R2, R3, R4 or R5 is other than hydrogen or fluorine; (g) provided that when R1 is methyl and both R2 and R5 are hydrogen, R3 is other than methyl or halo; (h) provided that when R3 is cyano, R1 is methyl; and any tautomer of the structure or a pharmaceutically acceptable salt, or biohydrolyzable ester, amide, or imide thereof. The compounds of the present invention are peripherally acting selective alpha-2 adrenergic compounds that lower CNS activity and that resist metabolic transformation into undesirable compounds.

  本发明涉及具有以下式（I）的结构的化合物，其中：（a）R1是烷基；（b）R2选自以下组：氢，烷基，甲氧基，氰基和卤素；（c）R3选自以下组：氢，甲基，羟基，氰基和卤素；（d）R4选自以下组：氢，甲基，乙基和异丙基；（e）R5选自以下组：氢，甲基，氨基，甲氧基，羟基，氰基和卤素；（f）至少有一个R2，R3，R4或R5不是氢或氟；（g）当R1是甲基且R2和R5均为氢时，R3不是甲基或卤素；（h）当R3是氰基时，R1是甲基；以及该结构的任何互变异构体或药学上可接受的盐，或可生物水解的酯，酰胺或亚胺。本发明的化合物是周围作用的选择性α-2肾上腺素化合物，可以降低中枢神经系统的活性，并抵抗代谢转化为不良化合物。
• [EN] METHODS OF MAKING 6-[(4,5-DIHYDRO-1H-IMIDAZOL-2-YL)AMINO-]-7-METHYL-1H-BENZIMIDAZOLE-4-CARBONITRILE AND ITS PREFERRED SALT FORM<br/>[FR] PROCEDES DE FABRICATION DE 6-[(4,5-DIHYDRO-1H-IMIDAZOL-2-YL)AMINO-]-7-METHYL-1H-BENZIMIDAZOLE-4-CARBONITRILE ET FORME PREFEREE D'UN SEL DE CELUI-CI
  申请人：PROCTER & GAMBLE

  公开号：WO2004074279A1

  公开（公告）日：2004-09-02

  6-[(4,5-Dihydro-1H-imidazol-2-yl)amino-]-7-methyl-1H-benzimidazole-4-carbonitrile substantially free of 2,3,7-triamino-4,6-dimethyl-1,9-phenazinedicarbonitrile, and the anhydrous monoacetate salt thereof, are useful in the treatment of alpha-2 mediated disorders such as ocular hypertension.

  6-[(4,5-二氢-1H-咪唑-2-基)氨基]-7-甲基-1H-苯并咪唑-4-羧腈，基本上不含2,3,7-三氨基-4,6-二甲基-1,9-菲嗪二羧腈，以及其无水单乙酸盐，在治疗α-2介导的疾病，如眼压增高方面具有用处。
• Novel benzimidazole derivatives
  申请人：Synaptic Pharmaceutical Corporation

  公开号：US20030181730A1

  公开（公告）日：2003-09-25

  This invention provides compounds having the structure: 1 wherein each of R 1 , R 2 , R 3 and R 9 is independently H; straight chain or branched, substituted or unsubstituted C 1 -C 7 alkyl, C 2 -C 7 alkenyl or alkynyl; C 3 -C 7 cycloalkyl or cycloalkenyl; acyl, phenyl, substituted phenyl, or heteroaryl; wherein each dashed line represents a single bond or a double bond with the proviso that if R 1 is present, R 3 is absent and there is a double bond between N at position 3 and C at position 2 and a single bond between C at position 2 and N at position 1 and if R 3 is present, R 1 is absent and there is a double bond between N at position 1 and C at position 2 and a single bond between C at position 2 and N at position 3; wherein each of R 4 , R 5 and R 6 is independently H, F, Cl, Br, I; straight chain or branched, substituted or unsubstituted C 1 -C 7 alkyl, C 2 -C 7 alkenyl or alkynyl; C 3 -C 7 cycloalkyl or cycloalkenyl; phenyl, substituted phenyl, heteroaryl, —OH, —OR 7 , —CN, —COR 7 , —CO 2 R 7 , —CON(R 7 ) 2 , —OCOR 7 , —SR 7 , —N(R 7 ) 2 , —NR 7 COR 7 , —(CH 2 ) n OR 7 , —(CH 2 ) n N(R 7 ) 2 , —(CH 2 ) n NR 7 COR 7 , wherein n is an integer from 1 to 4; and wherein each of R 7 and R 8 is independently H; straight chain or branched, substituted or unsubstituted C 1 -C 7 alkyl, C 2 -C 7 alkenyl or alkynyl; phenyl or substituted phenyl. These compounds are selective for cloned human alpha 2 receptors and are useful as analgesic, sedative or anaesthetic agents.

  本发明提供具有结构的化合物：1其中R1，R2，R3和R9中的每一个都是独立的H; 直链或支链，取代或未取代的C1-C7烷基，C2-C7烯基或炔基; C3-C7环烷基或环烯基; 酰基，苯基，取代苯基或杂环基; 其中每个虚线代表单键或双键，前提是如果R1存在，则R3不存在，并且在位置3处的N和位置2处的C之间有双键，在位置2处的C和位置1处的N之间有单键，如果R3存在，则R1不存在，并且在位置1处的N和位置2处的C之间有双键，在位置2处的C和位置3处的N之间有单键; 其中R4，R5和R6中的每一个都是独立的H，F，Cl，Br，I; 直链或支链，取代或未取代的C1-C7烷基，C2-C7烯基或炔基; C3-C7环烷基或环烯基; 苯基，取代苯基，杂环基，—OH，—OR7，—CN，—COR7，—CO2R7，—CON(R7)2，—OCOR7，—SR7，—N(R7)2，—NR7COR7，—(CH2)nOR7，—(CH2)nN(R7)2，—(CH2)nNR7COR7，其中n是1到4的整数; 其中R7和R8中的每一个都是独立的H; 直链或支链，取代或未取代的C1-C7烷基，C2-C7烯基或炔基; 苯基或取代苯基。 这些化合物对克隆的人类α2受体具有选择性，并可用作镇痛，镇静或麻醉剂。
• Methods of making 6-[(4,5-dihydro-1H-imidazol-2-yl)amino-]-7-methyl-1H-benzimidazole-4-carbonitrile and its preferred salt form
  申请人：Randall Lynn Jared

  公开号：US20060122248A1

  公开（公告）日：2006-06-08

  6-[(4,5-Dihydro-1H-imidazol-2-yl)amino-]-7-methyl-1H-benzimidazole-4-carbonitrile substantially free of 2,3,7-triamino-4,6-dimethyl-1,9-phenazinedicarbonitrile, and the anhydrous monoacetate salt thereof, are useful in the treatment of alpha-2 mediated disorders such as ocular hypertension.

  6-[(4,5-二氢-1H-咪唑-2-基)氨基]-7-甲基-1H-苯并咪唑-4-羧腈，基本上不含2,3,7-三氨基-4,6-二甲基-1,9-苯并二氰基的盐酸单乙酰化物，可用于治疗α-2介导的疾病，如眼压增高。