5-cyano-1-[3(piperid-4-yl)indol-5-yl]-1H-benzimidazole | 160906-89-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 5-cyano-1-[3(piperid-4-yl)indol-5-yl]-1H-benzimidazole
• 英文别名: 1-(3-piperidin-4-yl-1H-indol-5-yl)benzimidazole-5-carbonitrile
• CAS: 160906-89-8
• 化学式: C₂₁H₁₉N₅
• 分子量: 341.415
• InChiKey: KVKWRJDNIJTMGN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  69.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  5-Cyano-1-[3-(N-t-butoxycarbonylpiperid-4-yl)indol-5-yl]-1H-benzimidazole 以 二氯甲烷 为溶剂， 以afforded the title compound (64%) as a yellow solid的产率得到5-cyano-1-[3(piperid-4-yl)indol-5-yl]-1H-benzimidazole
  参考文献：
  名称：

  5-arylindole derivatives

  摘要：

  式(I)的化合物，其中R.sub.1是(a)，(b)，(c)或(d)；n为0，1或2；A，B，C和D各自独立地为氮或碳；R.sub.2，R.sub.3，R.sub.4和R.sub.5各自独立地为氢，C.sub.1至C.sub.6烷基，芳基，C.sub.1至C.sub.3烷基芳基，卤素（例如氟，氯，溴或碘），氰基，硝基，--(CH.sub.2).sub.m NR.sub.14 R.sub.15，--(CH.sub.2).sub.m OR.sub.9，--SR.sub.9，--SO.sub.2 NR.sub.14 R.sub.15，--(CH.sub.2).sub.m NR.sub.14 SO.sub.2 R.sub.15，--(CH.sub.2).sub.m NR.sub.14 CO.sub.2 R.sub.9，--(CH.sub.2).sub.m NR.sub.14 COR.sub.9，--(CH.sub.2).sub.m NR.sub.14 CONHR.sub.9，--CONR.sub.14 R.sub.15，或--CO.sub.2 R.sub.9；R.sub.2和R.sub.3，R.sub.3和R.sub.4，或R.sub.4和R.sub.5可以共同形成五到七元的烷基环，六元的芳基环，具有1个N、O或S杂原子的五到七元的杂烷基环或具有1或2个N、O或S杂原子的五到六元的杂芳基环及其药学上可接受的盐。这些化合物对治疗偏头痛和其他疾病有用。这些化合物是有用的心理治疗药物，是有效的5-羟色胺（5-HT.sub.1）激动剂和苯二氮平激动剂和拮抗剂，可用于治疗抑郁症、焦虑症、进食障碍、肥胖症、药物滥用、集群头痛、偏头痛、疼痛和慢性阵发性半侧头痛以及与缺乏5-羟色胺能神经递质有关的其他疾病。这些化合物还可用作中枢作用降压剂和扩血管剂。

  公开号：

  US05886008A1

文献信息

• 5-arylindolederivatives and their use as serotonin(5-ht1)agonists
  申请人：PFIZER INC.

  公开号：EP1094064A1

  公开（公告）日：2001-04-25

  A compound of the formula wherein R1 is n is 0, 1, or 2; A, B, C, and D are each independently nitrogen or carbon; R2, R3, R4, and R5 are each independently hydrogen, C1 to C6 alkyl, aryl, C1 to C3 alkyl-aryl, halogen, cyano, nitro, -(CH2)mNR14R15, -(CH2)mOR9, -SR9, -SO2NR14R15, -(CH2)mNR14SO2R15, -(CH2)mNR14CO2R9, -(CH2)mNR14COR9, -(CH2)mNR14CONHR9, -CONR14R15, or -CO2R9; R2 and R3, R3 and R4, or R4 and R5 may be taken together to form a five- to seven-membered alkyl ring, a six-membered aryl ring, a five- to seven-membered heteroalkyl ring having 1 heteroatom of N, O, or S, or a five- to six-membered heteroaryl ring having 1 or 2 heteroatoms of N, O, or S; R6 is hydrogen, -OR10, or -NHCOR10; R7, R8, R14, and R15 are each independently hydrogen, C1 to C6 alkyl, -(CH2)xOR11, C1 to C3 alkyl-aryl, aryl; R7 and R8 or R14 and R15 may be taken together to form a three- to six-membered ring; R9 is hydrogen, C1 to C6 alkyl, C1 to C3 alkyl-aryl, or aryl; R10 is hydrogen, C1 to C6 alkyl, or C1 to C3 alkyl-aryl; R11 is hydrogen, C1 to C6 alkyl, or C1 to C3 alkyl-aryl; m is 0, 1, 2, or 3; x is 2 or 3; a broken line represents an optional double bond; and the above aryl groups and the aryl moieties of the above alkyl-aryl groups are independently phenyl or substituted phenyl, wherein said substituted phenyl may be substituted with one to three of C1 to C4 alkyl, halogen, hydroxy, cyano, carboxamido, nitro, or C1 to C4 alkoxy; or a pharmaceutically acceptable satt thereof.

  式中的化合物 其中 R1 是 n为0、1或2；A、B、C和D各自独立地为氮或碳；-(CH2)mOR9、-SR9、-SO2NR14R15、-( )mNR14SO2R15、-( )mNR14CO2R9、-( )mNR14COR9、-( )mNR14CONHR9、-CONR14R15 或 -CO2R9；R2 和 R3、R3 和 R4 或 R4 和 R5 可组合成五至七元烷基环、六元芳基环、具有 1 个 N、O 或 S 杂原子的五至七元杂烷基环或具有 1 或 2 个 N、O 或 S 杂原子的五至六元杂芳基环；R6是氢、-OR10或-NHCOR10； R7、R8、R14和R15各自独立地是氢、C1至C6烷基、-( )xOR11、C1至C3烷基芳基、芳基；R7 和 R8 或 R14 和 R15 可结合在一起形成三至六元环；R9 是氢、C1 至 C6 烷基、C1 至 C3 烷基芳基或芳基；R10 是氢、C1 至 C6 烷基或 C1 至 C3 烷基芳基；R11 是氢、C1 至 C6 烷基或 C1 至 C3 烷基芳基；m 是 0、1、2 或 3；x 是 2 或 3；断线代表任选双键；上述芳基和上述烷基芳基的芳基独立地为苯基或取代苯基，其中所述取代苯基可被 C1 至 C4 烷基、卤素、羟基、氰基、羧酰胺基、硝基或 C1 至 C4 烷氧基中的一至三个取代；或其药学上可接受的酯。
• 5-ARYLINDOLE DERIVATIVES AND THEIR USE AS SEROTONIN (5-HT 1?) AGONISTS
  申请人：PFIZER INC.

  公开号：EP0666858A1

  公开（公告）日：1995-08-16
• 5-ARYLINDOLE DERIVATIVES AND THEIR USE AS SEROTONIN (5-HT 1) AGONISTS
  申请人：PFIZER INC.

  公开号：EP0666858B1

  公开（公告）日：2001-06-13
• US5886008A
  申请人：——

  公开号：US5886008A

  公开（公告）日：1999-03-23
• [EN] 5-ARYLINDOLE DERIVATIVES AND THEIR USE AS SEROTONIN (5-HT1) AGONISTS<br/>[FR] DERIVES DE 5-ARYLINDOLE ET LEUR UTILISATION COMME AGONISTES DE LA SEROTONINE (5-HT1)
  申请人：PFIZER INC.

  公开号：WO1994010171A1

  公开（公告）日：1994-05-11

  (EN) Compounds of formula (I), wherein R1 is (a), (b), (c) or (d); n is 0, 1 or 2; A, B, C and D are each independently nitrogen or carbon; R2, R3, R4 and R5 are each independently hydrogen, C1 to C6 alkyl, aryl, C1 to C3 alkyl-aryl, halogen (e.g. fluorine, chlorine, bromine or iodine), cyano, nitro, -(CH2)mNR14R15, -(CH2)mOR9, -SR9, -SO2NR14R15, -(CH2)mNR14SO2R15, -(CH2)mNR14CO2R9, -(CH2)mNR14COR9, -(CH2)mNR14CONHR9, -CONR14R15, or -CO2R9; R2 and R3, R3 and R4, or R4 and R5 may be taken together to form a five- to seven-membered alkyl ring, a six-membered aryl ring, a five- to seven-membered heteroalkyl ring having 1 heteroatom of N, O, or S, or a five- to six-membered heteroaryl ring having 1 or 2 heteroatoms of N, O, or S and the pharmaceutically acceptable salts thereof. These compounds are useful in treating migraine and other disorders. These compounds are useful psychotherapeutics and are potent serotonin (5-HT1) agonists and benzodiazepine agonists and antagonists and may be used in the treatment of depression, anxiety, eating disorders, obesity, drug abuse, cluster headache, migraine, pain and chronic paroxysmal hemicrania and headache associated with vascular disorders, and other disorders arising from deficient serotonergic neurotransmission. The compounds can also be used as centrally acting antihypertensives and vosodilators.(FR) L'invention concerne des composés de formule (I) dans laquelle R1 représente (a), (b), (c) ou (d); n vaut 0, 1 ou 2; A, B, C et D représentent chacun indépendamment azote ou carbone; R2, R3, R4 et R5 représentent chacun indépendamment hydrogène, alkyle C1 à C6, aryle, alkylaryle C1 à C3, halogène (par exemple fluor, chlore, brome ou iode), cyano, nitro, -(CH2)mNR14R15, -(CH2)mOR9, -SR9, -SO2NR14R15, -(CH2)mNR14SO2R15, -(CH2)mNR14CO2R9, -(CH2)mNR14COR9, -(CH2)mNR14CONHR9, -CONR14R15, ou bien -CO2R9; R2 et R3, R3 et R4, ou bien R4 et R5 peuvent être pris ensemble pour former un cycle alkyle présentant 5 à 7 éléments, un cycle aryle à 6 éléments, un cycle hétéroalkyle présentant 5 à 7 éléments et un hétéroatome de N, O ou bien S, ou bien un cycle hétéroaryle présentant 5 à 6 éléments et 1 ou 2 hétéroatomes de N, O ou bien S. L'invention concerne également les sels pharmaceutiquement acceptables desdits composés. Ces composés sont utiles dans le traitement de la migraine et d'autres troubles. Ils sont également utiles en tant que médicaments psychothérapeutiques et sont de puissants agonistes de la sérotonine (5-HT1) ainsi que des agonistes et des antagonistes de la benzodiazépine, et ils peuvent être utilisés dans le traitement de la dépression, de l'anxiété, des troubles de l'alimentation, de l'obésité, de la toxicomanie, de la céphalée vasculaire de Orton, de la migraine, de la douleur, de l'hécrimanie paroxystique chronique et des céphalées associées à des troubles vasculaires, et d'autres troubles dus à une neurotransmission sérotonergique déficiente. Les composés selon l'invention peuvent également être utilisés comme antihypertenseurs des vasodilatateurs agissant centralement.