1-丁基哌啶-4-甲酰胺 | 66073-48-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 中文名称: 1-丁基哌啶-4-甲酰胺
• 英文名称: 4-carboxamide-1-butylpiperidine
• 英文别名: 1-butyl-iso-nipecotamide；1-Butyl-4-carbamoylpiperidin；4-Piperidinecarboxamide, 1-butyl-；1-butylpiperidine-4-carboxamide
• CAS: 66073-48-1
• 化学式: C₁₀H₂₀N₂O
• mdl: MFCD20542445
• 分子量: 184.282
• InChiKey: PWVIGOPEAZKAPB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  46.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-丁基哌啶-4-甲酰胺 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 生成 4-氨甲基-1-(正丁基)哌啶
  参考文献：
  名称：

  Synthesis and pharmacological evaluation of carboxamide derivatives as selective serotoninergic 5-HT4 receptor agonists

  摘要：

  A number of new carboxamide derivatives were synthesized. The affinity of these compounds for the serotoninergic 5-HT4 receptor was evaluated by use of radioligand-binding techniques. The agonistic activity was evaluated as the contractile effect of the ascending colon isolated from guinea-pigs. Among these compounds, 4-amino-5-chloro-2-methoxy-N-[1-[2-[(methylsulfonyl)amino]ethly]-4-piperidinylmethyl]benzamide (24) showed a high affinity for the 5-HT4 receptor (Ki = 9.6 nM). Compound 24 displayed a higher affinity for 5-HT4 receptors than the other receptors, including, 5-HT3 and dopamine D-2 receptors. In addition, compound 24 was confirmed to be a potent 5-HT4 receptor agonist (ED50 - 7.0 nM). An interaction model between compound 24 and 5-HT4 receptor was proposed. (C) Elsevier, Paris.

  DOI：

  10.1016/s0223-5234(99)80083-x
• 作为产物：
  描述：

  正溴丁烷 、 哌啶-4-甲酰胺 在 potassium carbonate 作用下， 以 乙醇 为溶剂， 生成 1-丁基哌啶-4-甲酰胺
  参考文献：
  名称：

  （1-丁基-4-哌啶基）甲基8-氨基-7-氯-1,4-苯并二恶烷-5-羧酸盐酸盐：一种高效且选择性的从甲氧氯普胺衍生的5-HT4受体拮抗剂。

  摘要：

  DOI：

  10.1021/jm00077a018

文献信息

• [EN] 1H-INDAZOLE-3-CARBOXAMIDE COMPOUNDS AS CYCLIN DEPENDENT KINASES (CDK) INHIBITORS<br/>[FR] COMPOSES 1H-INDAZOLE-3-CARBOXAMIDE UTILISES EN TANT QU'INHIBITEURS DE KINASES CYCLINE-DEPENDANTES (CDK)
  申请人：ASTEX TECHNOLOGY LTD

  公开号：WO2004014864A1

  公开（公告）日：2004-02-19

  The invention provides a compound of the formula (I) for use in the prophylaxis or treatment of a disease state or condition mediated by a cyclin dependent kinase: wherein A is a group R2 or CH2-R2 where R2 is a carbocyclic or heterocyclic group having from 3 to 12 ring members; B is a bond or an acyclic linker group having a linking chain length of up to 3 atoms selected from C, N, S and O; R1 is hydrogen or a group selected from SO2Rb,SO2NR7R8,CONR7R8,NR7R9 and carbocyclic and heterocyclic groups having from 3 to 7 ring members; R3, to R9 are defined in the description but excluding the compounds N-[(morpholin-4-yl)phenyl-1H-indazole-3-carboxamide and N-[4-(acetylaminosulphonyl)phenyl-1H-indazole-3-carboxamide.

  本发明提供了一种式(I)化合物，用于预防或治疗由细胞周期蛋白依赖性激酶介导的疾病状态或条件：其中A是R2基团或CH2-R2，其中R2是具有3至12个环成员的碳环或杂环基团；B是键或具有最多3个原子（选自C、N、S和O）的链长的不饱和链连接基团；R1是氢或选自SO2Rb、SO2NR7R8、CONR7R8、NR7R9以及具有3至7个环成员的碳环和杂环基团；R3至R9在说明书中定义，但不包括化合物N-[(吗啉-4-基)苯基-1H-吲唑-3-甲酰胺]和N-[4-(乙酰氨基磺酰基)苯基-1H-吲唑-3-甲酰胺]。
• [EN] 1H-INDAZOLE-3-CARBOXAMIDE COMPOUNDS AS MAPKAP KINASE MODULATORS<br/>[FR] COMPOSES 1H-INDAZOLE-3-CARBOXAMIDE UTILISES COMME MODULATEURS DE LA MAPKAP KINASE
  申请人：ASTEX TECHNOLOGY LTD

  公开号：WO2005014554A1

  公开（公告）日：2005-02-17

  The invention provides compounds of the formula: (I) for use in the prophylaxis or treatment of a disease state or condition mediated by a MAPKAP kinase: wherein A is a bond or a group CH2; R1 is a carbocyclic or heterocyclic group having from 3 to 12 ring members; R3, R4, R5 and R6 are the same or different and are each selected from hydrogen, halogen, hydroxy, trifluoromethyl, cyano, nitro, carboxy, amino, carbocyclic and heterocyclic groups having from 3 to 12 ring members; a group Ra -Rb wherein Ra is a bond, 0, CO, X1C(X2), C(X2)Xl, X1C(X2)X1, S, SO, S02, NRc, SO2NRc or NRcS02; and Rb is selected from hydrogen, carbocyclic and heterocyclic groups having from 3 to 12 ring members, and a C1-8 hydrocarbyl group optionally substituted by one or more substituents selected from hydroxy, oxo, halogen, cyano, nitro, amino, mono or di-C1-4 hydrocarbylamino, carbocyclic and heterocyclic groups having from 3 to 12 ring members and wherein one or more carbon atoms of the C1-8 hydrocarbyl group may optionally be replaced by 0, S, SO, SO2, NRc, X1C(X2), C(X2)X1 or X1C(X2)X1; Rc is hydrogen or C1-4 hydrocarbyl; and X1 is O, S or NRc and X2 is =O, =S or =NRc.

  该发明提供了化合物的公式：（I），用于预防或治疗由MAPKAP激酶介导的疾病状态或病情：其中A是键或CH2基团; R1是具有3到12个环成员的碳环或杂环基团; R3，R4，R5和R6相同或不同，每个都选择自氢，卤素，羟基，三氟甲基，氰基，硝基，羧基，氨基，碳环和具有3到12个环成员的杂环基团中的一个; Ra-Rb基团，其中Ra是键，0，CO，X1C（X2），C（X2）Xl，X1C（X2）X1，S，SO，S02，NRc，SO2NRc或NRcS02; Rb选择自具有3到12个环成员的氢，碳环和杂环基团，以及C1-8烃基，可选地被一个或多个选择自羟基，氧化物，卤素，氰基，硝基，单或双C1-4烃基胺基，具有3到12个环成员的碳环和杂环基团的取代基取代，并且C1-8烃基的一个或多个碳原子可以选择性地被0，S，SO，SO2，NRc，X1C（X2），C（X2）X1或X1C（X2）X1取代; Rc是氢或C1-4烃基; X1是O，S或NRc，X2是=O，=S或=NRc。
• 1h-Indazole-3-carboxamide compounds as cyclin dependent kinase (cdk) inhibitors
  申请人：Berdino Valerio

  公开号：US20060135589A1

  公开（公告）日：2006-06-22

  The invention provides a compound of the formula (I) for use in the prophylaxis or treatment of a disease state or condition mediated by a cyclin dependent kinase: wherein A is a group R 2 or CH 2 —R 2 where R 2 is a carbocyclic or heterocyclic group having from 3 to 12 ring members; B is a bond or an acyclic linker group having a linking chain length of up to 3 atoms selected from C, N, S and O; R 1 is hydrogen or a group selected from SO 2 R b , SO 2 NR 7 R 8 , CONR 7 R 8 , NR 7 R 9 and carbocyclic and heterocyclic groups having from 3 to 7 ring members; R 3 , R 4 , R 5 and R 6 are the same or different and are each selected from hydrogen, halogen, hydroxy, trifluoromethyl, cyano, nitro, carboxy, amino, carbocyclic and heterocyclic groups having from 3 to 12 ring members; a group R a —R b wherein R a is a bond, O, CO, X 1 C(X 2 ), C(X 2 )X 1 , X 1 C(X 2 )X 1 , S, SO, SO 2 , NR c , SO 2 NR c or NR c SO 2 ; and R b is selected from hydrogen, carbocyclic and heterocyclic groups having from 3 to 12 ring members, and a C 1-8 hydrocarbyl group optionally substituted by one or more substituents selected from hydroxy, oxo, halogen, cyano, nitro, amino, mono- or di-C 1-4 hydrocarbylamino, carbocyclic and heterocyclic groups having from 3 to 12 ring members and wherein one or more carbon atoms of the C 1-8 hydrocarbyl group may optionally be replaced by O, S, SO, SO 2 , NR c , X 1 C(X 2 ), C(X 2 )X 1 or X 1 C(X 2 )X 1 ; R c is hydrogen or C 1-4 hydrocarbyl; X 1 is O, S or NR c and X 2 is ═O, ═S or ═NR c ; R 7 is selected from hydrogen and a C 1-8 hydrocarbyl group optionally substituted by one or more substituents selected from hydroxy, oxo, halogen, cyano, nitro, amino, mono- or di-C 1-4 hydrocarbylamino, carbocyclic and heterocyclic groups having from 3 to 12 ring members and wherein one or more carbon atoms of the C 1-8 hydrocarbyl group may optionally be replaced by O, S, SO, SO 2 , NR c , X 1 C(X 2 ), C(X 2 )X 1 or X 1 C(X 2 )X 1 ; R 8 is selected from R 7 and carbocyclic and heterocyclic groups having from 3 to 12 ring members; R 9 is selected from R 8 , COR 8 and SO 2 R 8 ; or NR 7 R 8 or NR 7 R 9 may each form a heterocyclic group having from 5 to 12 ring members; but excluding the compounds N-[(morpholin-4-yl)phenyl-1H-indazole-3-carboxamide and N-[4-(acetylaminosulphonyl)phenyl-1H-indazole-3-carboxamide.

  该发明提供了化合物(I)的使用，用于预防或治疗由细胞周期依赖性激酶介导的疾病状态或病情：其中A是R2基团或CH2-R2基团，其中R2是具有3到12个环成员的碳环或杂环基团；B是键或具有链长高达3个C、N、S和O中选择的原子的非环状连接基团；R1是氢或从SO2Rb、SO2NR7R8、CONR7R8、NR7R9和具有3到7个环成员的碳环或杂环基团中选择的基团；R3、R4、R5和R6相同或不同，且每个都从氢、卤素、羟基、三氟甲基、氰基、硝基、羧基、氨基、具有3到12个环成员的碳环或杂环基团中选择；Ra-Rb基团其中Ra是键、O、CO、X1C(X2)、C(X2)X1、X1C(X2)X1、S、SO、SO2、NRc、SO2NRc或NRcSO2；Rb从具有3到12个环成员的碳环或杂环基团和C1-8烃基组中选择，可选地被一个或多个从羟基、氧代、卤素、氰基、硝基、氨基、单个或双个C1-4烃基氨基、具有3到12个环成员的碳环或杂环基团中选择的取代基所取代，其中C1-8烃基组的一个或多个碳原子可选择被O、S、SO、SO2、NRc、X1C(X2)、C(X2)X1或X1C(X2)X1所取代；Rc是氢或C1-4烃基；X1是O、S或NRc，X2是═O、═S或═NRc；R7从氢和可选地被一个或多个从羟基、氧代、卤素、氰基、硝基、氨基、单个或双个C1-4烃基氨基、具有3到12个环成员的碳环或杂环基团中选择的取代基所取代的C1-8烃基中选择，其中C1-8烃基的一个或多个碳原子可选择被O、S、SO、SO2、NRc、X1C(X2)、C(X2)X1或X1C(X2)X1所取代；R8从R7和具有3到12个环成员的碳环或杂环基团中选择；R9从R8、COR8和SO2R8中选择；或NR7R8或NR7R9各自可以形成具有5到12个环成员的杂环基团；但不包括化合物N-[(morpholin-4-yl)phenyl-1H-indazole-3-carboxamide和N-[4-(acetylaminosulphonyl)phenyl-1H-indazole-3-carboxamide]。
• Synthesis and pharmacological evaluation of carboxamide derivatives as selective serotoninergic 5-HT4 receptor agonists
  作者：Katsuhiko Itoh、Koji Kanzaki、Tsuguo Ikebe、Takanobu Kuroita、Hideo Tomozane、Shuji Sonda、Noriko Sato、Keiichiro Haga、Takeshi Kawakita

  DOI：10.1016/s0223-5234(99)80083-x

  日期：1999.4

  A number of new carboxamide derivatives were synthesized. The affinity of these compounds for the serotoninergic 5-HT4 receptor was evaluated by use of radioligand-binding techniques. The agonistic activity was evaluated as the contractile effect of the ascending colon isolated from guinea-pigs. Among these compounds, 4-amino-5-chloro-2-methoxy-N-[1-[2-[(methylsulfonyl)amino]ethly]-4-piperidinylmethyl]benzamide (24) showed a high affinity for the 5-HT4 receptor (Ki = 9.6 nM). Compound 24 displayed a higher affinity for 5-HT4 receptors than the other receptors, including, 5-HT3 and dopamine D-2 receptors. In addition, compound 24 was confirmed to be a potent 5-HT4 receptor agonist (ED50 - 7.0 nM). An interaction model between compound 24 and 5-HT4 receptor was proposed. (C) Elsevier, Paris.
• BINIECKI S.; PROKOPCZYK B., ROCZ. CHEM. <ROCH-AC>, 1977, 51, NO 11, 2263-2265
  作者：BINIECKI S.、 PROKOPCZYK B.

  DOI：——

  日期：——