3-{[5-(2-Adamantan-1-yl-ethyl)-1-methyl-2-o-tolyl-1H-imidazole-4-carbonyl]-amino}-benzoic Acid Benzyl Ester | 269070-99-7

• 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: 3-{[5-(2-Adamantan-1-yl-ethyl)-1-methyl-2-o-tolyl-1H-imidazole-4-carbonyl]-amino}-benzoic Acid Benzyl Ester
• 英文别名: Benzyl 3-[[5-[2-(1-adamantyl)ethyl]-1-methyl-2-(2-methylphenyl)imidazole-4-carbonyl]amino]benzoate
• CAS: 269070-99-7
• 化学式: C₃₈H₄₁N₃O₃
• 分子量: 587.762
• InChiKey: HLYIDAIHNMFAAX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.7
• 重原子数：
  44
• 可旋转键数：
  10
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  73.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  5-(2-Adamantan-1-yl-ethyl)-1-methyl-2-o-tolyl-1H-imidazole-4-carboxylic Acid 、 3-{[5-(2-Adamantan-1-yl-ethyl)-2-(2-dimethylamino-phenyl)-1H-imidazole-4-carbonyl]-amino}-benzoic Acid Benzyl Ester 、 3-氨基苯甲酸苄酯 以71%的产率得到3-{[5-(2-Adamantan-1-yl-ethyl)-1-methyl-2-o-tolyl-1H-imidazole-4-carbonyl]-amino}-benzoic Acid Benzyl Ester
  参考文献：
  名称：

  Pharmaceutical compositions comprising proton pump inhibitors and gastrin/cholecystokinin receptor ligands

  摘要：

  含有质子泵抑制剂和公式（I）或其药学上可接受的盐的化合物的制剂，对治疗胃肠道疾病有用。其中，X和Y分别是═N—，—N（R5）—（其中R5选择自H，Me，Et，Pr，Bn，—OH和—CH2COOR6，其中R6代表H，Me，Et，Pr或Bn），═CH—，S—或—O—；n为1至4；R1为H或C1至C15的烃基，其中最多可有三个C原子被N，O和/或S原子取代，最多可有三个H原子被卤素原子取代；当n大于1时，R2选择自H，Me，Et，Pr和OH，每个R2独立选择自H，Me，Et，Pr和OH；当n为1时，R3选择自H，Me，Et和Pr；当n大于1时，每个R3独立选择自H，Me，Et和Pr，或被双键连接的相邻碳原子上的两个R3基团；或R2和R3在同一碳原子上连接形成C3到C6的环状碳基；或相邻碳原子上缺少两个R3基团，它们被双键连接；或R2和R3在同一碳原子上共同表示═O基团；R4为C1至C15的烃基，其中最多可有两个C原子被N，O和/或S原子取代，最多可有两个H原子被卤素原子取代；Z为—（NR7）a—CO—（NR8）b—（其中a为0或1，b为0或1，且R7和R8与上述R6中的基团独立选择），—CO—NR7—CH2—CO—NR8—，—CO—O—，—CH2—CH2—，—CH═CH—，—CH2—NR—或键；Q为—R9V，或（II）（其中R9为—CH2—；—CH2—CH2—；或（III）R9和R8与R8连接的氮原子一起形成被V取代的哌啶或吡咯烷环；V为—CO—NH—SO2-Ph，SO2—NH—CO-Ph，—CH2OH或公式—R10U的基团（其中U为—COOH，四唑基，—CONHOH—或—SO3H；R10为键；C1至C6的烃基，可选地被羟基，氨基或乙酰胺基取代；—O—（C1至C3的烷基）-；—SO2NR11—CHR12—；—CO—NR11—CHR12—，其中R11和R12独立选择自H和甲基；或—NH—（CO），—CH2—，其中c为0或1）；T为C1至C6的烃基，—NR6R7（其中R6和R7如上所定义），—OMe，—OH，—CH2OH，卤素或三卤甲基；m为1或2；p为0至3；q为0至2，但当Z为键时，q为1或2。

  公开号：

  US20030195240A1

文献信息

• Gastrin and cholecystokinin receptor ligands
  申请人：James Black Foundation Limited

  公开号：US06479531B1

  公开（公告）日：2002-11-12

  Compounds of formula (I) and their pharmaceutically acceptable salts are ligands at gastrin and/or cholecystokinin receptors. X and Y are independently ═N—, —N(R5)—═CH—, —S— or —O—. n is from 1 to 4; R1 is H or C1 to C15 hydrocarbyl R2 is selected from H, Me, Et, Pr and OH, R3 is selected from H, Me, Et and Pr; or (when n is greater than 1) each R3 is independently selected from H, Me, Et and Pr, or two R3 groups on neighbouring carbon atoms are linked to form a C3 to C6 carbocylic ring, or R2 and R3 on the same carbon atom together represent an ═O group; R4 is C1 to C15 hydrocarbyl Z is —(NR7)a—CO—(NR8)b— (wherein a is 0 or 1, b is 0 or 1, —CO—NR7—CH2—CO—NR8—, —CO—O—, —CH2—CH2—, —CH═CH—, —CH2—NR8— or a bond; Q is —R9V, or (II), (wherein R9 is —CH2—; —CH2—CH2—; or (III), R9 and R8, together with the nitrogen atom to which R8 is attached, form a piperidine or pyrrolidine ring which is substituted by V; V is —CO—NH—SO2—Ph, —SO2—NH—CO—Ph, —CH2OH, or a group of the formula —R10U, (wherein U is —COOH, tetrazolyl, —CONHOH— or —SO3H; and R10 is a bond; C1 to C6 hydrocarbylene, —O—(C1 to C3 alkylene)—; —SO2NR11—CHR12—; —CO—NR11—CHR12—, or —NH—(CO)c—CH2—, c being 0 or 1).

  化合物的结构式（I）及其药学上可接受的盐是胃泌素和/或胆囊收缩素受体的配体。X和Y独立地为═N—，—N(R5)—═CH—，—S—或—O—。n为1至4；R1为H或C1至C15烃基；R2从H，Me，Et，Pr和OH中选择；R3从H，Me，Et和Pr中选择；或（当n大于1时）每个R3独立地从H，Me，Et和Pr中选择，或相邻碳原子上的两个R3基团连接形成C3至C6碳环，或R2和R3在同一碳原子上共同表示一个═O基团；R4为C1至C15烃基；Z为—(NR7)a—CO—(NR8)b—（其中a为0或1，b为0或1，—CO—NR7—CH2—CO—NR8—，—CO—O—，—CH2—CH2—，—CH═CH—，—CH2—NR8—或键；Q为—R9V，或（II），（其中R9为—CH2—；—CH2—CH2—；或（III），R9和R8，与R8连接的氮原子一起形成被V取代的哌啶或吡咯烷环；V为—CO—NH—SO2—Ph，—SO2—NH—CO—Ph，—CH2OH，或具有式—R10U的基团，（其中U为—COOH，四唑基，—CONHOH—或—SO3H；R10为键；C1至C6烃基亚烷，—O—（C1至C3亚烷基）—；—SO2NR11—CHR12—；—CO—NR11—CHR12—，或—NH—（CO）c—CH2—，其中c为0或1）。
• [EN] PHARMACEUTICAL COMPOSITIONS COMPRISING PROTON PUMP INHIBITORS AND GASTRIN/CHOLECYSTOKININ RECEPTOR LIGANDS<br/>[FR] COMPOSITIONS PHARMACEUTIQUES COMPRENANT DES INHIBITEURS DE LA POMPE A PROTONS ET DES LIGANDS DU RECEPTEUR DES GASTRINES/CHOLECYSTOKININES
  申请人：BLACK JAMES FOUNDATION

  公开号：WO2001085167A1

  公开（公告）日：2001-11-15

  Pharmaceutical compositions comprising a proton pump inhibitor and a compound of the formula (I) or its pharmaceutically acceptable salts, are useful in treating gastrointestinal disorders. X and Y are independently =N-,-N(R5)- (R5 being selected from H, Me, Et, Pr, Bn, -OH and -CH¿2COOR?6, wherein R6 represents H, Me, Et, Pr or Bn), =CH-, -S- or -O-; n is from 1 to 4; R1 is H or C¿1? to C15 hydrocarbyl wherein up to three C atoms may optionally be replaced by N, O and/or S atoms and up to three H atoms may optionally be replaced by halogen atoms; R?2¿ is selected from H, Me, Et, Pr and OH, each R2 being independently selected from H, Me, Et, Pr and OH when n is greater than 1; R3 (when n is 1) is selected from H, Me, Et and Pr; or (when n is greater than 1) each R3 is independently selected from H, Me, Et, and Pr, or two R3 groups on neighbouring carbon atoms which are linked by a double bond; or R?2 and R3¿ on the same carbon atom are linked to form a C¿3? to C6 carbocylic ring, or two R3 groups are absent from neighbouring carbon atoms which are linked by a double bond; or R?2 and R3¿ on the same carbon atom together represent an =O group; R4 is C1 to C15 hydrocarbyl wherein up to two C atoms may optionally be replaced by N, O and/or S atoms and up to two H atoms may optionally be replaced by halogen atoms; Z is -(NR7)a-CO-(NR8)b- (wherein a is 0 or 1, b is 0 or 1, and R?7 and R8¿ are independently selected from the groups recited above for R6), -CO-NR7-CH2-CO-NR8-, -CO-O-, -CH¿2?-CH2-, -CH=CH-, -CH2-NR?8¿- or a bond; Q is -R9V, or (II) (wherein R9 is -CH¿2?-; -CH2-CH2-; or (III) R?9 and R8¿, together with the nitrogen atom to which R8 is attached, form a piperidine or pyrrolidine ring which is substitued by V; V is -CO-NH-SO¿2?-Ph, SO2-NH-CO-Ph, -CH2OH, or a group of the formula -R?10¿U, (wherein U is -COOH, tetrazolyl, -CONHOH- or -SO¿3?H; and R?10¿ is a bond; C¿1? to C6 hydrocarbylene, optionally substituted by hydroxy, amino or acetamido; -O-(C1 to C3 alkylene)-; -SO2NR?11-CHR12¿-;-CO-NR?11 -CHR12-, R11 and R12¿ being independently selected from H and methyl; or -NH-(CO)¿c?-CH2-, c being 0 or 1); T is C1 to C6 hydrocarbyl, -NR?6R7¿ (wherein R?6 and R7¿ are as defined above), -OMe, -OH, -CH¿2?OH, halogen or trihalomethyl; m is 1 or 2; p is from 0 to 3; and q is from 0 to 2, with the proviso that q is 1 or 2 when Z is a bond).

  含有质子泵抑制剂和公式(I)化合物或其药学上可接受的盐的制剂，可用于治疗胃肠道疾病。其中，X和Y独立地等于=N-，-N（R5）-（其中R5选择自H，Me，Et，Pr，Bn，-OH和-CH2COOR6，其中R6表示H，Me，Et，Pr或Bn），=CH-，-S-或-O-；n为1至4；R1为H或C1至C15烃基，其中最多可以用N，O和/或S原子替换最多三个C原子，并且最多可以用卤素原子替换最多三个H原子；当n大于1时，R2从H，Me，Et，Pr和OH中选择，每个R2独立地从H，Me，Et，Pr和OH中选择；当n为1时，R3从H，Me，Et和Pr中选择；或（当n大于1时）每个R3独立地从H，Me，Et和Pr中选择，或者相邻碳原子上的两个R3基团通过双键连接；或R2和R3在同一碳原子上连接形成C3至C6的环状碳基环，或相邻碳原子上缺少两个R3基团，这些碳原子由双键连接；或R2和R3在同一碳原子上一起表示=O基团；R4为C1至C15烃基，其中最多可以用N，O和/或S原子替换最多两个C原子，并且最多可以用卤素原子替换最多两个H原子；Z为-(NR7)a-CO-(NR8)b-（其中a为0或1，b为0或1，且R7和R8独立地从上述R6群中选择），-CO-NR7-CH2-CO-NR8-，-CO-O-，-CH2-CH2-，-CH=CH-，-CH2-NR8-或键；Q为-R9V，或（II）（其中R9为-CH2-，-CH2-CH2-或（III）R9和R8，连同R8所连接的氮原子，形成一个被V取代的哌啶或吡咯烷环；V为-CO-NH-SO2-Ph，SO2-NH-CO-Ph，-CH2OH或式-R10U的基团（其中U为-COOH，四唑基，-CONHOH-或-SO3H；R10为键；C1至C6烃基亚烷基，可选择性地被羟基，氨基或乙酰氨基取代；-O-（C1至C3烷基）-；-SO2NR11-CHR12-，-CO-NR11-CHR12-，其中R11和R12独立地选择自H和甲基；或-NH-（CO）c-CH2-，其中c为0或1）；T为C1至C6烃基，-NR6R7（其中R6和R7如上所定义），-OMe，-OH，-CH2OH，卤素或三卤甲基；m为1或2；p为0至3；q为0至2，但前提是当Z为键时，q为1或2。
• US6479531B1
  申请人：——

  公开号：US6479531B1

  公开（公告）日：2002-11-12
• Pharmaceutical compositions comprising proton pump inhibitors and gastrin/cholecystokinin receptor ligands
  申请人：——

  公开号：US20030195240A1

  公开（公告）日：2003-10-16

  Pharmaceutical compositions comprising a proton pump inhibitor and a compound of the formula (I) or its pharmaceutically acceptable salts, are useful in treating gastrointestinal disorders. X and Y are independently ═N—, —N(R 5 )— (R 5 being selected from H, Me, Et, Pr, Bn, —OH and —CH 2 COOR 6 , wherein R 6 represents H, Me, Et, Pr or Bn), ═CH—, S— or —O—; n is from 1 to 4; R 1 is H or C 1 to C 15 hydrocarbyl wherein up to three C atoms may optionally be replaced by N, O and/or S atoms and up to three H atoms may optionally be replaced by halogen atoms; R 2 is selected from H, Me, Et, Pr and OH, each R 2 being independently selected from H, Me, Et, Pr and OH when n is greater than 1; R 3 (when n is 1) is selected from H, Me, Et and Pr; or (when n is greater than 1) each R 3 is independently selected from H, Me, Et, and Pr, or two R 3 groups on neighbouring carbon atoms which are linked by a double bond; or R 2 and R 3 on the same carbon atom are linked to form a C 3 to C 6 carbocylic ring, or two R 3 groups are absent from neighbouring carbon atoms which are linked by a double bond; or R 2 and R 3 on the same carbon atom together represent an ═O group; R 4 is C 1 to C 15 hydrocarbyl wherein up to two C atoms may optionally be replaced by N, O and/or S atoms and up to two H atoms may optionally be replaced by halogen atoms; Z is —(NR 7 ) a —CO—(NR 8 ) b — (wherein a is 0 or 1, b is 0 or 1, and R 7 and R 8 are independently selected from the groups recited above for R 6 ), —CO—NR 7 —CH 2 —CO—NR 8 —, —CO—O—, —CH 2 —CH 2 —, —CH═CH—, —CH 2 —NR— or a bond; Q is —R 9 V, or (II) (wherein R 9 is —CH 2 —; —CH 2 —CH 2 —; or (III) R 9 and R 8 , together with the nitrogen atom to which R 8 is attached, form a piperidine or pyrrolidine ring which is substitued by V; V is —CO—NH—SO 2 -Ph, SO 2 —NH—CO-Ph, —CH 2 OH, or a group of the formula —R 10 U, (wherein U is —COOH, tetrazolyl, —CONHOH— or —SO 3 H; and R 10 is a bond; C 1 to C 6 hydrocarbylene, optionally substituted by hydroxy, amino or acetamido; —O—(C 1 to C 3 alkylene)-; —SO 2 NR 11 —CHR 12 —; —CO—NR 11 —CHR 12 —, R 11 and R 12 being independently selected from H and methyl; or —NH—(CO), —CH 2 —, c being 0 or 1); T is C 1 to C 6 hydrocarbyl, —NR 6 R 7 (wherein R 6 and R 7 are as defined above), —OMe, —OH, —CH 2 OH, halogen or trihalomethyl; m is 1 or 2; p is from 0 to 3; and q is from 0 to 2, with the proviso that q is 1 or 2 when Z is a bond). 1

  含有质子泵抑制剂和公式（I）或其药学上可接受的盐的化合物的制剂，对治疗胃肠道疾病有用。其中，X和Y分别是═N—，—N（R5）—（其中R5选择自H，Me，Et，Pr，Bn，—OH和—CH2COOR6，其中R6代表H，Me，Et，Pr或Bn），═CH—，S—或—O—；n为1至4；R1为H或C1至C15的烃基，其中最多可有三个C原子被N，O和/或S原子取代，最多可有三个H原子被卤素原子取代；当n大于1时，R2选择自H，Me，Et，Pr和OH，每个R2独立选择自H，Me，Et，Pr和OH；当n为1时，R3选择自H，Me，Et和Pr；当n大于1时，每个R3独立选择自H，Me，Et和Pr，或被双键连接的相邻碳原子上的两个R3基团；或R2和R3在同一碳原子上连接形成C3到C6的环状碳基；或相邻碳原子上缺少两个R3基团，它们被双键连接；或R2和R3在同一碳原子上共同表示═O基团；R4为C1至C15的烃基，其中最多可有两个C原子被N，O和/或S原子取代，最多可有两个H原子被卤素原子取代；Z为—（NR7）a—CO—（NR8）b—（其中a为0或1，b为0或1，且R7和R8与上述R6中的基团独立选择），—CO—NR7—CH2—CO—NR8—，—CO—O—，—CH2—CH2—，—CH═CH—，—CH2—NR—或键；Q为—R9V，或（II）（其中R9为—CH2—；—CH2—CH2—；或（III）R9和R8与R8连接的氮原子一起形成被V取代的哌啶或吡咯烷环；V为—CO—NH—SO2-Ph，SO2—NH—CO-Ph，—CH2OH或公式—R10U的基团（其中U为—COOH，四唑基，—CONHOH—或—SO3H；R10为键；C1至C6的烃基，可选地被羟基，氨基或乙酰胺基取代；—O—（C1至C3的烷基）-；—SO2NR11—CHR12—；—CO—NR11—CHR12—，其中R11和R12独立选择自H和甲基；或—NH—（CO），—CH2—，其中c为0或1）；T为C1至C6的烃基，—NR6R7（其中R6和R7如上所定义），—OMe，—OH，—CH2OH，卤素或三卤甲基；m为1或2；p为0至3；q为0至2，但当Z为键时，q为1或2。