N,N,5-trimethyl-2-nitrobenzamide | 178672-24-7

• 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: N,N,5-trimethyl-2-nitrobenzamide
• 英文别名: 5,N,N-trimethyl-2-nitrobenzamide
• CAS: 178672-24-7
• 化学式: C₁₀H₁₂N₂O₃
• 分子量: 208.217
• InChiKey: MHQHQCBLXZDDAD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  66.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N,N,5-trimethyl-2-nitrobenzamide 在 钯 氢气 、 silica gel 、 dichloromethane ethanol 作用下， 以 乙醇 为溶剂， 反应 26.0h， 以to give 2-amino-N,N,5-trimethylbenzamide (8 g, 44.9 mmol), m.p. 98°-99° C.的产率得到2-Amino-5,N,N-trimethyl-benzamide
  参考文献：
  名称：

  \x9b3-(4-phenylpiperazin-1-yl)propyl-amino, thio and oxy!-pyridine,

  摘要：

  本发明涉及一种新型的α1-肾上腺素受体拮抗剂，其化学式为I：##STR1## 其中：p为0或1；t为0、1或2；X为O、S或NR6（其中R6为氢或（C1-6）烷基）；Y和Z独立地为CH或N；R1为氢、羟基、卤素、硝基、氨基、氰基、（C1-4）烷基硫醇、乙酰氨基、三氟乙酰氨基、甲基磺酰氨基、（C1-6）烷基、（C3-6）环烷基、（C3-6）环烷基（C1-4）烷基、噁唑-2-基、芳基、杂环芳基、芳基（C1-4）烷基、杂环芳基（C1-4）烷基、（C1-6）烷氧基、（C3-6）环烷氧基、（C3-6）环烷基（C1-4）烷氧基、2-丙炔氧基、芳基氧基、杂环芳基氧基、芳基（C1-4）烷氧基或杂环芳基（C1-4）烷氧基（其中烷基可选地被1-3个卤素原子取代，芳基或杂环芳基可选地被1-2个独立选择自卤素和氰基的取代基取代）；R2为氢、羟基、卤素、氰基、（C1-6）烷基或（C1-6）烷氧基（其中烷基可选地被1-3个卤素原子取代）；R3为-C（O）R7（其中R7为（C1-6）烷基、（C3-6）环烷基、二（C1-4）烷基氨基、N-（C1-4）烷基-N-（C1-4）烷氧基氨基、（C1-4）烷基（（C1-4）烷氧基）氨基、吡咯烷-1-基、哌啶-1-基、吗啉-4-基或哌嗪-1-基）；R4为卤素、羟基、氰基、（C1-6）烷基或（C1-6）烷氧基；R5为（C1-6）烷基；以及其药学上可接受的盐和N-氧化物。

  公开号：

  US05688795A1
• 作为产物：
  描述：

  5-甲基-2-硝基苯甲酸 在 sodium hydroxide 、 草酰氯 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 N,N,5-trimethyl-2-nitrobenzamide
  参考文献：
  名称：

  N-Arylpiperazinyl-N‘-propylamino Derivatives of Heteroaryl Amides as Functional Uroselective α₁-Adrenoceptor Antagonists

  摘要：

  Novel arylpiperazines were identified as alpha(1)-adrenoceptor(BR) subtype-selective antagonists by functional in vitro screening. 3-[4-(ortho-Substituted phenyl)piperazin-1-yl]propylamines were derivatized with N,N-dimethyl anthranilamides, nicotinamides,;as well as carboxamides of quinoline, I,8-naphthyridine, pyrazolo[3,4-b]pyridine, isoxazolo[3,4-b]pyridine, imidazo[4,5-b]pyridine, and pyrazolo[1,5-a]pyrimidines. Strips of rabbit bladder neck were employed as a predictive assay for antagonism in the human lower tract. Rings of rat aorta;a were used as a ''negative screen'' for the test antagonists. Binding to alpha(1)-ARs was relatively sensitive to size and electronic features of the arylpiperazine portion of the antagonists and permissive to these features on the heteroaryl carboxamide side. These structure-affinity findings were exploited to produce nicotinamides (e.g, 13ii and 25x) and pyrazolo[3,4-b]pyridines (e.g. 37f and 37y) ligands with nanomolar affinity at the alpha(1)-AR subtype prevalent in the human lower urinary tract (pA(2) values: 8.8, 10.7, 9.3, and 9.9, respectively) and displaying 2-3 orders of magnitude selectivity over the alpha(1D)-AR.

  DOI：

  10.1021/jm970166j

文献信息

• \x9b3-(4-phenylpiperazin-1-yl)propyl-amino, thio and oxy!-pyridine,
  申请人：Syntex (U.S.A.) Inc.

  公开号：US05688795A1

  公开（公告）日：1997-11-18

  The present invention relates to novel .alpha..sub.1 -adrenoceptor antagonists of Formula I: ##STR1## in which: p is 0 or 1; t is 0, 1 or 2; X is O, S or NR.sup.6 (in which R.sup.6 is hydro or (C.sub.1-6)alkyl); Y and Z are independently CH or N; R.sup.1 is hydro, hydroxy, halo, nitro, amino, cyano, (C.sub.1-4)alkylthio, acetylamino, trifluoroacetylamino, methylsulfonylamino, (C.sub.1-6)alkyl, (C.sub.3-6)cycloalkyl, (C.sub.3-6)cycloalkyl (C.sub.1-4)alkyl, oxazol-2-yl, aryl, heteroaryl, aryl (C.sub.1-4)alkyl, heteroaryl (C.sub.1-4)alkyl, (C.sub.1-6)alkyloxy, (C.sub.3-6)cycloalkyloxy, (C.sub.3-6)cycloalkyl (C.sub.1-4)alkyloxy, 2-propynyloxy, aryloxy, heteroaryloxy, aryl (C.sub.1-4)alkyloxy or heteroaryl (C.sub.1-4)alkyloxy (wherein alkyl is optionally substituted with one to three halo atoms and aryl or heteroaryl is optionally substituted with one to two substituents independently selected from halo and cyano); R.sup.2 is hydro, hydroxy, halo, cyano, (C.sub.1-6)alkyl or (C.sub.1-6)alkyloxy (wherein alkyl is optionally substituted with one to three halo atoms); R.sup.3 is -C (O)R.sup.7 (wherein R.sup.7 is (C.sub.1-6)alkyl, (C.sub.3-6)cycloalkyl, di(C.sub.1-4)alkylamino, N-(C.sub.1-4)alkyl-N-(C.sub.1-4)alkyloxyamino, (C.sub.1-4)alkyl((C.sub.1-4)alkyloxy)amino, pyrrolidin-1-yl, piperidin-1-yl, morpholin-4-yl or piperazin-1-yl); R.sup.4 is halo, hydroxy, cyano, (C.sub.1-6)alkyl or (C.sub.1-6)alkyloxy; and R.sup.5 is (C.sub.1-6)alkyl; and the pharmaceutically acceptable salts and N-oxides thereof.

  本发明涉及一种新型的α1-肾上腺素受体拮抗剂，其化学式为I：##STR1## 其中：p为0或1；t为0、1或2；X为O、S或NR6（其中R6为氢或（C1-6）烷基）；Y和Z独立地为CH或N；R1为氢、羟基、卤素、硝基、氨基、氰基、（C1-4）烷基硫醇、乙酰氨基、三氟乙酰氨基、甲基磺酰氨基、（C1-6）烷基、（C3-6）环烷基、（C3-6）环烷基（C1-4）烷基、噁唑-2-基、芳基、杂环芳基、芳基（C1-4）烷基、杂环芳基（C1-4）烷基、（C1-6）烷氧基、（C3-6）环烷氧基、（C3-6）环烷基（C1-4）烷氧基、2-丙炔氧基、芳基氧基、杂环芳基氧基、芳基（C1-4）烷氧基或杂环芳基（C1-4）烷氧基（其中烷基可选地被1-3个卤素原子取代，芳基或杂环芳基可选地被1-2个独立选择自卤素和氰基的取代基取代）；R2为氢、羟基、卤素、氰基、（C1-6）烷基或（C1-6）烷氧基（其中烷基可选地被1-3个卤素原子取代）；R3为-C（O）R7（其中R7为（C1-6）烷基、（C3-6）环烷基、二（C1-4）烷基氨基、N-（C1-4）烷基-N-（C1-4）烷氧基氨基、（C1-4）烷基（（C1-4）烷氧基）氨基、吡咯烷-1-基、哌啶-1-基、吗啉-4-基或哌嗪-1-基）；R4为卤素、羟基、氰基、（C1-6）烷基或（C1-6）烷氧基；R5为（C1-6）烷基；以及其药学上可接受的盐和N-氧化物。
• Ester compound and medicinal use thereof
  申请人：Hagiwara Atsushi

  公开号：US20050075367A1

  公开（公告）日：2005-04-07

  A novel therapeutic agent for hyperlipidemia, which is an ester compound represented by the formula (1″) (wherein R 1 and R 2 are each hydrogen atom or optionally substituted aryl, etc.; X is —COO— or —CON(R 10 )—; R 3 and R 4 are each hydrogen atom, C 1 -C 6 alkyl or C 1 -C 6 alkoxy, etc.; R 5 , R 6 and R 7 are each hydrogen atom, C 1 -C 6 alkyl or C 1 -C 6 alkoxy, etc.; R 8 and R 9 are each independently hydrogen atom, C 1 -C 6 alkyl, —CON(R 18 )(R 19 ) or —COO(R 20 ), etc.; ring A, ring B and ring C are each independently aryl or heterocycle residue, etc.; Alk 1 and Alk 2 are each independently alkanediyl, etc.; l and m are each an integer of 0 or 1 to 3) or a prodrug thereof, or a pharmaceutically acceptable salt of either. The therapeutic agent selectively inhibits MTP in the small intestine, thus causes no such side effect as a fatty liver.

  一种治疗高脂血症的新型药物，其为酯化合物，由式（1”）所表示（其中，R1和R2分别为氢原子或可选取代的芳基等；X为—COO—或—CON(R10)—；R3和R4分别为氢原子、C1-C6烷基或C1-C6烷氧基等；R5、R6和R7分别为氢原子、C1-C6烷基或C1-C6烷氧基等；R8和R9分别独立地为氢原子、C1-C6烷基、—CON(R18)(R19)或—COO(R20)等；环A、环B和环C分别独立地为芳基或杂环残基等；Alk1和Alk2分别独立地为脂肪二亚基等；l和m分别为0或1至3的整数），或其前药，或其药学上可接受的盐。该治疗剂能够选择性地抑制小肠中的MTP，从而不会引起脂肪肝等副作用。
• ESTER COMPOUND AND MEDICAL USE THEREOF
  申请人：Hagiwara Atsushi

  公开号：US20100158996A1

  公开（公告）日：2010-06-24

  A novel therapeutic agent for hyperlipidemia, which is an ester compound represented by the formula (1″) (wherein R 1 and R 2 are each hydrogen atom or optionally substituted aryl, etc.; X is —COO— or —CON(R 10 )—; R 3 and R 4 are each hydrogen atom, C 1 -C 6 alkyl or C 1 -C 6 alkoxy, etc.; R 5 , R 6 and R 7 are each hydrogen atom, C 1 -C 6 alkyl or C 1 -C 6 alkoxy, etc.; R 9 and R 9 are each independently hydrogen atom, C 1 -C 6 alkyl, —CON(R 18 ) (R 19 ) or —COO(R 20 ), etc.; ring A, ring B and ring C are each independently aryl or heterocycle residue, etc.; Alk 1 and Alk 2 are each independently alkanediyl, etc.; l and m are each an integer of 0 or 1 to 3) or a prodrug thereof, or a pharmaceutically acceptable salt of either. The therapeutic agent selectively inhibits MTP in the small intestine, thus causes no such side effect as a fatty liver.

  一种治疗高脂血症的新型药物，其为酯化合物，由式（1″）所表示（其中R1和R2分别为氢原子或可选择取代的芳基等；X为—COO—或—CON(R10)—；R3和R4分别为氢原子、C1-C6烷基或C1-C6烷氧基等；R5、R6和R7分别为氢原子、C1-C6烷基或C1-C6烷氧基等；R8和R9分别独立地为氢原子、C1-C6烷基、—CON(R18)(R19)或—COO(R20)等；环A、环B和环C分别独立地为芳基或杂环残基等；Alk1和Alk2分别独立地为脂肪二亚基等；l和m分别为0或1至3的整数），或其前药，或其药学上可接受的盐。该治疗剂选择性地抑制小肠中的MTP，从而不会引起脂肪肝等副作用。
• 3-(4-phenylpiperazin-1-yl)propyl-amino, thio and oxy -pyridine, pyrimidine and benzene derivatives as alpha1-adrenoceptor antagonists
  申请人：F. Hoffmann-La Roche AG

  公开号：EP0711757A1

  公开（公告）日：1996-05-15

  The present invention relates to novel α₁-adrenoceptor antagonists of Formula I: in which: p is 0 or 1; t is 0, 1 or 2; X is O, S or NR⁶ (in which R⁶ is hydro or (C₁₋₆)alkyl); Y and Z are independently CH or N; R¹ is hydro, hydroxy, halo, nitro, amino, cyano, (C₁₋₄)alkylthio, acetylamino, trifluoroacetylamino, methylsulfonylamino, (C₁₋₆)alkyl, (C₃₋₆)cycloalkyl, (C₃₋₆)cycloalkyl(C₁₋₄)alkyl, oxazol-2-yl, aryl, heteroaryl, aryl(C₁₋₄)alkyl, heteroaryl(C₁₋₄)alkyl, (C₁₋₆)alkyloxy, (C₃₋₆)cycloalkyloxy, (C₃₋₆)cycloalkyl(C₁₋₄)alkyloxy, 2-propynyloxy, aryloxy, heteroaryloxy, aryl(C₁₋₄)alkyloxy or heteroaryl(C₁₋₄)alkyloxy (wherein alkyl is optionally substituted with one to three halo atoms and aryl or heteroaryl is optionally substituted with one to two substituents independently selected from halo and cyano); R² is hydro, hydroxy, halo, cyano, (C₁₋₆)alkyl or (C₁₋₆)alkyloxy (wherein alkyl is optionally substituted with one to three halo atoms); R³ is -C(O)R⁷ (wherein R⁷ is (C₁₋₆)alkyl, (C₃₋₆)cycloalkyl, di(C₁₋₄)alkylamino, N-(C₁₋₄)alkyl-N-(C₁₋₄)alkyloxyamino, (C₁₋₄)alkyl((C₁₋₄)alkyloxy)amino, pyrrolidin-1-yl, piperidin-1-yl, morpholin-4-yl or piperazin-1-yl); R⁴ is halo, hydroxy, cyano, (C₁₋₆)alkyl or (C₁₋₆)alkyloxy; and R⁵ is (C₁₋₆)alkyl; and the pharmaceutically acceptable salts and N-oxides thereof.

  本发明涉及式 I 的新型 α₁-肾上腺素受体拮抗剂： 其中 p 是 0 或 1； t 是 0、1 或 2 X 是 O、S 或 NR⁶（其中 R⁶ 是氢或 (C₁₋₆)烷基）； Y 和 Z 独立地为 CH 或 N； R¹是氢、羟基、卤代、硝基、氨基、氰基、(C₁₋₄)烷硫基、乙酰氨基、三氟乙酰氨基、甲磺酰氨基、(C₁₋₆)烷基、(C₃₋₆)环烷基、(C₃₋₆)环烷基(C₁₋₄)烷基、噁唑-2-基、芳基、杂芳基、芳基(C₁₋₄)烷基、杂芳基(C₁₋₄)烷基、(C₁₋₆)烷氧基、(C₃₋₆)环烷氧基、(C₃₋₆)环烷基(C₁₋₄)烷氧基，2-丙炔氧基，芳基氧基，杂芳基氧基、芳基（C₁₋₄）烷氧基或杂芳基（C₁₋₄）烷氧基（其中烷基任选被一至三个卤原子取代，芳基或杂芳基任选被一至两个独立选自卤素和氰基的取代基取代）； R² 是氢、羟基、卤代、氰基、(C₁₋₆)烷基或(C₁₋₆)烷氧基（其中烷基任选被一至三个卤原子取代）； R³ 是 -C(O)R⁷（其中 R⁷ 是 (C₁₋₆)烷基、(C₃₋₆)环烷基、二(C₁₋₄)烷基氨基、N-(C₁₋₄)烷基-N-(C₁₋₄)烷氧基氨基、(C₁₋₄)烷基((C₁₋₄烷氧基)氨基、吡咯烷-1-基、哌啶-1-基、吗啉-4-基或哌嗪-1-基)； R⁴ 是卤素、羟基、氰基、(C₁₋₆)烷基或 (C₁₋₆)烷氧基；和 R⁵ 是 (C₁₋₆)烷基；及其药学上可接受的盐和 N-氧化物。
• EP1479666
  申请人：——

  公开号：——

  公开（公告）日：——