cis-p-Amino-zimtsaeurenitril | 888476-02-6

• 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: cis-p-Amino-zimtsaeurenitril
• 英文别名: (Z)-3-(4-aminophenyl)prop-2-enenitrile
• CAS: 888476-02-6
• 化学式: C₉H₈N₂
• 分子量: 144.176
• InChiKey: YSLYJMRRAPPURP-UPHRSURJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  丙烯腈 、 对碘苯胺 在 palladium diacetate 、 三苯基膦 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以38%的产率得到(E)-3-(4-aminophenyl)acrylonitrile
  参考文献：
  名称：

  [EN] HIV INHIBITING 1,2,4-TRIAZInONE DERIVATIVES
  [FR] DÉRIVÉS DE 1,2,4-TRIAZINONE INHIBITEURS DU VIH

  摘要：

  本发明涉及公式(I)的HIV复制抑制剂，其中N-氧化物，药学上可接受的加盐物，季铵盐或其立体化学异构体形式，其中环A和环B代表苯基，吡啶基，吡啶并嗪基，嘧啶基或吡嗪基；n和m为1至4；R1代表氢；芳基；甲酰基；C1-6烷基羰基；C1-6烷氧羰基；可选择取代的C1-6烷基；C1-6烷氧基C1-6烷基羰基，其用作药物，用于制造用于治疗或预防HIV感染的药物的药物，其制备方法和包含它们的制药组合物。

  公开号：

  WO2006015985A1

文献信息

• Hiv Inhibiting 1,2,4-Triazin-6-One Derivatives
  申请人：Hoornaert Georges Joseph Cornelius

  公开号：US20090012092A1

  公开（公告）日：2009-01-08

  The present invention relates to HIV replication inhibitors of formula a N-oxide, a pharmaceutically acceptable addition salt, a quaternary amine or a stereochemically isomeric form thereof, wherein ring A and ring B represent phenyl, pyridyl, pyridazinyl, pyrimidinyl or pyrazinyl; n and m are 1 to 4; R 1 represents hydrogen; aryl; formyl; C 1-6 alkylcarbonyl; C 1-6 alkyloxycarbonyl; optionally substituted C 1-6 alkyl; C 1-6 alkyloxyC 1-6 alkylcarbonyl substituted with C 1-6 alkyloxycarbonyl; R 2 or R 4 represents hydrogen; hydroxy; halo; optionally substituted C 1-6 alkyl; optionally substituted C 2-6 alkenyl; optionally substituted C 2-6 alkynyl; C 3-7 cycloalkyl; C 1-6 alkyloxy; C 1-6 alkyloxycarbonyl; C 1-6 alkylcarbonyloxy; carboxyl; cyano; nitro; amino; mono- or di(C 1-6 alkyl)amino; polyhaloC 1-4 alkyl; polyhaloC 1-4 alkyloxy; polyhaloC 1-4 alkylthio; —S(═O) p R 6 ; —NH—S(═O) p R 6 ; —C(═O)R 6 ; —NHC(═O)H; —C(═O)NHNH 2 ; NHC(═O)R 6 ; C(═NH)R 6 ; or R 7 ; R 2a or R 3 represents cyano; aminocarbonyl; amino; halo; NHR 13 ; NR 13 R 14 —C(═O)—NHR 13 ; —C(═O)—NR 13 R 14 ; —C(═O)—R 15 ; —CH═N—NH—C(═O)—R 16 ; optionally substituted C 1-6 alkyl; optionally substituted C 1-6 alkyloxy; optionally substituted C 1-6 alkyloxyC 1-6 alkyl; optionally substituted C 2-6 alkenyl; optionally substituted C 2-6 alkynyl; —C(═N—O—R 8 )—C 1-4 alkyl; R 7 or —X 3 —R 7 ; X 1 or X 2 represents —NR 1 —; —NH—NH—; —N═N—; —O—; —C(═O)—; —C 1-4 alkanediyl-; —CHOH—; —S—; —S(═O) p —; —X 4 —C 1-4 alkanediyl-; —C 1-4 alkanediyl-X 4 —; or —C 1-4 alkanediyl-X 4 —C 1-4 alkanediyl-; their use as a medicine, their use for the manufacture of a medicament for the treatment or the prevention of HIV infection; their processes for preparation and pharmaceutical compositions comprising them.

  本发明涉及公式a的HIV复制抑制剂，其为N-氧化物、药学上可接受的加成盐、季铵盐或其立体化学异构体形式，其中环A和环B代表苯基、吡啶基、吡嗪基、嘧啶基或吡嗪基；n和m为1至4；R1代表氢；芳基；甲酰基；C1-6烷基羰基；C1-6烷氧羰基；可选取代的C1-6烷基；C1-6烷氧基C1-6烷基羰基，其被C1-6烷氧羰基取代；R2或R4代表氢；羟基；卤素；可选取代的C1-6烷基；可选取代的C2-6烯基；可选取代的C2-6炔基；C3-7环烷基；C1-6烷氧基；C1-6烷氧羰基；C1-6烷基羰酰氧基；羧基；氰基；硝基；氨基；单烷基或双烷基(C1-6)氨基；多卤素C1-4烷基；多卤素C1-4烷氧基；多卤素C1-4烷硫基；-S(═O)pR6；-NH-S(═O)pR6；-C(═O)R6；-NHC(═O)H；-C(═O)NHNH2；NHC(═O)R6；C(═NH)R6；或R7；R2a或R3代表氰基；氨基羰基；氨基；卤素；NHR13；NR13R14-C(═O)-NHR13；-C(═O)-NR13R14；-C(═O)-R15；-CH═N-NH-C(═O)-R16；可选取代的C1-6烷基；可选取代的C1-6烷氧基；可选取代的C1-6烷氧基C1-6烷基；可选取代的C2-6烯基；可选取代的C2-6炔基；-C(═N-O-R8)-C1-4烷基；R7或-X3-R7；X1或X2代表-NR1-；-NH-NH-；-N═N-；-O-；-C(═O)-；-C1-4烷二基-；-CHOH-；-S-；-S(═O)p-；-X4-C1-4烷二基-；-C1-4烷二基-X4-；或-C1-4烷二基-X4-C1-4烷二基-；其作为药物的用途，其用于制造用于治疗或预防HIV感染的药物，其制备过程和包含它们的制药组合物。
• Ligandless Heck Coupling between a Halogenated Aniline and Acrylonitrile Catalyzed by Pd/C: Development and Optimization of an Industrial-Scale Heck Process for the Production of a Pharmaceutical Intermediate
  作者：Didier Schils、Fred Stappers、Geoffrey Solberghe、Richard van Heck、Michelle Coppens、Dirk Van den Heuvel、Peter Van der Donck、Tom Callewaert、Frank Meeussen、Erika De Bie、Kristof Eersels、Ellen Schouteden

  DOI：10.1021/op8000383

  日期：2008.5.1

  The aniline derivative 3 is a key building block of rilpivirine (TMC278) 2, a new potent NNRTI compound under clinical evaluation. In this paper we describe the development of a new synthesis of 3 based on a Heck coupling between a halogenated aniline and acrylonitrile using low loading of Pd/C (0.5 mol %) as catalyst. This resulted in a process which has been successfully transferred into production on 2400 mol-scale (6000 L reactor)
• HIV INHIBITING 1.2.4-TRIAZIN-6-ONE DERIVATES
  申请人：Janssen Pharmaceutica NV

  公开号：EP1797050B1

  公开（公告）日：2013-10-23
• US7923554B2
  申请人：——

  公开号：US7923554B2

  公开（公告）日：2011-04-12
• [EN] HIV INHIBITING 1,2,4-TRIAZInONE DERIVATIVES<br/>[FR] DÉRIVÉS DE 1,2,4-TRIAZINONE INHIBITEURS DU VIH
  申请人：JANSSEN PHARMACEUTICA NV

  公开号：WO2006015985A1

  公开（公告）日：2006-02-16

  The present invention relates to HIV replication inhibitors of formula (I) a N-oxide, a pharmaceutically acceptable addition salt, a quaternary amine or a stereochemically isomeric form thereof, wherein ring A and ring B represent phenyl, pyridyl, pyridazinyl, pyrimidinyl or pyrazinyl; n and m are 1 to 4; R1 represents hydrogen; aryl; formyl; C1-6alkylcarbonyl; C1-6alkyloxycarbonyl; optionally substituted C1-6alkyl; C1-6alkyloxy C1-6alkylcarbonyl substituted with C1-6alkyloxycarbonyl; their use as a medicine, their use for the manufacture of a medicament for the treatment or the prevention of HIV infection; their processes for preparation and pharmaceutical compositions comprising them.

  本发明涉及公式(I)的HIV复制抑制剂，其中N-氧化物，药学上可接受的加盐物，季铵盐或其立体化学异构体形式，其中环A和环B代表苯基，吡啶基，吡啶并嗪基，嘧啶基或吡嗪基；n和m为1至4；R1代表氢；芳基；甲酰基；C1-6烷基羰基；C1-6烷氧羰基；可选择取代的C1-6烷基；C1-6烷氧基C1-6烷基羰基，其用作药物，用于制造用于治疗或预防HIV感染的药物的药物，其制备方法和包含它们的制药组合物。