Tert-butyl 4-(4-chloro-2-methylphenyl)piperidine-1-carboxylate | 1013025-93-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: Tert-butyl 4-(4-chloro-2-methylphenyl)piperidine-1-carboxylate
• 英文别名: tert-butyl 4-(4-chloro-2-methylphenyl)piperidine-1-carboxylate
• CAS: 1013025-93-8
• 化学式: C₁₇H₂₄ClNO₂
• 分子量: 309.836
• InChiKey: AZPVXSAWVMHBNE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  Tert-butyl 4-(4-chloro-2-methylphenyl)piperidine-1-carboxylate 、 氰化锌 在 Pd(Bu₃P)2 N-甲基吡咯烷酮 、 锌 作用下， 以76%的产率得到Tert-butyl 4-(4-cyano-2-methylphenyl)piperidine-1-carboxylate
  参考文献：
  名称：

  Conversion of an MMP-potent scaffold to an MMP-selective HER-2 sheddase inhibitor via scaffold hybridization and subtle permutations

  摘要：

  A series of beta-sulfonamide piperidine hydroxamates were prepared and shown to be potent inhibitors of the human epidermal growth factor receptor-2 (HER-2) sheddase with excellent selectivity against MMP-1, -2, -3, and -9. This was achieved by exploiting subtle differences within the otherwise highly conserved S-1' binding pocket of the active sites within the metalloprotease family. In addition, it was discovered that the introduction of polarity to the P-1 and P-1' groups reduced the projected human clearance. Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2007.11.086
• 作为产物：
  描述：

  Tert-butyl 4-(4-chloro-2-methylphenyl)-3,6-dihydropyridine-1(2h)-carboxylate 在 platinum on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 以68%的产率得到Tert-butyl 4-(4-chloro-2-methylphenyl)piperidine-1-carboxylate
  参考文献：
  名称：

  Conversion of an MMP-potent scaffold to an MMP-selective HER-2 sheddase inhibitor via scaffold hybridization and subtle permutations

  摘要：

  A series of beta-sulfonamide piperidine hydroxamates were prepared and shown to be potent inhibitors of the human epidermal growth factor receptor-2 (HER-2) sheddase with excellent selectivity against MMP-1, -2, -3, and -9. This was achieved by exploiting subtle differences within the otherwise highly conserved S-1' binding pocket of the active sites within the metalloprotease family. In addition, it was discovered that the introduction of polarity to the P-1 and P-1' groups reduced the projected human clearance. Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2007.11.086

文献信息

• 5-[3-[piperzin-1-yl]-3-oxo-propyl]-imidazolidine-2,4-dione derivatives as ADAMTS 4 and 5 inhibitors for treating E.G. osteoarthritis
  申请人：GALAPAGOS NV

  公开号：US10550100B2

  公开（公告）日：2020-02-04

  The present invention discloses compounds according to Formula I: Wherein R1, R2, R3a, R3b, R6, Cy, and the subscript n are as defined herein. The present invention relates to compounds inhibiting ADAMTS, methods for their production, pharmaceutical compositions comprising the same, and methods of treatment using the same, for the prophylaxis and/or treatment of inflammatory diseases, and/or diseases involving degradation of cartilage and/or disruption of cartilage homeostasis by administering the compound of the invention.

  本发明公开了符合式 I 的化合物： 其中 R1、R2、R3a、R3b、R6、Cy 和下标 n 如本文所定义。 本发明涉及抑制 ADAMTS 的化合物、其生产方法、包含本发明化合物的药物组合物和使用本发明化合物的治疗方法，通过施用本发明化合物预防和/或治疗炎症性疾病和/或涉及软骨降解和/或破坏软骨稳态的疾病。
• 5-[3-[PIPERIDIN-1-YL]-3-OXO-PROPYL]-IMIDAZOLIDINE-2,4-DIONE DERIVATIVES AS ADAMTS 4 AND 5 INHIBITORS FOR TREATING E.G. OSTEOARTHRITIS
  申请人：Galapagos NV

  公开号：EP3468961B1

  公开（公告）日：2020-06-10
• 5-[3-[PIPERAZIN-1-YL]-3-OXO-PROPYL]-IMIDAZOLIDINE-2,4-DIONE DERIVATIVES AS ADAMTS 4 AND 5 INHIBITORS FOR TREATING E.G. OSTEOARTHRITIS
  申请人：Galapagos NV

  公开号：US20190300503A1

  公开（公告）日：2019-10-03

  The present invention discloses compounds according to Formula I: Wherein R 1 , R 2 , R 3a , R 3b , R 6 , Cy, and the subscript n are as defined herein. The present invention relates to compounds inhibiting ADAMTS, methods for their production, pharmaceutical compositions comprising the same, and methods of treatment using the same, for the prophylaxis and/or treatment of inflammatory diseases, and/or diseases involving degradation of cartilage and/or disruption of cartilage homeostasis by administering the compound of the invention.
• [EN] SUBSTITUTED PHENYLPIPERIDINE DERIVATIVES AS MELANOCORTIN-4 RECEPTOR MODULATORS<br/>[FR] DÉRIVÉS DE PHÉNYLPIPÉRIDINE SUBSTITUÉS EN TANT QUE MODULATEURS DU RÉCEPTEUR DE LA MÉLANOCORTINE-4
  申请人：SANTHERA PHARMACEUTICALS CH

  公开号：WO2007115798A1

  公开（公告）日：2007-10-18

  [EN] The present invention relates to substituted phenylpiperidine derivatives as melanocortin-4 receptor modulators. Depending on the structure and the stereochemistry the compounds of the invention are either selective agonists or selective antagonists of the human melanocortin-4 receptor (MC-4R). The agonists can be used for the treatment of disorders and diseases such as obesity, diabetes and sexual dysfunction, whereas the antagonists are useful for the treatment of disorders and diseases such as cancer cachexia, muscle wasting, anorexia, anxiety and depression. Generally all diseases and disorders where the regulation of the MC-4R is involved can be treated with the compounds of the invention.
  [FR] La présente invention concerne des dérivés de phénylpipéridine substitués en tant que modulateurs des récepteurs de la mélanocortine-4. En fonction de la structure et de la stéréochimie, les composés de l'invention sont soit des agonistes sélectifs, soit des antagonistes sélectifs du récepteur humain de la mélanocortine-4 (MC-4R). Les agonistes peuvent être utilisés pour le traitement de troubles et de maladies tels que l'obésité, le diabète et une dysfonction sexuelle, alors que les antagonistes sont utiles pour le traitement de troubles et de maladies tels que le cancer, l'émaciation, l'atrophie musculaire, l'anorexie, l'anxiété et la dépression. Généralement, toutes les maladies et tous les troubles associés à la régulation du MC-4R peuvent être traités avec les composés de l'invention.
• Conversion of an MMP-potent scaffold to an MMP-selective HER-2 sheddase inhibitor via scaffold hybridization and subtle permutations
  作者：David M. Burns、Chunhong He、Yanlong Li、Peggy Scherle、Xiangdong Liu、Cindy A. Marando、Mayanne B. Covington、Gengjie Yang、Max Pan、Sharon Turner、Jordan S. Fridman、Gregory Hollis、Kris Vaddi、Swamy Yeleswaram、Robert Newton、Steve Friedman、Brian Metcalf、Wenqing Yao

  DOI：10.1016/j.bmcl.2007.11.086

  日期：2008.1

  A series of beta-sulfonamide piperidine hydroxamates were prepared and shown to be potent inhibitors of the human epidermal growth factor receptor-2 (HER-2) sheddase with excellent selectivity against MMP-1, -2, -3, and -9. This was achieved by exploiting subtle differences within the otherwise highly conserved S-1' binding pocket of the active sites within the metalloprotease family. In addition, it was discovered that the introduction of polarity to the P-1 and P-1' groups reduced the projected human clearance. Published by Elsevier Ltd.