(R)-(+)-2-piperidinecarboxylic acid (+)-tartrate | 15912-30-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (R)-(+)-2-piperidinecarboxylic acid (+)-tartrate
• 英文别名: (R)-pipecolinic acid (L)-tartrate salt；D-Pip L-(+)-tartrate salt；2,3-dihydroxybutanedioic acid;(2R)-piperidine-2-carboxylic acid
• CAS: 15912-30-8；35677-82-8；98626-57-4；109731-18-2；111478-73-0；112797-03-2；128684-94-6；138804-98-5
• 化学式: C₄H₆O₆*C₆H₁₁NO₂
• 分子量: 279.247
• InChiKey: DPNBCUQPARXJAN-NUBCRITNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.91
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  164
• 氢给体数：
  6
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (R)-(+)-2-piperidinecarboxylic acid (+)-tartrate 在 Amberlite IR-120 作用下， 以 水 为溶剂， 以81%的产率得到D-哌啶-2-甲酸
  参考文献：
  名称：

  Synthesis of 2-piperidinecarboxylic acid derivatives as potential anticonvulsants

  摘要：

  A variety of 2-piperidinecarboxamides were synthesized and evaluated for anticonvulsant activity using the MES and sc PTZ tests in mice and rats. Neurotoxicity was determined by the rotorod test. Several N-(benzyl)-2-piperidinecarboxamides exhibited potent MES activity in mice [2-CF3 14, ED50 = 29 mg/kg; 3-F 16, ED50 = 31 mg/kg; and 3-CF3 17, ED50 = 24 mg/kg]. The most active compounds in the MES test in mice were the 2,6-dimethylanilides [(R,S)-34, ED50 = 5.8 mg/kg; (R)-35, ED50 = 5.7 mg/kg; and (S)-36, ED50 = 14.8 mg/kg]. The enantiomer (S)-36 was about two-fold less potent in the MES test than (R)-35 and also was less neurotoxic. Acylation of the piperidine ring nitrogen of 12 and 34 led to a decrease in the MES activity. In the N-(alpha-methylbenzyl)-2-piperidine-carboxamides, the stereochemistry at either the 2-position of the piperidine ring or at the alpha-position of the N-(alpha-methylbenzyl) group does not significantly affect MES activity. (C) Elsevier, Paris.

  DOI：

  10.1016/s0223-5234(99)80072-5
• 作为产物：
  描述：

  L-酒石酸 、 六氢吡啶-alpha-羧酸 以 甲醇 为溶剂， 以59%的产率得到(R)-(+)-2-piperidinecarboxylic acid (+)-tartrate
  参考文献：
  名称：

  Synthesis of 2-piperidinecarboxylic acid derivatives as potential anticonvulsants

  摘要：

  A variety of 2-piperidinecarboxamides were synthesized and evaluated for anticonvulsant activity using the MES and sc PTZ tests in mice and rats. Neurotoxicity was determined by the rotorod test. Several N-(benzyl)-2-piperidinecarboxamides exhibited potent MES activity in mice [2-CF3 14, ED50 = 29 mg/kg; 3-F 16, ED50 = 31 mg/kg; and 3-CF3 17, ED50 = 24 mg/kg]. The most active compounds in the MES test in mice were the 2,6-dimethylanilides [(R,S)-34, ED50 = 5.8 mg/kg; (R)-35, ED50 = 5.7 mg/kg; and (S)-36, ED50 = 14.8 mg/kg]. The enantiomer (S)-36 was about two-fold less potent in the MES test than (R)-35 and also was less neurotoxic. Acylation of the piperidine ring nitrogen of 12 and 34 led to a decrease in the MES activity. In the N-(alpha-methylbenzyl)-2-piperidine-carboxamides, the stereochemistry at either the 2-position of the piperidine ring or at the alpha-position of the N-(alpha-methylbenzyl) group does not significantly affect MES activity. (C) Elsevier, Paris.

  DOI：

  10.1016/s0223-5234(99)80072-5

文献信息

• Sulfamide-metalloprotease inhibitors
  申请人：Syntex (U.S.A.) Inc.

  公开号：US05998412A1

  公开（公告）日：1999-12-07

  This invention relates to sulfamides of formula (I) ##STR1## that are inhibitors of metalloproteases, pharmaceutical compositions containing them, methods for their use and methods for preparing these compounds.

  这项发明涉及公式（I）的磺胺酰胺，它们是金属蛋白酶抑制剂，包含它们的药物组合物，其使用方法以及制备这些化合物的方法。
• N-substituted azaheterocyclic carboxylic acids and esters thereof
  申请人：Novo Nordisk A/S

  公开号：US06239148B1

  公开（公告）日：2001-05-29

  The present invention relates to novel N-substituted azaheterocyclic carboxylic acids and esters thereof in which a substituted alkyl chain forms part of the N-substituent or salts thereof, to methods for their preparation, to compositions containing them, and to their use for the clinical treatment of painful, hyperalgesic and/or inflammatory conditions in which C-fibers play a pathophysiological role by eliciting neurogenic pain or inflammation.

  本发明涉及新型N-取代的氮杂环羧酸和其酯类，其中取代的烷基链构成N-取代基或其盐，以及它们的制备方法、含有它们的组合物和它们在临床治疗中的使用，用于治疗C纤维通过诱发神经源性疼痛或炎症在疼痛、过敏和/或炎症病症中发挥病理生理作用。
• N-substituted azaheterocyclic carboxylic acids and their use
  申请人：Novo Nordisk A/S

  公开号：US06613791B1

  公开（公告）日：2003-09-02

  N-substituted azaheterocycyclic carboxylic acids and esters thereof of the formula I wherein Z, X, R1, R2 and r are defined in the specification. Compositions thereof and methods for preparing the compounds are disclosed. The compounds are useful for clinical treatment of painful, hyperalgesic and/or inflammatory conditions in which C-fibers play a pathophysiological role by eliciting neurogenic pain or inflammations.

  本发明公开了式I中Z、X、R1、R2和r在说明书中定义的N-取代的杂环羧酸及其酯类。公开了这些化合物的组成及其制备方法。这些化合物在临床治疗C纤维通过引起神经源性疼痛或炎症所起的病理生理作用的疼痛、高敏感和/或炎症病症中非常有用。
• Use of N-Fmoc amino acid chlorides and activated 2-(fluorenylmethoxy)-5(4H)-oxazolones in solid-phase peptide synthesis. Efficient syntheses of highly N-alkylated cyclic hexapeptide oxytocin antagonists related to L-365,209
  作者：Debra S. Perlow、Jill M. Erb、Norman P. Gould、Roger D. Tung、Roger M. Freidinger、Peter D. Williams、Daniel F. Veber

  DOI：10.1021/jo00042a016

  日期：1992.7

  Fmoc amino acid chlorides have been shown to be useful reagents in the solid-phase synthesis of hexapeptides containing up to four sequential secondary amino acids. The oxytocin antagonist cyclo-(D-Phe-Ile-D-Pip-Pip-D-(N-Me)Phe-Pro) (1) was prepared in 70% overall yield starting from Boc-L-Pro-O-(PAM)-resin. In the synthesis of 1, the high reactivity of Fmoc-L-pipecolic acid chloride used in the di- to tripeptide step averted diketopiperazine formation seen with active ester couplings. The use of Fmoc-amino acid chlorides in the subsequent couplings provided a rapid method for assembly of the linear hexapeptide. The two potent cyclic hexapeptide oxytocin antagonists L-366,682 and L-366,948 were prepared in 45-48% overall yield on a 20 mmol scale using the methodology developed for the synthesis of 1. A particularly difficult coupling was encountered that involved acylation of a sterically hindered N(delta)-Cbz-piperazic acid N-terminus with Fmoc-L-isoleucine. Excess Fmoc-L-isoleucine acid chloride in the presence of tertiary amine base gave only 30% conversion. The efficiency was improved to 76% by utilizing the acid chloride with AgCN in toluene. Further investigation revealed that this combination of reagents produces an activated form of the isoleucine 2-alkoxy-5(4H)-oxazolone derivative.
• McFarlane, Andrew K.; Thomas Gareth; Whiting, Andrew, Journal of the Chemical Society. Perkin transactions I, 1995, # 21, p. 2803 - 2810
  作者：McFarlane, Andrew K.、Thomas Gareth、Whiting, Andrew

  DOI：——

  日期：——