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维格列汀的合成 被引量：7

Synthesis of Vildagliptin
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摘要 L-脯氨酰胺经氯乙酰氯酰化得(S)-N-氯乙酰基-2-氨甲酰基吡咯烷(2),2经三氟乙酐脱水得(S)-N-氯乙酰基-2-氰基吡咯烷(3),3与3-氨基-1-金刚烷醇发生亲核取代反应制得2型糖尿病治疗药维格列汀,总收率约70%(以L-脯氨酰胺计)。 Vildagliptin, an antidiabetic drug, was synthesized from L-prolinamide, chloroacetyl chloride and triftuoroacetic anhydride to give （S） -N-chloroacetyl-2-cyanopyrrolidine, which was followed by reaction with 3-amino-1- adamantanol with an overall yield of about 70 % （based on L-prolinamide）.
作者 宋伟国 付永强 张晓攀 夏艳 徐文方
机构地区 山东大学药学院 寿光富康制药有限公司
出处 《中国医药工业杂志》 CAS CSCD 北大核心 2012年第12期965-967,共3页 Chinese Journal of Pharmaceuticals
关键词 维格列汀 2型糖尿病 合成 vildagliptin type 2 diabetes synthesis
分类号 R971.41 [医药卫生—药品]
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参考文献11

  • 1Croxtall JD, Keam SJ. Vildagliption: a review of its use in the management of type 2 diabetes mellitus [J]. Drugs, 2008, 68 (26) : 2387-2409.
  • 2Villhauer EB, Brinkman JA, Naderi GB, et al. 1-E [ (3-Hydroxy- 1-adamantyl) amino] -2-cyano-(S) - pyrrolidine: a potent selective, and orally bioavailable dipetpidyl peptidase inhibitor with antihyperglycemic properties [J]. J Med Chem, 2003, 46 (13) : 2774-2789.
  • 3Abrecht S, Bubendorf AG, Goetzoe S, et al. New salt and polymorphs of a DPP-IV inhibitor: WO, 2006100181 [P]. 2006-09-28.
  • 4Stephen W, Jordi B, Jordi PS, et al. Process for preparing vildagliptin: US, 20080167479 [P]. 2008-07-10.
  • 5Ales HM, Bozena KK, Tomas CJ. A method of preparation of highly pure vildagliptin: WO, 2010022690 [P]. 2010-03-04.
  • 6Fukushima H, Hiratate A, Takahashi M, et al. Synthesis and structure-activity relationships of potent 3- or 4-substituted- 2-cyanopyrrolidine dipeptidyl peptidase IV inhibitors [J]. Bioorg Med Chem, 2004, 12 (23) : 6053-6061.
  • 7Singh SK, Manne N, Pal M. Synthesis of (S) -1-(2- chloroacetyl) pyrrolidine-2-carbonitrile: a key intermediate for dipeptidyl peptidase IV inhibitors [J]. Beilstein J Org Chem, 2008, 4: 20.
  • 8Kuznetsov SA, Skomorokhov M. Synthesis of some 1-bromo-3- (N-substituted amino) adamantanes [J]. Izvestiya Vysshikh Uchebnykh Zavedeni Khimiyai Khimicheskeskaya Tekhnologiya, 2005, 48 (10) : 62-64.
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同被引文献53

  • 1王璐,邸阜生.肠促胰岛素类似物和DPP-Ⅳ抑制剂在2型糖尿病治疗中的作用[J].医学综述,2007,13(1):25-27. 被引量：6
  • 2Villhauer EB. N-Substituted 2-cyanopyrrolidines: WO, 0034241 [P]. 2000-06-15.
  • 3Fukushima H, Hiratate A, Takahashi M, et al. Synthesis and structure-activity relationships of potent 3- or 4-substituted- 2-cyanopyrrolidine dipeptidyl peptidase 1V inhibitors [J]. Bioorg Med Chem, 2004, 12 (23) : 6053-6061.
  • 4Villhauer EB, Brinkman JA, Naderi GB, et al. 1-[ [ (3-Hydroxy-l-adamantly) amino] acetyl] -2-cyano- (S)-prrrolidine: a potent, selective, and orally bioavailable dipeptidyl peptidase- IV inhibitor with antihyperglycemic properties [J]. JMed Chem, 2003, 46 (13) : 2774-2789.
  • 5Stephen W, Jordi B, Jordi PS, et al. Process for preparing vildagliptin: WO, 2008084383 [P]. 2008-10-01.
  • 6Santosh KS, Narendra M, Manojit P. Synthesis of (S)-1-(2- chloroacetyl) pyrrolidine-2-carbonitrile: a key intermediate for dipeptidyl peptidase IV inhibitors [J]. Beilstein J Org Chem, 2008, 4 (20) : 1-5.
  • 7Dudley JR, Thurston JT, Schaefer FC, et al. Cyanuric chloride derivatives. III. Alkoxy-s-triazines [J]. JAm Chem Soc, 1951, 73 (7) : 2986-2990.
  • 8Mathieu C. The scientific evidence: Vildagliptin and the benefits of islet enhancement[ J ]. Diabetes, Obesi- ty and Metabolism,2009 ,ll(s2) :9 -17.
  • 9Keating G M. Vildagliptin: A review of its use in type 2 diabetes mellitus [ J ]. Drugs,2014,74(5) :587 - 610.
  • 10Singh S K, Manne N, Pal M. Synthesis of (S)-I-(2- chloroacetyl) pyrrolidine-2-carbonitrile: A key interme- diate for dipeptidyl peptidase IV inhibitors [ J ]. Beil- stein Journal of Organic Chemistry.,2008,4( 1 ) :20.

引证文献7

二级引证文献12

中国医药工业杂志
2012年 第12期

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