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サキサグリプチン

サキサグリプチン 化学構造式
361442-04-8
CAS番号.
361442-04-8
化学名:
サキサグリプチン
别名:
サキサグリプチン;サクサグリプチン
英語化学名:
Saxagliptin
英語别名:
CS-199;Onglyza;xagliptin;BMS 477118;Saxagliptin;Saxagliptin API;Saxagliptin HCl;Saxagliptin 15ND2;Saxagliptin, >=98%;Salkeliptin impurity
CBNumber:
CB61856071
化学式:
C18H25N3O2
分子量:
315.41
MOL File:
361442-04-8.mol

サキサグリプチン 物理性質

沸点 :
548.7±35.0 °C(Predicted)
比重(密度) :
1.35
闪点 :
548.7℃
貯蔵温度 :
Sealed in dry,2-8°C
酸解離定数(Pka):
15.12±0.40(Predicted)

安全性情報

Rフレーズ  28-38-41-48
Sフレーズ  24/25-26-28-36/37/39
RIDADR  3077
HSコード  29339900
有毒物質データの 361442-04-8(Hazardous Substances Data)

サキサグリプチン 価格

メーカー 製品番号 製品説明 CAS番号 包装 価格 更新時間 購入

サキサグリプチン 化学特性,用途語,生産方法

効能

糖尿病治療薬, DPP-4阻害薬

化学的特性

White Solid

使用

Saxagliptin is a potent and selective reversible inhibitor of dipeptidyl peptidase-4, which is being developed for the treatment of type 2 diabetes. It is absorbed rapidly after oral administration an d has a pharmacokinetic profile compatible with once daily dosing.

使用

Saxagliptin is a potent and selective reversible inhibitor of dipeptidyl peptidase-4, which is being developed for the treatment of type 2 diabetes. It is absorbed rapidly after oral administration and has a pharmacokinetic profile compatible with once daily dosing.

定義

ChEBI: A monocarboxylic acid amide obtained by formal condensation of the carboxy group of (2S)-amino(3-hydroxyadamantan-1-yl)acetic acid with the amino group of (1S,3S,5S)-2-azabicyclo[3.1.0]hex ne-3-carbonitrile. Used in its monohydrate form for the treatment of Type II diabetes.

臨床応用

Saxagliptin, previously identified as BMS-477118, is an oral hypoglycemic of the dipeptidyl peptidase-4 (DPP-4) inhibitor class developed by Bristol-Myers Squibb for the treatment of type 2 diabetes. DPP-IV is the primary enzyme responsible for degradation of incretins, such as glucagon-like peptide-1 (GLP-1), which is a hormone responsible for the glucose-dependent stimulation of insulin in humans. Inhibitors of DPP-IV serve as effective glucose regulators by increasing the endogenous concentration of GLP-1.

Chemical Synthesis

The initial discovery route to saxagliptin was a 15-step, convergent synthesis focused on the production and use of compounds 109 and 113 (Schemes a and b). While the strategy of early drug delivery involved rapid synthesis to support preclinical activities and Phase I clinical trials, as saxagliptin entered Phase II, a greater emphasis was placed on defining and demonstrating a commercially viable synthetic process. Scheme a describes a more expedient route to the preparation of adamantylamino acid 109. Commercially available 1-adamantoic acid (106) was first converted to the corresponding acid halide through the use of thionyl chloride prior to a Grignard addition reaction utilizing iodomethane and magnesium metal to furnish ketone 107. This ketone was then subjected to oxidizing conditions involving potassium permanganate to provide the hydroxylated ketoacid 108. The amino acid 109 was furnished through the use of phenylalanine dehydrogenase in near-quantitative yield in 99% enantioselectivity.
The synthesis of 113 began with commercially available ethyl N-tert-butoxycarbonylpyroglutamate (110) (Scheme b). Selective reduction of the amide carbonyl within 110 through the use of lithium triethylborohydride followed by acylation and baseinduced elimination of the resulting aminal and careful hydrolysis gave rise to dihydropyrrole 111 with full retention of stereochemical configuration in 95% yield. Amidation followed by Simmons– Smith cyclopropanation employing methylene iodide converted 111 to the cyclopropanated product 112, which was then converted to the key coupling partner 113.
The core of saxagliptin was formed by the amide coupling of amino acid 109 and methanoprolinamide 113 to give amide 114 in 95% yield (Scheme c). Subsequent dehydration of the primary amide 114 using trifluoroacetic acid anhydride and ethyl nicotinate gave nitrile 115 in 98% yield. Removal of both the alcohol and amine protecting groups with HCl afforded saxagliptin (XVIII) in 88% yield.

サキサグリプチン 上流と下流の製品情報

原材料

準備製品


サキサグリプチン 生産企業

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361442-04-8(サキサグリプチン)キーワード:


  • 361442-04-8
  • (1S,3S,5S)-2-[(2S)-2-amino-2-(3-hydroxy-tricyclo[3.3.13,7]dec-1-yl)-1-oxoethyl]-2-azabicyclo-[3.1.0]hexane-3-carbonitrile
  • BMS 477118
  • Onglyza
  • Saxagliptin
  • (1S,3S,5S)-2-[(2S)-2-Amino-2-(3-hydroxytricyclo[3.3.1.13,7]dec-1-yl)acetyl]-2-azabicyclo[3.1.0]hexane-3-carbonitrile
  • Saxagliptin(BMS 477118)
  • Saxagliptin 15ND2
  • BMS477118;SAXAGLIPTIN
  • (1S,3S,5S)-2-[(2S)-2-aMino-2-(3-hydroxyadaMantan-1-yl)acetyl]-2-azabicyclo[3.1.0]hexane-3-carbonitrile
  • Saxagliptin HCl
  • Saxagliptin API
  • 2-Azabicyclo[3.1.0]hexane-3-carbonitrile, 2-[(2S)-2-amino-2-(3-hydroxytricyclo[3.3.1.13,7]dec-1-yl)acetyl]-, (1S,3S,5S)-
  • Saxagliptin (1S,3S,5S)-2-[(2S)-2-Amino-2-(3-hydroxytricyclo[3.3.1.1(3,7)]dec-1-yl)acetyl]-2-azabicyclo[3.1.0]hexane-3-carbonitrile
  • Saxagliptin Onglyza BMS 477118
  • Saxagliptin, 97%, selective and reversible DPP4 inhibitor
  • Saxagliptin, >=98%
  • CS-199
  • Saxagliptin-13C-d2 HCl
  • Saxagliptin ? BMS 477118 ?Onglyza
  • Saxagliptin , SAXAGLIPTIN
  • [13C2,15N]-Saxagliptin
  • xagliptin
  • Saxagliptin USP/EP/BP
  • Salkeliptin impurity
  • サキサグリプチン
  • サクサグリプチン
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