ラニナミビルオクタン酸エステル水和物

ラニナミビルオクタン酸エステル水和物 化学構造式
203120-46-1
CAS番号.
203120-46-1
化学名:
ラニナミビルオクタン酸エステル水和物
别名:
ラニナミビルオクタン酸エステル水和物;ラニナミビルオクタン酸エステル;ラニナミビルオクタン酸エステル水和物 (JAN);オクタン酸ラニナミビル;5,6-ジヒドロ-4α-グアニジノ-5β-(アセチルアミノ)-6-[(1R,2R)-2-ヒドロキシ-1-メトキシ-3-(オクタノイルオキシ)プロピル]-4H-ピラン-2-カルボン酸;(3R,4S)-4-カルバムイミドアミド-3-アセトアミド-2-[(1R,2R)-2-ヒドロキシ-1-メトキシ-3-(オクタノイルオキシ)プロピル]-3,4-ジヒドロ-2H-ピラン-6-カルボン酸;CS-8958
英語名:
laninamivir octanoate
英語别名:
CS 8958;laninamivir octanoate;Laninamivir Octanoate Hydrate;laninamivir octanoate USP/EP/BP;H2N2,CS8958,H3N2,inhaled,CS 8958,Laninamivir octanoate,neuraminidase,inhibit,Anti-influenza,Influenza Virus,Inhibitor;(2R,3R,4S)-3-Acetamido-4-guanidino-2-[(1R,2R)-2-hydroxy-1-methoxy-3-(octanoyloxy)propyl]-3,4-dihydro-2H-pyran-6-carboxylic acid;(4S,5R,6R)-5-Acetamido-4-guanidino-6-[(1R,2R)-2-hydroxy-1-methoxy-3-(octanoyloxy)propyl]-5,6-dihydro-4H-pyran-2-carboxylic acid;D-Glycero-D-galacto-non-2-enonic acid 5-(acetylamino)-4-[(aminoiminomethyl)amino]-2,6-anhydro-3,4,5-trideoxy-7-O-methyl-9-octanoate
CBNumber:
CB22511887
化学式:
C21H36N4O8
分子量:
472.53
MOL File:
203120-46-1.mol

ラニナミビルオクタン酸エステル水和物 物理性質

融点 :
224-228°C (dec.)
比重(密度) :
1.35
貯蔵温度 :
Hygroscopic, -20°C Freezer, Under Inert Atmosphere
溶解性:
DMSO(微量)、メタノール(微量)
外見 :
個体
酸解離定数(Pka):
3.80±0.70(Predicted)
色:
ホワイトからオフホワイト
安定性::
吸湿性

安全性情報

ラニナミビルオクタン酸エステル水和物 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
Sigma-Aldrich Japan SML3534 ≥98% (HPLC)
Laninamivir octanoate ≥98% (HPLC)
203120-46-1 5MG ¥9760 2024-03-01 購入
Sigma-Aldrich Japan SML3534 ≥98% (HPLC)
Laninamivir octanoate ≥98% (HPLC)
203120-46-1 25MG ¥39300 2024-03-01 購入

ラニナミビルオクタン酸エステル水和物 化学特性,用途語,生産方法

効能

抗ウイルス薬, ノイラミニダーゼ阻害薬

商品名

イナビル (第一三共)

臨床応用

Laninamivir octanote, a prodrug of a potent neuraminidase inhibitor (LANI), was approved and launched in 2010 in Japan for the treatment of influenza A and influenza B. This ester prodrug of a potent neuraminidase inhibitor was designed to permeate from the lung tissue to the plasma and then hydrolyze at such a rate to reveal the active form (laninamivir) as a long-acting therapeutic agent. Neuraminidase cleaves the glycosidic linkages of neuraminic acids which are responsible for binding new viruses to infected cells, thereby allowing viruses to release and infect other cells. Neuraminidase is essential for the replication of all influenza viruses. Like other neuraminidase inhibitors, laninamivir octanoate is a sialic acid analogue which is structurally similar to zanamivir, differing only by changing one of the hydroxy groups with a methyl ether substitution on the triol side chain. Laninamivir is administered via an inhalable formulation (20 mg, dry powder inhaler) and results from clinical trials of the drug have demonstrated that a single inhaled dose is as effective as a 5-day course of oseltamivir for treatment of influenza.

合成

The synthesis of laninamivir octanoate began with the well-documented sugar intermediate 101. Alcohol 101 was alkylated with dimethyl sulfate in the presence of NaH in DMF to give methyl ether 102 in 80% yield. Acetonide 102 was then deprotected and subsequently acylated with Ac2O, AcOH, and H2SO4 (10:10:1, v/v) which resulted in oxazoline formation along with elimination of the methoxy functionality to furnish |�|?-unsaturated ester 103. Exposure of oxazoline 103 to NaN3 in the presence of Dowex 50W/H+ produced the transamidoazide 104 in 70% yield over two steps. Azide 104 was then subjected to guanidine formation conditions utilizing N,N-bis(tertbutoxycarbonyl)-1H-pyrazole-1-carboxyamidine (106), which was prepared from pyrazole-1-carboxamidine (105) by consecutive protection of the amidine nitrogens, first by treatment with Boc anhydride and diisopropylethyl amine (DIEA) in DMF, and then subsequent treatment to Boc anhydride in the presence of NaH in THF to give 107 in 80% yield. The protected guanidine 107 was hydrolyzed under basic conditions to give the corresponding acid 108 in good yield. Acid 108 was esterified with diphenyl diazomethane in THF to provide 109 in 85% yield. Finally, the primary alcohol within diol 109 was selectively acylated with octanoyl chloride in the presence of TEA, followed by de-protection with TFA in CH2Cl2 to give laninamivir octanote (VIII) in 70% yield.

説明図

ラニナミビルオクタン酸エステル水和物 上流と下流の製品情報

原材料

準備製品


ラニナミビルオクタン酸エステル水和物 生産企業

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203120-46-1(ラニナミビルオクタン酸エステル水和物)キーワード:


  • 203120-46-1
  • (4S,5R,6R)-5-Acetamido-4-guanidino-6-[(1R,2R)-2-hydroxy-1-methoxy-3-(octanoyloxy)propyl]-5,6-dihydro-4H-pyran-2-carboxylic acid
  • CS 8958
  • D-Glycero-D-galacto-non-2-enonic acid 5-(acetylamino)-4-[(aminoiminomethyl)amino]-2,6-anhydro-3,4,5-trideoxy-7-O-methyl-9-octanoate
  • laninamivir octanoate
  • Laninamivir Octanoate Hydrate
  • (2R,3R,4S)-3-Acetamido-4-guanidino-2-[(1R,2R)-2-hydroxy-1-methoxy-3-(octanoyloxy)propyl]-3,4-dihydro-2H-pyran-6-carboxylic acid
  • laninamivir octanoate USP/EP/BP
  • H2N2,CS8958,H3N2,inhaled,CS 8958,Laninamivir octanoate,neuraminidase,inhibit,Anti-influenza,Influenza Virus,Inhibitor
  • ラニナミビルオクタン酸エステル水和物
  • ラニナミビルオクタン酸エステル
  • ラニナミビルオクタン酸エステル水和物 (JAN)
  • オクタン酸ラニナミビル
  • 5,6-ジヒドロ-4α-グアニジノ-5β-(アセチルアミノ)-6-[(1R,2R)-2-ヒドロキシ-1-メトキシ-3-(オクタノイルオキシ)プロピル]-4H-ピラン-2-カルボン酸
  • (3R,4S)-4-カルバムイミドアミド-3-アセトアミド-2-[(1R,2R)-2-ヒドロキシ-1-メトキシ-3-(オクタノイルオキシ)プロピル]-3,4-ジヒドロ-2H-ピラン-6-カルボン酸
  • CS-8958
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