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Naratriptan Produkt Beschreibung

Naratriptan Struktur
121679-13-8
CAS-Nr.
121679-13-8
Englisch Name:
Naratriptan
Synonyma:
Naratriptan;Naratriptan1;Naratriptane;Naratriptan(Amerge);AMERGE; NARAMIG; GR-85548A;N-methyl-3-(1-methyl-4-piperidinyl)-1H-Indole-5-ethanesulfonamide;N-methyl-2-[3-(1-methyl-4-piperidyl)-1H-indol-5-yl]ethanesulfonamide;N-Methyl-2-[3-(1-methylpiperidin-4-yl)-1H-indol-5-yl]ethanesulfonamide
CBNumber:
CB1874790
Summenformel:
C17H25N3O2S
Molgewicht:
335.46
MOL-Datei:
121679-13-8.mol

Naratriptan Eigenschaften

Schmelzpunkt:
170-171°
CAS Datenbank
121679-13-8

Sicherheit

Naratriptan Chemische Eigenschaften,Einsatz,Produktion Methoden

Originator

Amerge,Glaxo Wellcome,UK

Verwenden

Antimigraine.

Manufacturing Process

N-Methyl-3-(1,2,3,6-tetrahydro-1-methyl-4-pyridinyl)-1H-indole-5- ethanesulphonamide oxalate
A solution of N-methyl-1H-indole-5-ethanesulphonamide (1.0 g) in methanol (50 ml) containing potassium hydroxide (5.6 g) and N-methyl-4-piperidone (1.0 ml) was heated at reflux for 24 h, cooled, and the resulting solid filtered off (1.0 g). A sample of the solid (0.2 g) was dissolved in a hot methanolic solution of oxalic acid (0.06 g), the solution cooled, and the salt precipitated by adding ethyl acetate (20 ml) and dry ether (50 ml). The salt was filtered off, and dried in vacuo to give the title compound as a solid (0.12 g), m.p. 87°-90°C (shrinks).
Analysis Found: C,52.2; H,5.6; N,9.5. C17H23N3O2S · C2H2O4 · 0.6H2O requires C,52.5; H,6.0; N,9.7%.
N-Methyl-3-(1-methyl-4 -piperidinyl)-1H-indole-5-ethansulphonamide
N-Methyl-3-(1,2,3,6-tetrahydro-1-methyl-4-pyridinyl)-1H-indole-5- ethanesulphonamide oxalate (as the free base) (0.36 g, 0.001 mol) in absolute alcohol (70 ml) and anhydrous dimethylformamide (5 ml) was hydrogenated, in the presence of 5% palladium on activated carbon (0.36 g) at ambient temperature and atmospheric pressure. After 20 h, hydrogen absorption (25 cm3, theoretical = 24 cm3) ceased. The catalyst was filtered off and the solvent removed in vacuo to given an opaque gum which solidified as a soft white solid (0.3 g). Purification by flash chromatography (Sorbsil C60 silica gel, CH2Cl2/EtOH/0.88 ammonia; 50:80:1) gave a colorless oil (0.21 g) that was triturated with ether to give the title compound (0.17 g) m.p. 156°- 158°C. TLC SiO2(CH2Cl2/EtOH/0.88 ammonia; 50:8:1) Rf 0.4.
N-Methyl-3-(1-methyl-4-piperidinyl)-1H-indole-5-ethanesulphonamide may be prepared the another way.
A solution of 4-hydrazino-N-methyl-benzenethanesulphonamide (0.5 g) and 1- methyl-4-piperidineacetaldehyde (0.35 g) in a mixture of water (10 ml) of 2 N hydrochloric acid (1.0 ml, 2.00 mmol) was stirred for 2 days at room temperature. A further quantity of the aldehyde (0.35 g) was added and stirring continued for a further 30 min. The solution was then basified with 8% sodium bicarbonate to pH 8 and extracted with chloroform (3 times 50 ml). The combined organic extracts were dried (Na2SO4) and evaporated in vacuo to give the crude hydrazone as an oil (1.0 g). A solution of the hydrazone (1.0 g) in chloroform (20 ml) containing polyphosphate ester (10 g) was heated at reflux for 8 min. The solution was poured onto ice (200 g), stirred for 2 h treated with 2 M sodium carbonate (20 ml) and extracted with chloroform (3 times 50 ml). The combined organic extracts were dried (Na2SO4), evaporated in vacuo and the residue purified by flash chromatography (silica 9385, 100 g) eluting with CH2Cl2/EtOH/NH3(75:8:1) to give impure material as a yellow oil. Further flash chromatography (silica 9385, 100 g) eluting with CH2Cl2/EtOH/NH3 (100:8:1) gave the product as an oil (0.05 g). This was crystallised from ethyl acetate to give the title compound solid m.p. 156°-157°C. TLC SiO2(CH2Cl2/EtOH/NH3(50:8:1)) Rf 0.6.

Trademarks

Amerge (GlaxoSmithKline).

Therapeutic Function

Serotonin antagonist, Migraine therapy

Allgemeine Beschreibung

Naratriptan, the third triptan approved in 1998, is one of themost lipophilic triptans marketed to date. It has a much improvedbioavailability (63% in men and 74% in women), agreater affinity for 5-HT1B/1D receptors (3–6 times), and alower recurrence rate than sumatriptan because of its muchlonger elimination half-life. Naratritan also has a favorableCNS side effect profile when compared with sumatriptanor zolmitriptan because of its metabolic stability,thereby lacking a N-demethylated active metabolite and asignificant renal excretion ( 70% of naratriptan is excretedunchanged and the rest of the administered dose is degradedvia several CYP isozymes).

Naratriptan Upstream-Materialien And Downstream Produkte

Upstream-Materialien

Downstream Produkte


Naratriptan Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

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121679-13-8()Verwandte Suche:


  • Naratriptan
  • Naratriptane
  • N-methyl-2-[3-(1-methyl-4-piperidyl)-1H-indol-5-yl]ethanesulfonamide
  • Naratriptan(Amerge)
  • N-Methyl-2-[3-(1-methylpiperidin-4-yl)-1H-indol-5-yl]ethanesulfonamide
  • Naratriptan1
  • AMERGE; NARAMIG; GR-85548A
  • N-methyl-3-(1-methyl-4-piperidinyl)-1H-Indole-5-ethanesulfonamide
  • 121679-13-8
  • 21679-13-8
  • API
  • Indoline & Oxindole
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