99010-63-6

Basic information

• Product Name: Imiquimod Related Compound B (25 mg) (1-Isobutyl-1H-imidazo[4,5-c]quinoline 5-oxide)
• Synonyms: Imiquimod Related Compound B (25 mg) (1-Isobutyl-1H-imidazo[4,5-c]quinoline 5-oxide);IMiquiMod Related CoMpound B;DesaMino IMiquiMod N-Oxide;1-Isobutyl-1H-imidazo[4,5-c]quinoline N-oxide;Imiquimod USP Related Compound B
• CAS NO: 99010-63-6
• Molecular Formula: C₁₄H₁₅N₃O
• Molecular Weight: 241.2884
• Mol File: 99010-63-6.mol
• Article Data: 8

Chemical Properties

• Melting Point: 211-214℃ (methanol ethyl ether )
• Boiling Point: 452.8±55.0 °C(Predicted)
• Appearance: /
• Density: 1.24±0.1 g/cm3(Predicted)
• Storage Temp.: -20°C Freezer, Under inert atmosphere
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 4.16±0.30(Predicted)
• CAS DataBase Reference: Imiquimod Related Compound B (25 mg) (1-Isobutyl-1H-imidazo[4,5-c]quinoline 5-oxide)(CAS DataBase Reference)
• NIST Chemistry Reference: Imiquimod Related Compound B (25 mg) (1-Isobutyl-1H-imidazo[4,5-c]quinoline 5-oxide)(99010-63-6)
• EPA Substance Registry System: Imiquimod Related Compound B (25 mg) (1-Isobutyl-1H-imidazo[4,5-c]quinoline 5-oxide)(99010-63-6)

Safety Data

• Hazardous Substances Data: 99010-63-6(Hazardous Substances Data)

Usage

Uses

Desamino Imiquimod N-Oxide (Imiquimod USP Related Compound B) is a pharmacologically active compound related to Imiquimod (I475000), an immune response modifier. It stimulates the production of Interferon-a.

Upstream product

• 99010-09-0 3-Amino-4-(2-methylpropylamino)-quinoline 
• 122-51-0 orthoformic acid triethyl ester 
• 39061-97-7 4-chloro-3-nitroquinoline 
• 50332-66-6 3-nitro-quinolin-4-ol 
• 611-36-9 quinolin-4-ol 
• 99009-85-5 N-(2-methylpropyl)-3-nitro-4-quinolinamine 
• 99010-24-9 1-(2-methylpropyl)-1H-imidazo[4,5-c]quinoline 

Downstream Products

• 144660-62-8 N-benzoyl-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinolin-4-amine 
• 99011-02-6 imiqimod 

Relevant articles and documents

Preparation of 1H-imidazo[4,5-c]quinolin-4-amines via 1H-imidazo[4, 5-c]quinolin-4-phtalimide intermediates

The present invention provides process for the preparation of 4-amino-1H-imidazo[4,5-c]quinolines comprising the step of reacting a 1H-imidazo[4,5-c]quinolin-4-phthalimide with an amine selected from the group consisting of: alkylamine, aralkylamine, alkyldiamine, and aralkyldiamine.

A PROCESS FOR PREPARATION OF 4-AMINO-1-ISOBUTYL-1H-IMIDAZO[4,5-C]-QUINOLINE (IMIQUIMOD)

A process for preparation of imiquimod comprising oxidation of 1-Isobutyl-1H-imidazo quinoline quinoline (II) afforded 1-Isobutyl-lH- imidazo-[4,5-c]-quinoline-5-N-oxide (III) which is isolated in pure form as its hydrochloride salt (IV) followed by conversion to 4-chloro derivative(V) and conversion to corresponding 4-iodo derivative (VI) which is a new intermediate. This new intermediate is convened to imiquimod (VIII) and purified via its novel maleate salt.

PREPARATION OF 1H-IMIDAZO [4,5-C] QUINOLIN-4-AMINES VIA NOVEL 1H-IMIDAZO [4,5-C] QUINOLIN-4-CYANO AND 1H-IMIDAZO [4,5-C] QUINOLIN-4-CARBOXAMIDE INTERMEDIATES

The invention relates to a process for the synthesis of 1H-imidazo[4,5-c] quinoline 4-cyano and 1H-imidazo[4,5-c] quinoline 4- carboxamide intermediates useful in preparing 1H-imidazo[4,5-C] quinoline 4-amines, a process for preparing 1H-imidazo [4,5-C] quinoline 4-amines using such intermediates; and, to the 1H-imidazo[4,5-c] quinoline 4-cyano and 1H-imidazo[4,5-c] quinoline 4- carboxamide intermediates. More particularly, the invention relates to a process for the preparation of 1-isobutyl-1H-imidazo [4,5-C] quinoline 4-amine (Imiquimod) using two intermediates, 1-isobutyl-1H-imidazo[4,5-c]quinoline 4-cyano and 1-isobutyl-1H-imidazo[4,5-c]quinoline 4-carboxamide, and to the said intermediates.