99010-63-6

Usage

Uses

Used in Pharmaceutical Industry:
Imiquimod Related Compound B (25 mg) (1-Isobutyl-1H-imidazo[4,5-c]quinoline 5-oxide) is used as an immune response modifier for enhancing the body's natural defense mechanisms against various diseases and infections. Its primary application is in the stimulation of Interferon-a production, which helps in modulating the immune system and combating pathogens.
Additionally, due to its immune-stimulating properties, Imiquimod Related Compound B (25 mg) (1-Isobutyl-1H-imidazo[4,5-c]quinoline 5-oxide) may also be utilized in the development of treatments for various conditions, including cancer, viral infections, and other immune-related disorders. Its potential applications in these areas are currently under investigation, and further research is needed to fully understand its therapeutic potential.

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

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

Relevant academic research and scientific papers

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.

Process for the preparation of imidazo[4,5-c]-quinolin-4-amines

The present invention is a method for preparing a compound of the formula wherein R is hydrogen, C1 to C6 alkyl, C1 to C6 alkoxy or halo, R1 and R2 are independently hydrogen, C1 to C10 alkyl, C1 to C10 alkoxy, C3 to C10 cycloalkyl, C3 to C10 alkenyl, C5 to C10 cycloalkenyl, C2 to C10 alkynyl, C6 to C20 aryl or substituted C6 to C20 aryl and n is the integer 1 or 2 by reacting the corresponding N-oxide with an aqueous solution of ammonia and a C1 to C6 alkyl, C6 to C20 aryl or substituted C6 to C20 aryl chloroformate thereby forming said compound formula (1).

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.

Synthesis and structure - Activity-relationships of 1H-imidazo[4,5-c] quinolines that induce interferon production

1H-Imidazo-[4,5-c]quinolines were prepared while investigating novel nucleoside analogues as potential antiviral agents. While these compounds showed no direct antiviral activity when tested in a number of cell culture systems, some demonstrated potent inhibition of virus lesion development in an intravaginal guinea pig herpes simplex virus-2 assay. We have determined that the in vivo antiviral activity can be attributed to the ability of these molecules to induce the production of cytokines, especially interferon (IFN), in this model. Subsequently, we found that the compounds also induce in vitro production of IFN in human peripheral blood mononuclear cells (hPBMCs). The in vitro results reported herein and the in vivo results reported previously led to the discovery of imiquimod, 26, which was developed as a topical agent and has been approved for the treatment of genital warts, actinic keratosis, and superficial basal cell carcinoma.

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.

PREPARATION OF 1H-IMIDAZO[4,5-C]QUINOLIN-4-AMINES VIA1H-IMIDAZO [4,5-C]QUINOLIN-4-PHTHALIMIDE INTERMEDIATES

The invention provides 1H-imidazo(4,5-C) quinolin-4-phthalimide intermediates useful in the synthesis of 1H-imidazo(4,5-C) quinoline-4-amines, particularly Imiquimod. The invention further provides a method for making the intermediates and a method for making 1H-imidazo (4,5-C) quinoline-4-amines via the intermediates.

1H-IMIDAZO[4,5-C]QUINOLIN-4-AMINES AND ANTIVIRAL USE

1H-Imidazo[4,5-c]quinolin-4-amines which are antivirals. Pharmacological methods of using such compounds and pharmaceutical compositions containing such compounds are also described

1H-imidazo[4,5-c]quinolines and their use as bronchodilating agents

1H-imidazo[4,5-c]quinoline which are bronchodilators. Pharmacological methods of using the compounds as bronchodilators, pharmaceutical compositions containing the compounds, and synthetic intermediate for preparing the compounds are also described.