144875-48-9

Basic information

• Product Name: RESIQUIMOD
• Synonyms: RESIQUIMOD;1-[4-Amino-2-(ethoxymethyl)-1H-imidazo[4,5-C]quinolin-1-yl]-2-methylpropan-2-ol;Chebi:36706;4-Amino-2-(ethoxymethyl)-alpha,alpha-dimethyl-1H-imidazo[4,5-c]quinoline-1-ethanol;4-Amino-2-(ethoxymethyl)-alpha;alpha-dimethyl-1H-imidazo(4,5-c)quinoline-1-ethanol;resquimod;R848,Resiquimod
• CAS NO: 144875-48-9
• Molecular Formula: C₁₇H₂₂N₄O₂
• Molecular Weight: 314.387
• Product Categories: Agonist;Anti-virals;Aromatics;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 144875-48-9.mol

Chemical Properties

• Melting Point: 190-193°
• Boiling Point: 553.6°Cat760mmHg
• Flash Point: 288.6°C
• Appearance: white to tan/
• Density: 1.28
• Vapor Pressure: 4.33E-13mmHg at 25°C
• Refractive Index: 1.634
• Storage Temp.: ?20°C
• Solubility: DMSO: soluble10mg/mL, clear (warmed to 60 °C)
• PKA: 14.63±0.29(Predicted)
• Stability: Stable for 1 year from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20°C for up to 2 months.
• Merck: 14,8151
• CAS DataBase Reference: RESIQUIMOD(CAS DataBase Reference)
• NIST Chemistry Reference: RESIQUIMOD(144875-48-9)
• EPA Substance Registry System: RESIQUIMOD(144875-48-9)

Safety Data

• WGK Germany: 3
• RTECS: NJ5911320
• Hazardous Substances Data: 144875-48-9(Hazardous Substances Data)

Usage

Uses

Used in Antiviral Applications:
RESIQUIMOD is used as an antiviral agent for its potent activity against viruses such as herpes simplex virus. It modulates the immune response, leading to the inhibition of viral replication and the reduction of skin lesions associated with the infection.
Used in Cancer Treatment:
RESIQUIMOD is used as an immune adjuvant in cancer vaccines, enhancing the immune system's response to cancer cells. It has been employed in the stimulation of bone marrow-derived dendritic cells (BMDCs) and B cells, as well as a ligand for toll-like receptors (TLR7) in malignant melanoma cell line B16F10.
Used in Autoimmune Disease Research:
RESIQUIMOD is used as a model for systemic Lupus erythematosus, a systemic autoimmune disease. Topical treatment of wild-type mice with Resiquimod induces systemic autoimmune disease, providing valuable insights into the pathogenesis and potential treatments for this condition.
Used in Drug Delivery Systems:
RESIQUIMOD-carrying synthetic vaccine particles have been developed to augment the immune response to encapsulated antigens. These particles exhibit strong local immune activation without inducing systemic cytokine release, making them a promising approach for targeted drug delivery and enhanced therapeutic outcomes.
Used in Antiviral Research:
RESIQUIMOD has displayed potent antiviral activity (EC50 = 23.5 nM) in a murine norovirus replicon model, making it a valuable tool for studying and developing treatments for norovirus infections.

Biochem/physiol Actions

Resiquimod belongs to the class of imidazoquinolinamines compounds with immunomodulatory effects. Resiquimod increases the levels of cytokines such as TNF-α, IL-6 and IFN-α.

References

1) Jurk et al. (2002), Human TLR7 or TLR8 independently confer responsiveness to the antiviral compound R-848; Nat. Immunol., 3 499 2) Sabado et al. (2015), Resiquimod as an immunologic adjuvant for NY-ESO-1 protein vaccination in patients with high-risk melanoma; Cancer Immunol. Res., 3 278 3) Ilyinskii et al. (2014), Adjuvant-carrying synthetic vaccine particles augment the immune response to encapsulated antigen and exhibit strong local immune activation without inducing systemic cytokine release; Vaccine, 32 2882 4) Yokogawa et al. (2014), Epicutaneous application of toll-like receptor 7 agonists leads to systemic autoimmunity in wild-type mice: a new model of systemic Lupus erthematosus; Arthritis Rheumatol., 66 694 5) Tuipulotu et al. (2018), TLR7 Agonists Display Potent Antiviral Effects against Norovirus Infection via Innate Stimulation; Antimicrob. Agents Chemother., 62 e02417

InChI:InChI=1/C17H22N4O2/c1-4-23-9-13-20-14-15(21(13)10-17(2,3)22)11-7-5-6-8-12(11)19-16(14)18/h5-8,22H,4,9-10H2,1-3H3,(H2,18,19)

Upstream product

• 144876-01-7 4-chloro-α,α-dimethyl-2-ethoxymethyl-1H-imidazo[4,5-c]quinoline-1-ethanol 
• 144875-99-0 α,α-dimethyl-2-ethoxymethyl-1H-imidazo[4,5-c]quinoline-1-ethanol 
• 7440-44-0 pyrographite 
• 133860-77-2 1-[(2-chloro-3-nitro-4-quinolinyl)amino]-2-methyl-2-propanol 
• 133860-78-3 1-[(3-amino-2-chloro-4-quinolinyl)amino]-2-methyl-2-propanol 
• 253120-65-9 N-{2-chloro-4-[(2-hydroxy-2-methylpropyl)amino]quinolin-3-yl}-2-ethoxyacetamide 
• 15151-57-2 2,4-dihydroxy-3-nitroquinoline 
• 70254-44-3 2,4-dihydroxyquinoline 
• 132521-66-5 2,4-dichloro-3-nitroquinoline 

Downstream Products

• 102-76-1 triacetylglycerol 

Relevant articles and documents

IMIDAZOQUINOLINE-TYPE COMPOUNDS AND USES THEREOF

Provided in the present disclosure are imidazoquinoline-type compounds, methods for their preparation, pharmaceutical compositions thereof and their use, wherein the imidazoquinoline-type compounds, upon local administration, form depots inducing cell mediated immune response while mitigating a systemic proinflammatory immune response.

LOCALLY ACTING TOLL-LIKE RECEPTOR 7 (TLR7) AND/OR TLR8 AGONIST IMMUNOTHERAPY COMPOUNDS AND THEIR USES

Provided in the present disclosure are immunotherapy compounds, pharmaceutical compositions thereof and their use, wherein the immunotherapy compounds, upon local administration, form depots inducing cell mediated immune response while mitigating a systemic proinflammatory immune response.

IMMUNOMODULATORY CONJUGATES

The present invention provides an immunomodulatory compound comprising a carbohydrate polymer comprising mannose, wherein the carbohydrate polymer is conjugated to at least one immune modulator. The present invention also provides for the use of this compound in immunomodulatory compositions for vaccination and gene therapy methods, together with processes for its preparation.

METHOD FOR 1H-IMIDAZO[4,5-c]PYRIDINES AND ANALOGS THEREOF

Methods and intermediates for preparing compounds of the Formulas: (I and X) are disclosed. The methods include a method providing a compound of the Formula: (IV) and converting a compound of Formula IV to a compound of Formula I, a method providing a compound of the Formula: (VIII) and converting a compound of Formula VIII to a compound of Formula I, and a method providing a compound of the Formula: (XI) and converting a compound of Formula XI to a compound of Formula I.

1-substituted, 2-substituted 1H-imidazo[4,5-c]quinolin-4-amines

1-substituted, 2-substituted 1H-imidazo[4,5-c]-quinolin-4-amines are disclosed. These compounds function as antiviral agents, they induce biosynthesis of interferon, and they inhibit tumor formation in animal models. This invention also provides intermediates for preparing such compounds, pharmaceutical compositions containing such compounds, and pharmacological methods of using such compounds.

Process for preparing 1-substituted, 2-substituted 1H-imidazo[4, 5-c]quinoline-4-amines

Methods of preparing 1-substituted, 2-substituted 1H-imidazo [4-5c]-quinolin-4-amines are disclosed. The compounds function as antiviral agents, they induce the biosynthesis of various cytokines including interferon, and they inhibit tumor formation in animal models.

1-substituted, 2-substituted 1H-imidazo[4,5-c]quinolin-4-amines

1-substituted, 2-substituted 1H-imidazo[4,5-c]-quinolin-4-amines are disclosed. These compounds function as antiviral agents, they induce biosynthesis of interferon, and they inhibit tumor formation in animal models. This invention also provides intermediates for preparing such compounds, pharmaceutical compositions containing such compounds, and pharmacological methods of using such compounds.