1422509-99-6

Basic information

• Product Name: 1-(3-chloro-2,6-difluorophenyl)-3-iodopropan-1-one
• Synonyms: 1-(3-chloro-2,6-difluorophenyl)-3-iodopropan-1-one
• CAS NO: 1422509-99-6
• Molecular Weight: 330.5
• Mol File: 1422509-99-6.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: 1-(3-chloro-2,6-difluorophenyl)-3-iodopropan-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(3-chloro-2,6-difluorophenyl)-3-iodopropan-1-one(1422509-99-6)
• EPA Substance Registry System: 1-(3-chloro-2,6-difluorophenyl)-3-iodopropan-1-one(1422509-99-6)

Safety Data

• Hazardous Substances Data: 1422509-99-6(Hazardous Substances Data)

Upstream product

• 1422509-98-5 1-(3-chloro-2,6-difluorophenyl)prop-2-en-1-one 
• 1422509-97-4 1-(3-chloro-2,6-difluorophenyl)prop-2-en-1-ol 
• 190011-87-1 1-(3-chloro-2,6-difluoro-phenyl)-carboxaldehyde 

Downstream Products

• 1422511-13-4 methyl N-[(12E,15S)-18-chloro-15-{[3-(3-chloro-2,6-difluorophenyl)-3-oxopropyl]amino}-9-oxo-17-{[2-(trimethylsilyl)ethoxy]methyl}-8,17,19-triazatricyclo[14.2.1.0^2,7]nonadeca-1⁽¹⁸⁾,2,4,6,12,16⁽¹⁹⁾-hexaen-5-yl]carbamate 
• 1422508-12-0 methyl N-[(10R,14S)-14-[(6R)-6-(3-chloro-2,6-difluorophenyl)-2-oxo-1,3-oxazinan-3-yl]-10-methyl-9-oxo-8,16,18-triazatricyclo[13.2.1.0^2,7]octadeca-1⁽¹⁷⁾,2,4,6,15⁽¹⁸⁾-pentaen-5-yl]carbamate 
• 1422510-92-6 methyl N-[(10R,14S)-14-[6-(3-chloro-2,6-difluorophenyl)-2-oxo-1,3-oxazinan-3-yl]-10-methyl-9-oxo-16-{[2-(trimethylsilyl)ethoxy]methyl}-8,16,18-triazatricyclo[13.2.1.0^2,7]octadeca-1⁽¹⁷⁾,2,4,6,15⁽¹⁸⁾-pentaen-5-yl]carbamate 
• 1422510-91-5 methyl N-[(10R,14S)-14-{[3-(3-chloro-2,6-difluorophenyl)-3-hydroxypropyl]amino}-10-methyl-9-oxo-16-{[2-(trimethylsilyl)ethoxy]methyl}-8,16,18-triazatricyclo[13.2.1.0^2,7]octadeca-1⁽¹⁷⁾,2,4,6,15⁽¹⁸⁾-pentaen-5-yl]carbamate 
• 1422511-22-5 (1R)-1-(3-chloro-2,6-difluorophenyl)-3-iodopropan-1-ol 
• 1422511-23-6 (1S)-1-(3-chloro-2,6-difluorophenyl)-3-iodopropan-1-ol 
• 1422510-61-9 1-(3-chloro-2,6-difluorophenyl)-3-iodo(1-²H)propan-1-(²H)ol 

Relevant articles and documents

Discovery of a High Affinity, Orally Bioavailable Macrocyclic FXIa Inhibitor with Antithrombotic Activity in Preclinical Species

Oral factor XIa (FXIa) inhibitors may provide a promising new antithrombotic therapy with an improved benefit to bleeding risk profile over existing antithrombotic agents. Herein, we report application of a previously disclosed cyclic carbamate P1 linker which provided improved oral bioavailability in the imidazole-based 13-membered macrocycle to the 12-membered macrocycle. This resulted in identification of compound 4 with desired FXIa inhibitory potency and good oral bioavailability but high in vivo clearance. Further structure-activity relationship (SAR) studies of heterocyclic core modifications to replace the imidazole core as well as various linkers to the P1 group led to the discovery of compound 6f, a potent FXIa inhibitor with selectivity against most of the relevant serine proteases. Compound 6f also demonstrated excellent pharmacokinetics (PK) profile (high oral bioavailability and low clearance) in multiple preclinical species. Compound 6f achieved robust antithrombotic efficacy in a rabbit efficacy model at doses which preserved hemostasis.