892549-54-1

Basic information

• Product Name: 2-[9-chloro-6-(3-hydroxy-3-methylbut-1-yn-1-yl)-1H-phenanthro[9,10-d]imidazol-2-yl]isophthalonitrile
• Synonyms: 2-[9-chloro-6-(3-hydroxy-3-methylbut-1-yn-1-yl)-1H-phenanthro[9,10-d]imidazol-2-yl]isophthalonitrile
• CAS NO: 892549-54-1
• Molecular Weight: 457.716
• Mol File: 892549-54-1.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: 2-[9-chloro-6-(3-hydroxy-3-methylbut-1-yn-1-yl)-1H-phenanthro[9,10-d]imidazol-2-yl]isophthalonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 2-[9-chloro-6-(3-hydroxy-3-methylbut-1-yn-1-yl)-1H-phenanthro[9,10-d]imidazol-2-yl]isophthalonitrile(892549-54-1)
• EPA Substance Registry System: 2-[9-chloro-6-(3-hydroxy-3-methylbut-1-yn-1-yl)-1H-phenanthro[9,10-d]imidazol-2-yl]isophthalonitrile(892549-54-1)

Safety Data

• Hazardous Substances Data: 892549-54-1(Hazardous Substances Data)

Upstream product

• 892550-46-8 9-bromo-6-chloro-2-(2,6-dibromophenyl)-1H-phenanthro[9,10-d]imidazole 
• 122-01-0 4-chloro-benzoyl chloride 
• 57082-98-1 (E)-1-bromo-4-(4-chlorostyryl)benzene 
• 7461-38-3 4-chloro-N,N-diethyl-benzamide 
• 939034-63-6 C₁₁H₁₅BClNO₃ 
• 937053-63-9 6-chloro-phenanthren-9-ol 
• 892550-47-9 (2E)-2-(4-bromophenyl)-3-(4-chloro-2-nitrophenyl)acrylic acid 
• 892550-48-0 (2E)-3-(2-amino-4-chlorophenyl)-2-(4-bromophenyl)acrylic acid 
• 892550-44-6 3-bromo-6-chlorophenanthrene 
• 938070-94-1 9-bromo-6-chloro-2-(2,6-dibromophenyl)-1H-phenanthro[9,10-d]imidazole acetic acid salt 
• 892549-58-5 2-[9-chloro-6-(3-hydroxy-3-methylbut-1-yn-1-yl)-1H-phenanthro[9,10-d]imidazol-2-yl]isophthalonitrile 
• 143-33-9 sodium cyanide 
• 544-92-3 copper(I) cyanide 

Downstream Products

• 892549-58-5 C₂₈H₁₇ClN₄O 
• 892550-54-8 2-[6-chloro-9-(3-methylbut-3-en-1-yn-1-yl)-1H-phenanthro[9,10-d]imidazol-2-yl]isophthalonitrile 
• 892550-41-3 (+/-)-2-[9-chloro-6-(3,4-dihydroxy-3-methylbut-1-yn-1-yl)-1H-phenanthro[9,10-d]imidazol-2-yl]isophthalonitrile 
• 892550-35-5 2-[9-chloro-6-(3-hydroxy-3-methylbutyl)-1H-phenanthro[9,10-d]imidazol-2-yl]isophthalonitrile 
• 892549-58-5 2-[9-chloro-6-(3-hydroxy-3-methylbut-1-yn-1-yl)-1H-phenanthro[9,10-d]imidazol-2-yl]isophthalonitrile 

Relevant articles and documents

Discovery of disubstituted phenanthrene imidazoles as potent, selective and orally active mPGES-1 inhibitors

Phenanthrene imidazoles 26 and 44 have been identified as novel potent, selective and orally active mPGES-1 inhibitors. These inhibitors are significantly more potent than the previously reported chlorophenanthrene imidazole 1 (MF63) with a human whole blood IC50 of 0.20 and 0.14 μM, respectively. It exhibited a significant analgesic effect in a guinea pig hyperalgesia model at oral doses as low as 14 mg/kg. Both active and selective mPGES-1 inhibitors (26 and 44) have a relatively distinct pharmacokinetic profile and are suitable for clinical development. Crown Copyright

METHOD OF GENERATING AMORPHOUS SOLID FOR WATER-INSOLUBLE PHARMACEUTICALS

The invention encompasses a method for making an amorphous solid of a water-insoluble pharmaceutical comprising: (1) dissolving the water-insoluble pharmaceutical in a water-miscible solvent, optionally with water, to make a solution; (2)(i) rapidly mixing the solution with an antisolvent, wherein the antisolvent is water, at low temperature to precipitate an amorphous solid of the water-insoluble pharmaceutical, or (ii) rapidly mixing the solution with an antisolvent, wherein the antisolvent is water, to precipitate an amorphous solid of the water-insoluble pharmaceutical and subsequently cooling to low temperature; and (3) isolating the amorphous solid of the water-insoluble pharmaceutical. In an embodiment of the invention, the rapid mixing is conducted using an impinging jet device.

PROCESS FOE SYNTHESIZING 2-PHENYL-1H-PHENANTRHO[9,10-D]IMIDAZOLE DERIVATIVE

The present invention describes an efficient and economical process for the preparation of a 2,3-disubstituted 2-phenyl-1h-phenantrho[9,10-d]imidazole derivative that is useful for the large scale production of material for preclinical and clinical use. The process of the present invention represents a convergent approach to generate the 2,3-disubstituted 2-phenyl-1h-phenantrho[9,10-d]imidazole derivative in high overall yield. The compound made by the process of the invention is an inhibitor of the microsomal prostaglandin E synthase-1 (mPGES-1) enzyme and is therefore useful to treat pain and/or inflammation from a variety of diseases or conditions such as osteoarthritis, rheumatoid arthritis and acute or chronic pain