55601-21-3

Usage

Synthesis Reference(s)

The Journal of Organic Chemistry, 45, p. 5333, 1980 DOI: 10.1021/jo01314a024

Upstream product

• 7654-06-0 3-phenyl-2H-azirine 
• 383-19-7 2,2-difluoro-2-phenylacetamide 
• 591-50-4 iodobenzene 
• 1603-79-8 phenylglyoxylic acid ethyl ester 
• 2248-46-6 ethyl 2,2-difluoro-2-phenylacetate 

Downstream Products

• 524948-12-7 3-(2,2-difluoro-2-phenylethylamino)-1-[(2-ethoxycarbonyl)ethyl]-6-methylpyrazinone 
• 885068-32-6 (6-chloro-2-methoxy-pyrimidin-4-yl)-(2,2-difluoro-2-phenyl-ethyl)-amine 
• 950768-43-1 [3-chloro-6-(2,2-difluoro-2-phenyl-ethylamino)-pyridin-2-yl]-acetic acid ethyl ester 
• 1036862-65-3 C₁₉H₁₇F₃N₂O₂ 
• 1426152-47-7 C₁₅H₁₂F₂N₄OS 
• 1207283-00-8 [6-cyano-3-(2,2-difluoro-2-phenyl-ethylamino)-2-oxo-2H-pyrazin-1-yl]-acetic acid ethyl ester 
• 1207283-03-1 [3-(2,2-difluoro-2-phenyl-ethylamino)-2-oxo-2H-pyrazin-1-yl]acetic acid ethyl ester 
• 221136-76-1 3-(2,2-Difluoro-2-phenylethylamino)-1-(ethoxycarbonylmethyl)-6-methylpyrazinone 

Relevant academic research and scientific papers

Direct Approach to 3-Fluoroindoles and 3,3-Difluoroindolines from 2,2-Difluoro-2-phenylethan-1-amines via C-H/N-H Coupling

Herein, a direct method for the synthesis of 3-fluoroindoles and 3,3-difluoroindolines from easily accessible 2,2-difluoro-2-phenyl ethan-1-amines is presented. This protocol was performed by Pd-catalyzed direct C-H/N-H coupling and employed picolinamide as a directing group. By controlling the temperature for this transformation, various 3,3-difluoroindolines and 3-fluoroindoles could be isolated with moderate to good yields.

Orally efficacious thrombin inhibitors with cyanofluorophenylacetamide as the P2 motif

2-Cyano-6-fluorophenylacetamide was explored as a novel P2 scaffold in the design of thrombin inhibitors. Optimization around this structural motif culminated in 14, which is a potent thrombin inhibitor (Ki = 1.2 nM) that exhibits robust effica

A COMBINATION OF NIACIN AND A PROSTAGLANDIN D2 RECEPTOR ANTAGONIST

The present invention is directed to a pharmaceutical composition comprising Niacin or a pharmaceutically acceptable salt, solvate or N-oxide thereof, or a nicotinic acid receptor agonist, and a compound of formula (I) as defined herein, or an N-oxide thereof, or an ester prodrug thereof, or a pharmaceutically acceptable salt, hydrate, or solvate thereof, and its use for treating atherosclerosis, dyslipidemia, diabetes or a related condition while reducing substantial flushing.

PYRIDINES AND PYRIDINE N-OXIDES AS MODULATORS OF THROMBIN

The present invention describes compounds of Formula I: wherein W, X, Y, Z, and Q are defined herein, or a pharmaceutically acceptable salt thereof, for the prophylaxis, or treatment of diseases and conditions related to thrombin activity in a mammal.

2, 6-SUBSTITUTED-4-MONOSUBSTITUTEDAMINO-PYRIDIMIDINE AS PROSTAGLANDIN D2 RECEPTOR ANTAGONISTS

The present invention is directed a compound of Formula (I) as defined herein, a pharmaceutical composition comprising a pharmaceutically effective amount of one or more compounds according to Formula (I) in admixture with a pharmaceutically acceptable carrier, and a method of treating a patient suffering from a PGD2-mediated disorder including, but not limited to, allergic disease (such as allergic rhinitis, allergic conjunctivitis, atopic dermatitis, bronchial asthma and food allergy), systemic mastocytosis, discorders accompanied by systemic mast cell activation, anaphylaxis shock, bronchoconstriction, bronchitis, urticaria, eczema, diseases accompanied by itch (such as atopic dermatitis and urticaria), diseases (such as cataract, retinal detachment, inflammation, infection and sleeping disorders) which is generated secondarily as a result of behavior accompanied by itch (such as scratching and beating), inflammation, chronic obstructive pulmonary diseases, ischemic reperfusion injury, cerebrovascular accident, chronic rheumatoid arthritis, pleurisy, ulcerative colitis and the like by administering to said patient a pharmaceutically effective amount of a compound according to Formula (I).

Novel non-convalent thrombin inhibitors

The present invention provides compounds which have a pyrazinone or pyridinone ring at P3 and an optionally substituted heteroaryl group at P1. These compounds have biological activity as active and potent inhibitors of thrombin. Their pharmaceutically acceptable salts, pharmaceutical compositions thereof and methods of using these compounds and pharmaceutical compositions comprising these compounds as therapeutic agents for treatment of disease states in mammals which are characterized by abnormal thrombosis are also described.

Cyclic oxyguanidine pyrazinones as protease inhibitors

Cyclic oxyguanidine pyrazinone compounds are described, including compounds of the Formula I: wherein R3, R4, R5, W, and A are as set forth in the specification, as well as hydrates, solvates or pharmaceutically acceptable

Substituted biphenyl isoxazole sulfonamides

Compounds of the formula STR1 inhibit the activity of endothelin. The symbols are defined as follows: R1, R2, R3 and R4 are each directly bonded to a ring carbon and are each independently (a) hydrogen; (b) alkyl, alkenyl, alkynyl, alkoxy, cycloalkyl, cycloalkylalkyl, cycloalkenyl, cycloalkenylalkyl, aryl, aryloxy, aralkyl or aralkoxy, any of which may be substituted with Z1, Z2 and Z3 ; (c) halo; (d) hydroxyl; (e) cyano; (f) nitro; (g) --C(O)H or --C(O)R5 ; (h) --CO2 H or --CO2 R5 ; (i) --Z4 --NR6 R7 ; (j) --Z4 --N(R10)--Z5 --NR8 R9 ; or (k) R3 and R4 together may also be alkylene or alkenylene, either of which may be substituted with Z1, Z2 and Z3, completing a 4- to 8-membered saturated, unsaturated or aromatic ring together with the carbon atoms to which they are attached; and the remaining symbols are as defined in the specification.

New Convenient Synthesis of β,β-Difluoro Amines and β,β-Difluoro-α-amino Acid Alkyl Esters by the Addition of Hydrogen Fluoride to 1-Azirines

The reaction of hydrogen fluoride in pyridine solution with a series of substituted 1-azirines (1) was investigated. β,β-Difluoro amines (4) were obtained in good yields.The exceptions are the cases of 2-phenyl-3-methyl-1-azirine (1b) and 2,3-diphenyl-1-azirine (1c) for which the direct formation of a stabilized carbocation (6) from the azirinium ion 2 is probable.The former gave 54 percent of a pyrazine (11b) and 5 percent of α-fluoropropiophenone (9b) along with 20 percent of difluoro amine 4b, while the latter afforded only the corresponding α-fluoro ketone (9c).A mechanism is suggested.