76568-68-8

Usage

InChI:InChI=1/C11H10FNO3S/c1-13-6-10(17(2,15)16)11(14)8-4-3-7(12)5-9(8)13/h3-6H,1-2H3

Upstream product

• 372-19-0 meta-fluoroaniline 
• 154504-93-5 (+)-Flosequinan 
• 154504-94-6 (-)-Flosequinan 
• 154639-78-8 7-fluoro-3-methylsulfonyl-4-quinolone 
• 74-88-4 methyl iodide 
• 76568-02-0 flosequinan 
• 76561-14-3 7-fluoro-3-methylsulfinyl-4-quinolone 
• 76561-13-2 1-(2-amino-4-fluorophenyl)-2-methylsulfinylethanone 
• 128992-62-1 4-fluoro-N-methylanthranilic acid 
• 97927-92-9 7-fluoro-1-methyl-2H-benzo[d][1,3]oxazine-2,4(1H)-dione 
• 2252-51-9 2-choro-4-fluorobenzoic acid 
• 321-50-6 7-fluoro-1H-benzo[d][1,3]oxazine-2,4-dione 
• 154639-75-5 1-(4-fluoro-2-methylaminophenyl)-2-methylsulfinylethanone 

Relevant academic research and scientific papers

Stereoselective S-oxidation and reduction of flosequinan in rat

1. The stereoselective S-oxidation and reduction pathways of flosequinan [(±)-7-fluoro-1-methyl-3-methylsulphinyl-4-quinolone] in rat were investigated in vitro. 2. Cytosol from both the liver and kidney catalysed the reduction of R(+)-flosequinan (R-FSO) and S(-)-flosequinan (S-FSO) to flosequinan sulphide (FS, 7-fluoro-1-methyl-3-methylthio-4-quinolone). Flosequinan sulphone (FSO22, 7-fluoro-1-methyl-3-methyl-sulphonyl-4-quinolone) was not reduced to R-FSO or S-FSO. 3. Liver microsomes catalysed four different S-oxidation pathways in the presence of NADPH, namely oxidation of FS to R-FSO and S-FSO and from R-FSO and S-FSO to FSO2. The formation of R-FSO and S-FSO from FS each eshibited a biphasic kinetic pattern, indicating that at least two distinct enzymes were involved. The pathway from FS to R-FSO appeared mainly catalysed by flavin-containing monooxygenases (FMO). 4. S-oxidation of FS to R-FSO was more rapid than that of FS to S-FSO. S-oxidation of FS to either R-FSO or S-FSO in liver microsomes was more rapid than that of either R-FSO or S-FSO to FSO2. 5. Microsomes from both the kidney and lung catalysed the stereoselective S-oxidation of FS to R-FSO, and FMO was likely to have participated in these reactions.

Syntheses of Flosequinan: A Novel 4-Quinolone shown to be useful in Congestive Heart Failure

Two synthetic routes to flosequinan 1 and flosequinoxan 2 are described in which either ring closure of the β-keto sulfoxides 12 or 13 with ortho esters or cyclisation of the anilinoacrylates 23, 28 or 29 are the key steps.

Process for the preparation of 1-methyl-3-methylthio-4-quinolone and the sulfinyl, and sulfonyl analogs thereof

A process to prepare compounds of formula I STR1 in which n=0, 1 or 2 comprising the cyclisation of compounds of formula II STR2 in which n=0, 1 or 2. The cyclisation may be effected in the presence of an organic or inorganic base or thermally at a temper

Method of treating heart disease

A method for the treatment of heart failure in a mammal comprises the administration to the mammal of a quinolone of the general formula I, STR1 wherein m is 0 or 1; n is 0, 1 or 2; and R is hydrogen, halo, methyl or trifluoromethyl. A preferred method of the invention comprises the treatment of chronic heart failure in a mammal by the oral administration of a quinolone of formula I. Preferred compounds of formula I are 7-fluoro-1-methyl-3-methylsulphinyl-4-quinolone and 1-methyl-3-methylsulphonylmethyl-4-quinolone.

4-Quinolinones having antihypertensive activity

Compositions which contain a quinolone compound of the general formula STR1 wherein n is 0, 1 or 2; R1 is lower alkyl optionally substituted by hydroxy or C1-4 alkoxycarbonyl; allyl; propynyl or phenyl- lower alkyl in which the phenyl ring is optionally substituted by 1 or 2 C1-4 alkoxy groups; R2 is C1-4 alkyl with the proviso that when n is 0, R2 is methyl; and R3, R4 and R5, which may be the same or different, are hydrogen, lower alkyl, lower alkoxy, lower alkanoyl, halo, trifluoromethyl or lower alkylthio show antihypertensive activity. Compounds of general formula STR2 in which n, R1 R2, R3, R4 and R5 are as described above are novel subject to the following provisos (a) when R3, R4 and R4 and R5 are hydrogen R2 is methyl and R1 is lower alkyl, R1 contains more than one carbon atom, and (b) when R3 and R4 are hydrogen, R5 is hydrogen or 7-methyl, and R1 is ethyl, R2 contains more than one carbon atom. The specification describes and claims methods of making the compounds and novel intermediates used in such methods.