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US 4,045,451 AGranted
2-(Methylthio)naphtho[1,3-bc]pyran-3(2H)-one
AssigneeWarner-Lambert Company
InventorsDavid T. Connor, Maximilian VON Strandtmann
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AssigneeWarner-Lambert Company
InventorsDavid T. Connor, Maximilian VON Strandtmann
Estimating the term…
The invention relates to novel compounds having the formulas I and III: ##STR1## wherein, in formula I, X is --O-- or --N--COR wherein R is lower alkyl or aryl, and Z is ##STR2## WHEREIN R' is hydrogen, halogen or alkoxy. the compounds of this invention are prepared by a novel process which involves the cyclization of the corresponding aryl(methylsulfinyl)methyl ketones. The compounds of this invention having formulas I and III are useful in the treatment of hyperacidity and for alleviating allergic manifestations.
2-(Methylthio)naphtho[1,8-bc]pyran-3(2H)-one.
Dependencies are inferred from the claim text.
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Ortho- or peri-condensed with carbocyclic rings or ring systems: naphthofurans; Hydrogenated naphthofurans
Oxygen atoms: in position 3, e.g. adrenochrome
With hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals,…:…
Benzo [b] furans; Hydrogenated benzo [b] furans: with an oxygen atom directly attached in position 7
Term ended 30 Aug 1994 (estimated)
USPTO file history isn’t available for this patent, so only indexed dates are shown.
DESCRIPTION OF THE INVENTION The present invention relates to novel substituted-2-(methylthio)-3(2H)-benzofuranones and novel substituted-2-(methylthio)-3-indolinones having the formula I: ##STR3## wherein X is -- O-- or --N--COR wherein R is lower alkyl or aryl, and Z is ##STR4## WHEREIN R' is hydrogen, halogen or alkoxy; and to novel 2-(methylthio)naphtho[ 1,8-bc]pyran-3-(2H)-one having the formula III: ##STR5##
This invention also includes within its scope a novel process for preparing the above compounds as well as certain novel intermediates used in their preparation.
The novel compounds of the invention having formula I, as defined above, are prepared by cyclizing the corresponding aryl(methylsulfinyl)methyl ketone having the formula II: ##STR6## wherein X is -- 0-- or --N--COR wherein R is lower alkyl or aryl, and Z is ##STR7## WHEREIN R' is hydrogen, halogen or alkoxy.
To further illustrate the practice of this invention the following examples are included.
2-Hydroxy-1-[(methylsulfinyl)acetyl] benzene (1.5 g 0.0075m) and trifluoroacetic acid (1.5 g) are refluxed in benzene (25 ml) for one hour under nitrogen. The solvent is removed under reduced pressure to give a pale yellow oil which crystallizes on standing. Recrystallization from ethanol gave white crystals, (0.611 g 45%), m.p. 81.degree.-82.degree. C.
Anal. Calcd. for C.sub.9 H.sub.8 O.sub.2 S: C, 59.98; H, 4.47; S, 17.79. Found: C, 60.12; H, 4.49; S, 17.78.