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US4124587A Expired / Lapsed US ⏱️ 0.0 years remaining

4-Hydroxy-3-sulfinyl-quinolin-2(1H)-ones

Assignee: Sandoz Inc
•
Filing: 1976-03-01
•
Granted: 1978-11-07
•
Expires: 1996-03-01
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Abstract

Abstract Anti-allergic 4-hydroxy-3-sulfinyl-quinolin-2(1H)-ones are prepared by reacting an isatoic anhydride with the carbanion resulting from the treatment of sulfinyl acetic acid alkyl esters with a proton abstracting agent.

Inventors

  • 👤 Goetz E. Hardtmann

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-09 18:27
CPC Classifications
C; C07; C07D; C07D215/00; C07D215/02; C07D215/16; C07D215/36

Claims Analysis

Total Claims: 21
Claim 1
Independent Claim 267 words
A compound of the formula: ##STR8## wherein R o is hydrogen, alkyl of 1 to 6 carbon atoms, alkenyl of 3 to 6 carbon atoms, alkynyl of 3 to 6 carbon atoms, cycloalkyl of 3 to 6 carbon atoms, cycloalkylalkyl in which the cycloalkyl is of 3 to 6 carbon atoms and the alkyl portion is of 1 or 2 carbon atoms, or ##STR9## Mp is hydrogen or a cation forming a pharmaceutically acceptable salt, n is 0 or 1, Y and Y' are independently hydrogen, fluoro, chloro, or bromo, alkyl of 1 to 3 carbon atoms, alkoxy of 1 to 3 carbon atoms or trifluoromethyl, R and R' are independently hydrogen, fluoro, chloro, bromo, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, nitro or trifluoromethyl, with the proviso that only one of R and R' can be from the group consisting of nitro and trifluoromethyl, or R and R' together form 6,7-methylenedioxy, R 1 is alkyl of 1 to 6 carbon atoms, alkenyl of 3 to 6 carbon atoms, alkynyl of 3 to 6 carbon atoms, cycloalkyl of 3 to 6 carbon atoms, cycloalkylalkyl in which the cycloalkyl portion is of 3 to 6 carbon atoms and the alkyl portion is of 1 or 2 carbon atoms, or ##STR10## m is 0 or 1, and X and X' are independently hydrogen, fluoro, chloro, bromo, alkyl of 1 to 3 carbon atoms, alkoxy of 1 to 3 carbon atoms or trifluoromethyl with the further proviso that the unsaturation in any alkenyl or alkynyl is on other than the alpha carbon atom.
Claim 2
Dependent Claim 267 words
A compound of the formula: ##STR8## wherein R o is hydrogen, alkyl of 1 to 6 carbon atoms, alkenyl of 3 to 6 carbon atoms, alkynyl of 3 to 6 carbon atoms, cycloalkyl of 3 to 6 carbon atoms, cycloalkylalkyl in which the cycloalkyl is of 3 to 6 carbon atoms and the alkyl portion is of 1 or 2 carbon atoms, or ##STR9## Mp is hydrogen or a cation forming a pharmaceutically acceptable salt, n is 0 or 1, Y and Y' are independently hydrogen, fluoro, chloro, or bromo, alkyl of 1 to 3 carbon atoms, alkoxy of 1 to 3 carbon atoms or trifluoromethyl, R and R' are independently hydrogen, fluoro, chloro, bromo, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, nitro or trifluoromethyl, with the proviso that only one of R and R' can be from the group consisting of nitro and trifluoromethyl, or R and R' together form 6,7-methylenedioxy, R 1 is alkyl of 1 to 6 carbon atoms, alkenyl of 3 to 6 carbon atoms, alkynyl of 3 to 6 carbon atoms, cycloalkyl of 3 to 6 carbon atoms, cycloalkylalkyl in which the cycloalkyl portion is of 3 to 6 carbon atoms and the alkyl portion is of 1 or 2 carbon atoms, or ##STR10## m is 0 or 1, and X and X' are independently hydrogen, fluoro, chloro, bromo, alkyl of 1 to 3 carbon atoms, alkoxy of 1 to 3 carbon atoms or trifluoromethyl with the further proviso that the unsaturation in any alkenyl or alkynyl is on other than the alpha carbon atom.
Claim 3
Dependent Claim 11 words
A compound of claim 1 in which R 1 is alkyl.
Claim 4
Dependent Claim 11 words
A compound of claim 2 in which R o is alkyl.
Claim 5
Dependent Claim 11 words
A compound of claim 2 in which R o is alkenyl.
Claim 6
Dependent Claim 11 words
A compound of claim 2 in which R o is alkynyl.
Claim 7
Dependent Claim 13 words
A compound of claim 2 in which R o is cycloalkyl or cycloalkylalkyl.
Claim 8
Dependent Claim 11 words
A compound of claim 2 in which R o is ##STR11##
Claim 9
Dependent Claim 10 words
A compound of claim 7 in which n is 1.
Claim 10
Dependent Claim 11 words
A compound of claim 2 in which R o is hydrogen.
Claim 11
Dependent Claim 11 words
A compound of claim 1 in which R 1 is alkenyl.
Claim 12
Dependent Claim 11 words
A compound of claim 10 in which R o is hydrogen.
Claim 13
Dependent Claim 11 words
A compound of claim 10 in which R o is alkyl.
Claim 14
Dependent Claim 11 words
A compound of claim 10 in which R o is alkenyl.
Claim 15
Dependent Claim 8 words
The compound of claim 1 which is 1-methyl-4-hydroxy-3-methylsulfinyl-quinolin-2(1H)-one.
Claim 16
Dependent Claim 8 words
The compound of claim 1 which is 1-methyl-6,7-methylenedioxy-4-hydroxy-3-methylsulfinyl-quinolin-2(1H)-one.
Claim 17
Dependent Claim 8 words
The compound of claim 1 which is 1-allyl-4-hydroxy-3-methylsulfinyl-quinolin-2(1H)-one.
Claim 18
Dependent Claim 11 words
A compound of claim 1 in which M p is hydrogen.
Claim 19
Dependent Claim 33 words
A compound of claim 1 in which R and R' are independently hyrogen, fluoro, chloro, bromo, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, nitro or trifluoromethyl.
Claim 20
Dependent Claim 31 words
A compound of claim 18 in which R and R' are independently hydrogen, fluoro, chloro, bromo, alkoxy of 1 to 4 carbon atoms or alkoxy of 1 to 4 carbon atoms.
Claim 21
Dependent Claim 13 words
A compound of claim 1 in which R and R' together form 6,7-methylenedioxy.

References Cited (Backward Citations)

US3772301A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1981-11-06 1982-05-08 1982-11-07 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1985-11-06 1986-05-08 1986-11-07 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1989-11-06 1990-05-08 1990-11-07 $7700.00 Window Closed / Lapsed

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