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
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Expires: 1996-03-01
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 |