US4002749A
Expired / Lapsed
US
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Substituted indolinones
Assignee: ER Squibb and Sons LLC
•
Filing: 1975-08-12
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Granted: 1977-01-11
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Expires: 1995-08-12
Abstract
Abstract Indolinone compounds which exhibit anti-inflammatory activity have the following formula ##STR1## wherein R 1 , R 2 , R 3 , ##STR2## and n are as defined herein.
Inventors
- 👤 George C. Rovnyak
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-04 23:01
CPC Classifications
C; C07; C07D; C07D417/00; C07D417/02; C07D417/04
Claims Analysis
Total Claims: 26
Claim 1
Independent Claim
152 words
A compound of the formula ##STR73## wherein R 1 is selected from the group consisting of phenyl, naphthyl, thienyl, furyl, chlorofuryl, dichlorofuryl, pyrryl, pyridyl, coumarinyl, thiacoumarinyl, thiazolyl, isothiazolyl, imidazolyl, or phenyl or naphthyl substituted with one or more substituents selected from the group consisting of halogen, hydroxy, lower alkyl, nitro, CF 3 and lower alkoxy; R 2 is selected from the group consisting of hydrogen, lower alkyl, phenyl, naphthyl, lower alkylphenyl, or lower alkylnaphthyl; R 3 is selected from the group consisting of hydrogen, lower alkyl, trifluoromethyl, halo, lower alkoxy, nitro, cyano, amino, dilower alkylamino or ##STR74## wherein R is selected from the groups consisting of lower alkyl, lower alkenyl, phenyl, phenyl-lower alkyl, cycloalkyl, cycloalkenyl, cycloalkyl-lower alkyl, and cycloalkyl-lower alkenyl; ##STR75## represents a 5- or 6-membered ring selected from the group consisting of ##STR76## n is 1 or 2; the dotted line represents an optional bond; and pharmaceutically acceptable acid-addition salts thereof.
Claim 2
Dependent Claim
152 words
A compound of the formula ##STR73## wherein R 1 is selected from the group consisting of phenyl, naphthyl, thienyl, furyl, chlorofuryl, dichlorofuryl, pyrryl, pyridyl, coumarinyl, thiacoumarinyl, thiazolyl, isothiazolyl, imidazolyl, or phenyl or naphthyl substituted with one or more substituents selected from the group consisting of halogen, hydroxy, lower alkyl, nitro, CF 3 and lower alkoxy; R 2 is selected from the group consisting of hydrogen, lower alkyl, phenyl, naphthyl, lower alkylphenyl, or lower alkylnaphthyl; R 3 is selected from the group consisting of hydrogen, lower alkyl, trifluoromethyl, halo, lower alkoxy, nitro, cyano, amino, dilower alkylamino or ##STR74## wherein R is selected from the groups consisting of lower alkyl, lower alkenyl, phenyl, phenyl-lower alkyl, cycloalkyl, cycloalkenyl, cycloalkyl-lower alkyl, and cycloalkyl-lower alkenyl; ##STR75## represents a 5- or 6-membered ring selected from the group consisting of ##STR76## n is 1 or 2; the dotted line represents an optional bond; and pharmaceutically acceptable acid-addition salts thereof.
Claim 3
Dependent Claim
11 words
A compound as defined in claim 1 having the formula ##STR77##
Claim 4
Dependent Claim
11 words
A compound as defined in claim 1 having the formula ##STR78##
Claim 5
Dependent Claim
12 words
A compound as defined in claim 1 wherein R 2 is phenyl.
Claim 6
Dependent Claim
12 words
A compound as defined in claim 1 wherein R 3 is hydrogen.
Claim 7
Dependent Claim
12 words
A compound as defined in claim 1 wherein R 2 is hydrogen.
Claim 8
Dependent Claim
11 words
A compound as defined in claim 1 wherein n is 1.
Claim 9
Dependent Claim
11 words
A compound as defined in claim 1 wherein n is 2.
Claim 10
Dependent Claim
9 words
A compound as defined in claim 1 wherein ##STR79##
Claim 11
Dependent Claim
9 words
A compound as defined in claim 1 wherein ##STR80##
Claim 12
Dependent Claim
20 words
A compound as defined in claim 1 wherein R 1 is phenyl, alkoxyphenyl, halophenyl, dihalophenyl, hydroxyphenyl, (trifluoromethyl)phenyl, thienyl, or pyridyl.
Claim 13
Dependent Claim
20 words
A compound as defined in claim 1 wherein R 3 is hydrogen, halo, nitro, alkyl, amino, acyl, trifluoromethyl, or dialkyl.
Claim 14
Dependent Claim
26 words
A compound as defined in claim 2 wherein R 1 is phenyl, alkoxyphenyl, halophenyl, dihalophenyl, hydroxyphenyl, trifluoromethyl phenyl, thienyl or pyridyl, and R 3 is hydrogen.
Claim 15
Dependent Claim
19 words
A compound as defined in claim 3 wherein R 1 is phenyl or halophenyl and R 3 is hydrogen.
Claim 16
Dependent Claim
17 words
A pharmaceutical composition comprising a compound as defined in claim 1 and a pharmaceutically acceptable carrier therefor.
Claim 17
Dependent Claim
26 words
A method for treating inflammation in mammalian species, which comprises administering to the mammalian host a therapeutic amount of a compound as defined in claim 1.
Claim 18
Dependent Claim
11 words
A compound as defined in claim 1 having the name 1-(4,5-dihydro-2-thiazolyl)-1,3-dihydro-3-(phenylmethylene)-2H-indol-2-one
Claim 19
Dependent Claim
11 words
A compound as defined in claim 1 having the name 1-(5,6-dihydro-4H-1,3-thiazin-2-yl)-1,3-dihydro-3-(phenylmethylene)-2H-indol-2-one.
Claim 20
Dependent Claim
11 words
A compound as defined in claim 1 having the name 1-(4,5-dihydro-2-thiazolyl)-1,3-dihydro-3-[(4-methoxyphenyl)methylene]-2H-indol-2-one.
Claim 21
Dependent Claim
11 words
A compound as defined in claim 1 having the name 3-[(4-chlorophenyl)methylene]-1-(4,5-dihydro-2-thiazolyl)-1,3-dihydro-2H-indol-2-one.
Claim 22
Dependent Claim
11 words
A compound as defined in claim 1 having the name 3-[(3,4-dichlorophenyl)methylene]-1-(4,5-dihydro-2-thiazolyl)-1,3-dihydro-2H-indol-2-one.
Claim 23
Dependent Claim
11 words
A compound as defined in claim 1 having the name 1-(4,5-dihydro-2-thiazolyl)-1,3-dihydro-3-[(2-hydroxyphenyl)methylene]-2H-indol-2-one.
Claim 24
Dependent Claim
11 words
A compound as defined in claim 1 having the name 1-(4,5-dihydro-2-thiazolyl)-1,3-dihydro-3-(2-thienylmethylene)-2H-indol-2-one.
Claim 25
Dependent Claim
11 words
A compound as defined in claim 1 having the name 1-(4,5-dihydro-2-thiazolyl)-1,3-dihydro-3-(2-pyridinylmethylene)-2H-indol-2-one.
Claim 26
Dependent Claim
11 words
A compound as defined in claim 1 having the name 1-(5,6-dihydro-4H-1,3-thiazin-2-yl)-1,3-dihydro-3-(phenylmethyl)-2H-indol-2-one.
References Cited (Backward Citations)
US3853857A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1980-01-11 | 1980-07-12 | 1981-01-11 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1984-01-11 | 1984-07-12 | 1985-01-11 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1988-01-11 | 1988-07-12 | 1989-01-11 | $7700.00 | Window Closed / Lapsed |