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US4002749A Expired / Lapsed US ⏱️ 0.0 years remaining

Substituted indolinones

Assignee: ER Squibb and Sons LLC
•
Filing: 1975-08-12
•
Granted: 1977-01-11
•
Expires: 1995-08-12
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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

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