4-3-indolyl!-1H-pyrrolone
First Claim
1. A compound of the formula ##STR7## wherein R is hydrogen or hydroxy, R1 and R2 taken together are --CH2 -- and R7 is hydrogen;
- R3 is unsubstituted phenyl, naphthyl, 3-benzothienyl, 3-benzofuranyl or 3-indolyl or phenyl, naphthyl, 3-benzothienyl, 3-benzofuranyl or 3-indolyl substituted with one substituent selected from halogen, alkyl, hydroxy, alkoxy, haloalkyl, nitro, amino, acylamino, alkylthio, alkylsulfinyl and alkylsulfonyl;
R4, R5 and R6 each independently are hydrogen, halogen, alkyl, hydroxy, alkoxy, haloalkyl, nitro, amino, acylamino, alkylthio, alkylsulfinyl or alkylsulfonyl;
R8 is a group of the formula --(CH2)p --R9 or --(CH2)q --R10 ;
R9 is hydrogen, alkylcarbonyl, aminoalkylcarbonyl, cyano, amidino, alkoxycarbonyl, aryloxycarbonyl, alkylsulfonyl, aminocarbonyl or aminothiocarbonyl;
R10 is hydroxy, alkoxy, halogen, amino, monoalkylamino, dialkylamino, trialkylamino, azido, acylamino, alkylsulfonylamino, arylsulfonylamino, alkylthio, amino-carbonylamino, isothiocyanato, alkylcarbonyloxy, alkylsulfonyloxy or arylsulfonyloxy, or a group of the formula --U--C(V)--W;
U is S or NH;
V is NH, NNO2, NCN, CHNO2 ;
W is amino, monoalkylamino or dialkylamino;
one of X and Y is O and the other is O or (H,H);
Z is CH;
m is 1 or 2 and p and q are, independently, an integer from 0 to 5;
or a pharmaceutically acceptable salt of an acidic compound of formula I with a base or of a basic compound of formula I with an acid.
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Accused Products
Abstract
A compound of the formula ##STR1## wherein R is hydrogen or hydroxy, R1 and R2 taken together are a group of the formula --(CH2)m -- and R7 is hydrogen or R1 and R7 taken together are a group of the formula --(CH2)n -- and R2 is hydrogen; R3 is an aryl or aromatic heterocyclic group; R4, R5 and R6 each independently are hydrogen, halogen, alkyl, hydroxy, alkoxy, haloalkyl, nitro, amino, acylamino, alkylthio, alkylsulfinyl or alkylsulfonyl; R8 is a group of the formula --(CH2)p --R9 or --(CH2)q --R10 ; R9 is hydrogen, alkylcarbonyl, aminoalkylcarbonyl, cyano, amidino, alkoxycarbonyl, aryloxycarbonyl, alkylsulfonyl, aminocarbonyl or aminothiocarbonyl; R10 is hydroxy, alkoxy, halogen, amino, monoalkylamino, dialkylamino, trialkylamino, azido, acylamino, alkylsulfonylamino, a 5- or 6-membered saturated nitrogen-containing heterocycle; X and Y are oxygen; Z is CH; m, p and q are, independently, an integer from 0 to 5, and n an integer from 1 to 5,
as well as pharmaceutically acceptable salts thereof which are useful in the control of inflammatory, immunological, oncological, bronchopulmonary or cardiovascular disorders.
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Citations
18 Claims
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1. A compound of the formula ##STR7## wherein R is hydrogen or hydroxy, R1 and R2 taken together are --CH2 -- and R7 is hydrogen;
- R3 is unsubstituted phenyl, naphthyl, 3-benzothienyl, 3-benzofuranyl or 3-indolyl or phenyl, naphthyl, 3-benzothienyl, 3-benzofuranyl or 3-indolyl substituted with one substituent selected from halogen, alkyl, hydroxy, alkoxy, haloalkyl, nitro, amino, acylamino, alkylthio, alkylsulfinyl and alkylsulfonyl;
R4, R5 and R6 each independently are hydrogen, halogen, alkyl, hydroxy, alkoxy, haloalkyl, nitro, amino, acylamino, alkylthio, alkylsulfinyl or alkylsulfonyl;
R8 is a group of the formula --(CH2)p --R9 or --(CH2)q --R10 ;
R9 is hydrogen, alkylcarbonyl, aminoalkylcarbonyl, cyano, amidino, alkoxycarbonyl, aryloxycarbonyl, alkylsulfonyl, aminocarbonyl or aminothiocarbonyl;
R10 is hydroxy, alkoxy, halogen, amino, monoalkylamino, dialkylamino, trialkylamino, azido, acylamino, alkylsulfonylamino, arylsulfonylamino, alkylthio, amino-carbonylamino, isothiocyanato, alkylcarbonyloxy, alkylsulfonyloxy or arylsulfonyloxy, or a group of the formula --U--C(V)--W;
U is S or NH;
V is NH, NNO2, NCN, CHNO2 ;
W is amino, monoalkylamino or dialkylamino;
one of X and Y is O and the other is O or (H,H);
Z is CH;
m is 1 or 2 and p and q are, independently, an integer from 0 to 5;or a pharmaceutically acceptable salt of an acidic compound of formula I with a base or of a basic compound of formula I with an acid. - View Dependent Claims (2, 3, 4, 5, 6, 7, 8, 9, 10, 12)
- R3 is unsubstituted phenyl, naphthyl, 3-benzothienyl, 3-benzofuranyl or 3-indolyl or phenyl, naphthyl, 3-benzothienyl, 3-benzofuranyl or 3-indolyl substituted with one substituent selected from halogen, alkyl, hydroxy, alkoxy, haloalkyl, nitro, amino, acylamino, alkylthio, alkylsulfinyl and alkylsulfonyl;
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11. A compound of the formula ##STR8## wherein R1 and R2 taken together are --CH2 -- and R7 is hydrogen;
- R3 is unsubstituted phenyl, naphthyl, 3-benzothienyl, 3-benzofuranyl or 3-indolyl or phenyl, naphthyl, 3-benzothienyl, 3-benzofuranyl or 3-indolyl substituted with one substituent selected from halogen, alkyl, hydroxy, alkoxy, haloalkyl, nitro, amino, acylamino, alkylthio, alkylsulfinyl and alkylsulfonyl;
R4, R5 and R6 each independently are hydrogen, halogen, alkyl, hydroxy, alkoxy, haloalkyl, nitro, amino, acylamino, alkylthio, alkylsulfinyl or alkylsulfonyl;
R8 is a group of the formula --(CH2)p --R9 or --(CH2)q --R10 ;
R9 is hydrogen, alkylcarbonyl, aminoalkylcarbonyl, cyano, amidino, alkoxycarbonyl, aryloxycarbonyl, alkylsulfonyl, aminocarbonyl or aminothiocarbonyl;
R10 is hydroxy, alkoxy, halogen, amino, monoalkylamino, dialkylamino, trialkylamino, azido, acylamino, alkylsulfonylamino, arylsulfonylamino, alkylthio, amino-carbonylamino, isothiocyanato, alkylcarbonyloxy, alkylsulfonyloxy or arylsulfonyloxy, or a group of the formula --U--C(V)--W;
U is S or NH;
V is NH, NNO2, NCN, CHNO2 ;
W is amino, monoalkylamino or dialkylamino;
Z is CH;
m is 1 or 2 and p and q are, independently, an integer from 0 to 5.
- R3 is unsubstituted phenyl, naphthyl, 3-benzothienyl, 3-benzofuranyl or 3-indolyl or phenyl, naphthyl, 3-benzothienyl, 3-benzofuranyl or 3-indolyl substituted with one substituent selected from halogen, alkyl, hydroxy, alkoxy, haloalkyl, nitro, amino, acylamino, alkylthio, alkylsulfinyl and alkylsulfonyl;
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13. A pharmaceutical composition comprising an effective amount of a compound of the formula ##STR9## wherein R is hydrogen or hydroxy, R1 and R2 taken together are --CH2 -- and R7 is hydrogen;
- R3 is unsubstituted phenyl, naphthyl, 3-benzothienyl, 3-benzofuranyl or 3-indolyl or phenyl, naphthyl, 3-benzothienyl, 3-benzofuranyl or 3-indolyl substituted with one substituent selected from halogen, alkyl, hydroxy, alkoxy, haloalkyl, nitro, amino, acylamino, alkylthio, alkylsulfinyl and alkylsulfonyl;
R4, R5 and R6 each independently are hydrogen, halogen, alkyl, hydroxy, alkoxy, haloalkyl, nitro, amino, acylamino, alkylthio, alkylsulfinyl or alkylsulfonyl;
R8 is a group of the formula --(CH2)p --R9 or --(CH2)q --R10 ;
R9 is hydrogen, alkylcarbonyl, aminoalkylcarbonyl, cyano, amidino, alkoxycarbonyl, aryloxycarbonyl, alkylsulfonyl, aminocarbonyl or aminothiocarbonyl;
R10 is hydroxy, alkoxy, halogen, amino, monoalkylamino, dialkylamino, trialkylamino, azido, acylamino, alkylsulfonylamino, arylsulfonylamino, alkylthio, amino-carbonylamino, isothiocyanato, alkylcarbonyloxy, alkylsulfonyloxy or arylsulfonyloxy, or a group of the formula --U--C(V)--W;
U is S or NH;
V is NH, NNO2, NCN, CHNO2 ;
W is amino, monoalkylamino or dialkylamino;
one of X and Y is O and the other is O or (H,H);
Z is CH;
m is 1 or 2 and p and q are, independently, an integer from 0 to 5;or a pharmaceutically acceptable salt of an acidic compound of formula I with a base or of a basic compound of formula I with an acid, and an inert carrier material. - View Dependent Claims (14, 17)
- R3 is unsubstituted phenyl, naphthyl, 3-benzothienyl, 3-benzofuranyl or 3-indolyl or phenyl, naphthyl, 3-benzothienyl, 3-benzofuranyl or 3-indolyl substituted with one substituent selected from halogen, alkyl, hydroxy, alkoxy, haloalkyl, nitro, amino, acylamino, alkylthio, alkylsulfinyl and alkylsulfonyl;
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15. A method of inhibiting protein kinase which comprises administering an effective amount of a compound of the formula ##STR10## wherein R is hydrogen or hydroxy, R1 and R2 taken together are --CH2 -- and R7 is hydrogen;
- R3 is unsubstituted phenyl, naphthyl, 3-benzothienyl, 3-benzofuranyl or 3-indolyl or phenyl, naphthyl, 3-benzothienyl, 3-benzofuranyl or 3-indolyl substituted with one substituent selected from halogen, alkyl, hydroxy, alkoxy, haloalkyl, nitro, amino, acylamino, alkylthio, alkylsulfinyl and alkylsulfonyl;
R4, R5 and R6 each independently are hydrogen, halogen, alkyl, hydroxy, alkoxy, haloalkyl, nitro, amino, acylamino, alkylthio, alkylsulfinyl or alkylsulfonyl;
R8 is a group of the formula --(CH2)p --R9 or --(CH2)q --R10 ;
R9 is hydrogen, alkylcarbonyl, aminoalkylcarbonyl, cyano, amidino, alkoxycarbonyl, aryloxycarbonyl, alkylsulfonyl, aminocarbonyl or aminothiocarbonyl;
R10 is hydroxy, alkoxy, halogen, amino, monoalkylamino, dialkylamino, trialkylamino, azido, acylamino, alkylsulfonylamino, arylsulfonylamino, alkylthio, amino-carbonylamino, isothiocyanato, alkylcarbonyloxy, alkylsulfonyloxy or arylsulfonyloxy, or a group of the formula --U--C(V)--W;
U is S or NH;
V is NH, NNO2, NCN, CHNO2 ;
W is amino, monoalkylamino or dialkylamino;
one of X and Y is O and the other is O or (H,H);
Z is CH;
m is 1 or 2 and p and q are, independently, an integer from 0 to 5;or a pharmaceutically acceptable salt of an acidic compound of formula I with a base or of a basic compound of formula I with an acid. - View Dependent Claims (16, 18)
- R3 is unsubstituted phenyl, naphthyl, 3-benzothienyl, 3-benzofuranyl or 3-indolyl or phenyl, naphthyl, 3-benzothienyl, 3-benzofuranyl or 3-indolyl substituted with one substituent selected from halogen, alkyl, hydroxy, alkoxy, haloalkyl, nitro, amino, acylamino, alkylthio, alkylsulfinyl and alkylsulfonyl;
Specification