Oxindole derivatives

US 6,265,411 B1
Filed: 11/06/1998
Issued: 07/24/2001
Est. Priority Date: 05/06/1996
Status: Expired due to Fees

First Claim

Patent Images

1. A compound of the formula I:

wherein;

R²represents hydroxy, halogeno, C_1-3alkyl, C_1-3alkoxy, C_1-3alkanoyloxy, trifluoromethyl, cyano, amino, nitro, C_2-4alkanoyl, C_1-4alkanoylamino, C_1-4alkoxycarbonyl, C_1-4alkylthio, C_1-4alkylsulphinyl, C_1-4alkylsulphonyl, carbamoyl, N-C_1-4alkylcarbamoyl, N,N-di(C_1-4alkyl)carbamoyl, aminosulphonyl, N-C_1-4alkylaminosulphonyl, N,N-di(C_1-4alkyl)aminosulphonyl, C_1-4alkylsulphonylamino, or a group R⁴X¹wherein X¹represents a direct bond, C_2-4alkanoyl, —

CONR⁵R⁶—

, —

SO₂NR⁷R⁸—

or —

SO₂R⁹—

(wherein R⁵and R⁷, each independently represents hydrogen or C_1-2alkyl and R⁶, R⁸and R⁹each independently represents C_1-4alkyl and wherein R⁴is linked to R⁶, R⁸or R⁹) and R⁴represents phenyl or a 5 or 6-membered heterocyclic group with one or two heteroatoms, selected independently from O, S and N, which heterocyclic group may be saturated or unsaturated and which phenyl or heterocyclic group may bear one or two substituents selected from hydroxy, halogeno, C_1-3alkyl, C_1-3alkoxy, C_1-3alkanoyloxy, trifluoromethyl, cyano, amino, nitro and C_1-4alkoxyearbonyl;

n is an integer from 0 to 4;

R¹represents hydrogen, C_1-4alkyl, C_1-4alkoxymethyl, di(C_1-4alkoxy)methyl or C_1-4alkanoyl;

m is an integer from 0 to 4; and

R³represents hydroxy, halogeno, nitro, trifluoromethyl, C_1-3alkyl, cyano, amino or R¹⁰X²wherein X²represents —

O—

, —

CH₂—

, —

S—

, —

SO—

, —

SO₂—

, —

NR¹¹CO—

, —

CONR¹²—

, —

SO₂NR¹³—

, —

NR¹⁴SO₂—

or —

NR¹⁵—

(wherein R¹¹, R¹², R¹³, R¹⁴and R¹⁵each independently represents hydrogen, C_1-3alkyl or C_1-3alkoxyC_2-3alkyl), or X²represents a direct bond, and R¹⁰is selected from one of the following seventeen groups;

1) hydrogen or C_1-5alkyl which maybe unsubstituted or which may be substituted with one or more groups selected from hydroxy, fluoro and amino;

2) C_1-5alkylX³COR¹⁶(wherein X³represents —

O—

or —

NR¹⁷—

(in which R¹⁷represents hydrogen, C_1-3alkyl or C_1-3alkoxyC_2-3alkyl) and R¹⁶represents C_1-3alkyl, —

NR¹⁸R¹⁹—

or —

OR²⁰—

(wherein R¹⁸, R¹⁹and R²⁰which may be the same or different each represents hydrogen, C_1-3alkyl or C_1-3alkoxyC_2-3alkyl));

3) C_1-5alkylX⁴R²¹(wherein X⁴represents —

O—

, —

S—

, —

SO—

, —

SO₂—

, —

OCO—

, —

NR²²CO—

, —

CONR²³—

, —

SO₂NR²⁴—

, —

NR²⁵SO₂—

or —

NR²⁶—

(wherein R²², R²³, R²⁴, R²⁵and R²⁶each independently represents hydrogen, C_1-3alkyl or C_1-3alkoxyC_2-3alkyl) and R²¹represents hydrogen, C_1-3alkyl, cyclopentyl, cyclohexyl or a 5 or 6 membered saturated heterocyclic group with one or two heteroatoms, selected independently from O, S and N, which C_1-3alkyl group may bear one or two substituents selected from oxo, hydroxy, halogeno and C_1-4alkoxy and which cyclic group may bear one or two substituents selected from oxo, hydroxy, halogeno, C_1-4alkyl, C_1-4hydroxyalkyl and C_1-4alkoxy);

4) C_1-5alkylX⁵C_1-5alkylX6R²⁷(wherein X⁵and X⁶which may be the same or different are each —

O—

, —

S—

, —

SO—

, —

SO₂—

, —

NR²⁸CO—

, —

CONR²⁹—

, —

SO₂NR³⁰—

, —

NR³¹SO₂—

or —

NR³²—

(wherein R²⁸, R²⁹, R³⁰, R³¹and R³²each independently represents hydrogen, C_1-3alkyl or C_1-3alkoxyC_2-3alkyl) and R²⁷represents hydrogen or C_1-3alkyl);

5) C_1-5alkylR³³(wherein R³³is a 5 or 6 membered saturated heterocyclic group with one or two heteroatoms, selected independently from O, S and N, which heterocyclic group may bear one or two substituents selected from oxo, hydroxy, halogeno, C_1-4alkyl, C_1-4hydroxyalkyl and C^1-4alkoxy);

6) C_2-5alkenylR³³(wherein R³³is as defined herein);

7) C_2-5alkynylR³³(wherein R³³is as defined herein);

8) R³⁴(wherein R³⁴represents a pyridone group, a phenyl group or a 5 or 6-membered aromatic heterocyclic group with 1 to 3 heteroatoms selected from O, N and S, which pyridone, phenyl or heterocyclic group may carry up to 5 substituents selected from hydroxy, halogeno, amino, C_1-4alkyl, C_1-4alkoxy, C_1-4hydroxyalkyl, C_1-4aminoalkyl, C_1-4alkylamino, C^1-4hydroxyalkoxy, carboxy, cyano, —

CONR³⁵R³⁶and —

NR³⁷COR³⁸(wherein R³⁵, R³⁶, R³⁷and R³⁸, which may be the same or different, each represents hydrogen, C_1-4alkyl or C_1-3alkoxyC_2-3alkyl));

9) C_1-5alkylR³⁴(wherein R³⁴is as defined herein);

10) C_2-5alkenylR³⁴(wherein R³⁴is as defined herein);

11) C_2-5alkynylR³⁴(wherein R³⁴is as defined herein);

12) C_1-5alkylX⁷R³⁴(wherein X⁷represents —

O—

, —

S—

, —

SO—

, —

SO₂—

, —

NR³⁹CO—

, —

CONR⁴⁰—

, —

SO₂NR⁴¹—

, —

NR⁴²SO₂—

or —

NR⁴³—

(wherein R³⁹, R⁴⁰, R⁴¹, R⁴²and R⁴³each independently represents hydrogen, C_1-3alkyl or C_1-3alkoxyC_2-3alkyl) and R³⁴is as defined herein);

13) C_2-5alkenylX⁸R³⁴(wherein X⁸represents —

O—

, —

S—

, —

SO—

, —

SO₂—

, —

NR⁴⁴CO—

, —

CONR⁴⁵—

, —

SO₂NR⁴⁶—

, —

NR⁴⁷SO₂—

or —

NR⁴⁸—

(wherein R⁴⁴, R⁴⁵, R⁴⁶, R⁴⁷and R⁴⁸each independently represents hydrogen, C_1-3alkyl or C_1-3alkoxyC_2-3alkyl) and R³⁴is as defined herein);

14) C_2-5alkynylX⁹R³⁴(wherein X⁹represents —

O—

, —

S—

, —

SO—

, —

SO₂—

, —

NR⁴⁹CO—

, —

CONR⁵⁰—

, —

SO₂NR⁵¹—

, —

NR⁵²SO₂—

or —

NR⁵³—

(wherein R⁴⁹, R⁵⁰, R⁵¹, R⁵²and R⁵³each independently represents hydrogen, C_1-3alkyl or C_1-3alkoxyC_2-3alkyl) and R³⁴is as defined herein);

15) C_1-3alkylX¹⁰C_1-3alkylR³⁴(wherein X¹⁰represents —

O—

, —

S—

, —

SO—

, —

SO₂—

, —

NR⁵⁴CO—

, —

CONR⁵⁵—

, —

SO₂NR⁵⁶—

, —

NR⁵⁷SO₂—

or —

NR⁵⁸—

(wherein R⁵⁴, R⁵⁵, R⁵⁶, R⁵⁷and R⁵⁸each independently represents hydrogen, C_1-3alkyl or C_1-3alkoxyC_2-3alkyl) and R³⁴is as defined herein);

16) R³³(wherein R³³is as defined herein); and

17) C_1-3alkylX¹⁰C_1-3alkylR³³(wherein X¹⁰and R³³are as defined herein);

and salts thereof.

View all claims

3 Assignments

Timeline View

Assignment View

0 Petitions

Accused Products

Abstract

The invention relates to compounds of formula (I),

wherein:

R²represents hydroxy, halogeno, C_1-3alkyl, C_1-3alkoxy, C_1-3alkanoyloxy, trifluoromethyl, cyano, amino, nitro, C_2-4alkanoyl, C_1-4alkanoylamino, C_1-4alkoxycarbonyl, C_1-4alkylthio, C_1-4alkylsulphinyl, C_1-4alkylsulphonyl, carbamoyl, {overscore (N)}—C_1-4alkylcarbamoyl, {overscore (N)},{overscore (N)}-di(C_1-4alkyl)carbamoyl, aminosulphonyl, {overscore (N)}—C_1-4alkylaminosulphonyl, {overscore (N)},{overscore (N)}-di(C_1-4alkyl)aminosulphonyl, C_1-4alkylsulphonylamino, or a group R⁴X¹wherein X¹represents a direct bond, C_2-4alkanoyl, —CONR⁵R⁶—, —SO₂NR⁷R⁸— or —SO₂R⁹— (wherein R⁵and R⁷, each independently represents hydrogen or C_1-2alkyl and R⁶, R⁸and R⁹each independently represents C_1-4alkyl and wherein R⁴is linked to R⁶, R⁸or R⁹) and R⁴represents an optionally substituted group selected from phenyl and a 5 or 6-membered heterocyclic group; n is an integer from 0 to 4, R¹represents hydrogen, C_1-4alkyl, C_1-4alkoxymethyl, di(C_1-4alkoxy)methyl or C_1-4alkanoyl; m is an integer from 0 to 4; and R³represents hydroxy, halogeno, nitro, trifluoromethyl, C_1-3alkyl, cyano, amino or R¹⁰X²(wherein X²represents a direct bond, —CH₂—, or a single or double heteroatom linker group including —S—, —SO— and —NR¹⁵— (wherein R¹⁵represents hydrogen, C_1-3alkyl or C_1-3alkoxyC_2-3alkyl), and R¹⁰is an alkenyl or alkynyl chain optionally substituted by for example hydroxy, amino, nitro, alkyl, cycloalkyl, alkoxyalkyl, or an optionally substituted group selected from pyridone, phenyl and a heterocyclic ring, which alkyl, alkenyl or alkynyl chain may have a heteroatom linker group, or R¹⁰is an optionally substituted group selected from pyridone, phenyl and a heterocyclic ring. The compounds of formula (I) and the pharmaceutically acceptable salts thereof inhibit the effects of VEGF and FGF, properties of value in the treatment of a number of disease states including cancer and rheumatoid arthritis.

Citations

19 Claims

1. A compound of the formula I:
- wherein;
  
  R²represents hydroxy, halogeno, C_1-3alkyl, C_1-3alkoxy, C_1-3alkanoyloxy, trifluoromethyl, cyano, amino, nitro, C_2-4alkanoyl, C_1-4alkanoylamino, C_1-4alkoxycarbonyl, C_1-4alkylthio, C_1-4alkylsulphinyl, C_1-4alkylsulphonyl, carbamoyl, N-C_1-4alkylcarbamoyl, N,N-di(C_1-4alkyl)carbamoyl, aminosulphonyl, N-C_1-4alkylaminosulphonyl, N,N-di(C_1-4alkyl)aminosulphonyl, C_1-4alkylsulphonylamino, or a group R⁴X¹wherein X¹represents a direct bond, C_2-4alkanoyl, —
  
  CONR⁵R⁶—
  
  , —
  
  SO₂NR⁷R⁸—
  
  or —
  
  SO₂R⁹—
  
  (wherein R⁵and R⁷, each independently represents hydrogen or C_1-2alkyl and R⁶, R⁸and R⁹each independently represents C_1-4alkyl and wherein R⁴is linked to R⁶, R⁸or R⁹) and R⁴represents phenyl or a 5 or 6-membered heterocyclic group with one or two heteroatoms, selected independently from O, S and N, which heterocyclic group may be saturated or unsaturated and which phenyl or heterocyclic group may bear one or two substituents selected from hydroxy, halogeno, C_1-3alkyl, C_1-3alkoxy, C_1-3alkanoyloxy, trifluoromethyl, cyano, amino, nitro and C_1-4alkoxyearbonyl;
  
  n is an integer from 0 to 4;
  
  R¹represents hydrogen, C_1-4alkyl, C_1-4alkoxymethyl, di(C_1-4alkoxy)methyl or C_1-4alkanoyl;
  
  m is an integer from 0 to 4; and
  
  R³represents hydroxy, halogeno, nitro, trifluoromethyl, C_1-3alkyl, cyano, amino or R¹⁰X²wherein X²represents —
  
  O—
  
  , —
  
  CH₂—
  
  , —
  
  S—
  
  , —
  
  SO—
  
  , —
  
  SO₂—
  
  , —
  
  NR¹¹CO—
  
  , —
  
  CONR¹²—
  
  , —
  
  SO₂NR¹³—
  
  , —
  
  NR¹⁴SO₂—
  
  or —
  
  NR¹⁵—
  
  (wherein R¹¹, R¹², R¹³, R¹⁴and R¹⁵each independently represents hydrogen, C_1-3alkyl or C_1-3alkoxyC_2-3alkyl), or X²represents a direct bond, and R¹⁰is selected from one of the following seventeen groups;
  
  1) hydrogen or C_1-5alkyl which maybe unsubstituted or which may be substituted with one or more groups selected from hydroxy, fluoro and amino;
  
  2) C_1-5alkylX³COR¹⁶(wherein X³represents —
  
  O—
  
  or —
  
  NR¹⁷—
  
  (in which R¹⁷represents hydrogen, C_1-3alkyl or C_1-3alkoxyC_2-3alkyl) and R¹⁶represents C_1-3alkyl, —
  
  NR¹⁸R¹⁹—
  
  or —
  
  OR²⁰—
  
  (wherein R¹⁸, R¹⁹and R²⁰which may be the same or different each represents hydrogen, C_1-3alkyl or C_1-3alkoxyC_2-3alkyl));
  
  3) C_1-5alkylX⁴R²¹(wherein X⁴represents —
  
  O—
  
  , —
  
  S—
  
  , —
  
  SO—
  
  , —
  
  SO₂—
  
  , —
  
  OCO—
  
  , —
  
  NR²²CO—
  
  , —
  
  CONR²³—
  
  , —
  
  SO₂NR²⁴—
  
  , —
  
  NR²⁵SO₂—
  
  or —
  
  NR²⁶—
  
  (wherein R²², R²³, R²⁴, R²⁵and R²⁶each independently represents hydrogen, C_1-3alkyl or C_1-3alkoxyC_2-3alkyl) and R²¹represents hydrogen, C_1-3alkyl, cyclopentyl, cyclohexyl or a 5 or 6 membered saturated heterocyclic group with one or two heteroatoms, selected independently from O, S and N, which C_1-3alkyl group may bear one or two substituents selected from oxo, hydroxy, halogeno and C_1-4alkoxy and which cyclic group may bear one or two substituents selected from oxo, hydroxy, halogeno, C_1-4alkyl, C_1-4hydroxyalkyl and C_1-4alkoxy);
  
  4) C_1-5alkylX⁵C_1-5alkylX6R²⁷(wherein X⁵and X⁶which may be the same or different are each —
  
  O—
  
  , —
  
  S—
  
  , —
  
  SO—
  
  , —
  
  SO₂—
  
  , —
  
  NR²⁸CO—
  
  , —
  
  CONR²⁹—
  
  , —
  
  SO₂NR³⁰—
  
  , —
  
  NR³¹SO₂—
  
  or —
  
  NR³²—
  
  (wherein R²⁸, R²⁹, R³⁰, R³¹and R³²each independently represents hydrogen, C_1-3alkyl or C_1-3alkoxyC_2-3alkyl) and R²⁷represents hydrogen or C_1-3alkyl);
  
  5) C_1-5alkylR³³(wherein R³³is a 5 or 6 membered saturated heterocyclic group with one or two heteroatoms, selected independently from O, S and N, which heterocyclic group may bear one or two substituents selected from oxo, hydroxy, halogeno, C_1-4alkyl, C_1-4hydroxyalkyl and C^1-4alkoxy);
  
  6) C_2-5alkenylR³³(wherein R³³is as defined herein);
  
  7) C_2-5alkynylR³³(wherein R³³is as defined herein);
  
  8) R³⁴(wherein R³⁴represents a pyridone group, a phenyl group or a 5 or 6-membered aromatic heterocyclic group with 1 to 3 heteroatoms selected from O, N and S, which pyridone, phenyl or heterocyclic group may carry up to 5 substituents selected from hydroxy, halogeno, amino, C_1-4alkyl, C_1-4alkoxy, C_1-4hydroxyalkyl, C_1-4aminoalkyl, C_1-4alkylamino, C^1-4hydroxyalkoxy, carboxy, cyano, —
  
  CONR³⁵R³⁶and —
  
  NR³⁷COR³⁸(wherein R³⁵, R³⁶, R³⁷and R³⁸, which may be the same or different, each represents hydrogen, C_1-4alkyl or C_1-3alkoxyC_2-3alkyl));
  
  9) C_1-5alkylR³⁴(wherein R³⁴is as defined herein);
  
  10) C_2-5alkenylR³⁴(wherein R³⁴is as defined herein);
  
  11) C_2-5alkynylR³⁴(wherein R³⁴is as defined herein);
  
  12) C_1-5alkylX⁷R³⁴(wherein X⁷represents —
  
  O—
  
  , —
  
  S—
  
  , —
  
  SO—
  
  , —
  
  SO₂—
  
  , —
  
  NR³⁹CO—
  
  , —
  
  CONR⁴⁰—
  
  , —
  
  SO₂NR⁴¹—
  
  , —
  
  NR⁴²SO₂—
  
  or —
  
  NR⁴³—
  
  (wherein R³⁹, R⁴⁰, R⁴¹, R⁴²and R⁴³each independently represents hydrogen, C_1-3alkyl or C_1-3alkoxyC_2-3alkyl) and R³⁴is as defined herein);
  
  13) C_2-5alkenylX⁸R³⁴(wherein X⁸represents —
  
  O—
  
  , —
  
  S—
  
  , —
  
  SO—
  
  , —
  
  SO₂—
  
  , —
  
  NR⁴⁴CO—
  
  , —
  
  CONR⁴⁵—
  
  , —
  
  SO₂NR⁴⁶—
  
  , —
  
  NR⁴⁷SO₂—
  
  or —
  
  NR⁴⁸—
  
  (wherein R⁴⁴, R⁴⁵, R⁴⁶, R⁴⁷and R⁴⁸each independently represents hydrogen, C_1-3alkyl or C_1-3alkoxyC_2-3alkyl) and R³⁴is as defined herein);
  
  14) C_2-5alkynylX⁹R³⁴(wherein X⁹represents —
  
  O—
  
  , —
  
  S—
  
  , —
  
  SO—
  
  , —
  
  SO₂—
  
  , —
  
  NR⁴⁹CO—
  
  , —
  
  CONR⁵⁰—
  
  , —
  
  SO₂NR⁵¹—
  
  , —
  
  NR⁵²SO₂—
  
  or —
  
  NR⁵³—
  
  (wherein R⁴⁹, R⁵⁰, R⁵¹, R⁵²and R⁵³each independently represents hydrogen, C_1-3alkyl or C_1-3alkoxyC_2-3alkyl) and R³⁴is as defined herein);
  
  15) C_1-3alkylX¹⁰C_1-3alkylR³⁴(wherein X¹⁰represents —
  
  O—
  
  , —
  
  S—
  
  , —
  
  SO—
  
  , —
  
  SO₂—
  
  , —
  
  NR⁵⁴CO—
  
  , —
  
  CONR⁵⁵—
  
  , —
  
  SO₂NR⁵⁶—
  
  , —
  
  NR⁵⁷SO₂—
  
  or —
  
  NR⁵⁸—
  
  (wherein R⁵⁴, R⁵⁵, R⁵⁶, R⁵⁷and R⁵⁸each independently represents hydrogen, C_1-3alkyl or C_1-3alkoxyC_2-3alkyl) and R³⁴is as defined herein);
  
  16) R³³(wherein R³³is as defined herein); and
  
  17) C_1-3alkylX¹⁰C_1-3alkylR³³(wherein X¹⁰and R³³are as defined herein);
  
  and salts thereof.
- View Dependent Claims (2, 3, 4, 11, 13, 14, 15, 16, 17, 18, 19)
- - 2. A compound as claimed in claim 1 wherein R¹is hydrogen.
  - 3. A compound as claimed in claim 1 or claim 2 wherein R²is halogeno, trifluoromethyl, cyano, nitro, C_2-3alkanoyl, C_1-3alkoxycarbonyl, C_1-3alkylsulphinyl, C_1-3alkylsulphonyl, carbamoyl, N-C_1-3alkylcarbamoyl, N,N-di(C_1-3alkyl)carbamoyl, aminosulphonyl, N-C_1-3alkylaminosulphonyl, N,N-di(C_1-3alkyl)aminosulphonyl, or a group R⁴X¹, wherein
4. A compound as claimed in claim 1 or claim 2 wherein R³is hydroxy, halogeno, nitro, trifluoromethyl, C_1-3alkyl, cyano, amino or R¹⁰X²whereinX²is as defined in claim 1 and R¹⁰is selected from one of the following fifteen groups:
- 1) C_1-3alkyl which may be unsubstituted or substituted with one or more fluorine atoms, or C_2-3alkyl which may be unsubstituted or substituted with one or two groups selected from hydroxy and amino;
  
  2) 2-(3,3-dimethylureido)ethyl, 3-(3,3-dimethylureido)propyl, 2-(3-methylureido)ethyl, 3-(3-methylureido)propyl, 2-ureidoethyl, 3-ureidopropyl, 2-(N,N-dimethylcarbamoyloxy)ethyl, 3-(N,N-dimethylcarbamoyloxy)propyl, 2-(N-methylcarbamoyloxy)ethyl, 3-(N-methylcarbamoyloxy)propyl, 2-(carbamoyloxy)ethyl, 3-(carbamoyloxy)propyl;
  
  3) C_2-3alkylX⁴R²¹(wherein X⁴is as defined in claim 1 and R²¹is a group selected from C_1-2alkyl, cyclopentyl, cyclohexyl, pyrrolidinyl and piperidinyl which group is linked to X⁴through a carbon atom and which C_1-2alkyl group may bear one or two substituents selected from hydroxy, halogeno and C_1-2alkoxy and which cyclopentyl, cyclohexyl, pyrrolidinyl or piperidinyl group may carry one substituent selected from oxo, hydroxy, halogeno, C_1-2alkyl, C_1-2hydroxyalkyl and C_1-2alkoxy);
  
  4) C_2-3alkylX⁵C_2-3alkylX⁶R²⁷(wherein X⁵and X⁶are as defined in claim 1 and R²⁷represents hydrogen or C_1-2alkyl);
  
  5) C_1-2alkylR⁶²(wherein R⁶²is a group selected from pyrrolidinyl, piperazinyl, piperidinyl, 1,3-dioxolan-2-yl, 1,3-dioxan-2-yl, 1,3-dithiolan-2-yl and 1,3-dithian-2-yl, which group is linked to C_1-2alkyl through a carbon atom and which group may carry one substituent selected from oxo, hydroxy, halogeno, C_1-2alkyl, C_1-2hydroxyalkyl and C_1-2alkoxy) or C_2-3alkylR⁶³(wherein R⁶³is a group selected from morpholino, thiomorpholino, piperidino, piperazin-1-yl and pyrrolidin-1-yl which group may carry one substituent selected from oxo, hydroxy, halogeno, C_1-2alkyl, C_1-2hydroxyalkyl and C_1-2alkoxy);
  
  6) R³⁴(wherein R³⁴is as defined in claim 1);
  
  7) C_1-4alkylR³⁴(wherein R³⁴is as defined in claim 1);
  
  8) 1-R³⁴but-2-en-4-yl (wherein R³⁴is as defined in claim 1);
  
  9) 1-R³⁴but-2-yn-4-yl (wherein R³⁴is as defined in claim 1);
  
  10) C_1-5alkylX⁷R³⁴(wherein X⁷and R³⁴are as defined in claim 1);
  
  11) 1-(R³⁴X⁸)but-2-en-4-yl (wherein X⁸and R³⁴are as defined in claim 1);
  
  12) 1-(R³⁴X⁹)but-2-yn-4-yl (wherein X⁹and R³⁴are as defined in claim 1);
  
  13) ethylX¹⁰methylR³⁴(wherein X¹⁰and R³⁴are as defined in claim 1);
  
  14) R³³(wherein R³³is as defined in claim 1); and
  
  15) ethylX¹⁰methylR³³(wherein X¹⁰and R³³are as defined in claim 1).
11. A compound as claimed in claim 5 or claim 6 wherein R^5ais selected from one of the following fifteen groups:
- 1) C_1-3alkyl which may be unsubstituted or substituted with one or more fluorine atoms, or C_2-3alkyl which may be unsubstituted or substituted with one or two groups selected from hydroxy and amino;
  
  2) 2-(3,3-dimethylureido)ethyl, 3-(3,3-dimethylureido)propyl, 2-(3-methylureido)ethyl, 3-(3-methylureido)propyl, 2-ureidoethyl, 3-ureidopropyl, 2-(N,N-dimethylcarbamoyloxy)ethyl, 3-(N,N-dimethylcarbamoyloxy)propyl, 2-(N-methylcarbamoyloxy)ethyl, 3-(N-methylcarbamoyloxy)propyl, 2-(carbamoyloxy)ethyl, 3-(carbamoyloxy)propyl;
  
  3) C_2-3alkylX^4aR^24a(wherein X^4ais as defined in claim 5 and R^24ais a group selected from C_1-2alkyl, cyclopentyl, cyclohexyl, pyrrolidinyl and piperidinyl which group is linked to X^4athrough a carbon atom and which C_1-2alkyl group may bear one or two substituents selected from hydroxy, halogeno and C_1-2alkoxy and which cyclopentyl, cyclohexyl, pyrrolidinyl or piperidinyl group may carry one substituent selected from oxo, hydroxy, halogeno, C_1-2alkyl, C_1-2hydroxyalkyl and C_1-2alkoxy);
  
  4) C_2-3alkylX^5aC_2-3alkylX^6aR^30a(wherein X^5aand X^6aare as defined in claim 5 and R^30arepresents hydrogen or C_1-2alkyl);
  
  5) C_1-2alkylR^65a(wherein R^65ais a group selected from pyrrolidinyl, piperazinyl, piperidinyl, 1,3-dioxolan-2-yl, 1,3-dioxan-2-yl, 1,3-dithiolan-2-yl and 1,3-dithian-2-yl, which group is linked to C_1-2alkyl through a carbon atom and which group may carry one substituent selected from oxo, hydroxy, halogeno, C_1-2alkyl, C_1-2hydroxyalkyl and C_1-2alkoxy) or C_2-3alkylR^66a(wherein R^66ais a group selected from morpholino, thiomorpholino, piperidino, piperazin-1-yl and pyrrolidin-1-yl which group may carry one substituent selected from oxo, hydroxy, halogeno, C_1-2alkyl, C_1-2hydroxyalkyl and C_1-2alkoxy);
  
  6) R^37a(wherein R^37ais as defined in claim 5);
  
  7) C_1-4alkylR^37a(wherein R^37ais as defined in claim 5);
  
  8) 1-R^37abut-2-en-4-yl (wherein R^37ais as defined in claim 5);
  
  9) 1-R^37abut-2-yn-4-yl (wherein R^37ais as defined in claim 5);
  
  10) C_1-5alkylX^7aR^37a(wherein X^7aand R^37aare as defined in claim 5);
  
  11) 1-(R^37aX^8a)but-2-en-4-yl (wherein X^8aand R^37aare as defined in claim 5);
  
  12) 1-(R^37aX^9a)but-2-yn-4-yl (wherein X^9aand R^37aare as defined in claim 5);
  
  13) ethylX^10amethylR^37a(wherein X^10aand R^37aare as defined in claim 5);
  
  14) R^36a(wherein R^36ais as defined in claim 5); and
  
  15) ethylX^10amethylR^36a(wherein X^10aand R^36aare as defined in claim 5).
13. A compound as claimed in claim 1 selected from:
- 6,7-dimethoxy-4-(6-fluorooxindol-3-yl)quinazoline;
  
  6,7-dimethoxy-4-(oxindol-3-yl)quinazoline;
  
  7-(2-methoxyethoxy)-4-(oxindol-3-yl)quinazoline;
  
  4-(5-bromooxindol-3-yl)-6-methoxy-7-(2-methoxyethoxy)quinazoline;
  
  4-(5-hydroxyoxindol-3-yl)-6-methoxy-7-(3-morpholinopropoxy)quinazoline;
  
  6-methoxy-7-(3-morpholinopropoxy)-4-(6-trifluoromethyloxindol-3-yl)quinazoline;
  
  4-(5-aminosulponyloxindol-3-yl)-6-methoxy-7-(2-methoxyethoxy)quinazoline;
  
  4-(5-cyanooxindol-3-yl)-7-(3-morpholinopropoxy)quinazoline;
  
  6-methoxy-7-(2-(2-methoxyethoxy)ethoxy)-4-(oxindol-3-yl)quinazoline; and
  
  4-(5-aminosulphonyloxindol-3-yl)-6-methoxy-7-(2-(2-methoxyethoxy)ethoxy)quinazoline;
  
  and salts thereof.
14. A compound as claimed in claim 1 selected from:
- 4-(5-fluorooxindol-3-yl)-6-methoxy-7-(3-morpholinopropoxy)quinazoline;
  
  4-(5-fluorooxindol-3-yl)-6-methoxy-7-(2-methoxyethoxy)quinazoline;
  
  4-(5-cyanooxindol-3-yl)-7-(2-(imidazol-1-yl)ethoxy)-6-methoxyquinazoline; and
  
  7-(3-morpholinopropoxy)-4-(6-trifluoromethyloxindol-3-yl)quinazoline;
  
  and salts thereof.
15. A compound as claimed in claim 1 selected from:
- 4-(6-fluorooxindol-3-yl)-6-methoxy-7-(3-morpholinopropoxy)quinazoline;
  
  6-methoxy-7-(2-methoxyethoxy)-4-(oxindol-3-yl)quinazoline; and
  
  6-methoxy-7-(3-morpholinopropoxy)-4-(oxindol-3-yl)quinazoline;
  
  and salts thereof.
16. A compound as claimed in any one of claims 1, 5 and 12-15 in the form of a pharmaceutically acceptable salt.
17. A process for the preparation of a compound of formula I or salt thereof (as defined in claim 1) which comprises:
- (a) the reaction of a compound of the formula III;
  
  (wherein R³and m are as defined in claim 1 and L¹is a displaceable moiety), with a compound of the formula IV;
  
  (wherein R¹, R²and n are as defined in claim 1) whereby to obtain compounds of the formula I and salts thereof;
  
  (b) the deprotection of a compound of formula V;
  
  (wherein R², R³, n and m are as defined in claim 1 and P¹represents a protecting group);
  
  (c) for the preparation of compounds of formula I and salts thereof wherein R¹is hydrogen, the reduction and cyclisation of a compound of formula VI;
  
  (wherein R², R³, m and n are as defined in claim 1 and Y represents cyano, carboxy or C_1-4alkoxycarbonyl);
  
  (d) for the preparation of compounds of formula I and salts thereof wherein at least one of the R²groups is hydroxy the deprotection of a compound of formula VII;
  
  (wherein R¹, R², R³, n and m are as defined in claim 1, P²represents a phenolic hydroxy protecting group and p1 is an integer from 1 to 4 equal to the number of protected hydroxy groups and such that n−
  
  p1 is equal to the number of R²substituents which are not protected hydroxy);
  
  (e) for the preparation of those compounds of formula I and salts thereof wherein at least one R³is R¹⁰X²wherein R¹⁰is as defined in claim 1 and X²is —
  
  O—
  
  , —
  
  S—
  
  , —
  
  SO₂—
  
  , —
  
  CONR¹²—
  
  , —
  
  SO₂NR¹³—
  
  or —
  
  NR¹⁵—
  
  (wherein R¹², R¹³and R¹⁵each independently represents hydrogen, C_1-3alkyl or C_1-3alkoxyC_2-3alkyl), the reaction, of a compound of the formula VIII;
  
  (wherein R¹, R², R³, n and X²are as defined in claim 1 and s is an integer from 0 to
  
  3) with a compound of formula IX;
18. A pharmaceutical composition which comprises as active ingredient a compound of formula I as defined in claim 1 or a pharmaceutically acceptable salt thereof in association with a pharmaceutically acceptable excipient or carrier.
19. A method for producing an antiangiogenic and/or vascular permeability reducing effect in a warm-blooded animal in need of such treatment which comprises administering to said animal an effective amount of a compound of formula I as defined in any one of claims 1, and 13-15, or a pharmaceutically acceptable salt thereof.

5. A compound of the formula Ia:
- wherein;
  
  R²represents hydroxy, halogeno, C_1-3alkyl, C_1-3alkoxy, C_1-3alkanoyloxy, trifluoromethyl, cyano, amino, nitro, C_2-4alkanoyl, C_1-4alkanoylamino, C_1-4alkoxycarbonyl, C_1-4alkylthio, C_1-4alkylsulphinyl, C_1-4alkylsulphonyl, carbamoyl, N-C_1-4alkylcarbamoyl, N,N-di(C_1-4alkyl)carbamoyl, aminosulphonyl, N-C_1-4alkylaminosulphonyl, N,N-di(C_1-4alkyl)aminosulphonyl, C_1-4alkylsulphonylamino, or a group R⁴X¹wherein X¹represents a direct bond, C_2-4alkanoyl, —
  
  CONR⁵R⁶—
  
  , —
  
  SO₂NR⁷R⁸—
  
  or —
  
  SO₂R⁹—
  
  (wherein R⁵and R⁷, each independently represents hydrogen or C_1-2alkyl and R⁶, R⁸and R⁹each independently represents C_1-4alkyl and wherein R⁴is linked to R⁶, R⁸or R⁹) and R⁴represents phenyl or a 5 or 6-membered heterocyclic group with one or two heteroatoms, selected independently from O, S and N, which heterocyclic group may be saturated or unsaturated and which phenyl or heterocyclic group may bear one or two substituents selected from hydroxy, halogeno, C_1-3alkyl, C_1-3alkoxy, C_1-3alkanoyloxy, trifluoromethyl, cyano, amino, nitro and C_1-4alkoxycarbonyl;
  
  n is an integer from 0 to 4;
  
  R¹represents hydrogen, C_1-4alkyl, C_1-4alkoxymethyl, di(C_1-4alkoxy)methyl or C_1-4alkanoyl;
  
  R^3arepresents hydrogen, hydroxy, methoxy, amino, nitro or halogeno;
  
  R^4arepresents hydrogen, hydroxy, halogeno, cyano, nitro, trifluoromethyl, C_1-3alkyl, C_1-3alkoxy, C_1-3alkylthio, —
  
  NR^6aR^7a—
  
  (wherein R^6aand R^7a, which may be the same or different, each represents hydrogen or C_1-3alkyl) or R^8a(CH₂)_zaX^2a(wherein R^8ais a 5 or 6 membered saturated heterocyclic group with one or two heteroatoms, selected independently from O, S and N, which heterocyclic group may bear one or two substituents selected from oxo, hydroxy, halogeno, C_1-4alkyl, C_1-4hydroxyalkyl and C_1-4alkoxy, za is an integer from 0 to 4 and X^2arepresents a direct bond, —
  
  O—
  
  , —
  
  CH₂—
  
  , —
  
  S—
  
  , —
  
  SO—
  
  , —
  
  SO₂—
  
  , —
  
  NR^9aCO—
  
  , —
  
  CONR^10a, —
  
  SO₂NR^11a—
  
  , —
  
  NR^12aSO₂—
  
  or —
  
  NR^13a—
  
  (wherein R^9a, R^10a, R^11a, R^12aand R^13aeach independently represents hydrogen, C_1-3alkyl or C_1-3alkoxyC_2-3alkyl));
  
  X^1arepresents —
  
  O—
  
  , —
  
  CH₂—
  
  , —
  
  S—
  
  , —
  
  SO—
  
  , —
  
  SO₂—
  
  , —
  
  NR^14aCO—
  
  , —
  
  CONR^15a—
  
  , —
  
  SO₂NR^16a—
  
  , —
  
  NR^17aSO₂—
  
  or —
  
  NR^18a—
  
  (wherein R^14a, R^15a, R^16a, R^17aand R^18aeach independently represents hydrogen, C_1-3alkyl or C_1-3alkoxyC_2-3alkyl) or X^1arepresents a direct bond;
  
  R^5ais selected from one of the following seventeen groups;
  
  1) hydrogen or C_1-5alkyl which may be unsubstituted or which may be substituted with one or more groups selected from hydroxy, fluoro and amino;
  
  2) C_1-5alkylX^3aCOR^19a(wherein X^3arepresents —
  
  O—
  
  or —
  
  NR^20a—
  
  (in which R^20arepresents hydrogen, C_1-3alkyl or C_1-3alkoxyC_2-3alkyl) and R^19arepresents C_1-3alkyl, —
  
  NR^21aR^22a—
  
  or —
  
  OR^23a—
  
  (wherein R^21a, R^22aand R^23awhich may be the same or different each represents hydrogen, C_1-3alkyl or C_1-3alkoxyC_2-3alkyl));
  
  3) C_1-5alkylX^4aR^24a(wherein X^4arepresents —
  
  O—
  
  , —
  
  S—
  
  , —
  
  SO—
  
  , —
  
  SO₂—
  
  , —
  
  OCO—
  
  , —
  
  NR^25aCO—
  
  , —
  
  CONR^26a—
  
  , —
  
  SO₂NR^27a—
  
  , —
  
  NR^28aSO₂—
  
  or —
  
  NR_29a—
  
  (wherein R^25a, R^26a, R^27a, R^28aand R^29aeach independently represents hydrogen, C_1-3alkyl or C_1-3alkoxyC_2-3alkyl) and R^24arepresents hydrogen, C_1-3alkyl, cyclopentyl, cyclohexyl or a 5 or 6 membered saturated heterocyclic group with one or two heteroatoms, selected independently from O, S and N, which C_1-3alkyl group may bear one or two substituents selected from oxo, hydroxy, halogeno and C_1-4alkoxy and which cyclic group may bear one or two substituents selected from oxo, hydroxy, halogeno, C_1-4alkyl, C_1-4hydroxyalkyl and C_1-4alkoxy);
  
  4) C_1-5alkylX^5aC_1-5alkylX^6aR^30a(wherein X^5aand X^6awhich may be the same or different are each —
  
  O—
  
  , —
  
  S—
  
  , —
  
  SO—
  
  , —
  
  SO₂—
  
  , —
  
  NR^31aCO—
  
  , —
  
  CONR^32a—
  
  , —
  
  SO₂NR^33a—
  
  , —
  
  NR^34aSO₂—
  
  or —
  
  NR^35a—
  
  (wherein R^31a, R^32a, R^33a, R^34aand R^35aeach independently represents hydrogen, C_1-3alkyl or C_1-3alkoxyC_2-3alkyl) and R^30arepresents hydrogen or C_1-3alkyl);
  
  5) C_1-5alkylR^36a(wherein R^36ais a 5 or 6 membered saturated heterocyclic group with one or two heteroatoms, selected independently from O, S and N, which heterocyclic group may bear one or two substituents selected from oxo, hydroxy, halogeno, C_1-4alkyl, C_1-4hydroxyalkyl and C_1-4alkoxy);
  
  6) C_2-5alkenylR^36a(wherein R^36ais as defined herein);
  
  7) C_2-5alkynylR^36a(wherein R^36ais as defined herein);
  
  8) R^37a(wherein R^37arepresents a pyridone group, a phenyl group or a 5 or 6-membered aromatic heterocyclic group with 1 to 3 heteroatoms selected from O, N and S, which pyridone, phenyl or heterocyclic group may carry up to 5 substituents selected from hydroxy, halogeno, amino, C_1-4alkyl, C_1-4alkoxy, C_1-4hydroxyalkyl, C_1-4aminoalkyl, C_1-4alkylamino, C_1-4hydroxyalkoxy, carboxy, cyano, —
  
  CONR^38aR^39aand —
  
  NR^40aCOR^41a(wherein R^38a, R^39a, R^40aand R^41a, which may be the same or different, each represents hydrogen, C_1-4alkyl or C_1-3alkoxyC_2-3alkyl));
  
  9) C_1-5alkylR^37a(wherein R^37ais as defined herein);
  
  10) C_2-5alkenylR^37a(wherein R^37ais as defined herein);
  
  11) C_2-5alkynylR^37a(wherein R^37ais as defined herein);
  
  12) C_1-5alkylX^7aR^37a(wherein X^7arepresents —
  
  O—
  
  , —
  
  S—
  
  , —
  
  SO—
  
  , —
  
  SO₂—
  
  , —
  
  NR^42aCO—
  
  , —
  
  CONR^43a—
  
  , —
  
  SO₂NR^44a, —
  
  NR^45aSO₂—
  
  or NR^46a—
  
  (wherein R^42a, R^43a, R^44a, R^45aand R^46aeach independently represents hydrogen, C_1-3alkyl or C_1-3alkoxyC_2-3alkyl) and R^37ais as defined herein);
  
  13) C_2-5alkenylX^8aR^37a(wherein X^8arepresents —
  
  O—
  
  , —
  
  S—
  
  , —
  
  SO—
  
  , —
  
  SO₂—
  
  , —
  
  NR^47aCO—
  
  , —
  
  CONR^48a—
  
  , —
  
  SO₂NR^49a—
  
  , —
  
  NR^50aSO₂—
  
  or —
  
  NR^51a—
  
  (wherein R^47a, R^48a, R^49a, R^50aand R^51aeach independently represents hydrogen, C_1-3alkyl or C_1-3alkoxyC_2-3alkyl) and R^37ais as defined herein);
  
  14) C_2-5alkynylX^9aR^37a(wherein X^9arepresents —
  
  O—
  
  , —
  
  S—
  
  , —
  
  SO—
  
  , —
  
  SO₂—
  
  , —
  
  NR^52aCO—
  
  , —
  
  CONR^53a—
  
  , —
  
  SO₂NR^54a—
  
  , —
  
  NR^55aSO₂—
  
  or —
  
  NR^56a—
  
  (wherein R^52a, R^53a, R^54a, R^55aand R^56aeach independently represents hydrogen, C_1-3alkyl or C_1-3alkoxyC_2-3alkyl) and R^37ais as defined herein);
  
  15) C_1-3alkylX^10aC_1-3alkylR^37a(wherein X^10arepresents —
  
  O—
  
  , —
  
  S—
  
  , —
  
  SO—
  
  , —
  
  SO₂—
  
  , —
  
  NR^57aCO—
  
  , —
  
  CONR^58a—
  
  , —
  
  SO₂NR^59a—
  
  , —
  
  NR^60aSO₂—
  
  or —
  
  NR^61a—
  
  (wherein R^57a, R^58a, R^59a, R^60aand R^61aeach independently represents hydrogen, C_1-3alkyl or C_1-3alkoxyC_2-3alkyl) and R^37ais as defined herein);
  
  16) R^36a(wherein R^36ais as defined herein); and
  
  17) C_1-3alkylX^10aC_1-3alkylR^36a(wherein X^10aand R^36aare as defined herein);
  
  and salts thereof.
- View Dependent Claims (6, 7, 8, 9, 10)
- - 6. A compound as claimed in claim 5 wherein R¹is hydrogen.
  - 7. A compound as claimed in claim 5 or claim 6 wherein R²is halogeno, trifluoromethyl, cyano, nitro, C_2-3alkanoyl, C_1-3alkoxycarbonyl, C_1-3alkylsulphinyl, C_1-3alkylsulphonyl, carbamoyl, N-C_1-3alkylcarbamoyl, N,N-di(C_1-3alkyl)carbamoyl, aminosulphonyl, N-C_1-3alkylaminosulphonyl, N,N-di(C_1-3alkyl)aminosulphonyl, or a group R⁴X¹(wherein X¹is as defined in claim 5 and R⁴represents phenyl or a 5 or 6-membered heterocyclic group with one or two heteroatoms, selected independently from O, S and N, of which at least one is N, which heterocyclic group may be saturated or unsaturated and which phenyl or heterocyclic group may bear one or two substituents selected from hydroxy, halogeno, C_1-2alkyl, C_1-2alkoxy, C_1-2alkanoyloxy, trifluoromethyl, cyano, amino, nitro and C_1-4alkoxycarbonyl).
  - 8. A compound as claimed in claim 5 or claim 6 wherein R^3ais hydrogen.
  - 9. A compound as claimed in claim 5 or claim 6 wherein R^4ais hydrogen, hydroxy, cyano, nitro, trifluoromethyl, methyl, ethyl, methoxy, ethoxy, or R^8a(CH₂)_zaX^2a(wherein R^8ais a group selected from pyrrolidinyl, piperazinyl, piperidinyl, morpholino and thiomorpholino which group may carry one or two substituents selected from oxo, hydroxy, halogeno, C_1-2alkyl, C_1-2hydroxyalkyl and C_1-2alkoxy, X^2ais —
    - O—
      
      , —
      
      S—
      
      , —
      
      NR^9aCO—
      
      , —
      
      NR^12aSO₂—
      
      (wherein R^9aand R^12aeach independently represents hydrogen or C_1-2alkyl) or NH and za is an integer from 1 to
      
      3).
  - 10. A compound as claimed in claim 5 or claim 6 wherein X^1ais —
    - O—
      
      , —
      
      S—
      
      , —
      
      NR^14aCO—
      
      , —
      
      NR^17aSO₂—
      
      (wherein R^14aand R^17aeach independently represents hydrogen or C_1-2alkyl) or NH.

12. A compound of the formula Ib:
- wherein;
  
  R^1brepresents hydrogen;
  
  R^2brepresents halogeno, trifluoromethyl, cyano, nitro, C_2-3alkanoyl, C_1-3alkoxycarbonyl, C_1-3alkylsulphinyl, C_1-3alkylsulphonyl, carbamoyl, N-C_1-3alkylcarbamoyl, N,N-di(C_1-3alkyl)carbamoyl, aminosulphonyl, N-C_1-3alkylaminosulphonyl, N,N-di(C_1-3alkyl)aminosulphonyl, or a group R^6bX^2b(wherein X^2brepresents a direct bond, C_2-4alkanoyl, —
  
  CONR^7bR^8b—
  
  , —
  
  SO₂NR^9bR^10b—
  
  or —
  
  SO₂R^11b—
  
  (wherein R^7band R^9b, each independently represents hydrogen and R^8b, R^10band R^11beach independently represents C_1-3alkyl and wherein R^6bis linked to R^8b, R^10bor R^11b) and R^6brepresents pyrrolidinyl, piperazinyl, piperidinyl, morpholino, thiomorpholino, imidazolyl or triazolyl which heterocyclic group is linked to X^2bvia a nitrogen atom and which heterocyclic group may bear one or two substituents selected from hydroxy, halogeno, C_1-2alkyl, C_1-2alkoxy, C_1-2alkanoyloxy, trifluoromethyl, cyano, amino, nitro and C_1-4alkoxycarbonyl);
  
  nb is an integer from 0 to 2;
  
  R^3brepresents hydrogen;
  
  R^4brepresents hydrogen, hydroxy, cyano, nitro, trifluoromethyl, methyl, methoxy or a group R^12b(CH₂)_zbX^3b(wherein R^12brepresents a group selected from pyrrolidinyl, piperazinyl, piperidinyl, morpholino and thiomorpholino which group may carry one or two substituents selected from oxo, hydroxy, halogeno, C_1-2alkyl, C_1-2hydroxyalkyl and C_1-2alkoxy, zb is an integer from 1 to 3 and X^3brepresents —
  
  O—
  
  or —
  
  NR¹³CO—
  
  (wherein R^13brepresents hydrogen or C_1-2alkyl));
  
  X^1brepresents —
  
  O—
  
  or —
  
  NR^14bCO—
  
  (wherein R^14brepresents hydrogen or C_1-2alkyl); and
  
  R^5brepresents methyl, ethyl, trifluoromethyl, 2,2,2-trifluoroethyl, 2-hydroxyethyl, 3-hydroxypropyl, 2-methoxyethyl, 3-methoxypropyl, 2-(methylsulphinyl)ethyl, 2-(methylsulphonyl)ethyl, 2-(N,N-dimethylsulphamoyl)ethyl, 2-(N-methylsulphamoyl)ethyl, 2-sulphamoylethyl, 2-(N,N-dimethylamino)ethyl, 3-(N,N-dimethylamino)propyl, 2-morpholinoethyl, 3-morpholinopropyl, 2-piperidinoethyl, 3-piperidinopropyl, 2-(piperazin-1-yl)ethyl, 3-(piperazin-1-yl)propyl, 2-(pyrrolidin-1-yl)ethyl, 3-(pyrrolidin-1-yl)propyl, (1,3-dioxolan-2-yl)methyl, 2-(1,3-dioxolan-2-yl)ethyl, 2-(2-methoxyethylamino)ethyl, 2-(2-hydroxyethylamino)ethyl, 3-(2-methoxyethylamino)propyl, 3-(2-hydroxyethylamino)propyl, 2-methylthiazol-4-ylmethyl, 2-acetamidothiazol-4-ylmethyl, 1-methylimidazol-2-ylmethyl, 2-(imidazol-1-yl)ethyl, 2-(1,2,3-triazol-1-yl)ethyl, 2-(1,2,3-triazol-2-yl)ethyl, 2-(1,2,4-triazol-1-yl)ethyl, 2-(1,2,4-triazol-4-yl)ethyl, 4-pyridylmethyl, 2-(4-pyridyl)ethyl, 3-(4-pyridyl)propyl 2-(4-pyridyloxy)ethyl, 2-(4-pyridylamino)ethyl, 2-(4-oxo-1,4-dihydro-1-pyridyl)ethyl, 2-thiomorpholinoethyl, 3-thiomorpholinopropyl, 2-(2-methoxyethoxy)ethyl, 2-(4-methylpiperazin-1-yl)ethyl, 3-(4-methylpiperazin-1-yl)propyl, 3-(methylsulphinyl)propyl, 3-(methylsulphonyl)propyl, 2-(2-methylimidazol-1-yl)ethyl, 2-(5-methyl-1,2,4-triazol-1-yl)ethyl, morpholino, 2-((N-(1-methylimidazol-4-ylsulphonyl)-N-methyl)amino)ethyl, 2-((N-(3-morpholinopropylsulphonyl)-N-methyl)amino)ethyl, 2-((N-methyl-N-4-pyridyl)amino)ethyl or 3-(4-oxidomorpholino)propyl;
  
  and salts thereof.

Specification

Resources

Litigation Campaign Assessment

Current Assignee
Astrazeneca UK Limited (Astrazeneca PLC)
Original Assignee
Zeneca Incorporated (Astrazeneca PLC)
Inventors
Hennequin, Laurent Francois Andre, Thomas, Andrew Peter, Lohmann, Jean-Jacques Marcel, Ple, Patrick
Primary Examiner(s)
Shah, Mukund J.
Assistant Examiner(s)
Patel, Sudhaker B.

Application Number

US09/180,310
Time in Patent Office

991 Days
Field of Search

544/284, 514/259
US Class Current

514/266.2
CPC Class Codes

A61P 13/00   Drugs for disorders of the ...

A61P 13/12   of the kidneys

A61P 27/00   Drugs for disorders of the ...

A61P 27/02   Ophthalmic agents

A61P 3/00   Drugs for disorders of the ...

A61P 3/10   for hyperglycaemia, e.g. an...

A61P 35/00   Antineoplastic agents

A61P 37/00   Drugs for immunological or ...

A61P 43/00   Drugs for specific purposes...

A61P 9/00   Drugs for disorders of the ...

C07D 231/12   with only hydrogen atoms, h...

C07D 233/56   with only hydrogen atoms or...

C07D 249/08   1,2,4-Triazoles; Hydrogenat...

C07D 401/14   containing three or more he...

C07D 403/04   directly linked by a ring-m...

C07D 403/14   containing three or more he...

Oxindole derivatives

First Claim

3 Assignments

0 Petitions

Accused Products

Abstract

Citations

19 Claims

Specification

Solutions

Use Cases

Quick Links

Oxindole derivatives

First Claim

3 Assignments

Subscription Required

Subscription Required

0 Petitions

Subscription Required

Accused Products

Subscription Required

Abstract

Citations

19 Claims

Specification

Subscription Required

Solutions

Use Cases

Quick Links