# US 2013/0158005 A1 · Pyrimidine derivatives as fak inhibitors

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- Number: US 2013/0158005 A1
- Document ID: US20130158005A1
- Status: Published application
- Kind: A1
- Application number: 13/817,251
- Filed: 2011-07-19
- Published: 2013-06-20
- Earliest claimed: 2010-08-18
- Assignees: Merck Patent GmbH
- Inventors: Timo Heinrich; Christina Esdar; Hartmut Greiner
- Web page: https://patentgrep.com/patent/US20130158005A1

## CPC

- C07D 239/42: One nitrogen atom (nitro radicals C07D239/30)
- A61P 1/16: for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
- A61P 3/00: Drugs for disorders of the metabolism (of the blood or the extracellular fluid A61P7/00)
- A61P 3/10: for hyperglycaemia, e.g. antidiabetics
- A61P 7/00: Drugs for disorders of the blood or the extracellular fluid
- A61P 7/02: Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
- A61P 9/00: Drugs for disorders of the cardiovascular system
- A61P 9/10: for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
- A61P 13/02: of urine or of the urinary tract, e.g. urine acidifiers
- A61P 13/12: of the kidneys
- A61P 17/00: Drugs for dermatological disorders
- A61P 17/02: for treating wounds, ulcers, burns, scars, keloids, or the like
- A61P 17/06: Antipsoriatics
- A61P 19/00: Drugs for skeletal disorders
- A61P 19/02: for joint disorders, e.g. arthritis, arthrosis
- A61P 19/08: for bone diseases, e.g. rachitism, Paget's disease
- A61P 25/00: Drugs for disorders of the nervous system
- A61P 25/28: for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
- A61P 27/02: Ophthalmic agents
- A61P 29/00: Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- A61P 35/00: Antineoplastic agents
- A61P 35/02: specific for leukemia
- A61P 35/04: specific for metastasis
- A61P 37/02: Immunomodulators
- A61P 37/06: Immunosuppressants, e.g. drugs for graft rejection
- A61P 37/08: Antiallergic agents (antiasthmatic agents A61P11/06; ophthalmic antiallergics A61P27/14)
- A61P 43/00: Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C07D 233/88: Nitrogen atoms, e.g. allantoin
- C07D 401/04: directly linked by a ring-member-to-ring-member bond
- C07D 401/06: linked by a carbon chain containing only aliphatic carbon atoms
- C07D 401/12: linked by a chain containing hetero atoms as chain links
- C07D 401/14: containing three or more hetero rings
- C07D 403/04: directly linked by a ring-member-to-ring-member bond
- C07D 403/12: linked by a chain containing hetero atoms as chain links
- C07D 403/14: containing three or more hetero rings
- C07D 405/04: directly linked by a ring-member-to-ring-member bond
- C07D 413/12: linked by a chain containing hetero atoms as chain links
- C07D 413/14: containing three or more hetero rings
- C07D 417/04: directly linked by a ring-member-to-ring-member bond
- C07D 417/12: linked by a chain containing hetero atoms as chain links
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

Compounds of the formula (I), in which R1, R2 and R3 have the meanings indicated in Claim 1, are kinase inhibitors and can be employed, inter alia, for the treatment of tumours.

## Claims

### Claim 1

Compounds of the formula I
in which
R1 denotes (CH2)nAr1 or (CH2)nHet1,
R2 denotes Ar2 or Het2,
R3 denotes H, Hal, A, Het4 or CN,
Ar1 denotes phenyl which is unsubstituted or mono-, di-, tri-, tetra or pentasubstituted by Hal, A, (CH2)nOH, (CH2)nOA, (CH2)nCN, NO2, SO2A, COOH, COOA, NH2, NHA, NA2, NHCH2Ar1, CHO, COA, (CH2)nCONH2, (CH2)nCONHA, (CH2)nCONA2, Het3, NHCOHet3, SO2NH2, SO2NHA and/or NHCOA,
Ar2 denotes phenyl which is unsubstituted or mono-, di-, tri-, tetra or pentasubstituted by Hal, A, (CH2)nOH, (CH2)nOA, (CH2)nCN, NO2, SO2A, COOH, COOA, NH2, NHA, NA2, NHCH2Ar1, CHO, COA, (CH2)nCONH2, (CH2)nCONHA, (CH2)nCONA2, SO2NH2, NHSO2A, SO2NHA, NA′SO2A, C(R4R5)CN and/or NHCOA,
Het1 denotes a mono- or bicyclic aromatic, unsaturated or saturated heterocycle having 1 to 4 N, O and/or S atoms, which may be unsubstituted or mono-, di-, tri- or tetrasubstituted by Hal, A, NH2, NHA, NA2, COOH, CN, NHCOA, CN, NHCOA, COA, OAr, COOA, CONH2, CONHA, CONA2, CONHAr and/or ═O,
Het2 denotes a mono- or bicyclic aromatic heterocycle having 1 to 4 N, O and/or S atoms, which may be unsubstituted or mono-, di-, tri- or tetrasubstituted by Hal, A, NH2, NHA, NA2, COOH, COA, COOA, CONH2, CONHA, CONA2, CONHAr, C(R4R5)CN, NHSO2A, NASO2A, NHCOA, NA′COA, NACHO, NH(CH2)pNHCHO and/or ═O,
Ar denotes phenyl which is unsubstituted or mono-, di- or trisubstituted by Hal and/or A,
R4, R5 each, independently of one another, denote H or A,
R4 and R5 together also denote alkylene having 2-5 C atoms, in which one CH2 group may be replaced by NH, NA', O or S,
Het3 denotes a mono- or bicyclic aromatic, unsaturated or saturated heterocycle having 1 to 3 N, O and/or S atoms, which may be unsubstituted or mono- or disubstituted by A, NH2 and/or ═O,
Het4 denotes a monocyclic aromatic heterocycle having 1 to 3 N, O and/or S atoms, which may be unsubstituted or mono- or disubstituted by A,
A denotes unbranched or branched alkyl having 1-10 C atoms, in which 1-7H atoms may be replaced by F and/or in which one or two non-adjacent CH and/or CH2 groups may be replaced by O, NH, NA′, S, SO, SO2 and/or by CH═CH groups,
or
cyclic alkyl having 3-7 C atoms,
A′ denotes unbranched or branched alkyl having 1-6 C atoms,
Hal denotes F, Cl, Br or I,
n denotes 0, 1, 2, 3 or 4,
p denotes 1, 2, 3 or 4,
and pharmaceutically usable salts, tautomers and stereoisomers thereof, including mixtures thereof in all ratios.

### Claim 2 (depends on 1)

Compounds according to claim 1 in which
Ar1 phenyl which is mono-, di-, tri-, tetra or pentasubstituted by Hal, (CH2)nCN, SO2A, (CH2)nCONH2, (CH2)nCONHA, (CH2)nCONA2, Het3 and/or NHCOHet3,
and pharmaceutically usable salts, tautomers and stereoisomers thereof, including mixtures thereof in all ratios.

### Claim 3 (depends on 1)

Compounds according to claim 1 in which
Ar2 denotes phenyl which is mono-, di-, tri-, tetra or pentasubstituted by Hal, A, (CH2)nCN, SO2A, NHSO2A, NA′SO2A and/or C(R4R5)CN,
and pharmaceutically usable salts, tautomers and stereoisomers thereof, including mixtures thereof in all ratios.

### Claim 4 (depends on 1)

Compounds according to claim 1 in which
Het1 denotes furyl, thienyl, pyrrolyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, pyridyl, pyrimidinyl, triazolyl, tetrazolyl, oxadiazolyl, thiadiazolyl, pyridazinyl, pyrazinyl, benzimidazolyl, benzotriazolyl, quinolinyl, quinoxalinyl, quinazolinyl, pyrrolopyridinyl, purinyl, indolyl or indazolyl, tetrahydroquinolyl, dihydrobenzoxazolyl, dihydropyridazinyl, dihydrobenzimidazolyl, dihydrobenzothiazolyl, piperidinyl, pyrrolidinyl, morpholinyl, piperazinyl, imidazolidinyl, oxazolidinyl or tetrahydropyranyl, each of which is unsubstituted or mono-, di- or trisubstituted by A, CN, NHCOA, COA, OAr and/or ═O,
and pharmaceutically usable salts, tautomers and stereoisomers thereof, including mixtures thereof in all ratios.

### Claim 5 (depends on 1)

Compounds according to claim 1 in which
Het2 denotes furyl, thienyl, pyrrolyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, pyridyl, pyrimidinyl, triazolyl, tetrazolyl, oxadiazolyl, thiadiazolyl, pyridazinyl, pyrazinyl, benzimidazolyl, benzotriazolyl, quinolinyl, quinoxalinyl, quinazolinyl, pyrrolopyridinyl, purinyl, indolyl or indazolyl, each of which is mono-, di- or trisubstituted by C(R4R5)CN, NHSO2A, NASO2A, NHCOA, NA′COA, NACHO, NH(CH2)pNHCHO and/or ═O,
and pharmaceutically usable salts, tautomers and stereoisomers thereof, including mixtures thereof in all ratios.

### Claim 6 (depends on 1)

Compounds according to claim 1 in which
Het3 denotes furyl, thienyl, pyrrolyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, pyridyl, pyrimidinyl, triazolyl, tetrazolyl, oxadiazolyl, thiadiazolyl, pyridazinyl, pyrazinyl, benzimidazolyl, benzotriazolyl, quinolinyl, quinoxalinyl, quinazolinyl, pyrrolopyridinyl, purinyl, indolyl or indazolyl, tetrahydroquinolyl, dihydrobenzoxazolyl, dihydropyridazinyl, dihydrobenzimidazolyl, dihydrobenzothiazolyl, piperidinyl, pyrrolidinyl, morpholinyl, piperazinyl, imidazolidinyl, oxazolidinyl or tetrahydropyranyl, each of which is unsubstituted or mono-, di- or trisubstituted by A, NH2 and/or ═O,
and pharmaceutically usable salts, tautomers and stereoisomers thereof, including mixtures thereof in all ratios.

### Claim 7 (depends on 1)

Compounds according to claim 1 in which
A denotes unbranched or branched alkyl having 1-10 C atoms, in which 1-7H atoms may be replaced by F and/or in which one CH2 group may be replaced by O or NH,
and pharmaceutically usable salts, tautomers and stereoisomers thereof, including mixtures thereof in all ratios.

### Claim 8 (depends on 1)

Compounds according to claim 1 in which
R1 denotes (CH2)nAr1 or (CH2)nHet1,
R2 denotes Ar2 or Het2,
R3 denotes H, Hal, A or CN,
Ar1 denotes phenyl which is mono-, di-, tri-, tetra or pentasubstituted by Hal, (CH2)nCN, SO2A, (CH2)nCONH2, (CH2)nCONHA, (CH2)nCONA2, Het3 and/or NHCOHet3,
Ar2 denotes phenyl which is mono-, di-, tri-, tetra or pentasubstituted by Hal, A, (CH2)nCN, SO2A, NHSO2A, NA′SO2A and/or C(R4R5)CN,
Het1 denotes furyl, thienyl, pyrrolyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, pyridyl, pyrimidinyl, triazolyl, tetrazolyl, oxadiazolyl, thiadiazolyl, pyridazinyl, pyrazinyl, benzimidazolyl, benzotriazolyl, quinolinyl, quinoxalinyl, quinazolinyl, pyrrolopyridinyl, purinyl, indolyl or indazolyl, tetrahydroquinolyl, dihydrobenzoxazolyl, dihydropyridazinyl, dihydrobenzimidazolyl, dihydrobenzothiazolyl, piperidinyl, pyrrolidinyl, morpholinyl, piperazinyl, imidazolidinyl, oxazolidinyl or tetrahydropyranyl, each of which is unsubstituted or mono-, di- or trisubstituted by A, CN, NHCOA, COA, OAr and/or ═O,
Het2 denotes furyl, thienyl, pyrrolyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, pyridyl, pyrimidinyl, triazolyl, tetrazolyl, oxadiazolyl, thiadiazolyl, pyridazinyl, pyrazinyl, benzimidazolyl, benzotriazolyl, quinolinyl, quinoxalinyl, quinazolinyl, pyrrolopyridinyl, purinyl, indolyl or indazolyl, each of which is mono-, di- or trisubstituted by C(R4R5)CN, NHSO2A, NASO2A, NHCOA, NA′COA, NACHO, NH(CH2)pNHCHO and/or ═O,
Het3 denotes furyl, thienyl, pyrrolyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, pyridyl, pyrimidinyl, triazolyl, tetrazolyl, oxadiazolyl, thiadiazolyl, pyridazinyl, pyrazinyl, benzimidazolyl, benzotriazolyl, quinolinyl, quinoxalinyl, quinazolinyl, pyrrolopyridinyl, purinyl, indolyl or indazolyl, tetrahydroquinolyl, dihydro-benzoxazolyl, dihydropyridazinyl, dihydrobenzimidazolyl, dihydrobenzothiazolyl, piperidinyl, pyrrolidinyl, morpholinyl, piperazinyl, imidazolidinyl, oxazolidinyl or tetrahydropyranyl, each of which is unsubstituted or mono-, di- or trisubstituted by A, NH2 and/or ═O,
Ar denotes phenyl which is unsubstituted or mono-, di- or trisubstituted by Hal and/or A,
R4, R5 each, independently of one another, denote H or A,
R4 and R5 together also denote alkylene having 2-5 C atoms, in which one CH2 group may be replaced by NH, NA', O or S,
A denotes unbranched or branched alkyl having 1-10 C atoms, in which 1-7H atoms may be replaced by F and/or in which one CH2 group may be replaced by O or NH,
A′ denotes unbranched or branched alkyl having 1-6 C atoms,
Hal denotes F, Cl, Br or I,
n denotes 0, 1, 2, 3 or 4,
p denotes 1, 2, 3 or 4,
and pharmaceutically usable salts, tautomers and stereoisomers thereof, including mixtures thereof in all ratios.

### Claim 9 (depends on 1)

Compounds according to claim 1, selected from the group
No.
Name and/or structure
“A1”
N-(2-{2-[2-(4-Methanesulfonylphenylamino)pyrimidin-4-yl]-
ethyl}phenyl)-N-methylmethanesulfonamide
“A2”
N-Methyl-N-(2-{2-[2-(2-oxo-1,2,3,4-tetrahydroquinolin-6-
ylamino)pyrimidin-4-yl]ethyl}phenyl)methanesulfonamide
“A3”
6-{4-[2-(3-Methanesulfonylphenyl)ethyl]pyrimidin-2-ylamino}-
3,4-dihydro-1H-quinolin-2-one
“A4”
(4-Methanesulfonylphenyl)-{4-[2-(3-methanesulfonylphenyl)-
ethyl]pyrimidin-2-yl}amine
“A5”
N-Methyl-N-(2-{2-[2-(2-oxo-2,3-dihydro-1H-indol-5-ylamino)-
pyrimidin-4-yl]ethyl}phenyl)methanesulfonamide
“A6”
N-Methyl-N-(3-{2-[2-(2-oxo-2,3-dihydro-1H-indol-5-ylamino)-
pyrimidin-4-yl]ethyl}pyridin-2-yl)methanesulfonamide
“A7”
N-Methyl-N-(3-{2-[2-(2-oxo-1,2,3,4-tetrahydroquinolin-6-
ylamino)pyrimidin-4-yl]ethyl}pyridin-2-yl)methanesulfonamide
“A8”
N-(3-{2-[2-(4-Methanesulfonylphenylamino)pyrimidin-4-yl]-
ethyl}pyridin-2-yl)-N-methylmethanesulfonamide
“A9”
(2-{2-[2-(2-Oxo-2,3-dihydro-1H-indol-5-ylamino)pyrimidin-4-
yl]ethyl}phenyl)acetonitrile
“A10”
N-Methyl-N-(3-{2-[2-(2-oxo-2,3-dihydro-1H-indol-5-ylamino)-
pyrimidin-4-yl]ethyl}pyridin-2-yl)acetamide
“A11”
(4-Fluoro-2-{2-[2-(2-oxo-2,3-dihydro-1H-indol-5-ylamino)-
pyrimidin-4-yl]ethyl}phenyl)acetonitrile
“A12”
N-Methyl-N-(3-{2-[2-(2-oxo-2,3-dihydro-1H-indol-5-ylamino)-
pyrimidin-4-yl]ethyl}pyridin-2-yl)formamide
“A13”
1-(2-{2-[2-(2-Oxo-2,3-dihydro-1H-indol-5-ylamino)pyrimidin-
4-yl]ethyl}phenyl)cyclobutanecarbonitrile
“A14”
N-[2-(3-{2-[2-(2-Oxo-2,3-dihydro-1H-indol-5-ylamino)-
pyrimidin-4-yl]ethyl}pyridin-2-ylamino)ethyl]formamide
“A15”
(2-{2-[2-(2-Oxo-2,3-dihydro-1H-indol-5-ylamino)pyrimidin-4-
yl]ethyl}-5-trifluoromethylphenyl)acetonitrile
“A16”
3-(3-{2-[2-(2-Oxo-2,3-dihydro-1H-indol-5-ylamino)pyrimidin-
4-yl]ethyl}pyridin-2-yl)azetidine-3-carbonitrile
“A17”
(2-{2-[2-(2-Oxo-2,3-dihydro-1H-indol-5-ylamino)pyrimidin-4-
yl]ethyl}-4-trifluoromethylphenyl)acetonitrile
“A18”
(5-Fluoro-2-{2-[2-(2-oxo-2,3-dihydro-1H-indol-5-ylamino)-
pyrimidin-4-yl]ethyl}phenyl)acetonitrile
“A19”
1-(2-{2-[2-(2-Oxo-2,3-dihydro-1H-indol-5-ylamino)pyrimidin-
4-yl]ethyl}-4-trifluoromethylphenyl)cyclobutanecarbonitrile
“A20”
N-Methyl-N-(3-{2-[2-(2-oxo-2,3-dihydrobenzoxazol-6-
ylamino)pyrimidin-4-yl]ethyl}pyridin-2-yl)methanesulfonamide
“A21”
N-Methyl-N-(3-{2-[2-(1-methyl-2-oxo-2,3-dihydro-1H-indol-5-
ylamino)pyrimidin-4-yl]ethyl}pyridin-2-yl)methanesulfonamide
“A22”
N-(3-{2-[2-(3-Cyanophenylamino)pyrimidin-4-yl]ethyl}-
pyridin-2-yl)-N-methylmethanesulfonamide
“A23”
N-(3-{2-[2-(3-Cyano-4-fluorophenylamino)pyrimidin-4-yl]-
ethyl}pyridin-2-yl)-N-methylmethanesulfonamide
“A24”
N-Methyl-N-[3-(2-{2-[(6-oxo-1,6-dihydropyridazin-3-
ylmethyl)amino]pyrimidin-4-yl}ethyl)pyridin-2-yl]-
methanesulfonamide
“A25”
N-(3-{2-[2-(1,3-Dimethyl-2-oxo-2,3-dihydro-1H-benzimidazol-
5-ylamino)pyrimidin-4-yl]ethyl}pyridin-2-yl)-N-
methylmethanesulfonamide
“A26”
N-(3-{[5-Cyano-2-(2-oxo-2,3-dihydrobenzoxazol-6-ylamino)-
pyrimidin-4-ylamino]methyl}pyridin-2-yl)-N-
methylmethanesulfonamide
“A27”
N-Methyl-N-(2-{2-[2-(2-oxo-2,3-dihydrobenzoxazol-6-
ylamino)pyrimidin-4-yl]ethyl}phenyl)methanesulfonamide
“A28”
N-(2-{2-[2-(3-Cyanophenylamino)pyrimidin-4-yl]ethyl}-
phenyl)-N-methylmethanesulfonamide
“A29”
N-(2-{2-[2-(3-Cyano-4-fluorophenylamino)pyrimidin-4-yl]-
ethyl}phenyl)-N-methylmethanesulfonamide
“A30”
N-Methyl-N-(2-{2-[2-(2-oxo-2,3-dihydrobenzothiazol-5-
ylamino)pyrimidin-4-yl]ethyl}phenyl)methanesulfonamide
“A31”
N-(2-{2-[2-(1-Acetyl-2,3-dihydro-1H-indol-5-ylamino)-
pyrimidin-4-yl]ethyl}phenyl)-N-methylmethanesulfonamide
“A32”
2-[3-(4-{2-[2-(Methanesulfonylmethylamino)phenyl]ethyl}-
pyrimidin-2-ylamino)phenyl]-N-methylacetamide
“A33”
N-Methyl-N-[2-(2-{2-[4-(3-oxomorpholin-4-yl)phenylamino]-
pyrimidin-4-yl}ethyl)phenyl]methanesulfonamide
“A34”
N-[4-(4-{2-[2-(Methanesulfonylmethylamino)phenyl]ethyl}-
pyrimidin-2-ylamino)phenyl]nicotinamide
“A35”
N-Methyl-N-[2-(2-{2-[4-(2-oxopyrrolidin-1-yl)phenylamino]-
pyrimidin-4-yl}ethyl)phenyl]methanesulfonamide
“A36”
N-[2-(2-{2-[3,5-Dichloro-4-(2-oxopyrrolidin-1-yl)phenyl-
amino]pyrimidin-4-yl}ethyl)phenyl]-N-methylmethane-
sulfonamide
“A37”
N-[2-(2-{2-[3-Cyano-4-(2-oxopiperidin-1-yl)phenylamino]-
pyrimidin-4-yl}ethyl)phenyl]-N-methylmethanesulfonamide
“A38”
N-[2-(2-{2-[4-(1,3-Dioxo-1,3-dihydroisoindol-2-yl)phenyl-
amino]pyrimidin-4-yl}ethyl)phenyl]-N-methylmethane-
sulfonamide
“A39”
N-Methyl-N-[3-(2-{2-[4-(2-oxopyrrolidin-1-yl)phenylamino]-
pyrimidin-4-yl}ethyl)pyridin-2-yl]methanesulfonamide
“A40”
N-[4-(4-{2-[2-(Methanesulfonylmethylamino)pyridin-3-yl]-
ethyl}pyrimidin-2-ylamino)phenyl]nicotinamide
“A41”
N-Methyl-N-[3-(2-{2-[4-(3-oxomorpholin-4-yl)phenylamino]-
pyrimidin-4-yl}ethyl)pyridin-2-yl]methanesulfonamide
“A42”
N-[3-(2-{2-[3-Cyano-4-(2-oxopiperidin-1-yl)phenylamino]-
pyrimidin-4-yl}ethyl)pyridin-2-yl]-N-methylmethane-
sulfonamide
“A43”
N-[3-(2-{2-[4-(1,3-Dioxo-1,3-dihydroisoindol-2-yl)-
phenylamino]pyrimidin-4-yl}ethyl)pyridin-2-yl]-N-methyl-
methanesulfonamide
“A44”
N-Methyl-N-(5-methyl-3-{2-[2-(2-oxo-2,3-dihydro-1H-indol-5-
ylamino)pyrimidin-4-yl]ethyl}pyridin-2-yl)methanesulfonamide
“A45”
1-(4-Fluoro-2-{2-[2-(2-oxo-2,3-dihydro-1H-indol-5-ylamino)-
pyrimidin-4-yl]ethyl}phenyl)cyclobutanecarbonitrile
“A46”
1-(5-Fluoro-2-{2-[2-(2-oxo-2,3-dihydro-1H-indol-5-ylamino)-
pyrimidin-4-yl]ethyl}phenyl)cyclobutanecarbonitrile
“A47”
1-(2-{2-[2-(2-Oxo-2,3-dihydro-1H-indol-5-ylamino)pyrimidin-
4-yl]ethyl}-5-trifluoromethylphenyl)cyclobutanecarbonitrile
“A48”
(5-Fluoro-4-phenethylpyrimidin-2-yl)phenylamine
“A49”
(5-Methyl-4-phenethylpyrimidin-2-yl)phenylamine
“A50”
(4-Phenethyl-5-trifluoromethylpyrimidin-2-yl)phenylamine
“A52”
(5-Bromo-4-phenethylpyrimidin-2-yl)phenylamine
“A56”
6-{5-Fluoro-4-[2-(4-fluorophenyl)ethyl]pyrimidin-2-ylamino}-
3,4-dihydro-1H-quinolin-2-one
“A65”
6-{4-[2-(4-Fluorophenyl)ethyl]-5-methylpyrimidin-2-ylamino}-
3,4-dihydro-1H-quinolin-2-one
“A71”
[5-(1-Methyl-1H-pyrazol-4-yl)-4-phenethylpyrimidin-2-yl]-
phenylamine
“A74”
5-{4-[2-(4-Fluorophenyl)ethyl]-5-trifluoromethylpyrimidin-2-
ylamino}-1,3-dihydroindol-2-one
“A77”
6-{4-[2-(4-Fluorophenyl)ethyl]-5-trifluoromethylpyrimidin-2-
ylamino}-3,4-dihydro-1H-quinolin-2-one
“A101”
6-(5-Bromo-4-phenethylpyrimidin-2-ylamino)-3,4-dihydro-1H-
quinolin-2-one
“A102”
5-(4-Phenethyl-5-trifluoromethylpyrimidin-2-ylamino)-1,3-
dihydroindol-2-one
“A103”
6-(4-Phenethyl-5-trifluoromethylpyrimidin-2-ylamino)-3,4-
dihydro-1H-quinolin-2-one
“A104”
6-(5-Methyl-4-{2-[3-(propane-1-sulfonyl)phenyl]ethyl}-
pyrimidin-2-ylamino)-3,4-dihydro-1H-quinolin-2-one
“A105”
6-(5-Fluoro-4-{2-[3-(propane-1-sulfonyl)phenyl]ethyl}-
pyrimidin-2-ylamino)-3,4-dihydro-1H-quinolin-2-one
“A106”
[6-(4-tert-Butylphenoxy)pyridin-3-yl]-(5-fluoro-4-
phenethylpyrimidin-2-yl)amine
“A107”
(5-Fluoro-4-phenethylpyrimidin-2-yl)-(6-
trifluoromethylpyridin-3-yl)amine
“A108”
(5-Fluoro-4-phenethylpyrimidin-2-yl)-(6-fluoropyridin-3-yl)-
amine
“A109”
5-(5-Fluoro-4-phenethylpyrimidin-2-ylamino)pyridine-2-
carbonitrile
“A110”
N-[5-(5-Fluoro-4-phenethylpyrimidin-2-ylamino)pyridin-2-yl]-
acetamide
“A111”
N-Methyl-N-(2-{2-[2-(2-oxo-2,3-dihydro-1H-indol-5-ylamino)-
5-trifluoromethylpyrimidin-4-yl]ethyl}phenyl)-
methanesulfonamide
and pharmaceutically usable salts, tautomers and stereoisomers thereof, including mixtures thereof in all ratios.

### Claim 10 (depends on 1)

Process for the preparation of compounds of the formula I according to claim 1 and pharmaceutically usable salts, tautomers and stereoisomers thereof, characterised in that
a) a compound of the formula II
in which
R1, R2 and R3 have the meanings indicated in claim 1,
is hydrogenated,
or
b) a compound of the formula III
in which
R2, R3 have the meanings indicated in claim 1,
is reacted with a compound of the formula IV
R1—NH2 IV
in which R1 has the meaning indicated in claim 1,
and/or
a base or acid of the formula I is converted into one of its salts.

### Claim 11 (depends on 1)

Medicaments comprising at least one compound of the formula I according to claim 1 and/or pharmaceutically usable salts, tautomers and stereoisomers thereof, including mixtures thereof in all ratios, and optionally excipients and/or adjuvants.

### Claim 12 (depends on 1)

Compounds of the formula I according to claim 1 and pharmaceutically usable salts, tautomers and stereoisomers thereof, including mixtures thereof in all ratios, for use for the treatment of tumours, cancer, tumour formation, growth and spread, arteriosclerosis, eye diseases, such as age-induced macular degeneration, choroidal neovascularisation and diabetic retinopathy, inflammatory diseases, arthritis, thrombosis, fibrosis, glomerulonephritis, neurodegeneration, psoriasis, restenosis, wound healing, transplant rejection, metabolic and diseases of the immune system, autoimmune diseases, cirrhosis, diabetes and diseases of the blood vessels.