# US 10,308,629 B2 · 1H-pyrrol-3-amines

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- Number: US 10,308,629 B2
- Document ID: US10308629B2
- Status: Granted
- Kind: B2
- Application number: 15/750,103
- Filed: 2016-08-01
- Published: 2018-08-09
- Granted: 2019-06-04
- Earliest claimed: 2015-08-05
- Assignees: Bayer Pharma Aktiengesellschaft
- Applicants: Bayer Pharma Aktiengesellschaft
- Inventors: Keith Graham; Ulrich Klar; Hans Briem; Gerhard Siemeister; Ursula Mönning
- Web page: https://patentgrep.com/patent/US10308629B2

## CPC

- C07D 401/04: directly linked by a ring-member-to-ring-member bond
- A61K 31/4439: containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole (nicotine A61K31/465)
- A61K 45/06: Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
- A61P 35/00: Antineoplastic agents
- A61P 35/04: specific for metastasis
- A61P 43/00: Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C07D 401/14: containing three or more hetero rings
- C07D 403/04: directly linked by a ring-member-to-ring-member bond
- C07D 405/14: containing three or more hetero rings
- C07D 409/14: containing three or more hetero rings
- C07D 417/14: containing three or more hetero rings
- C07D 471/04: Ortho-condensed systems
- C07D 487/04: Ortho-condensed systems
- C07D 491/056: with two or more oxygen atoms as ring hetero atoms in the oxygen-containing ring
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

Compounds of formula (I) as described herein, processes for their production and their use as pharmaceuticals.

## Claims

### Claim 1

A compound of formula (I),
wherein:
G is a group selected from the group consisting of:
wherein * indicates the points of attachment of said group with the rest of the molecule;
X is CH2, CHORx, or C═O;
Rx is hydrogen or C1-C6-alkyl;
R1 is hydrogen or C1-C6-alkyl;
R2 is hydrogen, C1-C6-alkyl, R10—O—C(O)— or R7R8N—C(O)—;
R3 is hydrogen or C1-C6-alkyl;
A is a group selected from the group consisting of:
wherein * indicates the point of attachment of said group to the rest of the molecule and said group is optionally substituted, one or more times, independently from each other, with R4;
R4 is halogen, hydroxy, nitro, cyano, C1-C4-alkyl, C1-C4-alkoxy, C1-C4-haloalkyl, C1- C4-haloalkoxy, C1-C4-hydroxyalkyl, C1-C4-alkyl-C(O)—, R10—O—C(O)—, R7R8N—C(O)—, C1-C4-alkyl-C(O)—NH—, R7R8N—, or R7R8N—SO2—;
E is a group
wherein * indicates the point of attachment of said group to the rest of the molecule;
each R5 is independently halogen, hydroxy, nitro, cyano, R9R10N—, (R13—C(O)—)(R14—C(O)—)N—, C1-C4-alkyl, C3-C6-cycloalkyl, C1-C6-alkoxy, C1-C4-haloalkyl, C1-C6-haloalkoxy, R6—C(O)—NR9—, R6—O—C(O)—NR9—, R6—SO2—NR9— or R7R8N—C(O)—NR9—;
Q is O or N—OH;
each R6 is independently C1-C6-alkyl, C3-C6-cycloalkyl, 4- to 6-membered heterocycloalkyl, phenyl or heteroaryl,
wherein said C1-C6-alkyl is optionally substituted, one or more times, independently from each other, with halogen, hydroxy, nitro, cyano, C1-C4-alkoxy, C1-C4-haloalkoxy, C3-C6-cycloalkyl, R7R8N— or phenyl optionally substituted, one or more times, independently from each other, with R4,
wherein said C3-C6-cycloalkyl, 4- to 6-membered heterocycloalkyl, phenyl or heteroaryl groups are optionally substituted, one or more times, independently from each other, with halogen, hydroxy, nitro, cyano, C1-C6-alkyl, C1-C4-alkoxy, C1-C4-haloalkyl, R10—O—C(O)— or C1-C4-haloalkoxy;
R7 and R8 are independently hydrogen, C1-C6-alkyl, C3-C6-cycloalkyl, R10—O—C(O)— or phenyl,
wherein said C1-C6-alkyl is optionally substituted, one or more times, independently from each other, with halogen, hydroxy, C1-C4-alkoxy, C1-C4-haloalkoxy, C3-C6-cycloalkyl optionally substituted one time with hydroxy, 4- to 6-membered heterocycloalkyl, heteroaryl, or R9R10N—,
wherein said phenyl group is optionally substituted, one or more times, independently from each other, with R4;
or,
R7 and R8 together with the nitrogen atom to which they are attached form a 4- to 7-membered nitrogen containing heterocyclic ring, optionally containing one additional heteroatom selected from the group consisting of O, NR9 and S, and which may be optionally substituted one or more times, independently from each other, with R12;
whereby when two R12 substituents are attached to the same ring carbon atom, together with the carbon atom to which they are attached, can be linked to one another in such a way that they jointly form a cyclobutane, azetidine, or oxetane group;
said azetidine being optionally substituted one time with C1-C3-alkyl,
or,
R7 and R8 together with the nitrogen atom to which they are attached form a group selected from:
wherein * indicates the point of attachment of said group to the rest of the molecule,
R9 is hydrogen, or C1-C6-alkyl;
R10 is hydrogen, C1-C6-alkyl or C3-C6-cycloalkyl;
R12 is halogen, hydroxy, C1-C4-alkyl, C1-C4-alkoxy, C1-C4-haloalkyl, C1-C4-haloalkoxy, or R9R10N—;
R13 and R14 are independently C1-C4-alkyl, or C3-C6-cycloalkyl,
wherein said C3-C6-cycloalkyl is optionally substituted, one or more times, independently from each other, with halogen; and
m is 0, 1 or 2,
or an N-oxide, a salt, a tautomer or a stereoisomer of said compound, or a salt of said N-oxide, tautomer or stereoisomer.

### Claim 2 (depends on 1)

The compound of formula (I) according to claim 1, wherein:
G is a group selected from the group consisting of:
wherein * indicates the points of attachment of said group to the rest of the molecule;
X is CH2 or C═O;
R1 is hydrogen or C1-C4-alkyl;
R2 is hydrogen, C1-C4-alkyl, R10—O—C(O)—, or R7R8N—C(O)—;
R3 is hydrogen or C1-C4-alkyl;
A is a group selected from:
wherein * indicates the point of attachment of said group to the rest of the molecule and said group is optionally substituted, one or more times, independently from each other, with R4;
R4 is halogen, hydroxy, nitro, cyano, C1-C4-alkyl, C1-C4-alkoxy, C1-C4-haloalkyl, C1-C4-haloalkoxy, C1-C4-hydroxyalkyl, C1-C4-alkyl-C(O)—, or R10—O—C(O)—;
E is a group
wherein * indicates the point of attachment of said group to the rest of the molecule;
each R5 is independently halogen, hydroxy, nitro, cyano, R9R10N—, (R13—C(O)—)(R14—C(O)—)N—, C1-C3-alkyl, C3-C4-cycloalkyl, C1-C3-alkoxy, C1-C3-haloalkyl, C1-C3-haloalkoxy, R6—C(O)—NR9—, R6—O—C(O)—NR9—, R6—SO2—NR9—, or R7R8N—C(O)—NR9—,
Q is O;
each R6 is independently C1-C6-alkyl, C3-C6-cycloalkyl, 4- to 6-membered heterocycloalkyl, phenyl, or heteroaryl,
wherein said C1-C6-alkyl is optionally substituted, one or more times, independently from each other, with halogen, hydroxy, nitro, cyano, C1-C4-alkoxy, C1-C4-haloalkoxy, C3-C6-cycloalkyl, R7R8N— or phenyl optionally substituted, one or more times, independently from each other, with R4,
wherein said C3-C6-cycloalkyl, 4- to 6-membered heterocycloalkyl, phenyl or heteroaryl groups are optionally substituted, one or more times, independently from each other, with halogen, hydroxy, nitro, cyano, C1-C6-alkyl, C1-C4-alkoxy, C1-C4-haloalkyl, R10—O—C(O)—, or C1-C4-haloalkoxy;
R7 and R8 are independently hydrogen, C1-C6-alkyl, C3-C6-cycloalkyl, R10—O—C(O)—, or phenyl,
wherein said C1-C6-alkyl is optionally substituted, one or more times, independently from each other, with halogen, hydroxy, C1-C4-alkoxy, C1-C4-haloalkoxy, C3-C6-cycloalkyl optionally substituted one time with hydroxy, 4- to 6-membered heterocycloalkyl, heteroaryl, or R9R10N—,
wherein said phenyl group is optionally substituted, one or more times, independently from each other, with R4;
or,
R7 and R8 together with the nitrogen atom to which they are attached form a 5- to 6-membered nitrogen containing heterocyclic ring, optionally containing one additional heteroatom selected from the group consisting of O and NR9;
R9 is hydrogen or C1-C4-alkyl;
R10 is hydrogen, C1-C4-alkyl, or C3-C4-cycloalkyl;
R13 and R14 are independently C1-C3-alkyl, or C3-C4-cycloalkyl,
wherein said C3-C4-cycloalkyl is optionally substituted, one or more times, independently from each other, with halogen; and
m is 0, 1 or 2,
or an N-oxide, a salt, a tautomer or a stereoisomer of said compound, or a salt of said N-oxide, tautomer or stereoisomer.

### Claim 3 (depends on 1)

The compound of formula (I) according to claim 1, wherein:
G is a group selected from the group consisting of:
wherein * indicates the points of attachment of said group to the rest of the molecule;
X is CH2 or C═O;
R1 is hydrogen or C1-C4-alkyl;
R2 is hydrogen, or C1-C3-alkyl;
R3 is hydrogen or C1-C2-alkyl;
A is a group selected from:
wherein * indicates the point of attachment of said group to the rest of the molecule and said group is optionally substituted, one or more times, independently from each other, with R4;
R4 is halogen, hydroxy, nitro, cyano, C1-C2-alkyl, C1-C2-alkoxy, C1-C2-haloalkyl, C1-C2-haloalkoxy, or C1-C2-hydroxyalkyl;
E is a group
wherein * indicates the point of attachment of said group to the rest of the molecule;
each R5 is independently halogen, hydroxy, nitro, cyano, R9R10N—, C1-alkyl, C3-cycloalkyl, C1-alkoxy, C1-haloalkyl, C1-haloalkoxy, R6—C(O)—NR9—, R6—O—C(O)—NR9—, R6—SO2—NR9— or R7R8N—C(O)—NR9—;
Q is O;
each R6 is independently C1-C4-alkyl, C3-C4-cycloalkyl, 5- to 6-membered heterocycloalkyl, phenyl, or heteroaryl,
wherein said C1-C4-alkyl is optionally substituted, one or more times, independently from each other, with halogen, hydroxy, C1-alkoxy, or C1-haloalkoxy,
wherein said C3-C4-cycloalkyl, 5- to 6-membered heterocycloalkyl, phenyl or heteroaryl groups are optionally substituted, one or more times, independently from each other, with halogen, hydroxy, C1-alkyl, C1-alkoxy, or C1-haloalkyl;
R7 and R8 are independently hydrogen, C1-C4-alkyl, or C3-C4-cycloalkyl,
wherein said C1-C4-alkyl is optionally substituted, one or more times, independently from each other, with halogen, hydroxy, C1-alkoxy, C1-haloalkoxy, C3-C4-cycloalkyl optionally substituted one time with hydroxy, 5- to 6-membered heterocycloalkyl, heteroaryl, or R9R10N—,
R9 is hydrogen or C1-alkyl;
R10 is hydrogen or C1-alkyl; and
m is 0 or 1,
or an N-oxide, a salt, a tautomer or a stereoisomer of said compound, or a salt of said N-oxide, tautomer or stereoisomer.

### Claim 4 (depends on 1)

The compound of formula (I) according to claim 1, wherein:
G is a group selected from the group consisting of:
wherein * indicates the points of attachment of said group to the rest of the molecule;
X is CH2 or C═O;
R1 is hydrogen or C1-alkyl;
R2 is C1-alkyl;
R3 is hydrogen;
A is a group:
wherein * indicates the point of attachment of said group to the rest of the molecule;
E is a group
wherein * indicates the point of attachment of said group to the rest of the molecule;
Q is O;
each R6 is independently C1-C3-alkyl, C3-cycloalkyl, phenyl, or heteroaryl,
wherein said C1-C3-alkyl is optionally substituted, one or more times, with fluoro,
wherein said C3-cycloalkyl, phenyl or heteroaryl groups are optionally substituted, one or two times, independently from each other, with fluoro, C1-alkyl, or C1-alkoxy;
R7 and R8 are independently hydrogen, C1-C2-alkyl, or C3-cycloalkyl;
R9 is hydrogen;
R10 is hydrogen;
R15 is a hydrogen or a fluorine atom; and
R16 is hydrogen, R9R10N—, R6—C(O)—NR9—, R6—O—C(O)—NR9—, R6—SO2—NR9—, or R7R8N—C(O)—NR9—,
or an N-oxide, a salt, a tautomer or a stereoisomer of said compound, or a salt of said N-oxide, tautomer or stereoisomer.

### Claim 5 (depends on 1)

The compound according to claim 1, which is selected from the group consisting of:
rel-(5R,7S)-6,6-dimethyl-3-(phenylamino)-2-(pyridin-4-yl)-1,5,6,7-tetrahydro-4H-5,7-methanoindol-4-one,
rel-(5R,7S)-2-(2-aminopyridin-4-yl)-6,6-dimethyl-3-(phenylamino)-1,5,6,7-tetrahydro-4H-5,7-methanoindol-4-one,
(5R,7S)-2-(2-aminopyridin-4-yl)-6,6-dimethyl-3-(phenylamino)-1,5,6,7-tetrahydro-4H-5,7-methanoindol-4-one,
(5S,7R)-2-(2-aminopyridin-4-yl)-6,6-dimethyl-3-(phenylamino)-1,5,6,7-tetrahydro-4H-5,7-methanoindol-4-one,
N-4-[rel-(5R,7S)-6,6-dimethyl-4-oxo-3-(phenylamino)-4,5,6,7-tetrahydro-1H-5,7-methanoindol-2-yl]pyridin-2-ylacetamide,
N-4-[rel-(5R,7S)-6,6-dimethyl-4-oxo-3-(phenylamino)-4,5,6,7-tetrahydro-1H-5,7-methanoindol-2-yl]pyridin-2-ylcyclopropanecarboxamide,
methyl 4-[rel-(5R,7S)-6,6-dimethyl-4-oxo-3-(phenylamino)-4,5,6,7-tetrahydro-1H-5,7-methanoindol-2-yl]pyridin-2-ylcarbamate,
1-4-[rel-(5R,7S)-6,6-dimethyl-4-oxo-3-(phenylamino)-4,5,6,7-tetrahydro-1H-5,7-methanoindol-2-yl]pyridin-2-yl-3-ethylurea,
1-cyclopropyl-3-4-[rel-(5R,7S)-6,6-dimethyl-4-oxo-3-(phenylamino)-4,5,6,7-tetrahydro-1H-5,7-methanoindol-2-yl]pyridin-2-ylurea,
rel-(5R,7S)-2-(3-fluoropyridin-4-yl)-6,6-dimethyl-3-(phenylamino)-1,5,6,7-tetrahydro-4H-5,7-methanoindol-4-one,
rel-(4aR,7aS)-6-methyl-3-(phenylamino)-2-(pyridin-4-yl)-1,4a,5,6,7a,8-hexahydropyrrolo[3,4-f]indole-4,7-dione,
rel-(4aR,5aR)-3-(phenylamino)-2-(pyridin-4-yl)-4a,5,5a,6-tetrahydrocyclopropa[f]indol-4(1H)-one,
(4aR,5aR)-3-(phenylamino)-2-(pyridin-4-yl)-4a,5,5a,6-tetrahydrocyclopropa[f]indol-4(1H)-one,
(4aS,5aS)-3-(phenylamino)-2-(pyridin-4-yl)-4a,5,5a,6-tetrahydrocyclopropa[f]indol-4(1H)-one,
rel-(4aR,5aR)-N-4-[4-oxo-3-(phenylamino)-1,4,4a,5,5a,6-hexahydrocyclopropa[f]indol-2-yl]pyridin-2-ylacetamide,
rel-(4aR,5aR)-5a-methyl-3-(phenylamino)-2-(pyridin-4-yl)-4a,5,5a,6-tetrahydrocyclopropa[f]indol-4(1H)-one,
(4aR,5aR)-5a-methyl-3-(phenylamino)-2-(pyridin-4-yl)-4a,5,5a,6-tetrahydrocyclopropa[f]indol-4(1H)-one,
(4aS,5aS)-5a-methyl-3-(phenylamino)-2-(pyridin-4-yl)-4a,5,5a,6-tetrahydrocyclopropa[f]indol-4(1H)-one,
N-4-[(4aR,5aR)-5a-methyl-4-oxo-3-(phenylamino)-1,4,4a,5,5a,6-hexahydrocyclopropa[f]indol-2-yl]pyridin-2-ylacetamide,
N-4-[(4aS,5aS)-5a-methyl-4-oxo-3-(phenylamino)-1,4,4a,5,5a,6-hexahydrocyclopropa[f]indol-2-yl]pyridin-2-ylacetamide,
3-(phenylamino)-2-(pyridin-4-yl)cyclohepta[b]pyrrol-4(1H)-one,
3-(phenylamino)-2-(pyridin-4-yl)-5,6,7,8-tetrahydrocyclohepta[b]pyrrol-4(1H)-one,
2-(2-aminopyridin-4-yl)-7-methyl-3-(phenylamino)cyclohepta[b]pyrrol-4(1H)-one,
(7RS)-2-(2-aminopyridin-4-yl)-7-methyl-3-(phenylamino)-5,6,7,8-tetrahydrocyclohepta[b]pyrrol-4(1H)-one,
N-{4-[(7RS)-3-anilino-7-methyl-4-oxo-1,4,5,6,7,8-hexahydrocyclohepta[b]pyrrol-2-yl]pyridin-2-yl}acetamide,
rel-(4aR,5aR)-2-(2-aminopyridin-4-yl)-3-anilino-5a-methyl-4a,5,5a,6-tetrahydrocyclopropa[f]indol-4(1H)-one,
N-{4-[rel-(4aR,5aR)-3-anilino-5a-methyl-4-oxo-1,4,4a,5,5a,6-hexahydrocyclopropa[f]indol-2-yl]pyridin-2-yl}methanesulfonamide,
N-[4-(3-anilino-7-methyl-4-oxo-1,4-dihydrocyclohepta[b]pyrrol-2-yl)pyridin-2-yl]methanesulfonamide,
1-fluoro-N-4-[rel-(4aS,5aR)-5a-methyl-4,6-dioxo-3-(phenylamino)-1,4,4a,5,5a,6-hexahydrocyclopropa[f]indol-2-yl]pyridin-2-ylcyclopropanecarboxamide,
1-fluoro-N-4-[(4aS,5aS)-5a-methyl-4-oxo-3-(phenylamino)-1,4,4a,5,5a,6-hexahydrocyclopropa[f]indol-2-yl]pyridin-2-ylcyclopropanecarboxamide,
1-fluoro-N-4-[(4aR,5aR)-5a-methyl-4-oxo-3-(phenylamino)-1,4,4a,5,5a,6-hexahydrocyclopropa[f]indol-2-yl]pyridin-2-ylcyclopropanecarboxamide,
N-4-[rel-(4aS,5aR)-5a-methyl-4,6-dioxo-3-(phenylamino)-1,4,4a,5,5a,6-hexahydrocyclopropa[f]indol-2-yl]pyridin-2-ylcyclopropanecarboxamide,
N-{4-[rel-(4aR,5aS)-3-Anilino-5a-methyl-4,6-dioxo-1,4,4a,5,5a,6-hexahydrocyclopropa[f]indol-2-yl]pyridin-2-yl}-1-methylcyclopropanecarboxamide,
1-methyl-N-4-[rel-(4aS,5aR)-5a-methyl-4,6-dioxo-3-(phenylamino)-1,4,4a,5,5a,6-hexahydrocyclopropa[f]indol-2-yl]pyridin-2-yl-1H-pyrazole-3-carboxamide,
4-fluoro-3-methoxy-N-4-[rel-(4aS,5aR)-5a-methyl-4,6-dioxo-3-(phenylamino)-1,4,4a,5,5a,6-hexahydrocyclopropa[f]indol-2-yl]pyridin-2-ylbenzamide,
(1S,2S)-2-fluoro-N-4-[(4aS,5aS)-5a-methyl-4-oxo-3-(phenylamino)-1,4,4a,5,5a,6-hexahydrocyclopropa[f]indol-2-yl]pyridin-2-ylcyclopropanecarboxamide,
(1S,2S)-2-fluoro-N-4-[(4aR,5aR)-5a-methyl-4-oxo-3-(phenylamino)-1,4,4a,5,5a,6-hexahydrocyclopropa[f]indol-2-yl]pyridin-2-ylcyclopropanecarboxamide,
N-4-[(7S)-7-methyl-4-oxo-3-(phenylamino)-1,4,5,6,7,8-hexahydrocyclohepta[b]pyrrol-2-yl]pyridin-2-ylacetamide,
N-4-[(7R)-7-methyl-4-oxo-3-(phenylamino)-1,4,5,6,7,8-hexahydrocyclohepta[b]pyrrol-2-yl]pyridin-2-ylacetamide,
2-fluoro-2-methyl-N-4-[(4aS,5aS)-5a-methyl-4-oxo-3-(phenylamino)-1,4,4a,5,5a,6-hexahydrocyclopropa[f]indol-2-yl]pyridin-2-ylpropanamide,
2-fluoro-2-methyl-N-4-[(4aR,5aR)-5a-methyl-4-oxo-3-(phenylamino)-1,4,4a,5,5a,6-hexahydrocyclopropa[f]indol-2-yl]pyridin-2-ylpropanamide,
1-methyl-N-4-[(4aS,5aS)-5a-methyl-4-oxo-3-(phenylamino)-1,4,4a,5,5a,6-hexahydrocyclopropa[f]indol-2-yl]pyridin-2-yl-1H-pyrazole-5-carboxamide,
1-methyl-N-4-[(4aR,5aR)-5a-methyl-4-oxo-3-(phenylamino)-1,4,4a,5,5a,6-hexahydrocyclopropa[f]indol-2-yl]pyridin-2-yl-1H-pyrazole-5-carboxamide,
N-4-[(4aS,5aS)-5a-methyl-4-oxo-3-(phenylamino)-1,4,4a,5,5a,6-hexahydrocyclopropa[f]indol-2-yl]pyridin-2-yl-1H-pyrazole-3-carboxamide,
N-4-[(4aR,5aR)-5a-methyl-4-oxo-3-(phenylamino)-1,4,4a,5,5a,6-hexahydrocyclopropa[f]indol-2-yl]pyridin-2-yl-1H-pyrazole-3-carboxamide,
N-{4-[(4aR,5aR)-3-anilino-5a-methyl-4-oxo-1,4,4a,5,5a,6-hexahydrocyclopropa[f]indol-2-yl]pyridin-2-yl}-2,6-difluorobenzamide,
N-{4-[(4aS,5aS)-3-anilino-5a-methyl-4-oxo-1,4,4a,5,5a,6-hexahydrocyclopropa[f]indol-2-yl]pyridin-2-yl}-2,6-difluorobenzamide,
N-{4-[(4aR,5aR)-3-anilino-5a-methyl-4-oxo-1,4,4a,5,5a,6-hexahydrocyclopropa[f]indol-2-yl]pyridin-2-yl}-4-fluoro-2-methylbenzamide,
N-{4-[(4aS,5aS)-3-anilino-5a-methyl-4-oxo-1,4,4a,5,5a,6-hexahydrocyclopropa[f]indol-2-yl]pyridin-2-yl}-4-fluoro-2-methylbenzamide,
N-{4-[(4aR,5aR)-3-anilino-5a-methyl-4-oxo-1,4,4a,5,5a,6-hexahydrocyclopropa[f]indol-2-yl]pyridin-2-yl}-3-fluoro-4-methoxybenzamide, and
N-{4-[(4aS,5aS)-3-anilino-5a-methyl-4-oxo-1,4,4a,5,5a,6-hexahydrocyclopropa[f]indol-2-yl]pyridin-2-yl}-3-fluoro-4-methoxybenzamide,
or an N-oxide, a salt, a tautomer or a stereoisomer of said compound, or a salt of said N-oxide, tautomer or stereoisomer.

### Claim 6 (depends on 1)

A method for the treatment of a haematological tumor, solid tumor, and/or matastases thereof, comprising administering to a patient in need thereof a therapeutically effective amount of a compound according to claim 1, wherein the tumor is a cervical tumor, a breast tumor, a non-small cell lung tumor, a prostate tumor, a colon tumor, or a melanoma tumor and/or metastases thereof.

### Claim 7 (depends on 1)

A pharmaceutical composition comprising at least one compound according to claim 1, together with at least one pharmaceutically acceptable auxiliary.

### Claim 8 (depends on 7)

A method for the treatment of a haematological tumor, solid tumor, and/or matastases thereof, comprising administering to a patient in need thereof a therapeutically effective amount of a pharmaceutical composition according to claim 7, wherein the tumor is a cervical tumor, a breast tumor, a non-small cell lung tumor, a prostate tumor, a colon tumor, or a melanoma tumor and/or metastases thereof.