# US 9,040,529 B2 · 4-phenylamino-pyrimidine derivatives having protein kinase inhibitor activity

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- Number: US 9,040,529 B2
- Document ID: US9040529B2
- Status: Granted
- Kind: B2
- Application number: 13/517,120
- Filed: 2010-12-17
- Published: 2012-10-11
- Granted: 2015-05-26
- Earliest claimed: 2009-12-21
- Assignees: Vichem Chemie Kutató Kft.
- Applicants: Zoltán Greff; Zoltán Varga; György Kéri; Gábor Németh; László Örfi; Csaba Szántai Kis
- Inventors: Zoltán Greff; Zoltán Varga; György Kéri; Gábor Németh; László Örfi; Csaba Szántai Kis
- Web page: https://patentgrep.com/patent/US9040529B2

## CPC

- C07D 239/42: One nitrogen atom (nitro radicals C07D239/30)
- A61P 9/00: Drugs for disorders of the cardiovascular system
- A61P 25/04: Centrally acting analgesics, e.g. opioids
- A61P 29/00: Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- A61P 31/00: Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P 35/00: Antineoplastic agents
- A61P 43/00: Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C07D 401/04: directly linked by a ring-member-to-ring-member bond
- C07D 403/04: directly linked by a ring-member-to-ring-member bond
- C07D 403/14: containing three or more hetero rings
- C07D 409/14: containing three or more hetero rings
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

The invention relates compounds of general formula (I) and pharmaceutically acceptable salts and solvates thereof wherein R1 is halogen, vinylene-aryl, substituted aryl, heteroaryl or a benzo[1,3]dioxolil group, W is a group of formula —NH—SO2—R2 or heteroaryl group or NHR3 group where R3 is hydrogen or heteroaryl; and n is 1, 2, 3 or 4. Furthermore, the present invention is directed to pharmaceutical composition containing at least one compound of general formula (I) and/or pharmaceutically acceptable salts or solvates thereof and for the use of them for the preparation of pharmaceutical compositions for the prophylaxis and/or the treatment of protein kinase related, especially CDK9-related diseases e.g. cell proliferative disease, infectious disease, pain, cardiovascular disease and inflammation.

## Claims

### Claim 1

A compound of general formula (I) and pharmaceutically acceptable salts and solvates thereof
wherein
R1 is halogen;
vinylene-aryl;
aryl, which is substituted with one or more substituent selected from the following group:
alkoxy which is optionally substituted with one or more halogen or with aryl which is optionally substituted with one or more halogen, alkyl or alkoxy,
halogen,
alkyl which is optionally subsituted with one or more halogen or alkoxy,
alkylaryloxy which is optionally substituted with alkoxy which is optionally substituted with one or more halogen,
aminocarbonyl,
amino, which is optionally substituted with one or two alkyl;
alkylthio,
alkylsulfinyl or alkylsulfonyl,
aryloxy,
hydroxyl;
group of formula (a)
wherein m is 1, 2 or 3 and R′ is hydrogen, halogen, alkyl or alkoxy;
heteroaryl;
W is a
group of formula (b)
wherein R2 stands for
alkyl, alkoxy or aryl, which groups are optionally substituted with one or more halogen,
heteroaryl,
benzyl, which is optionally substituted with one or more halogen, alkyl or alkoxy,
amino, which is optionally substituted with one or two alkyl;
heteroaryl group, which is optionally substituted with a (CH2)k-heterocycloalkyl group, where k is 0, 1, 2 or 3;
NH—R3, wherein R3 is hydrogen, alkyl, alkoxy, aryl, aryloxy, heteroaryl, heteroaryloxy, aminoalkyl, aminoaryl or aminoheteroaryl, or R3 is —CO-aryl, —CO—NH-aryl where the aryl is optionally substituted with one or more halogen; and
n is 1, 2, 3 or 4.

### Claim 2 (depends on 1)

A compound according to claim 1, where the heteroaryl in the meaning of R1 is 5- or 6-membered heteroaryl containing 1 or 2 N-atom.

### Claim 3 (depends on 1)

A compound according to claim 1, where the heteroaryl in the meaning of R2 is 5- or 6-membered heteroaryl containing 1 or 2 S-atom.

### Claim 4 (depends on 1)

A compound according to claim 1, where the heteroaryl in the meaning of W is a fused bicyclic heteroaryl group containing at least one heteroatom selected from the group of N, O and S in one of the rings and the other ring is a benzene ring, optionally substituted with 1 or 2 oxo group in the nitrogen containing ring and with one or more halogen, alkyl or alkoxy in the benzene ring.

### Claim 5 (depends on 1)

A compound according to claim 1, where the heteroaryl in the meaning of W is a 1-benzoimidazolyl group.

### Claim 6 (depends on 1)

A compound according to claim 1, where the heterocyloalkyl substituent of the heteroaryl in the meaning of W is a saturated ring of 4 to 7 atoms, wherein 1 or 2 ring member(s) is/are selected from the group consisting of O, S and NRx, where Rx is hydrogen or alkyl.

### Claim 7 (depends on 1)

A compound according to claim 1, where the heteroaryl in the meaning of R3 is a bicyclic fused heteroaryl group containing at least one heteroatom selected from the group of N, O and S in one of the rings and the other ring is a benzene ring.

### Claim 8 (depends on 1)

A compound according to claim 1, where R3 is —CO-aryl or —CO—NH-aryl, where the aryl is optionally substituted with one or more halogen.

### Claim 9 (depends on 1)

Pharmaceutical composition containing as active ingredient one or more compound(s) of general formula (I) according to claim 1 together with one or more pharmaceutical auxiliary material(s).