# US 7,612,079 B2 · 2,6,9-substituted purine derivatives and their use in the treatment of proliferative disorders

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- Number: US 7,612,079 B2
- Document ID: US7612079B2
- Status: Granted
- Kind: B2
- Application number: 10/742,237
- Filed: 2003-12-18
- Published: 2005-01-13
- Granted: 2009-11-03
- Earliest claimed: 2001-06-27
- Assignees: Cyclacel Limited; Cancer Research Technology Limited
- Inventors: Peter Martin Fischer; Mike Jarman; Ted McDonald; Bernard Nutley; Florence Raynaud; Stuart Wilson; Paul Workman
- Web page: https://patentgrep.com/patent/US7612079B2

## CPC

- C07D 473/16: two nitrogen atoms
- A61P 17/06: Antipsoriatics
- 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 31/12: Antivirals
- A61P 35/00: Antineoplastic agents
- A61P 35/02: specific for leukemia
- A61P 43/00: Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

The present invention relates to compounds of formula I or a pharmaceutically acceptable salt thereof wherein R2 is 2-hydroxymethylpyrrolidin-1-yl, or NHCH(R4)CH(R3)OH, wherein R3 is hydrogen or methyl and R4 is methyl, ethyl or isopropyl; R6 is 3-nitrophenylamino, 3,4-dimethoxybenzylamino, 3-iodobenzyl-amino, pyrid-2-yl-methylamino, pyrid-4-yl-methylamino or indan-5-amino; R9 is isopropyl or cyclopentanyl. In a further aspect, the invention relates to pharmaceutical compositions comprising said compounds, and the use thereof in treating antiproliferative disorders and or viral disorders.

## Claims

### Claim 1

A compound of formula I
or a pharmaceutically acceptable salt thereof wherein
R2 is 3-hydroxypiperidin-1-yl, or NHCH(R4)CH(R3)OH, wherein R3 is hydrogen or methyl and
R4 is methyl, ethyl or isopropyl;
R6 is 3-nitrophenylamino or indan-5-ylamino; and
R9 is isopropyl or cyclopentanyl.

### Claim 2 (depends on 1)

A compound according to claim 1 wherein R2 is NHCH(CHMe2)CH2OH or NHCH(CH2Me)CH2OH.

### Claim 3 (depends on 1)

A compound according to claim 1 selected from the following:

### Claim 4

A compound selected from the following:
or a pharmaceutically acceptable salt thereof.

### Claim 5

A compound of formula I
or a pharmaceutically acceptable salt thereof wherein
R2 is NHCH(R4)CH(R3)OH, wherein R3 is hydrogen or methyl and R4 is methyl, ethyl or isopropyl;
R6 is 3,4-dimethoxybenzylamino, pyrid-2-yl-methylamino, or pyrid-4-yl-methylamino; and
R9 is cyclopentanyl.

### Claim 6

A compound selected from the following:

### Claim 7 (depends on 1, 4, 5)

A pharmaceutical composition, comprising a compound according to claim 1, 4, 5, or 6 admixed with a pharmaceutically acceptable diluent, excipient or carrier, or a mixture thereof.

### Claim 8 (depends on 7)

The pharmaceutical composition of claim 7, wherein said compound is present in an amount sufficient to treat a proliferative disorder.

### Claim 9 (depends on 8)

The pharmaceutical composition of claim 8, wherein said proliferative disorder is cancer or leukaemia.

### Claim 10 (depends on 8)

The pharmaceutical composition of claim 8, wherein said proliferative disorder is psoriasis.

### Claim 11 (depends on 1, 4, 5)

An optical isomer of a compound of claim 1, 4, 5, or 6, wherein said optical isomer is a dextrorotatory (+) isomer.

### Claim 12 (depends on 1, 4, 5)

A compound of claim 1, 4, 5, or 6, wherein said compound is in the form of a racemate.

### Claim 13 (depends on 7)

The pharmaceutical composition of claim 7, wherein said compound is present in an amount sufficient to treat a neurodegenerative disorder.

### Claim 14 (depends on 7)

The pharmaceutical composition of claim 7, wherein said compound is present in an amount sufficient to prevent neuronal apoptosis.

### Claim 15 (depends on 7)

The pharmaceutical composition of claim 7, wherein said compound is present in an amount sufficient to be an antiviral agent.

### Claim 16 (depends on 7)

The pharmaceutical composition of claim 7, wherein said compound is present in an amount sufficient to be an anti-mitotic agent.

### Claim 17 (depends on 7)

The pharmaceutical composition of claim 7, wherein said compound is present in an amount sufficient to inhibit at least one of CDK2, CDK7, CDK8, or CDK9.

### Claim 18 (depends on 1, 4, 5)

A method of treating cancer, said method comprising administering to a mammal a therapeutically effective amount of a compound according to claim 1, 4, 5, or 6, such that said cancer is treated, wherein said cancer is an ovarian carcinoma.

### Claim 19 (depends on 18)

The method according to claim 18, wherein said compound is administered orally.

### Claim 20 (depends on 1, 4, 5)

A method of inhibiting a cyclin dependent kinase, said method comprising contacting said cyclin dependent kinase with a compound according to claim 1, 4, 5, or 6, such that said cyclin dependent kinase is inhibited, and wherein said cyclin dependent kinase is CDK2, CDK7, or CDK9.

### Claim 21 (depends on 20)

The method according to claim 20, wherein said cyclin dependent kinase is CDK2.

### Claim 22 (depends on 1, 4, 5)

An optical isomer of a compound of claim 1, 4, 5, or 6, wherein said optical isomer is a laevorotatory (−) isomer.