# US 10,766,884 B2 · Cyclin dependent kinase inhibitors

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- Number: US 10,766,884 B2
- Document ID: US10766884B2
- Status: Granted
- Kind: B2
- Application number: 16/391,836
- Filed: 2019-04-23
- Published: 2019-10-31
- Granted: 2020-09-08
- Earliest claimed: 2018-04-26
- Assignees: Pfizer Inc.
- Applicants: Pfizer Inc.
- Inventors: Ping Chen; Sujin Cho-Schultz; Judith Gail Deal; Gary Michael Gallego; Mehran Jalaie; Robert Steven Kania; Sajiv Krishnan Nair; Sacha Ninkovic; Suvi Tuula Marjukka Orr; Cynthia Louise Palmer
- Web page: https://patentgrep.com/patent/US10766884B2

## CPC

- C07D 407/14: containing three or more hetero rings
- A61P 35/00: Antineoplastic agents
- C07D 401/14: containing three or more hetero rings
- C07D 405/14: containing three or more hetero rings
- C07D 487/04: Ortho-condensed systems
- C07D 498/04: Ortho-condensed systems
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

This invention relates to compounds of Formula (I) or a pharmaceutically acceptable salt thereof, in which R-groups R1 to R23, A, Q, U, V, W, X, Y, Z, n, p and q are as defined herein, to pharmaceutical compositions comprising such compounds and salts, and to methods of using such compounds, salts and compositions for the treatment of abnormal cell growth, including cancer, in a subject.

## Claims

### Claim 1

A compound of Formula (XI):
or a pharmaceutically acceptable salt thereof, wherein:
R1 is H, F, Cl, CN, C1-C2 alkyl or C1-C2 fluoroalkyl, where each said C1-C2 alkyl and C1-C2 fluoroalkyl is optionally substituted by R20;
R2 is H, C1-C5 alkyl, C1-C5 fluoroalkyl, C3-C8 cycloalkyl or 3-6 membered heterocyclyl, where each said C1-C5 alkyl and C1-C5 fluoroalkyl is optionally substituted by R20 and each said C3-C8 cycloalkyl and 3-6 membered heterocyclyl is optionally substituted by R21;
R4 is H, C1-C4 alkyl, C1-C4 fluoroalkyl, C1-C4 alkoxy or C1-C4 fluoroalkoxy, where each said C1-C4 alkyl, C1-C4 fluoroalkyl, C1-C4 alkoxy and C1-C4 fluoroalkoxy is optionally substituted by R20; or
R2 can be taken together with R4 to form a 5-7 membered heterocyclic ring, optionally containing an additional heteroatom selected from NR24, O and S(O)m as a ring member, which ring is optionally substituted by R21;
R6 is H, F, Cl, CN, CH3, CH2F, CHF2 or CF3;
R7 and R8 are independently H, F, Cl, CN, C1-C2 alkyl, C1-C2 fluoroalkyl, C1-C2 alkoxy or C1-C2 fluoroalkoxy, where each said C1-C2 alkyl, C1-C2 fluoroalkyl, C1-C2 alkoxy and C1-C2 fluoroalkoxy is optionally substituted by R20;
R9 is H, OH, NH2, NHCH3 or N(CH3)2;
each R10 is independently F, CN, C1-C2 alkyl or C1-C2 fluoroalkyl, where each said C1-C2 alkyl and C1-C2 fluoroalkyl is optionally substituted by R20;
each R20 is independently OH, C1-C2 alkoxy, C1-C2 fluoroalkoxy, CN or NR22R23;
each R21 is independently F, OH, CN, NR22R23, C1-C4 alkyl, C1-C4 fluoroalkyl, C1-C4 alkoxy or C1-C4 fluoroalkoxy, where each said C1-C4 alkyl, C1-C4 fluoroalkyl, C1-C4 alkoxy and C1-C4 fluoroalkoxy is optionally further substituted by OH, NH2, NHCH3 or N(CH3)2;
each R22 and R23 is independently H, C1-C2 alkyl or C1-C2 fluoroalkyl; or
R22 and R23 may be taken together with the nitrogen atom to which they are attached to form an azetidinyl ring, which is optionally substituted by F or OH;
R24 is H, C1-C4 alkyl, C1-C4 fluoroalkyl, SO2R25, SO2NR26R27, COR28, COOR28 or CONR29R30;
R25 is C1-C4 alkyl or C1-C4 fluoroalkyl;
each R26 and R27 is independently H or CH3;
R28 is C1-C4 alkyl or C1-C4 fluoroalkyl, where each said C1-C4 alkyl and C1-C4 fluoroalkyl is optionally substituted by OH, C1-C2 alkoxy, C1-C2 fluoroalkoxy, CN, NH2, NHCH3 or N(CH3)2;
each R29 and R30 is independently H, C1-C4 alkyl or C1-C4 fluoroalkyl, where each said C1-C4 alkyl and C1-C4 fluoroalkyl is optionally substituted by OH, C1-C2 alkoxy, C1-C2 fluoroalkoxy, CN, NH2, NHCH3 or N(CH3)2;
m is 0, 1 or 2; and
n is 0, 1, 2, 3 or 4.

### Claim 2 (depends on 1)

The compound of claim 1, or a pharmaceutically acceptable salt thereof, wherein R9 is OH.

### Claim 3

1,5-anhydro-3-({5-chloro-4-[4-fluoro-2-(2-hydroxypropan-2-yl)-1-(propan-2-yl)-1H-benzimidazol-6-yl]pyrimidin-2-yl}amino)-2,3-dideoxy-D-threo-pentitol, or a pharmaceutically acceptable salt thereof.

### Claim 4 (depends on 1)

A pharmaceutical composition comprising the compound of claim 1, or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable carrier or excipient.

### Claim 5 (depends on 3)

A pharmaceutical composition comprising the compound of claim 3, or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable carrier or excipient.

### Claim 6 (depends on 1)

A method for the treatment of cancer in a subject in need thereof, comprising administering to the subject a therapeutically effective amount of the compound of claim 1, or a pharmaceutically acceptable salt thereof.

### Claim 7 (depends on 3)

A method for the treatment of cancer in a subject in need thereof, comprising administering to the subject a therapeutically effective amount of the compound of claim 3, or a pharmaceutically acceptable salt thereof.

### Claim 8 (depends on 1)

The compound of claim 1, or a pharmaceutically acceptable salt thereof, wherein R1 is Cl.

### Claim 9 (depends on 1)

The compound of claim 1, or a pharmaceutically acceptable salt thereof, wherein R2 is C1-C5 alkyl.

### Claim 10 (depends on 1)

The compound of claim 1, or a pharmaceutically acceptable salt thereof, wherein R4 is C1-C4 alkyl optionally substituted by R20, where R20 is OH.

### Claim 11 (depends on 1)

The compound of claim 1, or a pharmaceutically acceptable salt thereof, wherein R6 is F, R7 is H, and R8 is H.

### Claim 12 (depends on 1)

The compound of claim 1, or a pharmaceutically acceptable salt thereof, wherein n is 0 and R10 is absent.

### Claim 13 (depends on 1)

The compound of claim 1, having the Formula (XI-A):
or a pharmaceutically acceptable salt thereof.

### Claim 14 (depends on 13)

The compound of claim 13, or a pharmaceutically acceptable salt thereof, wherein R9 is OH, n is 0 and R10 is absent.

### Claim 15 (depends on 13)

The compound of claim 13, or a pharmaceutically acceptable salt thereof, wherein R1 is Cl.

### Claim 16 (depends on 13)

The compound of claim 13, or a pharmaceutically acceptable salt thereof, wherein R2 is i-C3H7.

### Claim 17 (depends on 13)

The compound of claim 13, or a pharmaceutically acceptable salt thereof, wherein R4 is C1-C4 alkyl substituted by R20, where R20 is OH.

### Claim 18 (depends on 13)

The compound of claim 13, or a pharmaceutically acceptable salt thereof, wherein R6 is F, R7 is H, and R8 is H.

### Claim 19

1,5-anhydro-3-({5-chloro-4-[4-fluoro-2-(2-hydroxypropan-2-yl)-1-(propan-2-yl)-1H-benzimidazol-6-yl]pyrimidin-2-yl}amino)-2,3-dideoxy-D-threo-pentitol.

### Claim 20

A pharmaceutically acceptable salt of 1,5-anhydro-3-({5-chloro-4-[4-fluoro-2-(2-hydroxypropan-2-yl)-1-(propan-2-yl)-1H-benzimidazol-6-yl]pyrimidin-2-yl}amino)-2,3-dideoxy-D-threo-pentitol.