# US 2013/0158032 A1 · Aminopyrimidine derivatives as lrrk2 modulators

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- Number: US 2013/0158032 A1
- Document ID: US20130158032A1
- Status: Published application
- Kind: A1
- Application number: 13/687,411
- Filed: 2012-11-28
- Published: 2013-06-20
- Earliest claimed: 2011-11-29
- Assignees: Genentech, Inc.
- Inventors: Charles Baker-Glenn; Mark Chambers; Bryan K. Chan; Anthony Estrada; Daniel Shore; Zachary Kevin Sweeney; Huifen Chen
- Web page: https://patentgrep.com/patent/US20130158032A1

## CPC

- C07D 413/12: linked by a chain containing hetero atoms as chain links
- A61P 25/16: Anti-Parkinson drugs
- A61P 43/00: Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C07D 239/42: One nitrogen atom (nitro radicals C07D239/30)
- C07D 239/48: Two nitrogen atoms
- C07D 401/04: directly linked by a ring-member-to-ring-member bond
- C07D 401/12: linked by a chain containing hetero atoms as chain links
- 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 405/12: 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: or pharmaceutically acceptable salts thereof, wherein m, n. X, R1, R2, R3, R4 and R5 are as defined herein. Also disclosed are methods of making the compounds and using the compounds for treatment of diseases associated with LRRK2 receptor, such as Parkinson's disease.

## Claims

### Claim 1

A compound of formula I:
or pharmaceutically acceptable salts thereof,
wherein:
m is from 0 to 3;
X is: —NRa—; —O—; or —S(O)r— wherein r is from 0 to 2 and Ra is hydrogen or C1-6alkyl;
R1 is: C1-6alkyl; C1-6alkenyl; C1-6alkynyl; halo-C1-6alkyl; C1-6alkoxy-C1-6alkyl; hydroxy-C1-6alkyl; amino-C1-6alkyl; C1-6alkylsulfonyl-C1-6alkyl; C3-6cycloalkyl optionally substituted with C1-6alkyl; C3-6cycloalkyl-C1-6alkyl wherein the C3-6cycloalkyl portion is optionally substituted with C1-6alkyl; tetrahydrofuranyl; tetrahydrofuranyl-C1-6alkyl; oxetanyl; or oxetan-C1-6alkyl;
or R1 and Ra together with the atoms to which they are attached may form a three to six membered ring that may optionally include an additional heteroatom selected from O, N and S, and which is substituted with oxo, halo or C1-6alkyl;
R2 is: halo; C1-6alkoxy; cyano; C1-6alkynyl; C1-6alkenyl; halo-C1-6alkyl; halo-C1-6alkoxy; C3-6cycloalkyl wherein the C3-6cycloalkyl portion is optionally substituted with C1-6alkyl; C3-6cycloalkyl-C1-6alkyl wherein the C3-6cycloalkyl portion is optionally substituted with C1-6alkyl; tetrahydrofuranyl; tetrahydrofuranyl-C1-6alkyl; acetyl; oxetanyl; or oxetan-C1-6alkyl;
R3 and R4 each independently is: halo; C1-6alkyl; C1-6alkoxy; C3-6cycloalkyloxy; halo-C1-6alkyl; or halo-C1-6alkoxy;
or R3 and R4 together with the atoms to which they are attached may form a five- or six-membered ring that optionally includes one or two heteroatoms each independently selected from O, N and S, the ring being optionally substituted one or more times with R6;
R5 is: C1-6alkyl-sulfonyl; C3-6cycloalkylsulfonyl; C3-6cycloalkyl-C1-6alkylsulfonyl; cyano; cyano-C1-6alkyl; heterocyclyl optionally substituted one or more times with R6; heterocyclyl-C1-6alkyl wherein the heterocyclyl moiety is optionally substituted one or more times with R6; halo-C1-6alkyl; heterocyclyl-sulfonyl wherein the heterocyclyl moiety is optionally substituted one or more times with R6; or carboxy; and
R6 is: C1-6alkyl; halo; halo-C1-6alkyl; or oxo.

### Claim 2 (depends on 1)

The compound of claim 1, wherein m is 0 or 1.

### Claim 3 (depends on 1)

The compound of claim 1, wherein —NH— or —O—.

### Claim 4 (depends on 1)

The compound of claim 1, wherein R1 is C1-6alkyl.

### Claim 5 (depends on 1)

The compound of claim 1, wherein R1 is methyl.

### Claim 6 (depends on 1)

The compound of claim 1, wherein R2 is: halo; halo-C1-6alkyl; or cyano.

### Claim 7 (depends on 1)

The compound of claim 1, wherein R2 is chloro or trifluoromethyl.

### Claim 8 (depends on 1)

The compound of claim 1, wherein R3 is fluoro, chloro or methoxy.

### Claim 9 (depends on 1)

The compound of claim 1, wherein R3 is methoxy.

### Claim 10 (depends on 1)

The compound of claim 1, wherein R4 is fluoro, chloro, methyl or methoxy.

### Claim 11 (depends on 1)

The compound of claim 1, wherein R5 is C1-6alkyl-sulfonyl or cyano.

### Claim 12 (depends on 1)

The compound of claim 1, wherein R5 is C1-6alkyl-sulfonyl.

### Claim 13 (depends on 1)

The compound of claim 1, wherein R5 is: methanesulfonyl; cyano; morpholin-4-yl-methyl; morpholin-4-yl; morpholin-4-yl-sulfonyl; or trifluoromethyl.

### Claim 14 (depends on 1)

The compound of claim 1, wherein R5 is: methanesulfonyl; cyano; or morpholin-4-yl-methyl.

### Claim 15 (depends on 1)

The compound of claim 1, wherein R5 is: methanesulfonyl; or cyano.

### Claim 16 (depends on 1)

The compound of claim 1, wherein R5 is cyano.

### Claim 17 (depends on 1)

The compound of claim 1, wherein R5 is methanesulfonyl.

### Claim 18 (depends on 1)

A composition comprising:
(a) a pharmaceutically acceptable carrier; and
(b) a compound of claim 1.

### Claim 19 (depends on 1)

A method for treating Parkinson's disease, said method comprising administering to a subject in need thereof an effective amount of a compound of claim 1.