US Patent No. 9,758,538

PYRIMIDINE DERIVATIVES


Patent No. 9,758,538
Issue Date September 12, 2017
Title Pyrimidine Derivatives
Inventorship Ping Chen, San Diego, CA (US)
Hengmiao Cheng, San Diego, CA (US)
Gary Michael Gallego, San Diego, CA (US)
Mehran Jalaie, San Diego, CA (US)
John Charles Kath, La Mesa, CA (US)
Suvi Tuula Marjukka Orr, San Diego, CA (US)
Mason Alan Pairish, San Diego, CA (US)
Assignee PFIZER INC., New York, NY (US)

Claim of US Patent No. 9,758,538

1. A compound of formula (I)
or a pharmaceutically acceptable salt thereof,wherein
X is N or CR2;

R1 is hydrogen or methyl;

R2 is hydrogen, fluorine, or chlorine;

R3 is methyl or NH2;

Y is N or CR4;

R4 is hydrogen, cyano, or fluorine;

R5 is hydrogen, methyl, or CF3;

Z is NR6 or O;

R6 is hydrogen or C1-C3 alkyl;

R7 is hydrogen,

C1-C4 alkyl, optionally substituted by one, two, or three substituents selected from the group consisting of fluorine, hydroxy,
and NH2,

—CH2—(C3-C4 cycloalkyl),

—C(O)—(C1-C6 alkyl), optionally substituted by one, two, or three substituents selected from the group consisting of fluorine, NH2, hydroxy, methoxy, and phenyl,

—C(O)—(C3-C4 cycloalkyl), optionally substituted by one or two substituents selected from the group consisting of fluorine and C1-C4 alkyl,

—[(CH2)]p—C(O)-(4-5 membered heterocycloalkyl), optionally substituted by one or two substituents selected from the group consisting
of fluorine and C1-C4 alkyl,

—C(O)-(5-6 membered heteroaryl), optionally substituted by one or two substituents selected from the group consisting of fluorine
and C1-C4 alkyl,

—[(CH2)]p—C(O)—[N(R10)(R11)],

—C(O)O—(C1-C4 alkyl), optionally substituted by one, two, or three substituents selected from the group consisting of fluorine, NH2, hydroxy, methoxy, and phenyl,

—C(O)O—(C3-C4 cycloalkyl), optionally substituted by one or two substituents selected from the group consisting of fluorine and C1-C4 alkyl,

—S(O)2—(C1-C4 alkyl),

4-6 membered heterocycloalkyl, optionally substituted by one or two substituents selected from the group consisting of oxo
and C1-C4 alkyl, or

5-6 membered heteroaryl, optionally substituted by one or two substituents selected from the group consisting of oxo and C1-C4 alkyl;

R8 is —CH2OH or —CH2—O—P(O)(OH)2;

R9 is fluorine or methyl;

R10 is hydrogen or methyl;

R11 is C1-C4 alkyl, optionally substituted by one, two, or three fluorine atoms,

provided that R10 and R11 may form a 4-6 membered heterocycloalkyl ring, when p is 0;

m is 0, 1, or 2;
n is 0, 1, or 2; and
p is 0 or 1.