US Patent No. 9,290,496

PURINE DERIVATIVES


Patent No. 9,290,496
Issue Date March 22, 2015
Title Purine Derivatives
Inventorship Douglas Carl Behenna, San Juan Capistrano, CA (US)
Hengmiao Cheng, San Diego, CA (US)
Sujin Cho-Schultz, San Diego, CA (US)
Theodore Otto Johnson, Jr., San Diego, CA (US)
John Charles Kath, La Mesa, CA (US)
Asako Nagata, San Diego, CA (US)
Sajiv Krishnan Nair, Vista, CA (US)
Simon Paul Planken, San Diego, CA (US)
Assignee PFIZER INC., New York, NY (US)

Claim of US Patent No. 9,290,496

1. A compound of formula (IIIa):
wherein
R1 is hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, 4-6 membered heterocycloalkyl, or 4-6 membered heteroaryl, wherein the C1-C6 alkyl is optionally substituted by one, two or three substituents selected from the group consisting of halogen, hydroxy,
and C1-C3 alkoxy, further wherein the C3-C6 cycloalkyl, the 4-6 membered heterocycloalkyl, and the 4-6 membered heteroaryl are each independently optionally substituted
by one, two or three substituents selected from the group consisting of C1-C3 alkyl, hydroxy, and C1-C3 alkoxy;

R2 and R5 are each independently hydrogen, halogen, cyano, difluoromethyl, trifluoromethyl, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 alkoxy, —N(R10)(R11), C3-C5 cycloalkyl, or 4-6 membered heterocycloalkyl, wherein the C1-C6 alkyl is optionally substituted by one, two or three substituents selected from the group consisting of halogen, hydroxy,
C1-C6 alkoxy, and —N(R12)(R13),

provided that at least one of R2 or R5 is hydrogen;

R3 is hydrogen, halogen, C1-C6 alkyl, C2-C6 alkynyl, C1-C6 alkoxy, C3-C7 cycloalkyl, or 3-7 membered heterocycloalkyl, wherein the C1-C6 alkyl and the C1-C6 alkoxy are each optionally substituted by one, two or three R14 groups, and further wherein the C3-C7 cycloalkyl and the 3-7 membered heterocycloalkyl are each optionally substituted by one, two or three R15 groups;

R6 and R8 are each independently hydrogen, halogen, cyano, hydroxy, difluoromethyl, trifluoromethyl, C1-C3 alkyl, C1-C3 alkoxy, or C3-C5 cycloalkyl, wherein the C1-C3 alkyl is optionally substituted by hydroxy, difluoromethyl, trifluoromethyl, C1-C3 alkoxy, or C3-C5 cycloalkyl;

R7 is


G is —NR18—;

R10 and R11 are each independently hydrogen or C1-C6 alkyl; or R10 and R11 together with the nitrogen to which they are attached, may combine to form a 4-7 membered heterocycloalkyl ring, when R10 and R1l are each C1-C3 alkyl, wherein the 4-7 membered heterocycloalkyl ring formed is optionally substituted by one, two, three or four R15 groups;

R12 and R13 are each independently hydrogen or C1-C3 alkyl;

each R14 is independently halogen, cyano, C1-C3 alkyl, hydroxy, C1-C6 alkoxy,—N(R19)(R20), —CON(R21)(R22), or 3-7 membered heterocycloalkyl, wherein the 3-7 membered heterocycloalkyl is optionally substituted by one, two, three
or four R15 groups;

each R15 is independently halogen, C1-C3 alkyl, hydroxy, C1-C6 alkoxy, —NH2, —NHCH3, or —N(CH3)2;

R16 and R17 are each independently hydrogen or C1-C6 alkyl, wherein the C1-C6 alkyl is optionally substituted by —N(R23)(R24),

provided that R16 and R17 may form C3-C5 cycloakyl ring;

R18 is hydrogen or C1-C3 alkyl;

each R19, R20, R21, R22, R23, and R24 is independently hydrogen or C1-C3 alkyl;

n is 0, 1, or 2; and
p is 0, 1, or 2; or
a pharmaceutically acceptable salt thereof.