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US 2025/0073236 A1Published application
Pyrimidine compounds containing acidic groups
AssigneeApros Therapeutics, Inc.
InventorTom Yao-Hsiang WU
Life of this patent
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Abstract
The present disclosure relates to a class of pyrimidine derivatives having immunomodulating properties that act via TLR7 which are useful in the treatment of viral infections and cancers.
Claims59
A compound having the structure of Formula (1), or a pharmaceutically acceptable salt thereof,
- wherein
- R1a is selected from the group consisting of H, C1-C4 alkyl, —NH2, —NHAc, —COOH, —SO2CH3, —SCH3, —OCH3,
- and A,
- wherein the alkyl is optionally substituted with —OH, —NH2, —NHAc, —COOH, —SO2CH3, —SCH3, —OCH3,
- or A;
- R1b is C2-C5 alkyl;
- X is selected from the group consisting of H and C1-C4 alkyl, wherein the alkyl is optionally substituted with A, —OH, or —C(CH3)2OH;
- L1 is selected from the group consisting of a bond, —CH2—, —CF2—,
- —O—, —S—, —SO2—, —NH—, and —CH2CH2—;
- Y is selected from the group consisting of C1-C3 alkyl, aryl, and heteroaryl, wherein the alkyl, aryl, and heteroaryl are optionally substituted with 1-5 substituents that are independently selected from A, C1-C3 alkyl, and C1-C3 alkoxy;
- A is selected from the group consisting of
- L2 is selected from the group consisting of a bond, —(CH2)n—, —C(O)NH(CH2)n—,
- [O(CH2CH2)]n—, —[O(C1-C4 alkylene)]-, —[O(CH2CH2)]n—OCH2CH2CF2—;
- —C(O)NHCH2CH2—[O(CH2CH2)]m—;
- and —C(O)NHCH2CH2—[O(CH2CH2)]m—OCH2CH2CF2—;
- m is an integer from zero to four;
- n is an integer from one to four;
- wherein the compound is substituted with at least one A;
- and
- when X is —CH3;
- L1 is —CH2—;
- Y is aryl substituted with A;
- and L2 is —CH2—;
- then A is not —L2—COOH, except when R1a comprises —COOH or —SO2CH3;
- and
- when X is —CH3;
- L1 is —CH2—;
- Y is aryl substituted with A;
- L2 is —CH2—, O—(CH2)2—O(CH2)2—, or —O—(CH2)2—O(CH2)2 (CF2)—;
- and A is
- then A and L1 are not in a para position with respect to each other.
28 more elements
A compound having the structure of Formula (1), or a pharmaceutically acceptable salt thereof,
- wherein
- R1a is selected from the group consisting of H, C1-C4 alkyl, —NH2, —NHAc, —COOH, —SO2CH3, —SCH3, —OCH3, and
- wherein the alkyl is optionally substituted with —OH, —NH2, —NHAc, —COOH, —SO2CH3, —SCH3, —OCH3, or
- R1b is C2-C5 alkyl;
- X is selected from the group consisting of H and C1-C4 alkyl, wherein the alkyl is optionally substituted with A, —OH, or —C(CH3)2OH;
- L1 is selected from the group consisting of a bond, —CH2—, —CF2—,
- —O—, —S—, —SO2—, —NH—, and —CH2CH2—;
- Y is selected from the group consisting of C1-C3 alkyl, aryl, and heteroaryl, wherein the alkyl, aryl, and heteroaryl are optionally substituted with 1-5 substituents that are independently selected from A, C1-C3 alkyl, and C1-C3 alkoxy;
- A is selected from the group consisting of
- L2 is selected from the group consisting of a bond, —(CH2)n—, —C(O)NH(CH2)n—,
- [O(CH2CH2)]n—, —[O(C1-C4 alkylene)]-, —[O(CH2CH2)]n—OCH2CH2CF2—;
- —C(O)NHCH2CH2—[O(CH2CH2)]m—;
- and —C(O)NHCH2CH2—[O(CH2CH2)]m—OCH2CH2CF2—;
- m is an integer from zero to four;
- and
- n is an integer from one to four;
- and
- wherein the compound is substituted with at least one A;
- and
- when X is —CH3;
- L1 is —CH2—;
- Y is aryl substituted with A;
- and L2 is —CH2—;
- then A is not —L2—COOH, except when R1a comprises —COOH or —SO2CH3;
- and
- when X is —CH3;
- L1 is —CH2—;
- Y is aryl substituted with A;
- L2 is —CH2—, —O—(CH2)2—O(CH2)2—, or —O—(CH2)2—O(CH2)2 (CF2)—;
- and A is
- then A and L1 are not in a para position with respect to each other.
28 more elements
A compound, or a pharmaceutically acceptable salt, selected from the group consisting of:
- Com- pound
- —X
- —L1—Y
- Compound
- 1
- —CH3
- —(CH2)3CH3
- 2
- —CH3
- —(CH2)3CH3
- 3
- —CH3
- —(CH2)3CH3
- 4
- —CH3
- —(CH2)3CH3
- 5
- —CH3
- —(CH2)3CH3
- 6
- —CH3
- —(CH2)3CH3
- 7
- —CH3
- —(CH2)3CH3
- 8
- —CH3
- 9
- —CH3
- —(CH2)3CH3
- 10
- —CH3
- —(CH2)3CH3
- 11
- —CH3
- —(CH2)3CH3
- 12
- —CH3
- —(CH2)3CH3
- 13
- —CH3
- —(CH2)3CH3
- 14
- —CH3
- —(CH2)3CH3
- 15
- —(CH2)3CH3
- 16
- —CH3
- —(CH2)3CH3
- 17
- —CH3
- —(CH2)3CH3
- 18
- —CH3
- 19
- —(CH2)3CH3
- 20
- —CH3
- 20C
- —CH3
- 21
- —OCH3
- 22
- —CH3
- 23
- —CH3
- 24
- —CH3
- —(CH2)3CH3
- 25
- —CH3
- —(CH2)3CH3
- 26
- —CH3
- —(CH2)4CH3
- 27
- 28
- —CH3
- —(CH2)3CH3
- 29
- 30
- —CH3
- —(CH2)3CH3
- 31
- —CH3
- —(CH2)3CH3
- 32
- —CH3
- 33
- —CH3
- 34
- —CH3
- 35
- —CH3
- 36
- —CH3
- 37
- —(CH2)3CH3
- 38
- 39
- —CH3
- 40
- —(CH2)3CH3
- 41
- —CH3
- 42
- —CH3
- 43
- —(CH2)3CH3
- 44
- —CH3
- 45
- 46
- 47
- —(CH2)3CH3
- 48
- 49
- 50
- 51
- —CH3
118 more elements
Dependencies are inferred from the claim text.