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US 10,519,141 B2Granted
Pyrimidine compound and pharmaceutical use thereof
AssigneeHanmi Pharm. Co., Ltd.
InventorsYoung Jin Ham, Seok Jong Kang, Jae Yul Choi, Seo Hee Kim, Tae Woo Kim, In Hwan Bae, Young Gil Ahn, Kwee Hyun Suh
Life of this patent
Estimating the term…
Abstract
Provided are a pyrimidine compound represented by Formula 1, a method of preparing the same, and a pharmaceutical use of the pyrimidine compound for the prevention or treatment of cancer.
Claims11
A compound of Formula 1 or a pharmaceutically acceptable salt thereof:
- wherein, in Formula 1,
- R1 is hydrogen, a halogen, a hydroxy group, or a C1-4 alkoxy group,
- R2 is hydrogen, a halogen, a cyano group, a nitro group, an amino group, a carboxamide group, a formyl group, a halo C1-4 alkyl group, or a C1-4 alkyl group,
- R3 is hydrogen, a halo C1-4 alkyl group, a C1-4 alkyl group, a C2-4 alkenyl group, or a C2-4 alkynyl group,
- R4(s) are each independently a halogen, a hydroxy group, a cyano group, a nitro group, an amino group, —SRc, —S(═O)Rc, —S(═O)2Rc, a halo C1-4 alkyl group, a C1-4 alkoxy group, a hydroxy C1-4 alkyl group, a C1-4 alkyl group, a C2-4 alkenyl group, a C2-4 alkynyl group, —NRaRb, —CO2Rb, or —CO—NRaRb,
- wherein, Ra and Rb are each independently hydrogen or a C1-6 alkyl group, and
- Rc is a C1-4 alkyl group or —NRaRb,
- k is an integer from 0 to 4,
- R5 and R6 are each independently hydrogen, a halogen, a hydroxy group, a nitro group, an amino group, a C1-4 alkoxy group, a hydroxy C1-4 alkyl group, a C1-4 alkyl group, a C2-4 alkenyl group, a C2-4 alkynyl group, or a C3-10 cycloalkyl group,
- wherein, the C3-10 cycloalkyl group is each independently unsubstituted or substituted with a halogen, a C1-4 alkyl group, or a halo C1-4 alkyl group,
- R7 is hydrogen, a linear or branched C1-6 alkyl group, a C3-7 cycloalkyl group, a C3-9 heterocycloalkyl group, or a C1-4 alkoxy group,
- Y is a direct bond, —(CH2)m—, —O—, —O(CH2)m—, —(CH2)mO—, —C(═O)—, —NR9—, —(CH2)m—O—(CH2)n—, —CO(CH2)m—, —(CH2)m—CO—, —(CH2)m—CO—(CH2)n—, —(CH2)m—NR9—, —NR9(CH2)m—, —(CH2)m—NR9—(CH2)n—, —(CH2)mSO2—, —SO2(CH2)m—, or —(CH2)m—SO2—(CH2)n—,
- wherein R9 is hydrogen, a C1-4 alkyl group, a C3-10 cycloalkyl group, or a C3-9 heterocycloalkyl group, and
- m and n are each independently an integer from 1 to 3,
- Z is represented by Formula 2:
- wherein, in Formula 2,
- is a C3-10 cycloalkyl group or a C2-11 heterocycloalkyl group,
- R10 (s)) are each independently a halogen, a hydroxy group, a cyano group, a nitro group, an amino group, a thiol group, a formyl group, a linear or branched halo C1-4 alkyl group, a linear or branched C1-4 alkoxy group, a linear or branched hydroxy C1-4 alkyl group, a linear or branched C1-4 alkyl group, a linear or branched hydroxy C1-4 alkylcarbonyl group, a C2-4 alkenyl group, a C2-4 alkynyl group, a C3-10 cycloalkyl group, a C2-9 heterocycloalkyl group, a hydroxy C2-9 heterocycloalkyl group, —NR11NR12, COR13, —COOR13, or —SO2R14,
- R11 and R12 are each independently hydrogen, a linear or branched hydroxy C1-4 alkyl group, a linear or branched halo C1-4 alkyl group, a linear or branched C1-4 alkyl group, a C2-4 alkenyl group, or a C2-4 alkynyl group,
- R13 is hydrogen, a hydroxy group, a hydroxy C1-4 alkyl group, a halo C1-4 alkyl group, a C1-4 alkyl group, a C2-4 alkenyl group, a C2-4 alkynyl group, a C3-10 cycloalkyl group, or a C2-9 heterocycloalkyl group,
- R14 is a hydroxy group, a halo C1-4 alkyl group, a C1-4 alkyl group, a C2-4 alkenyl group, a C2-4 alkynyl group, a C3-10 cycloalkyl group, a C2-9 heterocycloalkyl group, an aryl group, or —NRaRb, and
- q is an integer from 0 to 5.
19 more elements
A pharmaceutical composition comprising a compound of Formula 1′ or a pharmaceutically acceptable thereof, and a pharmaceutically acceptable carrier:
- wherein, in Formula 1′,
- R1 is hydrogen, a halogen, a hydroxy group, or a C1-4 alkoxy group,
- R2 is hydrogen, a halogen, a cyano group, a nitro group, an amino group, a carboxamide group, a formyl group, a halo C1-4 alkyl group, or a C1-4 alkyl group,
- R3 is hydrogen, a halo C1-4 alkyl group, a C1-4 alkyl group, a C2-4 alkenyl group, or a C2-4 alkynyl group,
- R4(s) are each independently a halogen, a hydroxy group, a cyano group, a nitro group, an amino group, —SRc, —S(═O)Rc, —S(═O)2Rc, a halo C1-4 alkyl group, a C1-4 alkoxy group, a hydroxy C1-4 alkyl group, a C1-4 alkyl group, a C2-4 alkenyl group, a C2-4 alkynyl group, —NRaRb, —CO2Rb, or —CO—NRaRb,
- wherein, Ra and Rb are each independently hydrogen or a C1-6 alkyl group, and
- Rc is a C1-4 alkyl group or —NRaRb,
- k is an integer from 0 to 4,
- R5 and R6 are each independently hydrogen, a halogen, a hydroxy group, a nitro group, an amino group, a C1-4 alkoxy group, a hydroxy C1-4 alkyl group, a C1-4 alkyl group, a C2-4 alkenyl group, a C2-4 alkynyl group, or a C3-10 cycloalkyl group,
- wherein, the C3-10 cycloalkyl group is each independently unsubstituted or substituted with a halogen, a C1-4 alkyl group, or a halo C1-4 alkyl group,
- R7 is a C3-7 cycloalkyl group
- Y is a direct bond, —(CH2)m—, —O—, —O(CH2)m—, —(CH2)mO—, —C(═O)—, —NR9—, —SO2—, —(CH2)m—O—(CH2)n—, —CO(CH2)m—, —(CH2)mCO—, —(CH2)m—CO—(CH2)n—, —(CH2)m—NR9—, —NR9(CH2)m—, —(CH2)m—NR9—(CH2)n—, —(CH2)mSO2—, —SO2(CH2)m—, or —(CH2)m—SO2—(CH2)n—,
- wherein R9 is hydrogen, a C1-4 alkyl group, a C3-10 cycloalkyl group, or a C3-9 heterocycloalkyl group, and
- m and n are each independently an integer from 1 to 3,
- Z is represented by Formula 2:
- wherein, in Formula 2,
- is a C3-10 cycloalkyl group or a C2-11 heterocycloalkyl group,
- R10 (s)) are each independently a halogen, a hydroxy group, a cyano group, a nitro group, an amino group, a thiol group, a formyl group, a linear or branched halo C1-4 alkyl group, a linear or branched C1-4 alkoxy group, a linear or branched hydroxy C1-4 alkyl group, a linear or branched C1-4 alkyl group, a linear or branched hydroxy C1-4 alkylcarbonyl group, a C2-4 alkenyl group, a C2-4 alkynyl group, a C3-10 cycloalkyl group, a C2-9 heterocycloalkyl group, a hydroxy C2-9 heterocycloalkyl group, —NR11R12, —COR13, —COOR13, or —SO2R14,
- R11 and R12 are each independently hydrogen, a linear or branched hydroxy C1-4 alkyl group, a linear or branched halo C1-4 alkyl group, a linear or branched C1-4 alkyl group, a C2-4 alkenyl group, or a C2-4 alkynyl group,
- R13 is hydrogen, a hydroxy group, a hydroxy C1-4 alkyl group, a halo C1-4 alkyl group, a C1-4 alkyl group, a C2-4 alkenyl group, a C2-4 alkynyl group, a C3-10 cycloalkyl group, or a C2-9 heterocycloalkyl group,
- R14 is a hydroxy group, a halo C1-4 alkyl group, a C1-4 alkyl group, a C2-4 alkenyl group, a C2-4 alkynyl group, a C3-10 cycloalkyl group, a C2-9 heterocycloalkyl group, an aryl group, or —NRaRb, and
- q is an integer from 0 to 5.
19 more elements
Dependencies are inferred from the claim text.