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US 10,370,372 B2Granted
Fused pyrimidine compound or salt thereof
AssigneeTaiho Pharmaceutical Co., Ltd.
InventorsKazuhisa Minamiguchi, Shigeo Okajima, Takahiro Asai, Masanori Asai, Yoshio Ogino
Life of this patent
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Abstract
To provide a compound having an inhibitory activity for an androgen receptor. A fused pyrimidine compound represented by the following formula (I) or a pharmaceutically acceptable thereof (in the formula, X, Y, Z, R1, and R2 are as defined in the specification).
Claims14
A fused pyrimidine compound represented by formula (I):
- wherein, in the formula,
- X represents a cyano group or a nitro group;
- Y represents a halogen atom, a halogeno-C1-3 alkyl group, a C1-3 alkoxy group, or a C1-3 alkyl group;
- Z represents a hydrogen atom, a halogen atom, or a C1-3 alkyl group;
- R1 represents a C6-14 aryl group which is substituted with Ra and may be substituted simultaneously with Rb or a 5- or 6-membered heteroaryl group which is substituted with Ra and may be substituted simultaneously with Rb, wherein the Ra and Rb may be bonded to each other to form a fused ring together with the C6-14 aryl group or the heteroaryl group;
- and
- R2 represents a hydrogen atom, a C1-3 alkyl group, or a cyano group, wherein
- Ra represents a phenyl group, a hydroxy-C1-6 alkyl group, a hydroxy-C3-7 cycloalkyl group, a hydroxy-heterocycloalkyl group, a C1-6 alkoxy group which may be substituted with Rc, an amino-C1-6 alkyl group which may be substituted with Rf, a halogeno-C1-3 alkoxy group, a C3-7 cycloalkylaminosulfonyl group, a C1-3 alkylsulfonyl group, a 3- to 7-membered monocyclic heterocycloalkylsulfonyl group, a C1-3 alkoxycarbonylamino group which may be substituted with a halogen, a C1-3 alkylcarbonylamino group which may be substituted with a halogen, a 3- to 7-membered monocyclic heterocycloalkanecarbonyl group substituted with a hydroxy-C1-6 alkyl group, a bicyclic heterocycloalkyl group, or —(CH2)n—C(═O)—NRdRe;
- Rb represents a hydrogen atom, a halogen atom, a C1-3 alkyl group which may be substituted with a halogen atom, or a C1-4 alkoxy group which may be y substituted with a halogen atom;
- Rc represents a pyrazolyl group, triazolyl group, or tetrazolyl group which may be substituted or a piperazinyl group which may be substituted with Rf;
- Rd and Re each independently represent a hydrogen atom, a C1-3 alkyl group, a C2-6 alkynyl group, a C1-6 alkoxy group, a C3-7 cycloalkyl group, a halogeno-C1-3 alkyl group, a hydroxy-C1-6 alkyl group, a hydroxy-C3-7 cycloalkyl group, a hydroxy-C3-7 cycloalkyl-C1-6 alkyl group, a C1-4 alkoxy group, or a C1-6 alkyl group substituted with Rg, or NRdRe of the —(CH2)n—C(═O)—NRdRe may form a ring;
- Rf represents a C1-6 alkyl group, a C1-6 alkylcarbonyl group, a C1-6 alkylsulfonyl group, a C1-6 alkoxycarbonyl group, or a C1-6 alkylaminocarbonyl group;
- Rg represents a C1-6 alkylpyrazolyl group, a halogeno-C1-3 alkylthiazolyl group, an oxadiazolyl group, a halogeno-C1-3 alkyloxadiazolyl group, or a C1-6 alkoxycarbonylamino group;
- and
- n represents an integer of from 0 to 3,
- provided that:
- if X is a cyano group, Y is a halogen atom or a halogeno-C1-3 alkyl group, R2 is a hydrogen atom, Z is a hydrogen atom,
- R1 is a C6-14 aryl group which is substituted with Ra and may be substituted simultaneously with Rb or a 5- or 6-membered heteroaryl group which is substituted with Ra and may be substituted simultaneously with Rb, and
- Rb is a hydrogen atom, a halogen atom, or a C1-3 alkyl group which may be substituted with a halogen atom,
- then Ra is
- a hydroxy-heterocycloalkyl group,
- a C1-6 alkoxy group which may be substituted with Rc, wherein Rc represents a piperazinyl group which may be substituted with C1-6 alkyl, C1-6 alkylcarbonyl, C1-6 alkoxycarbonyl, or C1-6 alkylaminocarbonyl,
- an amino-C1-6 alkyl group which may be substituted with Rf, wherein Rf is as described above,
- a halogeno-C1-3 alkoxy group,
- a C1-3 alkylsulfonyl group,
- a bicyclic cycloheteroalkyl group, or
- —(CH2)n—C(═O)—NRdRe, wherein n, Rd, and Re are as described above, provided that if either one of Rd and Re is a halogeno-C1-3 alkyl group, a hydroxy-C1-6 alkyl group, a hydroxy-C3-7 cycloalkyl group, a hydroxy-C3-7 cycloalkyl-C1-6 alkyl group, or a C1-6 alkyl group substituted with C1-6 alkylpyrazolyl, halogeno-C1-3 alkylthiazolyl, oxadiazolyl, or halogeno-C1-3 alkyloxadiazolyl, then the other is not a hydrogen atom,
- or a pharmaceutically acceptable salt thereof.
25 more elements
Dependencies are inferred from the claim text.