1. A remote control device configured for use with a load control device, the remote control device comprising:
a housing supporting a capacitive touch surface, the housing having a resiliently deformable portion configured to be operated from a relaxed state to a deformed state and the capacitive touch surface being configured to provide and receive touch controls for controlling an electrical load using the load control device;
a printed circuit board (PCB) disposed in the housing, the PCB comprising a switch configured to awaken the remote control device from a sleep state; and
a conductive member in contact with the deformable portion of the housing,
wherein, when the deformable portion of the housing is deformed into the deformed state, the conductive member makes electrical contact with a portion of the switch such that the capacitive touch surface is awakened from the sleep state.
2. The remote control device of claim 1, wherein the capacitive touch surface comprises a front panel, and wherein the front panel comprises a plurality of touch icons displayed on an outer surface thereof corresponding to the touch controls for controlling the electrical load using the load control device.
3. The remote control device of claim 2, wherein awakening the capacitive touch surface from the sleep state causes the plurality of touch icons to be illuminated.
4. The remote control device of claim 1, wherein the switch comprises an open circuit pad defining an open circuit.
5. The remote control device of claim 4, wherein the conductive member comprises a membrane and an activated carbon structure, wherein the membrane comprises a rim and a partial spherical body attached to the rim having an inward facing surface and an opposed outward facing surface, wherein a top portion of the rim rests on a surface of the PCB supporting the switch, and wherein the activated carbon structure is attached to the inward facing surface of the partial spherical body.
6. The remote control device of claim 5, wherein the activated carbon structure attached to the inward facing surface of the partial spherical body is spaced apart from the open circuit pad of the switch.
7. The remote control device of claim 5, wherein the activated carbon structure attached to the inward facing surface of the partial spherical body is preloaded such that the activated carbon structure is at least partially inserted into the open circuit pad of the switch.
8. The remote control device of claim 5, wherein the deformable portion comprises an impedance member support on an interior surface thereof, and wherein the outward facing surface of the partial spherical body of the membrane abuts the impedance member support on the deformable portion of the housing.
9. The remote control device of claim 8, wherein the deformable portion comprises a convex shape in the relaxed state.
10. The remote control device of claim 8, wherein the housing further comprises sidewalls attached to the deformable portion, wherein the sidewalls are angled inward from the capacitive touch surface and outward from the deformable portion, and wherein the deformable portion comprises a concave shape in the relaxed state.
11. The remote control device of claim 8, wherein, when the deformable portion of the housing is flexed into the deformed state, the impedance member support forces the membrane and the activated carbon structure to be at least partially inserted into the open circuit pad such that the open circuit is at least partially closed causing the capacitive touch surface to awaken from the sleep state.
12. A remote control device for controlling an electrical load, the remote control device comprising:
a capacitive touch surface; and
a flexible housing supporting the capacitive touch surface, wherein flexing at least a portion of the housing causes the capacitive touch surface to awaken from a sleep state.
13. The remote control device of claim 12, wherein the capacitive touch surface comprises a front panel, and wherein the front panel comprises a plurality of touch icons displayed on an outer surface thereof configured to be actuated to control a lighting load.
14. The remote control device of claim 13, wherein awakening the remote control device causes the plurality of touch icons to be illuminated.
15. The remote control device of claim 13, wherein capacitive touch surface further comprises a capacitive touch electrode printed circuit board (PCB) with a first surface configured to abut an inner surface of the front panel, and wherein the capacitive electrode PCB comprises one or more openings therethrough and one or more capacitive sensing portions surrounding the openings on the first surface thereof.
16. The remote control device of claim 15, further comprising one or more light pipes configured to transport light from one or more light emitting diodes (LEDs) to the plurality of touch icons on the outer surface of the front panel for illumination thereof and a sub-bezel for housing the light pipes and the LEDs.
17. The remote control device of claim 16, wherein the sub-bezel defines a depressed base portion on a first surface thereof with an outer perimeter sized to receive the capacitive touch electrode PCB such that the second surface of the capacitive touch electrode PCB abuts the first surface of the sub-bezel and the capacitive touch electrode PCB is seated in the depressed base portion, and wherein the depressed base portion comprises one or more recesses defined therein sized to house the light pipes.
18. The remote control device of claim 17, wherein the sub-bezel further defines one or more receptacles on a second surface thereof sized to house the LEDs.
19. The remote control device of claim 18, further comprising a printed circuit board (PCB), wherein the PCB comprises the LEDs on a first surface thereof, and wherein the first surface of the PCB abuts the second surface of the sub-bezel such that the LEDs are seated and housed in the receptacles of the sub-bezel.
20. The remote control device of claim 19, wherein the PCB further comprises a switching circuit defined on a second surface thereof, and wherein the switching circuit comprises an open circuit pad defining an open circuit.
21. The remote control device of claim 20, further comprising a conductive member comprising a membrane and an activated carbon structure, wherein the membrane comprises a rim and a partial spherical body attached to the rim having an inward facing surface and an opposed outward facing surface, wherein a top portion of the rim rests on the second surface of the PCB, and wherein the activated carbon structure is attached to the inward facing surface of the partial spherical body.
22. The remote control device of claim 21, wherein the activated carbon structure attached to the inward facing surface of the partial spherical body is spaced apart from the second surface of the PCB and the open circuit pad of the switching circuit defined thereon.
23. The remote control device of claim 21, wherein the activated carbon structure attached to the inward facing surface of the partial spherical body is preloaded such that the activated carbon structure is at least partially inserted into the open circuit pad of the switching circuit on the second surface of the PCB.
24. The remote control device of claim 21, wherein the housing comprises a bottom portion, wherein the bottom portion comprises an impedance member support on an interior surface thereof, and wherein the outward facing surface of the partial spherical body of the membrane abuts the impedance member support on the bottom portion of the housing.
25. The remote control device of claim 24, wherein the bottom portion comprises a convex shape in a relaxed state.
26. The remote control device of claim 24, wherein the housing further comprises sidewalls attached to the bottom portion, wherein the sidewalls are angled inward from the front panel and outward from the bottom portion, and wherein the bottom portion comprises a concave shape in a relaxed state.
27. The remote control device of claim 24, wherein, when at least a portion of the housing is flexed, the impedance member support forces the membrane and the activated carbon structure to be at least partially inserted into the open circuit pad such that the open circuit is at least partially closed causing the capacitive touch surface to awaken from the sleep state.
28. A remote control device for controlling an electrical load, the remote control device comprising:
a housing that defines an interior and an exterior surface;
a switch that is enclosed within the interior of the housing; and
a capacitive touch surface supported by the exterior surface of the housing;
wherein the switch is configured to cause the remote control device to awaken from a sleep state in response to an actuation capacitive touch surface.
29. The remote control device of claim 28, wherein the capacitive touch surface comprises a front panel, and wherein the front panel comprises a plurality of touch icons displayed on an outer surface thereof corresponding to a respective capacitive touch control configured to be actuated to control the electrical load.
30. The remote control device of claim 29, wherein awakening the remote control device causes the plurality of touch icons to be illuminated.
31. The remote control device of claim 28, wherein the switch comprises an open circuit pad defining an open circuit.
32. The remote control device of claim 31, further comprising a conductive member comprising a membrane and an activated carbon structure, wherein the membrane comprises a rim and a partial spherical body attached to the rim having an inward facing surface and an opposed outward facing surface, wherein a top portion of the rim rests on a surface supporting the switch and, wherein the activated carbon structure is attached to the inward facing surface of the partial spherical body.
33. The remote control device of claim 32, wherein the activated carbon structure attached to the inward facing surface of the partial spherical body is spaced apart from the open circuit pad of the switch.
34. The remote control device of claim 32, wherein the activated carbon structure attached to the inward facing surface of the partial spherical body is preloaded such that the activated carbon structure is at least partially inserted into the open circuit pad of the switch.
35. The remote control device of claim 32, wherein the housing comprises a bottom portion, wherein the bottom portion comprises an impedance member support on an interior surface thereof, and wherein the outward facing surface of the partial spherical body of the membrane abuts the impedance member support on the bottom portion of the housing.
36. The remote control device of claim 35, wherein the bottom portion comprises a convex shape when the housing is in a relaxed state.
37. The remote control device of claim 35, wherein the housing further comprises sidewalls attached to the bottom portion, wherein the sidewalls are angled inward from the capacitive touch surface and outward from the bottom portion, and wherein the bottom portion comprises a concave shape when the housing is in a relaxed state.
38. The remote control device of claim 35, wherein, at least a portion of the housing is flexed into a deformed state such that the impedance member support forces the membrane and the activated carbon structure to be at least partially inserted into the open circuit pad causing the remote control device to awaken from the sleep state.
39. A remote control device for controlling an electrical load, the remote control device comprising:
a flexible housing supporting the capacitive touch surface, wherein flexing at least a portion of the housing causes the remote control device to awaken from a sleep state.
40. The remote control device of claim 39, wherein the housing comprises a bottom portion.
41. The remote control device of claim 40, wherein the bottom portion comprises a convex shape prior to flexing.
42. The remote control device of claim 41, wherein the bottom portion comprises a concave shape after flexing.
43. The remote control device of claim 40, wherein the housing further comprises sidewalls attached to the bottom portion, wherein the sidewalls are angled inward from the front panel and outward from the bottom portion, and wherein the bottom portion comprises a concave shape prior to flexing.
44. The remote control device of claim 43, wherein the bottom portion comprises a shape even more concave after flexing than the concave shape prior to flexing.
The claims below are in addition to those above.
All refrences to claim(s) which appear below refer to the numbering after this setence.
1. A compound of the formula I:
wherein
R1 and R2 are the same or different and a 6- to 10-membered monocyclic or bicyclic aryl group optionally substituted by one to three group(s) selected from a halogen atom, a cyano group, a C1-6 alkyl group optionally substituted by one to three halogen atom(s), a C1-6 alkyloxy group optionally substituted by one to three halogen atom(s), an amino group optionally substituted by one to two C1-6 alkyl group(s), a C1-6 alkylthio group, a C1-6 alkylsulfinyl group and a C1-6 alkylsulfonyl group,
Q is single bond, a methylene group or a group of the formula: \u2014N(RQ)\u2014,
RQ is a C1-6 alkyl group,
5-membered Ring A is a substituted pyrazole ring fused to the adjacent pyrimidine ring having the following formula (A), (B) or (C),
R3 and R4 are the same or different and each is (a) a hydrogen atom, (b) a cyano group, (c) a C1-6 alkyl group optionally substituted by one to three halogen atom(s), (d) a C1-6 alkyloxy group (the alkyl moiety of said group being optionally substituted by one to three group(s) selected from a halogen atom, a hydroxyl group, an amino group optionally substituted by one or two C1-6 alkyl group(s), a C1-6 alkyloxy group and a C1-6 alkylsulfonyl group), (e) a C1-6 alkylthio group, (f) a C1-6 alkylsulfinyl group, (g) a C1-6 alkylsulfonyl group or (h) a group of the formula: \u2014N(R\u2032)(R\u2033), R\u2032 and R\u2033 are the same or different and (a) a hydrogen atom, (b) a C1-6 alkyl group optionally substituted by one to three group(s) selected from a halogen atom, an amino group optionally substituted by one or two C1-6 alkyl group(s) and a C1-6 alkyloxy group, (c) an acyl group, (d) a C1-6 alkylsulfonyl group or (e) an amino sulfonyl group optionally substituted by one to two C1-6 alkyl group(s), or both R\u2032 and R\u2033 combine each other at their termini to form together with an adjacent nitrogen atom a saturated or unsaturated 5- to 6-membered nitrogen-containing heterocyclic group optionally substituted by a hydroxyl group or a C1-6 alkyloxy group,
E is one of the following groups (ii) to (v):
Q1 is a single bond, a C1-6 alkylene group or a group of the formula: \u2014N(R7)\u2014, R7 is a hydrogen atom or a C1-6 alkyl group,
Q2 is a single bond or a C1-6 alkylene group,
one of R5 and R6 is a hydrogen atom or a C1-6 alkyl group and the other is (A) a C1-6 alkyl group optionally substituted by one to three group(s) selected from the group consisting of (a) a halogen atom; (b) a cyano group; (c) a C1-6 alkyloxy group; (d) a C3-8 cycloalkyl group optionally substituted by one to two group(s) selected from a cyano group and a C1-6 alkyl group; (e) an amino group optionally substituted by one or two C1-6 alkyl group(s); (f) a C1-6 alkylthio group; (g) a C1-6 alkylsulfinyl group; (h) a C1-6 alkylsulfonyl group; (i) an acyl group; (j) a 6- to 10-membered monocyclic or bicyclic aryl group optionally substituted by one to two halogen atom(s); (k) a saturated or unsaturated 4- to 7-membered heteromonocyclic group (said heteromonocyclic group containing one to four heteroatom(s) selected from oxygen atom, sulfur atom and nitrogen atom); (1) a saturated or unsaturated 8- to 15-membered nitrogen-containing bi-cyclic or tri-cyclic heterocyclic group formed by fusing the aforementioned heteromonocyclic group with one or two other cyclic group(s) selected from a C3-8 cycloalkyl group, a 5- to 6-membered monocyclic aryl group and a saturated or unsaturated 4- to 7-membered heteromonocyclic group (said heteromonocyclic group containing one to four heteroatom(s) selected from oxygen atom, sulfur atom and nitrogen atom); and (m) a saturated or unsaturated 8- to 11-membered nitrogen-containing spiro-heterocyclic group, (B) a C3-8 cycloalkyl group optionally substituted by one to two group(s) selected from a cyano group and a C1-6 alkyl group, (C) a group of the formula: \u2014N(R8)(R9), (D) a 6- to 10-membered monocyclic or bicyclic aryl group optionally substituted by one to two halogen atom(s), or (E) a saturated or unsaturated heterocyclic group selected from the group consisting of i) a saturated or unsaturated 4- to 7-membered heteromonocyclic group (said heteromonocyclic group containing one to four heteroatom(s) selected from oxygen atom, sulfur atom and nitrogen atom), ii) a saturated or unsaturated 8- to 15-membered nitrogen-containing bi-cyclic or tri-cyclic heterocyclic group formed by fusing the aforementioned heteromonocyclic group with one or two other cyclic group(s) selected from a C3-8 cycloalkyl group, a 5- to 6-membered monocyclic aryl group and a saturated or unsaturated 4- to 7-membered heteromonocyclic group (said heteromonocyclic group containing one to four heteroatom(s) selected from oxygen atom, sulfur atom and nitrogen atom) and iii) a saturated or unsaturated 8- to 11-membered nitrogen-containing spiro-heterocyclic group, or both of R5 and R6 combine each other to form together with an adjacent nitrogen atom a saturated or unsaturated nitrogen-containing heterocyclic group selected from the group consisting of
(a) a saturated or unsaturated, 4- to 7-membered nitrogen-containing heteromonocyclic group, said heteromonocyclic group optionally containing two or more nitrogen atoms and optionally containing one to two heteroatom(s) other than such nitrogen atom(s) selected from oxygen atom and sulfur atom;
(b) a saturated or unsaturated, 8- to 15-membered nitrogen-containing bicyclic or tricyclic heterocyclic group formed by fusing the aforementioned heteromonocyclic group with one or two other cyclic group(s) selected from a C3-8 cycloalkyl group, a 5- to 6-membered monocyclic aryl group and a saturated or unsaturated, 4- to 7-membered heteromonocyclic group, said heteromonocyclic group containing one to four heteroatom(s) selected from oxygen atom, sulfur atom and nitrogen atom; and
(c) a saturated or unsaturated, 8- to 11-membered nitrogen-containing spiro-heterocyclic group,
R8 is a hydrogen atom or a C1-6 alkyl group,
R9 is (a) a C1-6 alkyl group optionally substituted by one to three group(s) selected from a halogen atom, a cyano group and a phenyl group, (b) a C3-8 cycloalkyl group, (c) a 6- to 10-membered monocyclic or bicyclic aryl group optionally substituted by one to two halogen atom(s) or (d) an acyl group or (e) a saturated or unsaturated heterocyclic group selected from the group consisting of i) a saturated or unsaturated 4- to 7-membered heteromonocyclic group said heteromonocyclic group containing one to four heteroatom(s) selected from oxygen atom, sulfur atom and nitrogen atom), ii) a saturated or unsaturated 8- to 15-membered nitrogen-containing bi-cyclic or tri-cyclic heterocyclic group formed by fusing the aforementioned heteromonocyclic group with one or two other cyclic group(s) selected from a C3-8 cycloalkyl group, a 5- to 6-membered monocyclic aryl group and a saturated or unsaturated 4- to 7-membered heteromonocyclic group (said heteromonocyclic group containing one to four heteroatom(s) selected from oxygen atom, sulfur atom and nitrogen atom) and iii) a saturated or unsaturated 8- to 11-membered nitrogen-containing spiro-heterocyclic group,
R50 is a hydrogen atom or a C1-6 alkyl group,
R60 is a hydrogen atom, a C1-6 alkyl group or an acyl group, or both of them combine together with the adjacent nitrogen atom to form a cyclic group of the following formula:
in which Ring A1 is a 5- to 7-membered aliphatic nitrogen-containing heterocyclic group optionally substituted by an oxo group,
R51 is an alkyl group or a 6- to 10-membered monocyclic or bicyclic arylsulfonyl group optionally substituted by one to two halogen atom(s),
R61 is a C1-6 alkylamino group or an azido group, and wherein (a) the above-mentioned saturated or unsaturated heterocyclic group in R5, R6, R8 or R9 may be substituted by one to four groups selected from the group consisting of a halogen atom;
a hydroxyl group;
a cyano group;
an oxo group;
a C1-6 alkyl group;
a C1-6 alkyl group substituted by one to three halogen atom(s);
a C1-6 alkyloxy-C1-6 alkyl group;
an amino-C1-6 alkyl group;
a C3-8 cycloalkyl group;
a phenyl-C1-6 alkyl group;
a C1-6 alkyloxy group;
a C1-6 alkyloxy group substituted by one to three halogen atom(s);
an acyl group;
an amino group optionally substituted by one to two C1-6 alkyl group(s);
an acylamino group;
a C1-6 alkylsulfonyl group;
an aminosulfonyl group optionally substituted by one to two C1-6 alkyl group(s);
a phenyl group optionally substituted by one to two halogen atom(s); and
a saturated or unsaturated 5- to 6-membered nitrogen-containing heterocyclic group, and
wherein
(b) the above-mentioned saturated or unsaturated heterocyclic group formed by combining R5 with R6 may be substituted by one to three group(s) selected from the group consisting of
a halogen atom;
a hydroxyl group;
a cyano group;
an oxo group;
a C1-6 alkyl group;
a C1-6 alkyl group substituted by one to three halogen atom(s);
a C1-6 alkyloxy-C1-6 alkyl group;
an amino-C1-6 alkyl group;
a C3-8 cycloalkyl group;
a phenyl-C1-6 alkyl group;
a C1-6 alkyloxy group;
a C1-6 alkyloxy group substituted by one to three halogen atom(s);
an acyl group;
an amino group optionally substituted by one to two C1-6 alkyl group(s);
an acylamino group;
a C1-6 alkylsulfonyl group;
an aminosulfonyl group optionally substituted by one to two C1-6 alkyl group(s); and
a phenyl group,
or a pharmaceutically acceptable salt thereof.
2. The compound according to claim 1 wherein the group of the formula (II) is one of the following groups (a) to (d):
\u2014C(\u2550O)\u2014N(R5)(R6),\u2003\u2003(a)
\u2014C(\u2550O)-Alk-N(R5)(R6),\u2003\u2003(b)
-Alk-C(\u2550O)\u2014N(R5)(R6),\u2003\u2003(c)
\u2014N(R7)\u2014C(\u2550O)\u2014N(R5)(R6)\u2003\u2003(d)
in which Alk is a straight or branched chain C1-6 alkylene group, or a pharmaceutically acceptable salt thereof.
3. A compound of the formula I:
wherein
R1 and R2 are the same or different and each is a phenyl group optionally substituted by one to two group(s) selected from a halogen atom and a trihalogeno-C1-6 alkyl group,
Q is a single bond,
R3 is (a) a hydrogen atom, (b) a cyano group, (c) a C1-6 alkyl group optionally substituted by one to three halogen atom(s), (d) a C1-6 alkyloxy group (the alkyl moiety of said group being optionally substituted by one to three group(s) selected from a halogen atom, a hydroxyl group, an amino group optionally substituted by one or two C1-6 alkyl group(s), a C1-6 alkyloxy group and a C1-6 alkylsulfonyl group), (e) a C1-6 alkylthio group, (f) a C1-6 alkylsulfinyl group, (g) a C1-6 alkylsulfonyl group or (h) a group of the formula: \u2014N(R\u2032)(R\u2033), wherein R\u2032 and R\u2033 are the same or different and each is (a) a hydrogen atom, (b) a C1-6 alkyl group optionally substituted by one to three group(s) selected from a halogen atom, an amino group optionally substituted by one or two C1-6 alkyl group(s) and a C1-6 alkyloxy group, (c) an acyl group, (d) a C1-6 alkylsulfonyl group or (e) an amino sulfonyl group optionally substituted by one to two C1-6 alkyl group(s), or both R\u2032 and R\u2033 combine each other at their termini to form together with an adjacent nitrogen atom a saturated or unsaturated 5- to 6-membered nitrogen-containing heterocyclic group optionally substituted by a hydroxyl group or a C1-6 alkyloxy group,
Ring A is a substituted pyrazole ring of the formula (A)
E is a group of the following formula: \u2014C(\u2550O)O\u2014R00 (i)
R4 is an amino group optionally substituted by one to two group(s) selected from a C1-6 alkyl group and a C1-6 alkylsulfonyl group,
or a pharmaceutically acceptable salt thereof.
4. The compound according to claim 3 wherein R1 is a chlorophenyl group or a trifluoro-C1-4 alkyl-phenyl group, R2 is a chlorophenyl group, R3 is a 4 alkyl group and R4 is (a) an amino group substituted by one to two group(s) selected from a C1-4 alkyl group and a C1-4 alkylsulfonyl group or (b) an aminosulfonyl group substituted by one to two C1-4 alkyl group(s), or a pharmaceutically acceptable salt thereof.
5. The compound according to claim 1 wherein
R1 and R2 are the same or different and a phenyl group optionally substituted by one to three group(s) selected from a halogen atom, a cyano group, a C1-6 alkyl group optionally substituted by one to three halogen atom(s), a C1-6 alkyloxy group optionally substituted by one to three halogen atom(s), an amino group optionally substituted by one to two C1-6 alkyl group(s) and a C1-6 alkylsulfonyl group,
Ring A is a substituted pyrazole ring of the formula (A) or (B),
E is one of the groups of the following formula (a) to (e):
\u2014C(\u2550O)\u2014N(R5)(R6),\u2003\u2003a)
\u2014C(\u2550O)-Alk-N(R5)(R6),\u2003\u2003b)
-Alk-C(\u2550O)\u2014N(R5)(R6),\u2003\u2003c)
\u2014N(R7)\u2014C(\u2550O)\u2014N(R5)(R6),\u2003\u2003d)
\u2014C(\u2550NR51)\u2014R61,\u2003\u2003e)
in which Alk is a straight or branched chain C1-6 alkylene group,
R3 is a hydrogen atom, a cyano group or a C1-6 alkyloxy group,
R4 is (a) a hydrogen atom, (b) a cyano group, (c) a C1-6 alkyl group optionally substituted by one to three group(s) selected from a halogen atom and a hydroxyl group, (d) a C1-6 alkyloxy group optionally substituted by one to three group(s) selected from a halogen atom, a hydroxyl group, an amino group optionally substituted by one to two C1-6 alkyl group(s), a C1-6 alkyloxy group and a C1-6 alkylsulfonyl group, (e) a C1-6 alkylthio group, (f) a C1-6 alkylsulfinyl group, (g) a C1-6 alkylsulfonyl group or (h) a group of the formula: \u2014N(R\u2032)(R\u2033),
R\u2032 and R\u2033 are the same or different and (a) a hydrogen atom, (b) a C1-6 alkyl group optionally substituted by one to three group(s) selected from a halogen atom, an amino group optionally substituted by one to two C1-6 alkyl group(s) and a C1-6 alkyloxy group, (c) an acyl group, (d) a C1-6 alkylsulfonyl group or (e) an aminosulfonyl group optionally substituted by one to two C1-6 alkyl group(s), or (f) both of them combine together with the adjacent nitrogen atom to form a saturated or unsaturated 5- to 6-membered nitrogen-containing heteromonocyclic group optionally substituted by a hydroxyl group or a C1-6 alkyloxy group,
R5 is a hydrogen atom or a C1-6 alkyl group,
R6 is
(1) an alkyl group optionally substituted by one to three group(s) selected from a halogen atom, a C1-6 alkyloxy group, a C3-8 cycloalkyl group, a C1-6 alkylthio group, a C1-6 alkylsulfonyl group, an amino group optionally substituted by one or two C1-6 alkyl group(s), a morpholinocarbonyl group, a phenyl group optionally substituted by a cyano group and a saturated or unsaturated 5- to 6-membered nitrogen-containing heteromonocyclic group, said heteromonocyclic group being optionally substituted by a group selected from a halogen atom, a C1-6 alkyl group and a trihalogeno-C1-6 alkyl group;
(2) a C3-8 cycloalkyl group optionally substituted by a cyano group or a C1-6 alkyl group;
(3) a group of the formula: \u2014N(R8)(R9); or
(4) a phenyl group; or
(5) a saturated or unsaturated 4- to 10-membered monocyclic- or bicyclic heterocyclic group optionally substituted by one to four group(s) selected from a halogen atom, a cyano group, a hydroxyl group, an oxo group, a C1-6 alkyl group optionally substituted by one to three halogen atom(s), a C3-8 cycloalkyl group, a C1-6 alkyl-carbonyl group, a C1-6 alkyloxycarbonyl group, a C1-6 alkylsulfonyl group, an aminosulfonyl group optionally substituted by one or two C1-6 alkyl group(s), a carbamoyl group optionally substituted by one to two C1-6 alkyl group(s), a C1-6 alkyloxycarbonyl group, a C1-6 alkyloxycarbonylamino group a phenyl group optionally substituted by one to two halogen atom(s) and saturated or unsaturated 5- to 6-membered heteromonocyclic group; or
(6) both of R5 and R6 combine each other together with the adjacent nitrogen atom to form a saturated or unsaturated 5- to 7-membered nitrogen-containing heterocyclic group optionally substituted by one to two group(s) selected from a halogen atom and an oxo group,
R8 is hydrogen atom or a C1-6 alkyl group,
R9 is (a) a C1-6 alkyl group optionally substituted by one to three group(s) selected from a halogen atom, a cyano group and a phenyl group; (b) a phenyl group optionally substituted by a group selected from a halogen atom, a cyano group, a C1-6 alkyl group, a trihalogeno-C1-6 alkyl group, a C3-8 cycloalkyl group, a trihalogeno-C1-6 alkyloxy group, a C1-6 alkyloxy group, a C1-6 alkylthio group and a C1-6 alkylsulfonyl group; (c) a C1-6 alkyloxycarbonyl group; or (d) a saturated or unsaturated 5- to 6-membered heteromonocyclic group optionally substituted by a group selected from a halogen atom, a cyano group, a C1-6 alkyl group, a C1-6 alkyloxy group and a trihalogeno-C1-6 alkyl group,
R7 is a hydrogen atom,
R51 is a C1-6 alkyl group or a phenylsulfonyl group optionally substituted by one to two halogen atom(s) and R61 is a C1-6 alkylamino group or an azido group,
or a pharmaceutically acceptable salt thereof.
6. The compound according to claim 5 wherein R1 is a phenyl group optionally substituted by one or two group(s) selected from a halogen atom, a cyano group, a dihalogeno-C1-6 alkyl group, a trihalogeno-C1-6 alkyl group, a C1-6 alkyloxy group, a C1-6 alkyloxy-C1-6alkyl group and di(C1-6alkyl)amino group,
R2 is a phenyl group optionally substituted by one or two group(s) selected from a halogen atom and a cyano group,
R3 is a hydrogen atom,
R4 is a hydrogen atom, a C1-6 alkyl group, a dihalogeno-C1-6 alkyl group, a hydroxy-C1-6 alkyl group, a trihalogeno-C1-6 alkyl group, a C1-6 alkyloxy-C1-6 alkyl group, a hydroxy-C1-6 alkyloxy group, a C1-6 alkyloxy-C1-6 alkyloxy group, a C1-6 alkylsulfonyl-C1-6 alkyl group or a group of the formula: \u2014N(R\u2032)(R\u2033),
one of R\u2032 and R\u2033 is a hydrogen atom or an alkyl group and the other is (a) an acyl group or (b) a C1-6 alkylsulfonyl group,
E is one of the groups of the following formula (a), (b) and (e):
\u2014C(\u2550O)\u2014N(R5)(R6),\u2003\u2003(a)
\u2014C(\u2550O)-Alk-N(R5)(R6),\u2003\u2003(b)
\u2014C(\u2550NR51)\u2014R61,\u2003\u2003(e)
one of R5 and R6 is a hydrogen atom or a C1-6 alkyl group, the other is (a) a C1-6 alkyl group, (b) a C3-8 cycloalkyl group, (c) a phenyl group, (d) a saturated or unsaturated 4- to 10-membered mono- or bi-cyclic heterocyclic group optionally substituted by one to four group(s) selected from a halogen atom, an oxo group, a cyano group, a hydroxyl group, a C1-6 alkyl group, a trihalogeno-C1-6 alkyl group, a C1-6 alkyloxy group, a C1-6 alkyloxy-C1-6 alkyl group, a C1-6 alkylcarbonyl group, a di(C1-6 alkyl)carbamoyl group, a C1-6 alkylsulfonyl group, a di(C1-6 alkyl)aminosulfonyl group, a phenyl group, a halogenophenyl group and a pyridyl group or (e) a group of the formula: \u2014N(R8)(R9), or (f) both of them combine together with the adjacent nitrogen atom to form a saturated or unsaturated 5- to 6-membered heteromonocyclic group optionally substituted by one to two group(s) selected from a halogen atom and an oxo group,
R8 is a C1-6 alkyl group,
R9 is (a) a C1-6 alkyl group, (b) a phenyl group optionally substituted by a halogen atom, (c) a C1-6 alkyl group optionally substituted by a pyridyl group or (d) a saturated or unsaturated 4- to 6-membered heteromonocyclic group optionally substituted by a group selected from a halogen atom, a C1-6 alkyl group, a trihalogeno-C1-6 alkyl group and a C1-6alkyloxy group,
R51 is an alkyl group or a halogenophenyl-sulfonyl group, and R61 is an alkylamino group or an azido group,
or a pharmaceutically acceptable salt thereof.
7. The compound according to claim 5 wherein R1 is a phenyl group optionally substituted by a group selected from a chlorine atom, a fluorine atom, a cyano group, a difluoro-C1-4 alkyl group and a trifluoro-C1-4 alkyl group,
R2 is a phenyl group optionally substituted by one to two groups selected from a chlorine atom, a fluorine atom, a bromine atom and a cyano group,
R3 is a hydrogen atom,
R4 is a hydrogen atom, a C1-4 alkyl group, a difluoro-C1-4 alkyl group, a trifluoro-C1-4 alkyl group, a C1-4 alkyloxy-C1-4 alkyl group or a C1-4 alkyl-carbonyl-amino group,
E is one of the groups of the following formula (a) and (b):
\u2014C(\u2550O)\u2014N(R5)(R6),\u2003\u2003(a)
\u2014C(\u2550O)-Alk-N(R5)(R6),\u2003\u2003(b)
R5 is a hydrogen atom,
R6 is a C1-4 alkyl group, a pyridyl-C1-4 alkyl group, a C5-7 cycloalkyl group, a chlorophenyl group, a saturated or unsaturated 4- to 6-membered heteromonocyclic group optionally substituted by one to two group(s) selected from a halogen atom, an oxo group and C1-4 alkyloxy-C1-4 alkyl group or a group of the formula: \u2014N(R8)(R9), or both of them combine together with the adjacent nitrogen atom to form a saturated or unsaturated 5- to 6-membered heteromonocyclic group optionally substituted by one to two oxo group(s),
R8 is a C1-4 alkyl group and R9 is a C1-4 alkyl group, a chlorophenyl group, a pyridyl group or a C1-4 alkyl-pyridyl group,
or a pharmaceutically acceptable salt thereof.
8. The compound according to claim 1 wherein R1 and R2 are the same or different and a phenyl group optionally substituted by one to two group(s) selected from a halogen atom and a trihalogeno-C1-6 alkyl group, Q is a single bond, Ring A is a substituted pyrazole ring of the formula (A), R3 is a hydrogen atom, R4 is a hydrogen atom or a C1-6 alkyl group, E is a group of the formula (iii):
R5 is a hydrogen atom or a C1-6 alkyl group,
R6 is (a) a C1-6 alkyl group, (b) a C3-8 cycloalkyl group or (c) a saturated or unsaturated 5- to 6-membered sulfur- or nitrogen-containing heteromonocyclic group, or (d) both of them combine together with the adjacent nitrogen atom to form a saturated or unsaturated 5- to 6-membered nitrogen-containing heterocyclic group optionally substituted by one to two oxo group(s),
or a pharmaceutically acceptable salt thereof.
9. The compound according to claim 8 wherein R1 is a trihalogeno-C1-6 alkyl-phenyl group, R2 is a halogenophenyl group,
R4 is a C1-6alkyl group,
R5 is a hydrogen atom or a C1-6 alkyl group,
R6 is (a) a C1-6 alkyl group, (b) a C3-8 cycloalkyl group, (c) a saturated or unsaturated 5- to 6-membered sulfur- or nitrogen-containing heteromonocyclic group optionally substituted by one to two oxo group(s), or (d) both of them combine together with the adjacent nitrogen atom to form a saturated or unsaturated 5- to 6-membered heteromonocyclic group optionally substituted by one to two oxo group(s),
or a pharmaceutically acceptable salt thereof.
10. The compound according to claim 1 wherein R1 and R2 are the same or different and a phenyl group optionally substituted by one to two group(s) selected from a halogen atom and a trihalogeno-C1-6 alkyl group, Ring A is a substituted pyrazole ring of the formula (A), R3 is a hydrogen atom, R4 is a hydrogen atom or a C1-6 alkyl group, E is a group of the formula (iv):
R50 is a hydrogen atom or a C1-6 alkyl group,
R60 is (a) a C1-6alkyl group or (b) an acyl group, or both of them combine together with the adjacent nitrogen atom to form a saturated or unsaturated 5- to 6-membered nitrogen-containing heterocyclic group optionally substituted by one to two oxo group(s), or a pharmaceutically acceptable salt thereof.
11. The compound according to claim 1 wherein R1 and R2 are the same or different and a phenyl group optionally substituted by one to two group(s) selected from a halogen atom and a trihalogeno-C1-6 alkyl group, Q is a single bond, Ring A is a substituted pyrazole ring of the formula (C), R3 is a hydrogen atom, R4 is a group of the formula \u2014N(R\u2032)(R\u2033), R\u2032 and R\u2033 are the same or different and a hydrogen atom or a C1-6 alkyl group, or both of them combine together with the adjacent nitrogen atom to form a saturated or unsaturated 5- to 6-membered nitrogen-containing heterocyclic group, or a pharmaceutically acceptable salt thereof.
12. A compound according to claim 1, selected from the group consisting of:
6-(2-chlorophenyl)-7-(4-chlorophenyl)-3-(N-piperidinocarbamoyl)pyrazolo1,5-a-pyrimidine;
6-(2-chlorophenyl)-7-(4-chlorophenyl)-3-(N\u2032-methyl-N\u2032-phenylhydrazino)-carbonylpyrazolo1,5-apyrimidine;
6-(2-chlorophenyl)-7-(4-chlorophenyl)-3-(N-cyclohexylcarbamoyl)pyrazolo pyrimidine;
6-(2-chlorophenyl)-7-(4-chlorophenyl)-3-(N\u2032,N\u2032-dimethylhydrazino)carbonyl-pyrazolo1,5-apyrimidine;
6-(2-chlorophenyl)-7-(4-chlorophenyl)-3-(N-pyrrolidinocarbamoyl)pyrazolo1,5-a-pyrimidine;
6-(2-chlorophenyl)-7-(4-chlorophenyl)-3-(N-cyclopentylcarbamoyl)pyrazolo1,5-a-pyrimidine;
6-(2-chlorophenyl)-7-(4-chlorophenyl)-3-N-(4-tetrahydropyranyl)carbamoyl-pyrazolo1,5-apyrimidine;
6-(2-chlorophenyl)-7-(4-chlorophenyl)-3-N-(1,1-dioxo-tetrahydrothiophen-3-yl)-carbamoylpyrazolo1,5-apyrimidine;
(R)-6-(2-chlorophenyl)-7-(4-difluoromethylphenyl)-3N-(1,1-dioxo-tetrahydro-thiophen-3-yl)carbamoylpyrazolo1,5-apyrimidine;
(R)-6-(2-chlorophenyl)-7(4-trifluoromethylphenyl)-2-methyl-3-N-(1,1-dioxo-tetrahydrothiophen-3-yl)carbamoylpyrazolo1,5-apyrimidine;
(S)-6-(2-chlorophenyl)-7-(4-trifluoromethylphenyl)-2-methyl-3-N-(1,1-dioxo-tetrahydrothiophen-3-yl)carbamoylpyrazolo1,5-apyrimidine;
6-(2-chlorophenyl)-7-(4-chlorophenyl)-3-N-2-(2-pyridyl)ethylcarbamoyl-pyrazolo1,5-apyrimidine;
6-(2-clorophenyl)-7-(4-clorophenyl)-3-(N-cyclopentylcarbamoyl)-2-methoxy-pyrazolo1,5-apyrimidine;
(R)-6-(2-chlorophenyl)-7-(4-chlorophenyl)-2-methyl-3-N-(1,1-dioxo-tetrahydro-thiophen-3-yl)carbamoylpyrazolo1,5-apyrimidine;
(S)-6-(2-chlorophenyl)-7-(4-chlorophenyl)-2-methyl-3-N-(1,1-dioxo-tetrahydro-thiophen-3-yl)carbamoylpyrazolo1,5-apyrimidine;
6-(2-bromophenyl)-7-(4-chlorophenyl)-3-(N-cyclopentylcarbamoyl)pyrazolo1,5-a-pyrimidine;
(R,S)-6-(2-bromophenyl)-7-(4-chlorophenyl)-3-N-(1,1-dioxo-tetrahydrothiophen-3-yl)carbamoylpyrazolo1,5-apyrimidine;
(S)-6-(2-chlorophenyl)-7-(4-trifluoromethylphenyl)-3-N-(1,1-dioxo-tetrahydro-thiophen-3-yl)carbamoylpyrazolo1,5-apyrimidine;
(R)-6-(2-chlorophenyl)-7-(4-trifluoromethylphenyl)-3-N-(1,1-dioxo-tetrahydro-thiophen-3-yl)carbamoylpyrazolo1,5-apyrimidine;
6(2-chlorophenyl)-7-(4-chlorophenyl)-3-N\u2014N-(3-chlorophenyl)-N-methylamino-carbamoylpyrazolo1,5-apyrimidine;
6-(2-cyanophenyl)-7-(4-chlorophenyl)-3-N\u2014N-methyl-N-(2-pyridyl)amino-carbamoylpyrazolo1,5-apyrimidine;
6-(2-chlorophenyl)-7-(4-chlorophenyl)-3-(N-isobutylcarbamoyl)pyrazolo1,5-apyrimidine;
6-(2-chlorophenyl)-7-(4-trifluoromethylphenyl)-3-N-(1,1-dioxo-tetrahydro-thiophen-3-yl)carbamoylpyrazolo1,5-apyrimidine;
6-(2-chlorophenyl)-7-(4-trifluoromethylphenyl)-3-(N-cyclopentylcarbamoyl)-pyrazolo1,5-apyrimidine;
6-(2-chlorophenyl)-7-(4-trifluoromethylphenyl)-3-N\u2014N-methyl-N-(2-pyridyl)-aminocarbamoylpyrazolo1,5-apyrimidine;
(R)-6-(2-chlorophenyl)-7-(4-chlorophenyl)-3N-(1,1-dioxo-tetrahydrothiophen-3-yl)carbamoylpyrazolo1,5-apyrimidine;
6-(2-chlorophenyl)-7-(4-cyanophenyl)-3-(N-cyclopentylcarbamoyl)pyrazolo1,5-a-pyrimidine;
(R,S)-6-(2-chlorophenyl)-7-(4-chlorophenyl)-2-methyl-3-N-(1,1-dioxo-tetrahydro-thiophen-3-ylcarbamoylpyrazolo1,5-apyrimidine;
6(2-chlorophenyl)-7-(4-fluorophenyl)-3-(N-cyclopentylcarbamoyl)pyrazolo1,5-a-pyrimidine;
6(2-chlorophenyl)-7-(4-chlorophenyl)-3-N\u2014N-methyl-N-(2-pyridyl)amino-carbamoylpyrazolo1,5-apyrimidine;
(S)-6-(2-chlorophenyl)-7-(4-chlorophenyl)-3-N-(1,1-dioxo-tetrahydrothiophen-3-yl)carbamoylpyrazolo1,5-apyrimidine;
6-(2-chlorophenyl)-7-(4-chlorophenyl)-3-(N-ethylcarbamoyl)pyrazolo1,5-a-pyrimidine;
6-(2-chlorophenyl)-7-(4-chlorophenyl)-3-(N-cyclopropylcarbamoyl)-pyrazolo1,5-apyrimidine;
(S)-6-(2-chlorophenyl)-7-(4-chloro-2-fluorophenyl)-3N-(1,1-dioxotetrahydro-thiophen-3-yl)carbamoylpyrazolo1,5-apyrimidine;
(S)-6-(2-chlorophenyl)-7-(4-difluoromethylphenyl)-3N-(1,1-dioxotetrahydro-thiophen-3-yl)carbamoylpyrazolo1,5-apyrimidine;
(R)-6-(2-cyanophenyl)-7-(4-trifluoromethylphenyl)-3-N-(1,1-dioxotetrahydro-thiophen-3-yl)carbamoyl-2-methylpyrazolo1,5-apyrimidine;
(S)-6-(2-cyanophenyl)-7-(4-trifluoromethylphenyl)-3-N-(1,1-dioxotetrahydro-thiophen-3-yl)carbamoyl-2-methylpyrazolo1,5-apyrimidine;
6-(2-chlorophenyl)-7-(4-chlorophenyl)-3-N\u2032-methyl-N\u2032-(2-methoxypyridin-5-yl)-hydrazinocarbonylpyrazolo1,5-apyrimidine;
6-(2-cyanophenyl)-7-(4-chlorophenyl)-3-N-(1-pyrrolidinyl)carbamoyl-pyrazolo1,5-apyrimidine;
(R)-6-(2-cyanophenyl)-7-(4-chlorophenyl)-3-N-(1,1-dioxotetrahydro-thiophen-3-yl)carbamoyl-2-methylpyrazolo1,5-apyrimidine;
6-(2-cyanophenyl)-7-(4-chlorophenyl)-3-N\u2032-methyl-N\u2032-(2-pyridyl)hydrazino-carbonyl-2-methylpyrazolo1,5-apyrimidine;
(R)-6-(2-chlorophenyl)-7-(4-chlorophenyl)-3-N-(1,1-dioxotetrahydro-thiophen-3-yl)carbamoyl-2-trifluoromethylpyrazolo1,5-apyrimidine;
6-(2-chlorophenyl)-7-(4-trifluoromethylphenyl)-3-(N\u2032,N\u2032-dimethylhydrazino)-carbonyl-2-acetylaminopyrazolo1,5-apyrimidine;
6-(2-chlorophenyl)-7-(4-chlorophenyl)-3N-methyl-N\u2032-(2-pyridyl)hydrazino-carbonyl-2-acetylaminopyrazolo1,5-apyrimidine;
6-(2-chlorophenyl)-7-(4-chlorophenyl)-3-N\u2032-methyl-N\u2032-(2-pyridyl)hydrazino-carbonyl-2-(trifluoromethyl)pyrazolo1,5-apyrimidine;
6-(2-chlorophenyl)-7-(4-chlorophenyl)-3-N-(1-pyrrolidinyl)carbamoyl-2-difluoromethylpyrazolo1,5-apyrimidine;
(R)-6-(2-chlorophenyl)-7-(4-trifluoromethylphenyl)-3-N-(1,1-dioxotetrahydro-thiophen-3-yl)carbamoyl-2-difluoromethylpyrazolo1,5-apyrimidine;
(S)-6-(2-chlorophenyl)-7-(4-trifluoromethylphenyl)-3-N-(1,1-dioxotetrahydro-thiophen-3-yl)carbamoyl-2-difluoromethylpyrazolo1,5-apyrimidine;
6-(2-cyanophenyl)-7-(4-chlorophenyl)-3-(N-piperidinocarbamoyl)-2-difluoromethylpyrazolo1,5-apyrimidine;
6-(2-chlorophenyl)-7-(4-chlorophenyl)-3N-(1,1-dioxothiacyclobutan-3-yl)-carbamoylpyrazolo1,5-apyrimidine;
7-(4-chlorophenyl)-6-(2-cyano-4-fluorophenyl)-3-N-(1-pyrrolidinyl)carbamoyl-pyrazolo1,5-apyrimidine;
7-(4-chlorophenyl)-6-(2-cyanophenyl)-3-(N-piperidinocarbamoyl)-2-methyl-pyrazolo1,5-apyrimidine;
7-(4-chlorophenyl)-6-(2-cyanophenyl)-3-N-(1-pyrrolidinyl)carbamoyl-2-methyl-pyrazolo1,5-apyrimidine;
(S)-6-(2-chlorophenyl)-7-(4-chlorophenyl)-3-N-(2-methoxymethyl-1-pyrrolidinyl)-carbamoylpyrazolo1,5-apyrimidine;
6-(2-chlorophenyl)-7-(4-chlorophenyl)-3(N-(4-fluoropiperidino)carbamoyl-pyrazolo1,5-apyrimidine;
(R)-7-(4-chloro-2-fluorophenyl)-6-(2-cyanophenyl)-3-N-(1,1-dioxotetrahydro-thiophen-3-yl)carbamoyl-2-methylpyrazolo1,5-apyrimidine;
6-(2-chlorophenyl)-7-(4-chlorophenyl)-3-N\u2032-methyl-N\u2032-(2-ethoxypyridin-5-yl)-hydrazinocarbonylpyrazolo1,5-apyrimidine;
(R)-6-(2-chlorophenyl)-7-(4-chlorophenyl)-3-N-(1,1-dioxotetrahydro-thiophen-3-yl)carbamoyl-2-methoxymethylpyrazolo1,5-apyrimidine;
(S)-6-(2-chlorophenyl)-7-(4-chlorophenyl)-3N-(1,1-dioxotetrahydro-thiophen-3-yl)carbamoyl-2-methoxymethylpyrazolo1,5-apyrimidine;
6-(2-chlorophenyl)-7-(4-chlorophenyl)-3-N\u2032-methyl-N\u2032-(2-pyridyl)hydrazino-carbonyl-2-methoxymethylpyrazolo1,5-apyrimidine;
6-(2-chlorophenyl)-7-(4-chlorophenyl)-3-N-(1-pyrrolidinyl)carbamoyl-2-methoxymethylpyrazolo1,5-apyrimidine;
7-(4-chloro-2-fluorophenyl)-6-(2-cyanophenyl)-3N-(1-pyrrolidinyl)carbamoyl-2-methylpyrazolo1,5-apyrimidine;
6-(2-chlorophenyl)-7-(4-chlorophenyl)-3-2-(1,1-dioxothiomorpholino)acetyl-2-methylpyrazolo1,5-apyrimidine;
6-(2-cyanophenyl)-7-(4-chlorophenyl)-3-N-(4-fluoropiperidino)carbamoyl-2-methylpyrazolo1,5-apyrimidine; and
6-(2-chlorophenyl)-7-(4-trifluoromethylphenyl)-3-N-(tetrahydrothiophen-3-yl)-carbamoylpyrazolo1,5-apyrimidine,
or a pharmaceutically acceptable salt thereof.
13. The compound according to claim 1, wherein the compound is:
or a pharmaceutically acceptable salt thereof.
14. The compound according to claim 1, wherein the compound is:
or a pharmaceutically acceptable salt thereof.
15. The compound according to claim 1, wherein the compound is:
or a pharmaceutically acceptable salt thereof.
16. The compound according to claim 1, wherein the compound is:
or a pharmaceutically acceptable salt thereof.
17. A pharmaceutical composition comprising as an active ingredient a pyrazolo1,5-apyrimidine compound of the formula I:
wherein
R1 and R2 are the same or different and a 6- to 10-membered monocyclic or bicyclic aryl group optionally substituted by one to three group(s) selected from a halogen atom, a cyano group, a C1-6 alkyl group optionally substituted by one to three halogen atom(s), a C1-6 alkyloxy group optionally substituted by one to three halogen atom(s), an amino group optionally substituted by one to two C1-6 alkyl group(s), a C1-6 alkylthio group, a alkylsulfinyl group and a C1-6 alkylsulfonyl group,
Q is single bond, a methylene group or a group of the formula: \u2014N(RQ)\u2014,
RQ is a C1-6 alkyl group,
5-membered Ring A is a substituted pyrazole ring fused to the adjacent pyrimidine ring having the following formula (A), (B) or (C),
R3 and R4 are the same or different and (a) a hydrogen atom, (b) a cyano group, (c) a C1-6 alkyl group optionally substituted by one to three halogen atom(s), (d) a C1-6 alkyloxy group (the alkyl moiety of said group being optionally substituted by one to three group(s) selected from a halogen atom, a hydroxyl group, an amino group optionally substituted by one or two C1-6 alkyl group(s), a C1-6 alkyloxy group and a C1-6 alkylsulfonyl group), (e) a C1-6 alkylthio group, (f) a C1-6 alkylsulfinyl group, (g) a C1-6 alkylsulfonyl group or (h) a group of the formula: \u2014N(R\u2032)(R\u2033),
R\u2032 and R\u2033 are the same or different and (a) a hydrogen atom, (b) a C1-6 alkyl group optionally substituted by one to three group(s) selected from a halogen atom, an amino group optionally substituted by one or two C1-6 alkyl group(s) and a C1-6 alkyloxy group, (c) an acyl group, (d) a C1-6 alkylsulfonyl group or (e) an amino sulfonyl group optionally substituted by one to two C1-6 alkyl group(s), or both R\u2032 and R\u2033 combine each other at their termini to form together with an adjacent nitrogen atom a saturated or unsaturated 5- to 6-membered nitrogen-containing heterocyclic group optionally substituted by a hydroxyl group or a C1-6 alkyloxy group,
E is one of the following groups (ii) to (v):
Q1 is a single bond, a C1-6 alkylene group or a group of the formula: \u2014N(R7)\u2014, R7 is a hydrogen atom or a C1-6 alkyl group,
Q2 is a single bond or a C1-6 alkylene group,
one of R5 and R6 is a hydrogen atom or a C1-6 alkyl group and the other is (A) a C1-6 alkyl group optionally substituted by one to three group(s) selected from the group consisting of (a) a halogen atom; (b) a cyano group; (c) a C1-6 alkyloxy group; (d) a C3-8 cycloalkyl group optionally substituted by one to two group(s) selected from a cyano group and a C1-6 alkyl group; (e) an amino group optionally substituted by one or two a C1-6 alkyl group(s); (f) a C1-6 alkylthio group; (g) a C1-6 alkylsulfinyl group; (h) a C1-6 alkylsulfonyl group; (i) an acyl group; (j) a 6- to 10-membered monocyclic or bicyclic aryl group optionally substituted by one to two halogen atom(s); (k) a saturated or unsaturated 4- to 7-membered heteromonocyclic group (said heteromonocyclic group containing one to four heteroatom(s) selected from oxygen atom, sulfur atom and nitrogen atom); (l) a saturated or unsaturated 8- to 15-membered nitrogen-containing bi-cyclic or tri-cyclic heterocyclic group formed by fusing the aforementioned heteromonocyclic group with one or two other cyclic group(s) selected from a C3-8 cycloalkyl group, a 5- to 6-membered monocyclic aryl group and a saturated or unsaturated 4- to 7-membered heteromonocyclic group (said heteromonocyclic group containing one to four heteroatom(s) selected from oxygen atom, sulfur atom and nitrogen atom); and (m) a saturated or unsaturated 8- to 11-membered nitrogen-containing spiro-heterocyclic group,
(B) a C3-8 cycloalkyl group optionally substituted by one to two group(s) selected from a cyano group and a C1-6 alkyl group,
(C) a group of the formula: \u2014N(R8)(R9),
(D) a 6- to 10-membered monocyclic or bicyclic aryl group optionally substituted by one to two halogen atom(s), or
(E) a saturated or unsaturated heterocyclic group selected from the group consisting of i) a saturated or unsaturated 4- to 7-membered heteromonocyclic group (said heteromonocyclic group containing one to four heteroatom(s) selected from oxygen atom, sulfur atom and nitrogen atom), ii) a saturated or unsaturated 8- to 15-membered nitrogen-containing bi-cyclic or tri-cyclic heterocyclic group formed by fusing the aforementioned heteromonocyclic group with one or two other cyclic group(s) selected from a C3-8 cycloalkyl group, a 5- to 6-membered monocyclic aryl group and a saturated or unsaturated 4- to 7-membered heteromonocyclic group (said heteromonocyclic group containing one to four heteroatom(s) selected from oxygen atom, sulfur atom and nitrogen atom) and iii) a saturated or unsaturated 8- to 11-membered nitrogen-containing spiro-heterocyclic group, or
both R5 and R6 combine each other to form together with an adjacent nitrogen atom a saturated or unsaturated nitrogen-containing heterocyclic group selected from the group consisting of
(a) a saturated or unsaturated, 4- to 7-membered nitrogen-containing heteromonocyclic group, said heteromonocyclic group optionally containing two or more nitrogen atoms and optionally containing one to two heteroatom(s) other than such nitrogen atom(s) selected from oxygen atom and sulfur atom,
(b) a saturated or unsaturated, 8- to 15-membered nitrogen-containing bicyclic or tricyclic heterocyclic group formed by fusing the aforementioned heteromonocyclic group with one or two other cyclic group(s) selected from a C3-8 cycloalkyl group, a 5- to 6-membered monocyclic aryl group and a saturated or unsaturated, 4- to 7-membered heteromonocyclic group, said heteromonocyclic group containing one to four heteroatom(s) selected from oxygen atom, sulfur atom and nitrogen atom; and
(c) a saturated or unsaturated, 8- to 11-membered nitrogen-containing spiro-heterocyclic group,
R8 is a hydrogen atom or a C1-6 alkyl group,
R9 is
(a) a C1-6 alkyl group optionally substituted by one to three group(s) selected from a halogen atom, a cyano group and a phenyl group,
(b) a C3-8 cycloalkyl group,
(c) a 6- to 10-membered monocyclic or bicyclic aryl group optionally substituted by one to two halogen atom(s) or
(d) an acyl group or
(e) a saturated or unsaturated heterocyclic group selected from the group consisting of i) a saturated or unsaturated 4- to 7-membered heteromonocyclic group (said heteromonocyclic group containing one to four heteroatom(s) selected from oxygen atom, sulfur atom and nitrogen atom), ii) a saturated or unsaturated 8- to 15-membered nitrogen-containing bi-cyclic or tri-cyclic heterocyclic group formed by fusing the aforementioned heteromonocyclic group with one or two other cyclic group(s) selected from a C3-8 cycloalkyl group, a 5- to 6-membered monocyclic aryl group and a saturated or unsaturated 4- to 7-membered heteromonocyclic group (said heteromonocyclic group containing one to four heteroatom(s) selected from oxygen atom, sulfur atom and nitrogen atom) and iii) a saturated or unsaturated 8- to 11-membered nitrogen-containing spiro-heterocyclic group,
R50 is a hydrogen atom or a C1-6 alkyl group,
R60 is a hydrogen atom, a C1-6 alkyl group or an acyl group, or both of them combine together with the adjacent nitrogen atom to form a cyclic group of the following formula:
in which Ring A1 is a 5- to 7-membered aliphatic nitrogen-containing heterocyclic group optionally substituted by an oxo group,
R51 is an alkyl group or a 6- to 10-membered monocyclic or bicyclic aryl-sulfonyl group optionally substituted by one to two halogen atom(s),
R61 is a C1-6 alkylamino group or an azido group, and wherein
(a) the above-mentioned saturated or unsaturated heterocyclic group in R5, R6, R8 or R9 may be substituted by one to four groups selected from the group consisting of
a halogen atom;
a hydroxyl group;
a cyano group;
an oxo group;
a C1-6 alkyl group;
a C1-6 alkyl group substituted by one to three halogen atom(s);
a C1-6 alkyloxy-C1-6 alkyl group;
an amino-C1-6 alkyl group;
a C3-8 cycloalkyl group;
a phenyl-C1-6 alkyl group;
a C1-6 alkyloxy group;
a C1-6 alkyloxy group substituted by one to three halogen atom(s);
an acyl group;
an amino group optionally substituted by one to two C1-6 alkyl group(s);
an acylamino group;
a C1-6 alkylsulfonyl group;
an aminosulfonyl group optionally substituted by one to two C1-6 alkyl group(s);
a phenyl group optionally substituted by one to two halogen atom(s); and
a saturated or unsaturated 5- to 6-membered nitrogen-containing heterocyclic group, and
wherein
(b) the above-mentioned saturated or unsaturated heterocyclic group formed by combining R5 with R6 may be substituted by one to three group(s) selected from the group consisting of
a halogen atom;
a hydroxyl group;
a cyano group;
an oxo group;
a C1-6 alkyl group;
a C1-6 alkyl group substituted by one to three halogen atom(s);
a C1-6 alkyloxy-C1-6 alkyl group;
an amino-C1-6 alkyl group;
a C3-8 cycloalkyl group;
a phenyl-C1-6 alkyl group;
a C1-6 alkyloxy group;
a C1-6 alkyloxy group substituted by one to three halogen atom(s);
an acyl group;
an amino group optionally substituted by one to two C1-6 alkyl group(s);
an acylamino group;
a C1-6 alkylsulfonyl group;
an aminosulfonyl group optionally substituted by one to two C1-6 alkyl group(s); and
a phenyl group,
or a pharmaceutically acceptable salt thereof.