| US 7,566,781 B2 | ||
| Imidazopyridine compound | ||
| Shunji Sakuraba, Tsukuba (Japan); Minoru Moriya, Tsukuba (Japan); Hidekazu Takahashi, Tsukuba (Japan); Hiroyuki Kishino, Tsukubamirai (Japan); Makoto Jitsuoka, Moriya (Japan); Minoru Kameda, Adachi (Japan); and Akio Kanatani, Ushiku (Japan) | ||
| Assigned to Banyu Pharmaceutical Co., Ltd., Tokyo (Japan) | ||
| Appl. No. 11/579,570 PCT Filed May 09, 2005, PCT No. PCT/JP2005/008819 § 371(c)(1), (2), (4) Date Nov. 06, 2006, PCT Pub. No. WO2005/108399, PCT Pub. Date Nov. 17, 2005. |
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| Claims priority of application No. 2004-139909 (JP), filed on May 10, 2004. | ||
| Prior Publication US 2007/0249659 A1, Oct. 25, 2007 | ||
| Int. Cl. C07D 491/02 (2006.01); C07D 237/02 (2006.01); C07F 9/02 (2006.01); A61K 31/519 (2006.01) | ||
| U.S. Cl. 544—281 [544/229; 544/244; 514/258; 514/259; 514/300; 514/43; 514/80; 546/121] | 18 Claims |
1. A compound of formula I or its pharmaceutically-acceptable salt:
 R1 R2 are each independently selected from the group consisting of:
(1) a hydrogen atom,
(2) a halogen atom,
(3) a C1-6 alkyl group,
(4) a C2-6 alkenyl group,
(5) a C3-8 cycloalkyl-C0-4 alkyl group,
(6) a C1-6 alkylamino group,
(7) a di-C1-6 alkylamino group,
(8) a C1-6 alkylcarbonylamino group,
(9) a C1-6 alkylcarbonyl(C1-6 alkyl)amino group,
(10) a 3- to 8-membered heterocycloalkyl-C0-4 alkyl group, and
(11) a pyrazolyl-C1-4 alkyl group,
wherein any hydrogen atom in the alkyl moiety may be optionally substituted with R5, any hydrogen atom in the cycloalkyl or heterocycloalkyl moiety may be optionally substituted with R6, and R1 and R2 must not be hydrogen atoms at the same time, or
R1 and R2 together form, along with the carbon atom bonding thereto, a 5- to 8-membered carbon ring optionally substituted with R6;
R3 is a hydrogen atom, a halogen atom, a C1-6 alkyl group, or a C1-6 alkyloxy group;
R4 is a hydrogen atom, or a C1-6 alkyl group;
R5 is selected from the group consisting of a halogen atom, a cyano group, a hydroxyl group, an amino group, a C1-6 alkyl group optionally substituted with a fluorine atom or a hydroxyl group, a mono-C1-6 alkylamino group, a di-C1-6 alkylamino group, a C1-6 alkyloxy group optionally substituted with a fluorine atom, a C1-6 alkyloxy-C1-6 alkyl group, a C1-6 alkyloxycarbonyl group, a C1-6 alkyloxycarbonylamino group, a C1-6 alkyloxycarbonyl(C1-6 alkyl)amino group, a C1-6 alkylcarbonyl group, a C1-6 alkylcarbonyloxy group, a C1-6 alkylcarbonylamino group, a C1-6 alkylcarbonyl(C1-6 alkyl)amino group, a carbamoyl group, a mono-C1-6 alkylcarbamoyl group, a di-C1-6 alkylcarbamoyl group, a carbamoylamino group, a mono-C1-6 alkylcarbamoylamino group, a di-C1-6 alkylcarbamoylamino group, a mono-C1-6 alkylcarbamoyl(C1-6 alkyl)amino group, a di-C1-6 alkylcarbamoyl(C1-6 alkyl)amino group, a carbamoyloxy group, a mono-C1-6 alkylcarbamoyloxy group, a di-C1-6 alkylcarbamoyloxy group, a C1-6 alkylsulfonyl group, a C1-6 alkylsulfonylamino group, a C1-6 alkylsulfonyl(C1-6 alkyl)amino group, a sulfamoyl group, a mono-C1-6 alkylsulfamoyl group, a di-C1-6 alkylsulfamoyl group, a sulfamoylamino group, a (mono-C1-6 alkylsulfamoyl)amino group, a (di-C1-6 alkylsulfamoyl)amino group, a mono-C1-6 alkylsulfamoyl(C1-6 alkyl)amino group, and a di-C1-6 alkylsulfamoyl(C1-6 alkyl)amino group;
R6 is R5 or an oxo group;
W is:
(a) —(CH2)m+1—,
(b) —(CH2)m—CH═CH—(CH2)n—,
(c) —(CH2)m—O—(CH2)n—,
(d) —O—(CH2)m+1—O—,
(e) —(CH2)m—S(O)y1—(CH2)n—,
(f) —(CH2)m—C(O)—(O)y2—(CH2)n—,
(g) —(CH2)m—C(O)—NH—(CH2)n—,
(h) —(CH2)m—NH—C(O)—(CH2)n—, or
(i) —(CH2)m—NH—(CH2)n—,
wherein any hydrogen atom in the alkylene moiety of the substituent may be optionally substituted with R5;
m and n are each independently an integer of from 0 to 10, satisfying 0≤m+n≤10;
y1 is 0, 1 or 2; y2 is 0 or 1;
Ar1 is a divalent substituent, selected from
(a) a monocyclic or bicyclic, 3- to 8-membered aromatic or aliphatic heterocyclic group optionally substituted with R5, and
(b) a monocyclic or bicyclic, 3- to 8-membered aromatic or aliphatic carbocyclic group optionally substituted with R5;
Ar2 is a 5- or 6-membered aromatic carbocyclic group optionally having a substituent, or a 5- or 6-membered aromatic heterocyclic
group optionally having a substituent selected from: a chlorine group, a fluorine group, a bromine group, a methyl group,
an ethyl group, an isopropyl group, a 1-hydroxy-1-methylethyl group, a difluoromethyl group, a trifluoromethyl group, a methoxy
group, an ethoxy group, an isopropyloxy group, a difluoromethoxy group, a trifluoromethoxy group, a cyclopropyl group, a cyclopropyloxy
group, a methylsulfonyl group, a methylsulfinyl group, a methylsulfanyl group, an ethylsulfonyl group, a nitrile group, and
a dimethylamino group.
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