| US 7,601,850 B2 | ||
| Phenyl-thiophene type vitamin D receptor modulators | ||
| Karl Robert Dahnke, Carmel, Ind. (US); Robert Peter Gajewski, Indianapolis, Ind. (US); Charles David Jones, Indianapolis, Ind. (US); Jared Harris Linebarger, Indianapolis, Ind. (US); Jianliang Lu, Fishers, Ind. (US); Tianwei Ma, Carmel, Ind. (US); Sunil Nagpal, Carmel, Ind. (US); Todd Parker Simard, Fishers, Ind. (US); Ying Kwong Yee, Carmel, Ind. (US); Emilio Enrique Bunel, Thousand Oaks, Calif. (US); and Ryan Edward Stites, Indianapolis, Ind. (US) | ||
| Assigned to Eli Lilly and Company, Indianapolis, Ind. (US) | ||
| Appl. No. 10/515,403 PCT Filed May 22, 2003, PCT No. PCT/US03/14539 § 371(c)(1), (2), (4) Date Jan. 25, 2006, PCT Pub. No. WO03/101978, PCT Pub. Date Dec. 11, 2003. |
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| Claims priority of provisional application 60/384151, filed on May 29, 2002. | ||
| Prior Publication US 2006/0287536 A1, Dec. 21, 2006 | ||
| Int. Cl. C07D 333/06 (2006.01); C07D 333/26 (2006.01) | ||
| U.S. Cl. 549—80 | 19 Claims |
1. A compound represented by formula I or a pharmaceutically acceptable salt thereof:
 R and R′ are independently C1-C5 alkyl, C1-C5 fluoroalkyl, or together R and R′ form a substituted or unsubstituted, saturated or unsaturated carbocyclic ring having from
3 to 8 carbon atoms;
Ring atoms Q1 and Q2 are independently selected from carbon or sulfur, with the proviso that one atom is sulfur and the other atom is carbon;
RP is C1—C5 alkyl;
RT is selected from hydrogen, C1-C5 alkyl, C1-C5 fluoroalkyl, —O—C1-C5 alkyl;
(Lp) and (LT) are divalent linking groups independently selected from the group consisting of
 Zp and ZT are independently selected from
—(C1-C5 alkyl),
—(C1-C5 alkyl)-C(O)—(C1-C5 alkyl),
—(C1-C5 alkyl)-C(O)—(O—C1-C5 alkyl),
—(C1-C5 alkyl)-C(O)—OH,
—(C1-C5 alkyl)-SO2—(C1-C5 alkyl),
—(C1-C5 alkyl)-S(O)—(C1-C5 alkyl),
—(C1-C5 alkyl)-N(C(O)(C1-C5 alkyl)CH2C(O)OH,
—(C1-C5 alkyl)-N(C(O)(C1-C5 alkyl)CH2C(O)—(C1-C5 alkyl),
—CH(OH)—(C1-C5 alkyl)
—C(O)—O—(C1-C5 alkyl),
—C(O)—NH(OH),
—C(O)—N—(C1-C5 alkyl)2
—C(O)—NH—(C1-C5 alkyl)-SO2—(C1-C5 alkyl),
—C(O)—NH—(C1-C5 alkyl)-S(O)—(C1-C5 alkyl),
—C(O)—NH—CH2—C(O)OH,
—C(O)—NH—CH2—C(O)—(O—C1-C5 alkyl),
—C(O)—N—(C1-C5 alkyl)(C(O)OH),
—C(O)—N—(C1-C5 alkyl)(C(O)—(O—C1-C5 alkyl)),
—C(O)—NH—CH((CH2)(CO2H))(CO2H),
—C(O)—NH—CH((CH2)(C(O)—(C1-C5 alkyl)))(C(O)—(O—C1C5 alkyl)),
—C(O)—NH—CH((CH2)(C(O)—(—O—C1-C5 alkyl)))(C(O)—(O—C1C5 alkyl)),
—C(O)—NH—CH((CH2OH)(CO2H)),
—C(O)—NH—CH((CH2OH)(C(O)(O—C1-C5 alkyl)),
—C(O)—NH—C((C1-C5 alkyl)(C1-C5 alkyl))(CO2H),
—C(O)—NH—C((C1-C5 alkyl)(C1-C5 alkyl))(C(O)—(O—C1-C5 alkyl)),
—C(O)—NH—5-tetrazolyl,
—C(O)—N-pyrrolidin-2-(CO2H),
—C(O)—N-pyrrolidin-2-(C(O)—(O—C1-C5 alkyl)),
—C(O)—N—(C1-C5 alkyl))CH2(CO2H),
—O—(C1-C5 alkyl)-C(O)—OH,
—O—(C1-C5 alkyl)-C(O)—NH—5-tetrazolyl,
—O—(C1-C5 alkyl)-C(O)—(C1-C5 alkyl),
—O—(C1-C5 alkyl)-C(O)—(O—C1-C5 alkyl),
—O—(C1-C5 alkyl)-S(O)—(C1-C5 alkyl),
—O—SO2—(C1-C5 alkyl),
—SO2—(C1-C5 alkyl),
—SO2—NH2,
—SO2—NH—(C1-C5 alkyl)-C(O)OH,
—SO2—NH—(C1-C5 alkyl)-C(O)(O—C1-C5 alkyl),
—SO2—NHC(O)—(C3-C6 cycloalkyl),
—SO2—NH—C(O)—(C1-C5 alkyl),
—SO2—N—(C1-C5 alkyl)2,
—SO2—N═CHN(C1-C5 alkyl)2,
—N(OH)(CH3),
 —I,
—Br
—Cl
—F, provided that the combined groups of formula I represented by
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