Patent number: 7511062
Abstract: The invention claims compounds of the formula wherein is a 5-membered heteroaryl; X is S or O; R1 is H, alkyl, cycloalkyl, cylcoalkylalkyl-, —CH2F, —CHF2, —CF3, —C(O)alkyl or —C(O)NR18R19; R3 and R4 H, alkyl, hydroxyalkyl or —C(O)Oalkyl; R5 and R6 are H, alkyl, hydroxyalkyl, alkoxyalkyl, mercaptoalkyl, —CH2F, —CHF2, —CF3, —C(O)OH or —C(O)Oalkyl; R7 is H, alkyl, alkenyl, hydroxyalkyl, cycloalkyl, alkoxyalkyl, aminoalkyl, (R17-phenyl)alkyl or —CH2—C(O)—O-alkyl; and R8 comprises alkyl, heteroaryl, phenyl or cycloalkyl, or heterocycloalkyl, all optionally substituted, or a cycloalkyl- or heterocycloalkyl-substituted amide; or R7 and R8 and the nitrogen to which they are attached together form an optionally substituted ring; and the remaining variables are as defined in the specification. Also claimed are pharmaceutical compositions, the use of the compounds as PDE4 inhibitors, and combinations with other actives.
Type:
Grant
Filed:
May 16, 2005
Date of Patent:
March 31, 2009
Assignee:
Schering Corporation
Inventors:
Rongze Kuang, David Blythin, Neng-Yang Shih, Ho-Jane Shue, Xiao Chen, Jianhua Cao, Danlin Gu, Ying Huang, John H. Schwerdt, Pauline C. Ting, Shing-Chun Wong, Li Xiao
Publication number: 20060106062
Abstract: The invention claims compounds of the formula wherein is a 5-membered heteroaryl; X is S or O; R1 is H, alkyl, cycloalkyl, cylcoalkylalkyl-, —CH2F, —CHF2, —CF3, —C(O)alkyl or —C(O)NR18R19; R3 and R4H, alkyl, hydroxyalkyl or —C(O)Oalkyl; R5 and R6 are H, alkyl, hydroxyalkyl, alkoxyalkyl, mercaptoalkyl, —CH2F, —CHF2, —CF3, —C(O)OH or —C(O)Oalkyl; R7 is H, alkyl, alkenyl, hydroxyalkyl, cycloalkyl, alkoxyalkyl, aminoalkyl, (R17-phenyl)alkyl or —CH2—C(O)—O-alkyl; and R8 comprises alkyl, heteroaryl, phenyl or cycloalkyl, or heterocycloalkyl, all optionally substituted, or a cycloalkyl- or heterocycloalkyl-substituted amide; or R7 and R8 and the nitrogen to which they are attached together form an optionally substituted ring; and the remaining variables are as defined in the specification. Also claimed are pharmaceutical compositions, the use of the compounds as PDE4 inhibitors, and combinations with other actives.
Type:
Application
Filed:
May 16, 2005
Publication date:
May 18, 2006
Inventors:
Rongze Kuang, David Blythin, Neng-Yang Shih, Ho-Jane Shue, Xiao Chen, Jianhua Cao, Danlin Gu, Ying Huang, John Schwerdt, Pauline Ting, Shing-Chun Wong, Li Xiao
Patent number: 6635630
Abstract: Compound represented by the structural formula
or a pharmaceutically acceptable salt thereof, wherein
Ar1 and Ar2 are optionally substituted heteroaryl or optionally substituted phenyl;
X1 is —O—, —S—, —SO—, —SO2—, —NR12—, —NCOR12— or —NR12SO2R15;
is selected from the group consisting of
X2 is —O—, —S— or —NR5—;
Y is ═O, ═S or ═NR11;
Y1 is H, C1-C6 alkyl, —NR17R13, —SCH3, R19-aryl(CH2)n6—, R19-heteroaryl-(CH2)n6—, —(CH2)n6—heterocycloalkyl, —(C1-C3)alkyl-NH—C(O)O(C1-C6)alkyl or —NHC(O)R15;
R5 is H or —(CH2)n1—G, wherein n1 is 0-5, G is H, —CF3, —CHF2, —CH2F, —OH, —O—(C1-C6 alkyl), —SO2R13, —O—(C3-C8 cycloalkyl), —NR13R14, —SO2NR13R14, —NR13SO2R15, —NR13COR12, —NR12(CONR13
Type:
Grant
Filed:
June 6, 2002
Date of Patent:
October 21, 2003
Assignee:
Schering Corporation
Inventors:
Neng-Yang Shih, Ho-Jane Shue, Gregory A. Reichard, Sunil Paliwal, David J. Blythin, John J. Piwinski, Dong Xiao, Xiao Chen
Patent number: 6436928
Abstract: A compound represented by the structural formula
or a pharmaceutically acceptable salt thereof, wherein
Ar1 and Ar2 are optionally substituted heteroaryl or optionally substituted phenyl;
X1 is —O—, —SO0-2—, —NR12—, —NCOR12— or —NR12SO2R15;
is
X2 is —O—, —S— or optionally substituted nitrogen;
Y is ═O, ═S or ═NR11;
Y1 is H, alkyl, —NR17R13, —SCH3, R19-aryl(CH2)n6—, R19-heteroaryl-(CH2)n6—, —(CH2)n6-heterocycloalkyl, -alkyl-NH—C(O)O-alkyl or —NHC(O)R15;
R1, R2, R3 and R7 are H, alkyl, OH-alkyl, cycloalkyl, —CHF2, —CH2F or —CF3; or R1 and R2 form an alkylene ring; or R1 and R2 together are ═O;
R6 is H, alkyl, —OR13 or —SR12;
and the remaining variables are as defined in the specification, is disclosed, as well as a pharmaceutical compositions comprising said compound, methods of
Type:
Grant
Filed:
December 14, 2000
Date of Patent:
August 20, 2002
Assignee:
Schering Corporation
Inventors:
Neng-Yang Shih, Ho-Jane Shue, Gregory A. Reichard, Sunil Paliwal, David J. Blythin, John J. Piwinski, Dong Xiao, Xiao Chen
Patent number: 5011845
Abstract: Compounds of the formula ##STR1## wherein R.sup.5 represents C.sub.1 to C.sub.6 -alkyl or the group--(CH.sub.2).sub.n --Z--(CH.sub.2).sub.m --Ar wherein Z represents O, S or --CH.sub.2 --and Ar is phenyl, optionally substituted by one or two groups selected from the group consisting of hydrogen, C.sub.1 to C.sub.6 -alkyl, C.sub.1 to C.sub.6 -alkoxy, Cl,F,Br,I,NO.sub.2, CF.sub.3, CN, R.sup.6 -S(O).sub.x, R.sup.7 --CO--,(R.sup.8 R.sup.9)NCO-and phenyl, wherein x is 0, 1 or 2, and each R.sup.6, R.sup.7, R.sup.8 and R.sup.9 is independently C.sub.1 to C.sub.6 alkyl or two adjacent groups on Ar may form together an additional fused benzenoid ring; n and m independently represent integers of from 1 to 8; and ring Q represents one of the rings Q.sub.1, Q.sub.2, Q.sub.3 or Q.sub.4 below: ##STR2## X is N or C--R.sup.1 ; Y is N or C--R.sup.4 ;W represents O or S;each of R.sup.1, R.sup.2, R.sup.3 and R.sup.4 is independently selected from hydrogen, C.sub.1 to C.sub.6 -alkyl, C.sub.1 to C.sub.6 -alkoxy, Cl,F,Br,I,NO.sub.
Type:
Grant
Filed:
June 13, 1990
Date of Patent:
April 30, 1991
Assignee:
Schering Corporation
Inventors:
David J. Blythin, Ho-Jane Shue, Ashit K. Ganguly
