US2003220365A1PendingUtilityA1
Cell adhesion-inhibiting antiinflammatory compounds
Priority: Jun 4, 1998Filed: Mar 12, 2003Published: Nov 27, 2003
Est. expiryJun 4, 2018(expired)· nominal 20-yr term from priority
Inventors:Andrew O. StewartSteven A. BoydDavid L. ArendsenPramila BhatiaKevin Ronald CondroskiJennifer FreemanIndrani W. GunawardanaGui-Dong ZhuKraig LarteyCatherine M. MccartyNicholas A. MortMeena PatelMichael A. StaegerDavid M. Stout
C07D 493/04C07D 513/04C07D 495/04
49
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Claims
Abstract
Compounds having Formula I are useful for treating inflammation. Also disclosed are pharmaceutical compositions comprising compounds of Formula I, and methods of inhibiting/treating inflammatory diseases in a mammal.
Claims
exact text as granted — not AI-modifiedWhat is claimed is:
1 . A compound having Formula I
or a pharmaceutically acceptable salt or prodrug thereof, where the symbol z, 900 represents a single bond or a double bond, provided that when one bond is a double bond, the adjacent bond is a single bond;
E, F, and G are independently selected from.
(1) carbon,:
(2) nitrogen, and
(3) N + —O − ,
provided that at least one of E, F or G is nitrogen or N + —O − , and further provided that at least one of E, F or G is carbon;
Y and Z are independently selected from
(b 1 ) carbon,
(2) nitrogen,
(3) oxygen, and
(4) S(O) t where t is an integer 0-2,
provided that at least one of Y or Z is other than carbon;
L A is selected from
(1) a covalent bond,
(2) —O—,
(3) —S(O) t —,
(4) —NR 6 — where R 6 is selected from
(a) hydrogen,
(b) alkyl of one to ten carbons optionally substituted with 1 or 2 substituents independently selected from,
(i) aryl and
(ii) cycloalkyl of three to ten carbons,
(c) alkanoyl where the alkyl part is of one to ten carbons, and
(d) cycloalkyl of three to ten carbons,
(5) —C(W)— where W is selected from
(a) O and
(b) S, and
(6) alkenylene;
X A is selected from
(1) halo,
(2) alkyl of one to ten carbons optionally substituted with 1, 2, or 3 substituents independently selected from
(a) oxo,
(b) cycloalkyl of three to ten carbons,
(c) —CO 2 R 7 where R 7 is selected from
(i) hydrogen and
(ii) alkyl of one to ten carbons optionally substituted with 1, or 2 substituents independently selected from
aryl and
cycloalkyl of three to ten carbons,
(d) —NR 8 R 9 where R 8 and R 9 are independently selected from
(i) hydrogen,
(ii) alkyl of one to six carbons optionally substituted with 1 or 2 substituents independently selected from
—OH,
aryl,
heterocycle,
cycloalkyl of three to ten carbons, and
—NR A R B where R A and R B are independently selected from:
hydrogen and
alkyl of one to six carbons optionally substituted with 1 or 2 substituents selected from —OH,
(iii) alkanoyl where the alkyl part is of one to to ten carbons,
(iv) cycloalkyl of three to ten carbons,
(v) alkoxy,
(vi) heterocycle, and
(vii) aryl,
where (vi) and (vii) are substituted with 1 or 2 substituents independently selected from
alkyl of one to six carbons and
halo,
(e) —C(W)R 10 where W is previously defined and R 10 is selected from
(i) hydrogen,
(ii) alkyl of one to ten carbons optionally substituted with 1, or 2 substituents independently selected from
aryl and
cycloalkyl of three to ten carbons,
(iii) —NR 8 R 9 , and
(iv) —OR 7 ,
(f) —OH,
(g) aryl, and
(h) heterocycle,
where (g) and (h) can be optionally substituted with 1, 2, 3, 4, or 5 substituents independently selected from
(i) alkyl of one to twenty carbons,
(ii) —NR 8 R 9 ,
(iii) alkoxy of one to ten carbons,
(iv) thioalkoxy of one to ten carbons,
(v) halo,
(vi) perfluoroalkyl of one to three carbons,
(vii) alkenyl of two to ten carbons,
(viii) alkyl of one to ten carbons optionally substituted with 1 or 2 substituents independently selected from
alkoxy of one to ten carbons and
—OH,
(ix) —CO 2 R 7 ,
(x) aryl, and
(xi) —CHO,
(3) cycloalkyl of three to ten carbons,,
(4) aryl,
(5) heterocycle
where (4) and (5) can be optionally substituted with 1, 2, 3, 4, or 5 substituents independently selected from
(a) alkyl of one to twenty carbons,
(b) alkyl of one to ten carbons substituted with 1, 2, or 3 substituents independently selected from
(i) —OR 11 where R 11 is selected from hydrogen,
—C(W)R 12 where R 12 is selected from
alkyl of one to ten carbons,
cycloalkyl of three to ten carbons,
aryl, and
heterocycle, and
heterocycle optionally substituted with 1, 2, 3, or 4 substituents independently selected from
—OH and
alkyl of one to six carbons optionally substituted with 1 or 2 substituents selected from —OH,
(ii) alkoxy of one to ten carbons optionally substituted with 1 or 2 substituents independently selected from
alkoxy and
alkoxyalkoxy,
(iii) spiroalkyl of three to ten carbons, and
(iv) halo,
(c) alkoxy of one to ten carbons optionally substituted with 1 or 2 substituents independently selected from;
(i) alkoxy and
(ii) alkoxyalkoxy,:
(d) thioalkoxy of one to ten carbons,
(e) halo,
(f) perfluoroalkyl of one to three carbons,
(g) alkenyl of two to ten carbons optionally substituted with 1 or 2 substituents independently selected from
(i) —C(W)R 10 and
(ii) —C(W)R 12 ,
(h) —CO 2 R 7 ,
(i) —NR 8 R 9 ,
(j) aryl,
(k) —C(W)R 12 ,
(l) —CHO,
(m) —C(O)NR 8 R 9 ,
(n) —CN,
(o) heterocycle optionally substituted with 1 or 2 substituents independently selected from
(i) alkyl of one to ten carbons and
(ii) perfluoroalkyl of one to three carbons,
(p) —C(W)R 10 ,
(q) ethylenedioxy, and
(r) —OCF 3 ,
(6): —OR 7 ,
(7) hydrogen, and
(8) —NR 8 R 9 ;
L B is selected from
(1) a covalent bond,
(2) —O—,
(3) —S(O) t —,
(4) —NR 6 —,
(5) —C(W)—; and
(6) —C(═NR 13 )— where R 13 is selected from
(a) hydrogen,
(b) —NO 2 ,
(c) —CN, and
(d) —OR 14 where R 14 is selected from
(i) hydrogen,
(ii) aryl, and
(iii) alkyl of one to ten carbons optionally substituted with 1 or 2 substituents independently selected from
aryl and
—C(O)R 15 where R 15 is selected from:
hydrogen,
—OH,
alkoxy, and
NR A R B ;
X B is selected from
(1) hydrogen,
(2) alkyl of one to ten carbons optionally substituted with 1, 2, or 3 substituents independently selected from
(a) —CO 2 R 7 ,
(b) —NR 8 R 9 ,
(c) —C(W)NR 8 R 9 ,
(d) heterocycle,
(e) aryl optionally substituted with 1 or 2 substituents independently selected from
(i) alkyl of one to ten carbons,
(ii) —NO 2 , and
(iii) —NR A R B ,
(f) —OR 16 where R 16 is selected from
(i) hydrogen and
(ii) —C(W)NR A R B , and
(g) —NR A C(W)NR 8 R 9 ,
(3) alkenyl of two to six carbons optionally substituted with 1 or 2 substituents independently selected from
(a) —C(W)NR A R B ,
(b) —CO 2 R 7 , and
(c) heterocycle,
(4) —NR 17 R 18 where R 17 and R 18 are independently selected from
(a) hydrogen,
(b) alkyl of one to ten carbons optionally substituted with 1, 2, or 3 substituents independently selected from
(i) —OH,
(ii) —C(W)R 10 ,
(iii) —NR A C(═NR13)NR B R 19 where R A , R B , and R 13 are previously defined and R 19 is selected from
hydrogen,
alkyl of one to ten carbons, and
—NO 2 ,
(iv) heterocycle,
(v) aryl,
(vi) halo, and
(vii) —NR A R B ,
(c) alkoxy,
(d): aryl optionally substituted with 1, 2, or 3 substituents independently selected from
(i) halo,
(ii) alkyl of one to ten carbons,
(iii) alkoxy of one to ten carbons, and
(iv) perfluoroalkyl of one to three carbons,
(e) heterocycle,
(f) —NR A R B ,
(g) —C(O)R 20 where R 20 is selected from
(i) hydrogen,
(ii) alkyl of one to ten carbons,
(iii) —OR 12 , and
(iv) —NR A R B ,
(h) cycloalkyl of three to ten carbons, and
(i) —OH,
(5) alkoxy,
(6) —OH,
(7) —NR A C(═NR 13 )NR B R 19 ,
(8) —C(W)NR 8 R 9 ,
(9) aryl,
(10) heterocycle,
where (9) and (10) can be optionally substituted with 1, 2, 3, 4, or 5 substituents independently selected from
(a) halo,
(b) alkyl of one to ten carbons optionally substituted with 1, 2, or 3 substituents independently selected from
(i) halo,
(ii) alkoxy of one to ten carbons,
(iii) —NR A R B ,
(iv) —OH,
(v) —CO 2 R 7 ,
(vi) —C(W)NR A R B , and
(vii) aryl,
(c) —NR A R B ,
(d) alkoxy of one to ten carbons,
(e) thioalkoxy of one to ten carbons,
(f) perfluoroalkyl of one to three carbons,
(g) —OH,
(h) —C(W)NR 8 R 9 ,
(i) —CO 2 R 7 ,
(j) —NR A C(W)OR 21 where R A is previously defined and R 21 is selected from
(i) alkyl of one to ten carbons optionally substituted with 1 or 2 substituents selected from
aryl and
cycloalkyl of three to ten carbons,
(ii) aryl, and
(iii) cycloalkyl of three to ten carbons,
(k) alkenyl of two to ten carbons,
(l) heterocycle,
(m) aryl, and
(n) —NO 2 ,
(11) —CN,
(12) —CHO,
(13) halo, and
(14) —B(OR A )(OR B );
provided that when R 1 , R 2 , R 3 , R 4 , and R 5 are hydrogen or absent, -L A - is a covalent bond, and -L B - is a covalent bond, then one of X A or X B is other than hydrogen; and
R 1 , R 2 , R 3 , R 4 , and R 5 are absent or independently selected from
(1) hydrogen,
(2) alkyl of one to six carbons optionally substituted with 1 or 2 substituents independently selected from
(a) —OC(O)R 22 , where R 22 is selected from
(i) alkyl,
(ii) alkoxy, and
(iii) NR A R B ,
(b) alkoxy,
(c) —OH,
(d) —NR A R B ,
(e) heterocycle, and.
(f) aryl,
(3) —CO 2 R 7 ,
(4) —C(O)NR A R B ,
(5) —SR 23 where R 23 is selected from
(a) hydrogen,
(b) alkyl of one to six carbons,
(c) aryl optionally substituted with 1 or 2 substituents selected from
(i) alkyl of one to six carbons and
(ii) halo,
(6) —NR A R B ,
(7) halo,
(8) alkoxy,
(9) perfluoroalkyl of one to three carbons,
(10) —OH, and
(11) heterocycle,
provided that when E, F, and Y are carbon, G is nitrogen, Z is sulfur, -L A - is a covalent bond, and X A is halo, R 1 is other than —CO 2 R 7 .
2 . A compound according to claim 1 where F and Y are carbon, E and G are independently nitrogen or N + —O − , and Z is S(O) t .
3 . A compound according to claim 2 selected from the group consisting of methyl 2-[(6-ethylthieno[2,3-d]pyrimidin-4-yl)thio]acetate,
6-ethyl-4-[(4-methylphenyl)thio]thieno[2,3-d]pyrimidine,
6-ethyl-4-(2-pyridinylthio)thieno[2,3-d]pyrimidine,
6-ethyl-4-[(2-methylethyl)thio]thieno[2,3-d]pyrimidine,
6-ethyl-4-[(phenylmethyl)thio]thieno[2,3-d]pyrimidine,
6-ethyl-4-[(5 -methyl-1,3,4-thiadiazol-2-yl)thio]thieno[2,3-d]pyrimidine, ethyl 6-ethyl-4-[(4-methylphenyl)thio]thieno[2,3-d]pyrimidine-6-carboxylate,
6-ethyl-N-(phenylmethyl)thieno[2,3-d]pyrimidin-4-amine,
6-ethyl-N-(5-methyl-1,3,4-thiadiazol-2-yl)thieno[2,3-d]pyrimidin-4-amine,
4-[(5-amino-1,3,4-thiadiazol-2-yl)thio]-6-ethyl-2-(phenylmethyl)thieno[2,3-d]pyrimidine,
4-chloro-6-ethyl-2-(phenylmethyl)thieno[2,3-d]pyrimidine, and
4-[(5-amino-1,3,4-thiadiazol-2-yl)thio]-6-ethyl-2-(phenylmethyl)thieno[2,3-d]pyrimidine.
4 . A compound according to claim 1 where F and Z are carbon, E and G are independently nitrogen or N + —O − , and Y is S(O) t .
5 . A compound according to claim 4 selected from the group consisting of
7-methyl-4-[(4-methylphenyl)thio]thieno[3,2-d]pyrimidine,
7-methyl-4-[(5-methyl-1,3,4-thiadiazol-2-yl)thio]thieno[3,2-d]pyrimidine,
7-methyl-4-[[5-(methylthio)-1,3,4-thiadiazol-2-yl]thio]thieno[3,2-d]pyrimidine,
4-[(5-amino-1,3,4-thiadiazol-2-yl)thio]-7-methylthieno[3,2-d]pyrimidine,
7-methyl-N-[(4-(methylthio)phenyl]thieno[3,2-d]pyrimidin-7-amine, and
7-methyl-4-[(4-methylphenyl)thio]thieno[3,2-d]pyrimidine-6-carboxamide.
6 . A compound according to claim 1 where E, G and Y are carbon, F is nitrogen or N + —O − , and Z is S(O) t .
7 . A compound according to claim 6 selected from the group consisting of
methyl 4-[(4-methylphenyl)thio]thieno[2,3-c]pyridine-2-carboxylate,
4-[(4-methylphenyl)thio]thieno[2,3-c]pyridine-2-carboxylic acid,
4-[(4-methylphenyl)thio]thieno[2,3-c]pyridine-2-carboxamide,
4-(2-pyridinylthio)thieno[2,3-c]pyridine-2-carboxamide,
4-[(4-chlorophenyl)thio]thieno[2,3-c]pyridine-2-carboxamide, N-methoxy-N-methyl-4-[(4-methylphenyl)thio]thieno[2,3-c]pyridine-2-carboxamide,
N-methoxy-4-[(4-methylphenyl)thio]thieno[2,3-c]pyridine-2-carboxamide, N-(4-chlorophenyl)-4-[(4-methylphenyl)thio]thieno[2,3-c]pyridine-2-carboxamide,
4-[(4-methylphenyl)thio]thieno[2,3-c]pyridine-2-carboxaldehyde,
4-[(4-methylphenyl)thio]thieno[2,3 -c]pyridine-2-carboxaldehyde, O-methyloxime,
4-[(4-methylphenyl)thio]thieno[2,3-c]pyridine-2-carboxaldehyde, O-(phenylmethyl)oxime,
2-[[[4-[(4-methylphenyl)thio]thieno[2,3-c]pyridin-2-ylmethylene]amino]oxy]acetic acid,
4-[(4-methylphenyl)thio]thieno[2,3-c]pyridine-2-carboxaldehyde, O-phenyloxime,
4-[(4-methylphenyl)thio]thieno[2,3-c]pyridine-2-carboxaldehyde, oxime
2-[[[4-[(4-methylphenyl)thio]thieno[2,3-c]pyridine-2-ylmethylene]amino]oxy]acetamide,
(E)-3-[(4-methylphenyl)thio]thieno[2,3-c]pyridin-2-yl]-2-propenamide,
1-4-[(4-methylphenyl)thio]thieno[2,3-c]pyridin-2-yl]ethanone,
2-benzoyl-4-[(4-methylphenyl)thio]thieno[2,3-c]pyridine,
2-ethyl-4-[(4-methylphenyl)thio]thieno[2,3-c]pyridine,
1-[4-[(4-methylphenyl)thio]thieno[2,3-c]pyridin-2-yl]ethanone, oxime, N-(2,3-dihydroxypropyl)-4-[(4-methylphenyl)thio]thieno[2,3-c]pyridine-2-carboxamide,
4-[(4-methylphenyl)thio]thieno[2,3-c]pyridine-2-carboxylic acid, hydrazide, N 2 -4-[(4-methylphenyl)thio]thieno[2,3-c]pyridin-2-yl]carbonyl]-N 6 -[(nitroamino)iminomethyl]-L-lysine, methyl ester, N-(aminoiminomethyl)-4-[(4-methylphenyl)thio]thieno[2,3-c]pyridine-2-carboxamide,
4-[(4-methylphenyl)thio]thieno[2,3-c]pyridine-2-carbothioamide, 4-[(4-methylphenyl)thio]thieno[2,3-c]pyridine, methyl 4-[(2-methoxy-2-oxoethyl)thio]thieno[2,3-c]pyridine-2-carboxylate,
4-[(2-amino-2-oxoethyl)thio]thieno[2,3-c]pyridine-2-carboxamide,
4-[(4-bromophenyl)thio]thieno[2,3-c]pyridine-2-carboxamide,
4-(phenylthio)thieno[2,3-c]pyridine-2-carboxamide,
4-[[4-(trifluoromethyl)phenyl]thio]thieno[2,3-c]pyridine-2-carboxamide,
4-[(2-methylphenyl)thio]thieno[2,3-c]pyridine-2-carboxamide,
4-[(3-methylphenyl)thio]thieno[2,3-c]pyridine-2-carboxamide,
4-[(3,4-dimethylphenyl)thio]thieno[2,3-c]pyridine-2-carboxamide,
4-[(3,5-dimethylphenyl)thio]thieno[2,3-c]pyridine-2-carboxamide,
4-[(2,4-dimethylphenyl)thio]thieno[2,3-c]pyridine-2-carboxamide,
4-[(2-methyl-3-furanyl)thio]thieno[2,3-c]pyridine-2-carboxamide,
4-[[(4-chlorophenyl)methyl]thio]thieno[2,3-c]pyridine-2-carboxamide,
4-[(3,4-dichlorophenyl)thio]thieno[2,3-c]pyridine-2-carboxamide,
4-[(4-methoxyphenyl)thio]thieno[2,3-c]pyridine-2-carboxamide,
4-(cyclohexylthio)thieno[2,3-c]pyridine-2-carboxamide,
4-[(4-Methylphenyl)thio]-N-[3-(4-morpholinyl)propyl]thieno[2,3-c]pyridine-2-carboxamide,trifluoromethylacetate salt,
4-[(4-methylphenyl)sulfinyl]thieno[2,3-c]pyridine-2-carboxamide,; methyl 4-[(4-methylphenyl)sulfinyl]thieno[2,3-c]pyridine-2-carboxylate,
4-(4-methylphenoxy)thieno[2,3-c]pyridine-2-carboxamide, methyl 4-(4-methylphenoxy)thieno[2,3-c]pyridine-2-carboxylate,
4-(4-chlorophenoxy)thieno[2,3-c]pyridine-2-carboxamide, methyl 4-(4-chlorophenoxy)thieno[2,3-c]pyridine-2-carboxylate,
4-[4-(trifluoromethyl)phenoxy]thieno[2,3-c]pyridine-2-carboxamide,
4-(4-octylphenoxy)thieno[2,3 -c]pyridine-2-carboxamide,
4-[4-(1-methylethyl)phenoxy]thieno[2,3-c]pyridine-2-carboxamide,
4-(2-bromo-4-chlorophenoxy)thieno[2,3-c]pyridine-2-carboxamide,
4-(4-ethylphenoxy)thieno[2,3-c]pyridine-2-carboxamide,
4-(4-ethenylphenoxy)thieno[2,3-c]pyridine-2-carboxamide,
4-[4-(1,2-dihydroxyethyl)phenoxy]thieno[2,3-c]pyridine-2-carboxamide,
4-[2-(2-propenyl)phenoxy]thieno[2,3-c]pyridine-2-carboxamide,
4-[2-(2,3-dihydroxypropyl)phenoxy]thieno[2,3-c]pyridine-2-carboxamide,
4-[4-(trifluoromethyl)phenoxy]thieno[2,3-c]pyridine-2-carboxamide, 1-oxide,
4-[3-(pentadecyl)phenoxy]thieno[2,3-c]pyridine-2-carboxamide,
4-(4-bromophenoxy)thieno[2,3-c]pyridine-2-carboxamide,
4-(3 -chlorophenoxy)thieno[2,3-c]pyridine-2-carboxamide,
4-(4-t-butylphenoxy)thieno[2,3-c]pyridine-2-carboxamide,
4-(4-chloro-3-methylphenoxy)thieno[2,3-c]pyridine-2-carboxamide,
4-(4-chloro-2-methylphenoxy)thieno[2,3-c]pyridine-2-carboxamide,
4-(4-methoxyphenoxy)thieno[2,3-c]pyridine-2-carboxamide, ethyl 3-[[2-(aminocarbonyl)thieno[2,3-c]pyridin-4-yl]oxy]benzoate,
4-Phenoxythieno[2,3-c]pyridine-2-carboxamide,
4-(3-Bromophenoxy)thieno[2,3-c]pyridine-2-carboxamide,
4-(4-Fluorophenoxy)thieno[2,3-c]pyridine-2-carboxamide,
4-(3,5-Dimethylphenoxy)thieno[2,3-c]pyridine-2-carboxamide,
4-(3—Chloro-4-methylphenoxy)thieno[2,3-c]pyridine 2-carboxamide,
4-(4-iodophenoxy)thieno[2,3-c]pyridine-2-carboxamide,
4-(4-(Methoxymethyl)phenoxy)thieno[2,3-c]pyridine-2-carboxamide,
2-(aminocarbonyl)-4-(4-chlorophenoxy)thieno[2,3-c]pyridinium, iodide,
4-(4-Chlorophenoxy)thieno[2,3-c]pyridine-2-carboxylic acid, N-(4-(4-Chlorophenoxy)thieno[2,3-c]pyridin-2-yl)-O-(3-tetrahydrofuranyl)carbamate,
4-(4-Chlorophenoxy)thieno[2,3-c]pyridine-2-methanol, (E)-3-[4-( 4 -chlorophenoxy)thieno[2,3-c]pyridin-2-yl]-2-propenoic acid,
4-(4-Chlorophenoxy)thieno[2,3-c]pyridine-2-carboxaldehyde, (E)-3-[4-(4-chlorophenoxy)thieno[2,3-c]pyridin-2-yl]-2-propenamide,
4-bromothieno[2,3-c]pyridine-2-carboxamide, methyl 4-bromothieno[2,3-c]pyridine-2-carboxylate, 4-chlorothieno[2,3-c]pyridine-2-carboxamide, 4-[4-(trifluoromethyl)phenyl]thieno[2,3-c]pyridine-2-carboxamide, methyl 4-[4-(trifluoromethyl)phenyl]thieno[2,3-c]pyridine-2-carboxylate, N-methyl-4-[4-(trifluoromethyl)phenyl]thieno[2,3-c]pyridine-2-carboxamide,
4-phenylthieno[2,3-c]pyridine-2-carboxamide, methyl 4-phenylthieno[2,3-c]pyridine-2-carboxylate,
4-([1,1′-biphenyl]-4-ylthio)thieno[2,3-c]pyridine-2-carboxamide,
4-(5-formyl-2-furanyl)thieno[2,3-c]pyridine-2-carboxamide, ethyl 4-[[2-(aminocarbonyl)thieno[2,3-c]pyridin-4-yl]oxy]benzoate,
4-[[2-(aminocarbonyl)thieno[2,3-c]pyridin-4-yl]oxy]benzoic acid,
4-(1-phenylethenyl)thieno[2,3-c]pyridine-2-carboxamide, methyl 4-(1-phenylethenyl)thieno[2,3-c]pyridine-2-carboxalate,
4-[(4-methylphenyl)thio]thieno[2,3-c]pyridine-2-methanol,
4-(4-Chlorophenoxy)-N-methylthieno[2,3-c]pyridine-2-carboxamide,
4-(4-chlorophenoxy)-N,N-dimethylthieno[2,3-c]pyridine-2-carboxamide,
4-(4-chlorophenoxy)-N,N-diethylthieno[2,3-c]pyridine-2-carboxamide,
4-(4-chlorophenoxy)-N-cyclopropylthieno[2,3-c]pyridine-2-carboxamide,
1-[[4-(4-chlorophenoxy)thieno[2,3-c]pyridin-2-yl]carbonyl]pyrrolidine,
1-[[4-(4-chlorophenoxy)thieno[2,3-c]pyridin-2-yl]carbonyl]piperidine,
4-[[4-(4-chlorophenoxy)thieno[2,3-c]pyridin-2-yl]carbonyl]morpholine,
1-[[4-(4-chlorophenoxy)thieno[2,3-c]pyridin-2-yl]carbonyl]-4-methylpiperazine,
1-[[4-(4-chlorophenoxy)thieno[2,3-c]pyridin-2-yl]carbonyl]-4-phenyllpiperazine,
1-[[4-(4-chlorophenoxy)thieno[2,3-c]pyridin-2-yl]carbonyl]-4-(phenylmethyl)piperazine,
1-[[4-(4-chlorophenoxy)thieno[2,3-c]pyridin-2-yl]carbonyl]-4-(2-pyridinyl)piperazine,
4-(4-chlorophenoxy)-N-(2-hydroxyethyl)lthieno[2,3-c]pyridine-2-carboxamide,
4-[[4-(4-chlorophenoxy)thieno[2,3-c]pyridin-2-yl]carbonyl]-N-(1-methylethyl)-1-piperazineacetamide, trifluoroacetate salt,
4-(4-chlorophenoxy)-N-[1-(hydroxymethyl)ethyl]thieno[2,3-c]pyridine-2-carboxamide,
4-(4-chlorophenoxy)-N-[1,1-bis(hydroxymethyl)ethyl]thieno[2,3-c]pyridine-2-carboxamide,
(D,L)-4-(4-chlorophenoxy)-N-(2-hydroxypropyl)thieno[2,3-c]pyridine-2-carboxamide,
4-(4-chlorophenoxy)-N-[2-(4-morpholinyl)ethyl]thieno[2,3-c]pyridine-2-carboxamide,
4-(4-chlorophenoxy)thieno[2,3-c]pyridine-2-sulfonamide,
4-(4-morpholinyl)thieno[2,3-c]pyridine-2-carboxamide,
4-(4-chlorophenoxy)thieno[2,3 -c]pyridine-2-carboxamide, N-oxide, methyl (4-chlorophenoxy)thieno[2,3-c]pyridine-2-carboxylic acid, N-oxide,
4-(4-chlorophenoxy)-2-(2-methoxyphenyl)thieno[2,3-c]pyridine,
4-(4-chlorophenoxy)thieno[2,3-c]pyridine,
4-(4-chlorophenoxy)-3-methylthieno[2,3-c]pyridine-2-carboxamide, Methyl 4-(4-chlorophenoxy)-3-methylthieno[2,3-c]pyridine-2-carboxylate,
3-amino-4-(4-chlorophenoxy)thieno[2,3-c]pyridine-2-carboxamide, methyl 3-amino-4-(4-chlorophenoxy)thieno[2,3 -c]pyridine-2-carboxylate,
3-amino-4-(4-chlorophenoxy)thieno[2,3-c]pyridine-2-carboxylic acid,
4-(4-chlorophenoxy)thieno[2,3-c]pyridine-2-carbothioamide,
4-(4-chlorophenoxy)-N-ethylthieno[2,3-c]pyridine-2-carboxamide,
4-(4-chlorophenoxy)-N-(2,3-dihydroxypropyl)thieno[2,3-c]pyridine-2-carboxamide,
4-(4-bromophenoxy)-N-(2,3-dihydroxypropyl)thieno[2,3-c]pyridine-2-carboxamide,
N-(2-chloroethyl)-4-(4-chlorophenoxy)thieno[2,3-c]pyridine-2-carboxamide, 4-(4-bromophenoxy)-N-(2-hydroxyethyl)thieno[2,3-d]pyridine-2-carboxamide,
4-(2-bromo-4-chlorophenoxy)-N-(2-hydroxyethyl)thieno[2,3-c]pyridine-2-carboxamide,
N-(2-hydroxyethyl)-4-[4-(trifluoromethyl)phenoxy]thieno[2,3-c]pyridine-2-carboxamide,
N-(2-aminoethyl)-4-(4-chlorophenoxy)thieno[2,3-c]pyridine-2-carboxamide,
4-(4-chlorophenoxy)-N-hydroxythieno[2,3-c]pyridine-2-carboxamide,
4-(4-chlorophenoxy)thieno[2,3-c]pyridine-2-carbohydrazide,
4-(4-bromophenoxy)thieno[2,3-c]pyridine-2-carbohydrazide,
4-[4-(trifluoromethyl)phenoxy]thieno[2,3-c]pyridine-2-carbohydrazide,
4-(4-chlorophenoxy)-N-hydroxythieno[2,3-c]pyridine-2-carboxamide,
2-({[4-(4-chlorophenoxy)thieno[2,3-c]pyridin-2-yl]carbonyl}amino)acetic acid,
N-(2-amino-2-oxoethyl)-4-(4-chlorophenoxy)thieno[2,3-c]pyridine-2-carboxamide,
N-(2-amino-2oxoethyl)-4-(4-bromophenoxy)thieno[2,3-c]pyridine-2-carboxamide,
(2S)-2-({[4-(4-chlorophenoxy)thieno[2,3-c]pyridin-2-yl]carbonyl}amino)-3-hydroxypropanoic acid,
N-[(1S)-2-amino-1-(hydroxymethyl)-2-oxoethyl]-4-(4-chlorophenoxy)thieno[2,3-c]pyridine-2-carboxamide,
(2R)-2-({[4-(4-chlorophenoxy)thieno[2,3-c]pyridin-2-yl]carbonyl}amino)-3-hydroxypropanoic acid,
(2R)-2-({[4-(4-chlorophenoxy)thieno[2,3-c]pyridin-2-yl]carbonyl}amino)propanoic acid,
4-(4-chlorophenoxy)-N-[(1R)-1-methyl-2-(methylamino)-2-oxoethyl]thieno[2,3-c]pyridine-2-carboxamide,
(2S)-2-({[4-(4-chlorophenoxy)thieno[2,3-c]pyridin-2-yl]carbonyl}amino)propanoic acid,
4-(4-chlorophenoxy)-N-[(1S)-1-methyl-2-(methylamino)-2-oxoethyl]thieno[2,3-c]pyridine-2-carboxamide,
4-(4-chlorophenoxy)-N-[(1R)-1-(hydroxymethyl)-2-(methylamino)-2-oxoethyl]thieno[2,3-c]pyridine-2-carboxamide,
4-(4-chlorophenoxy)-N-[(1S)-1-(hydroxymethyl)-2-(methylamino)-2-oxoethyl]thieno[2,3-c]pyridine-2-carboxamide,
4-(3-pyridinyloxy)thieno[2,3-c]pyridine-2-carboxamide,
4-(4-bromophenoxy)-N-methylthieno[2,3-c]pyridine-2-carboxamide,
4-(4-bromophenoxy)-N,N-dimethylthieno[2,3-c]pyridine-2-carboxamide,
N,N-dimethyl-4-[4-(trifluoromethyl)phenoxy]thieno[2,3-c]pyridine-2-carboxamide,
4-(4-chloro-3-fluorophenoxy)-N-methylthieno[2,3-c]pyridine-2-carboxamide,
4-(4-chloro-3-fluorophenoxy)thieno[2,3 -c]pyridine-2-carboxamide,
4-(4-chloro-3-ethylphenoxy)thieno[2,3-c]pyridine-2-carboxamide,
4-(3-fluorophenoxy)thieno[2,3-c]pyridine-2-carboxamide,
4-(2,3-difluorophenoxy)thieno[2,3-c]pyridine-2-carboxamide,
4-(2,3-difluorophenoxy)-N-methylthieno[2,3-c]pyridine-2-carboxamide,
4-(3-fluorophenoxy)-N-methylthieno[2,3-c]pyridine-2-carboxamide,
N-methyl-4-(2,3,4-trifluorophenoxy)thieno[2,3-c]pyridine-2-carboxamide,
4-(2,3,4-trifluorophenoxy)thieno[2,3-c]pyridine-2-carboxamide,
N-methyl-4-[4-(trifluoromethyl)phenoxy]thieno [2 3-c]pyridine-2carboxamide,
4-[3-(trifluoromethyl)phenoxy]thieno[2,3-c]pyridine-2-carboxamide,
N,N-dimethyl-4-(4-vinylphenoxy)thieno[2,3-c]pyridine-2-carboxamide,
4-(4-cyanophenoxy)-N-methylthieno[2,3-c]pyridine-2-carboxamide,
4-(4-cyanophenoxy)thieno[2,3-c]pyridine-2-carboxamide,
4-(4-aminophenoxy)thieno[2,3-c]pyridine-2-carboxamide,
4-[4-(acetylamino)phenoxy]thieno[2,3-c]pyridine-2-carboxamide,
N-methyl-4-[4-(4-morpholinyl)phenoxy]thieno[2,3-c]pyridine-2-carboxamide,
4-[4-(hydroxymethyl)phenoxy]thieno[2,3-c]pyridine-2-carboxamide,
4-[4-(hydroxymethyl)phenoxy]-N-methylthieno[2,3-c]pyridine-2-carboxamide,
4-[4-(2-methoxyethyl) phenoxy]-N-methylthieno[2,3-c]pyridine-2-carboxamide,
4-{4-[(2-methoxyethoxy)methyl]phenoxy}thieno[2,3-c]pyridine-2-carboxamide,
4-{4-[(2-methoxyethoxy)methyl]phenoxy}-N-methylthieno[2,3-c]pyridine-2-carboxamide,
4-(4-{[2-(2-methoxyethoxy)ethoxy]methyl}phenoxy)thieno[2,3-c]pyridine-2-carboxamide,
4-(4-{[2-(2-methoxyethoxy)ethoxy]methyl}phenoxy)-N-methylthieno[2,3-c]pyridine-2-carboxamide,
4-{4-[(tetrahydro-2H-pyran-2-yloxy)methyl]phenoxy}thieno[2,3-c]pyridine-2-carboxamide,
N-methyl-4-{4-[(tetrahydro-2H-pyran-2-yloxy)methyl]phenoxy}thieno[2,3-c]pyridine-2-carboxamide,
4-{[2-(aminocarbonyl)thieno[2,3-c]pyridin-4-yl]oxy}benzyl 2-furoate,
4-[4-({[(2R,4R,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl]oxy}methyl)phenoxy]-N-methylthieno[2,3-c]pyridine-2-carboxamide,
4-(4-acetylphenoxy)-N-methylthieno[2,3-c]pyridine-2-carboxamide,
4-[4-(4-morpholinylcarbonyl)phenoxy]thieno [2,3-c]pyridine-2-carboxamide, N-methyl-4-[4-(4-morpholinylcarbonyl)phenoxy]thieno[2,3-c]pyridine-2-230 carboxamide,
4-[4-({[2-(4-morpholinyl)ethyl]amino}carbonyl)phenoxy]thieno[2,3-c]pyridine-2-carboxamide,
N-methyl-4-[4-({[2-(4-morpholinyl)ethyl]amino}carbonyl)phenoxy]thieno[2,3-c]pyridine-2-carboxamide,
4-(4-[(E)-3-(4-morpholinyl)-3-oxo-1-propenyl]phenoxy}thieno[2,3-c]pyridine-2-carboxamide,
4-[4-((E)-3-{[2-(4-morpholinyl)ethyl]amino}-3-oxo-1-propenyl)phenoxy]thieno[2,3-c]pyridine-2-carboxamide,
N-methyl-4-[4-((E)-3-{[2-(4-morpholinyl)ethyl]amino}-3-oxo-1-propenyl)phenoxy]thieno[2,3-c]pyridine-2-carboxamide,
4-(4-{(E)-3-[(2,3-dihydroxypropyl)amino]-3-oxo-1-propenyl}phenoxy)thieno[2,3-c]pyridine-2-carboxamide,
4-(4-{(E)-3-[(2,3 -dihydroxypropyl)amino]-3-oxo-1-propenyl}phenoxy)-N-methylthieno[2,3-c]pyridine-2-carboxamide,
4-[4-((E)-3-{[2-(1H-imidazol-4-yl)ethyl]amino}-3-oxo-1-propenyl)phenoxy]-N-methylthieno[2,3-c]pyridine-2-carboxamide,
4-{4-[(E)-3-({2-[bis(2-hydroxyethyl)amino]ethyl}amino)-3-oxo-1-propenyl]phenoxy3-N-methylthieno [2,3-c]pyridine-2-carboxamide,
4-14-[(E)-3-({2-[bis(2-hydroxyethyl)amino]ethyl}amino)-3-oxo-1-propenyl]phenoxy}thieno[2,3-c]pyridine-2-carboxamide,
4-[4-(1H-imidazol-1-yl)phenoxy]thieno[2,3-c]pyridine-2-carboxamide,
N-methyl-4-[4-(1H-pyrazol-1-yl)phenoxy]thieno[2,3-c]pyridine-2-carboxamide,
N-methyl-4-[4-(1H-1,2,4-triazol-1-yl)phenoxy]thieno[2,3-c]pyridine-2-carboxamide,
N-methyl-4-{4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenoxy}thieno[2,3-c]pyridine-2-carboxamide,
4-[4-(4,5-dihydro-1H-imidazol-2-yl)phenoxy]-N-methylthieno[2,3-c]pyridine-2-carboxamide,
N-methyl-4-[4-(2-thienyl)phenoxy]thieno[2,3-c]pyridine-2-carboxamide,
4-([1,1′-biphenyl]-4-yloxy)-N-methylthieno[2,3-c]pyridine-2-carboxamide,
N-methyl-4-[4-(1-methyl-1H-imidazol-5-yl)phenoxy]thieno[2,3-c]pyridine-2-carboxamide,
4-{4-[1-(hydroxymethyl)cyclopropyl]phenoxy}-N-methylthieno[2,3-c]pyridine-2-carboxamide,
4-[4-(1-{[2-(2-ethoxyethoxy)ethoxy]methyl}cyclopropyl)phenoxy]-N-methylthieno[2,3-c]pyridine-2-carboxamide,
N-methyl-4-[4-(trifluoromethoxy)phenoxy]thieno[2,3-c]pyridine-2-carboxamide,
5-{4-[4-(1-{[2-(2-ethoxyethoxy)ethoxy]methyl}cyclopropyl)phenoxy]thieno[2,3-c]pyridin-2-yl}-1,3,4-oxadiazol-2-amine,
4-[4-(1,1-difluoro-2-hydroxyethyl)phenoxy]-N-methylthieno[2,3-c]pyridine-2-carboxamide,
4-(4-{2-[2-(2-ethoxyethoxy)ethoxy]-1,1-difluoroethyl}phenoxy)-N-methylthieno[2,3-c]pyridine-2-carboxamide,
4-(4-chlorophenoxy)-6-{[(2,2-dimethylpropanoyl)oxy]methyl}-2-[(methylamino)carbonyl]thieno[2,3-c]pyridin-6-ium,
4-(4-bromophenoxy)-6-{[(2,2-dimethylpropanoyl)oxy]methyl}-2-[(methylamino)carbonyl]thieno[2,3-c]pyridin-6-ium,
2-(aminocarbonyl)-4-(4-chlorophenoxy)-6-{[(isopropoxycarbonyl)oxy]methyl}thieno[2,3-c]pyridin-6-ium,
4-(benzyloxy)thieno[2,3-c]pyridine-2-carboxamide,
4-[(4-chlorophenyl)(hydroxy)methyl]thieno[2,3-c]pyridine-2-carboxamide,
4-(4-chlorobenzoyl)-N-methylthieno[2,3-c]pyridine-2-carboxamide,
N 4 -(4-chlorophenyl)thieno[2,3-c]pyridine-2,4-dicarboxamide,
[4-(4-bromophenoxy)thieno[2,3-c]pyridin-2-yl]methanol,
4-(4-bromophenoxy)thieno[2,3-c]pyridine-2-carbaldehyde,
4-(4-chlorophenoxy)thieno[2,3-c]pyridine-2-carbaldehyde oxime;
4 -(4-chlorophenoxy)thieno[2,3-c]pyridine-2-carbaldehyde O-methyloxime,
1-[4-(4-chlorophenoxy)thieno[2,3-c]pyridin-2-yl]-1-ethanone O-methyloxime,
1-[4-(4-chlorophenoxy)thieno[2,3-c]pyridin-2-yl]-1-ethanone O-methyloxime,
1-[4-(4-chlorophenoxy)thieno[2,3-c]pyridin-2-yl]-1-ethanone oxime,
1-[4-(4-chlorophenoxy)thieno[2,3-c]pyridin-2-yl]-1-ethanone oxime,
1-[4-(4-chlorophenoxy)thieno[2,3-c]pyridin-2-yl]-1-propanone,
1-[4-(4-chlorophenoxy)thieno[2,3-c]pyridin-2-yl]-1-propanone oxime,
2-[4-(4-chlorophenoxy)thieno[2,3-c]pyridin-2-yl]-N-methoxy-N-methyl-2-oxoacetamide,
4-(4-chlorophenoxy)thieno[2,3-c]pyridine-2-carbonitrile,
4-(4-chlorophenoxy)-N′-hydroxythieno[2,3-c]pyridine-2-carboximidamide,
4-(4-chlorophenoxy)-N′-cyanothieno[2,3-c]pyridine-2-carboximidamide,
[4-(4-chlorophenoxy)thieno[2,3-c]pyridin-2-yl](2-nitrophenyl)methanol,
[4-(4-chlorophenoxy)thieno[2,3-c]pyridin-2-yl](2-nitrophenyl)methanone,
(2-aminophenyl)[4-(4-chlorophenoxy)thieno[2,3-c]pyridin-2-yl]methanone,
(2-aminophenyl)[4-(4-chlorophenoxy)thieno[2,3-c]pyridin-2-yl]methanol,
[4-(4-chlorophenoxy)thieno[2,3-c]pyridin-2-yl](3-nitrophenyl)methanol,
(3-aminophenyl)[4-(4-chlorophenoxy)thieno[2,3-c]pyridin-2-yl]methanone,
(3-aminophenyl)[4-(4-chlorophenoxy)thieno[2,3-c]pyridin-2-yl]methanol,
4-(4-bromophenoxy)-2-vinylthieno[2,3-c]pyridine,
1-[4-(4-chlorophenoxy)thieno[2,3-c]pyridin-2-yl]-1,2-ethanediol,
1-[4-(4-bromophenoxy)thieno[2,3-c]pyridin-2-yl]-1,2-ethanediol,
[4-(4-chlorophenoxy)thieno[2,3-c]pyridin-2-yl]methanamine,
[4-(4-chlorophenoxy)thieno[2,3-c]pyridin-2-yl]methyl carbamate,
N-{[4-(4-chlorophenoxy)thieno[2,3-c]pyridin-2-yl]methyl}urea,
(E)-3-[4-(4-bromophenoxy)thieno[2,3-c]pyridin-2-yl]-2-propenamide,
(E)-3-[4-(4-bromophenoxy)thieno[2,3-c]pyridin-2-yl]-N-ethyl-2-propenamide,
3-[4-(4-bromophenoxy)thieno[2,3-c]pyridin-2yl]-2,3-dihydroxy-N-methylpropanamide,
4-(4-chlorophenoxy)thieno[2,3-c]pyridin-2-ylamine,
4-(4-chlorophenoxy)thieno[2,3-c]pyridin-2-ylformamide,
N-[4-(4-chlorophenoxy)thieno[2,3-c]pyridin-2-yl]urea,
N-[4-(4-chlorophenoxy)thieno[2,3-c]pyridin-2-yl]-N′-methylthiourea,
4-(4-chlorophenoxy)-N-methylthieno[2,3-c]pyridine-2-sulfonamide,
4-(4-chlorophenoxy)-N-(2,3-dihydroxypropyl)thieno[2,3-c]pyridine-2-sulfonamide,.
4-(4-chlorophenoxy)-N-(2-hydroxyethyl)thieno[2,3-c]pyridine-2-sulfonamide,
4-[4-(4-chlorophenoxy)thieno[2,3-c]pyridin-2-yl]phenol,
3-[4-(4-chlorophenoxy)thieno[2,3-c]pyridin-2-yl]aniline,
4-[4-(4-chlorophenoxy)thieno[2,3-c]pyridin-2-yl]aniline,
4-(4-chlorophenoxy)-2-(5-nitro-2-pyridinyl)thieno[2,3-c]pyridine,
6-[4-(4-chlorophenoxy)thieno[2,3-c]pyridin-2-yl]-3-pyridinamine,
5-[4-(4-chlorophenoxy)thieno[2,3-c]pyridin-2-yl]-2-pyridinamine,
5-[4-(4-chlorophenoxy)thieno[2,3-c]pyridin-2-yl]-1,3,4-oxadiazol-2-amine,
5-[4-(4-bromophenoxy)thieno[2,3-c]pyridin-2-yl]-1,3,4-oxadiazol-2-ylamine,
5-[4-(4-chlorophenoxy)thieno[2,3-c]pyridin-2-]-4H-1,2,4-triazol-3-amine,
5-[4-(4-chlorophenoxy)thieno[2,3-c]pyridin-2-yl]-1,3,4-thiadiazol-2-amine,
4-(4-chlorophenoxy)-2-(5-methyl-1,2,4-oxadiazol-3-yl)thieno[2,3-c]pyridine,
5-{4-[4-(trifluoromethyl)phenoxy]thieno[2,3-c]pyridin-2-yl}-1,3,4-oxadiazol-2-amine,
4-(4-chlorophenoxy)-2-[5-(methylsulfanyl)-1,3 ,4-oxadiazol-2-yl]thieno[2,3-c]pyridine,
4-(4-chlorophenoxy)-2-(2-methyl-2H-1,2,3,4-tetraazol-5-yl)thieno[2,3-c]pyridine,
5-[4-(4-chlorophenoxy)thieno[2,3-c]pyridin-2-yl]-4-methyl-4H-1,2,4-triazol-3-amine,
4-(4-chlorophenoxy)-2-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]thieno[2,3-c]pyridine,
5-[4-(4-chlorophenoxy)thieno[2,3-c]pyridin-2-yl]-1,2,4-oxadiazol-3-amine,
5-[4-(4-chlorophenoxy)thieno[2,3-c]pyridin-2-yl]-N-methyl-1,3,4-thiadiazol-2-amine,
4-(4-chlorophenoxy)-2-(1,2,4-oxadiazol-3-yl)thieno[2,3-c]pyridine,
2-(1,3,4-oxadiazol-2-yl)-4-[4-(trifluoromethyl)phenoxy]thieno[2,3-c]pyridine,
3-[4-(4-chlorophenoxy)thieno[2,3-c]pyridin-2-yl}-1,2,4-oxadiazol-5-amine,
2-(5-methyl-1,3,4-oxadiazol-2-yl)-4-[4-(trifluoromethyl)phenoxy]thieno[2,3-c]pyridine,
methyl 2-[4-(4-chlorophenoxy)thieno[2,3-c]pyridin-2-yl]-l 3-thiazole-4-carboxylate,
2-[4-(4-chlorophenoxy)thieno[2,3-c]pyridin-2-yl]-1,3-thiazole-4-carboxamide,
tert-butyl 2-[4-(4-chlorophenoxy)thieno[2,3-c]pyridin-2-yl]-1,3-thiazol-4-ylcarbamate,
2-[4-(4-chlorophenoxy)thieno[2,3-c]pyridin-2-yl]-1,3-thiazol-4-amine,
4-chloro-3-methylthieno[2,3-c]pyridine-2-carboxamide,
3-amino-4-chlorothieno[2,3-c]pyridine-2-carboxamide,
4-(4-chlorophenoxy)-N,3-dimethylthieno[2,3-c]pyridine-2-carboxamide,
4-(4-bromophenoxy)-3-methylthieno[2,3-c]pyridine-2-carboxamide,
7-chloro-4-(4-chlorophenoxy)-3-methylthieno [2,3-c]pyridine-2-carboxamide,
tert-butyl 2-(aminocarbonyl)-4-(4-chlorophenoxy)thieno[2,3-c]pyridine-3-carboxylate,
N-methyl-4-(4-toluidino)thieno[2,3-c]pyridine-2-carboxamide,
4-(4-chloroanilino)-N-methylthieno[2,3-c]pyridine-2-carboxamide,
N-methyl-4-(4morpholinyl)thieno[2,3-c]pyridine-2-carboxamide,
7-chloro-4-(4-chlorophenoxy)thieno[2,3-c]pyridine-2-carboxamide,
7-chloro-4-(4-chlorophenoxy)-N-methylthieno[2,3-c]pyridine-2-carboxamide,
7-chloro-4-(4-chlorophenoxy)-N-(2-hydroxyethyl)thieno[2,3-c]pyridine-2-carboxamide,
7-bromo-4-(4-chlorophenoxy)thieno[2,3-c]pyridine-2-carboxamide,
7-bromo-4-(4-chlorophenoxy)-N-methylthieno[2,3-c]pyridine-2-carboxamide,
4-(4-bromophenoxy)-7-chlorothieno[2,3-c]pyridine-2-carboxamide,
4-(4-bromophenoxy)-7-chloro-N-methylthieno[2,3-c]pyridine-2-carboxamide,
7-chloro-4-[4-(trifluoromethyl)phenoxy]thieno[2,3-c]pyridine-2-carboxamide,
7-chloro-N-methyl-4-[4-(trifluoromethyl)phenoxy]thieno[2,3-c]pyridine-2-carboxamide,
7-chloro-N-(2-hydroxyethyl)-4-[4-(trifluoromethyl)phenoxy]thieno[2,3-c]pyridine-2-carboxamide,
4-(4-chlorophenoxy)-N,7-dimethylthieno[2,3-c]pyridine-2-carboxamide,
4-(4-chlorophenoxy)-7-methoxythieno[2,3-c]pyridine-2-carboxamide,
4-(4-chlorophenoxy)-N-methyl-7-(methylamino)thieno[2,3-c]pyridine-2-carboxamide,
4-[(E)-2-phenylethenyl]thieno[2,3-c]pyridine-2-carboxamide,
4-(4-chlorophenyl)thieno[2,3-c]pyridine-2-carboxamide,
4-[3-(trifluoromethyl)phenyl]thieno[2,3-c]pyridine-2-carboxamide,
4-(3-chlorophenyl)thieno[2,3-c]pyridine-2-carboxamide,
4-(4-bromophenyl)thieno[2,3-c]pyridine-2-carboxamide,
4-(3-aminophenyl)thieno[2,3-c]pyridine-2-carboxamide,
4-(3,5-dichlorophenyl)thieno[2,3-c]pyridine-2-carboxamide,
4-(2,4-dichlorophenyl)thieno[2,3-c]pyridine-2-carboxamide,
4-(3,4-dichlorophenyl)thieno[2,3-c]pyridine-2-carboxamide,
4-(2,4-difluorophenyl)thieno[2,3-c]pyridine-2-carboxamide,
4-(4-fluorophenyl)thieno[2,3-c]pyridine-2-carboxamide, and
4-(4-bromophenoxy)-5-chlorothieno[2,3-c]pyridine-2-carboxamide.
8 . A compound according to claim 1 where E, F and Y are carbon, G is nitrogen or N + —O − , and Z is S(O) t .
9 . A compound according to claim 8 selected from the group consisting of
4-[(4-methylphenyl)thio]thieno[2,3-b]pyridine,
4-[(4-methylphenyl)thio]thieno[2,3-b]pyridine-2-carboxamide,
4-chloro-N-(4-chlorophenyl)thieno[2,3-b]pyridine-5-carboxamide,
ethyl 4-[(5-methyl-1,3,4-thiadiazol-2-yl)thio]thieno[2,3-b]pyridine-5-carboxylate,
methyl 6-[(4-methylphenyl)thio]thieno[2,3-b]pyridine-2-carboxylate, and methyl 3-amino-6-chlorothieno[2,3-b]pyridine-2-carboxylate.
10 . A compound according to claim 1 where E, F, and Z are carbon, G is nitrogen or N + —O − , and Y is S(O) t .
11 . A compound according to claim 10 which is
7-[(4-methylphenyl)thio]thieno[3,2-b]pyridine-2-carboxamide.
12 . A compound according to claim 1 where F, G, and Y are carbon, E is nitrogen or N + —O − , and Z is S(O) t .
13 . A compound according to claim 12 selected from the group consisting of
2-bromo-4-[(4-methylphenyl)thio]thieno[3,2-c]pyridine,
4-[(4-methylphenyl)thio]thieno[3,2-c]pyridine-2-carboxamide,
4-[(4-methylphenyl)thio]thieno[3,2-c]pyridine-2-carbonitrile,
4-(4-Methylphenoxy)thieno[3,2-c]pyridine-2-carboxamide, and
4-(4-Methylphenoxy)thieno[3,2-c]pyridine-2-carbonitrile.
14 . A compound according to claim 1 where E and G are carbon, F and Y are independently nitrogen or N + —O − , and Z is S(O) t .
15 . A compound according to claim 14 selected from the group consisting of
methyl 7-(4-methylphenoxy)[1,3]thiazolo[5,4-c]pyridine-2-carboxylate, 7-(4-methylphenoxy)[1,3]thiazolo[5,4-c]pyridine-2-carboxamide, and N-methyl-7-(4-methylphenoxy)[1,3]thiazolo[5,4-c]pyridine-2-carboxamide.
16 . A compound according to claim 1 where E and G are carbon, F is nitrogen or N + —O − , and Y and Z are nitrogen.
17 . A compound according to claim 1 where G and Y are carbon, E and F are independently nitrogen or N + —O − , and Z is S(O) t .
18 . A compound according to claim 1 where E, G and Z are carbon, F is nitrogen or N + —O − , and Y is S(O) t .
19 . A compound according to claim 1 where E and G are carbon, F is nitrogen or N + —O − , Y is nitrogen, and Z is oxygen.
20 . A compound according to claim 1 where E, G and Y are carbon, F is nitrogen or N + —O − , and Z is O.
21 . A compound according to claim 20 selected from the group consisting of
4-(4-chlorophenoxy)furo[2,3-c]pyridine-2-carboxamide and
4-(4-chlorophenoxy)furo[2,3-c]pyridine-2-carbothioamide.
22 . A compound selected from the group consisting of
methyl 2-[(6-ethylthieno[2,3-d]pyrimidin-4-yl)thio]acetate, 6-ethyl-4-[(4-methylphenyl)thio]thieno[2,3-d]pyrimidine, 6-ethyl-4-(2-pyridinylthio)thieno[2,3-d]pyrimidine, 6-ethyl-4-[(2-methylethyl)thio]thieno[2,3-d]pyrimidine, 6-ethyl-4-[(phenylmethyl)thio]thieno[2,3-d]pyrimidine, 6-ethyl-4-[(5-methyl-1,3,4-thiadiazol-2-yl)thio]thieno[2,3-d]pyrimidine, ethyl 6-ethyl-4-[(4-methylphenyl)thio]thieno[2,3-d]pyrimidine-6-carboxylate, 6-ethyl-N-(phenylmethyl)thieno[2,3-d]pyrimidin-4-amine, 6-ethyl-N-(5-methyl-1,3,4-thiadiazol-2-yl)thieno[2,3-d]pyrimidin-4-amine, 4-[(5-amino-1,3,4-thiadiazol-2-yl)thio]-6-ethyl-2-(phenylmethyl)thieno[2,3-d]pyrimidine, 4-chloro-6-ethyl-2-(phenylmethyl)thieno[2,3-d]pyrimidine, 4-[(5-amino-1,3,4-thiadiazol-2-yl)thio]-6-ethyl-2-(phenylmethyl)thieno[2,3-d]pyrimidine, 7-methyl-4-[(4-methylphenyl)thio]thieno[3,2-d]pyrimidine, 7-methyl-4-[(5-methyl-1,3,4-thiadiazol-2-yl)thio]thieno[3,2-d]pyrimidine, 7-methyl-4-[[5-(methylthio)-1,3,4-thiadiazol-2-yl]thio]thieno[3,2-d]pyrimidine, 4-[(5-amino-1,3,4-thiadiazol-2-yl)thio]-7-methylthieno[3,2-d]pyrimidine, 7-methyl-N-[(4-(methylthio)phenyl]thieno[3,2-d]pyrimidin-7-amine, 7-methyl-4-[(4-methylphenyl)thio]thieno[3,2-d]pyrimidine-6-carboxamide, methyl 4-[(4-methylphenyl)thio]thieno[2,3-c]pyridine-2-carboxylate, 4-[(4-methylphenyl)thio]thieno[2,3-c]pyridine-2-carboxylic acid, 4-[(4-methylphenyl)thio]thieno[2,3-c]pyridine-2-carboxamide, 4-(2-pyridinylthio)thieno[2,3-c]pyridine-2-carboxamide, 4-[(4-chlorophenyl)thio]thieno[2,3-c]pyridine-2-carboxamide, N-methoxy-N-methyl-4-(4-methylphenyl)thio]thieno[2,3-c]pyridine-2-carboxamide, N-methoxy-4-[(4-methylphenyl)thio]thieno[2,3-c]pyridine-2-carboxamide, N-(4-chlorophenyl)-4-[(4-methylphenyl)thio]thieno[2,3-c]pyridine-2-carboxamide, 4-[(4-methylphenyl)thio]thieno[2,3-c]pyridine-2-carboxaldehyde, 4-[(4-methylphenyl)thio]thieno[2,3-c]pyridine-2-carboxaldehyde, O-methyloxime, 4-[(4-methylphenyl)thio]thieno[2,3-c]pyridine-2-carboxaldehyde, O-(phenylmethyl)oxime, 2-[[[4-[(4-methylphenyl)thio]thieno[2,3-c]pyridin-2-ylmethylene]amino]oxy]acetic acid, 4-[(4-methylphenyl)thio]thieno[2,3-c]pyridine-2-carboxaldehyde, O-phenyloxime, 4-[(4-methylphenyl)thio]thieno[2,3-c]pyridine-2-carboxaldehyde, oxime, 2-[[[4-[(4-methylphenyl)thio]thieno[2,3-c]pyridine-2-ylmethylene]-amino]oxy]acetamide, (E)-3-[(4-methylphenyl)thio]thieno[2,3-c]pyridin-2-yl]-2-propenamide, 1-[4-[(4-methylphenyl)thio]thieno[2,3-c]pyridin-2-yl]ethanone, 2-benzoyl-4-[(4-methylphenyl)thio]thieno[2,3-c]pyridine, 2-ethyl-4-[(4-methylphenyl)thio]thieno[2,3-c]pyridine, 1-[4-[(4-methylphenyl)thio]thieno[2,3 -c]pyridin-2-yl]ethanone, oxime, N-(2,3-dihydroxypropyl)-4-[(4-methylphenyl)thio]thieno[2,3-c]pyridine-2-carboxamide, 4-[(4-methylphenyl)thio]thieno [2,3-c]pyridine-2-carboxylic acid, hydrazide, N 2 N-4-[(4-methylphenyl)thio]thieno[2.3-c]pyridin-2-yl]carbonyl]-N 6 -[(nitroamino)iminomethyl]-L-lysine, methyl ester, N-(aminoiminomethyl)-4-[(4-methylphenyl)thio]thieno[2,3-c]pyridine-2-carboxamide, 4-[(4-methylphenyl)thio]thieno[2,3-c]pyridine-2-carbothioamide, 4-[(4-methylphenyl)thio]thieno[2,3-c]pyridine, methyl 4-[(2-methoxy-2-oxoethyl)thio]thieno[2,3-c]pyridine-2-carboxylate, 4-[(2-amino-2-oxoethyl)thio]thieno[2,3-c]pyridine-2-carboxamide, 4-[(4-bromophenyl)thio]thieno[2,3-c]pyridine-2-carboxamide, 4-(phenylthio)thieno[2,3-c]pyridine-2-carboxamide, 4-[[4-(trifluoromethyl)phenyl]thio]thieno [2,3-c]pyridine-2-carboxamide, 4-[(2-methylphenyl)thio]thieno[2,3c]pyridine-2-carboxamide, 4-[(3-methylphenyl)thio]thieno[2,3-c]pyridine-2-carboxamide, 4-[(3,4-methylphenyl)thio]thieno[2,3-]pyridine-2-carboxamide, 4-[(3,5-dimethylphenyl)thio]thieno[2,3-c]pyridine-2-carboxamide, 4-[(2,4-dimethylphenyl)thio]thieno[2,3-c]pyridine-2-carboxamide, 4-[(2-methyl-3-furanyl)thio]thieno[2,3-c]pyridine-2-carboxamide, 4-[[(4-chlorophenyl)methyl]thio]thieno[2,3-c]pyridine-2-carboxamide, 4-[(3,4-dichlorophenyl)thio]thieno[2,3-c]pyridine-2-carboxamide, 4-[(4-methoxyphenyl)thio]thieno[2,3-c]pyridine-2-carboxamide, 4-(cyclohexylthio)thieno[2,3 -c]pyridine-2-carboxamide, 4-[(4-methylphenyl)thio]-N-[3-(4-morpholinyl)propyl]thieno[2,3-c]pyridine-2-carboxamide,trifluoromethylacetate salt, 4-[(4-methylphenyl)sulfinyl]thieno[2,3-c]pyridine-2-carboxamide, methyl 4-[(4-methylphenyl)sulfinyl]thieno[2,3-c]pyridine-2-carboxylate, 4-(4-methylphenoxy)thieno[2,3-c]pyridine-2-carboxamide, methyl 4-(4-methylphenoxy)thieno[2,3-c]pyridine-2-carboxylate, 4-(4-chlorophenoxy)thieno[2,3-c]pyridine-2-carboxamide, methyl 4-(4-chlorophenoxy)thieno [2,3-c]pyridine-2-carboxylate, 4-[4-(trifluoromethyl)phenoxy]thieno[2 3-c]pyridine-2-carboxamide, 4-(4-octylphenoxy)thieno[2,3-c]pyridine-2-carboxamide, 4-[4-(1-methylethyl)phenoxy]thieno[2,3-c]pyridine-2-carboxamide, 4-(2-bromo-4-chlorophenoxy)thieno[2,3-c]pyridine-2-carboxamide, 4-(4-ethylphenoxy)thieno[2,3-c]pyridine-2-carboxamide, 4-(4-ethenylphenoxy)thieno[2,3-c]pyridine-2-carboxamide, 4-[4-(1,2-dihydroxyethyl)phenoxy]thieno [2,3-c]pyridine-2-carboxamide, 4-[2-(2-propenyl)phenoxy]thieno[2,3-c]pyridine-2-carboxamide, 4-[2-(2,3-dihydroxypropyl)phenoxy]thieno[2,3-c]pyridine-2-carboxamide, 4-[4-(trifluoromethyl)phenoxy]thieno[2,3-c]pyridine-2-carboxamide, 1-oxide, 4-[3-(pentadecyl)phenoxy]thieno[2,3-c]pyridine-2-carboxamide, 4-(4-bromophenoxy)thieno[2,3-c]pyridine-2-carboxamide, 4-(3-chlorophenoxy)thieno[2,3-c]pyridine-2-carboxamide, 4-(4-t-butylphenoxy)thieno[2,3-c]pyridine-2-carboxamide, 4-(4-chloro-3-methylphenoxy)thieno[2,3-c]pyridine-2-carboxamide, 4-(4-chloro-2-methylphenoxy)thieno[2,3-c]pyridine-2-carboxamide, 4-(4-methoxyphenoxy)thieno[2,3-c]pyridine-2-carboxamide, ethyl 3-[[2-(aminocarbonyl)thieno[2,3-c]pyridin-4-yl]oxy]benzoate, 4-phenoxythieno[2,3-c]pyridine-2-carboxamide, 4-(3-bromophenoxy)thieno[2,3-c]pyridine-2-carboxamide, 4-(4-fluorophenoxy)thieno[2,3-c]pyridine-2-carboxamide, 4-(3,5-dimethylphenoxy)thieno[2,3-c]pyridine-2-carboxamide, 4-(3-chloro-4-methylphenoxy)thieno[2,3-c]pyridine-2-carboxamide, 4-(4-iodophenoxy)thieno[2,3-c]pyridine-2-carboxamide, 4-(4-(methoxymethyl)phenoxy)thieno[2,3-c]pyridine-2-carboxamide, 2-(aminocarbonyl)-4-(4-chlorophenoxy)thieno[2,3-c]pyridinium, iodide, 4-(4-chlorophenoxy)thieno[2,3-c]pyridine-2-carboxylic acid, N-(4-(4-chlorophenoxy)thieno[2,3-c]pyridin-2-yl)-O-(3-tetrahydrofuranyl)carbamate, 4-(4-chlorophenoxy)thieno[2,3-c]pyridine-2-methanol, (E)-3-[4-(4-chlorophenoxy)thieno[2,3-c]pyridin-2-yl]-2-propenoic acid, 4-(4-chlorophenoxy)thieno[2,3-c]pyridine-2-carboxaldehyde, (E)-3-[4-(4-chlorophenoxy)thieno[2,3-c]pyridin-2-yl]-2-propenamide, 4-bromothieno[2,3-c]pyridine-2-carboxamide, methyl 4-bromothieno[2,3-c]pyridine-2-carboxylate, 4-chlorothieno[2,3-c]pyridine-2-carboxamide, 4-[4-(trifluoromethyl)phenyl]thieno[2,3-c]pyridine-2-carboxamide, methyl 4-[4-(trifluoromethyl)phenyl]thieno[2,3-c]pyridine-2-carboxylate, N-methyl-4-[4-(trifluoromethyl)phenyl]thieno[2,3-c]pyridine-2-carboxamide, 4-phenylthieno[2,3-c]pyridine-2-carboxamide, methyl 4-phenylthieno[2,3-c]pyridine-2-carboxylate, 4-([1,1′-biphenyl]-4-ylthio)thieno[2,3-c]pyridine-2-carboxamide, 4-(5-formyl-2-furanyl)thieno[2,3-c]pyridine-2-carboxamide, ethyl 4-[[2-(aminocarbonyl)thieno[2,3-c]pyridin-4-yl]oxy]benzoate, 4-[[2-(aminocarbonyl)thieno[2,3-c]pyridin-4-yl]oxy]benzoic acid, 4-(1-phenylethenyl)thieno[2,3-c]pyridine-2-carboxamide, methyl 4-(1-phenylethenyl)thieno[2,3-c]pyridine-2-carboxalate, 4-[(4-methylphenyl)thio]thieno[2,3-c]pyridine-2-methanol, 4-(4-Chlorophenoxy)-N-methylthieno[2,3-c]pyridine-2-carboxamide, 4-(4-chlorophenoxy)-N,N-dimethylthieno[2,3-c]pyridine-2-carboxamide, 4-(4-chlorophenoxy)-N,N-diethylthieno[2,3 -c]pyridine-2-carboxamide, 4-(4-chlorophenoxy)-N-cyclopropylthieno[2,3-c]pyridine-2-carboxamide, 1-[[4-(4-chlorophenoxy)thieno[2,3-c]pyridin-2-yl]carbonyl]pyrrolidine, 1-[[4-(4-chlorophenoxy)thieno[2,3-c]pyridin-2-yl]carbonyl]piperidine, 4-[[4-(4-chlorophenoxy)thieno[2,3-c]pyridin-2-yl]carbonyl]morpholine, 1-[[4-(4-chlorophenoxy)thieno[2,3-c]pyridin-2-yl]carbonyl]-4-methylpiperazine, 1-[[4-(4-chlorophenoxy)thieno[2,3-c]pyridin-2-yl]carbonyl]-4-phenyllpiperazine, 1-[[4-(4-chlorophenoxy)thieno[2,3-c]pyridin-2-yl]carbonyl]-4-(phenylmethyl)-piperazine, 1-[[4-(4-chlorophenoxy)thieno[2,3-c]pyridin-2-yl]carbonyl]-4-(2-pyridinyl)-piperazine, 4-(4-chlorophenoxy)-N-(2-hydroxyethyl)thieno[2,3-c]pyridine-2-carboxamide, 4-[[4-(4-chlorophenoxy)thieno[2,3-c]pyridin-2-yl]carbonyl]-N-(1-methylethyl)-1-piperazineacetamide, trifluoroacetate salt, 4-(4-chlorophenoxy)-N-[1-(hydroxymethyl)ethyl]thieno[2,3-c]pyridine-2-carboxamide, 4-(4-chlorophenoxy)-N-[1,1-bis(hydroxymethyl)ethyl]thieno[2,3-c]pyridine-2-carboxamide, (D,L)-4-(4-chlorophenoxy)-N-(2-hydroxypropyl)thieno[2,3-c]pyridine-2-carboxamide, 4-(4-chlorophenoxy)-N-[2-(4-morpholinyl)ethyl]thieno[2,3-c]pyridine-2-carboxamide, 4-(4-chlorophenoxy)thieno[2,3-c]pyridine-2-sulfonamide, 4-(4-morpholinyl)thieno[2,3-c]pyridine-2-carboxamide, 4-(4-chlorophenoxy)thieno[2,3-c]pyridine-2-carboxamide, N-oxide, methyl (4-chlorophenoxy)thieno[2,3-c]pyridine-2-carboxylic acid, N-oxide, 4-(4-chlorophenoxy)-2-(2-methoxyphenyl)thieno[2,3-c]pyridine, 4-(4-Chlorophenoxy)thieno[2,3-c]pyridine, 4-(4-Chlorophenoxy)-3-methylthieno[2,3-c]pyridine-2-carboxamide, Methyl 4-(4-chlorophenoxy)-3-methylthieno[2,3-c]pyridine-2-carboxylate, 3-amino-4-(4-chlorophenoxy)thieno[2,3-c]pyridine-2-carboxamide, methyl 3-amino-4-(4-chlorophenoxy)thieno[2,3-c]pyridine-2-carboxylate, 3-amino-4-(4-chlorophenoxy)thieno[2,3-c]pyridine-2-carboxylic acid, 4-[(4-methylphenyl)thio]thieno[2,3-b]pyridine, 4-[(4-methylphenyl)thio]thieno[2,3-b]pyridine-2-carboxamide, 4-chloro-N-(4-chlorophenyl)thieno[2,3-b]pyridine-5-carboxamide, ethyl 4-[(5-methyl-1,3,4-thiadiazol-2-yl)thio]thieno[2,3-b]pyridine-5-carboxylate, 7-[(4-methylphenyl)thio]thieno[3,2-b]pyridine-2-carboxamide, methyl 6-[(4-methylphenyl)thio]thieno[2,3-b]pyridine-2-carboxylate, methyl 3-amino-6-chlorothieno[2,3-b]pyridine-2-carboxylate, 2-bromo-4-[(4-methylphenyl)thio]thieno[3,2-c]pyridine, 4-[(4-methylphenyl)thio]thieno[3,2-c]pyridine-2-carboxamide, 4-[(4-methylphenyl)thio]thieno[3,2-c]pyridine-2-carbonitrile, 4-(4-Methylphenoxy)thieno[3,2-c]pyridine-2-carboxamide, 4-(4-Methylphenoxy)thieno[3,2-c]pyridine 2-carbonitrile, 7-(4-methylphenoxy)[1,3]thiazolo[5,4-c]pyridine-2-carboxamide, methyl 7-(4-methylphenoxy)[1,3]thiazolo[5,4-c]pyridine-2-carboxylate, 4-(4-chlorophenoxy)thieno[2,3-c]pyridine-2-carbothioamide, 4-(4-chlorophenoxy)-N-ethylthieno[2,3-c]pyridine-2-carboxamide, 4-(4-chlorophenoxy)-N-(2,3-dihydroxypropyl)thieno[2,3-c]pyridine-2-carboxamide, 4-(4-bromophenoxy)-N-(2,3-dihydroxypropyl)thieno[2,3-c]pyridine-2-carboxamide, N-(2-chloroethyl)-4-(4-chlorophenoxy)thieno[2,3-c]pyridine-2-carboxamide, 4-(4-bromophenoxy)-N-(2-hydroxyethyl)thieno[2,3 -c]pyridine-2-carboxamide, 4-(2-bromo-4-chlorophenoxy)-N-(2-hydroxyethyl)thieno[2,3-c]pyridine-2-carboxamide, N-(2-hydroxyethyl)-4-[4-(trifluoromethyl)phenoxy]thieno[2,3-c]pyridine-2-carboxamide, N-(2-aminoethyl)-4-(4-chlorophenoxy)thieno[2,3-c]pyridine-2-carboxamide, 4-(4-chlorophenoxy)-N-hydroxy thieno[2,3-c]pyridine-2-carboxamide, 4-(4-chlorophenoxy)thieno[2,3c]pyridine-2-carbohydrazide, 4-(4-bromophenoxy)thieno[2,3-c]pyridine-2-carbohydrazide, 4-[4-(trifluoromethyl)phenoxy]thieno[2,3-c]pyridine-2-carbohydrazide, 4-(4-chlorophenoxy)-N-hydroxythieno[2,3-c]pyridine-2-carboxamide, 2-({[4-(4-chlorophenoxy)thieno[2,3-c]pyridin-2-yl]carbonyl}amino)acetic acid, N-(2-amino-2-oxoethyl)-4-(4-chlorophenoxy)thieno[2,3-c]pyridine-2-carboxamide, N-(2-amino-2-oxoethyl)-4-(4-bromophenoxy)thieno[2,3-c]pyridine-2-carboxamide, (2S)-2-({[4-(4-chlorophenoxy)thieno[2,3-c]pyridin-2-yl]carbonyl]amino)-3-hydroxypropanoic acid, N-[(1S)-2-amino-1-(hydroxymethyl)-2-oxoethyl]-4-(4-chlorophenoxy)thieno[2,3-c]pyridine-2-carboxamide, (2R)-2-({[4-(4-chlorophenoxy)thieno[2,3-c]pyridin-2-yl]carbonyl}amino)-3-hydroxypropanoic acid, (2R)-2-({[4-(4-chlorophenoxy)thieno[2,3-c]pyridin-2-yl]carbonyl}amino)propanoic acid, 4-(4-chlorophenoxy)-N-[(1R)-1-methyl-2-(methylamino)-2-oxoethyl]thieno[2,3-c]pyridine-2-carboxamide, (2S)-2-({[4-(4-chlorophenoxy)thieno[2,3-c]pyridin-2-yl]carbonyl}amino)propanoic acid, 4-(4-chlorophenoxy)-N-[(1S)-1-methyl-2-(methylamino)-2-oxoethyl]thieno[2,3-c]pyridine-2-carboxamide, 4-(4-chlorophenoxy)-N-[(1R)-1-(hydroxymethyl)-2-(methylamino)-2-oxoethyl]thieno[2,3-c]pyridine-2-carboxamide, 4-(4-chlorophenoxy)-N-[(1S)-1-(hydroxymethyl)-2-(methylamino)-2-oxoethyl]thieno[2,3-c]pyridine-2-carboxamide, 4-(3-pyridinyloxy)thieno[2,3-c]pyridine-2-carboxamide, 4-(4-bromophenoxy)-N-methylthieno[2,3-c]pyridine-2-carboxamide, 4-(4-bromophenoxy)-N,N-dimethylthieno[2,3-c]pyridine-2-carboxamide, N,N-dimethyl-4-[4-(trifluoromethyl)phenoxy]thieno[2,3-c]pyridine-2-carboxamide, 4-(4-chloro-3-fluorophenoxy)-N-methylthieno[2,3-c]pyridine-2-carboxamide, 4-(4-chloro-3-fluorophenoxy)thieno[2,3-c]pyridine-2-carboxamide, 4-(4-chloro-3-ethylphenoxy)thieno[2,3-c]pyridine-2-carboxamide, 4-(3-fluorophenoxy)thieno[2,3-c]pyridine-2-carboxamide, 4-(2,3-difluorophenoxy)thieno[2,3-c]pyridine-2-carboxamide, 4-(2,3-difluorophenoxy)-N-methylthieno[2,3-c]pyridine-2-carboxamide, 4-(3-fluorophenoxy)-N-methylthieno[2,3-c]pyridine-2-carboxamide, N-methyl-4-(2,3,4-trifluorophenoxy)thieno[2,3-c]pyridine-2-carboxamide, 4-(2,3,4-trifluorophenoxy)thieno[2,3-c]pyridine-2-carboxamide, N-ethyl-4-[4-(trifluoromethyl)phenoxy]thieno[2,3-c]pyridine-2-carboxamide, 4-[3-(trifluoromethyl)phenoxy]thieno[2,3 c]pyridine-2-carboxamide, N,N-dimethyl-4-(4-vinylphenoxy)thieno[2,3-c]pyridine-2-carboxamide, 4-(4-cyanophenoxy)-N-methylthieno[2,3 -c]pyridine-2-carboxamide, 4-(4-cyanophenoxy)thieno[2,3-c]pyridine-2-carboxamide, 4-(4-aminophenoxy)thieno[2,3-c]pyridine-2-carboxamide, 4-[4-(acetylamino)phenoxy]thieno[2,3-c]pyridine-2-carboxamide, N-methyl-4-[4-(4-morpholinyl)phenoxy]thieno[2,3-c]pyridine-2-carboxamide, 4-[4-(hydroxymethyl)phenoxy]thieno[2,3-c]pyridine-2-carboxamide, 4-[4-(hydroxymethyl)phenoxy]-N-methylthieno[2,3-c]pyridine-2-carboxamide, 4-[4-(methoxymethyl)phenoxy]-N-methylthieno[2,3-c]pyridine-2-carboxamide, 4-{4-[(2-methoxyethoxy)methyl]phenoxy}thieno [2,3 -c]pyridine-2-carboxamide, 4-{4-[(2-methoxyethoxy)methyl]phenoxy}-N-methylthieno[2,3-c]pyridine-2-carboxamide, 4-(4-{[2-(2-methoxyethoxy)ethoxy]methyl}phenoxy)thieno[2,3-c]pyridine-2-carboxamide, 4-(4-{[2-(2-methoxyethoxy)ethoxy]methyl}phenoxy)-N-methylthieno[2,3 -c]pyridine-2-carboxamide, 4-{4-[(tetrahydro-2H-pyran-2-yloxy)methyl]phenoxy}thieno[2,3-c]pyridine-2-carboxamide, N-methyl-4-{4-[(tetrahydro-2H-pyran-2-yloxy)methyl]phenoxy}thieno[2,3-c]pyridine-2-carboxamide, 4-{[2-(aminocarbonyl)thieno[2,3-c]pyridin-4-yl]oxy}benzyl 2-furoate, 4-[4-({[(2R,4R,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl]oxy}methyl)phenoxy]-N-methylthieno[2,3-c]pyridine-2-carboxamide, 4-(4-acetylphenoxy)-N-methylthieno[2,3-c]pyridine-2-carboxamide, 4-[4-(4-morpholinylcarbonyl)phenoxy]thieno[2,3-c]pyridine-2-carboxamide, N-methyl-4-[4-(4-morpholinylcarbonyl)phenoxy]thieno[2,3-c]pyridine-2-carboxamide, 4-[4-({[2-(4-morpholinyl)ethyl]amino}carbonyl)phenoxy]thieno[2,3-c]pyridine-2-carboxamide, N-methyl-4-[4-({[2-(4-morpholinyl)ethyl]amino}carbonyl)phenoxy]thieno[2,3-c]pyridine-2-carboxamide, 4-{4-[(E)-3 -(4-morpholinyl)-3 -oxo-1 -propenyl]phenoxy}thieno[2,3 -c]pyridine-2-carboxamide, 4-[4-((E)-3-{[2-(4-morpholinyl)ethyl]amino}-3-oxo-1-propenyl)phenoxy]thieno[2,3-c]pyridine-2-carboxamide, N-methyl-4-[4-((E)-3-{[2-(4-morpholinyl)ethyl]amino}-3-oxo-1-propenyl)phenoxy]thieno[2,3 -c]pyridine-2-carboxamide, 4-(4-{(E)-3-[(2,3-dihydroxypropyl)amino]-3-oxo-1-propenyl}phenoxy)thieno[2,3-c]pyridine-2-carboxamide, 4-(4-{(E)-3-[(2,3-dihydroxypropyl)amino]-3-oxo-1-propenyl}phenoxy)-N-methylthieno[2,3-c]pyridine-2-carboxamide, 4-[4-((E)-3-{[2-(1H-imidazol-4-yl)ethyl]amino}-3-oxo-1-propenyl)phenoxy]-N-methylthieno[2,3-c]pyridine-2-carboxamide, 4-{4-[(E)-3-({2-[bis(2-hydroxyethyl)amino]ethyl}amino)-3-oxo-1-propenyl]phenoxy}-N-methylthieno[2,3-c]pyridine-2-carboxamide, 4-14-[(E)-3-({2-[bis(2-hydroxyethyl)amino]ethyl}amino)-3-oxo-1-propenyl]phenoxy}thieno[2,3-c]pyridine-2-carboxamide, 4-[4-(1H-imidazol-1-yl)phenoxy]thieno[2,3-c]pyridine-2-carboxamide, N-methyl-4-[4-(1H-pyrazol-1-yl)phenoxy]thieno[2,3-c]pyridine-2-carboxamide, N-methyl-4-[4-(1H-1,2,4-triazol-1-yl)phenoxy]thieno[2,3-c]pyridine-2-carboxamide, N-methyl-4-{4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenoxy}thieno[2,3-c]pyridine-2-carboxamide, 4-[4-(4,5-dihydro-1H-imidazol-2-yl)phenoxy]-N-methylthieno[2,3-c]pyridine-2-carboxamide, N-methyl-4-[4-(2-thienyl)phenoxy]thieno[2,3 -c]pyridine-2-carboxamide, 4-([1,1′-biphenyl]-4-yloxy)-N-methylthieno[2,3-c]pyridine-2-carboxamide, N-methyl4-[4-(1-methyl-1H-imidazol-5-yl)phenoxy]thieno[2,3-c]pyridine-2-carboxamide, 4-(4-[1-(hydroxymethyl)cyclopropyl]phenoxy}-N-methylthieno[2,3-c]pyridine-2-carboxamide, 4-[4-(1-{[2-(2-ethoxyethoxy)ethoxy]methyl}cyclopropyl)phenoxy]-N-methylthieno[2,3-c]pyridine-2-carboxamide, N-methyl-4-[4-(trifluoromethoxy)phenoxy]thieno[2,3-c]pyridin -2-carboxamide, 5-{4-[4-(1-{[2-(2-ethoxyethoxy)ethoxy]methyl}cyclopropyl)phenoxy]thieno[2,3-c]pyridin-2-yl}-1,3,4-oxadiazol-2-amine, 4-[4-(1,1-difluoro-2-hydroxyethyl)phenoxy]-N-methylthieno[2,3-c]pyridine-2-carboxamide, 4-(4-{2-[2-(2-ethoxyethoxy)ethoxy]-1,1-difluoroethyl}phenoxy)-N-methylthieno[2,3-c]pyridine-2-carboxamide, 4-(4-chlorophenoxy)-6-{[(2,2-dimethylpropanoyl)oxy]methyl}-2-[(methylamino)carbonyl]thieno[2,3-c]pyridin-6-ium, 4-(4-bromophenoxy)-6-{[(2,2-dimethylpropanoyl)oxy]methyl}-2-[(methylamino)carbonyl]thieno[2,3-c]pyridin-6-ium, 2-(aminocarbonyl)-4-(4-chlorophenoxy)-6-{[(isopropoxycarbonyl)oxy]methyl}thieno[2,3-c]pyridin-6-ium, 4-(benzyloxy)thieno[2,3-c]pyridine-2-carboxamide, 4-[(4-chlorophenyl)(hydroxy)methyl]thieno[2,3-c]pyridine-2-carboxamide, 4-(4-chlorobenzoyl)-N-methylthieno[2,3-c]pyridine-2-carboxamide, N 4 -(4-chlorophenyl)thieno[2,3-c]pyridine-2,4-dicarboxamide, [4-(4-bromophenoxy)thieno[2,3-c]pyridin-2-yl]methanol, 4-(4-bromophenoxy)thieno[2,3-c]pyridine-2-carbaldehyde, 4-(4-chlorophenoxy)thieno[2,3-c]pyridine-2-carbaldehyde oxime, 4-(4-chlorophenoxy)thieno[2,3-c]pyridine-2-carbaldehyde O-methyloxime, 1-[4-(4-chlorophenoxy)thieno[2,3-c]pyridin-2-yl]-1-ethanone O-methyloxime, 1-[4-(4-chlorophenoxy)thieno[2,3-c]pyridin-2-yl]-1-ethanone O-methyloxime, 1-[4-(4-chlorophenoxy)thieno[2,3-c]pyridin-2-yl]-1-ethanone oxime, 1-[4-(4-chlorophenoxy)thieno[2,3-c]pyridin-2-yl]-1-ethanone oxime, 1-[4-(4-chlorophenoxy)thieno[2,3-c]pyridin-2-yl]-1-propanone, 1-[4-(4-chlorophenoxy)thieno[2,3-c]pyridin-2-yl]-1-propanone oxime, 2-[4-(4-chlorophenoxy)thieno[2,3-c]pyridin-2-yl]-N-methoxy-N-methyl-2-oxoacetamide, 4-(4-chlorophenoxy)thieno[2,3-c]pyridine-2-carbonitrile, 4-(4-chlorophenoxy)-N′-hydroxythieno[2,3-c]pyridine-2-carboximidamide, 4-(4-chlorophenoxy)-N′-cyanothieno[2,3-c]pyridine-2-carboximidamide [4-(4-chlorophenoxy)thieno[2,3 -c]pyridin-2-yl](2-nitrophenyl)methanol, [4-(4-chlorophenoxy)thieno[2,3 -c]pyridin-2-yl](2-nitrophenyl)methanone, (2-aminophenyl)[4-(4-chlorophenoxy)thieno[2,3-c]pyridin-2-yl]methanone, (2-aminophenyl)[4-(4-chlorophenoxy)thieno[2,3-c]pyridin-2-yl]methanol, [4-(4-chlorophenoxy)thieno[2,3-c]pyridin-2-yl](3 -nitrophenyl)methanol, (3 -aminophenyl)[4-(4-chlorophenoxy)thieno[2,3-c]pyridin-2-yl]methanone, (3 -aminophenyl)[4-(4-chlorophenoxy)thieno[2,3-c]pyridin-2-yl]methanol, 4-(4-bromophenoxy)-2-vinylthieno[2,3-c]pyridine, 1-[4-(4-chlorophenoxy)thieno[2,3-c]pyridin-2-yl]-1,2-ethanediol, 1-[4-(4-bromophenoxy)thieno[2,3-c]pyridin-2-yl]-1,2-ethanediol, [4-(4-chlorophenoxy)thieno[2,3-c]pyridin-2-yl]methanamine, [4-(4-chlorophenoxy)thieno[2,3-c]pyridin-2-yl]methyl carbamate, N-{[4-(4-chlorophenoxy)thieno[2,3-c]pyridin-2-yl]methyl}urea, (E)-3-[4-(4-bromophenoxy)thieno[2,3-c]pyridin-2-yl]-2-propenamide, (E)-3-[4-(4-bromophenoxy)thieno[2,3-c]pyridin-2-yl]-N-methyl-2-propenamide, 3-[4-(4-bromophenoxy)thieno[2,3-c]pyridin-2-yl]-2,3-dihydroxy-N-methylpropanamide, 4-(4-chlorophenoxy)thieno[2,3-c]pyridin-2-ylamine, 4-(4-chlorophenoxy)thieno[2,3-c]pyridin-2-ylformamide, N-[4-(4-chlorophenoxy)thieno[2,3-c]pyridin-2-yl]urea, N-[4-(4-chlorophenoxy)thieno[2,3-c]pyridin-2-yl]-N′-methylthiourea, 4-(4-chlorophenoxy)-N-methylthieno[2,3-c]pyridine-2-sulfonamide, 4-(4-chlorophenoxy)-N-(2,3-dihydroxypropyl)thieno[2,3-c]pyridine-2-sulfonamide, 4-(4-chlorophenoxy)-N-(2-hydroxyethyl)thieno[2,3-c]pyridine-2-sulfonamide, 4-[4-(4-chlorophenoxy)thieno[2,3-c]pyridin-2-yl]phenol, 3-[4-(4-chlorophenoxy)thieno[2,3-c]pyridin-2-yl]aniline, 4-[4-(4-chlorophenoxy)thieno[2,3-c]pyridin-2-yl]aniline, 4-(4-chlorophenoxy)-2-(5-nitro-2-pyridinyl)thieno[2,3-c]pyridine, 6-[4-(4-chlorophenoxy)thieno[2,3-c]pyridin-2-yl]-3-pyridinamine, 5-[4-(4-chlorophenoxy)thieno[2,3-c]pyridin-2-yl]-2-pyridinamine, 5-[4-(4-chlorophenoxy)thieno[2,3-c]pyridin-2-yl]-1,3,4-oxadiazol-2-amine, 5-[4-(4-bromophenoxy)thieno[2,3-c]pyridin-2-yl]-1,3,4-oxadiazol-2-ylamine, 5-[4-(4-chlorophenoxy)thieno[2,3-c]pyridin-2-yl]-4H-1,2,4-triazol-3-amine, 5-[4-(4-chlorophenoxy)thieno[2,3-c]pyridin-2-yl]-1,3,4-thiadiazol-2-amine, 4-(4-chlorophenoxy)-2-(5-methyl-1,2,4-oxadiazol-3-yl)thieno[2,3-c]pyridine, 5-{4-[4-(trifluoromethyl)phenoxy]thieno[2,3-c]pyridin-2-yl}-1,3,4-oxadiazol-2-amine, 4-(4-chlorophenoxy)-2-[5-(methylsulfanyl)-1,3,4-oxadiazol-2-yl]thieno[2,3-c]pyridine, 4-(4-chlorophenoxy)-2-(2-methyl-2H-1,2,3,4-tetraazol-5-yl)thieno[2,3-c]pyridine, 5-[4-(4-chlorophenoxy)thieno[2,3-c]pyridin-2-yl]-4-methyl-4H-1,2,4-triazol-3-amine, 4-(4-chlorophenoxy)-2-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]thieno[2,3-c]pyridine, 5-[4-(4-chlorophenoxy)thieno[2,3-c]pyridin-2-yl]-1,2,4-oxadiazol-3-amine, 5-[4-(4-chlorophenoxy)thieno[2,3-c]pyridin-2-yl]-N-methyl-1,3,4-thiadiazol-2-amine, 4-(4-chlorophenoxy)-2-(1,2,4-oxadiazol-3-yl)thieno[2,3-c]pyridine, 2-(1,3,4-oxadiazol-2-yl)-4-[4-(trifluoromethyl)phenoxy]thieno[2,3-c]pyridine, 3-[4-(4-chlorophenoxy)thieno[2,3-c]pyridin-2-yl]-1,2,4-oxadiazol-5-amine, 2-(5-methyl-1,3,4-oxadiazol-2-yl)-4-[4-(trifluoromethyl)phenoxy]thieno[2,3-c]pyridine, methyl 2-[4-(4-chlorophenoxy)thieno[2,3-c]pyridin-2-yl]-1,3-thiazole-4-carboxylate, 2-[4-(4-chlorophenoxy)thieno[2,3-c]pyridin-2-yl]-1,3-thiazole-4-carboxamide, tert-butyl 2-[4-(4-chlorophenoxy)thieno[2,3-c]pyridin-2-yl]-1,3-thiazol-4-ylcarbamate, 2-[4-(4-chlorophenoxy)thieno[2,3-c]pyridin-2-yl]-1,3-thiazol-4-amine, 4-chloro-3-methylthieno[2,3-c]pyridine-2-carboxamide, 3-amino-4-chlorothieno[2,3-c]pyridine-2-carboxamide, 4-(4-chlorophenoxy)-N,3-dimethylthieno[2,3-c]pyridine-2-carboxamide, 4-(4-bromophenoxy)-3-methylthieno[2,3-c]pyridine-2-carboxamide, 7-chloro-4-(4-chlorophenoxy)-3-methylthieno[2,3-c]pyridine-2-carboxamide, tert-butyl 2-(aminocarbonyl)-4-(4-chlorophenoxy)thieno[2,3-c]pyridine-3-carboxylate, N-methyl-4-(4-toluidino)thieno[2,3-c]pyridine-2-carboxamide, 4-(4-chloroanilino)-N-methylthieno[2,3-c]pyridine-2-carboxamide, N-methyl-4-(4-morpholinyl)thieno[2,3-c]pyridine-2-carboxamide, 7-chloro-4-(4-chlorophenoxy)thieno[2,3-c]pyridine-2-carboxamide, 7-chloro-4-(4-chlorophenoxy)-N-methylthieno[2,3-c]pyridine-2-carboxamide, 7-chloro-4-(4-chlorophenoxy)-N-(2-hydroxyethyl)thieno[2,3-c]pyridine-2-carboxamide, 7-bromo-4-(4-chlorophenoxy)thieno[2,3-c]pyridine-2-carboxamide, 7-bromo-4-(4-chlorophenoxy)-N-methylthieno[2,3-c]pyridine-2-carboxamide, 4-(4-bromophenoxy)-7-chlorothieno[2,3-c]pyridine-2-carboxamide, 4-(4-bromophenoxy)-7-chloro-N-methylthieno[2,3-c]pyridine-2-carboxamide, 7-chloro-4-[4-(trifluoromethyl)phenoxy]thieno[2,3-c]pyridine-2-carboxamide, 7-chloro-N-methyl-4-[4-(trifluoromethyl)phenoxy]thieno[2,3-c]pyridine-2-carboxamide, 7-chloro-N-(2-hydroxyethyl)-4-[4-(trifluoromethyl)phenoxy]thieno[2,3 -c]pyridine-2-carboxamide, 4-(4-chlorophenoxy)-N,7-dimethylthieno[2,3-c]pyridine-2-carboxamide, 4-(4-chlorophenoxy)-7-methoxythieno[2,3-c]pyridine-2-carboxamide, 4-(4-chlorophenoxy)-7-oxo-6,7-dihydrothieno[2,3-c]pyridine-2-carboxamide, 4-(4-chlorophenoxy)-N-methyl-7-(methylamino)thieno[2 3-c]pyridine-2-carboxamide, N-methyl-7-(4-methylphenoxy)[1,3]thiazolo[5,4-c]pyridine-2-carboxamide, 4-(4-chlorophenoxy)furo[2,3-c]pyridine-2-carboxamide, 4-(4-chlorophenoxy)furo[2,3-c]pyridine-2-carbothioamide, 4-[(E)-2-phenylethenyl]thieno[2,3-c]pyridine-2-carboxamide, 4-(4-chlorophenyl)thieno[2,3-c]pyridine-2-carboxamide, 4-[3-(trifluoromethyl)phenyl]thieno[2;3-c]pyridine-2-carboxamide, 4-(3-chlorophenyl)thieno[2,3-c]pyridine-2-carboxamide, 4-(4-bromophenyl)thieno[2,3-c]pyridine-2-carboxamide, 4-(3-aminophenyl)thieno[2,3-c]pyridine-2-carboxamide, 4-(3,5-dichlorophenyl)thieno[2 3-c]pyridine-2-carboxamide, 4-(2,4-dichlorophenyl)thieno[2,3-c]pyridine-2-carboxamide, 4-(3,4-dichlorophenyl)thieno[2,3-c]pyridine-2-carboxamide, 4-(2,4-difluorophenyl)thieno[2,3-c]pyridine-2-carboxamide, 4-(4(4-fluorophenyl)thieno[2,3-c]pyridine-2-carboxamide, and 4-(4-bromophenoxy)-5-chlorothieno[2,3-c]pyridine-2-carboxamide.
23 . A method for treating reperfusion injuries and inflammatory diseases comprising administering an effective amount of a compound of claim 1.Join the waitlist — get patent alerts
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