US 2014/0155415 A1Published application

Benzodioxepine and benzodioxine compounds that interact with glucokinase regulatory protein for the treatment of diabetes

OwnerMichael David Bartberger, Michael D. Croghan +6inventors

InventorsMichael David Bartberger, Michael D. Croghan, Christopher H. Fotsch, Mark H. Norman, Lewis Dale Pennington, Andreas Reichelt, David J. St. Jean, JR., Christopher M. Tegley

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Abstract

The present invention relates to compounds of formula I or II, or pharmaceutically acceptable salts thereof, that interact with glucokinase regulatory protein. In addition, the present invention relates to methods of treating type 2 diabetes, and other diseases and/or conditions where glucokinase regulatory protein is involved using the compounds, or pharmaceutically acceptable salts thereof, and pharmaceutical compositions that contain the compounds, or pharmaceutically acceptable salts thereof.

Claims22

Dependent claims

A compound of formula I or II, or a pharmaceutically acceptable salt thereof, wherein:

the symbol * represents a chiral center that has the R configuration or is a mixture of the R and S configurations;
n is 0 or 1;
R1 is a five or six membered monocyclic aryl group or monocyclic heteroaryl group, wherein the heteroatoms are independently selected from N, O or S, which groups can be optionally substituted at the (1) positions with respect to its point of attachment to the rest of the compound, when possible, with a substituent selected from —C1-8alkyl, —C1-8alkoxy, halo, —SC1-8alkyl, —C2-8alkenyl, —C2-8alkynyl, —C1-8hydroxyalkyl, haloalkyl, perfluoroalkyl or —OCF3;
or at the (2) positions, when possible, with a substituent selected from fluorine,
—OH or —NH2;
or at the (3) position, when possible, with fluorine;
R2 is a nine or ten membered bicyclic aryl group or bicyclic heteroaryl group, wherein the heteroatoms are independently selected from N, O or S, which groups can be optionally substituted with from 1 to 7 substituents independently selected from halo, C1-6 alkyl, C1-6alkoxy, —OH or a five or six membered aryl or heteroaryl group, which aryl or heteroaryl group that can be optionally substituted with from 1 to 3 substituents independently selected from C1-6 alkyl, C1-6alkoxy, —OH, —NH2, —C(CF3)(OH)(CF3) or —C(CF3)(OH)(CH3);
each R3 is independently hydrogen, —OH or halo when n is 1, or hydrogen, —OH, halo or —CH3 when n is 0;
and
each R4 is independently hydrogen or halo;
provided that the compound is not N-(1-benzofuran-2-yl(phenyl)methyl)-3,4-dihydro-2H-1,5-benzodioxepine-7-sulfonamide.

8 more elements

A compound, or a pharmaceutically acceptable salt, selected from:

N-(1-benzofuran-2-yl(2-methylphenyl)methyl)-3,4-dihydro-2H-1,5-benzodioxepine-7-sulfonamide;
N-(1-benzofuran-2-yl(4-fluoro-2-methylphenyl)methyl)-3,4-dihydro-2H-1,5-benzodioxepine-7-sulfonamide;
N-(1-benzofuran-2-yl(5-fluoro-2-methylphenyl)methyl)-3,4-dihydro-2H-1,5-benzodioxepine-7-sulfonamide;
N-(1-benzofuran-2-yl(2-fluoro-6-methylphenyl)methyl)-3,4-dihydro-2H-1,5-benzodioxepine-7-sulfonamide;
N-(1-benzofuran-2-yl(2-ethylphenyl)methyl)-3,4-dihydro-2H-1,5-benzodioxepine-7-sulfonamide;
N-(1-benzofuran-2-yl(2-ethenylphenyl)methyl)-3,4-dihydro-2H-1,5-benzodioxepine-7-sulfonamide;
N-(1-benzofuran-2-yl(2-ethynylphenyl)methyl)-3,4-dihydro-2H-1,5-benzodioxepine-7-sulfonamide;
N-(1-benzofuran-2-yl(2-(1-methylethyl)phenyl)methyl)-3,4-dihydro-2H-1,5-benzodioxepine-7-sulfonamide;
N-(1-benzofuran-2-yl (2,6-dimethylphenyl)methyl)-3,4-dihydro-2H-1,5-benzodioxepine-7-sulfonamide;
N-(1-benzofuran-2-yl(2-propylphenyl)methyl)-3,4-dihydro-2H-1,5-benzodioxepine-7-sulfonamide;
N-(1-benzofuran-2-yl(2-(trifluoromethyl)phenyl)methyl)-3,4-dihydro-2H-1,5-benzodioxepine-7-sulfonamide;
N-(1-benzofuran-2-yl(3-hydroxyphenyl)methyl)-3,4-dihydro-2H-1,5-benzodioxepine-7-sulfonamide;
N-((3-aminophenyl)(1-benzofuran-2-yl)methyl)-3,4-dihydro-2H-1,5-benzodioxepine-7-sulfonamide;
N-(1-benzofuran-2-yl(2-(hydroxymethyl)phenyl)methyl)-3,4-dihydro-2H-1,5-benzodioxepine-7-sulfonamide;
N-(1-benzofuran-2-yl(2-(2-hydroxyethyl)phenyl)methyl)-3,4-dihydro-2H-1,5-benzodioxepine-7-sulfonamide;
N-(1-benzofuran-2-yl(2-methoxyphenyl)methyl)-3,4-dihydro-2H-1,5-benzodioxepine-7-sulfonamide;
N-(1-benzofuran-2-yl(2-(trifluoromethoxy)phenyl)methyl)-3,4-dihydro-2H-1,5-benzodioxepine-7-sulfonamide;
N-(1-benzofuran-2-yl(2-(methylsulfanyl)phenyl)methyl)-3,4-dihydro-2H-1,5-benzodioxepine-7-sulfonamide;
N-(1-benzofuran-2-yl(2-chlorophenyl)methyl)-3,4-dihydro-2H-1,5-benzodioxepine-7-sulfonamide;
N-(1-benzofuran-2-yl(2-iodophenyl)methyl)-3,4-dihydro-2H-1,5-benzodioxepine-7-sulfonamide;
N-(1-benzofuran-2-yl(2-bromophenyl)methyl)-3,4-dihydro-2H-1,5-benzodioxepine-7-sulfonamide;
N-(1-benzofuran-2-yl(2-fluorophenyl)methyl)-3,4-dihydro-2H-1,5-benzodioxepine-7-sulfonamide;
N-(1-benzofuran-2-yl(3-fluorophenyl)methyl)-3,4-dihydro-2H-1,5-benzodioxepine-7-sulfonamide;
N-(1-benzofuran-2-yl(2-pyridinyl)methyl)-3,4-dihydro-2H-1,5-benzodioxepine-7-sulfonamide;
N-(1-benzofuran-2-yl(3-methyl-2-pyridinyl)methyl)-3,4-dihydro-2H-1,5-benzodioxepine-7-sulfonamide;
N-(1-benzofuran-2-yl(2-chloro-3-pyridinyl)methyl)-3,4-dihydro-2H-1,5-benzodioxepine-7-sulfonamide;
N-(1-benzofuran-2-yl(3-chloro-4-pyridinyl)methyl)-3,4-dihydro-2H-1,5-benzodioxepine-7-sulfonamide;
N-(1-benzofuran-2-yl(2-pyrimidinyl)methyl)-3,4-dihydro-2H-1,5-benzodioxepine-7-sulfonamide;
N-(1-benzofuran-2-yl(3-methoxy-2-pyridinyl)methyl)-3,4-dihydro-2H-1,5-benzodioxepine-7-sulfonamide;
N-(1-benzofuran-2-yl(2-thiophenyl)methyl)-3,4-dihydro-2H-1,5-benzodioxepine-7-sulfonamide;
N-(1-benzofuran-2-yl(3-thiophenyl)methyl)-3,4-dihydro-2H-1,5-benzodioxepine-7-sulfonamide;
N-(1-benzofuran-2-yl(3-methyl-2-thiophenyl)methyl)-3,4-dihydro-2H-1,5-benzodioxepine-7-sulfonamide;
N-(1-benzofuran-2-yl(1,3-thiazol-2-yl)methyl)-3,4-dihydro-2H-1,5-benzodioxepine-7-sulfonamide;
N-(1-benzofuran-2-yl(phenyl)methyl)-3-fluoro-3,4-dihydro-2H-1,5-benzodioxepine-7-sulfonamide;
N-(1-benzothiophen-2-yl(2-methylphenyl)methyl)-3,4-dihydro-2H-1,5-benzodioxepine-7-sulfonamide;
N-(1-benzothiophen-2-yl(2-ethylphenyl)methyl)-3,4-dihydro-2H-1,5-benzodioxepine-7-sulfonamide;
N-(1-benzothiophen-2-yl(2-ethenylphenyl)methyl)-3,4-dihydro-2H-1,5-benzodioxepine-7-sulfonamide;
N-(1-benzothiophen-2-yl(2-ethynylphenyl)methyl)-3,4-dihydro-2H-1,5-benzodioxepine-7-sulfonamide;
N-(1-benzothiophen-2-yl(2-methoxyphenyl)methyl)-3,4-dihydro-2H-1,5-benzodioxepine-7-sulfonamide;
N-(1-benzothiophen-2-yl(2-(methylsulfanyl)phenyl)methyl)-3,4-dihydro-2H-1,5-benzodioxepine-7-sulfonamide;
N-(1-benzothiophen-2-yl(2-chlorophenyl)methyl)-3,4-dihydro-2H-1,5-benzodioxepine-7-sulfonamide;
N-(1-benzothiophen-2-yl(3-methoxy-2-pyridinyl)methyl)-3,4-dihydro-2H-1,5-benzodioxepine-7-sulfonamide;
N-((3-methyl-1-benzofuran-2-yl)(phenyl)methyl)-3,4-dihydro-2H-1,5-benzodioxepine-7-sulfonamide;
N-((3-methyl-1-benzofuran-2-yl)(2-methylphenyl)methyl)-3,4-dihydro-2H-1,5-benzodioxepine-7-sulfonamide;
N-(phenyl(thieno[2,3-b]pyridin-2-yl)methyl)-3,4-dihydro-2H-1,5-benzodioxepine-7-sulfonamide;
N-((2-methoxyphenyl)(thieno[2,3-b]pyridin-2-yl)methyl)-3,4-dihydro-2H-1,5-benzodioxepine-7-sulfonamide;
N-((2-(methylsulfanyl)phenyl)(thieno[2,3-b]pyridin-2-yl)methyl)-3,4-dihydro-2H-1,5-benzodioxepine-7-sulfonamide;
N-((3-methoxy-2-pyridinyl)(thieno[2,3-b]pyridin-2-yl)methyl)-3,4-dihydro-2H-1,5-benzodioxepine-7-sulfonamide;
N-((3-methoxy-4-pyridinyl)(thieno[2,3-b]pyridin-2-yl)methyl)-3,4-dihydro-2H-1,5-benzodioxepine-7-sulfonamide;
N-(1,3-benzothiazol-2-yl(2-methoxyphenyl)methyl)-3,4-dihydro-2H-1,5-benzodioxepine-7-sulfonamide;
N-(1,3-benzothiazol-2-yl(2-(methylsulfanyl)phenyl)methyl)-3,4-dihydro-2H-1,5-benzodioxepine-7-sulfonamide;
N-(1,3-benzothiazol-2-yl(3-methoxy-2-pyridinyl)methyl)-3,4-dihydro-2H-1,5-benzodioxepine-7-sulfonamide;
N-(1,3-benzoxazol-2-yl(phenyl)methyl)-3,4-dihydro-2H-1,5-benzodioxepine-7-sulfonamide;
N-(2-naphthalenyl(phenyl)methyl)-3,4-dihydro-2H-1,5-benzodioxepine-7-sulfonamide;
N-(phenyl(2-quinolinyl)methyl)-3,4-dihydro-2H-1,5-benzodioxepine-7-sulfonamide;
N-(1-benzothiophen-2-yl(phenyl)methyl)-3,4-dihydro-2H-1,5-benzodioxepine-7-sulfonamide;
N-((5-methoxy-1-benzothiophen-2-yl)(phenyl)methyl)-3,4-dihydro-2H-1,5-benzodioxepine-7-sulfonamide;
N-(1,3-benzothiazol-2-yl(phenyl)methyl)-3,4-dihydro-2H-1,5-benzodioxepine-7-sulfonamide;
N-(phenyl(thieno[2,3-c]pyridin-2-yl)methyl)-3,4-dihydro-2H-1,5-benzodioxepine-7-sulfonamide;
N-(phenyl(thieno[3,2-b]pyridin-2-yl)methyl)-3,4-dihydro-2H-1,5-benzodioxepine-7-sulfonamide;
N-(phenyl(thieno[3,2-c]pyridin-2-yl)methyl)-3,4-dihydro-2H-1,5-benzodioxepine-7-sulfonamide;
N-((5-hydroxy-1-benzothiophen-2-yl)(phenyl)methyl)-3,4-dihydro-2H-1,5-benzodioxepine-7-sulfonamide;
N-((2-(methylsulfanyl)phenyl)(thieno[2,3-c]pyridin-2-yl)methyl)-3,4-dihydro-2H-1,5-benzodioxepine-7-sulfonamide;
N-((2-(methylsulfanyl)phenyl)([1,3]thiazolo[5,4-b]pyridin-2-yl)methyl)-3,4-dihydro-2H-1,5-benzodioxepine-7-sulfonamide;
N-((2-methoxyphenyl)(thieno[2,3-c]pyridin-2-yl)methyl)-3,4-dihydro-2H-1,5-benzodioxepine-7-sulfonamide;
N-((2-methoxyphenyl)([1,3]thiazolo[5,4-b]pyridin-2-yl)methyl)-3,4-dihydro-2H-1,5-benzodioxepine-7-sulfonamide;
N-((2-chlorophenyl)([1,3]thiazolo[5,4-b]pyridin-2-yl)methyl)-3,4-dihydro-2H-1,5-benzodioxepine-7-sulfonamide;
N-((3-methoxy-2-pyridinyl)([1,3]thiazolo[5,4-b]pyridin-2-yl)methyl)-3,4-dihydro-2H-1,5-benzodioxepine-7-sulfonamide;
N-(phenyl(7-(4-(2,2,2-trifluoro-1-hydroxy-1-methylethyl)-2-pyridinyl)-1-benzothiophen-2-yl)methyl)-3,4-dihydro-2H-1,5-benzodioxepine-7-sulfonamide;
N-(phenyl(7-(2-pyridinyl)-1-benzothiophen-2-yl)methyl)-3,4-dihydro-2H-1,5-benzodioxepine-7-sulfonamide;
N-((7-chloro-1-benzothiophen-2-yl)(phenyl)methyl)-3,4-dihydro-2H-1,5-benzodioxepine-7-sulfonamide;
N-(phenyl(7-phenyl-1-benzothiophen-2-yl)methyl)-3,4-dihydro-2H-1,5-benzodioxepine-7-sulfonamide;
N-(1-benzothiophen-2-yl(2-(methylsulfanyl)phenyl)methyl)-3,4-dihydro-2H-1,5-benzodioxepine-7-sulfonamide;
or
N-(1-benzothiophen-2-yl(2-(methylsulfanyl)phenyl)methyl)-2,3-dihydro-1,4-benzodioxine-6-sulfonamide.

72 more elements

A compound, or a pharmaceutically acceptable salt, selected from:

N—((R)-1-benzofuran-2-yl(phenyl)methyl)-3,4-dihydro-2H-1,5-benzodioxepine-7-sulfonamide;
N—((S)-1-benzofuran-2-yl(phenyl)methyl)-3,4-dihydro-2H-1,5-benzodioxepine-7-sulfonamide;
N—((R)-1-benzofuran-2-yl(2-methylphenyl)methyl)-3,4-dihydro-2H-1,5-benzodioxepine-7-sulfonamide;
N—((R)-1-benzofuran-2-yl(4-fluoro-2-methylphenyl)methyl)-3,4-dihydro-2H-1,5-benzodioxepine-7-sulfonamide;
N—((R)-1-benzofuran-2-yl(5-fluoro-2-methylphenyl)methyl)-3,4-dihydro-2H-1,5-benzodioxepine-7-sulfonamide;
N—((R)-1-benzofuran-2-yl(2-fluoro-6-methylphenyl)methyl)-3,4-dihydro-2H-1,5-benzodioxepine-7-sulfonamide;
N—((R)-1-benzofuran-2-yl(2-ethylphenyl)methyl)-3,4-dihydro-2H-1,5-benzodioxepine-7-sulfonamide;
N—((R)-1-benzofuran-2-yl(2-ethenylphenyl)methyl)-3,4-dihydro-2H-1,5-benzodioxepine-7-sulfonamide;
N—((R)-1-benzofuran-2-yl(2-ethynylphenyl)methyl)-3,4-dihydro-2H-1,5-benzodioxepine-7-sulfonamide;
N—((R)-1-benzofuran-2-yl(2-(1-methylethyl)phenyl)methyl)-3,4-dihydro-2H-1,5-benzodioxepine-7-sulfonamide;
N—((R)-1-benzofuran-2-yl (2,6-dimethylphenyl)methyl)-3,4-dihydro-2H-1,5-benzodioxepine-7-sulfonamide;
N—((R)-1-benzofuran-2-yl(2-propylphenyl)methyl)-3,4-dihydro-2H-1,5-benzodioxepine-7-sulfonamide;
N—((R)-1-benzofuran-2-yl(2-(trifluoromethyl)phenyl)methyl)-3,4-dihydro-2H-1,5-benzodioxepine-7-sulfonamide;
N—((R)-1-benzofuran-2-yl(3-hydroxyphenyl)methyl)-3,4-dihydro-2H-1,5-benzodioxepine-7-sulfonamide;
N—((R)-(3-aminophenyl)(1-benzofuran-2-yl)methyl)-3,4-dihydro-2H-1,5-benzodioxepine-7-sulfonamide;
N—((R)-1-benzofuran-2-yl(2-(hydroxymethyl)phenyl)methyl)-3,4-dihydro-2H-1,5-benzodioxepine-7-sulfonamide;
N—((R)-1-benzofuran-2-yl(2-(2-hydroxyethyl)phenyl)methyl)-3,4-dihydro-2H-1,5-benzodioxepine-7-sulfonamide;
N—((R)-1-benzofuran-2-yl(2-methoxyphenyl)methyl)-3,4-dihydro-2H-1,5-benzodioxepine-7-sulfonamide;
N—((R)-1-benzofuran-2-yl(2-(trifluoromethoxy)phenyl)methyl)-3,4-dihydro-2H-1,5-benzodioxepine-7-sulfonamide;
N—((R)-1-benzofuran-2-yl(2-(methylsulfanyl)phenyl)methyl)-3,4-dihydro-2H-1,5-benzodioxepine-7-sulfonamide;
N—((R)-1-benzofuran-2-yl(2-chlorophenyl)methyl)-3,4-dihydro-2H-1,5-benzodioxepine-7-sulfonamide;
N—((R)-1-benzofuran-2-yl(2-iodophenyl)methyl)-3,4-dihydro-2H-1,5-benzodioxepine-7-sulfonamide;
N—((R)-1-benzofuran-2-yl(2-bromophenyl)methyl)-3,4-dihydro-2H-1,5-benzodioxepine-7-sulfonamide;
N—((R)-1-benzofuran-2-yl(2-fluorophenyl)methyl)-3,4-dihydro-2H-1,5-benzodioxepine-7-sulfonamide;
N—((R)-1-benzofuran-2-yl(3-fluorophenyl)methyl)-3,4-dihydro-2H-1,5-benzodioxepine-7-sulfonamide;
N—((R)-1-benzofuran-2-yl(2-pyridinyl)methyl)-3,4-dihydro-2H-1,5-benzodioxepine-7-sulfonamide;
N—((R)-1-benzofuran-2-yl(3-methyl-2-pyridinyl)methyl)-3,4-dihydro-2H-1,5-benzodioxepine-7-sulfonamide;
N—((R)-1-benzofuran-2-yl(2-chloro-3-pyridinyl)methyl)-3,4-dihydro-2H-1,5-benzodioxepine-7-sulfonamide;
N—((R)-1-benzofuran-2-yl(3-chloro-4-pyridinyl)methyl)-3,4-dihydro-2H-1,5-benzodioxepine-7-sulfonamide;
N—((R)-1-benzofuran-2-yl(2-pyrimidinyl)methyl)-3,4-dihydro-2H-1,5-benzodioxepine-7-sulfonamide;
N—((R)-1-benzofuran-2-yl(3-methoxy-2-pyridinyl)methyl)-3,4-dihydro-2H-1,5-benzodioxepine-7-sulfonamide;
N—((R)-1-benzofuran-2-yl(2-thiophenyl)methyl)-3,4-dihydro-2H-1,5-benzodioxepine-7-sulfonamide;
N—((R)-1-benzofuran-2-yl(3-thiophenyl)methyl)-3,4-dihydro-2H-1,5-benzodioxepine-7-sulfonamide;
N—((R)-1-benzofuran-2-yl(3-methyl-2-thiophenyl)methyl)-3,4-dihydro-2H-1,5-benzodioxepine-7-sulfonamide;
N—((R)-1-benzofuran-2-yl(1,3-thiazol-2-yl)methyl)-3,4-dihydro-2H-1,5-benzodioxepine-7-sulfonamide;
N—((R)-1-benzofuran-2-yl(phenyl)methyl)-3-fluoro-3,4-dihydro-2H-1,5-benzodioxepine-7-sulfonamide;
N—((R)-1-benzothiophen-2-yl(2-methylphenyl)methyl)-3,4-dihydro-2H-1,5-benzodioxepine-7-sulfonamide;
N—((R)-1-benzothiophen-2-yl(2-ethylphenyl)methyl)-3,4-dihydro-2H-1,5-benzodioxepine-7-sulfonamide;
N—((R)-1-benzothiophen-2-yl(2-ethenylphenyl)methyl)-3,4-dihydro-2H-1,5-benzodioxepine-7-sulfonamide;
N—((R)-1-benzothiophen-2-yl(2-ethynylphenyl)methyl)-3,4-dihydro-2H-1,5-benzodioxepine-7-sulfonamide;
N—((R)-1-benzothiophen-2-yl(2-methoxyphenyl)methyl)-3,4-dihydro-2H-1,5-benzodioxepine-7-sulfonamide;
N—((R)-1-benzothiophen-2-yl(2-(methylsulfanyl)phenyl)methyl)-3,4-dihydro-2H-1,5-benzodioxepine-7-sulfonamide;
N—((R)-1-benzothiophen-2-yl(2-chlorophenyl)methyl)-3,4-dihydro-2H-1,5-benzodioxepine-7-sulfonamide;
N—((R)-1-benzothiophen-2-yl(3-methoxy-2-pyridinyl)methyl)-3,4-dihydro-2H-1,5-benzodioxepine-7-sulfonamide;
N—((R)-(3-methyl-1-benzofuran-2-yl)(phenyl)methyl)-3,4-dihydro-2H-1,5-benzodioxepine-7-sulfonamide;
N—((R)-(3-methyl-1-benzofuran-2-yl)(2-methylphenyl)methyl)-3,4-dihydro-2H-1,5-benzodioxepine-7-sulfonamide;
N—((R)-phenyl(thieno[2,3-b]pyridin-2-yl)methyl)-3,4-dihydro-2H-1,5-benzodioxepine-7-sulfonamide;
N—((R)-(2-methoxyphenyl)(thieno[2,3-b]pyridin-2-yl)methyl)-3,4-dihydro-2H-1,5-benzodioxepine-7-sulfonamide;
N—((R)-(2-(methylsulfanyl)phenyl)(thieno[2,3-b]pyridin-2-yl)methyl)-3,4-dihydro-2H-1,5-benzodioxepine-7-sulfonamide;
N—((R)-(3-methoxy-2-pyridinyl)(thieno[2,3-b]pyridin-2-yl)methyl)-3,4-dihydro-2H-1,5-benzodioxepine-7-sulfonamide;
N—((R)-(3-methoxy-4-pyridinyl)(thieno[2,3-b]pyridin-2-yl)methyl)-3,4-dihydro-2H-1,5-benzodioxepine-7-sulfonamide;
N—((R)-1,3-benzothiazol-2-yl(2-methoxyphenyl)methyl)-3,4-dihydro-2H-1,5-benzodioxepine-7-sulfonamide;
N—((R)-1,3-benzothiazol-2-yl(2-(methylsulfanyl)phenyl)methyl)-3,4-dihydro-2H-1,5-benzodioxepine-7-sulfonamide;
N—((R)-1,3-benzothiazol-2-yl(3-methoxy-2-pyridinyl)methyl)-3,4-dihydro-2H-1,5-benzodioxepine-7-sulfonamide;
N—((R)-1,3-benzoxazol-2-yl(phenyl)methyl)-3,4-dihydro-2H-1,5-benzodioxepine-7-sulfonamide;
N—((R)-2-naphthalenyl(phenyl)methyl)-3,4-dihydro-2H-1,5-benzodioxepine-7-sulfonamide;
N—((R)-phenyl(2-quinolinyl)methyl)-3,4-dihydro-2H-1,5-benzodioxepine-7-sulfonamide;
N—((R)-1-benzothiophen-2-yl(phenyl)methyl)-3,4-dihydro-2H-1,5-benzodioxepine-7-sulfonamide;
N—((R)-(5-methoxy-1-benzothiophen-2-yl)(phenyl)methyl)-3,4-dihydro-2H-1,5-benzodioxepine-7-sulfonamide;
N—((R)-1,3-benzothiazol-2-yl(phenyl)methyl)-3,4-dihydro-2H-1,5-benzodioxepine-7-sulfonamide;
N—((R)-phenyl(thieno[2,3-c]pyridin-2-yl)methyl)-3,4-dihydro-2H-1,5-benzodioxepine-7-sulfonamide;
N—((R)-phenyl(thieno[3,2-b]pyridin-2-yl)methyl)-3,4-dihydro-2H-1,5-benzodioxepine-7-sulfonamide;
N—((R)-phenyl(thieno[3,2-c]pyridin-2-yl)methyl)-3,4-dihydro-2H-1,5-benzodioxepine-7-sulfonamide;
N—((R)-(5-hydroxy-1-benzothiophen-2-yl)(phenyl)methyl)-3,4-dihydro-2H-1,5-benzodioxepine-7-sulfonamide;
N—((R)-2-(methylsulfanyl)phenyl)(thieno[2,3-c]pyridin-2-yl)methyl)-3,4-dihydro-2H-1,5-benzodioxepine-7-sulfonamide;
N—((R)-2-(methylsulfanyl)phenyl)([1,3]thiazolo[5,4-b]pyridin-2-yl)methyl)-3,4-dihydro-2H-1,5-benzodioxepine-7-sulfonamide;
N—((R)-2-methoxyphenyl)(thieno[2,3-c]pyridin-2-yl)methyl)-3,4-dihydro-2H-1,5-benzodioxepine-7-sulfonamide;
N—((R)-2-methoxyphenyl)([1,3]thiazolo[5,4-b]pyridin-2-yl)methyl)-3,4-dihydro-2H-1,5-benzodioxepine-7-sulfonamide;
N—((R)-2-chlorophenyl)([1,3]thiazolo[5,4-b]pyridin-2-yl)methyl)-3,4-dihydro-2H-1,5-benzodioxepine-7-sulfonamide;
N—((R)-3-methoxy-2-pyridinyl)([1,3]thiazolo[5,4-b]pyridin-2-yl)methyl)-3,4-dihydro-2H-1,5-benzodioxepine-7-sulfonamide;
N—((R)-phenyl(7-(4-(2,2,2-trifluoro-1-hydroxy-1-methylethyl)-2-pyridinyl)-1-benzothiophen-2-yl)methyl)-3,4-dihydro-2H-1,5-benzodioxepine-7-sulfonamide;
N—((R)-phenyl(7-(2-pyridinyl)-1-benzothiophen-2-yl)methyl)-3,4-dihydro-2H-1,5-benzodioxepine-7-sulfonamide;
N—((R)-7-chloro-1-benzothiophen-2-yl)(phenyl)methyl)-3,4-dihydro-2H-1,5-benzodioxepine-7-sulfonamide;
N—((R)-phenyl(7-phenyl-1-benzothiophen-2-yl)methyl)-3,4-dihydro-2H-1,5-benzodioxepine-7-sulfonamide;
N—((R)-1-benzothiophen-2-yl(phenyl)methyl)-3,4-dimethoxybenzenesulfonamide;
or
N—((R)-1-benzothiophen-2-yl(phenyl)methyl)-2,3-dihydro-1,4-benzodioxine-6-sulfonamide.

74 more elements

Dependencies are inferred from the claim text.

Facts

Application: 14/110,129Filed 4 Apr 2012
Priority: 5 Apr 2011
Published: 5 Jun 2014
Term ends: Not estimatedThe source records don’t support an estimate.

Classification34 codes

A61K 31/506
Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim: not condensed and containing further heterocyclic rings
A61K 31/155
Amines: amidines , e.g. guanidine , isourea , isothiourea
A61K 31/357
Having oxygen as the only ring hetero atom, e.g. fungichromin: having two or more oxygen atoms in the same ring, e.g. crown ethers, guanadrel
A61K 31/381
Having sulfur as a ring hetero atom: having five-membered rings

Family

Application61/472,059Us provisional application · filed 5 Apr 2011
US 2014/0155415 A1This patent

From the US filing history. Foreign family members aren’t listed.

Timeline

Citations

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