Benzo thiadiazine matrix metalloproteinase inhibitors
First Claim
Patent Images
1. A compound of Formula I or a pharmaceutically acceptable salt thereof, wherein:
- n is 0, 1, or 2;
X is O or NH;
R2 is H, C1-C6 alkyl, or C1-C6 substituted alkyl;
R1 and R3 independently are H, acyl, substituted acyl, C1-C6 alkyl, C1-C6 substituted alkyl, C2-C6 alkenyl, C2-C6 substituted alkenyl, C2-C6 alkynyl, C1-C6 substituted alkynyl, (CH2)m aryl, (CH2)m substituted aryl, (CH2)m heteroaryl, (CH2)m substituted heteroaryl, (CH2)m cycloalkyl, or (CH2)m substituted cycloalkyl; and
each m independently is an integer of from 0 to 6, with the proviso that R3 is not (CH2)m biphenyl or (CH2)m substituted biphenyl and R1 and R3 are not both selected from H and C1-C6 alkyl;
wherein substituted aryl and substituted heteroaryl contain from 1 to 3 substituents independently selected from the group consisting of alkyl, alkoxy, thio, thioalkyl, thioalkoxy, (CH2)mN(R4)S(O)2(C1-C6 alkyl), (CH2)mS(O)2NR4R5, S(O)2NR4R5, C(O)NR4R5, N(H)C(O)NR4R5, O—
C(O)NR4R5, halo, hydroxy, —
COOR6, trifluoromethyl, nitro, amino of the formula —
NR4R5, C(O)NR4R5, S(O)C1-C6 alkyl, S(O)2C1-C6 alkyl, 5-membered heteroaryl, N(R5)C(O)O(C1-C6 alkyl), T(CH2)pQR4, T(CH2)pCO2R4, and phenyl, substituted alkyl, substituted alkenyl, substituted alkoxy, and substituted alkynyl contain from 1 to 3 substituents independently selected from NR4R5, phenyl, substituted phenyl, (CH2)m—
C(O) phenyl, (CH2)mC(O) substituted phenyl, (CH2)m—
S(O)0-2 phenyl, (CH2)mS(O)0-2 substituted phenyl, (CH2)m—
C(O) heteroaryl, (CH2)mC(O) substituted heteroaryl, (CH2)m—
S(O)0-2 heteroaryl, (CH2)m—
S(O)0-2 substituted heteroaryl, (CH2)m cycloalkyl, heterocycle, thio C1-C6 alkyl, C1-C6 alkoxy, hydroxy, acyl, carboxy, alkanoyl, C1-C6 alkoxycarbonyl, halo, nitro, nitrile, cycloalkyl, and a 5- or 6-membered carbocyclic ring or heterocyclic ring having 1 or 2 heteroatoms selected from nitrogen, substituted nitrogen, oxygen, and sulfur, substituted cycloalkyl contain a substituent hydroxy or keto;
p is 1 to 6, T is O, S, SO, SO2, NR4, N(O)R4, NR4R6Y, or CR4R5, Q is O, S, SO, SO2, NR5, N(O)R5, or NR5R6Y, Y is a counter ion of halo, R6 is H, C1-C6 alkyl, or substituted C1-C6 alkyl, R4 and R5 independently are hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, acyl, (CH2)m aryl, (CH2)m heteroaryl, (CH2)m cycloalkyl, wherein these groups may be unsubstituted or substituted as described herein, or R4 and R5 are taken together with the nitrogen atom to which they are attached to form a 3- to 7-membered ring containing carbon atoms, the nitrogen atom bearing R4 and R5, and optionally 1 or 2 heteroatoms selected from O, S, NH, and NR2, wherein R2 is as defined above, the ring optionally may be substituted with oxo (“
═
O”
) on a carbon atom, heterocycle is selected from oxiranyl, pyrrolidinyl, piperidyl, tetrahydropyranyl, and morpholinyl, acyl is C(O)—
(C1-C6 alkyl), C(O)-phenyl, or C(O)-naphthyl, aryl is phenyl or naphthyl, and heteroaryl is 5-membered heteroaryl selected from furanyl, pyrrolyl, pyrazolyl, imidazolyl, thiazolyl, thienyl, oxazolyl, isoxazolyl, isothiazolyl, and tetrazolyl, 6-membered heteroaryl selected from pyridyl, or 9-membered heteroaryl selected from benzothienyl, indolyl, benzotriazolyl, indazolyl, benzofuranyl, benzo[1,2,5]oxadiazolyl, (2,1,3)benzothiadiazolyl, and benzisoxazolyl.
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Abstract
Selective MMP-13 inhibitors are benzo thiadiazines of the Formula
or a pharmaceutically acceptable salt thereof, wherein R2 is hydrogen or alkyl; R1 and R3 include hydrogen, alkyl, and aryl, with the proviso that R3 is not (CH2)m biphenyl or (CH2)m substituted biphenyl; X is O or NH, n is 0, 1, or 2. The compounds of Formula I, or a pharmaceutically acceptable salt thereof, is useful for treating diseases mediated by an MMP-13 enzyme, including diseases selected from osteoarthritis, rheumatoid arthritis, cancer, inflammation, and heart failure.
57 Citations
16 Claims
-
1. A compound of Formula I
or a pharmaceutically acceptable salt thereof, wherein: -
n is 0, 1, or 2;
X is O or NH;
R2 is H, C1-C6 alkyl, or C1-C6 substituted alkyl;
R1 and R3 independently are H, acyl, substituted acyl, C1-C6 alkyl, C1-C6 substituted alkyl, C2-C6 alkenyl, C2-C6 substituted alkenyl, C2-C6 alkynyl, C1-C6 substituted alkynyl, (CH2)m aryl, (CH2)m substituted aryl, (CH2)m heteroaryl, (CH2)m substituted heteroaryl, (CH2)m cycloalkyl, or (CH2)m substituted cycloalkyl; and
each m independently is an integer of from 0 to 6, with the proviso that R3 is not (CH2)m biphenyl or (CH2)m substituted biphenyl and R1 and R3 are not both selected from H and C1-C6 alkyl;
wherein substituted aryl and substituted heteroaryl contain from 1 to 3 substituents independently selected from the group consisting of alkyl, alkoxy, thio, thioalkyl, thioalkoxy, (CH2)mN(R4)S(O)2(C1-C6 alkyl), (CH2)mS(O)2NR4R5, S(O)2NR4R5, C(O)NR4R5, N(H)C(O)NR4R5, O—
C(O)NR4R5, halo, hydroxy, —
COOR6, trifluoromethyl, nitro, amino of the formula —
NR4R5, C(O)NR4R5, S(O)C1-C6 alkyl, S(O)2C1-C6 alkyl, 5-membered heteroaryl, N(R5)C(O)O(C1-C6 alkyl), T(CH2)pQR4, T(CH2)pCO2R4, and phenyl,substituted alkyl, substituted alkenyl, substituted alkoxy, and substituted alkynyl contain from 1 to 3 substituents independently selected from NR4R5, phenyl, substituted phenyl, (CH2)m—
C(O) phenyl, (CH2)mC(O) substituted phenyl, (CH2)m—
S(O)0-2 phenyl, (CH2)mS(O)0-2 substituted phenyl, (CH2)m—
C(O) heteroaryl, (CH2)mC(O) substituted heteroaryl, (CH2)m—
S(O)0-2 heteroaryl, (CH2)m—
S(O)0-2 substituted heteroaryl, (CH2)m cycloalkyl, heterocycle, thio C1-C6 alkyl, C1-C6 alkoxy, hydroxy, acyl, carboxy, alkanoyl, C1-C6 alkoxycarbonyl, halo, nitro, nitrile, cycloalkyl, and a 5- or 6-membered carbocyclic ring or heterocyclic ring having 1 or 2 heteroatoms selected from nitrogen, substituted nitrogen, oxygen, and sulfur,substituted cycloalkyl contain a substituent hydroxy or keto;
p is 1 to 6, T is O, S, SO, SO2, NR4, N(O)R4, NR4R6Y, or CR4R5, Q is O, S, SO, SO2, NR5, N(O)R5, or NR5R6Y, Y is a counter ion of halo, R6 is H, C1-C6 alkyl, or substituted C1-C6 alkyl, R4 and R5 independently are hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, acyl, (CH2)m aryl, (CH2)m heteroaryl, (CH2)m cycloalkyl, wherein these groups may be unsubstituted or substituted as described herein, or R4 and R5 are taken together with the nitrogen atom to which they are attached to form a 3- to 7-membered ring containing carbon atoms, the nitrogen atom bearing R4 and R5, and optionally 1 or 2 heteroatoms selected from O, S, NH, and NR2, wherein R2 is as defined above, the ring optionally may be substituted with oxo (“
═
O”
) on a carbon atom,heterocycle is selected from oxiranyl, pyrrolidinyl, piperidyl, tetrahydropyranyl, and morpholinyl, acyl is C(O)—
(C1-C6 alkyl), C(O)-phenyl, or C(O)-naphthyl,aryl is phenyl or naphthyl, and heteroaryl is 5-membered heteroaryl selected from furanyl, pyrrolyl, pyrazolyl, imidazolyl, thiazolyl, thienyl, oxazolyl, isoxazolyl, isothiazolyl, and tetrazolyl, 6-membered heteroaryl selected from pyridyl, or 9-membered heteroaryl selected from benzothienyl, indolyl, benzotriazolyl, indazolyl, benzofuranyl, benzo[1,2,5]oxadiazolyl, (2,1,3)benzothiadiazolyl, and benzisoxazolyl. - View Dependent Claims (3, 5)
-
-
2. A compound of Formula II
or a pharmaceutically acceptable salt thereof, wherein: -
X is O or NH;
R2 is H, or C1-C6 alkyl, or C1-C6 substituted alkyl;
R1 and R3 independently are H, acyl, substituted acyl, C1-C6 alkyl, C1-C6 substituted alkyl, C2-C6 alkenyl, C2-C6 substituted alkenyl, C2-C6 alkynyl, C1-C6 substituted alkynyl, (CH2)m aryl, (CH2)m substituted aryl, (CH2)m heteroaryl, (CH2)m substituted heteroaryl, (CH2)m cycloalkyl, or (CH2)m substituted cycloalkyl; and
each m independently is an integer of from 0 to 6, with the proviso that R3 is not (CH2)m biphenyl or (CH2)m substituted biphenyl and R1 and R3 are not both selected from H and C1-C6 alkyl;
wherein substituted aryl and substituted heteroaryl contain from 1 to 3 substituents independently selected from the group consisting of alkyl, alkoxy, thio, thioalkyl, thioalkoxy, (CH2)mN(R4)S(O)2(C1-C6 alkyl), (CH2)mS(O)2NR4R5, S(O)2NR4R5, C(O)NR4R5, N(H)C(O)NR4R5, O—
C(O)NR4R5, halo, hydroxy, —
COOR6, trifluoromethyl, nitro, amino of the formula —
NR4R5, C(O)NR4R5, S(O)C1-C6 alkyl, S(O)2C1-C6 alkyl, 5-membered heteroaryl, N(R5)C(O)O(C1-C6 alkyl), T(CH2)pQR4, T(CH2)pCO2R4, and phenyl,substituted alkyl, substituted alkenyl, substituted alkoxy, and substituted alkynyl contain from 1 to 3 substituents independently selected from NR4R5, phenyl, substituted phenyl, (CH2)m—
C(O) phenyl, (CH2)mC(O) substituted phenyl, (CH2)m—
S(O)0-2 phenyl, (CH2)mS(O)0-2 substituted phenyl, (CH2)m—
C(O) heteroaryl, (CH2)mC(O) substituted heteroaryl, (CH2)m—
S(O)0-2 heteroaryl, (CH2)m—
S(O)0-2 substituted heteroaryl, (CH2)m cycloalkyl, heterocycle, thio C1-C6 alkyl, C1-C6 alkoxy, hydroxy, acyl, carboxy, alkanoyl, C1-C6 alkoxycarbonyl, halo, nitro, nitrile, cycloalkyl, and a 5- or 6-membered carbocyclic ring or heterocyclic ring having 1 or 2 heteroatoms selected from nitrogen, substituted nitrogen, oxygen, and sulfur,substituted cycloalkyl contain a substituent hydroxy or keto;
p is 1 to 6, T is O, S, SO, SO2, NR4, N(O)R4, NR4R6Y, or CR4R5, Q is O, S, SO, SO2, NR5, N(O)R5, or NR5R6Y, Y is a counter ion of halo, R6 is H, C1-C6 alkyl, or substituted C1-C6 alkyl, R4 and R5 independently are hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, acyl, (CH2)m aryl, (CH2)m heteroaryl, (CH2)m cycloalkyl, wherein these groups may be unsubstituted or substituted as described herein, or R4 and R5 are taken together with the nitrogen atom to which they are attached to form a 3- to 7-membered ring containing carbon atoms, the nitrogen atom bearing R4 and R5, and optionally 1 or 2 heteroatoms selected from O, S, NH, and NR2, wherein R2 is as defined above, the ring optionally may be substituted with oxo (“
═
O”
) on a carbon atom,heterocycle is selected from oxiranyl, pyrrolidinyl, piperidyl, tetrahydropyranyl, and morpholinyl, acyl is C(O)—
(C1-C6 alkyl), C(O)-phenyl, or C(O)-naphthyl,aryl is phenyl or naphthyl, and heteroaryl is 5-membered heteroaryl selected from furanyl, pyrrolyl, pyrazolyl, imidazolyl, thiazolyl, thienyl, oxazolyl, isoxazolyl, isothiazolyl, and tetrazolyl, 6-membered heteroaryl selected from pyridyl, or 9-membered heteroaryl selected from benzothienyl, indolyl, benzotriazolyl, indazolyl, benzofuranyl, benzo[1,2,5]oxadiazolyl, (2,1,3)benzothiadiazolyl, and benzisoxazolyl. - View Dependent Claims (4)
-
-
6. A compound of Formula I
or a pharmaceutically acceptable salt thereof, wherein: -
n is 0, 1, or 2;
X is O or NH;
R2 is H, C1-C6 alkyl, or C1-C6 substituted alkyl;
R1 and R3 independently are H, C1-C6 alkyl, C1-C6 substituted alkyl, C2-C6 alkenyl or C2-C6 substituted alkenyl, C2-C6 alkynyl or C1-C6 substituted alkynyl, (CH2)m aryl, (CH2)m heteroaryl, or (CH2)m cycloalkyl; and
m is an integer from 0 to 6;
wherein and R1 and R3 are not both selected from H and C1-C6 alkyl;
wherein substituted aryl and substituted heteroaryl contain from 1 to 3 substituents independently selected from the group consisting of alkyl, alkoxy, thio, thioalkyl, thioalkoxy, (CH2)mN(R4)S(O)2(C1-C6 alkyl), (CH2)mS(O)2NR4R5, S(O)2NR4R5, C(O)NR4R5, N(H)C(O)NR4R5, O—
C(O)NR4R5, halo, hydroxy, —
COOR6, trifluoromethyl, nitro, amino of the formula —
NR4R5, C(O)NR4R5, S(O)C1-C6 alkyl, S(O)2C1-C6 alkyl, 5-membered heteroaryl, N(R5)C(O)O(C1-C6 alkyl), T(CH2)pQR4, T(CH2)pCO2R4, and phenyl,substituted alkyl, substituted alkenyl, substituted alkoxy, and substituted alkynyl contain from 1 to 3 substituents independently selected from NR4R5, phenyl, substituted phenyl, (CH2)m—
C(O) phenyl, (CH2)mC(O) substituted phenyl, (CH2)m—
S(O)0-2 phenyl, (CH2)mS(O)0-2 substituted phenyl, (CH2)m—
C(O) heteroaryl, (CH2)mC(O) substituted heteroaryl, (CH2)m—
S(O)0-2 heteroaryl, (CH2)m—
S(O)0-2 substituted heteroaryl, (CH2)m cycloalkyl, heterocycle, thio C1-C6 alkyl, C1-C6 alkoxy, hydroxy, acyl, carboxy, alkanoyl, C1-C6 alkoxycarbonyl, halo, nitro, nitrile, cycloalkyl, and a 5- or 6-membered carbocyclic ring or heterocyclic ring having 1 or 2 heteroatoms selected from nitrogen, substituted nitrogen, oxygen, and sulfur,substituted cycloalkyl contain a substituent hydroxy or keto;
p is 1 to 6, T is O, S, SO, SO2, NR4, N(O)R4, NR4R6Y, or CR4R5, Q is O, S, SO, SO2, NR5, N(O)R5, or NR5R6Y, Y is a counter ion of halo, R6 is H, C1-C6 alkyl, or substituted C1-C6 alkyl, R4 and R5 independently are hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, acyl, (CH2)m aryl, (CH2)m heteroaryl, (CH2)m cycloalkyl, wherein these groups may be unsubstituted or substituted as described herein, or R4 and R5 are taken together with the nitrogen atom to which they are attached to form a 3- to 7-membered ring containing carbon atoms, the nitrogen atom bearing R4 and R5, and optionally 1 or 2 heteroatoms selected from O, S, NH, and NR2, wherein R2 is as defined above, the ring optionally may be substituted with oxo (“
═
O”
) on a carbon atom,heterocycle is selected from oxiranyl, pyrrolidinyl, piperidyl, tetrahydropyranyl, and morpholinyl, acyl is C(O)—
(C1-C6 alkyl), C(O)-phenyl, or C(O)-naphthyl,aryl is phenyl or naphthyl, and heteroaryl is 5-membered heteroaryl selected from furanyl, pyrrolyl, pyrazolyl, imidazolyl, thiazolyl, thienyl, oxazolyl, isoxazolyl, isothiazolyl, and tetrazolyl, 6-membered heteroaryl selected from pyridyl, or 9-membered heteroaryl selected from benzothienyl, indolyl, benzotriazolyl, indazolyl, benzofuranyl, benzo[1,2,5]oxadiazolyl, (2,1,3)benzothiadiazolyl, and benzisoxazolyl. - View Dependent Claims (9, 11)
-
-
7. A compound of Formula II
or a pharmaceutically acceptable salt thereof, wherein: -
X is O or NH;
R2 is H, or C1-C6 alkyl, or C1-C6 substituted alkyl;
R1 and R3 independently are H, C1-C6 alkyl, C1-C6 substituted alkyl, C2-C6 alkenyl or C2-C6 substituted alkenyl, C2-C6 alkynyl or C1-C6 substituted alkynyl, (CH2)m aryl, (CH2)m heteroaryl, or (CH2)m cycloalkyl; and
m is an integer from 0 to 6;
wherein and R1 and R3 are not both selected from H and C1-C6 alkyl;
wherein substituted aryl and substituted heteroaryl contain from 1 to 3 substituents independently selected from the group consisting of alkyl, alkoxy, thio, thioalkyl, thioalkoxy, (CH2)mN(R4)S(O)2(C1-C6 alkyl), (CH2)mS(O)2NR4R5, S(O)2NR4R5, C(O)NR4R5, N(H)C(O)NR4R5, O—
C(O)NR4R5, halo, hydroxy, —
COOR6, trifluoromethyl, nitro, amino of the formula —
NR4R5, C(O)NR4R5, S(O)C1-C6 alkyl, S(O)2C1-C6 alkyl, 5-membered heteroaryl, N(R5)C(O)O(C1-C6 alkyl), T(CH2)pQR4, T(CH2)pCO2R4, and phenyl,substituted alkyl, substituted alkenyl, substituted alkoxy, and substituted alkynyl contain from 1 to 3 substituents independently selected from NR4R5, phenyl, substituted phenyl, (CH2)m—
C(O) phenyl, (CH2)mC(O) substituted phenyl, (CH2)m—
S(O)0-2 phenyl, (CH2)mS(O)0-2 substituted phenyl, (CH2)m—
C(O) heteroaryl, (CH2)mC(O) substituted heteroaryl, (CH2)m—
S(O)0-2 heteroaryl, (CH2)m—
S(O)0-2 substituted heteroaryl, (CH2)m cycloalkyl, heterocycle, thio C1-C6 alkyl, C1-C6 alkoxy, hydroxy, acyl, carboxy, alkanoyl, C1-C6 alkoxycarbonyl, halo, nitro, nitrile, cycloalkyl, and a 5- or 6-membered carbocyclic ring or heterocyclic ring having 1 or 2 heteroatoms selected from nitrogen, substituted nitrogen, oxygen, and sulfur,substituted cycloalkyl contain a substituent hydroxy or keto;
p is 1 to 6, T is O, S, SO, SO2, NR4, N(O)R4, NR4R6Y, or CR4R5, Q is O, S, SO, SO2, NR5, N(O)R5, or NR5R6Y, Y is a counter ion of halo, R6 is H, C1-C6 alkyl, or substituted C1-C6 alkyl, R4 and R5 independently are hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, acyl, (CH2)m aryl, (CH2)m heteroaryl, (CH2)m cycloalkyl, wherein these groups may be unsubstituted or substituted as described herein, or R4 and R5 are taken together with the nitrogen atom to which they are attached to form a 3- to 7-membered ring containing carbon atoms, the nitrogen atom bearing R4 and R5, and optionally 1 or 2 heteroatoms selected from O, S, NH, and NR2, wherein R2 is as defined above, the ring optionally may be substituted with oxo (“
═
O”
) on a carbon atom,heterocycle is selected from oxiranyl, pyrrolidinyl, piperidyl, tetrahydropyranyl, and morpholinyl, acyl is C(O)—
(C1-C6 alkyl), C(O)-phenyl, or C(O)-naphthyl,aryl is phenyl or naphthyl, and heteroaryl is 5-membered heteroaryl selected from furanyl, pyrrolyl, pyrazolyl, imidazolyl, thiazolyl, thienyl, oxazolyl, isoxazolyl, isothiazolyl, and tetrazolyl, 6-membered heteroaryl selected from pyridyl, or 9-membered heteroaryl selected from benzothienyl, indolyl, benzotriazolyl, indazolyl, benzofuranyl, benzo[1,2,5]oxadiazolyl, (2,1,3)benzothiadiazolyl, and benzisoxazolyl. - View Dependent Claims (10)
-
-
8. A compound selected from the group consisting of:
-
2-Benzyl-4-methyl-1,1,3-trioxo-1,2,3,4-tetrahydro-1l6-benzo[1,2,4]thiadiazine-7-carboxylic acid benzyl ester;
2-Benzyl-4-methyl-1,1,3-trioxo-1,2,3,4-tetrahydro-1l6-benzo[1,2,4]thiadiazine-7-carboxylic acid benzylamide; and
2-Benzyl-4-methyl-1,1,3-trioxo-1,2,3,4-tetrahydro-1l6-benzo[1,2,4]thiadiazine-7-carboxylic acid (pyridin-4-ylmethyl)-amide.
-
-
12. A compound selected from the group consisting of:
-
2-Benzyl-4-methyl-1,1,3-trioxo-1,2,3,4-tetrahydro-1l6-benzo[1,2,4]thiadiazine-7-carboxylic acid 3-methoxy-benzylamide;
4-(7-Benzylcarbamoyl-4-methyl-1,1,3-trioxo-3,4-dihydro-1H-1l6-benzo[1,2,4]thiadiazin-2-ylmethyl)-benzoic acid;
4-[7-(4-Methoxy-benzylcarbamoyl)-4-methyl-1,1,3-trioxo-3,4-dihydro-1H-1l6-benzo[1,2,4]thiadiazin-2-ylmethyl)-benzoic acid;
4-[7-(3-Methoxy-benzylcarbamoyl)-4-methyl-1,1,3-trioxo-3,4-dihydro-1H-1l6-benzo[1,2,4]thiadiazin-2-ylmethyl)-benzoic acid;
{4-[7-(4-Methoxy-benzylcarbamoyl)-4-methyl-1,1,3-trioxo-3,4-dihydro-1H-1l6-benzo[1,2,4]thiadiazin-2-ylmethyl)-phenyl}-acetic acid; and
4-Methyl-2-(4-methylsulfamoyl-benzyl)-1,1,3-trioxo-1,2,3,4-tetrahydro-1l6-benzo[1,2,4]thiadiazine-7-carboxylic acid 4-methoxy-benzylamide.
-
-
13. A compound selected from the group consisting of:
-
2-Benzyl-4-methyl-1,1,3-trioxo-1,2,3,4-tetrahydro-1l6-benzo[1,2,4]thiadiazine-7-carboxylic acid (1H-indol-5-ylmethyl)-amide;
2-Benzyl-4-methyl-1,1,3-trioxo-1,2,3,4-tetrahydro-1l6-benzo[1,2,4]thiadiazine-7-carboxylic acid (1H-indol-5-ylmethyl)-amide;
2-Benzyl-4-methyl-1,1,3-trioxo-1,2,3,4-tetrahydro-1l6-benzo[1,2,4]thiadiazine-7-carboxylic acid 4-fluoro-benzylamide;
4-Methyl-2-(4-nitro-benzyl)-1,1,3-trioxo-1,2,3,4-tetrahydro-1l6-benzo[1,2,4]thiadiazine-7-carboxylic acid 4-methoxy-benzylamide;
4-Methyl-2-[4-(morpholine-4-sulfonyl)-benzyl]-1,1,3-trioxo-1,2,3,4-tetrahydro-1l6-benzo[1,2,4]thiadiazine-7-carboxylic acid 4-methoxy-benzylamide;
4-[7-(4-Fluoro-benzylcarbamoyl)-4-methyl-1,1,3-trioxo-3,4-dihydro-1H-1l6-benzo[1,2,4]thiadiazin-2-ylmethyl]-benzoic acid methyl ester;
2-Benzyl-4-methyl-1,1,3-trioxo-1,2,3,4-tetrahydro-1l6-benzo[1,2,4]thiadiazine-7-carboxylic acid (2-methoxy-pyridin-4-ylmethyl)-amide;
4-Methyl-2-naphthalen-2-ylmethyl-1,1,3-trioxo-1,2,3,4-tetrahydro-1l6-benzo[1,2,4]thiadiazine-7-carboxylic acid 4-methoxy-benzylamide;
2-Benzyl-4-methyl-1,1,3-trioxo-1,2,3,4-tetrahydro-1l6-benzo[1,2,4]thiadiazine-7-carboxylic acid (2,1,3-benzothiadiazol-5-ylmethyl)-amide;
4-[7-(4-Fluoro-benzylcarbamoyl)-4-methyl-1,1,3-trioxo-3,4-dihydro-1H-1l6-benzo[1,2,4]thiadiazin-2-ylmethyl]-benzoic acid;
4-Methyl-1,1,3-trioxo-2-[4-(piperidine-1-carbonyl)-benzyl]-1,2,3,4-tetrahydro-1l6-benzo[1,2,4]thiadiazine-7-carboxylic acid 4-methoxy-benzylamide;
2-{4-[7-(4-Methoxy-benzylcarbamoyl)-4-methyl-1,1,3-trioxo-3,4-dihydro-1H-1l6-benzo[1,2,4]thiadiazin-2-ylmethyl]-benzoylamino}-3-methyl-butyric acid;
2-(4-Cyano-benzyl)-4-methyl-1,1,3-trioxo-1,2,3,4-tetrahydro-1l6-benzo[1,2,4]thiadiazine-7-carboxylic acid 4-methoxy-benzylamide;
4-Methyl-1,1,3-trioxo-2-[4-(2H-tetrazol-5-yl)-benzyl]-1,2,3,4-tetrahydro-1λ
6-benzo[1,2,4]thiadiazine-7-carboxylic acid 4-methoxy-benzylamide; and
2-Benzo[1,2,5]oxadiazol-5-ylmethyl-4-methyl-1,1,3-trioxo-1,2,3,4-tetrahydro-1l6-benzo[1,2,4]thiadiazine-7-carboxylic acid 4-methoxy-benzylamide.
-
-
14. A compound selected from the group consisting of:
-
2-Benzyl-4-methyl-1,1,3-trioxo-1,2,3,4-tetrahydro-1l6-benzo[1,2,4]thiadiazine-7-carboxylic acid 4-methoxy-benzylamide;
4-(7-Benzylcarbamoyl-4-methyl-1,1,3-trioxo-3,4-dihydro-1H-1l6-benzo[1,2,4]thiadiazin-2-ylmethyl)-benzoic acid tert-butyl ester;
2-(4-Methanesulfonyl-benzyl)-4-methyl-1,1,3-trioxo-1,2,3,4-tetrahydro-1l6-benzo[1,2,4]thiadiazine-7-carboxylic acid benzylamide; and
2-(4-Methanesulfonyl-benzyl)-4-methyl-1,1,3-trioxo-1,2,3,4-tetrahydro-1l6-benzo[1,2,4]thiadiazine-7-carboxylic acid 4-methoxy-benzylamide.
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15. A compound selected from the group consisting of:
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2-Benzyl-4-methyl-1,1,3-trioxo-1,2,3,4-tetrahydro-1l6-benzo[1,2,4]thiadiazine-7-carboxylic acid 4-(2-tert-butylsulfamoyl-ethyl)-benzylamide;
2-Benzyl-4-methyl-1,1,3-trioxo-1,2,3,4-tetrahydro-1l6-benzo[1,2,4]thiadiazine-7-carboxylic acid (1H-indol-2-ylmethyl)-amide;
2-Benzyl-4-methyl-1,1,3-trioxo-1,2,3,4-tetrahydro-1l6-benzo[1,2,4]thiadiazine-7-carboxylic acid 4-(2-sulfamoyl-ethyl)-benzylamide;
4-[7-(4-Methoxy-benzylcarbamoyl)-4-methyl-1,1,3-trioxo-3,4-dihydro-1H-1l6-benzo[1,2,4]thiadiazin-2-ylmethyl]-benzoic acid tert-butyl ester;
2-Biphenyl-4-ylmethyl-4-methyl-1,1,3-trioxo-1,2,3,4-tetrahydro-1l6-benzo[1,2,4]thiadiazine-7-carboxylic acid 4-methoxy-benzylamide;
4-[7-(4-Methoxy-benzylcarbamoyl)-4-methyl-1,1,3-trioxo-3,4-dihydro-1H-1l6-benzo[1,2,4]thiadiazin-2-ylmethyl]-benzoic acid 2-dimethylamino-ethyl ester hydrochloride;
2-(4-Amino-benzyl)-4-methyl-1,1,3-trioxo-1,2,3,4-tetrahydro-1λ
6-benzo[1,2,4]thiadiazine-7-carboxylic acid 4-methoxy-benzylamide;
4-Methyl-1,1,3-trioxo-2-pent-2-ynyl-1,2,3,4-tetrahydro-1l6-benzo[1,2,4]thiadiazine-7-carboxylic acid 4-methoxy-benzylamide;
4-Methyl-1,1,3-trioxo-2-(1-phenyl-ethyl)-1,2,3,4-tetrahydro-1l6-benzo[1,2,4]thiadiazine-7-carboxylic acid 4-methoxy-benzylamide; and
2-(5-Cyano-pentyl)-4-methyl-1,1,3-trioxo-1,2,3,4-tetrahydro-1l6-benzo[1,2,4]thiadiazine-7-carboxylic acid 4-methoxy-benzylamide.
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16. A compound selected from the group consisting of:
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2-(E)-But-2-enyl-4-methyl-1,1,3-trioxo-1,2,3,4-tetrahydro-1l6-benzo[1,2,4]thiadiazine-7-carboxylic acid 4-methoxy-benzylamide;
4-Methyl-1,1,3-trioxo-2-(E)-pent-2-enyl-1,2,3,4-tetrahydro-1l6-benzo[1,2,4]thiadiazine-7-carboxylic acid 4-methoxy-benzylamide;
4-Methyl-2-(2-methyl-allyl)-1,1,3-trioxo-1,2,3,4-tetrahydro-1l6-benzo[1,2,4]thiadiazine-7-carboxylic acid 4-methoxy-benzylamide;
4-Methyl-2-(3-methyl-but-2-enyl)-1,1,3-trioxo-1,2,3,4-tetrahydro-1l6-benzo[1,2,4]thiadiazine-7-carboxylic acid 4-methoxy-benzylamide;
4-Methyl-1,1,3-trioxo-2-[2-(toluene-4-sulfonyl)-ethyl]-1,2,3,4-tetrahydro-1l6-benzo[1,2,4]thiadiazine-7-carboxylic acid 4-methoxy-benzylamide;
2-[3-(4-Fluoro-phenyl)-3-oxo-propyl]-4-methyl-1,1,3-trioxo-1,2,3,4-tetrahydro-1l6-benzo[1,2,4]thiadiazine-7-carboxylic acid 4-methoxy-benzylamide;
4-Methyl-1,1,3-trioxo-2-{2-[(1-phenyl-methanoyl)-amino]-ethyl}-1,2,3,4-tetrahydro-1l6-benzo[1,2,4]thiadiazine-7-carboxylic acid 4-methoxy-benzylamide;
{5-[7-(4-Methoxy-benzylcarbamoyl)-4-methyl-1,1,3-trioxo-3,4-dihydro-1H-1l6-benzo[1,2,4}thiadiazin-2-ylmethyl]-isoxazol-3-yl}-carbamic acid methyl ester; and
4-Methyl-1,1,3-trioxo-2-thiazol-4-ylmethyl-1,2,3,4-tetrahydro-1l6-benzo[1,2,4]thiadiazine-7-carboxylic acid 4-methoxy-benzylamide.
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Specification
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Current AssigneeWarner-Lambert Company (Pfizer Inc.)
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Original AssigneeWarner-Lambert Company (Pfizer Inc.)
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InventorsWilson, Michael William, Picard, Joseph Armand
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Primary Examiner(s)Ford, John M.
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Application NumberUS10/074,646Publication NumberTime in Patent Office657 DaysField of Search544/12, 544/13, 540/599, 514/223.2, 514/222.8, 514/217.05, 514/211.15, 514/211.08, 514/212.08US Class Current514/223.2CPC Class CodesA61P 1/02 Stomatological preparations...A61P 1/04 for ulcers, gastritis or re...A61P 19/02 for joint disorders, e.g. a...A61P 19/10 for osteoporosisA61P 25/00 Drugs for disorders of the ...A61P 29/00 Non-central analgesic, anti...A61P 35/00 Antineoplastic agentsA61P 35/04 specific for metastasisA61P 43/00 Drugs for specific purposes...A61P 9/02 Non-specific cardiovascular...A61P 9/04 Inotropic agents, i.e. stim...A61P 9/10 for treating ischaemic or a...C07D 285/22 condensed with one six-memb...C07D 285/24 with oxygen atoms directly ...C07D 417/12 linked by a chain containin...
