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US 2025/0064761 A1Published application
Substituted benzamides and their use in therapy
AssigneePharmacyl AB
InventorsAnders BJÖRK, Gunnar HEDLUND
Life of this patent
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Abstract
A compound of formula (I) or a pharmaceutically acceptable salt or solvate thereof, and a pharmaceutical composition comprising the compound. The compound is useful for the treatment a disease resulting from pathologic inflammation, such as inflammatory bowel disease, psoriasis or rheumatoid arthritis.
Claims18
A method for the treatment of a disease resulting from pathologic inflammation, comprising administering a therapeutically effective amount of a compound of formula (I)
- or a pharmaceutically acceptable salt or solvate thereof;
- wherein
- R1 is selected from C1-C6 alkyl and C3-C6 cycloalkyl;
- R2 is selected from H and C1-C3 alkyl;
- R3, R4, R5, and R6 are independently selected from hydrogen, C1-C3 alkyl, C1-C3 alkoxy, C1-C3 alkylthio, fluoro, chloro, bromo, phenyl and benzyl, wherein any alkyl is optionally substituted with one or more fluoro;
- R7 is selected from hydrogen and C1-C3 alkyl;
- R8 and R9 are independently selected from C1-C6 alkyl, or
- R8 and R9 together with the nitrogen atom to which they are both attached form a moiety of
- formula (II)
- r is 0 or 1;
- R10 is selected from C1-C3 alkyl and C3-C4 cycloalkyl;
- said alkyl and cycloalkyl optionally being substituted with hydroxy, halogen, cyano, COOR12, or NHR13,
- Q is selected from CHR11, NR11 and O;
- R11 is selected from hydrogen, C1-C3 alkyl and C3-C4 cycloalkyl;
- said alkyl and cycloalkyl optionally being substituted with hydroxy, halogen, cyano, COOR12, or NHR13;
- R12 and R13 are independently selected from hydrogen, C1-C3 alkyl and C3-C4 cycloalkyl;
- p is 1, 2, or 3 when Q is CHR11;
- and
- p is 2 or 3 when Q is selected from NR11 and O;
- to a mammal in need of such treatment, provided that the disease is not an acute or chronic respiratory tract inflammation associated with eosinophil infiltration.
17 more elements
A compound of formula (I)
- or a pharmaceutically acceptable salt or solvate thereof;
- wherein
- R1 is selected from C1-C6 alkyl and C3-C6 cycloalkyl;
- R2 is selected from H and C1-C3 alkyl;
- R3, R4, R5, and R6 are independently selected from hydrogen, C1-C3 alkyl, C1-C3 alkoxy, C1-C3 alkylthio, fluoro, chloro, bromo, phenyl and benzyl, wherein any alkyl is optionally substituted with one or more fluoro;
- R7 is selected from hydrogen and C1-C3 alkyl;
- R8 and R9 are independently selected from C1-C6 alkyl, or
- R8 and R9 together with the nitrogen atom to which they are both attached form a moiety of
- formula (II)
- r is 0 or 1;
- R10 is selected from C1-C3 alkyl and C3-C4 cycloalkyl;
- said alkyl and cycloalkyl optionally being substituted with hydroxy, halogen, cyano, COOR12, or NHR13;
- Q is selected from CHR11, NR11 and O;
- R11 is selected from hydrogen, C1-C3 alkyl and C3-C4 cycloalkyl;
- said alkyl and cycloalkyl optionally being substituted with a hydroxy, halogen, cyano, COOR12, or NHR13;
- R12 and R13 are independently selected from hydrogen, C1-C3 alkyl and C3-C4 cycloalkyl;
- p is 1, 2, or 3 when Q is CHR11;
- and
- p is 2 or 3 when Q is selected from NR11 and O;
- provided that the compound is not:
- N-[2-(diethylamino)ethyl]-4-(propanoylamino)benzamide,
- 4-acetamido-3-chloro-N-[2-(diethylamino)ethyl]benzamide,
- 4-acetamido-N-[2-(diethylamino)ethyl]-2-methoxybenzamide,
- 4-acetamido-5-chloro-N-[2-(diethylamino)ethyl]-2-methoxybenzamide,
- N-[2-(diethylamino)ethyl]-2-methoxy-4-(propanoylamino)benzamide,
- N-[2-[di(propan-2-yl)amino]ethyl]-2-ethoxy-4-(propanoylamino)benzamide,
- N-[2-(diethylamino)ethyl]-2-ethoxy-4-(propanoylamino)benzamide,
- 4-[acetyl(methyl)amino]-N-[2-(diethylamino)ethyl]benzamide,
- 4-(butanoylamino)-N-[2-(diethylamino)ethyl]benzamide,
- N-[2-(diethylamino)ethyl]-4-(pentanoylamino)benzamide,
- N-[2-(diethylamino)ethyl]-2-methoxy-4-(4-methylpentanoylamino)benzamide,
- 4-acetamido-N-[2-(diethylamino)ethyl]benzamide,
- 4-propanoylamino-2-methoxy-N-(2-morpholin-4-yl-ethyl)benzamide,
- 4-acetylamino-N-(2-morpholin-4-yl-ethyl)benzamide,
- N-(2-morpholin-4-ylethyl)-4-(pentanoylamino)benzamide,
- 4-propanoylamino-N-(2-diisopropylamino-ethyl)-2-ethoxybenzamide,
- 4-propanoylamino-N-(2-dibutylamino-ethyl)-2-ethoxybenzamide,
- 4-propanoylamino-2-methoxy-N-(2-piperidin-1-yl-ethyl)benzamide, or
- 4-propanoylamino-2-methoxy-N-(2-pyrrolidin-1-yl-ethyl)benzamide.
36 more elements
A pharmaceutical composition comprising a compound of formula (I)
- or a pharmaceutically acceptable salt or solvate thereof;
- wherein
- R1 is selected from C1-C6 alkyl and C3-C6 cycloalkyl;
- R2 is selected from H and C1-C3 alkyl;
- R3, R4, R5, and R6 are independently selected from hydrogen, C1-C3 alkyl, C1-C3 alkoxy, C1-C3 alkylthio, fluoro, chloro, bromo, phenyl and benzyl, wherein any alkyl is optionally substituted with one or more fluoro;
- R7 is selected from hydrogen and C1-C3 alkyl;
- R8 and R9 are independently selected from C1-C6 alkyl, or
- R8 and R9 together with the nitrogen atom to which they are both attached form a moiety of
- formula (II)
- r is 0 or 1;
- R10 is selected from C1-C3 alkyl and C3-C4 cycloalkyl;
- said alkyl and cycloalkyl optionally being substituted with hydroxy, halogen, cyano, COOR12, or NHR13;
- Q is selected from CHR11, NR11 and O;
- R11 is selected from hydrogen, C1-C3 alkyl and C3-C4 cycloalkyl;
- said alkyl and cycloalkyl optionally being substituted with a hydroxy, halogen, cyano, COOR12, or NHR13;
- R12 and R13 are independently selected from hydrogen, C1-C3 alkyl and C3-C4 cycloalkyl;
- p is 1, 2, or 3 when Q is CHR11;
- and
- p is 2 or 3 when Q is selected from NR11 and O;
- provided that the compound is not selected from:
- 4-acetamido-3-chloro-N-[2-(diethylamino)ethyl]benzamide,
- 4-acetamido-5-chloro-N-[2-(diethylamino)ethyl]-2-methoxybenzamide,
- N-[2-(diethylamino)ethyl]-4-(pentanoylamino)benzamide, and
- 4-acetamido-N-[2-(diethylamino)ethyl]benzamide.
21 more elements
Dependencies are inferred from the claim text.