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US 2007/0191426 A1Published application
Derivatives of 3-aminocarbonylquinoline, pharmaceutical compositions containing them and processes and intermediates for their preparation
OwnerChristopher Edlin, Colin Eldred +4inventors
InventorsChristopher Edlin, Colin Eldred, Christopher Lunniss, Alison Redgrave, John Robinson, Michael Woodrow
Life of this patent
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Abstract
Compounds of formula (I) or pharmaceutically acceptable salts thereof are inhibitors of phosphodiesterase type IV (PDE4) and are of use in the treatment of inflammatory and/or allergic diseases.
Claims17
A compound of formula (I) or a pharmaceutically acceptable salt thereof:
- wherein:
- R1 is
- Aryl optionally substituted by one or more substituents selected from the group consisting of:
- C1-6 alkoxy, halogen, —CN, C1-6 alkyl optionally substituted by one or more halogens, —OH, and C1-6 alkylCO;
- Heteroaryl optionally substituted by C1-3 alkyl;
- C3-7 cycloalkyl;
- Heterocyclyl;
- or
- Aryl fused to a heterocyclyl ring;
- R2 is hydrogen or C1-6 alkyl;
- R3 is
- Hydrogen;
- C1-6 alkyl optionally substituted by one or more substituents selected from the group consisting of:
- heterocyclyl (itself optionally substituted by C1-6 alkyl), R7R8NCO—, R9CONR10—, C1-6 alkoxy, R11R12N—, and C1-3 alkyl sulfonyl;
- C3-7 cycloalkyl;
- Aryl(CH2)m— wherein the aryl is optionally substituted by one or more substituents selected from the group consisting of:
- halogen and C1-6 alkoxy;
- Aryl fused to a heterocyclyl ring;
- Aryl fused to a C4-7 cycloalkyl wherein the cycloalkyl is optionally substituted by ═O;
- Heteroaryl(CH2)m— wherein the heteroaryl is optionally substituted by one or more substituents selected from the group consisting of:
- C1-6 alkyl, halogen and C1-6 alkoxy;
- or
- Heterocyclyl(CH2)m— wherein the heterocyclyl is optionally substituted by one or more substituents selected from the group consisting of:
- C1-6 alkylCO, C1-6 alkyl;
- R4 is hydrogen or C1-6 alkyl;
- R3 and R4 together with the nitrogen atom to which they are attached may form a heterocyclyl ring, which is optionally substituted by one or more substituents selected from the group consisting of:
- C1-6 alkylCO, C1-6alkoxy, C3-7cycloalkyl, OH, halogen, C1-6 alkyl, —(CH2)mNR13R14, —(CH2)mCONR15R16, —(CH2)mNR17COR18, heteroaryl, heteroarylC1-4alkyl, heteroarylCO, —CO2C1-6alkyl and C1-6alkoxyC1-4alkyl;
- R5 is hydrogen or C1-6 alkyl;
- R6 is hydrogen, C1-6 alkyl, C1-6alkoxy, fluorine, chlorine, or bromine;,
- m is 0-6;
- R7-18 all independently represent hydrogen, or C1-6 alkyl;
- R7 and R8 together with the nitrogen atom to which they are attached may form a heterocyclyl ring;
- R11 and R12 together with the nitrogen atom to which they are attached may form a heterocyclyl ring;
- and
- R13 and R14 together with the nitrogen atom to which they are attached may form a heterocyclyl ring.
32 more elements
A compound of formula (I) selected from the group consisting of:
- 4-{[3-(methyloxy)phenyl]amino}-N6-phenyl-3,6-quinolinedicarboxamide,
- 4-{[3-(methyloxy)phenyl]amino}-6-(4-morpholinylcarbonyl)-3-quinolinecarboxamide,
- N6,N6-dimethyl-4-{[3-(methyloxy)phenyl]amino}-3,6-quinolinedicarboxamide,
- N6-1,3-benzothiazol-6-yl-4-{[3-(methyloxy)phenyl]amino}-3,6-quinolinedicarboxamide,
- N6-(1-methyl-1H-benzimidazol-5-yl)-4-{[3-(methyloxy)phenyl]amino}-3,6-quinolinedicarboxamide,
- 4-{[3-(methyloxy)phenyl]amino}-N6-3-pyridinyl-3,6-quinolinedicarboxamide,
- N6-[3-(methyloxy)phenyl]-4-{[3-(methyloxy)phenyl]amino}-3,6-quinolinedicarboxamide,
- N6-1,3-benzodioxol-5-yl-4-{([3-(methyloxy)phenyl]amino}-3,6-quinolinedicarboxamide,
- 4-{[3-(methyloxy)phenyl]amino}-N6-(3-oxo-2,3-dihydro-1H-inden-5-yl)-3,6-quinolinedicarboxamide,
- 4-{[3-(methyloxy)phenyl]amino}-N6-[6-(methyloxy)-3-pyridinyl]-3,6-quinolinedicarboxamide,
- N6-(4-chlorophenyl)-4-{[3-(methyloxy)phenyl]amino}-3,6-quinolinedicarboxamide,
- 4-{[3-(methyloxy)phenyl]amino}-6-(1-piperidinylcarbonyl)-3-quinolinecarboxamide,
- 4-{[3-(methyloxy)phenyl]amino}-N6-(1,3-thiazol-2-ylmethyl)-3,6-quinolinedicarboxamide,
- N6-(1,3-dihydro-2-benzofuran-5-yl)-4-{[3-(methyloxy)phenyl]amino}-3,6-quinolinedicarboxamide,
- N6-[(3-methyl-5-isoxazolyl)methyl]-4-{[3-(methyloxy)phenyl]amino}-3,6-quinolinedicarboxamide,
- N6-[(5-chloro-2-pyridinyl)methyl]-4-{[3-(methyloxy)phenyl]amino}-3,6-quinolinedicarboxamide,
- 4-(2,3-dihydro-1-benzofuran-4-ylamino)-N˜6˜,8-dimethyl-N˜6˜-[2-(methyloxy)ethyl]-3,6-quinolinedicarboxamide
- 4-(2,3-dihydro-1-benzofuran-4-ylamino)-8-methyl-6-(4-morpholinylcarbonyl)-3-quinolinecarboxamide,
- 8-methyl-4-[(1-methyl-1H-indazol-6-yl)amino]-6-(4-morpholinylcarbonyl)-3-quinolinecarboxamide,
- 4-{[4-fluoro-3-(methyloxy)phenyl]amino}-8-methyl-6-(4-morpholinylcarbonyl)-3-quinolinecarboxamide,
- 4-{[4-fluoro-3-(methyloxy)phenyl]amino}-N˜6˜,8-dimethyl-N˜6˜-[2-(methyloxy)ethyl]-3,6-quinolinedicarboxamide,
- 4-{[4-fluoro-3-(methyloxy)phenyl]amino}-N˜6˜,8-dimethyl-N˜6˜-[2-(methylsulfonyl)ethyl]-3,6-quinolinedicarboxamide,
- 6-[(4-acetyl-1-piperazinyl)carbonyl]-4-{[4-fluoro-3-(methyloxy)phenyl]amino}-8-methyl-3-quinolinecarboxamide,
- 4-(2,3-dihydro-1-benzofuran-4-ylamino)-N˜6˜,N˜6˜,8-trimethyl-3,6-quinolinedicarboxamide,
- 4-(2,3-dihydro-1-benzofuran-4-ylamino)-8-methyl-6-({4-[2-(methyloxy)ethyl]-1-piperazinyl}carbonyl)-3-quinolinecarboxamide,
- 4-(2,3-dihydro-1-benzofuran-4-ylamino)-6-[(2,6-dimethyl-4-morpholinyl)carbonyl]-8-methyl-3-quinolinecarboxamide,
- 4-(2,3-dihydro-1-benzofuran-4-ylamino)-6-{[4-(dimethylamino)-1-piperidinyl]carbonyl}-8-methyl-3-quinolinecarboxamide,
- 4-(2,3-dihydro-1-benzofuran-4-ylamino)-N˜6˜,8-dimethyl-N˜6˜-(4-pyridinylmethyl)-3,6-quinolinedicarboxamide,
- 6-[(4-acetyl-1-piperazinyl)carbonyl]-4-(2,3-dihydro-1-benzofuran-4-ylamino)-8-methyl-3-quinolinecarboxamide,
- 4-(2,3-dihydro-1-benzofuran-4-ylamino)-8-methyl-N˜6˜-4-pyridinyl-3,6-quinolinedicarboxamide,
- 4-(2,3-dihydro-1-benzofuran-4-ylamino)-8-methyl-N˜6˜-(tetrahydro-2H-pyran-4-yl)-3,6-quinolinedicarboxamide,
- 4-(2,3-dihydro-1-benzofuran-4-ylamino)-8-methyl-N˜6˜-(1-methyl-1H-pyrazol-5-yl)-3,6-quinolinedicarboxamide.
- and pharmaceutically acceptable salts thereof.
30 more elements
-14. (canceled)
Dependencies are inferred from the claim text.