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US 8,299,070 B2Granted
Indole compounds and pharmaceutical use thereof
AssigneeJapan Tobacco Inc.
InventorsTeruhiko Inoue, Tetsudo Kaya, Shinichi Kikuchi, Koji Matsumura, Ritsuki Masuo, Motoya Suzuki, Michihide Maekawa
Life of this patent
Estimating the term…
Abstract
Provided is an agent for the treatment or prophylaxis of inflammatory diseases, allergic diseases, autoimmune diseases, transplant rejection or the like. A compound represented by the following formula [I] or a pharmaceutically acceptable salt thereof, or a solvate thereof: wherein each symbol is as described in the specification.
Claims49
A compound represented by the following formula [I] or a pharmaceutically acceptable salt thereof:
- wherein,
- R1 is
- (1) a hydrogen atom,
- (2) a hydroxy group, or
- (3) a C1-6 alkoxy group optionally substituted by C6-10 aryl group(s);
- R2 and R3 are the same or different and each is
- (1) a hydrogen atom, or
- (2) a C1-6 alkyl group optionally substituted by 1 to 3 substituents selected from
- (a) a hydroxy group, and
- (b) a C1-6 alkoxy group;
- and
- R4 is a group represented by
- which is bonded to the 5-position or the 6-position of the indole ring,
- wherein
- R5 is
- (1) a hydrogen atom, or
- (2) a C1-6 alkyl group, and
- R6 is
- (1) a hydrogen atom,
- (2) a C1-6 alkyl group optionally substituted by 1 to 3 substituents selected from
- (a) a hydroxy group,
- (b) a C1-6 alkoxy group,
- (c) a carboxy group,
- (d) a C1-6 alkoxy-carbonyl group,
- (e) a C6-10 aryl group,
- (f) a C6-10 aryloxy group,
- (g) an amino group optionally mono- or di-substituted by C1-6 alkyl group(s),
- (h) a 5- or 6-membered unsaturated heterocyclic group optionally substituted by C1-6 alkyl group(s), and
- (i) a 5- or 6-membered saturated heterocyclic group,
- (3) a C1-6 alkoxy group,
- (4) a C6-10 aryl group, or
- (5) a 5- or 6-membered unsaturated heterocyclic group optionally substituted by 1 to 3 substituents selected from
- (a) a hydroxy group, and
- (b) a C1-6 alkoxy group, or
- R5 and R6 form, together with the nitrogen atom they are bonded to, a 5- or 6-membered cyclic amine (said cyclic amine is optionally condensed with 5- or 6-membered unsaturated heterocycle) optionally substituted by 1 to 3 substituents selected from
- (a) a hydroxy group,
- (b) a C1-6 alkyl group,
- (c) a C1-6 alkoxy group, and
- (d) a C1-6 alkoxy-carbonyl group;
- R7 is
- (1) a hydrogen atom, or
- (2) a C1-6 alkyl group optionally substituted by 1 to 3 substituents selected from
- (a) a hydroxy group,
- (b) a C1-6 alkoxy group, and
- (c) an amino group optionally mono- or di-substituted by C1-6 alkyl group(s), and
- R8 is
- (1) a C1-6 alkyl group optionally substituted by 1 to 3 substituents selected from
- (a) a hydroxy group,
- (b) a C1-6 alkoxy group optionally substituted by C6-10 aryl group(s),
- (c) a C3-6 cycloalkyl group optionally substituted by C1-6 alkoxy group(s),
- (d) a C6-10 aryl group,
- (e) a 5- or 6-membered unsaturated heterocyclic group optionally substituted by oxo group(s),
- (f) a 5- to 8-membered saturated heterocyclic group optionally substituted by 1 to 3 substituents selected from
- (i) a hydroxy group,
- (ii) a C1-6 alkyl group optionally substituted by 1 to 3 substituents selected from a hydroxy group and a C1-6 alkoxy group,
- (iii) a C1-6 alkoxy group, and
- (iv) an oxo group,
- (g) a C3-6 cycloalkyloxy group,
- (h) a C6-10 aryloxy group,
- (i) a 5- or 6-membered unsaturated heterocyclyloxy group,
- (j) a 5- or 6-membered saturated heterocyclyloxy group, and
- (k) an amino group optionally mono- or di-substituted by substituents selected from
- (i) a C1-6 alkyl group optionally substituted by 1 to 3 substituents selected from a hydroxy group, a carboxy group and a carboxy-C1-6 alkoxy group,
- (ii) a C1-6 alkyl-carbonyl group optionally substituted by 1 to 3 substituents selected from a hydroxy group and a C1-6 alkoxy group,
- (iii) a C1-6 alkoxy-carbonyl group optionally substituted by C6-10 aryl group(s), and
- (iv) a C3-6 cycloalkyl-carbonyl group optionally substituted by C1-6 alkoxy group(s),
- (2) a C1-6 alkoxy group optionally substituted by C6-10 aryl group(s),
- (3) a C3-6 cycloalkyl group optionally substituted by 1 to 3 substituents selected from
- (a) a hydroxy group, and
- (b) a C1-6 alkoxy group,
- (4) a C6-10 aryl group optionally substituted by C1-6 alkyl group(s) optionally substituted by 1 to 3 halogen atoms,
- (5) an amino group optionally mono- or di-substituted by C1-6 alkyl group(s) optionally substituted by C6-10 aryl group(s),
- (6) a 5- or 6-membered unsaturated heterocyclic group optionally substituted by C1-6 alkyl group(s),
- (7) a 5- or 6-membered saturated heterocyclic group optionally substituted by 1 to 3 substituents selected from
- (a) a C1-6 alkyl group,
- (b) a C1-6 alkyl-carbonyl group, and
- (c) an oxo group,
- (8) a C3-6 cycloalkyloxy group, or
- (9) a C6-10 aryl-carbonyl group, or
- R7 and R8 form, together with the nitrogen atom and carbon atom they are bonded to, a 5- or 6-membered cyclic amine substituted by an oxo group and optionally further substituted by 1 to 3 substituents selected from
- (a) a hydroxy group,
- (b) a C1-6 alkyl group optionally substituted by hydroxy group(s),
- (c) a C1-6 alkoxy group, and
- (d) a C3-6 cycloalkyl group.
81 more elements
A compound represented by the following formula [I-a] or a pharmaceutically acceptable salt thereof:
- wherein,
- R1 is
- (1) a hydrogen atom,
- (2) a hydroxy group, or
- (3) a C1-6 alkoxy group optionally substituted by C6-10 aryl group(s);
- R2 and R3 are the same or different and each is
- (1) a hydrogen atom, or
- (2) a C1-6 alkyl group optionally substituted by 1 to 3 substituents selected from
- (a) a hydroxy group, and
- (b) a C1-6 alkoxy group;
- R7′ is a C1-6 alkyl group optionally substituted by 1 to 3 substituents selected from
- (a) a hydroxy group,
- (b) a C1-6 alkoxy group, and
- (c) an amino group optionally mono- or di-substituted by C1-6 alkyl group(s), and
- R8 is
- (1) a C1-6 alkyl group optionally substituted by 1 to 3 substituents selected from
- (a) a hydroxy group,
- (b) a C1-6 alkoxy group optionally substituted by C6-10 aryl group(s),
- (c) a C3-6 cycloalkyl group optionally substituted by C1-6 alkoxy group(s),
- (d) a C6-10 aryl group,
- (e) a 5- or 6-membered unsaturated heterocyclic group optionally substituted by oxo group(s),
- (f) a 5- to 8-membered saturated heterocyclic group optionally substituted by 1 to 3 substituents selected from
- (i) a hydroxy group,
- (ii) a C1-6 alkyl group optionally substituted by 1 to 3 substituents selected from a hydroxy group and a C1-6 alkoxy group,
- (iii) a C1-6 alkoxy group, and
- (iv) an oxo group,
- (g) a C3-6 cycloalkyloxy group,
- (h) a C6-10 aryloxy group,
- (i) a 5- or 6-membered unsaturated heterocyclyloxy group,
- (j) a 5- or 6-membered saturated heterocyclyloxy group, and
- (k) an amino group optionally mono- or di-substituted by substituents selected from
- (i) a C1-6 alkyl group optionally substituted by 1 to 3 substituents selected from a hydroxy group, a carboxy group and a carboxy-C1-6 alkoxy group,
- (ii) a C1-6 alkyl-carbonyl group optionally substituted by 1 to 3 substituents selected from a hydroxy group and a C1-6 alkoxy group,
- (iii) a C1-6 alkoxy-carbonyl group optionally substituted by C6-10 aryl group(s), and
- (iv) a C3-6 cycloalkyl-carbonyl group optionally substituted by C1-6 alkoxy group(s),
- (2) a C1-6 alkoxy group optionally substituted by C6-10 aryl group(s),
- (3) a C3-6 cycloalkyl group optionally substituted by 1 to 3 substituents selected from
- (a) a hydroxy group, and
- (b) a C1-6 alkoxy group,
- (4) a C6-10 aryl group optionally substituted by C1-6 alkyl group(s) optionally substituted by 1 to 3 halogen atoms,
- (5) an amino group optionally mono- or di-substituted by C1-6 alkyl group(s) optionally substituted by C6-10 aryl group(s),
- (6) a 5- or 6-membered unsaturated heterocyclic group optionally substituted by C1-6 alkyl group(s),
- (7) a 5- or 6-membered saturated heterocyclic group optionally substituted by 1 to 3 substituents selected from
- (a) a C1-6 alkyl group,
- (b) a C1-6 alkyl-carbonyl group, and
- (c) an oxo group,
- (8) a C3-6 cycloalkyloxy group, or
- (9) a C6-10 aryl-carbonyl group, or
- R7′ and R8 form, together with the nitrogen atom and carbon atom they are bonded to, a 5- or 6-membered cyclic amine substituted by an oxo group and optionally further substituted by 1 to 3 substituents selected from
- (a) a hydroxy group,
- (b) a C1-6 alkyl group optionally substituted by hydroxy group(s),
- (c) a C1-6 alkoxy group, and
- (d) a C3-6 cycloalkyl group.
50 more elements
A compound selected from the following formulas:
- and a pharmaceutically acceptable salt thereof.
Dependencies are inferred from the claim text.