2,3-dihydro-4H-1,3-benzoxazin-4-one derivatives as modulators of cholinergic muscarinic M1 receptor

1. A method for the treatment of Alzheimer's disease, schizophrenia, cognitive impairment associate with schizophrenia, pain, sleep disorder, Parkinson's disease dementia, Parkinson's disease, or dementia with Lewy bodies in a mammal, which comprises administering to the mammal an effective amount of a compound represented by the formula

wherein

R 1 and R 2 are each independently a hydrogen atom or a substituent, or

a partial structure:

is optionally

(wherein X 1 and X 2 are each independently CH or N),

R 3 is a hydrogen atom, an optionally substituted C 1-6 alkyl group or an optionally substituted cyclic group, and

ring A is a ring which is optionally further substituted,

excluding 6-[(2,4-dioxothiazolidin-5-yl)methyl]-3-[((4-trifluoromethyl)phenyl)methyl]-1,3-benzoxazin-4-one,

or a salt thereof.

2. The method according to claim 1 , wherein R 3 is (1) a hydrogen atom, (2) a C 1-6 alkyl group optionally substituted by 1 to 3 substituents selected from a hydroxy group and a 3- to 14-membered non-aromatic heterocyclic group, (3) a C 3-10 cycloalkyl group optionally substituted by 1 to 3 hydroxy groups, (4) a C 6-14 aryl group optionally substituted by 1 to 3 halogen atoms or (5) a 3- to 14-membered non-aromatic heterocyclic group optionally substituted by 1 to 3 hydroxy groups.

3. The method according to claim 1 , wherein the ring A is an optionally further substituted 6-membered aromatic ring.

4. The method according to claim 1 , wherein the ring A is a 6-membered aromatic ring optionally further substituted by 1 to 5 substituents selected from

(i) a halogen atom,

(ii) a cyano group,

(iii) a C 1-6 alkyl group,

(iv) a C 2-6 alkenyl group,

(v) a C 2-6 alkynyl group optionally substituted by a tri-C 1-6 alkylsilyl group,

(vi) a C 1-6 alkoxy group and

(vii) a 5- to 14-membered aromatic heterocyclic group optionally substituted by 1 to 3 substituents selected from a halogen atom and a C 1-6 alkyl group.

5. The method according to claim 1 , wherein at least one of R 1 and R 2 is a substituent.

6. The method according to claim 1 , wherein R 1 is a hydrogen atom, a halogen atom or a C 1-6 alkyl group;

R 2 is a hydrogen atom, a halogen atom, a C 1-6 alkyl group, a C 2-6 alkenyl group or a C 1-6 alkoxy group; or

the partial structure:

(wherein X 1 and X 2 are each CH);

R 3 is a hydrogen atom, an optionally substituted C 1-6 alkyl group, an optionally substituted C 3-10 cycloalkyl group, an optionally substituted C 6-14 aryl group or an optionally substituted 3- to 14-membered non-aromatic heterocyclic group; and

ring A is a C 6-14 aromatic hydrocarbon ring, a 3- to 14-membered non-aromatic heterocycle or a 5- to 14-membered aromatic heterocycle, each of which is optionally further substituted.

7. The method according to claim 1 , wherein R 1 is a hydrogen atom, a halogen atom or a C 1-6 alkyl group;

R 2 is a hydrogen atom, a halogen atom, a C 1-6 alkyl group, a C 2-6 alkenyl group or a C 1-6 alkoxy group; or

the partial structure:

(wherein X 1 and X 2 are each CH);

R 3 is

(1) a hydrogen atom,

(2) a C 1-6 alkyl group optionally substituted by 1 to 3 substituents selected from a hydroxy group and a 3- to 14-membered non-aromatic heterocyclic group,

(3) a C 3-10 cycloalkyl group optionally substituted by 1 to 3 hydroxy groups,

(4) a C 6-14 aryl group optionally substituted by 1 to 3 halogen atoms or

(5) a 3- to 14-membered non-aromatic heterocyclic group optionally substituted by 1 to 3 hydroxy groups; and

ring A is a C 6-14 aromatic hydrocarbon ring, a 3- to 14-membered non-aromatic heterocycle or a 5- to 14-membered aromatic heterocycle, each of which is optionally further substituted by 1 to 5 substituents selected from

(i) a halogen atom,

(ii) a cyano group,

(iii) an oxo group,

(iv) a C 1-6 alkyl group optionally substituted by 1 to 3 halogen atoms,

(v) a C 2-6 alkenyl group,

(vi) a C 2-6 alkynyl group optionally substituted by a tri-C 1-6 alkylsilyl group,

(vii) a C 1-6 alkoxy group,

(viii) a C 1-6 alkoxy-carbonyl group and

(ix) a 5- to 14-membered aromatic heterocyclic group optionally substituted by 1 to 3 substituents selected from a halogen atom and a C 1-6 alkyl group.

8. The method according to claim 1 , wherein R 1 is a hydrogen atom, a halogen atom or a C 1-6 alkyl group;

R 2 is a hydrogen atom, a halogen atom, a C 1-6 alkyl group, a C 2-6 alkenyl group or a C 1-6 alkoxy group; or

the partial structure:

(wherein X 1 and X 2 are each CH);

R 3 is

(1) a hydrogen atom,

(2) a C 1-6 alkyl group optionally substituted by 1 to 3 substituents selected from a hydroxy group and a 3- to 14-membered non-aromatic heterocyclic group,

(3) a C 3-10 cycloalkyl group optionally substituted by 1 to 3 hydroxy groups,

(4) a C 6-14 aryl group optionally substituted by 1 to 3 halogen atoms or

(5) a 3- to 14-membered non-aromatic heterocyclic group optionally substituted by 1 to 3 hydroxy groups; and

ring A is a 6-membered aromatic ring optionally further substituted by 1 to 5 substituents selected from

(i) a halogen atom,

(ii) a cyano group,

(iii) a C 1-6 alkyl group,

(iv) a C 2-6 alkenyl group,

(v) a C 2-6 alkynyl group optionally substituted by a tri-C 1-6 alkylsilyl group,

(vi) a C 1-6 alkoxy group and

(vii) a 5- to 14-membered aromatic heterocyclic group optionally substituted by 1 to 3 substituents selected from a halogen atom and a C 1-6 alkyl group.

9. The method according to claim 1 , wherein R 1 is a hydrogen atom, a halogen atom or a C 1-6 alkyl group;

R 2 is a C 1-6 alkyl group, a C 2-6 alkenyl group or a C 1-6 alkoxy group; or

the partial structure:

(wherein X 1 and X 2 are each CH);

R 3 is

(1) a C 3-10 cycloalkyl group optionally substituted by 1 to 3 hydroxy groups or

(2) a 3- to 14-membered non-aromatic heterocyclic group optionally substituted by 1 to 3 hydroxy groups; and

ring A is a C 6-14 aromatic hydrocarbon ring, a 3- to 14-membered non-aromatic heterocycle or a 5- to 14-membered aromatic heterocycle, each of which is optionally further substituted by 1 to 5 substituents selected from

(i) a halogen atom,

(ii) a cyano group,

(iii) a C 1-6 alkyl group,

(iv) a C 1-6 alkoxy group and

(v) a 5- to 14-membered aromatic heterocyclic group optionally substituted by 1 to 3 C 1-6 alkyl groups.

10. The method according to claim 1 , wherein R 1 is a hydrogen atom, a halogen atom or a C 1-6 alkyl group:

R 2 is a C 1-6 alkyl group, a C 2-6 alkenyl group or a C 1-6 alkoxy group:

R 3 is

(1) a C 3-10 cycloalkyl group optionally substituted by 1 to 3 hydroxy groups or

(2) a 3- to 14-membered non-aromatic heterocyclic group optionally substituted by 1 to 3 hydroxy groups: and

ring A is a C 6-14 aromatic hydrocarbon ring, a 3- to 14-membered non-aromatic heterocycle or a 5- to 14-membered aromatic heterocycle, each of which is optionally further substituted by 1 to 5 substituents selected from

(i) a halogen atom,

(ii) a cyano group,

(iii) a C 1-6 alkyl group,

(iv) a C 1-6 alkoxy group and

(v) a 5- to 14-membered aromatic heterocyclic group optionally substituted by 1 to 3 C 1-6 alkyl groups.

11. The method according to claim 1 , wherein R 1 is a hydrogen atom or a halogen atom:

R 2 is a C 1-6 alkyl group:

R 3 is

(1) a C 3-10 cycloalkyl group optionally substituted by 1 to 3 hydroxy groups or

(2) a 3- to 14-membered non-aromatic heterocyclic group optionally substituted by 1 to 3 hydroxy groups: and

ring A is a C 6-14 aromatic hydrocarbon ring or a 5- to 14-membered aromatic heterocycle, each of which is optionally further substituted by 1 to 5 substituents selected from

(i) a halogen atom,

(ii) a C 1-6 alkyl group and

(iii) a 5- to 14-membered aromatic heterocyclic group optionally substituted by 1 to 3 C 1-6 alkyl groups.