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US 2009/0036684 A1Published application
Method for producing 4-oxoquinoline compound
AssigneeJapan Tobacco Inc.
InventorsKoji Matsuda, Koji Ando, Shigeki Ohki, Jun-ichi Hoshi, Takahiro Yamasaki
Life of this patent
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Abstract
The present invention provides a compound useful as a synthetic intermediate for an anti-HIV agent having an integrase inhibitory activity, and a production method thereof, and a production method of an anti-HIV agent using the synthetic intermediate. Specifically, for example, a compound represented by the formula (2′): wherein R is a fluorine atom or a methoxy group, and R400 is a hydrogen atom or a C1-C4 alkyl group, or a salt thereof, and a production method thereof, and a production method of an anti-HIV agent using the synthetic intermediate.
Claims33
A compound represented by the formula (2′):
- wherein R is a fluorine atom or a methoxy group, and R400 is a hydrogen atom or a C1-C4 alkyl group,
- or a salt thereof.
Use of a compound represented by the formula (8-1):
- wherein X100 is a halogen atom for the production of a compound represented by the formula (2′):
- wherein R is a fluorine atom or a methoxy group, and R400 is a hydrogen atom or a C1-C4 alkyl group,
- or a salt thereof.
Use of a compound represented by the formula (8-1):
- wherein X100 is a halogen atom, and
- a compound represented by the formula (2-1):
- wherein R is a fluorine atom or a methoxy group, R300 is a C1-C4 alkyl group, and X200 is a halogen atom, in the presence of a metal atom M1, for the production of a compound represented by the formula (2′):
- wherein R is a fluorine atom or a methoxy group, and R400 is a hydrogen atom or a C1-C4 alkyl group,
- or a salt thereof.
2 more elements
Use of a compound represented by the formula (2′):
- wherein R is a fluorine atom or a methoxy group, and R400 is a hydrogen atom or a C1-C4 alkyl group,
- or a salt thereof, for the production of compound (10):
- or a salt thereof.
Use of a compound represented by the formula (8-1):
- wherein X100 is a halogen atom, a compound represented by the formula (2-1):
- wherein R is a fluorine atom or a methoxy group, R300 is a C1-C4 alkyl group, and X200 is a halogen atom, and a compound
- represented by the formula (2′):
- wherein R is a fluorine atom or a methoxy group, and R400 is a hydrogen atom or a C1-C4 alkyl group, or a salt thereof, for the production of compound (10):
- or a salt thereof.
2 more elements
Use of a compound represented by the formula (2-2):
- wherein R is a fluorine atom or a methoxy group, and R300 is a C1-C4 alkyl group, a compound represented by the formula (2-3):
- wherein R is a fluorine atom or a methoxy group, or a salt thereof, a compound represented by the formula (3):
- wherein R is a fluorine atom or a methoxy group, a compound represented by the formula (4):
- wherein R is a fluorine atom or a methoxy group, and R100 is a C1-C4 alkyl group, or a salt thereof, a compound represented by the formula (5):
- wherein R is a fluorine atom or a methoxy group, and R100 is a C1-C4 alkyl group, and a compound represented by the formula (6):
- wherein R is a fluorine atom or a methoxy group, and R100 is a C1-C4 alkyl group, for the production of compound (10):
- or a salt thereof.
4 more elements
Use of a compound represented by the formula (2-2-A):
- wherein R300 is a C1-C4 alkyl group, compound (2-3-A):
- or a salt thereof, compound (3-A):
- a compound represented by the formula (4-A):
- wherein R100 is a C1-C4 alkyl group, or a salt thereof, a compound represented by the formula (5-A):
- wherein R100 is a C1-C4 alkyl group, a compound represented by the formula (6-A):
- wherein R100 is a C1-C4 alkyl group, a compound represented by the formula (7):
- wherein R100 is a C1-C4 alkyl group, and R200 is a hydroxyl-protecting group, and a compound represented by the formula (9):
- wherein R100 is a C1-C4 alkyl group, and R200 is a hydroxyl-protecting group, for the production of compound (10):
- or a salt thereof.
6 more elements
Use of a compound represented by the formula (2-2-B):
- wherein R300 is a C1-C4 alkyl group, compound (2-3-B)
- or a salt thereof, compound (3-B):
- a compound represented by the formula (4-B):
- wherein R100 is a C1-C4 alkyl group, or a salt thereof, a compound represented by the formula (5-B):
- wherein R100 is a C1-C4 alkyl group, a compound represented by the formula (6-B):
- wherein R100 is a C1-C4 alkyl group, and a compound represented by the formula (8):
- wherein R100 is a C1-C4 alkyl group, for the production of compound (10):
- or a salt thereof.
5 more elements
Use of a compound represented by the formula (1):
- wherein R is a fluorine atom or a methoxy group, or a salt thereof, a compound represented by the formula (2):
- wherein R is a fluorine atom or a methoxy group, and X200 is a halogen atom, or a salt thereof, a compound represented by the formula (2-1):
- wherein R is a fluorine atom or a methoxy group, R300 is a C1-C4 alkyl group, and X200 is a halogen atom, a compound represented by the formula (2-2):
- wherein R is a fluorine atom or a methoxy group, and R300 is a C1-C4 alkyl group, a compound represented by the formula (2-3):
- wherein R is a fluorine atom or a methoxy group, or a salt thereof, a compound represented by the formula (3):
- wherein R is a fluorine atom or a methoxy group, a compound represented by the formula (4):
- wherein R is a fluorine atom or a methoxy group, and R100 is a C1-C4 alkyl group, or a salt thereof, a compound represented by the formula (5):
- wherein R is a fluorine atom or a methoxy group, and R100 is a C1-C4 alkyl group, and a compound represented by the formula (6):
- wherein R is a fluorine atom and a methoxy group, and R100 is a C1-C4 alkyl group, for the production of compound (10):
- or a salt thereof.
7 more elements
Use of compound (1-A):
- or a salt thereof, a compound represented by the formula (2-A):
- wherein X200 is a halogen atom, or a salt thereof, a compound represented by the formula (2-1-A):
- wherein R300 is a C1-C4 alkyl group, and X200 is a halogen atom, a compound represented by the formula (2-2-A):
- wherein R300 is a C1-C4 alkyl group, compound (2-3-A):
- or a salt thereof, compound (3-A):
- a compound represented by the formula (4-A):
- wherein R100 is a C1-C4 alkyl group, or a salt thereof, a compound represented by the formula (5-A):
- wherein R100 is a C1-C4 alkyl group, a compound represented by the formula (6-A):
- wherein R100 is a C1-C4 alkyl group, a compound represented by the formula (7):
- wherein R100 is a C1-C4 alkyl group, and R200 is a hydroxyl-protecting group, and a compound represented by the formula (9):
- wherein R100 is a C1-C4 alkyl group, and R200 is a hydroxyl-protecting group, for the production of compound (10):
- or a salt thereof.
9 more elements
Use of compound (1-B):
- or a salt thereof, a compound represented by the formula (2-B):
- wherein X200 is a halogen atom, or a salt thereof, a compound represented by the formula (2-1-B):
- wherein R300 is a C1-C4 alkyl group, and X200 is a halogen atom, a compound represented by the formula (2-2-B):
- wherein R300 is a C1-C4 alkyl group, compound (2-3-B):
- or a salt thereof, compound (3-B):
- a compound represented by the formula (4-B):
- wherein R100 is a C1-C4 alkyl group, or a salt thereof, a compound represented by the formula (5-B):
- wherein R100 is a C1-C4 alkyl group, a compound represented by the formula (6-B):
- wherein R100 is a C1-C4 alkyl group, and a compound represented by the formula (8):
- wherein R100 is a C1-C4 alkyl group, for the production of compound (10):
- or a salt thereof.
8 more elements
A method of producing a compound represented by the formula (2′):
- wherein R is a fluorine atom or a methoxy group, and R400 is a hydrogen atom or a C1-C4 alkyl group, or a salt thereof, which comprises reacting a compound represented by the formula (8-1):
- wherein X100 is a halogen atom, with a compound represented by the formula (2-1):
- wherein R is a fluorine atom or a methoxy group, R300 is a C1-C4 alkyl group, and X200 is a halogen atom in the presence of a metal atom M1.
A method of producing compound (10):
- or a salt thereof, from a compound represented by the formula (2′):
- wherein R is a fluorine atom or a methoxy group, and R400 is a hydrogen atom or a C1-C4 alkyl group, or a salt thereof.
A method of producing compound (10):
- or a salt thereof, which comprises
- a step of producing compound (2-3-A):
- or a salt thereof, from a compound represented by the formula (2-2-A):
- wherein R300 is a C1-C4 alkyl group;
- a step of producing compound (3-A):
- from the above-mentioned compound (2-3-A) or a salt thereof;
- a step of producing a compound represented by the formula (4-A):
- wherein R100 is a C1-C4 alkyl group, or a salt thereof, from the above-mentioned compound (3-A);
- a step of producing a compound represented by the formula (5-A):
- wherein R100 is a C1-C4 alkyl group, from said compound represented by the formula (4-A) or a salt thereof;
- a step of producing a compound represented by the formula (6-A):
- wherein R100 is a C1-C4 alkyl group, from said compound represented by the formula (5-A);
- a step of producing a compound represented by the formula (7):
- wherein R100 is a C1-C4 alkyl group, and R200 is a hydroxyl-protecting group, from said compound represented by the formula (6-A);
- a step of producing a compound represented by the formula (9):
- wherein R100 is a C1-C4 alkyl group, and R200 is a hydroxyl-protecting group, from said compound represented by the formula (7);
- and
- a step of producing the above-mentioned compound (10) or a salt thereof from said compound represented by the formula (9).
15 more elements
A method of producing compound (10):
- or a salt thereof, which comprises
- a step of producing compound (2-3-B):
- or a salt thereof, from a compound represented by the formula (2-2-B):
- wherein R300 is a C1-C4 alkyl group;
- a step of producing compound (3-B):
- from the above-mentioned compound (2-3-B) or a salt thereof;
- a step of producing a compound represented by the formula (4-B):
- wherein R100 is a C1-C4 alkyl group, or a salt thereof, from the above-mentioned compound (3-B);
- a step of producing a compound represented by the formula (5-B):
- wherein R100 is a C1-C4 alkyl group, from said compound represented by the formula (4-B) or a salt thereof;
- a step of producing a compound represented by the formula (6-B):
- wherein R100 is a C1-C4 alkyl group, from said compound represented by the formula (5-B);
- a step of producing a compound represented by the formula (8):
- wherein R100 is a C1-C4 alkyl group, from said compound represented by the formula (6-B);
- and
- a step of producing the above-mentioned compound (10) or a salt thereof from said compound represented by the formula (8).
13 more elements
A compound represented by the formula (2-B):
- wherein X200 is a halogen atom, or a salt thereof.
A compound represented by the formula (2-1):
- wherein R is a fluorine atom or a methoxy group, R300 is a C1-C4 alkyl group, and X200 is a halogen atom.
A compound represented by the formula (3):
- wherein R is a fluorine atom or a methoxy group.
A compound represented by the formula (4):
- wherein R is a fluorine atom or a methoxy group, and R100 is a C1-C4 alkyl group, or a salt thereof.
A compound represented by the formula (4-1)
- wherein R is a fluorine atom or a methoxy group, and R100 is a C1-C4 alkyl group, or a salt thereof.
A compound represented by the formula (4-2-B):
- wherein R100 is a C1-C4 alkyl group, or a salt thereof.
Use of a compound represented by the formula (4-1):
- wherein R is a fluorine atom or a methoxy group, and R100 is a C1-C4 alkyl group, or a salt thereof, for the production of a compound represented by the formula (4):
- wherein R is a fluorine atom or a methoxy group, and R100 is a C1-C4 alkyl group, or a salt thereof.
Use of a compound represented by the formula (4-2-B):
- wherein R100 is a C1-C4 alkyl group, or a salt thereof, for the production of a compound represented by the formula (4-B):
- wherein R100 is a C1-C4 alkyl group, or a salt thereof.
Use of a compound represented by the formula (3):
- wherein R is a fluorine atom or a methoxy group, and a compound represented by the formula (4-1):
- wherein R is a fluorine atom or a methoxy group, and R100 is a C1-C4 alkyl group, or a salt thereof, for the production of a compound represented by the formula (4):
- wherein R is a fluorine atom or a methoxy group, and R100 is a C1-C4 alkyl group, or a salt thereof.
Use of compound (3-B):
- and a compound represented by the formula (4-2-B):
- wherein R100 is a C1-C4 alkyl group, or a salt thereof, for the production of a compound represented by the formula (4-B):
- wherein R100 is a C1-C4 alkyl group, or a salt thereof.
A compound represented by the formula (5):
- wherein R is a fluorine atom or a methoxy group, and R100 is a C1-C4 alkyl group.
A compound represented by the formula (6):
- wherein R is a fluorine atom or a methoxy group, and R100 is a C1-C4 alkyl group.
A compound represented by the formula (7):
- wherein R100 is a C1-C4 alkyl group, and R200 is a hydroxyl-protecting group.
A compound represented by the formula (9):
- wherein R100 is a C1-C4 alkyl group, and R200 is a hydroxyl-protecting group.
A compound represented by the formula (8):
- wherein R100 is a C1-C4 alkyl group.
Dependencies are inferred from the claim text.