IP Library › Granted Patent US 11,104,667
Granted Patent B2
US 11,104,667 · App. 16/263,881 · Granted Aug 31, 2021

Method for producing indole compound

Inventors: Teruhiko Inoue (Takatsuki, JP); Koji Matsumura (Takatsuki, JP); Shinichi Kikuchi (Takatsuki, JP)
Assignee: JAPAN TOBACCO INC.
C07D403/04C07C269/00C07C271/28C07D231/56C07D405/04C07D405/14A61K31/5377
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Quick Facts
Patent No.
US 11,104,667
App. No.
16/263,881
Granted
Aug 31, 2021
Kind
B2
Abstract

The present invention aims to provide a new method for producing an indole compound or a salt thereof, which has an ITK inhibitory action, and is useful for the prophylaxis or treatment of inflammatory disease. The present invention is a method for producing N-[2-(6,6-dimethyl-4,5,6,7-tetrahydro-1H-indazol-3-yl)-1H-indol-6-yl]-N-methyl-(2S)-2-(morpholin-4-yl)propanamide, which comprises a step of reacting

Claims (32)

1. A method of producing a compound of the formula [I]

which comprises a step of removing the protecting group from a compound of the formula [III]

to give a compound of the formula [I].

2. A method of producing a compound of the formula [II]

which comprises a step of removing the protecting group from a compound of the formula [III]

to give a compound of the formula [I], and

a step of treating a compound of the formula [I]

with hydrogen chloride to give a compound of the formula [II].

3. The method of claim 1 or 2 , which further comprises a step of reacting a compound of the formula [V]

with a compound of the formula [IV]

or a reactive derivative thereof or a salt thereof to give a compound of the formula [III]

4. The method of claim 3 , which further comprises a step of subjecting a compound of the formula [VI]

wherein R 1 and R 2 are each independently hydrogen, C 1-6 alkyl or C 1-6 alkoxy, to a reduction reaction to give a compound of the formula [V]

5. The method of claim 4 , which further comprises a step of reacting a compound of the formula [VII]

wherein R 1 is as defined in claim 4 ,

with a compound of the formula [XI]

wherein R 2 is as defined in claim 4 ,

to give a compound of the formula [VI]

wherein R 1 and R 2 are as defined above.

6. The method of claim 5 , which further comprises a step of subjecting a compound of the formula [VIII]

wherein R 1 is as defined in claim 4 ,

to tetrahydropyranylation to give a compound of the formula [VII]

wherein R 1 is as defined above.

7. The method of claim 6 , which further comprises a step of reacting a compound of the formula [IX]

with a compound of the formula [IX]

wherein

M is sodium or potassium, and

R 1 is as defined in claim 4 ,

to give a compound of the formula [VIII]

wherein R 1 is as defined above.

8. The method of claim 2 , which further comprises a step of purifying a compound of the formula [II]

with 1-propanol.

Priority Claims (1)
JP 2014-138654 · Jul 4, 2014 · national
Continuity (2)
Continuation 15323851
Related Publication 20190161475A1 · May 30, 2019
Cited By (1)
US 12,458,646