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Method For Producing Indole Compound

Abstract: Provided is a novel method for producing an indole compound or salt thereof having an ITK inhibiting effect and being useful in the treatment or prevention of inflammatory diseases and the like. 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 including a step for reacting (V) and (IV).

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Notices, Deadlines & Correspondence

Patent Information

Application #
Filing Date
01 February 2017
Publication Number
22/2017
Publication Type
INA
Invention Field
CHEMICAL
Status
Email
email@anandandanand.com
Parent Application
Patent Number
Legal Status
Grant Date
2020-04-24
Renewal Date

Applicants

1. JAPAN TOBACCO INC
2-1, Toranomon 2-chome, Minato-ku, Tokyo 105- 8422. Japan.

Inventors

1. INOUE, Teruhiko
c/o Central Pharmaceutical Research Institute, Japan Tobacco Inc., 1-l Murasaki-cho, Takatsuki-shi, Osaka 569-1125, Japan.
2. MATSUMURA, Koji
c/o Central Pharmaceutical Research Institute, Japan Tobacco Inc., 1-1 Murasaki-cho, Takatsuki-shi, Osaka 569-t125, Japan
3. KIKUCHI, Shinichi
c/o Central Pharmaceutical Research Institute, Japan Tobacco Inc., 1-1 Murasaki-cho, Takatsuki-shi, Osaka 569-1125, Japan

Specification

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

I
with hydrogen chloride to give a compound of the formula [II]. 3. 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].

4. The method of claim 1 or 3, 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]
5. The method of claim 4, which further comprises a step of subjecting a compound of the formula [VI]

wherein R1 and R2 are each independently hydrogen, Ci-6 alkyl or
Ci-6 alkoxy,
to a reduction reaction to give a compound of the formula [V]
6. The method of claim 5, which further comprises a step of reacting a compound of the formula [VII]

wherein R1 is as defined in claim 5, with a compound of the formula [XI]
wherein R2 is as defined in claim 5, 5 to give a compound of the formula [VI]
r
wherein R1 and R2 are as defined above.
7. The method of claim 6, which further comprises a step of 10 subjecting a compound of the formula [VIII]
r
wherein R1 is as defined in claim 5,
to tetrahydropyranylation to give a compound of the formula
[VII]

wherein R is as defined above.
8. The method of claim 1, which further comprises a step of reacting a compound of the formula [IX]
IN
H
with a compound of the formula [X]
wherein
M is sodium or potassium, and
R1 is as defined in claim 5,
to give a compound of the formula [VIII]
wherein R1 is as defined above.
9. The method of claim 2 or 3, which further comprises a step
of purifying a compound of the formula [II]

with 1-propanol.
10. A method of producing a compound of the formula [XI]
wherein R2 is hydrogen, Ci-g alkyl or Ci-6 alkoxy,
which comprises a step of subjecting a compound of the formula
[XII]
wherein R2 is as defined above, to methylation.
11. A compound of the formula [V]

12. A compound of the formula [III]
13. A compound of the formula [VI]
f
wherein R1 and R2 are each independently hydrogen, Ci-g alkyl or Ci-6 alkoxy.
14. A compound of the formula [VII]

wherein R1 is hydrogen, Ci_s alkyl or Ci-6 alkoxy. 15. A compound of the formula [VIII]
y wherein R1 is hydrogen, Ci_6 alkyl or Ci-e alkoxy. 16. A compound of the formula [XI]
t
wherein R2 is hydrogen, Ci-e alkyl or Ci-e alkoxy.
10

Documents

Application Documents

# Name Date
1 Translated Copy of Priority Document [01-02-2017(online)].pdf 2017-02-01
2 PROOF OF RIGHT [01-02-2017(online)].pdf 2017-02-01
3 Priority Document [01-02-2017(online)].pdf 2017-02-01
4 Power of Attorney [01-02-2017(online)].pdf 2017-02-01
5 Form 5 [01-02-2017(online)].pdf 2017-02-01
6 Form 3 [01-02-2017(online)].pdf 2017-02-01
7 Drawing [01-02-2017(online)].pdf 2017-02-01
8 Description(Complete) [01-02-2017(online)].pdf_429.pdf 2017-02-01
9 Description(Complete) [01-02-2017(online)].pdf 2017-02-01
10 201747003662.pdf 2017-02-02
11 Correspondence by Agent_Executed Form1_03-02-2017.pdf 2017-02-03
12 201747003662-FORM 3 [28-07-2017(online)].pdf 2017-07-28
13 201747003662-FORM 3 [01-02-2018(online)].pdf 2018-02-01
14 201747003662-RELEVANT DOCUMENTS [03-07-2018(online)].pdf 2018-07-03
15 201747003662-MARKED COPIES OF AMENDEMENTS [03-07-2018(online)].pdf 2018-07-03
16 201747003662-FORM 18 [03-07-2018(online)].pdf 2018-07-03
17 201747003662-AMMENDED DOCUMENTS [03-07-2018(online)].pdf 2018-07-03
18 201747003662-Amendment Of Application Before Grant - Form 13 [03-07-2018(online)].pdf 2018-07-03
19 201747003662-FORM 3 [12-07-2018(online)].pdf 2018-07-12
20 201747003662-RELEVANT DOCUMENTS [14-09-2018(online)].pdf 2018-09-14
21 201747003662-Changing Name-Nationality-Address For Service [14-09-2018(online)].pdf 2018-09-14
22 201747003662-AMENDED DOCUMENTS [14-09-2018(online)].pdf 2018-09-14
23 Correspondence by Agent_Power of Attorney_20-09-2018.pdf 2018-09-20
24 201747003662-Verified English translation (MANDATORY) [16-11-2018(online)].pdf 2018-11-16
25 Correspondence by Agent _Verified English Translation_22-11-2018.pdf 2018-11-22
26 201747003662-FORM 3 [27-12-2018(online)].pdf 2018-12-27
27 201747003662-FORM 3 [07-06-2019(online)].pdf 2019-06-07
28 201747003662-FER.pdf 2019-10-29
29 201747003662-Information under section 8(2) [10-02-2020(online)].pdf 2020-02-10
30 201747003662-FORM 3 [10-02-2020(online)].pdf 2020-02-10
31 201747003662-OTHERS [04-04-2020(online)].pdf 2020-04-04
32 201747003662-FER_SER_REPLY [04-04-2020(online)].pdf 2020-04-04
33 201747003662-DRAWING [04-04-2020(online)].pdf 2020-04-04
34 201747003662-COMPLETE SPECIFICATION [04-04-2020(online)].pdf 2020-04-04
35 201747003662-CLAIMS [04-04-2020(online)].pdf 2020-04-04
36 201747003662-ABSTRACT [04-04-2020(online)].pdf 2020-04-04
37 201747003662-PatentCertificate24-04-2020.pdf 2020-04-24
38 201747003662-Marked up Claims_Granted 335986_24-04-2020.pdf 2020-04-24
39 201747003662-IntimationOfGrant24-04-2020.pdf 2020-04-24
40 201747003662-Drawings_Granted 335986_24-04-2020.pdf 2020-04-24
41 201747003662-Description_Granted 335986_24-04-2020.pdf 2020-04-24
42 201747003662-Claims_Granted 335986_24-04-2020.pdf 2020-04-24
43 201747003662-Abstract_Granted 335986_24-04-2020.pdf 2020-04-24
44 201747003662-RELEVANT DOCUMENTS [25-07-2022(online)].pdf 2022-07-25
45 201747003662-RELEVANT DOCUMENTS [09-08-2022(online)].pdf 2022-08-09
46 201747003662-RELEVANT DOCUMENTS [19-06-2023(online)].pdf 2023-06-19

Search Strategy

1 search_16-10-2019.pdf

ERegister / Renewals

3rd: 07 Jul 2020

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4th: 07 Jul 2020

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