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).
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
| # | 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 |
| 1 | search_16-10-2019.pdf |