Abstract: Provided are an efficient method for producing a nitrogen containing compound or salt thereof to be used in the production of a treatment agent for diseases involving an integrin. Also provided is a production intermediate of the same. A method for producing a novel nitrogen containing compound or salt thereof said method comprising: (1) a step for obtaining a compound represented by general formula [10] or salt thereof by an amidation reaction; and (2) a step for deprotecting the compound represented by general formula [10] or salt thereof.
1. A method for manufacturing a compound represented by Formula [11] or a salt thereof, comprising:
(1) a step of reacting a compound represented by Formula [1] or a salt thereof
1 9
(in the formula, R represents a hydrogen atom or an amino-protecting group; R represents a carboxyl-protecting group; L1 represents a group represented by Formula [2a]
(in the formula, R3a, R4a, R5a, and R6a are the same as or different from each other and represent a hydrogen atom or a Ci_6 alkyl group; p represents an integer of 1 to 3; q represents an integer of 0 to 3; and r represents an integer of 1 to 6); and L represents a group represented by Formula [2b]
(in the formula, R3b, R4b, R5b, and R6b are the same as or different from each other and
9 9
represent a hydrogen atom or a Ci-6 alkyl group; p represents an integer of 1 to 3, q
represents an integer of 0 to 3; and r2 represents an integer of 1 to 6)) with a compound represented by Formula [3] or a salt thereof
"2
(in the formula, L represents a group represented by Formula [2c]
(in the formula, R3c, R4c, R5c, and R6c are the same as or different from each other and represent a hydrogen atom or a Ci-6 alkyl group; p represents an integer of 1 to 3; q represents an integer of 0 to 3; and r represents an integer of 1 to 6); A represents any one of the groups represented by Formulae [4] to [9]
n
(in the formulae, * represents a binding position; and R 's are the same as or different from each other and represent a carboxyl-protecting group); and m represents an integer of 1 to 3)) so as to obtain a compound represented by Formula [10] or a salt thereof;
(in the formula, R,R,L,L,L,A, and m have the same definition as R , R , L , L , L , A , and m described above); and
(2) a step of deprotecting the compound represented by Formula [10] or a salt thereof,
(in the formula, A represents any one of the groups represented by Formulae [12] to
1 9 "2
(in the formulae, * represents a binding position); and L , L , L , and m have the same definition as L , L , L ' and m described above).
2. The manufacturing method according to claim 1,
wherein R is a C1-6 alkyl group which may be substituted or a benzyl group which may be substituted.
3. The manufacturing method according to claim 1 or 2,
(in the formula, R5c and R6c may be the same as or different from each other and represent a hydrogen atom or a Ci-6 alkyl group; and r represents an integer of 1 to 6).
4. The manufacturing method according to any one claims 1 to 3, wherein L1 is a group represented by Formula [18a]
(in the formula, R5a and R6a are the same as or different from each other and represent a hydrogen atom or a Ci_6 alkyl group; and r1 represents an integer of 1 to 6).
5. The manufacturing method according to any one of claims 1 to 4, wherein L is a group represented by Formula [18b]
(in the formula, R5b and R6b are the same as or different from each other and represent a hydrogen atom or a Ci-6 alkyl group; and r represents an integer of 1 to 6).
6. The manufacturing method according to any one of claims 1 to 5,
wherein R1 is a hydrogen atom, a Ci_6 alkoxycarbonyl group which may be substituted, an arylsulfonyl group which may be substituted, or a heterocyclic sulfonyl group
7. The manufacturing method according to any one of claims 1 to 6,
wherein R7 is a Ci_6 alkyl group which may be substituted or a benzyl group which may be substituted.
8. The manufacturing method according to any one of claims 1 to 7,
wherein the step of deprotecting is a step of deprotecting by using an acid.
9. A method for manufacturing a metal complex, comprising:
a step of reacting the compound represented by Formula [11] or a salt thereof obtained by the manufacturing method according to any one of claims 1 to 7 with a metal ion.
10. A compound represented by Formula [19] or a salt thereof
1 S
(in the formula, R represents a hydrogen atom or an amino-protecting group; R represents a C2-6 alkyl group which may be substituted or a benzyl group which may be substituted; R9 represents a hydrogen atom, an amino-protecting group, or a group represented by Formula [20]
(in the formula, * represents a binding position, L represents a group represented by Formula [2c]
—. _ p_ _
(in the formula, R3c, R4c, R5c, and R6c are the same as or different from each other and represent a hydrogen atom or a Cj.6 alkyl group; p represents an integer of 1 to 3; q represents an integer of 0 to 3; and r represents an integer of 1 to 6); A represents any one of the groups represented by Formulae [4] to [9]
n
(in the formulae, * represents a binding position; and R represents a carboxyl-protecting group); and m represents an integer of 1 to 3); L represents a group represented by Formula [2b]
(in the formula, R , R , R , and R are the same as or different from each other and represent a hydrogen atom or a Ci-6 alkyl group; p represents an integer of 1 to 3; q represents an integer of 0 to 3; and r represents an integer of 1 to 6); and L represents a group represented by Formula [2a]
(in the formula, R3a, R4a, R5a, and R6a are the same as or different from each other and represent a hydrogen atom or a Ci_6 alkyl group; p1 represents an integer of 1 to 3; q1 represents an integer of 0 to 3; and r represents an integer of 1 to 6)).
11. The compound according to claim 10 or a salt thereof,
o
wherein R is a C2-6 alkyl group which may be substituted.
12. The compound according to claim 10 or 11 or a salt thereof,
wherein L is a group represented by Formula [18c]
(in the formula, R5c and R6c are the same as or different from each other and represent a hydrogen atom or a Ci_6 alkyl group; and r represents an integer of 1 to 6).
13. The compound according to any one of claims 10 to 12 or a salt thereof, wherein L1 is a group represented by Formula [18a]
(in the formula, R5a and R6a are the same as or different from each other and represent
a hydrogen atom or a Cj.6 alkyl group; and r1 represents an integer of 1 to 6).
14. The compound according to any one of claims 10 to 13 or a salt thereof, wherein L2 represents a group represented by Formula [18b]
(in the formula, R and R are the same as or different from each other and represent a hydrogen atom or a Ci-6 alkyl group; and r represents an integer of 1 to 6).
15. The compound according to any one of claims 10 to 14 or a salt thereof,
wherein R1 is a hydrogen atom, a Ci-6 alkoxycarbonyl group which may be substituted, an arylsulfonyl group which may be substituted, or a heterocyclic sulfonyl group which may be substituted.
16. The compound according to any one of claims 10 to 15 or a salt thereof,
wherein R7 is a Ci_6 alkyl group which may be substituted or a benzyl group which may be substituted.
17. A compound represented by Formula [3] or a salt thereof
(in the formula, R3c, R4c, R5c, and R6c are the same as or different from each other and represent a hydrogen atom or a Ci_6 alkyl group; p represents an integer of 1 to 3; q
n 1
represents an integer of 0 to 3; and r represents an integer of 1 to 6); A represents any one of the groups represented by Formulae [4] to [9]
(in the formulae, * represents a binding position; and R7 represents a carboxyl-protecting group); and m represents an integer of 1 to 3).
| # | Name | Date |
|---|---|---|
| 1 | 201747033642-FORM-27 [30-09-2024(online)].pdf | 2024-09-30 |
| 1 | 201747033642-TRANSLATIOIN OF PRIOIRTY DOCUMENTS ETC. [22-09-2017(online)].pdf | 2017-09-22 |
| 2 | 201747033642-STATEMENT OF UNDERTAKING (FORM 3) [22-09-2017(online)].pdf | 2017-09-22 |
| 2 | 201747033642-RELEVANT DOCUMENTS [29-09-2023(online)].pdf | 2023-09-29 |
| 3 | 201747033642-REQUEST FOR EXAMINATION (FORM-18) [22-09-2017(online)].pdf | 2017-09-22 |
| 3 | 201747033642-RELEVANT DOCUMENTS [20-09-2023(online)]-1.pdf | 2023-09-20 |
| 4 | 201747033642-RELEVANT DOCUMENTS [20-09-2023(online)].pdf | 2023-09-20 |
| 4 | 201747033642-PROOF OF RIGHT [22-09-2017(online)].pdf | 2017-09-22 |
| 5 | 201747033642-RELEVANT DOCUMENTS [14-08-2023(online)].pdf | 2023-08-14 |
| 5 | 201747033642-PRIORITY DOCUMENTS [22-09-2017(online)].pdf | 2017-09-22 |
| 6 | 201747033642-RELEVANT DOCUMENTS [14-09-2022(online)].pdf | 2022-09-14 |
| 6 | 201747033642-POWER OF AUTHORITY [22-09-2017(online)].pdf | 2017-09-22 |
| 7 | 201747033642-RELEVANT DOCUMENTS [26-08-2022(online)].pdf | 2022-08-26 |
| 7 | 201747033642-FORM 18 [22-09-2017(online)].pdf | 2017-09-22 |
| 8 | 201747033642-IntimationOfGrant31-01-2021.pdf | 2021-01-31 |
| 8 | 201747033642-FORM 1 [22-09-2017(online)].pdf | 2017-09-22 |
| 9 | 201747033642-PatentCertificate31-01-2021.pdf | 2021-01-31 |
| 9 | 201747033642-DRAWINGS [22-09-2017(online)].pdf | 2017-09-22 |
| 10 | 201747033642-DECLARATION OF INVENTORSHIP (FORM 5) [22-09-2017(online)].pdf | 2017-09-22 |
| 10 | 201747033642-FORM 3 [27-08-2020(online)].pdf | 2020-08-27 |
| 11 | 201747033642-COMPLETE SPECIFICATION [22-09-2017(online)].pdf | 2017-09-22 |
| 11 | 201747033642-FORM 3 [21-10-2019(online)].pdf | 2019-10-21 |
| 12 | 201747033642-ABSTRACT [19-08-2019(online)].pdf | 2019-08-19 |
| 12 | 201747033642-CLAIMS UNDER RULE 1 (PROVISIO) OF RULE 20 [22-09-2017(online)].pdf | 2017-09-22 |
| 13 | 201747033642-CLAIMS [19-08-2019(online)].pdf | 2019-08-19 |
| 13 | 201747033642.pdf | 2017-09-26 |
| 14 | 201747033642-COMPLETE SPECIFICATION [19-08-2019(online)].pdf | 2019-08-19 |
| 14 | 201747033642-RELEVANT DOCUMENTS [05-10-2017(online)].pdf | 2017-10-05 |
| 15 | 201747033642-DRAWING [19-08-2019(online)].pdf | 2019-08-19 |
| 15 | 201747033642-MARKED COPIES OF AMENDEMENTS [05-10-2017(online)].pdf | 2017-10-05 |
| 16 | 201747033642-Annexure [05-10-2017(online)].pdf | 2017-10-05 |
| 16 | 201747033642-FER_SER_REPLY [19-08-2019(online)].pdf | 2019-08-19 |
| 17 | 201747033642-AMMENDED DOCUMENTS [05-10-2017(online)].pdf | 2017-10-05 |
| 17 | 201747033642-FORM 3 [19-08-2019(online)].pdf | 2019-08-19 |
| 18 | 201747033642-Amendment Of Application Before Grant - Form 13 [05-10-2017(online)].pdf | 2017-10-05 |
| 18 | 201747033642-Information under section 8(2) (MANDATORY) [19-08-2019(online)].pdf | 2019-08-19 |
| 19 | 201747033642-Proof of Right (MANDATORY) [13-10-2017(online)].pdf | 2017-10-13 |
| 19 | 201747033642-OTHERS [19-08-2019(online)].pdf | 2019-08-19 |
| 20 | 201747033642-PETITION UNDER RULE 137 [19-08-2019(online)].pdf | 2019-08-19 |
| 20 | Correspondence by Agent_ Executed FORM 1_27-10-2017.pdf | 2017-10-27 |
| 21 | 201747033642-FORM 3 [12-12-2017(online)].pdf | 2017-12-12 |
| 21 | 201747033642-FORM 3 [29-04-2019(online)].pdf | 2019-04-29 |
| 22 | 201747033642-FER.pdf | 2019-02-26 |
| 22 | 201747033642-FORM 3 [17-05-2018(online)].pdf | 2018-05-17 |
| 23 | 201747033642-FER.pdf | 2019-02-26 |
| 23 | 201747033642-FORM 3 [17-05-2018(online)].pdf | 2018-05-17 |
| 24 | 201747033642-FORM 3 [12-12-2017(online)].pdf | 2017-12-12 |
| 24 | 201747033642-FORM 3 [29-04-2019(online)].pdf | 2019-04-29 |
| 25 | Correspondence by Agent_ Executed FORM 1_27-10-2017.pdf | 2017-10-27 |
| 25 | 201747033642-PETITION UNDER RULE 137 [19-08-2019(online)].pdf | 2019-08-19 |
| 26 | 201747033642-OTHERS [19-08-2019(online)].pdf | 2019-08-19 |
| 26 | 201747033642-Proof of Right (MANDATORY) [13-10-2017(online)].pdf | 2017-10-13 |
| 27 | 201747033642-Amendment Of Application Before Grant - Form 13 [05-10-2017(online)].pdf | 2017-10-05 |
| 27 | 201747033642-Information under section 8(2) (MANDATORY) [19-08-2019(online)].pdf | 2019-08-19 |
| 28 | 201747033642-AMMENDED DOCUMENTS [05-10-2017(online)].pdf | 2017-10-05 |
| 28 | 201747033642-FORM 3 [19-08-2019(online)].pdf | 2019-08-19 |
| 29 | 201747033642-Annexure [05-10-2017(online)].pdf | 2017-10-05 |
| 29 | 201747033642-FER_SER_REPLY [19-08-2019(online)].pdf | 2019-08-19 |
| 30 | 201747033642-DRAWING [19-08-2019(online)].pdf | 2019-08-19 |
| 30 | 201747033642-MARKED COPIES OF AMENDEMENTS [05-10-2017(online)].pdf | 2017-10-05 |
| 31 | 201747033642-COMPLETE SPECIFICATION [19-08-2019(online)].pdf | 2019-08-19 |
| 31 | 201747033642-RELEVANT DOCUMENTS [05-10-2017(online)].pdf | 2017-10-05 |
| 32 | 201747033642-CLAIMS [19-08-2019(online)].pdf | 2019-08-19 |
| 32 | 201747033642.pdf | 2017-09-26 |
| 33 | 201747033642-ABSTRACT [19-08-2019(online)].pdf | 2019-08-19 |
| 33 | 201747033642-CLAIMS UNDER RULE 1 (PROVISIO) OF RULE 20 [22-09-2017(online)].pdf | 2017-09-22 |
| 34 | 201747033642-COMPLETE SPECIFICATION [22-09-2017(online)].pdf | 2017-09-22 |
| 34 | 201747033642-FORM 3 [21-10-2019(online)].pdf | 2019-10-21 |
| 35 | 201747033642-DECLARATION OF INVENTORSHIP (FORM 5) [22-09-2017(online)].pdf | 2017-09-22 |
| 35 | 201747033642-FORM 3 [27-08-2020(online)].pdf | 2020-08-27 |
| 36 | 201747033642-DRAWINGS [22-09-2017(online)].pdf | 2017-09-22 |
| 36 | 201747033642-PatentCertificate31-01-2021.pdf | 2021-01-31 |
| 37 | 201747033642-IntimationOfGrant31-01-2021.pdf | 2021-01-31 |
| 37 | 201747033642-FORM 1 [22-09-2017(online)].pdf | 2017-09-22 |
| 38 | 201747033642-RELEVANT DOCUMENTS [26-08-2022(online)].pdf | 2022-08-26 |
| 38 | 201747033642-FORM 18 [22-09-2017(online)].pdf | 2017-09-22 |
| 39 | 201747033642-RELEVANT DOCUMENTS [14-09-2022(online)].pdf | 2022-09-14 |
| 39 | 201747033642-POWER OF AUTHORITY [22-09-2017(online)].pdf | 2017-09-22 |
| 40 | 201747033642-RELEVANT DOCUMENTS [14-08-2023(online)].pdf | 2023-08-14 |
| 40 | 201747033642-PRIORITY DOCUMENTS [22-09-2017(online)].pdf | 2017-09-22 |
| 41 | 201747033642-RELEVANT DOCUMENTS [20-09-2023(online)].pdf | 2023-09-20 |
| 41 | 201747033642-PROOF OF RIGHT [22-09-2017(online)].pdf | 2017-09-22 |
| 42 | 201747033642-REQUEST FOR EXAMINATION (FORM-18) [22-09-2017(online)].pdf | 2017-09-22 |
| 42 | 201747033642-RELEVANT DOCUMENTS [20-09-2023(online)]-1.pdf | 2023-09-20 |
| 43 | 201747033642-RELEVANT DOCUMENTS [29-09-2023(online)].pdf | 2023-09-29 |
| 43 | 201747033642-STATEMENT OF UNDERTAKING (FORM 3) [22-09-2017(online)].pdf | 2017-09-22 |
| 44 | 201747033642-FORM-27 [30-09-2024(online)].pdf | 2024-09-30 |
| 44 | 201747033642-TRANSLATIOIN OF PRIOIRTY DOCUMENTS ETC. [22-09-2017(online)].pdf | 2017-09-22 |
| 1 | search_21-02-2019.pdf |