JPWO2020051503A5 - - Google Patents
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- Publication number
- JPWO2020051503A5 JPWO2020051503A5 JP2021512696A JP2021512696A JPWO2020051503A5 JP WO2020051503 A5 JPWO2020051503 A5 JP WO2020051503A5 JP 2021512696 A JP2021512696 A JP 2021512696A JP 2021512696 A JP2021512696 A JP 2021512696A JP WO2020051503 A5 JPWO2020051503 A5 JP WO2020051503A5
- Authority
- JP
- Japan
- Prior art keywords
- optionally substituted
- formula
- compound
- mixture
- alkyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 239000000203 mixture Substances 0.000 claims description 35
- 150000001875 compounds Chemical class 0.000 claims description 27
- 125000000217 alkyl group Chemical group 0.000 claims description 20
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 20
- 239000003638 reducing agent Substances 0.000 claims description 14
- -1 9-fluorenyl Chemical group 0.000 claims description 10
- 230000003287 optical Effects 0.000 claims description 10
- 239000003880 polar aprotic solvent Substances 0.000 claims description 10
- 239000011541 reaction mixture Substances 0.000 claims description 10
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 8
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 8
- 230000027455 binding Effects 0.000 claims description 6
- 239000003446 ligand Substances 0.000 claims description 6
- 238000003756 stirring Methods 0.000 claims description 6
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 6
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 4
- 125000003358 C2-C20 alkenyl group Chemical group 0.000 claims description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 4
- 125000000304 alkynyl group Chemical group 0.000 claims description 4
- 150000001450 anions Chemical class 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 238000005966 aza-Michael addition reaction Methods 0.000 claims description 4
- 125000006244 carboxylic acid protecting group Chemical group 0.000 claims description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical group CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 4
- 125000001072 heteroaryl group Chemical group 0.000 claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- 239000012535 impurity Substances 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 238000010791 quenching Methods 0.000 claims description 4
- 230000000171 quenching Effects 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 3
- 238000003818 flash chromatography Methods 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 3
- 238000000926 separation method Methods 0.000 claims description 3
- 125000001989 1,3-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([H])C([*:2])=C1[H] 0.000 claims description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 2
- 239000007848 Bronsted acid Substances 0.000 claims description 2
- IUBQJLUDMLPAGT-UHFFFAOYSA-N Potassium bis(trimethylsilyl)amide Chemical group C[Si](C)(C)N([K])[Si](C)(C)C IUBQJLUDMLPAGT-UHFFFAOYSA-N 0.000 claims description 2
- KXDHJXZQYSOELW-UHFFFAOYSA-M carbamate Chemical group NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 2
- 238000001816 cooling Methods 0.000 claims description 2
- 238000002156 mixing Methods 0.000 claims description 2
- BDOLXPFAFMNDOK-UHFFFAOYSA-N oxazaborolidine Chemical compound B1CCON1 BDOLXPFAFMNDOK-UHFFFAOYSA-N 0.000 claims description 2
- 230000000717 retained Effects 0.000 claims description 2
- 239000000741 silica gel Substances 0.000 claims description 2
- 229910002027 silica gel Inorganic materials 0.000 claims description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 239000011780 sodium chloride Substances 0.000 claims 1
- 239000000543 intermediate Substances 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N methylene dichloride Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 239000000463 material Substances 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- OZMJKQBMQWNYBS-VXGBXAGGSA-N C(C)(C)(C)OC(=O)N([C@H](C[C@@H](O)C=1SC=C(N=1)C(=O)O)C(C)C)C Chemical compound C(C)(C)(C)OC(=O)N([C@H](C[C@@H](O)C=1SC=C(N=1)C(=O)O)C(C)C)C OZMJKQBMQWNYBS-VXGBXAGGSA-N 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201862728639P | 2018-09-07 | 2018-09-07 | |
| US62/728,639 | 2018-09-07 | ||
| PCT/US2019/050023 WO2020051503A1 (en) | 2018-09-07 | 2019-09-06 | Alternative processes for the preparation of tubulysins and intermediates thereof |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2021536475A JP2021536475A (ja) | 2021-12-27 |
| JPWO2020051503A5 true JPWO2020051503A5 (zh) | 2022-09-14 |
| JP7511543B2 JP7511543B2 (ja) | 2024-07-05 |
Family
ID=68000124
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2021512696A Active JP7511543B2 (ja) | 2018-09-07 | 2019-09-06 | チューブリシンおよびそれらの中間体の調製のための代替プロセス |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US20230002440A1 (zh) |
| EP (1) | EP3847161A1 (zh) |
| JP (1) | JP7511543B2 (zh) |
| KR (1) | KR20210073525A (zh) |
| CN (1) | CN112996778A (zh) |
| AU (1) | AU2019336231A1 (zh) |
| BR (1) | BR112021004317A2 (zh) |
| CA (1) | CA3111149A1 (zh) |
| EA (1) | EA202190699A1 (zh) |
| IL (1) | IL281090A (zh) |
| MA (1) | MA53550A (zh) |
| MX (1) | MX2021002570A (zh) |
| SG (1) | SG11202102126VA (zh) |
| TW (1) | TWI825169B (zh) |
| WO (1) | WO2020051503A1 (zh) |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2723671C (en) * | 2007-05-10 | 2018-06-19 | R & D Biopharmaceuticals Gmbh | Tubulysine derivatives |
| IT1394860B1 (it) | 2009-07-22 | 2012-07-20 | Kemotech S R L | Composti farmaceutici |
| MX2018006218A (es) | 2015-12-04 | 2018-09-05 | Seattle Genetics Inc | Conjugados de compuestos de tubulisina cuaternizada. |
| US11389543B2 (en) | 2017-09-08 | 2022-07-19 | Seagen Inc. | Process for the preparation of tubulysins and intermediates thereof |
-
2019
- 2019-09-06 CA CA3111149A patent/CA3111149A1/en active Pending
- 2019-09-06 AU AU2019336231A patent/AU2019336231A1/en active Pending
- 2019-09-06 WO PCT/US2019/050023 patent/WO2020051503A1/en active Application Filing
- 2019-09-06 US US17/273,693 patent/US20230002440A1/en active Pending
- 2019-09-06 BR BR112021004317-9A patent/BR112021004317A2/pt unknown
- 2019-09-06 TW TW108132162A patent/TWI825169B/zh active
- 2019-09-06 CN CN201980071734.XA patent/CN112996778A/zh active Pending
- 2019-09-06 MX MX2021002570A patent/MX2021002570A/es unknown
- 2019-09-06 MA MA053550A patent/MA53550A/fr unknown
- 2019-09-06 EA EA202190699A patent/EA202190699A1/ru unknown
- 2019-09-06 EP EP19773284.5A patent/EP3847161A1/en active Pending
- 2019-09-06 KR KR1020217010157A patent/KR20210073525A/ko active Search and Examination
- 2019-09-06 JP JP2021512696A patent/JP7511543B2/ja active Active
- 2019-09-06 SG SG11202102126VA patent/SG11202102126VA/en unknown
-
2021
- 2021-02-24 IL IL281090A patent/IL281090A/en unknown
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