JP2020519583A5 - - Google Patents
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- Publication number
- JP2020519583A5 JP2020519583A5 JP2019561210A JP2019561210A JP2020519583A5 JP 2020519583 A5 JP2020519583 A5 JP 2020519583A5 JP 2019561210 A JP2019561210 A JP 2019561210A JP 2019561210 A JP2019561210 A JP 2019561210A JP 2020519583 A5 JP2020519583 A5 JP 2020519583A5
- Authority
- JP
- Japan
- Prior art keywords
- compound
- formula
- amine compound
- alkyl
- cycloalkyl
- 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.)
- Abandoned
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- -1 amine compound Chemical class 0.000 claims description 121
- 150000001875 compounds Chemical class 0.000 claims description 45
- 150000003839 salts Chemical class 0.000 claims description 43
- 238000000034 method Methods 0.000 claims description 39
- 125000000217 alkyl group Chemical group 0.000 claims description 31
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 25
- 239000011549 crystallization solution Substances 0.000 claims description 16
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
- 125000006239 protecting group Chemical group 0.000 claims description 9
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 8
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 150000002367 halogens Chemical class 0.000 claims description 8
- 125000000623 heterocyclic group Chemical group 0.000 claims description 8
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 claims description 8
- 229910052717 sulfur Inorganic materials 0.000 claims description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 6
- 125000002252 acyl group Chemical group 0.000 claims description 6
- 125000004423 acyloxy group Chemical group 0.000 claims description 6
- 150000008052 alkyl sulfonates Chemical class 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 125000001072 heteroaryl group Chemical group 0.000 claims description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 6
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims description 6
- 229940080328 Arginase inhibitor Drugs 0.000 claims description 5
- 125000005227 alkyl sulfonate group Chemical group 0.000 claims description 5
- 125000005228 aryl sulfonate group Chemical group 0.000 claims description 5
- 125000003143 4-hydroxybenzyl group Chemical group [H]C([*])([H])C1=C([H])C([H])=C(O[H])C([H])=C1[H] 0.000 claims description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 4
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 4
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 4
- 238000006197 hydroboration reaction Methods 0.000 claims description 4
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 4
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims description 4
- 239000002243 precursor Substances 0.000 claims description 4
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- 239000000243 solution Substances 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
- 125000000025 triisopropylsilyl group Chemical group C(C)(C)[Si](C(C)C)(C(C)C)* 0.000 claims description 4
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
- 150000003335 secondary amines Chemical class 0.000 claims description 3
- 238000002425 crystallisation Methods 0.000 claims description 2
- 230000008025 crystallization Effects 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 238000001640 fractional crystallisation Methods 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 2
- 239000006228 supernatant Substances 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 16
- 229910052799 carbon Inorganic materials 0.000 claims 14
- 229910052739 hydrogen Inorganic materials 0.000 claims 12
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 claims 2
- BMQDAIUNAGXSKR-UHFFFAOYSA-N (3-hydroxy-2,3-dimethylbutan-2-yl)oxyboronic acid Chemical group CC(C)(O)C(C)(C)OB(O)O BMQDAIUNAGXSKR-UHFFFAOYSA-N 0.000 claims 1
- 150000008055 alkyl aryl sulfonates Chemical class 0.000 claims 1
- 229940045714 alkyl sulfonate alkylating agent Drugs 0.000 claims 1
- 230000002862 amidating effect Effects 0.000 claims 1
- 125000006242 amine protecting group Chemical group 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- 239000000126 substance Substances 0.000 description 13
- 238000007112 amidation reaction Methods 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201762505282P | 2017-05-12 | 2017-05-12 | |
| US62/505,282 | 2017-05-12 | ||
| PCT/US2018/032407 WO2018209290A1 (en) | 2017-05-12 | 2018-05-11 | Method of preparing (3r,4s)-3-acetamido-4-allyl-n-(tert-butyl)pyrrolidine-3-carboxamide |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2020519583A JP2020519583A (ja) | 2020-07-02 |
| JP2020519583A5 true JP2020519583A5 (https=) | 2021-07-26 |
Family
ID=62387001
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2019561210A Abandoned JP2020519583A (ja) | 2017-05-12 | 2018-05-11 | （３ｒ，４ｓ）−３−アセトアミド−４−アリル−ｎ−（ｔｅｒｔ−ブチル）ピロリジン−３−カルボキサミドの製造方法 |
Country Status (21)
| Country | Link |
|---|---|
| US (3) | US10494339B2 (https=) |
| EP (1) | EP3621954B1 (https=) |
| JP (1) | JP2020519583A (https=) |
| KR (1) | KR20200008578A (https=) |
| CN (1) | CN110709383A (https=) |
| AU (1) | AU2018265873A1 (https=) |
| BR (1) | BR112019023582A2 (https=) |
| CA (1) | CA3062851A1 (https=) |
| CL (1) | CL2019003212A1 (https=) |
| CO (1) | CO2019013923A2 (https=) |
| CR (1) | CR20190562A (https=) |
| EA (1) | EA201992695A1 (https=) |
| IL (2) | IL278757B (https=) |
| MA (1) | MA48626A (https=) |
| MX (1) | MX2019013533A (https=) |
| PE (1) | PE20200339A1 (https=) |
| PH (1) | PH12019502505A1 (https=) |
| SG (1) | SG10201912946TA (https=) |
| TW (1) | TW201900609A (https=) |
| WO (1) | WO2018209290A1 (https=) |
| ZA (1) | ZA201908267B (https=) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK2632927T3 (en) | 2010-10-26 | 2016-04-11 | Mars Inc | Boronates AS ARGINSASEINHIBITORER |
| SMT202100573T1 (it) | 2016-12-22 | 2021-11-12 | Calithera Biosciences Inc | Composizioni e metodi per l'inibizione dell'attivita' dell'arginasi |
| WO2018209290A1 (en) * | 2017-05-12 | 2018-11-15 | Calithera Biosciences, Inc. | Method of preparing (3r,4s)-3-acetamido-4-allyl-n-(tert-butyl)pyrrolidine-3-carboxamide |
| EP3774843B1 (en) | 2018-03-29 | 2022-05-25 | Molecure SA | Dipeptide piperidine derivatives |
| CN110734456A (zh) * | 2019-11-06 | 2020-01-31 | 南京谷睿生物科技有限公司 | 一种化合物及其制备方法和医药上的应用 |
| US20220041630A1 (en) | 2020-07-17 | 2022-02-10 | Incyte Corporation | Processes for the preparation of arginase inhibitors and their synthetic intermediates |
| CN113866289A (zh) * | 2021-09-03 | 2021-12-31 | 上海凌凯医药科技有限公司 | 2,3-二苯甲酰氧基-4-二甲基氨基-4-氧代丁酸的手性分离检测方法 |
Family Cites Families (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1999019295A1 (en) | 1997-10-10 | 1999-04-22 | Trustees Of The University Of Pennsylvania | Compositions and methods for inhibiting arginase activity |
| US20040063666A1 (en) | 1998-10-09 | 2004-04-01 | David Christianson | Compositions for inhibiting arginase activity |
| JP2004502948A (ja) | 2000-07-06 | 2004-01-29 | ファル ダイアグノスティクス | アルギニン化合物の検出のための方法及びキット |
| CA2431080A1 (en) | 2003-06-02 | 2004-12-02 | Catherine Adele O'brien | Enhancement of anticancer immunity through inhibition of arginase |
| WO2007005620A2 (en) | 2005-07-01 | 2007-01-11 | The Johns Hopkins University | Arginase ii: a target treatment of aging heart and heart failure |
| SI2389352T1 (sl) | 2009-01-26 | 2019-08-30 | The Trustees Of The University Of Pennsylvania, Center For Technology Transfer | Inhibitorji arginaze in postopki uporabe |
| CN103068830B (zh) | 2010-04-22 | 2016-06-29 | 马尔斯公司 | 精氨酸酶抑制剂及其治疗应用 |
| DK2632927T3 (en) | 2010-10-26 | 2016-04-11 | Mars Inc | Boronates AS ARGINSASEINHIBITORER |
| CA2824599C (en) | 2010-12-31 | 2020-03-10 | Astrazeneca Uk Limited | Arginase inhibitors and methods of use thereof |
| US9266908B2 (en) | 2011-10-19 | 2016-02-23 | Mars, Incorporated | Inhibitors of arginase and their therapeutic applications |
| RU2014120166A (ru) | 2011-10-20 | 2015-11-27 | ГЛЭКСОСМИТКЛАЙН ЭлЭлСи | Замещенные бициклические аза-гетероциклы и их аналоги в качестве модуляторов сиртуина |
| CA2870526C (en) | 2012-04-18 | 2020-05-05 | Mars, Incorporated | Ring constrained analogs as arginase inhibitors |
| JP6508785B2 (ja) | 2013-10-25 | 2019-05-08 | ファーマサイクリックス エルエルシー | ブルトンチロシンキナーゼ阻害剤および免疫療法を使用する処置 |
| CN105879030A (zh) | 2014-09-30 | 2016-08-24 | 复旦大学 | 治疗肿瘤的增效药物复合物及其制备方法 |
| CN107405404A (zh) | 2015-03-20 | 2017-11-28 | 塞米·欧尤·奥皮约 | 苏拉明和精氨酸酶抑制剂在恶性肿瘤中的用途 |
| KR20180021117A (ko) | 2015-06-23 | 2018-02-28 | 칼리테라 바이오사이언시즈, 인코포레이티드 | 아르기나제 활성 억제를 위한 조성물 및 방법 |
| WO2017075363A1 (en) * | 2015-10-30 | 2017-05-04 | Calithera Biosciences, Inc. | Compositions and methods for inhibiting arginase activity |
| WO2018209290A1 (en) * | 2017-05-12 | 2018-11-15 | Calithera Biosciences, Inc. | Method of preparing (3r,4s)-3-acetamido-4-allyl-n-(tert-butyl)pyrrolidine-3-carboxamide |
-
2018
- 2018-05-11 WO PCT/US2018/032407 patent/WO2018209290A1/en not_active Ceased
- 2018-05-11 BR BR112019023582-5A patent/BR112019023582A2/pt not_active Application Discontinuation
- 2018-05-11 PE PE2019002393A patent/PE20200339A1/es unknown
- 2018-05-11 EA EA201992695A patent/EA201992695A1/ru unknown
- 2018-05-11 MA MA048626A patent/MA48626A/fr unknown
- 2018-05-11 JP JP2019561210A patent/JP2020519583A/ja not_active Abandoned
- 2018-05-11 KR KR1020197036665A patent/KR20200008578A/ko not_active Ceased
- 2018-05-11 AU AU2018265873A patent/AU2018265873A1/en not_active Abandoned
- 2018-05-11 CN CN201880031547.4A patent/CN110709383A/zh active Pending
- 2018-05-11 EP EP18727970.8A patent/EP3621954B1/en active Active
- 2018-05-11 SG SG10201912946TA patent/SG10201912946TA/en unknown
- 2018-05-11 CA CA3062851A patent/CA3062851A1/en active Pending
- 2018-05-11 CR CR20190562A patent/CR20190562A/es unknown
- 2018-05-11 MX MX2019013533A patent/MX2019013533A/es unknown
- 2018-05-11 US US15/977,948 patent/US10494339B2/en active Active
- 2018-05-14 TW TW107116349A patent/TW201900609A/zh unknown
-
2019
- 2019-11-07 PH PH12019502505A patent/PH12019502505A1/en unknown
- 2019-11-08 CL CL2019003212A patent/CL2019003212A1/es unknown
- 2019-11-18 US US16/687,394 patent/US10906872B2/en active Active
- 2019-12-11 CO CONC2019/0013923A patent/CO2019013923A2/es unknown
- 2019-12-11 ZA ZA201908267A patent/ZA201908267B/en unknown
-
2020
- 2020-11-17 IL IL278757A patent/IL278757B/en unknown
-
2021
- 2021-02-01 US US17/164,825 patent/US11370754B2/en active Active
- 2021-08-02 IL IL285299A patent/IL285299A/en unknown
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