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 (enExample) | 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 (enExample) |
| EP (1) | EP3621954B1 (enExample) |
| JP (1) | JP2020519583A (enExample) |
| KR (1) | KR20200008578A (enExample) |
| CN (1) | CN110709383A (enExample) |
| AU (1) | AU2018265873A1 (enExample) |
| BR (1) | BR112019023582A2 (enExample) |
| CA (1) | CA3062851A1 (enExample) |
| CL (1) | CL2019003212A1 (enExample) |
| CO (1) | CO2019013923A2 (enExample) |
| CR (1) | CR20190562A (enExample) |
| EA (1) | EA201992695A1 (enExample) |
| IL (2) | IL278757B (enExample) |
| MA (1) | MA48626A (enExample) |
| MX (1) | MX2019013533A (enExample) |
| PE (1) | PE20200339A1 (enExample) |
| PH (1) | PH12019502505A1 (enExample) |
| SG (1) | SG10201912946TA (enExample) |
| TW (1) | TW201900609A (enExample) |
| WO (1) | WO2018209290A1 (enExample) |
| ZA (1) | ZA201908267B (enExample) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HRP20160305T1 (hr) | 2010-10-26 | 2016-07-01 | Mars, Incorporated | Borati kao inhibitori arginaze |
| CN114989205A (zh) | 2016-12-22 | 2022-09-02 | 卡里塞拉生物科学股份公司 | 用于抑制精氨酸酶活性的组合物和方法 |
| KR20200008578A (ko) * | 2017-05-12 | 2020-01-28 | 칼리테라 바이오사이언시즈, 인코포레이티드 | (3R,4S)-3-아세트아미도-4-알릴-N-(tert-부틸)피롤리딘-3-카복스아미드의 제조방법 |
| WO2019186497A1 (en) | 2018-03-29 | 2019-10-03 | Oncoarendi Therapeutics S.A. | 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 |
| TW202216662A (zh) | 2020-07-17 | 2022-05-01 | 美商英塞特公司 | 製備精胺酸酶抑制劑及其合成中間物之方法 |
| 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 |
|---|---|---|---|---|
| AU9797998A (en) | 1997-10-10 | 1999-05-03 | Trustees Of The University Of Pennsylvania, The | Compositions and methods for inhibiting arginase activity |
| US20040063666A1 (en) | 1998-10-09 | 2004-04-01 | David Christianson | Compositions for inhibiting arginase activity |
| CA2415174A1 (en) | 2000-07-06 | 2002-01-17 | Thomas W. Bell | Methods and kits for the detection of arginine compounds |
| 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 |
| LT2389352T (lt) | 2009-01-26 | 2019-06-10 | The Trustees Of The University Of Pennsylvania | Arginazės inhibitoriai ir naudojimo būdai |
| SG10201503168VA (en) | 2010-04-22 | 2015-06-29 | Mars Inc | Inhibitors of arginase and their therapeutic applications |
| HRP20160305T1 (hr) | 2010-10-26 | 2016-07-01 | Mars, Incorporated | Borati kao inhibitori arginaze |
| CA2824599C (en) | 2010-12-31 | 2020-03-10 | Astrazeneca Uk Limited | Arginase inhibitors and methods of use thereof |
| WO2013059437A1 (en) | 2011-10-19 | 2013-04-25 | Mars, Incorporated | Inhibitors of arginase and their therapeutic applications |
| JP6073343B2 (ja) | 2011-10-20 | 2017-02-01 | グラクソスミスクライン・リミテッド・ライアビリティ・カンパニーＧｌａｘｏＳｍｉｔｈＫｌｉｎｅ ＬＬＣ | サーチュイン調節因子としての置換された二環式アザ複素環およびアナログ |
| CN104540836B (zh) * | 2012-04-18 | 2016-11-09 | 马尔斯公司 | 作为精氨酸酶抑制剂的环约束类似物 |
| EA201690746A1 (ru) | 2013-10-25 | 2016-12-30 | Фармасайкликс Элэлси | Лечение с применением ингибиторов тирозинкиназы брутона и иммунотерапии |
| 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 |
| US10143699B2 (en) * | 2015-06-23 | 2018-12-04 | Calithera Biosciences, Inc. | Compositions and methods for inhibiting arginase activity |
| SG11201802961PA (en) * | 2015-10-30 | 2018-05-30 | Calithera Biosciences Inc | Compositions and methods for inhibiting arginase activity |
| KR20200008578A (ko) * | 2017-05-12 | 2020-01-28 | 칼리테라 바이오사이언시즈, 인코포레이티드 | (3R,4S)-3-아세트아미도-4-알릴-N-(tert-부틸)피롤리딘-3-카복스아미드의 제조방법 |
-
2018
- 2018-05-11 KR KR1020197036665A patent/KR20200008578A/ko not_active Ceased
- 2018-05-11 CA CA3062851A patent/CA3062851A1/en active Pending
- 2018-05-11 PE PE2019002393A patent/PE20200339A1/es unknown
- 2018-05-11 CR CR20190562A patent/CR20190562A/es unknown
- 2018-05-11 EA EA201992695A patent/EA201992695A1/ru unknown
- 2018-05-11 CN CN201880031547.4A patent/CN110709383A/zh active Pending
- 2018-05-11 MA MA048626A patent/MA48626A/fr unknown
- 2018-05-11 EP EP18727970.8A patent/EP3621954B1/en active Active
- 2018-05-11 MX MX2019013533A patent/MX2019013533A/es unknown
- 2018-05-11 JP JP2019561210A patent/JP2020519583A/ja not_active Abandoned
- 2018-05-11 AU AU2018265873A patent/AU2018265873A1/en not_active Abandoned
- 2018-05-11 WO PCT/US2018/032407 patent/WO2018209290A1/en not_active Ceased
- 2018-05-11 SG SG10201912946TA patent/SG10201912946TA/en unknown
- 2018-05-11 BR BR112019023582-5A patent/BR112019023582A2/pt not_active Application Discontinuation
- 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 ZA ZA201908267A patent/ZA201908267B/en unknown
- 2019-12-11 CO CONC2019/0013923A patent/CO2019013923A2/es 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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