JP2016513709A5 - - Google Patents
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- Publication number
- JP2016513709A5 JP2016513709A5 JP2016502520A JP2016502520A JP2016513709A5 JP 2016513709 A5 JP2016513709 A5 JP 2016513709A5 JP 2016502520 A JP2016502520 A JP 2016502520A JP 2016502520 A JP2016502520 A JP 2016502520A JP 2016513709 A5 JP2016513709 A5 JP 2016513709A5
- Authority
- JP
- Japan
- Prior art keywords
- formula
- compound
- chloro
- phenyl
- amino
- 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.)
- Granted
Links
- 238000000034 method Methods 0.000 claims 14
- -1 acylated aniline compound Chemical class 0.000 claims 10
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 6
- 150000001875 compounds Chemical class 0.000 claims 6
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical group [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 claims 6
- VDLXWVJCSVAOKZ-UHFFFAOYSA-N 1-(2-amino-4-chlorophenyl)-2-chloroethanone Chemical compound NC1=CC(Cl)=CC=C1C(=O)CCl VDLXWVJCSVAOKZ-UHFFFAOYSA-N 0.000 claims 4
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims 4
- RENMDAKOXSCIGH-UHFFFAOYSA-N Chloroacetonitrile Chemical compound ClCC#N RENMDAKOXSCIGH-UHFFFAOYSA-N 0.000 claims 4
- 108090000790 Enzymes Proteins 0.000 claims 4
- 102000004190 Enzymes Human genes 0.000 claims 4
- 229910052783 alkali metal Inorganic materials 0.000 claims 4
- 230000002152 alkylating effect Effects 0.000 claims 4
- 229910052782 aluminium Inorganic materials 0.000 claims 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims 4
- 229910052796 boron Inorganic materials 0.000 claims 4
- SBMIBRAEESOEIP-UHFFFAOYSA-N diethyl 2-acetamido-2-[2-(2-amino-4-chlorophenyl)-2-oxoethyl]propanedioate Chemical compound CCOC(=O)C(C(=O)OCC)(NC(C)=O)CC(=O)C1=CC=C(Cl)C=C1N SBMIBRAEESOEIP-UHFFFAOYSA-N 0.000 claims 4
- OVTRJMNZIRSECO-UHFFFAOYSA-N 2-acetamido-4-(2-amino-4-chlorophenyl)-4-oxobutanoic acid Chemical compound CC(=O)NC(C(O)=O)CC(=O)C1=CC=C(Cl)C=C1N OVTRJMNZIRSECO-UHFFFAOYSA-N 0.000 claims 3
- SMNXWBKWPNTECZ-UHFFFAOYSA-N acetamide;diethyl propanedioate Chemical compound CC(N)=O.CCOC(=O)CC(=O)OCC SMNXWBKWPNTECZ-UHFFFAOYSA-N 0.000 claims 2
- 108010003977 aminoacylase I Proteins 0.000 claims 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 2
- 230000000593 degrading effect Effects 0.000 claims 2
- 238000010438 heat treatment Methods 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 235000009518 sodium iodide Nutrition 0.000 claims 2
- 239000012453 solvate Substances 0.000 claims 2
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 claims 1
- PNPCRKVUWYDDST-UHFFFAOYSA-N 3-chloroaniline Chemical compound NC1=CC=CC(Cl)=C1 PNPCRKVUWYDDST-UHFFFAOYSA-N 0.000 claims 1
- 241000228212 Aspergillus Species 0.000 claims 1
- 241000981399 Aspergillus melleus Species 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- HEDRZPFGACZZDS-UHFFFAOYSA-N chloroform Substances ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical group 0.000 claims 1
- 150000002431 hydrogen Chemical group 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 125000000547 substituted alkyl group Chemical group 0.000 claims 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
- QLOLLPPRFVBYSM-QMMMGPOBSA-N C=Nc1ccccc1C(C[C@@H](C(O)=O)N)=O Chemical compound C=Nc1ccccc1C(C[C@@H](C(O)=O)N)=O QLOLLPPRFVBYSM-QMMMGPOBSA-N 0.000 description 1
- PPIMFXHQDQRWGJ-UHFFFAOYSA-N CC(NC(CC(c1ccccc1N)=O)C(O)=O)=O Chemical compound CC(NC(CC(c1ccccc1N)=O)C(O)=O)=O PPIMFXHQDQRWGJ-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201361785807P | 2013-03-14 | 2013-03-14 | |
| US61/785,807 | 2013-03-14 | ||
| PCT/US2014/027694 WO2014152752A1 (en) | 2013-03-14 | 2014-03-14 | Methods for the synthesis of chiral kynurenine compounds |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2018093249A Division JP6618569B2 (ja) | 2013-03-14 | 2018-05-14 | キラルキヌレニン化合物の合成方法 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2016513709A JP2016513709A (ja) | 2016-05-16 |
| JP2016513709A5 true JP2016513709A5 (enExample) | 2017-10-05 |
| JP6340409B2 JP6340409B2 (ja) | 2018-06-06 |
Family
ID=51581307
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016502520A Expired - Fee Related JP6340409B2 (ja) | 2013-03-14 | 2014-03-14 | キラルキヌレニン化合物の合成方法 |
| JP2018093249A Expired - Fee Related JP6618569B2 (ja) | 2013-03-14 | 2018-05-14 | キラルキヌレニン化合物の合成方法 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2018093249A Expired - Fee Related JP6618569B2 (ja) | 2013-03-14 | 2018-05-14 | キラルキヌレニン化合物の合成方法 |
Country Status (6)
| Country | Link |
|---|---|
| US (2) | US9834801B2 (enExample) |
| EP (1) | EP2970097B1 (enExample) |
| JP (2) | JP6340409B2 (enExample) |
| CN (2) | CN107417558A (enExample) |
| CA (1) | CA2941559A1 (enExample) |
| WO (1) | WO2014152752A1 (enExample) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107417558A (zh) | 2013-03-14 | 2017-12-01 | 维斯塔津治疗公司 | 用于合成手性犬尿氨酸化合物的方法 |
| ES2925274T3 (es) | 2015-05-22 | 2022-10-14 | Designados Vistagen Therapeutics Inc | Usos terapéuticos de la L-4-cloroquinurenina |
| US20180327351A1 (en) * | 2015-09-08 | 2018-11-15 | Cephalon, Inc. | Prodrugs of chlorokynurenines |
| US20190201360A1 (en) | 2016-08-31 | 2019-07-04 | Ampio Pharmaceuticals, Inc. | Treatment of disease with n-acetyl kynurenine |
| JP6761896B2 (ja) | 2017-03-29 | 2020-09-30 | 富士フイルム株式会社 | 構造体および光センサ |
| JP7431163B2 (ja) * | 2018-02-09 | 2024-02-14 | ヴィスタゲン セラピューティクス、インコーポレイテッド | 4-クロロキヌレニンおよび中間体の合成 |
| CN113549661B (zh) * | 2020-04-26 | 2022-08-30 | 赤壁生合元科技有限公司 | 生物催化合成L-4-Cl-犬尿氨酸或L-4-Br-犬尿氨酸的方法及应用 |
| CN113549662B (zh) * | 2020-04-26 | 2022-06-03 | 赤壁市高质量发展研究院有限公司 | 一种用MOF载酶技术高效制备抗抑郁药前药L-4-Cl-犬尿氨酸的方法及应用 |
| AU2023300118A1 (en) | 2022-06-30 | 2025-01-09 | A-Clip Institute, Co., Ltd. | Method for testing diseased state of vasculitis or exacerbation risk of COVID-19, testing kit, companion diagnostic agent, and testing marker |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3766261A (en) | 1970-08-21 | 1973-10-16 | Us Agriculture | Process of producing kynurenine |
| US3702255A (en) * | 1970-08-21 | 1972-11-07 | Us Agriculture | Kynurenine derivatives as sweetening agents |
| US3765261A (en) * | 1973-01-02 | 1973-10-16 | Hurst Performance | Unitary stick transfer case shifter |
| US5519055A (en) | 1993-08-06 | 1996-05-21 | University Of Maryland At Baltimore | Substituted kynurenines and process for their preparation |
| US5789434A (en) * | 1994-11-15 | 1998-08-04 | Bayer Corporation | Derivatives of substituted 4-biarylbutyric acid as matrix metalloprotease inhibitors |
| GB9522615D0 (en) * | 1995-11-03 | 1996-01-03 | Pharmacia Spa | 4-Phenyl-4-oxo-butanoic acid derivatives with kynurenine-3-hydroxylase inhibiting activity |
| ITMI20041626A1 (it) | 2004-08-06 | 2004-11-06 | Roberto Pellicciari | Inibitori della chinurenina-ammino-trasferasi |
| US7622495B2 (en) * | 2006-10-03 | 2009-11-24 | Neurim Pharmaceuticals (1991) Ltd. | Substituted aryl-indole compounds and their kynurenine/kynuramine-like metabolites as therapeutic agents |
| JP5232247B2 (ja) * | 2008-12-11 | 2013-07-10 | 東洋紡株式会社 | L−サクシニルアミノアシラーゼ、およびこれを用いたl−アミノ酸の製造方法 |
| CN107417558A (zh) * | 2013-03-14 | 2017-12-01 | 维斯塔津治疗公司 | 用于合成手性犬尿氨酸化合物的方法 |
-
2014
- 2014-03-14 CN CN201710718531.8A patent/CN107417558A/zh active Pending
- 2014-03-14 CA CA2941559A patent/CA2941559A1/en not_active Abandoned
- 2014-03-14 JP JP2016502520A patent/JP6340409B2/ja not_active Expired - Fee Related
- 2014-03-14 EP EP14770640.2A patent/EP2970097B1/en not_active Not-in-force
- 2014-03-14 CN CN201480023992.8A patent/CN105164100B/zh not_active Expired - Fee Related
- 2014-03-14 WO PCT/US2014/027694 patent/WO2014152752A1/en not_active Ceased
- 2014-03-14 US US14/775,287 patent/US9834801B2/en active Active
-
2017
- 2017-11-14 US US15/812,599 patent/US10294502B2/en active Active
-
2018
- 2018-05-14 JP JP2018093249A patent/JP6618569B2/ja not_active Expired - Fee Related
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