JP2012522803A5 - - Google Patents
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- Publication number
- JP2012522803A5 JP2012522803A5 JP2012503725A JP2012503725A JP2012522803A5 JP 2012522803 A5 JP2012522803 A5 JP 2012522803A5 JP 2012503725 A JP2012503725 A JP 2012503725A JP 2012503725 A JP2012503725 A JP 2012503725A JP 2012522803 A5 JP2012522803 A5 JP 2012522803A5
- Authority
- JP
- Japan
- Prior art keywords
- salt
- composition
- crystalline form
- ornithine
- solution
- 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
- 239000000203 mixture Substances 0.000 claims 24
- 238000000034 method Methods 0.000 claims 16
- LRSYFEZBIMVWRY-VWMHFEHESA-N (2s)-2,5-diaminopentanoic acid;2-phenylacetic acid Chemical compound NCCC[C@H](N)C(O)=O.OC(=O)CC1=CC=CC=C1 LRSYFEZBIMVWRY-VWMHFEHESA-N 0.000 claims 14
- 238000000634 powder X-ray diffraction Methods 0.000 claims 10
- AHLPHDHHMVZTML-BYPYZUCNSA-N L-Ornithine Chemical class NCCC[C@H](N)C(O)=O AHLPHDHHMVZTML-BYPYZUCNSA-N 0.000 claims 8
- 150000003839 salts Chemical class 0.000 claims 8
- 239000008194 pharmaceutical composition Substances 0.000 claims 7
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims 6
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 claims 5
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical group [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 3
- IPBVNPXQWQGGJP-UHFFFAOYSA-N acetic acid phenyl ester Natural products CC(=O)OC1=CC=CC=C1 IPBVNPXQWQGGJP-UHFFFAOYSA-N 0.000 claims 3
- -1 alkali metal salt Chemical class 0.000 claims 3
- 230000001965 increasing effect Effects 0.000 claims 3
- 238000002844 melting Methods 0.000 claims 3
- 230000008018 melting Effects 0.000 claims 3
- 229940049953 phenylacetate Drugs 0.000 claims 3
- 239000005711 Benzoic acid Substances 0.000 claims 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 claims 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 2
- 206010020575 Hyperammonaemia Diseases 0.000 claims 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 claims 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims 2
- 229910052783 alkali metal Inorganic materials 0.000 claims 2
- 235000010233 benzoic acid Nutrition 0.000 claims 2
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 claims 2
- 229910052709 silver Inorganic materials 0.000 claims 2
- 239000004332 silver Substances 0.000 claims 2
- 239000002904 solvent Substances 0.000 claims 2
- APJYDQYYACXCRM-UHFFFAOYSA-N tryptamine Chemical compound C1=CC=C2C(CCN)=CNC2=C1 APJYDQYYACXCRM-UHFFFAOYSA-N 0.000 claims 2
- UIQPERPLCCTBGX-UHFFFAOYSA-N 2-phenylacetic acid;silver Chemical compound [Ag].OC(=O)CC1=CC=CC=C1 UIQPERPLCCTBGX-UHFFFAOYSA-N 0.000 claims 1
- CSDQQAQKBAQLLE-UHFFFAOYSA-N 4-(4-chlorophenyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine Chemical compound C1=CC(Cl)=CC=C1C1C(C=CS2)=C2CCN1 CSDQQAQKBAQLLE-UHFFFAOYSA-N 0.000 claims 1
- AHLPHDHHMVZTML-UHFFFAOYSA-N Orn-delta-NH2 Natural products NCCCC(N)C(O)=O AHLPHDHHMVZTML-UHFFFAOYSA-N 0.000 claims 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims 1
- 150000001558 benzoic acid derivatives Chemical class 0.000 claims 1
- 229910000019 calcium carbonate Inorganic materials 0.000 claims 1
- 230000001747 exhibiting effect Effects 0.000 claims 1
- 208000007386 hepatic encephalopathy Diseases 0.000 claims 1
- 230000001939 inductive effect Effects 0.000 claims 1
- FRIJBUGBVQZNTB-UHFFFAOYSA-M magnesium;ethane;bromide Chemical compound [Mg+2].[Br-].[CH2-]C FRIJBUGBVQZNTB-UHFFFAOYSA-M 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 229960003104 ornithine Drugs 0.000 claims 1
- 239000003002 pH adjusting agent Substances 0.000 claims 1
- 229960003424 phenylacetic acid Drugs 0.000 claims 1
- 239000003279 phenylacetic acid Substances 0.000 claims 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 claims 1
- 239000002244 precipitate Substances 0.000 claims 1
- 238000003825 pressing Methods 0.000 claims 1
- CLDWGXZGFUNWKB-UHFFFAOYSA-M silver;benzoate Chemical group [Ag+].[O-]C(=O)C1=CC=CC=C1 CLDWGXZGFUNWKB-UHFFFAOYSA-M 0.000 claims 1
- 229910000029 sodium carbonate Inorganic materials 0.000 claims 1
- 239000012312 sodium hydride Substances 0.000 claims 1
- 229910000104 sodium hydride Inorganic materials 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US16667609P | 2009-04-03 | 2009-04-03 | |
| US61/166,676 | 2009-04-03 | ||
| PCT/US2010/029708 WO2010115055A1 (en) | 2009-04-03 | 2010-04-01 | L-ornithine phenyl acetate and methods of making thereof |
Related Child Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015031199A Division JP6010154B2 (ja) | 2009-04-03 | 2015-02-20 | Ｌ−オルニチンフェニルアセテートおよびその製造方法 |
| JP2016237164A Division JP6328737B2 (ja) | 2009-04-03 | 2016-12-07 | Ｌ−オルニチンフェニルアセテートおよびその製造方法 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2012522803A JP2012522803A (ja) | 2012-09-27 |
| JP2012522803A5 true JP2012522803A5 (enExample) | 2013-05-16 |
| JP6144488B2 JP6144488B2 (ja) | 2017-06-07 |
Family
ID=42828717
Family Applications (6)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2012503725A Active JP6144488B2 (ja) | 2009-04-03 | 2010-04-01 | Ｌ−オルニチンフェニルアセテートおよびその製造方法 |
| JP2015031199A Active JP6010154B2 (ja) | 2009-04-03 | 2015-02-20 | Ｌ−オルニチンフェニルアセテートおよびその製造方法 |
| JP2016237164A Active JP6328737B2 (ja) | 2009-04-03 | 2016-12-07 | Ｌ−オルニチンフェニルアセテートおよびその製造方法 |
| JP2018079490A Expired - Fee Related JP6647336B2 (ja) | 2009-04-03 | 2018-04-18 | Ｌ−オルニチンフェニルアセテートおよびその製造方法 |
| JP2020003346A Active JP7086118B2 (ja) | 2009-04-03 | 2020-01-14 | Ｌ－オルニチンフェニルアセテートおよびその製造方法 |
| JP2022049427A Pending JP2022088504A (ja) | 2009-04-03 | 2022-03-25 | Ｌ－オルニチンフェニルアセテートおよびその製造方法 |
Family Applications After (5)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015031199A Active JP6010154B2 (ja) | 2009-04-03 | 2015-02-20 | Ｌ−オルニチンフェニルアセテートおよびその製造方法 |
| JP2016237164A Active JP6328737B2 (ja) | 2009-04-03 | 2016-12-07 | Ｌ−オルニチンフェニルアセテートおよびその製造方法 |
| JP2018079490A Expired - Fee Related JP6647336B2 (ja) | 2009-04-03 | 2018-04-18 | Ｌ−オルニチンフェニルアセテートおよびその製造方法 |
| JP2020003346A Active JP7086118B2 (ja) | 2009-04-03 | 2020-01-14 | Ｌ－オルニチンフェニルアセテートおよびその製造方法 |
| JP2022049427A Pending JP2022088504A (ja) | 2009-04-03 | 2022-03-25 | Ｌ－オルニチンフェニルアセテートおよびその製造方法 |
Country Status (26)
| Country | Link |
|---|---|
| US (9) | US8173706B2 (enExample) |
| EP (4) | EP3263100B1 (enExample) |
| JP (6) | JP6144488B2 (enExample) |
| KR (6) | KR102217081B1 (enExample) |
| CN (3) | CN106810464B (enExample) |
| AU (1) | AU2010232521B2 (enExample) |
| BR (1) | BRPI1013657A2 (enExample) |
| CA (5) | CA2757373C (enExample) |
| CY (1) | CY1119843T1 (enExample) |
| DK (3) | DK3263100T3 (enExample) |
| EA (2) | EA034409B1 (enExample) |
| ES (3) | ES2928586T3 (enExample) |
| HR (2) | HRP20171962T1 (enExample) |
| HU (2) | HUE060371T2 (enExample) |
| IL (2) | IL215449B (enExample) |
| LT (2) | LT2413924T (enExample) |
| MX (4) | MX375111B (enExample) |
| NO (1) | NO2413924T3 (enExample) |
| NZ (3) | NZ619235A (enExample) |
| PL (2) | PL2413924T3 (enExample) |
| PT (2) | PT2413924T (enExample) |
| SG (3) | SG10202010988WA (enExample) |
| SI (1) | SI2413924T1 (enExample) |
| SM (2) | SMT201700601T1 (enExample) |
| WO (1) | WO2010115055A1 (enExample) |
| ZA (1) | ZA201107189B (enExample) |
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PT2319581E (pt) | 2004-11-26 | 2015-06-30 | Ucl Business Plc | Composições compreendendo ornitina e fenilacetato ou fenilbutirato para tratamento de encefalopatia hepática |
| DK3263100T3 (da) | 2009-04-03 | 2020-05-11 | Ocera Therapeutics Inc | L-ornithinphenylacetat og fremgangsmåder til fremstilling deraf |
| AU2010258888B2 (en) | 2009-06-08 | 2014-08-07 | Ocera Therapeutics, Inc. | Treatment of portal hypertension and restoration of liver function using L-ornithine phenylacetate |
| US8068011B1 (en) | 2010-08-27 | 2011-11-29 | Q Street, LLC | System and method for interactive user-directed interfacing between handheld devices and RFID media |
| MX360062B (es) | 2010-10-06 | 2018-10-22 | Ocera Therapeutics Inc | Metodos de elaboracion de fenilacetato de l-ornitina. |
| CN102993037B (zh) * | 2012-11-20 | 2015-03-04 | 南京工业大学 | 一种l-鸟氨酸苯乙酸盐的制备方法 |
| CN105481725B (zh) * | 2014-09-18 | 2019-01-22 | 博瑞生物医药（苏州）股份有限公司 | L-精氨酸苯乙酸盐的晶型及其制备方法 |
| CN107206021B (zh) | 2014-11-24 | 2021-09-03 | Ucl商业有限公司 | 使用降氨疗法治疗与肝星状细胞激活相关的疾病 |
| CN107708684A (zh) | 2015-04-20 | 2018-02-16 | 欧塞拉治疗有限公司 | L‑鸟氨酸苯乙酸盐制剂 |
| EP3337473A4 (en) | 2015-08-18 | 2019-04-17 | Ocera Therapeutics, Inc. | TREATMENT AND PREVENTION OF MUSCLE WOUND BY L-ORNITHIN IN COMBINATION WITH AT LEAST ONE PHENYL ACETATE AND PHENYL BUTYRATE |
| WO2017053613A1 (en) * | 2015-09-25 | 2017-03-30 | Ocera Therapeutics, Inc. | Treatment and prevention of neuronal cell loss using l-ornithine in combination with at least one of phenylacetate and phenylbutyrate |
| US11219611B2 (en) * | 2015-11-13 | 2022-01-11 | Ocera Therapeutics, Inc. | Formulations of L-ornithine phenylacetate |
| MX389926B (es) | 2015-11-13 | 2025-03-20 | Ocera Therapeutics Inc | Formulaciones de fenilacetato de l-ornitina |
| JOP20190146A1 (ar) | 2016-12-19 | 2019-06-18 | Axcella Health Inc | تركيبات حمض أميني وطرق لمعالجة أمراض الكبد |
| CN110740988A (zh) * | 2017-05-11 | 2020-01-31 | 欧塞拉治疗有限公司 | 制备l-鸟氨酸苯乙酸盐的方法 |
| MA49906A (fr) | 2017-08-14 | 2020-06-24 | Axcella Health Inc | Acides aminés à chaîne ramifiée pour le traitement d'une maladie du foie |
| EP3810123A1 (en) | 2018-06-20 | 2021-04-28 | Axcella Health Inc. | Compositions and methods for the treatment of fat infiltration in muscle |
| CN113966194A (zh) | 2019-05-09 | 2022-01-21 | 欧塞拉治疗有限公司 | 评估和治疗肝性脑病的方法 |
| CN110707221B (zh) * | 2019-09-25 | 2023-09-01 | 北京大学深圳研究生院 | 氨基酸离子液体在制备钙钛矿光电器件中钙钛矿层的应用 |
| KR20220110727A (ko) * | 2019-10-16 | 2022-08-09 | 오세라 테라퓨틱스, 아이엔씨. | 고암모니아혈증의 치료를 위한 오르니틴 페닐아세테이트의 투여량 및 용도 |
| WO2023240081A1 (en) * | 2022-06-06 | 2023-12-14 | Yale University | Treatment, amelioration, and/or prevention of inflammatory and autoimmune diseases |
| WO2024261477A1 (en) | 2023-06-20 | 2024-12-26 | Yaqrit Limited | Combination of tlr4 antagonist, ornithine and phenylacetate or phenylbutyrate |
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| CN107708684A (zh) | 2015-04-20 | 2018-02-16 | 欧塞拉治疗有限公司 | L‑鸟氨酸苯乙酸盐制剂 |
| EP3337473A4 (en) | 2015-08-18 | 2019-04-17 | Ocera Therapeutics, Inc. | TREATMENT AND PREVENTION OF MUSCLE WOUND BY L-ORNITHIN IN COMBINATION WITH AT LEAST ONE PHENYL ACETATE AND PHENYL BUTYRATE |
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