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) | EP3686183B1 (enExample) |
| JP (6) | JP6144488B2 (enExample) |
| KR (6) | KR102399540B1 (enExample) |
| CN (3) | CN102421432B (enExample) |
| AU (1) | AU2010232521B2 (enExample) |
| BR (1) | BRPI1013657A2 (enExample) |
| CA (5) | CA2998434C (enExample) |
| CY (1) | CY1119843T1 (enExample) |
| DK (3) | DK2413924T3 (enExample) |
| EA (2) | EA023051B1 (enExample) |
| ES (3) | ES2791524T3 (enExample) |
| HR (2) | HRP20171962T1 (enExample) |
| HU (2) | HUE035921T2 (enExample) |
| IL (2) | IL215449B (enExample) |
| LT (2) | LT2413924T (enExample) |
| MX (4) | MX356608B (enExample) |
| NO (1) | NO2413924T3 (enExample) |
| NZ (3) | NZ595706A (enExample) |
| PL (2) | PL2413924T3 (enExample) |
| PT (2) | PT3686183T (enExample) |
| SG (3) | SG174982A1 (enExample) |
| SI (1) | SI2413924T1 (enExample) |
| SM (2) | SMT202200395T1 (enExample) |
| WO (1) | WO2010115055A1 (enExample) |
| ZA (1) | ZA201107189B (enExample) |
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PL1824563T3 (pl) | 2004-11-26 | 2010-07-30 | Ucl Business Plc | Kompozycje zawierające ornitynę i fenylooctan lub fenylomaślan do leczenia encefalopatii wątrobowej |
| SG174982A1 (en) | 2009-04-03 | 2011-11-28 | Ocera Therapeutics Inc | L-ornithine phenyl acetate and methods of making thereof |
| JP5749255B2 (ja) | 2009-06-08 | 2015-07-15 | ユーシーエル ビジネス ピーエルシー | Ｌ−オルニチンフェニル酢酸塩を用いる門脈圧亢進の治療及び肝機能の修復 |
| 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 |
| JP6087284B2 (ja) | 2010-10-06 | 2017-03-01 | オセラ セラピューティクス， インコーポレイテッド | Ｌ−オルニチンフェニルアセテートを製造するための方法 |
| 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 |
| IL281349B (en) | 2014-11-24 | 2022-09-01 | Ucl Business Ltd | Treatment of diseases related to hepatic stellate cell activity using ammonia-lowering treatments |
| CA2983146C (en) | 2015-04-20 | 2023-09-12 | Ocera Therapeutics, Inc. | Formulations of l-ornithine phenylacetate |
| US10835506B2 (en) | 2015-08-18 | 2020-11-17 | Ocera Therapeutics, Inc. | Treatment and prevention of muscle loss using L-ornithine in combination with at least one of phenylacetate and phenylbutyrate |
| HK1257679A1 (zh) * | 2015-09-25 | 2019-10-25 | Ocera Therapeutics, Inc. | 使用l-鸟苷酸与苯乙酸根和苯基丁酸根中至少一种的结合治疗和预防神经元细胞损失 |
| SG11201802987UA (en) | 2015-11-13 | 2018-05-30 | Ocera Therapeutics Inc | Formulation of l-ornithine phenylacetate |
| US11219611B2 (en) | 2015-11-13 | 2022-01-11 | Ocera Therapeutics, Inc. | Formulations of L-ornithine phenylacetate |
| JOP20190146A1 (ar) | 2016-12-19 | 2019-06-18 | Axcella Health Inc | تركيبات حمض أميني وطرق لمعالجة أمراض الكبد |
| CA3063134A1 (en) * | 2017-05-11 | 2018-11-15 | Ocera Therapeutics, Inc. | Processes of making l-ornithine phenylacetate |
| US10682325B2 (en) | 2017-08-14 | 2020-06-16 | Axcella Health Inc. | Compositions and methods for the treatment of liver diseases and disorders associated with one or both of hyperammonemia or muscle wasting |
| JP2021527670A (ja) | 2018-06-20 | 2021-10-14 | アクセラ・ヘルス・インコーポレイテッドＡｘｃｅｌｌａ Ｈｅａｌｔｈ Ｉｎｃ． | 筋肉中の脂肪浸潤の治療のための組成物及び方法 |
| JP2022533569A (ja) | 2019-05-09 | 2022-07-25 | オセラ セラピューティクス， インコーポレイテッド | 肝性脳症を評価および処置する方法 |
| 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 |
| US20220362192A1 (en) * | 2019-10-16 | 2022-11-17 | Ocera Therapeutics, Inc. | Dosages and uses of ornithine phenylacetate for treating hyperammonemia |
| 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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| JP2011236160A (ja) | 2010-05-11 | 2011-11-24 | Shinshu Univ | 非アルコール性肝疾患治療薬 |
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