JP2013542935A5 - - Google Patents
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- Publication number
- JP2013542935A5 JP2013542935A5 JP2013532925A JP2013532925A JP2013542935A5 JP 2013542935 A5 JP2013542935 A5 JP 2013542935A5 JP 2013532925 A JP2013532925 A JP 2013532925A JP 2013532925 A JP2013532925 A JP 2013532925A JP 2013542935 A5 JP2013542935 A5 JP 2013542935A5
- Authority
- JP
- Japan
- Prior art keywords
- ornithine
- salt
- benzoate
- ppm
- less
- 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 33
- 239000000203 mixture Substances 0.000 claims 15
- OPWXRPAHCDZTNU-VWMHFEHESA-N benzoic acid;(2s)-2,5-diaminopentanoic acid Chemical compound NCCC[C@H](N)C(O)=O.OC(=O)C1=CC=CC=C1 OPWXRPAHCDZTNU-VWMHFEHESA-N 0.000 claims 11
- AHLPHDHHMVZTML-BYPYZUCNSA-N L-Ornithine Chemical class NCCC[C@H](N)C(O)=O AHLPHDHHMVZTML-BYPYZUCNSA-N 0.000 claims 10
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical class OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 claims 8
- 150000003839 salts Chemical class 0.000 claims 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 6
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims 6
- 239000002904 solvent Substances 0.000 claims 6
- 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 5
- -1 alkali metal alkoxides Chemical class 0.000 claims 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 3
- 229910052783 alkali metal Inorganic materials 0.000 claims 3
- 239000002585 base Substances 0.000 claims 3
- 229910052709 silver Inorganic materials 0.000 claims 3
- 239000004332 silver Substances 0.000 claims 3
- GGTYBZJRPHEQDG-WCCKRBBISA-N (2s)-2,5-diaminopentanoic acid hydrochloride Chemical group Cl.NCCC[C@H](N)C(O)=O GGTYBZJRPHEQDG-WCCKRBBISA-N 0.000 claims 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims 2
- 150000001450 anions Chemical class 0.000 claims 2
- 150000001558 benzoic acid derivatives Chemical class 0.000 claims 2
- 150000001768 cations Chemical class 0.000 claims 2
- 230000001747 exhibiting effect Effects 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 239000003279 phenylacetic acid Substances 0.000 claims 2
- 229960003424 phenylacetic acid Drugs 0.000 claims 2
- 238000000634 powder X-ray diffraction Methods 0.000 claims 2
- CLDWGXZGFUNWKB-UHFFFAOYSA-M silver;benzoate Chemical group [Ag+].[O-]C(=O)C1=CC=CC=C1 CLDWGXZGFUNWKB-UHFFFAOYSA-M 0.000 claims 2
- 229910052708 sodium Inorganic materials 0.000 claims 2
- 239000011734 sodium Substances 0.000 claims 2
- INIRLMDMLPBYJS-SCGRZTRASA-N (2S)-2,5-diaminopentanoic acid hydrochloride Chemical compound Cl.NCCC[C@H](N)C(O)=O.NCCC[C@H](N)C(O)=O INIRLMDMLPBYJS-SCGRZTRASA-N 0.000 claims 1
- UIQPERPLCCTBGX-UHFFFAOYSA-N 2-phenylacetic acid;silver Chemical compound [Ag].OC(=O)CC1=CC=CC=C1 UIQPERPLCCTBGX-UHFFFAOYSA-N 0.000 claims 1
- ITIONVBQFUNVJV-UHFFFAOYSA-N Etomidoline Chemical group C12=CC=CC=C2C(=O)N(CC)C1NC(C=C1)=CC=C1OCCN1CCCCC1 ITIONVBQFUNVJV-UHFFFAOYSA-N 0.000 claims 1
- FOIXSVOLVBLSDH-UHFFFAOYSA-N Silver ion Chemical compound [Ag+] FOIXSVOLVBLSDH-UHFFFAOYSA-N 0.000 claims 1
- IPBVNPXQWQGGJP-UHFFFAOYSA-N acetic acid phenyl ester Natural products CC(=O)OC1=CC=CC=C1 IPBVNPXQWQGGJP-UHFFFAOYSA-N 0.000 claims 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims 1
- CLLNPYSXOIKTLL-UHFFFAOYSA-L disilver diacetate Chemical compound [Ag+].[Ag+].CC([O-])=O.CC([O-])=O CLLNPYSXOIKTLL-UHFFFAOYSA-L 0.000 claims 1
- 229940049953 phenylacetate Drugs 0.000 claims 1
- 229940006198 sodium phenylacetate Drugs 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US39058510P | 2010-10-06 | 2010-10-06 | |
| US61/390,585 | 2010-10-06 | ||
| PCT/US2011/054983 WO2012048043A1 (en) | 2010-10-06 | 2011-10-05 | Methods of making l-ornithine phenyl acetate |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2013542935A JP2013542935A (ja) | 2013-11-28 |
| JP2013542935A5 true JP2013542935A5 (enExample) | 2014-11-20 |
| JP6087284B2 JP6087284B2 (ja) | 2017-03-01 |
Family
ID=45928120
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2013532925A Expired - Fee Related JP6087284B2 (ja) | 2010-10-06 | 2011-10-05 | 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 |
Country Status (16)
| Country | Link |
|---|---|
| US (2) | US8946473B2 (enExample) |
| EP (1) | EP2625162B1 (enExample) |
| JP (1) | JP6087284B2 (enExample) |
| KR (1) | KR101888215B1 (enExample) |
| CN (1) | CN103502203B (enExample) |
| AU (1) | AU2011312042B2 (enExample) |
| BR (1) | BR112013008054B1 (enExample) |
| CA (1) | CA2813563C (enExample) |
| EA (1) | EA028395B1 (enExample) |
| ES (1) | ES2720148T3 (enExample) |
| IL (1) | IL225512A (enExample) |
| MX (1) | MX360062B (enExample) |
| NZ (1) | NZ609191A (enExample) |
| SG (1) | SG189231A1 (enExample) |
| TR (1) | TR201903978T4 (enExample) |
| WO (1) | WO2012048043A1 (enExample) |
Families Citing this family (15)
| 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 |
| 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 |
| 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 |
| US11219611B2 (en) | 2015-11-13 | 2022-01-11 | Ocera Therapeutics, Inc. | Formulations of L-ornithine phenylacetate |
| SG11201802987UA (en) * | 2015-11-13 | 2018-05-30 | Ocera Therapeutics Inc | Formulation 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 |
| WO2024261477A1 (en) | 2023-06-20 | 2024-12-26 | Yaqrit Limited | Combination of tlr4 antagonist, ornithine and phenylacetate or phenylbutyrate |
Family Cites Families (45)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB965637A (en) | 1962-04-23 | 1964-08-06 | Tanabe Seiyaku Co | L-ornithine l-aspartate |
| NL302572A (enExample) | 1962-12-27 | |||
| GB1067742A (en) | 1963-09-16 | 1967-05-03 | Kyowa Hakko Kogyo Kk | Process for the preparation of l-ornithine l-aspartate |
| ZA716628B (en) | 1970-10-15 | 1972-06-28 | Richardson Merrell Spa | Composition and method for treatment of hepatic disease and mental fatigue |
| US4100161A (en) | 1974-04-15 | 1978-07-11 | The Johns Hopkins University | Promotion of protein synthesis and suppression of urea formation in the body by keto analogs of essential amino acids |
| US3950529A (en) | 1975-02-03 | 1976-04-13 | Massachusetts General Hospital | Amino acid formulations for patients with liver disease and method of using same |
| US4228099A (en) | 1978-03-17 | 1980-10-14 | The Johns Hopkins University | Ornithine and arginine salts of branched chain keto acids and uses in treatment of hepatic and renal disorders |
| US4320146A (en) | 1978-03-17 | 1982-03-16 | The Johns Hopkins University | Treatment of hepatic and renal disorders with ornithine and arginine salts of branched chain keto acids |
| US4352814A (en) | 1979-04-18 | 1982-10-05 | The Johns Hopkins University | Treatment of hepatic and renal disorders with mixed salts of essential or semi-essential amino acids and nitrogen-free analogs |
| US4284647A (en) | 1980-03-31 | 1981-08-18 | The Johns Hopkins University | Process for waste nitrogen removal |
| US4457942A (en) | 1982-08-20 | 1984-07-03 | Brusilow Saul W | Process for waste nitrogen removal |
| US5591613A (en) | 1990-07-02 | 1997-01-07 | Degussa Aktiengesellschaft | Method for the preparation of D-arginine and L-ornithine |
| DE4020980C1 (enExample) | 1990-07-02 | 1991-09-26 | Degussa Ag, 6000 Frankfurt, De | |
| JP3127484B2 (ja) | 1991-02-28 | 2001-01-22 | 味の素株式会社 | 肝炎治療薬 |
| US5767086A (en) | 1992-04-03 | 1998-06-16 | Terrapin Technologies, Inc. | Bone marrow stimulation by certain glutathione analogs |
| ATE153299T1 (de) | 1992-09-09 | 1997-06-15 | Fisons Plc | Pharmazeutisches verpacken |
| US5571783A (en) | 1993-03-09 | 1996-11-05 | Clintec Nutrition Company | Composition and method for treating patients with hepatic disease |
| JP3273578B2 (ja) * | 1993-09-21 | 2002-04-08 | 第一化学薬品株式会社 | オルニチンと酸性アミノ酸類又はケト酸類との塩の製造法 |
| US5840891A (en) | 1994-07-28 | 1998-11-24 | Syntex (U.S.A.) Inc. | 2-(2-amino-1,6-dihydro-6-oxo-purin-9-yl) methoxy-1,3-propanediol derivative |
| WO1997030167A1 (en) | 1996-02-13 | 1997-08-21 | The Trustees Of The University Of Pennsylvania | Method of treating liver disorders |
| ZA986614B (en) | 1997-07-25 | 1999-01-27 | Gilead Sciences | Nucleotide analog composition |
| GB9815567D0 (en) | 1998-07-18 | 1998-09-16 | Glaxo Group Ltd | Antiviral compound |
| US6258849B1 (en) | 1998-07-23 | 2001-07-10 | Stanislaw R. Burzynski | Treatment regimen for administration of phenylacetylglutamine, phenylacetylisoglutamine, and/or phenylacetate |
| CA2374273A1 (en) | 1999-05-21 | 2000-11-30 | Takeda Chemical Industries, Ltd. | Liver function controlling agents |
| US6768024B1 (en) | 2000-08-04 | 2004-07-27 | Lion Bioscience Ag | Triamine derivative melanocortin receptor ligands and methods of using same |
| JP3211824B1 (ja) | 2000-10-26 | 2001-09-25 | 味の素株式会社 | 分岐鎖アミノ酸含有医薬用顆粒製剤とその製造方法 |
| EP1374863B1 (en) | 2001-03-15 | 2009-09-02 | Riken | Amino acid compositions for ameliorating liver failure |
| US6503530B1 (en) | 2001-11-01 | 2003-01-07 | Chunghee Kimberly Kang | Method of preventing development of severe metabolic derangement in inborn errors of metabolism |
| US20030105104A1 (en) | 2001-11-27 | 2003-06-05 | Burzynski Stanislaw R. | Formulation of amino acids and riboflavin useful to reduce toxic effects of cytotoxic chemotherapy |
| US20030195255A1 (en) | 2002-04-12 | 2003-10-16 | Summar Marshall L. | Method for treating hepatic encephalopathies |
| US20040229948A1 (en) | 2002-04-12 | 2004-11-18 | Summar Marshall L. | Method for preventing hepatic encephalopathic episodes |
| CN1383815A (zh) | 2002-05-08 | 2002-12-11 | 刘万忠 | 防治肝病、肝性脑病的鸟氨酸和门冬氨酸的复方制剂及其制备方法 |
| US20040152784A1 (en) | 2002-07-23 | 2004-08-05 | Special Products Limited | Pharmaceutical composition and method for treatment of a urea cycle deficiency or sickle-cell anaemia |
| EP1541141A1 (en) | 2002-08-30 | 2005-06-15 | Ajinomoto Co., Inc. | Therapeutic agent for hepatic disease |
| US20050059150A1 (en) | 2003-09-17 | 2005-03-17 | Becton, Dickinson And Company | Environments that maintain function of primary liver cells |
| MXPA03009902A (es) * | 2003-10-29 | 2005-05-03 | Manuel Francisco Lara Och Jose | Compuestos para reducir la hiperamonemia en pacientes con cirrosis u otras incapacidad para la eliminacion de amonio. |
| EP1718667B1 (en) | 2004-02-23 | 2013-01-09 | Genentech, Inc. | Heterocyclic self-immolative linkers and conjugates |
| CN101010087B (zh) | 2004-05-06 | 2012-06-27 | 奥斯泰奥洛吉斯公司 | 用于制备金属有机盐的高收率和快速的合成方法 |
| US20060045912A1 (en) | 2004-08-30 | 2006-03-02 | Peter Truog | 4-phenylbutyric acid controlled-release formulations for therapeutic use |
| PL1824563T3 (pl) | 2004-11-26 | 2010-07-30 | Ucl Business Plc | Kompozycje zawierające ornitynę i fenylooctan lub fenylomaślan do leczenia encefalopatii wątrobowej |
| HRP20140476T1 (hr) | 2005-11-17 | 2014-07-18 | Silverstone Pharma Est. | Stabilni oblik amorfnih soli perindoprila, postupak njihove pripreme, posebno industrijske pripreme i njihova uporaba u lijeäśenju hipertenzije |
| CN201421432Y (zh) * | 2009-02-20 | 2010-03-10 | 山东师范大学 | 一种相干衍射成像处理装置 |
| 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 |
| 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 |
-
2011
- 2011-10-05 JP JP2013532925A patent/JP6087284B2/ja not_active Expired - Fee Related
- 2011-10-05 EP EP11831546.4A patent/EP2625162B1/en active Active
- 2011-10-05 CN CN201180058441.1A patent/CN103502203B/zh not_active Expired - Fee Related
- 2011-10-05 TR TR2019/03978T patent/TR201903978T4/tr unknown
- 2011-10-05 KR KR1020137011664A patent/KR101888215B1/ko active Active
- 2011-10-05 EA EA201390403A patent/EA028395B1/ru not_active IP Right Cessation
- 2011-10-05 MX MX2013003764A patent/MX360062B/es active IP Right Grant
- 2011-10-05 CA CA2813563A patent/CA2813563C/en active Active
- 2011-10-05 WO PCT/US2011/054983 patent/WO2012048043A1/en not_active Ceased
- 2011-10-05 SG SG2013024559A patent/SG189231A1/en unknown
- 2011-10-05 ES ES11831546T patent/ES2720148T3/es active Active
- 2011-10-05 NZ NZ609191A patent/NZ609191A/en not_active IP Right Cessation
- 2011-10-05 US US13/878,146 patent/US8946473B2/en active Active
- 2011-10-05 AU AU2011312042A patent/AU2011312042B2/en not_active Ceased
- 2011-10-05 BR BR112013008054-0A patent/BR112013008054B1/pt not_active IP Right Cessation
-
2013
- 2013-04-02 IL IL225512A patent/IL225512A/en active IP Right Grant
-
2015
- 2015-01-21 US US14/601,591 patent/US9260379B2/en active Active
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