CA2813563C - Methods of making l-ornithine phenyl acetate - Google Patents
Methods of making l-ornithine phenyl acetate Download PDFInfo
- Publication number
- CA2813563C CA2813563C CA2813563A CA2813563A CA2813563C CA 2813563 C CA2813563 C CA 2813563C CA 2813563 A CA2813563 A CA 2813563A CA 2813563 A CA2813563 A CA 2813563A CA 2813563 C CA2813563 C CA 2813563C
- Authority
- CA
- Canada
- Prior art keywords
- salt
- ornithine
- phenyl acetate
- benzoate
- composition comprises
- 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.)
- Active
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/14—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof
- C07C227/18—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof by reactions involving amino or carboxyl groups, e.g. hydrolysis of esters or amides, by formation of halides, salts or esters
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/192—Carboxylic acids, e.g. valproic acid having aromatic groups, e.g. sulindac, 2-aryl-propionic acids, ethacrynic acid
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/195—Carboxylic acids, e.g. valproic acid having an amino group
- A61K31/197—Carboxylic acids, e.g. valproic acid having an amino group the amino and the carboxyl groups being attached to the same acyclic carbon chain, e.g. gamma-aminobutyric acid [GABA], beta-alanine, epsilon-aminocaproic acid or pantothenic acid
- A61K31/198—Alpha-amino acids, e.g. alanine or edetic acid [EDTA]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C229/04—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C229/26—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having more than one amino group bound to the carbon skeleton, e.g. lysine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/41—Preparation of salts of carboxylic acids
- C07C51/412—Preparation of salts of carboxylic acids by conversion of the acids, their salts, esters or anhydrides with the same carboxylic acid part
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/30—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing six-membered aromatic rings
- C07C57/32—Phenylacetic acid
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Epidemiology (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Gastroenterology & Hepatology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
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 (2)
| Publication Number | Publication Date |
|---|---|
| CA2813563A1 CA2813563A1 (en) | 2012-04-12 |
| CA2813563C true CA2813563C (en) | 2019-02-26 |
Family
ID=45928120
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2813563A Active CA2813563C (en) | 2010-10-06 | 2011-10-05 | Methods of making l-ornithine phenyl acetate |
Country Status (16)
| Country | Link |
|---|---|
| US (2) | US8946473B2 (OSRAM) |
| EP (1) | EP2625162B1 (OSRAM) |
| JP (1) | JP6087284B2 (OSRAM) |
| KR (1) | KR101888215B1 (OSRAM) |
| CN (1) | CN103502203B (OSRAM) |
| AU (1) | AU2011312042B2 (OSRAM) |
| BR (1) | BR112013008054B1 (OSRAM) |
| CA (1) | CA2813563C (OSRAM) |
| EA (1) | EA028395B1 (OSRAM) |
| ES (1) | ES2720148T3 (OSRAM) |
| IL (1) | IL225512A (OSRAM) |
| MX (1) | MX360062B (OSRAM) |
| NZ (1) | NZ609191A (OSRAM) |
| SG (1) | SG189231A1 (OSRAM) |
| TR (1) | TR201903978T4 (OSRAM) |
| WO (1) | WO2012048043A1 (OSRAM) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2006056794A1 (en) | 2004-11-26 | 2006-06-01 | Ucl Business Plc | Compositions comprising ornithine and phenylacetate or phenylbutyrate for treating hepatic encephalopathy |
| SMT201700601T1 (it) * | 2009-04-03 | 2018-03-08 | Ocera Therapeutics Inc | L-ornitina fenilacetato e metodi per la sua fabbricazione |
| EP2799067B1 (en) | 2009-06-08 | 2019-04-03 | UCL Business PLC | Treatment of brain inflammation using L-Ornithine Phenylacetate |
| NZ609191A (en) * | 2010-10-06 | 2015-06-26 | Ocera Therapeutics Inc | Methods of making l-ornithine phenyl acetate |
| KR20230018526A (ko) | 2014-11-24 | 2023-02-07 | 유씨엘 비즈니스 리미티드 | 암모니아-저감 치료를 이용한 간성상세포 활성화와 연관된 질병의 치료 |
| KR20180006904A (ko) * | 2015-04-20 | 2018-01-19 | 오세라 테라퓨틱스, 아이엔씨. | L-오르니틴 페닐아세테이트의 제형 |
| HK1249434A1 (zh) | 2015-08-18 | 2018-11-02 | Ocera Therapeutics, Inc. | 使用与苯乙酸盐和苯丁酸盐中的至少一种组合的l-鸟氨酸治疗和预防肌肉损失 |
| US11219611B2 (en) | 2015-11-13 | 2022-01-11 | Ocera Therapeutics, Inc. | Formulations of L-ornithine phenylacetate |
| CA3004331A1 (en) | 2015-11-13 | 2017-05-18 | 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 |
| IL270413B (en) * | 2017-05-11 | 2022-08-01 | Ocera Therapeutics Inc | Processes of making l-ornithine phenylacetate |
| BR112020002419A2 (pt) | 2017-08-14 | 2020-07-28 | Axcella Health Inc. | aminoácido para o tratamento de doença do fígado |
| CN112839643A (zh) | 2018-06-20 | 2021-05-25 | 胺细拉健康公司 | 用于治疗肌肉中脂肪浸润的组合物及方法 |
| 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 (OSRAM) | 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 |
| DE4020980C1 (OSRAM) | 1990-07-02 | 1991-09-26 | Degussa Ag, 6000 Frankfurt, De | |
| US5591613A (en) | 1990-07-02 | 1997-01-07 | Degussa Aktiengesellschaft | Method for the preparation of D-arginine and L-ornithine |
| 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 |
| NZ255541A (en) | 1992-09-09 | 1996-05-28 | Fisons Plc | Blister package for medicament-containing capsules with an aperture for dispensing the medicament; the package base has a sealing means to seal the capsule aperture |
| 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 |
| US6083953A (en) | 1994-07-28 | 2000-07-04 | Syntex (U.S.A.) Inc. | 2- (2-amino-1,6-dihydro-6-oxo-purin-9-yl) methoxy-1,3- propanediol derivative |
| AU2251897A (en) | 1996-02-13 | 1997-09-02 | Trustees Of The University Of Pennsylvania, The | 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 |
| EP1179347A4 (en) | 1999-05-21 | 2002-06-26 | Takeda Chemical Industries Ltd | CONTROL SUBSTANCES FOR LIVER FUNCTION |
| 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 |
| JPWO2004019928A1 (ja) | 2002-08-30 | 2005-12-15 | 味の素株式会社 | 肝疾患治療剤 |
| 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. |
| JP5064037B2 (ja) | 2004-02-23 | 2012-10-31 | ジェネンテック， インコーポレイテッド | 複素環式自壊的リンカーおよび結合体 |
| AU2005240257B2 (en) | 2004-05-06 | 2011-11-24 | Osteologix A/S | High yield and rapid syntheses methods for producing metallo-organic salts |
| US20060045912A1 (en) | 2004-08-30 | 2006-03-02 | Peter Truog | 4-phenylbutyric acid controlled-release formulations for therapeutic use |
| WO2006056794A1 (en) | 2004-11-26 | 2006-06-01 | Ucl Business Plc | Compositions comprising ornithine and phenylacetate or phenylbutyrate for treating hepatic encephalopathy |
| PL1948224T3 (pl) | 2005-11-17 | 2014-10-31 | Silverstone Pharma Est | Trwały preparat amorficznych soli peryndoprylu, sposób ich wytwarzania, zwłaszcza wytwarzania w skali przemysłowej oraz ich zastosowanie w terapii nadciśnienia |
| 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 |
| SMT201700601T1 (it) | 2009-04-03 | 2018-03-08 | Ocera Therapeutics Inc | L-ornitina fenilacetato e metodi per la sua fabbricazione |
| EP2799067B1 (en) | 2009-06-08 | 2019-04-03 | UCL Business PLC | Treatment of brain inflammation using L-Ornithine Phenylacetate |
| NZ609191A (en) | 2010-10-06 | 2015-06-26 | Ocera Therapeutics Inc | Methods of making l-ornithine phenyl acetate |
-
2011
- 2011-10-05 NZ NZ609191A patent/NZ609191A/en not_active IP Right Cessation
- 2011-10-05 CN CN201180058441.1A patent/CN103502203B/zh not_active Expired - Fee Related
- 2011-10-05 EP EP11831546.4A patent/EP2625162B1/en active Active
- 2011-10-05 TR TR2019/03978T patent/TR201903978T4/tr unknown
- 2011-10-05 AU AU2011312042A patent/AU2011312042B2/en not_active Ceased
- 2011-10-05 MX MX2013003764A patent/MX360062B/es active IP Right Grant
- 2011-10-05 WO PCT/US2011/054983 patent/WO2012048043A1/en not_active Ceased
- 2011-10-05 JP JP2013532925A patent/JP6087284B2/ja not_active Expired - Fee Related
- 2011-10-05 CA CA2813563A patent/CA2813563C/en active Active
- 2011-10-05 US US13/878,146 patent/US8946473B2/en active Active
- 2011-10-05 SG SG2013024559A patent/SG189231A1/en unknown
- 2011-10-05 BR BR112013008054-0A patent/BR112013008054B1/pt not_active IP Right Cessation
- 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 ES ES11831546T patent/ES2720148T3/es active Active
-
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
Also Published As
| Publication number | Publication date |
|---|---|
| JP6087284B2 (ja) | 2017-03-01 |
| TR201903978T4 (tr) | 2019-04-22 |
| SG189231A1 (en) | 2013-05-31 |
| NZ609191A (en) | 2015-06-26 |
| MX2013003764A (es) | 2013-05-20 |
| IL225512A (en) | 2017-12-31 |
| AU2011312042B2 (en) | 2015-08-20 |
| US20150133684A1 (en) | 2015-05-14 |
| KR20140053807A (ko) | 2014-05-08 |
| JP2013542935A (ja) | 2013-11-28 |
| CN103502203A (zh) | 2014-01-08 |
| US20130211135A1 (en) | 2013-08-15 |
| MX360062B (es) | 2018-10-22 |
| AU2011312042A1 (en) | 2013-05-02 |
| EP2625162A1 (en) | 2013-08-14 |
| US8946473B2 (en) | 2015-02-03 |
| EA201390403A1 (ru) | 2013-09-30 |
| CN103502203B (zh) | 2016-09-07 |
| BR112013008054A2 (pt) | 2016-06-14 |
| CA2813563A1 (en) | 2012-04-12 |
| US9260379B2 (en) | 2016-02-16 |
| KR101888215B1 (ko) | 2018-09-20 |
| EA028395B1 (ru) | 2017-11-30 |
| IL225512A0 (en) | 2013-06-27 |
| EP2625162B1 (en) | 2019-03-13 |
| EP2625162A4 (en) | 2014-06-25 |
| ES2720148T3 (es) | 2019-07-18 |
| WO2012048043A1 (en) | 2012-04-12 |
| BR112013008054B1 (pt) | 2019-04-09 |
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| AU2017202081B2 (en) | L-ornithine phenyl acetate and methods of making thereof | |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request |
Effective date: 20160912 |