CH434285A - Verfahren zur Herstellung des L-Asparaginsäuresalzes des L-Ornithins bzw. dessen Monohydrats - Google Patents
Verfahren zur Herstellung des L-Asparaginsäuresalzes des L-Ornithins bzw. dessen MonohydratsInfo
- Publication number
- CH434285A CH434285A CH502063A CH502063A CH434285A CH 434285 A CH434285 A CH 434285A CH 502063 A CH502063 A CH 502063A CH 502063 A CH502063 A CH 502063A CH 434285 A CH434285 A CH 434285A
- Authority
- CH
- Switzerland
- Prior art keywords
- ornithine
- aspartic acid
- monohydrate
- production
- acid salt
- Prior art date
Links
- AHLPHDHHMVZTML-BYPYZUCNSA-N L-Ornithine Chemical compound NCCC[C@H](N)C(O)=O AHLPHDHHMVZTML-BYPYZUCNSA-N 0.000 title claims description 32
- AHLPHDHHMVZTML-UHFFFAOYSA-N Orn-delta-NH2 Natural products NCCCC(N)C(O)=O AHLPHDHHMVZTML-UHFFFAOYSA-N 0.000 title claims description 24
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical class OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 title claims description 19
- 229960003104 ornithine Drugs 0.000 title claims description 18
- 238000000034 method Methods 0.000 title claims description 9
- 150000004682 monohydrates Chemical class 0.000 title claims description 6
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- 229960005261 aspartic acid Drugs 0.000 claims description 16
- CKLJMWTZIZZHCS-UHFFFAOYSA-N D-OH-Asp Natural products OC(=O)C(N)CC(O)=O CKLJMWTZIZZHCS-UHFFFAOYSA-N 0.000 claims description 11
- CKLJMWTZIZZHCS-UWTATZPHSA-N L-Aspartic acid Natural products OC(=O)[C@H](N)CC(O)=O CKLJMWTZIZZHCS-UWTATZPHSA-N 0.000 claims description 11
- AHLPHDHHMVZTML-SCSAIBSYSA-N D-Ornithine Chemical compound NCCC[C@@H](N)C(O)=O AHLPHDHHMVZTML-SCSAIBSYSA-N 0.000 claims description 2
- 238000001640 fractional crystallisation Methods 0.000 claims description 2
- VZLDSDZYNAJGLX-ZBRNBAAYSA-N (2s)-2,4-diamino-4-oxobutanoic acid;(2s)-2,5-diaminopentanoic acid Chemical compound NCCC[C@H](N)C(O)=O.OC(=O)[C@@H](N)CC(N)=O VZLDSDZYNAJGLX-ZBRNBAAYSA-N 0.000 claims 1
- 230000001419 dependent effect Effects 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 239000000203 mixture Substances 0.000 description 8
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 7
- 239000000047 product Substances 0.000 description 6
- UTJLXEIPEHZYQJ-UHFFFAOYSA-N Ornithine Natural products OC(=O)C(C)CCCN UTJLXEIPEHZYQJ-UHFFFAOYSA-N 0.000 description 4
- 235000003704 aspartic acid Nutrition 0.000 description 4
- OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 description 4
- 238000000354 decomposition reaction Methods 0.000 description 4
- 239000000155 melt Substances 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 229910021529 ammonia Inorganic materials 0.000 description 3
- 239000008280 blood Substances 0.000 description 3
- 210000004369 blood Anatomy 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 239000012452 mother liquor Substances 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000004060 metabolic process Effects 0.000 description 2
- GGTYBZJRPHEQDG-WCCKRBBISA-N (2s)-2,5-diaminopentanoic acid hydrochloride Chemical compound Cl.NCCC[C@H](N)C(O)=O GGTYBZJRPHEQDG-WCCKRBBISA-N 0.000 description 1
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 1
- 206010020575 Hyperammonaemia Diseases 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 230000001133 acceleration Effects 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 229940024606 amino acid Drugs 0.000 description 1
- 235000001014 amino acid Nutrition 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- XKMRRTOUMJRJIA-UHFFFAOYSA-N ammonia nh3 Chemical compound N.N XKMRRTOUMJRJIA-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 150000001510 aspartic acids Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000003729 cation exchange resin Substances 0.000 description 1
- 229920001429 chelating resin Polymers 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000002440 hepatic effect Effects 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- KHPXUQMNIQBQEV-UHFFFAOYSA-N oxaloacetic acid Chemical compound OC(=O)CC(=O)C(O)=O KHPXUQMNIQBQEV-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 230000004102 tricarboxylic acid cycle Effects 0.000 description 1
Classifications
-
- 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
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
- A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
- A23L27/20—Synthetic spices, flavouring agents or condiments
- A23L27/21—Synthetic spices, flavouring agents or condiments containing amino acids
-
- 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
- A61K31/16—Amides, e.g. hydroxamic acids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
- A61K38/04—Peptides having up to 20 amino acids in a fully defined sequence; Derivatives thereof
- A61K38/05—Dipeptides
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Medicinal Chemistry (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Engineering & Computer Science (AREA)
- Polymers & Plastics (AREA)
- Immunology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Gastroenterology & Hepatology (AREA)
- Nutrition Science (AREA)
- Food Science & Technology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1654062 | 1962-04-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH434285A true CH434285A (de) | 1967-04-30 |
Family
ID=11919082
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH502063A CH434285A (de) | 1962-04-23 | 1963-04-22 | Verfahren zur Herstellung des L-Asparaginsäuresalzes des L-Ornithins bzw. dessen Monohydrats |
Country Status (7)
| Country | Link |
|---|---|
| AT (1) | AT246344B (enrdf_load_stackoverflow) |
| BR (1) | BR6348588D0 (enrdf_load_stackoverflow) |
| CH (1) | CH434285A (enrdf_load_stackoverflow) |
| DE (1) | DE1518361B1 (enrdf_load_stackoverflow) |
| DK (1) | DK109694C (enrdf_load_stackoverflow) |
| FR (1) | FR4048M (enrdf_load_stackoverflow) |
| GB (1) | GB965637A (enrdf_load_stackoverflow) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE789856A (fr) * | 1971-10-13 | 1973-02-01 | Tixier Georges | Medicament a base de derives de la lysine susceptibles de stimuler differents metabolismes, en particulier la genese des leucocytes |
| US3832465A (en) * | 1971-12-09 | 1974-08-27 | H Ghadimi | Injectable amino acid composition commensurate to the anabolic need of the body and method of using same |
| FR2495608A1 (fr) * | 1980-12-04 | 1982-06-11 | Morelle Jean | Nouveaux derives de l'acide aspartique et leurs usages |
| US4972634A (en) * | 1989-01-19 | 1990-11-27 | Dresden Gregory M | Portable walling |
| ATE116285T1 (de) * | 1990-09-28 | 1995-01-15 | Kyowa Hakko Kogyo Kk | Verfahren zur herstellung von kristallen eines salzes von sauerer aminosäure und basischer aminosäure. |
| PT1824563E (pt) | 2004-11-26 | 2010-05-17 | Ucl Business Plc | Composições compreendendo ornitina e fenilacetato ou fenilbutirato para tratamento de encefalopatia hepática |
| AU2010232521B2 (en) | 2009-04-03 | 2015-07-16 | Ocera Therapeutics, Inc. | L-ornithine phenyl acetate and methods of making thereof |
| CA2997484C (en) | 2009-06-08 | 2020-05-12 | Ucl Business Plc | Treatment of portal hypertension and restoration of liver function using l-ornithine phenylacetate |
| 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 |
| SG11201704011XA (en) | 2014-11-24 | 2017-06-29 | Ucl Business Plc | Treatment of diseases associated with hepatic stellate cell activation using ammonia-lowering therapies |
| AU2016299246B2 (en) * | 2015-07-24 | 2021-10-21 | Evonik Operations Gmbh | Effervescent formulations of ornithine aspartate |
| CA2995823A1 (en) | 2015-08-18 | 2017-02-23 | Ocera Therapeutics, Inc. | Treatment and prevention of muscle loss using l-ornithine in combination with at least one of phenylacetate and phenylbutyrate |
| KR20200024145A (ko) | 2017-05-11 | 2020-03-06 | 오세라 테라퓨틱스, 아이엔씨. | L-오르니틴 페닐아세테이트의 제조방법 |
-
1963
- 1963-04-10 GB GB14309/63A patent/GB965637A/en not_active Expired
- 1963-04-19 DK DK184763AA patent/DK109694C/da active
- 1963-04-22 BR BR148588/63A patent/BR6348588D0/pt unknown
- 1963-04-22 DE DE19631518361 patent/DE1518361B1/de active Pending
- 1963-04-22 CH CH502063A patent/CH434285A/de unknown
- 1963-04-23 AT AT327763A patent/AT246344B/de active
- 1963-07-19 FR FR931676A patent/FR4048M/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DE1518361B1 (de) | 1969-11-13 |
| GB965637A (en) | 1964-08-06 |
| AT246344B (de) | 1966-04-12 |
| BR6348588D0 (pt) | 1973-07-03 |
| DK109694C (da) | 1968-06-10 |
| FR4048M (enrdf_load_stackoverflow) | 1966-04-04 |
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