DE1493615A1 - Verfahren zum Herstellen von 4-Hydroxybutyrat des Lysins - Google Patents
Verfahren zum Herstellen von 4-Hydroxybutyrat des LysinsInfo
- Publication number
- DE1493615A1 DE1493615A1 DE19621493615 DE1493615A DE1493615A1 DE 1493615 A1 DE1493615 A1 DE 1493615A1 DE 19621493615 DE19621493615 DE 19621493615 DE 1493615 A DE1493615 A DE 1493615A DE 1493615 A1 DE1493615 A1 DE 1493615A1
- Authority
- DE
- Germany
- Prior art keywords
- lysine
- hydroxybutyrate
- preparation
- des
- 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.)
- Pending
Links
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 title claims description 14
- 239000004472 Lysine Substances 0.000 title claims description 14
- SJZRECIVHVDYJC-UHFFFAOYSA-M 4-hydroxybutyrate Chemical compound OCCCC([O-])=O SJZRECIVHVDYJC-UHFFFAOYSA-M 0.000 title claims description 8
- 238000000034 method Methods 0.000 title claims description 8
- 238000002360 preparation method Methods 0.000 title claims description 3
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 claims description 8
- 229930188620 butyrolactone Natural products 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 4
- 238000002425 crystallisation Methods 0.000 claims description 3
- 230000008025 crystallization Effects 0.000 claims description 3
- 239000012736 aqueous medium Substances 0.000 claims description 2
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 239000000243 solution Substances 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- SJZRECIVHVDYJC-UHFFFAOYSA-N 4-hydroxybutyric acid Chemical compound OCCCC(O)=O SJZRECIVHVDYJC-UHFFFAOYSA-N 0.000 description 2
- 229940006015 4-hydroxybutyric acid Drugs 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- 238000011835 investigation Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000002609 medium Substances 0.000 description 2
- 150000003138 primary alcohols Chemical group 0.000 description 2
- 230000001624 sedative effect Effects 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 241000024188 Andala Species 0.000 description 1
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 1
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000001632 acidimetric titration Methods 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 229940035674 anesthetics Drugs 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- SOCTUWSJJQCPFX-UHFFFAOYSA-N dichromate(2-) Chemical compound [O-][Cr](=O)(=O)O[Cr]([O-])(=O)=O SOCTUWSJJQCPFX-UHFFFAOYSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229960004279 formaldehyde Drugs 0.000 description 1
- 235000019256 formaldehyde Nutrition 0.000 description 1
- 239000003193 general anesthetic agent Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 230000008925 spontaneous activity Effects 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 125000001874 trioxidanyl group Chemical group [*]OOO[H] 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR865283A FR1468616A (fr) | 1961-06-17 | 1961-06-17 | Procédé de préparation du 4-hydroxybutyrate de lysine |
| FR865284A FR1411M (fr) | 1961-06-17 | 1961-06-17 | Médicament a propriétés sédatives et d'épargne protidique a base de 4-hydroxy-butyrate de lysine. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1493615A1 true DE1493615A1 (de) | 1969-08-07 |
Family
ID=26191080
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19621493615 Pending DE1493615A1 (de) | 1961-06-17 | 1962-06-15 | Verfahren zum Herstellen von 4-Hydroxybutyrat des Lysins |
Country Status (6)
| Country | Link |
|---|---|
| BE (1) | BE618534A (enExample) |
| DE (1) | DE1493615A1 (enExample) |
| FR (2) | FR1468616A (enExample) |
| GB (1) | GB954270A (enExample) |
| LU (1) | LU41842A1 (enExample) |
| NL (1) | NL279760A (enExample) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4771074A (en) * | 1982-02-23 | 1988-09-13 | Solvay & Cie (Societe Anonyme) | Pharmaceutical compositions containing a salt derived from 3-hydroxybutanoic acid |
| CN112341331A (zh) * | 2019-08-07 | 2021-02-09 | 辽宁科硕营养科技股份有限公司 | 一种3-羟基丁酸盐及其制备方法与应用 |
-
0
- NL NL279760D patent/NL279760A/xx unknown
-
1961
- 1961-06-17 FR FR865283A patent/FR1468616A/fr not_active Expired
- 1961-06-17 FR FR865284A patent/FR1411M/fr not_active Expired
-
1962
- 1962-06-05 GB GB21617/62A patent/GB954270A/en not_active Expired
- 1962-06-05 BE BE618534A patent/BE618534A/fr unknown
- 1962-06-06 LU LU41842D patent/LU41842A1/xx unknown
- 1962-06-15 DE DE19621493615 patent/DE1493615A1/de active Pending
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4771074A (en) * | 1982-02-23 | 1988-09-13 | Solvay & Cie (Societe Anonyme) | Pharmaceutical compositions containing a salt derived from 3-hydroxybutanoic acid |
| CN112341331A (zh) * | 2019-08-07 | 2021-02-09 | 辽宁科硕营养科技股份有限公司 | 一种3-羟基丁酸盐及其制备方法与应用 |
| CN112341331B (zh) * | 2019-08-07 | 2023-04-07 | 辽宁科硕营养科技股份有限公司 | 一种3-羟基丁酸盐及其制备方法与应用 |
Also Published As
| Publication number | Publication date |
|---|---|
| GB954270A (en) | 1964-04-02 |
| FR1468616A (fr) | 1967-02-10 |
| FR1411M (fr) | 1962-07-23 |
| BE618534A (fr) | 1962-10-01 |
| NL279760A (enExample) | |
| LU41842A1 (enExample) | 1962-08-06 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| SH | Request for examination between 03.10.1968 and 22.04.1971 |