DE1593980A1 - Betain-N-gentisat und Verfahren zu seiner Herstellung - Google Patents
Betain-N-gentisat und Verfahren zu seiner HerstellungInfo
- Publication number
- DE1593980A1 DE1593980A1 DE19671593980 DE1593980A DE1593980A1 DE 1593980 A1 DE1593980 A1 DE 1593980A1 DE 19671593980 DE19671593980 DE 19671593980 DE 1593980 A DE1593980 A DE 1593980A DE 1593980 A1 DE1593980 A1 DE 1593980A1
- Authority
- DE
- Germany
- Prior art keywords
- betaine
- sec
- gentisic acid
- salt
- gentisate
- 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
- 238000000034 method Methods 0.000 title claims description 12
- 229940114119 gentisate Drugs 0.000 title description 6
- 238000002360 preparation method Methods 0.000 title description 2
- WXTMDXOMEHJXQO-UHFFFAOYSA-N 2,5-dihydroxybenzoic acid Chemical compound OC(=O)C1=CC(O)=CC=C1O WXTMDXOMEHJXQO-UHFFFAOYSA-N 0.000 claims description 26
- 150000003839 salts Chemical class 0.000 claims description 12
- 229960005219 gentisic acid Drugs 0.000 claims description 10
- 230000001476 alcoholic effect Effects 0.000 claims description 4
- 239000003456 ion exchange resin Substances 0.000 claims description 3
- 229920003303 ion-exchange polymer Polymers 0.000 claims description 3
- 239000007791 liquid phase Substances 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- 239000012071 phase Substances 0.000 claims description 2
- 239000007788 liquid Substances 0.000 claims 1
- 235000008001 rakum palm Nutrition 0.000 claims 1
- KWIUHFFTVRNATP-UHFFFAOYSA-N glycine betaine Chemical compound C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 description 53
- 229960003237 betaine Drugs 0.000 description 26
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 22
- 241000700198 Cavia Species 0.000 description 8
- 241001465754 Metazoa Species 0.000 description 8
- 239000000243 solution Substances 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- 210000000941 bile Anatomy 0.000 description 5
- 239000007924 injection Substances 0.000 description 5
- 238000002347 injection Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- LCTONWCANYUPML-UHFFFAOYSA-M Pyruvate Chemical compound CC(=O)C([O-])=O LCTONWCANYUPML-UHFFFAOYSA-M 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 210000004185 liver Anatomy 0.000 description 4
- 239000000975 dye Substances 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 230000000144 pharmacologic effect Effects 0.000 description 3
- 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 2
- YKXUOESQDCXGIW-UHFFFAOYSA-N 2-hydroxypropane-1,2,3-tricarboxylic acid;2-(trimethylazaniumyl)acetate Chemical compound C[N+](C)(C)CC(O)=O.OC(=O)CC(O)(C(O)=O)CC([O-])=O YKXUOESQDCXGIW-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 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 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 229960002609 betaine citrate Drugs 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- -1 etc. Chemical class 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 229910017053 inorganic salt Inorganic materials 0.000 description 2
- 150000004702 methyl esters Chemical class 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 241000700199 Cavia porcellus Species 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 206010067125 Liver injury Diseases 0.000 description 1
- 241001461123 Matrona Species 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 208000027418 Wounds and injury Diseases 0.000 description 1
- 239000003463 adsorbent Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 239000003957 anion exchange resin Substances 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 1
- 239000010428 baryte Substances 0.000 description 1
- 229910052601 baryte Inorganic materials 0.000 description 1
- 210000000013 bile duct Anatomy 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 238000011088 calibration curve Methods 0.000 description 1
- QJWNYSRCYOCRGE-UHFFFAOYSA-O carboxymethyl(trimethyl)azanium;nitrate Chemical compound [O-][N+]([O-])=O.C[N+](C)(C)CC(O)=O QJWNYSRCYOCRGE-UHFFFAOYSA-O 0.000 description 1
- 239000003729 cation exchange resin Substances 0.000 description 1
- 229940023913 cation exchange resins Drugs 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 230000029142 excretion Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 231100000234 hepatic damage Toxicity 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 208000014674 injury Diseases 0.000 description 1
- 239000007925 intracardiac injection Substances 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 230000007775 late Effects 0.000 description 1
- 230000003212 lipotrophic effect Effects 0.000 description 1
- 230000008818 liver damage Effects 0.000 description 1
- 241000238565 lobster Species 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 230000009965 odorless effect Effects 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 239000002574 poison Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 231100000572 poisoning Toxicity 0.000 description 1
- 230000000607 poisoning effect Effects 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C65/00—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C65/01—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing hydroxy or O-metal groups
- C07C65/03—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing hydroxy or O-metal groups monocyclic and having all hydroxy or O-metal groups bound to the ring
- C07C65/05—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing hydroxy or O-metal groups monocyclic and having all hydroxy or O-metal groups bound to the ring o-Hydroxy carboxylic acids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR49796A FR1479304A (fr) | 1966-02-16 | 1966-02-16 | Nouveaux dérivés aminés de l'acide gentisique et procédés de fabrication |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1593980A1 true DE1593980A1 (de) | 1970-10-29 |
Family
ID=8601481
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19671593980 Pending DE1593980A1 (de) | 1966-02-16 | 1967-02-15 | Betain-N-gentisat und Verfahren zu seiner Herstellung |
Country Status (7)
| Country | Link |
|---|---|
| BE (1) | BE693697A (enrdf_load_stackoverflow) |
| CH (1) | CH476670A (enrdf_load_stackoverflow) |
| DE (1) | DE1593980A1 (enrdf_load_stackoverflow) |
| ES (1) | ES336870A1 (enrdf_load_stackoverflow) |
| FR (1) | FR1479304A (enrdf_load_stackoverflow) |
| GB (1) | GB1126605A (enrdf_load_stackoverflow) |
| NL (1) | NL6702210A (enrdf_load_stackoverflow) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1196356B (it) * | 1984-12-05 | 1988-11-16 | Pavese Ist Biochim | Sale solubile avente attivita' anti-infiammatoria,procedimento per la sua preparazione e forme farmaceutiche contenenti lo stesso |
-
1966
- 1966-02-16 FR FR49796A patent/FR1479304A/fr not_active Expired
-
1967
- 1967-02-06 BE BE693697D patent/BE693697A/xx unknown
- 1967-02-07 CH CH174867A patent/CH476670A/fr not_active IP Right Cessation
- 1967-02-08 GB GB596667A patent/GB1126605A/en not_active Expired
- 1967-02-14 NL NL6702210A patent/NL6702210A/xx unknown
- 1967-02-15 ES ES336870A patent/ES336870A1/es not_active Expired
- 1967-02-15 DE DE19671593980 patent/DE1593980A1/de active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| GB1126605A (en) | 1968-09-11 |
| ES336870A1 (es) | 1968-01-01 |
| NL6702210A (enrdf_load_stackoverflow) | 1967-08-17 |
| CH476670A (fr) | 1969-08-15 |
| FR1479304A (fr) | 1967-05-05 |
| BE693697A (enrdf_load_stackoverflow) | 1967-07-17 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2128607C3 (de) | Neues D-Morphinanderivat | |
| DE1802162A1 (de) | Neue N-Pyridylmethyliden-homocystein-thiolacton-Verbindung und Verfahren zu ihrer Herstellung | |
| DE753235C (de) | Verfahren zur Herstellung waessriger Lactoflavinloesungen | |
| DE1593980A1 (de) | Betain-N-gentisat und Verfahren zu seiner Herstellung | |
| DE2108237C3 (de) | Salz des Pyridoxin-a-ketoglutarats mit 5-Hydroxytryptophan und Verfahren zu seiner Herstellung | |
| DE1936723C2 (de) | Salze von Chinarindenalkoloiden und Verfahren zu ihrer Herstellung | |
| DE1493618A1 (de) | Cumarinderivate und ein Verfahren zu ihrer Herstellung | |
| DE2357864A1 (de) | Nicotinsaure salze von derivaten des biguanids, verfahren zu ihrer herstellung, sowie diese salze enthaltende arzneimittel | |
| DE629662C (de) | Verfahren zur Herstellung einer konzentrierten, haltbaren, waessrigen Theophyllinloesung | |
| DE728804C (de) | Verfahren zur Herstellung von Salzen des Morphins mit Aralkylcarbonsaeuren | |
| DE907293C (de) | Verfahren zur Herstellung von Polyschwefelsaeureesteren und Salzen derselben | |
| DE2413802A1 (de) | Gemischte salze von sulfoglykopeptiden mit metallbasen und organischen basen und verfahren zu ihrer herstellung | |
| DE738499C (de) | Verfahren zur Darstellung von Additionsverbindungen des Hexamethylentetramins | |
| AT356277B (de) | Verfahren zur herstellung waesseriger injektionsloesungen mit einem gehalt an valproinsaeure | |
| DE519053C (de) | Verfahren zur Herstellung von Salzen der Camphersaeure mit Scopolamin, Hyoscyamin und Atropin | |
| DE2244461C3 (de) | 3-Chlor-4,4'-disulfoxydiphenyl-(2-pvridyl)-methansalze, Verfahren zu deren Herstellung sowie diese Salze enthaltende pharmazeutische Zusammensetzungen | |
| DE2420153C3 (de) | Arzneimittel mit lokalanästhetischer Wirkung | |
| DE561314C (de) | Verfahren zur Herstellung von leicht loeslichen Salzen hochmolekularer jodierter Fettsaeuren | |
| DE495336C (de) | Verfahren zur Darstellung von basischen Oximaethern und ihren Salzen | |
| AT345271B (de) | Verfahren zur herstellung des kristallwasserfreien magnesium-2- (p-chlorphenoxy) -isobutyrats | |
| DE951756C (de) | Verfahren zur Herstellung konzentrierter haltbarer waessriger Loesungen von Furanochromonen | |
| DE1695328C3 (de) | Cinnamylpiperazinverbindungen, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneipräparate | |
| DE629841C (de) | Verfahren zur Herstellung einer waessrigen Chininloesung fuer Injektionszwecke | |
| DE574564C (de) | Verfahren zur Herstellung von Salzen zweibasischer organischer Saeuren | |
| AT239443B (de) | Verfahren zur Herstellung von insbesondere für Injektionszwecke geeigneten wässerigen Lösungen der Orotsäure |