DE1695358A1 - Derivate des Tris(hydroxymethyl)aminomethans - Google Patents
Derivate des Tris(hydroxymethyl)aminomethansInfo
- Publication number
- DE1695358A1 DE1695358A1 DE19671695358 DE1695358A DE1695358A1 DE 1695358 A1 DE1695358 A1 DE 1695358A1 DE 19671695358 DE19671695358 DE 19671695358 DE 1695358 A DE1695358 A DE 1695358A DE 1695358 A1 DE1695358 A1 DE 1695358A1
- Authority
- DE
- Germany
- Prior art keywords
- tris
- acid
- hydroxymethyl
- aminomethane
- salt
- 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
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical class OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 title claims description 39
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 26
- 150000003839 salts Chemical class 0.000 claims description 22
- 238000000034 method Methods 0.000 claims description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 20
- 239000002253 acid Substances 0.000 claims description 19
- 239000000243 solution Substances 0.000 claims description 17
- 235000019136 lipoic acid Nutrition 0.000 claims description 14
- 239000002904 solvent Substances 0.000 claims description 14
- 229960002663 thioctic acid Drugs 0.000 claims description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 12
- 239000007983 Tris buffer Substances 0.000 claims description 12
- 230000008569 process Effects 0.000 claims description 12
- PXQPEWDEAKTCGB-UHFFFAOYSA-N orotic acid Chemical compound OC(=O)C1=CC(=O)NC(=O)N1 PXQPEWDEAKTCGB-UHFFFAOYSA-N 0.000 claims description 11
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 8
- 238000009835 boiling Methods 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 7
- 239000000843 powder Substances 0.000 claims description 6
- VYEYJCBEXFTGBN-UHFFFAOYSA-N acetic acid;1,3-dimethyl-7h-purine-2,6-dione Chemical compound CC(O)=O.O=C1N(C)C(=O)N(C)C2=C1NC=N2 VYEYJCBEXFTGBN-UHFFFAOYSA-N 0.000 claims description 5
- 239000013078 crystal Substances 0.000 claims description 5
- 229960005010 orotic acid Drugs 0.000 claims description 5
- 238000003756 stirring Methods 0.000 claims description 4
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 3
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 3
- 230000015572 biosynthetic process Effects 0.000 claims description 2
- 229940106978 pangamate Drugs 0.000 claims description 2
- 239000002798 polar solvent Substances 0.000 claims 9
- AGBQKNBQESQNJD-UHFFFAOYSA-N lipoic acid Chemical compound OC(=O)CCCCC1CCSS1 AGBQKNBQESQNJD-UHFFFAOYSA-N 0.000 claims 6
- RVSTWRHIGKXTLG-WCXIOVBPSA-N Pangamic acid Chemical compound CC(C)N(C(C)C)C(N(C(C)C)C(C)C)C(=O)OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RVSTWRHIGKXTLG-WCXIOVBPSA-N 0.000 claims 5
- RVSTWRHIGKXTLG-UHFFFAOYSA-N Pangamic acid Natural products CC(C)N(C(C)C)C(N(C(C)C)C(C)C)C(=O)OCC(O)C(O)C(O)C(O)C(O)=O RVSTWRHIGKXTLG-UHFFFAOYSA-N 0.000 claims 5
- 238000001914 filtration Methods 0.000 claims 5
- 229940055705 pangamic acid Drugs 0.000 claims 5
- 108700024047 pangamic acid Proteins 0.000 claims 5
- 229910017053 inorganic salt Inorganic materials 0.000 claims 4
- 150000002763 monocarboxylic acids Chemical class 0.000 claims 2
- 150000007513 acids Chemical class 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 238000001704 evaporation Methods 0.000 claims 1
- 230000008020 evaporation Effects 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 230000000630 rising effect Effects 0.000 claims 1
- 238000001291 vacuum drying Methods 0.000 claims 1
- 238000005406 washing Methods 0.000 claims 1
- 235000019441 ethanol Nutrition 0.000 description 17
- 208000010444 Acidosis Diseases 0.000 description 13
- 230000007950 acidosis Effects 0.000 description 12
- 208000026545 acidosis disease Diseases 0.000 description 12
- 239000000047 product Substances 0.000 description 10
- 150000001875 compounds Chemical class 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- AGBQKNBQESQNJD-UHFFFAOYSA-M lipoate Chemical compound [O-]C(=O)CCCCC1CCSS1 AGBQKNBQESQNJD-UHFFFAOYSA-M 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 6
- 239000008280 blood Substances 0.000 description 5
- 238000001990 intravenous administration Methods 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 210000004369 blood Anatomy 0.000 description 4
- 239000000872 buffer Substances 0.000 description 4
- 238000011282 treatment Methods 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- -1 hydroxy- Chemical class 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- 229960000278 theophylline Drugs 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- 206010027417 Metabolic acidosis Diseases 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- 208000003826 Respiratory Acidosis Diseases 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 229910000831 Steel Inorganic materials 0.000 description 2
- 210000001124 body fluid Anatomy 0.000 description 2
- 239000010839 body fluid Substances 0.000 description 2
- 230000003139 buffering effect Effects 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 230000001079 digestive effect Effects 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000001788 irregular Effects 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 230000004060 metabolic process Effects 0.000 description 2
- 230000000241 respiratory effect Effects 0.000 description 2
- 239000010959 steel Substances 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- 231100000331 toxic Toxicity 0.000 description 2
- 230000002588 toxic effect Effects 0.000 description 2
- 208000007848 Alcoholism Diseases 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 208000005156 Dehydration Diseases 0.000 description 1
- 208000001380 Diabetic Ketoacidosis Diseases 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- 206010023388 Ketonuria Diseases 0.000 description 1
- 208000007976 Ketosis Diseases 0.000 description 1
- 208000002720 Malnutrition Diseases 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 206010037660 Pyrexia Diseases 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 231100000645 Reed–Muench method Toxicity 0.000 description 1
- 206010047700 Vomiting Diseases 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 201000007930 alcohol dependence Diseases 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 229940125717 barbiturate Drugs 0.000 description 1
- 229960000182 blood factors Drugs 0.000 description 1
- 230000036772 blood pressure Effects 0.000 description 1
- 230000001914 calming effect Effects 0.000 description 1
- 235000014633 carbohydrates Nutrition 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 230000001413 cellular effect Effects 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 1
- 229940106681 chloroacetic acid Drugs 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 230000000994 depressogenic effect Effects 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000002934 diuretic Substances 0.000 description 1
- 230000001882 diuretic effect Effects 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 230000029142 excretion Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 230000001434 glomerular Effects 0.000 description 1
- 230000010224 hepatic metabolism Effects 0.000 description 1
- 239000008240 homogeneous mixture Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 231100000566 intoxication Toxicity 0.000 description 1
- 230000035987 intoxication Effects 0.000 description 1
- 230000003834 intracellular effect Effects 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 230000007794 irritation Effects 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 230000003908 liver function Effects 0.000 description 1
- 230000001071 malnutrition Effects 0.000 description 1
- 235000000824 malnutrition Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical class C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- NQMRYBIKMRVZLB-UHFFFAOYSA-N methylamine hydrochloride Chemical compound [Cl-].[NH3+]C NQMRYBIKMRVZLB-UHFFFAOYSA-N 0.000 description 1
- IZXGZAJMDLJLMF-UHFFFAOYSA-N methylaminomethanol Chemical compound CNCO IZXGZAJMDLJLMF-UHFFFAOYSA-N 0.000 description 1
- 239000004570 mortar (masonry) Substances 0.000 description 1
- 231100000956 nontoxicity Toxicity 0.000 description 1
- 208000015380 nutritional deficiency disease Diseases 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 230000002685 pulmonary effect Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 230000008844 regulatory mechanism Effects 0.000 description 1
- 210000001034 respiratory center Anatomy 0.000 description 1
- 230000029058 respiratory gaseous exchange Effects 0.000 description 1
- 229940058287 salicylic acid derivative anticestodals Drugs 0.000 description 1
- 150000003872 salicylic acid derivatives Chemical class 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- MKVDFFROCUECAJ-CKDSBIORSA-M sodium;(2r,3s,4r,5r)-6-[2-(dimethylamino)acetyl]oxy-2,3,4,5-tetrahydroxyhexanoate Chemical compound [Na+].CN(C)CC(=O)OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O MKVDFFROCUECAJ-CKDSBIORSA-M 0.000 description 1
- QVGLHVDBDYLFON-UHFFFAOYSA-M sodium;1,3-dimethylpurin-7-ide-2,6-dione Chemical compound [Na+].O=C1N(C)C(=O)N(C)C2=C1[N-]C=N2 QVGLHVDBDYLFON-UHFFFAOYSA-M 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229940068511 thioctate Drugs 0.000 description 1
- 239000003440 toxic substance Substances 0.000 description 1
- 230000002110 toxicologic effect Effects 0.000 description 1
- 231100000027 toxicology Toxicity 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 0.000 description 1
- 230000008673 vomiting Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/52—Two oxygen atoms
- C07D239/54—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals
- C07D239/545—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals with other hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/557—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals with other hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms, e.g. orotic acid
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D339/00—Heterocyclic compounds containing rings having two sulfur atoms as the only ring hetero atoms
- C07D339/02—Five-membered rings
- C07D339/04—Five-membered rings having the hetero atoms in positions 1 and 2, e.g. lipoic acid
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/02—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6
- C07D473/04—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms
- C07D473/06—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms with radicals containing only hydrogen and carbon atoms, attached in position 1 or 3
- C07D473/08—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms with radicals containing only hydrogen and carbon atoms, attached in position 1 or 3 with methyl radicals in positions 1 and 3, e.g. theophylline
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H23/00—Compounds containing boron, silicon or a metal, e.g. chelates or vitamin B12
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ES0323195A ES323195A1 (es) | 1966-02-17 | 1966-02-17 | Procedimiento de obtenciën de compuestos de acciën antiacidëtica |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1695358A1 true DE1695358A1 (de) | 1972-04-13 |
Family
ID=8442738
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19671695358 Pending DE1695358A1 (de) | 1966-02-17 | 1967-02-16 | Derivate des Tris(hydroxymethyl)aminomethans |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US3562273A (cs) |
| BE (1) | BE694127A (cs) |
| CH (1) | CH469659A (cs) |
| DE (1) | DE1695358A1 (cs) |
| ES (1) | ES323195A1 (cs) |
| FR (1) | FR1511911A (cs) |
| GB (1) | GB1113600A (cs) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0318891A1 (de) * | 1987-12-04 | 1989-06-07 | ASTA Medica Aktiengesellschaft | Injizierbare Lösung des Thioctsäuresalzes mit Trometamol und/oder basischen Aminosäuren |
| EP0702953A2 (de) | 1994-09-22 | 1996-03-27 | ASTA Medica Aktiengesellschaft | Darreichungsformen enthaltend Thioctsäure, oder feste Salze von Thioctsäure mit verbesserter Freisetzung und Bioverfügbarkeit |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL162361C (nl) * | 1974-09-10 | Dufour Claude Etude | Werkwijze ter bereiding van een zout van theofylline- -azijnzuur en van een farmaceutisch preparaat met mucolytische werking, dat dit zout bevat, alsmede farmaceutische voorwerpen. | |
| GB2024087B (en) * | 1978-06-29 | 1982-08-25 | Yoshino Kogyosho Co Ltd | Blow moulding polyester container |
| US5136096A (en) * | 1989-08-31 | 1992-08-04 | University Of South Florida | Multifunctional synthons as used in the preparation of cascade polymers or unimolecular micelles |
| DE10137381A1 (de) * | 2001-07-31 | 2003-02-13 | Viatris Gmbh | Neue Modifikationen des Trometamolsalzes der R-Thioctsäure sowie Verfahren zu ihrer Herstellung |
| EP1984348A2 (en) * | 2006-02-10 | 2008-10-29 | Multi Formulations Ltd. | Method for improving the oral administration of alpha-lipoic acid |
| US8334402B2 (en) * | 2008-04-17 | 2012-12-18 | Thomas Daly | Biological buffers with wide buffering ranges |
| US9090638B2 (en) | 2008-04-17 | 2015-07-28 | Thomas Daly | Biological buffers with wide buffering ranges |
| US9447310B2 (en) | 2008-04-17 | 2016-09-20 | Thomas P. Daly | Biological buffers with wide buffering ranges |
| US20170313920A1 (en) | 2010-10-06 | 2017-11-02 | Thomas P. Daly | Biological Buffers with Wide Buffering Ranges |
| US7939659B2 (en) * | 2008-04-17 | 2011-05-10 | Thomas Daly | Biological buffers with wide buffering ranges |
| US8519141B2 (en) | 2008-04-17 | 2013-08-27 | Thomas Daly | Biological buffers with wide buffering ranges |
| US8822728B2 (en) | 2008-04-17 | 2014-09-02 | Thomas Daly | Biological buffers with wide buffering ranges |
| US7635791B2 (en) * | 2008-04-17 | 2009-12-22 | Tpat Ip Llc | Biological buffers with wide buffering ranges |
| US8034951B2 (en) * | 2008-04-17 | 2011-10-11 | Thomas Daly | Biological buffers with wide buffering ranges |
| KR100935554B1 (ko) | 2009-06-24 | 2010-01-07 | 주식회사 셀트리온제약 | 피페라진 다이티옥트산염 및 이를 포함하는 약제학적 조성물 |
| US9475754B2 (en) | 2011-10-06 | 2016-10-25 | Thomas P. Daly | Biological buffers with wide buffering ranges |
| CN103360393B (zh) * | 2013-07-29 | 2016-01-06 | 上海万巷制药有限公司 | 茶碱乙酸的制备方法 |
| CN113200959A (zh) * | 2020-12-16 | 2021-08-03 | 南京海融制药有限公司 | 一种硫辛酸氨丁三醇盐晶型及其制备方法 |
-
1966
- 1966-02-17 ES ES0323195A patent/ES323195A1/es not_active Expired
-
1967
- 1967-02-15 GB GB7186/67A patent/GB1113600A/en not_active Expired
- 1967-02-16 DE DE19671695358 patent/DE1695358A1/de active Pending
- 1967-02-16 BE BE694127D patent/BE694127A/xx unknown
- 1967-02-17 CH CH240367A patent/CH469659A/fr unknown
- 1967-02-17 US US616780A patent/US3562273A/en not_active Expired - Lifetime
- 1967-02-17 FR FR95468A patent/FR1511911A/fr not_active Expired
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0318891A1 (de) * | 1987-12-04 | 1989-06-07 | ASTA Medica Aktiengesellschaft | Injizierbare Lösung des Thioctsäuresalzes mit Trometamol und/oder basischen Aminosäuren |
| EP0702953A2 (de) | 1994-09-22 | 1996-03-27 | ASTA Medica Aktiengesellschaft | Darreichungsformen enthaltend Thioctsäure, oder feste Salze von Thioctsäure mit verbesserter Freisetzung und Bioverfügbarkeit |
| DE4433764A1 (de) * | 1994-09-22 | 1996-03-28 | Asta Medica Ag | Darreichungsformen enthaltend alpha-Liponsäure, feste Salze von R-Thioctsäure mit verbesserter Freisetzung und Bioverfügbarkeit |
Also Published As
| Publication number | Publication date |
|---|---|
| GB1113600A (en) | 1968-05-15 |
| ES323195A1 (es) | 1966-12-01 |
| CH469659A (fr) | 1969-03-15 |
| FR1511911A (fr) | 1968-02-02 |
| US3562273A (en) | 1971-02-09 |
| BE694127A (cs) | 1967-07-31 |
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