CH469659A - Procédé d'obtention de dérivés du tri-hydroxy-méthyl-aminométhane - Google Patents
Procédé d'obtention de dérivés du tri-hydroxy-méthyl-aminométhaneInfo
- Publication number
- CH469659A CH469659A CH240367A CH240367A CH469659A CH 469659 A CH469659 A CH 469659A CH 240367 A CH240367 A CH 240367A CH 240367 A CH240367 A CH 240367A CH 469659 A CH469659 A CH 469659A
- Authority
- CH
- Switzerland
- Prior art keywords
- aminomethane
- methyl
- tri
- acid
- hydroxy
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 21
- HKLYDUXIXBVZOQ-UHFFFAOYSA-N 2-aminoethane-1,1,1-triol Chemical class NCC(O)(O)O HKLYDUXIXBVZOQ-UHFFFAOYSA-N 0.000 title 1
- FYFFGSSZFBZTAH-UHFFFAOYSA-N methylaminomethanetriol Chemical class CNC(O)(O)O FYFFGSSZFBZTAH-UHFFFAOYSA-N 0.000 claims description 27
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 18
- 150000003839 salts Chemical class 0.000 claims description 16
- 208000010444 Acidosis Diseases 0.000 claims description 15
- 208000026545 acidosis disease Diseases 0.000 claims description 14
- 239000002904 solvent Substances 0.000 claims description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 10
- AGBQKNBQESQNJD-UHFFFAOYSA-N lipoic acid Chemical compound OC(=O)CCCCC1CCSS1 AGBQKNBQESQNJD-UHFFFAOYSA-N 0.000 claims description 10
- HCYFGRCYSCXKNQ-UHFFFAOYSA-N 2-(1,3-dimethyl-2,6-dioxo-7-purinyl)acetic acid Chemical compound O=C1N(C)C(=O)N(C)C2=C1N(CC(O)=O)C=N2 HCYFGRCYSCXKNQ-UHFFFAOYSA-N 0.000 claims description 8
- 229950003769 acefylline Drugs 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 8
- 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 6
- PXQPEWDEAKTCGB-UHFFFAOYSA-N orotic acid Chemical compound OC(=O)C1=CC(=O)NC(=O)N1 PXQPEWDEAKTCGB-UHFFFAOYSA-N 0.000 claims description 6
- AGBQKNBQESQNJD-SSDOTTSWSA-N (R)-lipoic acid Chemical compound OC(=O)CCCC[C@@H]1CCSS1 AGBQKNBQESQNJD-SSDOTTSWSA-N 0.000 claims description 5
- 238000009835 boiling Methods 0.000 claims description 5
- 239000013078 crystal Substances 0.000 claims description 5
- 235000019136 lipoic acid Nutrition 0.000 claims description 5
- 229940068511 thioctate Drugs 0.000 claims description 5
- 229960002663 thioctic acid Drugs 0.000 claims description 5
- 238000006243 chemical reaction Methods 0.000 claims description 4
- 230000000694 effects Effects 0.000 claims description 4
- 150000007513 acids Chemical class 0.000 claims description 2
- 150000002763 monocarboxylic acids Chemical class 0.000 claims description 2
- 229960005010 orotic acid Drugs 0.000 claims description 2
- 239000002798 polar solvent Substances 0.000 claims 6
- 238000001914 filtration Methods 0.000 claims 4
- 229910017053 inorganic salt Inorganic materials 0.000 claims 4
- 230000015572 biosynthetic process Effects 0.000 claims 2
- 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 1
- 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 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 229940055705 pangamic acid Drugs 0.000 claims 1
- 108700024047 pangamic acid Proteins 0.000 claims 1
- 235000019441 ethanol Nutrition 0.000 description 14
- ZUFVXZVXEJHHBN-UHFFFAOYSA-N hydron;1,2,3,4-tetrahydroacridin-9-amine;chloride Chemical class [Cl-].C1=CC=C2C([NH3+])=C(CCCC3)C3=NC2=C1 ZUFVXZVXEJHHBN-UHFFFAOYSA-N 0.000 description 13
- 239000000047 product Substances 0.000 description 11
- 239000000243 solution Substances 0.000 description 11
- 230000007950 acidosis Effects 0.000 description 10
- 150000001875 compounds Chemical class 0.000 description 10
- 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
- 239000008280 blood 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
- 210000004369 blood Anatomy 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
- 239000000872 buffer Substances 0.000 description 4
- 239000000843 powder 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
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
- 208000035475 disorder Diseases 0.000 description 3
- 230000000241 respiratory effect Effects 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 229960000278 theophylline Drugs 0.000 description 3
- MCHZKGNHFPNZDP-UHFFFAOYSA-N 2-aminoethane-1,1,1-triol;hydrochloride Chemical compound Cl.NCC(O)(O)O MCHZKGNHFPNZDP-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 208000007976 Ketosis 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
- 230000003139 buffering effect Effects 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
- 230000008030 elimination Effects 0.000 description 2
- 238000003379 elimination reaction Methods 0.000 description 2
- 230000003834 intracellular effect Effects 0.000 description 2
- 150000002576 ketones Chemical class 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
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 229940106978 pangamate Drugs 0.000 description 2
- 230000002685 pulmonary effect Effects 0.000 description 2
- 239000010959 steel Substances 0.000 description 2
- 230000002194 synthesizing effect Effects 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
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- 241000282472 Canis lupus familiaris Species 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
- 206010023379 Ketoacidosis Diseases 0.000 description 1
- 206010023388 Ketonuria Diseases 0.000 description 1
- 208000002720 Malnutrition Diseases 0.000 description 1
- 206010027417 Metabolic acidosis Diseases 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 208000004880 Polyuria Diseases 0.000 description 1
- 206010037660 Pyrexia Diseases 0.000 description 1
- IUJDSEJGGMCXSG-UHFFFAOYSA-N Thiopental Chemical compound CCCC(C)C1(CC)C(=O)NC(=S)NC1=O IUJDSEJGGMCXSG-UHFFFAOYSA-N 0.000 description 1
- 206010047700 Vomiting Diseases 0.000 description 1
- 230000002159 abnormal effect Effects 0.000 description 1
- 230000005856 abnormality Effects 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
- 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
- 230000036772 blood pressure Effects 0.000 description 1
- 230000023852 carbohydrate metabolic process Effects 0.000 description 1
- 235000021256 carbohydrate metabolism Nutrition 0.000 description 1
- 235000014633 carbohydrates Nutrition 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 230000001413 cellular effect 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
- 239000012141 concentrate Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000006735 deficit Effects 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 230000000881 depressing effect Effects 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 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
- 238000002474 experimental method Methods 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 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
- 239000008240 homogeneous mixture Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- -1 hydrogen ions Chemical class 0.000 description 1
- 230000007794 irritation Effects 0.000 description 1
- 210000003734 kidney Anatomy 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
- 230000007246 mechanism Effects 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 230000002503 metabolic effect Effects 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000004570 mortar (masonry) Substances 0.000 description 1
- 231100000956 nontoxicity Toxicity 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- 235000011837 pasties Nutrition 0.000 description 1
- 229940043200 pentothal Drugs 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
- 231100000572 poisoning Toxicity 0.000 description 1
- 230000000607 poisoning effect Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000008844 regulatory mechanism Effects 0.000 description 1
- 210000001034 respiratory center Anatomy 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 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
- UUDFBRWLHZIIQX-UHFFFAOYSA-M sodium;5-(dithiolan-3-yl)pentanoate Chemical compound [Na+].[O-]C(=O)CCCCC1CCSS1 UUDFBRWLHZIIQX-UHFFFAOYSA-M 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007921 spray Substances 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
- 230000002110 toxicologic effect Effects 0.000 description 1
- 231100000027 toxicology Toxicity 0.000 description 1
- 239000003053 toxin Substances 0.000 description 1
- 231100000765 toxin Toxicity 0.000 description 1
- 235000000112 undernutrition Nutrition 0.000 description 1
- 230000008673 vomiting Effects 0.000 description 1
- 238000005303 weighing Methods 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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (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 |
|---|---|---|---|
| ES0323195A ES323195A1 (es) | 1966-02-17 | 1966-02-17 | Procedimiento de obtenciën de compuestos de acciën antiacidëtica |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH469659A true CH469659A (fr) | 1969-03-15 |
Family
ID=8442738
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH240367A CH469659A (fr) | 1966-02-17 | 1967-02-17 | Procédé d'obtention de dérivés du tri-hydroxy-méthyl-aminométhane |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US3562273A (en(2012)) |
| BE (1) | BE694127A (en(2012)) |
| CH (1) | CH469659A (en(2012)) |
| DE (1) | DE1695358A1 (en(2012)) |
| ES (1) | ES323195A1 (en(2012)) |
| FR (1) | FR1511911A (en(2012)) |
| GB (1) | GB1113600A (en(2012)) |
Families Citing this family (20)
| 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 |
| DE3867445D1 (de) * | 1987-12-04 | 1992-02-13 | Asta Pharma Ag | Injizierbare loesung des thioctsaeuresalzes mit trometamol und/oder basischen aminosaeuren. |
| 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 |
| 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 |
| 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 |
| US8519141B2 (en) | 2008-04-17 | 2013-08-27 | Thomas Daly | Biological buffers with wide buffering ranges |
| US7939659B2 (en) * | 2008-04-17 | 2011-05-10 | Thomas Daly | Biological buffers with wide buffering ranges |
| US20170313920A1 (en) | 2010-10-06 | 2017-11-02 | Thomas P. Daly | Biological Buffers with Wide Buffering Ranges |
| US7635791B2 (en) * | 2008-04-17 | 2009-12-22 | Tpat Ip Llc | Biological buffers with wide buffering ranges |
| US8822728B2 (en) | 2008-04-17 | 2014-09-02 | 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 |
| US8034951B2 (en) * | 2008-04-17 | 2011-10-11 | Thomas Daly | Biological buffers with wide buffering ranges |
| US9090638B2 (en) | 2008-04-17 | 2015-07-28 | 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 US US616780A patent/US3562273A/en not_active Expired - Lifetime
- 1967-02-17 FR FR95468A patent/FR1511911A/fr not_active Expired
- 1967-02-17 CH CH240367A patent/CH469659A/fr unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ES323195A1 (es) | 1966-12-01 |
| FR1511911A (fr) | 1968-02-02 |
| US3562273A (en) | 1971-02-09 |
| BE694127A (en(2012)) | 1967-07-31 |
| GB1113600A (en) | 1968-05-15 |
| DE1695358A1 (de) | 1972-04-13 |
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