DE1141639B - Verfahren zur Herstellung wasserloeslicher Cholinphosphorsaeure-diglyceridester-Verbindungen - Google Patents
Verfahren zur Herstellung wasserloeslicher Cholinphosphorsaeure-diglyceridester-VerbindungenInfo
- Publication number
- DE1141639B DE1141639B DEN19273A DEN0019273A DE1141639B DE 1141639 B DE1141639 B DE 1141639B DE N19273 A DEN19273 A DE N19273A DE N0019273 A DEN0019273 A DE N0019273A DE 1141639 B DE1141639 B DE 1141639B
- Authority
- DE
- Germany
- Prior art keywords
- acid diglyceride
- phosphoric acid
- water
- acid
- ester
- 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
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 title claims description 21
- 238000000034 method Methods 0.000 title claims description 12
- 229910000147 aluminium phosphate Inorganic materials 0.000 title claims description 11
- 229960001231 choline Drugs 0.000 title claims description 11
- OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 title claims description 10
- -1 ester compounds Chemical class 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 4
- 150000002148 esters Chemical class 0.000 claims description 22
- KXGVEGMKQFWNSR-LLQZFEROSA-N deoxycholic acid Chemical compound C([C@H]1CC2)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(O)=O)C)[C@@]2(C)[C@@H](O)C1 KXGVEGMKQFWNSR-LLQZFEROSA-N 0.000 claims description 20
- 229960003964 deoxycholic acid Drugs 0.000 claims description 19
- 150000001875 compounds Chemical class 0.000 claims description 17
- GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 claims description 14
- 239000002253 acid Substances 0.000 claims description 11
- 229940087168 alpha tocopherol Drugs 0.000 claims description 7
- 229960000984 tocofersolan Drugs 0.000 claims description 7
- 239000002076 α-tocopherol Substances 0.000 claims description 7
- 235000004835 α-tocopherol Nutrition 0.000 claims description 7
- 235000004626 essential fatty acids Nutrition 0.000 claims description 6
- 235000021122 unsaturated fatty acids Nutrition 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 4
- ASWBNKHCZGQVJV-UHFFFAOYSA-N (3-hexadecanoyloxy-2-hydroxypropyl) 2-(trimethylazaniumyl)ethyl phosphate Chemical compound CCCCCCCCCCCCCCCC(=O)OCC(O)COP([O-])(=O)OCC[N+](C)(C)C ASWBNKHCZGQVJV-UHFFFAOYSA-N 0.000 claims description 3
- SUHOOTKUPISOBE-UHFFFAOYSA-N O-phosphoethanolamine Chemical compound NCCOP(O)(O)=O SUHOOTKUPISOBE-UHFFFAOYSA-N 0.000 claims description 3
- 239000007864 aqueous solution Substances 0.000 claims description 3
- 239000000243 solution Substances 0.000 description 14
- 239000003613 bile acid Substances 0.000 description 13
- KXGVEGMKQFWNSR-UHFFFAOYSA-N deoxycholic acid Natural products C1CC2CC(O)CCC2(C)C2C1C1CCC(C(CCC(O)=O)C)C1(C)C(O)C2 KXGVEGMKQFWNSR-UHFFFAOYSA-N 0.000 description 10
- 150000004665 fatty acids Chemical class 0.000 description 10
- 235000014113 dietary fatty acids Nutrition 0.000 description 9
- 239000000194 fatty acid Substances 0.000 description 9
- 229930195729 fatty acid Natural products 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 8
- 230000001476 alcoholic effect Effects 0.000 description 6
- 239000003925 fat Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 150000007513 acids Chemical class 0.000 description 5
- 239000011261 inert gas Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- HSINOMROUCMIEA-FGVHQWLLSA-N (2s,4r)-4-[(3r,5s,6r,7r,8s,9s,10s,13r,14s,17r)-6-ethyl-3,7-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-17-yl]-2-methylpentanoic acid Chemical compound C([C@@]12C)C[C@@H](O)C[C@H]1[C@@H](CC)[C@@H](O)[C@@H]1[C@@H]2CC[C@]2(C)[C@@H]([C@H](C)C[C@H](C)C(O)=O)CC[C@H]21 HSINOMROUCMIEA-FGVHQWLLSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 3
- XWJTYEGVQBFZHI-IMPNNSMHSA-N Apocholic acid Chemical compound C([C@H]1CC2)[C@H](O)CC[C@]1(C)[C@@H]1C2=C2CC[C@H]([C@@H](CCC(O)=O)C)[C@@]2(C)[C@@H](O)C1 XWJTYEGVQBFZHI-IMPNNSMHSA-N 0.000 description 3
- 210000000941 bile Anatomy 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 150000002632 lipids Chemical class 0.000 description 3
- GVJHHUAWPYXKBD-UHFFFAOYSA-N (±)-α-Tocopherol Chemical compound OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-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
- 235000021355 Stearic acid Nutrition 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 230000009918 complex formation Effects 0.000 description 2
- 230000007717 exclusion Effects 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 239000000787 lecithin Substances 0.000 description 2
- 229940067606 lecithin Drugs 0.000 description 2
- 235000010445 lecithin Nutrition 0.000 description 2
- 230000004060 metabolic process Effects 0.000 description 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 235000011837 pasties Nutrition 0.000 description 2
- 150000003904 phospholipids Chemical class 0.000 description 2
- 239000008117 stearic acid Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- BHQCQFFYRZLCQQ-UHFFFAOYSA-N (3alpha,5alpha,7alpha,12alpha)-3,7,12-trihydroxy-cholan-24-oic acid Natural products OC1CC2CC(O)CCC2(C)C2C1C1CCC(C(CCC(O)=O)C)C1(C)C(O)C2 BHQCQFFYRZLCQQ-UHFFFAOYSA-N 0.000 description 1
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 239000004380 Cholic acid Substances 0.000 description 1
- ZAKOWWREFLAJOT-CEFNRUSXSA-N D-alpha-tocopherylacetate Chemical compound CC(=O)OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C ZAKOWWREFLAJOT-CEFNRUSXSA-N 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 241000871495 Heeria argentea Species 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- 229930003427 Vitamin E Natural products 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 239000003833 bile salt Substances 0.000 description 1
- 229940093761 bile salts Drugs 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 210000002421 cell wall Anatomy 0.000 description 1
- 230000019522 cellular metabolic process Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- BHQCQFFYRZLCQQ-OELDTZBJSA-N cholic acid Chemical compound C([C@H]1C[C@H]2O)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(O)=O)C)[C@@]2(C)[C@@H](O)C1 BHQCQFFYRZLCQQ-OELDTZBJSA-N 0.000 description 1
- 229960002471 cholic acid Drugs 0.000 description 1
- 235000019416 cholic acid Nutrition 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- ZAKOWWREFLAJOT-UHFFFAOYSA-N d-alpha-Tocopheryl acetate Natural products CC(=O)OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C ZAKOWWREFLAJOT-UHFFFAOYSA-N 0.000 description 1
- 229940009976 deoxycholate Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000001962 electrophoresis Methods 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 235000021588 free fatty acids Nutrition 0.000 description 1
- 210000000232 gallbladder Anatomy 0.000 description 1
- LNTHITQWFMADLM-UHFFFAOYSA-N gallic acid Chemical class OC(=O)C1=CC(O)=C(O)C(O)=C1 LNTHITQWFMADLM-UHFFFAOYSA-N 0.000 description 1
- WIGCFUFOHFEKBI-UHFFFAOYSA-N gamma-tocopherol Natural products CC(C)CCCC(C)CCCC(C)CCCC1CCC2C(C)C(O)C(C)C(C)C2O1 WIGCFUFOHFEKBI-UHFFFAOYSA-N 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 239000011435 rock Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 235000021391 short chain fatty acids Nutrition 0.000 description 1
- 150000004666 short chain fatty acids Chemical class 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 229940042585 tocopherol acetate Drugs 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 229940046009 vitamin E Drugs 0.000 description 1
- 235000019165 vitamin E Nutrition 0.000 description 1
- 239000011709 vitamin E Substances 0.000 description 1
- 238000012982 x-ray structure analysis Methods 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0019—Injectable compositions; Intramuscular, intravenous, arterial, subcutaneous administration; Compositions to be administered through the skin in an invasive manner
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/28—Steroids, e.g. cholesterol, bile acids or glycyrrhetinic acid
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C07F9/10—Phosphatides, e.g. lecithin
- C07F9/103—Extraction or purification by physical or chemical treatment of natural phosphatides; Preparation of compositions containing phosphatides of unknown structure
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J75/00—Processes for the preparation of steroids in general
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J9/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of more than two carbon atoms, e.g. cholane, cholestane, coprostane
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Biochemistry (AREA)
- Dermatology (AREA)
- Molecular Biology (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Steroid Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (10)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE610853D BE610853A (US08158827-20120417-C00057.png) | 1960-12-05 | ||
| NL260444D NL260444A (US08158827-20120417-C00057.png) | 1960-12-05 | ||
| NL126750D NL126750C (US08158827-20120417-C00057.png) | 1960-12-05 | ||
| DEN19273A DE1141639B (de) | 1960-12-05 | 1960-12-05 | Verfahren zur Herstellung wasserloeslicher Cholinphosphorsaeure-diglyceridester-Verbindungen |
| SE1203/61A SE310977B (US08158827-20120417-C00057.png) | 1960-12-05 | 1961-02-06 | |
| CH538261A CH423766A (de) | 1960-12-05 | 1961-05-08 | Verfahren zum Herstellen wasserlöslicher Verbindungen von Cholinphosphorsäurediglyceridestern |
| GB18086/61A GB953899A (en) | 1960-12-05 | 1961-05-18 | Process for the preparation of natural choline phosphoric acid diglyceride ester compounds |
| DK224361AA DK130619B (da) | 1960-12-05 | 1961-06-01 | Fremgangsmåde til fremstilling af vandopløselige alfa-tocopherol-lecitin-desoxycholsyreforbindelser. |
| US114286A US3197368A (en) | 1960-12-05 | 1961-06-02 | Process for the preparation of natural choline phosphoric acid diglyceride ester compounds |
| FR880887A FR1643M (fr) | 1960-12-05 | 1961-12-04 | Médicament a base de complexes solubles dans l'eau, d'esters diglycériques naturels d'acide choline-phosphorique et de sels d'acides biliaires. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEN19273A DE1141639B (de) | 1960-12-05 | 1960-12-05 | Verfahren zur Herstellung wasserloeslicher Cholinphosphorsaeure-diglyceridester-Verbindungen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1141639B true DE1141639B (de) | 1962-12-27 |
Family
ID=7340822
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEN19273A Pending DE1141639B (de) | 1960-12-05 | 1960-12-05 | Verfahren zur Herstellung wasserloeslicher Cholinphosphorsaeure-diglyceridester-Verbindungen |
Country Status (9)
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1202370B (it) * | 1976-07-12 | 1989-02-09 | Hoffmann La Roche | Soluzioni inietabili in cui l'atti vita' emolitica degli agenti di formazione di micelle naturali e' evitata mediante l'aggiunta di lipoidi e relativi prodotti |
| DE3047048A1 (de) | 1980-12-13 | 1982-07-29 | A. Nattermann & Cie GmbH, 5000 Köln | Verfahren zur abtrennung von oel und/oder phosphatidylethanolamin aus diese enthaltenden alkoholloeslichen phosphatidylcholin-produkten |
| DE3229179C2 (de) * | 1982-08-05 | 1986-04-17 | A. Nattermann & Cie GmbH, 5000 Köln | Lungensurfactant |
| US4649155A (en) * | 1983-07-22 | 1987-03-10 | Hoffmann-La Roche Inc. | Injectable solutions |
| US4866044A (en) * | 1985-07-09 | 1989-09-12 | Takeda Chemical Industries, Ltd. | Solubilized composition of poorly-soluble pharmaceutical product |
| JPS62106018A (ja) * | 1985-11-01 | 1987-05-16 | Santen Pharmaceut Co Ltd | 高濃度ビタミンｅ水性製剤 |
| CA1319886C (en) * | 1987-02-03 | 1993-07-06 | Alberto Ferro | Mixed micelle solutions |
| USRE42190E1 (en) | 1998-11-20 | 2011-03-01 | Arena Pharmaceuticals, Inc. | Method of identifying a compound for inhibiting or stimulating human G protein-coupled receptors |
| US20030017528A1 (en) * | 1998-11-20 | 2003-01-23 | Ruoping Chen | Human orphan G protein-coupled receptors |
| US7816492B2 (en) * | 1998-11-20 | 2010-10-19 | Arena Pharmaceuticals, Inc. | Human G protein-coupled receptors |
| US20030180813A1 (en) * | 2000-12-01 | 2003-09-25 | Takahide Ohishi | Method of screening remedy for diabetes |
| CA2489405A1 (en) * | 2002-09-11 | 2004-03-25 | Yamanouchi Pharmaceutical Co., Ltd. | Screening method of agents for increasing insulin content |
| EP1898931B1 (en) * | 2005-07-07 | 2014-12-31 | Postech Foundation | Glucose uptake modulator and method for treating diabetes or diabetic complications |
| US8314080B2 (en) | 2010-04-06 | 2012-11-20 | Kuwait University | Method of treating type I diabetes |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2055083A (en) * | 1932-07-13 | 1936-09-22 | Winthrop Chem Co Inc | Pharmaceutical preparation |
-
0
- BE BE610853D patent/BE610853A/xx unknown
- NL NL260444D patent/NL260444A/xx unknown
- NL NL126750D patent/NL126750C/xx active
-
1960
- 1960-12-05 DE DEN19273A patent/DE1141639B/de active Pending
-
1961
- 1961-02-06 SE SE1203/61A patent/SE310977B/xx unknown
- 1961-05-08 CH CH538261A patent/CH423766A/de unknown
- 1961-05-18 GB GB18086/61A patent/GB953899A/en not_active Expired
- 1961-06-01 DK DK224361AA patent/DK130619B/da unknown
- 1961-06-02 US US114286A patent/US3197368A/en not_active Expired - Lifetime
- 1961-12-04 FR FR880887A patent/FR1643M/fr active Active
Also Published As
| Publication number | Publication date |
|---|---|
| GB953899A (en) | 1964-04-02 |
| US3197368A (en) | 1965-07-27 |
| CH423766A (de) | 1966-11-15 |
| DK130619B (da) | 1975-03-17 |
| NL126750C (US08158827-20120417-C00057.png) | |
| SE310977B (US08158827-20120417-C00057.png) | 1969-05-19 |
| DK130619C (US08158827-20120417-C00057.png) | 1975-08-25 |
| BE610853A (US08158827-20120417-C00057.png) | |
| FR1643M (fr) | 1963-01-07 |
| NL260444A (US08158827-20120417-C00057.png) |
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