DE2226267A1 - Aspartic acid complexes - which lower blood and urine sugar levels - Google Patents
Aspartic acid complexes - which lower blood and urine sugar levelsInfo
- Publication number
- DE2226267A1 DE2226267A1 DE2226267A DE2226267A DE2226267A1 DE 2226267 A1 DE2226267 A1 DE 2226267A1 DE 2226267 A DE2226267 A DE 2226267A DE 2226267 A DE2226267 A DE 2226267A DE 2226267 A1 DE2226267 A1 DE 2226267A1
- Authority
- DE
- Germany
- Prior art keywords
- trivalent rare
- zinc
- aspartic acid
- complex compounds
- complex
- 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.)
- Granted
Links
- 239000008280 blood Substances 0.000 title abstract description 4
- 210000004369 blood Anatomy 0.000 title abstract description 4
- 210000002700 urine Anatomy 0.000 title abstract description 3
- 150000001509 aspartic acid derivatives Chemical class 0.000 title 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims abstract description 10
- 229910052725 zinc Inorganic materials 0.000 claims abstract description 10
- 239000011701 zinc Substances 0.000 claims abstract description 10
- 150000003839 salts Chemical class 0.000 claims abstract description 9
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 claims abstract description 7
- 229910052761 rare earth metal Inorganic materials 0.000 claims abstract description 7
- 150000002910 rare earth metals Chemical class 0.000 claims abstract description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 6
- 235000003704 aspartic acid Nutrition 0.000 claims abstract description 6
- OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 claims abstract description 6
- 150000003863 ammonium salts Chemical class 0.000 claims abstract description 5
- 239000003054 catalyst Substances 0.000 claims abstract description 5
- 229910052684 Cerium Inorganic materials 0.000 claims abstract description 3
- 150000001408 amides Chemical class 0.000 claims abstract description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims description 20
- 239000004480 active ingredient Substances 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 5
- 229910052777 Praseodymium Inorganic materials 0.000 claims description 4
- PUDIUYLPXJFUGB-UHFFFAOYSA-N praseodymium atom Chemical compound [Pr] PUDIUYLPXJFUGB-UHFFFAOYSA-N 0.000 claims description 4
- 230000009918 complex formation Effects 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 150000004649 carbonic acid derivatives Chemical class 0.000 claims description 2
- ZMIGMASIKSOYAM-UHFFFAOYSA-N cerium Chemical compound [Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce] ZMIGMASIKSOYAM-UHFFFAOYSA-N 0.000 claims description 2
- 229940079593 drug Drugs 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims description 2
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 2
- 150000003751 zinc Chemical class 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims 1
- 150000002978 peroxides Chemical class 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract description 9
- 230000000694 effects Effects 0.000 abstract description 5
- PFUVRDFDKPNGAV-UHFFFAOYSA-N sodium peroxide Chemical compound [Na+].[Na+].[O-][O-] PFUVRDFDKPNGAV-UHFFFAOYSA-N 0.000 abstract description 4
- 230000003389 potentiating effect Effects 0.000 abstract description 2
- GWXLDORMOJMVQZ-UHFFFAOYSA-N cerium Chemical compound [Ce] GWXLDORMOJMVQZ-UHFFFAOYSA-N 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 241000196324 Embryophyta Species 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 235000011121 sodium hydroxide Nutrition 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 description 2
- 229960001763 zinc sulfate Drugs 0.000 description 2
- 229910000368 zinc sulfate Inorganic materials 0.000 description 2
- 229940123208 Biguanide Drugs 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 1
- 244000046052 Phaseolus vulgaris Species 0.000 description 1
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- -1 ammonium ions Chemical class 0.000 description 1
- DCXYFEDJOCDNAF-UHFFFAOYSA-M asparaginate Chemical compound [O-]C(=O)C(N)CC(N)=O DCXYFEDJOCDNAF-UHFFFAOYSA-M 0.000 description 1
- 150000004283 biguanides Chemical class 0.000 description 1
- GHLITDDQOMIBFS-UHFFFAOYSA-H cerium(3+);tricarbonate Chemical compound [Ce+3].[Ce+3].[O-]C([O-])=O.[O-]C([O-])=O.[O-]C([O-])=O GHLITDDQOMIBFS-UHFFFAOYSA-H 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229930182478 glucoside Natural products 0.000 description 1
- 150000008131 glucosides Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 229940126601 medicinal product Drugs 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 230000001960 triggered effect Effects 0.000 description 1
- 230000002485 urinary effect Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/003—Compounds containing elements of Groups 3 or 13 of the Periodic Table without C-Metal linkages
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
-
- 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
- C07F3/00—Compounds containing elements of Groups 2 or 12 of the Periodic Table
- C07F3/003—Compounds containing elements of Groups 2 or 12 of the Periodic Table without C-Metal linkages
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Diabetes (AREA)
- Emergency Medicine (AREA)
- Endocrinology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Description
Komplexverbindungen von asparaginsäure, ihre anwendung und Verfahren zur Herstellung derselben Bekanntlich können durch perorale Verabreichung von bulfonylderivaten und Produkten auf der Basis von Biguaniden sowie durch die gleiche Medikation pSlanzlicher Totalextraktivstoff, , beispielsweise von Bohnenschalen, Beeinflussungen der -Blut- und Harnzuckerwerte ausgelöst werden. Ferner ist es aus der deutschen Patentschrift 936 592 bekannt, daß derartige Wirkungen durch eine Verbindung aus trioxyflavonglukosidhaltigen Pflanzenteilen mit seltenen Erden beziehungsweise deren Salzen erzielt werden können.Complex compounds of aspartic acid, their application and method for the preparation of the same, as is known, by oral administration of sulfonyl derivatives and products based on biguanides as well as plant-based with the same medication Total extractives, for example from bean shells, influences the -blood- and urinary sugar levels are triggered. It is also from the German patent specification 936 592 known that such effects by a compound of trioxyflavone glucoside-containing Plant parts with rare earths or their salts can be achieved.
Es wurde nun überraschenderweise festgestellt, daß durch Komplexverbindungen von asparaginsäure mit 3-wertigen seltenen Erden und Zink besonders gute blut- und harnzuckersenkende Wirkungen erzielt werden. It has now been found, surprisingly, that by complex compounds of aspartic acid with trivalent rare earths and zinc are particularly good for blood and urine-lowering effects can be achieved.
Gegenstand der Erfindung sind daher Komplexverbindungen von hsparaginsäure mit 3-wertigen seltenen Erden und Zink. Die 3-wertige seltene Erde ist vorzugsweise er beziehungsweise Praseodym. als itsparaginsäure ist l-sparaginsäure bevorzugt. Es wird angenommen, daß in den erfindungsgemäßen Verbindungen sowohl der Wasserstoff des bäurerestes der asparaginsäure durch Metall substituiert ist als auch eine Komplexbindung zur Amidgruppe vorliegt, wobei die bubstitution durch die seltene Erde erfolgt. The invention therefore relates to complex compounds of hpartic acid with trivalent rare earths and zinc. The 3-valent rare earth is preferred he or praseodymium. than it ispartic acid l-spartic acid preferred. It is believed that in the compounds of the invention both the hydrogen of the aspartic acid residue is substituted by metal as well as a complex bond to the amide group is present, the bubstitution by the rare earth takes place.
Ferner sind erfindungsgemäß arzneimittelpräparate, welche 1 beziehungsweise mehrere der obigen Verbindungen als Wirkstoff beziehungsweise Wirkstoffe enthalten beziehungsweise aus dieser beziehungsweise diesen bestehen, vorgesehen. Furthermore, according to the invention, pharmaceutical preparations which 1 or contain several of the above compounds as active ingredients or active ingredients or consist of this or these are provided.
Es wurde auch festgestellt, daß die erfindungsgemäßen Komplexverbindungen die Wirkung der oben genannten Trioxyflavonverbindungen zu potenzieren vermögen. Nach einer wusführungsform der erfindung sind daher arzneimittelpräparate, die auch 1 oder mehr Komplexverbindungen von Trioxyflavon mit 3-wertigen seltenen erden als Wirkstoff beziehungsweise Wirkstoffe enthalten, vorgesehen. It was also found that the complex compounds according to the invention able to potentiate the effect of the above-mentioned trioxyflavone compounds. According to one embodiment of the invention, there are therefore medicinal products that also 1 or more complex compounds of trioxyflavone with trivalent rare earths than Containing active ingredient or active ingredients, provided.
Gegenstand der Erfindung ist auch ein Verfahren zur Herstellung der erfindungsgemäßen Verbindungen, welches dadurch gekennzeichnet ist, daß nach bberführen des Amidstickstoffes von asparaginsäure in ein Ämmoniumsalz (inneres Salz) ein Doppelsalz einer 3-wertigen seltenen Erde und von Zink unter Komplexbildung angelagert wird, wobei Natriumperoxyd als katalysator verwendet wird, und die Anlagerungsverbindung mit ljatrpnlauge gefällt und mit 77fO-igem Alkohol zur Eristallisation gebracht wird. The invention also provides a method for producing the Compounds according to the invention, which is characterized in that after transfer of the amide nitrogen of aspartic acid into an ammonium salt (inner salt) a double salt a trivalent rare earth and zinc is deposited with complex formation, whereby Sodium peroxide is used as a catalyst, and the addition compound precipitated with lyatrp liquor and brought to eristallization with 77% alcohol will.
Im einzelnen kann dabei wie folgt vorgegangen werden: Die wusgangssubstanz Asparaginsäure wird durch saure Hydrolyse, beispielsweise mit salzsäure, in an sich bekannter Weise in ein ammoniumsalz überführt, indem der gebundene smidstickstoff-in die vorgenannte Verbindung über die Zwischenstufe des ammoniaks gebracht wird. Hierdurch wird bewirkt, daß durch die vorhandenen ammoniumionen die Grundlage der späteren Bildung von komplexen Verbindungen erzielt wird. You can proceed as follows: The starting substance Aspartic acid is produced by acid hydrolysis, for example with hydrochloric acid, in itself in a known way converted into an ammonium salt by the bound smidnitrogen-in the aforementioned compound is brought via the intermediate stage of ammonia. Through this is caused by the existing ammonium ions the basis of the later Formation of complex connections is achieved.
Nach Erzielung dieser Vorstufe werden dem säurehaltigen Hydrolysat boppelsalze 3-wertiger seltener Erden und Zinksalze unter gleichzeitigem Erwärmen und in Gegenwart von Natriumperoxyd als Eatalysator zugesetzt. Die so analog der Bildung von Glykokoll-Kupfer entstandenen Komplexverbindungen werden in kaltem Zustand unter Einhalten des isoelektrischen Punktes im Neutralbereich mit Natronlauge gefällt, anschließend mit 67%-igem Äthanol gewaschen und getrocknet. After reaching this preliminary stage, the acidic hydrolyzate double salts of trivalent rare earths and zinc salts with simultaneous heating and added in the presence of sodium peroxide as a catalyst. Which is so analogous to the Complex compounds formed by the formation of glycocopper-copper are in a cold state precipitated with caustic soda while maintaining the isoelectric point in the neutral range, then washed with 67% ethanol and dried.
Als besonders vorteilhaft erwiesen sich für die Änlagerungen in Bezug auf die technische Durchführung und ausbeute die Carbonate des Cers und eraseodyms und die bulfate des Zinks. Relative to the deposits proved to be particularly advantageous on the technical implementation and yield the carbonates of cerium and eraseodymium and the bulfates of zinc.
Die erfindung wird an Hand der folgenden nicht als Beschränkung aufzufassenden Beispiele näher erläutert. The invention is not to be construed as a limitation on the basis of the following Examples explained in more detail.
Beispiel 1 Es wurden 532,4 g l-Asparaginsäure in 500 cm3 destilliertem Wasser und ## cm³ einer 37%-igen Salzsäure unter gleichzeitigem Überführen des ßmidstickstoffes in ein ammoniumsalz hydrolysiert.Example 1 532.4 g of 1-aspartic acid were distilled in 500 cm3 Hydrolyzed water and ## cm³ of a 37% hydrochloric acid with simultaneous conversion of the ßmidnitrogen into an ammonium salt.
Danach wurden 550,37 g Cercarbonat und 161,44 g Zinksulfat zugesetzt und die Mischung wurde nach Zugabe von 0,1 g Natriumperoxyd als Katalyzator auf 400C erwärmt. Then 550.37 g cerium carbonate and 161.44 g zinc sulfate were added and the mixture was used as a catalyst after adding 0.1 g of sodium peroxide 400C heated.
Die so gewonnene Lösung wurde nach abtrennen eventueller vom verwendeten Cercarbonat herrührender Verunreinigungen nach dem Filtrieren bei 300C abgekühlt und bei Zimmertemperatur mit 15 cm3 einer 20%-igen Natronlauge versetzt. Der gebildete Niederschlag wurde abfiltriert und mit 77ß-igem Alkohol gewaschen. Das Waschen wurde 3-mal wiederholt. Der gewonnene rückstand wurde bei 4000 im Trockenschrank getrocknet und stellt eine komplexe 0er/Zink/sparaginat-Verbindung dar. The solution obtained in this way was used after separating any Cercarbonate-originating impurities cooled after filtering at 300C and 15 cm3 of 20% sodium hydroxide solution are added at room temperature. The educated Precipitate was filtered off and washed with 77 [beta] alcohol. The washing was Repeated 3 times. The residue obtained was dried at 4000 in a drying cabinet and represents a complex 0er / zinc / sparaginate compound.
Die ausbeute betrug etwa 850 g. Der Schmelzpunkt der kristallinen Masse war 243,500. Das Holekulargewicht betrug 994,21. The yield was about 850 g. The melting point of the crystalline Mass was 243,500. The molecular weight was 994.21.
Beispiel 2 Unter den gleichen Herstellungsoedingungen wie im Beispiel 1 und ebenfalls unter Verwendung von l-sparaginsäure als ausgangssubstanz wurde die Komplexbildung mit Praseodym an Stelle von ber durchgeführt. Example 2 Under the same manufacturing conditions as in the example 1 and also using l-spartic acid as the starting substance the complex formation was carried out with praseodymium instead of ber.
Wesentlich für die Erfindung ist, daß das asparaginat mit 3-wertigen seltenen Erden und Zinksulfat gebildet ist und mit ihm blut- und harnzuckersenkende Wirkungen erzielt werden. It is essential for the invention that the asparaginate with trivalent rare earths and zinc sulfate is formed and with it blood and urine lowering Effects are achieved.
Claims (6)
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19722226267 DE2226267B2 (en) | 1972-05-30 | 1972-05-30 | COMPLEX COMPOUND OF ASPARAGINATE, CER (III) AND ZINC IONS, PROCESS FOR THEIR PRODUCTION AND MEDICINAL PRODUCTS CONTAINING THESE |
| CH724873A CH575381A5 (en) | 1972-05-30 | 1973-05-22 | |
| JP5988473A JPS536206B2 (en) | 1972-05-30 | 1973-05-30 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19722226267 DE2226267B2 (en) | 1972-05-30 | 1972-05-30 | COMPLEX COMPOUND OF ASPARAGINATE, CER (III) AND ZINC IONS, PROCESS FOR THEIR PRODUCTION AND MEDICINAL PRODUCTS CONTAINING THESE |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2226267A1 true DE2226267A1 (en) | 1973-12-13 |
| DE2226267B2 DE2226267B2 (en) | 1977-06-02 |
Family
ID=5846319
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19722226267 Granted DE2226267B2 (en) | 1972-05-30 | 1972-05-30 | COMPLEX COMPOUND OF ASPARAGINATE, CER (III) AND ZINC IONS, PROCESS FOR THEIR PRODUCTION AND MEDICINAL PRODUCTS CONTAINING THESE |
Country Status (3)
| Country | Link |
|---|---|
| JP (1) | JPS536206B2 (en) |
| CH (1) | CH575381A5 (en) |
| DE (1) | DE2226267B2 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1364647A1 (en) * | 2001-01-31 | 2003-11-26 | Japan Science and Technology Corporation | Hypoglycemic agent |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4606978A (en) * | 1982-09-24 | 1986-08-19 | Gte Products Corporation | Ductile brazing alloy foil containing reactive metals and precious metals |
| US4690876A (en) * | 1984-11-16 | 1987-09-01 | Gte Products Corporation | Article comprising a ductile brazing alloy foil containing reactive metals and precious metals |
| US4599152A (en) * | 1985-05-24 | 1986-07-08 | Albion Laboratories | Pure amino acid chelates |
| CH678949A5 (en) * | 1989-06-27 | 1991-11-29 | Muller Ludwig Sa | |
| JP2001220348A (en) * | 1999-11-30 | 2001-08-14 | Japan Science & Technology Corp | Hypoglycemic comprising zinc (ii) organic complex |
-
1972
- 1972-05-30 DE DE19722226267 patent/DE2226267B2/en active Granted
-
1973
- 1973-05-22 CH CH724873A patent/CH575381A5/xx not_active IP Right Cessation
- 1973-05-30 JP JP5988473A patent/JPS536206B2/ja not_active Expired
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1364647A1 (en) * | 2001-01-31 | 2003-11-26 | Japan Science and Technology Corporation | Hypoglycemic agent |
| EP1364647A4 (en) * | 2001-01-31 | 2006-04-05 | Japan Science & Tech Agency | HYPOGLYKEMIC AGENT |
| US7226935B2 (en) | 2001-01-31 | 2007-06-05 | Japan Science And Technology Corporation | Hypoglycemic agent |
| EP1897541A2 (en) * | 2001-01-31 | 2008-03-12 | Japan Science and Technology Agency | Hypoglycemic agent |
| EP1900366A2 (en) * | 2001-01-31 | 2008-03-19 | Japan Science and Technology Agency | Hypoglycemic agent |
| EP1900367A2 (en) * | 2001-01-31 | 2008-03-19 | Japan Science and Technology Agency | Hypoglycemic agent |
| EP1905438A2 (en) * | 2001-01-31 | 2008-04-02 | Japan Science and Technology Agency | Hypoglycemic agent |
| EP1897541A3 (en) * | 2001-01-31 | 2008-05-28 | Japan Science and Technology Agency | Hypoglycemic agent |
| EP1900366A3 (en) * | 2001-01-31 | 2008-06-25 | Japan Science and Technology Agency | Hypoglycemic agent |
| EP1900367A3 (en) * | 2001-01-31 | 2008-07-02 | Japan Science and Technology Agency | Hypoglycemic agent |
| EP1905438A3 (en) * | 2001-01-31 | 2008-07-02 | Japan Science and Technology Agency | Hypoglycemic agent |
Also Published As
| Publication number | Publication date |
|---|---|
| DE2226267B2 (en) | 1977-06-02 |
| JPS4948813A (en) | 1974-05-11 |
| CH575381A5 (en) | 1976-05-14 |
| JPS536206B2 (en) | 1978-03-06 |
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