DE1445146C3 - Salts of 2- (benzenesulfonamido) -5methoxyethoxypyrimidine derivatives and their preparation - Google Patents
Salts of 2- (benzenesulfonamido) -5methoxyethoxypyrimidine derivatives and their preparationInfo
- Publication number
- DE1445146C3 DE1445146C3 DE19611445146 DE1445146A DE1445146C3 DE 1445146 C3 DE1445146 C3 DE 1445146C3 DE 19611445146 DE19611445146 DE 19611445146 DE 1445146 A DE1445146 A DE 1445146A DE 1445146 C3 DE1445146 C3 DE 1445146C3
- Authority
- DE
- Germany
- Prior art keywords
- benzenesulfonamido
- salts
- preparation
- derivatives
- inorganic
- 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.)
- Expired
Links
- 150000003839 salts Chemical class 0.000 title claims description 8
- 239000011780 sodium chloride Substances 0.000 title claims description 8
- QFWPJPIVLCBXFJ-UHFFFAOYSA-N Glymidine sodium Chemical class N1=CC(OCCOC)=CN=C1NS(=O)(=O)C1=CC=CC=C1 QFWPJPIVLCBXFJ-UHFFFAOYSA-N 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 150000007530 organic bases Chemical class 0.000 description 5
- 150000003456 sulfonamides Chemical class 0.000 description 5
- 229940093912 Gynecological Sulfonamides Drugs 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 150000007529 inorganic bases Chemical class 0.000 description 4
- 229940079867 intestinal antiinfectives Sulfonamides Drugs 0.000 description 4
- 229940005938 ophthalmologic antiinfectives Sulfonamides Drugs 0.000 description 4
- 229940026752 topical Sulfonamides Drugs 0.000 description 4
- 229910052801 chlorine Chemical group 0.000 description 3
- 125000001309 chloro group Chemical group Cl* 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- -1 2 - Benzenesulfonamido - 5 - methoxyethoxypyrimidine calcium Chemical compound 0.000 description 2
- 210000004369 Blood Anatomy 0.000 description 2
- AXCZMVOFGPJBDE-UHFFFAOYSA-L Calcium hydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 2
- PJURMBJCMOPSHW-UHFFFAOYSA-N N-[5-(2-methoxyethoxy)pyrimidin-2-yl]benzenesulfonamide;sodium Chemical compound [Na].N1=CC(OCCOC)=CN=C1NS(=O)(=O)C1=CC=CC=C1 PJURMBJCMOPSHW-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- 239000000920 calcium hydroxide Substances 0.000 description 2
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 2
- 125000004435 hydrogen atoms Chemical group [H]* 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- HZAXFHJVJLSVMW-UHFFFAOYSA-N ethanolamine Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 1
- YZCKVEUIGOORGS-UHFFFAOYSA-N hydrogen atom Chemical compound [H] YZCKVEUIGOORGS-UHFFFAOYSA-N 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910000000 metal hydroxide Inorganic materials 0.000 description 1
- 150000004692 metal hydroxides Chemical class 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Description
worin R ein Wasserstoff- oder Chloratom oder eine Methylgruppe bedeutet, mit anorganischen oder organischen Basen.wherein R is a hydrogen or chlorine atom or a methyl group, with inorganic or organic bases.
2. 2 - Benzolsulfonamido - 5 - methoxyäthoxypyrimidin-natrium. 2. 2 - Benzenesulfonamido - 5 - methoxyethoxypyrimidine sodium.
3. 2 - Benzolsulfonamido - 5 - methoxyäthoxypyrimidin-calcium. 3. 2 - Benzenesulfonamido - 5 - methoxyethoxypyrimidine calcium.
4. Verfahren zur Herstellung der Salze nach Anspruch 1—3, dadurch gekennzeichnet, daß man ein 2-(Benzolsulfonamido)-5-methoxyäthoxy-pyrimidinderivat der allgemeinen Formel I4. Process for the preparation of the salts according to claims 1-3, characterized in that a 2- (benzenesulfonamido) -5-methoxyethoxy-pyrimidine derivative of the general formula I
N^
{ Vo-CH2-CH2-OCH3 N ^
{ Vo-CH 2 -CH 2 -OCH 3
N=/N = /
worin R ein Wasserstoff- oder Chloratom oder eine Methylgruppe bedeutet, im Anschluß an seine Herstellung nach Hauptanmeldung P 14 45 142.4 in an sich bekannter Weise mit anorganischen oder organischen Basen umsetzt und die erhaltenen Salze in üblicher Weise isoliert. in which R denotes a hydrogen or chlorine atom or a methyl group, subsequently to its production according to main application P 14 45 142.4 in a manner known per se converts inorganic or organic bases and the salts obtained are isolated in a conventional manner.
Methylgruppe bedeutet, sowie ein Verfahren zur Herstellung dieser Verbindungen zum Gegenstand hat, Salze der Verbindungen der obigen allgemeinen Formel I mit anorganischen oder organischen Basen und ein Verfahren zur Herstellung dieser Salze, das dadurch gekennzeichnet ist, daß man die Verbindungen der allgemeinen Formel I im Anschluß an ihre Herstellung nach Hauptpatent 14 45 142 in an sich bekannter Weise mit anorganischen oder organischen Basen umsetzt und die erhaltenen Salze in üblicher Weise isoliert.Means methyl group, and a process for the preparation of these compounds is the subject matter has, salts of the compounds of the above general formula I with inorganic or organic bases and a process for the preparation of these salts, which is characterized in that the compounds of the general formula I following their preparation according to main patent 14 45 142 in per se in a known manner with inorganic or organic bases and the salts obtained in the usual way Way isolated.
Es wurde gefunden, daß die anorganischen oder organischen Salze der gemäß Hauptpatent 14 45 142 herstellbaren Sulfonamide der obigen Formel, die bei oraler Verabreichung eine starke und lang anhaltende Blutzuckersenkung bewirken und sich weiter durch eine geringe Toxizität auszeichnen, überraschend gut, d. h. schnell und vollständig, resorbiert werden, wodurch bereits im Verlauf der etwa ersten halben Stunde nach erfolgter Applikation beim Menschen eine Senkung des Blutzuckers um etwa 35% eintritt, während bei Verwendung der gleichen Dosis freien Sulfonamide dieser Erfolg erst nach etwa 3 Stunden zu beobachten ist. Zur Herstellung der Sulfonamidsalze aus den freien Sulfonamiden werden beispielsweise die freien Sulfonamide mit vorzugsweise äquivalenten Mengen eines Metallhydroxyds wie Natrium- und Calciumhydroxyd oder mit einer organischen Base, wie Äthanolamin, und in Gegenwart eines Lösungsmittels, wie Äthanol oder Wasser, bei gegebenenfalls erhöhter Temperatur umgesetzt.It has been found that the inorganic or organic salts according to main patent 14 45 142 preparable sulfonamides of the above formula, which when administered orally are strong and long-lasting Cause blood sugar lowering and are further characterized by a low toxicity, surprisingly good, d. H. quickly and completely, being absorbed, thereby already in the course of about the first half an hour after application in humans a decrease in blood sugar of about 35% occurs, while If the same dose of free sulfonamides is used, this success can only be observed after about 3 hours is. For the preparation of the sulfonamide salts from the free sulfonamides, for example free sulfonamides with preferably equivalent amounts of a metal hydroxide such as sodium and Calcium hydroxide or with an organic base, such as ethanolamine, and in the presence of a solvent, such as ethanol or water, reacted at optionally elevated temperature.
Die Erfindung betrifft in weiterer Ausgestaltung des Patents 1445142 die 2-(Benzolsulfonamido)-5-methoxyäthoxypyrimidinderivate der allgemeinen Formel IIn a further embodiment of the patent 1445142, the invention relates to the 2- (benzenesulfonamido) -5-methoxyethoxypyrimidine derivatives of the general formula I.
Κ-ζ VSO2-NH-^ VOCH2-CH2-OCH3 Κ-ζ VSO 2 -NH- ^ VOCH 2 -CH 2 -OCH 3
N=/ XT=/N = / XT = /
(D
worin R ein Wasserstoff- oder Chloratom oder eine 31 g 2-Benzolsulfonamido-5-methoxyäthoxypyrimidin
werden mit 4 g Natriumhydroxyd in 250 ml Äthanol gelöst. Die Lösung wird anschließend filtriert
und zur Trockne eingedampft. Der Rückstand wird mit 300 ml Aceton verrührt und abgesaugt.
Nach dem Trocknen werden so 27 g 2-Benzolsulfonamido
- 5 - methoxyäthoxvpyrimidinnatrium vom Schmelzpunkt 220—223° C erhalten. (D
wherein R is a hydrogen or chlorine atom or 31 g of 2-benzenesulfonamido-5-methoxyethoxypyrimidine are dissolved with 4 g of sodium hydroxide in 250 ml of ethanol. The solution is then filtered and evaporated to dryness. The residue is stirred with 300 ml of acetone and filtered off with suction. After drying, 27 g of 2-benzenesulfonamido-5-methoxyethoxy-pyrimidine sodium with a melting point of 220-223 ° C. are obtained.
B e i s ρ i e 1 2B e i s ρ i e 1 2
Analog Beispiel 1 werden aus 31 g 2-Benzolsulfonamido-5-methoxyäthoxypyrimidin und 3,7 g Calciumhydroxyd 29 g 2-Benzolsulfonamido-5-methoxyäthoxypyrimidin-calcium vom Schmelzpunkt 1500C erhalten. Analogously to Example 1-benzenesulfonamido-5-methoxyäthoxypyrimidin 2 of 31 g and 3.7 g calcium hydroxide 29 g 2-benzenesulfonamido-5-methoxyäthoxypyrimidin-calcium with a melting point of 150 0 C obtained.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DESC030267 | 1961-09-09 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1445146C3 true DE1445146C3 (en) | 1977-08-04 |
Family
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