DE2238260C3 - Phosphoric acid monoester of 5- (2-dimethylaminoethoxy) -carvacrol, process for its preparation and pharmaceuticals containing it - Google Patents
Phosphoric acid monoester of 5- (2-dimethylaminoethoxy) -carvacrol, process for its preparation and pharmaceuticals containing itInfo
- Publication number
- DE2238260C3 DE2238260C3 DE19722238260 DE2238260A DE2238260C3 DE 2238260 C3 DE2238260 C3 DE 2238260C3 DE 19722238260 DE19722238260 DE 19722238260 DE 2238260 A DE2238260 A DE 2238260A DE 2238260 C3 DE2238260 C3 DE 2238260C3
- Authority
- DE
- Germany
- Prior art keywords
- phosphoric acid
- dimethylaminoethoxy
- carvacrol
- acid monoester
- preparation
- 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
- NBIIXXVUZAFLBC-UHFFFAOYSA-N phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 title claims description 18
- 239000003814 drug Substances 0.000 title description 3
- 238000000034 method Methods 0.000 title description 3
- 238000002360 preparation method Methods 0.000 title description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- -1 alkali metal salts Chemical class 0.000 description 5
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 239000011780 sodium chloride Substances 0.000 description 4
- XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical compound OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 4
- 125000003635 2-dimethylaminoethoxy group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])O* 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- RECUKUPTGUEGMW-UHFFFAOYSA-N carvacrol Natural products CC(C)C1=CC=C(C)C(O)=C1 RECUKUPTGUEGMW-UHFFFAOYSA-N 0.000 description 3
- 150000002168 ethanoic acid esters Chemical class 0.000 description 3
- 230000002093 peripheral Effects 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- XHXFXVLFKHQFAL-UHFFFAOYSA-N Phosphoryl chloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- UCTWMZQNUQWSLP-UHFFFAOYSA-N adrenaline Chemical compound CNCC(O)C1=CC=C(O)C(O)=C1 UCTWMZQNUQWSLP-UHFFFAOYSA-N 0.000 description 2
- 235000007746 carvacrol Nutrition 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000005712 crystallization Effects 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 description 2
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Inorganic materials [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- UZOMBHOFSZKLPJ-UHFFFAOYSA-N 2-[2-(dimethylamino)ethoxy]-6-methyl-3-propan-2-ylphenol Chemical compound CC(C)C1=CC=C(C)C(O)=C1OCCN(C)C UZOMBHOFSZKLPJ-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 210000000826 Nictitating Membrane Anatomy 0.000 description 1
- HHFOOWPWAXNJNY-UHFFFAOYSA-N Promoxolane Chemical compound CC(C)C1(C(C)C)OCC(CO)O1 HHFOOWPWAXNJNY-UHFFFAOYSA-N 0.000 description 1
- 229950008352 Promoxolane Drugs 0.000 description 1
- 206010047141 Vasodilatation Diseases 0.000 description 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 238000007792 addition Methods 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 229940079593 drugs Drugs 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000001834 epinephrinelike Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N iso-propanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000002441 reversible Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000002792 vascular Effects 0.000 description 1
- 230000000304 vasodilatating Effects 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
Description
CH-,CH-,
CH3 CH 3
CH,CH,
CH, '5 r CH, '5 r
und Alkalimetallsalze hiervon.and alkali metal salts thereof.
2. Verfahren zur Herstellung des Phosphorsäuremonoesters von 5-(2-Dimethylaminoäthoxy|- carvacrol nach Anspruch 1, dadurch gekennzeichnet. daß man 2- Dimethylaminoäthoxyearvacrol der Formel2. Process for the preparation of the phosphoric acid monoester of 5- (2-dimethylaminoethoxy | - carvacrol according to claim 1, characterized. that one 2-Dimethylaminoäthoxyearvacrol the formula
HOHO
CH,CH,
CH,CH,
O—CH,—CH,O — CH, —CH,
seiner Herstellung sowie Arzneimittel, die diese Verbindungen als Wirkstoffe enthalten. Die erfindungsgemäßen Verbindungen stellen wertvolle pharmazeutische Substanzen, insbesondere periphere Düa toren, dar. und sind im Gegensatz zu anderen peripheren Dilatatoren bei peroraler Applikation voll wirksam.its manufacture as well as drugs that contain these compounds contained as active ingredients. The invention Compounds are valuable pharmaceutical substances, especially peripheral devices gates, and, in contrast to other peripheral dilators, are full when administered perorally effective.
Es ist bekannt, beispielsweise aus der DT-OS 19 26 011. daß der Essigsäureester des 5-(2-Dimethylaminoäthoxylcarvacrols eine vasodilatorische Wirksamkeit aufweist. Es war jedoch überraschend, daß sich durch einen Ersatz des Essigsäurerestes durch den Phosphorsäurerest das Wirkungsprofil erheblich verbessern läßt und die akute Toxizität drastisch gesenkt werden konnte.It is known, for example from DT-OS 19 26 011. that the acetic acid ester of 5- (2-dimethylaminoethoxylcarvacrol has a vasodilatory effect. It was surprising, however, that By replacing the acetic acid residue with the phosphoric acid residue, the effectiveness profile increases considerably can improve and the acute toxicity could be reduced drastically.
Bei der ein klassisches Modell zum Nachweis der peripheren Gefaßerweiterung bildenden sogenannten Adrenalinumkehr zeigt der bekannte Essigsäureester selbst bei 8mal höherer Dosierung als der erfmdungsgemäße Phosphorsäuremonoester keinen Adrenalinumkehreffekt. Bei dem ebenfalls zur Ermittlung der peripheren Gefä'ßerWeiterung durchgeführten Versuch einer Nickhautkontraktion durch Adrenalinstimulierung zeigte der erfindungsgemäße Phosphorsäuremonoester selbst bei niedrigster Dosierung, bei der der Essigsäureester noch keine Wirkung entfaltet, bereits eine SOfache Wirksamkeit.In the so-called, which is a classic model for the detection of peripheral vascular dilation The known acetic acid ester shows a reversal of adrenaline even at 8 times higher doses than the one according to the invention Phosphoric acid monoester has no adrenaline effect. Also used to determine the peripheral vasodilatation experiment The phosphoric acid monoester according to the invention exhibited a nictitating membrane contraction due to adrenaline stimulation even at the lowest dosage, at which the acetic acid ester does not yet have any effect, already SO-fold effectiveness.
Das Ausgangscarvaerol der FormelThe starting carvaerol of the formula
cncn
CH3 CH,CH 3 CH,
in an sich bekannter Weise mit Phosphoroxychiorid umsetzt und das Phosphorsäureesterchlorid verseift.reacts in a manner known per se with phosphorus oxychloride and the phosphoric acid ester chloride saponified.
3. Arzneimittel, dadurch gekennzeichnet, daß es als Wirkstoff einen Phosphorsäuremonoester von 5 - (2 - Dimethylaminoäthoxy)carvacrol der Formel3. Medicament, characterized in that it is a phosphoric acid monoester as the active ingredient of 5 - (2 - dimethylaminoethoxy) carvacrol of the formula
cncn
HOHO
0--CH1-CH,- N0-CH 1 -CH, -N
CHCH
CIiCIi
CW, CH3 CW, CH 3
(OH)1OP-O(OH) 1 OP-O
CH,CH,
0-CH2-CH1-N0-CH 2 -CH 1 -N
CHCH
wird in bekannter Weise hergestellt (deutsche Patentschrift 9 05 738. A. B u ζ a sr und Mitarbeitet. Bull. Soc. chim. France. 1959. 839 bis 849).is produced in a known manner (German patent specification 9 05 738. A. B u ζ as r and employees. Bull. Soc. chim. France. 1959. 839 to 849).
CH, Der erfindungsgemäße PhosphorsäuremonoesterCH, the phosphoric acid monoester according to the invention
wird in an sich bekannter Weise (H ο übe η We yl. Bd. 12 2, S. 143ff.) durch Umsetzung von 2-l)imeih\laminoäthoxycarvacrol der Formelis used in a manner known per se (H ο übe η We yl. Vol. 12 2, p. 143ff.) By converting 2-l) imeih \ laminoäthoxycarvacrol the formula
CH, CH,
oder ein Alkalimetaiisalz hiervon enthält.CH, CH,
or an alkali metal salt thereof.
HOHO
CH3 CH 3
C) --CH1 CC) --CH 1 C
Die Erfindung betrifft den Phosphoisäuremonoester von 5-(2-Dimethylaminoäthoxy)carvacrol der FormelThe invention relates to the phosphoic acid monoester of 5- (2-dimethylaminoethoxy) carvacrol of the formula
CW
CH, CH, CW
CH, CH,
CH,CH,
ClCl
(OH)2OP -O(OH) 2 OP -O
CH,CH,
mit POCI, und Verseifen des auftretenden Phosphorsäureesterchlorids hergestellt.with POCI, and saponification of the phosphoric acid ester chloride that occurs manufactured.
CII,CII,
C)-CH1-CH1-NC) -CH 1 -CH 1 -N
CHCH
cn, cn,cn, cn,
und die Alkaümetallsal/e hiervon, ein Verfahren zu
Herstellung der Ausgangscarvacrolc
5-(2-Dimethyiaminoäthoxy)carvacryl-hydrogensulfaland the alkali metal salt thereof, a process for making the parent carvacrolc
5- (2-dimethyiaminoethoxy) carvacryl-hydrogen sulfal
23.7 g (0,1 Mol) 5 - (2 - Dimethylaminoälhoxv)-CH3 6s carvacrol werden zusammen mit 31,6 g (0,4MoI) Pyridin und 21.4 g (0,22 Mol) Amidnsulfonsäure 45 Minuten unter Rühren auf 95 C erhitzt, überschüssiges Pyridin wird im Vakuum abdestilliert. der23.7 g (0.1 mol) of 5 - (2 - dimethylaminoalhoxv) -CH 3 6s carvacrol together with 31.6 g (0.4 mol) of pyridine and 21.4 g (0.22 mol) of amidesulfonic acid are heated to 95 ° C. for 45 minutes with stirring heated, excess pyridine is distilled off in vacuo. the
Rückstand in Wasser gelöst, mit 15 g K2CO, versetzt und mit Chloroform extrahiert. Die wäßrige Phase wird mit 2n-H2SO4 auf pH 7,5 eingestellt. Man saugt das ausgefallene Produkt über eine Nutsche ab und wäscht es einige Male mit kaltem Wasser. Ausbeute nach zweimaliger Umkristallisation aus Wasser: 20,'.) <i (66% der Theorie), Fp.: 255 bis 257 C (Zers.).The residue is dissolved in water , mixed with 15 g of K 2 CO and extracted with chloroform. The aqueous phase is adjusted to pH 7.5 with 2N H 2 SO 4. The precipitated product is suctioned off through a suction filter and washed a few times with cold water. Yield after two recrystallization from water: 20%) <i (66% of theory), melting point: 255 to 257 ° C. (decomp.).
5-(2-Dimethylaminoäthoxy)carv;icryi-hydrogensulfat5- (2-dimethylaminoethoxy) carv; icryi hydrogen sulfate
135 g 5-(2-DimethyIaminoütlioxy)carvaaOl werden in 365 ml Dimethylaniün gelöst und unter Eiskühlung und Rühren mit 80 g Chlorsulfonsäure versetzt. Nach beendeter Chlorsulfonsäure-Zugabe wird das Gemisch mit wäßriger, 50%iger KOH-Lösung alkalisiert, filtriert und das Dimethylaniün durch Ätherextraktion entfernt. Die wäßrige Phase wird auf etwa 1Z3 eingeengt und mit 2H-H2SO4. auf pH 7,5 eingestellt. Das ausgefallene Produkt wird abgesaugt und mit kaltem Wasser gewaschen. Ausbeute nach dreimaliger Umkristallijation aus Wasser: 94,6 g. Fp.: 256 bis 258 C.135 g of 5- (2-DimethyIaminoutlioxy) carvaaOl are dissolved in 365 ml of Dimethylaniün and mixed with 80 g of chlorosulfonic acid while cooling with ice and stirring. After the addition of chlorosulfonic acid has ended, the mixture is made alkaline with an aqueous 50% KOH solution and filtered, and the dimethylane is removed by extraction with ether. The aqueous phase is concentrated to about 1 line 3 and treated with 2H-H 2 SO 4 . adjusted to pH 7.5. The precipitated product is filtered off with suction and washed with cold water. Yield after three recrystallizations from water: 94.6 g. Fp .: 256 to 258 C.
Phosphorsäuremono-5-(2-dimethylaminoäthox\)-carvacrylcsterdi-kaliumsalz Phosphoric acid mono-5- (2-dimethylaminoethox \) -carvacrylcsterdi-potassium salt
Eine Lösung von 11.9 g (0.05 Mol) 5-(2-DimelhyI-aminoäthoxyjearvacro! in 50 ml Chloroform (frei von Äthanol) wird zu 30,7 g (0.2 Mol) POCl, getropft und das Gemisch 2 Stunden zum Sieden erhitzt. Chloroform und überschüssiges POCl, werden abdestilliert, der Rückstand mit K2CO, alkalisiert. alkaliunlösliche Produkte durch Älherextraktion entfernt. Die wäßrige Phase w ird im Vakuum zur Trockne eingeengt und das gewünschte Reaktionsprodukt mit Äthanol aus dem Rückstand herausgelöst. NachA solution of 11.9 g (0.05 mol) of 5- (2-dimethylaminoethoxyjearvacro! In 50 ml of chloroform (free of ethanol) is added dropwise to 30.7 g (0.2 mol) of POCl and the mixture is heated to the boil for 2 hours and excess POCl are distilled off, the residue is made alkaline with K 2 CO. Alkali-insoluble products are removed by extraction with ether. The aqueous phase is evaporated to dryness in vacuo and the desired reaction product is dissolved out of the residue with ethanol
Filtration wird das Äthanol abdestilliert und der Rückwand aus Isopropanol umkrisiallisicrt. Ausbeute: 13,4 g (67,9% der Theorie).Filtration, the ethanol is distilled off and the back wall is crystallized from isopropanol. Yield: 13.4 g (67.9% of theory).
!!hosphorsäuremono-5-(2-dimethyiaminoäthoxv)-carvaerylesier ! ! phosphoric acid mono-5- (2-dimethyiaminoethoxv) -carvaerylesier
i2,4 g Phosphorsäuremono- 5-(2-dimethylaminoäthox\)carvL;cry!estcrdi-kaliumsalz werden in Wasser gelöst und unter Rühren mit verdünnter HCl auf pH 4 eingestellt. Das ausgefallene Produkt wird mil einer Nutsche abgesaugt und mit kaltem Wasser chloridfrei gewaschen. Ausbeute: 8.4 ü. Fp.: 270 bis 271 C.2.4 g of phosphoric acid mono- 5- (2-dimethylaminoethoxy) carvL; cry! estcr di-potassium salt are dissolved in water and diluted with dilute HCl while stirring pH adjusted to 4. The precipitated product is suctioned off with a suction filter and with cold water Washed free of chloride. Yield: 8.4 ü. Fp .: 270 to 271 C.
Analyse:Analysis:
Berechne! ... C 53,0. JJ 7.62. N 4.41. (J 25.2.Calculate! ... C 53.0. YY 7.62. N 4.41. (J 25.2.
P 9.76;
gefunden .... C 53.34. H 7.51. N 4.!3. O 25.32P 9.76;
found .... C 53.34. H 7.51. N 4th! 3. O 25.32
P 9,63.P 9.63.
Phosphorsäurernono-5-(2-dirneihylaminoäihox\ I-carvacrylestermono-Na-SaIz Phosphoric acid mono-5- (2-dirneihylaminoäihox \ I-carvacrylestermono-Na-SaIz
Phosphorsäuremono-5-(2-dimethylaminoäl hox ylcarvacrylester wird in Wasser suspendiert und mit Jer berechneten Menge 1 n-NaOH versetzt. Die klarePhosphoric acid mono-5- (2-dimethylaminoal hoxylcarvacrylester is suspended in water and mixed with Jer calculated amount of 1N NaOH. The clear one
yo Lösung wird im Vakuum zur Trockne eingeengt, der Rückstand aus 50%igem wäßrigem Äthanol umkristallisiert. Das so erhaltene Salz enthält drei Kristallwasser (Bestimmung nach Karl F i s c Ii e r). Das Kristallwasser geht beim Trocknen bei < 100 C über P2O5 verloren. The solution is concentrated to dryness in vacuo, and the residue is recrystallized from 50% aqueous ethanol. The salt obtained in this way contains three waters of crystallization (determination according to Karl Fisc Ii er). The water of crystallization is lost on drying at <100 C above P 2 O 5 .
Claims (1)
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19722238260 DE2238260C3 (en) | 1972-08-03 | Phosphoric acid monoester of 5- (2-dimethylaminoethoxy) -carvacrol, process for its preparation and pharmaceuticals containing it | |
| AU58632/73A AU479920B2 (en) | 1972-08-03 | 1973-07-27 | Sulfuric and phosphoric acid esters of 5-(2-aminoethoxy)-carvacrols and processes for their preparation |
| GB3615373A GB1389984A (en) | 1972-08-03 | 1973-07-30 | Sulphuric and phosphoric acid esters of substituted carvacrols |
| CA178,013A CA995684A (en) | 1972-08-03 | 1973-08-02 | Sulfuric and phosphoric acid esters of 5-(2-amino-ethoxy)-carvacrols and processes for their preparation |
| FR7328548A FR2194445B1 (en) | 1972-08-03 | 1973-08-03 | |
| JP8692673A JPS5318022B2 (en) | 1972-08-03 | 1973-08-03 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19722238260 DE2238260C3 (en) | 1972-08-03 | Phosphoric acid monoester of 5- (2-dimethylaminoethoxy) -carvacrol, process for its preparation and pharmaceuticals containing it |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2238260A1 DE2238260A1 (en) | 1974-02-21 |
| DE2238260B2 DE2238260B2 (en) | 1975-08-07 |
| DE2238260C3 true DE2238260C3 (en) | 1976-03-18 |
Family
ID=
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