CH299530A - Process for the preparation of 4- (B-amino-γ-bromo-propyl) -imidazole-dihydrobromide. - Google Patents
Process for the preparation of 4- (B-amino-γ-bromo-propyl) -imidazole-dihydrobromide.Info
- Publication number
- CH299530A CH299530A CH299530DA CH299530A CH 299530 A CH299530 A CH 299530A CH 299530D A CH299530D A CH 299530DA CH 299530 A CH299530 A CH 299530A
- Authority
- CH
- Switzerland
- Prior art keywords
- dihydrobromide
- amino
- imidazole
- bromo
- propyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 8
- 238000000354 decomposition reaction Methods 0.000 claims description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 3
- 239000000155 melt Substances 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 2
- UQDJGEHQDNVPGU-UHFFFAOYSA-N serine phosphoethanolamine Chemical compound [NH3+]CCOP([O-])(=O)OCC([NH3+])C([O-])=O UQDJGEHQDNVPGU-UHFFFAOYSA-N 0.000 claims description 2
- JGJLWPGRMCADHB-UHFFFAOYSA-N hypobromite Inorganic materials Br[O-] JGJLWPGRMCADHB-UHFFFAOYSA-N 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 2
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- -1 amino-y-bromo-propyl Chemical group 0.000 description 1
- 230000003276 anti-hypertensive effect Effects 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000004042 decolorization Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
Verfahren zur Herstellung von 4#(ss=Amino-y-brom-propyl)-imidazol-dihydrobromid. Es wurde gefunden, dass das 4-(ss-Amino- y-brom-propyl)-imidazol-dihydrobromid fol gender Strukturformel
EMI0001.0008
eine starke protrahierte blutdrucksenkende Wirkung besitzt. Diese Eigenschaft kommt sowohl dem Racemat als auch beiden optischen Antipoden zu.
Zur Herstellung des 4-(ss-Amino-y-brom- propyl) -imidazol-dihydrobromids lässt man Bromwasserstoff auf ss - Amino - y - imidazolyl- (4)-propanol oder eines seiner Salze, gegebe nenfalls in Gegenwart von Wasser oder Eis essig, einwirken. Dadurch wird die Hydroxyl- gruppe durch ein Bromatom ersetzt. Die ent stehende Base bildet mit der überschüssigen Säure das Dihydrobromid, welches als solches isoliert wird.
Die neue Verbindung soll als Arzneimittel Verwendung finden.
Gegenstand des Patentes ist nun ein Ver fahren zur Herstellung von 4-(ss-Amino-y- brom-propyl)-imidazol-dihydrobromid, das dadurch gekennzeichnet ist, dass man Brom wasserstoff auf ss-Amino-y-imidazölyl-(4)-pro- panol-dihydrobromid einwirken lässt.
Die neue Verbindung ist in Wasser und Methanol leicht, in Äthanol schwerer löslich und in Äther unlöslich; die D-Form schmilzt bei 210-212 unter Zersetzung, -die L-Form bei 210-212 unter Zersetzung und das Race- mat bei 229-230 unter Zersetzung.
<I>Beispiel:</I> 1 Gewichtsteil D-ss-Amino-y-imidazolyl-(4)- propanol-dihydrobromid wird mit 25 Gewichts teilen einer gesättigten Lösung von Bromwas- serstoffsäure in Eisessig im Bombenrohr vier Stunden lang auf 105 geheizt. Nach dem Erkalten wird die Lösung mit Wasserver dünnt und zur Trockne eingeengt. Den festen Rückstand löst man in Wasser und dampft nach Entfärbung mit Kohle erneut zur Trockne ein. Schliesslich wird nun der Rück stand in absolutem Methanol gelöst und durch Zugabe von Äther zur Kristallisation gebracht.
Das D-4-(ss-Amino-y-brom-propyl)-imidazol- dihydrobromid wird genutscht und mit Alko- kol und Äther gewaschen. Ausbeute: 1 Ge wichtsteil. Dieses Salz schmilzt unter Zer setzung bei 210-212 .
EMI0001.0051
Process for the preparation of 4 # (ss = amino-y-bromo-propyl) -imidazole-dihydrobromide. It was found that the 4- (ss-amino-y-bromo-propyl) -imidazole-dihydrobromide following gender structural formula
EMI0001.0008
Has a strong protracted antihypertensive effect. This property applies to both the racemate and both optical antipodes.
To prepare 4- (ß-amino-γ-bromopropyl) -imidazole dihydrobromide, hydrogen bromide is allowed to add to ß-amino-γ-imidazolyl- (4) propanol or one of its salts, if necessary in the presence of water or ice vinegar, act. This replaces the hydroxyl group with a bromine atom. The resulting base forms the dihydrobromide with the excess acid, which is isolated as such.
The new compound is said to be used as a drug.
The subject of the patent is now a process for the production of 4- (ss-amino-y-bromo-propyl) -imidazole-dihydrobromide, which is characterized in that hydrogen bromide is added to ss-amino-y-imidazölyl- (4) -pro- panol-dihydrobromide.
The new compound is easily soluble in water and methanol, sparingly soluble in ethanol and insoluble in ether; the D-form melts at 210-212 with decomposition, the L-form at 210-212 with decomposition and the racemate at 229-230 with decomposition.
<I> Example: </I> 1 part by weight of D-ss-amino-y-imidazolyl- (4) -propanol-dihydrobromide is heated to 105 for four hours with 25 parts by weight of a saturated solution of hydrobromic acid in glacial acetic acid in a sealed tube . After cooling, the solution is diluted with Wasserver and evaporated to dryness. The solid residue is dissolved in water and, after decolorization with charcoal, evaporated to dryness again. Finally, the residue is now dissolved in absolute methanol and crystallized by adding ether.
The D-4- (ss-amino-y-bromo-propyl) -imidazole dihydrobromide is sucked off and washed with alcohol and ether. Yield: 1 part by weight. This salt melts with decomposition at 210-212.
EMI0001.0051
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH299530T | 1951-09-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH299530A true CH299530A (en) | 1954-06-15 |
Family
ID=4490346
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH299530D CH299530A (en) | 1951-09-19 | 1951-09-19 | Process for the preparation of 4- (B-amino-γ-bromo-propyl) -imidazole-dihydrobromide. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH299530A (en) |
-
1951
- 1951-09-19 CH CH299530D patent/CH299530A/en unknown
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