DE138443C - - Google Patents
Info
- Publication number
- DE138443C DE138443C DENDAT138443D DE138443DA DE138443C DE 138443 C DE138443 C DE 138443C DE NDAT138443 D DENDAT138443 D DE NDAT138443D DE 138443D A DE138443D A DE 138443DA DE 138443 C DE138443 C DE 138443C
- Authority
- DE
- Germany
- Prior art keywords
- atropinium
- nitrate
- ethyl
- nitrates
- alkyl
- 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.)
- Active
Links
- RKUNBYITZUJHSG-SPUOUPEWSA-O atropinium Chemical compound O([C@H]1C[C@H]2CC[C@@H](C1)[NH+]2C)C(=O)C(CO)C1=CC=CC=C1 RKUNBYITZUJHSG-SPUOUPEWSA-O 0.000 claims description 11
- -1 atropinium alkyl nitrates Chemical class 0.000 claims description 10
- 238000001704 evaporation Methods 0.000 claims description 5
- 229930006677 A03BA01 - Atropine Natural products 0.000 claims description 4
- RKUNBYITZUJHSG-SPUOUPEWSA-N Atropine Chemical compound O([C@H]1C[C@H]2CC[C@@H](C1)N2C)C(=O)C(CO)C1=CC=CC=C1 RKUNBYITZUJHSG-SPUOUPEWSA-N 0.000 claims description 4
- 229960000396 Atropine Drugs 0.000 claims description 4
- IWOUKMZUPDVPGQ-UHFFFAOYSA-N Barium nitrate Chemical compound [Ba+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O IWOUKMZUPDVPGQ-UHFFFAOYSA-N 0.000 claims description 4
- TZCXTZWJZNENPQ-UHFFFAOYSA-L Barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- IDNUEBSJWINEMI-UHFFFAOYSA-N Ethyl nitrate Chemical compound CCO[N+]([O-])=O IDNUEBSJWINEMI-UHFFFAOYSA-N 0.000 claims description 3
- YPNVIBVEFVRZPJ-UHFFFAOYSA-L Silver sulfate Chemical compound [Ag+].[Ag+].[O-]S([O-])(=O)=O YPNVIBVEFVRZPJ-UHFFFAOYSA-L 0.000 claims description 3
- 239000007864 aqueous solution Substances 0.000 claims description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 3
- 150000002823 nitrates Chemical class 0.000 claims description 3
- 229910000367 silver sulfate Inorganic materials 0.000 claims description 3
- 239000000706 filtrate Substances 0.000 claims description 2
- 238000002844 melting Methods 0.000 claims description 2
- 229910052751 metal Inorganic materials 0.000 claims description 2
- 239000002184 metal Substances 0.000 claims description 2
- 150000002739 metals Chemical class 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 150000003467 sulfuric acid derivatives Chemical class 0.000 claims description 2
- RDHPKYGYEGBMSE-UHFFFAOYSA-N Bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 claims 1
- KIWBPDUYBMNFTB-UHFFFAOYSA-M ethyl sulfate Chemical compound CCOS([O-])(=O)=O KIWBPDUYBMNFTB-UHFFFAOYSA-M 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 230000004048 modification Effects 0.000 claims 1
- 238000006011 modification reaction Methods 0.000 claims 1
- LRMHVVPPGGOAJQ-UHFFFAOYSA-N Methyl nitrate Chemical compound CO[N+]([O-])=O LRMHVVPPGGOAJQ-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 4
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 3
- RLJMLMKIBZAXJO-UHFFFAOYSA-N Lead(II) nitrate Chemical compound [O-][N+](=O)O[Pb]O[N+]([O-])=O RLJMLMKIBZAXJO-UHFFFAOYSA-N 0.000 description 2
- INQOMBQAUSQDDS-UHFFFAOYSA-N Methyl iodide Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
- 235000019441 ethanol Nutrition 0.000 description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- NEHMKBQYUWJMIP-UHFFFAOYSA-N Chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 1
- PIJPYDMVFNTHIP-UHFFFAOYSA-L Lead sulfate Chemical compound [PbH4+2].[O-]S([O-])(=O)=O PIJPYDMVFNTHIP-UHFFFAOYSA-L 0.000 description 1
- 229940050176 Methyl Chloride Drugs 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D451/00—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof
- C07D451/02—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof
- C07D451/04—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof with hetero atoms directly attached in position 3 of the 8-azabicyclo [3.2.1] octane or in position 7 of the 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring system
- C07D451/06—Oxygen atoms
- C07D451/10—Oxygen atoms acylated by aliphatic or araliphatic carboxylic acids, e.g. atropine, scopolamine
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Inorganic Compounds Of Heavy Metals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
JV! 138443 KLASSE 12/?. JV! 138443 CLASS 12 / ?.
Das Hauptpatent betrifft ein Verfahren zur Darstellung der therapeutisch werthvollen Atropiniumalkylnitrate der allgemeinen Formel:The main patent relates to a method for the preparation of therapeutically valuable Atropinium alkyl nitrates of the general formula:
HO. CH2 NO3 HO. CH 2 NO 3
welches darin besteht, dafs man entweder Atropiniumalkylhydroxyde mit Salpetersäure behandelt oder die Atropiniumalkylhalogenide (wie z. B. das Atropiniummethyljodid) mit den salpetersauren Salzen der Schwermetalle umsetzt. which consists in either treating atropinium alkyl hydroxides with nitric acid treated or the atropinium alkyl halides (such as, for example, the atropinium methyl iodide) with the converts nitric acid salts of heavy metals.
Es wurde nun gefunden, dafs man die oben erwähnten Atropiniumalkylnitrate auch dadurch erhalten kann, dafs man Atropin mit Alkylnitraten (wie z. B. Methylnitrat) in Reaction bringt, oder die Atropiniumalkylsulfate [wie z. B. AtropiniummethylsulfatIt has now been found that the above-mentioned atropinium alkyl nitrates can also be used in this way can be obtained by reacting atropine with alkyl nitrates (such as methyl nitrate) brings, or the atropinium alkyl sulfates [such as. B. atropinium methyl sulfate
(C17H2, N O3 C H3J2 SO,}(C 17 H 2 , NO 3 CH 3 J 2 SO,}
mit den Nitraten solcher Metalle umsetzt, die schwerlösliche, oder unlösliche Sulfate bilden, wie die Nitrate der alkalischen Erden, Bleinitrat und dergl.reacts with the nitrates of metals that form sparingly soluble or insoluble sulfates, like the nitrates of alkaline earths, lead nitrate and the like.
Beispiel 1.Example 1.
Eine Lösung von 28,9 g Atropin in 100 g Methylalkohol wird nach Zusatz von 7,7 g Methylnitrat im geschlossenen Gefäfs 2 Stunden lang auf ungefähr iio° erhitzt. Nach dem Verdunsten des Methylalkohols krystallisirt das Atropiniummethylni trat vom Schmelzpunkt 163° aus.A solution of 28.9 g of atropine in 100 g of methyl alcohol is obtained after adding 7.7 g Heat methyl nitrate in a closed vessel to about 10 ° for 2 hours. After this Evaporation of the methyl alcohol crystallizes, and the atropinium methylene rose from its melting point 163 ° off.
70,4 g Atropiniummethylsulfat, welches man durch Umsetzen von Atropiniummethylchlorid mit Silbersulfat als ein in Aether unlösliches Produkt erhält, werden in Wasser gelöst und mit einer wässerigen Lösung von 26,1 g Bariumnitrat versetzt. Nach dem Abfiltriren des ausgeschiedenen Bariumsulfats wird aus der filtrirten Flüssigkeit das Atropiniummethylnitrat durch Eindunsten gewonnen.70.4 g of atropinium methyl sulfate, which is obtained by reacting atropinium methyl chloride obtained with silver sulfate as a product insoluble in ether are dissolved in water and mixed with an aqueous solution of 26.1 g of barium nitrate. After filtering off the excreted Barium sulphate becomes atropinium methyl nitrate from the filtered liquid obtained by evaporation.
70,4 g Atropiniummethylsulfat, welches man durch Umsetzen von Atropiniummethyljodid mit Silbersulfat als ein in Aether unlösliches Produkt erhält, werden in Wasser gelöst und mit einer wässerigen Lösung von 33,1 g Bleinitrat versetzt. Man filtrirt von dem ausgeschiedenen Bleisulfat ab und gewinnt aus dem Filtrat durch Eindunsten das Atropiniummethylnitrat. 70.4 g of atropinium methyl sulfate, which is obtained by reacting atropinium methyl iodide obtained with silver sulfate as a product insoluble in ether are dissolved in water and mixed with an aqueous solution of 33.1 g of lead nitrate. The precipitated is filtered off Lead sulfate and wins the atropinium methyl nitrate from the filtrate by evaporation.
28,9 g Atropin werden in 100 g Aethylalkohol gelöst und nach Zusatz von 9,1 g Aethylnitrat im geschlossenen Gefäfse 2 Stunden auf ungefähr iio° erhitzt. Nach dem Verdunsten des Alkohols krystallisirt das Atropinium-28.9 g of atropine are dissolved in 100 g of ethyl alcohol and, after the addition of 9.1 g of ethyl nitrate Heated in a closed vessel to about 10 ° for 2 hours. After evaporation of alcohol crystallizes the atropinium
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE138443C true DE138443C (en) |
Family
ID=406251
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT138443D Active DE138443C (en) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE138443C (en) |
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0
- DE DENDAT138443D patent/DE138443C/de active Active
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