DE131741C - - Google Patents
Info
- Publication number
- DE131741C DE131741C DENDAT131741D DE131741DA DE131741C DE 131741 C DE131741 C DE 131741C DE NDAT131741 D DENDAT131741 D DE NDAT131741D DE 131741D A DE131741D A DE 131741DA DE 131741 C DE131741 C DE 131741C
- Authority
- DE
- Germany
- Prior art keywords
- pyrazolone
- dimethyl
- phenyl
- saccharin
- compound
- 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
- 229940081974 Saccharin Drugs 0.000 claims description 17
- 235000019204 saccharin Nutrition 0.000 claims description 17
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 claims description 17
- CVHZOJJKTDOEJC-UHFFFAOYSA-N Saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 claims description 12
- 150000001875 compounds Chemical class 0.000 claims description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 2
- 238000002425 crystallisation Methods 0.000 claims 1
- 230000005712 crystallization Effects 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 150000003839 salts Chemical class 0.000 description 11
- 239000011780 sodium chloride Substances 0.000 description 11
- 229930013930 alkaloids Natural products 0.000 description 6
- -1 saccharin compound Chemical class 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 3
- LOUPRKONTZGTKE-WZBLMQSHSA-N Quinine Chemical compound C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-WZBLMQSHSA-N 0.000 description 2
- QMGVPVSNSZLJIA-FVWCLLPLSA-N Strychnine Chemical compound O([C@H]1CC(N([C@H]2[C@H]1[C@H]1C3)C=4C5=CC=CC=4)=O)CC=C1CN1[C@@H]3[C@]25CC1 QMGVPVSNSZLJIA-FVWCLLPLSA-N 0.000 description 2
- 206010047700 Vomiting Diseases 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 231100000331 toxic Toxicity 0.000 description 2
- 230000002588 toxic Effects 0.000 description 2
- KMPWYEUPVWOPIM-CFGMGRTJSA-N (S)-[(2R,4S,5S)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl]-quinolin-4-ylmethanol Chemical compound C1=CC=C2C([C@@H]([C@@H]3N4CC[C@H]([C@@H](C4)C=C)C3)O)=CC=NC2=C1 KMPWYEUPVWOPIM-CFGMGRTJSA-N 0.000 description 1
- 235000001258 Cinchona calisaya Nutrition 0.000 description 1
- 241000434299 Cinchona officinalis Species 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- BQJCRHHNABKAKU-KBQPJGBKSA-N Morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 description 1
- VEQOALNAAJBPNY-UHFFFAOYSA-N Phenazone Chemical compound CN1C(C)=CC(=O)N1C1=CC=CC=C1 VEQOALNAAJBPNY-UHFFFAOYSA-N 0.000 description 1
- 229960000948 Quinine Drugs 0.000 description 1
- 241001279009 Strychnos toxifera Species 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000003797 alkaloid derivatives Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000002478 diastatic Effects 0.000 description 1
- 230000029087 digestion Effects 0.000 description 1
- 230000002045 lasting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229960005181 morphine Drugs 0.000 description 1
- 229930014694 morphine Natural products 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical compound O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 1
- 230000000979 retarding Effects 0.000 description 1
- 229960005453 strychnine Drugs 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000001225 therapeutic Effects 0.000 description 1
- 231100000925 very toxic Toxicity 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D231/18—One oxygen or sulfur atom
- C07D231/20—One oxygen atom attached in position 3 or 5
- C07D231/22—One oxygen atom attached in position 3 or 5 with aryl radicals attached to ring nitrogen atoms
- C07D231/26—1-Phenyl-3-methyl-5- pyrazolones, unsubstituted or substituted on the phenyl ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
In der Patentschrift 35933 haben Fahlberg und List ein Verfahren beschrieben, nach welchem Salze aus Saccharin und den vier nachfolgenden Alkaloiden erhalten werden können, und zwar dem Chinin, Cinchonin, Strychnin und Morphin.In the patent specification 35933 Fahlberg and List have described a method according to which Salts can be obtained from saccharin and the four subsequent alkaloids, namely the quinine, cinchonine, strychnine and morphine.
Das Herstellungsverfahren besteht einfach darin, dafs man das Saccharin- mit dem betreffenden Alkaloid neutralisirt, so dafs es sich hier um eine zur Gewinnung von Salzen ganz allgemein übliche Methode handelt.The manufacturing process consists simply of mixing the saccharin with the substance in question Alkaloid neutralized, so that it is a question here for the production of salts common method.
Nun hat aber das Verfahren von Fahlberg und List keine praktische Bedeutung gewonnen, entweder weil die Salze der vier in dem betreffenden Patente angegebenen Alkaloide keinen Werth besitzen, oder weil die erhaltenen Salze ungefähr dieselben Eigenschaften aufweisen wie die Alkaloide, von denen sie abstammen, oder endlich weil die Herstellung von reinen Salzen mit Schwierigkeiten verbunden war.Now, however, the Fahlberg and List method has gained no practical significance, either because the salts of the four alkaloids specified in the relevant patent are none Have value, or because the salts obtained have approximately the same properties as the alkaloids from which they are derived, or finally because the production of pure salts was fraught with difficulty.
Demgegenüber haben die Erfinder versucht, Verbindungen des Saccharins nicht mit Alkaloiden, sondern mit anderen organischen Basen als Alkaloide durch directe Einwirkung des Saccharins auf diese Basen zu gewinnen.In contrast, the inventors tried to avoid compounds of saccharine with alkaloids, but with organic bases other than alkaloids through the direct action of the To win saccharin on these bases.
Unter den Verbindungen,- welche die Versuche ergeben haben, kennzeichnet sich die Verbindung aus Saccharin und i-Phenyl-2, 3-dimethyl-5-pyrazolon durch sehr interessante und werthvolle Eigenschaften.Among the compounds - which the tests have shown, the Compound of saccharin and i-phenyl-2, 3-dimethyl-5-pyrazolone by very interesting and valuable properties.
Dieses Salz wird in folgender Weise hergestellt: This salt is made in the following way:
183 Theile Saccharin und 188 Theile i-Phenyl-2, 3-dimethyl-5-pyrazolon werden in einer so kleinen183 parts saccharin and 188 parts i-phenyl-2, 3-dimethyl-5-pyrazolone are made in such a small way
Mengelot
kochenden Wassers aufgelöst wie nur möglich. Während der Abkühlung krystallisirt das Product aus, und zwar nähert sich die Ausbeute der theoretischen.dissolved in boiling water as much as possible. While cooling down The product crystallizes out, and the yield approaches the theoretical one.
Die auf diese Weise erhaltene Verbindung von i-Phenyl-2, 3-dimethyl-5-pyrazolon mit Saccharin besteht aus nicht sehr gut ausgebildeten prismatischen Krystallen, welche bei 145 bis 1500 schmelzen.The compound I-phenyl-2 thus obtained, 3-dimethyl-5-pyrazolone with saccharin consists of non very well trained prismatic crystals, melting at 145 to 150 0th
100 Theile Wasser von 1 8° lösen 0,50 Theile dieses Salzes auf. Bei 370 werden 0,74 und bei ioo° 25 Theile aufgelöst.100 parts of water at 18 ° dissolve 0.50 part of this salt. At 37 0 0.74 and dissolved at 25 ° ioo parts.
Im Vergleich zu dem i-Phenyl-2, 3-dimethyl-5-pyrazolon weist die Saccharinverbindung besondere Eigenschaften auf.Compared to the i-phenyl-2,3-dimethyl-5-pyrazolone the saccharin compound has special properties.
Das i-Phenyl-2, 3-dimethyl-5-pyrazolon geht nämlich mit Säuren nur sehr schwer Verbindungen ein, und es haben die Salze, welche trotz der grofsen Schwierigkeiten erhalten werden konnten, keine praktische Verwendung gefunden, sei es, weil diese Salze sehr toxisch sind, sei es, weil dieselben einen unangenehmen Geschmack besitzen.The i-phenyl-2,3-dimethyl-5-pyrazolone is very difficult to combine with acids one, and they have the salts which are obtained in spite of the great difficulties could not have found any practical use, either because these salts are very toxic are, be it because they have an unpleasant taste.
Demgegenüber gelingt die Darstellung der neuen Verbindung aus i-Phenyl-2, 3-dimethyl-5-pyrazolon und Saccharin sehr leicht, und die Reaction geht glatt vor sich.In contrast, the preparation of the new compound from i-phenyl-2,3-dimethyl-5-pyrazolone succeeds and saccharin very easily, and the reaction proceeds smoothly.
Des Weiteren weist das neue Salz mehrere neue technische Fortschritte auf.Furthermore, the new salt shows several new technical advances.
Die Verbindung von i-Phenyl-2, 3-dimethyl-5-pyrazolon mit Saccharin besitzt viel vortrefflichere therapeutische Eigenschaften als die bisher zu demselben Zwecke verwendeten Körper, wie z. B. das i-Phenyl-2, 3-dimethyl-5-pyrazolon. The compound of i-phenyl-2, 3-dimethyl-5-pyrazolone with saccharin has much more excellent therapeutic properties than that previously used for the same purpose body such. B. i-phenyl-2,3-dimethyl-5-pyrazolone.
Die Saccharinverbindung ist nämlich bei gleichen Gewichtsmengen weniger toxisch als das i-Phenyl-2, 3-dimethyl-5-pyrazolon selbst, und beim Einnehmen des neuen Productes durch Patienten tritt niemals Erbrechen ein, wie dies bei der Verwendung von i-Phenyl-2, 3-dimethyl - 5 - pyrazolon häufig vorkommt.Namely, the saccharin compound is less toxic than in equal amounts by weight the i-phenyl-2,3-dimethyl-5-pyrazolone itself, and vomiting never occurs when the patient ingests the new product, as this often occurs when i-phenyl-2, 3-dimethyl - 5 - pyrazolone is used.
Die an Thieren sowohl wie an Menschen vorgenommenen Versuche haben ergeben, dafs i-Phenyl-2, 3-dimethyl-5-pyrazolon und dessen Saccharinverbindung bei gleichen Gewichtsmengen ähnliche Wirkungen hervorrufen, so dafs also die Wirkung des neuen Productes nicht etwa im Verhältnisse zu dem darin enthaltenen i-Phenyl-2, 3-dimethyl-5 - pyrazolon steht, sondern viel höher ist. Es ist aufserdem zu berücksichtigen, dafs die Saccharinverbindung bei gleichen Gewichtsmengen weniger toxisch ist als das i-Phenyl-2, 3 -dimethyl-5-pyrazolon. The experiments made on animals as well as on humans have shown that i-Phenyl-2, 3-dimethyl-5-pyrazolone and its saccharin compound produce similar effects at equal amounts by weight, see above so that the effect of the new product is not in relation to that contained in it i-phenyl-2, 3-dimethyl-5 - pyrazolone stands, but is much higher. It is also to take into account that the saccharin compound is less for the same weight is more toxic than i-phenyl-2,3-dimethyl-5-pyrazolone.
Ferner ist die physiologische Wirkung der Saccharinverbindung andauernder als diejenige des i-Phenyl-2, 3-dimethyl-5-pyrazolons und aufserdem constanter, was durch zahlreiche Versuche nachgewiesen worden ist.Furthermore, the physiological effect of the saccharin compound is more lasting than that of i-phenyl-2, 3-dimethyl-5-pyrazolone and moreover constant, which has been proven by numerous experiments.
Ferner übt die Verbindung von i-Phenyl-2, 3-dimethyl-5"pyrazolon mit Saccharin, welche ein Salz ist, nicht dieselbe verzögernde Wirkung auf die Verdauung aus wie freies i-Phenyl-2, 3-dimethyl-5-pyrazolon. Des Weiteren läfst der neue Körper den diastatischen Vergährungserscheinungen ihren freien Lauf, und wahrscheinlich aus diesem Grunde ruft die Saccharinverbindung nicht dieselben Brecherscheinungen hervor wie 1-Phenyl-2, 3-dimethyl-5-pyrazolon. Furthermore, the compound of i-phenyl-2, 3-dimethyl-5 "pyrazolone with saccharin, which is a salt, does not have the same retarding effect on digestion like free i-phenyl-2, 3-dimethyl-5-pyrazolone. Furthermore you run the new body the diastatic deterioration its free run, and probably for this reason the saccharin compound does not cause the same vomiting phenomena such as 1-phenyl-2, 3-dimethyl-5-pyrazolone.
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE131741C true DE131741C (en) |
Family
ID=400051
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT131741D Active DE131741C (en) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE131741C (en) |
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0
- DE DENDAT131741D patent/DE131741C/de active Active
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