DE254487C - - Google Patents
Info
- Publication number
- DE254487C DE254487C DENDAT254487D DE254487DA DE254487C DE 254487 C DE254487 C DE 254487C DE NDAT254487 D DENDAT254487 D DE NDAT254487D DE 254487D A DE254487D A DE 254487DA DE 254487 C DE254487 C DE 254487C
- Authority
- DE
- Germany
- Prior art keywords
- dimethyl
- pyrazolone
- iodophenyl
- bromo
- chloroform
- 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
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 11
- 229910052740 iodine Inorganic materials 0.000 claims description 11
- 239000011630 iodine Substances 0.000 claims description 11
- HEDRZPFGACZZDS-UHFFFAOYSA-N chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 10
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 8
- WKBOTKDWSSQWDR-UHFFFAOYSA-N bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 2
- 210000001772 Blood Platelets Anatomy 0.000 claims 1
- 238000001035 drying Methods 0.000 claims 1
- 238000002844 melting Methods 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 4
- 239000000203 mixture Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- RXXLWJKVDZLVHR-UHFFFAOYSA-N 4-benzyl-5-methylpyrazol-3-one Chemical compound O=C1N=NC(C)=C1CC1=CC=CC=C1 RXXLWJKVDZLVHR-UHFFFAOYSA-N 0.000 description 2
- VEQOALNAAJBPNY-UHFFFAOYSA-N Phenazone Chemical compound CN1C(C)=CC(=O)N1C1=CC=CC=C1 VEQOALNAAJBPNY-UHFFFAOYSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 230000002084 anti-luetic Effects 0.000 description 1
- 230000001754 anti-pyretic Effects 0.000 description 1
- 239000002221 antipyretic Substances 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000002349 favourable Effects 0.000 description 1
- 235000021190 leftovers Nutrition 0.000 description 1
- 229960005222 phenazone Drugs 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000001624 sedative Effects 0.000 description 1
- 239000000932 sedative agent Substances 0.000 description 1
- 230000001225 therapeutic Effects 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.
PATENTSCHRIFTPATENT LETTERING
M 254487 KLASSE XIp. GRUPPEM 254487 CLASS XIp. GROUP
und l-p-Jodphenyl-2-3-dimethyl-4-brom-5-pyrazolon.and 1-p-iodophenyl-2-3-dimethyl-4-bromo-5-pyrazolone.
Patentiert im Deutschen Reiche vom 18. Mai 1911 ab.Patented in the German Empire on May 18, 1911.
Es wurde gefunden, daß man zu therapeutisch wertvollen Verbindungen gelangt, wenn man in das Molekül des i-Phenyl-2 · 3-dimethyl-5-pyrazolons gleichzeitig Brom und Jod einführt.It has been found that therapeutically valuable compounds can be obtained if you get into the molecule of i-phenyl-2 · 3-dimethyl-5-pyrazolons simultaneously introduces bromine and iodine.
Zu diesem Zwecke geht man z. B. vom i-p-Bromphenyl-2 · 3-dimethyl-5-pyrazolon oder vom i-p-Jodphenyl-2 · 3-dimethyl-5-pyrazolon aus und ersetzt in diesen Verbindungen ein Wasserstoffatom in 4-Stellung des Pyrazolkerns nach den hierfür üblichen Methoden durch Jod bzw. durch Brom.For this purpose one goes z. B. from i-p-bromophenyl-2 · 3-dimethyl-5-pyrazolone or from i-p-iodophenyl-2 · 3-dimethyl-5-pyrazolone and replaces one in these compounds Hydrogen atom in the 4-position of the pyrazole nucleus by means of iodine according to the methods customary for this purpose or by bromine.
Die neuen Verbindungen besitzen gleichzeitig den Stoffwechsel befördernde, antiluetische
(Jod), sedative (Brom) und antipyretische (Antipyrin) Wirkung, und zwar enthalten
sie das Brom, Jod und Phenyldimethylpyrazolon in einem solch günstigen Verhältnis,
daß jede der drei Komponenten einen vollen therapeutischen Effekt auslösen kann. Sie
sollen dazu dienen, den sehr häufig bei Jodgebrauch auftretenden Erscheinungen des Jodismus
vorzubeugen bzw. sie zu beseitigen.
Einfachen Gemischen aus Phenyldimethylpyrazolon, Brom- und Jodalkalien gegenüber
zeichnen sich die neuen einheitlichen Dihalogen verbin düngen vor allem dadurch aus, daß
das in ihnen fest gebundene Brom und Jod keines besonderen Alkaliträgers bedarf, um vom
menschlichen Organismus leicht aufgenommen zu werden.The new compounds have at the same time the metabolism-promoting, antiluetic (iodine), sedative (bromine) and antipyretic (antipyrin) effect, and indeed they contain the bromine, iodine and phenyldimethylpyrazolone in such a favorable ratio that each of the three components has a full therapeutic effect can trigger. They are intended to prevent or eliminate the symptoms of iodine which occur very often when iodine is used.
Simple mixtures of phenyldimethylpyrazolone, bromine and iodine alkalis, compared to the new uniform dihalogen compounds, are mainly characterized by the fact that the bromine and iodine firmly bound in them do not require any special alkali carriers to be easily absorbed by the human organism.
i. In eine Lösung von 267 Teilen i-p-Bromphenyl-2 · 3-dimethyl-5-pyrazolon (Ber. 33 [1900],i. In a solution of 267 parts of i-p-bromophenyl-2 3-dimethyl-5-pyrazolone (Ber. 33 [1900],
S. 2609) in 800 Teilen Benzol trägt man unter Rühren 254 Teile gepulvertes Jod ein und erwärmt noch zwei Stunden, auf 50 bis 60°. Nach Zusatz einer Lösung von 75 Teilen wasserfreiem Natriumcarbonat in 450 Teilen Wasser digeriert man 4 bis 6 Stunden am Rückflußkühler auf dem Wasserbad. Die Benzollösung wird von der wäßrigen Schicht getrennt, zwecks Beseitigung des überschüssigen Jods mit verdünnter Bisulfitlösung, und dann mit Natriumcarbonat gewaschen, getrocknet, filtriert und abdestilliert. Das zurückbleibende Reaktionsprodukt wird aus Alkohol umkristallisiert und so die neue Verbindung in farblosen Kristallen erhalten.P. 2609) in 800 parts of benzene, 254 parts of powdered iodine are introduced with stirring and the mixture is heated to 50 to 60 ° for a further two hours. After adding a solution of 75 parts of anhydrous sodium carbonate in 450 parts Water is digested for 4 to 6 hours in a reflux condenser on a water bath. The benzene solution is separated from the aqueous layer to remove the excess iodine with dilute bisulfite solution, and then washed with sodium carbonate, dried, filtered and distilled off. The leftover Reaction product is recrystallized from alcohol and so the new compound becomes colorless Get crystals.
i-p-Bromphenyl-2 · 3-dimethyl-4-jod-5-pyrazolon i-p-Bromophenyl-2 • 3-dimethyl-4-iodo-5-pyrazolone
CH3 CH 3
Br-<Br- < C-JC-J
-N-—-CO-N -—- CO
5555
6060
bildet farblose Kristalle, die bei 163 ° schmelzen. In Wasser ist es kaum löslich, schwer in verdünnter Säure, leicht in warmem Alkohol und Benzol.forms colorless crystals that melt at 163 °. It is hardly soluble in water, difficult in dilute acid, lightly in warm alcohol and benzene.
2. 31,4 g i-p-Jodphenyl-2 ■ 3-dimethyl-5-pyrazolon (vgl. Journ. f. pr. Chemie N. F. 74 [1906], S. 315) werden in 100 ecm Chloroform gelöst. Unter Rühren und Kühlen mit kaltem Wasser läßt man eine Lösung von 16 g Brom in 10 ecm Chloroform langsam zufließen. Gegen Ende der Reaktion scheidet sich das Dibromid des i-p-Jodphenyl-2 · 3-dimethyl-5-pyrazolons kristallinisch aus. Zu diesem Gemenge läßt man unter fortwährendem Rühren eine Lösung2. 31.4 g of i-p-iodophenyl-2,3-dimethyl-5-pyrazolone (cf. Journ. f. pr. Chemie N.F. 74 [1906], p. 315) are dissolved in 100 ecm of chloroform solved. A solution of 16 g of bromine is left with stirring and cooling with cold water slowly flow in in 10 ecm chloroform. Towards the end of the reaction, the dibromide separates of i-p-iodophenyl-2 · 3-dimethyl-5-pyrazolone crystalline out. Allows for this mixture a solution with continued stirring
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE254487C true DE254487C (en) |
Family
ID=512672
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT254487D Active DE254487C (en) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE254487C (en) |
-
0
- DE DENDAT254487D patent/DE254487C/de active Active
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