DE185962C - - Google Patents
Info
- Publication number
- DE185962C DE185962C DENDAT185962D DE185962DA DE185962C DE 185962 C DE185962 C DE 185962C DE NDAT185962 D DENDAT185962 D DE NDAT185962D DE 185962D A DE185962D A DE 185962DA DE 185962 C DE185962 C DE 185962C
- Authority
- DE
- Germany
- Prior art keywords
- urea
- bromoisovalerianyl
- bromide
- chloride
- acid
- 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
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 10
- 239000004202 carbamide Substances 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 4
- UEBARDWJXBGYEJ-UHFFFAOYSA-N 2-bromo-3-methylbutanoic acid Chemical compound CC(C)C(Br)C(O)=O UEBARDWJXBGYEJ-UHFFFAOYSA-N 0.000 description 3
- HFAUMPWMNPYULN-UHFFFAOYSA-N 2-bromo-3-methylbutanoyl bromide Chemical compound CC(C)C(Br)C(Br)=O HFAUMPWMNPYULN-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M NaHCO3 Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 235000013832 Valeriana officinalis Nutrition 0.000 description 2
- 240000006745 Valeriana officinalis Species 0.000 description 2
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N Valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 235000016788 valerian Nutrition 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- MVYUMPZRKNBHOP-UHFFFAOYSA-N 2-bromo-3-methylbutanoyl chloride Chemical compound CC(C)C(Br)C(Cl)=O MVYUMPZRKNBHOP-UHFFFAOYSA-N 0.000 description 1
- CMCCHHWTTBEZNM-UHFFFAOYSA-N 2-bromo-N-carbamoyl-3-methylbutanamide Chemical compound CC(C)C(Br)C(=O)NC(N)=O CMCCHHWTTBEZNM-UHFFFAOYSA-N 0.000 description 1
- ISULZYQDGYXDFW-UHFFFAOYSA-N 3-methylbutanoyl chloride Chemical compound CC(C)CC(Cl)=O ISULZYQDGYXDFW-UHFFFAOYSA-N 0.000 description 1
- FTOAOBMCPZCFFF-UHFFFAOYSA-N Barbital Chemical compound CCC1(CC)C(=O)NC(=O)NC1=O FTOAOBMCPZCFFF-UHFFFAOYSA-N 0.000 description 1
- 229960002319 Barbital Drugs 0.000 description 1
- 206010022437 Insomnia Diseases 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
- BZRZRAJFBZQJRU-UHFFFAOYSA-N N-bromo-N-carbamoyl-3-methylbutanamide Chemical compound CC(C)CC(=O)N(Br)C(N)=O BZRZRAJFBZQJRU-UHFFFAOYSA-N 0.000 description 1
- CESKLHVYGRFMFP-UHFFFAOYSA-N Sulfonmethane Chemical compound CCS(=O)(=O)C(C)(C)S(=O)(=O)CC CESKLHVYGRFMFP-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229960005181 morphine Drugs 0.000 description 1
- 229930014694 morphine Natural products 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 231100000486 side effect Toxicity 0.000 description 1
- 230000035943 smell Effects 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 230000001225 therapeutic Effects 0.000 description 1
- 229940005605 valeric acid Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C273/00—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C273/18—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups of substituted ureas
- C07C273/1854—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups of substituted ureas by reactions not involving the formation of the N-C(O)-N- moiety
- C07C273/1863—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups of substituted ureas by reactions not involving the formation of the N-C(O)-N- moiety from urea
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
Die bis jetzt bekannten therapeutisch angewendeten Verbindungen der Valeriansäure und α-Bromisovaleriansäure, besonders deren dialkylierte Amide, haben ihre therapeutische Wirksamkeit nicht sowohl in der schlafmachenden Richtung als vielmehr in der Richtung der typischen Baldrianwirkung entfaltet (vergl. Kionka, Deutschemed. Wochenschrift 1901, S. 849, und D. R. P. 129967/12).The previously known therapeutically used compounds of valeric acid and α-bromoisovaleric acid, especially their Dialkylated amides do not have their therapeutic efficacy in both sleep-inducing Direction rather than in the direction of the typical valerian effect unfolded (cf. Kionka, Deutschemed. Wochenschrift 1901, p. 849, and D. R. P. 129967/12).
Es wurde nun gefunden, daß durch Festlegen der Carboxylgruppe in der Bromisovaleriansäure durch Harnstoff ein . in der Literatur bis jetzt noch nicht beschriebener neuer Körper erhalten wird, der frei von allen schädlichen Nebenwirkungen die Baldrianwirkung nicht mehr besitzt, sondern ein ausgezeichnetes Schlafmittel darstellt, das in allen denjenigen Fällen von Schlaflosigkeit ;: angewendet werden kann, deren Ursachen nicht körperliche Schmerzen, sondern nervöse Zustände sind, bei denen der Arzt gern von . den mehr oder weniger bedenklichen Schlafmitteln, wie Morphium, Sulfonal, Veronal usw., absieht. Der Bromisovalerianylharnstoff wird erhalten durch Einwirkung von Harnstoff auf α-Bromisovalerianylbromid oder a-Bromisovalerianylchlorid.It has now been found that by fixing the carboxyl group in the bromoisovaleric acid by urea. not yet described in the literature New body is obtained that is free from all the harmful side effects of the valerian effects no longer possesses, but is an excellent sleeping aid, which in all those cases of insomnia ;: Can be used if the cause is not physical pain, but nervous Are conditions that the doctor would like to hear from. the more or less questionable sleeping pills, such as morphine, sulfonal, veronal, etc., excludes. The bromoisovalerianylurea is obtained by the action of Urea on α-bromoisovalerianyl bromide or α-bromoisovalerianyl chloride.
Folgende Beispiele mögen das Verfahren erläutern:The following examples may explain the process:
i. 2 kg α-Bromisovalerianylbromid werden mit ι kg fein gepulvertem und gut getrocknetem Harnstoff innig vermischt. Es findet allmählich eine Lösung des Harnstoffes statt, und das Gemisch erwärmt sich von selbst bis auf ungefähr 70 °. Bei dieser Temperatur wird es einige Stunden gehalten, bis das Bromid nicht mehr durch Geruch wahrnehmbar ist. Dann wird die Masse mit Natriumbicarbonat behandelt, um etwa ent-, standene α - Bromisovaleriansäure und den Bromwasserstoff zu entfernen. Das zurückgebliebene Produkt wird getrocknet und aus Toluol oder Wasser umkristallisiert.i. 2 kg of α-bromoisovalerianyl bromide are finely powdered and well dried with ι kg Urea mixed intimately. The urea gradually dissolves, and the mixture heats up by itself to about 70 °. At this temperature it is held for a few hours until the bromide is no longer noticeable by smell is. Then the mass is treated with sodium bicarbonate in order to to remove the α - bromoisovaleric acid and the hydrogen bromide. The left behind Product is dried and recrystallized from toluene or water.
Der a-Bromisovalerianylharnstoff kristallisiert aus Toluol in Blättchen und schmilzt bei ungefähr 1490.The α-bromoisovalerianylurea crystallizes from toluene in flakes and melts at approximately 149 ° .
2. Zu 331 g Isovalerianylchlorid läßt man 480 g Brom hinzufließen und erhitzt dann auf dem Wasserbade so lange, bis die Farbe des Broms verschwunden ist. Hierauf unterwirft man die Flüssigkeit im Vakuum einer fraktionierten Destillation, wobei man bei 20 mm Druck und einer Temperatur von 90 bis iio° eine klare Flüssigkeit erhält, die das 0-Bromisovalerianylchlorid darstellt.2. 480 g of bromine are allowed to flow into 331 g of isovalerianyl chloride and then heated on the water bath until the color of the bromine has disappeared. Submit to this one the liquid in the vacuum of a fractional distillation, whereby one at 20 mm pressure and a temperature of 90 until a clear liquid is obtained which is the 0-bromoisovalerianyl chloride.
Mit diesem wird wie unter 1. weiter verfahren. Proceed with this as under 1.
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE185962C true DE185962C (en) |
Family
ID=449759
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT185962D Active DE185962C (en) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE185962C (en) |
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0
- DE DENDAT185962D patent/DE185962C/de active Active
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