DE222809C - - Google Patents
Info
- Publication number
- DE222809C DE222809C DENDAT222809D DE222809DA DE222809C DE 222809 C DE222809 C DE 222809C DE NDAT222809 D DENDAT222809 D DE NDAT222809D DE 222809D A DE222809D A DE 222809DA DE 222809 C DE222809 C DE 222809C
- Authority
- DE
- Germany
- Prior art keywords
- parts
- acid
- chloride
- propionic acids
- reaction
- 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
- 150000001408 amides Chemical class 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- 150000004672 propanoic acids Chemical class 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- GWYFCOCPABKNJV-UHFFFAOYSA-N 3-Methylbutanoic acid Chemical class CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- NOOLISFMXDJSKH-UTLUCORTSA-N (+)-Neomenthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@@H]1O NOOLISFMXDJSKH-UTLUCORTSA-N 0.000 description 1
- VUAXHMVRKOTJKP-UHFFFAOYSA-N 2,2-dimethylbutyric acid Chemical compound CCC(C)(C)C(O)=O VUAXHMVRKOTJKP-UHFFFAOYSA-N 0.000 description 1
- GWYFCOCPABKNJV-UHFFFAOYSA-M 3-Methylbutanoic acid Natural products CC(C)CC([O-])=O GWYFCOCPABKNJV-UHFFFAOYSA-M 0.000 description 1
- ZAGGRKWDTCOZRM-UHFFFAOYSA-N 3-ethylpentanoyl chloride Chemical compound CCC(CC)CC(Cl)=O ZAGGRKWDTCOZRM-UHFFFAOYSA-N 0.000 description 1
- 229960004873 LEVOMENTHOL Drugs 0.000 description 1
- 229940041616 Menthol Drugs 0.000 description 1
- 150000007945 N-acyl ureas Chemical class 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N Phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 1
- 241000490025 Schefflera digitata Species 0.000 description 1
- 210000002784 Stomach Anatomy 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 230000036528 appetite Effects 0.000 description 1
- 235000019789 appetite Nutrition 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 235000015250 liver sausages Nutrition 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L na2so4 Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 230000001264 neutralization Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 230000001624 sedative Effects 0.000 description 1
- 239000000932 sedative agent Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 230000001225 therapeutic Effects 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C275/46—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups containing any of the groups, X being a hetero atom, Y being any atom, e.g. acylureas
- C07C275/48—Y being a hydrogen or a carbon atom
- C07C275/50—Y being a hydrogen or an acyclic carbon atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
Es wurde gefunden, daß die Derivate der ß-ß-dialkylierten Propionsäuren der Formel:It has been found that the derivatives of the ß-ß-dialkylated propionic acids of the formula:
H-C H2-COOHHC H 2 -COOH
(R1 bedeutet Alkyl, R2 Alkyl mit Ausnahme von Methyl und Äthyl), wie Ester, Amide und Ureide wertvolle therapeutische Eigenschaften besitzen. Die neuen Körper sind fast geschmacklos. Da sie außerdem vom (R 1 denotes alkyl, R 2 denotes alkyl with the exception of methyl and ethyl), such as esters, amides and ursides, have valuable therapeutic properties. The new bodies are almost tasteless. Since they are also dated
ίο Magen sehr gut vertragen werden und den Appetit nicht beeinflussen, haben sich die neuen Produkte, als wertvolle Sedativa erwiesen. Sie besitzen die therapeutisch wertvollen . Eigenschaften der Isovaleriansäurederivate in erhöhtem Maße.ίο be tolerated very well and the stomach Do not affect appetite, the new products have proven to be valuable sedatives. You own the therapeutically valuable ones. Properties of the isovaleric acid derivatives in increased degree.
Zur Darstellung der neuen Verbindungen verfährt man in der Weise, daß man die ß-ß-dialkylierten Propionsäuren der obigen Formel in üblicher Weise in die Amide, Harnstoffverbindungeri oder Ester überführt.To represent the new connections one proceeds in such a way that one uses the ß-ß-dialkylated propionic acids of the above formula in the usual way into the amides, urea compounds or ester converted.
Zu 130 Teilen ß-ß-Diäthylpropionsäure läßt man langsam 150 Teile Phosphortrichlorid zutropfen und erwärmt das Gemisch 3 bis 4 Stunden auf dem Wasserbad. Durch fraktionierte Destillation wird das Chlorid isoliert. Es siedet bei 150 bis 155 °.Leaves to 130 parts of ß-ß-diethylpropionic acid 150 parts of phosphorus trichloride are slowly added dropwise and the mixture is heated to 3 to 4 hours on the water bath. The chloride is isolated by fractional distillation. It boils at 150 to 155 °.
Zur Darstellung des Säureamids werden 150 Teile des Chlorids zu einem Überschuß von kaltem wäßrigem Ammoniak zugefügt und das abgeschiedene Amid isoliert und aus Benzol umkristallisiert. Schmelzpunkt 127,5°.To prepare the acid amide, 150 parts of the chloride are used in excess added by cold aqueous ammonia and the deposited amide isolated and removed Benzene recrystallized. Melting point 127.5 °.
Beispiel 2. „,Example 2. ",
150 Teile ß-ß-Diäthylpropionylchlorid werden mit 170 Teilen fein gepulvertem Harnstoff verrieben und das Gemisch nach beendeter Reaktion noch 2 bis 3 Stunden auf dem Wasserbade erwärmt. Man wäscht darauf das Reaktionsprodukt mit heißem Wasser und kristallisiert den so erhaltenen ß-ß-Diäthylpropionylharnstoff aus verdünntem Alkohol um. Schmelzpunkt 197 °.150 parts of ß-ß-diethylpropionyl chloride will be Triturated with 170 parts of finely powdered urea and the mixture after completion Reaction warmed on the water bath for another 2 to 3 hours. One washes on it the reaction product with hot water and crystallizes the ß-ß-diethylpropionylurea thus obtained from diluted alcohol. Melting point 197 °.
■D ■ ■ 1 ■ D ■ ■ 1
Zu 150 Teilen Menthol in 100 Teilen Pyridin werden unter Kühlung 150 Teile Diäthylpropionylchlorid zugegeben. Nach beendeter Reaktion nimmt man das Gemisch mit verdünnter Schwefelsäure auf, wäscht den Ester mit Wasser bis zur neutralen Reaktion und destilliert den ölig abgeschiedenen Ester nach dem Trocknen über Natriumsulfat im Vakuum. Er stellt eine wasserhelle Flüssigkeit dar, die bei 155 ° und 12 mm siedet.To 150 parts of menthol in 100 parts of pyridine 150 parts of diethylpropionyl chloride are added with cooling. After finished In the reaction, the mixture is taken up with dilute sulfuric acid and the ester is washed with water until the reaction is neutral and the oily ester which has separated out is re-distilled drying over sodium sulfate in vacuo. It represents a water-white liquid that boils at 155 ° and 12 mm.
Pate ν τ-Α ν SPRU c η :Pate ν τ-Α ν SPRU c η:
Verfahren zur Darstellung von Derivaten der ß-ß-dialkylierten Propionsäuren (mit Ausnahme der Isovaleriansäure und der Methyläthylpropionsäure), darin bestehend, daß man diese substituierten Propionsäuren in ihre Ester, Amide oder Ureide überführt.Process for the preparation of derivatives of ß-ß-dialkylated propionic acids (with the exception of isovaleric acid and methylethylpropionic acid), consisting of that one converts these substituted propionic acids into their esters, amides or ureides.
BERLIN. '-'GEDRUCKT IN DER REICHSDRUCKERIiI.BERLIN. '-'PRINTED IN THE REICHSDRUCKERIiI.
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE222809C true DE222809C (en) |
Family
ID=483671
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT222809D Active DE222809C (en) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE222809C (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0005422A2 (en) * | 1978-05-03 | 1979-11-14 | Sanofi S.A. | Derivatives of omega-dialkylalkanoic acids, processes for their preparation and their therapeutical use |
-
0
- DE DENDAT222809D patent/DE222809C/de active Active
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0005422A2 (en) * | 1978-05-03 | 1979-11-14 | Sanofi S.A. | Derivatives of omega-dialkylalkanoic acids, processes for their preparation and their therapeutical use |
| EP0005422A3 (en) * | 1978-05-03 | 1979-12-12 | Sanofi, Societe Anonyme | Derivatives of omega-dialkylalkanoic acids, processes for their preparation and their therapeutical use |
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