CH280370A - Process for the preparation of a substance which lowers the level of prothrombin in the blood. - Google Patents
Process for the preparation of a substance which lowers the level of prothrombin in the blood.Info
- Publication number
- CH280370A CH280370A CH280370DA CH280370A CH 280370 A CH280370 A CH 280370A CH 280370D A CH280370D A CH 280370DA CH 280370 A CH280370 A CH 280370A
- Authority
- CH
- Switzerland
- Prior art keywords
- lowers
- blood
- substance
- prothrombin
- level
- Prior art date
Links
- 102100027378 Prothrombin Human genes 0.000 title claims description 4
- 108010094028 Prothrombin Proteins 0.000 title claims description 4
- 239000008280 blood Substances 0.000 title claims description 4
- 210000004369 blood Anatomy 0.000 title claims description 4
- 238000000034 method Methods 0.000 title claims description 4
- 229940039716 prothrombin Drugs 0.000 title claims description 4
- 239000000126 substance Substances 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 3
- 238000002844 melting Methods 0.000 claims description 3
- 230000008018 melting Effects 0.000 claims description 3
- OYQPQLGDSALAQP-UHFFFAOYSA-N 2-(4-hydroxy-2-oxochromen-3-yl)acetic acid Chemical compound C1=CC=C2OC(=O)C(CC(=O)O)=C(O)C2=C1 OYQPQLGDSALAQP-UHFFFAOYSA-N 0.000 claims description 2
- 239000013078 crystal Substances 0.000 claims description 2
- 239000012024 dehydrating agents Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 238000010992 reflux Methods 0.000 claims description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 2
- 239000003960 organic solvent Substances 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- ORHBXUUXSCNDEV-UHFFFAOYSA-N umbelliferone Chemical group C1=CC(=O)OC2=CC(O)=CC=C21 ORHBXUUXSCNDEV-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/42—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms in positions 2 and 4
- C07D311/44—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms in positions 2 and 4 with one hydrogen atom in position 3
- C07D311/46—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms in positions 2 and 4 with one hydrogen atom in position 3 unsubstituted in the carbocyclic ring
- C07D311/48—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms in positions 2 and 4 with one hydrogen atom in position 3 unsubstituted in the carbocyclic ring with two such benzopyran radicals linked together by a carbon chain
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung einer das Prothrombinniveau im Blut herabsetzenden Substanz. Gegenstand der Erfindung ist ein Verfah ren zur Herstellung einer das Prothrombin- niveau im Blut herabsetzenden Substanz, wel- ehes dadurch gekennzeichnet ist, dass eine Ver bindung der Formel
EMI0001.0006
mit einer Verbindung der Formel (CFI3)2CH . Y, wobei X und Y reaktionsfähige, bei der Reak tion mit Ausnahme eines in einem von ihnen enthaltenen Sauerstoffatoms sieh abspaltende Reste bedeuten, umgesetzt wird.
Der so erhal tene Bis- (4-oxy-cumarinyl)-essigsäure-isopro- pylester bildet farblose, in Wasser unlösliche Kristalle vom Schmelzpunkt 204 bis 205 C.
Die Einführung der Isopropylgruppe ohne gleichzeitige Veresterung der Hydroxylgrup- pen in den Oxycumarinresten erfolgt zweck mässig durch Behandlung der Carbonsäure mit Isopropanol in Gegenwart eines wasserentzie henden Mittels, wie von trockenem Chlorwas serstoff oder konzentrierter Schwefelsäure. <I>Beispiel:</I> 70 g Bis- (4-oxy-cumarinyl)-essigsäure wur den in 600 em3 3n-isopropanolischer Salzsäure suspendiert und unter Umrühren etwa fünf Stunden am Rückflusskühler erhitzt.
Der nach Abkühlung des Reaktionsgutes auskristalli sierte Ester wurde abgesaugt, mit Äther aus gewaschen und getrocknet; Ausbeute 62 g. Nach Umkristallisieren aus Aceton zeigte das gereinigte Produkt den Schmelzpunkt 204 bis 205 C.
Process for the preparation of a substance which lowers the level of prothrombin in the blood. The subject matter of the invention is a method for producing a substance which lowers the prothrombin level in the blood, which is characterized in that a compound of the formula
EMI0001.0006
with a compound of the formula (CFI3) 2CH. Y, where X and Y are reactive, in the reaction with the exception of an oxygen atom contained in one of them means separating radicals, is implemented.
The bis (4-oxy-coumarinyl) -acetic acid isopropyl ester obtained in this way forms colorless, water-insoluble crystals with a melting point of 204 to 205 C.
The introduction of the isopropyl group without simultaneous esterification of the hydroxyl groups in the oxycoumarin residues is expediently carried out by treating the carboxylic acid with isopropanol in the presence of a dehydrating agent such as dry hydrogen chloride or concentrated sulfuric acid. <I> Example: </I> 70 g of bis- (4-oxy-coumarinyl) -acetic acid were suspended in 600 cubic meters of 3N-isopropanolic hydrochloric acid and heated on the reflux condenser for about five hours while stirring.
The ester crystallized out after the reaction mixture had cooled down was filtered off with suction, washed off with ether and dried; Yield 62g. After recrystallization from acetone, the purified product had a melting point of 204 to 205 C.
Claims (1)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS2482512X | 1946-08-31 | ||
| CH280370T | 1946-11-06 | ||
| GB3687646A GB632805A (en) | 1946-12-13 | 1946-12-13 | Process for the production of compounds reducing the prothrombin level in the blood |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH280370A true CH280370A (en) | 1952-01-15 |
Family
ID=32233754
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH280370D CH280370A (en) | 1946-08-31 | 1946-11-06 | Process for the preparation of a substance which lowers the level of prothrombin in the blood. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH280370A (en) |
-
1946
- 1946-11-06 CH CH280370D patent/CH280370A/en unknown
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