CH304880A - Process for the production of a sparingly soluble penicillin compound. - Google Patents
Process for the production of a sparingly soluble penicillin compound.Info
- Publication number
- CH304880A CH304880A CH304880DA CH304880A CH 304880 A CH304880 A CH 304880A CH 304880D A CH304880D A CH 304880DA CH 304880 A CH304880 A CH 304880A
- Authority
- CH
- Switzerland
- Prior art keywords
- production
- sparingly soluble
- penicillin
- compound
- penicillin compound
- Prior art date
Links
- 229930182555 Penicillin Natural products 0.000 title claims description 6
- 229940049954 penicillin Drugs 0.000 title claims description 6
- 238000000034 method Methods 0.000 title claims description 4
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- -1 penicillin compound Chemical class 0.000 title claims description 3
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 claims description 7
- 150000001875 compounds Chemical class 0.000 claims description 3
- 238000000354 decomposition reaction Methods 0.000 claims description 3
- 150000001447 alkali salts Chemical class 0.000 claims description 2
- 239000000155 melt Substances 0.000 claims description 2
- 229940056360 penicillin g Drugs 0.000 claims description 2
- XRSQZFJLEPBPOZ-UHFFFAOYSA-N 4-amino-2-methylbenzoic acid Chemical compound CC1=CC(N)=CC=C1C(O)=O XRSQZFJLEPBPOZ-UHFFFAOYSA-N 0.000 claims 1
- 125000004494 ethyl ester group Chemical group 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- KZDCMKVLEYCGQX-UDPGNSCCSA-N 2-(diethylamino)ethyl 4-aminobenzoate;(2s,5r,6r)-3,3-dimethyl-7-oxo-6-[(2-phenylacetyl)amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid;hydrate Chemical compound O.CCN(CC)CCOC(=O)C1=CC=C(N)C=C1.N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 KZDCMKVLEYCGQX-UDPGNSCCSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 210000001124 body fluid Anatomy 0.000 description 1
- 239000010839 body fluid Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 239000003405 delayed action preparation Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical class CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D499/00—Heterocyclic compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. penicillins, penems; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
verfahren zur Herstellung einer schwerlöslichen Penicillinverbindung.- Das Procainsalz des Penicillins zeichnet sich durch eine protrahierte Wirkung aus und findet in der Therapie als Depotpräparat breiteste Anwendung. Der Penicillinspiegel im Blut hält im Durchschnitt etwa 20 Std.
vor und ist durch die Löslichkeit des Procain- penicillins in der Körperflüssigkeit bedingt.
Gegenstand des vorliegenden Patentes ist ein Verfahren zur Herstellung einer schwer löslichen Penieililinverbindung, das dadurch gekennzeichnet ist, dass man. 2-Methyl4 aminobenzoesäu:rediäthylaminäthylester-chlor- hydrat mit einem Alkalisalz von Penicillin G umsetzt.
Die neue kristalline Verbindung schmilzt unter Zersetzung bei 130 und soll als Depot penicillin dienen. <I>Beispiel:</I> 2,87 g 2-Methyl-4-aminobenzoesäurediäthyl- aminäthylester-chlorhydrat werden in 10 em3 Wasser gelöst,. und eine Lösung von 3,56 g Penieülin-G-Natrium in 12 cm3 Wasser wird hinzugefügt.
Beim Anreiben setzt spontane Kristallisation ein. Das in Prismen kristalli- sierende Salz wird abgesaugt, mit kaltem Wasser nachgewaschen und im. Exsiccator ge trocknet. Schmelzpunkt unter Zersetzung: 130 ; die Ausbeute beträgt 92%.
process for the production of a sparingly soluble penicillin compound.- The procaine salt of penicillin is characterized by a protracted effect and is widely used in therapy as a depot preparation. The penicillin level in the blood lasts about 20 hours on average.
and is due to the solubility of procaine penicillin in the body fluid.
The present patent relates to a process for the preparation of a poorly soluble penieililin compound, which is characterized in that one. 2-Methyl4 aminobenzoesäu: rediethylamineethyl ester chlorohydrate with an alkali salt of penicillin G is reacted.
The new crystalline compound melts with decomposition at 130 and is intended to serve as a depot penicillin. <I> Example: </I> 2.87 g of 2-methyl-4-aminobenzoic acid diethyl amine ethyl ester chlorohydrate are dissolved in 10 cubic meters of water. and a solution of 3.56 g of Penilin G sodium in 12 cm3 of water is added.
Spontaneous crystallization sets in when rubbed. The salt, which crystallizes in prisms, is sucked off, washed with cold water and im. Desiccator dried. Melting point with decomposition: 130; the yield is 92%.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE304880X | 1951-03-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH304880A true CH304880A (en) | 1955-01-31 |
Family
ID=6120153
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH304880D CH304880A (en) | 1951-03-30 | 1952-02-19 | Process for the production of a sparingly soluble penicillin compound. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH304880A (en) |
-
1952
- 1952-02-19 CH CH304880D patent/CH304880A/en unknown
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