GB748886A - Penicillin salts of diphenylamides - Google Patents
Penicillin salts of diphenylamidesInfo
- Publication number
- GB748886A GB748886A GB4599/53A GB459953A GB748886A GB 748886 A GB748886 A GB 748886A GB 4599/53 A GB4599/53 A GB 4599/53A GB 459953 A GB459953 A GB 459953A GB 748886 A GB748886 A GB 748886A
- Authority
- GB
- United Kingdom
- Prior art keywords
- penicillin
- base
- salt
- solution
- acetic 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.)
- Expired
Links
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical class C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 title abstract 4
- 150000002960 penicillins Chemical class 0.000 title abstract 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 abstract 6
- 239000000243 solution Substances 0.000 abstract 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 4
- 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 abstract 4
- 150000003839 salts Chemical class 0.000 abstract 4
- 229930182555 Penicillin Natural products 0.000 abstract 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 abstract 3
- 229940049954 penicillin Drugs 0.000 abstract 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 abstract 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 abstract 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 abstract 1
- 239000007864 aqueous solution Substances 0.000 abstract 1
- FCPVYOBCFFNJFS-LQDWTQKMSA-M benzylpenicillin sodium Chemical compound [Na+].N([C@H]1[C@H]2SC([C@@H](N2C1=O)C([O-])=O)(C)C)C(=O)CC1=CC=CC=C1 FCPVYOBCFFNJFS-LQDWTQKMSA-M 0.000 abstract 1
- 239000003610 charcoal Substances 0.000 abstract 1
- 239000000284 extract Substances 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- JEFJSEIUEJBMSR-UHFFFAOYSA-N hydron;n-phenylaniline;chloride Chemical compound Cl.C=1C=CC=CC=1NC1=CC=CC=C1 JEFJSEIUEJBMSR-UHFFFAOYSA-N 0.000 abstract 1
- 238000001556 precipitation Methods 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 238000000746 purification Methods 0.000 abstract 1
- 238000001953 recrystallisation Methods 0.000 abstract 1
- 238000010992 reflux Methods 0.000 abstract 1
- 229910000029 sodium carbonate Inorganic materials 0.000 abstract 1
- 159000000000 sodium salts Chemical class 0.000 abstract 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)
Abstract
An injectable penicillin salt having a depot action is produced by reacting penicillin, or a salt thereof, with a base of general formula <f/1> wherein R1 is hydrogen or alkyl of 1-3 C atoms; R2 alkyl of up to 3 C atoms; or <FORM:0748886/IV(a)/1> is a heterocyclic radical; or a salt of such a base. The salts are reacted in aqueous solution; the acid and base in organic solution, e.g. in ethyl acetate solution. Examples illustrate the preparation of the penicillin G salt of (a) o -pyrrolidino acetic acid diphenylamide, (b) o -diethylamino-acetic acid diphenylamide, and (c) o -n-propylamino-acetic acid diphenylamide. The salts used are the sodium salt of penicillin and the hydrochloride of the base. Penicillin per se is obtained by adding phosphoric acid to a solution of sodium penicillin to a pH 2.0 and extracting with ethyl acetate. o -Pyrrolidino-acetic acid diphenylamide hydrochloride is prepared by refluxing o -chloracetic acid diphenylamide and pyrrolidine in benzene, decanting, adding ether to the benzene solution and extracting with hydrochloric acid. Further purification involves precipitation of the base by adding sodium carbonate to the extracts, treatment of an ether solution of the base with charcoal and recrystallization of the hydrochloride from acetone.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE748886X | 1952-02-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB748886A true GB748886A (en) | 1956-05-16 |
Family
ID=6649104
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB4599/53A Expired GB748886A (en) | 1952-02-18 | 1953-02-18 | Penicillin salts of diphenylamides |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB748886A (en) |
-
1953
- 1953-02-18 GB GB4599/53A patent/GB748886A/en not_active Expired
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