BE524386A - - Google Patents
Info
- Publication number
- BE524386A BE524386A BE524386DA BE524386A BE 524386 A BE524386 A BE 524386A BE 524386D A BE524386D A BE 524386DA BE 524386 A BE524386 A BE 524386A
- Authority
- BE
- Belgium
- Prior art keywords
- penicillin
- dibenzylamine
- salt
- reacted
- solution
- Prior art date
Links
- 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 26
- BWLUMTFWVZZZND-UHFFFAOYSA-N Dibenzylamine Chemical compound C=1C=CC=CC=1CNCC1=CC=CC=C1 BWLUMTFWVZZZND-UHFFFAOYSA-N 0.000 claims description 24
- 150000003839 salts Chemical class 0.000 claims description 22
- 229930182555 Penicillin Natural products 0.000 claims description 21
- 229940049954 penicillin Drugs 0.000 claims description 20
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 239000003960 organic solvent Substances 0.000 claims description 5
- 229940056360 penicillin g Drugs 0.000 claims description 4
- AZCVBVRUYHKWHU-MBNYWOFBSA-N Penicillin X Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=C(O)C=C1 AZCVBVRUYHKWHU-MBNYWOFBSA-N 0.000 claims description 3
- AZCVBVRUYHKWHU-UHFFFAOYSA-N penicillin X Natural products O=C1N2C(C(O)=O)C(C)(C)SC2C1NC(=O)CC1=CC=C(O)C=C1 AZCVBVRUYHKWHU-UHFFFAOYSA-N 0.000 claims description 3
- 238000000034 method Methods 0.000 claims 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 6
- 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 description 5
- 239000002244 precipitate Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- -1 PENICILLIN DIBENZYLAMINE SALTS Chemical class 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 150000002960 penicillins Chemical class 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- OZXIZRZFGJZWBF-UHFFFAOYSA-N 1,3,5-trimethyl-2-(2,4,6-trimethylphenoxy)benzene Chemical compound CC1=CC(C)=CC(C)=C1OC1=C(C)C=C(C)C=C1C OZXIZRZFGJZWBF-UHFFFAOYSA-N 0.000 description 1
- CPIVYSAVIPTCCX-UHFFFAOYSA-N 4-methylpentan-2-yl acetate Chemical compound CC(C)CC(C)OC(C)=O CPIVYSAVIPTCCX-UHFFFAOYSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 229940072049 amyl acetate Drugs 0.000 description 1
- PGMYKACGEOXYJE-UHFFFAOYSA-N anhydrous amyl acetate Natural products CCCCCOC(C)=O PGMYKACGEOXYJE-UHFFFAOYSA-N 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- MNWFXJYAOYHMED-UHFFFAOYSA-M heptanoate Chemical compound CCCCCCC([O-])=O MNWFXJYAOYHMED-UHFFFAOYSA-M 0.000 description 1
- SHOJXDKTYKFBRD-UHFFFAOYSA-N mesityl oxide Natural products CC(C)=CC(C)=O SHOJXDKTYKFBRD-UHFFFAOYSA-N 0.000 description 1
- RXTNIJMLAQNTEG-UHFFFAOYSA-N methylamyl acetate Natural products CCCCC(C)OC(C)=O RXTNIJMLAQNTEG-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- QEUMNQFVAMSSNS-UHFFFAOYSA-N n-benzyl-1-phenylmethanamine;hydrochloride Chemical compound [Cl-].C=1C=CC=CC=1C[NH2+]CC1=CC=CC=C1 QEUMNQFVAMSSNS-UHFFFAOYSA-N 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 239000002904 solvent Substances 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
<Desc/Clms Page number 1>
BRISTOL LABORATORIES INC., résidant à NEW YORK.
SELS DE DIBENZYLAMINE DE PENICILLINE.
La présente invention concerne un nouveau sel d'amine de pénicil- line susceptible d'exercer une action antibiotique de réserve.
Le nouveau sel- de pénicilline de l'invention présente la formu- le suivante :
EMI1.1
où Pen désigne un radical acide de pénicilline ou sa partie active, suscep- tible de former un sel d'addition avéc la dibenzylamine.
L'invention sera mieux comprise en se reportant aux exemples ci-après.
EXEMPLE 1. -
On ajoute 2,3 cm3 de HG1 1 N à 0,66 g de dibenzylamine dans 10 cm3 d'eau, de. façon à former une mole du chlorhydrate d'addition de la di- benzylamine. On ajoute alors 1,32 gr de pénicilline sodique à 40 cm3 d'eau pour obtenir une solution de 51.550 unités par cm3 de pénicilline sodique.
La solution aqueuse de chlorhydrate de dibenzylamine est ajoutée à la solu- tion aqueuse de pénicilline sodique et il se forme immédiatement 1,62 g d'un précipité cristallin blanc ayant une activité de 713 unités par mg. Rende- ment : 2,0 g.
<Desc/Clms Page number 2>
EXEMPLE 2. - On ajoute 0,19 g de dibenzylamine à 0,8 cm3 de HCl 1 N et 1 cm3 d'eau. A ce mélange, on ajoute 0,66 g de pénicilline sodique dans 20 cm3 d'eau. Par refroidissement, il se forme immédiatement un précipité blanc.
On sépare ce précipité par filtration et on le sèche par le vide, obtenant ainsi le sel cristallin de dibenzylamine-pnicilline ayant une activité de 1075 unités par mg.
EXEMPLE 3. -
On ajoute à 0,66 g de dibenzylamine dissous dans l'éther une so- lution séchée dans l'éther d'une quantité de pénicilline acide obtenue à ; partir de 1,32 g de pénicilline sodique. On obtient immédiatement un préci- pité cristallin blanc de dibenzylamine-pénicilline. Le précipité est séparé par filtration et séché par le vide avec un rendement de 1,8 g. Activité 1190 unités par mg.
Bien entendu, le terme pénicilline utilisé ci+dessus s'applique aux pénicillines naturelles comme la pénicilline G, F, dihydro F, X, et K par exemple, et également aux pénicillines synthétiques décrites par exem- ple dans la demande de brevet anglais N 1430.
On notera également que la réaction peut s'effectuer dans des solvants organiques autres que l'éther. Des exemples de ces solvants sont le butanol, le propanol, l'acétate d'amyle, le méthyl-amyl-acétate, l'éther d'isopropyle, l'oxyde de mésityle et la méthyl-isobutyl-céton.ew
Diverses modifications peuvent etre apportées aux exemples cités sans s'écarter de l'invention. Ces exemples ne sont donnés qu'à titre d'illustration et ne limitent pas l'invention.
REVENDICATIONS.
1. - A titre de produit industriel nouveau, un sel de pénicilli- ne et de dibenzylamine.
2. - A titre de produit industriel nouveau, un sel de pénicilli- ne G et de dibenzylamine.
3- - A titre de produit industriel nouveau, un sel de pénicilli- ne X et de dibenzylamine.
4. - A titre de produit industriel nouveau, un sel de pénicilli- ne dihydro F et de dibenzylamine.
5. - Procédé de préparation d'un sel de pénicilline et de dibe. zylamine, caractérisé en ce qu'on fait réagir un sel soluble de pénicilline avec la dibenzylamine en solution aqueuse.
6. - Procédé de préparation d'un sel de pénicilline et de diben- zylamine, caractérisé en ce qu'on fait réagir un sel soluble de pénicilline avec la dibenzylamine en solution dans un solvant organique.
7. - Procédé de préparation d'un sel de pénicilline G et de di- benzylamine, caractérisé en ce qu'on fait réagir un sel soluble de pénicil- line avec la dibenzylamine en solution aqueuse.
8.- Procédé de préparation d'un sel de pénicilline X et de dibenzylamine, caractérisé en ce qu'on fait réagir un sel soluble de péni- cilline avec la dibenzylamine en solution aqueuse.
9.- Procédé de préparation d'un sel de pénicilline dihydro F et de dibenzylamine, caractérisé en ce qu'on fait réagir un sel soluble de pénicilline avec la dibenzylamine en solution aqueuse.
**ATTENTION** fin du champ DESC peut contenir debut de CLMS **.
<Desc / Clms Page number 1>
BRISTOL LABORATORIES INC., Residing in NEW YORK.
PENICILLIN DIBENZYLAMINE SALTS.
The present invention relates to a novel amine salt of penicillin capable of exerting a reserve antibiotic action.
The novel penicillin salt of the invention has the following formula:
EMI1.1
where Pen denotes an acid radical of penicillin or its active part, capable of forming an addition salt with dibenzylamine.
The invention will be better understood by referring to the examples below.
EXAMPLE 1. -
2.3 cm3 of 1N HG1 are added to 0.66 g of dibenzylamine in 10 cm3 of water, of. so as to form one mole of the di-benzylamine addition hydrochloride. 1.32 g of sodium penicillin are then added to 40 cm3 of water to obtain a solution of 51,550 units per cm3 of sodium penicillin.
The aqueous solution of dibenzylamine hydrochloride is added to the aqueous solution of penicillin sodium and immediately 1.62 g of a white crystalline precipitate formed having an activity of 713 units per mg. Yield: 2.0 g.
<Desc / Clms Page number 2>
EXAMPLE 2. 0.19 g of dibenzylamine is added to 0.8 cm3 of 1N HCl and 1 cm3 of water. To this mixture, 0.66 g of sodium penicillin in 20 cm3 of water is added. On cooling, a white precipitate immediately forms.
This precipitate is filtered off and dried in vacuo, thereby obtaining the crystalline salt of dibenzylamine-pnicillin having an activity of 1075 units per mg.
EXAMPLE 3. -
To 0.66 g of dibenzylamine dissolved in ether is added a dried solution in ether of an amount of acidic penicillin obtained at; from 1.32 g of sodium penicillin. A white crystalline precipitate of dibenzylamine-penicillin is immediately obtained. The precipitate is filtered off and dried in vacuo with a yield of 1.8 g. Activity 1190 units per mg.
Of course, the term penicillin used above applies to natural penicillins such as penicillin G, F, dihydro F, X, and K for example, and also to synthetic penicillins described for example in the British patent application N 1430.
It will also be noted that the reaction can be carried out in organic solvents other than ether. Examples of such solvents are butanol, propanol, amyl acetate, methyl-amyl-acetate, isopropyl ether, mesityl oxide, and methyl-isobutyl-keton.
Various modifications can be made to the cited examples without departing from the invention. These examples are given only by way of illustration and do not limit the invention.
CLAIMS.
1. - As a new industrial product, a salt of penicillin and dibenzylamine.
2. - As a new industrial product, a salt of penicillin G and dibenzylamine.
3- - As a new industrial product, a salt of penicillin X and dibenzylamine.
4. - As a new industrial product, a salt of penicillin dihydro F and dibenzylamine.
5. - Process for preparing a salt of penicillin and dibe. zylamine, characterized in that a soluble salt of penicillin is reacted with dibenzylamine in aqueous solution.
6. - Process for preparing a salt of penicillin and dibenzylamine, characterized in that a soluble salt of penicillin is reacted with dibenzylamine in solution in an organic solvent.
7. - Process for preparing a salt of penicillin G and dibenzylamine, characterized in that a soluble salt of penicillin is reacted with dibenzylamine in aqueous solution.
8. A process for preparing a salt of penicillin X and of dibenzylamine, characterized in that a soluble salt of penicillin is reacted with dibenzylamine in aqueous solution.
9. A process for preparing a salt of dihydro F penicillin and dibenzylamine, characterized in that a soluble salt of penicillin is reacted with dibenzylamine in aqueous solution.
** ATTENTION ** end of DESC field can contain start of CLMS **.
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BE524386A true BE524386A (en) |
Family
ID=159020
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BE524386D BE524386A (en) |
Country Status (1)
| Country | Link |
|---|---|
| BE (1) | BE524386A (en) |
-
0
- BE BE524386D patent/BE524386A/fr unknown
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