BE862630A - NEW PHTHALIMIDO-SULFAMIDES AND PROCESS FOR THEIR PREPARATION - Google Patents
NEW PHTHALIMIDO-SULFAMIDES AND PROCESS FOR THEIR PREPARATIONInfo
- Publication number
- BE862630A BE862630A BE184096A BE184096A BE862630A BE 862630 A BE862630 A BE 862630A BE 184096 A BE184096 A BE 184096A BE 184096 A BE184096 A BE 184096A BE 862630 A BE862630 A BE 862630A
- Authority
- BE
- Belgium
- Prior art keywords
- emi
- preparation
- phthalimido
- new
- mono
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
- C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
- C07D261/10—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D261/14—Nitrogen atoms
- C07D261/16—Benzene-sulfonamido isoxazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/36—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems
- C07D241/38—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems with only hydrogen or carbon atoms directly attached to the ring nitrogen atoms
- C07D241/40—Benzopyrazines
- C07D241/44—Benzopyrazines with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the hetero ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Indole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
Nouveaux phtalimido-sulfamides et
procédé pour leur préparation La présente invention concerne de nouveaux dérivés de sulfamides et un procédé pour leur préparation.
Les nouveaux dérivés de l'invention répondent
à la formule de structure générale
<EMI ID=1.1>
<EMI ID=2.1>
molécule de sulfamide de l'une des formules
<EMI ID=3.1>
<EMI ID=4.1>
Ces nouveaux dérivés peuvent être préparés en faisant réagir l'anhydride phtalique en milieu basique,
<EMI ID=5.1>
Dans le premier cas, on obtient le mono-phtalimide de la sulfaquinoxaline de la formule
<EMI ID=6.1>
dans le deuxième cas, le mono-phtalimide du sulfamétoxazole de la formule
<EMI ID=7.1>
La préparation des nouveaux dérivés de l'invention est illustrée par les exemples non limitatifs de modes de réalisation ci-après.
Exemple 1
Préparation du monophtalimide de sulfaquinoxaline Dans un erlenmeyer avec agitateur mécanique,
on introduit 75 ml d'eau et 13 g (43,3 idoles) de sulfaquinoxaline, on y ajoute une solution aqueuse à 48% d'hydroxyde de sodium jusqu'au pH de 10,7, puis par petites portions
un total de 6,75 g (45,6 mmoles) d'anhydride phtalique pulvérulent, le pH étant maintenu au voisinage de 9,4.
Après addition complète de l'anhydride phtalique,
on agite le mélange réactionnel pendant 2 heures en ajoutant
<EMI ID=8.1>
de sodium suffisante pour maintenir le pH entre 8 et 9,4.
Après filtration de la solution réactionnelle
<EMI ID=9.1> avec de l'acide chlorhydrique concentré au pH de 5, puis avec de l'acide acétique jusqu'au pH de 3.
<EMI ID=10.1>
et lavé à l'eau jusqu'à neutralité. Par séchage à 4[deg.]C sous vide, on obtient 17,3 g d'un produit solide, qui est
<EMI ID=11.1>
est chauffée à reflux pendant 2 heures, puis filtrée et
<EMI ID=12.1>
Le précipité, qui se forme au refroidissement, est séparé par filtration, lavé à l'acétate d'éthyle et séché sous vide. On obtient 10 g, soit 51% du rendement théorique, du composé indiqué en tête, d'un point de fusion
de 191-192[deg.]C (avec décomposition).
Analyse :
<EMI ID=13.1>
Exemple 2
Préparation du mono-phtalimide du sulfaméthoxazole
<EMI ID=14.1>
solution aqueuse à 48% d'hydroxyde de sodium, puis ajoute par petites portions et en maintenant le pH à 9,4 un total de 7,95 g (53,7 mmoles) d'anhydride phtalique pulvérulent.
Ce mélange réactionnel est agité jusqu'à dissolution complète avec addition périodique de solution, à 48% d'hydroxyde de sodium pour maintenir le pH entre 8 et 10.
<EMI ID=15.1>
Apres une agitation de 60 mn, la solution est filtrée pour éliminer le résidu insoluble et le filtrat est acidifié au pH de 3.
Le précipité formé est séparé par filtration et lavé à l'eau, puis séché dans une étuve à vide à 40[deg.]C.
On obtient 14 g, soit 80,5% du rendement théorique, du composé indiqué en tête, d'un point de fusion de 196-198[deg.]C. Analyse :
calculé : C 53,86 ; H 3,76 ; N 10,47 ; S 7,99 % ;
trouvé : C 53,67 ; H 3,60 ; N 10,74 ; S 8, 08 %.
REVENDICATIONS
1. Mono-phtalimido-sulfamide de la formule de structure générale :
<EMI ID=16.1>
dans laquelle le symbole R représente le reste d'une molécule de sulfamide de l'une des formules
<EMI ID=17.1>
<EMI ID=18.1>
2. Procédé de préparation d'un mono-phtalimido-
New phthalimido-sulfonamides and
Process for their preparation The present invention relates to novel sulfonamide derivatives and to a process for their preparation.
The new derivatives of the invention meet
to the general structure formula
<EMI ID = 1.1>
<EMI ID = 2.1>
sulfonamide molecule of one of the formulas
<EMI ID = 3.1>
<EMI ID = 4.1>
These new derivatives can be prepared by reacting phthalic anhydride in a basic medium,
<EMI ID = 5.1>
In the first case, we obtain the mono-phthalimide of sulfaquinoxaline of the formula
<EMI ID = 6.1>
in the second case, sulfametoxazole mono-phthalimide of the formula
<EMI ID = 7.1>
The preparation of the new derivatives of the invention is illustrated by the non-limiting examples of embodiments below.
Example 1
Preparation of sulfaquinoxaline monophthalimide In an Erlenmeyer flask with mechanical stirrer,
75 ml of water and 13 g (43.3 idols) of sulfaquinoxaline are introduced, a 48% aqueous solution of sodium hydroxide is added to it up to the pH of 10.7, then in small portions
a total of 6.75 g (45.6 mmol) of powdery phthalic anhydride, the pH being maintained in the vicinity of 9.4.
After complete addition of phthalic anhydride,
the reaction mixture is stirred for 2 hours adding
<EMI ID = 8.1>
sodium sufficient to maintain the pH between 8 and 9.4.
After filtration of the reaction solution
<EMI ID = 9.1> with concentrated hydrochloric acid to pH 5, then with acetic acid to pH 3.
<EMI ID = 10.1>
and washed with water until neutral. By drying at 4 [deg.] C under vacuum, 17.3 g of a solid product are obtained, which is
<EMI ID = 11.1>
is heated at reflux for 2 hours, then filtered and
<EMI ID = 12.1>
The precipitate, which forms on cooling, is separated by filtration, washed with ethyl acetate and dried in vacuo. 10 g, or 51% of the theoretical yield, of the compound indicated at the head, with a melting point are obtained
of 191-192 [deg.] C (with decomposition).
Analysis:
<EMI ID = 13.1>
Example 2
Preparation of sulfamethoxazole mono-phthalimide
<EMI ID = 14.1>
48% aqueous sodium hydroxide solution, then added in small portions and maintaining the pH at 9.4 a total of 7.95 g (53.7 mmol) of powdered phthalic anhydride.
This reaction mixture is stirred until complete dissolution with periodic addition of a 48% sodium hydroxide solution to maintain the pH between 8 and 10.
<EMI ID = 15.1>
After stirring for 60 minutes, the solution is filtered to remove the insoluble residue and the filtrate is acidified to pH 3.
The precipitate formed is separated by filtration and washed with water, then dried in a vacuum oven at 40.degree.
14 g, ie 80.5% of the theoretical yield, of the compound indicated at the head, with a melting point of 196-198 [deg.] C are obtained. Analysis:
calculated: C 53.86; H 3.76; N 10.47; S 7.99%;
found: C 53.67; H 3.60; N 10.74; S, 8.08%.
CLAIMS
1. Mono-phthalimido-sulfonamide of the general structural formula:
<EMI ID = 16.1>
in which the symbol R represents the remainder of a sulfonamide molecule of one of the formulas
<EMI ID = 17.1>
<EMI ID = 18.1>
2. Process for preparing a mono-phthalimido-
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ES462774A ES462774A1 (en) | 1977-09-29 | 1977-09-29 | Procedure for the obtaining of new ftalil derivatives of sulfamides. (Machine-translation by Google Translate, not legally binding) |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BE862630A true BE862630A (en) | 1978-05-02 |
Family
ID=8474602
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BE184096A BE862630A (en) | 1977-09-29 | 1978-01-04 | NEW PHTHALIMIDO-SULFAMIDES AND PROCESS FOR THEIR PREPARATION |
Country Status (2)
| Country | Link |
|---|---|
| BE (1) | BE862630A (en) |
| ES (1) | ES462774A1 (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2001049685A3 (en) * | 1999-12-31 | 2002-02-14 | Texas Biotechnology Corp | Sulfonamides and derivatives thereof that modulate the activity of endothelin |
| US6541498B2 (en) | 1993-05-20 | 2003-04-01 | Texas Biotechnology | Benzenesulfonamides and the use thereof to modulate the activity of endothelin |
-
1977
- 1977-09-29 ES ES462774A patent/ES462774A1/en not_active Expired
-
1978
- 1978-01-04 BE BE184096A patent/BE862630A/en unknown
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6541498B2 (en) | 1993-05-20 | 2003-04-01 | Texas Biotechnology | Benzenesulfonamides and the use thereof to modulate the activity of endothelin |
| WO2001049685A3 (en) * | 1999-12-31 | 2002-02-14 | Texas Biotechnology Corp | Sulfonamides and derivatives thereof that modulate the activity of endothelin |
| US6686382B2 (en) | 1999-12-31 | 2004-02-03 | Encysive Pharmaceuticals Inc. | Sulfonamides and derivatives thereof that modulate the activity of endothelin |
Also Published As
| Publication number | Publication date |
|---|---|
| ES462774A1 (en) | 1978-05-16 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0719254B1 (en) | Method for the preparation of high purity substituted benz e]indoles and the alkaline salts thereof | |
| US5889183A (en) | β-Aminoethanesulphonylazide their use for the preparation of 2-aminoethane-sulphonamide (taurylamide), taurolidine or taurultam and their acid addition salts | |
| EP0325537B1 (en) | Process for the synthesis of 3'-azido-3'-deoxythymidine and the like | |
| BE862630A (en) | NEW PHTHALIMIDO-SULFAMIDES AND PROCESS FOR THEIR PREPARATION | |
| BE779775A (en) | DERIVATIVES OF UREA, METHOD FOR PREPARING THEM AND THEIR APPLICATIONS | |
| US4692545A (en) | Method for preparation of mercaptobenzoates | |
| JP2518014B2 (en) | Method for purifying α-substituted acetic acid | |
| US4236017A (en) | Process for synthesizing 2-substituted semicarbazones and carbalkoxy hydrazones | |
| JP3089373B2 (en) | Method for producing 2-mercapto-phenothiazine | |
| EP0363263B1 (en) | Process for the preparation of propionic-acid derivatives | |
| US4751314A (en) | Preparation of tetrachloro-3-iminoisoindolin-1-one | |
| BE858864A (en) | NEW ESTERS OF PHENYL- AND PYRIDINE-3-CARBOXYLIC ACIDS AND PROCESS FOR THEIR PREPARATION | |
| FR2574792A1 (en) | PROCESS FOR THE PREPARATION OF PYRROLIDINE DERIVATIVES | |
| EP0627403B1 (en) | Method for the production of hydroxyphenylacetic acids | |
| US4546203A (en) | Facile synthesis of β-hydroxy-β-methylglutaric acid | |
| JPH07330729A (en) | Production of 1,3-diiminoisoindoline derivative | |
| FR2513638A1 (en) | PROCESS FOR THE PREPARATION OF VINCAMINE ACID ESTERS | |
| JPS60169493A (en) | Preparation of 5-deoxy-l-arabinose | |
| JPS59186986A (en) | Preparation of 1',2'-diacyl-l-biopterin | |
| FR2536393A1 (en) | New aminoketones, process for preparing them and their therapeutic use | |
| BE890069A (en) | PROCESS FOR THE PREPARATION OF ALIPHATIC HYDROXY-PHENYL ACID DERIVATIVES AND CATALYST USEFUL THEREFOR | |
| FR2725201A1 (en) | PROCESS FOR THE PREPARATION OF NITROBENZENE DERIVATIVES | |
| CA2086923A1 (en) | Vinylsulphonyl pristinamycin and preparation thereof | |
| FR2495143A1 (en) | PROCESS FOR THE PREPARATION OF 1- (3,5-DIMETHOXY-4-HYDROXY PHENYL) -2- (N-METHYLAMINO) ETHANOL HYDROCHLORIDE | |
| JPS63280084A (en) | Manufacture of 1-alkyl-3-carboxy-4-cinnolones |