CH366546A - Process for the preparation of methylene-5- (p-aminobenzenesulfonylamido) -1-phenyl-pyrazole - Google Patents
Process for the preparation of methylene-5- (p-aminobenzenesulfonylamido) -1-phenyl-pyrazoleInfo
- Publication number
- CH366546A CH366546A CH5866158A CH5866158A CH366546A CH 366546 A CH366546 A CH 366546A CH 5866158 A CH5866158 A CH 5866158A CH 5866158 A CH5866158 A CH 5866158A CH 366546 A CH366546 A CH 366546A
- Authority
- CH
- Switzerland
- Prior art keywords
- phenyl
- pyrazole
- methylene
- preparation
- aminobenzenesulfonylamido
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims description 5
- 238000000034 method Methods 0.000 title claims description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 13
- 239000002253 acid Substances 0.000 claims description 4
- 150000007513 acids Chemical class 0.000 claims description 4
- -1 methylene-5- (p-amino-benzenesulfonamido) -1-phenyl-pyrazole Chemical compound 0.000 claims description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Chemical compound OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
- 239000000825 pharmaceutical preparation Substances 0.000 description 2
- HFFXLYHRNRKAPM-UHFFFAOYSA-N 2,4,5-trichloro-n-(5-methyl-1,2-oxazol-3-yl)benzenesulfonamide Chemical compound O1C(C)=CC(NS(=O)(=O)C=2C(=CC(Cl)=C(Cl)C=2)Cl)=N1 HFFXLYHRNRKAPM-UHFFFAOYSA-N 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 208000035473 Communicable disease Diseases 0.000 description 1
- 239000001828 Gelatine Substances 0.000 description 1
- 229930040373 Paraformaldehyde Natural products 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 239000008098 formaldehyde solution Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 239000004312 hexamethylene tetramine Substances 0.000 description 1
- 235000010299 hexamethylene tetramine Nutrition 0.000 description 1
- 210000000936 intestine Anatomy 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- 229920002866 paraformaldehyde Polymers 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000000069 prophylactic effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 description 1
- QWCJHSGMANYXCW-UHFFFAOYSA-N sulfaphenazole Chemical compound C1=CC(N)=CC=C1S(=O)(=O)NC1=CC=NN1C1=CC=CC=C1 QWCJHSGMANYXCW-UHFFFAOYSA-N 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three 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
- C07D231/38—Nitrogen atoms
- C07D231/42—Benzene-sulfonamido pyrazoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/54—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame
- A61K31/542—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame ortho- or peri-condensed with heterocyclic ring systems
- A61K31/545—Compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins, cefaclor, or cephalexine
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
Verfahren zur Herstellung von Methylen-5-(p-amino-benzolsulfonylamido)-1-phenyl-pyrazol Gegenstand der Erfindung ist die Herstellung von Methylen-5-(p-amino-benzolsulfonylamido)-1-phenyl- pyrazol.
Diese neue Verbindung besitzt wertvolle thera peutische Eigenschaften. So ist sie unter anderem be sonders gegen Coli-Bakterien wirksam und kann des halb als Heilmittel und Prophylaktikum, speziell bei infektiösen Erkrankungen des Darmes, Verwendung finden.
Das Methylen-5-(p-amino-benzolsu@lfonylamid'o)- 1-phenyl-pyrazol wird erhalten, wenn man 5-(p- Amino-benzolsulfonamido)-1-phenyl-pyrazol in Ge genwart von verdünnten Säuren mit Formaldehyd um setzt. Statt Formaldehyd selbst können auch Form aldehyd abgebende Mittel, wie Paraformald'ehyd oder Hexamethylentetramin verwendet werden. Die Um setzung wird vorteilhaft in Gegenwart von Wasser und bei Raumtemperatur oder unter mildem Erwär men durchgeführt.
Als Säuren kommen in erster Linie starke anorganische Säuren, wie Halogenwasserstoff säuren, Schwefelsäure, Perchlorsäure, Phosphorsäure und dergleichen, in Betracht.
Das neue Sulfonamidderivat kann als Heilmittel, z. B. in Form pharmazeutischer Präparate, Verwen dung finden, welche es in Mischung mit einem insbe sondere für die enterale Applikation geeigneten phar mazeutischen organischen oder anorganischen, festen oder flüssigen Trägermaterial enthalten. Für die Bil dung desselben kommen solche Stoffe in Frage, die mit der neuen Verbindung nicht reagieren, wie z. B.
Wasser, Gelatine, Milchzucker, Stärke, Magnesium stearat, Talk, pflanzliche öle, Benzylalkohole, Gummi, Polyalkylenglykole oder andere bekannte Arzneimit- telträger. Die pharmazeutischen Präparate können z. B. als Tabletten, Dragees oder in flüssiger Form als Lösungen, Suspensionen oder Emulsionen vorlie gen.
Gegebenenfalls können sie sterilisiert sein und bzw. oder Hilfsstoffe enthalten, wie Konservierungs-, Stabilisierungs-, Netz- oder Emulgiermittel, Salze zur Veränderung des osmotischen Druckes oder Puffer. Sie können auch noch andere therapeutisch wertvolle Stoffe enthalten. Die Präparate können nach üblichen Methoden gewonnen werden.
Die Temperaturen sind im folgenden Beispiel in Celsiusgraden angegeben.
<I>Beispiel</I> Eine Lösung von 31,4 g 5-(p-Amino-benzolsul- fonamido)-1-phenyl-pyrazal in 600 cm3 3n Salzsäure wird unter Rühren innerhalb 5 Minuten mit 25 cm3 40 % iger wässriger Formaldehydlösung versetzt. Nach etwa 10 Minuten wird mit einer wässrigen konzen trierten Natronlaugelösung auf
pH = 7 gestellt. Main nutscht dann ab und wäscht mit warmem Wasser gut nach. Das schwerlösliche Methylen-5-(p-amino-ben- zolsulfon.amido)-1-phenyl-pyrazol wird so in weissen Kristallen vom F. 208-210 erhalten.
Process for the preparation of methylene-5- (p-aminobenzenesulfonylamido) -1-phenyl-pyrazole The invention relates to the preparation of methylene-5- (p-aminobenzenesulfonylamido) -1-phenylpyrazole.
This new compound has valuable therapeutic properties. Among other things, it is particularly effective against coliform bacteria and can therefore be used as a remedy and prophylactic, especially for infectious diseases of the intestine.
The methylene-5- (p-amino-benzenesulfonylamid'o) -1-phenyl-pyrazole is obtained when 5- (p-amino-benzenesulfonamido) -1-phenyl-pyrazole in the presence of dilute acids with formaldehyde implements. Instead of formaldehyde itself, formaldehyde-releasing agents such as paraformaldehyde or hexamethylenetetramine can also be used. The implementation is advantageously carried out in the presence of water and at room temperature or under mild warming men.
As acids, strong inorganic acids such as hydrohalic acids, sulfuric acid, perchloric acid, phosphoric acid and the like are primarily suitable.
The new sulfonamide derivative can be used as a remedy, e.g. B. in the form of pharmaceutical preparations, uses which contain it as a mixture with a particular special for enteral application suitable phar maceutical organic or inorganic, solid or liquid carrier material. For the formation of the same substances come into question that do not react with the new compound, such. B.
Water, gelatine, milk sugar, starch, magnesium stearate, talc, vegetable oils, benzyl alcohol, gum, polyalkylene glycols or other known drug carriers. The pharmaceutical preparations can e.g. B. as tablets, coated tablets or in liquid form as solutions, suspensions or emulsions.
If necessary, they can be sterilized and / or contain auxiliary substances, such as preservatives, stabilizers, wetting agents or emulsifiers, salts for changing the osmotic pressure or buffers. They can also contain other therapeutically valuable substances. The preparations can be obtained by conventional methods.
In the following example, the temperatures are given in degrees Celsius.
<I> Example </I> A solution of 31.4 g of 5- (p-amino-benzenesulfonamido) -1-phenyl-pyrazal in 600 cm3 of 3N hydrochloric acid is stirred with 25 cm3 of 40% aqueous solution over the course of 5 minutes Formaldehyde solution added. After about 10 minutes, an aqueous concentrated sodium hydroxide solution is added
pH = 7. Main then sucks off and washes well with warm water. The sparingly soluble methylene-5- (p-amino-benzenesulfon.amido) -1-phenyl-pyrazole is obtained in this way in white crystals from F. 208-210.
Claims (1)
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH5866158A CH366546A (en) | 1958-04-23 | 1958-04-23 | Process for the preparation of methylene-5- (p-aminobenzenesulfonylamido) -1-phenyl-pyrazole |
| ES0248157A ES248157A1 (en) | 1958-04-23 | 1959-03-25 | Procedure for obtaining a new sulfonamid derivative (Machine-translation by Google Translate, not legally binding) |
| FR835239A FR116M (en) | 1958-04-23 | 1960-08-08 | New sulfonamide derivative usable in therapy. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH5866158A CH366546A (en) | 1958-04-23 | 1958-04-23 | Process for the preparation of methylene-5- (p-aminobenzenesulfonylamido) -1-phenyl-pyrazole |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH366546A true CH366546A (en) | 1963-01-15 |
Family
ID=4521837
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH5866158A CH366546A (en) | 1958-04-23 | 1958-04-23 | Process for the preparation of methylene-5- (p-aminobenzenesulfonylamido) -1-phenyl-pyrazole |
Country Status (3)
| Country | Link |
|---|---|
| CH (1) | CH366546A (en) |
| ES (1) | ES248157A1 (en) |
| FR (1) | FR116M (en) |
-
1958
- 1958-04-23 CH CH5866158A patent/CH366546A/en unknown
-
1959
- 1959-03-25 ES ES0248157A patent/ES248157A1/en not_active Expired
-
1960
- 1960-08-08 FR FR835239A patent/FR116M/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| ES248157A1 (en) | 1960-04-16 |
| FR116M (en) | 1961-01-09 |
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