CH228551A - Process for the preparation of p-aminobenzenesulfonyl- (a-aminopyridyl) -methylene sulfonic acid hexamethylenetetramine. - Google Patents
Process for the preparation of p-aminobenzenesulfonyl- (a-aminopyridyl) -methylene sulfonic acid hexamethylenetetramine.Info
- Publication number
- CH228551A CH228551A CH228551DA CH228551A CH 228551 A CH228551 A CH 228551A CH 228551D A CH228551D A CH 228551DA CH 228551 A CH228551 A CH 228551A
- Authority
- CH
- Switzerland
- Prior art keywords
- aminobenzenesulfonyl
- aminopyridyl
- sulfonic acid
- preparation
- hexamethylenetetramine
- Prior art date
Links
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 title claims description 18
- 239000004312 hexamethylene tetramine Substances 0.000 title claims description 9
- 235000010299 hexamethylene tetramine Nutrition 0.000 title claims description 9
- 238000000034 method Methods 0.000 title claims description 5
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 title description 4
- -1 p-aminobenzenesulfonyl Chemical group 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- 238000002844 melting Methods 0.000 claims description 3
- 230000008018 melting Effects 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 2
- 230000001225 therapeutic effect Effects 0.000 claims description 2
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 claims 1
- 230000002378 acidificating effect Effects 0.000 claims 1
- 229910052709 silver Inorganic materials 0.000 claims 1
- 239000004332 silver Substances 0.000 claims 1
- 229960004011 methenamine Drugs 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 4
- 239000002253 acid Substances 0.000 description 3
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 150000007530 organic bases Chemical class 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-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
- 239000000999 acridine dye Substances 0.000 description 1
- 229930013930 alkaloid Natural products 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229940051880 analgesics and antipyretics pyrazolones Drugs 0.000 description 1
- 229940111121 antirheumatic drug quinolines Drugs 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000000987 azo dye Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 150000002537 isoquinolines Chemical class 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 150000004893 oxazines Chemical class 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 125000000561 purinyl group Chemical class N1=C(N=C2N=CNC2=C1)* 0.000 description 1
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical class O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- UOULCEYHQNCFFH-UHFFFAOYSA-M sodium;hydroxymethanesulfonate Chemical compound [Na+].OCS([O-])(=O)=O UOULCEYHQNCFFH-UHFFFAOYSA-M 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 150000004897 thiazines Chemical class 0.000 description 1
- 150000003557 thiazoles Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/72—Nitrogen atoms
- C07D213/76—Nitrogen atoms to which a second hetero atom is attached
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/30—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/37—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups having the sulfur atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/81—Amides; Imides
- C07D213/82—Amides; Imides in position 3
-
- 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
- C07D231/44—Oxygen and nitrogen or sulfur and nitrogen atoms
- C07D231/46—Oxygen atom in position 3 or 5 and nitrogen atom in position 4
- C07D231/48—Oxygen atom in position 3 or 5 and nitrogen atom in position 4 with hydrocarbon radicals attached to said nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/02—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Darstellung von p-aminobenzolsulfonyl-(a-aminopyridyl)- methylensulfosaurem Hexamethylentetramin. Es ist bereits bekannt, dass man durch Einwirkung von Formaldehydnatriumbisulfit auf p-Aminobenzolsulfonyl-a-aminopyridin das p-aminobenzolsulfonyl - (a - aminopyridyl) - me- thylensulfosaure Natrium erhält. Aus diesem kann auf einfache Weise, nämlich durch Ansäuern mit anorganischen Säuren, die freie Sulfosäure der Formel
EMI0001.0011
in kristallinischer Form isoliert werden.
Ihr Schmelzpunkt beträgt 184-186 .
Es wurde nun gefunden, dass eine Reihe von Salzen dieser Säure hohen therapeutischen Wert besitzt und sich zum Teil durch gute Wasserlöslichkeit auszeichnet, und dass man diese Salze erhält, wenn man die genannte Säure mit organischen Basen umsetzt. Als organische Basen können z.
B. folgende ver wendet werden: aliphatische oder aromatische ein- oder mehrwertige Amine, Hexamethylen- tetramin, aliphatische oder aromatische Car- bonsäureamide, Pyrazolone, Pyridine, Thia- zole, Chinoline oder Isochinoline, Azine, Purine, Oxazine, Thiazine,
basische Acridin- oder Azofarbstoffe, oder Alkaloide. Die so erhaltenen, bisher noch nicht beschriebenen Salze sollen als Therapeutica Verwendung finden.
Gegenstand des vorliegenden Patentes ist ein Verfahren zur Herstellung des p-amino benzolsulfonyl-(a-aminopyridyll-methylensulfo- sauren Hexamethylentetramins, welches da durch gekennzeichnet ist, dass man auf p-Ami- nobenzolsulfonyl- (a - aminopyridyl) -methylen- sulfosäure der Formel
EMI0001.0042
Hexamethylentetramin einwirken lässt.
<I>Beispiel:</I> 68<B>)</B>6 g p-Aminobenzolsulfonyl-(a-amino- pyridyl)-methylensulfosäure der Formel
EMI0001.0046
werden in 200 cm' Alkohol aufgeschwemmt und mit einer Lösung von 24 g Hexamethylen- tetramin in 400 cm' Wasser geschüttelt, gegebenenfalls unter Anwendung von geringer Wärme.
Nach kurzer Zeit kristallisiert das p-aminobenzolsulfonyl - (a - aminopyridyl) - me- thylensulfosaure Hexamethylentetramin in weissen silberglänzenden Schuppen. Das Salz kann aus einem geeigneten Lösungsmittel. umkristallisiert werden; es ist leicht wasser löslich und hat den Schmelzpunkt 170-1711'.
Process for the preparation of p-aminobenzenesulfonyl- (a-aminopyridyl) -methylene sulfonic acid hexamethylenetetramine. It is already known that the action of sodium formaldehyde bisulfite on p-aminobenzenesulfonyl-a-aminopyridine gives p-aminobenzenesulfonyl- (a-aminopyridyl) -methylenesulfonic acid sodium. From this, in a simple manner, namely by acidification with inorganic acids, the free sulfonic acid of the formula
EMI0001.0011
can be isolated in crystalline form.
Their melting point is 184-186.
It has now been found that a number of salts of this acid have a high therapeutic value and are in some cases characterized by good solubility in water, and that these salts are obtained when the acid mentioned is reacted with organic bases. As organic bases, for.
B. the following are used: aliphatic or aromatic mono- or polyvalent amines, hexamethylene tetramine, aliphatic or aromatic carboxamides, pyrazolones, pyridines, thiazoles, quinolines or isoquinolines, azines, purines, oxazines, thiazines,
basic acridine or azo dyes, or alkaloids. The salts obtained in this way, not yet described, are intended to be used as therapeutic agents.
The subject of the present patent is a process for the preparation of p-amino benzenesulfonyl- (a-aminopyridyll-methylene-sulfo-acidic hexamethylenetetramine, which is characterized in that p-aminobenzenesulfonyl- (a - aminopyridyl) -methylene sulfonic acid is used formula
EMI0001.0042
Let hexamethylenetetramine act.
<I> Example: </I> 68 <B>) </B> 6 g of p-aminobenzenesulfonyl- (a-aminopyridyl) -methylene sulfonic acid of the formula
EMI0001.0046
are suspended in 200 cm 'of alcohol and shaken with a solution of 24 g of hexamethylene tetramine in 400 cm' of water, optionally using low heat.
After a short time, the p-aminobenzenesulfonyl - (a - aminopyridyl) - methylene sulfonic acid hexamethylenetetramine crystallizes in white, silvery scales. The salt can be obtained from a suitable solvent. be recrystallized; it is easily soluble in water and has a melting point of 170-1711 '.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH228551T | 1943-04-06 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH228551A true CH228551A (en) | 1943-08-31 |
Family
ID=4455626
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH228551D CH228551A (en) | 1943-04-06 | 1942-05-02 | Process for the preparation of p-aminobenzenesulfonyl- (a-aminopyridyl) -methylene sulfonic acid hexamethylenetetramine. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH228551A (en) |
-
1942
- 1942-05-02 CH CH228551D patent/CH228551A/en unknown
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