CH235948A - Process for the preparation of p-amino-benzenesulfonyl-amino-pyridine-Bz-N-methylensulfosaurem piperazine. - Google Patents
Process for the preparation of p-amino-benzenesulfonyl-amino-pyridine-Bz-N-methylensulfosaurem piperazine.Info
- Publication number
- CH235948A CH235948A CH235948DA CH235948A CH 235948 A CH235948 A CH 235948A CH 235948D A CH235948D A CH 235948DA CH 235948 A CH235948 A CH 235948A
- Authority
- CH
- Switzerland
- Prior art keywords
- sep
- amino
- piperazine
- pyridine
- benzenesulfonyl
- Prior art date
Links
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 title claims description 14
- 238000000034 method Methods 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 3
- 238000000354 decomposition reaction Methods 0.000 claims description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- -1 methylene sulfonic acid Chemical compound 0.000 claims 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 230000029142 excretion Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
Verfahren zur Herstellung von p-amino-benzolsulfonyl-a-amino-pyridin-Bz-N- methylensulfosaurem Piperazin. - Im Hauptpatent ist ein Verfahren zur Herstellung von p-amino-benzolsulfonyl-a- amino -pyridin - Bz -N'i,-methylensulfosaurem Hegamethylentetramin durch Umsetzung der freien Säure mit Hegamethylentetramin be schrieben.
Es wurde nun ,gefunden, dass man ein therapeutisch ebenso wertvolles Salz erhält, wenn man p-Amino-benzolsulfonyl-a--:amino- pyridän-Bz-N-methylensuI-fos@äure in Gegen wart eines Alikohals auf Piperazin einwirken lässt.
Beispiel: 8,61 g Piperazin werden in 500 cm' Wasser gelöst und allmählich unter Um rühren eine Aufschwemmung von 34,38 g fein pulverisierter p-Amino-benzoleulfonyl-a- amino-pyridin-Bz-N-methylensulfosäure in 250 cm' eines Alkohols, beispielsweise Iso- propylalko#hol, zugegeben.
Es erfolgt, gege benenfalls unter Erwärmen, Auflösung und fast gleichzeitig Ausscheidung von p-a@mino- benzo-I ulfonyl - a - amino - pyridin - Bz --N - methylensul@osaurem Piperazin. Durch Um- kristallisation aus wässsferigem Alkohol erhält man weisse Plättchen vom Schmelzpunkt 172 (unter Zersetzung);
das sulfosaure Piperazin soll therapeutisch Verwendung finden.
Process for the preparation of p-aminobenzenesulfonyl-a-aminopyridine-Bz-N-methylensulfosaurem piperazine. - In the main patent, a process for the preparation of p-amino-benzenesulfonyl-a-amino-pyridine - Bz -N'i, -methylensulfosaurem hegamethylenetetramine by reacting the free acid with hegamethylenetetramine be written.
It has now been found that a therapeutically equally valuable salt is obtained if p-amino-benzenesulfonyl-a-: aminopyridän-Bz-N-methylene-sulfonyl-acid is allowed to act on piperazine in the presence of an alico neck.
Example: 8.61 g of piperazine are dissolved in 500 cm 'of water and gradually stirring a suspension of 34.38 g of finely powdered p-amino-benzenesulfonyl-a-aminopyridine-Bz-N-methylene sulfonic acid in 250 cm' of a Alcohol, for example isopropyl alcohol, added.
It takes place, if necessary with heating, dissolution and almost at the same time excretion of p-a @ minobenzo-lulfonyl - a - amino - pyridine - Bz --N - methylensulf @ osaurem piperazine. Recrystallization from aqueous alcohol gives white platelets with a melting point of 172 (with decomposition);
the sulfonic acid piperazine is said to be used therapeutically.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH235948T | 1942-05-02 | ||
| CH228551T | 1943-04-06 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH235948A true CH235948A (en) | 1944-12-31 |
Family
ID=25727227
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH235948D CH235948A (en) | 1942-05-02 | 1942-05-02 | Process for the preparation of p-amino-benzenesulfonyl-amino-pyridine-Bz-N-methylensulfosaurem piperazine. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH235948A (en) |
-
1942
- 1942-05-02 CH CH235948D patent/CH235948A/en unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CH235948A (en) | Process for the preparation of p-amino-benzenesulfonyl-amino-pyridine-Bz-N-methylensulfosaurem piperazine. | |
| CH339624A (en) | Process for the preparation of a drug compound | |
| AT138027B (en) | Process for the preparation of 8-oxyquinoline. | |
| US1863676A (en) | Amino-hydroxy pyridine and process of preparing the same | |
| CH164730A (en) | Process for the preparation of a new sulfonic acid. | |
| CH255001A (en) | Process for the preparation of a p-amino-benzenesulfonacylamide. | |
| CH233109A (en) | Process for the preparation of N- (p-aminobenzenesulfonyl) -N'-methylurea. | |
| CH178944A (en) | Process for the preparation of 2-oxydiphenyl ether-5-carboxylic acid. | |
| CH180314A (en) | Process for the preparation of a derivative of 2-ethoxy-5-propionylaminopyridine. | |
| CH217346A (en) | Process for the preparation of a benzenesulfonic acid derivative. | |
| CH235950A (en) | Process for the preparation of p-amino-benzenesulfonyl-amino-pyridine-Bz-N-methylensulfosaurem nicotinic acid amide. | |
| CH235949A (en) | Process for the preparation of p-amino-benzenesulfonyl-amino-pyridine-Bz-N-methylene-sulfonic acid morpholine. | |
| CH180313A (en) | Process for the preparation of a derivative of 2-ethoxy-5-butyrylaminopyridine. | |
| CH235496A (en) | Process for the production of a sugar derivative. | |
| CH242291A (en) | Process for the preparation of a p-amino-benzenesulfonamide. | |
| CH235947A (en) | Process for the preparation of p-amino-benzenesulfonyl-amino-pyridine-Bz-N-methylensulfosaurem ephedrine. | |
| CH240580A (en) | Process for the preparation of p-amino-benzenesulfonylguanidine. | |
| CH293020A (en) | Process for the preparation of a thiosemicarbazone of a heterocyclic aldehyde. | |
| CH311589A (en) | Process for making a new salt. | |
| CH206630A (en) | Process for preparing an aminobenzenesulfonic acid amide compound. | |
| CH299240A (en) | Process for the preparation of a quaternary ammonium compound of a bis-aminoalkoxy-alkane. | |
| CH247123A (en) | Process for the preparation of a salt of N- (4-amino-benzenesulfone) -N'-benzyl urea. | |
| CH212592A (en) | Process for the preparation of a quinoline compound containing a basic substituted amino group in the 4-position. | |
| CH235946A (en) | Process for the preparation of p-amino-benzenesulfonyl-amino-pyridine-Bz-N-methylensulfonic acid 4-dimethylamino-1-phenyl-2,3-dimethylpyrazolone. | |
| CH234253A (en) | Process for the preparation of a sulfonamide compound. |