CH237329A - Verfahren zur Herstellung von p-amino-benzolsulfonyl-a-amino-pyridin-Bz-N-methylensulfosaurem Chinin. - Google Patents
Verfahren zur Herstellung von p-amino-benzolsulfonyl-a-amino-pyridin-Bz-N-methylensulfosaurem Chinin.Info
- Publication number
- CH237329A CH237329A CH237329DA CH237329A CH 237329 A CH237329 A CH 237329A CH 237329D A CH237329D A CH 237329DA CH 237329 A CH237329 A CH 237329A
- Authority
- CH
- Switzerland
- Prior art keywords
- amino
- benzenesulfonyl
- quinine
- sulfonic acid
- aminopyridine
- Prior art date
Links
- LOUPRKONTZGTKE-WZBLMQSHSA-N Quinine Chemical compound C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-WZBLMQSHSA-N 0.000 title claims description 12
- LOUPRKONTZGTKE-UHFFFAOYSA-N cinchonine Natural products C1C(C(C2)C=C)CCN2C1C(O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-UHFFFAOYSA-N 0.000 title claims description 9
- 235000001258 Cinchona calisaya Nutrition 0.000 title claims description 6
- 229960000948 quinine Drugs 0.000 title claims description 6
- 238000000034 method Methods 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title description 4
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 title 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
- 229910052751 metal Inorganic materials 0.000 claims description 4
- 239000002184 metal Substances 0.000 claims description 4
- AKYHKWQPZHDOBW-UHFFFAOYSA-N (5-ethenyl-1-azabicyclo[2.2.2]octan-7-yl)-(6-methoxyquinolin-4-yl)methanol Chemical compound OS(O)(=O)=O.C1C(C(C2)C=C)CCN2C1C(O)C1=CC=NC2=CC=C(OC)C=C21 AKYHKWQPZHDOBW-UHFFFAOYSA-N 0.000 claims description 3
- 239000001576 FEMA 2977 Substances 0.000 claims description 3
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 3
- 229960003110 quinine sulfate Drugs 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- 230000001476 alcoholic effect Effects 0.000 claims description 2
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 3
- 229930013930 alkaloid Natural products 0.000 description 2
- 150000003797 alkaloid derivatives Chemical class 0.000 description 2
- 235000010299 hexamethylene tetramine Nutrition 0.000 description 2
- 239000004312 hexamethylene tetramine Substances 0.000 description 2
- BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 description 2
- XQYZDYMELSJDRZ-UHFFFAOYSA-N papaverine Chemical compound C1=C(OC)C(OC)=CC=C1CC1=NC=CC2=CC(OC)=C(OC)C=C12 XQYZDYMELSJDRZ-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 229930008281 A03AD01 - Papaverine Natural products 0.000 description 1
- 159000000009 barium salts Chemical class 0.000 description 1
- GKQTUHKAQKWLIN-UHFFFAOYSA-L barium(2+);dihydroxide;hydrate Chemical compound O.[OH-].[OH-].[Ba+2] GKQTUHKAQKWLIN-UHFFFAOYSA-L 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229960005181 morphine Drugs 0.000 description 1
- 229960001789 papaverine Drugs 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000010792 warming Methods 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D453/00—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids
- C07D453/02—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids containing not further condensed quinuclidine ring systems
- C07D453/04—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids containing not further condensed quinuclidine ring systems having a quinolyl-4, a substituted quinolyl-4 or a alkylenedioxy-quinolyl-4 radical linked through only one carbon atom, attached in position 2, e.g. quinine
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-methylensulfosaur em Chinin. Im Hauptpatent ist ein Verfahren zur Herstellung von p - amino - benzolsulfonyl - a amino,- pyridin-Bz -N@-;methylensulfosaurem Hexamethylentetramin durch Umsetzung der freien Säure mit Hexamethylentetramin be schrieben.
Es wurde nun gefunden, dass man thera peutisch ebenso wertvolle Salze der genann ten Säure erhalten kann, wenn man diese auf ein Alkaloid, z. B. auf ein Chinaalkaloid oder auf Morphin oder Päpaverin einwirken lässt.
Gegenstand des vorliegenden Patentes ist ein Verfahren zur Herstellung von p-amino- benzolsulfonyl- a-amino-pyridin-Bz-N-methy- lensulfosaurem Chinin, welches dadurch ge kennzeichnet ist, dass man die p-Amino-ben zolsulfonyl-a-amino-pyridin-Bz-N-methylen- sulfosäure zunächst mit dem Hydroxyd eines Metalles, dessen Sulfat in Alkohol nicht oder schwer löslich ist, neutralisiert und das so erhaltene Metallsalz in alkoholischer Lösung mit Chininsulfat umsetzt.
<I>Beispiel:</I> 10,29 g p- Amino-benzolsulfonyl-a-amino- pyridin-Bz-N-methylensulfosäure werden mit 4,71g Bariumhydroxydhydrat (es kommen auch andere Hydroxyde, z. B. Ca(OH): in Frage) in 160 em3 Wasser zum entsprechen den, löslichen p - Amino-benzolsulfonyl - a - a.mino-pyridin-Bz-N-methylen-sulfonat umge setzt und unter Kühlung, gegebenenfalls im Vakuum, zur Kristallisation gebracht.
Das p-amino - benzolsulfonyl -la-amino-pyridin-Bz- N-methylensulfosaure Barium bildet Kristall büschel aus weissen Nadeln und Blättchen. 9,0 g des getrockneten Bariumsalzes löst man unter Erwärmen in einem Gemisch von 45 em3 Wasser und 22,5 cm' eines Alkohols.
beispielsweise Äthanol, und mischt heiss mit einer Lösung von 8,55 g Chininsulfat in 270 cm3 eines Alkohols, beispielsweise Ätha- nol. Das ausgefallene Bäriumsulfat wird nach einigem Stehen noch warm abfiltriert und die klare Lösung der Kristallisation überlassen.
Das p-amino-ben7olsulfonyl-a- a.mino-py ridin-Bz-N-metliylensulfosaure Chi nin bildet feine weisse Nädelchen vom Schmelzpunkt 187-188' C; es enthält 48, 5 Chinin und soll therapeutisch Verwendung finden.
Claims (1)
- PATENTANSPRUCH: Verfahren zur Herstellung von p-.@mino- benzolsulfonyl-a-a,mirio - pyridin-Bz-N-methy- lensulfosaurem Chinin, dadurch gekennzeich net, dass man die p-Amino-benzolsulfonyl-a- amino-pyridiii-Bz-N-methylensulfosäure mit dem ITvdrozvd eines Metalles. dessen Sulfat in Alkohol nicht oder schwer löslich ist, neu tralisiert und das erhaltene Metallsalz in alkoholischer Lösung mit Chininsulfat um setzt.Das erhaltene neue Produkt bildet feine weisse Mädelchen vorn F. P. 187-188 C. Es enthält 48,5 % Chinin.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH228551T | 1943-04-06 | ||
| CH237329T | 1943-04-06 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH237329A true CH237329A (de) | 1945-04-15 |
Family
ID=25727231
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH237329D CH237329A (de) | 1943-04-06 | 1943-04-06 | Verfahren zur Herstellung von p-amino-benzolsulfonyl-a-amino-pyridin-Bz-N-methylensulfosaurem Chinin. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH237329A (de) |
-
1943
- 1943-04-06 CH CH237329D patent/CH237329A/de unknown
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