CH214351A - Verfahren zur Darstellung eines Derivates des 2-Aminopyridins. - Google Patents
Verfahren zur Darstellung eines Derivates des 2-Aminopyridins.Info
- Publication number
- CH214351A CH214351A CH214351DA CH214351A CH 214351 A CH214351 A CH 214351A CH 214351D A CH214351D A CH 214351DA CH 214351 A CH214351 A CH 214351A
- Authority
- CH
- Switzerland
- Prior art keywords
- aminopyridine
- derivative
- preparation
- alcohol
- alkali
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 6
- 238000002360 preparation method Methods 0.000 title claims description 4
- 150000003930 2-aminopyridines Chemical class 0.000 title description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- IMRWILPUOVGIMU-UHFFFAOYSA-N 2-bromopyridine Chemical compound BrC1=CC=CC=N1 IMRWILPUOVGIMU-UHFFFAOYSA-N 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 150000007513 acids Chemical class 0.000 claims description 2
- 239000003513 alkali Substances 0.000 claims description 2
- 208000015181 infectious disease Diseases 0.000 claims description 2
- ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 claims 2
- HCRKCZRJWPKOAR-SNVBAGLBSA-N (4s)-4-(ethylamino)-2-(3-methoxypropyl)-1,1-dioxo-3,4-dihydrothieno[3,2-e]thiazine-6-sulfonamide Chemical compound CCN[C@@H]1CN(CCCOC)S(=O)(=O)C2=C1C=C(S(N)(=O)=O)S2 HCRKCZRJWPKOAR-SNVBAGLBSA-N 0.000 claims 1
- 241000501667 Etroplus Species 0.000 claims 1
- FZERHIULMFGESH-UHFFFAOYSA-N N-phenylacetamide Chemical compound CC(=O)NC1=CC=CC=C1 FZERHIULMFGESH-UHFFFAOYSA-N 0.000 claims 1
- 150000001447 alkali salts Chemical class 0.000 claims 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- -1 2- (p -acetylaminobenzenesulfonyl) - aminopyridine Chemical compound 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 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
- 150000001875 compounds Chemical class 0.000 description 1
- PKOFBDHYTMYVGJ-UHFFFAOYSA-N n-(4-sulfamoylphenyl)acetamide Chemical compound CC(=O)NC1=CC=C(S(N)(=O)=O)C=C1 PKOFBDHYTMYVGJ-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229940124530 sulfonamide Drugs 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
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
Verfahren zur Darstellung eines Derivates des 2-Aminopyridins. Die Erfindung betrifft ein Verfahren zur Darstellung eines Derivates des 2-Amino- py.ridinss, walohes,d#aaduroh gekennzeichnet ist, dass man 2,-Brompyridin mit einem Alka-Ii- sa.lz des p-Acetylaminobenzolsulfonamids zur Reaktion bringt. Das dabei unter Austritt von Alkalibromid sich : bildende 2-(p-Acetyl- aminobenzoIsulfonyl)-aminopyrridin soll thera- peuti",#ch verwendet werden, da es sich, als zur Bekämpfung von gokkeninfektionen' @vertvoll erwiesen hat. Die Darstellung dieser Verbindung er folgt beispielsweise folgendermassen: 15,8 g 2-Brompyridin und 23,6 g p-Ace- tylam-inobenzolGulfonamid-Natrium werden mit wenig Xylol während 2 Stunden am Rückfluss.kühler erhitzt. Hierauf wird das vom Xylol getrennte Reaktions; gemisoh mit Wasser behandelt und das zurückbleibende 2- (p -Acetylaminobenzolsulfonyl) - aminopyri- din aus heissem Alkohol umkristallisiert. Das Verfahrensprodukt bildet farblose Nadeln (aus Alkohol), die bei 220-222 C schmelzen. Es ist leicht löslich in verdünnten Säuren und Alkalien, wenig löslich in Alko hol, Azeton und Äther, sehr schwer löslich in kaltem und warmem Wasser.
Claims (1)
- PATENTANSPRUCH: Verfahren zur Darstellung eines Deriva- tes -des 2-Aminopyridins, .dadurch gekenn zeichnet, dass man 2-Brompyridin mit einem Alkalisalz des p-Acetylaminobenzolsulfon- amid6 zur Reaktion bringt, wobei unter Aus tritt von Alkalihromid 2-(p-Aeetylamä@no- benzolsulf(>nyl)-anminopyridingebildet wird. Das Verfahrensprodukt soll therapeu- tisch, insbesondere gegen gokkeninfektionen Verwendung finden. Es bildet farblose Nadeln (aus Alkohol), die bei 220-222' C schmelzen. Es ist leicht löslich in ver4ünn- ten ;Säuren und. Alkalien, wenig löslich in Alkohol, Azeton und Äther, sehr schwer lös lich in kaltem und warmem Wasser.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH212060T | 1938-08-30 | ||
| CH214351T | 1939-05-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH214351A true CH214351A (de) | 1941-04-15 |
Family
ID=25725131
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH214351D CH214351A (de) | 1938-08-30 | 1939-05-20 | Verfahren zur Darstellung eines Derivates des 2-Aminopyridins. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH214351A (de) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2003016309A1 (en) * | 2001-08-17 | 2003-02-27 | Merck & Co., Inc. | Process for preparing 5-sulfonamido-8-hydroxy-1, 6-naphthyridine-7-carboxamides |
-
1939
- 1939-05-20 CH CH214351D patent/CH214351A/de unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2003016309A1 (en) * | 2001-08-17 | 2003-02-27 | Merck & Co., Inc. | Process for preparing 5-sulfonamido-8-hydroxy-1, 6-naphthyridine-7-carboxamides |
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