PL60795B1 - - Google Patents
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- Publication number
- PL60795B1 PL60795B1 PL121669A PL12166967A PL60795B1 PL 60795 B1 PL60795 B1 PL 60795B1 PL 121669 A PL121669 A PL 121669A PL 12166967 A PL12166967 A PL 12166967A PL 60795 B1 PL60795 B1 PL 60795B1
- Authority
- PL
- Poland
- Prior art keywords
- acid
- naphthyridone
- water
- benzo
- derivatives
- Prior art date
Links
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 13
- 229920000137 polyphosphoric acid Polymers 0.000 claims description 12
- 125000005605 benzo group Chemical group 0.000 claims description 7
- 239000011541 reaction mixture Substances 0.000 claims description 5
- -1 3-carboxy-2-anilinopyridic acid Chemical compound 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000004435 hydrogen atoms Chemical class [H]* 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 238000000034 method Methods 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 235000019796 monopotassium phosphate Nutrition 0.000 claims description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 239000000203 mixture Substances 0.000 description 11
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- 238000002425 crystallisation Methods 0.000 description 7
- 230000005712 crystallization Effects 0.000 description 7
- 239000002244 precipitate Substances 0.000 description 7
- XHXFXVLFKHQFAL-UHFFFAOYSA-N Phosphoryl chloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 6
- 238000007363 ring formation reaction Methods 0.000 description 6
- 238000001816 cooling Methods 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- UUMMTMQODCACRH-UHFFFAOYSA-N 2-anilinopyridine-3-carboxylic acid Chemical compound OC(=O)C1=CC=CN=C1NC1=CC=CC=C1 UUMMTMQODCACRH-UHFFFAOYSA-N 0.000 description 2
- JUEUIJDWZRGSAK-UHFFFAOYSA-N NC=1C(=CC=CC=1)C1=CC=NC=C1C(=O)O Chemical compound NC=1C(=CC=CC=1)C1=CC=NC=C1C(=O)O JUEUIJDWZRGSAK-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 235000019441 ethanol Nutrition 0.000 description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 2
- PVNIIMVLHYAWGP-UHFFFAOYSA-N nicotinic acid Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- BEXZOAJWOZFOSM-UHFFFAOYSA-N 2-(2-methoxyanilino)pyridine-3-carboxylic acid Chemical compound COC1=CC=CC=C1NC1=NC=CC=C1C(O)=O BEXZOAJWOZFOSM-UHFFFAOYSA-N 0.000 description 1
- ZAYXWXOVWFNPTQ-UHFFFAOYSA-N 2-(2-methylanilino)pyridine-3-carboxylic acid Chemical compound CC1=CC=CC=C1NC1=NC=CC=C1C(O)=O ZAYXWXOVWFNPTQ-UHFFFAOYSA-N 0.000 description 1
- YEXIXVLEDGNAKM-UHFFFAOYSA-N 2-(4-CHLORO-PHENYLAMINO)-NICOTINIC ACID Chemical compound OC(=O)C1=CC=CN=C1NC1=CC=C(Cl)C=C1 YEXIXVLEDGNAKM-UHFFFAOYSA-N 0.000 description 1
- OFKCFBVBBOJSMC-UHFFFAOYSA-N 2-(4-methylanilino)pyridine-3-carboxylic acid Chemical compound C1=CC(C)=CC=C1NC1=NC=CC=C1C(O)=O OFKCFBVBBOJSMC-UHFFFAOYSA-N 0.000 description 1
- RXARQPJWGRWGDI-UHFFFAOYSA-N 2-anilino-6-methylpyridine-3-carboxylic acid Chemical compound CC1=CC=C(C(O)=O)C(NC=2C=CC=CC=2)=N1 RXARQPJWGRWGDI-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N Carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- VMPITZXILSNTON-UHFFFAOYSA-N O-Anisidine Chemical compound COC1=CC=CC=C1N VMPITZXILSNTON-UHFFFAOYSA-N 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000000875 corresponding Effects 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxyl anion Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 229960003512 nicotinic acid Drugs 0.000 description 1
- 235000001968 nicotinic acid Nutrition 0.000 description 1
- 239000011664 nicotinic acid Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 230000000506 psychotropic Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR1585099D FR1585099A (fi) | 1967-07-13 | 1968-07-10 | |
| CH1029168A CH498841A (fr) | 1967-07-13 | 1968-07-10 | Procédé de préparation de benzo-(b,1,8)-naphtyridones-5 substituées |
| DE19681770839 DE1770839C3 (de) | 1967-07-13 | 1968-07-10 | 7-Chlor-10-(3-dimethylaminopropyl)- benzo [b] [13 eckige Klammer zu naphthyridon-5(10H) und dessen Salze, ein Verfahren zu seiner Herstellung sowie eine pharmazeutische Zubereitung |
| GB1228196D GB1228196A (fi) | 1967-07-13 | 1968-07-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PL60795B1 true PL60795B1 (fi) | 1970-06-25 |
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