PL60793B1 - - Google Patents
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- Publication number
- PL60793B1 PL60793B1 PL121670A PL12167067A PL60793B1 PL 60793 B1 PL60793 B1 PL 60793B1 PL 121670 A PL121670 A PL 121670A PL 12167067 A PL12167067 A PL 12167067A PL 60793 B1 PL60793 B1 PL 60793B1
- Authority
- PL
- Poland
- Prior art keywords
- hydrogen
- general formula
- carried out
- naphthyridone
- derivatives
- Prior art date
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- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 3
- 125000005605 benzo group Chemical class 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 239000008096 xylene Substances 0.000 claims description 3
- 238000000034 method Methods 0.000 claims 6
- 125000000217 alkyl group Chemical group 0.000 claims 3
- 238000009833 condensation Methods 0.000 claims 3
- 230000005494 condensation Effects 0.000 claims 3
- 125000004103 aminoalkyl group Chemical group 0.000 claims 2
- 229910052736 halogen Inorganic materials 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims 1
- 229910052783 alkali metal Inorganic materials 0.000 claims 1
- -1 alkali metal alkoxide Chemical class 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims 1
- 125000003710 aryl alkyl group Chemical group 0.000 claims 1
- 239000011230 binding agent Substances 0.000 claims 1
- 238000009835 boiling Methods 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 229910000039 hydrogen halide Inorganic materials 0.000 claims 1
- 239000012433 hydrogen halide Substances 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- 239000003960 organic solvent Substances 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- 239000011541 reaction mixture Substances 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-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
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 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
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Description
Przyklad XIV. Do 25 ml metanolu dodano 1 g sodu, a nastepnie 300 ml ksylenu. Oddestylo¬ wano 30 ml metanolu z ksylenem, dodano 10 g 7-chlorobenzo-[b] [1,8]-naftyrydonu-5 i ogrzewano w temperaturze wrzenia mieszaniny w ciagu 1 go¬ dziny. Nastepnie wkroplono 12 g l-piperydyno-3- -chloropropanu i ogrzewano dalsze 5 godzin. Po¬ dano 500 ml wody i 10 ml kwasu solnego, rozdzie¬ lono warstwy, warstwe wodna zalkalizowano.Otrzymany surowy 10-(3-pirydynopropylo)-7-chlo- robenzonaftyrydon-5 oczyszczono przez krystaliza¬ cje z etanolu uzyskujac produkt o temperaturze topnienia 95—97°C.Analogicznie jak w przykladach I—XIV wycho¬ dzac z trójpodstawionych pochodnych benzo- [b] [l,8]-naftyrydonów-5 (10 H) otrzymuje sie równiez benzo-[b] [1,8]-naftyrydon-5 o wzorze ogólnym 1, w którym Ri, R2, R3 i R4 maja wyzej podane zna¬ czenie, lecz nie oznaczaja wodoru. PL PL
Claims (4)
1. Zastrzezenia patentowe 1. Sposób wytwarzania 10-podstawionych po¬ chodnych benzo-[b] [1,8]-naftyrydonów-5 o wzorze ogólnym 1, w którym Rx i Rj oznaczaja atom wo¬ doru, chlorowca nizsza grupe alkoksylowa lub alki¬ lowa, Rj oznacza atom wodoru lub grupe metylo¬ wa, a R4 oznacza nizsza grupe alkilowa, aryloalki- lowa lub aminoalkilowa z jednym lub dwoma ato¬ mami wodoru podstawionymi przez nizsze grupy alkilowe lub aminoalkilowe, które lacznie z sasied¬ nim atomem azotu moga tworzyc pierscien hetero¬ cykliczny, znamienny tym, ze benzo-[b] [l,8]-naf- tyrydon-5 (10 H) lub jego pochodne o wzorze ogól¬ nym 2, w którym Ri, R2 i Rj maja podane wyzej znaczenie, kondensuje sie ze zwiazkami o wzorze ogólnym R4X lub ich solami, w którym R4 ma po¬ dane wyzej znaczenie, a X oznacza chlorowiec.
2. Sposób wedlug zastrz. 1, znamienny tym, ze kondensacje prowadzi sie w roztworze rozpuszczal¬ nika organicznego, takiego jak alkohol alifatyczny lub weglowodór aromatyczny, taki jak ksylen.
3. Sposób wedlug zastrz, 1, znamienny tym, ze kondensacje prowadzi sie wi temperaturze wrze¬ nia mieszaniny reakcyjnej.
4. Sposób wedlug zastrz. 1, znamienny tym, ze kondensacje prowadzi sie w obecnosci srodków wiazacych chlorowcowodór, takich jak alkoholan lub wodorotlenek metalu alkalicznego.KI. 12 p, 10/10 60793 MKP C 07 d, 39/10 t Wzór A /A*3 Wzór 2 LZGraf. Zam, 1580, 27.Y.70. 230. PL PL
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR1585099D FR1585099A (pl) | 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 (pl) | 1967-07-13 | 1968-07-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PL60793B1 true PL60793B1 (pl) | 1970-06-25 |
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