DK142911B - Fremgangsmåde til fremstilling af pyrido(1,2-a)pyrimidin- eller pyrimido(1,2-a)quinolinderivater eller salte deraf. - Google Patents
Fremgangsmåde til fremstilling af pyrido(1,2-a)pyrimidin- eller pyrimido(1,2-a)quinolinderivater eller salte deraf. Download PDFInfo
- Publication number
- DK142911B DK142911B DK219978A DK219978A DK142911B DK 142911 B DK142911 B DK 142911B DK 219978 A DK219978 A DK 219978A DK 219978 A DK219978 A DK 219978A DK 142911 B DK142911 B DK 142911B
- Authority
- DK
- Denmark
- Prior art keywords
- carbon atoms
- pyrido
- pyrimidine
- isopropylidene
- oxo
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 40
- 150000003839 salts Chemical class 0.000 title claims description 11
- VFMCUTPRJLZEEW-UHFFFAOYSA-N 4h-pyrido[1,2-a]pyrimidine Chemical compound C1=CC=CN2CC=CN=C21 VFMCUTPRJLZEEW-UHFFFAOYSA-N 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title claims description 5
- APEJRAFJAXCCER-UHFFFAOYSA-N 1h-pyrimido[1,2-a]quinoline Chemical class C1=CC=C2N3CC=CN=C3C=CC2=C1 APEJRAFJAXCCER-UHFFFAOYSA-N 0.000 title claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 74
- 125000004432 carbon atom Chemical group C* 0.000 claims description 50
- 239000001257 hydrogen Substances 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 4
- 125000004414 alkyl thio group Chemical group 0.000 claims description 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 150000007513 acids Chemical class 0.000 claims description 2
- 125000004423 acyloxy group Chemical group 0.000 claims description 2
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 2
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 2
- 125000005530 alkylenedioxy group Chemical group 0.000 claims description 2
- 125000005133 alkynyloxy group Chemical group 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 61
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 37
- 239000011541 reaction mixture Substances 0.000 description 34
- -1 amino alcohols Chemical class 0.000 description 29
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 16
- 150000001875 compounds Chemical class 0.000 description 14
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- 238000007363 ring formation reaction Methods 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- CSOYDALHEQEMAK-UHFFFAOYSA-N 2h-pyrimidine-1-carboxylic acid Chemical compound OC(=O)N1CN=CC=C1 CSOYDALHEQEMAK-UHFFFAOYSA-N 0.000 description 5
- 150000002431 hydrogen Chemical group 0.000 description 5
- ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
- 229920000137 polyphosphoric acid Polymers 0.000 description 4
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 4
- LOAUVZALPPNFOQ-UHFFFAOYSA-M quinaldate Chemical compound C1=CC=CC2=NC(C(=O)[O-])=CC=C21 LOAUVZALPPNFOQ-UHFFFAOYSA-M 0.000 description 4
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 3
- GCMNJUJAKQGROZ-UHFFFAOYSA-N 1,2-Dihydroquinolin-2-imine Chemical compound C1=CC=CC2=NC(N)=CC=C21 GCMNJUJAKQGROZ-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- YGHFAYBPBVHKHY-UHFFFAOYSA-N 4-oxopyrido[1,2-a]pyrimidine-3-carboxylic acid Chemical compound C1=CC=CN2C(=O)C(C(=O)O)=CN=C21 YGHFAYBPBVHKHY-UHFFFAOYSA-N 0.000 description 2
- IQOVZHAKTOILRG-UHFFFAOYSA-N CC(=CCOC(=O)C1=CC(=NC=C1)NC2OC(=O)CC(=O)O2)C Chemical compound CC(=CCOC(=O)C1=CC(=NC=C1)NC2OC(=O)CC(=O)O2)C IQOVZHAKTOILRG-UHFFFAOYSA-N 0.000 description 2
- BYICBZGKJUJWEQ-UHFFFAOYSA-N CC(=COC1=CC(=NC2=CC=CC=C21)NC3OC(=O)CC(=O)O3)C Chemical compound CC(=COC1=CC(=NC2=CC=CC=C21)NC3OC(=O)CC(=O)O3)C BYICBZGKJUJWEQ-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 150000007529 inorganic bases Chemical class 0.000 description 2
- 150000002690 malonic acid derivatives Chemical class 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- MHCVCKDNQYMGEX-UHFFFAOYSA-N 1,1'-biphenyl;phenoxybenzene Chemical group C1=CC=CC=C1C1=CC=CC=C1.C=1C=CC=CC=1OC1=CC=CC=C1 MHCVCKDNQYMGEX-UHFFFAOYSA-N 0.000 description 1
- WOXFMYVTSLAQMO-UHFFFAOYSA-N 2-Pyridinemethanamine Chemical class NCC1=CC=CC=N1 WOXFMYVTSLAQMO-UHFFFAOYSA-N 0.000 description 1
- WZBLRECZRPSYTO-UHFFFAOYSA-N 2-[(6-methylpyridin-2-yl)-(propan-2-ylideneamino)methylidene]propanedioic acid Chemical compound CC1=NC(=CC=C1)C(=C(C(=O)O)C(=O)O)N=C(C)C WZBLRECZRPSYTO-UHFFFAOYSA-N 0.000 description 1
- 150000005013 2-aminoquinolines Chemical class 0.000 description 1
- OUCYVWHQGFOXJE-UHFFFAOYSA-N 2-ethylpyrido[1,2-a]pyrimidin-4-one Chemical compound C1=CC=CC2=NC(CC)=CC(=O)N21 OUCYVWHQGFOXJE-UHFFFAOYSA-N 0.000 description 1
- LOVXREQUMZKFCM-UHFFFAOYSA-N 4-[2-[1-(1,3-benzodioxol-5-yl)propan-2-ylamino]-1-hydroxyethyl]benzene-1,2-diol;hydron;chloride Chemical compound Cl.C=1C=C2OCOC2=CC=1CC(C)NCC(O)C1=CC=C(O)C(O)=C1 LOVXREQUMZKFCM-UHFFFAOYSA-N 0.000 description 1
- VJLHZZYJMCIFCR-UHFFFAOYSA-N 4-oxopyrido[1,2-a]pyrimidine-3,8-dicarboxylic acid Chemical compound O=C1C(=CN=C2N1C=CC(=C2)C(=O)O)C(=O)O VJLHZZYJMCIFCR-UHFFFAOYSA-N 0.000 description 1
- BGVXSKKYJAOHOM-UHFFFAOYSA-N 6-methyl-4-oxopyrido[1,2-a]pyrimidine-3-carboxylic acid Chemical compound C1=C(C(O)=O)C(=O)N2C(C)=CC=CC2=N1 BGVXSKKYJAOHOM-UHFFFAOYSA-N 0.000 description 1
- OMOKAARFXLVOEA-UHFFFAOYSA-N C1=CC=C(C=C1)COC(=O)C2=CN=C3C=CC4=CC=CC=C4N3C2=O Chemical compound C1=CC=C(C=C1)COC(=O)C2=CN=C3C=CC4=CC=CC=C4N3C2=O OMOKAARFXLVOEA-UHFFFAOYSA-N 0.000 description 1
- HODINOYTAIJOAM-UHFFFAOYSA-N CC(=C1C(N=C2C=CC=CC2=C1Cl)NC3OC(=O)CC(=O)O3)C Chemical compound CC(=C1C(N=C2C=CC=CC2=C1Cl)NC3OC(=O)CC(=O)O3)C HODINOYTAIJOAM-UHFFFAOYSA-N 0.000 description 1
- MZOJEZWFHFCHDP-UHFFFAOYSA-N CC(=C1CCCCN1C2=CC(=NC3=CC=CC=C32)NC4OC(=O)CC(=O)O4)C Chemical compound CC(=C1CCCCN1C2=CC(=NC3=CC=CC=C32)NC4OC(=O)CC(=O)O4)C MZOJEZWFHFCHDP-UHFFFAOYSA-N 0.000 description 1
- FGBPMCDPQSVVON-UHFFFAOYSA-N CC(=CCOC1=CC(=NC2=CC=CC=C21)NC3OC(=O)CC(=O)O3)C Chemical compound CC(=CCOC1=CC(=NC2=CC=CC=C21)NC3OC(=O)CC(=O)O3)C FGBPMCDPQSVVON-UHFFFAOYSA-N 0.000 description 1
- 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
- 206010022998 Irritability Diseases 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 description 1
- 206010035148 Plague Diseases 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 238000005904 alkaline hydrolysis reaction Methods 0.000 description 1
- 150000001414 amino alcohols Chemical class 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 230000003266 anti-allergic effect Effects 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 239000003899 bactericide agent Substances 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000006114 decarboxylation reaction Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- HVVIHYDKLGENKS-UHFFFAOYSA-N diethyl 4-oxopyrido[1,2-a]pyrimidine-3,7-dicarboxylate Chemical compound C1=C(C(=O)OCC)C(=O)N2C=C(C(=O)OCC)C=CC2=N1 HVVIHYDKLGENKS-UHFFFAOYSA-N 0.000 description 1
- LELKDPCCSLMHPV-UHFFFAOYSA-N diethyl 4-oxopyrido[1,2-a]pyrimidine-3,8-dicarboxylate Chemical compound C1=C(C(=O)OCC)C=CN2C1=NC=C(C(=O)OCC)C2=O LELKDPCCSLMHPV-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- SDMSGNXFHZBVSF-UHFFFAOYSA-N ethyl 1-oxopyrimido[1,2-a]quinoline-2-carboxylate Chemical compound C1=CC2=CC=CC=C2N2C1=NC=C(C(=O)OCC)C2=O SDMSGNXFHZBVSF-UHFFFAOYSA-N 0.000 description 1
- ZLYHSYOPYSDSHB-UHFFFAOYSA-N ethyl 6-methyl-4-oxopyrido[1,2-a]pyrimidine-3-carboxylate Chemical compound C1=CC=C(C)N2C(=O)C(C(=O)OCC)=CN=C21 ZLYHSYOPYSDSHB-UHFFFAOYSA-N 0.000 description 1
- ZXNPJNYRDHFJBV-UHFFFAOYSA-N ethyl 9-methyl-4-oxopyrido[1,2-a]pyrimidine-3-carboxylate Chemical compound CC1=CC=CN2C(=O)C(C(=O)OCC)=CN=C21 ZXNPJNYRDHFJBV-UHFFFAOYSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 239000000374 eutectic mixture Substances 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 125000000654 isopropylidene group Chemical group C(C)(C)=* 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- GXHFUVWIGNLZSC-UHFFFAOYSA-N meldrum's acid Chemical class CC1(C)OC(=O)CC(=O)O1 GXHFUVWIGNLZSC-UHFFFAOYSA-N 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- DDBREPKUVSBGFI-UHFFFAOYSA-N phenobarbital Chemical compound C=1C=CC=CC=1C1(CC)C(=O)NC(=O)NC1=O DDBREPKUVSBGFI-UHFFFAOYSA-N 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- FHOWXRRMROGVRH-UHFFFAOYSA-N propan-2-yl 6-methyl-4-oxopyrido[1,2-a]pyrimidine-3-carboxylate Chemical compound C(C)(C)OC(=O)C1=CN=C2N(C1=O)C(=CC=C2)C FHOWXRRMROGVRH-UHFFFAOYSA-N 0.000 description 1
- YTDVVJLYXSIROL-UHFFFAOYSA-N propyl 1-oxopyrimido[1,2-a]quinoline-2-carboxylate Chemical compound C1=CC2=CC=CC=C2N2C1=NC=C(C(=O)OCCC)C2=O YTDVVJLYXSIROL-UHFFFAOYSA-N 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- LOAUVZALPPNFOQ-UHFFFAOYSA-N quinaldic acid Chemical compound C1=CC=CC2=NC(C(=O)O)=CC=C21 LOAUVZALPPNFOQ-UHFFFAOYSA-N 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DK219978A DK142911B (da) | 1978-05-18 | 1978-05-18 | Fremgangsmåde til fremstilling af pyrido(1,2-a)pyrimidin- eller pyrimido(1,2-a)quinolinderivater eller salte deraf. |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DK219978A DK142911B (da) | 1978-05-18 | 1978-05-18 | Fremgangsmåde til fremstilling af pyrido(1,2-a)pyrimidin- eller pyrimido(1,2-a)quinolinderivater eller salte deraf. |
| DK219978 | 1978-05-18 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DK219978A DK219978A (en, 2012) | 1979-11-19 |
| DK142911B true DK142911B (da) | 1981-02-23 |
| DK142911C DK142911C (en, 2012) | 1981-10-05 |
Family
ID=8110743
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK219978A DK142911B (da) | 1978-05-18 | 1978-05-18 | Fremgangsmåde til fremstilling af pyrido(1,2-a)pyrimidin- eller pyrimido(1,2-a)quinolinderivater eller salte deraf. |
Country Status (1)
| Country | Link |
|---|---|
| DK (1) | DK142911B (en, 2012) |
-
1978
- 1978-05-18 DK DK219978A patent/DK142911B/da unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DK142911C (en, 2012) | 1981-10-05 |
| DK219978A (en, 2012) | 1979-11-19 |
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