DK142323B - Fremgangsmåde til fremstilling af pyrimido(4,5-b)quinolin-4(3H)-on-2-carboxylsyrealkylestere. - Google Patents
Fremgangsmåde til fremstilling af pyrimido(4,5-b)quinolin-4(3H)-on-2-carboxylsyrealkylestere. Download PDFInfo
- Publication number
- DK142323B DK142323B DK143876AA DK143876A DK142323B DK 142323 B DK142323 B DK 142323B DK 143876A A DK143876A A DK 143876AA DK 143876 A DK143876 A DK 143876A DK 142323 B DK142323 B DK 142323B
- Authority
- DK
- Denmark
- Prior art keywords
- quinoline
- carbon atoms
- pyrimido
- preparation
- aminoquinoline
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 12
- 238000002360 preparation method Methods 0.000 title claims description 7
- -1 benzyloxy, methylthio Chemical group 0.000 claims description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 13
- 238000006243 chemical reaction Methods 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 239000002904 solvent Substances 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 239000011734 sodium Substances 0.000 claims description 6
- 229910052708 sodium Inorganic materials 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 239000012442 inert solvent Substances 0.000 claims 1
- 239000000047 product Substances 0.000 description 9
- GXZOXGRLLFZVGF-UHFFFAOYSA-N 2-aminoquinoline-3-carboxamide Chemical compound C1=CC=C2N=C(N)C(C(=O)N)=CC2=C1 GXZOXGRLLFZVGF-UHFFFAOYSA-N 0.000 description 6
- 239000000376 reactant Substances 0.000 description 6
- WYACBZDAHNBPPB-UHFFFAOYSA-N diethyl oxalate Chemical compound CCOC(=O)C(=O)OCC WYACBZDAHNBPPB-UHFFFAOYSA-N 0.000 description 5
- PXBFMLJZNCDSMP-UHFFFAOYSA-N 2-Aminobenzamide Chemical compound NC(=O)C1=CC=CC=C1N PXBFMLJZNCDSMP-UHFFFAOYSA-N 0.000 description 4
- 150000001298 alcohols Chemical class 0.000 description 4
- 239000006227 byproduct Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000004703 alkoxides Chemical class 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 238000007363 ring formation reaction Methods 0.000 description 3
- KKORZNPFZXORNH-UHFFFAOYSA-N 4-oxo-3h-quinoline-2-carboxylic acid Chemical class C1=CC=C2C(=O)CC(C(=O)O)=NC2=C1 KKORZNPFZXORNH-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 239000005909 Kieselgur Substances 0.000 description 2
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 2
- JKRZOJADNVOXPM-UHFFFAOYSA-N Oxalic acid dibutyl ester Chemical compound CCCCOC(=O)C(=O)OCCCC JKRZOJADNVOXPM-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- BMCAWNQKVVTNFP-UHFFFAOYSA-N ethyl 4-oxo-1h-quinazoline-2-carboxylate Chemical compound C1=CC=C2NC(C(=O)OCC)=NC(=O)C2=C1 BMCAWNQKVVTNFP-UHFFFAOYSA-N 0.000 description 2
- VLCMRTMCMQJSKM-UHFFFAOYSA-N phenyl-[4-phenyl-8-(trifluoromethyl)quinolin-3-yl]methanone Chemical compound C=1C=CC=CC=1C(=O)C1=CN=C2C(C(F)(F)F)=CC=CC2=C1C1=CC=CC=C1 VLCMRTMCMQJSKM-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000005809 transesterification reaction Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- HQCJPLVCEVRXIE-UHFFFAOYSA-N 2-amino-6-fluoroquinoline-3-carboxamide Chemical compound FC1=CC=C2N=C(N)C(C(=O)N)=CC2=C1 HQCJPLVCEVRXIE-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 230000003266 anti-allergic effect Effects 0.000 description 1
- 239000000043 antiallergic agent Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- YFGANJBLBODUKY-UHFFFAOYSA-N ethyl 7-fluoro-4-oxo-1h-pyrimido[4,5-b]quinoline-2-carboxylate Chemical compound C1=C(F)C=C2C=C(C(=O)NC(C(=O)OCC)=N3)C3=NC2=C1 YFGANJBLBODUKY-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000011031 large-scale manufacturing process Methods 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000004043 responsiveness Effects 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/12—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains three hetero rings
- C07D491/14—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Quinoline Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US57131875A | 1975-04-24 | 1975-04-24 | |
| US57131875 | 1975-04-24 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DK143876A DK143876A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1976-10-25 |
| DK142323B true DK142323B (da) | 1980-10-13 |
| DK142323C DK142323C (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1981-06-29 |
Family
ID=24283193
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK143876AA DK142323B (da) | 1975-04-24 | 1976-03-30 | Fremgangsmåde til fremstilling af pyrimido(4,5-b)quinolin-4(3H)-on-2-carboxylsyrealkylestere. |
Country Status (20)
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5361243A (en) * | 1976-11-12 | 1978-06-01 | Fujitsu Ltd | 1-chip arithmetic circuit device |
| JP2006503094A (ja) * | 2002-10-16 | 2006-01-26 | スミスクライン ビーチャム コーポレーション | 化合物 |
-
1976
- 1976-01-01 AR AR262884A patent/AR207814A1/es active
- 1976-03-09 SE SE7603133A patent/SE7603133L/xx unknown
- 1976-03-10 CA CA247,583A patent/CA1065863A/en not_active Expired
- 1976-03-25 MX MX000113U patent/MX3019E/es unknown
- 1976-03-26 YU YU00791/76A patent/YU79176A/xx unknown
- 1976-03-30 ES ES446498A patent/ES446498A1/es not_active Expired
- 1976-03-30 DK DK143876AA patent/DK142323B/da not_active IP Right Cessation
- 1976-03-30 NL NL7603293.A patent/NL161155C/xx active
- 1976-04-07 SU SU762343061A patent/SU638261A3/ru active
- 1976-04-07 CH CH439876A patent/CH609056A5/fr not_active IP Right Cessation
- 1976-04-13 JP JP51041749A patent/JPS51127098A/ja active Granted
- 1976-04-13 AT AT270076A patent/AT351549B/de not_active IP Right Cessation
- 1976-04-13 BG BG032890A patent/BG27356A3/xx unknown
- 1976-04-14 FI FI761020A patent/FI761020A7/fi not_active Application Discontinuation
- 1976-04-15 DD DD192403A patent/DD125208A5/xx unknown
- 1976-04-16 LU LU74787A patent/LU74787A1/xx unknown
- 1976-04-16 HU HU76PI00000521A patent/HU172062B/hu unknown
- 1976-04-17 RO RO7685654A patent/RO68966A/ro unknown
- 1976-04-17 PL PL1976188875A patent/PL101824B1/pl unknown
- 1976-04-19 PT PT65023A patent/PT65023B/pt unknown
Also Published As
| Publication number | Publication date |
|---|---|
| BG27356A3 (bg) | 1979-10-12 |
| PT65023B (en) | 1977-09-09 |
| MX3019E (es) | 1980-02-13 |
| AT351549B (de) | 1979-07-25 |
| SE7603133L (sv) | 1976-10-25 |
| NL7603293A (nl) | 1976-10-26 |
| HU172062B (hu) | 1978-05-28 |
| CH609056A5 (en) | 1979-02-15 |
| JPS51127098A (en) | 1976-11-05 |
| ATA270076A (de) | 1979-01-15 |
| SU638261A3 (ru) | 1978-12-15 |
| CA1065863A (en) | 1979-11-06 |
| NL161155B (nl) | 1979-08-15 |
| JPS543880B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1979-02-27 |
| PT65023A (en) | 1976-05-01 |
| YU79176A (en) | 1982-05-31 |
| NL161155C (nl) | 1980-01-15 |
| DK142323C (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1981-06-29 |
| FI761020A7 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1976-10-25 |
| PL101824B1 (pl) | 1979-02-28 |
| LU74787A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1977-02-07 |
| ES446498A1 (es) | 1977-06-16 |
| AR207814A1 (es) | 1976-10-29 |
| DK143876A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1976-10-25 |
| DD125208A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1977-04-06 |
| RO68966A (ro) | 1981-05-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PBP | Patent lapsed |