JPH0212232B2 - - Google Patents
Info
- Publication number
- JPH0212232B2 JPH0212232B2 JP56121365A JP12136581A JPH0212232B2 JP H0212232 B2 JPH0212232 B2 JP H0212232B2 JP 56121365 A JP56121365 A JP 56121365A JP 12136581 A JP12136581 A JP 12136581A JP H0212232 B2 JPH0212232 B2 JP H0212232B2
- Authority
- JP
- Japan
- Prior art keywords
- hydrocarbon group
- acid
- formula
- polyphosphoric acid
- ethyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims description 20
- 229920000137 polyphosphoric acid Polymers 0.000 claims description 19
- 150000002430 hydrocarbons Chemical group 0.000 claims description 17
- DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 claims description 13
- -1 methylene malonic acid cyclic ester Chemical class 0.000 claims description 11
- 150000008518 pyridopyrimidines Chemical class 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 3
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 11
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 239000000203 mixture Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 229930195733 hydrocarbon Chemical group 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- SBQOIKRRZODEHA-UHFFFAOYSA-N 2-(4-benzylpiperazin-1-yl)-8-ethyl-5-oxopyrido[2,3-d]pyrimidine-6-carboxylic acid Chemical compound N1=C2N(CC)C=C(C(O)=O)C(=O)C2=CN=C1N(CC1)CCN1CC1=CC=CC=C1 SBQOIKRRZODEHA-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 125000000654 isopropylidene group Chemical group C(C)(C)=* 0.000 description 2
- QAXZWHGWYSJAEI-UHFFFAOYSA-N n,n-dimethylformamide;ethanol Chemical compound CCO.CN(C)C=O QAXZWHGWYSJAEI-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- DJDDYWYYTKNZPM-UHFFFAOYSA-N 2-amino-1,3-dioxane-4,6-dione Chemical compound NC1OC(=O)CC(=O)O1 DJDDYWYYTKNZPM-UHFFFAOYSA-N 0.000 description 1
- DVLSQHLXPRYYRC-UHFFFAOYSA-N 5-(methoxymethylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione Chemical compound COC=C1C(=O)OC(C)(C)OC1=O DVLSQHLXPRYYRC-UHFFFAOYSA-N 0.000 description 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- YDHWWBZFRZWVHO-UHFFFAOYSA-N [hydroxy(phosphonooxy)phosphoryl] phosphono hydrogen phosphate Chemical compound OP(O)(=O)OP(O)(=O)OP(O)(=O)OP(O)(O)=O YDHWWBZFRZWVHO-UHFFFAOYSA-N 0.000 description 1
- LSYVCAOPFHHUHM-UHFFFAOYSA-N [hydroxy-[hydroxy-[hydroxy(phosphonooxy)phosphoryl]oxyphosphoryl]oxyphosphoryl] phosphono hydrogen phosphate Chemical compound OP(O)(=O)OP(O)(=O)OP(O)(=O)OP(O)(=O)OP(O)(=O)OP(O)(O)=O LSYVCAOPFHHUHM-UHFFFAOYSA-N 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 150000005005 aminopyrimidines Chemical class 0.000 description 1
- QTPILKSJIOLICA-UHFFFAOYSA-N bis[hydroxy(phosphonooxy)phosphoryl] hydrogen phosphate Chemical compound OP(O)(=O)OP(O)(=O)OP(O)(=O)OP(O)(=O)OP(O)(O)=O QTPILKSJIOLICA-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- XPPKVPWEQAFLFU-UHFFFAOYSA-N diphosphoric acid Chemical compound OP(O)(=O)OP(O)(O)=O XPPKVPWEQAFLFU-UHFFFAOYSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- YPOXGDJGKBXRFP-UHFFFAOYSA-N pyrimidine-4-carboxylic acid Chemical compound OC(=O)C1=CC=NC=N1 YPOXGDJGKBXRFP-UHFFFAOYSA-N 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 229940005657 pyrophosphoric acid Drugs 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- UNXRWKVEANCORM-UHFFFAOYSA-N triphosphoric acid Chemical compound OP(O)(=O)OP(O)(=O)OP(O)(O)=O UNXRWKVEANCORM-UHFFFAOYSA-N 0.000 description 1
- 229940048102 triphosphoric acid Drugs 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Nitrogen Condensed Heterocyclic Rings (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP56121365A JPS5823692A (ja) | 1981-08-04 | 1981-08-04 | ピリドピリミジン誘導体の製造法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP56121365A JPS5823692A (ja) | 1981-08-04 | 1981-08-04 | ピリドピリミジン誘導体の製造法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5823692A JPS5823692A (ja) | 1983-02-12 |
| JPH0212232B2 true JPH0212232B2 (fr) | 1990-03-19 |
Family
ID=14809438
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP56121365A Granted JPS5823692A (ja) | 1981-08-04 | 1981-08-04 | ピリドピリミジン誘導体の製造法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5823692A (fr) |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS52139094A (en) * | 1976-05-18 | 1977-11-19 | Sumitomo Chem Co Ltd | 1-fluoralkyl-1,4-dihydro-4-oxo-3-pyridinecarboxylic acid derivatives |
-
1981
- 1981-08-04 JP JP56121365A patent/JPS5823692A/ja active Granted
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS52139094A (en) * | 1976-05-18 | 1977-11-19 | Sumitomo Chem Co Ltd | 1-fluoralkyl-1,4-dihydro-4-oxo-3-pyridinecarboxylic acid derivatives |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5823692A (ja) | 1983-02-12 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP3713724B2 (ja) | イミダゾピリジン誘導体の製造方法 | |
| MXPA00004532A (es) | Proceso para la sistesis de analogos de nucleosidos. | |
| EP0909270B1 (fr) | Procede d'elaboration de 2,4-dihydroxypyridine et de 2,4-dihydroxy-3-nitropyridine | |
| JP3117731B2 (ja) | インドーロカルバゾール誘導体、その製造方法及びその使用。 | |
| WO1993016076A1 (fr) | 3-(1H^_-TETRAZOL-5-YL)-4H^_-PYRIDO[1,2-a^_]PYRIMIDINE-4-ONES, COMPOSITIONS PHARMACEUTIQUES LES CONTENANT, ET LEUR PREPARATION | |
| EP0260491B1 (fr) | 9-Déazaguanines | |
| PL181219B1 (pl) | Sposób wytwarzania pochodnych puryny | |
| CN113292506B (zh) | 一种2-氨基-4,6-二氯-5-硝基嘧啶的制备方法 | |
| CZ20013658A3 (cs) | Syntéza a krystalizace sloučenin obsahujících piperazinový kruh | |
| WO2009085797A1 (fr) | Procédés de préparation d'inhibiteurs de la transcriptase inverse du vih | |
| JPH0212232B2 (fr) | ||
| JPH0212231B2 (fr) | ||
| PL188477B1 (pl) | Sposób syntezy pośrednich związków chloropuryny | |
| US4039546A (en) | Method of preparing N1 -(2'-furanidyl)-5-substituted uracils | |
| CA2101789A1 (fr) | Methode de preparation d'imidazopyridines | |
| CA1297479C (fr) | Procede pour la preparation de la 6-amino-1,2-dihydro-1-hydroxy-2-imino-4-piperidinopyrimidin e | |
| US6861525B2 (en) | Process for the preparation imidazo[1,2-A]pyridine-3-acetamides | |
| KR880000154B1 (ko) | 아미노니트로피리딘의 제조방법 | |
| AU627609B2 (en) | New quinoline derivatives and process for the preparation thereof | |
| JP3303050B2 (ja) | アゾニアアダマンタン化合物およびこのものからのアザアダマンタン化合物の製造方法並びに該アゾニアアダマンタン化合物の製造方法 | |
| JPH05279345A (ja) | ４，６−ジアルコキシピリミジンの製造方法 | |
| US6593475B1 (en) | Preparation of derivative of 3-sulfonamido-4-phenylaminopyridine | |
| EP0435995A1 (fr) | Nouveaux derives de quinoleine et procede de preparation de ceux-ci | |
| JP4004082B2 (ja) | 環状ニトログアニジン誘導体の製造法 | |
| EP0786460A2 (fr) | 2-Arylquinoléines et procédé pour leur préparation |