DE2519816A1 - Verfahren zur herstellung von pyrido- eckige klammer auf 1,2-a eckige klammer zu pyrimidincarbonsaeure - Google Patents
Verfahren zur herstellung von pyrido- eckige klammer auf 1,2-a eckige klammer zu pyrimidincarbonsaeureInfo
- Publication number
- DE2519816A1 DE2519816A1 DE19752519816 DE2519816A DE2519816A1 DE 2519816 A1 DE2519816 A1 DE 2519816A1 DE 19752519816 DE19752519816 DE 19752519816 DE 2519816 A DE2519816 A DE 2519816A DE 2519816 A1 DE2519816 A1 DE 2519816A1
- Authority
- DE
- Germany
- Prior art keywords
- pyrido
- acid
- amino
- orthoformate
- cyclizing
- 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.)
- Pending
Links
- CUONGYYJJVDODC-UHFFFAOYSA-N malononitrile Chemical compound N#CCC#N CUONGYYJJVDODC-UHFFFAOYSA-N 0.000 title claims abstract description 8
- 239000002253 acid Substances 0.000 title claims abstract description 4
- ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 title description 3
- NHLLQCBSWYJLRI-UHFFFAOYSA-N pyrido[3,2-d]pyrimidine-2-carboxylic acid Chemical compound N1=CC=CC2=NC(C(=O)O)=NC=C21 NHLLQCBSWYJLRI-UHFFFAOYSA-N 0.000 title 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims abstract description 17
- -1 4H-pyrido 1 Chemical class 0.000 claims abstract description 7
- 238000000034 method Methods 0.000 claims abstract description 6
- 229920000137 polyphosphoric acid Polymers 0.000 claims abstract description 5
- 150000007513 acids Chemical class 0.000 claims abstract description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 10
- 150000002905 orthoesters Chemical class 0.000 claims description 4
- WXMLNSBINBLHPM-UHFFFAOYSA-N 4h-pyrido[1,2-a]pyrimidine-2-carboxylic acid Chemical class C1=CC=CC2=NC(C(=O)O)=CCN21 WXMLNSBINBLHPM-UHFFFAOYSA-N 0.000 claims description 3
- 150000003927 aminopyridines Chemical class 0.000 claims description 3
- 238000007363 ring formation reaction Methods 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 2
- 239000013067 intermediate product Substances 0.000 claims 1
- HLLRKOPFFAKBRC-UHFFFAOYSA-N 6-oxo-1h-pyrimidine-2-carboxylic acid Chemical compound OC(=O)C1=NC=CC(O)=N1 HLLRKOPFFAKBRC-UHFFFAOYSA-N 0.000 abstract 1
- 125000003282 alkyl amino group Chemical group 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 229960000583 acetic acid Drugs 0.000 description 4
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 238000002329 infrared spectrum Methods 0.000 description 2
- 238000001819 mass spectrum Methods 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- BRBUBVKGJRPRRD-UHFFFAOYSA-N 4,6-dimethylpyridin-2-amine Chemical compound CC1=CC(C)=NC(N)=C1 BRBUBVKGJRPRRD-UHFFFAOYSA-N 0.000 description 1
- ORLGLBZRQYOWNA-UHFFFAOYSA-N 4-methylpyridin-2-amine Chemical compound CC1=CC=NC(N)=C1 ORLGLBZRQYOWNA-UHFFFAOYSA-N 0.000 description 1
- QUXLCYFNVNNRBE-UHFFFAOYSA-N 6-methylpyridin-2-amine Chemical compound CC1=CC=CC(N)=N1 QUXLCYFNVNNRBE-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 150000005005 aminopyrimidines Chemical class 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- ZFCHNZDUMIOWFV-UHFFFAOYSA-N pyrimidine-2-carboxylic acid Chemical class OC(=O)C1=NC=CC=N1 ZFCHNZDUMIOWFV-UHFFFAOYSA-N 0.000 description 1
- 239000000725 suspension 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH414175A CH593282A5 (enrdf_load_stackoverflow) | 1975-04-02 | 1975-04-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2519816A1 true DE2519816A1 (de) | 1976-10-21 |
Family
ID=4270581
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19752519816 Pending DE2519816A1 (de) | 1975-04-02 | 1975-05-03 | Verfahren zur herstellung von pyrido- eckige klammer auf 1,2-a eckige klammer zu pyrimidincarbonsaeure |
Country Status (2)
| Country | Link |
|---|---|
| CH (1) | CH593282A5 (enrdf_load_stackoverflow) |
| DE (1) | DE2519816A1 (enrdf_load_stackoverflow) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4474953A (en) * | 1982-09-09 | 1984-10-02 | Riker Laboratories, Inc. | Process and intermediates for the preparation of 3(1H-tetrazol-5-yl)-4H-pyrido[1,2-a]pyrimidin-4-ones |
| US4507477A (en) * | 1982-09-09 | 1985-03-26 | Riker Laboratories, Inc. | Process for tetrazolyl-pyrimidinone derivatives |
-
1975
- 1975-04-02 CH CH414175A patent/CH593282A5/xx not_active IP Right Cessation
- 1975-05-03 DE DE19752519816 patent/DE2519816A1/de active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4474953A (en) * | 1982-09-09 | 1984-10-02 | Riker Laboratories, Inc. | Process and intermediates for the preparation of 3(1H-tetrazol-5-yl)-4H-pyrido[1,2-a]pyrimidin-4-ones |
| US4507477A (en) * | 1982-09-09 | 1985-03-26 | Riker Laboratories, Inc. | Process for tetrazolyl-pyrimidinone derivatives |
Also Published As
| Publication number | Publication date |
|---|---|
| CH593282A5 (enrdf_load_stackoverflow) | 1977-11-30 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0590428B1 (de) | Azachinoxaline, Verfahren zu ihrer Herstellung und ihre Verwendung | |
| US5508281A (en) | Derivatives of pyrido [2,3-d] and [3,2-d] pyrimidine and methods of using these derivatives | |
| DE3789599T2 (de) | Verfahren zur Herstellung von kondensierten Pyridinverbindungen. | |
| EP0645389A1 (de) | Verfahren zur Herstellung von Imidazopyridinderivaten | |
| DD231355A5 (de) | Verfahren zur herstellung von neuen 2-phenyl-unidazolen | |
| DE3324115A1 (de) | Neue imidazole, ihre herstellung und diese verbindungen enthaltende arzneimittel | |
| DE2720085C2 (enrdf_load_stackoverflow) | ||
| DD223151A5 (de) | Verfahren zur herstellung von 1,6-naphthyridinon-derivaten | |
| CH396927A (de) | Verfahren zur Herstellung neuer Pyrazolopyrimidine | |
| DE2519816A1 (de) | Verfahren zur herstellung von pyrido- eckige klammer auf 1,2-a eckige klammer zu pyrimidincarbonsaeure | |
| LAPPIN et al. | Cyclization of 2-aminopyridine derivatives. ii. the reaction of substituted 2-aminopyridines with ethyl malonate1 | |
| DE1153023B (de) | Verfahren zur Herstellung von 4-Hydroxy-pyrazolo[3,4-d] pyrimidinen | |
| DE2133998A1 (de) | 2,3-dihydro-oxo-imidazo eckige klammer auf 1,2-a eckige klammer zu -pyrimidine, deren saeureadditionssalze und verfahren zu deren herstellung | |
| DE69521174T2 (de) | Anthrachinonderivate mit antitumorwirkung und ihre verwendung | |
| DE3445299A1 (de) | Neue imidazoderivate, diese verbindungen enthaltende arzneimittel und verfahren zu ihrer herstellung | |
| EP0645388A1 (de) | Verfahren zur Herstellung von Imidazopyridinderivaten | |
| Khattab et al. | Pyrido [2, 3-d] pyrimidines, II. One step synthesis of pyrido [2, 3-d] pyrimidines and pyrimido [4, 5-b] quinolines from 6-amino uracils | |
| EP0180833B1 (de) | 4-Oxo-pyrido[2,3]pyrimidin-Derivate, Verfahren zur deren Herstellung und diese ethaltende Arzneimittel | |
| DE2025363A1 (en) | Bactericidal cycloalkanoquinolone derivs from - cycloalkanoquinoline derivs | |
| Brown et al. | Simple pyrimidines. Xvi. A synthetic route to some 2-(pyrimidin-2'-yl) acetic acids and esters | |
| DE1933870C3 (de) | Verfahren zur Herstellung von I socarbostyril-Verbindungen | |
| US3836533A (en) | 10-hydroxy-2-phenyl-5h-pyrido(1,2-a)pyrimido(4,5-d)-pyrimidin-5-one and processes thereto | |
| DE60120398T2 (de) | Imidazopyridin-8-one | |
| DE3023567A1 (de) | Substituierte (beta) -carbolin-3-carbonsaeurederivate | |
| DE2732906C2 (de) | In 5-Stellung durch einen Aminoalkylrest substituierte Imidazo-isochinolin-dione, Verfahren zu ihrer Herstellung und Arzneimittel |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHJ | Non-payment of the annual fee |