JPS638953B2 - - Google Patents
Info
- Publication number
- JPS638953B2 JPS638953B2 JP54030623A JP3062379A JPS638953B2 JP S638953 B2 JPS638953 B2 JP S638953B2 JP 54030623 A JP54030623 A JP 54030623A JP 3062379 A JP3062379 A JP 3062379A JP S638953 B2 JPS638953 B2 JP S638953B2
- Authority
- JP
- Japan
- Prior art keywords
- formula
- acid
- hydroxyl group
- compound
- reaction
- 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
Links
- 150000001875 compounds Chemical class 0.000 claims description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 150000007522 mineralic acids Chemical class 0.000 claims description 3
- 238000007363 ring formation reaction Methods 0.000 claims description 3
- FULCMGRANBCDAK-UHFFFAOYSA-N 10h-chromeno[3,2-b]pyridine Chemical class C1=CN=C2CC3=CC=CC=C3OC2=C1 FULCMGRANBCDAK-UHFFFAOYSA-N 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 3
- -1 methoxy, ethoxy, propoxy Chemical group 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 206010039085 Rhinitis allergic Diseases 0.000 description 1
- 201000010105 allergic rhinitis Diseases 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 230000003266 anti-allergic effect Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 229940071870 hydroiodic acid Drugs 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
Landscapes
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3062379A JPS55122785A (en) | 1979-03-15 | 1979-03-15 | Preparation of benzopyranopyridine derivative |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3062379A JPS55122785A (en) | 1979-03-15 | 1979-03-15 | Preparation of benzopyranopyridine derivative |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS55122785A JPS55122785A (en) | 1980-09-20 |
| JPS638953B2 true JPS638953B2 (zh) | 1988-02-25 |
Family
ID=12308977
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP3062379A Granted JPS55122785A (en) | 1979-03-15 | 1979-03-15 | Preparation of benzopyranopyridine derivative |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS55122785A (zh) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2567516B1 (fr) * | 1984-07-12 | 1988-09-16 | Sandoz Sa | Procede de preparation de xanthones et de thioxanthones et utilisation de ces composes comme initiateurs de photopolymerisation |
| BR9714497A (pt) * | 1996-12-27 | 2000-03-21 | Nippon Soda Co | Derivados de piperidinadiona substituìda, e, herbicidas. |
| CA2288274A1 (en) * | 1997-04-28 | 1998-11-05 | University Of Vermont | Regioisomeric benzothiopyranopyridines having antitumor activity |
| CN113121550B (zh) * | 2019-12-30 | 2024-04-02 | 武汉先路医药科技股份有限公司 | 一种7-乙氧羰基-5H-苯并吡喃[2,3-b]吡啶-5-酮的制备方法 |
| CN112047955B (zh) * | 2020-08-12 | 2023-02-28 | 上海诺精生物科技有限公司 | 一类用于抑制前列腺癌细胞迁移的化合物 |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4834865A (zh) * | 1971-09-08 | 1973-05-22 | ||
| JPS4956982A (zh) * | 1972-10-05 | 1974-06-03 | ||
| JPS4992072A (zh) * | 1972-09-06 | 1974-09-03 | ||
| JPS5093972A (zh) * | 1973-12-21 | 1975-07-26 |
-
1979
- 1979-03-15 JP JP3062379A patent/JPS55122785A/ja active Granted
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4834865A (zh) * | 1971-09-08 | 1973-05-22 | ||
| JPS4992072A (zh) * | 1972-09-06 | 1974-09-03 | ||
| JPS4956982A (zh) * | 1972-10-05 | 1974-06-03 | ||
| JPS5093972A (zh) * | 1973-12-21 | 1975-07-26 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS55122785A (en) | 1980-09-20 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE3147276A1 (de) | Verfahren zur herstellung von indolderivaten, deren verwendung als wertvolle zwischenprodukte und neue 4-hydroxyindole | |
| JPS63275582A (ja) | ２−アミノイミダゾ〔４，５−ｂ〕ピリジン誘導体の製造方法 | |
| EP0117474B1 (de) | Chinoloncarbonsäuren, Verfahren zu ihrer Herstellung sowie diese enthaltende antibakterielle Mittel | |
| JPH0130823B2 (zh) | ||
| DE69512495T2 (de) | Verfahren zur Herstellung von Chinolin-2-yl-benzoesäure | |
| JPS638953B2 (zh) | ||
| JPH0148911B2 (zh) | ||
| JP2693987B2 (ja) | キノリンカルボン酸の製造方法 | |
| DE2929414A1 (de) | Pyrimido- eckige klammer auf 5',4' zu 5,6 eckige klammer zu -pyrido- eckige klammer auf 1,2-a eckige klammer zu -benzimidazole, verfahren zu ihrer herstellung und deren verwendung | |
| EP1253149B1 (en) | Sulfate salt of quinolonecarboxylic acid derivative and use thereof | |
| DE2254944A1 (de) | 2,4,5-trisubstituierte oxazole | |
| JPS61134351A (ja) | ４‐アシルオキシ‐３‐オキソ‐酪酸エステル類の製造方法 | |
| JPH01128982A (ja) | ベンゾ〔ｉｊ〕キノリジン−２−カルボン酸誘導体の合成方法 | |
| DE1445025A1 (de) | Verfahren zur Herstellung von Benzimidazolen | |
| JPS6031824B2 (ja) | ヒドロキシフェニルピペリジニルメタノ−ル誘導体の製法 | |
| JPH0378384B2 (zh) | ||
| US3074956A (en) | Oxazoline compounds and method for producing same | |
| JP4380963B2 (ja) | フルオロキノロンカルボン酸の改良された製造方法 | |
| CA1044239A (en) | 6-alkoxy-7-hydroxyquinoline-3-carboxylic acids and derivatives thereof | |
| WO1991001315A1 (en) | New quinoline derivatives and process for the preparation thereof | |
| JPH11292873A (ja) | キノロンカルボン酸誘導体の製造方法およびその中間体 | |
| Gottlieb-Billroth | Derivatives of dibenzo-arsenole | |
| JPH05112554A (ja) | 新規なキノロンカルボン酸誘導体 | |
| US4216325A (en) | 4-(p-Fluorobenzoyl)-1-[3-(p-fluorobenzoyl)propyl]piperidine | |
| JPS5916878A (ja) | ２，４−ジヒドロキシ−３−アセチルキノリン類の製造方法 |