CH616680A5 - Process for the preparation of a substituted benzopyrano[3,4-c]pyridine - Google Patents
Process for the preparation of a substituted benzopyrano[3,4-c]pyridine Download PDFInfo
- Publication number
- CH616680A5 CH616680A5 CH80576A CH80576A CH616680A5 CH 616680 A5 CH616680 A5 CH 616680A5 CH 80576 A CH80576 A CH 80576A CH 80576 A CH80576 A CH 80576A CH 616680 A5 CH616680 A5 CH 616680A5
- Authority
- CH
- Switzerland
- Prior art keywords
- compound
- formula
- benzopyrano
- pyridine
- hydrogen
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 9
- XYUGMLBMMWWINJ-UHFFFAOYSA-N 5h-chromeno[3,4-c]pyridine Chemical class C1=NC=C2COC3=CC=CC=C3C2=C1 XYUGMLBMMWWINJ-UHFFFAOYSA-N 0.000 title claims abstract description 8
- 238000002360 preparation method Methods 0.000 title claims abstract description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 18
- 238000006722 reduction reaction Methods 0.000 claims abstract description 7
- 230000005494 condensation Effects 0.000 claims abstract description 6
- 238000006482 condensation reaction Methods 0.000 claims abstract description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 239000003054 catalyst Substances 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 125000003107 substituted aryl group Chemical group 0.000 claims description 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
- 229940124630 bronchodilator Drugs 0.000 abstract description 3
- 150000001412 amines Chemical class 0.000 abstract description 2
- 238000006243 chemical reaction Methods 0.000 abstract description 2
- UWYCVSAHAGGILC-UHFFFAOYSA-N 1,2,3,4-tetrahydrochromeno[3,4-c]pyridin-5-one Chemical class C1CNCC2=C1C(C=CC=C1)=C1OC2=O UWYCVSAHAGGILC-UHFFFAOYSA-N 0.000 abstract 2
- 238000009833 condensation Methods 0.000 abstract 1
- 150000002576 ketones Chemical class 0.000 abstract 1
- 150000003053 piperidines Chemical class 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
- 238000004458 analytical method Methods 0.000 description 10
- 239000000047 product Substances 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 238000001704 evaporation Methods 0.000 description 6
- 230000008020 evaporation Effects 0.000 description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 229910052763 palladium Inorganic materials 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 235000011087 fumaric acid Nutrition 0.000 description 3
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 3
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000001530 fumaric acid Substances 0.000 description 2
- -1 methylene-dioxy group Chemical group 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 1
- LOBSVGRXQAHJDT-UHFFFAOYSA-N 1-morpholin-4-ylpropan-2-one Chemical compound CC(=O)CN1CCOCC1 LOBSVGRXQAHJDT-UHFFFAOYSA-N 0.000 description 1
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 1
- OVUPMFPSSFVDRJ-UHFFFAOYSA-N 8,9-dimethoxy-3-(2-morpholin-4-ylpropyl)-2,4-dihydro-1h-chromeno[3,4-c]pyridin-5-one Chemical compound C1CC=2C=3C=C(OC)C(OC)=CC=3OC(=O)C=2CN1CC(C)N1CCOCC1 OVUPMFPSSFVDRJ-UHFFFAOYSA-N 0.000 description 1
- NVKXEASZAMIQAR-UHFFFAOYSA-N 8,9-dimethoxy-3-(2-pyrrolidin-1-ylpropyl)-2,4-dihydro-1h-chromeno[3,4-c]pyridin-5-one Chemical compound C1CC=2C=3C=C(OC)C(OC)=CC=3OC(=O)C=2CN1CC(C)N1CCCC1 NVKXEASZAMIQAR-UHFFFAOYSA-N 0.000 description 1
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 1
- 208000009079 Bronchial Spasm Diseases 0.000 description 1
- 208000014181 Bronchial disease Diseases 0.000 description 1
- 206010006482 Bronchospasm Diseases 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- 241000700198 Cavia Species 0.000 description 1
- 206010010904 Convulsion Diseases 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 239000000168 bronchodilator agent Substances 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- BULLHNJGPPOUOX-UHFFFAOYSA-N chloroacetone Chemical compound CC(=O)CCl BULLHNJGPPOUOX-UHFFFAOYSA-N 0.000 description 1
- 239000002026 chloroform extract Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 230000036461 convulsion Effects 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
Classifications
-
- 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
- C07D491/02—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 two hetero rings
- C07D491/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US54829875A | 1975-02-10 | 1975-02-10 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH616680A5 true CH616680A5 (en) | 1980-04-15 |
Family
ID=24188227
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH80576A CH616680A5 (en) | 1975-02-10 | 1976-01-23 | Process for the preparation of a substituted benzopyrano[3,4-c]pyridine |
Country Status (11)
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2411847A1 (de) * | 1973-03-21 | 1974-10-10 | Warner Lambert Co | Substituierte benzopyrano eckige klammer auf 3,4-c eckige klammer zu pyridine und diese verbindungen enthaltende arzneimittel |
-
1975
- 1975-04-08 DE DE19752515226 patent/DE2515226A1/de active Pending
- 1975-07-21 JP JP50088444A patent/JPS5195098A/ja active Pending
-
1976
- 1976-01-14 ZA ZA00760216A patent/ZA76216B/xx unknown
- 1976-01-23 CH CH80576A patent/CH616680A5/fr not_active IP Right Cessation
- 1976-02-02 FR FR7602740A patent/FR2299866A1/fr active Granted
- 1976-02-06 BE BE6045355A patent/BE838361A/xx unknown
- 1976-02-09 SE SE7601361A patent/SE7601361L/xx unknown
- 1976-02-09 DK DK51576AA patent/DK140145B/da unknown
- 1976-02-09 LU LU74318A patent/LU74318A1/xx unknown
- 1976-02-09 JP JP51013122A patent/JPS51105099A/ja active Pending
- 1976-02-10 NL NL7601350A patent/NL7601350A/xx not_active Application Discontinuation
- 1976-02-10 ES ES445048A patent/ES445048A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DK140145B (da) | 1979-06-25 |
| SE7601361L (sv) | 1976-08-11 |
| LU74318A1 (enrdf_load_stackoverflow) | 1976-08-13 |
| ZA76216B (en) | 1976-12-29 |
| NL7601350A (nl) | 1976-08-12 |
| ES445048A1 (es) | 1977-05-16 |
| DK51576A (enrdf_load_stackoverflow) | 1976-08-11 |
| DK140145C (enrdf_load_stackoverflow) | 1979-11-19 |
| JPS51105099A (enrdf_load_stackoverflow) | 1976-09-17 |
| BE838361A (fr) | 1976-08-06 |
| AU8030475A (en) | 1976-10-21 |
| JPS5195098A (en) | 1976-08-20 |
| DE2515226A1 (de) | 1976-08-19 |
| FR2299866A1 (fr) | 1976-09-03 |
| FR2299866B1 (enrdf_load_stackoverflow) | 1979-09-21 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US3403179A (en) | Novel 7-(1, 2-bis-substituted-hydrazino)-tetracyclines and methods of preparing same | |
| US5380935A (en) | Process for preparing 5-aminolevulinic acid | |
| Cho et al. | Synthesis of quinolines via ortho-lithiated N-acylanilines. A modified Friedlaender synthesis | |
| EP0602151A1 (fr) | Procede de synthese de glucuronides d'epoxy-4,5 morphinanes | |
| US2908691A (en) | Hydroxyphenalkylaminoalkylindoles and ethers corresponding thereto | |
| US7763748B2 (en) | Process for preparation of highly pure isotretinoin | |
| CH623584A5 (enrdf_load_stackoverflow) | ||
| CH616680A5 (en) | Process for the preparation of a substituted benzopyrano[3,4-c]pyridine | |
| LU80124A1 (fr) | Procede de production de derives 1-n-alkyles de la kanamycine | |
| HU204497B (en) | Process for producing phenfluramine | |
| US3062884A (en) | Catalytic hydrogenation of 2, 5-dialkoxy-beta-nitrostyrene to produce beta-aminoethylhydroquinone | |
| KR950008970B1 (ko) | t-부틸 에르골린 유도체의 제조방법 | |
| US2878254A (en) | N, n'-alkylene-bis-(3-hydroxypiperidine) compounds and preparation thereof | |
| CH380134A (fr) | Procédé de préparation de nouveaux dérivés de la phénothiazine | |
| US4474986A (en) | Preparation of propafenone | |
| CA1183849A (fr) | ¬alkyl- et alcenyl-3 piperidyl-4)-2 ethyl|-3 indoles et leur utilisation comme medicaments | |
| FR1464537A (fr) | Nouveaux aminophénanthrènes et leur procédé de fabrication | |
| JP4222206B2 (ja) | アミノスチルベン誘導体の製造方法 | |
| CA1121354A (en) | Derivatives of 4-[3-(4-quinolyl)propyl]- piperidine and their use as medicines | |
| BE1000112A5 (fr) | Procede de preparation d'encainide. | |
| JP2762106B2 (ja) | ３―ヒドロキシピロリジンの製造方法 | |
| Inoue et al. | Unsaturated crown ethers: Stilbeno-crown ethers | |
| SU1287746A3 (ru) | Способ получени производных 1-фенилимидазолидин-2-она или их кислотно-аддитивных солей | |
| EP0017523A1 (fr) | Nouveaux dérivés du dithiépinno (1,4)(2,3-c)pyrrole, leur préparation et les médicaments qui les contiennent | |
| EP0362309B1 (fr) | (ethylenedioxo-3,3 cyclohexyl)-4 acetophenone et derives de ce compose, procedes pour leur preparation et utilisation de ces composes |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |