CH378339A - Verfahren zur Herstellung von substituierten 2-Phenyl-7-aminoalkoxy-chromonen - Google Patents
Verfahren zur Herstellung von substituierten 2-Phenyl-7-aminoalkoxy-chromonenInfo
- Publication number
- CH378339A CH378339A CH7340459A CH7340459A CH378339A CH 378339 A CH378339 A CH 378339A CH 7340459 A CH7340459 A CH 7340459A CH 7340459 A CH7340459 A CH 7340459A CH 378339 A CH378339 A CH 378339A
- Authority
- CH
- Switzerland
- Prior art keywords
- sep
- phenyl
- chromones
- substituted
- hydrochloride
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 10
- 238000002360 preparation method Methods 0.000 title claims description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 8
- -1 alkali metal salts Chemical class 0.000 claims description 6
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- 230000001419 dependent effect Effects 0.000 claims 1
- 239000003960 organic solvent Substances 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 15
- 238000002844 melting Methods 0.000 description 11
- 230000008018 melting Effects 0.000 description 11
- 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
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 230000001476 alcoholic effect Effects 0.000 description 3
- 235000019441 ethanol Nutrition 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- XQYZDYMELSJDRZ-UHFFFAOYSA-N papaverine Chemical compound C1=C(OC)C(OC)=CC=C1CC1=NC=CC2=CC(OC)=C(OC)C=C12 XQYZDYMELSJDRZ-UHFFFAOYSA-N 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- PXPNSQMWVPLERM-UHFFFAOYSA-N 2-methylchromen-4-one Chemical class C1=CC=C2OC(C)=CC(=O)C2=C1 PXPNSQMWVPLERM-UHFFFAOYSA-N 0.000 description 2
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- SXFPNMRWIWIAGS-UHFFFAOYSA-N Khellin Natural products COC1C2CCOC2C(OC)C3OC(C)CC(=O)C13 SXFPNMRWIWIAGS-UHFFFAOYSA-N 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- OTAFHZMPRISVEM-UHFFFAOYSA-N chromone Chemical compound C1=CC=C2C(=O)C=COC2=C1 OTAFHZMPRISVEM-UHFFFAOYSA-N 0.000 description 2
- HSMPDPBYAYSOBC-UHFFFAOYSA-N khellin Chemical compound O1C(C)=CC(=O)C2=C1C(OC)=C1OC=CC1=C2OC HSMPDPBYAYSOBC-UHFFFAOYSA-N 0.000 description 2
- 229960002801 khellin Drugs 0.000 description 2
- 230000003170 musculotropic effect Effects 0.000 description 2
- 229960001789 papaverine Drugs 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 125000000547 substituted alkyl group Chemical group 0.000 description 2
- ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 2
- RVCSYOQWLPPAOA-QKYUOBHYSA-M trospium chloride Chemical compound [Cl-].[N+]12([C@@H]3CC[C@H]2C[C@H](C3)OC(=O)C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CCCC1 RVCSYOQWLPPAOA-QKYUOBHYSA-M 0.000 description 2
- JRPNCILONFCLQX-UHFFFAOYSA-N 1,2-dichloro-n,n-dimethylethanamine Chemical compound CN(C)C(Cl)CCl JRPNCILONFCLQX-UHFFFAOYSA-N 0.000 description 1
- NYYRRBOMNHUCLB-UHFFFAOYSA-N 3-chloro-n,n-dimethylpropan-1-amine Chemical compound CN(C)CCCCl NYYRRBOMNHUCLB-UHFFFAOYSA-N 0.000 description 1
- 229930008281 A03AD01 - Papaverine Natural products 0.000 description 1
- 241000700198 Cavia Species 0.000 description 1
- 241000700199 Cavia porcellus Species 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- 230000017531 blood circulation Effects 0.000 description 1
- 239000000812 cholinergic antagonist Substances 0.000 description 1
- YECBRSTWAYLPIM-UHFFFAOYSA-N chromium;hydrochloride Chemical compound Cl.[Cr] YECBRSTWAYLPIM-UHFFFAOYSA-N 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 210000005069 ears Anatomy 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- VHBFFQKBGNRLFZ-UHFFFAOYSA-N flavone Chemical class O1C2=CC=CC=C2C(=O)C=C1C1=CC=CC=C1 VHBFFQKBGNRLFZ-UHFFFAOYSA-N 0.000 description 1
- 230000000297 inotrophic effect Effects 0.000 description 1
- 231100001231 less toxic Toxicity 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 239000004570 mortar (masonry) Substances 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 229960000278 theophylline Drugs 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 230000002792 vascular Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
- C07D311/26—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3
- C07D311/28—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 2 only
- C07D311/30—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 2 only not hydrogenated in the hetero ring, e.g. flavones
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEC16925A DE1054091B (de) | 1958-05-30 | 1958-05-30 | Verfahren zur Herstellung von N-substituierten 2-Phenyl-7-aminoalkoxy-chromonen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH378339A true CH378339A (de) | 1964-06-15 |
Family
ID=7016141
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH7340459A CH378339A (de) | 1958-05-30 | 1959-05-20 | Verfahren zur Herstellung von substituierten 2-Phenyl-7-aminoalkoxy-chromonen |
Country Status (5)
| Country | Link |
|---|---|
| BE (1) | BE579151A (en(2012)) |
| CH (1) | CH378339A (en(2012)) |
| DE (1) | DE1054091B (en(2012)) |
| FR (1) | FR478M (en(2012)) |
| NL (1) | NL103682C (en(2012)) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0064165A1 (en) * | 1981-05-01 | 1982-11-10 | Pennwalt Corporation | Antihypertensive agents |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1218452B (de) * | 1959-10-14 | 1966-06-08 | Recordati S P A | Verfahren zur Herstellung von Hydrochloriden basischer Ester der 3-Methylflavon-8-carbonsaeure |
| DE1244192B (de) * | 1959-10-20 | 1967-07-13 | Recordati S P A | Verfahren zur Herstellung von Hydrochloriden basisch substituierter 3-Methyl-flavone bzw. -chromone |
| DE1223849B (de) * | 1960-10-11 | 1966-09-01 | Hans Voigt Chem Pharm Fabrik D | Verfahren zur Herstellung von milchsaurem 7-(N-beta-Dimethylaminoaethoxy)-flavon |
| DE1134384B (de) * | 1960-10-18 | 1962-08-09 | Hans Voigt Chem Pharm Fabrik D | Verfahren zur Herstellung von Salzen aus Xanthinessigsaeure- und Flavonderivaten |
| DE1174311B (de) * | 1960-10-25 | 1964-07-23 | Woelm Fa M | Verfahren zur Herstellung von N-substituierten 4'-Aminoalkoxy-2', 4-dihydroxy-chalkonen und deren Salzen |
| DE1222072B (de) * | 1961-03-06 | 1966-08-04 | Voigt Dr Med Hans | Verfahren zur Herstellung von N-substituierten 7-Aminoalkoxyflavonen |
| DE1193511B (de) * | 1961-03-16 | 1965-05-26 | Cassella Farbwerke Mainkur Ag | Verfahren zur Herstellung von Derivaten des 7-Oxychromons |
| DE1210882B (de) * | 1961-07-14 | 1966-02-17 | Cassella Farbwerke Mainkur Ag | Verfahren zur Herstellung von Derivaten des 7-Oxychromons |
| DE1270567B (de) * | 1961-05-19 | 1968-06-20 | Klinge Co Chem Pharm Fab | Verfahren zur Herstellung von basisch substituierten Flavonen |
| US3079402A (en) * | 1961-07-04 | 1963-02-26 | Hans Voigt Chem Pharm Fabrik D | Cero-chromonamino compounds |
| DE1210883B (de) * | 1961-11-09 | 1966-02-17 | Cassella Farbwerke Mainkur Ag | Verfahren zur Herstellung von Derivaten des 7-Oxycumarins |
| US5278174A (en) * | 1990-06-04 | 1994-01-11 | Scios Nova, Inc. | Sigma binding site agents |
| FR2689127B1 (fr) * | 1992-03-31 | 1994-05-06 | Adir Cie | Nouvelles 3', 5' -ditertbutyl-4'-hydroxy flavones, leur procede de preparation et les compositions pharmaceutiques les renfermant. |
-
1958
- 1958-05-30 DE DEC16925A patent/DE1054091B/de active Pending
-
1959
- 1959-05-20 CH CH7340459A patent/CH378339A/de unknown
- 1959-05-29 BE BE579151A patent/BE579151A/fr unknown
- 1959-05-29 NL NL239670A patent/NL103682C/xx active
-
1960
- 1960-08-30 FR FR795451A patent/FR478M/fr active Active
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0064165A1 (en) * | 1981-05-01 | 1982-11-10 | Pennwalt Corporation | Antihypertensive agents |
Also Published As
| Publication number | Publication date |
|---|---|
| NL103682C (en(2012)) | 1963-01-15 |
| BE579151A (fr) | 1959-11-30 |
| FR478M (en(2012)) | 1961-05-02 |
| DE1054091B (de) | 1959-04-02 |
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