GB1087539A - 3,6-disubstituted flavan derivatives and their preparation - Google Patents
3,6-disubstituted flavan derivatives and their preparationInfo
- Publication number
- GB1087539A GB1087539A GB43600/66A GB4360066A GB1087539A GB 1087539 A GB1087539 A GB 1087539A GB 43600/66 A GB43600/66 A GB 43600/66A GB 4360066 A GB4360066 A GB 4360066A GB 1087539 A GB1087539 A GB 1087539A
- Authority
- GB
- United Kingdom
- Prior art keywords
- formula
- disubstituted
- flavan
- general formula
- derivative
- 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
- QOLIPNRNLBQTAU-UHFFFAOYSA-N flavan Chemical class C1CC2=CC=CC=C2OC1C1=CC=CC=C1 QOLIPNRNLBQTAU-UHFFFAOYSA-N 0.000 title abstract 5
- 239000002253 acid Substances 0.000 abstract 4
- -1 pyrrolidino, piperidino Chemical group 0.000 abstract 4
- 150000003839 salts Chemical class 0.000 abstract 3
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 abstract 2
- 229910052794 bromium Inorganic materials 0.000 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- 238000006243 chemical reaction Methods 0.000 abstract 2
- 229910052801 chlorine Inorganic materials 0.000 abstract 2
- 239000000460 chlorine Substances 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract 2
- 150000003856 quaternary ammonium compounds Chemical class 0.000 abstract 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 1
- DQFBYFPFKXHELB-UHFFFAOYSA-N Chalcone Natural products C=1C=CC=CC=1C(=O)C=CC1=CC=CC=C1 DQFBYFPFKXHELB-UHFFFAOYSA-N 0.000 abstract 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 1
- OEIJRRGCTVHYTH-UHFFFAOYSA-N Favan-3-ol Chemical compound OC1CC2=CC=CC=C2OC1C1=CC=CC=C1 OEIJRRGCTVHYTH-UHFFFAOYSA-N 0.000 abstract 1
- CITFYDYEWQIEPX-UHFFFAOYSA-N Flavanol Natural products O1C2=CC(OCC=C(C)C)=CC(O)=C2C(=O)C(O)C1C1=CC=C(O)C=C1 CITFYDYEWQIEPX-UHFFFAOYSA-N 0.000 abstract 1
- 239000007818 Grignard reagent Substances 0.000 abstract 1
- ZONYXWQDUYMKFB-UHFFFAOYSA-N SJ000286395 Natural products O1C2=CC=CC=C2C(=O)CC1C1=CC=CC=C1 ZONYXWQDUYMKFB-UHFFFAOYSA-N 0.000 abstract 1
- GAMYVSCDDLXAQW-AOIWZFSPSA-N Thermopsosid Natural products O(C)c1c(O)ccc(C=2Oc3c(c(O)cc(O[C@H]4[C@H](O)[C@@H](O)[C@H](O)[C@H](CO)O4)c3)C(=O)C=2)c1 GAMYVSCDDLXAQW-AOIWZFSPSA-N 0.000 abstract 1
- 239000004480 active ingredient Substances 0.000 abstract 1
- 230000010933 acylation Effects 0.000 abstract 1
- 238000005917 acylation reaction Methods 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 230000029936 alkylation Effects 0.000 abstract 1
- 238000005804 alkylation reaction Methods 0.000 abstract 1
- 150000001450 anions Chemical class 0.000 abstract 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 1
- 235000005513 chalcones Nutrition 0.000 abstract 1
- 230000005494 condensation Effects 0.000 abstract 1
- 238000009833 condensation Methods 0.000 abstract 1
- 239000003937 drug carrier Substances 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 235000011987 flavanols Nutrition 0.000 abstract 1
- 229930003949 flavanone Natural products 0.000 abstract 1
- 150000002207 flavanone derivatives Chemical class 0.000 abstract 1
- 235000011981 flavanones Nutrition 0.000 abstract 1
- 229930003944 flavone Natural products 0.000 abstract 1
- 150000002212 flavone derivatives Chemical class 0.000 abstract 1
- 235000011949 flavones Nutrition 0.000 abstract 1
- NWKFECICNXDNOQ-UHFFFAOYSA-N flavylium Chemical class C1=CC=CC=C1C1=CC=C(C=CC=C2)C2=[O+]1 NWKFECICNXDNOQ-UHFFFAOYSA-N 0.000 abstract 1
- 150000004795 grignard reagents Chemical class 0.000 abstract 1
- 125000000687 hydroquinonyl group Chemical class C1(O)=C(C=C(O)C=C1)* 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 abstract 1
- 229910052740 iodine Inorganic materials 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 abstract 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 125000001453 quaternary ammonium group Chemical group 0.000 abstract 1
- 238000007127 saponification reaction Methods 0.000 abstract 1
- DQFBYFPFKXHELB-VAWYXSNFSA-N trans-chalcone Chemical compound C=1C=CC=CC=1C(=O)\C=C\C1=CC=CC=C1 DQFBYFPFKXHELB-VAWYXSNFSA-N 0.000 abstract 1
- VHBFFQKBGNRLFZ-UHFFFAOYSA-N vitamin p Natural products O1C2=CC=CC=C2C(=O)C=C1C1=CC=CC=C1 VHBFFQKBGNRLFZ-UHFFFAOYSA-N 0.000 abstract 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
- C07D311/58—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4
- C07D311/60—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4 with aryl radicals attached in position 2
- C07D311/62—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4 with aryl radicals attached in position 2 with oxygen atoms directly attached in position 3, e.g. anthocyanidins
-
- 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
- C07D311/58—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4
- C07D311/60—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4 with aryl radicals attached in position 2
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Pyridine Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEM0067001 | 1965-10-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1087539A true GB1087539A (en) | 1967-10-18 |
Family
ID=7312020
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB43600/66A Expired GB1087539A (en) | 1965-10-20 | 1966-09-29 | 3,6-disubstituted flavan derivatives and their preparation |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US3555047A (enExample) |
| BE (1) | BE688588A (enExample) |
| CH (1) | CH487141A (enExample) |
| DE (1) | DE1518038C3 (enExample) |
| DK (1) | DK116739B (enExample) |
| ES (1) | ES332458A1 (enExample) |
| FR (1) | FR7297M (enExample) |
| GB (1) | GB1087539A (enExample) |
| IL (1) | IL26629A (enExample) |
| NL (1) | NL6614645A (enExample) |
| SE (1) | SE353536B (enExample) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0025599A1 (en) * | 1979-09-13 | 1981-03-25 | The Wellcome Foundation Limited | Benzopyran compounds, useful as chemotherapeutic agents |
| EP0652006A1 (en) * | 1993-11-05 | 1995-05-10 | Eli Lilly And Company | Use of 2-phenyl-3-aryl-dihychobenzopyrans for lowering serum cholesterol |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4153617A (en) * | 1974-07-30 | 1979-05-08 | Beecham Group Limited | Anorexic chromans |
| WO2003074044A1 (en) * | 2002-03-01 | 2003-09-12 | Eli Lilly And Company | Substituted benzopyrans as selective estrogen receptor-beta agonists |
-
1965
- 1965-10-20 DE DE1518038A patent/DE1518038C3/de not_active Expired
-
1966
- 1966-09-09 CH CH1306366A patent/CH487141A/de not_active IP Right Cessation
- 1966-09-29 GB GB43600/66A patent/GB1087539A/en not_active Expired
- 1966-10-03 IL IL26629A patent/IL26629A/xx unknown
- 1966-10-18 NL NL6614645A patent/NL6614645A/xx unknown
- 1966-10-19 US US587667A patent/US3555047A/en not_active Expired - Lifetime
- 1966-10-19 ES ES0332458A patent/ES332458A1/es not_active Expired
- 1966-10-19 DK DK540666AA patent/DK116739B/da unknown
- 1966-10-20 BE BE688588D patent/BE688588A/xx unknown
- 1966-10-20 FR FR80735A patent/FR7297M/fr not_active Expired
- 1966-10-20 SE SE14261/66A patent/SE353536B/xx unknown
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0025599A1 (en) * | 1979-09-13 | 1981-03-25 | The Wellcome Foundation Limited | Benzopyran compounds, useful as chemotherapeutic agents |
| EP0652006A1 (en) * | 1993-11-05 | 1995-05-10 | Eli Lilly And Company | Use of 2-phenyl-3-aryl-dihychobenzopyrans for lowering serum cholesterol |
Also Published As
| Publication number | Publication date |
|---|---|
| DK116739B (da) | 1970-02-09 |
| ES332458A1 (es) | 1967-11-01 |
| IL26629A (en) | 1970-08-19 |
| DE1518038C3 (de) | 1975-01-23 |
| FR7297M (enExample) | 1969-11-12 |
| US3555047A (en) | 1971-01-12 |
| CH487141A (de) | 1970-03-15 |
| NL6614645A (enExample) | 1967-04-21 |
| BE688588A (enExample) | 1967-04-20 |
| SE353536B (enExample) | 1973-02-05 |
| DE1518038A1 (de) | 1969-06-26 |
| DE1518038B2 (de) | 1974-06-06 |
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