CH641796A5 - Procedimento selettivo per la preparazione di derivati della 7-idrossicumarina. - Google Patents
Procedimento selettivo per la preparazione di derivati della 7-idrossicumarina. Download PDFInfo
- Publication number
- CH641796A5 CH641796A5 CH975079A CH975079A CH641796A5 CH 641796 A5 CH641796 A5 CH 641796A5 CH 975079 A CH975079 A CH 975079A CH 975079 A CH975079 A CH 975079A CH 641796 A5 CH641796 A5 CH 641796A5
- Authority
- CH
- Switzerland
- Prior art keywords
- derivatives
- methyl
- selective process
- hydroxycoumarin
- preparation
- Prior art date
Links
- 238000000034 method Methods 0.000 title description 8
- 238000002360 preparation method Methods 0.000 title description 2
- ORHBXUUXSCNDEV-UHFFFAOYSA-N umbelliferone Chemical class C1=CC(=O)OC2=CC(O)=CC=C21 ORHBXUUXSCNDEV-UHFFFAOYSA-N 0.000 title 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 239000000203 mixture Substances 0.000 description 5
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 238000002425 crystallisation Methods 0.000 description 4
- 230000008025 crystallization Effects 0.000 description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 4
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 3
- VEUUMBGHMNQHGO-UHFFFAOYSA-N ethyl chloroacetate Chemical compound CCOC(=O)CCl VEUUMBGHMNQHGO-UHFFFAOYSA-N 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
- 235000015320 potassium carbonate Nutrition 0.000 description 3
- 229960001755 resorcinol Drugs 0.000 description 3
- 125000001424 substituent group Chemical group 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
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- KLOIYEQEVSIOOO-UHFFFAOYSA-N carbocromen Chemical class CC1=C(CCN(CC)CC)C(=O)OC2=CC(OCC(=O)OCC)=CC=C21 KLOIYEQEVSIOOO-UHFFFAOYSA-N 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- OVARTBFNCCXQKS-UHFFFAOYSA-N propan-2-one;hydrate Chemical compound O.CC(C)=O OVARTBFNCCXQKS-UHFFFAOYSA-N 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- SWZVJOLLQTWFCW-UHFFFAOYSA-N 2-chlorobenzene-1,3-diol Chemical compound OC1=CC=CC(O)=C1Cl SWZVJOLLQTWFCW-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- AOJDZKCUAATBGE-UHFFFAOYSA-N bromomethane Chemical compound Br[CH2] AOJDZKCUAATBGE-UHFFFAOYSA-N 0.000 description 1
- 229960005003 carbocromen Drugs 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 125000005111 carboxyalkoxy group Chemical group 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- HQCYVSPJIOJEGA-UHFFFAOYSA-N methoxycoumarin Chemical compound C1=CC=C2OC(=O)C(OC)=CC2=C1 HQCYVSPJIOJEGA-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000007858 starting material Substances 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
- C07D311/06—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2
- C07D311/08—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring
- C07D311/16—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring substituted in position 7
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyrane Compounds (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT29466/78A IT1100069B (it) | 1978-11-06 | 1978-11-06 | Procedimento selettivo per la preparazione di derivati della 7-idrossicumarina |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH641796A5 true CH641796A5 (it) | 1984-03-15 |
Family
ID=11227039
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH975079A CH641796A5 (it) | 1978-11-06 | 1979-10-31 | Procedimento selettivo per la preparazione di derivati della 7-idrossicumarina. |
Country Status (16)
| Country | Link |
|---|---|
| JP (1) | JPS5569575A (de) |
| AT (1) | AT372380B (de) |
| BE (1) | BE879821A (de) |
| CA (1) | CA1113948A (de) |
| CH (1) | CH641796A5 (de) |
| DE (1) | DE2944376A1 (de) |
| ES (1) | ES485745A1 (de) |
| FI (1) | FI793400A7 (de) |
| FR (1) | FR2440948A1 (de) |
| GB (1) | GB2036017B (de) |
| GR (1) | GR68055B (de) |
| IT (1) | IT1100069B (de) |
| NL (1) | NL7907983A (de) |
| PT (1) | PT70412A (de) |
| YU (1) | YU40580B (de) |
| ZA (1) | ZA795805B (de) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5484951A (en) * | 1990-10-19 | 1996-01-16 | Octamer, Incorporated | 5-iodo-6-amino-6-nitroso-1,2-benzopyrones useful as cytostatic and antiviral agents |
| US5877185A (en) * | 1991-10-22 | 1999-03-02 | Octamer, Inc. | Synergistic compositions useful as anti-tumor agents |
| US5482975A (en) * | 1991-10-22 | 1996-01-09 | Octamer, Inc. | Adenosine diphosphoribose polymerase binding nitroso aromatic compounds useful as retroviral inactivating agents, anti-retroviral agents and anti-tumor agents |
| US5783599A (en) * | 1993-02-24 | 1998-07-21 | Octamer Inc | Methods of treating cancer and viral infections with 5-iodo-6-amino-and 5-iodo-6-nitroso-1 2-benzopyrones |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2361M (fr) * | 1961-08-12 | 1964-02-24 | Cassella Farbwerke Mainkur Ag | Médicament coronaro-dilatateur renfermant un dérivé de la 7-hydroxy-coumarine. |
| DE2039867A1 (de) * | 1970-08-11 | 1972-02-17 | Troponwerke Dinklage & Co | Pharmakologisch wirksame Coumarin-Drivate und Verfahren zu ihrer Darstellung |
| IT1088554B (it) * | 1977-11-17 | 1985-06-10 | F I D I A Spa | Procedimento sellettivo per la preparazione di derivati della 7-indrossi cumarina |
-
1978
- 1978-11-06 IT IT29466/78A patent/IT1100069B/it active
-
1979
- 1979-10-30 ZA ZA00795805A patent/ZA795805B/xx unknown
- 1979-10-31 CH CH975079A patent/CH641796A5/it not_active IP Right Cessation
- 1979-10-31 FI FI793400A patent/FI793400A7/fi not_active Application Discontinuation
- 1979-10-31 NL NL7907983A patent/NL7907983A/nl not_active Application Discontinuation
- 1979-11-02 DE DE19792944376 patent/DE2944376A1/de not_active Withdrawn
- 1979-11-05 GB GB7938197A patent/GB2036017B/en not_active Expired
- 1979-11-05 PT PT70412A patent/PT70412A/pt unknown
- 1979-11-05 YU YU2696/79A patent/YU40580B/xx unknown
- 1979-11-05 JP JP14376579A patent/JPS5569575A/ja active Pending
- 1979-11-05 BE BE0/197963A patent/BE879821A/fr not_active IP Right Cessation
- 1979-11-05 CA CA339,137A patent/CA1113948A/en not_active Expired
- 1979-11-05 GR GR60422A patent/GR68055B/el unknown
- 1979-11-06 ES ES485745A patent/ES485745A1/es not_active Expired
- 1979-11-06 FR FR7927350A patent/FR2440948A1/fr active Granted
- 1979-11-06 AT AT0712979A patent/AT372380B/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| DE2944376A1 (de) | 1980-05-14 |
| FI793400A7 (fi) | 1981-01-01 |
| YU269679A (en) | 1983-01-21 |
| IT1100069B (it) | 1985-09-28 |
| ATA712979A (de) | 1983-02-15 |
| NL7907983A (nl) | 1980-05-08 |
| AT372380B (de) | 1983-09-26 |
| FR2440948B1 (de) | 1983-06-24 |
| ES485745A1 (es) | 1980-07-01 |
| JPS5569575A (en) | 1980-05-26 |
| GB2036017A (en) | 1980-06-25 |
| CA1113948A (en) | 1981-12-08 |
| YU40580B (en) | 1986-02-28 |
| ZA795805B (en) | 1980-10-29 |
| FR2440948A1 (fr) | 1980-06-06 |
| IT7829466A0 (it) | 1978-11-06 |
| PT70412A (en) | 1979-12-01 |
| GB2036017B (en) | 1983-03-23 |
| BE879821A (fr) | 1980-03-03 |
| GR68055B (de) | 1981-10-29 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |