CA1113948A - Selective process for the preparation of 7-hydroxycoumarin derivatives - Google Patents
Selective process for the preparation of 7-hydroxycoumarin derivativesInfo
- Publication number
- CA1113948A CA1113948A CA339,137A CA339137A CA1113948A CA 1113948 A CA1113948 A CA 1113948A CA 339137 A CA339137 A CA 339137A CA 1113948 A CA1113948 A CA 1113948A
- Authority
- CA
- Canada
- Prior art keywords
- product
- selective process
- methyl
- reaction
- preparation
- 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
- 238000000034 method Methods 0.000 title claims abstract description 10
- 238000002360 preparation method Methods 0.000 title claims abstract description 5
- 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 claims abstract description 12
- 229910000027 potassium carbonate Inorganic materials 0.000 claims abstract description 7
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 claims abstract description 4
- VEUUMBGHMNQHGO-UHFFFAOYSA-N ethyl chloroacetate Chemical compound CCOC(=O)CCl VEUUMBGHMNQHGO-UHFFFAOYSA-N 0.000 claims abstract description 4
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 claims abstract description 3
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims abstract 8
- 235000015320 potassium carbonate Nutrition 0.000 claims abstract 4
- OMQHDIHZSDEIFH-UHFFFAOYSA-N 3-Acetyldihydro-2(3H)-furanone Chemical compound CC(=O)C1CCOC1=O OMQHDIHZSDEIFH-UHFFFAOYSA-N 0.000 claims abstract 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 8
- 238000001953 recrystallisation Methods 0.000 claims description 4
- OVARTBFNCCXQKS-UHFFFAOYSA-N propan-2-one;hydrate Chemical compound O.CC(C)=O OVARTBFNCCXQKS-UHFFFAOYSA-N 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 2
- 239000000047 product Substances 0.000 abstract description 3
- 239000012467 final product Substances 0.000 abstract 1
- 239000000460 chlorine Substances 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 3
- 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
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- KLOIYEQEVSIOOO-UHFFFAOYSA-N carbocromen Chemical compound CC1=C(CCN(CC)CC)C(=O)OC2=CC(OCC(=O)OCC)=CC=C21 KLOIYEQEVSIOOO-UHFFFAOYSA-N 0.000 description 2
- 229960005003 carbocromen Drugs 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- ZUXNHFFVQWADJL-UHFFFAOYSA-N 3,4,5-trimethoxy-n-(2-methoxyethyl)-n-(4-phenyl-1,3-thiazol-2-yl)benzamide Chemical compound N=1C(C=2C=CC=CC=2)=CSC=1N(CCOC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 ZUXNHFFVQWADJL-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000003218 coronary vasodilator agent Substances 0.000 description 1
- 229960000956 coumarin Drugs 0.000 description 1
- 235000001671 coumarin Nutrition 0.000 description 1
- -1 ethoxy-carbonylmethoxy- Chemical class 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000001475 halogen functional group Chemical group 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 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
- 239000011541 reaction mixture Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 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 (2)
| 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 |
| IT29466A/78 | 1978-11-06 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1113948A true CA1113948A (en) | 1981-12-08 |
Family
ID=11227039
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA339,137A Expired CA1113948A (en) | 1978-11-06 | 1979-11-05 | Selective process for the preparation of 7-hydroxycoumarin derivatives |
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 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 GR GR60422A patent/GR68055B/el unknown
- 1979-11-05 GB GB7938197A patent/GB2036017B/en not_active Expired
- 1979-11-05 CA CA339,137A patent/CA1113948A/en not_active Expired
- 1979-11-06 FR FR7927350A patent/FR2440948A1/fr active Granted
- 1979-11-06 ES ES485745A patent/ES485745A1/es not_active Expired
- 1979-11-06 AT AT0712979A patent/AT372380B/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| GB2036017A (en) | 1980-06-25 |
| NL7907983A (nl) | 1980-05-08 |
| IT1100069B (it) | 1985-09-28 |
| FR2440948A1 (fr) | 1980-06-06 |
| CH641796A5 (it) | 1984-03-15 |
| IT7829466A0 (it) | 1978-11-06 |
| YU40580B (en) | 1986-02-28 |
| ZA795805B (en) | 1980-10-29 |
| AT372380B (de) | 1983-09-26 |
| YU269679A (en) | 1983-01-21 |
| ES485745A1 (es) | 1980-07-01 |
| DE2944376A1 (de) | 1980-05-14 |
| GB2036017B (en) | 1983-03-23 |
| PT70412A (en) | 1979-12-01 |
| ATA712979A (de) | 1983-02-15 |
| JPS5569575A (en) | 1980-05-26 |
| FR2440948B1 (de) | 1983-06-24 |
| FI793400A7 (fi) | 1981-01-01 |
| GR68055B (de) | 1981-10-29 |
| BE879821A (fr) | 1980-03-03 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| RU2120445C1 (ru) | СПОСОБ ПОЛУЧЕНИЯ ФИНАСТЕРИДА, 17β-[N-ТРЕТ-БУТИЛКАРБАМОИЛ]-4-АЗА-5α-АНДРОСТ-1-ЕН-3-ОН В ПОЛИМОРФНОЙ ФОРМЕ I ИЛИ II, СПОСОБЫ ИХ ПОЛУЧЕНИЯ | |
| SU1223842A3 (ru) | Способ получени производных бензофенонгидразонов | |
| US4562263A (en) | Process for producing 3-(3,4-dihydroxyphenyl) serine | |
| EP0008833B1 (de) | Optisch aktive Derivate von Mercaptoisobuttersäure und ein Verfahren zu ihrer Herstellung | |
| KR920002295B1 (ko) | 프롤리디논 유도체의 제조방법 | |
| FI59086B (fi) | Foerfarande foer framstaellning av 2,5-disubstituerade bensamider | |
| JPH04297461A (ja) | ２−チオヒダントイン誘導体 | |
| KR100519691B1 (ko) | 알킬옥시 퓨라논 유도체의 제조방법, 상기 방법으로 얻은화합물 및 상기 화합물의 용도 | |
| GB2036017A (en) | Selective Process for the Preparation of 7-hydroxycoumarin Derivatives | |
| JP2001521498A (ja) | Ｏ−（３−アミノ−２−ヒドロキシ−プロピル）−ヒドロキシミック酸ハロゲン化物の製造方法 | |
| JPH0520425B2 (de) | ||
| JPH082865B2 (ja) | 抗潰瘍作用を有する化合物の製法 | |
| EP2105431A1 (de) | Verfahren zur Herstellung einer Chromonverbindung | |
| JPS6346743B2 (de) | ||
| CH639085A5 (en) | Process for the preparation of xanthone derivatives | |
| RU2151209C1 (ru) | Способ экстракционного разделения платины и палладия | |
| EP0044091A2 (de) | Verfahren zur Herstellung von N-Alkylamino-benzophenonen | |
| JP2001181265A (ja) | メルカプトテトラゾール化合物の製造方法 | |
| KR890002251B1 (ko) | 옥사졸 화합물의 제조방법 | |
| JP2002503648A (ja) | 葉酸拮抗薬を製造するのに有用な方法および中間体 | |
| KR100208297B1 (ko) | 신규한 세펨 유도체의 제조방법 | |
| JP2918136B2 (ja) | ３−ジアルキルアミノ−２−置換ベンゾイルアクリル酸化合物 | |
| JP2536000B2 (ja) | α−ベンジリデン−アセトニルホスホネ―ト類の製法 | |
| JPH0527617B2 (de) | ||
| JPS6259106B2 (de) |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |