CS201009B2 - Způsob výroby derivátů 9-methoxy-7H-furo-(3,2-g)(1)-benzopyran-7-onu - Google Patents
Způsob výroby derivátů 9-methoxy-7H-furo-(3,2-g)(1)-benzopyran-7-onu Download PDFInfo
- Publication number
- CS201009B2 CS201009B2 CS443978A CS443978A CS201009B2 CS 201009 B2 CS201009 B2 CS 201009B2 CS 443978 A CS443978 A CS 443978A CS 443978 A CS443978 A CS 443978A CS 201009 B2 CS201009 B2 CS 201009B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- iii
- mmol
- ether
- compound
- methoxy
- Prior art date
Links
- QXKHYNVANLEOEG-UHFFFAOYSA-N Methoxsalen Chemical class C1=CC(=O)OC2=C1C=C1C=COC1=C2OC QXKHYNVANLEOEG-UHFFFAOYSA-N 0.000 claims description 17
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 17
- 150000001875 compounds Chemical class 0.000 claims description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 6
- HPYNZHMRTTWQTB-UHFFFAOYSA-N 2,3-dimethylpyridine Chemical compound CC1=CC=CN=C1C HPYNZHMRTTWQTB-UHFFFAOYSA-N 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 claims description 3
- 238000003684 Perkin reaction Methods 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 claims description 3
- 150000001907 coumarones Chemical class 0.000 claims description 3
- 239000003054 catalyst Substances 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 3
- 150000002431 hydrogen Chemical group 0.000 claims 2
- 150000003232 pyrogallols Chemical class 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 66
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 24
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 20
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 13
- 239000000243 solution Substances 0.000 description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 239000012071 phase Substances 0.000 description 11
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 10
- 238000001816 cooling Methods 0.000 description 10
- 229960004469 methoxsalen Drugs 0.000 description 10
- 239000003208 petroleum Substances 0.000 description 9
- 229910052938 sodium sulfate Inorganic materials 0.000 description 9
- 235000011152 sodium sulphate Nutrition 0.000 description 9
- GOFQRLNJZFQDGG-UHFFFAOYSA-N 6-hydroxy-7-methoxy-1-benzofuran-5-carbaldehyde Chemical compound COC1=C(O)C(C=O)=CC2=C1OC=C2 GOFQRLNJZFQDGG-UHFFFAOYSA-N 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 6
- 239000008346 aqueous phase Substances 0.000 description 6
- ZRGFVGWYWMJNOH-UHFFFAOYSA-N (5-formyl-7-methoxy-1-benzofuran-6-yl) acetate Chemical compound C(=O)C=1C(=C(C2=C(C=CO2)C=1)OC)OC(C)=O ZRGFVGWYWMJNOH-UHFFFAOYSA-N 0.000 description 5
- -1 2,4-diformyl-5-acetoxy-6-methoxyphenoxy Chemical group 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 229940040526 anhydrous sodium acetate Drugs 0.000 description 5
- 239000012074 organic phase Substances 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- MOKWZUTYQWEYSV-UHFFFAOYSA-N C(=O)C=1C(=C(C2=C(C=C(O2)C(=O)O)C1)OC)O Chemical compound C(=O)C=1C(=C(C2=C(C=C(O2)C(=O)O)C1)OC)O MOKWZUTYQWEYSV-UHFFFAOYSA-N 0.000 description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
- PCWZKQSKUXXDDJ-UHFFFAOYSA-N Xanthotoxin Natural products COCc1c2OC(=O)C=Cc2cc3ccoc13 PCWZKQSKUXXDDJ-UHFFFAOYSA-N 0.000 description 4
- BERDEBHAJNAUOM-UHFFFAOYSA-N copper(i) oxide Chemical compound [Cu]O[Cu] BERDEBHAJNAUOM-UHFFFAOYSA-N 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000003480 eluent Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- JYYNAJVZFGKDEQ-UHFFFAOYSA-N 2,4-Dimethylpyridine Chemical compound CC1=CC=NC(C)=C1 JYYNAJVZFGKDEQ-UHFFFAOYSA-N 0.000 description 2
- WANKRKFIRRJAMD-UHFFFAOYSA-N C(=O)C=1C(=C(C2=C(C=C(O2)C(=O)O)C1)OC)OC(C)=O Chemical compound C(=O)C=1C(=C(C2=C(C=C(O2)C(=O)O)C1)OC)OC(C)=O WANKRKFIRRJAMD-UHFFFAOYSA-N 0.000 description 2
- MJGKDOBOYBLLEO-UHFFFAOYSA-N COC1=C(C(=CC(=C1OCC(=O)O)C=O)C=O)O Chemical compound COC1=C(C(=CC(=C1OCC(=O)O)C=O)C=O)O MJGKDOBOYBLLEO-UHFFFAOYSA-N 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
- 241001435619 Lile Species 0.000 description 2
- 201000004681 Psoriasis Diseases 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- KRFJLUBVMFXRPN-UHFFFAOYSA-N cuprous oxide Chemical compound [O-2].[Cu+].[Cu+] KRFJLUBVMFXRPN-UHFFFAOYSA-N 0.000 description 2
- 229940112669 cuprous oxide Drugs 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- SQBBOVROCFXYBN-UHFFFAOYSA-N methoxypsoralen Natural products C1=C2OC(=O)C(OC)=CC2=CC2=C1OC=C2 SQBBOVROCFXYBN-UHFFFAOYSA-N 0.000 description 2
- 230000020477 pH reduction Effects 0.000 description 2
- DDBREPKUVSBGFI-UHFFFAOYSA-N phenobarbital Chemical compound C=1C=CC=CC=1C1(CC)C(=O)NC(=O)NC1=O DDBREPKUVSBGFI-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- PFTNSNIUPJYFRB-UHFFFAOYSA-N 4,6-dihydroxy-5-methoxybenzene-1,3-dicarbaldehyde Chemical compound OC1=C(C=C(C=O)C(=C1OC)O)C=O PFTNSNIUPJYFRB-UHFFFAOYSA-N 0.000 description 1
- BUNGCZLFHHXKBX-UHFFFAOYSA-N 8-methoxypsoralen Natural products C1=CC(=O)OC2=C1C=C1CCOC1=C2OC BUNGCZLFHHXKBX-UHFFFAOYSA-N 0.000 description 1
- 229940027041 8-mop Drugs 0.000 description 1
- HAGREJWEXYKQEV-UHFFFAOYSA-N 9-methoxy-7-oxofuro[3,2-g]chromene-6-carboxylic acid Chemical compound C1=C(C(O)=O)C(=O)OC2=C1C=C1C=COC1=C2OC HAGREJWEXYKQEV-UHFFFAOYSA-N 0.000 description 1
- RDJHCKHLMLNWND-UHFFFAOYSA-N CC(=O)OC1=C(C=C(C(=C1OC)OCC(=O)O)C=O)C=O Chemical compound CC(=O)OC1=C(C=C(C(=C1OC)OCC(=O)O)C=O)C=O RDJHCKHLMLNWND-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical class [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- LZLOFGMGFADIKQ-UHFFFAOYSA-N benzene;1,4-dioxane Chemical compound C1COCCO1.C1=CC=CC=C1 LZLOFGMGFADIKQ-UHFFFAOYSA-N 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- VJBCBLLQDMITLJ-UHFFFAOYSA-N chromen-7-one Chemical compound C1=COC2=CC(=O)C=CC2=C1 VJBCBLLQDMITLJ-UHFFFAOYSA-N 0.000 description 1
- 230000001684 chronic effect Effects 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 125000000332 coumarinyl group Chemical group O1C(=O)C(=CC2=CC=CC=C12)* 0.000 description 1
- 206010012601 diabetes mellitus Diseases 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- JDNTWHVOXJZDSN-UHFFFAOYSA-N iodoacetic acid Chemical compound OC(=O)CI JDNTWHVOXJZDSN-UHFFFAOYSA-N 0.000 description 1
- 238000009533 lab test Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- VOVZXURTCKPRDQ-CQSZACIVSA-N n-[4-[chloro(difluoro)methoxy]phenyl]-6-[(3r)-3-hydroxypyrrolidin-1-yl]-5-(1h-pyrazol-5-yl)pyridine-3-carboxamide Chemical compound C1[C@H](O)CCN1C1=NC=C(C(=O)NC=2C=CC(OC(F)(F)Cl)=CC=2)C=C1C1=CC=NN1 VOVZXURTCKPRDQ-CQSZACIVSA-N 0.000 description 1
- 239000005445 natural material Substances 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 238000005192 partition Methods 0.000 description 1
- 239000000419 plant extract Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 230000001185 psoriatic effect Effects 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 208000017520 skin disease Diseases 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/86—Benzo [b] furans; Hydrogenated benzo [b] furans with an oxygen atom directly attached in position 7
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Cosmetics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT512877A AT362369B (de) | 1977-07-15 | 1977-07-15 | Verfahren zur herstellung von furocumarin- derivaten |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS201009B2 true CS201009B2 (cs) | 1980-10-31 |
Family
ID=3572227
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS443978A CS201009B2 (cs) | 1977-07-15 | 1978-07-04 | Způsob výroby derivátů 9-methoxy-7H-furo-(3,2-g)(1)-benzopyran-7-onu |
Country Status (8)
| Country | Link |
|---|---|
| AT (1) | AT362369B (pl) |
| CS (1) | CS201009B2 (pl) |
| DD (1) | DD137587A5 (pl) |
| HU (1) | HU175083B (pl) |
| NL (1) | NL7807394A (pl) |
| PL (1) | PL208406A1 (pl) |
| SU (1) | SU876058A3 (pl) |
| YU (1) | YU156378A (pl) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7129274B1 (en) | 1999-11-05 | 2006-10-31 | Emisphere Technologies Inc. | Phenoxy carboxylic acid compounds and compositions for delivering active agents |
| US7279597B1 (en) | 1999-11-05 | 2007-10-09 | Emisphere Technologies, Inc. | Phenyl amine carboxylic acid compounds and compositions for delivering active agents |
| RU2282633C9 (ru) * | 2005-04-04 | 2007-01-20 | Государственное образовательное учреждение высшего профессионального образования "Кубанский государственный технологический университет" (ГОУВПО "КубГТУ") | Способ получения 1,11-диалкил-3,5-дигидрофуро[2',3':3,4]циклогепта[c]изохроменов |
-
1977
- 1977-07-15 AT AT512877A patent/AT362369B/de not_active IP Right Cessation
-
1978
- 1978-06-30 YU YU156378A patent/YU156378A/xx unknown
- 1978-07-04 CS CS443978A patent/CS201009B2/cs unknown
- 1978-07-07 NL NL7807394A patent/NL7807394A/xx not_active Application Discontinuation
- 1978-07-10 HU HU78GE1036A patent/HU175083B/hu unknown
- 1978-07-14 PL PL20840678A patent/PL208406A1/pl unknown
- 1978-07-14 SU SU782636897A patent/SU876058A3/ru active
- 1978-07-14 DD DD20672878A patent/DD137587A5/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| YU156378A (en) | 1982-10-31 |
| AT362369B (de) | 1981-05-11 |
| NL7807394A (nl) | 1979-01-17 |
| ATA512877A (de) | 1980-10-15 |
| PL208406A1 (pl) | 1979-06-04 |
| SU876058A3 (ru) | 1981-10-23 |
| DD137587A5 (de) | 1979-09-12 |
| HU175083B (hu) | 1980-05-28 |
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