SU876058A3 - Способ получени производных фурокумарина - Google Patents

Способ получени производных фурокумарина Download PDF

Info

Publication number: SU876058A3
Authority: SU; USSR - Soviet Union
Prior art keywords: formula; mmol; hydrogen atom; ether; carboxylic acid
Prior art date: 1977-07-15

Application number

SU782636897A

Other languages

English (en)

Russian (ru)

Inventor

Биндер Дитер

Ноэ Кристиан

Билек Вальтер

Original Assignee

Герот-Фармацойтика Гмбх (Фирма)

Priority date (The priority date 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 date listed.)

1977-07-15

Filing date

1978-07-14

Publication date

1981-10-23

1978-07-14 Application filed by Герот-Фармацойтика Гмбх (Фирма) filed Critical Герот-Фармацойтика Гмбх (Фирма)

1981-10-23 Application granted granted Critical

1981-10-23 Publication of SU876058A3 publication Critical patent/SU876058A3/ru

Links

238000000034 method Methods 0.000 title description 3
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 30
150000001875 compounds Chemical class 0.000 claims description 9
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 6
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 claims description 6
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 claims description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
229910052708 sodium Inorganic materials 0.000 claims description 4
235000011056 potassium acetate Nutrition 0.000 claims description 3
239000001632 sodium acetate Substances 0.000 claims description 3
235000017281 sodium acetate Nutrition 0.000 claims description 3
238000003684 Perkin reaction Methods 0.000 claims description 2
150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 2
150000001734 carboxylic acid salts Chemical class 0.000 claims description 2
239000003054 catalyst Substances 0.000 claims description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
HPYNZHMRTTWQTB-UHFFFAOYSA-N 2,3-dimethylpyridine Chemical compound CC1=CC=CN=C1C HPYNZHMRTTWQTB-UHFFFAOYSA-N 0.000 claims 2
239000002585 base Substances 0.000 claims 2
IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims 1
GIJHDGJRTUSBJR-UHFFFAOYSA-N Bergaptol Natural products O1C(=O)C=CC2=C1C=C1OC=CC1=C2O GIJHDGJRTUSBJR-UHFFFAOYSA-N 0.000 claims 1
QXKHYNVANLEOEG-UHFFFAOYSA-N Methoxsalen Chemical compound C1=CC(=O)OC2=C1C=C1C=COC1=C2OC QXKHYNVANLEOEG-UHFFFAOYSA-N 0.000 claims 1
PCWZKQSKUXXDDJ-UHFFFAOYSA-N Xanthotoxin Natural products COCc1c2OC(=O)C=Cc2cc3ccoc13 PCWZKQSKUXXDDJ-UHFFFAOYSA-N 0.000 claims 1
YXCORZFYRFZUOV-UHFFFAOYSA-N Xanthotoxol Natural products COc1c2OC(O)C=Cc2cc3ccoc13 YXCORZFYRFZUOV-UHFFFAOYSA-N 0.000 claims 1
125000001931 aliphatic group Chemical group 0.000 claims 1
150000001447 alkali salts Chemical class 0.000 claims 1
125000000499 benzofuranyl group Chemical class O1C(=CC2=C1C=CC=C2)* 0.000 claims 1
229960004469 methoxsalen Drugs 0.000 claims 1
SQBBOVROCFXYBN-UHFFFAOYSA-N methoxypsoralen Natural products C1=C2OC(=O)C(OC)=CC2=CC2=C1OC=C2 SQBBOVROCFXYBN-UHFFFAOYSA-N 0.000 claims 1
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
150000003232 pyrogallols Chemical class 0.000 claims 1
238000003786 synthesis reaction Methods 0.000 claims 1
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
JWVYQQGERKEAHW-UHFFFAOYSA-N xanthotoxol Chemical compound C1=CC(=O)OC2=C1C=C1C=COC1=C2O JWVYQQGERKEAHW-UHFFFAOYSA-N 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 24
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
239000000243 solution Substances 0.000 description 18
238000002844 melting Methods 0.000 description 13
230000008018 melting Effects 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
238000001816 cooling Methods 0.000 description 10
239000003208 petroleum Substances 0.000 description 9
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 8
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 8
229910052938 sodium sulfate Inorganic materials 0.000 description 8
235000011152 sodium sulphate Nutrition 0.000 description 8
QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 7
229940040526 anhydrous sodium acetate Drugs 0.000 description 7
229920006395 saturated elastomer Polymers 0.000 description 7
239000002904 solvent Substances 0.000 description 7
238000003756 stirring Methods 0.000 description 7
239000008346 aqueous phase Substances 0.000 description 5
238000006243 chemical reaction Methods 0.000 description 5
239000012074 organic phase Substances 0.000 description 5
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 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
238000010438 heat treatment Methods 0.000 description 3
238000010992 reflux Methods 0.000 description 3
239000012047 saturated solution Substances 0.000 description 3
JYYNAJVZFGKDEQ-UHFFFAOYSA-N 2,4-Dimethylpyridine Chemical compound CC1=CC=NC(C)=C1 JYYNAJVZFGKDEQ-UHFFFAOYSA-N 0.000 description 2
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 2
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 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
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
239000002253 acid Substances 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
239000000203 mixture Substances 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
239000000741 silica gel Substances 0.000 description 2
229910002027 silica gel Inorganic materials 0.000 description 2
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 1
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 1
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
ZXKIFUWANBZSKF-UHFFFAOYSA-N [I].CC(O)=O Chemical compound [I].CC(O)=O ZXKIFUWANBZSKF-UHFFFAOYSA-N 0.000 description 1
125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 1
150000001299 aldehydes Chemical class 0.000 description 1
239000003513 alkali Substances 0.000 description 1
238000013329 compounding Methods 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 1
238000001035 drying Methods 0.000 description 1
238000000605 extraction Methods 0.000 description 1
230000020477 pH reduction Effects 0.000 description 1
238000012856 packing Methods 0.000 description 1
238000007363 ring formation reaction Methods 0.000 description 1
238000007127 saponification reaction Methods 0.000 description 1
239000011734 sodium Substances 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)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Cosmetics (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)

SU782636897A 1977-07-15 1978-07-14 Способ получени производных фурокумарина SU876058A3 (ru)

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
SU876058A3 true SU876058A3 (ru)	1981-10-23

Family

ID=3572227

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SU782636897A SU876058A3 (ru)	1977-07-15	1978-07-14	Способ получени производных фурокумарина

Country Status (8)

Country	Link
AT (1)	AT362369B (de)
CS (1)	CS201009B2 (de)
DD (1)	DD137587A5 (de)
HU (1)	HU175083B (de)
NL (1)	NL7807394A (de)
PL (1)	PL208406A1 (de)
SU (1)	SU876058A3 (de)
YU (1)	YU156378A (de)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
RU2282633C1 (ru) *	2005-04-04	2006-08-27	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
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

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 DD DD20672878A patent/DD137587A5/de unknown
- 1978-07-14 PL PL20840678A patent/PL208406A1/xx unknown
- 1978-07-14 SU SU782636897A patent/SU876058A3/ru active

Cited By (6)

* Cited by examiner, † Cited by third party
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
US7951971B1 (en)	1999-11-05	2011-05-31	Emisphere Technologies, Inc.	Phenoxy carboxylic acid compounds and compositions for delivering active agents
US8410309B2 (en)	1999-11-05	2013-04-02	Emisphere Technologies, Inc.	Phenoxy carboxylic acid compounds and compositions for delivering active agents
RU2282633C1 (ru) *	2005-04-04	2006-08-27	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
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

Also Published As

Publication number	Publication date
PL208406A1 (pl)	1979-06-04
NL7807394A (nl)	1979-01-17
YU156378A (en)	1982-10-31
CS201009B2 (cs)	1980-10-31
ATA512877A (de)	1980-10-15
HU175083B (hu)	1980-05-28
DD137587A5 (de)	1979-09-12
AT362369B (de)	1981-05-11

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