SU995706A3 - Способ получени 2-циклопропилхромонов или их солей - Google Patents

Способ получени 2-циклопропилхромонов или их солей Download PDF

Info

Publication number: SU995706A3
Authority: SU; USSR - Soviet Union
Prior art keywords: trans; carboxy; chromone; cyclopropyl; propyl
Prior art date: 1978-06-30

Application number

SU782644251A

Other languages

English (en)

Russian (ru)

Inventor

Дория Джанфедерико

Ромео Чириако

Луиза Корно Мария

Лаурия Франческо

Сберзе Пьеро

Тиболла Марчеллино

Original Assignee

Фармиталия Карло Эрба С.П.А. (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.)

1978-06-30

Filing date

1978-08-01

Publication date

1983-02-07

1978-08-01 Application filed by Фармиталия Карло Эрба С.П.А. (Фирма) filed Critical Фармиталия Карло Эрба С.П.А. (Фирма)

1983-02-07 Application granted granted Critical

1983-02-07 Publication of SU995706A3 publication Critical patent/SU995706A3/ru

Links

150000003839 salts Chemical class 0.000 title claims description 11
YNYQZWOWYAQXDE-UHFFFAOYSA-N 2-cyclopropylchromen-4-one Chemical class O1C2=CC=CC=C2C(=O)C=C1C1CC1 YNYQZWOWYAQXDE-UHFFFAOYSA-N 0.000 title claims description 3
238000004519 manufacturing process Methods 0.000 title 1
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 39
150000001875 compounds Chemical class 0.000 claims description 39
-1 2,5-dimethylphenyl Chemical group 0.000 claims description 29
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 29
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 29
239000002244 precipitate Substances 0.000 claims description 20
239000000243 solution Substances 0.000 claims description 20
238000000034 method Methods 0.000 claims description 17
238000003756 stirring Methods 0.000 claims description 17
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 16
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 15
239000000203 mixture Substances 0.000 claims description 14
239000005457 ice water Substances 0.000 claims description 13
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 10
238000001816 cooling Methods 0.000 claims description 10
230000007935 neutral effect Effects 0.000 claims description 10
239000011541 reaction mixture Substances 0.000 claims description 9
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 8
125000000217 alkyl group Chemical group 0.000 claims description 8
238000010992 reflux Methods 0.000 claims description 8
239000002253 acid Substances 0.000 claims description 7
OTAFHZMPRISVEM-UHFFFAOYSA-N chromone Chemical compound C1=CC=C2C(=O)C=COC2=C1 OTAFHZMPRISVEM-UHFFFAOYSA-N 0.000 claims description 7
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 7
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 5
238000002329 infrared spectrum Methods 0.000 claims description 5
125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims description 5
238000001953 recrystallisation Methods 0.000 claims description 5
BPLKQGGAXWRFOE-UHFFFAOYSA-M trimethylsulfoxonium iodide Chemical compound [I-].C[S+](C)(C)=O BPLKQGGAXWRFOE-UHFFFAOYSA-M 0.000 claims description 5
125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims description 4
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 4
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 4
239000000047 product Substances 0.000 claims description 4
239000012312 sodium hydride Substances 0.000 claims description 4
229910000104 sodium hydride Inorganic materials 0.000 claims description 4
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
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 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 3
238000006243 chemical reaction Methods 0.000 claims description 3
238000001704 evaporation Methods 0.000 claims description 3
230000008020 evaporation Effects 0.000 claims description 3
239000012044 organic layer Substances 0.000 claims description 3
239000011734 sodium Substances 0.000 claims description 3
229910052708 sodium Inorganic materials 0.000 claims description 3
159000000000 sodium salts Chemical class 0.000 claims description 3
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
150000002148 esters Chemical class 0.000 claims description 2
125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims description 2
239000003960 organic solvent Substances 0.000 claims description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 4
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 claims 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims 3
238000010790 dilution Methods 0.000 claims 3
239000012895 dilution Substances 0.000 claims 3
BFSVOASYOCHEOV-UHFFFAOYSA-N 2-diethylaminoethanol Chemical compound CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 claims 2
229940013085 2-diethylaminoethanol Drugs 0.000 claims 2
HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 claims 2
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims 2
125000004076 pyridyl group Chemical group 0.000 claims 2
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims 2
125000001617 2,3-dimethoxy phenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C(OC([H])([H])[H])=C1[H] 0.000 claims 1
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims 1
MELCWEWUZODSIS-UHFFFAOYSA-N 2-[2-(diethylamino)ethoxy]-n,n-diethylethanamine Chemical compound CCN(CC)CCOCCN(CC)CC MELCWEWUZODSIS-UHFFFAOYSA-N 0.000 claims 1
RLWICWUBNUTKAA-UHFFFAOYSA-N 2-propylchromen-4-one Chemical compound C1=CC=C2OC(CCC)=CC(=O)C2=C1 RLWICWUBNUTKAA-UHFFFAOYSA-N 0.000 claims 1
AKDQCVKDNMUHGF-UONOGXRCSA-N 3-methoxy-4-oxo-2-[(1R,2R)-2-phenylcyclopropyl]chromene-6-carboxylic acid Chemical compound C(=O)(O)C=1C=C2C(C(=C(OC2=CC=1)[C@H]1[C@@H](C1)C1=CC=CC=C1)OC)=O AKDQCVKDNMUHGF-UONOGXRCSA-N 0.000 claims 1
241000065675 Cyclops Species 0.000 claims 1
125000004423 acyloxy group Chemical group 0.000 claims 1
125000003342 alkenyl group Chemical group 0.000 claims 1
150000001412 amines Chemical class 0.000 claims 1
LSSIDIPYIGSAIJ-UHFFFAOYSA-N benzene;n,n-diethylethanamine;ethyl acetate Chemical compound CCOC(C)=O.C1=CC=CC=C1.CCN(CC)CC LSSIDIPYIGSAIJ-UHFFFAOYSA-N 0.000 claims 1
GGRHYQCXXYLUTL-UHFFFAOYSA-N chloromethyl 2,2-dimethylpropanoate Chemical compound CC(C)(C)C(=O)OCCl GGRHYQCXXYLUTL-UHFFFAOYSA-N 0.000 claims 1
238000004587 chromatography analysis Methods 0.000 claims 1
229910052804 chromium Inorganic materials 0.000 claims 1
239000011651 chromium Substances 0.000 claims 1
125000004617 chromonyl group Chemical group O1C(=CC(C2=CC=CC=C12)=O)* 0.000 claims 1
125000005805 dimethoxy phenyl group Chemical group 0.000 claims 1
DKWOHBPRFZIUQL-UHFFFAOYSA-N dimethyl-methylidene-oxo-$l^{6}-sulfane Chemical compound C[S+](C)([CH2-])=O DKWOHBPRFZIUQL-UHFFFAOYSA-N 0.000 claims 1
238000004090 dissolution Methods 0.000 claims 1
239000003480 eluent Substances 0.000 claims 1
125000004494 ethyl ester group Chemical group 0.000 claims 1
238000001914 filtration Methods 0.000 claims 1
125000002541 furyl group Chemical group 0.000 claims 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
229910000027 potassium carbonate Inorganic materials 0.000 claims 1
235000015320 potassium carbonate Nutrition 0.000 claims 1
239000000741 silica gel Substances 0.000 claims 1
229910002027 silica gel Inorganic materials 0.000 claims 1
238000003786 synthesis reaction Methods 0.000 claims 1
125000001544 thienyl group Chemical group 0.000 claims 1
241000700159 Rattus Species 0.000 description 5
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230000008025 crystallization Effects 0.000 description 5
239000004480 active ingredient Substances 0.000 description 4
230000003266 anti-allergic effect Effects 0.000 description 4
230000000694 effects Effects 0.000 description 4
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
239000000825 pharmaceutical preparation Substances 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
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XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 3
239000000843 powder Substances 0.000 description 3
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IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 2
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
OZFGYKMNASTSDC-DLBZAZTESA-N 4-oxo-2-[(1R,2R)-2-phenylcyclopropyl]-3-propylchromene-6-carboxylic acid Chemical compound C1([C@@H]2C[C@H]2C2=C(C(C3=CC(=CC=C3O2)C(O)=O)=O)CCC)=CC=CC=C1 OZFGYKMNASTSDC-DLBZAZTESA-N 0.000 description 2
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CSRZQMIRAZTJOY-UHFFFAOYSA-N trimethylsilyl iodide Chemical compound C[Si](C)(C)I CSRZQMIRAZTJOY-UHFFFAOYSA-N 0.000 description 2
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FVIZARNDLVOMSU-UHFFFAOYSA-N ginsenoside K Natural products C1CC(C2(CCC3C(C)(C)C(O)CCC3(C)C2CC2O)C)(C)C2C1C(C)(CCC=C(C)C)OC1OC(CO)C(O)C(O)C1O FVIZARNDLVOMSU-UHFFFAOYSA-N 0.000 description 1
229960001340 histamine Drugs 0.000 description 1
150000004678 hydrides Chemical class 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
208000030603 inherited susceptibility to asthma Diseases 0.000 description 1
238000010253 intravenous injection Methods 0.000 description 1
239000006210 lotion Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Substances [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
239000000594 mannitol Substances 0.000 description 1
235000010355 mannitol Nutrition 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
GIUCRBXWXPTZTI-ZWKOTPCHSA-N methyl 4-oxo-2-[(1R,2R)-2-phenylcyclopropyl]-3-propylchromene-6-carboxylate Chemical compound C1([C@@H]2C[C@H]2C2=C(C(C3=CC(=CC=C3O2)C(=O)OC)=O)CCC)=CC=CC=C1 GIUCRBXWXPTZTI-ZWKOTPCHSA-N 0.000 description 1
229920000609 methyl cellulose Polymers 0.000 description 1
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235000010981 methylcellulose Nutrition 0.000 description 1
238000002156 mixing Methods 0.000 description 1
239000006199 nebulizer Substances 0.000 description 1
238000006386 neutralization reaction Methods 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
239000002736 nonionic surfactant Substances 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
238000004806 packaging method and process Methods 0.000 description 1
239000006072 paste Substances 0.000 description 1
239000008177 pharmaceutical agent Substances 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
230000002265 prevention Effects 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
238000007363 ring formation reaction Methods 0.000 description 1
CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
230000035945 sensitivity Effects 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
208000017520 skin disease Diseases 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
239000007921 spray Substances 0.000 description 1
239000008107 starch Substances 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
238000010254 subcutaneous injection Methods 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
125000005537 sulfoxonium group Chemical group 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
239000012049 topical pharmaceutical composition Substances 0.000 description 1
235000010487 tragacanth Nutrition 0.000 description 1
239000000196 tragacanth Substances 0.000 description 1
229940116362 tragacanth Drugs 0.000 description 1
231100000397 ulcer Toxicity 0.000 description 1
238000009736 wetting Methods 0.000 description 1

Landscapes

Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

SU782644251A 1978-06-30 1978-08-01 Способ получени 2-циклопропилхромонов или их солей SU995706A3 (ru)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
IT25157/78A IT1109516B (it)	1978-06-30	1978-06-30	Procedimento per la preparazione di 2-ciclopropil-cromoni sostituiti

Publications (1)

Publication Number	Publication Date
SU995706A3 true SU995706A3 (ru)	1983-02-07

Family

ID=11215872

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SU782644251A SU995706A3 (ru)	1978-06-30	1978-08-01	Способ получени 2-циклопропилхромонов или их солей

Country Status (3)

Country	Link
CS (1)	CS207642B2 (cs)
IT (1)	IT1109516B (cs)
SU (1)	SU995706A3 (cs)

1978
- 1978-06-30 IT IT25157/78A patent/IT1109516B/it active
- 1978-07-28 CS CS501878A patent/CS207642B2/cs unknown
- 1978-08-01 SU SU782644251A patent/SU995706A3/ru active

Also Published As

Publication number	Publication date
IT7825157A0 (it)	1978-06-30
IT1109516B (it)	1985-12-16
CS207642B2 (cs)	1981-08-31

Publication	Publication Date	Title
DE69305189T2 (de)	1997-03-13	Arylcycloalkylderivate, deren Herstellung und Verwendung
US4159330A (en)	1979-06-26	2-Disubstituted phenyl-3,4-dihydro-4-oxo-quinazoline derivatives and process for their preparation
DE3035086C2 (cs)	1991-01-03
EP0625511B1 (en)	1999-02-17	Heterocyclic compounds and their use in pharmaceutical
EP0072960B1 (de)	1989-06-07	1,5-Diphenylpyrazolin-3-on-Verbindungen sowie Verfahren und Zwischenprodukte zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel
SU995706A3 (ru)	1983-02-07	Способ получени 2-циклопропилхромонов или их солей
JP3037991B2 (ja)	2000-05-08	新規なアコニチン系化合物および鎮痛・抗炎症剤
本間靖 et al.	1982	Studies on antiallergic agents. I. Phenyl-substituted heterocycles with a 5-tetrazolyl or N-(5-tetrazolyl) carbamoyl group.
SU957766A3 (ru)	1982-09-07	Способ получени замещенных 2-циклопропилхромонов или их солей
US4192944A (en)	1980-03-11	Optionally substituted 4-oxo-4H-pyrido[1,2-a]pyrimidine-3-N-(1H-tetrazol-4-yl)carboxamides and their use as antiallergy agents
EP0012925B1 (de)	1982-11-10	Neue Chinoloncarbonsäure-Derivate, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende pharmazeutische Präparate
DE2424671A1 (de)	1974-12-12	Triazoloisochinolinderivate und verfahren zu deren herstellung
US3470165A (en)	1969-09-30	Furochromone derivatives
US4496568A (en)	1985-01-29	Antiinflammatory thieno [2,3-c]pyridine derivatives
EP0000488A1 (de)	1979-02-07	3-Oxaloamino-4-oxo-4H-1-benzopyranderivaten, Verfahren zu deren Herstellung und deren pharmazeutischen Verwendung
DE2461670A1 (de)	1975-07-10	5,6-benzo-gamma-pyronderivate, verfahren zu ihrer herstellung und ihre verwendung in pharmazeutischen zubereitungen
US4157334A (en)	1979-06-05	6-Carboxy-flavone derivatives and process for their preparation
Anderson et al.	1976	Carboxyarylindoles as nonsteroidal antiinflammatory agents
US4307102A (en)	1981-12-22	Phenanthro[2,3-c]pyrazole
CA1154772A (en)	1983-10-04	Substituted 2-(pyridyl-cyclopropyl)-chromones and process for their preparation
US3974161A (en)	1976-08-10	Fused pyrimidin-4(3H)-ones as antiallergy agents
DK156724B (da)	1989-09-25	Analogifremgangsmaade til fremstilling af cyclopropylchromonderivater
US4066670A (en)	1978-01-03	N-dimethylaminopropyl-5-(2-nitrophenyl)-2-furancarboximidamide dihydrochloride monohydrate
EP0094245A2 (en)	1983-11-16	Dihydronaphthyridine derivatives, their preparation and compositions containing them
US5292751A (en)	1994-03-08	5,7-dihydroxy-2-methyl-8-(4-(3-hydroxy-1-(1-propyl))piperidinyl)-4H-1-benzopyran-4-one, its preparation and its use