CS202213B1 - Derivatives of 3,9-diethyl-7-oxo-7h-benzo/c/ fluorene - Google Patents
Derivatives of 3,9-diethyl-7-oxo-7h-benzo/c/ fluorene Download PDFInfo
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- CS202213B1 CS202213B1 CS158478A CS158478A CS202213B1 CS 202213 B1 CS202213 B1 CS 202213B1 CS 158478 A CS158478 A CS 158478A CS 158478 A CS158478 A CS 158478A CS 202213 B1 CS202213 B1 CS 202213B1
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- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 title 2
- 150000001875 compounds Chemical class 0.000 claims description 21
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 15
- 239000011541 reaction mixture Substances 0.000 claims description 12
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 238000009835 boiling Methods 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 239000007858 starting material Substances 0.000 claims description 4
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 claims description 3
- -1 3,9-Diethyl-7-oxo-7H-benzo (c) fluorene derivatives Chemical class 0.000 claims description 3
- YFULOKPMQSJFEA-UHFFFAOYSA-N 3,9-diethyl-5-hydroxybenzo[c]fluoren-7-one Chemical compound C1=C(CC)C=CC2=C3C4=CC=C(CC)C=C4C(=O)C3=CC(O)=C21 YFULOKPMQSJFEA-UHFFFAOYSA-N 0.000 claims description 2
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 239000012442 inert solvent Substances 0.000 claims description 2
- 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 description 2
- 238000004519 manufacturing process Methods 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 206010028980 Neoplasm Diseases 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 238000003402 intramolecular cyclocondensation reaction Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000011877 solvent mixture Substances 0.000 description 2
- LLUAMDVHHNCVFX-UHFFFAOYSA-N 3,9-diethyl-5-hydroxy-7-oxobenzo[c]fluorene-6-carboxylic acid Chemical compound C12=CC=C(CC)C=C2C(O)=C(C(O)=O)C2=C1C1=CC=C(CC)C=C1C2=O LLUAMDVHHNCVFX-UHFFFAOYSA-N 0.000 description 1
- SDPFUOAFZHCWAP-UHFFFAOYSA-N 6-ethyl-1-(4-ethylphenyl)-4-methoxynaphthalene-2,3-dicarbonitrile Chemical compound C1=CC(CC)=CC=C1C1=C(C#N)C(C#N)=C(OC)C2=CC(CC)=CC=C12 SDPFUOAFZHCWAP-UHFFFAOYSA-N 0.000 description 1
- BLIUWJRHDOWUGL-UHFFFAOYSA-N 6-ethyl-9-(4-ethylphenyl)-4-methoxybenzo[f][2]benzofuran-1,3-dione Chemical compound C1=CC(CC)=CC=C1C1=C(C(=O)OC2=O)C2=C(OC)C2=CC(CC)=CC=C12 BLIUWJRHDOWUGL-UHFFFAOYSA-N 0.000 description 1
- FZXOFLQOCKRLPO-UHFFFAOYSA-N C1=CC(CC)=CC=C1C1=C(C#N)C(C#N)=C(O)C2=CC(CC)=CC=C12 Chemical compound C1=CC(CC)=CC=C1C1=C(C#N)C(C#N)=C(O)C2=CC(CC)=CC=C12 FZXOFLQOCKRLPO-UHFFFAOYSA-N 0.000 description 1
- AWJVNVPRYGDYHX-UHFFFAOYSA-N C1=CC(CC)=CC=C1C1=C(C#N)C(C#N)=C(OC(C)=O)C2=CC(CC)=CC=C12 Chemical compound C1=CC(CC)=CC=C1C1=C(C#N)C(C#N)=C(OC(C)=O)C2=CC(CC)=CC=C12 AWJVNVPRYGDYHX-UHFFFAOYSA-N 0.000 description 1
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 1
- 102000014150 Interferons Human genes 0.000 description 1
- 108010050904 Interferons Proteins 0.000 description 1
- 238000006898 Intramolecular Friedel-Crafts reaction Methods 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 206010039491 Sarcoma Diseases 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000003463 adsorbent Substances 0.000 description 1
- 230000000118 anti-neoplastic effect Effects 0.000 description 1
- 230000000840 anti-viral effect Effects 0.000 description 1
- 239000002246 antineoplastic agent Substances 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- UXTMROKLAAOEQO-UHFFFAOYSA-N chloroform;ethanol Chemical compound CCO.ClC(Cl)Cl UXTMROKLAAOEQO-UHFFFAOYSA-N 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229940127089 cytotoxic agent Drugs 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 229940079322 interferon Drugs 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 125000002560 nitrile group Chemical group 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Vynález se týká derivátů 3,9-diethyl-7oxo-TH-benzo(c)fluorenu obecného vzorce IThe invention relates to 3,9-diethyl-7-oxo-TH-benzo (c) fluorene derivatives of the general formula I
Látka obecného vzorce I, ve kterém R značí atom vodíku, se podle vynálezu připravuje z látky obecného vzorce IIAccording to the invention, a compound of formula I in which R is hydrogen is prepared from a compound of formula II
ve kterém R značí atom vodíku nebo skupinu karboxylovou, jakož i způsobu výroby uvedených látek.wherein R represents a hydrogen atom or a carboxyl group, as well as a process for the preparation of said compounds.
Látky obecného vzorce I, o výše uvedeném významu R, vykázaly při biologickém hodnocení na zvířatech s transplantovanými nádory antineoplastický účinek a jsou potenciálními chemoterapeutiky lidských nádorových onemocnění. Např. 3,9-diethyl5-hydroxy-7-oxo-7H-benzo (c) f luoren-6-karboxylová kyselina, v dávce 100 mg/kg/den, podávaná myším s. c., kontinuálně po dobu 10 dní prodloužila významně dobu života léčených zvířat se sarkomem S 37, ve srovnání s kontrolní skupinou zvířat neléčených. Mimo to jsou látky obecného vzorce I, o výše uvedeném významu R, cennými MteicKými meziprodukty pro synthesu dalších farmakologicky účinných látek, zvláště pak látek s protivirovým a interferon generujícím účinkem.The compounds of formula I, having the above-mentioned meaning of R, have shown an antineoplastic effect in animal tumors transplanted in animals and are potential chemotherapeutic agents for human cancer. E.g. 3,9-diethyl-5-hydroxy-7-oxo-7H-benzo (c) fluorene-6-carboxylic acid, at a dose of 100 mg / kg / day, administered to sc mice continuously for 10 days significantly prolonged the life of the treated animals with sarcoma S 37 compared to the untreated control group. In addition, the compounds of formula (I), as defined above for R, are valuable intermediates for the synthesis of other pharmacologically active substances, in particular those having antiviral and interferon generating activity.
ve kterém R1 značí atom vodíku, methylnebo acetylskupinu, hydrolýzou nitrilových skupin působením zředěné kyseliny sírové (20 až 90 % J v prostředí kyseliny octové, při teplotách od 100 °C až do teploty varu reakční směsi, po dobu 1 až 10 hodin.wherein R 1 is hydrogen, methyl or acetyl by hydrolyzing nitrile groups with dilute sulfuric acid (20-90% J in acetic acid, at temperatures from 100 ° C to the boiling point of the reaction mixture for 1 to 10 hours.
Reakční směs po hydrolyse se zpracuje obvyklým způsobem, např. po nalití reakční směsi do vody se vyloučený organický podíl ve formě sraženiny odsaje a přečistí se krystalizaci nebo sloupcovou chromatografií na vhodném adsorbentu.After hydrolysis, the reaction mixture is worked up in the usual manner, for example after pouring the reaction mixture into water, the precipitated organic fraction is filtered off with suction and purified by crystallization or by column chromatography on a suitable adsorbent.
Vznik látky obecného vzorce I, ve kterémFormation of a compound of formula (I) wherein:
R značí atom vodíku, z výchozí látky obecného vzorce II, o výše uvedeném významuR is hydrogen from the starting material of formula (II) as defined above
R1, spočívá v intramolekulární cyklisaciR 1 is based on intramolecular cyclization
202 213202 213
202 213 přechodně vzniklé karboxylové kyseliny působením kyseliny sírové.202 213 carboxylic acids formed temporarily by the action of sulfuric acid.
Látky obecného vzorce II, kde R1 má výše uvedený význam, jsou látky známé a snadno připravitelné podle naší čs. pat. přihlášky A. O. 194 589.Compounds of formula (II), wherein R 1 is as defined above, are known and readily prepared according to U.S. Pat. U.S. Pat. AO 194 589.
Látka obecného vzorce I, kde R značí skupinu karboxylovou, se podle vynálezu připravuje z látek obecného vzorce III,According to the invention, a compound of formula I wherein R is a carboxyl group is prepared from a compound of formula III,
ve kterém R2 značí methyl- nebo ethylskupinu, intramolekulární Friedel-Craftsovou cyklisací, za užití 1 až 2 molekvivalentůj1 bezvodého chloridu hlinitého v prostředí inertního rozpouštědla, výhodně dichlorethanu, při teplotě od 20 °C až do teploty varu reakční směsi, po dobu 1 až 8 hodin.wherein R 2 is methyl or ethyl, by intramolecular Friedel-Crafts cyclization, using 1 to 2 mol equivalents of 1 anhydrous aluminum chloride in an inert solvent, preferably dichloroethane, at a temperature of from 20 ° C to the boiling point of the reaction mixture for 1 up to 8 hours.
Reakční směs po Friedel-Craftově reakci se zpracuje obvyklým způsobem pro tento typ reakcí a surový produkt se přečistí krystalizací z vhodného rozpouštědla nebo směsi rozpouštědel.The reaction mixture after the Friedel-Craft reaction is worked up in the usual manner for this type of reaction and the crude product is purified by crystallization from a suitable solvent or solvent mixture.
Látky obecného vzorce III, o výše uvedeném významu R jsou snadno získatelné ve vysokém výtěžku a vyhovující čistotě.Compounds of formula (III), as defined above, R are readily obtainable in high yield and of satisfactory purity.
K intramolekulární cyklisaci látek vzorce III, o výše uvedeném významu R2, lze použít i jiných kysele reagujících katalysátorů, jako kyseliny sírové, polyfosforečné, chloridu cíničitého, titaničitého nebo bortrifluoretherátu, za užití vhodného prostředí a reakčních podmínek. Tyto způsoby však poskytují požadovanou látku v nižším výtěžku a z tohoto hlediska jsou méně vhodné.The intramolecular cyclization of compounds of formula III, the abovementioned meaning of R 2 may be applied to other acid-forming catalysts such as sulfuric acid, polyphosphoric, stannic chloride, titanium tetrachloride, or bortrifluoretherátu, by using a suitable medium and the reaction conditions. However, these methods provide the desired compound in a lower yield and are less suitable in this respect.
Podrobnější údaje o přípravě látek obecného vzorce I, o výše uvedeném významu R, vyplynou z následujících příkladů provedení, které však rozsah vynálezu nikterak neomezují. V příkladech provedení uvedené teploty tání jsou stanoveny na Koflerově bloku a nejsou korigovány; hodnoty teplot jsou uvedeny ve stupních Celsia.More detailed information on the preparation of the compounds of formula (I), with the meaning of R given above, will be apparent from the following non-limiting examples. In the exemplary embodiments, said melting points are determined on a Kofler block and are not corrected; temperature values are given in degrees Celsius.
Příklady provedeníExamples
Příklad 1Example 1
3,9-Diethyl-5-hydroxy-7-oxo-7H-benzo (c J fluoren3,9-Diethyl-5-hydroxy-7-oxo-7H-benzo (c) fluorene
a) k suspensi 5,0 g (13,6 mmol) 7-ethyl4- (4-ethylfenyl) -2,3-dikyan-l-acetoxynaftalenu ve 140 ml kyseliny octové a 80 ml vody se přikape 120 ml koncentrované kyseliny sírové, reakční směs se refluxuje po dobu 3 hodin, po ochlazení se nalije do vody a vyloučená látka se odsaje, promyje vodou a po vysušení se překrystalisuje ze směsi ehloroform-ethanol. Rekrystalisací z téže směsi rozpouštědel se získá produkt o t. t. 255 až 257°.(a) to a suspension of 5,0 g (13,6 mmol) of 7-ethyl-4- (4-ethylphenyl) -2,3-dicyano-1-acetoxynaphthalene in 140 ml of acetic acid and 80 ml of water are added dropwise 120 ml of concentrated sulfuric acid; the reaction mixture is refluxed for 3 hours, poured into water after cooling and the precipitate is filtered off with suction, washed with water and, after drying, recrystallized from chloroform-ethanol. Recrystallization from the same solvent mixture gave the product, m.p. 255-257 °.
bj k suspensi 1,0 g (3,05 mmol) 7-ethyl4- (4-ethylfenyl) -2,3-dikyan-alf a-naftolu ve 20 ml kyseliny octové a 10 ml vody se přikape za míchání 20 Oml koncentrované kyseliny sírové a reakční směs se refluxuje 2 hodiny a zpracuje se stejným způsobem jako v případě aj.bj to a suspension of 1.0 g (3.05 mmol) of 7-ethyl-4- (4-ethylphenyl) -2,3-dicyano-alpha-naphthol in 20 ml of acetic acid and 10 ml of water dropwise with stirring 20 ml of concentrated acid the sulfur and reaction mixture was refluxed for 2 hours and worked up in the same manner as in the case of a.
cj k suspensi 20,5 g (0,06 mol) 7-ethyl4- (4-ethylfenyl) -2,3-dikyan-l-methoxynaf talenu v 500 ml kyseliny octové a 150 ml vody se přikape 500 ml koncentrované kyseliny sírové a reakční směs se refluxuje 5 hodin a reakční směs se zpracuje stejným způsobem jako v případě a).cj to a suspension of 20.5 g (0.06 mol) of 7-ethyl-4- (4-ethylphenyl) -2,3-dicyano-1-methoxynaphthalene in 500 ml of acetic acid and 150 ml of water was added dropwise 500 ml of concentrated sulfuric acid; the reaction mixture is refluxed for 5 hours and the reaction mixture is treated in the same manner as in a).
Příklad 2Example 2
Kyselina 3,9-diethyl-5-hydroxy-7-oxo-7H-benzo (c) f luor en-6-kar boxylová3,9-Diethyl-5-hydroxy-7-oxo-7H-benzo (c) fluoro-6-carboxylic acid
K roztoku 14,4 g (0,04 mol) anhydridu kyseliny 7-ethyl-4- (4-ethylfenyl j -1-methoxynaftalen-2,3-dikarboxylové v 240 ml dichlorethanolu se přidá při teplotě 20 až 25° 10,6 g (0,08 mól) bezvodého chloridu hlinitého a reakční směs se refluxuje 4 hodiny, pak se ochladí a rozloží se nalitím do směsi obsahující 540 ml vody a 160 ml kyseliny solné. Vyloučený surový produkt se vyjme do chloroformu a přečistí se krystalisací ze směsi chloroforethanol (1:1); získá se látka o t. t. 257 až 260°.To a solution of 14.4 g (0.04 mol) of 7-ethyl-4- (4-ethylphenyl) -1-methoxynaphthalene-2,3-dicarboxylic acid anhydride in 240 ml of dichloroethane is added 10.6 at 20-25 °. g (0.08 mol) of anhydrous aluminum chloride was added and the reaction mixture was refluxed for 4 hours, then cooled and quenched by pouring into a mixture containing 540 ml of water and 160 ml of hydrochloric acid, and the precipitated crude product was taken up in chloroform. chloroform: ethanol (1: 1), mp 257-260 °.
Stejný produkt se získá za užití anhydridu kyseliny 7-ethyl-4-(-ethylfenylj-l-ethoxynaftalen-2,3-dikarboxylové jako výchozí látky.The same product was obtained starting from 7-ethyl-4- (ethylphenyl) -1-ethoxynaphthalene-2,3-dicarboxylic acid anhydride.
202 213202 213
Claims (8)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS158478A CS202213B1 (en) | 1978-03-13 | 1978-03-13 | Derivatives of 3,9-diethyl-7-oxo-7h-benzo/c/ fluorene |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS158478A CS202213B1 (en) | 1978-03-13 | 1978-03-13 | Derivatives of 3,9-diethyl-7-oxo-7h-benzo/c/ fluorene |
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| Publication Number | Publication Date |
|---|---|
| CS202213B1 true CS202213B1 (en) | 1980-12-31 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS158478A CS202213B1 (en) | 1978-03-13 | 1978-03-13 | Derivatives of 3,9-diethyl-7-oxo-7h-benzo/c/ fluorene |
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| Country | Link |
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| CS (1) | CS202213B1 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109912512A (en) * | 2017-12-13 | 2019-06-21 | 上海科胜药物研发有限公司 | A kind of new Telmisartan impurity compound and its preparation method and application |
-
1978
- 1978-03-13 CS CS158478A patent/CS202213B1/en unknown
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109912512A (en) * | 2017-12-13 | 2019-06-21 | 上海科胜药物研发有限公司 | A kind of new Telmisartan impurity compound and its preparation method and application |
| CN109912512B (en) * | 2017-12-13 | 2023-05-30 | 上海科胜药物研发有限公司 | New telmisartan impurity compound and preparation method and application thereof |
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