CS201121B1 - Beta-4-pentoxybenzoyl-alpha,alpha'-dialoxy-propionic acid,esters thereof and process for their preparation - Google Patents
Beta-4-pentoxybenzoyl-alpha,alpha'-dialoxy-propionic acid,esters thereof and process for their preparation Download PDFInfo
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- CS201121B1 CS201121B1 CS498676A CS498676A CS201121B1 CS 201121 B1 CS201121 B1 CS 201121B1 CS 498676 A CS498676 A CS 498676A CS 498676 A CS498676 A CS 498676A CS 201121 B1 CS201121 B1 CS 201121B1
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- Prior art keywords
- pentoxybenzoyl
- acid
- alpha
- beta
- esters
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- 150000002148 esters Chemical class 0.000 title claims description 4
- 238000000034 method Methods 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 title 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 21
- 239000002253 acid Substances 0.000 claims description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 159000000000 sodium salts Chemical class 0.000 claims description 4
- 239000011541 reaction mixture Substances 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 238000009835 boiling Methods 0.000 claims description 2
- 125000004494 ethyl ester group Chemical group 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 3
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims 2
- HMDKQELOKBDEQQ-UHFFFAOYSA-N 2-bromo-4-oxo-4-(4-pentoxyphenyl)but-2-enoic acid Chemical compound CCCCCOC1=CC=C(C(=O)C=C(Br)C(O)=O)C=C1 HMDKQELOKBDEQQ-UHFFFAOYSA-N 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- 239000000203 mixture Substances 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- -1 4-Pentoxybenzoyl- Chemical group 0.000 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 description 3
- 241001465754 Metazoa Species 0.000 description 3
- 206010028980 Neoplasm Diseases 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- PBEDUQUTJMOUEZ-UHFFFAOYSA-N 2-benzoyl-3-bromo-3-pentan-2-yloxyprop-2-enoic acid Chemical compound CCCC(C)OC(Br)=C(C(O)=O)C(=O)C1=CC=CC=C1 PBEDUQUTJMOUEZ-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 150000004702 methyl esters Chemical class 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 230000000118 anti-neoplastic effect Effects 0.000 description 1
- 239000012223 aqueous fraction Substances 0.000 description 1
- SLUNEGLMXGHOLY-UHFFFAOYSA-N benzene;hexane Chemical compound CCCCCC.C1=CC=CC=C1 SLUNEGLMXGHOLY-UHFFFAOYSA-N 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- BUBWTSJXUHKBBX-UHFFFAOYSA-N ethyl acetate;sodium Chemical compound [Na].CCOC(C)=O BUBWTSJXUHKBBX-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 125000004492 methyl ester group Chemical group 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 238000002054 transplantation Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Vynález se týká kyseliny A-4-pentoxybenzoyl-X , X -dialkoxypropionové a jejích esterů obecného vzorce IThe present invention relates to A-4-pentoxybenzoyl-X, X-dialkoxypropionic acid and its esters of formula I
ve kterém R1 a Rg značí bučí methyl-, nebo ethylskupinu a R^ značí atom vodíku nebo methyl- nebo ethylskupinu, jakož i způsobu výroby látek obecného vzorce I.wherein R 1 and R 8 are either methyl or ethyl, and R 6 is hydrogen or methyl or ethyl, as well as a process for the preparation of the compounds of formula I.
Látky obecného vzorce I vykazují antineoplastické účinky, tlumí růst experimentálních nádorů pokusných zvířat. Tak například kyselina /5 -4-pentoxybenzoyl-e^ ,o^-dimethoxypropionová, podávaná myším kmene H s adenokaroinomem mléčné žlázy v denní dávce 100 mg/kg per os, po dobu 10 dnů, počínaje 7. dnem po transplantaci nádoru, tlumila jeho růst o 30 % při současném přežití zvířat o 41 %(ve srovnání s kontrolní skupinou zvířat neléčených). Kyselina 4 -4-pentoxybenzoyl-íC ,Z -diethoxypropionová, podávaná v denní dávce 200 mg/kg per os zvířatům s týmž nádorem, tlumila jeho růst o 30 % a prodloužila život zvířat o 30 %.The compounds of formula (I) exhibit antineoplastic effects, inhibiting the growth of experimental tumors in experimental animals. For example, β-4-pentoxybenzoyl-ε, ω-dimethoxypropionic acid, administered to mouse strain H with mammary adenocaroin at a daily dose of 100 mg / kg orally for 10 days, starting on day 7 after tumor transplantation, inhibited its growth by 30% while the survival of the animals by 41% (compared to the untreated control group). 4 -4-Pentoxybenzoyl-1, 2-diethoxypropionic acid, administered at a daily dose of 200 mg / kg orally to animals with the same tumor, inhibited its growth by 30% and prolonged the life of the animals by 30%.
201 121201 121
201 121201 121
Látky obecného vzorce I se podle vynálezu připravují tak, že se methyl- neboethylester nebo sodná sůl kyseliny 4-4-pentoxybenzoyl- A -bromakrylové nebo kyseliny A -4-pentoxybenzoyl-Z/ -bromakrylové nechá reagovat s 1 ař 2 ekvivalenty methylátu nebe ethylátu sodného, v prostředí methanolu nebo ethanolu, při teplotě bodu varu reakční směsi.The compounds of the formula I according to the invention are prepared by reacting methyl or ethyl ester or sodium salt of 4-4-pentoxybenzoyl-N-bromoacrylic acid or A-4-pentoxybenzoyl-N-bromoacrylic acid with 1 to 2 equivalents of methylate or ethyl acetate sodium, in methanol or ethanol, at the boiling point of the reaction mixture.
Po ukončení reakce se reakční směs obvykle zpracovává tak, že se použité rozpouštědlo oddestiluje za sníženého tlaku a odparek se zpracuje chromatografií na sloupci silikagelu, za užití benzenu nebo jeho směsi s ethanolem jako eluČního činidla.After completion of the reaction, the reaction mixture is usually worked up by distilling off the solvent under reduced pressure and subjecting the residue to silica gel column chromatography using benzene or a mixture thereof with ethanol as the eluent.
Výchozí kyselina & -4-pentoxybenzoyl- &-bromakrylové je známá (čs. patent spis č. 131764), rovněž i kyselina fi> -4-pentoxybenzoyl-<6 -bromakrylové (čs, autorské osvědčení č. 195 856).The starting β-4-pentoxybenzoyl-β-bromoacrylic acid is known (U.S. Pat. No. 131764), as well as β-4-pentoxybenzoyl-β-bromoacrylic acid (Czech, author's certificate no. 195 856).
Bližší podrobnosti způsobu výroby látek obecného vzorce I jsou zřejmé 2 příkladů provedení.Further details of the process for the preparation of the compounds of the general formula (I) are apparent from 2 exemplary embodiments.
Příklady provedeníExamples
Příklad 1Example 1
Methylester kyseliny-4-pentoxybenzoyl-,«6 -dimethoxypropionové4-Pentoxybenzoyl-, 6-dimethoxypropionic acid methyl ester
3,55 g (0,01 mol) methylesteru kyseliny -4-pentoxybenzoyl-A -bromakrylové se refluxuje 1 h. s roztokem 0,23 g sodíku (0,01 mol) ve 100 ml methanolu pod uzávěrem s pevným hydroxidem draselným. Potom se methanol oddestiluje za sníženého tlaku a odparek se roz třepe ve směsi 25 ml vody a 50 ml etheru. Vodný podíl se Ijrotřepe 2x po 50 ml etheru, etherickó podíly se spojí, vysuší síranem sodným, zfiltrují a odpaří ve vakuu. OXejovitý odparek (2,44 g, 72 %) se chromatografuje na sloupci 50 g silikagelu za užití benzenu jako elučního činidla. Jednotné frakce produktu se spojí (2 g, 59 %) a k analýze usuší při teplotě 60 °C a tlaku 0,1 torrů. Methylester kyseliny -4-pentoxybenzoyl- , -dimethoxypropionové tvoří bezbarvý olej s n^ => 1,5171.3.55 g (0.01 mol) of 4-pentoxybenzoyl-N-bromoacrylic acid methyl ester is refluxed for 1 h. With a solution of 0.23 g of sodium (0.01 mol) in 100 ml of methanol under a solid potassium hydroxide cap. The methanol was then distilled off under reduced pressure and the residue was shaken in a mixture of 25 ml of water and 50 ml of ether. The aqueous fraction was shaken twice with 50 ml of ether each time, the ether fractions were combined, dried over sodium sulfate, filtered and evaporated in vacuo. The oily residue (2.44 g, 72%) was chromatographed on a 50 g silica gel column eluting with benzene. Combined product fractions (2 g, 59%) were dried at 60 ° C and 0.1 torr for analysis. -4-Pentoxybenzoyl-, -dimethoxypropionic acid methyl ester forms a colorless oil with n => 1.5171.
Příklad 2Example 2
Kyselina -4-pentoxybenzoyl- , 06-dimethoxypropionové 25,86 (0,0728 mol) methylesteru kyseliny -4-pentoxybenzoyl- A -bromakrylové se refluxuje 1 h, s roztokem 3,35 g sodíku (0,145 mol) v 600 ml methanolu, pod uzávěrem s pevným hydroxidem draselným. Methanol se oddestiluje za sníženého tlaku, odparek se za tepla extrahuje 60 ml benzenu a nerozpuštěný anorganický podíl se oddělí. Filtrát se chromatografuje na sloupci 80 g silikagelu za užití benzenu jako elučního činidla, popřípadě jeho směsi s 10 % methanolu při vymytí koncových frakcí. Spojením předních jednotných frakcí se získá 5,7 g (23 %, η^θ» 1»5174 methylesteru kyseliny /^-4-pentoxybenzoyl-«^,«ó -dimethoxypropionové. Ze spojených koncových jednotných podílů se získá 14,93 g (59,2 %, b.t, 153 °C) sodné soli kyseliny /2 -4-pentoxybenzoyi-<x^ , ř^-dimethoxypropionové. Jejím roztřepáním ve směsi 10%ní kyseliny sírové s etherem, ochlazené na4-Pentoxybenzoyl-, 6,6-dimethoxypropionic acid 25.86 (0.0728 mol) -4-pentoxybenzoyl-N-bromoacrylic acid methyl ester is refluxed for 1 h, with a solution of 3.35 g of sodium (0.145 mol) in 600 ml of methanol, under a cap with solid potassium hydroxide. The methanol is distilled off under reduced pressure, the residue is extracted with hot 60 ml of benzene and the insoluble inorganic fraction is separated off. The filtrate is chromatographed on a column of 80 g of silica gel, eluting with benzene or a 10% methanol mixture thereof, eluting the end fractions. Combine the front uniform fractions to give 5.7 g (23%, η 4 -15-methyl-4-pentoxybenzoyl-6,6-dimethoxypropionic acid methyl ester) to give 14.93 g ( 59.2%, mp, 153 [deg.] C.) [2- (4-pentoxybenzoyl), [eta] < 6 > -dimethoxypropionic acid, sodium salt, by shaking it in a mixture of 10% sulfuric acid with ether, cooled to
201 121 °C a odpařením etherickěho podílu se získá ze sodné soli téměř v kvantitativním výtěžku kyselina /3 -4-pentoxybenzoyl-Z/,«6-dimethoxypropionová s t.t, 87 až 89 °C (benzen-hexan).201 DEG-121 DEG C. and evaporation of the ether fraction gave (3 -4-pentoxybenzoyl-2), 1,6-dimethoxypropionic acid, m.p. 87 DEG-89 DEG C. (benzene-hexane) from the sodium salt in almost quantitative yield.
Příklad 3Example 3
Kyselina -4-pentoxybenzoyl-Z, , -diethoxypropionová 9,25 g (0,025 mol) ethylesteru kyseliny /0’ -4-pentoxybenzoyl-®^ -bromakrylové se refluxuje 1 h, s roztokem 1,15 g sodíku (0,05 mol) ve 150 ml ethanolu, pod uzávěrem s pevným hydroxidem draselným. Potom se ethanol oddestiluje za sníženého tlaku, odparek se roztřepe ve směsi 125 ml vody a 250 ml etheru. Organický podíl se vytřepe 20 ml 5%ního roztoku kyselého uhličitanu sodného a 2x po 10 ml vody, vysuší síranem sodným a ether oddestiluje za sníženého tlaku. Olejovitý odparek (1,4 g 15%) ethylesteru kyseliny Zl -4-pentoxybenzoyl- *6 , «ó-diethoxypropionové se přečistí chromatografií na sloupci 25 g silikagelu, za užití benzenu jako elučnxho činidla, n^ 1,5047. Alkalický vodný podíl po vytřepání etherem se při tepřotě 0 °C okyselí zředěnou kyselinou sírovou (1:3) a vytřepe 3x po 50 ml etheru. Spojené etherické výtřepky se vysuší síranem sodným, odpaří za sníženého tlaku a odparek (7,4 g) se překrystaluje z cyklohexanu. Získá se 6,6 g (75,2%) kyseliny & -4-pentoxybenzoyl-*^- , -diethoxypropionové s t.t. 75 až 78 °C, která po opakované krystalizaci z cyklohexanu taje při 79 až 82 °C.4-Pentoxybenzoyl-2'-diethoxypropionic acid 9.25 g (0.025 mol) of ethyl 0 '-4-pentoxybenzoyl-2'-bromoacrylic acid is refluxed for 1 h, with a solution of 1.15 g of sodium (0.05 mol) ) in 150 ml of ethanol, under a cap with solid potassium hydroxide. The ethanol is then distilled off under reduced pressure, and the residue is triturated in a mixture of 125 ml of water and 250 ml of ether. The organic layer was shaken with 20 ml of 5% sodium bicarbonate solution and twice with 10 ml of water each, dried over sodium sulfate and the ether was distilled off under reduced pressure. The oily residue (1.4 g, 15%) of ethyl Z1-4-pentoxybenzoyl-6,6-diethoxypropionate was purified by column chromatography on 25 g of silica gel using benzene as eluent, n = 1.5047. The alkaline aqueous portion, after shaking with ether, is acidified at 0 ° C with dilute sulfuric acid (1: 3) and shaken 3 times with 50 ml of ether each time. The combined ether extracts were dried over sodium sulfate, concentrated in vacuo and the residue (7.4 g) was recrystallized from cyclohexane. 6.6 g (75.2%) of -44-pentoxybenzoyl-4-dimethoxypropionic acid, m.p. 75-78 ° C, which melts at 79-82 ° C after repeated crystallization from cyclohexane.
Claims (2)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS498676A CS201121B1 (en) | 1976-07-29 | 1976-07-29 | Beta-4-pentoxybenzoyl-alpha,alpha'-dialoxy-propionic acid,esters thereof and process for their preparation |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS498676A CS201121B1 (en) | 1976-07-29 | 1976-07-29 | Beta-4-pentoxybenzoyl-alpha,alpha'-dialoxy-propionic acid,esters thereof and process for their preparation |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS201121B1 true CS201121B1 (en) | 1980-10-31 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS498676A CS201121B1 (en) | 1976-07-29 | 1976-07-29 | Beta-4-pentoxybenzoyl-alpha,alpha'-dialoxy-propionic acid,esters thereof and process for their preparation |
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| Country | Link |
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| CS (1) | CS201121B1 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1996003364A1 (en) * | 1994-07-27 | 1996-02-08 | Mitsubishi Chemical Corporation | Benzoylethylene derivative |
-
1976
- 1976-07-29 CS CS498676A patent/CS201121B1/en unknown
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1996003364A1 (en) * | 1994-07-27 | 1996-02-08 | Mitsubishi Chemical Corporation | Benzoylethylene derivative |
| US5789448A (en) * | 1994-07-27 | 1998-08-04 | Mitsubishi Chemical Corporation | Benzoylethylene derivative |
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