CS214312B1 - Method for the production of 3-trans-dimethylamino-4-phenyl-4-trans-carbetoxy-1-cyclohexene - Google Patents
Method for the production of 3-trans-dimethylamino-4-phenyl-4-trans-carbetoxy-1-cyclohexene Download PDFInfo
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- CS214312B1 CS214312B1 CS739680A CS739680A CS214312B1 CS 214312 B1 CS214312 B1 CS 214312B1 CS 739680 A CS739680 A CS 739680A CS 739680 A CS739680 A CS 739680A CS 214312 B1 CS214312 B1 CS 214312B1
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- trans
- isomer
- formula
- cyclohexene
- phenyl
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- 238000000034 method Methods 0.000 title claims description 11
- DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 claims description 16
- 150000003839 salts Chemical class 0.000 claims description 13
- 239000000203 mixture Substances 0.000 claims description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 238000002955 isolation Methods 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- CARJPEPCULYFFP-UHFFFAOYSA-N 5-Sulfo-1,3-benzenedicarboxylic acid Chemical compound OC(=O)C1=CC(C(O)=O)=CC(S(O)(=O)=O)=C1 CARJPEPCULYFFP-UHFFFAOYSA-N 0.000 claims description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- 125000001931 aliphatic group Chemical group 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 4
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- RXKJFZQQPQGTFL-UHFFFAOYSA-N dihydroxyacetone Chemical compound OCC(=O)CO RXKJFZQQPQGTFL-UHFFFAOYSA-N 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims description 3
- DIORMHZUUKOISG-UHFFFAOYSA-N sulfoformic acid Chemical compound OC(=O)S(O)(=O)=O DIORMHZUUKOISG-UHFFFAOYSA-N 0.000 claims description 3
- 150000004292 cyclic ethers Chemical class 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- LJQKCYFTNDAAPC-UHFFFAOYSA-N ethanol;ethyl acetate Chemical compound CCO.CCOC(C)=O LJQKCYFTNDAAPC-UHFFFAOYSA-N 0.000 claims 1
- XTLNYNMNUCLWEZ-UHFFFAOYSA-N ethanol;propan-2-one Chemical compound CCO.CC(C)=O XTLNYNMNUCLWEZ-UHFFFAOYSA-N 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- OVARTBFNCCXQKS-UHFFFAOYSA-N propan-2-one;hydrate Chemical compound O.CC(C)=O OVARTBFNCCXQKS-UHFFFAOYSA-N 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 238000001816 cooling Methods 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- XTEGVFVZDVNBPF-UHFFFAOYSA-N naphthalene-1,5-disulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1S(O)(=O)=O XTEGVFVZDVNBPF-UHFFFAOYSA-N 0.000 description 4
- 239000003208 petroleum Substances 0.000 description 4
- ATBYBMLVINVDKZ-UHFFFAOYSA-N 5-sulfobenzene-1,3-dicarboxylic acid;hydrate Chemical compound O.OC(=O)C1=CC(C(O)=O)=CC(S(O)(=O)=O)=C1 ATBYBMLVINVDKZ-UHFFFAOYSA-N 0.000 description 3
- -1 aromatic sulfocarboxylic acids Chemical class 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- 238000010899 nucleation Methods 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Vynález sa týká spSsobu přípravy 3-trans-dimetyl· amine/-4 -fenyl-4-trans-karbetoxy-l-cyklohexénu vzorce IThe present invention relates to a process for the preparation of 3-trans-dimethyl-amino / -4-phenyl-4-trans-carbethoxy-1-cyclohexene of the formula I
ktorý sa používá v medicíně ako analgetikum.which is used in medicine as an analgesic.
Doposial* sa táto zlúčenina připravovala izoláciou zo zmesi trans-izoméru vzorca I a cis-izoméru, t.j. 3-eis-dimetylamino-4-fenyl-4cis-karbetoxy-l-cyklohexénu vzorca IITo date, this compound has been prepared by isolation from a mixture of the trans-isomer of Formula I and the cis-isomer, i. 3-Eis-dimethylamino-4-phenyl-4-cis-carbetoxy-1-cyclohexene of formula II
CHCH
CHCH
3\.3 \.
214 312 /11/214 312/10 /
2i4 312 frakčnou kryštalizáciou ich hydrochloridov /DOS 1 923 619/, pomocou komplexu cis-izoméru s chloridom zinočnatým /DOS 1 923 620 a Nem.pat. 1 618 476/, alebo pomooou adičnej soli transizoméru I s kyselinou naftalén-1,5-disulfónovou /Nem.pat. 1 768 704 a DOS 2 134 821/.2,414,312 by fractional crystallization of their hydrochlorides (DOS 1,923,619), using the cis-isomer complex with zinc chloride (DOS 1,923,620 and Nem.pat. No. 1,618,476], or by using a naphthalene-1,5-disulfonic acid addition salt of transomer I (Nem. Pat. No. 1,768,704 and DOS 2,134,821 /.
Podstatou tohto vynálezu je příprava čistého trans-izoméru vzorca I, izoláciou zo· zmesi izomérov I a II pomocou aromatických sulfokarboxylových kyselin, s výhodou pomocou 5-sulfoizoftalovej kyseliny vzorca IIIThe present invention relates to the preparation of the pure trans-isomer of formula I by isolation from a mixture of isomers I and II with aromatic sulfocarboxylic acids, preferably with 5-sulfoisophthalic acid of formula III
s ktorou tvoří trans-izomér vzorca I v prostředí alifatického alkoholu s počtom uhlíkov 1 až 4, s výhodou v etanole, v prostředí alifatického ketonu s počtom uhlíkov 3 až 7, s výhodou v acetone, alebo ich zmesiach s vodou, estermi alifatických kyselin s počtom uhlíkov 2 až 6, s výhodou s etylacetátom, alebo s alifatickými alebo cyklickými étermi s počtom uhlíkov 3 až 8 a počtom kvslíkov 1 alebo 2, s výhodou s tetrahydrofuránom resp. dioxánom, izolovateťnd sol' vzorca IVwith which they form the trans-isomer of formula I in an aliphatic alcohol having a carbon number of 1 to 4, preferably in ethanol, an aliphatic ketone having a carbon number of 3 to 7, preferably acetone, or mixtures thereof with water, aliphatic acid esters with the number of carbons 2 to 6, preferably with ethyl acetate, or with aliphatic or cyclic ethers with a number of carbons of 3 to 8 and a number of yeasts of 1 or 2, preferably with tetrahydrofuran and 3-6, respectively. dioxane, an isolate salt of formula IV
Postup podťa vynálezu sa uskutočňuje tak, že sa k roztoku aromatickej sulfokarboxylovej kyseliny, s výhodou 5-sulfoizoftalovej kyseliny vzorca III, a alifatickém alkohole, s výhodou v etanole, alebo alifatickom ketone, s výhodou v acetone, přidá roztok izomérov I a II v alkohole, ketone, esteri alebo éteri, s výhodou v etanole, acetone, etiylacetáte alebo dioxáne resp. tetrahydrofuráne, pričom sa zmes samovolYie zahřeje na 30 až 50 °C. Po ochladení na -10 až +25 °C, s výhodou na 0 až +5 °C, vykrystalizuje sol1 aromatickej sulfokarboxylovej kyseliny s trans-izomérom vzorca IV, kým analogická sol* cis-izoméru II zostane v roztoku. Vyléčená sol1 sa odsaje, sespenduje vo vodě a přidáním silnej anorganickej alebo organické j bázy sa zo soli uvolní trans-izomér I. Tento sa vyextrahuje ineroným organickým rozpúšťadlom, najlepšie petroléterom, extrakt sa vysučí a rozpúštíadlo sa oddestiluje. Získá sa trans-izomér I vo výtažku 60 - 65 % s obsahom cis-izoméru II max. 1 % váh.The process according to the invention is carried out by adding a solution of the isomers I and II in an alcohol to a solution of an aromatic sulfocarboxylic acid, preferably 5-sulfoisophthalic acid of the formula III, and an aliphatic alcohol, preferably ethanol or an aliphatic ketone, preferably acetone. , ketone, ester or ether, preferably in ethanol, acetone, ethyl acetate or dioxane, respectively. tetrahydrofuran, the mixture being spontaneously heated to 30-50 ° C. After cooling to -10 to + 25 ° C, preferably to 0 to + 5 ° C, the aromatic sulfocarboxylic acid salt 1 of the trans-isomer of formula IV crystallizes while the analogous salt of the cis-isomer II remains in solution. The treated salt 1 is aspirated, suspended in water and the trans-isomer I is liberated from the salt by addition of a strong inorganic or organic base. This is extracted with an inorganic organic solvent, preferably petroleum ether, the extract is dried and the solvent is distilled off. The trans-isomer I is obtained in a yield of 60-65% with a content of cis-isomer II of max. 1% by weight
Výhodou tohto postupu oproti prv popísanému postupu s naftalén-1,5-disulfónovou kyselinou je použitie kyseliny čsl. proveniencie. Oproti daťším popísaným postupom je výhoda toh to postupu v zíkaní trans-izoméru I ve vačšej čistotě.The advantage of this process over the naphthalene-1,5-disulfonic acid process described above is the use of the acid no. provenance. Compared to the other processes described above, the advantage of this process is to obtain a higher purity of the trans-isomer I.
V dalšom je predmet vynálzú popísan^ v príkladoch provedenla bez toho že by sa na tieto obmedzoval.In the following, the subject of the invention described in the examples has been carried out without being limited thereto.
214 312214 312
Příklad 1 *Example 1 *
Do predom připraveného roztoku z 3,16 kg /11,97 mól/ kyseliny 5-sulfoizoftalovej monohjdrátu v 4·,4 1 etanolu sa za miešania a chladenia přidá roztok 4,56 kg bázy, obsahujúcej 60 % váh. trans-izoméru I /10 mól/ v 4,4 1 etylacetátu. Po ochladení roztoku a čiastočnom vypadnutí krvštálu sa přidá ešte 4,8 1 etylacetátu a zmes nechá miešať ešte 1,5 hod. Potom sa vypadnutá sol' odsaje, suspenduje sa v zmesi 41 etanolu a 6 1 etylacetátu a nechá sa mie šať pri izbovej teplote cca 20 min. Potom sa znova odsaje, přečištěný ktyštál sa suspenduje v 8 1 vody a báza sa. uvol'ní přidáním 50 %-ného roztoku hydroxydu sodného do pH 13. Vyléčená báza sa extrahuje petroléterom, petroléterový extrakt sa vysuší bezv. síranom sodným a petroléter sa oddestiluje. Získá sa 1,67 J&g. bázy s obsahom 95,15 % váh. 3-trans-dimetylamino-4-fenyl-4-trans-karbetoxy-l-cyklohexénu a menej ako 1 % váh. 3-cis-dimetylamino-4-fenyl-4-cis-karbetoxy-l-cyklohexénu vzorce II. Výtažek činí 61,1 %. Z matečných lúhov po oddesti lovaní rozpúšťadla sa vyššie spomínaný® postupom získá 1,16 kg bázy obsahujúcej 65 % váh. 3-cis-dimetylamino-4-fenyl-4-cis-karbetoxy-l-cyklohexénu a 15 % váh. 3-trans-dimety-amino-4 -fenyl-4-trans-karbetoxy-l-cyklohexénu vzorca I.To a previously prepared solution of 3.16 kg (11.97 mol) of 5-sulfoisophthalic acid monohydrate in 4 L of ethanol, a solution of 4.56 kg of a base containing 60% by weight is added under stirring and cooling. of the trans-isomer I (10 mol) in 4.4 L of ethyl acetate. After cooling the solution and partially precipitating the crystal, 4.8 L of ethyl acetate was added and the mixture was allowed to stir for 1.5 hours. The precipitated salt is then filtered off with suction, suspended in a mixture of 41 ethanol and 6 l of ethyl acetate and allowed to stir at room temperature for about 20 minutes. It is then aspirated again, the purified crystal is suspended in 8 l of water and the base is collected. The resulting base is extracted with petroleum ether, the petroleum ether extract is dried freely. sodium sulfate and the petroleum ether was distilled off. 1.67 J < g is obtained. base containing 95.15% by weight. 3-trans-dimethylamino-4-phenyl-4-trans-carbethoxy-1-cyclohexene and less than 1% by weight. 3-cis-dimethylamino-4-phenyl-4-cis-carbetoxy-1-cyclohexene of formula II. The yield was 61.1%. From the mother liquors after distilling off the solvent, 1.16 kg of a base containing 65% by weight are obtained as described above. % Of 3-cis-dimethylamino-4-phenyl-4-cis-carbethoxy-1-cyclohexene; 3-Trans-dimethylamino-4-phenyl-4-trans-carbethoxy-1-cyclohexene of formula I.
Příklad 2Example 2
K suspenzi! 28,8 g /0,11 mól/ kyseliny S-sulfoizoftalovej monohydrátu v 50 ml acetonu a 5 ml vody sa přidá pri teplote 30 až 40 °C za miešania roztok 40 g bázy obsahujúcej25 g trans-izoméru I /0,09 mól/ v 30 ml acetonu. Po ochladení vykryštaluzuje sol’ 3-trans-dimetylamino-4-fenyl-4-trans-karbetoxy-l-cyklohexénu-5-sulfoizoftalátu, ktorá sa čťalej spracuje ako v příklade 1. Získá sa 13,7 g bázy obsahujúcej 96 % váh. trans-izoméru I.To the suspension! 28.8 g (0.11 mol) of S-sulfoisophthalic acid monohydrate in 50 ml of acetone and 5 ml of water are added at 30 to 40 ° C with stirring a solution of 40 g of base containing 25 g of the trans-isomer I (0.09 mol). in 30 ml acetone. Upon cooling, the salt of 3-trans-dimethylamino-4-phenyl-4-trans-carbethoxy-1-cyclohexene-5-sulfoisophthalate crystallizes, which is further processed as in Example 1. 13.7 g of base are obtained, containing 96% by weight. trans-isomer I.
Příklad 3Example 3
K suspenzii 28,8 g /0,11 mól/ 5-sulfoizoftalovej kyseliny monohydrátu v 50 ml acetonu a 15 ml etanolu sa pri teplote 30 až 40 °C přidá za miešania roztok 40 g bázy obsahujúcej 25 g trans-izoméru I / 0,09 mól/ v 30 ml acetonu. Po ochladení vykryštalizuje sol1 3-trans-dimetylamino-4-fenyl-4-trans-karbetoxy-l-cyklohexénu 5-sulfoizoftalátu, ktorá sa po odsátí a přečištění spracuje ako v příklade 1. Získá sa 13,3 g bázy obsahujúcej 92 % váh.transizoméru I.To a suspension of 28.8 g (0.11 mol) of 5-sulfoisophthalic acid monohydrate in 50 ml of acetone and 15 ml of ethanol at a temperature of 30 to 40 ° C is added, with stirring, a solution of 40 g of base containing 25 g of the trans-isomer I / O. 09 mol / v 30 ml acetone. After cooling the crystallized salt 1 3-trans-dimethylamino-4-phenyl-4-carbethoxy-trans-l-cyclohexene 5-sulfoisophthalate to be the aspiration and purification processes as in Example 1 to give 13.3 g of a base consisting of 92% weight of transisomer I.
Příklad 4Example 4
K roztoku 18 g /0,068 mól/ 5-sulfoizoftalovej kyseliny monohydrátu v 60 ml dioxánu sa přidá roztok 20 g bázy obsahujúcej 12 g trans-izoméru I /0,044 mól/ rozpustenej v 20 ml dioxánu. Po naočkování za miešania a chladenia vykryštalizuje sol1 3-transTdimetylamino-4-fenyl-4-trans-karbetoxy-l-cyklohexénu 5-sulfoizoftalátu. Sol1 sa spracuje podobným postupom ako v příklade 1. Takto sa získá 6,2 g bázy obsahujúcéj 98 % váh. trans-izoméru I.To a solution of 18 g (0.068 mol) of 5-sulfoisophthalic acid monohydrate in 60 ml of dioxane is added a solution of 20 g of base containing 12 g of trans-isomer I (0.044 mol) dissolved in 20 ml of dioxane. After seeding with stirring and cooling crystallized salt of 3-1 transTdimetylamino-4-phenyl-4-carbethoxy-trans-l-cyclohexene 5-sulfoisophthalate. Sol 1 was treated in a similar manner to Example 1. 6.2 g of a base containing 98% by weight were obtained. trans-isomer I.
Claims (4)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS739680A CS214312B1 (en) | 1980-11-03 | 1980-11-03 | Method for the production of 3-trans-dimethylamino-4-phenyl-4-trans-carbetoxy-1-cyclohexene |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS739680A CS214312B1 (en) | 1980-11-03 | 1980-11-03 | Method for the production of 3-trans-dimethylamino-4-phenyl-4-trans-carbetoxy-1-cyclohexene |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS214312B1 true CS214312B1 (en) | 1982-04-09 |
Family
ID=5423016
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS739680A CS214312B1 (en) | 1980-11-03 | 1980-11-03 | Method for the production of 3-trans-dimethylamino-4-phenyl-4-trans-carbetoxy-1-cyclohexene |
Country Status (1)
| Country | Link |
|---|---|
| CS (1) | CS214312B1 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AT500119A1 (en) * | 1998-04-28 | 2005-10-15 | Russinsky Ltd | TILIDINE METHANSULFONATE, PROCESS FOR ITS PREPARATION AND PHARMACEUTICAL MASS HEREVON |
-
1980
- 1980-11-03 CS CS739680A patent/CS214312B1/en unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AT500119A1 (en) * | 1998-04-28 | 2005-10-15 | Russinsky Ltd | TILIDINE METHANSULFONATE, PROCESS FOR ITS PREPARATION AND PHARMACEUTICAL MASS HEREVON |
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