NO871976L - 4-ALKOSY-3-PYRROLIN-2-ON-1-YL-ACETIC ACID AMIDES AND THE PREPARATION AND USE OF THEREOF. - Google Patents
4-ALKOSY-3-PYRROLIN-2-ON-1-YL-ACETIC ACID AMIDES AND THE PREPARATION AND USE OF THEREOF.Info
- Publication number
- NO871976L NO871976L NO871976A NO871976A NO871976L NO 871976 L NO871976 L NO 871976L NO 871976 A NO871976 A NO 871976A NO 871976 A NO871976 A NO 871976A NO 871976 L NO871976 L NO 871976L
- Authority
- NO
- Norway
- Prior art keywords
- acetic acid
- pyrrolin
- alkyl
- compounds according
- preparation
- Prior art date
Links
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 title claims description 9
- 238000002360 preparation method Methods 0.000 title claims description 4
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 9
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 5
- 239000012467 final product Substances 0.000 claims description 5
- IHLAQQPQKRMGSS-UHFFFAOYSA-N oxiracetam Chemical compound NC(=O)CN1CC(O)CC1=O IHLAQQPQKRMGSS-UHFFFAOYSA-N 0.000 claims description 4
- 229910000033 sodium borohydride Inorganic materials 0.000 claims description 4
- 239000012279 sodium borohydride Substances 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- 239000003513 alkali Substances 0.000 claims description 3
- 229910021529 ammonia Inorganic materials 0.000 claims description 3
- 229910000042 hydrogen bromide Inorganic materials 0.000 claims description 3
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims description 3
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 3
- 239000013067 intermediate product Substances 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 230000002378 acidificating effect Effects 0.000 claims description 2
- 230000007306 turnover Effects 0.000 claims 2
- 125000006526 (C1-C2) alkyl group Chemical group 0.000 claims 1
- 150000001298 alcohols Chemical class 0.000 claims 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 5
- -1 aliphatic alcohols Chemical class 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- FCPNSEAKHSMNCT-UHFFFAOYSA-N 2-(3-methoxy-5-oxo-2h-pyrrol-1-yl)acetic acid Chemical compound COC1=CC(=O)N(CC(O)=O)C1 FCPNSEAKHSMNCT-UHFFFAOYSA-N 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- LJSRSOQMKIBVRH-UHFFFAOYSA-N ethyl 2-(3-methoxy-5-oxo-2h-pyrrol-1-yl)acetate Chemical compound CCOC(=O)CN1CC(OC)=CC1=O LJSRSOQMKIBVRH-UHFFFAOYSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 229910000069 nitrogen hydride Inorganic materials 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/24—Oxygen or sulfur atoms
- C07D207/26—2-Pyrrolidones
- C07D207/273—2-Pyrrolidones with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to other ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/36—Oxygen or sulfur atoms
- C07D207/38—2-Pyrrolones
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyrrole Compounds (AREA)
- Electric Clocks (AREA)
Description
De nye forbindelser ifølge oppfinnelsen er verdifulle mellomprodukter ved fremstilling av det cerebralt virksomme 4-hydroksy-2-okso-pyrrolidin-l-yl-acetamid. The new compounds according to the invention are valuable intermediates in the production of the cerebrally active 4-hydroxy-2-oxo-pyrrolidin-1-yl-acetamide.
Hittil er det kjent flere fremgangsmåter for å fremstille det ovenfornevnte virkestoff. Dårlige utbytter og dyre utgangs-produkter gjør imidlertid disse veier urentable (G. Pifferi, H. Pinza, Il Farmaco, Ed.Sc, 1977, 32, 602). To date, several methods have been known for producing the above-mentioned active substance. However, poor yields and expensive starting products make these routes unprofitable (G. Pifferi, H. Pinza, Il Farmaco, Ed.Sc, 1977, 32, 602).
Det besto derfor den oppgave å finne en vei som ikke er beheftet med disse ulemper. The task was therefore to find a way that is not affected by these disadvantages.
Ved oppfinnelsen av de nye 4-(Ci-C2)-alkoksy-3-pyrrolin-2-on-l-yl-eddiksyreamider ifølge krav 1, kunne denne oppgaven løses forbausende enkelt. With the invention of the new 4-(C1-C2)-Alkoxy-3-pyrrolin-2-on-1-yl-acetic acid amides according to claim 1, this task could be solved surprisingly simply.
De nye mellomprodukter, fortrinnsvis 4-metoksy-3-pyrrolin-3-on-l-yl-eddiksyreamidet, fremstilles etter en fremgangsmåte ifølge krav 2 ut fra 4-alkoksy-3-pyrrolin-2-on-l-yl-eddiksyre-Ci-C4-alkylestere ved omsetning av dem med ammoniak. The new intermediates, preferably the 4-methoxy-3-pyrrolin-3-on-l-yl-acetic acid amide, are prepared according to a method according to claim 2 from 4-methoxy-3-pyrrolin-2-on-l-yl-acetic acid Ci-C4 alkyl esters by reacting them with ammonia.
4-alkoksy-3-pyrrolin-2-on-l-yl-eddiksyre-Ci -C4-alkylesterene kan fremstilles på enkel måte ifølge Sveitsisk patentsøknad nr. 4119/85. 4-Alkoxy-3-pyrrolin-2-on-1-yl-acetic acid C 1 -C 4 alkyl esters can be prepared in a simple manner according to Swiss Patent Application No. 4119/85.
Hensiktsmessig oppløser man 4-alkoksy-3-pyrrolin-2-on-l-yl-eddiksyre-Ci-C4-alkylesteren i en alkohol som løsningsmiddel. Fortrinnsvis kommer lavere alifatiske alkoholer så som etanol eller metanol, særlig foretrukket metanol til anvendelse. It is expedient to dissolve the 4-Alkoxy-3-pyrrolin-2-on-1-yl-acetic acid C1-C4 alkyl ester in an alcohol as solvent. Preferably, lower aliphatic alcohols such as ethanol or methanol, particularly preferably methanol, are used.
Deretter mettes løsningen normalt i en autoklav hensiktsmessig med gassformig ammoniak ved temperaturer rundt 0°C. The solution is then normally saturated in an autoclave appropriately with gaseous ammonia at temperatures around 0°C.
Ved reaksjonstemperaturer mellom 40 og 70° C er reaksjonen som regel avsluttet etter 5 til 10 timer. At reaction temperatures between 40 and 70° C, the reaction is usually finished after 5 to 10 hours.
Opparbeidingen kan foretas på enkel måte ved fordampning av løsningsmiddelet og eventuelt ved en etterfølgende rensning ved omkrystallisering. The processing can be carried out in a simple way by evaporation of the solvent and possibly by a subsequent purification by recrystallization.
Etter denne fremgangsmåten er det mulig å oppnå nesten kvantitative utbytter og ytterst rene produkter. Following this procedure, it is possible to obtain almost quantitative yields and extremely pure products.
Ifølge krav 4 kan de nye forbindelser ifølge oppfinnelsen med fordel anvendes som mellomprodukter ved fremstilling av det cerebralt virksomme 4-hydroksy-pyrrolin-2-on-l-yl-acetamid. According to claim 4, the new compounds according to the invention can advantageously be used as intermediates in the production of the cerebrally active 4-hydroxy-pyrrolin-2-on-1-yl-acetamide.
For dette omsettes hensiktsmessig det tilsvarende mellomprodukt i et vannfritt surt medium i et første trinn og omsettes så med et alkaliborhydrid til sluttproduktet. For this, the corresponding intermediate product is suitably reacted in an anhydrous acidic medium in a first step and then reacted with an alkali borohydride to the final product.
Som vannfritt medium anvendes hensiktsmessig hydrogenklorid eller hydrogenbromid oppløst i en Ci -C-» -karboksylsyre. Hydrogen chloride or hydrogen bromide dissolved in a C 1 -C 2 -carboxylic acid is suitably used as an anhydrous medium.
Særlig foretrukket er det å anvende hydrogenbromid i eddiksyre. It is particularly preferred to use hydrogen bromide in acetic acid.
I forhold til 1 mol anvendt alkoksypyrrolinonylacetamid anvendes hydrogenklorid hhv. hydrogenbromid i mengder på hensiktsmessig 1 til 2 mol. In relation to 1 mol of alkoxypyrrolinyl acetamide used, hydrogen chloride is used or hydrogen bromide in amounts of suitably 1 to 2 mol.
Reaksjonstemperaturen beveger seg hensiktsmessig mellom 40 og 50° C. The reaction temperature is suitably between 40 and 50° C.
Det midlertidige dannede hydrohalogenid av 2,4-dioksy-pyrrolin-l-yl-acetamid omsettes som regel direkte med et alkaliborhydrid, fortrinnsvis med natriumborhydrid. Dette reaksjons-trinnet utføres hensiktsmessig i dimetylformamid som løsnings-middel ved temperaturer fra 0 til 40°C, hensiktsmessig fra 20 til 30 °C. The temporarily formed hydrohalide of 2,4-dioxy-pyrrolin-1-yl-acetamide is usually reacted directly with an alkali borohydride, preferably with sodium borohydride. This reaction step is suitably carried out in dimethylformamide as solvent at temperatures from 0 to 40°C, suitably from 20 to 30°C.
Opparbeidingen kan utføres på vanlig måte ved f.eks. surgjøring av reaksjonsblandingen, ekstrahering av produktet og eventuelt ved etterfølgende omkrystallisering. Processing can be carried out in the usual way by e.g. acidification of the reaction mixture, extraction of the product and possibly by subsequent recrystallization.
På denne måten lykkes det å få et sluttprodukt i gode utbytter og med høy kvalitet. In this way, it is possible to obtain a final product in good yields and of high quality.
EKSEMPELEXAMPLE
Fremstilling av 4- metoksy- 3- pyrrolin- 2- on- l- yl- acetamid Preparation of 4-methoxy-3-pyrroline-2-on-1-yl-acetamide
25,0 g (0,10 mol) 4-metoksy-3-pyrrolin-2-on-l-yl-eddiksyre-etylester med et innhold ifølge GC på 78,7% ble oppløst i 300 ml metanol og mettet med gassformid NH3ved 0°C. Reaksjonsblandingen ble rørt i en autoklav i 5 timer ved 60°C. Etter inndamping av reaksjonsløsningen ble resten omkrystallisert varmt fra metanol. 25.0 g (0.10 mol) of 4-methoxy-3-pyrrolin-2-on-1-yl-acetic acid ethyl ester with a content according to GC of 78.7% was dissolved in 300 ml of methanol and saturated with gas formamide NH3 at 0°C. The reaction mixture was stirred in an autoclave for 5 hours at 60°C. After evaporation of the reaction solution, the residue was recrystallized hot from methanol.
Man fikk 16,6 g (=97,5% av teoretisk utbytte) tynnskikt-kromatografisk rent produkt med et smeltepunkt på 184 til 186°C. 16.6 g (=97.5% of theoretical yield) of thin-layer chromatographically pure product with a melting point of 184 to 186°C was obtained.
NMR (DMSO-de , 300 MHz):NMR (DMSO-de, 300 MHz):
7,4 (br. s, 1H), 7,06 (br. s, 1H), 5,16 (s, 1H), 3,97 (s, 2H), 3,85 (s, 2H), 3,68 (s, 3H). 7.4 (br. s, 1H), 7.06 (br. s, 1H), 5.16 (s, 1H), 3.97 (s, 2H), 3.85 (s, 2H), 3 .68 (p, 3H).
Fremstilling av 4- hydroksy- pyrrolidin- 2- on- l- yl- acetamid Preparation of 4-hydroxy-pyrrolidin-2-on-1-yl-acetamide
10,0 g (0,0058 mol) 4-metoksy-3-pyrrolin-2-on-l-yl-acetamid ble oppløst i 117 ml eddiksyre og blandet med 14,4 g (0,0058 mol) av en 33 %-ig løsning av hydrogenbromid i eddiksyre. Man lot reaksjonsløsningen røre i 5 timer ved 40°C. Under røringen falt en hvit felling ut som ble frafiltrert, vasket med 50 ml metylen-klorid og tørket. Fellingen ble satt porsjonsvis under nitrogen ved romtemperatur til en løsning av 2,6 g (0,069 mol) natriumborhydrid i 130 ml dimetylformamid. Så ble reaksjonsløsningen surgjort med konsentrert saltsyre og inndampet med rotasjonsfor-damper. Resten ble utkokt med isopropanol, deretter filtrert, filtratet inndampet på nytt og resten utkrystallisert to ganger varmet fra metanol. 10.0 g (0.0058 mol) of 4-methoxy-3-pyrrolin-2-one-l-yl-acetamide was dissolved in 117 ml of acetic acid and mixed with 14.4 g (0.0058 mol) of a 33% -ig solution of hydrogen bromide in acetic acid. The reaction solution was allowed to stir for 5 hours at 40°C. During stirring, a white precipitate fell out which was filtered off, washed with 50 ml of methylene chloride and dried. The precipitate was added portionwise under nitrogen at room temperature to a solution of 2.6 g (0.069 mol) of sodium borohydride in 130 ml of dimethylformamide. The reaction solution was then acidified with concentrated hydrochloric acid and evaporated with a rotary evaporator. The residue was boiled off with isopropanol, then filtered, the filtrate evaporated again and the residue recrystallized twice heated from methanol.
Man fikk 5,0 g (= 54,5% av teoretisk utbytte) hvitt, krystallinsk produkt med et smeltepunkt på 167 til 168°C. 5.0 g (= 54.5% of theoretical yield) of white, crystalline product with a melting point of 167 to 168°C were obtained.
Claims (7)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1959/86A CH668067A5 (en) | 1986-05-14 | 1986-05-14 | 4-ALKOXY-3-pyrroline-2-ON-1-YL-ESSIGSAEUREAMIDE, PRODUCTION AND USE THEREOF. |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO871976D0 NO871976D0 (en) | 1987-05-13 |
| NO871976L true NO871976L (en) | 1987-11-16 |
Family
ID=4222604
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO871976A NO871976L (en) | 1986-05-14 | 1987-05-13 | 4-ALKOSY-3-PYRROLIN-2-ON-1-YL-ACETIC ACID AMIDES AND THE PREPARATION AND USE OF THEREOF. |
Country Status (7)
| Country | Link |
|---|---|
| EP (1) | EP0249018A1 (en) |
| JP (1) | JPS62273950A (en) |
| CH (1) | CH668067A5 (en) |
| DK (1) | DK243887A (en) |
| HU (1) | HUT44234A (en) |
| IL (1) | IL82467A0 (en) |
| NO (1) | NO871976L (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH680293A5 (en) * | 1990-06-26 | 1992-07-31 | Lonza Ag |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AR211398Q (en) * | 1975-08-13 | 1977-12-15 | Isf Spa | A PROCEDURE FOR PREPARING (-PIRROLIN -2- ON -1- IL) -ACILAMIDE DERIVATIVES |
-
1986
- 1986-05-14 CH CH1959/86A patent/CH668067A5/en not_active IP Right Cessation
-
1987
- 1987-04-27 EP EP87106098A patent/EP0249018A1/en not_active Withdrawn
- 1987-05-10 IL IL82467A patent/IL82467A0/en unknown
- 1987-05-11 JP JP62114401A patent/JPS62273950A/en active Pending
- 1987-05-13 HU HU872148A patent/HUT44234A/en unknown
- 1987-05-13 DK DK243887A patent/DK243887A/en not_active Application Discontinuation
- 1987-05-13 NO NO871976A patent/NO871976L/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| JPS62273950A (en) | 1987-11-28 |
| DK243887D0 (en) | 1987-05-13 |
| NO871976D0 (en) | 1987-05-13 |
| DK243887A (en) | 1987-11-15 |
| CH668067A5 (en) | 1988-11-30 |
| EP0249018A1 (en) | 1987-12-16 |
| IL82467A0 (en) | 1987-11-30 |
| HUT44234A (en) | 1988-02-29 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| NO151876B (en) | PROCEDURE AND APPARATUS FOR ANIMAL LINING | |
| GARBRECHT | Synthesis of Amides of Lysergic Acid1 | |
| NO140101B (en) | PROCEDURES FOR THE PREPARATION OF SUBSTITUTED AMINOBENZO ACID DERIVATIVES | |
| NO173059B (en) | ANALOGY PROCEDURE FOR THE PREPARATION OF THERAPEUTIC ACTIVE HYDANTOIN DERIVATIVES | |
| AU612000B2 (en) | A process for the preparation of pyrrolidone derivatives | |
| DE2903891C2 (en) | ||
| EP0252353B1 (en) | 4-benzyloxy-3-pyrrolin-2-one-1-yl-acetamide, preparation and use | |
| NO871976L (en) | 4-ALKOSY-3-PYRROLIN-2-ON-1-YL-ACETIC ACID AMIDES AND THE PREPARATION AND USE OF THEREOF. | |
| BOSE et al. | Some Derivatives of Glycineamidine1 | |
| SU584774A3 (en) | Method of preparing azoxazole derivatives | |
| SU1556538A3 (en) | Method of producing pyrimidine derivatives | |
| US4855451A (en) | 4-benzyloxy-3-pyrrolin-2-one, its production and use for synthesis of tetramic acid | |
| SU922108A1 (en) | Process for producing derivatives of 6-methyl-8-beta-hydrazinomethylergolin or their salts | |
| SU1313856A1 (en) | Method for producing derivatives of cis- or trans-diaminodibenzoyl-dibenzo-18-crown-6 | |
| CH692506A5 (en) | A process for producing aminocyanoacetamide. | |
| US2786849A (en) | Production of 5-(delta-hydroxybutyl) hydantoin | |
| US2701798A (en) | Ch-cha | |
| SU418036A1 (en) | METHOD FOR OBTAINING DERIVATIVES OF 8H-PYRIMIDO- [5.4- &] [1,4] -OXAZINON-7 | |
| CS257300B2 (en) | Process for preparing 4-hydroxy-2-oxo-pyrrolidin-1-yl-acetamide | |
| Pan et al. | Diastereospecific synthesis of trans-2, 3-diaryl-1-aminocyclopropanecarboxylic acids | |
| NO852794L (en) | 9- AND 11-SUBSTITUTED APOVINCAMIC ACID DERIVATIVES AND PROCEDURES FOR THEIR PREPARATION | |
| SU717053A1 (en) | Method of preparing 3,4,6-trisubstituted pyrones-2 | |
| US4271290A (en) | 3,4-Xylidine-N-ribityl | |
| NO154881B (en) | Ol derivative. | |
| Fozard et al. | 530. Quinolizines. Part. VII. Rearrangement products from 1, 2, 3, 4-tetrahydro-1-hydroxyiminoquinolizinium bromides |