SE460604B - AZIRIDE DERIVATIVES AND PROCEDURES FOR ITS PREPARATION - Google Patents
AZIRIDE DERIVATIVES AND PROCEDURES FOR ITS PREPARATIONInfo
- Publication number
- SE460604B SE460604B SE8502780A SE8502780A SE460604B SE 460604 B SE460604 B SE 460604B SE 8502780 A SE8502780 A SE 8502780A SE 8502780 A SE8502780 A SE 8502780A SE 460604 B SE460604 B SE 460604B
- Authority
- SE
- Sweden
- Prior art keywords
- preparation
- methyl
- aziride
- procedures
- derivatives
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/52—Radicals substituted by nitrogen atoms not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D203/00—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom
- C07D203/04—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D203/06—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D203/08—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring nitrogen atom
- C07D203/12—Radicals substituted by nitrogen atoms not forming part of a nitro radical
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Furan Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
Description
4eo 604 2 , 2lx~ 1 Aziridinderivatet med formel IV kan framställas endl att] etylenimin omsättes med en nitroetenamin med formeln“» V ~å 'Å Ém°2 ' V ~ ' -1 L'-CNHMe » = (V) ' .E där L' betecknar en avspjälkbar grupp, t.ex. en C1_¿-alkoxigrupp : eller en C1_4-alkyltiogrup, företrädesvis metyltio. Reaktionen kan genomföras i ett lämpligt aprotiskt lösningsmedel, såso aceto- ä nitril. The aziridine derivative of the formula IV can be prepared by reacting the ethyleneimine with a nitroethenamine of the formula '' V ~ å 'Å Ém ° 2' V ~ '-1 L'-CNHMe »= (V)'. E where L 'represents a leaving group, e.g. a C 1-4 alkoxy group: or a C 1-4 alkylthio group, preferably methylthio. The reaction can be carried out in a suitable aprotic solvent, such as acetonitrile.
Uppfinningen illustreras genom följande exempel. Exempel 1 illustrerar framställning av den nya förneingen enligt uppfin- ningen, och exempel 2 illustrerar användning av denna förening för framställning av ranitidin.The invention is illustrated by the following examples. Example 1 illustrates the preparation of the novel compound of the invention, and Example 2 illustrates the use of this compound for the preparation of ranitidine.
Exempel 1. N-metyl-a-(nitrometylen)-1-aziridinmetanamin.Example 1. N-methyl-α- (nitromethylene) -1-aziridinemethanamine.
En lösning av 0,47 g etylenimin och 1,48 g N-metyl-(1-metyl- tio)-2-nitroetenamin i S ml acetonitril omrördes vid rumstemperatur under 2 dygn. Den resulterande suspensionen indunstades i vakuum vid rumstemperatur, och återstoden extraherades med 100 ml varmt etylacetat. Extraktet indunstades i vakuum, och återstoden sus- penderades i S0 ml etylacetat, varpå den resulterande suspensionen filtrerades. Filtratet indunstades till en volym av ca 5 ml och kromatograferades på kiseldioxid med användning av etylacetat så- som elueringsmede1.' Man indunstades i vakuum det eluat, vilket gav ett Rf-värde av 0,28 vid tunnskiktskromatografi på kiseldioxid med användning av etylacetat såsom elueringsmedel. Härvid erhölls 0,33 g av titelföreningen med en smältpunkt av 118-119°C.A solution of 0.47 g of ethyleneimine and 1.48 g of N-methyl- (1-methylthio) -2-nitroethenamine in 5 ml of acetonitrile was stirred at room temperature for 2 days. The resulting suspension was evaporated in vacuo at room temperature, and the residue was extracted with 100 ml of hot ethyl acetate. The extract was evaporated in vacuo, and the residue was suspended in 50 ml of ethyl acetate, after which the resulting suspension was filtered. The filtrate was evaporated to a volume of about 5 ml and chromatographed on silica using ethyl acetate as eluent. The eluate was evaporated in vacuo to give an Rf value of 0.28 by thin layer chromatography on silica using ethyl acetate as eluent. This gave 0.33 g of the title compound, m.p. 118-119 ° C.
Exempel 2. N-[2-[ZS-Lïdimetylamino)metyl]-2-furanylmetyl]- tiqfetylf-N'-metyl-2-nitro-1,1-etendiamin. A Till en blandning av 0,156 g 5-L(dimetylamino)metyl]-2-furan- metantiol-oxalat (1:1), 0,05 g natriumditionit och 0,15 g vatten- fritt natriumkarbonat i 0,4 ml vatten sattes 15 ml eter och ett överskott av vattenfritt natriumkarbonat. Den resulterande bland- ningen filtrerades, och filtratet indunstades i vakuum. Till åter- stoden sattes 0,072 g N-metyl-u-(nitrometylen)-1-aziridinmetan- amin och 2 ml metanol, och den erhållna lösningen indunstades till torrhet. återstoden upphettades vid 98-100°C under 1,25 timar, och produkten kromatograferades på kiseldioxid, varvid man såsom elueringsmedel använde en blandning av metanol och 0,88 amoniak i volymförhållandet 79:1. bet lämplga eluatet indunstades i va- kuum, varvid man erhöll 0,113 g av titelföreningen med en smält-Example 2. N- [2- [2S-Lidimethylamino) methyl] -2-furanylmethyl] -phetyl [N'-methyl-2-nitro-1,1-ethenediamine. To a mixture of 0.156 g of 5-L (dimethylamino) methyl] -2-furan-methanethiol oxalate (1: 1), 0.05 g of sodium dithionite and 0.15 g of anhydrous sodium carbonate in 0.4 ml of water was added 15 ml of ether and an excess of anhydrous sodium carbonate. The resulting mixture was filtered, and the filtrate was evaporated in vacuo. To the residue were added 0.072 g of N-methyl-u- (nitromethylene) -1-aziridinemethanamine and 2 ml of methanol, and the resulting solution was evaporated to dryness. the residue was heated at 98-100 ° C for 1.25 hours, and the product was chromatographed on silica using a mixture of methanol and 0.88 ammonia in a volume ratio of 79: 1 as eluent. The appropriate eluate was evaporated in vacuo to give 0.113 g of the title compound with a melting point.
Claims (2)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8000581 | 1980-01-08 | ||
| GB8000580 | 1980-01-08 | ||
| GB8039336 | 1980-12-08 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| SE8502780L SE8502780L (en) | 1985-06-05 |
| SE8502780D0 SE8502780D0 (en) | 1985-06-05 |
| SE460604B true SE460604B (en) | 1989-10-30 |
Family
ID=27260837
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE8100074A SE449747B (en) | 1980-01-08 | 1981-01-08 | PROCEDURE FOR PREPARING N- / 2 - // 5 - / (DIMETHYLAMINO) METHYL / -2-FURANYLMETHYL / -TIO / ETHYL / N'-METHYL-2-NITRO-1,1-ETHENYAMINE (RANITIDINE) |
| SE8502780A SE460604B (en) | 1980-01-08 | 1985-06-05 | AZIRIDE DERIVATIVES AND PROCEDURES FOR ITS PREPARATION |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE8100074A SE449747B (en) | 1980-01-08 | 1981-01-08 | PROCEDURE FOR PREPARING N- / 2 - // 5 - / (DIMETHYLAMINO) METHYL / -2-FURANYLMETHYL / -TIO / ETHYL / N'-METHYL-2-NITRO-1,1-ETHENYAMINE (RANITIDINE) |
Country Status (14)
| Country | Link |
|---|---|
| JP (1) | JPH02167259A (en) |
| AR (1) | AR225940A1 (en) |
| AT (1) | AT376966B (en) |
| CH (1) | CH650257A5 (en) |
| DE (1) | DE3100364A1 (en) |
| DK (1) | DK157865C (en) |
| ES (1) | ES498389A0 (en) |
| FI (1) | FI80450C (en) |
| FR (1) | FR2473044A1 (en) |
| HU (1) | HU182272B (en) |
| NL (1) | NL8100068A (en) |
| PT (1) | PT72320B (en) |
| SE (2) | SE449747B (en) |
| YU (1) | YU42372B (en) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3213509A1 (en) * | 1982-04-10 | 1983-10-20 | Basf Ag, 6700 Ludwigshafen | N-SUBSTITUTED IMIDAZOLE DERIVATIVES, THEIR PRODUCTION, THE MEDICINES CONTAINING THEM AND THEIR USE |
| YU42819B (en) * | 1982-11-22 | 1988-12-31 | Lek Tovarna Farmacevtskih | Process for preparing n-/2-///5-(dimethyl-amino)-methyl-2-furanyl/methyl/thio/ethyl-n'-methyl-2-nitro-1,1-ethene diamine |
| NL8303965A (en) * | 1982-12-08 | 1984-07-02 | Degussa | NEW FOOD DIAMINE AND GUANIDINE DERIVATIVES; METHOD FOR PREPARING THEREOF MEDICINES CONTAINING THEM; METHOD FOR PREPARING SUCH MEDICINES; APPLICATION OF THE COMPOUNDS FOR THE PREPARATION OF MEDICINAL PRODUCTS AND IN MEDICINE. |
| DE3343884A1 (en) * | 1982-12-08 | 1984-06-14 | Degussa Ag, 6000 Frankfurt | Novel ethenediamine and guanidine derivatives |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1565966A (en) * | 1976-08-04 | 1980-04-23 | Allen & Hanburys Ltd | Aminoalkyl furan derivatives |
| IL56265A (en) | 1977-12-28 | 1982-08-31 | Om Lab Sa | Process for preparing imidazolyl methylthio guanidine derivatives and a novel intermediate therefor |
| NO784350L (en) * | 1977-12-30 | 1979-07-03 | Crc Ricerca Chim | PROCEDURE FOR ALKYLATION OF 4 (5) -MERCAPTOMETHYL-IMIDAZOLES WITH AZIRIDINE DERIVATIVES |
| ZA792608B (en) * | 1978-05-30 | 1980-06-25 | Smith Kline French Lab | Nitro compounds |
| FI811376L (en) * | 1980-05-13 | 1981-11-14 | Crc Ricerca Chim | PROCEDURE FOR FRAMSTATING AV N- / 2 - /// 5- (DIALKYLAMINO) -METHYL-2-FURANYL / -METHYL / -THIO / EECL / -N'-ALKYL-2-NITRO-1,1-ETENDIAMINER OCH DERAS MELLANPRODUKTER |
-
1981
- 1981-01-07 PT PT7232081A patent/PT72320B/en unknown
- 1981-01-08 HU HU3981A patent/HU182272B/en unknown
- 1981-01-08 NL NL8100068A patent/NL8100068A/en active Search and Examination
- 1981-01-08 DK DK7181A patent/DK157865C/en not_active IP Right Cessation
- 1981-01-08 SE SE8100074A patent/SE449747B/en not_active IP Right Cessation
- 1981-01-08 ES ES498389A patent/ES498389A0/en active Granted
- 1981-01-08 DE DE19813100364 patent/DE3100364A1/en active Granted
- 1981-01-08 FR FR8100206A patent/FR2473044A1/en active Granted
- 1981-01-08 YU YU2781A patent/YU42372B/en unknown
- 1981-01-08 AR AR28390081A patent/AR225940A1/en active
- 1981-01-08 CH CH8681A patent/CH650257A5/en not_active IP Right Cessation
- 1981-01-08 AT AT3781A patent/AT376966B/en not_active IP Right Cessation
- 1981-01-08 FI FI810039A patent/FI80450C/en not_active IP Right Cessation
-
1985
- 1985-06-05 SE SE8502780A patent/SE460604B/en not_active IP Right Cessation
-
1989
- 1989-10-25 JP JP27829589A patent/JPH02167259A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| SE8502780L (en) | 1985-06-05 |
| DK157865B (en) | 1990-02-26 |
| YU2781A (en) | 1983-06-30 |
| SE449747B (en) | 1987-05-18 |
| PT72320A (en) | 1981-02-01 |
| PT72320B (en) | 1982-07-23 |
| FI810039L (en) | 1981-07-09 |
| FI80450C (en) | 1990-06-11 |
| ES8200673A1 (en) | 1981-11-16 |
| AT376966B (en) | 1985-01-25 |
| FI80450B (en) | 1990-02-28 |
| ES498389A0 (en) | 1981-11-16 |
| JPH02167259A (en) | 1990-06-27 |
| CH650257A5 (en) | 1985-07-15 |
| SE8100074L (en) | 1981-07-09 |
| ATA3781A (en) | 1984-06-15 |
| FR2473044B1 (en) | 1984-04-13 |
| DK157865C (en) | 1990-07-30 |
| HU182272B (en) | 1983-12-28 |
| NL8100068A (en) | 1981-08-03 |
| DE3100364C2 (en) | 1989-12-28 |
| FR2473044A1 (en) | 1981-07-10 |
| SE8502780D0 (en) | 1985-06-05 |
| DK7181A (en) | 1981-07-09 |
| JPH0346465B2 (en) | 1991-07-16 |
| AR225940A1 (en) | 1982-05-14 |
| YU42372B (en) | 1988-08-31 |
| DE3100364A1 (en) | 1981-11-19 |
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