SE460604B - Aziridinderivat och foerfarande foer dess framstaellning - Google Patents
Aziridinderivat och foerfarande foer dess framstaellningInfo
- 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.
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.
Exempel 1. N-metyl-a-(nitrometylen)-1-aziridinmetanamin.
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.
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-
Claims (2)
1. N-metyl-a-(nitrometylen)-1-aziridín-metanamin.
2. Förfarande för framställning av N-metyl-a-(nitromety1en)-1- -aziridin-metanamin, k ä n n e t e c k n a t a v att etylenímín omsättes med en nitroetanamin med fcrmeln CHNO2 L”-CNHH% (V) där L' betecknar en C1_4-alkoxigrupp eller en C1_4-alkyltíogzupp.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8000580 | 1980-01-08 | ||
| GB8000581 | 1980-01-08 | ||
| GB8039336 | 1980-12-08 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| SE8502780D0 SE8502780D0 (sv) | 1985-06-05 |
| SE8502780L SE8502780L (sv) | 1985-06-05 |
| SE460604B true SE460604B (sv) | 1989-10-30 |
Family
ID=27260837
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE8100074A SE449747B (sv) | 1980-01-08 | 1981-01-08 | Forfarande for framstellning av n-/2-//5-/(dimetylamino) metyl/-2-furanylmetyl/-tio/etyl/n'-metyl-2-nitro-1,1-etendiamin (ranitidin) |
| SE8502780A SE460604B (sv) | 1980-01-08 | 1985-06-05 | Aziridinderivat och foerfarande foer dess framstaellning |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE8100074A SE449747B (sv) | 1980-01-08 | 1981-01-08 | Forfarande for framstellning av n-/2-//5-/(dimetylamino) metyl/-2-furanylmetyl/-tio/etyl/n'-metyl-2-nitro-1,1-etendiamin (ranitidin) |
Country Status (14)
| Country | Link |
|---|---|
| JP (1) | JPH02167259A (sv) |
| AR (1) | AR225940A1 (sv) |
| AT (1) | AT376966B (sv) |
| CH (1) | CH650257A5 (sv) |
| DE (1) | DE3100364A1 (sv) |
| DK (1) | DK157865C (sv) |
| ES (1) | ES498389A0 (sv) |
| FI (1) | FI80450C (sv) |
| FR (1) | FR2473044A1 (sv) |
| HU (1) | HU182272B (sv) |
| NL (1) | NL8100068A (sv) |
| PT (1) | PT72320B (sv) |
| SE (2) | SE449747B (sv) |
| YU (1) | YU42372B (sv) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3213509A1 (de) * | 1982-04-10 | 1983-10-20 | Basf Ag, 6700 Ludwigshafen | N-substituierte imidazol-derivate, ihre herstellung, diese enthaltende arzneimittel und ihre verwendung |
| 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 (nl) * | 1982-12-08 | 1984-07-02 | Degussa | Nieuwe etheendiamine- en guanidine-derivaten; werkwijze voor het bereiden daarvan; geneesmiddelen die ze bevatten; werkwijze voor het bereiden van dergelijke geneesmiddelen; toepassing van de verbindingen voor het bereiden van geneesmiddelen en in de geneeskunde. |
| DE3343884A1 (de) * | 1982-12-08 | 1984-06-14 | Degussa Ag, 6000 Frankfurt | Neue ethendiamin- und guanidin-derivate |
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 |
| GR65283B (en) * | 1977-12-30 | 1980-08-01 | Crc Ricerca Chim | Method for the alkyliosis of 4(5)-merka ptomethyl-imidazoles with aziridin derivatives |
| IL57416A (en) * | 1978-05-30 | 1983-03-31 | Smith Kline French Lab | Nitro compounds,processes for preparing them and compositions containing them |
| NO811501L (no) * | 1980-05-13 | 1981-11-16 | Crc Ricerca Chim | Fremgangsmaate ved fremstilling av etendiaminderivater, samt mellomprodukter for disse |
-
1981
- 1981-01-07 PT PT7232081A patent/PT72320B/pt unknown
- 1981-01-08 DE DE19813100364 patent/DE3100364A1/de active Granted
- 1981-01-08 CH CH8681A patent/CH650257A5/fr not_active IP Right Cessation
- 1981-01-08 NL NL8100068A patent/NL8100068A/nl active Search and Examination
- 1981-01-08 AT AT3781A patent/AT376966B/de not_active IP Right Cessation
- 1981-01-08 AR AR28390081A patent/AR225940A1/es active
- 1981-01-08 YU YU2781A patent/YU42372B/xx unknown
- 1981-01-08 HU HU3981A patent/HU182272B/hu unknown
- 1981-01-08 ES ES498389A patent/ES498389A0/es active Granted
- 1981-01-08 SE SE8100074A patent/SE449747B/sv not_active IP Right Cessation
- 1981-01-08 DK DK7181A patent/DK157865C/da not_active IP Right Cessation
- 1981-01-08 FR FR8100206A patent/FR2473044A1/fr active Granted
- 1981-01-08 FI FI810039A patent/FI80450C/sv not_active IP Right Cessation
-
1985
- 1985-06-05 SE SE8502780A patent/SE460604B/sv not_active IP Right Cessation
-
1989
- 1989-10-25 JP JP27829589A patent/JPH02167259A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| FI80450B (fi) | 1990-02-28 |
| DK157865B (da) | 1990-02-26 |
| DK7181A (da) | 1981-07-09 |
| ATA3781A (de) | 1984-06-15 |
| DE3100364A1 (de) | 1981-11-19 |
| YU42372B (en) | 1988-08-31 |
| FR2473044A1 (fr) | 1981-07-10 |
| DK157865C (da) | 1990-07-30 |
| FR2473044B1 (sv) | 1984-04-13 |
| SE8100074L (sv) | 1981-07-09 |
| AT376966B (de) | 1985-01-25 |
| FI810039L (fi) | 1981-07-09 |
| SE449747B (sv) | 1987-05-18 |
| SE8502780D0 (sv) | 1985-06-05 |
| SE8502780L (sv) | 1985-06-05 |
| JPH02167259A (ja) | 1990-06-27 |
| AR225940A1 (es) | 1982-05-14 |
| NL8100068A (nl) | 1981-08-03 |
| JPH0346465B2 (sv) | 1991-07-16 |
| HU182272B (en) | 1983-12-28 |
| CH650257A5 (fr) | 1985-07-15 |
| DE3100364C2 (sv) | 1989-12-28 |
| FI80450C (sv) | 1990-06-11 |
| PT72320A (en) | 1981-02-01 |
| PT72320B (en) | 1982-07-23 |
| YU2781A (en) | 1983-06-30 |
| ES8200673A1 (es) | 1981-11-16 |
| ES498389A0 (es) | 1981-11-16 |
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| NAL | Patent in force |
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| NUG | Patent has lapsed |
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