CH654830A5 - Aziridine derivative - Google Patents
Aziridine derivative Download PDFInfo
- Publication number
- CH654830A5 CH654830A5 CH2979/84A CH297984A CH654830A5 CH 654830 A5 CH654830 A5 CH 654830A5 CH 2979/84 A CH2979/84 A CH 2979/84A CH 297984 A CH297984 A CH 297984A CH 654830 A5 CH654830 A5 CH 654830A5
- Authority
- CH
- Switzerland
- Prior art keywords
- formula
- group
- methyl
- ethylene
- nitromethylene
- Prior art date
Links
- 150000001541 aziridines Chemical class 0.000 title claims abstract description 6
- 238000000034 method Methods 0.000 claims abstract description 7
- 229960000620 ranitidine Drugs 0.000 claims abstract description 5
- 238000004519 manufacturing process Methods 0.000 claims abstract description 3
- 238000002360 preparation method Methods 0.000 claims abstract description 3
- VMXUWOKSQNHOCA-LCYFTJDESA-N ranitidine Chemical compound [O-][N+](=O)/C=C(/NC)NCCSCC1=CC=C(CN(C)C)O1 VMXUWOKSQNHOCA-LCYFTJDESA-N 0.000 claims abstract description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 18
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 12
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 8
- -1 nitromethylene Chemical group 0.000 claims description 8
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 claims description 6
- ZVIREQPONFZPLQ-UHFFFAOYSA-N 1-nitroethenamine Chemical compound NC(=C)[N+]([O-])=O ZVIREQPONFZPLQ-UHFFFAOYSA-N 0.000 claims description 4
- 125000004414 alkyl thio group Chemical group 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 4
- 238000001704 evaporation Methods 0.000 claims description 4
- 150000002240 furans Chemical class 0.000 claims description 4
- 239000000377 silicon dioxide Substances 0.000 claims description 4
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 2
- 229940122957 Histamine H2 receptor antagonist Drugs 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 229940100198 alkylating agent Drugs 0.000 claims description 2
- 239000002168 alkylating agent Substances 0.000 claims description 2
- 239000000010 aprotic solvent Substances 0.000 claims description 2
- 238000004587 chromatography analysis Methods 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 230000008020 evaporation Effects 0.000 claims description 2
- 239000000706 filtrate Substances 0.000 claims description 2
- 239000003485 histamine H2 receptor antagonist Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 239000000725 suspension Substances 0.000 claims description 2
- 125000003396 thiol group Chemical class [H]S* 0.000 claims description 2
- BKPFPICPGCKKAA-UHFFFAOYSA-N 1-(aziridin-1-yl)-n-methyl-2-nitroethenamine Chemical compound [O-][N+](=O)C=C(NC)N1CC1 BKPFPICPGCKKAA-UHFFFAOYSA-N 0.000 abstract 1
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
- 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
-
- 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)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The aziridine derivative: N-methyl- alpha -(nitromethylene)-1-aziridinemethanamine is described as well as a process of manufacture. This is a useful intermediate in the preparation of ranitidine.
Description
**ATTENTION** debut du champ DESC peut contenir fin de CLMS **.
REVENDICATIONS
1. N-méthyI-a-(nitrométhylène)- 1 -aziridineméthanamine.
2. Procédé de préparation de la N-méthyl-a-(nitrométhylène)-laziridineméthanamine, caractérisé en ce que l'on fait réagir de l'éthy léne-imine avec une nitroéthénamine de formule (V):
EMI1.1
où L" est un groupe partant.
3. Procédé selon la revendication 2, caractérisé en ce que L" est un groupe alkoxy C1-4 ou un groupe alkylthio C1-4.
L'invention se rapporte à un dérivé d'aziridine.
Le dérivé furannique de formule (I):
EMI1.2
est connu sous le nom de ranitidine et est décrit dans le brevet suisse
N 640846 comme un antagoniste-H2 puissant et sélectif.
Le brevet principal N 650257-0 décrit un procédé de préparation du dérivé furannique de formule (I) qui consiste à faire réagir un thiol de formule (Il):
EMI1.3
avec un agent alkylant de formule (III):
EMI1.4
où R1 est le groupe - CH2CH2L, dans lequel L est un groupe partant, et R2 est un atome d'hydrogène, ou R1 et R2, ensemble avec l'atome d'azote auquel ils sont rattachés, forment un groupe éthylène-imino.
Ce procédé est un moyen nouveau et utile de préparation du composé ranitidine.
La présente invention concerne le composé défini ci-dessus par la formule (III) dans laquelle R1 R2N est un groupe éthylène-imino, c'est-à-dire la N-méthyl-a-(nitrométhylène)-l -aziridineméthanamine de formule (IV):
EMI1.5
Le dérivé d'aziridine de formule (IV) peut être préparé par réaction de l'éthylene-imine avec une nitroéthénamine de formule (V):
EMI1.6
dans laquelle L" est un groupe partant, par exemple un groupe alcoxy C14 ou un groupe alkylthio C14, de préférence méthylthio. La réaction peut être conduite dans un solvant aprotique convenable tel que l'acétonitrile.
L'invention est illustrée par l'exemple suivant:
Exemple:
N-métllyl-a- (nitroniéthyléize) -I-aeiridinemétllanamine
On agite à température ambiante pendant 2 d une solution d'éthyléne-imine (0,47 g) et de N-méthyl-(l-méthylthio)-2-nitroéthénamine (1,48 g) dans l'acétonitrile. On évapore la suspension sous vide à température ambiante et on extrait le résidu avec de l'acétate d'éthyle chaud (100 ml).
Par évaporation sous vide de l'extrait, on obtient un résidu qui est suspendu dans de l'acétate d'éthyle (50 ml) et filtré. On évapore le filtrat jusqu'à 5 ml environ et on chromatographie (silicelacétate d'éthyle). Par évaporation sous vide de l'éluat approprié [couche mince (silice/acétate d'éthyle) Rf 0,281, on obtient le composé cité en titre (0,33 g), Pf 118-119 C.
** ATTENTION ** start of the DESC field may contain end of CLMS **.
CLAIMS
1. N-methyl-a- (nitromethylene) - 1 -aziridinemethanamine.
2. Process for the preparation of N-methyl-a- (nitromethylene) -laziridinemethanamine, characterized in that ethylene-imine is reacted with a nitroethenamine of formula (V):
EMI1.1
where L "is a leaving group.
3. Method according to claim 2, characterized in that L "is a C1-4 alkoxy group or a C1-4 alkylthio group.
The invention relates to an aziridine derivative.
The furan derivative of formula (I):
EMI1.2
is known as ranitidine and is described in the Swiss patent
N 640846 as a powerful and selective H2 antagonist.
The main patent N 650257-0 describes a process for preparing the furan derivative of formula (I) which consists in reacting a thiol of formula (II):
EMI1.3
with an alkylating agent of formula (III):
EMI1.4
where R1 is the group - CH2CH2L, in which L is a leaving group, and R2 is a hydrogen atom, or R1 and R2, together with the nitrogen atom to which they are attached, form an ethylene-imino group.
This process is a new and useful means of preparing the ranitidine compound.
The present invention relates to the compound defined above by formula (III) in which R1 R2N is an ethylene-imino group, that is to say N-methyl-a- (nitromethylene) -l -aziridinmethanamine of formula (IV):
EMI1.5
The aziridine derivative of formula (IV) can be prepared by reaction of ethyleneimine with a nitroethenamine of formula (V):
EMI1.6
in which L ″ is a leaving group, for example a C14 alkoxy group or a C14 alkylthio group, preferably methylthio. The reaction can be carried out in a suitable aprotic solvent such as acetonitrile.
The invention is illustrated by the following example:
Example:
N-metllyl-a- (nitroniethylize) -I-aeiridinemetallanamine
Stirred at room temperature for 2 d a solution of ethylene imine (0.47 g) and N-methyl- (1-methylthio) -2-nitroethenamine (1.48 g) in acetonitrile. The suspension is evaporated in vacuo at room temperature and the residue is extracted with hot ethyl acetate (100 ml).
By evaporating the extract under vacuum, a residue is obtained which is suspended in ethyl acetate (50 ml) and filtered. The filtrate is evaporated to approximately 5 ml and chromatography (ethyl silica acetate). By evaporation under vacuum of the appropriate eluate [thin layer (silica / ethyl acetate) Rf 0.281, the title compound is obtained (0.33 g), Pf 118-119 C.
Claims (3)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8000580 | 1980-01-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH654830A5 true CH654830A5 (en) | 1986-03-14 |
Family
ID=10510510
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH2979/84A CH654830A5 (en) | 1980-01-08 | 1981-01-08 | Aziridine derivative |
Country Status (5)
| Country | Link |
|---|---|
| JP (1) | JPS56103171A (en) |
| KR (1) | KR840002007B1 (en) |
| BE (1) | BE886997A (en) |
| CH (1) | CH654830A5 (en) |
| GB (1) | GB2067991B (en) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ATE13058T1 (en) * | 1980-12-30 | 1985-05-15 | Glaxo Group Ltd | PROCESS FOR THE PREPARATION OF A FURAN DERIVATIVE. |
| PT74235B (en) * | 1980-12-30 | 1984-01-04 | Glaxo Group Ltd | Process for the preparation of a furan derivative |
| JPS57150640A (en) * | 1981-02-03 | 1982-09-17 | Glaxo Group Ltd | Therapeutical nitrovinyl derivatives and medicinal composition containing them |
| PT74459B (en) * | 1981-02-20 | 1984-10-09 | Glaxo Group Ltd | Process for the preparation of a furan derivative |
| 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 |
| AT389873B (en) * | 1983-07-15 | 1990-02-12 | Richter Gedeon Vegyeszet | METHOD FOR PRODUCING THE 1- (2- (5- / |
| US5686588A (en) * | 1995-08-16 | 1997-11-11 | Yoo; Seo Hong | Amine acid salt compounds and process for the production thereof |
-
1981
- 1981-01-08 CH CH2979/84A patent/CH654830A5/en not_active IP Right Cessation
- 1981-01-08 BE BE0/203425A patent/BE886997A/en not_active IP Right Cessation
- 1981-01-08 GB GB8100477A patent/GB2067991B/en not_active Expired
- 1981-01-08 KR KR1019810000033A patent/KR840002007B1/en active
- 1981-01-08 JP JP83381A patent/JPS56103171A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0224827B2 (en) | 1990-05-30 |
| GB2067991A (en) | 1981-08-05 |
| JPS56103171A (en) | 1981-08-18 |
| GB2067991B (en) | 1983-10-19 |
| KR840002007B1 (en) | 1984-10-27 |
| KR830005191A (en) | 1983-08-03 |
| BE886997A (en) | 1981-07-08 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |