NO761978L - - Google Patents
Info
- Publication number
- NO761978L NO761978L NO761978A NO761978A NO761978L NO 761978 L NO761978 L NO 761978L NO 761978 A NO761978 A NO 761978A NO 761978 A NO761978 A NO 761978A NO 761978 L NO761978 L NO 761978L
- Authority
- NO
- Norway
- Prior art keywords
- group
- methyl
- alkyl group
- ethyl
- aminocrotonate
- Prior art date
Links
- 125000000217 alkyl group Chemical group 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 125000005599 alkyl carboxylate group Chemical group 0.000 description 4
- 150000002576 ketones Chemical class 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 150000002081 enamines Chemical class 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- FLNJZNHUCKTVEA-NTMALXAHSA-N methyl (z)-3-[(1-ethylpyrrolidin-2-yl)methylamino]but-2-enoate Chemical compound CCN1CCCC1CN\C(C)=C/C(=O)OC FLNJZNHUCKTVEA-NTMALXAHSA-N 0.000 description 3
- VDOMTIYXBZIWNT-DQMXGCRQSA-N methyl (z)-3-[(1-ethylpyrrolidin-2-yl)methylamino]but-2-enoate;hydrochloride Chemical compound Cl.CCN1CCCC1CN\C(C)=C/C(=O)OC VDOMTIYXBZIWNT-DQMXGCRQSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 125000002252 acyl group Chemical group 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- SKOLWUPSYHWYAM-UHFFFAOYSA-N carbonodithioic O,S-acid Chemical compound SC(S)=O SKOLWUPSYHWYAM-UHFFFAOYSA-N 0.000 description 2
- HRKQOINLCJTGBK-UHFFFAOYSA-N dihydroxidosulfur Chemical compound OSO HRKQOINLCJTGBK-UHFFFAOYSA-N 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 150000003568 thioethers Chemical class 0.000 description 2
- UNRBEYYLYRXYCG-UHFFFAOYSA-N (1-ethylpyrrolidin-2-yl)methanamine Chemical compound CCN1CCCC1CN UNRBEYYLYRXYCG-UHFFFAOYSA-N 0.000 description 1
- WRQNANDWMGAFTP-UHFFFAOYSA-N Methylacetoacetic acid Chemical compound COC(=O)CC(C)=O WRQNANDWMGAFTP-UHFFFAOYSA-N 0.000 description 1
- MUCRYNWJQNHDJH-OADIDDRXSA-N Ursonic acid Chemical class C1CC(=O)C(C)(C)[C@@H]2CC[C@@]3(C)[C@]4(C)CC[C@@]5(C(O)=O)CC[C@@H](C)[C@H](C)[C@H]5C4=CC[C@@H]3[C@]21C MUCRYNWJQNHDJH-OADIDDRXSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 230000001225 therapeutic effect Effects 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
- C07D207/04—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 no double bonds between ring members or between ring members and non-ring members
- C07D207/08—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 no double bonds between ring members or between ring members and non-ring members with hydrocarbon radicals, substituted by hetero atoms, attached to ring carbon atoms
- C07D207/09—Radicals substituted by nitrogen atoms, not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/26—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D223/00—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom
- C07D223/02—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D223/04—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom not condensed with other rings with only hydrogen atoms, halogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyrrole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Description
Nye enaminer.
Gjenstanden for foreliggende oppfinnelse er ny<i enaminer med den følgende generelle formel:
der: R kan være en C-^^-alkylgruppe eller C2_^-alkenylgruppe, eventuelt inneholdende en reaktiv funksjon slik som en alkohol, tioalkohol, keton, tioketon, eter eller tioeter, kan være en alkylgruppe med 1-5 karbonatomer eller en alkylkarboksylatgruppe, eller en acylgruppe, kan være hydrogen eller en alkylgruppe med 1-5 karbonatomer, FU kan være en alkylgruppe med 1-5 karbonatomer, eller en alkylkarboksylatgruppe, R2og kan være bundet sammen via en metylengruppe, og n og m er 1, 2 eller 33såvel som høyre- og venstredreine isomerer derav, syreaddisjonssalter, og kvaternære ammoniumsalter derav, samt en fremgangsmåte for fremstilling av disse.
Forbindelsene ifølge oppfinnelsen kan f.eks. benyttes for syntetisering av forbindelser med verdifulle tera-peutiske egenskaper.
Forbindelsene ifølge oppfinnelsen kan fremstilles ved omsetning av ketoner med et mobilt hydrogenatom i a-stilling, alifatiske B-diketoner eller g-ketonestere med et amin med følg-ende generelle formel:
der: n,m og R har den ovenfor angitte betydning.
Det følgende eksempel skal illustrere oppfinnelsen: Metyl-N-(l-etyl-2-pyrrolidylmetyl)-3-aminocrotonat-hydroklorid. 38j4 g eller 0,3 mol N-etyl-2-aminometylpyrrolidin og en dråpe saltsyre (d = l,l8) ble tilsatt til en 25.0 ml kolbe ut-styrt med et røreverk, et termometer, en Kondensator og en dryppe-trakt; 34,8 g eller 0,3 mol metylacetoacetat ble tilsatt dråpevis. Temperaturen nådde 54°C ved enden av tilføringen. Blandingen ble deretter bragt tilbake til omgivelsestemperatur under omrøring og 150 ml metylenklorid og 5 g magnesiumsulfat ble tilsatt. Blandingen ble omrørt i 1 time, filtrert og oppløsningsmidlet ble for-dampet i vakuum, og resten ble destillert. Det ble oppnådd 55 g metyl-N-(l-etyl-2-pyrrolidylmetyl)3-aminocrotonat. Utbyttet var 81,156 og kokepunktet ved 3 mm/Hg var 132-134°C. 55 g eller 0,24 mol metyl-N-(l-etyl-2-pyrrolidyl-metyl)-3-aminocrotonat, 250 ml acetaon og en tilstrekkelig mengde etanolisk saltsyre til å bringe pH-verdien til 1 ble tilsatt til et 500 ml begerglass under omrøring av blandingen. Produktet ble tillatt å krystallisere ut og ble deretter filtrert og tørket i en ovn ved 50°C.
Det ble oppnådd 60,8 g metyl-N-(l-etyl-2-pyrroli-dylmetyl)-3-aminocrotonathydroklorid i et utbytte på 95, 2% og med et smeltepunkt på 140°C.
1. Enaminer,karakterisert ved
den generelle formel:
der: R kan være en C1_^-alkylgruppe eller C2_^-alkenylgruppe, eventuelt inneholdende en reaktiv funksjon som en alkohol, tioalkohol, et keton, et tioketon, en eter eller en tioeter, R^kan være en alkylgruppe med 1-5 karbonatomer eller en alkylkarboksylatgruppe eller en acylgruppe, R2kan være hydrogen eller en alkylgruppe inneholdende 1-5 karbonatomer, R-^kan være en alkylgruppe med 1-5 karbonatomer eller en alkylkarboksylatgruppe, R ? og R^sammen kan være en metylengruppe, og n og m kan ha verdien 1, 2 eller 3?såvel som høyre- og venstredreine isomerer derav, syreaddisjonssalter og kvaternære ammoniumsalter derav. 2. Produkt ifølge krav 1, i form av metyl-N-(1-etyl-2- pyrrolidylmetyl)-3-aminocrotonathydroklorid. 3- Fremgangangsmåte for fremstilling av forbindelser ifølge krav 1,karakterisert' ved behandlig av ketoner med et mobilt hydrogenatom i a-stilling, alifatiske (3-diketoner eller 3-ketonestere, med et racemisk høyre- eller venstredreiene amin med den generelle formel:
hvori n, m og R har den ovenfor angitte betydning, og deretter eventuelt behandling av den oppnådde forbindelse med en mineral-syre eller en organisk syre eller med et middel for fremstilling av et kvaternært ammoniumsalt. 4. Fremgangsmåte ifølge krav 3>for fremstilling av metyl-N-(l-etyl-2-pyrrolidylmetyl)-3-aminocrotonat.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7518344A FR2314179A1 (fr) | 1975-06-12 | 1975-06-12 | Nouvelles enamines et leur procede de preparation |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO761978L true NO761978L (no) | 1976-12-14 |
Family
ID=9156406
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO761978A NO761978L (no) | 1975-06-12 | 1976-06-09 |
Country Status (38)
| Country | Link |
|---|---|
| US (1) | US4077976A (no) |
| JP (1) | JPS6016414B2 (no) |
| AR (1) | AR211016A1 (no) |
| AT (1) | AT361461B (no) |
| AU (1) | AU498622B2 (no) |
| BE (1) | BE842060A (no) |
| BG (1) | BG34184A3 (no) |
| CA (1) | CA1069911A (no) |
| CH (1) | CH615420A5 (no) |
| CS (1) | CS195311B2 (no) |
| DE (1) | DE2623076A1 (no) |
| DK (1) | DK260276A (no) |
| EG (1) | EG13535A (no) |
| FI (1) | FI63749C (no) |
| FR (1) | FR2314179A1 (no) |
| GB (1) | GB1500225A (no) |
| HK (1) | HK47079A (no) |
| HU (1) | HU171358B (no) |
| IE (1) | IE43002B1 (no) |
| IL (1) | IL49597A (no) |
| IN (1) | IN142641B (no) |
| LU (1) | LU75105A1 (no) |
| MC (1) | MC1103A1 (no) |
| MW (1) | MW1776A1 (no) |
| MX (1) | MX3617E (no) |
| NL (1) | NL7606353A (no) |
| NO (1) | NO761978L (no) |
| NZ (1) | NZ181073A (no) |
| OA (1) | OA05349A (no) |
| PH (1) | PH13943A (no) |
| PL (1) | PL106501B1 (no) |
| PT (1) | PT65166B (no) |
| RO (1) | RO69115A (no) |
| SE (1) | SE410791B (no) |
| SU (1) | SU629874A3 (no) |
| YU (1) | YU39542B (no) |
| ZA (1) | ZA763043B (no) |
| ZM (1) | ZM6676A1 (no) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4370335A (en) * | 1982-02-02 | 1983-01-25 | Mcneilab, Inc. | Antisecretory 4-diphenylmethyl-1-[(oxoalkyl)imino]methyl-piperidines and their derivatives |
| DE3670080D1 (de) * | 1985-12-23 | 1990-05-10 | Zambeletti Spa L | Azacyclische verbindungen, verfahren zur ihrer herstellung und ihre verwendung als pharmazeutika. |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3878223A (en) * | 1973-03-12 | 1975-04-15 | Abbott Lab | N-Substituted acrylamides |
-
1975
- 1975-06-12 FR FR7518344A patent/FR2314179A1/fr active Granted
-
1976
- 1976-05-17 IL IL49597A patent/IL49597A/xx unknown
- 1976-05-20 MC MC761195A patent/MC1103A1/fr unknown
- 1976-05-21 ZA ZA763043A patent/ZA763043B/xx unknown
- 1976-05-21 BE BE1007405A patent/BE842060A/xx not_active IP Right Cessation
- 1976-05-22 DE DE19762623076 patent/DE2623076A1/de not_active Withdrawn
- 1976-05-24 AR AR263375A patent/AR211016A1/es active
- 1976-05-27 IN IN927/CAL/1976A patent/IN142641B/en unknown
- 1976-05-27 AU AU14361/76A patent/AU498622B2/en not_active Expired
- 1976-05-28 YU YU1319/76A patent/YU39542B/xx unknown
- 1976-06-01 RO RO7686313A patent/RO69115A/ro unknown
- 1976-06-01 IE IE1168/76A patent/IE43002B1/en unknown
- 1976-06-01 AT AT400276A patent/AT361461B/de not_active IP Right Cessation
- 1976-06-01 PT PT65166A patent/PT65166B/pt unknown
- 1976-06-01 SU SU762362104A patent/SU629874A3/ru active
- 1976-06-02 EG EG327/76A patent/EG13535A/xx active
- 1976-06-03 ZM ZM66/76A patent/ZM6676A1/xx unknown
- 1976-06-04 NZ NZ181073A patent/NZ181073A/xx unknown
- 1976-06-04 BG BG033363A patent/BG34184A3/xx unknown
- 1976-06-04 CS CS763722A patent/CS195311B2/cs unknown
- 1976-06-07 PH PH18544A patent/PH13943A/en unknown
- 1976-06-08 SE SE7606426A patent/SE410791B/xx not_active IP Right Cessation
- 1976-06-08 LU LU75105A patent/LU75105A1/xx unknown
- 1976-06-09 OA OA55846A patent/OA05349A/xx unknown
- 1976-06-09 MX MX76293U patent/MX3617E/es unknown
- 1976-06-09 CA CA254,483A patent/CA1069911A/en not_active Expired
- 1976-06-09 NO NO761978A patent/NO761978L/no unknown
- 1976-06-10 PL PL1976190303A patent/PL106501B1/pl unknown
- 1976-06-10 JP JP51068623A patent/JPS6016414B2/ja not_active Expired
- 1976-06-10 MW MW17/76A patent/MW1776A1/xx unknown
- 1976-06-10 GB GB24113/76A patent/GB1500225A/en not_active Expired
- 1976-06-11 NL NL7606353A patent/NL7606353A/xx not_active Application Discontinuation
- 1976-06-11 US US05/694,877 patent/US4077976A/en not_active Expired - Lifetime
- 1976-06-11 CH CH745176A patent/CH615420A5/fr not_active IP Right Cessation
- 1976-06-11 HU HU76SO00001172A patent/HU171358B/hu unknown
- 1976-06-11 FI FI761679A patent/FI63749C/fi not_active IP Right Cessation
- 1976-06-11 DK DK260276A patent/DK260276A/da not_active Application Discontinuation
-
1979
- 1979-07-12 HK HK470/79A patent/HK47079A/xx unknown
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