DK142414B - Analogifremgangsmåde til fremstilling af 5-(indol-3-yl-methylen)-1,3-dimethyl-2-methylimino-4-imidazolidinoner. - Google Patents
Analogifremgangsmåde til fremstilling af 5-(indol-3-yl-methylen)-1,3-dimethyl-2-methylimino-4-imidazolidinoner. Download PDFInfo
- Publication number
- DK142414B DK142414B DK395977AA DK395977A DK142414B DK 142414 B DK142414 B DK 142414B DK 395977A A DK395977A A DK 395977AA DK 395977 A DK395977 A DK 395977A DK 142414 B DK142414 B DK 142414B
- Authority
- DK
- Denmark
- Prior art keywords
- dimethyl
- methylene
- methylimino
- indol
- imidazolidinone
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 12
- GXBMTEAMDOVNLO-UHFFFAOYSA-N 5-(1h-indol-3-ylmethylidene)-1,3-dimethyl-2-methyliminoimidazolidin-4-one Chemical class CN1C(=NC)N(C)C(=O)C1=CC1=CNC2=CC=CC=C12 GXBMTEAMDOVNLO-UHFFFAOYSA-N 0.000 title claims description 6
- 238000002360 preparation method Methods 0.000 title claims description 4
- OLNJUISKUQQNIM-UHFFFAOYSA-N indole-3-carbaldehyde Chemical compound C1=CC=C2C(C=O)=CNC2=C1 OLNJUISKUQQNIM-UHFFFAOYSA-N 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- XVVSBYAGYRRHBW-UHFFFAOYSA-N 1,3-dimethyl-2-methyliminoimidazolidin-4-one Chemical compound CN=C1N(C)CC(=O)N1C XVVSBYAGYRRHBW-UHFFFAOYSA-N 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 10
- 150000001875 compounds Chemical class 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 238000010992 reflux Methods 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- AZGOVLGMSGAOMP-UHFFFAOYSA-N 2-imino-5-(1h-indol-3-ylmethylidene)-1,3-dimethylimidazolidin-4-one Chemical compound O=C1N(C)C(=N)N(C)C1=CC1=CNC2=CC=CC=C12 AZGOVLGMSGAOMP-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- RERZNCLIYCABFS-UHFFFAOYSA-N harmaline Chemical compound C1CN=C(C)C2=C1C1=CC=C(OC)C=C1N2 RERZNCLIYCABFS-UHFFFAOYSA-N 0.000 description 4
- -1 indol-3-yl-methylene Chemical group 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- MKJIEFSOBYUXJB-HOCLYGCPSA-N (3S,11bS)-9,10-dimethoxy-3-isobutyl-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-a]isoquinolin-2-one Chemical compound C1CN2C[C@H](CC(C)C)C(=O)C[C@H]2C2=C1C=C(OC)C(OC)=C2 MKJIEFSOBYUXJB-HOCLYGCPSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 206010015995 Eyelid ptosis Diseases 0.000 description 3
- 241000699670 Mus sp. Species 0.000 description 3
- GXBMTEAMDOVNLO-PHUZRPDESA-N N1C=C(C2=CC=CC=C12)C=C1C(N(/C(/N1C)=N/C)C)=O Chemical compound N1C=C(C2=CC=CC=C12)C=C1C(N(/C(/N1C)=N/C)C)=O GXBMTEAMDOVNLO-PHUZRPDESA-N 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 201000003004 ptosis Diseases 0.000 description 3
- 229960005333 tetrabenazine Drugs 0.000 description 3
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 description 2
- DPWPWRLQFGFJFI-UHFFFAOYSA-N Pargyline Chemical compound C#CCN(C)CC1=CC=CC=C1 DPWPWRLQFGFJFI-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 230000003042 antagnostic effect Effects 0.000 description 2
- 230000001430 anti-depressive effect Effects 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- BCGWQEUPMDMJNV-UHFFFAOYSA-N imipramine Chemical compound C1CC2=CC=CC=C2N(CCCN(C)C)C2=CC=CC=C21 BCGWQEUPMDMJNV-UHFFFAOYSA-N 0.000 description 2
- 229960004801 imipramine Drugs 0.000 description 2
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000012022 methylating agents Substances 0.000 description 2
- 229960001779 pargyline Drugs 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- RHDADYXNUCMTQG-DMLYUBSXSA-N (3s,11bs)-9,10-dimethoxy-3-(2-methylpropyl)-1,3,4,6,7,11b-hexahydrobenzo[a]quinolizin-2-one;methanesulfonic acid Chemical compound CS(O)(=O)=O.C1CN2C[C@H](CC(C)C)C(=O)C[C@H]2C2=C1C=C(OC)C(OC)=C2 RHDADYXNUCMTQG-DMLYUBSXSA-N 0.000 description 1
- NQLHETVWDMRIPV-UHFFFAOYSA-N 2-imino-1,3-dimethylimidazolidin-4-one Chemical compound CN1CC(=O)N(C)C1=N NQLHETVWDMRIPV-UHFFFAOYSA-N 0.000 description 1
- VLIUKLMESJCYRF-UHFFFAOYSA-N 2-imino-1,3-dimethylimidazolidin-4-one;hydroiodide Chemical compound I.CN1CC(=O)N(C)C1=N VLIUKLMESJCYRF-UHFFFAOYSA-N 0.000 description 1
- JFJBLIGOGSDXNE-UHFFFAOYSA-N 5-(1H-indol-3-ylmethyl)-1,3-dimethyl-2-methyliminoimidazolidin-4-one Chemical class N1C=C(C2=CC=CC=C12)CC1C(N(C(N1C)=NC)C)=O JFJBLIGOGSDXNE-UHFFFAOYSA-N 0.000 description 1
- LZERQSJGPXFAKB-UHFFFAOYSA-N 6-methyl-1h-indole-3-carbaldehyde Chemical compound CC1=CC=C2C(C=O)=CNC2=C1 LZERQSJGPXFAKB-UHFFFAOYSA-N 0.000 description 1
- QEUZHSQSOKEWLH-KGQVPBNKSA-N CC1=CC=C2C(=CNC2=C1)C=C1C(N(/C(/N1C)=N/C)C)=O Chemical compound CC1=CC=C2C(=CNC2=C1)C=C1C(N(/C(/N1C)=N/C)C)=O QEUZHSQSOKEWLH-KGQVPBNKSA-N 0.000 description 1
- 208000020401 Depressive disease Diseases 0.000 description 1
- 241000264871 Dictyoceratida Species 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 229940040526 anhydrous sodium acetate Drugs 0.000 description 1
- 230000001078 anti-cholinergic effect Effects 0.000 description 1
- 239000000935 antidepressant agent Substances 0.000 description 1
- 229940005513 antidepressants Drugs 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- 230000002526 effect on cardiovascular system Effects 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- GVONPBONFIJAHJ-UHFFFAOYSA-N imidazolidin-4-one Chemical compound O=C1CNCN1 GVONPBONFIJAHJ-UHFFFAOYSA-N 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 230000011987 methylation Effects 0.000 description 1
- 238000007069 methylation reaction Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/415—1,2-Diazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/14—Radicals substituted by nitrogen atoms, not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/96—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB36997/76A GB1567911A (en) | 1976-09-07 | 1976-09-07 | 5-(indol-3-ylmethylene)-1,3-dimethyl-2-methylimino-4-imidazolidinone |
| GB3699776 | 1976-09-07 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DK395977A DK395977A (cs) | 1978-03-08 |
| DK142414B true DK142414B (da) | 1980-10-27 |
| DK142414C DK142414C (cs) | 1981-03-23 |
Family
ID=10392885
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK395977AA DK142414B (da) | 1976-09-07 | 1977-09-06 | Analogifremgangsmåde til fremstilling af 5-(indol-3-yl-methylen)-1,3-dimethyl-2-methylimino-4-imidazolidinoner. |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US4195179A (cs) |
| CA (1) | CA1096385A (cs) |
| DE (1) | DE2740151A1 (cs) |
| DK (1) | DK142414B (cs) |
| GB (1) | GB1567911A (cs) |
| IT (1) | IT1084226B (cs) |
| PH (1) | PH13622A (cs) |
| ZA (1) | ZA775365B (cs) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4570857B2 (ja) * | 2003-03-31 | 2010-10-27 | 富士フイルム株式会社 | 感光性組成物及び平版印刷版原版 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2833771A (en) * | 1958-05-06 | Process for the preparation of | ||
| US1849576A (en) * | 1926-02-13 | 1932-03-15 | Hoffmann La Roche | Glucoside of adonis vernalis l. and process for making same |
| US2364041A (en) * | 1942-01-05 | 1944-11-28 | Burton T Bush Inc | Process of preparing musk materials and product thereof |
| US2431127A (en) * | 1944-04-29 | 1947-11-18 | Gen Foods Corp | Process of treating cashew nut shell liquid |
| US3441563A (en) * | 1958-08-22 | 1969-04-29 | Bayer Ag | Process for the production of substituted pyrazolones and of monomethine dyestuffs thereof |
| US3904629A (en) * | 1970-07-17 | 1975-09-09 | American Home Prod | 4-alkyl cycloalkyl-1-piperazino-imidazolidin-2-ones or thiones |
| SU485113A1 (ru) * | 1974-02-22 | 1975-09-25 | Химико-Металлургический Институт Ан Казахской Сср | Способ получени скатилгидантоина |
-
1976
- 1976-09-07 GB GB36997/76A patent/GB1567911A/en not_active Expired
-
1977
- 1977-09-02 US US05/830,242 patent/US4195179A/en not_active Expired - Lifetime
- 1977-09-06 ZA ZA00775365A patent/ZA775365B/xx unknown
- 1977-09-06 DE DE19772740151 patent/DE2740151A1/de not_active Withdrawn
- 1977-09-06 CA CA286,134A patent/CA1096385A/en not_active Expired
- 1977-09-06 DK DK395977AA patent/DK142414B/da not_active IP Right Cessation
- 1977-09-06 PH PH20204A patent/PH13622A/en unknown
- 1977-09-07 IT IT27364/77A patent/IT1084226B/it active
Also Published As
| Publication number | Publication date |
|---|---|
| DK142414C (cs) | 1981-03-23 |
| DK395977A (cs) | 1978-03-08 |
| PH13622A (en) | 1980-08-07 |
| DE2740151A1 (de) | 1978-03-16 |
| GB1567911A (en) | 1980-05-21 |
| IT1084226B (it) | 1985-05-25 |
| CA1096385A (en) | 1981-02-24 |
| ZA775365B (en) | 1978-07-26 |
| US4195179A (en) | 1980-03-25 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PBP | Patent lapsed |