CH629798A5 - Process for the preparation of cyclic compounds - Google Patents
Process for the preparation of cyclic compounds Download PDFInfo
- Publication number
- CH629798A5 CH629798A5 CH540281A CH540281A CH629798A5 CH 629798 A5 CH629798 A5 CH 629798A5 CH 540281 A CH540281 A CH 540281A CH 540281 A CH540281 A CH 540281A CH 629798 A5 CH629798 A5 CH 629798A5
- Authority
- CH
- Switzerland
- Prior art keywords
- dimethyl
- indol
- imidazolidinone
- methylimino
- lower alkyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 7
- 238000002360 preparation method Methods 0.000 title claims description 4
- 150000001923 cyclic compounds Chemical class 0.000 title description 2
- -1 Indol-3-yl-methylene Chemical group 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- 239000012022 methylating agents Substances 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 206010015995 Eyelid ptosis Diseases 0.000 description 3
- 241000699670 Mus sp. Species 0.000 description 3
- 201000003004 ptosis Diseases 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 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 2
- GXBMTEAMDOVNLO-UHFFFAOYSA-N 5-(1h-indol-3-ylmethylidene)-1,3-dimethyl-2-methyliminoimidazolidin-4-one Chemical compound CN1C(=NC)N(C)C(=O)C1=CC1=CNC2=CC=CC=C12 GXBMTEAMDOVNLO-UHFFFAOYSA-N 0.000 description 2
- AZGOVLGMSGAOMP-UHFFFAOYSA-N Aplysinopsin Natural products O=C1N(C)C(=N)N(C)C1=CC1=CNC2=CC=CC=C12 AZGOVLGMSGAOMP-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- RHVPEFQDYMMNSY-UHFFFAOYSA-N Harmalol Natural products N1C2=CC(O)=CC=C2C2=C1C(C)=NCC2 RHVPEFQDYMMNSY-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- 230000003042 antagnostic effect Effects 0.000 description 2
- 230000001430 anti-depressive effect Effects 0.000 description 2
- 239000000935 antidepressant agent Substances 0.000 description 2
- 229940005513 antidepressants Drugs 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- RERZNCLIYCABFS-UHFFFAOYSA-N harmaline Chemical compound C1CN=C(C)C2=C1C1=CC=C(OC)C=C1N2 RERZNCLIYCABFS-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
- YAMHXTCMCPHKLN-UHFFFAOYSA-N imidazolidin-2-one Chemical compound O=C1NCCN1 YAMHXTCMCPHKLN-UHFFFAOYSA-N 0.000 description 2
- 229960004801 imipramine Drugs 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
- OLNJUISKUQQNIM-UHFFFAOYSA-N indole-3-carbaldehyde Chemical class C1=CC=C2C(C=O)=CNC2=C1 OLNJUISKUQQNIM-UHFFFAOYSA-N 0.000 description 2
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 239000000825 pharmaceutical preparation Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 229960005333 tetrabenazine Drugs 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
- TYKJILJOXAHUFO-UHFFFAOYSA-N 2-amino-1,4-dihydroimidazol-5-one Chemical compound NC1=NC(=O)CN1 TYKJILJOXAHUFO-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
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- 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 1
- DPWPWRLQFGFJFI-UHFFFAOYSA-N Pargyline Chemical compound C#CCN(C)CC1=CC=CC=C1 DPWPWRLQFGFJFI-UHFFFAOYSA-N 0.000 description 1
- 241000243142 Porifera Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 230000001078 anti-cholinergic effect Effects 0.000 description 1
- 239000000872 buffer Substances 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
- 239000002775 capsule Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 230000002526 effect on cardiovascular system Effects 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 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
- 239000008101 lactose Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 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
- 230000003204 osmotic effect Effects 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 229960001779 pargyline Drugs 0.000 description 1
- 235000019271 petrolatum Nutrition 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 238000010998 test method Methods 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
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Landscapes
- 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 |
| US05/821,854 US4176230A (en) | 1977-08-04 | 1977-08-04 | 5-(6-Alkylindol-3-ylmethylene)-1,3-dimethyl-2-(methylimino)-4-imidazolidinones |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH629798A5 true CH629798A5 (en) | 1982-05-14 |
Family
ID=26263303
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH540281A CH629798A5 (en) | 1976-09-07 | 1981-08-21 | Process for the preparation of cyclic compounds |
Country Status (11)
| Country | Link |
|---|---|
| JP (1) | JPS5350166A (cs) |
| AT (1) | AT364840B (cs) |
| AU (1) | AU514371B2 (cs) |
| BE (1) | BE858424A (cs) |
| CH (1) | CH629798A5 (cs) |
| FR (1) | FR2363567A1 (cs) |
| IE (1) | IE45583B1 (cs) |
| IL (1) | IL52895A (cs) |
| LU (1) | LU78081A1 (cs) |
| NL (1) | NL7709842A (cs) |
| NZ (1) | NZ185093A (cs) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2007059195A1 (en) * | 2005-11-14 | 2007-05-24 | University Of Southern California | Integrin-binding small molecules |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2435399A (en) * | 1944-10-23 | 1948-02-03 | Dow Chemical Co | Process for the preparation of indolalhydantoin |
-
1977
- 1977-09-05 FR FR7726835A patent/FR2363567A1/fr active Granted
- 1977-09-05 IL IL52895A patent/IL52895A/xx unknown
- 1977-09-05 NZ NZ18509377A patent/NZ185093A/xx unknown
- 1977-09-06 LU LU78081A patent/LU78081A1/xx unknown
- 1977-09-06 BE BE180686A patent/BE858424A/xx unknown
- 1977-09-06 JP JP10637777A patent/JPS5350166A/ja active Pending
- 1977-09-06 AT AT0639177A patent/AT364840B/de not_active IP Right Cessation
- 1977-09-06 AU AU28585/77A patent/AU514371B2/en not_active Expired
- 1977-09-07 NL NL7709842A patent/NL7709842A/xx not_active Application Discontinuation
- 1977-09-07 IE IE185077A patent/IE45583B1/en unknown
-
1981
- 1981-08-21 CH CH540281A patent/CH629798A5/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| FR2363567B1 (cs) | 1980-01-18 |
| JPS5350166A (en) | 1978-05-08 |
| AU514371B2 (en) | 1981-02-05 |
| IE45583B1 (en) | 1982-10-06 |
| IL52895A0 (en) | 1977-11-30 |
| LU78081A1 (cs) | 1978-10-17 |
| NZ185093A (en) | 1980-05-08 |
| BE858424A (fr) | 1978-03-06 |
| FR2363567A1 (fr) | 1978-03-31 |
| AT364840B (de) | 1981-11-25 |
| IL52895A (en) | 1981-01-30 |
| AU2858577A (en) | 1979-03-15 |
| NL7709842A (nl) | 1978-03-09 |
| ATA639177A (de) | 1981-04-15 |
| IE45583L (en) | 1978-03-07 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |