FI63400C - Foerfarande foer framstaellning av fenylaminoergoliner och syraadditionssalter daerav med dopaminverkan - Google Patents
Foerfarande foer framstaellning av fenylaminoergoliner och syraadditionssalter daerav med dopaminverkan Download PDFInfo
- Publication number
- FI63400C FI63400C FI782589A FI782589A FI63400C FI 63400 C FI63400 C FI 63400C FI 782589 A FI782589 A FI 782589A FI 782589 A FI782589 A FI 782589A FI 63400 C FI63400 C FI 63400C
- Authority
- FI
- Finland
- Prior art keywords
- formula
- compound
- och
- fenylaminoergoliner
- dopaminverkan
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims description 27
- 238000000034 method Methods 0.000 claims description 11
- 150000003839 salts Chemical class 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- DVFIFSNQKRLRNB-GERZZCHPSA-N C1[C@H]2[C@@H](CC3=CNC4=CC=CC2=C34)NCC1NC5=CC=CC=C5 Chemical class C1[C@H]2[C@@H](CC3=CNC4=CC=CC2=C34)NCC1NC5=CC=CC=C5 DVFIFSNQKRLRNB-GERZZCHPSA-N 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 claims description 3
- 230000002829 reductive effect Effects 0.000 claims description 3
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- 210000005036 nerve Anatomy 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 4
- 229960000583 acetic acid Drugs 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 239000012362 glacial acetic acid Substances 0.000 description 3
- YKYIFUROKBDHCY-ONEGZZNKSA-N (e)-4-ethoxy-1,1,1-trifluorobut-3-en-2-one Chemical group CCO\C=C\C(=O)C(F)(F)F YKYIFUROKBDHCY-ONEGZZNKSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 229960003638 dopamine Drugs 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000010828 elution Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- YMVPBQLZTLJMEJ-CKALXEAQSA-N (6aR,10aR)-9-(4-ethoxyphenyl)-7-methyl-4,6,6a,8,10,10a-hexahydroindolo[4,3-fg]quinolin-9-amine Chemical compound C(C)OC1=CC=C(C=C1)C1(CN([C@@H]2CC3=CNC4=CC=CC([C@H]2C1)=C34)C)N YMVPBQLZTLJMEJ-CKALXEAQSA-N 0.000 description 1
- YMVPBQLZTLJMEJ-WPYKKVEZSA-N (6aR,9R,10aS)-9-(4-ethoxyphenyl)-7-methyl-4,6,6a,8,10,10a-hexahydroindolo[4,3-fg]quinolin-9-amine Chemical compound C(C)OC1=CC=C(C=C1)[C@]1(CN([C@@H]2CC3=CNC4=CC=CC([C@@H]2C1)=C34)C)N YMVPBQLZTLJMEJ-WPYKKVEZSA-N 0.000 description 1
- SPIPOSYHHHHGKN-DSKINZAPSA-N (6aR,9R,10aS)-9-(4-fluorophenyl)-7-methyl-4,6,6a,8,10,10a-hexahydroindolo[4,3-fg]quinolin-9-amine Chemical compound FC1=CC=C(C=C1)[C@]1(CN([C@@H]2CC3=CNC4=CC=CC([C@@H]2C1)=C34)C)N SPIPOSYHHHHGKN-DSKINZAPSA-N 0.000 description 1
- YMVPBQLZTLJMEJ-XKCSPQBFSA-N (6aR,9S,10aS)-9-(4-ethoxyphenyl)-7-methyl-4,6,6a,8,10,10a-hexahydroindolo[4,3-fg]quinolin-9-amine Chemical compound C(C)OC1=CC=C(C=C1)[C@@]1(CN([C@@H]2CC3=CNC4=CC=CC([C@@H]2C1)=C34)C)N YMVPBQLZTLJMEJ-XKCSPQBFSA-N 0.000 description 1
- WZWHHCYTJDBJPY-TZMCWYRMSA-N (6ar,10ar)-7-methyl-4,6,6a,8,10,10a-hexahydroindolo[4,3-fg]quinoline-9-one Chemical compound C1=CC([C@H]2CC(=O)CN([C@@H]2C2)C)=C3C2=CNC3=C1 WZWHHCYTJDBJPY-TZMCWYRMSA-N 0.000 description 1
- KGUBZNRUCSWDAU-HCGVIMEBSA-N (6ar,10ar)-7-methyl-6,6a,8,9,10,10a-hexahydro-4h-indolo[4,3-fg]quinoline-9-amine Chemical compound C1=CC([C@H]2CC(N)CN([C@@H]2C2)C)=C3C2=CNC3=C1 KGUBZNRUCSWDAU-HCGVIMEBSA-N 0.000 description 1
- FWWOWPGPERBCNJ-UHFFFAOYSA-N 2-hydroxy-4-(2-hydroxyethoxy)-4-oxobutanoic acid Chemical compound OCCOC(=O)CC(O)C(O)=O FWWOWPGPERBCNJ-UHFFFAOYSA-N 0.000 description 1
- -1 3-pyridyl amino side chain Chemical group 0.000 description 1
- IMPPGHMHELILKG-UHFFFAOYSA-N 4-ethoxyaniline Chemical compound CCOC1=CC=C(N)C=C1 IMPPGHMHELILKG-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 208000018737 Parkinson disease Diseases 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D457/00—Heterocyclic compounds containing indolo [4, 3-f, g] quinoline ring systems, e.g. derivatives of ergoline, of the formula:, e.g. lysergic acid
- C07D457/10—Heterocyclic compounds containing indolo [4, 3-f, g] quinoline ring systems, e.g. derivatives of ergoline, of the formula:, e.g. lysergic acid with hetero atoms directly attached in position 8
- C07D457/12—Nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Wrappers (AREA)
- Laminated Bodies (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1073277 | 1977-09-02 | ||
| CH1073277 | 1977-09-02 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI782589A7 FI782589A7 (fi) | 1979-03-03 |
| FI63400B FI63400B (fi) | 1983-02-28 |
| FI63400C true FI63400C (fi) | 1983-06-10 |
Family
ID=4366242
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI782589A FI63400C (fi) | 1977-09-02 | 1978-08-24 | Foerfarande foer framstaellning av fenylaminoergoliner och syraadditionssalter daerav med dopaminverkan |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US4219556A (it) |
| EP (1) | EP0001062B1 (it) |
| JP (2) | JPS5448880A (it) |
| AT (1) | AT368500B (it) |
| AU (1) | AU520880B2 (it) |
| CA (1) | CA1109864A (it) |
| DE (1) | DE2860653D1 (it) |
| DK (1) | DK374778A (it) |
| ES (1) | ES472993A1 (it) |
| FI (1) | FI63400C (it) |
| IL (1) | IL55466A (it) |
| IT (1) | IT1098421B (it) |
| NZ (1) | NZ188299A (it) |
| PH (1) | PH15739A (it) |
| PT (1) | PT68491A (it) |
| ZA (1) | ZA785003B (it) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0021206B1 (de) * | 1979-06-13 | 1983-06-22 | Schering Aktiengesellschaft | Neue (Ergolin-yl)-N', N'-diäthylharnstoff-Derivate, ihre Herstellung und sie enthaltende Arzneimittel |
| US4526892A (en) * | 1981-03-03 | 1985-07-02 | Farmitalia Carlo Erba, S.P.A. | Dimethylaminoalkyl-3-(ergoline-8'βcarbonyl)-ureas |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3185695A (en) * | 1965-05-25 | Dbwethyl-ergoline ii derivatives | ||
| US2997470A (en) * | 1956-03-05 | 1961-08-22 | Lilly Co Eli | Lysergic acid amides |
| FI751031A7 (it) * | 1974-04-16 | 1975-10-17 | Sandoz Ag | |
| US4004011A (en) * | 1974-04-16 | 1977-01-18 | Sandoz Ltd. | 3-Pyridylamine substituted ergolines |
-
1978
- 1978-07-11 JP JP8451578A patent/JPS5448880A/ja active Pending
- 1978-08-18 DE DE7878100701T patent/DE2860653D1/de not_active Expired
- 1978-08-18 EP EP78100701A patent/EP0001062B1/de not_active Expired
- 1978-08-24 DK DK374778A patent/DK374778A/da not_active Application Discontinuation
- 1978-08-24 FI FI782589A patent/FI63400C/fi not_active IP Right Cessation
- 1978-08-31 CA CA310,469A patent/CA1109864A/en not_active Expired
- 1978-08-31 AU AU39450/78A patent/AU520880B2/en not_active Expired
- 1978-08-31 PH PH21553A patent/PH15739A/en unknown
- 1978-08-31 PT PT68491A patent/PT68491A/pt unknown
- 1978-08-31 NZ NZ188299A patent/NZ188299A/xx unknown
- 1978-08-31 ES ES472993A patent/ES472993A1/es not_active Expired
- 1978-08-31 IL IL55466A patent/IL55466A/xx unknown
- 1978-09-01 ZA ZA785003A patent/ZA785003B/xx unknown
- 1978-09-01 US US05/939,105 patent/US4219556A/en not_active Expired - Lifetime
- 1978-09-01 IT IT27256/78A patent/IT1098421B/it active
- 1978-09-01 JP JP10803378A patent/JPS5448800A/ja active Pending
- 1978-09-01 AT AT0633678A patent/AT368500B/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| IL55466A (en) | 1981-09-13 |
| PT68491A (fr) | 1978-09-01 |
| CA1109864A (en) | 1981-09-29 |
| FI63400B (fi) | 1983-02-28 |
| IL55466A0 (en) | 1978-10-31 |
| AT368500B (de) | 1982-10-11 |
| ES472993A1 (es) | 1979-11-16 |
| US4219556A (en) | 1980-08-26 |
| JPS5448800A (en) | 1979-04-17 |
| DE2860653D1 (en) | 1981-08-06 |
| ZA785003B (en) | 1980-04-30 |
| EP0001062B1 (de) | 1981-04-29 |
| PH15739A (en) | 1983-03-18 |
| AU520880B2 (en) | 1982-03-04 |
| NZ188299A (en) | 1981-03-16 |
| DK374778A (da) | 1979-03-03 |
| IT7827256A0 (it) | 1978-09-01 |
| ATA633678A (de) | 1982-02-15 |
| AU3945078A (en) | 1980-03-06 |
| JPS5448880A (en) | 1979-04-17 |
| FI782589A7 (fi) | 1979-03-03 |
| EP0001062A1 (de) | 1979-03-21 |
| IT1098421B (it) | 1985-09-07 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM | Patent lapsed |
Owner name: SANDOZ AG |