DE2407904A1 - D-2-subst.-6-alkyl-8-subst.-ergoline und verfahren zu ihrer herstellung - Google Patents
D-2-subst.-6-alkyl-8-subst.-ergoline und verfahren zu ihrer herstellungInfo
- Publication number
- DE2407904A1 DE2407904A1 DE19742407904 DE2407904A DE2407904A1 DE 2407904 A1 DE2407904 A1 DE 2407904A1 DE 19742407904 DE19742407904 DE 19742407904 DE 2407904 A DE2407904 A DE 2407904A DE 2407904 A1 DE2407904 A1 DE 2407904A1
- Authority
- DE
- Germany
- Prior art keywords
- compound
- formula
- ergoline
- methyl
- subst
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- 238000000034 method Methods 0.000 title claims description 14
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 21
- 229910052801 chlorine Inorganic materials 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- AWFDCTXCTHGORH-HGHGUNKESA-N 6-[4-[(6ar,9r,10ar)-5-bromo-7-methyl-6,6a,8,9,10,10a-hexahydro-4h-indolo[4,3-fg]quinoline-9-carbonyl]piperazin-1-yl]-1-methylpyridin-2-one Chemical class O=C([C@H]1CN([C@H]2[C@@H](C=3C=CC=C4NC(Br)=C(C=34)C2)C1)C)N(CC1)CCN1C1=CC=CC(=O)N1C AWFDCTXCTHGORH-HGHGUNKESA-N 0.000 claims description 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 3
- 150000007513 acids Chemical class 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- ATDGTVJJHBUTRL-UHFFFAOYSA-N cyanogen bromide Chemical compound BrC#N ATDGTVJJHBUTRL-UHFFFAOYSA-N 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- 230000007062 hydrolysis Effects 0.000 claims description 2
- 238000006460 hydrolysis reaction Methods 0.000 claims description 2
- 229910052740 iodine Inorganic materials 0.000 claims description 2
- 231100000252 nontoxic Toxicity 0.000 claims description 2
- 230000003000 nontoxic effect Effects 0.000 claims description 2
- 230000017858 demethylation Effects 0.000 claims 1
- 238000010520 demethylation reaction Methods 0.000 claims 1
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 239000000460 chlorine Substances 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 4
- 102000003946 Prolactin Human genes 0.000 description 4
- 108010057464 Prolactin Proteins 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 229940097325 prolactin Drugs 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- -1 secondary amine compound Chemical class 0.000 description 3
- 150000003335 secondary amines Chemical class 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 150000001350 alkyl halides Chemical class 0.000 description 2
- 230000029936 alkylation Effects 0.000 description 2
- 238000005804 alkylation reaction Methods 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 230000002285 radioactive effect Effects 0.000 description 2
- NNDATQSUZGLGQT-BXUZGUMPSA-N 6-methylergoline Chemical class C1=CC([C@H]2CCCN([C@@H]2C2)C)=C3C2=CNC3=C1 NNDATQSUZGLGQT-BXUZGUMPSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- RHGUXDUPXYFCTE-ZWNOBZJWSA-N ergoline Chemical class C1=CC([C@@H]2[C@H](NCCC2)C2)=C3C2=CNC3=C1 RHGUXDUPXYFCTE-ZWNOBZJWSA-N 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- FKHIFSZMMVMEQY-UHFFFAOYSA-N talc Chemical compound [Mg+2].[O-][Si]([O-])=O FKHIFSZMMVMEQY-UHFFFAOYSA-N 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 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
- C07D457/02—Heterocyclic compounds containing indolo [4, 3-f, g] quinoline ring systems, e.g. derivatives of ergoline, of the formula:, e.g. lysergic acid with hydrocarbon or substituted hydrocarbon radicals, attached in position 8
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US419566A US3920664A (en) | 1972-07-21 | 1973-11-28 | D-2-halo-6-alkyl-8-substituted ergolines and related compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2407904A1 true DE2407904A1 (de) | 1975-06-05 |
Family
ID=23662805
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19742407904 Withdrawn DE2407904A1 (de) | 1973-11-28 | 1974-02-19 | D-2-subst.-6-alkyl-8-subst.-ergoline und verfahren zu ihrer herstellung |
Country Status (25)
| Country | Link |
|---|---|
| JP (2) | JPS5084598A (it) |
| AR (1) | AR212072A1 (it) |
| AT (1) | AT333982B (it) |
| BE (1) | BE811610R (it) |
| BG (1) | BG22399A3 (it) |
| CA (1) | CA1011334A (it) |
| CH (1) | CH592088A5 (it) |
| CS (1) | CS175474B2 (it) |
| DD (1) | DD116828A6 (it) |
| DE (1) | DE2407904A1 (it) |
| DK (1) | DK140480B (it) |
| ES (1) | ES423817A1 (it) |
| FR (1) | FR2252091B2 (it) |
| GB (1) | GB1451724A (it) |
| HU (1) | HU169190B (it) |
| IE (1) | IE39042B1 (it) |
| IL (1) | IL44160A (it) |
| NL (1) | NL7402611A (it) |
| PH (1) | PH11140A (it) |
| PL (1) | PL98288B1 (it) |
| RO (1) | RO71304A (it) |
| SE (1) | SE416809B (it) |
| SU (1) | SU493965A3 (it) |
| YU (1) | YU49074A (it) |
| ZA (1) | ZA74758B (it) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0160842A2 (de) * | 1984-04-09 | 1985-11-13 | Schering Aktiengesellschaft | 2-substituierte Ergolin-Derivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0409785D0 (en) | 2004-04-30 | 2004-06-09 | Resolution Chemicals Ltd | Preparation of cabergoline |
| GB0505965D0 (en) | 2005-03-23 | 2005-04-27 | Resolution Chemicals Ltd | Preparation of cabergoline |
| US7339060B2 (en) | 2005-03-23 | 2008-03-04 | Resolution Chemicals, Ltd. | Preparation of cabergoline |
-
1973
- 1973-07-16 PH PH15493A patent/PH11140A/en unknown
-
1974
- 1974-02-05 GB GB534674A patent/GB1451724A/en not_active Expired
- 1974-02-05 ZA ZA740758A patent/ZA74758B/xx unknown
- 1974-02-06 IE IE00222/74A patent/IE39042B1/xx unknown
- 1974-02-06 CA CA191,927A patent/CA1011334A/en not_active Expired
- 1974-02-06 IL IL44160A patent/IL44160A/en unknown
- 1974-02-19 DE DE19742407904 patent/DE2407904A1/de not_active Withdrawn
- 1974-02-22 AT AT146974A patent/AT333982B/de not_active IP Right Cessation
- 1974-02-22 AR AR252504A patent/AR212072A1/es active
- 1974-02-26 YU YU00490/74A patent/YU49074A/xx unknown
- 1974-02-26 NL NL7402611A patent/NL7402611A/xx not_active Application Discontinuation
- 1974-02-27 BE BE1005751A patent/BE811610R/xx active
- 1974-02-27 FR FR7406665A patent/FR2252091B2/fr not_active Expired
- 1974-02-28 CH CH283374A patent/CH592088A5/xx not_active IP Right Cessation
- 1974-02-28 DK DK106674AA patent/DK140480B/da unknown
- 1974-02-28 SE SE7402672A patent/SE416809B/xx unknown
- 1974-02-28 DD DD176871A patent/DD116828A6/xx unknown
- 1974-02-28 JP JP49022919A patent/JPS5084598A/ja active Pending
- 1974-03-01 ES ES423817A patent/ES423817A1/es not_active Expired
- 1974-03-11 PL PL1974169434A patent/PL98288B1/pl unknown
- 1974-03-14 HU HUEI533A patent/HU169190B/hu unknown
- 1974-03-14 SU SU2004671A patent/SU493965A3/ru active
- 1974-03-14 BG BG26052A patent/BG22399A3/xx unknown
- 1974-03-15 CS CS1906A patent/CS175474B2/cs unknown
- 1974-03-15 RO RO7478047A patent/RO71304A/ro unknown
-
1982
- 1982-10-29 JP JP57190684A patent/JPS5888379A/ja active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0160842A2 (de) * | 1984-04-09 | 1985-11-13 | Schering Aktiengesellschaft | 2-substituierte Ergolin-Derivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel |
| EP0160842A3 (en) * | 1984-04-09 | 1989-03-15 | Schering Aktiengesellschaft Berlin Und Bergkamen | 2-substituted ergoline derivatives, processes for their preparation, and their use as medicaments |
Also Published As
| Publication number | Publication date |
|---|---|
| PL98288B1 (pl) | 1978-04-29 |
| FR2252091B2 (it) | 1978-07-28 |
| BE811610R (fr) | 1974-08-27 |
| CH592088A5 (it) | 1977-10-14 |
| YU49074A (en) | 1982-02-28 |
| AT333982B (de) | 1976-12-27 |
| SU493965A3 (ru) | 1975-11-28 |
| ATA146974A (de) | 1976-04-15 |
| JPS5888379A (ja) | 1983-05-26 |
| RO71304A (ro) | 1981-09-24 |
| ES423817A1 (es) | 1976-10-16 |
| GB1451724A (en) | 1976-10-06 |
| AU6531574A (en) | 1975-08-07 |
| IE39042L (en) | 1975-05-28 |
| CS175474B2 (it) | 1977-05-31 |
| SE416809B (sv) | 1981-02-09 |
| SE7402672L (it) | 1975-05-29 |
| AR212072A1 (es) | 1978-05-15 |
| CA1011334A (en) | 1977-05-31 |
| IL44160A (en) | 1977-03-31 |
| HU169190B (it) | 1976-10-28 |
| DK106674A (it) | 1975-07-28 |
| BG22399A3 (it) | 1977-02-20 |
| ZA74758B (en) | 1974-12-24 |
| JPS5084598A (it) | 1975-07-08 |
| DK140480C (it) | 1980-03-03 |
| DK140480B (da) | 1979-09-10 |
| NL7402611A (nl) | 1975-05-30 |
| IE39042B1 (en) | 1978-07-19 |
| FR2252091A2 (it) | 1975-06-20 |
| DD116828A6 (it) | 1975-12-12 |
| PH11140A (en) | 1977-10-27 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OD | Request for examination | ||
| 8128 | New person/name/address of the agent |
Representative=s name: SPOTT, G., DIPL.-CHEM. DR.RER.NAT., PAT.-ANW., 800 |
|
| 8130 | Withdrawal |