DE3229665A1 - Regiospezifisches verfahren zur herstellung von ergolinderivaten - Google Patents
Regiospezifisches verfahren zur herstellung von ergolinderivatenInfo
- Publication number
- DE3229665A1 DE3229665A1 DE19823229665 DE3229665A DE3229665A1 DE 3229665 A1 DE3229665 A1 DE 3229665A1 DE 19823229665 DE19823229665 DE 19823229665 DE 3229665 A DE3229665 A DE 3229665A DE 3229665 A1 DE3229665 A1 DE 3229665A1
- Authority
- DE
- Germany
- Prior art keywords
- group
- hydrogen atom
- stands
- formula
- ergoline derivatives
- 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.)
- Ceased
Links
- 238000000034 method Methods 0.000 title claims abstract description 16
- 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 title claims abstract description 7
- 238000002360 preparation method Methods 0.000 title abstract description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims abstract description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims abstract description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 6
- 239000002904 solvent Substances 0.000 claims abstract description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims abstract description 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims abstract description 3
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims abstract description 3
- 125000005843 halogen group Chemical group 0.000 claims abstract description 3
- 150000002430 hydrocarbons Chemical group 0.000 claims abstract description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 3
- 239000001257 hydrogen Substances 0.000 claims abstract description 3
- 239000012948 isocyanate Substances 0.000 claims abstract description 3
- 150000002513 isocyanates Chemical class 0.000 claims abstract description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 3
- 125000003373 pyrazinyl group Chemical group 0.000 claims abstract description 3
- 125000002098 pyridazinyl group Chemical group 0.000 claims abstract description 3
- 125000000714 pyrimidinyl group Chemical group 0.000 claims abstract description 3
- 125000000335 thiazolyl group Chemical group 0.000 claims abstract description 3
- -1 ergoline amide Chemical class 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 abstract description 2
- 125000004076 pyridyl group Chemical group 0.000 abstract description 2
- 150000001875 compounds Chemical class 0.000 description 8
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- WUDNUHPRLBTKOJ-UHFFFAOYSA-N ethyl isocyanate Chemical compound CCN=C=O WUDNUHPRLBTKOJ-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000001718 carbodiimides Chemical class 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- XPPKVPWEQAFLFU-UHFFFAOYSA-N diphosphoric acid Chemical class OP(O)(=O)OP(O)(O)=O XPPKVPWEQAFLFU-UHFFFAOYSA-N 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture 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
- 239000007858 starting material Substances 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 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
- C07D457/04—Heterocyclic compounds containing indolo [4, 3-f, g] quinoline ring systems, e.g. derivatives of ergoline, of the formula:, e.g. lysergic acid with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 8
- C07D457/06—Lysergic acid amides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8124549 | 1981-08-11 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE3229665A1 true DE3229665A1 (de) | 1983-02-24 |
Family
ID=10523868
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19823229665 Ceased DE3229665A1 (de) | 1981-08-11 | 1982-08-09 | Regiospezifisches verfahren zur herstellung von ergolinderivaten |
Country Status (3)
| Country | Link |
|---|---|
| JP (1) | JPS5838282A (enrdf_load_stackoverflow) |
| BE (1) | BE894060A (enrdf_load_stackoverflow) |
| DE (1) | DE3229665A1 (enrdf_load_stackoverflow) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2525104A1 (en) * | 2003-05-08 | 2004-11-25 | Ivax Pharmaceuticals S.R.O. | Polymorphs of cabergoline |
-
1982
- 1982-08-09 BE BE0/208772A patent/BE894060A/fr not_active IP Right Cessation
- 1982-08-09 JP JP13745982A patent/JPS5838282A/ja active Granted
- 1982-08-09 DE DE19823229665 patent/DE3229665A1/de not_active Ceased
Non-Patent Citations (1)
| Title |
|---|
| WEYGAND-HILGETAG: Org.-Chem. Experimentierkunst, 1970, S.420/21 * |
Also Published As
| Publication number | Publication date |
|---|---|
| BE894060A (fr) | 1982-12-01 |
| JPH0321030B2 (enrdf_load_stackoverflow) | 1991-03-20 |
| JPS5838282A (ja) | 1983-03-05 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2729859C2 (de) | Verfahren zur Herstellung von 6a,10a-cis- oder -trans-1-Hydroxy-3-alkyl-6,6-dimethyl-6,6a,7,8,10,10a-hexahydro-9H-dibenzo[b,d]pyran-9-onen | |
| EP0019726B1 (de) | N-Azidosulfonylaryl-maleinimide sowie deren Verwendung | |
| DE1159462B (de) | Verfahren zur Herstellung von s-Triazinderivaten | |
| DE2621092A1 (de) | Verfahren zur herstellung von 2-amino- 2-alkylthio-1-nitroaethylenen | |
| DE3730748A1 (de) | Neue polyoxygenierte labdanderivate, ein verfahren zu ihrer herstellung und ihre verwendung als arzneimittel | |
| DE2719008C2 (enrdf_load_stackoverflow) | ||
| DE2822876C2 (enrdf_load_stackoverflow) | ||
| DE2029099C3 (de) | Verfahren zur Herstellung von Acetidino [3,2-d] thiazolen | |
| DE3229665A1 (de) | Regiospezifisches verfahren zur herstellung von ergolinderivaten | |
| DE2404948C2 (de) | 7α-Acylthio-Steroidspirolactonderivate | |
| DE2241680C2 (de) | 17-Hydroxy-7-alkoxycarbonyl-3-oxo-17α-pregn-4-en-21-carbonsäure-γ-Lactone und Verfahren und Zwischenprodukte zu ihrer Herstellung | |
| CH659464A5 (de) | Verfahren zur herstellung von 1,8-dihydroxy-10-acyl-9-anthronen. | |
| DE1643965A1 (de) | Neue Karbamid-Derivate und Verfahren zu ihrer Herstellung | |
| DE1912941A1 (de) | Verfahren zur Herstellung von 6-Alkoxy-Pyridaziniumverbindungen | |
| DE2446256B2 (de) | Verfahren zur herstellung von hexahydrothieno eckige klammer auf 3,4- d eckige klammer zu -imidazol-2,4-dionen | |
| DE1232577B (de) | Verfahren zur Herstellung von delta 4,9-3-Oxo-11beta-hydroperoxy-19-nor-steroiden | |
| DE2141765A1 (de) | 4-chlor-4-thiazolin-2-one und verfahren zu deren herstellung | |
| DE962608C (de) | Verfahren zur Herstellung von Phosphorsaeure- bzw. Thiophosphorsaeureestern | |
| DE2246376B2 (de) | Verfahren zur Herstellung von Cyanacetylcarbamaten | |
| DE1007770B (de) | Verfahren zur Herstellung neuer Thionophosphorsaeureester | |
| EP0513700A1 (de) | Verfahren zur Herstellung von Imidazothiazolon-Derivaten | |
| DE1929237A1 (de) | Verfahren zur Herstellung von N-Acyl-3,4-epoxy-pyrrolidin-Derivaten | |
| DE1158499B (de) | Verfahren zur Herstellung von Isonitrilen | |
| AT225857B (de) | Verfahren zur Herstellung von Lysergsäure- und Dihydrolysergsäure-Derivaten | |
| DE2655004B2 (de) | Verfahren zur Herstellung von bicyclischen Laktonen |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| 8127 | New person/name/address of the applicant |
Owner name: FARMITALIA CARLO ERBA S.R.L., MAILAND/MILANO, IT |
|
| 8128 | New person/name/address of the agent |
Representative=s name: KRAUS, W., DIPL.-CHEM. DR.RER.NAT. WEISERT, A., DI |
|
| 8131 | Rejection |