GB816273A - Cycloalkylamides of d-lysergic acid and method for producing the same - Google Patents
Cycloalkylamides of d-lysergic acid and method for producing the sameInfo
- Publication number
- GB816273A GB816273A GB22280/57A GB2228057A GB816273A GB 816273 A GB816273 A GB 816273A GB 22280/57 A GB22280/57 A GB 22280/57A GB 2228057 A GB2228057 A GB 2228057A GB 816273 A GB816273 A GB 816273A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acid
- amides
- lysergic
- cycloalkylamides
- isolysergic
- 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.)
- Expired
Links
- ZAGRKAFMISFKIO-UHFFFAOYSA-N Isolysergic acid Natural products C1=CC(C2=CC(CN(C2C2)C)C(O)=O)=C3C2=CNC3=C1 ZAGRKAFMISFKIO-UHFFFAOYSA-N 0.000 title abstract 5
- ZAGRKAFMISFKIO-QMTHXVAHSA-N lysergic acid Chemical compound C1=CC(C2=C[C@H](CN([C@@H]2C2)C)C(O)=O)=C3C2=CNC3=C1 ZAGRKAFMISFKIO-QMTHXVAHSA-N 0.000 title abstract 4
- 238000004519 manufacturing process Methods 0.000 title 1
- 150000001408 amides Chemical class 0.000 abstract 5
- 239000002253 acid Substances 0.000 abstract 3
- 150000002688 maleic acid derivatives Chemical class 0.000 abstract 3
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- 238000002360 preparation method Methods 0.000 abstract 2
- YONLFQNRGZXBBF-ZIAGYGMSSA-N (2r,3r)-2,3-dibenzoyloxybutanedioic acid Chemical compound O([C@@H](C(=O)O)[C@@H](OC(=O)C=1C=CC=CC=1)C(O)=O)C(=O)C1=CC=CC=C1 YONLFQNRGZXBBF-ZIAGYGMSSA-N 0.000 abstract 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 abstract 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 abstract 1
- 150000001540 azides Chemical class 0.000 abstract 1
- 239000006227 byproduct Substances 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- ZIQIQOUPRHPOIT-UHFFFAOYSA-N cyclobutylazanide Chemical compound [NH-]C1CCC1 ZIQIQOUPRHPOIT-UHFFFAOYSA-N 0.000 abstract 1
- VXVVUHQULXCUPF-UHFFFAOYSA-N cycloheptanamine Chemical compound NC1CCCCCC1 VXVVUHQULXCUPF-UHFFFAOYSA-N 0.000 abstract 1
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 abstract 1
- NISGSNTVMOOSJQ-UHFFFAOYSA-N cyclopentanamine Chemical compound NC1CCCC1 NISGSNTVMOOSJQ-UHFFFAOYSA-N 0.000 abstract 1
- HWDVTQAXQJQROO-UHFFFAOYSA-N cyclopropylazanide Chemical compound [NH-]C1CC1 HWDVTQAXQJQROO-UHFFFAOYSA-N 0.000 abstract 1
- 238000006345 epimerization reaction Methods 0.000 abstract 1
- 238000005194 fractionation Methods 0.000 abstract 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 abstract 1
- 239000011976 maleic acid Substances 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 230000006340 racemization Effects 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 abstract 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
The invention comprises cycloalkylamides of d-lysergic acid, containing 3-7 carbon atoms in the cycloalkyl ring, and their acid maleates, and the preparation thereof by reacting, at temperatures up to 35 DEG C., and in ethereal solution, an azide of d-lysergic or d- or dl-isolysergic acid with at least two equivalents of a cycloalkylamine having 3-7 carbon atoms in the ring, and converting the resulting crude cycloalkylamides into pure cycloalkylamides of d-lysergic acid, which, if desired, are further converted into their acid maleates by mixing solutions thereof and of maleic acid in a solvent which does not readily dissolve the resulting salt. The working up of the crude amides involves such processes as chromatographic fractionation, epimerization of d-isolysergic amides to d-lysergic amides by means of alkali metal hydroxides, resolution of racemic amides by means of dibenzoyl-d-tartaric acid, and racemization of l-amides. Examples describe the preparation of the cyclopropylamide, cyclobutylamide, cyclopentylamide, cyclohexylamide and cycloheptylamide of d-lysergic acid, and their acid maleates, and, as by-products in some cases, the corresponding d-isolysergic amides.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS816273X | 1956-08-09 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB816273A true GB816273A (en) | 1959-07-08 |
Family
ID=5455762
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB22280/57A Expired GB816273A (en) | 1956-08-09 | 1957-07-15 | Cycloalkylamides of d-lysergic acid and method for producing the same |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB816273A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4931447A (en) * | 1987-06-15 | 1990-06-05 | Eli Lilly And Company | Cycloalkylamides of (8β)-1-alkyl-6-(substituted) ergolines |
| US4981859A (en) * | 1987-06-15 | 1991-01-01 | Cycloalkylamides of (8 beta )-1-alkyl-6-(substituted)ergolines | |
| US5441961A (en) * | 1992-08-27 | 1995-08-15 | Eli Lilly And Company | Substituted cyclo or bicycloalkylamides of (8β)-6-(substituted) ergolines |
| US5674875A (en) * | 1993-05-04 | 1997-10-07 | Eli Lilly And Company | Method of blocking human 5-hydroxytryptamine-2 receptors |
-
1957
- 1957-07-15 GB GB22280/57A patent/GB816273A/en not_active Expired
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4931447A (en) * | 1987-06-15 | 1990-06-05 | Eli Lilly And Company | Cycloalkylamides of (8β)-1-alkyl-6-(substituted) ergolines |
| US4981859A (en) * | 1987-06-15 | 1991-01-01 | Cycloalkylamides of (8 beta )-1-alkyl-6-(substituted)ergolines | |
| US5441961A (en) * | 1992-08-27 | 1995-08-15 | Eli Lilly And Company | Substituted cyclo or bicycloalkylamides of (8β)-6-(substituted) ergolines |
| US5739146A (en) * | 1992-08-27 | 1998-04-14 | Eli Lilly And Company | Substituted cyclo or bicycloalkylamides of (8β)-6-(substituted) ergolines |
| US5674875A (en) * | 1993-05-04 | 1997-10-07 | Eli Lilly And Company | Method of blocking human 5-hydroxytryptamine-2 receptors |
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