GB785173A - Amide-like derivatives of lysergic and isolysergic acids - Google Patents
Amide-like derivatives of lysergic and isolysergic acidsInfo
- Publication number
- GB785173A GB785173A GB1252/56A GB125256A GB785173A GB 785173 A GB785173 A GB 785173A GB 1252/56 A GB1252/56 A GB 1252/56A GB 125256 A GB125256 A GB 125256A GB 785173 A GB785173 A GB 785173A
- Authority
- GB
- United Kingdom
- Prior art keywords
- lysergic
- isolysergic
- acid
- morpholide
- 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.)
- Expired
Links
- ZAGRKAFMISFKIO-IINYFYTJSA-N (6ar,9s)-7-methyl-6,6a,8,9-tetrahydro-4h-indolo[4,3-fg]quinoline-9-carboxylic acid Chemical class C1=CC(C2=C[C@@H](CN([C@@H]2C2)C)C(O)=O)=C3C2=CNC3=C1 ZAGRKAFMISFKIO-IINYFYTJSA-N 0.000 title abstract 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N Alumina Chemical compound [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 abstract 3
- 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 abstract 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 abstract 3
- 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 abstract 3
- RSEBUVRVKCANEP-UHFFFAOYSA-N 2-pyrroline Chemical compound C1CC=CN1 RSEBUVRVKCANEP-UHFFFAOYSA-N 0.000 abstract 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 abstract 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 abstract 2
- NCIHPOHJJSIWSC-IINYFYTJSA-N (6aR,9S)-7-methyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-9-carbonyl azide Chemical compound C(=O)([C@@H]1CN(C)[C@@H]2CC3=CNC4=CC=CC(C2=C1)=C34)N=[N+]=[N-] NCIHPOHJJSIWSC-IINYFYTJSA-N 0.000 abstract 1
- GENAHGKEFJLNJB-IINYFYTJSA-N (6ar,9s)-7-methyl-6,6a,8,9-tetrahydro-4h-indolo[4,3-fg]quinoline-9-carboxamide Chemical class C1=CC(C2=C[C@@H](CN([C@@H]2C2)C)C(N)=O)=C3C2=CNC3=C1 GENAHGKEFJLNJB-IINYFYTJSA-N 0.000 abstract 1
- FEWJPZIEWOKRBE-LWMBPPNESA-L D-tartrate(2-) Chemical compound [O-]C(=O)[C@@H](O)[C@H](O)C([O-])=O FEWJPZIEWOKRBE-LWMBPPNESA-L 0.000 abstract 1
- OTQWCDNEJVKXKG-RDTXWAMCSA-N [(6ar,9r)-7-methyl-6,6a,8,9-tetrahydro-4h-indolo[4,3-fg]quinoline-9-yl]-morpholin-4-ylmethanone Chemical compound O=C([C@H]1CN([C@H]2C(C=3C=CC=C4NC=C(C=34)C2)=C1)C)N1CCOCC1 OTQWCDNEJVKXKG-RDTXWAMCSA-N 0.000 abstract 1
- SETDYMMXQQXCRP-RDTXWAMCSA-N [(6ar,9r)-7-methyl-6,6a,8,9-tetrahydro-4h-indolo[4,3-fg]quinoline-9-yl]-pyrrolidin-1-ylmethanone Chemical compound O=C([C@H]1CN([C@H]2C(C=3C=CC=C4NC=C(C=34)C2)=C1)C)N1CCCC1 SETDYMMXQQXCRP-RDTXWAMCSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 238000004587 chromatography analysis Methods 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 239000007788 liquid Substances 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- ZVJHJDDKYZXRJI-UHFFFAOYSA-N pyrroline Natural products C1CC=NC1 ZVJHJDDKYZXRJI-UHFFFAOYSA-N 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention comprises amide-like lysergic and isolysergic acid derivatives of the general formula <FORM:0785173/IV (a)/1> wherein R represents <FORM:0785173/IV (a)/2> and their salts with acids, and the preparation thereof by reacting isolysergic acid azide in solution with pyrrolidine, piperidine, pyrroline or morpholine and separating the lysergic and isolysergic acid amides from the resulting mixture thereof (e.g. by chromatography on aluminium oxide). The reaction is preferably effected at a temperature of from room temperature to 70 DEG C., suitable solvents being inert organic liquids or excess of the amine used in the reaction. The products are pharmaceutically useful. Examples describe the preparation of compounds corresponding to each of the meanings given above for R. The dimaleates of lysergic acid pyrrolidide, morpholide and pyrrolinide and the D-tartrate of lysergic acid piperidide and morpholide are described.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH785173X | 1955-01-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB785173A true GB785173A (en) | 1957-10-23 |
Family
ID=4536526
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1252/56A Expired GB785173A (en) | 1955-01-21 | 1956-01-13 | Amide-like derivatives of lysergic and isolysergic acids |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB785173A (en) |
-
1956
- 1956-01-13 GB GB1252/56A patent/GB785173A/en not_active Expired
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