GB994486A - Improvements in or relating to lysergic acid amide derivatives - Google Patents
Improvements in or relating to lysergic acid amide derivativesInfo
- Publication number
- GB994486A GB994486A GB892/62A GB89262A GB994486A GB 994486 A GB994486 A GB 994486A GB 892/62 A GB892/62 A GB 892/62A GB 89262 A GB89262 A GB 89262A GB 994486 A GB994486 A GB 994486A
- Authority
- GB
- United Kingdom
- Prior art keywords
- radical
- acid
- reacting
- alkyl
- compounds
- 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
- GENAHGKEFJLNJB-QMTHXVAHSA-N lysergamide Chemical class C1=CC(C2=C[C@H](CN([C@@H]2C2)C)C(N)=O)=C3C2=CNC3=C1 GENAHGKEFJLNJB-QMTHXVAHSA-N 0.000 title 1
- 239000002253 acid Substances 0.000 abstract 5
- 150000003839 salts Chemical class 0.000 abstract 5
- 150000001875 compounds Chemical class 0.000 abstract 4
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 abstract 2
- 150000001412 amines Chemical class 0.000 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 abstract 2
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 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 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- -1 alkali metal salt Chemical class 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 abstract 1
- 150000001540 azides Chemical class 0.000 abstract 1
- RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 abstract 1
- 229910001863 barium hydroxide Inorganic materials 0.000 abstract 1
- 229910001422 barium ion Inorganic materials 0.000 abstract 1
- 150000001735 carboxylic acids Chemical class 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 229960003133 ergot alkaloid Drugs 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 229940042795 hydrazides for tuberculosis treatment Drugs 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 238000005984 hydrogenation reaction Methods 0.000 abstract 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 abstract 1
- 230000002401 inhibitory effect Effects 0.000 abstract 1
- 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 1
- 150000007522 mineralic acids Chemical class 0.000 abstract 1
- 150000007524 organic acids Chemical class 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 238000001556 precipitation Methods 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 230000003236 psychic effect Effects 0.000 abstract 1
- 239000000376 reactant Substances 0.000 abstract 1
- 229940076279 serotonin Drugs 0.000 abstract 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- 235000011149 sulphuric acid Nutrition 0.000 abstract 1
- 239000001117 sulphuric acid Substances 0.000 abstract 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
-
- 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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention comprises compounds of the general formula <FORM:0994486/C2/1> wherein R1 represents a C1- 4 alkyl radical, a C2- 4 alkenyl radical or a C7- 10 aralkyl radical, R2 represents a C3- 8 cycloalkyl radical or a C7- 10 aralkyl radical and R3 represents a hydrogen atom, a C1- 6 alkyl or hydroxyalkyl radical, a C3- 8 cycloalkyl radical or a C7- 10 aralkyl radical, but R2 and R3 do not both represent cycloalkyl or aralkyl radicals, or R2 and R3 together represent a C5 alkylene radical, and \sG represents <FORM:0994486/C2/2> and their acid addition salts, and the preparation of compounds of formula I (and their acid addition salts) wherein R2 may additionally represent a hydrogen atom (when R3 is other than hydrogen), a C1- 6 hydroxyalkyl radical (when R3 is other than hydroxyalkyl) or a C1- 6 alkyl radical and R2 and R3 together may additionally represent a C4 alkylene radical, by reacting an alkali metal salt of the corresponding carboxylic acid with sulphur trioxide and reacting the product with an amine R2NHR3, or by converting the hydrazide of such acid into the corresponding azide and reacting this with said amine, and in either case, if desired, converting the product into an addition salt with an inorganic or organic acid. 1 - R1 - Lysergic and - 9,10 - dihydrolysergic acids and their hydrazides are prepared by introducing the desired substituent R1 into the 1-position of an ergot alkaloid (especially one that is therapeutically useless) and subjecting the product (if necessary after hydrogenation in the 9,10-position) to heating with barium hydroxide in alcohol (followed by precipitation of barium ions with sulphuric acid) or to reaction with hydrazine (one or both of the reactants preferably being in the form of an acid addition salt in the case of the non-hydrogenated compounds). 1-Alkyl-D-lysergic acid is prepared by reacting D-lysergic acid with sodamide and allyl bromide. Pharmaceutical compositions, suitable for inhibiting the action of serotonin and for treating psychic illnesses, comprise compounds I (or salts) as first defined above, together with a physiologically acceptable carrier.
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH104661A CH390265A (en) | 1961-01-30 | 1961-01-30 | Process for the preparation of heterocyclic compounds |
| CH128461A CH401075A (en) | 1961-02-03 | 1961-02-03 | Process for the preparation of heterocyclic compounds |
| CH189261 | 1961-02-16 | ||
| CH263661 | 1961-03-03 | ||
| CH1288361 | 1961-11-07 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB994486A true GB994486A (en) | 1965-06-10 |
Family
ID=27508920
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB892/62A Expired GB994486A (en) | 1961-01-30 | 1962-01-09 | Improvements in or relating to lysergic acid amide derivatives |
Country Status (4)
| Country | Link |
|---|---|
| FI (2) | FI40466B (en) |
| GB (1) | GB994486A (en) |
| LU (1) | LU41167A1 (en) |
| SE (2) | SE308320B (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0029082A1 (en) * | 1979-11-14 | 1981-05-27 | VEB Arzneimittelwerk Dresden | 1-Benzylated ergometrine derivatives, process for their preparation and pharmaceutical compositions containing them |
| EP0040685A2 (en) * | 1980-04-15 | 1981-12-02 | Meditest Institut für medizinisch-pharmazeutische Untersuchungen GmbH & Co. KG | Lysergic-acid derivatives and their pharmaceutical compositions |
-
1962
- 1962-01-09 GB GB892/62A patent/GB994486A/en not_active Expired
- 1962-01-29 FI FI0185/62A patent/FI40466B/fi active
- 1962-01-29 LU LU41167D patent/LU41167A1/xx unknown
- 1962-01-29 SE SE979/62A patent/SE308320B/xx unknown
-
1965
- 1965-09-30 SE SE12691/65A patent/SE309044B/xx unknown
-
1967
- 1967-05-26 FI FI671494A patent/FI47485C/en active
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0029082A1 (en) * | 1979-11-14 | 1981-05-27 | VEB Arzneimittelwerk Dresden | 1-Benzylated ergometrine derivatives, process for their preparation and pharmaceutical compositions containing them |
| EP0040685A2 (en) * | 1980-04-15 | 1981-12-02 | Meditest Institut für medizinisch-pharmazeutische Untersuchungen GmbH & Co. KG | Lysergic-acid derivatives and their pharmaceutical compositions |
| EP0040685A3 (en) * | 1980-04-15 | 1982-10-13 | Meditest Institut für medizinisch-pharmazeutische Untersuchungen GmbH & Co. KG | Lysergic-acid derivatives and their pharmaceutical compositions |
Also Published As
| Publication number | Publication date |
|---|---|
| FI47485C (en) | 1973-12-10 |
| SE309044B (en) | 1969-03-10 |
| LU41167A1 (en) | 1962-07-30 |
| SE308320B (en) | 1969-02-10 |
| FI47485B (en) | 1973-08-31 |
| FI40466B (en) | 1968-10-31 |
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