ES336531A1 - Lysergic Acid Derivatives - Google Patents
Lysergic Acid DerivativesInfo
- Publication number
- ES336531A1 ES336531A1 ES336531A ES336531A ES336531A1 ES 336531 A1 ES336531 A1 ES 336531A1 ES 336531 A ES336531 A ES 336531A ES 336531 A ES336531 A ES 336531A ES 336531 A1 ES336531 A1 ES 336531A1
- Authority
- ES
- Spain
- Prior art keywords
- acid
- lysergic
- lysergic acid
- carbons
- dihydro
- 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-QMTHXVAHSA-N lysergic acid Chemical class C1=CC(C2=C[C@H](CN([C@@H]2C2)C)C(O)=O)=C3C2=CNC3=C1 ZAGRKAFMISFKIO-QMTHXVAHSA-N 0.000 title abstract 3
- 239000002253 acid Substances 0.000 abstract 3
- 150000001875 compounds Chemical class 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
- ORBSYPFBZQJNJE-MPKXVKKWSA-N (6ar,9r,10ar)-7-methyl-6,6a,8,9,10,10a-hexahydro-4h-indolo[4,3-fg]quinoline-9-carboxylic acid Chemical compound C1=CC([C@H]2C[C@H](CN([C@@H]2C2)C)C(O)=O)=C3C2=CNC3=C1 ORBSYPFBZQJNJE-MPKXVKKWSA-N 0.000 abstract 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 abstract 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-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
- 239000004480 active ingredient Substances 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 150000008064 anhydrides Chemical class 0.000 abstract 1
- 230000003042 antagnostic effect Effects 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- 150000005840 aryl radicals Chemical class 0.000 abstract 1
- 150000001540 azides Chemical class 0.000 abstract 1
- 125000001246 bromo group Chemical group Br* 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- 239000000460 chlorine Substances 0.000 abstract 1
- GLUUGHFHXGJENI-UHFFFAOYSA-N diethylenediamine Natural products C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 abstract 1
- 230000001747 exhibiting effect Effects 0.000 abstract 1
- 238000002347 injection Methods 0.000 abstract 1
- 239000007924 injection Substances 0.000 abstract 1
- 230000003993 interaction Effects 0.000 abstract 1
- 239000003176 neuroleptic agent Substances 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- -1 piperazine compound Chemical class 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 229940076279 serotonin Drugs 0.000 abstract 1
- 239000000243 solution Substances 0.000 abstract 1
- 235000011149 sulphuric acid Nutrition 0.000 abstract 1
- 239000001117 sulphuric acid Substances 0.000 abstract 1
- 239000000829 suppository Substances 0.000 abstract 1
- 235000020357 syrup Nutrition 0.000 abstract 1
- 239000006188 syrup Substances 0.000 abstract 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
- A61K31/48—Ergoline derivatives, e.g. lysergic acid, ergotamine
-
- 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
- C07D457/08—Lysergic acid amides in which the amide nitrogen is a member of a heterocyclic ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Novel lysergic acid derivatives (and acid addition salts thereof) of the general formula wherein R1 is H or Me, R2 is aralkyl of from 7 to 9 carbons on an aryl radical which may be substituted by one or more Me, alkoxy, having 1 to 4 carbons, chlorine or bromine substituents and x#y is are prepared by the interaction of a functional acid derivative of the appropriate d-lysergic acid or 9,10-dihydro-d-lysergic acid (e.g. acid chloride hydrochloride, acid azide or a mixed anhydride with sulphuric acid) and the appropriate piperazine compound. Compounds of the invention wherein R1 is H may be methylated to the corresponding N-methyl derivative and those wherein x#y is may be hydrogenated in the presence of a catalyst to afford a 9,10-dihydro-compound. Pharmaceutical compositions exhibiting sedative-neuroleptic properties and also having a sympathomimetio and serotonin antagonistic effect contain as the active ingredient the above novel compounds and may be provided in the form of tablets, dragÚes, syrups, injection solutions and suppositories.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH175666A CH475252A (en) | 1966-02-08 | 1966-02-08 | Process for the production of new lysergic acid derivatives |
| CH1753066A CH493521A (en) | 1966-02-08 | 1966-12-09 | (A) Compds. (I):- where R1 = H or Me; R2 = 7-9 C aralkyl or aryl (opt. substd. by one or more methyl or 1-4 C alkoxy groups, Br or Cl); X Y = CH |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES336531A1 true ES336531A1 (en) | 1968-04-01 |
Family
ID=25688570
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES336531A Expired ES336531A1 (en) | 1966-02-08 | 1967-02-07 | Lysergic Acid Derivatives |
Country Status (8)
| Country | Link |
|---|---|
| CH (2) | CH475252A (en) |
| DE (1) | DE1695682A1 (en) |
| DK (1) | DK125175B (en) |
| ES (1) | ES336531A1 (en) |
| FI (1) | FI47189C (en) |
| FR (2) | FR1510553A (en) |
| GB (1) | GB1154682A (en) |
| SE (1) | SE324785B (en) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE564825A (en) * | 1957-02-15 | |||
| IL41409A (en) * | 1972-02-04 | 1977-04-29 | Richter Gedeon Vegyeszet | Lysergic acid amides and process for their preparation |
| HU169073B (en) * | 1974-05-28 | 1976-09-28 | ||
| GB9711043D0 (en) * | 1997-05-29 | 1997-07-23 | Ciba Geigy Ag | Organic compounds |
-
1966
- 1966-02-08 CH CH175666A patent/CH475252A/en not_active IP Right Cessation
- 1966-12-09 CH CH1753066A patent/CH493521A/en not_active IP Right Cessation
-
1967
- 1967-01-12 GB GB181367A patent/GB1154682A/en not_active Expired
- 1967-02-04 DE DE19671695682 patent/DE1695682A1/en active Pending
- 1967-02-06 FI FI33867A patent/FI47189C/en active
- 1967-02-07 SE SE1702/67A patent/SE324785B/xx unknown
- 1967-02-07 ES ES336531A patent/ES336531A1/en not_active Expired
- 1967-02-07 FR FR93979A patent/FR1510553A/en not_active Expired
- 1967-02-07 DK DK66267A patent/DK125175B/en unknown
- 1967-05-03 FR FR105145A patent/FR6554M/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DK125175B (en) | 1973-01-08 |
| CH493521A (en) | 1970-07-15 |
| DE1695682A1 (en) | 1971-04-08 |
| FI47189C (en) | 1973-10-10 |
| CH475252A (en) | 1969-07-15 |
| FR6554M (en) | 1968-12-23 |
| FR1510553A (en) | 1968-01-19 |
| FI47189B (en) | 1973-07-02 |
| SE324785B (en) | 1970-06-15 |
| GB1154682A (en) | 1969-06-11 |
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