PL443018A1 - Derivatives of N-((9-chloro-3,4-dihydro-2H-benzo[b][1,4]dioxepin-7-yl)methyl)-2-(6-fluoro-1H-indol-3-yl) ethane-1-amine, method of their preparation and use - Google Patents
Derivatives of N-((9-chloro-3,4-dihydro-2H-benzo[b][1,4]dioxepin-7-yl)methyl)-2-(6-fluoro-1H-indol-3-yl) ethane-1-amine, method of their preparation and useInfo
- Publication number
- PL443018A1 PL443018A1 PL443018A PL44301822A PL443018A1 PL 443018 A1 PL443018 A1 PL 443018A1 PL 443018 A PL443018 A PL 443018A PL 44301822 A PL44301822 A PL 44301822A PL 443018 A1 PL443018 A1 PL 443018A1
- Authority
- PL
- Poland
- Prior art keywords
- sub
- benzo
- dihydro
- chloro
- application
- Prior art date
Links
- HYQZZYOFKWMTPW-UHFFFAOYSA-N n-[(6-chloro-3,4-dihydro-2h-1,5-benzodioxepin-8-yl)methyl]-2-(6-fluoro-1h-indol-3-yl)ethanamine Chemical class O1CCCOC2=CC(CNCCC=3C4=CC=C(C=C4NC=3)F)=CC(Cl)=C21 HYQZZYOFKWMTPW-UHFFFAOYSA-N 0.000 title abstract 2
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 abstract 4
- APJYDQYYACXCRM-UHFFFAOYSA-N tryptamine Chemical compound C1=CC=C2C(CCN)=CNC2=C1 APJYDQYYACXCRM-UHFFFAOYSA-N 0.000 abstract 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 abstract 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 3
- QTNVDKAISCZLHR-UHFFFAOYSA-N 2-(4-fluoro-1h-indol-3-yl)ethanamine Chemical compound C1=CC(F)=C2C(CCN)=CNC2=C1 QTNVDKAISCZLHR-UHFFFAOYSA-N 0.000 abstract 2
- ZKIORVIXEWIOGB-UHFFFAOYSA-N 2-(5-fluoro-1h-indol-3-yl)ethanamine Chemical compound C1=C(F)C=C2C(CCN)=CNC2=C1 ZKIORVIXEWIOGB-UHFFFAOYSA-N 0.000 abstract 2
- QRAWNNQNLQPNIZ-UHFFFAOYSA-N 2-(7-fluoro-1h-indol-3-yl)ethanamine Chemical compound C1=CC=C2C(CCN)=CNC2=C1F QRAWNNQNLQPNIZ-UHFFFAOYSA-N 0.000 abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- BQTOKMYKZPCPRW-UHFFFAOYSA-N 2-(6-fluoro-1h-indol-3-yl)ethanamine Chemical compound FC1=CC=C2C(CCN)=CNC2=C1 BQTOKMYKZPCPRW-UHFFFAOYSA-N 0.000 abstract 1
- LCSVYSVGXQQHSI-UHFFFAOYSA-N 3,4-dihydro-2h-1,5-benzodioxepine-7-carbaldehyde Chemical compound O1CCCOC2=CC(C=O)=CC=C21 LCSVYSVGXQQHSI-UHFFFAOYSA-N 0.000 abstract 1
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 abstract 1
- 102000040125 5-hydroxytryptamine receptor family Human genes 0.000 abstract 1
- 108091032151 5-hydroxytryptamine receptor family Proteins 0.000 abstract 1
- PFMDPBFEHLDZOY-UHFFFAOYSA-N 6-chloro-3,4-dihydro-2h-1,5-benzodioxepine-8-carbaldehyde Chemical compound O1CCCOC2=C1C=C(C=O)C=C2Cl PFMDPBFEHLDZOY-UHFFFAOYSA-N 0.000 abstract 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 abstract 1
- 230000000049 anti-anxiety effect Effects 0.000 abstract 1
- 239000000935 antidepressant agent Substances 0.000 abstract 1
- 229940005513 antidepressants Drugs 0.000 abstract 1
- 239000002249 anxiolytic agent Substances 0.000 abstract 1
- 230000009286 beneficial effect Effects 0.000 abstract 1
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 1
- 238000002425 crystallisation Methods 0.000 abstract 1
- 230000008025 crystallization Effects 0.000 abstract 1
- PSLIMVZEAPALCD-UHFFFAOYSA-N ethanol;ethoxyethane Chemical compound CCO.CCOCC PSLIMVZEAPALCD-UHFFFAOYSA-N 0.000 abstract 1
- 238000000605 extraction Methods 0.000 abstract 1
- 125000001153 fluoro group Chemical group F* 0.000 abstract 1
- 239000003446 ligand Substances 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 230000003414 procognitive effect Effects 0.000 abstract 1
- 208000020016 psychiatric disease Diseases 0.000 abstract 1
- 102000005962 receptors Human genes 0.000 abstract 1
- 108020003175 receptors Proteins 0.000 abstract 1
- 229910000033 sodium borohydride Inorganic materials 0.000 abstract 1
- 239000012279 sodium borohydride Substances 0.000 abstract 1
- 229910052938 sodium sulfate Inorganic materials 0.000 abstract 1
- 235000011152 sodium sulphate Nutrition 0.000 abstract 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
- A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Biomedical Technology (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Przedmiotem zgłoszenia są pochodne N-((9-chloro-3,4-dihydro-2H-benzo[b][1,4]dioksepin-7-ylo)metylo)-2-(6-fluoro-1H-indol-3-ylo)etano-1-aminy o wzorze ogólnym 1, gdzie R<sub>1</sub> oznacza podstawnik chlorowy lub wodór, natomiast R<sub>2</sub> oznacza podstawnik fluorowy lub wodór. Związki będące przedmiotem zgłoszenia otrzymuje się w reakcji 4-, 5- lub 7-fluorotryptaminy lub tryptaminy z 9-chloro-3,4-dihydro-2H-benzo[b][1,4]dioksepino-7-karbaldehydem; 4-, 5-, 6- lub 7- fluorotryptaminy lub tryptaminy z 3,4-dihydro-2H-benzo[b][1,4]dioksepino-7-karbaldehydem w warunkach bezwodnych, bez dostępu powietrza, prowadząc reakcję w metanolu zawierającym siarczan sodu przez 4 godziny i kontynuując ją przez 12 godzin po dodaniu borowodorku sodu, a otrzymany po ekstrakcji dichlorometanem produkt przekształca się w chlorowodorek, który oczyszcza się za pomocą krystalizacji z etanolu lub mieszaniny etanolu z eterem. Związki będące przedmiotem zgłoszenia są wielocelowymi ligandami monoamin, w szczególności receptorów serotoninowych 5-HT<sub>1A</sub> i 5-HT<sub>2A</sub>, mogącymi ze względu na profil receptorowy wykazywać działanie przeciw lękowe, prokognitywne i przeciwdepresyjne korzystne w leczeniu chorób psychicznych, w szczególności depresji.The subject of the application are derivatives of N-((9-chloro-3,4-dihydro-2H-benzo[b][1,4]dioxepin-7-yl)methyl)-2-(6-fluoro-1H-indol-3 -yl)ethan-1-amine of the general formula 1, where R<sub>1</sub> represents a chlorine substituent or hydrogen and R<sub>2</sub> represents a fluorine substituent or hydrogen. The compounds subject to the application are obtained by reacting 4-, 5- or 7-fluorotryptamine or tryptamine with 9-chloro-3,4-dihydro-2H-benzo[b][1,4]dioxepine-7-carbaldehyde; 4-, 5-, 6- or 7-fluorotryptamine or tryptamine with 3,4-dihydro-2H-benzo[b][1,4]dioxepine-7-carbaldehyde in anhydrous conditions, in the absence of air, reacting in methanol containing sodium sulfate for 4 hours and continuing for 12 hours after adding sodium borohydride, and the product obtained after extraction with dichloromethane is converted into the hydrochloride salt, which is purified by crystallization from ethanol or an ethanol-ether mixture. The compounds subject to the application are multi-target monoamine ligands, in particular 5-HT<sub>1A</sub> and 5-HT<sub>2A</sub> serotonin receptors, which, due to their receptor profile, may have anti-anxiety, pro-cognitive and antidepressants beneficial in the treatment of mental illnesses, especially depression.
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL443018A PL443018A1 (en) | 2022-12-01 | 2022-12-01 | Derivatives of N-((9-chloro-3,4-dihydro-2H-benzo[b][1,4]dioxepin-7-yl)methyl)-2-(6-fluoro-1H-indol-3-yl) ethane-1-amine, method of their preparation and use |
| ES202330969A ES2964230A1 (en) | 2022-12-01 | 2023-11-23 | N-((9-chloro-3,4-dihydro-2H-benzo[b][1,4]dioxepin-7-yl)methyl)-2-(6-fluoro-1H-indol-3-yl) derivatives Ethane-1-amine, its method of obtaining and its use (Machine-translation by Google Translate, not legally binding) |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL443018A PL443018A1 (en) | 2022-12-01 | 2022-12-01 | Derivatives of N-((9-chloro-3,4-dihydro-2H-benzo[b][1,4]dioxepin-7-yl)methyl)-2-(6-fluoro-1H-indol-3-yl) ethane-1-amine, method of their preparation and use |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PL443018A1 true PL443018A1 (en) | 2024-06-03 |
Family
ID=90526820
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL443018A PL443018A1 (en) | 2022-12-01 | 2022-12-01 | Derivatives of N-((9-chloro-3,4-dihydro-2H-benzo[b][1,4]dioxepin-7-yl)methyl)-2-(6-fluoro-1H-indol-3-yl) ethane-1-amine, method of their preparation and use |
Country Status (2)
| Country | Link |
|---|---|
| ES (1) | ES2964230A1 (en) |
| PL (1) | PL443018A1 (en) |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2511021C (en) * | 2002-12-20 | 2012-08-21 | Merck Patent Gesellschaft Mit Beschraenkter Haftung | Substituted benzodioxepines |
-
2022
- 2022-12-01 PL PL443018A patent/PL443018A1/en unknown
-
2023
- 2023-11-23 ES ES202330969A patent/ES2964230A1/en active Pending
Non-Patent Citations (2)
| Title |
|---|
| KACZOR ET AL.: "Chem. Med. Chem. 2016, 11, 7, 718-729, 18.03.2016", STRUCTURE-BASED VIRTUAL SCREENING FOR DOPAMINE D2 RECEPTOR LIGANDS AS POTENTIAL ANTIPSYCHOTICS * |
| STEPHEN M. STAHL: "CNS Spectrums 2017, 22, 5, 375-385, 2.10.2017", DRUGS FOR PSYCHOSIS AND MOOD: UNIQUE ACTIONS AT D3, D2, AND D1 DOPAMINE RECEPTOR SUBTYPES * |
Also Published As
| Publication number | Publication date |
|---|---|
| ES2964230A1 (en) | 2024-04-04 |
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