CN114829341B - 合成方法 - Google Patents
合成方法 Download PDFInfo
- Publication number
- CN114829341B CN114829341B CN202080087092.5A CN202080087092A CN114829341B CN 114829341 B CN114829341 B CN 114829341B CN 202080087092 A CN202080087092 A CN 202080087092A CN 114829341 B CN114829341 B CN 114829341B
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- China
- Prior art keywords
- compound
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- formula iii
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- Prior art date
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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
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
- A61K31/404—Indoles, e.g. pindolol
- A61K31/4045—Indole-alkylamines; Amides thereof, e.g. serotonin, melatonin
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/14—Radicals substituted by nitrogen atoms, not forming part of a nitro radical
- C07D209/16—Tryptamines
-
- 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
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- 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
- A61P25/22—Anxiolytics
-
- 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
-
- 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
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/18—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D209/20—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals substituted additionally by nitrogen atoms, e.g. tryptophane
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/05—Isotopically modified compounds, e.g. labelled
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- General Chemical & Material Sciences (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Epidemiology (AREA)
- Addiction (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1916210.6 | 2019-11-07 | ||
| GBGB1916210.6A GB201916210D0 (en) | 2019-11-07 | 2019-11-07 | High purity tryptamines and methods of synthesis thereof |
| GBGB1917320.2A GB201917320D0 (en) | 2019-11-28 | 2019-11-28 | Novel compounds |
| GB1917320.2 | 2019-11-28 | ||
| GB2008303.6A GB2585978B (en) | 2019-06-03 | 2020-06-02 | Therapeutic compositions |
| GB2008303.6 | 2020-06-02 | ||
| PCT/EP2020/081503 WO2021089873A1 (en) | 2019-11-07 | 2020-11-09 | Method of synthesis |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN114829341A CN114829341A (zh) | 2022-07-29 |
| CN114829341B true CN114829341B (zh) | 2024-03-08 |
Family
ID=75849570
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202080087092.5A Active CN114829341B (zh) | 2019-11-07 | 2020-11-09 | 合成方法 |
| CN202080087091.0A Active CN114829340B (zh) | 2019-11-07 | 2020-11-09 | 化合物 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202080087091.0A Active CN114829340B (zh) | 2019-11-07 | 2020-11-09 | 化合物 |
Country Status (18)
| Country | Link |
|---|---|
| US (6) | US11643390B2 (https=) |
| EP (3) | EP3844147B1 (https=) |
| JP (3) | JP7422473B2 (https=) |
| KR (2) | KR20220082092A (https=) |
| CN (2) | CN114829341B (https=) |
| AU (2) | AU2020378647B2 (https=) |
| BR (1) | BR112022008919A2 (https=) |
| CA (2) | CA3160337C (https=) |
| DK (1) | DK3844147T3 (https=) |
| ES (2) | ES2940811T3 (https=) |
| HR (2) | HRP20220797T1 (https=) |
| HU (2) | HUE061482T2 (https=) |
| IL (2) | IL292754B2 (https=) |
| MX (1) | MX2022005399A (https=) |
| NZ (1) | NZ788543A (https=) |
| PL (2) | PL3844147T3 (https=) |
| PT (2) | PT3844147T (https=) |
| WO (2) | WO2021089873A1 (https=) |
Families Citing this family (42)
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| GB201907871D0 (en) | 2019-06-03 | 2019-07-17 | Small Pharma Ltd | Therapeutic compositions |
| EP3753923A1 (en) | 2019-06-19 | 2020-12-23 | GH Research Limited | Recrystallisation of 5-methoxy-n,n-dimethyltryptamine (5-meo-dmt) in methyl tert.-butyl ether (mtbe) without adding an anti-solvent |
| KR20220082092A (ko) | 2019-11-07 | 2022-06-16 | 스몰 파마 엘티디 | 화합물 |
| KR20220137081A (ko) | 2020-02-04 | 2022-10-11 | 마인드셋 파마 인크. | Cns 장애의 치료를 위한 세로토닌성 사이키델릭 작용제로서의 실로신 유도체 |
| US11332441B2 (en) * | 2020-03-23 | 2022-05-17 | Caamtech, Inc. | Crystalline N-methyl tryptamine derivatives |
| WO2021226416A1 (en) | 2020-05-08 | 2021-11-11 | Psilera Inc. | Novel compositions of matter and pharmaceutical compositions |
| US12240813B2 (en) | 2020-05-19 | 2025-03-04 | Cybin Irl Limited | Deuterated tryptamine derivatives and methods of use |
| US12042564B2 (en) | 2020-06-02 | 2024-07-23 | Cybin Uk Ltd | Therapeutic solid dosage forms |
| US11773062B2 (en) | 2021-03-22 | 2023-10-03 | Small Pharma Ltd | Deuterated compounds |
| MX2022014900A (es) * | 2020-06-02 | 2023-03-27 | Small Pharma Ltd | Composiciones terapeuticas que comprenden compuestos n,n-dimetiltriptamina deuterada o parcialmente deuterada. |
| EP3902541B1 (en) * | 2020-06-02 | 2022-09-14 | Small Pharma Ltd | Therapeutic compositions comprising deuterated or partially deuterated n,n-dimethyltryptamine compounds |
| BR112022025306A2 (pt) | 2020-06-12 | 2023-02-28 | Beckley Psytech Ltd | Composição compreendendo um sal benzoato de 5-metóxin, n-dimetiltriptamina |
| US11406619B2 (en) | 2020-08-28 | 2022-08-09 | Small Pharma Ltd | Injectable formulations |
| US12521370B2 (en) | 2020-12-01 | 2026-01-13 | Cybin Uk Ltd | Inhalable formulations |
| US11660289B2 (en) | 2020-12-01 | 2023-05-30 | Small Pharma Ltd. | Deuterated or partially deuterated N,N-dimethyltryptamine compounds |
| US12534441B2 (en) | 2021-01-15 | 2026-01-27 | Beckley Psytech Limited | Tryptamine analogues |
| EP4155306A1 (en) | 2021-01-15 | 2023-03-29 | Beckley Psytech Limited | Neuroactive ergoline analogue |
| US11312684B1 (en) | 2021-02-10 | 2022-04-26 | Eleusis Therapeutics Us, Inc. | Pharmaceutically acceptable salts of psilocin and uses thereof |
| CA3218110A1 (en) | 2021-05-25 | 2022-12-01 | Majed Fawaz | New n,n-dimethyltryptamine salts and crystalline salt forms |
| AU2022287974A1 (en) | 2021-06-09 | 2024-01-04 | Atai Therapeutics, Inc. | Novel prodrugs and conjugates of dimethyltryptamine |
| EP4122916A1 (en) * | 2021-07-22 | 2023-01-25 | GH Research Ireland Limited | Method for preparing an organic compound |
| EP4373807A1 (en) * | 2021-07-22 | 2024-05-29 | GH Research Ireland Limited | Method for preparing a tryptamine derivative |
| US11697638B2 (en) * | 2021-09-08 | 2023-07-11 | Small Pharma Ltd | 5-methoxy-N,N-dimethyltryptamine crystalline forms |
| EP4159192A1 (en) | 2021-09-30 | 2023-04-05 | Biomind Labs Inc | Dimethyltriptamine-based nasal spray for the personalised treatment of neurological and psychiatric disorders |
| EP4433049A1 (en) | 2021-11-18 | 2024-09-25 | Cybin UK Ltd | Injectable and inhalable formulations |
| US12318477B2 (en) | 2021-11-18 | 2025-06-03 | Cybin Uk Ltd | Injectable and inhalable formulations |
| WO2023108174A1 (en) * | 2021-12-10 | 2023-06-15 | Terran Biosciences, Inc. | Analogs of 6-methoxy- n, n-dimethyltryptamine |
| WO2023129956A2 (en) | 2021-12-30 | 2023-07-06 | ATAI Life Sciences AG | Dimethyltryptamine analogues as nitric oxide delivery drugs |
| WO2023147423A1 (en) * | 2022-01-28 | 2023-08-03 | Miralogx Llc | Anxiolytic compounds, pharmaceutical compositions, and methods of treating anxiety and other disorders |
| WO2023168023A1 (en) | 2022-03-04 | 2023-09-07 | Reset Pharmaceuticals, Inc. | Co-crystals or salts comprising psilocin |
| US20230346718A1 (en) * | 2022-04-27 | 2023-11-02 | Yale University | Method of treating, ameliorating and/or preventing depression |
| US12264131B2 (en) * | 2022-08-19 | 2025-04-01 | Beckley Psytech Limited | Pharmaceutically acceptable salts and compositions thereof |
| GB202212116D0 (en) | 2022-08-19 | 2022-10-05 | Beckley Psytech Ltd | Pharmaceutically acceptable salts and Compositions thereof |
| AU2023361184A1 (en) | 2022-10-13 | 2025-04-24 | Cybin Uk Ltd | Method of administration of a parenteral formulation comprising a psychedelic agent |
| WO2024108195A1 (en) | 2022-11-17 | 2024-05-23 | Remedi, Inc. | Combinations of monoamine oxidase inhibitors and serotonin receptor agonists and their therapeutic use |
| TW202430149A (zh) * | 2022-12-01 | 2024-08-01 | 美商雅特益醫療公司 | Ｎ，ｎ－二甲基色胺之結晶形式及其使用方法 |
| CN121038789A (zh) | 2023-01-23 | 2025-11-28 | 赛本英国有限公司 | 通过肠胃外施用单一有效肠胃外剂量的短效致幻剂治疗精神或神经障碍 |
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| KR20220082092A (ko) | 2019-11-07 | 2022-06-16 | 스몰 파마 엘티디 | 화합물 |
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| KR20220137081A (ko) | 2020-02-04 | 2022-10-11 | 마인드셋 파마 인크. | Cns 장애의 치료를 위한 세로토닌성 사이키델릭 작용제로서의 실로신 유도체 |
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| US12240813B2 (en) | 2020-05-19 | 2025-03-04 | Cybin Irl Limited | Deuterated tryptamine derivatives and methods of use |
| US12042564B2 (en) | 2020-06-02 | 2024-07-23 | Cybin Uk Ltd | Therapeutic solid dosage forms |
| EP3902541B1 (en) | 2020-06-02 | 2022-09-14 | Small Pharma Ltd | Therapeutic compositions comprising deuterated or partially deuterated n,n-dimethyltryptamine compounds |
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| US11406619B2 (en) | 2020-08-28 | 2022-08-09 | Small Pharma Ltd | Injectable formulations |
| JP7422474B2 (ja) | 2020-08-28 | 2024-01-26 | サイビン ユーケー リミテッド | 注射用製剤 |
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| US12318477B2 (en) | 2021-11-18 | 2025-06-03 | Cybin Uk Ltd | Injectable and inhalable formulations |
-
2020
- 2020-11-09 KR KR1020227018623A patent/KR20220082092A/ko not_active Ceased
- 2020-11-09 AU AU2020378647A patent/AU2020378647B2/en active Active
- 2020-11-09 BR BR112022008919A patent/BR112022008919A2/pt not_active Application Discontinuation
- 2020-11-09 JP JP2022526073A patent/JP7422473B2/ja active Active
- 2020-11-09 PL PL20816376.6T patent/PL3844147T3/pl unknown
- 2020-11-09 EP EP20816376.6A patent/EP3844147B1/en active Active
- 2020-11-09 IL IL292754A patent/IL292754B2/en unknown
- 2020-11-09 DK DK20816376.6T patent/DK3844147T3/da active
- 2020-11-09 CN CN202080087092.5A patent/CN114829341B/zh active Active
- 2020-11-09 HU HUE20816375A patent/HUE061482T2/hu unknown
- 2020-11-09 PL PL20816375.8T patent/PL3873883T3/pl unknown
- 2020-11-09 HU HUE20816376A patent/HUE059403T2/hu unknown
- 2020-11-09 MX MX2022005399A patent/MX2022005399A/es unknown
- 2020-11-09 AU AU2020381103A patent/AU2020381103B2/en active Active
- 2020-11-09 EP EP20816375.8A patent/EP3873883B1/en active Active
- 2020-11-09 HR HRP20220797TT patent/HRP20220797T1/hr unknown
- 2020-11-09 IL IL292753A patent/IL292753B2/en unknown
- 2020-11-09 PT PT208163766T patent/PT3844147T/pt unknown
- 2020-11-09 CN CN202080087091.0A patent/CN114829340B/zh active Active
- 2020-11-09 PT PT208163758T patent/PT3873883T/pt unknown
- 2020-11-09 CA CA3160337A patent/CA3160337C/en active Active
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Non-Patent Citations (3)
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| Binding of Serotonin to the Human Serotonin Transporter. Molecular Modeling and Experimental Validation;Leyla Celik等;J. AM. CHEM. SOC.;第130卷(第130期);3853-3865 * |
| INDOLEALKYLAMINE METABOLISM. SYNTHESIS OF DEUTERATED INDOLEALKYLAMINES AS METABOLIC PROBES;Philip E. Morris等;Jouml of Labelled Compod and Radiopharmaceuticals;第33卷(第33期);455-465 * |
| Reaction of N,N‑Dimethyltryptamine with Dichloromethane Under Common Experimental Conditions;Lee E. Dunlap等;ACS Omega(第3期);4968-4973 * |
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