CA3220850A1 - Fluorinated tryptamine compounds, analogues thereof, and methods using same - Google Patents
Fluorinated tryptamine compounds, analogues thereof, and methods using same Download PDFInfo
- Publication number
- CA3220850A1 CA3220850A1 CA3220850A CA3220850A CA3220850A1 CA 3220850 A1 CA3220850 A1 CA 3220850A1 CA 3220850 A CA3220850 A CA 3220850A CA 3220850 A CA3220850 A CA 3220850A CA 3220850 A1 CA3220850 A1 CA 3220850A1
- Authority
- CA
- Canada
- Prior art keywords
- fluoro
- ethyl
- indo1
- amine
- optionally substituted
- 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.)
- Pending
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- 238000000034 method Methods 0.000 title claims description 62
- APJYDQYYACXCRM-UHFFFAOYSA-N tryptamine Chemical class C1=CC=C2C(CCN)=CNC2=C1 APJYDQYYACXCRM-UHFFFAOYSA-N 0.000 title abstract description 12
- 208000020016 psychiatric disease Diseases 0.000 claims abstract description 45
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 522
- 150000001875 compounds Chemical class 0.000 claims description 398
- -1 methylallyl Chemical group 0.000 claims description 282
- 229910052739 hydrogen Inorganic materials 0.000 claims description 98
- 125000003118 aryl group Chemical group 0.000 claims description 85
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 72
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 72
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 71
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 63
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims description 59
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 57
- 125000000217 alkyl group Chemical group 0.000 claims description 55
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 54
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- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 claims description 51
- 125000001072 heteroaryl group Chemical group 0.000 claims description 47
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- YECAJNWCKIRMJU-UHFFFAOYSA-N cyclobutanamine Chemical compound NC1C[CH]C1 YECAJNWCKIRMJU-UHFFFAOYSA-N 0.000 claims description 31
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- 229940113081 5 Hydroxytryptamine 3 receptor antagonist Drugs 0.000 claims description 4
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- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 description 1
- 229910052722 tritium Inorganic materials 0.000 description 1
- 238000000825 ultraviolet detection Methods 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 239000013598 vector Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 239000012224 working solution Substances 0.000 description 1
- 125000001834 xanthenyl group Chemical group C1=CC=CC=2OC3=CC=CC=C3C(C12)* 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- 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
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
-
- 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
- A61P25/22—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
-
- 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
- C07D209/12—Radicals substituted by oxygen atoms
-
- 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
-
- 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
-
- 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
- C07D209/26—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 with an acyl radical attached to the ring nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Epidemiology (AREA)
- Pain & Pain Management (AREA)
- Psychiatry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Steroid Compounds (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US202163195943P | 2021-06-02 | 2021-06-02 | |
| US63/195,943 | 2021-06-02 | ||
| US202163288313P | 2021-12-10 | 2021-12-10 | |
| US63/288,313 | 2021-12-10 | ||
| PCT/US2022/032000 WO2022256554A1 (en) | 2021-06-02 | 2022-06-02 | Fluorinated tryptamine compounds, analogues thereof, and methods using same |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA3220850A1 true CA3220850A1 (en) | 2022-12-08 |
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| CA3220850A Pending CA3220850A1 (en) | 2021-06-02 | 2022-06-02 | Fluorinated tryptamine compounds, analogues thereof, and methods using same |
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| US (1) | US20240286998A1 (enExample) |
| EP (1) | EP4347559A4 (enExample) |
| JP (1) | JP2024523822A (enExample) |
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| IL (1) | IL308944A (enExample) |
| MX (1) | MX2023014437A (enExample) |
| WO (1) | WO2022256554A1 (enExample) |
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| IL311211A (en) | 2021-09-03 | 2024-05-01 | Alexander Shulgin Res Institute Inc | Asymmetric allyl tryptamines |
| US20250091993A1 (en) * | 2022-01-27 | 2025-03-20 | Terran Biosciences Inc. | Salts and solid forms of n-ethyl-2-(5-fluoro-1h-indol-3-yl)-n-methylethan-1-amine |
| US12129234B1 (en) | 2023-08-03 | 2024-10-29 | Gilgamesh Pharmaceuticals, Inc. | Crystalline salts of N-ethyl-(5-fluoro-1H-indol-3-yl)-N-methylethan-1-amine |
| US12157722B1 (en) * | 2023-08-03 | 2024-12-03 | Gilgamesh Pharmaceuticals, Inc. | Crystalline hydrochloride salts of N-ethyl-2-(5-fluoro-1H-indol-3-yl)-N-methylethan-1-amine |
| WO2025052388A1 (en) * | 2023-09-07 | 2025-03-13 | Yissum Research Development Company Of The Hebrew University Of Jerusalem Ltd. | Psychedelic compounds, methods of their preparation and uses thereof |
| WO2025104491A1 (en) * | 2023-11-14 | 2025-05-22 | Mindset Pharma Inc. | Indole derivatives as serotonergic agents useful for the treatment of disorders related thereto |
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| WO1996039383A1 (en) * | 1995-06-06 | 1996-12-12 | Schering Corporation | Substituted benzene-fused hetero- and carbocyclics as neurokinin antagonists |
| DE19615232A1 (de) * | 1996-04-18 | 1997-10-23 | Merck Patent Gmbh | Neue Carbamoylderivate und deren Verwendung als 5-HT ¶1¶¶A¶-Antagonisten |
| AR021509A1 (es) * | 1998-12-08 | 2002-07-24 | Lundbeck & Co As H | Derivados de benzofurano, su preparacion y uso |
| US6800637B2 (en) * | 2002-09-12 | 2004-10-05 | Wyeth | Antidepressant indolealkyl derivatives of heterocycle-fused benzodioxan methylamines |
| CA3052974A1 (en) * | 2017-02-09 | 2018-08-16 | CaaMTech, LLC | Compositions and methods comprising a psilocybin derivative |
| WO2019222552A1 (en) * | 2018-05-16 | 2019-11-21 | University Of Florida Research Foundation | Methods and compositions for substituted 2,5-diketopiperazine analogs |
| GB201907871D0 (en) * | 2019-06-03 | 2019-07-17 | Small Pharma Ltd | Therapeutic compositions |
| MX2022009528A (es) * | 2020-02-04 | 2022-11-14 | Mindset Pharma Inc | Derivados de 3-pirrolidina-indol como agentes psicodélicos serotoninérgicos para el tratamiento de trastornos del snc. |
| JP7242969B2 (ja) * | 2020-02-18 | 2023-03-20 | ギルガメッシュ・ファーマシューティカルズ・インコーポレイテッド | 気分障害の処置での使用に特異的なトリプタミン |
| CN116348106A (zh) * | 2020-09-01 | 2023-06-27 | 恩维瑞克生物科学加拿大公司 | 卤代裸盖菇素衍生物及使用方法 |
| CA3192617A1 (en) * | 2020-09-20 | 2022-03-24 | Matthew BAGGOTT | Advantageous tryptamine compositions for mental disorders or enhancement |
| CN116917305A (zh) * | 2020-12-07 | 2023-10-20 | 明德赛特制药公司 | 用于治疗cns病症的作为血清素能剂的3-环状胺-吲哚衍生物 |
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- 2022-06-02 MX MX2023014437A patent/MX2023014437A/es unknown
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| US20240286998A1 (en) | 2024-08-29 |
| BR112023025340A2 (pt) | 2024-02-20 |
| AU2022287013A1 (en) | 2023-12-07 |
| EP4347559A4 (en) | 2025-04-09 |
| CO2023018652A2 (es) | 2024-01-25 |
| IL308944A (en) | 2024-01-01 |
| WO2022256554A1 (en) | 2022-12-08 |
| EP4347559A1 (en) | 2024-04-10 |
| JP2024523822A (ja) | 2024-07-02 |
| MX2023014437A (es) | 2024-03-08 |
| KR20240017363A (ko) | 2024-02-07 |
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