CA3149602A1 - Alkyl quarternary ammonium tryptamines and their therapeutic uses - Google Patents
Alkyl quarternary ammonium tryptamines and their therapeutic uses Download PDFInfo
- Publication number
- CA3149602A1 CA3149602A1 CA3149602A CA3149602A CA3149602A1 CA 3149602 A1 CA3149602 A1 CA 3149602A1 CA 3149602 A CA3149602 A CA 3149602A CA 3149602 A CA3149602 A CA 3149602A CA 3149602 A1 CA3149602 A1 CA 3149602A1
- Authority
- CA
- Canada
- Prior art keywords
- compound
- iodide
- formula
- xrpd pattern
- crystalline
- 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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- 230000001225 therapeutic effect Effects 0.000 title abstract description 5
- 125000000217 alkyl group Chemical group 0.000 title description 10
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 90
- 239000000203 mixture Substances 0.000 claims abstract description 43
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 21
- 239000000546 pharmaceutical excipient Substances 0.000 claims abstract description 17
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 95
- 238000000634 powder X-ray diffraction Methods 0.000 claims description 56
- 239000013078 crystal Substances 0.000 claims description 47
- 229910052739 hydrogen Inorganic materials 0.000 claims description 30
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 25
- 239000001257 hydrogen Substances 0.000 claims description 23
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 20
- 229910052757 nitrogen Inorganic materials 0.000 claims description 20
- QKTAAWLCLHMUTJ-UHFFFAOYSA-N psilocybin Chemical class C1C=CC(OP(O)(O)=O)=C2C(CCN(C)C)=CN=C21 QKTAAWLCLHMUTJ-UHFFFAOYSA-N 0.000 claims description 19
- 238000000034 method Methods 0.000 claims description 18
- 208000002193 Pain Diseases 0.000 claims description 16
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 15
- 239000003814 drug Substances 0.000 claims description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
- 229940079593 drug Drugs 0.000 claims description 11
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- 150000003505 terpenes Chemical class 0.000 claims description 8
- 235000007586 terpenes Nutrition 0.000 claims description 8
- 150000001450 anions Chemical class 0.000 claims description 7
- 229940065144 cannabinoids Drugs 0.000 claims description 7
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 6
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 4
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 4
- 235000010323 ascorbic acid Nutrition 0.000 claims description 4
- 239000011668 ascorbic acid Substances 0.000 claims description 4
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 3
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- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 150000002431 hydrogen Chemical group 0.000 claims 4
- 241000764238 Isis Species 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 abstract description 6
- -1 alkyl quaternary ammonium tryptamine compounds Chemical class 0.000 description 22
- 238000012937 correction Methods 0.000 description 21
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- 238000013480 data collection Methods 0.000 description 15
- 239000000243 solution Substances 0.000 description 14
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
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- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 9
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- GLZPCOQZEFWAFX-UHFFFAOYSA-N Geraniol Chemical compound CC(C)=CCCC(C)=CCO GLZPCOQZEFWAFX-UHFFFAOYSA-N 0.000 description 6
- DMULVCHRPCFFGV-UHFFFAOYSA-N N,N-dimethyltryptamine Chemical compound C1=CC=C2C(CCN(C)C)=CNC2=C1 DMULVCHRPCFFGV-UHFFFAOYSA-N 0.000 description 6
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- 239000002244 precipitate Substances 0.000 description 6
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- APJYDQYYACXCRM-UHFFFAOYSA-N tryptamine Chemical compound C1=CC=C2C(CCN)=CNC2=C1 APJYDQYYACXCRM-UHFFFAOYSA-N 0.000 description 6
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- 102100022738 5-hydroxytryptamine receptor 1A Human genes 0.000 description 5
- 101710138638 5-hydroxytryptamine receptor 1A Proteins 0.000 description 5
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- 101710138091 5-hydroxytryptamine receptor 2A Proteins 0.000 description 5
- 238000005481 NMR spectroscopy Methods 0.000 description 5
- FAMPSKZZVDUYOS-UHFFFAOYSA-N alpha-Caryophyllene Natural products CC1=CCC(C)(C)C=CCC(C)=CCC1 FAMPSKZZVDUYOS-UHFFFAOYSA-N 0.000 description 5
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- XMBWDFGMSWQBCA-UHFFFAOYSA-M iodide Chemical compound [I-] XMBWDFGMSWQBCA-UHFFFAOYSA-M 0.000 description 5
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical group IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 5
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- ZLYNXDIDWUWASO-UHFFFAOYSA-N 6,6,9-trimethyl-3-pentyl-8,10-dihydro-7h-benzo[c]chromene-1,9,10-triol Chemical compound CC1(C)OC2=CC(CCCCC)=CC(O)=C2C2=C1CCC(C)(O)C2O ZLYNXDIDWUWASO-UHFFFAOYSA-N 0.000 description 4
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- HFTAFOQKODTIJY-UHFFFAOYSA-N umbelliferone Natural products Cc1cc2C=CC(=O)Oc2cc1OCC=CC(C)(C)O HFTAFOQKODTIJY-UHFFFAOYSA-N 0.000 description 1
- WCTNXGFHEZQHDR-UHFFFAOYSA-N valencene Natural products C1CC(C)(C)C2(C)CC(C(=C)C)CCC2=C1 WCTNXGFHEZQHDR-UHFFFAOYSA-N 0.000 description 1
- 235000012141 vanillin Nutrition 0.000 description 1
- MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 description 1
- FGQOOHJZONJGDT-UHFFFAOYSA-N vanillin Natural products COC1=CC(O)=CC(C=O)=C1 FGQOOHJZONJGDT-UHFFFAOYSA-N 0.000 description 1
- 229960004688 venlafaxine Drugs 0.000 description 1
- PNVNVHUZROJLTJ-UHFFFAOYSA-N venlafaxine Chemical compound C1=CC(OC)=CC=C1C(CN(C)C)C1(O)CCCCC1 PNVNVHUZROJLTJ-UHFFFAOYSA-N 0.000 description 1
- NCYCYZXNIZJOKI-UHFFFAOYSA-N vitamin A aldehyde Natural products O=CC=C(C)C=CC=C(C)C=CC1=C(C)CCCC1(C)C NCYCYZXNIZJOKI-UHFFFAOYSA-N 0.000 description 1
- 229960002263 vortioxetine Drugs 0.000 description 1
- YQNWZWMKLDQSAC-UHFFFAOYSA-N vortioxetine Chemical compound CC1=CC(C)=CC=C1SC1=CC=CC=C1N1CCNCC1 YQNWZWMKLDQSAC-UHFFFAOYSA-N 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- USDOQCCMRDNVAH-KKUMJFAQSA-N β-cadinene Chemical compound C1C=C(C)C[C@H]2[C@H](C(C)C)CC=C(C)[C@@H]21 USDOQCCMRDNVAH-KKUMJFAQSA-N 0.000 description 1
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201962891388P | 2019-08-25 | 2019-08-25 | |
| US62/891,388 | 2019-08-25 | ||
| US202063007653P | 2020-04-09 | 2020-04-09 | |
| US63/007,653 | 2020-04-09 | ||
| US202063053976P | 2020-07-20 | 2020-07-20 | |
| US63/053,976 | 2020-07-20 | ||
| PCT/US2020/047791 WO2021041407A1 (en) | 2019-08-25 | 2020-08-25 | Alkyl quarternary ammonium tryptamines and their therapeutic uses |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA3149602A1 true CA3149602A1 (en) | 2021-03-04 |
Family
ID=74684268
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA3149602A Pending CA3149602A1 (en) | 2019-08-25 | 2020-08-25 | Alkyl quarternary ammonium tryptamines and their therapeutic uses |
Country Status (4)
| Country | Link |
|---|---|
| EP (1) | EP4017859A4 (de) |
| AU (1) | AU2020337903A1 (de) |
| CA (1) | CA3149602A1 (de) |
| WO (1) | WO2021041407A1 (de) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20180021326A1 (en) | 2016-07-23 | 2018-01-25 | Paul Edward Stamets | Compositions and methods for enhancing neuroregeneration and cognition by combining mushroom extracts containing active ingredients psilocin or psilocybin with erinacines or hericenones enhanced with niacin |
| US20210069170A1 (en) | 2016-07-23 | 2021-03-11 | Paul Edward Stamets | Tryptamine compositions for enhancing neurite outgrowth |
| US11701348B1 (en) | 2016-07-23 | 2023-07-18 | Turtle Bear Holdings, Llc | Psilocybin compositions |
| AU2020386445A1 (en) | 2019-11-19 | 2022-06-02 | Paul Edward Stamets | Tryptamine compositions for enhancing neurite outgrowth |
| CA3169783A1 (en) * | 2020-03-19 | 2021-09-23 | Andrew R. Chadeayne | Crystalline psilacetin derivatives |
| AU2021267859B9 (en) | 2020-05-04 | 2023-07-27 | Caamtech, Inc. | Crystalline dimethyl tryptamine analogues |
| IL297492A (en) | 2020-05-19 | 2022-12-01 | Cybin Irl Ltd | Denatured Tryptamine Derivatives and Methods of Use |
| KR20230024378A (ko) | 2020-06-12 | 2023-02-20 | 벡클리 싸이테크 리미티드 | 5-메톡시-n, n-디메틸트립타민의 벤조에이트 염을 포함하는 조성물 |
| WO2023018864A1 (en) | 2021-08-12 | 2023-02-16 | Psilosterics, Llc | Hallucinogenic and non-hallucinogenic serotonin receptor agonists and methods of making and using the same |
| WO2023023298A1 (en) * | 2021-08-20 | 2023-02-23 | Psilosterics, Llc | Hallucinogenic and non-hallucinogenic compounds and methods of making and using the same |
| CA3235016A1 (en) * | 2021-10-15 | 2023-04-20 | Andrew R. Chadeayne | Crystalline tryptamine compounds |
| US11746087B1 (en) | 2022-03-18 | 2023-09-05 | Enveric Biosciences Canada Inc. | C4-carboxylic acid-substituted tryptamine derivatives and methods of using |
| WO2023173227A1 (en) * | 2022-03-18 | 2023-09-21 | Enveric Biosciences Canada Inc. | C4-substituted tryptamine derivatives and methods of using |
| WO2023205768A2 (en) * | 2022-04-21 | 2023-10-26 | Caamtech, Inc. | Crystalline quaternary salts of 4-substituted tryptamines |
| WO2023250465A2 (en) * | 2022-06-24 | 2023-12-28 | Caamtech, Inc. | Tryptamine derivatives |
| WO2024026291A1 (en) * | 2022-07-25 | 2024-02-01 | Caamtech, Inc. | Methyl substituted quaternary tryptamine derivatives |
| GB202212116D0 (en) | 2022-08-19 | 2022-10-05 | Beckley Psytech Ltd | Pharmaceutically acceptable salts and Compositions thereof |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2783520B1 (fr) * | 1998-09-21 | 2000-11-10 | Oreal | Nouveaux 4-hydroxyindoles cationiques, leur utilisation pour la teinture d'oxydation des fibres keratiniques, compositions tinctoriales et procede de teinture |
| US9440920B2 (en) * | 2014-07-03 | 2016-09-13 | Wisconsin Alumni Research Foundation | Antimicrobial compounds, compositions and methods of use thereof |
| US20190142851A1 (en) * | 2017-11-16 | 2019-05-16 | CaaMTech, LLC | Compositions comprising a psilocybin derivative and a cannabinoid |
| AU2018217829A1 (en) * | 2017-02-09 | 2019-09-12 | CaaMTech, LLC | Compositions and methods comprising a psilocybin derivative |
-
2020
- 2020-08-25 AU AU2020337903A patent/AU2020337903A1/en active Pending
- 2020-08-25 CA CA3149602A patent/CA3149602A1/en active Pending
- 2020-08-25 EP EP20858480.5A patent/EP4017859A4/de active Pending
- 2020-08-25 WO PCT/US2020/047791 patent/WO2021041407A1/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| EP4017859A1 (de) | 2022-06-29 |
| WO2021041407A1 (en) | 2021-03-04 |
| EP4017859A4 (de) | 2023-08-23 |
| AU2020337903A1 (en) | 2022-03-31 |
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Effective date: 20231220 |