CA3179161C - Therapeutic compositions comprising deuterated or partially deuterated n,n-dimethyltryptamine compounds - Google Patents
Therapeutic compositions comprising deuterated or partially deuterated n,n-dimethyltryptamine compounds Download PDFInfo
- Publication number
- CA3179161C CA3179161C CA3179161A CA3179161A CA3179161C CA 3179161 C CA3179161 C CA 3179161C CA 3179161 A CA3179161 A CA 3179161A CA 3179161 A CA3179161 A CA 3179161A CA 3179161 C CA3179161 C CA 3179161C
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- Prior art keywords
- compound
- dimethyltryptamine
- deuterated
- compounds
- formula
- Prior art date
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- 239000000203 mixture Substances 0.000 title claims abstract description 200
- 230000001225 therapeutic effect Effects 0.000 title claims description 10
- DMULVCHRPCFFGV-UHFFFAOYSA-N N,N-dimethyltryptamine Chemical class C1=CC=C2C(CCN(C)C)=CNC2=C1 DMULVCHRPCFFGV-UHFFFAOYSA-N 0.000 title abstract description 164
- 150000001875 compounds Chemical class 0.000 claims abstract description 210
- 150000003839 salts Chemical class 0.000 claims abstract description 69
- -1 deuterated N,N-dimethyltryptamine compound Chemical class 0.000 claims abstract description 54
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 21
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical group OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 37
- 229940125904 compound 1 Drugs 0.000 claims description 13
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 12
- 229940125898 compound 5 Drugs 0.000 claims description 8
- 229940125782 compound 2 Drugs 0.000 claims description 4
- 239000002552 dosage form Substances 0.000 claims 7
- 102100038954 60S ribosomal export protein NMD3 Human genes 0.000 claims 1
- 101000603190 Homo sapiens 60S ribosomal export protein NMD3 Proteins 0.000 claims 1
- 239000006201 parenteral dosage form Substances 0.000 claims 1
- 239000007909 solid dosage form Substances 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 64
- 229910052805 deuterium Inorganic materials 0.000 abstract description 26
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 abstract description 23
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- 241000720974 Protium Species 0.000 abstract description 8
- 238000002560 therapeutic procedure Methods 0.000 abstract description 8
- 239000001257 hydrogen Substances 0.000 abstract description 7
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- 239000007822 coupling agent Substances 0.000 description 64
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 60
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 54
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 45
- 239000002904 solvent Substances 0.000 description 42
- 239000000243 solution Substances 0.000 description 35
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 33
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 33
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- 239000007787 solid Substances 0.000 description 16
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- ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 9
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Landscapes
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Applications Claiming Priority (19)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PCT/EP2020/065244 WO2020245133A1 (en) | 2019-06-03 | 2020-06-02 | Therapeutic compositions comprising deuterated or partially deuterated n,n-dimethyltryptamine compounds |
| US16/890,664 US11771681B2 (en) | 2019-06-03 | 2020-06-02 | Therapeutic compounds |
| GB2008303.6 | 2020-06-02 | ||
| US16/890,664 | 2020-06-02 | ||
| EPPCT/EP2020/065244 | 2020-06-02 | ||
| GB2008303.6A GB2585978B (en) | 2019-06-03 | 2020-06-02 | Therapeutic compositions |
| US17/108,679 | 2020-12-01 | ||
| US17/108,938 US20220169606A1 (en) | 2020-12-01 | 2020-12-01 | Compositions and compounds for bioanalysis |
| US17/108,938 | 2020-12-01 | ||
| GB2018950.2 | 2020-12-01 | ||
| GBGB2018955.1A GB202018955D0 (en) | 2020-12-01 | 2020-12-01 | Compositions and compounds for bioanalysis |
| GB2018955.1 | 2020-12-01 | ||
| GBGB2018950.2A GB202018950D0 (en) | 2020-12-01 | 2020-12-01 | Parenteral formulation |
| US17/108,679 US20220168274A1 (en) | 2020-12-01 | 2020-12-01 | Parenteral Formulation |
| US17/208,583 | 2021-03-22 | ||
| US17/208,583 US11773062B2 (en) | 2021-03-22 | 2021-03-22 | Deuterated compounds |
| GB2103981.3 | 2021-03-22 | ||
| GB2103981.3A GB2605144A (en) | 2021-03-22 | 2021-03-22 | Deuterated compounds |
| PCT/EP2021/060750 WO2021116503A2 (en) | 2020-06-02 | 2021-04-23 | Deuterated compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA3179161A1 CA3179161A1 (en) | 2021-06-17 |
| CA3179161C true CA3179161C (en) | 2023-10-31 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA3179161A Active CA3179161C (en) | 2020-06-02 | 2021-04-23 | Therapeutic compositions comprising deuterated or partially deuterated n,n-dimethyltryptamine compounds |
Country Status (10)
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| CN (1) | CN116056763B (ko) |
| AU (1) | AU2021204158B2 (ko) |
| CA (1) | CA3179161C (ko) |
| ES (1) | ES2928395T3 (ko) |
| IL (1) | IL298541B2 (ko) |
| MX (1) | MX2022014900A (ko) |
| NZ (1) | NZ794833A (ko) |
| PL (1) | PL3902541T3 (ko) |
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| CA2666149A1 (en) * | 2006-10-19 | 2008-04-24 | Auspex Pharmaceuticals, Inc. | Substituted indoles |
| WO2019081764A1 (en) * | 2017-10-26 | 2019-05-02 | Consejo Superior De Investigaciones Científicas (Csic) | ASSOCIATION PRODUCT FOR THE TREATMENT OF NEUROLOGICAL AND / OR PSYCHIATRIC DISORDERS |
| GB201907871D0 (en) * | 2019-06-03 | 2019-07-17 | Small Pharma Ltd | Therapeutic compositions |
| MX2022005399A (es) * | 2019-11-07 | 2022-07-05 | Small Pharma Ltd | Compuestos. |
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2021
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- 2021-04-23 ES ES21720509T patent/ES2928395T3/es active Active
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| AU2021204158B2 (en) | 2023-03-02 |
| CN116056763A (zh) | 2023-05-02 |
| KR20230007547A (ko) | 2023-01-12 |
| AU2021204158A1 (en) | 2023-01-05 |
| KR102589605B1 (ko) | 2023-10-13 |
| IL298541A (en) | 2023-01-01 |
| NZ794833A (en) | 2023-03-31 |
| JP2023520256A (ja) | 2023-05-16 |
| IL298541B1 (en) | 2024-04-01 |
| ES2928395T3 (es) | 2022-11-17 |
| PL3902541T3 (pl) | 2022-11-14 |
| JP7288154B2 (ja) | 2023-06-06 |
| CN116056763B (zh) | 2024-03-05 |
| CA3179161A1 (en) | 2021-06-17 |
| MX2022014900A (es) | 2023-03-27 |
| IL298541B2 (en) | 2024-08-01 |
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