JPWO2022038299A5 - - Google Patents
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- Publication number
- JPWO2022038299A5 JPWO2022038299A5 JP2023512327A JP2023512327A JPWO2022038299A5 JP WO2022038299 A5 JPWO2022038299 A5 JP WO2022038299A5 JP 2023512327 A JP2023512327 A JP 2023512327A JP 2023512327 A JP2023512327 A JP 2023512327A JP WO2022038299 A5 JPWO2022038299 A5 JP WO2022038299A5
- Authority
- JP
- Japan
- Prior art keywords
- psilocin
- derivative according
- derivative
- indol
- cooh
- 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
Links
- ZBWSBXGHYDWMAK-UHFFFAOYSA-N psilocin Chemical class C1=CC=C(O)[C]2C(CCN(C)C)=CN=C21 ZBWSBXGHYDWMAK-UHFFFAOYSA-N 0.000 claims description 55
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 claims description 22
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 20
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 12
- 239000002904 solvent Substances 0.000 claims description 12
- 201000010099 disease Diseases 0.000 claims description 10
- 208000035475 disorder Diseases 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 239000003795 chemical substances by application Substances 0.000 claims description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
- 239000008194 pharmaceutical composition Substances 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 7
- 208000019901 Anxiety disease Diseases 0.000 claims description 6
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims description 6
- 206010048909 Boredom Diseases 0.000 claims description 6
- 208000006561 Cluster Headache Diseases 0.000 claims description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 6
- 208000030814 Eating disease Diseases 0.000 claims description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 6
- 208000019454 Feeding and Eating disease Diseases 0.000 claims description 6
- 208000019695 Migraine disease Diseases 0.000 claims description 6
- 206010028813 Nausea Diseases 0.000 claims description 6
- 208000018737 Parkinson disease Diseases 0.000 claims description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical group CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 6
- 206010047700 Vomiting Diseases 0.000 claims description 6
- 208000029499 cancer-related condition Diseases 0.000 claims description 6
- 208000018912 cluster headache syndrome Diseases 0.000 claims description 6
- 230000003247 decreasing effect Effects 0.000 claims description 6
- 235000014632 disordered eating Nutrition 0.000 claims description 6
- 206010027599 migraine Diseases 0.000 claims description 6
- 230000008450 motivation Effects 0.000 claims description 6
- 230000008693 nausea Effects 0.000 claims description 6
- 208000002815 pulmonary hypertension Diseases 0.000 claims description 6
- 201000000980 schizophrenia Diseases 0.000 claims description 6
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 6
- 229940076279 serotonin Drugs 0.000 claims description 6
- 208000011580 syndromic disease Diseases 0.000 claims description 6
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 6
- 230000008673 vomiting Effects 0.000 claims description 6
- 206010065369 Burnout syndrome Diseases 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 5
- AHYFYYVVAXRMKB-KRWDZBQOSA-N (2s)-3-(1h-indol-3-yl)-2-(phenylmethoxycarbonylamino)propanoic acid Chemical compound N([C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)O)C(=O)OCC1=CC=CC=C1 AHYFYYVVAXRMKB-KRWDZBQOSA-N 0.000 claims description 4
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 claims description 4
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical group OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 4
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 claims description 4
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 4
- 230000003213 activating effect Effects 0.000 claims description 4
- 239000012298 atmosphere Substances 0.000 claims description 4
- 239000012043 crude product Substances 0.000 claims description 4
- 239000007789 gas Substances 0.000 claims description 4
- 125000002140 imidazol-4-yl group Chemical group [H]N1C([H])=NC([*])=C1[H] 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- 230000001681 protective effect Effects 0.000 claims description 4
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 229940039748 oxalate Drugs 0.000 claims description 3
- VUKCNAATVIWRTF-INIZCTEOSA-N (2s)-4-oxo-4-phenylmethoxy-2-(phenylmethoxycarbonylamino)butanoic acid Chemical compound C([C@@H](C(=O)O)NC(=O)OCC=1C=CC=CC=1)C(=O)OCC1=CC=CC=C1 VUKCNAATVIWRTF-INIZCTEOSA-N 0.000 claims description 2
- BDNKZNFMNDZQMI-UHFFFAOYSA-N 1,3-diisopropylcarbodiimide Chemical compound CC(C)N=C=NC(C)C BDNKZNFMNDZQMI-UHFFFAOYSA-N 0.000 claims description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 2
- JWUJQDFVADABEY-UHFFFAOYSA-N 2-methyltetrahydrofuran Chemical compound CC1CCCO1 JWUJQDFVADABEY-UHFFFAOYSA-N 0.000 claims description 2
- FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 claims description 2
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims description 2
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 claims description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 2
- CJUMAFVKTCBCJK-UHFFFAOYSA-N N-benzyloxycarbonylglycine Chemical compound OC(=O)CNC(=O)OCC1=CC=CC=C1 CJUMAFVKTCBCJK-UHFFFAOYSA-N 0.000 claims description 2
- SPCIYGNTAMCTRO-UHFFFAOYSA-N Psilocine Natural products C1=CC(O)=C2C(CCN(C)C)=CNC2=C1 SPCIYGNTAMCTRO-UHFFFAOYSA-N 0.000 claims description 2
- 239000012190 activator Substances 0.000 claims description 2
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- 150000001718 carbodiimides Chemical class 0.000 claims description 2
- 238000004440 column chromatography Methods 0.000 claims description 2
- 239000002274 desiccant Substances 0.000 claims description 2
- BGRWYRAHAFMIBJ-UHFFFAOYSA-N diisopropylcarbodiimide Natural products CC(C)NC(=O)NC(C)C BGRWYRAHAFMIBJ-UHFFFAOYSA-N 0.000 claims description 2
- 238000010790 dilution Methods 0.000 claims description 2
- 239000012895 dilution Substances 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims description 2
- 238000001035 drying Methods 0.000 claims description 2
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical group CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- 229940049920 malate Drugs 0.000 claims description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 2
- BJEPYKJPYRNKOW-UHFFFAOYSA-N malic acid Chemical compound OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 claims description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
- 239000012074 organic phase Substances 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
- 238000010791 quenching Methods 0.000 claims description 2
- 230000000171 quenching effect Effects 0.000 claims description 2
- 238000001953 recrystallisation Methods 0.000 claims description 2
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 claims description 2
- 239000007858 starting material Substances 0.000 claims description 2
- 238000003756 stirring Methods 0.000 claims description 2
- 239000000725 suspension Substances 0.000 claims description 2
- 229940095064 tartrate Drugs 0.000 claims description 2
- DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 claims description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 2
- -1 N-methyl-N-ethyltryptamine-4-yl-ethyl carbonate Chemical compound 0.000 description 2
- QVDSEJDULKLHCG-UHFFFAOYSA-N Psilocybine Natural products C1=CC(OP(O)(O)=O)=C2C(CCN(C)C)=CNC2=C1 QVDSEJDULKLHCG-UHFFFAOYSA-N 0.000 description 2
- QKTAAWLCLHMUTJ-UHFFFAOYSA-N psilocybin Chemical compound C1C=CC(OP(O)(O)=O)=C2C(CCN(C)C)=CN=C21 QKTAAWLCLHMUTJ-UHFFFAOYSA-N 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 1
- 206010028347 Muscle twitching Diseases 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 230000036461 convulsion Effects 0.000 description 1
- 125000000814 indol-3-yl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([H])=C([*])C2=C1[H] 0.000 description 1
- 230000001337 psychedelic effect Effects 0.000 description 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102020121965.2 | 2020-08-21 | ||
| DE102020121965.2A DE102020121965A1 (de) | 2020-08-21 | 2020-08-21 | Neuartige Derivate des Psilocins mit Prodrug-Eigenschaften |
| US202063118842P | 2020-11-27 | 2020-11-27 | |
| US63/118,842 | 2020-11-27 | ||
| PCT/EP2021/073303 WO2022038299A1 (en) | 2020-08-21 | 2021-08-23 | Novel psilocin derivatives having prodrug properties |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2023538402A JP2023538402A (ja) | 2023-09-07 |
| JP2023538402A5 JP2023538402A5 (https=) | 2024-08-09 |
| JPWO2022038299A5 true JPWO2022038299A5 (https=) | 2024-08-09 |
Family
ID=77739049
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2023512327A Pending JP2023538402A (ja) | 2020-08-21 | 2021-08-23 | プロドラッグ特性を有する新規サイロシン誘導体 |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US20230295086A1 (https=) |
| EP (1) | EP4200279A1 (https=) |
| JP (1) | JP2023538402A (https=) |
| KR (1) | KR20230054397A (https=) |
| CN (2) | CN116075499B (https=) |
| AU (1) | AU2021328726A1 (https=) |
| BR (1) | BR112023003153A2 (https=) |
| CA (1) | CA3188636A1 (https=) |
| CO (1) | CO2023003282A2 (https=) |
| GB (2) | GB2632056B (https=) |
| IL (1) | IL300455A (https=) |
| MX (1) | MX2023002133A (https=) |
| WO (1) | WO2022038299A1 (https=) |
| ZA (1) | ZA202301693B (https=) |
Families Citing this family (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US11974984B2 (en) | 2017-02-09 | 2024-05-07 | Caamtech, Inc. | Compositions and methods comprising a combination of serotonergic drugs |
| US12414936B2 (en) * | 2017-02-09 | 2025-09-16 | Caamtech, Inc. | Compositions comprising a serotonergic tryptamine compound |
| CN114787363A (zh) | 2019-10-01 | 2022-07-22 | 恩派瑞安神经科学公司 | 对真菌进行遗传工程化以调节色胺表达 |
| PH12022551981A1 (en) | 2020-02-04 | 2023-10-16 | Mindset Pharma Inc | Psilocin derivatives as serotonergic psychedelic agents for the treatment of cns disorders |
| WO2022120181A1 (en) * | 2020-12-03 | 2022-06-09 | Mydecine Innovations Group Inc. | Novel psilocin analog compositions and methods of synthesizing the same |
| US12343328B2 (en) | 2020-12-09 | 2025-07-01 | Caamtech, Inc. | Dialkyl tryptamines and their therapeutic uses |
| US12534441B2 (en) | 2021-01-15 | 2026-01-27 | Beckley Psytech Limited | Tryptamine analogues |
| EP4126857A1 (en) | 2021-01-15 | 2023-02-08 | Beckley Psytech Limited | Ergoline analogues |
| US11312684B1 (en) | 2021-02-10 | 2022-04-26 | Eleusis Therapeutics Us, Inc. | Pharmaceutically acceptable salts of psilocin and uses thereof |
| WO2023023347A1 (en) * | 2021-08-20 | 2023-02-23 | Terran Biosciences Inc. | Prodrugs and derivatives of psilocin and uses thereof |
| EP4452939A4 (en) * | 2021-12-24 | 2025-12-10 | Kuleon Llc | SEROTONINERGIC COMPOUNDS, POLYPODS, AND PROMEDICINAL PRODIGITS OF SEROTONIN RECEPTOR AGONISTS AND ANTAGONISTS |
| EP4457336A4 (en) | 2021-12-31 | 2026-01-14 | Empyrean Neuroscience Inc | ORGANISMS GENETICALLY MODIFIED TO PRODUCE PSYCHOTROPIC ALKALOIDS |
| WO2023168023A1 (en) | 2022-03-04 | 2023-09-07 | Reset Pharmaceuticals, Inc. | Co-crystals or salts comprising psilocin |
| US12065404B2 (en) | 2022-03-18 | 2024-08-20 | Enveric Biosciences Canada Inc. | C4-carboxylic acid-substituted tryptamine derivatives and methods of using |
| US11707447B1 (en) | 2022-03-18 | 2023-07-25 | Enveric Biosciences Canada Inc. | C4-carbonothioate-substituted tryptamine derivatives and methods of using |
| EP4493544A4 (en) * | 2022-03-18 | 2026-03-04 | Enveric Biosciences Canada Inc | TRYPTAMINE DERIVATIVE SALTS SUBSTITUTED WITH C4-CARBOXYLIC ACID AND C4-CARBONOTHIOATE AND METHODS OF USE |
| WO2023201293A2 (en) * | 2022-04-13 | 2023-10-19 | Caamtech, Inc. | Tryptamine derivatives |
| EP4522167A1 (en) * | 2022-05-10 | 2025-03-19 | Mydecine Innovations Group Inc. | Novel psilocin prodrug compounds and methods of synthesizing the same |
| WO2023219789A1 (en) * | 2022-05-10 | 2023-11-16 | Mydecine Innovations Group Inc. | Novel psilocin prodrug compounds and methods of synthesizing the same |
| JP2025527296A (ja) * | 2022-08-05 | 2025-08-20 | マインドセット ファーマ インコーポレイテッド | セロトニンに関する障害の治療に有用であるセロトニン作動薬としての３－エチルアミノ－インドール二量体 |
| CA3261814A1 (en) * | 2022-08-05 | 2024-02-08 | Mindset Pharma Inc. | 3-PYRROLIDINE-INDOLE DIMERS USED AS SEROTONINERGY AGENTS USEFUL FOR THE TREATMENT OF DISORDERS ASSOCIATED WITH THESE |
| US12264131B2 (en) | 2022-08-19 | 2025-04-01 | Beckley Psytech Limited | Pharmaceutically acceptable salts and compositions thereof |
| WO2024055106A1 (en) * | 2022-09-12 | 2024-03-21 | Bionxt Solutions Inc. | Amino acid and carbohydrate psilocin derivatives |
| US20240269113A1 (en) * | 2023-01-24 | 2024-08-15 | Compass Pathfinder Limited | 3-(2-(DIMETHYLAMINO)ETHYL)-1H-INDOL-4-yl DERIVATIVES |
| US12246005B2 (en) | 2023-06-13 | 2025-03-11 | Beckley Psytech Limited | 5-methoxy-n,n-dimethyltryptamine (5-MeO-DMT) formulations |
| EP4592276A1 (en) | 2024-01-29 | 2025-07-30 | Universität Heidelberg | Novel acyloxymethyl prodrugs of psilocin and related 4-hydroxytryptamines obtained by an efficient synthetic approach |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3075992A (en) | 1958-09-12 | 1963-01-29 | Sandoz Ltd | Esters of indoles |
| CH386442A (de) | 1959-03-18 | 1965-01-15 | Ciba Geigy | Verfahren zur Herstellung neuer 7-Aza-benzimidazole |
| AU2005300045A1 (en) * | 2004-09-27 | 2006-05-04 | Organix, Inc. | Indole compounds useful as serotonin selective agents |
| JP2010507585A (ja) * | 2006-10-19 | 2010-03-11 | オースペックス・ファーマシューティカルズ・インコーポレイテッド | 置換インドール |
| 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 |
| CA3052974A1 (en) * | 2017-02-09 | 2018-08-16 | CaaMTech, LLC | Compositions and methods comprising a psilocybin derivative |
| PH12022551981A1 (en) * | 2020-02-04 | 2023-10-16 | Mindset Pharma Inc | Psilocin derivatives as serotonergic psychedelic agents for the treatment of cns disorders |
| WO2023023347A1 (en) * | 2021-08-20 | 2023-02-23 | Terran Biosciences Inc. | Prodrugs and derivatives of psilocin and uses thereof |
| US20240269113A1 (en) * | 2023-01-24 | 2024-08-15 | Compass Pathfinder Limited | 3-(2-(DIMETHYLAMINO)ETHYL)-1H-INDOL-4-yl DERIVATIVES |
| US20250066394A1 (en) * | 2023-08-25 | 2025-02-27 | Compass Pathfinder Limited | 3-(2-(DIMETHYLAMINO)ETHYL)-1H-INDOL-4-yl DERIVATIVES |
-
2021
- 2021-08-23 GB GB2412449.7A patent/GB2632056B/en active Active
- 2021-08-23 CN CN202180051296.8A patent/CN116075499B/zh active Active
- 2021-08-23 AU AU2021328726A patent/AU2021328726A1/en active Pending
- 2021-08-23 EP EP21769676.4A patent/EP4200279A1/en active Pending
- 2021-08-23 IL IL300455A patent/IL300455A/en unknown
- 2021-08-23 GB GB2304067.8A patent/GB2613993B/en active Active
- 2021-08-23 BR BR112023003153A patent/BR112023003153A2/pt unknown
- 2021-08-23 US US18/021,243 patent/US20230295086A1/en active Pending
- 2021-08-23 CN CN202510790017.XA patent/CN120904096A/zh active Pending
- 2021-08-23 WO PCT/EP2021/073303 patent/WO2022038299A1/en not_active Ceased
- 2021-08-23 JP JP2023512327A patent/JP2023538402A/ja active Pending
- 2021-08-23 KR KR1020237008542A patent/KR20230054397A/ko active Pending
- 2021-08-23 CA CA3188636A patent/CA3188636A1/en active Pending
- 2021-08-23 MX MX2023002133A patent/MX2023002133A/es unknown
-
2023
- 2023-02-10 ZA ZA2023/01693A patent/ZA202301693B/en unknown
- 2023-03-16 CO CONC2023/0003282A patent/CO2023003282A2/es unknown
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