JPWO2021155467A5 - - Google Patents
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- JPWO2021155467A5 JPWO2021155467A5 JP2022548039A JP2022548039A JPWO2021155467A5 JP WO2021155467 A5 JPWO2021155467 A5 JP WO2021155467A5 JP 2022548039 A JP2022548039 A JP 2022548039A JP 2022548039 A JP2022548039 A JP 2022548039A JP WO2021155467 A5 JPWO2021155467 A5 JP WO2021155467A5
- Authority
- JP
- Japan
- Prior art keywords
- substituted
- unsubstituted
- alkyl
- hydrogen
- cycloalkyl
- 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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- 125000000753 cycloalkyl group Chemical group 0.000 claims description 116
- 150000001875 compounds Chemical class 0.000 claims description 102
- 229910052739 hydrogen Inorganic materials 0.000 claims description 100
- 239000001257 hydrogen Substances 0.000 claims description 100
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 72
- 150000002431 hydrogen Chemical class 0.000 claims description 69
- 125000005843 halogen group Chemical group 0.000 claims description 68
- 125000004429 atom Chemical group 0.000 claims description 54
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 51
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 51
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 49
- 229910005965 SO 2 Inorganic materials 0.000 claims description 41
- 229910020008 S(O) Inorganic materials 0.000 claims description 39
- 125000001424 substituent group Chemical group 0.000 claims description 38
- 125000000623 heterocyclic group Chemical group 0.000 claims description 36
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 33
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 33
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 33
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims description 32
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 32
- 125000002947 alkylene group Chemical group 0.000 claims description 32
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 30
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 29
- 229910052717 sulfur Inorganic materials 0.000 claims description 26
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical group [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 25
- 229910052805 deuterium Chemical group 0.000 claims description 25
- 125000003358 C2-C20 alkenyl group Chemical group 0.000 claims description 24
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 24
- 125000003118 aryl group Chemical group 0.000 claims description 23
- 229910052799 carbon Inorganic materials 0.000 claims description 23
- 125000004432 carbon atom Chemical group C* 0.000 claims description 23
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 22
- 125000001188 haloalkyl group Chemical group 0.000 claims description 22
- 125000001072 heteroaryl group Chemical group 0.000 claims description 22
- 125000006643 (C2-C6) haloalkenyl group Chemical group 0.000 claims description 18
- 208000035475 disorder Diseases 0.000 claims description 18
- 229910052736 halogen Inorganic materials 0.000 claims description 17
- 150000002367 halogens Chemical class 0.000 claims description 17
- 229910052760 oxygen Inorganic materials 0.000 claims description 16
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 12
- 125000000232 haloalkynyl group Chemical group 0.000 claims description 12
- 125000003341 7 membered heterocyclic group Chemical group 0.000 claims description 10
- 125000005275 alkylenearyl group Chemical group 0.000 claims description 10
- 125000005218 alkyleneheteroaryl group Chemical group 0.000 claims description 10
- 150000003839 salts Chemical class 0.000 claims description 10
- 239000012453 solvate Substances 0.000 claims description 10
- 229940002612 prodrug Drugs 0.000 claims description 9
- 239000000651 prodrug Substances 0.000 claims description 9
- 125000006644 (C2-C6) haloalkynyl group Chemical group 0.000 claims description 7
- -1 C1-C20 haloalkyl Chemical group 0.000 claims description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
- 125000005842 heteroatom Chemical group 0.000 claims description 7
- 208000028017 Psychotic disease Diseases 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 125000000304 alkynyl group Chemical group 0.000 claims description 6
- 229910052794 bromium Inorganic materials 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 201000010099 disease Diseases 0.000 claims description 6
- 229910052731 fluorine Inorganic materials 0.000 claims description 6
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 5
- 102000040125 5-hydroxytryptamine receptor family Human genes 0.000 claims description 5
- 108091032151 5-hydroxytryptamine receptor family Proteins 0.000 claims description 5
- 208000019901 Anxiety disease Diseases 0.000 claims description 5
- 239000003814 drug Substances 0.000 claims description 5
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 5
- 208000020016 psychiatric disease Diseases 0.000 claims description 5
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 4
- 125000006649 (C2-C20) alkynyl group Chemical group 0.000 claims description 4
- 208000024827 Alzheimer disease Diseases 0.000 claims description 4
- 208000021384 Obsessive-Compulsive disease Diseases 0.000 claims description 4
- 208000028173 post-traumatic stress disease Diseases 0.000 claims description 4
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims description 3
- 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims description 3
- 230000004913 activation Effects 0.000 claims description 3
- 230000036506 anxiety Effects 0.000 claims description 3
- 208000015802 attention deficit-hyperactivity disease Diseases 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- 101710085469 CD2 homolog Proteins 0.000 claims description 2
- 108050005493 CD3 protein, epsilon/gamma/delta subunit Proteins 0.000 claims description 2
- 102100036364 Cadherin-2 Human genes 0.000 claims description 2
- 208000030814 Eating disease Diseases 0.000 claims description 2
- 208000019454 Feeding and Eating disease Diseases 0.000 claims description 2
- 101000714537 Homo sapiens Cadherin-2 Proteins 0.000 claims description 2
- 208000019022 Mood disease Diseases 0.000 claims description 2
- 101001043818 Mus musculus Interleukin-31 receptor subunit alpha Proteins 0.000 claims description 2
- 235000014632 disordered eating Nutrition 0.000 claims description 2
- 238000010494 dissociation reaction Methods 0.000 claims description 2
- 230000005593 dissociations Effects 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 206010013663 drug dependence Diseases 0.000 claims description 2
- 230000003938 response to stress Effects 0.000 claims description 2
- 208000011117 substance-related disease Diseases 0.000 claims description 2
- 208000024891 symptom Diseases 0.000 claims description 2
- 208000011580 syndromic disease Diseases 0.000 claims description 2
- 206010011906 Death Diseases 0.000 claims 1
- 208000011688 Generalised anxiety disease Diseases 0.000 claims 1
- 208000030990 Impulse-control disease Diseases 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 claims 1
- 201000011510 cancer Diseases 0.000 claims 1
- 208000029364 generalized anxiety disease Diseases 0.000 claims 1
- 125000000262 haloalkenyl group Chemical group 0.000 claims 1
- 208000024714 major depressive disease Diseases 0.000 claims 1
- 208000019906 panic disease Diseases 0.000 claims 1
- 238000000034 method Methods 0.000 description 13
- 208000012902 Nervous system disease Diseases 0.000 description 7
- 208000025966 Neurological disease Diseases 0.000 description 5
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 3
- 230000003213 activating effect Effects 0.000 description 3
- 231100000871 behavioral problem Toxicity 0.000 description 3
- 210000003169 central nervous system Anatomy 0.000 description 3
- 208000000103 Anorexia Nervosa Diseases 0.000 description 2
- 206010006550 Bulimia nervosa Diseases 0.000 description 2
- 208000028698 Cognitive impairment Diseases 0.000 description 2
- 208000018737 Parkinson disease Diseases 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 208000014679 binge eating disease Diseases 0.000 description 2
- 239000012472 biological sample Substances 0.000 description 2
- 210000004027 cell Anatomy 0.000 description 2
- 208000015114 central nervous system disease Diseases 0.000 description 2
- 208000010877 cognitive disease Diseases 0.000 description 2
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 230000003834 intracellular effect Effects 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 2
- 229940124597 therapeutic agent Drugs 0.000 description 2
- 208000014912 Central Nervous System Infections Diseases 0.000 description 1
- 208000011990 Corticobasal Degeneration Diseases 0.000 description 1
- 206010012239 Delusion Diseases 0.000 description 1
- 206010012289 Dementia Diseases 0.000 description 1
- 208000026097 Factitious disease Diseases 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- 208000001640 Fibromyalgia Diseases 0.000 description 1
- 201000004311 Gilles de la Tourette syndrome Diseases 0.000 description 1
- 208000004547 Hallucinations Diseases 0.000 description 1
- 208000023105 Huntington disease Diseases 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- 208000009829 Lewy Body Disease Diseases 0.000 description 1
- 201000002832 Lewy body dementia Diseases 0.000 description 1
- 208000037490 Medically Unexplained Symptoms Diseases 0.000 description 1
- 208000019695 Migraine disease Diseases 0.000 description 1
- 208000029726 Neurodevelopmental disease Diseases 0.000 description 1
- 206010057342 Onychophagia Diseases 0.000 description 1
- 206010033799 Paralysis Diseases 0.000 description 1
- 206010036631 Presenile dementia Diseases 0.000 description 1
- 208000005793 Restless legs syndrome Diseases 0.000 description 1
- 208000006289 Rett Syndrome Diseases 0.000 description 1
- 208000034189 Sclerosis Diseases 0.000 description 1
- 206010039966 Senile dementia Diseases 0.000 description 1
- 208000023906 Sexual and Gender disease Diseases 0.000 description 1
- 206010048327 Supranuclear palsy Diseases 0.000 description 1
- 206010043118 Tardive Dyskinesia Diseases 0.000 description 1
- 208000000323 Tourette Syndrome Diseases 0.000 description 1
- 208000016620 Tourette disease Diseases 0.000 description 1
- 208000026911 Tuberous sclerosis complex Diseases 0.000 description 1
- 201000004810 Vascular dementia Diseases 0.000 description 1
- 230000016571 aggressive behavior Effects 0.000 description 1
- 208000029560 autism spectrum disease Diseases 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 231100000868 delusion Toxicity 0.000 description 1
- 208000027688 depersonalization disease Diseases 0.000 description 1
- 125000004431 deuterium atom Chemical group 0.000 description 1
- 206010015037 epilepsy Diseases 0.000 description 1
- 208000013403 hyperactivity Diseases 0.000 description 1
- 230000005032 impulse control Effects 0.000 description 1
- 208000035231 inattentive type attention deficit hyperactivity disease Diseases 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 208000014674 injury Diseases 0.000 description 1
- 206010027599 migraine Diseases 0.000 description 1
- 208000012268 mitochondrial disease Diseases 0.000 description 1
- 201000006417 multiple sclerosis Diseases 0.000 description 1
- 230000004770 neurodegeneration Effects 0.000 description 1
- 208000015122 neurodegenerative disease Diseases 0.000 description 1
- 208000033808 peripheral neuropathy Diseases 0.000 description 1
- 229940001470 psychoactive drug Drugs 0.000 description 1
- 239000004089 psychotropic agent Substances 0.000 description 1
- 201000000980 schizophrenia Diseases 0.000 description 1
- 208000017520 skin disease Diseases 0.000 description 1
- 208000019116 sleep disease Diseases 0.000 description 1
- 208000022925 sleep disturbance Diseases 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 230000008733 trauma Effects 0.000 description 1
- 208000002271 trichotillomania Diseases 0.000 description 1
- 208000009999 tuberous sclerosis Diseases 0.000 description 1
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US202062969894P | 2020-02-04 | 2020-02-04 | |
US62/969,894 | 2020-02-04 | ||
PCT/CA2021/050122 WO2021155467A1 (en) | 2020-02-04 | 2021-02-04 | 3-pyrrolidine-indole derivatives as serotonergic psychedelic agents for the treatment of cns disorders |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2023512821A JP2023512821A (ja) | 2023-03-29 |
JPWO2021155467A5 true JPWO2021155467A5 (zh) | 2024-02-13 |
Family
ID=77199114
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2022548039A Pending JP2023512821A (ja) | 2020-02-04 | 2021-02-04 | 中枢神経系障害の治療のためのセロトニン作動性幻覚薬としての3-ピロリジンインドール誘導体 |
Country Status (11)
Country | Link |
---|---|
US (2) | US11453689B2 (zh) |
EP (1) | EP4100403A4 (zh) |
JP (1) | JP2023512821A (zh) |
KR (1) | KR20220137085A (zh) |
CN (1) | CN115380028A (zh) |
AU (1) | AU2021215709A1 (zh) |
BR (1) | BR112022015379A2 (zh) |
CA (1) | CA3166940A1 (zh) |
IL (1) | IL295374A (zh) |
MX (1) | MX2022009528A (zh) |
WO (1) | WO2021155467A1 (zh) |
Families Citing this family (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20230219889A1 (en) | 2020-05-19 | 2023-07-13 | Cybin Irl Limited | Deuterated tryptamine derivatives and methods of use |
AU2022229037A1 (en) * | 2021-03-02 | 2023-09-28 | Mindset Pharma Inc. | Indole derivatives as serotonergic agents useful for the treatment of disorders related thereto |
WO2023019367A1 (en) * | 2021-08-20 | 2023-02-23 | Mindset Pharma Inc. | Indole derivatives as serotonergic agents useful for the treatment of disorders related thereto |
WO2023122320A1 (en) * | 2021-12-24 | 2023-06-29 | Kuleon Llc | Polypodal serotonergic compounds and prodrugs of serotonin receptor agonists and antagonists |
WO2023150547A2 (en) * | 2022-02-01 | 2023-08-10 | Caamtech, Inc. | Psychedelic compounds and their therapeutic uses |
US20230202978A1 (en) | 2022-03-04 | 2023-06-29 | Reset Pharmaceuticals, Inc. | Co-crystal or salt |
WO2023201423A1 (en) * | 2022-04-19 | 2023-10-26 | Mindset Pharma Inc. | Indoline derivatives as serotonergic agents useful for the treatment of disorders related thereto |
Family Cites Families (46)
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US5559129A (en) | 1990-10-15 | 1996-09-24 | Pfizer Inc | Indole derivatives |
US5545644A (en) | 1990-10-15 | 1996-08-13 | Pfizer Inc. | Indole derivatives |
US5607951A (en) | 1990-10-15 | 1997-03-04 | Pfizer Inc | Indole derivatives |
US5120749A (en) | 1991-02-20 | 1992-06-09 | Abbott Laboratories | Platelet activating antagonists |
TW288010B (zh) * | 1992-03-05 | 1996-10-11 | Pfizer | |
KR0179072B1 (ko) * | 1992-04-07 | 1999-03-20 | 알렌 제이. 스피겔 | 5-ht1 작동약으로서의 인돌 유도체 |
CN1121348A (zh) * | 1993-04-22 | 1996-04-24 | 辉瑞研究及发展公司 | 吲哚衍生物作为5-ht1类激动剂用于治疗周期性偏头痛 |
AP486A (en) * | 1993-04-27 | 1996-04-16 | Pfizer | Indole derivatives. |
FR2735774B1 (fr) | 1995-06-21 | 1997-09-12 | Sanofi Sa | Utilisation de composes agonistes du recepteur cb2 humain pour la preparation de medicaments immunomodulateurs, nouveaux composes agonistes du recepteur cb2 et les compositions pharmaceutiques les contenant |
ATE258050T1 (de) | 1996-10-31 | 2004-02-15 | Harbor Branch Oceanographic | Verwendung neurogen-entzuendungshemmender verbindungen und zusammensetzungen |
US6100291A (en) | 1998-03-16 | 2000-08-08 | Allelix Biopharmaceuticals Inc. | Pyrrolidine-indole compounds having 5-HT6 affinity |
GB9816263D0 (en) | 1998-07-24 | 1998-09-23 | Merck Sharp & Dohme | Therapeutic agents |
US6218423B1 (en) | 1998-08-14 | 2001-04-17 | Gpi Nil Holdings, Inc. | Pyrrolidine derivatives for vision and memory disorders |
GB9923314D0 (en) | 1999-10-01 | 1999-12-08 | Pfizer Ltd | Acylation process |
WO2001094310A1 (en) | 2000-06-07 | 2001-12-13 | The State Of Oregon Acting By And Through The State Board Of Higher Education On Behalf Of Oregon State University | Methods for making bis-heterocyclic alkaloids |
US7135479B2 (en) | 2002-09-12 | 2006-11-14 | Wyeth | Antidepressant azaheterocyclylmethyl derivatives of heterocycle-fused benzodioxans |
WO2004106298A1 (en) | 2003-05-30 | 2004-12-09 | Janssen Pharmaceutica N.V. | Indole derivatives with an improved antipsychotic activity |
NZ553646A (en) | 2004-09-22 | 2010-07-30 | Janssen Pharmaceutica Nv | Inhibitors of the interaction between MDM2 and p53 |
BRPI0607517A2 (pt) | 2005-04-13 | 2009-09-08 | Neuraxon Inc | compostos de indol substituìdo, composição farmacêutica compreendendo o mesmo, método para tratar e uso do mesmo |
US8003624B2 (en) | 2005-08-25 | 2011-08-23 | Schering Corporation | Functionally selective ALPHA2C adrenoreceptor agonists |
AU2007206950B2 (en) | 2006-01-19 | 2012-02-02 | Janssen Pharmaceutica N.V. | Substituted indolyl-alkyl-amino-derivatives as inhibitors of histone deacetylase |
EP2029136A4 (en) * | 2006-05-22 | 2010-01-06 | Vanda Pharmaceuticals Inc | TREATMENT FOR DEPRESSION DISEASES |
US7964728B2 (en) | 2006-07-06 | 2011-06-21 | Solvay Pharmaceuticals B.V. | Azaindole derivatives with a combination of partial nicotinic acetyl-choline receptor agonism and dopamine reuptake inhibition |
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US20090014868A1 (en) | 2007-07-10 | 2009-01-15 | International Business Machines Corporation | Manufacturing ic chip in portions for later combining, and related structure |
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EP3160464B1 (en) * | 2014-06-26 | 2018-07-18 | Contera Pharma APS | 6-hydroxybuspirone for use in the treatment of movement disorders |
GB201511382D0 (en) | 2015-06-29 | 2015-08-12 | Imp Innovations Ltd | Novel compounds and their use in therapy |
MA42769B1 (fr) * | 2015-09-10 | 2019-12-31 | Suven Life Sciences Ltd | Dérivés de fluoroindole en tant que modulateurs allostériques positifs du récepteur muscarinique m1 |
US20200030309A1 (en) | 2016-09-29 | 2020-01-30 | The Regents Of The University Of California | Compounds for increasing neural plasticity |
US20190358238A1 (en) | 2016-11-16 | 2019-11-28 | University Of South Florida | ALLOSTERIC ANTAGONISTS OF GPRC6a AND THEIR USE IN MITIGATING PROTEINOPATHIES |
GB2571696B (en) | 2017-10-09 | 2020-05-27 | Compass Pathways Ltd | Large scale method for the preparation of Psilocybin and formulations of Psilocybin so produced |
US12090145B2 (en) | 2018-08-20 | 2024-09-17 | Yale University | Combination therapy for treating or preventing depression or other mood diseases |
EP3917537A4 (en) | 2019-01-30 | 2022-09-07 | Diamond Therapeutics Inc. | METHODS AND COMPOSITIONS USING A 5HT RECEPTOR AGONIST FOR THE TREATMENT OF MENTAL, COGNITIVE, BEHAVIORAL AND/OR MODIFICATIONS |
BR112021017621A2 (pt) | 2019-03-07 | 2021-11-23 | Arbormentis LLC | Composições e métodos de uso compreendendo substâncias com ações de plasticidade neural administradas em dosagens e formulações não psicodélicas/psicotomiméticas |
GB201907871D0 (en) | 2019-06-03 | 2019-07-17 | Small Pharma Ltd | Therapeutic compositions |
CA3160793A1 (en) | 2019-12-04 | 2021-06-10 | Neonmind Biosciences Inc. | Use of psilocin, psilocybin or analogs thereof in weight loss, treatment of obesity and compulsive eating disorder |
EP4099995A1 (en) | 2020-02-05 | 2022-12-14 | Yale University | Psychedelic treatment for headache disorders |
US20230219889A1 (en) | 2020-05-19 | 2023-07-13 | Cybin Irl Limited | Deuterated tryptamine derivatives and methods of use |
WO2021116503A2 (en) | 2020-06-02 | 2021-06-17 | Small Pharma Ltd | Deuterated compounds |
IL299506A (en) | 2020-06-30 | 2023-02-01 | Reunion Neuroscience Canada Inc | Prodrugs of tryptamine |
WO2022018709A1 (en) | 2020-07-21 | 2022-01-27 | Ai Pharmaceuticals Jamaica Limited | Compositions and methods for treatment of psychoses and psychotic disorders |
US11000534B1 (en) | 2020-10-08 | 2021-05-11 | Lennham Pharmaceuticals, Inc. | Deuterated derivatives of psilocybin and uses thereof |
-
2021
- 2021-02-04 EP EP21751045.2A patent/EP4100403A4/en active Pending
- 2021-02-04 BR BR112022015379A patent/BR112022015379A2/pt unknown
- 2021-02-04 WO PCT/CA2021/050122 patent/WO2021155467A1/en active Application Filing
- 2021-02-04 IL IL295374A patent/IL295374A/en unknown
- 2021-02-04 AU AU2021215709A patent/AU2021215709A1/en active Pending
- 2021-02-04 JP JP2022548039A patent/JP2023512821A/ja active Pending
- 2021-02-04 CA CA3166940A patent/CA3166940A1/en active Pending
- 2021-02-04 KR KR1020227030622A patent/KR20220137085A/ko unknown
- 2021-02-04 MX MX2022009528A patent/MX2022009528A/es unknown
- 2021-02-04 CN CN202180026721.8A patent/CN115380028A/zh active Pending
- 2021-07-28 US US17/387,864 patent/US11453689B2/en active Active
-
2022
- 2022-08-02 US US17/879,320 patent/US12054504B2/en active Active
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