JPWO2022183288A5 - - Google Patents
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- JPWO2022183288A5 JPWO2022183288A5 JP2023553664A JP2023553664A JPWO2022183288A5 JP WO2022183288 A5 JPWO2022183288 A5 JP WO2022183288A5 JP 2023553664 A JP2023553664 A JP 2023553664A JP 2023553664 A JP2023553664 A JP 2023553664A JP WO2022183288 A5 JPWO2022183288 A5 JP WO2022183288A5
- Authority
- JP
- Japan
- Prior art keywords
- deuterium
- atoms
- alkyl
- hydrogen
- optionally replaced
- 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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- 150000001875 compounds Chemical class 0.000 claims description 80
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 69
- 229910052805 deuterium Inorganic materials 0.000 claims description 69
- 229910052739 hydrogen Inorganic materials 0.000 claims description 66
- 239000001257 hydrogen Substances 0.000 claims description 55
- 150000002431 hydrogen Chemical class 0.000 claims description 48
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 34
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 32
- 125000000217 alkyl group Chemical group 0.000 claims description 29
- 125000004429 atom Chemical group 0.000 claims description 25
- 229910020008 S(O) Inorganic materials 0.000 claims description 24
- 125000000623 heterocyclic group Chemical group 0.000 claims description 24
- 229910005965 SO 2 Inorganic materials 0.000 claims description 22
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 19
- 125000000232 haloalkynyl group Chemical group 0.000 claims description 17
- 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
- 229910052717 sulfur Inorganic materials 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 15
- 125000001424 substituent group Chemical group 0.000 claims description 14
- 229910052799 carbon Inorganic materials 0.000 claims description 13
- 208000035475 disorder Diseases 0.000 claims description 13
- 229940002612 prodrug Drugs 0.000 claims description 12
- 239000000651 prodrug Substances 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 12
- 239000012453 solvate Substances 0.000 claims description 12
- 125000004431 deuterium atom Chemical group 0.000 claims description 11
- 125000005843 halogen group Chemical group 0.000 claims description 10
- 125000005842 heteroatom Chemical group 0.000 claims description 10
- 125000001153 fluoro group Chemical group F* 0.000 claims description 9
- 208000012902 Nervous system disease Diseases 0.000 claims description 7
- 210000003169 central nervous system Anatomy 0.000 claims description 6
- 201000010099 disease Diseases 0.000 claims description 6
- 229910052731 fluorine Inorganic materials 0.000 claims description 6
- 208000020016 psychiatric disease Diseases 0.000 claims description 6
- 208000025966 Neurological disease Diseases 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 125000001072 heteroaryl group Chemical group 0.000 claims description 3
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- 125000003709 fluoroalkyl group Chemical group 0.000 claims description 2
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 16
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 15
- 125000006643 (C2-C6) haloalkenyl group Chemical group 0.000 claims 14
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 10
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 7
- -1 C 2 -C 6 haloalkynyl Chemical group 0.000 claims 3
- 101710085469 CD2 homolog Chemical group 0.000 claims 3
- 108050005493 CD3 protein, epsilon/gamma/delta subunit Chemical group 0.000 claims 3
- 102100036364 Cadherin-2 Human genes 0.000 claims 3
- 101000714537 Homo sapiens Cadherin-2 Chemical group 0.000 claims 3
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 2
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 2
- JNCMHMUGTWEVOZ-UHFFFAOYSA-N F[CH]F Chemical group F[CH]F JNCMHMUGTWEVOZ-UHFFFAOYSA-N 0.000 claims 2
- 108010081348 HRT1 protein Hairy Chemical group 0.000 claims 2
- 102100021881 Hairy/enhancer-of-split related with YRPW motif protein 1 Human genes 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims 1
- 125000006644 (C2-C6) haloalkynyl group Chemical group 0.000 claims 1
- 101100495923 Schizosaccharomyces pombe (strain 972 / ATCC 24843) chr2 gene Chemical group 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 description 18
- 125000001188 haloalkyl group Chemical group 0.000 description 18
- 125000000304 alkynyl group Chemical group 0.000 description 17
- 125000000262 haloalkenyl group Chemical group 0.000 description 16
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 6
- 102000040125 5-hydroxytryptamine receptor family Human genes 0.000 description 4
- 108091032151 5-hydroxytryptamine receptor family Proteins 0.000 description 4
- 125000003341 7 membered heterocyclic group Chemical group 0.000 description 4
- 125000002947 alkylene group Chemical group 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 208000024827 Alzheimer disease Diseases 0.000 description 3
- 208000021384 Obsessive-Compulsive disease Diseases 0.000 description 3
- 230000004913 activation Effects 0.000 description 3
- 210000004027 cell Anatomy 0.000 description 3
- 208000015122 neurodegenerative disease Diseases 0.000 description 3
- 208000000103 Anorexia Nervosa Diseases 0.000 description 2
- 208000019901 Anxiety disease Diseases 0.000 description 2
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 description 2
- 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 description 2
- 206010006550 Bulimia nervosa Diseases 0.000 description 2
- 208000018737 Parkinson disease Diseases 0.000 description 2
- 208000028017 Psychotic disease Diseases 0.000 description 2
- 230000003213 activating effect Effects 0.000 description 2
- 208000015802 attention deficit-hyperactivity disease Diseases 0.000 description 2
- 231100000871 behavioral problem Toxicity 0.000 description 2
- 208000014679 binge eating disease Diseases 0.000 description 2
- 239000012472 biological sample Substances 0.000 description 2
- 208000010877 cognitive disease Diseases 0.000 description 2
- 125000000392 cycloalkenyl group Chemical group 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 230000004770 neurodegeneration Effects 0.000 description 2
- 208000028173 post-traumatic stress disease Diseases 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
- 102100036321 5-hydroxytryptamine receptor 2A Human genes 0.000 description 1
- 101710138091 5-hydroxytryptamine receptor 2A Proteins 0.000 description 1
- 208000009575 Angelman syndrome Diseases 0.000 description 1
- 208000014912 Central Nervous System Infections Diseases 0.000 description 1
- 208000028698 Cognitive impairment Diseases 0.000 description 1
- 208000011990 Corticobasal Degeneration Diseases 0.000 description 1
- 206010012239 Delusion Diseases 0.000 description 1
- 206010067889 Dementia with Lewy bodies Diseases 0.000 description 1
- 206010012335 Dependence Diseases 0.000 description 1
- 206010048768 Dermatosis Diseases 0.000 description 1
- 208000019749 Eye movement disease 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
- 208000001914 Fragile X 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
- 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
- 206010027603 Migraine headaches Diseases 0.000 description 1
- 208000019022 Mood disease Diseases 0.000 description 1
- 208000029726 Neurodevelopmental disease Diseases 0.000 description 1
- 206010057342 Onychophagia Diseases 0.000 description 1
- 208000027089 Parkinsonian disease Diseases 0.000 description 1
- 206010034010 Parkinsonism 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
- 206010039966 Senile dementia Diseases 0.000 description 1
- 208000023906 Sexual and Gender disease Diseases 0.000 description 1
- 208000010112 Spinocerebellar Degenerations 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
- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 description 1
- 230000036506 anxiety Effects 0.000 description 1
- 208000029560 autism spectrum disease Diseases 0.000 description 1
- 230000003542 behavioural effect Effects 0.000 description 1
- 208000015114 central nervous system disease Diseases 0.000 description 1
- 206010008129 cerebral palsy 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
- 208000018459 dissociative disease Diseases 0.000 description 1
- 206010013663 drug dependence Diseases 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
- 230000003834 intracellular effect Effects 0.000 description 1
- 208000012268 mitochondrial disease Diseases 0.000 description 1
- 201000006417 multiple sclerosis Diseases 0.000 description 1
- 210000000653 nervous system Anatomy 0.000 description 1
- 230000001123 neurodevelopmental effect Effects 0.000 description 1
- 208000028780 ocular motility 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
- 230000003938 response to stress Effects 0.000 description 1
- 230000002207 retinal effect Effects 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
- 208000011117 substance-related disease Diseases 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 208000011580 syndromic disease Diseases 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 |
|---|---|---|---|
| US202163155634P | 2021-03-02 | 2021-03-02 | |
| US63/155,634 | 2021-03-02 | ||
| PCT/CA2022/050296 WO2022183288A1 (en) | 2021-03-02 | 2022-03-02 | Indole derivatives as serotonergic agents useful for the treatment of disorders related thereto |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2024508922A JP2024508922A (ja) | 2024-02-28 |
| JP2024508922A5 JP2024508922A5 (https=) | 2025-03-04 |
| JPWO2022183288A5 true JPWO2022183288A5 (https=) | 2025-03-04 |
Family
ID=83153685
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2023553664A Pending JP2024508922A (ja) | 2021-03-02 | 2022-03-02 | セロトニン作動性薬に関係する障害の治療に有用なセロトニン作動性薬としてのインドール誘導体 |
| JP2023553660A Pending JP2024508545A (ja) | 2021-03-02 | 2022-03-02 | セロトニン作動性薬に関係する障害の治療に有用なセロトニン作動性薬としてのインドール誘導体 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2023553660A Pending JP2024508545A (ja) | 2021-03-02 | 2022-03-02 | セロトニン作動性薬に関係する障害の治療に有用なセロトニン作動性薬としてのインドール誘導体 |
Country Status (11)
| Country | Link |
|---|---|
| US (2) | US20240166630A1 (https=) |
| EP (2) | EP4301730A4 (https=) |
| JP (2) | JP2024508922A (https=) |
| KR (2) | KR20230154220A (https=) |
| CN (2) | CN117500788A (https=) |
| AU (2) | AU2022229037A1 (https=) |
| BR (1) | BR112023017754A2 (https=) |
| CA (2) | CA3210275A1 (https=) |
| IL (2) | IL305622A (https=) |
| MX (2) | MX2023010316A (https=) |
| WO (2) | WO2022183287A1 (https=) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20240096817A (ko) | 2020-05-19 | 2024-06-26 | 사이빈 아이알엘 리미티드 | 중수소화된 트립타민 유도체 및 사용 방법 |
| KR20250053871A (ko) * | 2022-08-31 | 2025-04-22 | 사이빈 아이알엘 리미티드 | 트립타민 화합물, 조성물, 및 사용 방법 |
| US12396981B2 (en) | 2023-03-09 | 2025-08-26 | William Shulman | Methods of using DMT |
| CN121752545A (zh) * | 2023-11-06 | 2026-03-27 | 宜昌人福药业有限责任公司 | 一种n,n-二甲基色胺衍生物及其药物组合物、制备方法和用途 |
| WO2025104490A1 (en) * | 2023-11-14 | 2025-05-22 | Mindset Pharma Inc. | Indole derivatives as serotonergic agents useful for the treatment of disorders related thereto |
| WO2025104491A1 (en) * | 2023-11-14 | 2025-05-22 | Mindset Pharma Inc. | Indole derivatives as serotonergic agents useful for the treatment of disorders related thereto |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5578612A (en) * | 1990-10-15 | 1996-11-26 | Pfizer Inc. | Indole derivatives |
| PL170330B1 (pl) * | 1990-10-15 | 1996-11-29 | Pfizer | Sposób wytwarzania nowych pochodnych indolu PL PL PL PL PL PL |
| DE60222396T2 (de) * | 2001-03-29 | 2008-05-15 | Eli Lilly And Co., Indianapolis | N-(2-arylethyl) benzylamine als 5-ht6 rezeptor-antagoniste |
| TWI318621B (en) * | 2006-08-03 | 2009-12-21 | Nat Bureau Of Controlled Drugs Dept Of Health | A series of deuterium labelled compounds as drug testing standards and their preparations |
| US20090062367A1 (en) * | 2007-08-29 | 2009-03-05 | Protia, Llc | Deuterium-enriched eletriptan |
| EP2753605B1 (en) * | 2011-09-09 | 2019-03-27 | Lantheus Medical Imaging, Inc. | Compositions, methods, and systems for the synthesis and use of imaging agents |
| US20190358238A1 (en) * | 2016-11-16 | 2019-11-28 | University Of South Florida | ALLOSTERIC ANTAGONISTS OF GPRC6a AND THEIR USE IN MITIGATING PROTEINOPATHIES |
| EP4219498A1 (en) * | 2019-03-07 | 2023-08-02 | Arbormentis LLC | Compositions and methods of use comprising substances with neural plasticity actions administered at non-psychedelic / psychotomimetic dosages and formulations |
| GB201907871D0 (en) * | 2019-06-03 | 2019-07-17 | Small Pharma Ltd | Therapeutic compositions |
| PH12022551981A1 (en) * | 2020-02-04 | 2023-10-16 | Mindset Pharma Inc | Psilocin derivatives as serotonergic psychedelic agents for the treatment of cns disorders |
| 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. |
| TW202144369A (zh) * | 2020-04-26 | 2021-12-01 | 大陸商江蘇恆瑞醫藥股份有限公司 | 海鞘素類衍生物及其製備方法與醫藥用途 |
| WO2021234608A1 (en) * | 2020-05-19 | 2021-11-25 | Cybin Irl Limited | Deuterated tryptamine derivatives and methods of use |
| KR20240096817A (ko) * | 2020-05-19 | 2024-06-26 | 사이빈 아이알엘 리미티드 | 중수소화된 트립타민 유도체 및 사용 방법 |
-
2022
- 2022-03-02 AU AU2022229037A patent/AU2022229037A1/en active Pending
- 2022-03-02 IL IL305622A patent/IL305622A/en unknown
- 2022-03-02 CA CA3210275A patent/CA3210275A1/en active Pending
- 2022-03-02 EP EP22762289.1A patent/EP4301730A4/en active Pending
- 2022-03-02 JP JP2023553664A patent/JP2024508922A/ja active Pending
- 2022-03-02 KR KR1020237033368A patent/KR20230154220A/ko active Pending
- 2022-03-02 MX MX2023010316A patent/MX2023010316A/es unknown
- 2022-03-02 WO PCT/CA2022/050295 patent/WO2022183287A1/en not_active Ceased
- 2022-03-02 JP JP2023553660A patent/JP2024508545A/ja active Pending
- 2022-03-02 WO PCT/CA2022/050296 patent/WO2022183288A1/en not_active Ceased
- 2022-03-02 CN CN202280032370.6A patent/CN117500788A/zh active Pending
- 2022-03-02 AU AU2022229695A patent/AU2022229695A1/en active Pending
- 2022-03-02 US US18/279,293 patent/US20240166630A1/en active Pending
- 2022-03-02 KR KR1020237033351A patent/KR20230154219A/ko active Pending
- 2022-03-02 MX MX2023010317A patent/MX2023010317A/es unknown
- 2022-03-02 IL IL305481A patent/IL305481A/en unknown
- 2022-03-02 CN CN202280032373.XA patent/CN117242065A/zh active Pending
- 2022-03-02 CA CA3210270A patent/CA3210270A1/en active Pending
- 2022-03-02 BR BR112023017754A patent/BR112023017754A2/pt unknown
- 2022-03-02 US US18/279,290 patent/US20240166599A1/en active Pending
- 2022-03-02 EP EP22762290.9A patent/EP4301747A4/en active Pending
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