CA2715282A1 - Indole compounds and methods of use thereof - Google Patents
Indole compounds and methods of use thereof Download PDFInfo
- Publication number
- CA2715282A1 CA2715282A1 CA2715282A CA2715282A CA2715282A1 CA 2715282 A1 CA2715282 A1 CA 2715282A1 CA 2715282 A CA2715282 A CA 2715282A CA 2715282 A CA2715282 A CA 2715282A CA 2715282 A1 CA2715282 A1 CA 2715282A1
- Authority
- CA
- Canada
- Prior art keywords
- alkyl
- compound
- amino
- subject
- substituents
- 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.)
- Abandoned
Links
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- 150000002475 indoles Chemical class 0.000 title abstract description 8
- 150000001875 compounds Chemical class 0.000 claims abstract description 669
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 26
- 125000000217 alkyl group Chemical group 0.000 claims description 579
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 433
- -1 cyano, hydroxy Chemical group 0.000 claims description 398
- 125000001424 substituent group Chemical group 0.000 claims description 377
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 366
- 229910052736 halogen Inorganic materials 0.000 claims description 245
- 125000003545 alkoxy group Chemical group 0.000 claims description 227
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 226
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- 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims description 211
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 196
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 195
- 235000019000 fluorine Nutrition 0.000 claims description 162
- 238000011282 treatment Methods 0.000 claims description 161
- 150000002367 halogens Chemical class 0.000 claims description 149
- 239000000203 mixture Substances 0.000 claims description 133
- 125000001153 fluoro group Chemical group F* 0.000 claims description 105
- 125000005843 halogen group Chemical group 0.000 claims description 97
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 78
- 229910052731 fluorine Inorganic materials 0.000 claims description 72
- 239000011737 fluorine Substances 0.000 claims description 72
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- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 6
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- BLGXFZZNTVWLAY-SCYLSFHTSA-N yohimbine Chemical compound C1=CC=C2C(CCN3C[C@@H]4CC[C@H](O)[C@@H]([C@H]4C[C@H]33)C(=O)OC)=C3NC2=C1 BLGXFZZNTVWLAY-SCYLSFHTSA-N 0.000 description 1
- 229960000317 yohimbine Drugs 0.000 description 1
- AADVZSXPNRLYLV-UHFFFAOYSA-N yohimbine carboxylic acid Natural products C1=CC=C2C(CCN3CC4CCC(C(C4CC33)C(O)=O)O)=C3NC2=C1 AADVZSXPNRLYLV-UHFFFAOYSA-N 0.000 description 1
- 239000002076 α-tocopherol Substances 0.000 description 1
- 235000004835 α-tocopherol Nutrition 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/10—Drugs for genital or sexual disorders; Contraceptives for impotence
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/08—Antiepileptics; Anticonvulsants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Diabetes (AREA)
- Psychiatry (AREA)
- Endocrinology (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Emergency Medicine (AREA)
- Child & Adolescent Psychology (AREA)
- Addiction (AREA)
- Hospice & Palliative Care (AREA)
- Pain & Pain Management (AREA)
- Dermatology (AREA)
- Gynecology & Obstetrics (AREA)
- Reproductive Health (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US2782508P | 2008-02-11 | 2008-02-11 | |
| US61/027,825 | 2008-02-11 | ||
| PCT/US2009/033822 WO2009102805A1 (en) | 2008-02-11 | 2009-02-11 | Indole compounds and methods of use thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2715282A1 true CA2715282A1 (en) | 2009-08-20 |
Family
ID=40445507
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2715282A Abandoned CA2715282A1 (en) | 2008-02-11 | 2009-02-11 | Indole compounds and methods of use thereof |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US20090318527A1 (https=) |
| EP (1) | EP2254865A1 (https=) |
| JP (1) | JP2011511810A (https=) |
| AU (1) | AU2009214724A1 (https=) |
| CA (1) | CA2715282A1 (https=) |
| WO (1) | WO2009102805A1 (https=) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20200030309A1 (en) * | 2016-09-29 | 2020-01-30 | The Regents Of The University Of California | Compounds for increasing neural plasticity |
| US12325710B2 (en) | 2019-02-27 | 2025-06-10 | The Regents Of The University Of California | Substituted 1,2,3,4,5,6-hexahydroazepino[4,5-b]indoles for treating brain disorders |
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7655691B2 (en) * | 2004-09-27 | 2010-02-02 | Sard Howard P | Indole compounds useful as serotonin selective agents |
| EP2459533A4 (en) * | 2009-07-30 | 2013-01-16 | Univ Singapore | SMALL MOLECULAR ISOPRENYLCYSTONE CARBOXYL METHYLTRANSFERASE HEMMER WITH POTENTIAL ANTIBODY EFFECT |
| EP2464227A4 (en) * | 2009-08-10 | 2013-02-20 | Galenea Corp | COMPOUNDS AND METHODS OF USE |
| WO2015066344A1 (en) | 2013-11-01 | 2015-05-07 | Arena Pharmaceuticals, Inc. | 5-ht2c receptor agonists and compositions and methods of use |
| 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 |
| US12459965B2 (en) | 2017-10-09 | 2025-11-04 | Compass Pathfinder Limited | Preparation of psilocybin, different polymorphic forms, intermediates, formulations and their use |
| WO2020072675A1 (en) | 2018-10-02 | 2020-04-09 | Northwestern University | Beta-carbolines as positive allosteric modulators of the human serotonin receptor 2c (5-ht2c) |
| CA3132731A1 (en) * | 2019-03-07 | 2020-09-10 | University Of Padova | Compositions and methods of use comprising substances with neural plasticity actions administered at non-psychedelic/psychotomimetic dosages and formulations |
| US12377112B2 (en) | 2019-04-17 | 2025-08-05 | Compass Pathfinder Limited | Methods of treating neurocognitive disorders, chronic pain and reducing inflammation |
| 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 |
| KR20220137081A (ko) * | 2020-02-04 | 2022-10-11 | 마인드셋 파마 인크. | Cns 장애의 치료를 위한 세로토닌성 사이키델릭 작용제로서의 실로신 유도체 |
| US12240813B2 (en) | 2020-05-19 | 2025-03-04 | Cybin Irl Limited | Deuterated tryptamine derivatives and methods of use |
| KR20230109765A (ko) | 2020-12-09 | 2023-07-20 | 캄테크, 인크. | 다이알킬 트립타민 및 이의 치료적 용도 |
| JP2024520485A (ja) * | 2021-05-26 | 2024-05-24 | ブライト マインズ バイオサイエンスィズ インコーポレイテッド | 複素環式化合物及びその調製方法 |
| WO2023115167A1 (en) * | 2021-12-24 | 2023-06-29 | Psylo Pty Ltd | Compounds |
| WO2023173196A1 (en) | 2022-03-18 | 2023-09-21 | Enveric Biosciences Canada Inc. | C4-carboxylic acid-substituted tryptamine derivatives and methods of using |
| CA3261749A1 (en) * | 2022-07-15 | 2024-01-18 | Caamtech, Inc. | TRYPTAMINE DERIVATIVES |
| IL318840A (en) * | 2022-08-11 | 2025-04-01 | Gilgamesh Pharmaceuticals Inc | Tryptamines and methods of treating mood disorders |
| WO2024052895A1 (en) | 2022-09-06 | 2024-03-14 | Hadasit Medical Research Services And Development Ltd | Combinations comprising psychedelics for the treatment of schizophrenia and other neuropsychiatric and neurologic disorders |
| WO2025000051A1 (en) | 2023-06-28 | 2025-01-02 | Psylo Pty Ltd | Pyrrolopyridine compounds for the treatment of mental illnesses |
| WO2025000053A1 (en) | 2023-06-28 | 2025-01-02 | Psylo Pty Ltd | Compounds |
| WO2025099725A1 (en) | 2023-11-09 | 2025-05-15 | Hadasit Medical Research Services And Development Ltd. | Conjugates and uses thereof |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK1859798T3 (en) * | 2001-03-29 | 2016-03-21 | Lilly Co Eli | N- (2-arylethyl) -BENZYLAMINER as antagonists of 5-HT6 receptor |
| US7655691B2 (en) * | 2004-09-27 | 2010-02-02 | Sard Howard P | Indole compounds useful as serotonin selective agents |
-
2009
- 2009-02-11 AU AU2009214724A patent/AU2009214724A1/en not_active Abandoned
- 2009-02-11 CA CA2715282A patent/CA2715282A1/en not_active Abandoned
- 2009-02-11 EP EP09710775A patent/EP2254865A1/en not_active Withdrawn
- 2009-02-11 JP JP2010546107A patent/JP2011511810A/ja not_active Withdrawn
- 2009-02-11 WO PCT/US2009/033822 patent/WO2009102805A1/en not_active Ceased
- 2009-02-11 US US12/369,659 patent/US20090318527A1/en not_active Abandoned
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20200030309A1 (en) * | 2016-09-29 | 2020-01-30 | The Regents Of The University Of California | Compounds for increasing neural plasticity |
| US12343337B2 (en) * | 2016-09-29 | 2025-07-01 | The Regents Of The University Of California | Compounds for increasing neural plasticity |
| US12325710B2 (en) | 2019-02-27 | 2025-06-10 | The Regents Of The University Of California | Substituted 1,2,3,4,5,6-hexahydroazepino[4,5-b]indoles for treating brain disorders |
Also Published As
| Publication number | Publication date |
|---|---|
| AU2009214724A1 (en) | 2009-08-20 |
| JP2011511810A (ja) | 2011-04-14 |
| EP2254865A1 (en) | 2010-12-01 |
| US20090318527A1 (en) | 2009-12-24 |
| WO2009102805A1 (en) | 2009-08-20 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |
Effective date: 20140211 |