AU2009308708B2 - Azepino [4, 5-b] indoles and methods of use - Google Patents
Azepino [4, 5-b] indoles and methods of use Download PDFInfo
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- AU2009308708B2 AU2009308708B2 AU2009308708A AU2009308708A AU2009308708B2 AU 2009308708 B2 AU2009308708 B2 AU 2009308708B2 AU 2009308708 A AU2009308708 A AU 2009308708A AU 2009308708 A AU2009308708 A AU 2009308708A AU 2009308708 B2 AU2009308708 B2 AU 2009308708B2
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- Prior art keywords
- substituted
- unsubstituted
- alkyl
- taken together
- independently
- Prior art date
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Links
- 238000000034 method Methods 0.000 title claims description 25
- ZMKPMNLSLLYATH-UHFFFAOYSA-N azepino[4,5-b]indole Chemical class C1=CN=CC=C2C3=CC=CC=C3N=C21 ZMKPMNLSLLYATH-UHFFFAOYSA-N 0.000 title abstract description 24
- 150000001875 compounds Chemical class 0.000 claims abstract description 426
- 102000000543 Histamine Receptors Human genes 0.000 claims abstract description 35
- 108010002059 Histamine Receptors Proteins 0.000 claims abstract description 35
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 435
- -1 perhaloalkyl Chemical group 0.000 claims description 414
- 125000000217 alkyl group Chemical group 0.000 claims description 342
- 125000005843 halogen group Chemical group 0.000 claims description 277
- 125000003118 aryl group Chemical group 0.000 claims description 227
- 125000000623 heterocyclic group Chemical group 0.000 claims description 200
- 125000001072 heteroaryl group Chemical group 0.000 claims description 179
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 170
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 165
- 125000005102 carbonylalkoxy group Chemical group 0.000 claims description 163
- 229910052799 carbon Inorganic materials 0.000 claims description 161
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 157
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 150
- 125000003545 alkoxy group Chemical group 0.000 claims description 141
- 125000004442 acylamino group Chemical group 0.000 claims description 134
- 150000003839 salts Chemical class 0.000 claims description 123
- 125000000266 alpha-aminoacyl group Chemical group 0.000 claims description 121
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 119
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 115
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 112
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- 125000003342 alkenyl group Chemical group 0.000 claims description 99
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 96
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- 125000003710 aryl alkyl group Chemical group 0.000 claims description 81
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- 208000024891 symptom Diseases 0.000 claims description 57
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- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 52
- 125000004076 pyridyl group Chemical group 0.000 claims description 50
- 229910052739 hydrogen Inorganic materials 0.000 claims description 48
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 27
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 24
- 230000019771 cognition Effects 0.000 claims description 22
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- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 20
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- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 17
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 16
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 16
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- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 14
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 14
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 claims description 13
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- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 6
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- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 claims description 6
- WGCNASOHLSPBMP-UHFFFAOYSA-N Glycolaldehyde Chemical compound OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 6
- 125000006367 bivalent amino carbonyl group Chemical group [H]N([*:1])C([*:2])=O 0.000 claims description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 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
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- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 claims description 2
- 230000000561 anti-psychotic effect Effects 0.000 claims description 2
- IFLVGRRVGPXYON-UHFFFAOYSA-N adci Chemical compound C12=CC=CC=C2C2(C(=O)N)C3=CC=CC=C3CC1N2 IFLVGRRVGPXYON-UHFFFAOYSA-N 0.000 claims 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims 1
- KVMHGXYFIRJLAX-UHFFFAOYSA-N methyl(methylidyne)azanium Chemical compound C[N+]#C KVMHGXYFIRJLAX-UHFFFAOYSA-N 0.000 claims 1
- 150000002475 indoles Chemical class 0.000 abstract description 2
- 229940075993 receptor modulator Drugs 0.000 description 48
- 201000010099 disease Diseases 0.000 description 45
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- GAOZYPMEPKXQBB-UHFFFAOYSA-N 2-(1h-azepino[4,5-b]indol-6-yl)acetamide Chemical compound C1=CN=CCC2=C1N(CC(=O)N)C1=CC=CC=C12 GAOZYPMEPKXQBB-UHFFFAOYSA-N 0.000 description 36
- 125000005121 aminocarbonylalkoxy group Chemical group 0.000 description 35
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 34
- 125000001309 chloro group Chemical group Cl* 0.000 description 33
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Classifications
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
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- 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
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- 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
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- 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
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- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
Landscapes
- Health & Medical Sciences (AREA)
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- Chemical Kinetics & Catalysis (AREA)
- Biomedical Technology (AREA)
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- Neurosurgery (AREA)
- Epidemiology (AREA)
- Psychiatry (AREA)
- Hospice & Palliative Care (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
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| RU2544856C2 (ru) | 2008-01-25 | 2015-03-20 | Сергей Олегович Бачурин | НОВЫЕ ПРОИЗВОДНЫЕ 2,3,4,5-ТЕТРАГИДРО-1-ПИРИДО[4,3-b]ИНДОЛА И СПОСОБЫ ИХ ПРИМЕНЕНИЯ |
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| US8546381B2 (en) | 2008-03-24 | 2013-10-01 | Medivation Technologies, Inc. | Bridged heterocyclic compounds and methods of use |
| EP2346332A4 (en) * | 2008-10-31 | 2012-08-08 | Medivation Technologies Inc | PYRIDOÝ4,3-BINDOLES CONTAINING RIGID FRAGMENTS |
| JP5551708B2 (ja) | 2008-10-31 | 2014-07-16 | メディベイション テクノロジーズ， インコーポレイテッド | アゼピノ［４，５−ｂ］インドール化合物およびその使用方法 |
| AU2009308687A1 (en) * | 2008-11-03 | 2010-05-06 | Chemocentryx, Inc. | Compounds for the treatment of osteoporosis and cancers |
| US8362277B2 (en) | 2009-01-09 | 2013-01-29 | Board Of Regents Of The University Of Texas System | Pro-neurogenic compounds |
| US9162980B2 (en) | 2009-01-09 | 2015-10-20 | Board Of Regents Of The University Of Texas System | Anti-depression compounds |
| US9962368B2 (en) | 2009-01-09 | 2018-05-08 | Board Of Regents Of The University Of Texas System | Pro-neurogenic compounds |
| CN107595841A (zh) | 2009-01-09 | 2018-01-19 | 得克萨斯州大学系统董事会 | 前神经原性化合物 |
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| EP2424364A4 (en) | 2009-04-29 | 2012-12-19 | Medivation Technologies Inc | PYRIDO [4.3-B] INDOLES AND METHODS OF USE |
| JP5827943B2 (ja) | 2009-04-29 | 2015-12-02 | メディベイション テクノロジーズ， インコーポレイテッド | ピリド［４，３−ｂ］インドールおよびその使用方法 |
| US20120172350A1 (en) * | 2009-09-11 | 2012-07-05 | Sunovion Pharmaceuticals Inc. | Histamine h3 inverse agonists and antagonists and methods of use thereof |
| WO2011038164A1 (en) | 2009-09-23 | 2011-03-31 | Medivation Technologies, Inc. | Bridged heterocyclic compounds and methods of use |
| JP5779183B2 (ja) | 2009-09-23 | 2015-09-16 | メディベイション テクノロジーズ， インコーポレイテッド | ピリド［４，３−ｂ］インドールおよび使用方法 |
| CA2775133A1 (en) | 2009-09-23 | 2011-03-31 | Medivation Technologies, Inc. | Pyrido[3,4-b]indoles and methods of use |
| WO2011103460A1 (en) | 2010-02-18 | 2011-08-25 | Medivation Technologies, Inc. | Fused tetracyclic pyrido[4,3-b]indole and pyrido[3,4-b]ondole derivatives and methods of use |
| WO2011103433A1 (en) | 2010-02-18 | 2011-08-25 | Medivation Technologies, Inc. | Pyrido[4,3-b]indole and pyrido[3,4-b]indole derivatives and methods of use |
| US9040519B2 (en) | 2010-02-18 | 2015-05-26 | Medivation Technologies, Inc. | Fused tetracyclic pyrido [4,3-B] indole and pyrido [3,4-B] indole derivatives and methods of use |
| US9187471B2 (en) | 2010-02-19 | 2015-11-17 | Medivation Technologies, Inc. | Pyrido [4,3-b] indole and pyrido [3,4-b] indole derivatives and methods of use |
| DK2590647T3 (en) | 2010-07-07 | 2018-02-12 | Univ Texas | Pro-neurogenic compounds |
| WO2012112962A1 (en) | 2011-02-18 | 2012-08-23 | Medivation Technologies, Inc. | Compounds and methods of treating diabetes |
| US9035056B2 (en) | 2011-02-18 | 2015-05-19 | Medivation Technologies, Inc. | Pyrido[4,3-b]indole and pyrido[3,4-b]indole derivatives and methods of use |
| US8815843B2 (en) | 2011-02-18 | 2014-08-26 | Medivation Technologies, Inc. | Compounds and methods of treating diabetes |
| WO2012112965A1 (en) * | 2011-02-18 | 2012-08-23 | Medivation Technologies, Inc. | Compounds and methods of treating diabetes |
| EP2887805A4 (en) * | 2012-08-22 | 2016-08-17 | Medivation Technologies Inc | COMPOUNDS AND METHOD FOR TREATING BLOOD HIGH PRESSURE |
| CA2882826A1 (en) | 2012-08-24 | 2014-02-27 | Board Of Regents Of The University Of Texas System | Pro-neurogenic compounds |
| EP2746257A1 (en) | 2012-12-21 | 2014-06-25 | Basf Se | Substituted [1,2,4]triazole and imidazole compounds |
| EP2746258A1 (en) | 2012-12-21 | 2014-06-25 | Basf Se | Substituted [1,2,4]triazole and imidazole compounds |
| WO2015070237A1 (en) | 2013-11-11 | 2015-05-14 | Board Of Regents Of The University Of Texas System | Neuroprotective chemicals and methods for identifying and using same |
| EP3068388A4 (en) | 2013-11-11 | 2017-04-12 | Board of Regents of the University of Texas System | Neuroprotective compounds and use thereof |
| CN105037298B (zh) * | 2015-07-08 | 2017-09-26 | 华南理工大学 | 一种含三氟甲基取代连续季碳中心环氧丙烷衍生物及合成方法 |
| EP3519816A4 (en) | 2016-09-29 | 2020-05-06 | The Regents of the University of California | Compounds for increasing neural plasticity |
| CA3129749A1 (en) * | 2019-02-13 | 2020-08-20 | Centre For Addiction And Mental Health | Compositions and methods relating to use of agonists of alpha5-containing gabaa receptors |
| AU2020229779B9 (en) | 2019-02-27 | 2025-09-18 | The Regents Of The University Of California | Azepino-indoles and other heterocycles for treating brain disorders |
| CN110526935A (zh) * | 2019-09-04 | 2019-12-03 | 天津理工大学 | 一种双硼氮杂菲及其衍生物的合成方法 |
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- 2009-10-30 CA CA2742322A patent/CA2742322A1/en not_active Abandoned
- 2009-10-30 US US12/610,152 patent/US8569287B2/en not_active Expired - Fee Related
- 2009-10-30 TW TW098137049A patent/TWI482773B/zh not_active IP Right Cessation
- 2009-10-30 AR ARP090104221A patent/AR073924A1/es unknown
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| CA2742322A1 (en) | 2010-05-06 |
| US9481676B2 (en) | 2016-11-01 |
| EP2348847A4 (en) | 2012-05-23 |
| US20130190295A1 (en) | 2013-07-25 |
| CN102316732A (zh) | 2012-01-11 |
| JP2012507567A (ja) | 2012-03-29 |
| AU2009308708A1 (en) | 2010-05-06 |
| BRPI0921798A2 (pt) | 2019-09-24 |
| HK1164641A1 (en) | 2012-09-28 |
| US9409910B2 (en) | 2016-08-09 |
| US20140213577A1 (en) | 2014-07-31 |
| CN102316732B (zh) | 2015-04-01 |
| WO2010051503A1 (en) | 2010-05-06 |
| AR073924A1 (es) | 2010-12-09 |
| TWI482773B (zh) | 2015-05-01 |
| US8569287B2 (en) | 2013-10-29 |
| EP2348847A1 (en) | 2011-08-03 |
| US20100152163A1 (en) | 2010-06-17 |
| US20140088087A1 (en) | 2014-03-27 |
| TW201022270A (en) | 2010-06-16 |
| JP5551708B2 (ja) | 2014-07-16 |
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