CZ20033314A3 - Použití Q@halogentryptaminových derivátů jako ligandů Q@HT@ a@nebo Q@HT@ receptorů pro serotonin - Google Patents
Použití Q@halogentryptaminových derivátů jako ligandů Q@HT@ a@nebo Q@HT@ receptorů pro serotonin Download PDFInfo
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- CZ20033314A3 CZ20033314A3 CZ20033314A CZ20033314A CZ20033314A3 CZ 20033314 A3 CZ20033314 A3 CZ 20033314A3 CZ 20033314 A CZ20033314 A CZ 20033314A CZ 20033314 A CZ20033314 A CZ 20033314A CZ 20033314 A3 CZ20033314 A3 CZ 20033314A3
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Classifications
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- C—CHEMISTRY; METALLURGY
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- 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
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- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
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- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
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- A61K31/405—Indole-alkanecarboxylic acids; Derivatives thereof, e.g. tryptophan, indomethacin
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Landscapes
- Health & Medical Sciences (AREA)
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- Anesthesiology (AREA)
- Hospice & Palliative Care (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Indole Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT2001RM000356A ITRM20010356A1 (it) | 2001-06-21 | 2001-06-21 | "5-alogeno derivati della triptamina utili come ligandi del recettore5-ht6 e/o 5-ht7 della serotonina. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CZ20033314A3 true CZ20033314A3 (cs) | 2004-08-18 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CZ20033314A CZ20033314A3 (cs) | 2001-06-21 | 2002-06-17 | Použití Q@halogentryptaminových derivátů jako ligandů Q@HT@ a@nebo Q@HT@ receptorů pro serotonin |
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| EP (1) | EP1404317B1 (enExample) |
| JP (2) | JP4683839B2 (enExample) |
| KR (1) | KR100885308B1 (enExample) |
| CN (1) | CN100482223C (enExample) |
| AT (1) | ATE416767T1 (enExample) |
| AU (1) | AU2002317482B2 (enExample) |
| BR (1) | BR0210538A (enExample) |
| CA (1) | CA2455296C (enExample) |
| CY (1) | CY1108879T1 (enExample) |
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| DK (1) | DK1404317T3 (enExample) |
| ES (1) | ES2319107T3 (enExample) |
| HU (1) | HUP0400250A3 (enExample) |
| IT (1) | ITRM20010356A1 (enExample) |
| MX (1) | MXPA03011510A (enExample) |
| PL (1) | PL367618A1 (enExample) |
| PT (1) | PT1404317E (enExample) |
| SK (1) | SK287828B6 (enExample) |
| WO (1) | WO2003000252A1 (enExample) |
Families Citing this family (35)
| Publication number | Priority date | Publication date | Assignee | Title |
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| AR039127A1 (es) * | 2002-03-27 | 2005-02-09 | Glaxo Group Ltd | Compuesto de quinolina, procedimiento para su preparacion, composicion farmaceutica que lo comprende y uso del mismo para la fabricacion de un medicamento |
| NZ544331A (en) | 2003-07-22 | 2010-03-26 | Arena Pharm Inc | Diaryl and arylheteroaryl urea derivatives as modulators of the 5-HT2A serotonin receptor useful for the prophylaxis and treatment of disorders related thereto |
| US8086315B2 (en) | 2004-02-12 | 2011-12-27 | Asap Medical, Inc. | Cardiac stimulation apparatus and method for the control of hypertension |
| CA2557158A1 (en) * | 2004-02-20 | 2005-09-01 | Astellas Pharma Inc. | Prophylactic antimigraine agents |
| US20080171788A1 (en) * | 2005-02-08 | 2008-07-17 | Shinobu Akuzawa | Medicament For Irritable Bowel Syndrome |
| EP1923387B1 (en) | 2005-08-08 | 2011-10-19 | Astellas Pharma Inc. | Acylguanidine derivative or salt thereof |
| WO2007046112A1 (en) * | 2005-10-19 | 2007-04-26 | Suven Life Sciences Inc. | Arylthioether tryptamine derivatives as functional 5-ht6 ligands |
| WO2007097276A1 (ja) * | 2006-02-20 | 2007-08-30 | Astellas Pharma Inc. | ピロール誘導体またはその塩 |
| EP2120950B1 (en) * | 2007-03-21 | 2012-07-04 | Glaxo Group Limited | Use of quinoline derivatives in the treatment of pain |
| EP2209380A4 (en) * | 2007-10-09 | 2011-09-14 | Mark T Hamann | METHOD OF USE OF COMPOSITIONS WITH ANTIDEPRESSIVE EFFICACY, MOOD EFFICACY AND OTHER NEUROLOGICAL EFFECTIVENESS AND COMPOSITIONS THEREOF |
| EP2254564A1 (en) | 2007-12-12 | 2010-12-01 | Glaxo Group Limited | Combinations comprising 3-phenylsulfonyl-8-piperazinyl-1yl-quinoline |
| WO2009123714A2 (en) | 2008-04-02 | 2009-10-08 | Arena Pharmaceuticals, Inc. | Processes for the preparation of pyrazole derivatives useful as modulators of the 5-ht2a serotonin receptor |
| US9126946B2 (en) | 2008-10-28 | 2015-09-08 | Arena Pharmaceuticals, Inc. | Processes useful for the preparation of 1-[3-(4-bromo-2-methyl-2H-pyrazol-3-yl)-4-methoxy-phenyl]-3-(2,4-difluoro-phenyl)urea and crystalline forms related thereto |
| CA2842455A1 (en) * | 2011-08-05 | 2013-02-14 | Sucampo Ag | Method for treating schizophrenia |
| CN102816103B (zh) * | 2012-08-20 | 2014-05-07 | 冉瑞琼 | 硫化天冬氨酸修饰的退黑素衍生物及其应用 |
| US9008769B2 (en) | 2012-12-21 | 2015-04-14 | Backbeat Medical, Inc. | Methods and systems for lowering blood pressure through reduction of ventricle filling |
| US9370662B2 (en) | 2013-12-19 | 2016-06-21 | Backbeat Medical, Inc. | Methods and systems for controlling blood pressure by controlling atrial pressure |
| CN104529865B (zh) * | 2014-12-12 | 2017-02-01 | 广东东阳光药业有限公司 | 苄胺类衍生物及其在药物上的应用 |
| JP2018516992A (ja) | 2015-06-12 | 2018-06-28 | アクソファント サイエンシーズ ゲーエムベーハーＡｘｏｖａｎｔ Ｓｃｉｅｎｃｅｓ Ｇｍｂｈ | レム睡眠行動障害の予防および処置のために有用なジアリールおよびアリールヘテロアリール尿素誘導体 |
| CN108472285A (zh) | 2015-07-15 | 2018-08-31 | 阿速万科学有限责任公司 | 用于预防和治疗与神经退行性疾病相关联的幻觉的二芳基和芳基杂芳基脲衍生物 |
| US10342982B2 (en) | 2015-09-11 | 2019-07-09 | Backbeat Medical, Inc. | Methods and systems for treating cardiac malfunction |
| US10485658B2 (en) | 2016-04-22 | 2019-11-26 | Backbeat Medical, Inc. | Methods and systems for controlling blood pressure |
| CN108926565A (zh) * | 2017-05-26 | 2018-12-04 | 中国科学院上海生命科学研究院 | 五羟色胺受体亚型6小分子激活剂及拮抗剂在防治阿尔茨海默症中的应用 |
| EP3813810A4 (en) * | 2018-06-21 | 2022-03-30 | Robert John Petcavich | METHODS OF INDUCING DENDRITICAL AND SYNAPTIC GENESIS IN CHRONIC NEURODEGENERATIVE DISEASES |
| GB201907871D0 (en) * | 2019-06-03 | 2019-07-17 | Small Pharma Ltd | Therapeutic compositions |
| LT4084791T (lt) * | 2020-02-18 | 2025-02-25 | Gilgamesh Pharmaceuticals, Inc. | Specifiniai triptaminai, skirti nuotaikos sutrikimams gydyti |
| IL297861A (en) | 2020-05-08 | 2023-01-01 | Psilera Inc | Novel compositions of matter and pharmaceutical compositions |
| IL312785B2 (en) | 2020-05-19 | 2026-06-01 | Cybin Irl Ltd | Deuterated tryptamine derivatives and methods of use |
| WO2021116503A2 (en) * | 2020-06-02 | 2021-06-17 | Small Pharma Ltd | Deuterated compounds |
| WO2022061196A1 (en) * | 2020-09-18 | 2022-03-24 | Mydecine Innovations Group Inc. | Novel formulations of psilocybin and psilocin compounds as serotonin agonists in combination with 3,4 methylenedioxymethamphetamine (mdma) |
| KR20240013170A (ko) | 2021-05-25 | 2024-01-30 | 아타이 테라퓨틱스, 인크. | 신규 n,n-디메틸트립타민 염 및 결정질 염 형태 |
| IL309210A (en) | 2021-06-09 | 2024-02-01 | Atai Therapeutics Inc | Parent drugs and conjugates of dimethyltryptamine |
| US20240343692A1 (en) * | 2021-08-09 | 2024-10-17 | University Of Pittsburgh - Of The Commonwealth System Of Higher Education | Selective psychedelic compounds |
| CA3238440A1 (en) * | 2021-12-30 | 2023-07-06 | Atai Therapeutics, Inc. | Dimethyltryptamine analogues as nitric oxide delivery drugs |
| CN114573578B (zh) * | 2022-02-16 | 2023-11-17 | 烟台宁远药业有限公司 | 一种烷基取代氮杂吲哚的制备方法 |
Family Cites Families (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2825734A (en) * | 1955-04-11 | 1958-03-04 | Upjohn Co | Reduction of carbonylic radicals in indolyl-3 compounds |
| GB966562A (en) * | 1961-04-06 | 1964-08-12 | Parke Davis & Co | Amine compounds and means of producing the same |
| FR2315277A1 (fr) * | 1975-06-25 | 1977-01-21 | Anvar | Nouveaux derives pentacycliques, leur preparation et les compositions qui les contiennent |
| US4428877A (en) * | 1978-07-12 | 1984-01-31 | Richter Gedeon Vegyeszeti Gyar Rt. | Cis-10-bromo-E-homoeburnanes |
| GB8531612D0 (en) * | 1985-12-23 | 1986-02-05 | Beecham Wuelfing Gmbh & Co Kg | Compounds |
| US5300645A (en) * | 1993-04-14 | 1994-04-05 | Eli Lilly And Company | Tetrahydro-pyrido-indole |
| FR2712591B1 (fr) * | 1993-11-19 | 1996-02-09 | Pf Medicament | Nouvelles arylpipérazines dérivées d'indole, leur préparation et leur utilisation thérapeutique. |
| US5688807A (en) * | 1994-03-11 | 1997-11-18 | Eli Lilly And Company | Method for treating 5HT2B receptor related conditions |
| US5504101A (en) * | 1994-05-06 | 1996-04-02 | Allelix Biopharmaceuticals, Inc. | 5-HT-1D receptor ligands |
| WO1998000400A1 (en) * | 1996-06-28 | 1998-01-08 | Meiji Seika Kaisha, Ltd. | Tetrahydrobenzindole compounds |
| US6100291A (en) * | 1998-03-16 | 2000-08-08 | Allelix Biopharmaceuticals Inc. | Pyrrolidine-indole compounds having 5-HT6 affinity |
| US6251893B1 (en) * | 1998-06-15 | 2001-06-26 | Nps Allelix Corp. | Bicyclic piperidine and piperazine compounds having 5-HT6 receptor affinity |
| AU767009B2 (en) * | 1998-12-11 | 2003-10-30 | Virginia Commonwealth University | Selective 5-HT6 receptor ligands |
| US6403808B1 (en) * | 1999-12-10 | 2002-06-11 | Virginia Commonwealth University | Selective 5-HT6 receptor ligands |
| EP1173432B9 (en) * | 1999-04-21 | 2008-10-15 | NPS Allelix Corp. | Piperidine-indole compounds having 5-ht6 affinity |
| AU779832B2 (en) | 1999-08-12 | 2005-02-10 | Nps Pharmaceuticals, Inc. | Azaindoles having serotonin receptor affinity |
| WO2004041781A1 (en) * | 2002-11-07 | 2004-05-21 | Suven Life Sciences Limited | Preparation of 3-aminoalkyl-substituted indole derivatives from phenylhydrazines and aminoketones |
-
2001
- 2001-06-21 IT IT2001RM000356A patent/ITRM20010356A1/it unknown
-
2002
- 2002-06-17 PL PL02367618A patent/PL367618A1/xx not_active IP Right Cessation
- 2002-06-17 CZ CZ20033314A patent/CZ20033314A3/cs unknown
- 2002-06-17 CN CNB02814337XA patent/CN100482223C/zh not_active Expired - Fee Related
- 2002-06-17 AU AU2002317482A patent/AU2002317482B2/en not_active Ceased
- 2002-06-17 MX MXPA03011510A patent/MXPA03011510A/es active IP Right Grant
- 2002-06-17 EP EP02745793A patent/EP1404317B1/en not_active Expired - Lifetime
- 2002-06-17 AT AT02745793T patent/ATE416767T1/de active
- 2002-06-17 SK SK38-2004A patent/SK287828B6/sk not_active IP Right Cessation
- 2002-06-17 KR KR1020037016564A patent/KR100885308B1/ko not_active Expired - Fee Related
- 2002-06-17 PT PT02745793T patent/PT1404317E/pt unknown
- 2002-06-17 DE DE60230270T patent/DE60230270D1/de not_active Expired - Lifetime
- 2002-06-17 ES ES02745793T patent/ES2319107T3/es not_active Expired - Lifetime
- 2002-06-17 US US10/481,433 patent/US7098233B2/en not_active Expired - Fee Related
- 2002-06-17 DK DK02745793T patent/DK1404317T3/da active
- 2002-06-17 CA CA2455296A patent/CA2455296C/en not_active Expired - Fee Related
- 2002-06-17 JP JP2003506898A patent/JP4683839B2/ja not_active Expired - Fee Related
- 2002-06-17 BR BR0210538-1A patent/BR0210538A/pt not_active Application Discontinuation
- 2002-06-17 HU HU0400250A patent/HUP0400250A3/hu unknown
- 2002-06-17 WO PCT/IT2002/000398 patent/WO2003000252A1/en not_active Ceased
-
2009
- 2009-03-06 CY CY20091100260T patent/CY1108879T1/el unknown
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2010
- 2010-09-13 JP JP2010204733A patent/JP2011016835A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| DE60230270D1 (de) | 2009-01-22 |
| PT1404317E (pt) | 2009-02-23 |
| BR0210538A (pt) | 2004-06-22 |
| CY1108879T1 (el) | 2014-07-02 |
| KR100885308B1 (ko) | 2009-02-24 |
| AU2002317482B2 (en) | 2007-08-16 |
| ITRM20010356A1 (it) | 2002-12-23 |
| ES2319107T3 (es) | 2009-05-04 |
| DK1404317T3 (da) | 2009-02-23 |
| HUP0400250A2 (hu) | 2004-08-30 |
| JP2011016835A (ja) | 2011-01-27 |
| CA2455296C (en) | 2010-08-17 |
| WO2003000252A1 (en) | 2003-01-03 |
| JP4683839B2 (ja) | 2011-05-18 |
| MXPA03011510A (es) | 2004-03-18 |
| HK1068792A1 (zh) | 2005-05-06 |
| JP2004534816A (ja) | 2004-11-18 |
| ITRM20010356A0 (it) | 2001-06-21 |
| SK382004A3 (en) | 2004-05-04 |
| CA2455296A1 (en) | 2003-01-03 |
| SK287828B6 (sk) | 2011-11-04 |
| PL367618A1 (en) | 2005-03-07 |
| US7098233B2 (en) | 2006-08-29 |
| EP1404317A1 (en) | 2004-04-07 |
| KR20040032113A (ko) | 2004-04-14 |
| US20040235899A1 (en) | 2004-11-25 |
| CN1535146A (zh) | 2004-10-06 |
| ATE416767T1 (de) | 2008-12-15 |
| EP1404317B1 (en) | 2008-12-10 |
| CN100482223C (zh) | 2009-04-29 |
| HUP0400250A3 (en) | 2008-03-28 |
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