JP2004517070A5 - - Google Patents
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- Publication number
- JP2004517070A5 JP2004517070A5 JP2002543495A JP2002543495A JP2004517070A5 JP 2004517070 A5 JP2004517070 A5 JP 2004517070A5 JP 2002543495 A JP2002543495 A JP 2002543495A JP 2002543495 A JP2002543495 A JP 2002543495A JP 2004517070 A5 JP2004517070 A5 JP 2004517070A5
- Authority
- JP
- Japan
- Prior art keywords
- triazolo
- imidazo
- benzodiazepine
- ethyl
- carboxylate
- 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.)
- Granted
Links
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 40
- 150000001875 compounds Chemical class 0.000 claims description 28
- NZTCFMPWFGWRBN-UHFFFAOYSA-N 3H-[1,2,4]triazolo[4,3-d][1,4]benzodiazepine-10-carboxylic acid Chemical compound N1=NCN2C=CN=C3C(=C21)C=C(C=C3)C(=O)O NZTCFMPWFGWRBN-UHFFFAOYSA-N 0.000 claims description 23
- 125000000217 alkyl group Chemical group 0.000 claims description 19
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- 239000001257 hydrogen Substances 0.000 claims description 13
- 229910052736 halogen Inorganic materials 0.000 claims description 11
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- 150000002367 halogens Chemical class 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 125000001424 substituent group Chemical group 0.000 claims description 5
- SFPHNARDXIEZPB-UHFFFAOYSA-N C1=NNN2C=CN=C3C(=C21)C=C(C=C3)C(=O)O Chemical compound C1=NNN2C=CN=C3C(=C21)C=C(C=C3)C(=O)O SFPHNARDXIEZPB-UHFFFAOYSA-N 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 125000001766 1,2,4-oxadiazol-3-yl group Chemical group [H]C1=NC(*)=NO1 0.000 claims description 3
- 125000004505 1,2,4-oxadiazol-5-yl group Chemical group O1N=CN=C1* 0.000 claims description 3
- 125000004414 alkyl thio group Chemical group 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims description 3
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- -1 3-Cyclopropyl-1,2,4-oxadiazol-5-yl Chemical group 0.000 claims 18
- 239000003814 drug Substances 0.000 claims 6
- 150000002431 hydrogen Chemical class 0.000 claims 6
- GUJAGMICFDYKNR-UHFFFAOYSA-N 1,4-benzodiazepine Chemical compound N1C=CN=CC2=CC=CC=C12 GUJAGMICFDYKNR-UHFFFAOYSA-N 0.000 claims 5
- 238000000034 method Methods 0.000 claims 5
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 2
- 125000000980 1H-indol-3-ylmethyl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([H])=C(C([H])([H])[*])C2=C1[H] 0.000 claims 2
- 125000006497 3-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C(OC([H])([H])[H])=C1[H])C([H])([H])* 0.000 claims 2
- 208000024827 Alzheimer disease Diseases 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 125000001246 bromo group Chemical group Br* 0.000 claims 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims 2
- 208000010877 cognitive disease Diseases 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- FTNJQNQLEGKTGD-UHFFFAOYSA-N 1,3-benzodioxole Chemical compound C1=CC=C2OCOC2=C1 FTNJQNQLEGKTGD-UHFFFAOYSA-N 0.000 claims 1
- NKWDDGCMDWGDLU-UHFFFAOYSA-N 3H-[1,2,4]triazolo[4,3-d][1,4]benzodiazepine Chemical compound N1=NCN2C=CN=C3C(=C21)C=CC=C3 NKWDDGCMDWGDLU-UHFFFAOYSA-N 0.000 claims 1
- LRKWILPMCIMYSF-UHFFFAOYSA-N 3h-triazolo[1,5-d][1,4]benzodiazepine Chemical class C1=CN2NN=CC2=C2C=CC=CC2=N1 LRKWILPMCIMYSF-UHFFFAOYSA-N 0.000 claims 1
- 125000000173 4-trifluoromethoxy benzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC(F)(F)F)C([H])([H])* 0.000 claims 1
- 150000007513 acids Chemical class 0.000 claims 1
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 229960003692 gamma aminobutyric acid Drugs 0.000 claims 1
- BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 claims 1
- 125000006503 p-nitrobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1[N+]([O-])=O)C([H])([H])* 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- LZOISVDTQDUWEU-UHFFFAOYSA-N 2,4,8,10,11-pentazatetracyclo[11.4.0.02,6.08,12]heptadeca-1(17),4,6,9,11,13,15-heptaene Chemical class C=1N2C=NN=C2C2=CC=CC=C2N2CN=CC2=1 LZOISVDTQDUWEU-UHFFFAOYSA-N 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP00124332 | 2000-11-16 | ||
| PCT/EP2001/012887 WO2002040487A2 (en) | 2000-11-16 | 2001-11-08 | Benzodiazepine derivatives as gaba a receptor modulators |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2004517070A JP2004517070A (ja) | 2004-06-10 |
| JP2004517070A5 true JP2004517070A5 (enExample) | 2005-05-26 |
| JP4088151B2 JP4088151B2 (ja) | 2008-05-21 |
Family
ID=8170315
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2002543495A Expired - Fee Related JP4088151B2 (ja) | 2000-11-16 | 2001-11-08 | Ｇａｂａａ受容体モデュレーターとしてのベンゾジアゼピン誘導体 |
Country Status (40)
Families Citing this family (29)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6686352B2 (en) | 2001-05-18 | 2004-02-03 | Hoffmann-La Roche Inc. | Substituted imidazo [1,5-a] pyrimido [5,4-d] [1] benzazepine derivatives |
| US7626029B2 (en) * | 2003-06-19 | 2009-12-01 | Daiichi Pharmaceutical Co., Ltd. | Method of selectively introducing amino substituent |
| PT1691811E (pt) | 2003-12-11 | 2014-10-30 | Sunovion Pharmaceuticals Inc | Combinação de um sedativo e de um modulador de neurotransmissores e métodos para melhorar a qualidade do sono e tratamento da depressão |
| EP1784390A2 (en) | 2004-08-13 | 2007-05-16 | Amgen Inc. | Substituted benzofused heterocycles |
| ATE402707T1 (de) | 2004-10-12 | 2008-08-15 | Hoffmann La Roche | Imidazoä1,5aütriazoloä1,5dübenzodiazepin- derivative zur behandlung kognitiver störungen |
| NZ554439A (en) * | 2004-10-20 | 2009-09-25 | Hoffmann La Roche | Imidazo-benzodiazepine derivatives |
| RU2007114763A (ru) * | 2004-10-20 | 2008-11-27 | Ф.Хоффманн-Ля Рош Аг (Ch) | Галогенозамещенные производные бензодиазепинов |
| WO2006063708A1 (en) | 2004-12-14 | 2006-06-22 | F.Hoffmann-La Roche Ag | Tetracyclic imidazo-benzodiazepines as gaba receptors modulators |
| EP1924712B1 (en) * | 2005-08-03 | 2018-10-03 | The Johns Hopkins University | Methods for characterizing and treating cognitive impairment in aging and disease |
| US8510055B2 (en) | 2005-08-03 | 2013-08-13 | The Johns Hopkins University | Methods for characterizing and treating cognitive impairment in aging and disease |
| JP4885967B2 (ja) * | 2005-10-11 | 2012-02-29 | エフ．ホフマン−ラ ロシュ アーゲー | イミダゾベンゾジアゼピン誘導体 |
| EP2314289A1 (en) | 2005-10-31 | 2011-04-27 | Braincells, Inc. | Gaba receptor mediated modulation of neurogenesis |
| WO2009139916A1 (en) * | 2008-05-16 | 2009-11-19 | Synta Pharmaceuticals Corp. | Tricyclic triazole compounds that modulate hsp90 activity |
| PE20110590A1 (es) | 2008-11-18 | 2011-08-31 | Hoffmann La Roche | Alquilciclohexileteres de dihidrotetraazabenzoazulenos |
| BRPI0922303B1 (pt) * | 2008-11-28 | 2019-11-12 | Hoffmann La Roche | arilciclo-hexiléteres de di-hidrotetra-azabenzoazulenos, seu processo de preparação, composição farmacêutica que os compreende e uso |
| CU20090172A7 (es) | 2009-10-09 | 2011-10-05 | Ct De Investigación Y Desarrollo De Medicamentos | Sistemas tricíclicos y tetracíclicos con actividad sobre el sistema nervioso central y vascular |
| AU2011328993B2 (en) | 2010-11-15 | 2017-03-02 | Agenebio, Inc. | Pyridazine derivatives, compositions and methods for treating cognitive impairment |
| US20150374705A1 (en) | 2012-02-14 | 2015-12-31 | Shanghai Institues for Biological Sciences | Substances for treatment or relief of pain |
| CA2885148A1 (en) * | 2012-09-21 | 2014-03-27 | Uwm Research Foundation, Inc. | Novel gabaa agonists and methods of using to control airway hyperresponsiveness and inflammation in asthma |
| EP4032889B1 (en) * | 2013-12-20 | 2026-05-06 | Agenebio, Inc. | Benzodiazepine derivatives, compositions, and methods for treating cognitive impairment |
| EP3310785B1 (en) * | 2015-06-19 | 2024-11-20 | Agenebio, Inc. | Benzodiazepine derivatives, compositions, and methods for treating cognitive impairment |
| US10059718B2 (en) * | 2016-01-04 | 2018-08-28 | Tabomedex Biosciences, LLC | Fused quadracyclic compounds, compositions and uses thereof |
| US10973479B2 (en) | 2016-05-16 | 2021-04-13 | Canon Medical Systems Corporation | X-ray diagnosis apparatus, X-ray diagnosis apparatus controlling method, and X-ray diagnosis system |
| US20180170941A1 (en) * | 2016-12-19 | 2018-06-21 | Agenebio, Inc. | Benzodiazepine derivatives, compositions, and methods for treating cognitive impairment |
| KR102512548B1 (ko) | 2017-12-22 | 2023-03-22 | 삼성디스플레이 주식회사 | 유기 전계 발광 소자 및 유기 전계 발광 소자용 함질소 화합물 |
| AU2019288382B2 (en) * | 2018-06-19 | 2024-07-25 | Agenebio, Inc. | Benzodiazepine derivatives, compositions, and methods for treating cognitive impairment |
| KR102151969B1 (ko) * | 2019-12-11 | 2020-09-04 | 주식회사 지투비 | 투과도 가변창의 제조방법 및 그에 의해 제조된 투과도 가변창 |
| CN112979658B (zh) * | 2021-02-22 | 2022-05-31 | 南湖实验室 | 一种氟马西尼的制备方法 |
| EP4572852A1 (en) | 2022-08-19 | 2025-06-25 | Agenebio, Inc. | Benzazepine derivatives, compositions, and methods for treating cognitive impairment |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK174086D0 (da) | 1986-04-16 | 1986-04-16 | Ferrosan As | Nye benzodiazepinderivater samt fremgangsmaade til fremstilling af samme |
| TW201311B (enExample) | 1991-06-17 | 1993-03-01 | Hoffmann La Roche |
-
2001
- 2001-11-07 TW TW090127658A patent/TWI239333B/zh not_active IP Right Cessation
- 2001-11-08 DK DK01996541T patent/DK1337535T3/da active
- 2001-11-08 PL PL01362925A patent/PL362925A1/xx not_active Application Discontinuation
- 2001-11-08 SK SK723-2003A patent/SK7232003A3/sk unknown
- 2001-11-08 JP JP2002543495A patent/JP4088151B2/ja not_active Expired - Fee Related
- 2001-11-08 PT PT01996541T patent/PT1337535E/pt unknown
- 2001-11-08 AT AT01996541T patent/ATE268776T1/de not_active IP Right Cessation
- 2001-11-08 IL IL15581301A patent/IL155813A0/xx unknown
- 2001-11-08 MX MXPA03004251A patent/MXPA03004251A/es active IP Right Grant
- 2001-11-08 BR BR0115393-5A patent/BR0115393A/pt not_active IP Right Cessation
- 2001-11-08 KR KR10-2003-7006609A patent/KR100504300B1/ko not_active Expired - Fee Related
- 2001-11-08 TR TR2004/02073T patent/TR200402073T4/xx unknown
- 2001-11-08 YU YU35603A patent/YU35603A/sh unknown
- 2001-11-08 CN CNB018189415A patent/CN1191255C/zh not_active Expired - Fee Related
- 2001-11-08 NZ NZ525413A patent/NZ525413A/en unknown
- 2001-11-08 CZ CZ20031597A patent/CZ295256B6/cs not_active IP Right Cessation
- 2001-11-08 CA CA002427576A patent/CA2427576C/en not_active Expired - Fee Related
- 2001-11-08 SI SI200130125T patent/SI1337535T1/xx unknown
- 2001-11-08 ES ES01996541T patent/ES2220831T3/es not_active Expired - Lifetime
- 2001-11-08 AU AU1700702A patent/AU1700702A/xx active Pending
- 2001-11-08 US US10/007,883 patent/US6743789B2/en not_active Expired - Fee Related
- 2001-11-08 WO PCT/EP2001/012887 patent/WO2002040487A2/en not_active Ceased
- 2001-11-08 EP EP01996541A patent/EP1337535B1/en not_active Expired - Lifetime
- 2001-11-08 RU RU2003116895/04A patent/RU2278865C2/ru not_active IP Right Cessation
- 2001-11-08 DE DE60103776T patent/DE60103776T2/de not_active Expired - Lifetime
- 2001-11-08 HU HU0303281A patent/HUP0303281A3/hu unknown
- 2001-11-08 AU AU2002217007A patent/AU2002217007B2/en not_active Ceased
- 2001-11-08 HR HR20030360A patent/HRP20030360A2/hr not_active Application Discontinuation
- 2001-11-12 JO JO2001183A patent/JO2359B1/en active
- 2001-11-13 GC GCP20011724 patent/GC0000375A/en active
- 2001-11-14 PE PE2001001135A patent/PE20020583A1/es not_active Application Discontinuation
- 2001-11-15 GT GT200100230A patent/GT200100230A/es unknown
- 2001-11-15 PA PA20018532401A patent/PA8532401A1/es unknown
- 2001-11-15 AR ARP010105323A patent/AR031345A1/es not_active Application Discontinuation
- 2001-11-15 UY UY27026A patent/UY27026A1/es not_active Application Discontinuation
- 2001-11-15 MY MYPI20015253A patent/MY141675A/en unknown
-
2003
- 2003-05-05 ZA ZA200303435A patent/ZA200303435B/en unknown
- 2003-05-15 EC EC2003004607A patent/ECSP034607A/es unknown
- 2003-05-15 NO NO20032208A patent/NO324706B1/no unknown
- 2003-05-16 MA MA27163A patent/MA26962A1/fr unknown
- 2003-05-16 BG BG107817A patent/BG107817A/bg unknown
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