JP2011529477A5 - - Google Patents
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- Publication number
- JP2011529477A5 JP2011529477A5 JP2011520509A JP2011520509A JP2011529477A5 JP 2011529477 A5 JP2011529477 A5 JP 2011529477A5 JP 2011520509 A JP2011520509 A JP 2011520509A JP 2011520509 A JP2011520509 A JP 2011520509A JP 2011529477 A5 JP2011529477 A5 JP 2011529477A5
- Authority
- JP
- Japan
- Prior art keywords
- fluoro
- indacene
- aza
- oxa
- dihydro
- 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
- 150000001875 compounds Chemical class 0.000 claims 14
- 125000000217 alkyl group Chemical group 0.000 claims 9
- 125000000753 cycloalkyl group Chemical group 0.000 claims 7
- 229910052739 hydrogen Inorganic materials 0.000 claims 6
- 239000001257 hydrogen Substances 0.000 claims 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 3
- 150000002431 hydrogen Chemical class 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- 239000012453 solvate Substances 0.000 claims 3
- 208000024827 Alzheimer disease Diseases 0.000 claims 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 2
- YJPIGAIKUZMOQA-UHFFFAOYSA-N Melatonin Natural products COC1=CC=C2N(C(C)=O)C=C(CCN)C2=C1 YJPIGAIKUZMOQA-UHFFFAOYSA-N 0.000 claims 2
- 208000013738 Sleep Initiation and Maintenance disease Diseases 0.000 claims 2
- 229910052801 chlorine Inorganic materials 0.000 claims 2
- 239000000460 chlorine Substances 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 230000004064 dysfunction Effects 0.000 claims 2
- 229910052731 fluorine Inorganic materials 0.000 claims 2
- 239000011737 fluorine Substances 0.000 claims 2
- 206010022437 insomnia Diseases 0.000 claims 2
- DRLFMBDRBRZALE-UHFFFAOYSA-N melatonin Chemical compound COC1=CC=C2NC=C(CCNC(C)=O)C2=C1 DRLFMBDRBRZALE-UHFFFAOYSA-N 0.000 claims 2
- 229960003987 melatonin Drugs 0.000 claims 2
- 230000001105 regulatory effect Effects 0.000 claims 2
- ZFIUBPQUDIACCN-UHFFFAOYSA-N 2,2,2-trifluoro-n-[2-(4-fluoro-2,6-dihydro-1h-furo[3,2-e]indol-8-yl)ethyl]acetamide Chemical compound C1=2CCOC=2C(F)=CC2=C1C(CCNC(=O)C(F)(F)F)=CN2 ZFIUBPQUDIACCN-UHFFFAOYSA-N 0.000 claims 1
- DMNDNXXVYMRGSK-UHFFFAOYSA-N 2,2,2-trifluoro-n-[2-(4-fluoro-2-methyl-2,6-dihydro-1h-furo[3,2-e]indol-8-yl)ethyl]acetamide Chemical compound O1C(C)CC2=C1C(F)=CC1=C2C(CCNC(=O)C(F)(F)F)=CN1 DMNDNXXVYMRGSK-UHFFFAOYSA-N 0.000 claims 1
- VWXOZJSJOFFAPK-UHFFFAOYSA-N 2,2,2-trifluoro-n-[2-(4-fluoro-2-methyl-2,6-dihydro-1h-furo[3,2-e]indol-8-yl)propyl]acetamide Chemical compound FC1=C2OC(C)CC2=C2C(C(CNC(=O)C(F)(F)F)C)=CNC2=C1 VWXOZJSJOFFAPK-UHFFFAOYSA-N 0.000 claims 1
- RHWRYDLLTJPJSW-UHFFFAOYSA-N 2-fluoro-n-[2-(4-fluoro-2-methyl-2,6-dihydro-1h-furo[3,2-e]indol-8-yl)ethyl]propanamide Chemical compound FC1=C2OC(C)CC2=C2C(CCNC(=O)C(F)C)=CNC2=C1 RHWRYDLLTJPJSW-UHFFFAOYSA-N 0.000 claims 1
- -1 4-fluoro-2-methyl-1,6-dihydro-2H-3-oxa-6-aza-as-indacene-8-yl Chemical group 0.000 claims 1
- 208000019901 Anxiety disease Diseases 0.000 claims 1
- 208000027559 Appetite disease Diseases 0.000 claims 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- 208000019888 Circadian rhythm sleep disease Diseases 0.000 claims 1
- 208000019454 Feeding and Eating disease Diseases 0.000 claims 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
- 208000001456 Jet Lag Syndrome Diseases 0.000 claims 1
- 208000019695 Migraine disease Diseases 0.000 claims 1
- 208000008589 Obesity Diseases 0.000 claims 1
- 206010033664 Panic attack Diseases 0.000 claims 1
- 208000018737 Parkinson disease Diseases 0.000 claims 1
- 206010039966 Senile dementia Diseases 0.000 claims 1
- 150000001263 acyl chlorides Chemical class 0.000 claims 1
- 230000032683 aging Effects 0.000 claims 1
- 230000036506 anxiety Effects 0.000 claims 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 230000002490 cerebral effect Effects 0.000 claims 1
- FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 claims 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 1
- 206010012601 diabetes mellitus Diseases 0.000 claims 1
- 208000024829 digestive system symptom Diseases 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 208000035475 disorder Diseases 0.000 claims 1
- 230000002526 effect on cardiovascular system Effects 0.000 claims 1
- 206010015037 epilepsy Diseases 0.000 claims 1
- 206010016256 fatigue Diseases 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 230000003301 hydrolyzing effect Effects 0.000 claims 1
- 239000012948 isocyanate Substances 0.000 claims 1
- 150000002513 isocyanates Chemical class 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 208000033915 jet lag type circadian rhythm sleep disease Diseases 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 206010027599 migraine Diseases 0.000 claims 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 1
- DQJLXFAMNCWBCP-UHFFFAOYSA-N n-[2-(4-fluoro-2,6-dihydro-1h-furo[3,2-e]indol-8-yl)ethyl]-2-methylpropanamide Chemical compound FC1=C2OCCC2=C2C(CCNC(=O)C(C)C)=CNC2=C1 DQJLXFAMNCWBCP-UHFFFAOYSA-N 0.000 claims 1
- TYGDUZXIKLXZFD-UHFFFAOYSA-N n-[2-(4-fluoro-2,6-dihydro-1h-furo[3,2-e]indol-8-yl)ethyl]acetamide Chemical compound FC1=C2OCCC2=C2C(CCNC(=O)C)=CNC2=C1 TYGDUZXIKLXZFD-UHFFFAOYSA-N 0.000 claims 1
- VGRRAWQCYWLJHU-UHFFFAOYSA-N n-[2-(4-fluoro-2,6-dihydro-1h-furo[3,2-e]indol-8-yl)ethyl]butanamide Chemical compound FC1=C2OCCC2=C2C(CCNC(=O)CCC)=CNC2=C1 VGRRAWQCYWLJHU-UHFFFAOYSA-N 0.000 claims 1
- BWVDPRLISOGKNL-UHFFFAOYSA-N n-[2-(4-fluoro-2,6-dihydro-1h-furo[3,2-e]indol-8-yl)ethyl]cyclopropanecarboxamide Chemical compound C1=2C=3CCOC=3C(F)=CC=2NC=C1CCNC(=O)C1CC1 BWVDPRLISOGKNL-UHFFFAOYSA-N 0.000 claims 1
- BTPWZFQDKRPHAG-UHFFFAOYSA-N n-[2-(4-fluoro-2,6-dihydro-1h-furo[3,2-e]indol-8-yl)ethyl]propanamide Chemical compound FC1=C2OCCC2=C2C(CCNC(=O)CC)=CNC2=C1 BTPWZFQDKRPHAG-UHFFFAOYSA-N 0.000 claims 1
- AQEPHMMANBGGJK-UHFFFAOYSA-N n-[2-(4-fluoro-2-methyl-2,6-dihydro-1h-furo[3,2-e]indol-8-yl)ethyl]acetamide Chemical compound O1C(C)CC2=C1C(F)=CC1=C2C(CCNC(C)=O)=CN1 AQEPHMMANBGGJK-UHFFFAOYSA-N 0.000 claims 1
- JHCGRXOAGBNRGU-UHFFFAOYSA-N n-[2-(4-fluoro-2-methyl-2,6-dihydro-1h-furo[3,2-e]indol-8-yl)ethyl]butanamide Chemical compound FC1=C2OC(C)CC2=C2C(CCNC(=O)CCC)=CNC2=C1 JHCGRXOAGBNRGU-UHFFFAOYSA-N 0.000 claims 1
- AUHVFDIYRLDHNA-UHFFFAOYSA-N n-[2-(4-fluoro-2-methyl-2,6-dihydro-1h-furo[3,2-e]indol-8-yl)ethyl]cyclopropanecarboxamide Chemical compound O1C(C)CC(C2=3)=C1C(F)=CC=3NC=C2CCNC(=O)C1CC1 AUHVFDIYRLDHNA-UHFFFAOYSA-N 0.000 claims 1
- VMCLAVZYYYJZPE-UHFFFAOYSA-N n-[2-(4-fluoro-2-methyl-2,6-dihydro-1h-furo[3,2-e]indol-8-yl)ethyl]pentanamide Chemical compound FC1=C2OC(C)CC2=C2C(CCNC(=O)CCCC)=CNC2=C1 VMCLAVZYYYJZPE-UHFFFAOYSA-N 0.000 claims 1
- VORROLINQFTIKK-UHFFFAOYSA-N n-[2-(4-fluoro-2-methyl-2,6-dihydro-1h-furo[3,2-e]indol-8-yl)ethyl]propanamide Chemical compound FC1=C2OC(C)CC2=C2C(CCNC(=O)CC)=CNC2=C1 VORROLINQFTIKK-UHFFFAOYSA-N 0.000 claims 1
- JMMQOOATJCSHOX-UHFFFAOYSA-N n-[2-(4-fluoro-2-methyl-2,6-dihydro-1h-furo[3,2-e]indol-8-yl)propyl]acetamide Chemical compound FC1=C2OC(C)CC2=C2C(C(CNC(C)=O)C)=CNC2=C1 JMMQOOATJCSHOX-UHFFFAOYSA-N 0.000 claims 1
- KRPFEJXGEHWCPZ-UHFFFAOYSA-N n-[2-(4-fluoro-2-methyl-2,6-dihydro-1h-furo[3,2-e]indol-8-yl)propyl]cyclopropanecarboxamide Chemical compound C=1NC2=CC(F)=C3OC(C)CC3=C2C=1C(C)CNC(=O)C1CC1 KRPFEJXGEHWCPZ-UHFFFAOYSA-N 0.000 claims 1
- VGQAPYLJXLDUDH-UHFFFAOYSA-N n-[2-(4-fluoro-2-methyl-2,6-dihydro-1h-furo[3,2-e]indol-8-yl)propyl]propanamide Chemical compound FC1=C2OC(C)CC2=C2C(C(C)CNC(=O)CC)=CNC2=C1 VGQAPYLJXLDUDH-UHFFFAOYSA-N 0.000 claims 1
- 235000020824 obesity Nutrition 0.000 claims 1
- 208000019906 panic disease Diseases 0.000 claims 1
- 230000001575 pathological effect Effects 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 claims 1
- 229940080818 propionamide Drugs 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 208000020016 psychiatric disease Diseases 0.000 claims 1
- 201000000980 schizophrenia Diseases 0.000 claims 1
- 208000012672 seasonal affective disease Diseases 0.000 claims 1
- 208000019116 sleep disease Diseases 0.000 claims 1
- 208000020685 sleep-wake disease Diseases 0.000 claims 1
- 230000035882 stress Effects 0.000 claims 1
- 208000024891 symptom Diseases 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP08161485 | 2008-07-30 | ||
| EP08161485.1 | 2008-07-30 | ||
| PCT/EP2009/059829 WO2010012789A1 (en) | 2008-07-30 | 2009-07-29 | 1,6-dihydro-2h-3-oxa-6-aza-as-indacene compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2011529477A JP2011529477A (ja) | 2011-12-08 |
| JP2011529477A5 true JP2011529477A5 (enExample) | 2012-08-30 |
Family
ID=41138660
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011520509A Abandoned JP2011529477A (ja) | 2008-07-30 | 2009-07-29 | １，６−ジヒドロ−２ｈ−３−オキサ−６−アザ−ａｓ−インダセン化合物 |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US8227501B2 (enExample) |
| EP (1) | EP2350088A1 (enExample) |
| JP (1) | JP2011529477A (enExample) |
| KR (1) | KR20110041495A (enExample) |
| CN (1) | CN102112480A (enExample) |
| AR (1) | AR075262A1 (enExample) |
| AU (1) | AU2009275918A1 (enExample) |
| BR (1) | BRPI0916395A2 (enExample) |
| CA (1) | CA2731405A1 (enExample) |
| CL (1) | CL2011000184A1 (enExample) |
| MX (1) | MX2011001062A (enExample) |
| PE (1) | PE20110208A1 (enExample) |
| RU (1) | RU2011107443A (enExample) |
| TW (1) | TW201018695A (enExample) |
| UY (1) | UY32016A (enExample) |
| WO (1) | WO2010012789A1 (enExample) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102219725B (zh) * | 2010-04-16 | 2013-10-09 | 中国科学院上海药物研究所 | 苯并杂环类化合物及其制备方法和用途 |
| AR091699A1 (es) * | 2012-07-10 | 2015-02-25 | Astellas Pharma Inc | Derivado de indol carboxamida |
| CN104109143B (zh) * | 2013-04-22 | 2018-04-27 | 上海阳帆医药科技有限公司 | 一类褪黑激素(mt1-mt2)受体激动剂及其制备方法与用途 |
| CN104326916B (zh) * | 2014-10-10 | 2017-09-22 | 青岛农业大学 | 2‑氟‑4‑烯丙基‑6‑硝基苯酚与2‑氟‑4‑硝基‑6‑烯丙基苯酚的联合制备及用途 |
| MY203941A (en) * | 2016-06-17 | 2024-07-25 | Daewoong Pharmaceutical Co Ltd | Method for producing diphenylmethane derivative |
| EP4452937A4 (en) * | 2021-12-24 | 2025-12-03 | Psylo Pty Ltd | CONNECTIONS |
| KR20240044190A (ko) * | 2022-09-28 | 2024-04-04 | 주식회사 대웅제약 | 이나보글리플로진의 신규한 결정형 및 이의 제조방법 |
Family Cites Families (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3466215D1 (en) * | 1983-05-18 | 1987-10-22 | Univ Monash | The use of melatonin for the manufacture of a medicament |
| US4600723A (en) * | 1983-05-18 | 1986-07-15 | Monash University | Method for minimizing disturbances in circadian rhythms of bodily performance and function |
| WO1989001472A1 (en) | 1987-08-17 | 1989-02-23 | Nelson Research & Development Co. | Melatonin analogues |
| FR2680366B1 (fr) * | 1991-08-13 | 1995-01-20 | Adir | Nouveaux derives d'arylethylamines, leurs procedes de preparation et les compositions pharmaceutiques qui les contiennent. |
| GB9326192D0 (en) * | 1993-12-22 | 1994-02-23 | Glaxo Group Ltd | Chemical compounds |
| AU6241796A (en) * | 1995-06-27 | 1997-01-30 | Takeda Chemical Industries Ltd. | 4-acylamino(halogeno) alkyl-quinoline derivatives, their preparation and their use as melatonin agonists |
| US5732360A (en) | 1995-09-08 | 1998-03-24 | At & T Wireless Services And Atmel Corp | Mobile telecommunication device and method used for changing wireless communication between base stations of different kinds |
| US6034239A (en) * | 1996-03-08 | 2000-03-07 | Takeda Chemical Industries, Ltd. | Tricyclic compounds, their production and use |
| CN1900067A (zh) | 1996-03-08 | 2007-01-24 | 武田药品工业株式会社 | 三环化合物及其制备和用途 |
| FR2771739B1 (fr) * | 1997-11-28 | 2001-04-20 | Adir | Nouveaux composes naphtaleniques, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| FR2784375B1 (fr) * | 1998-10-12 | 2000-11-24 | Adir | Nouveaux derives cycliques a chaine cycloalkylenique, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| FR2793793B1 (fr) * | 1999-05-19 | 2004-02-27 | Adir | Nouveaux derives dimeriques substitues, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| AU6595100A (en) | 1999-08-20 | 2001-03-19 | Takeda Chemical Industries Ltd. | Percutaneous absorption agents |
| FR2799757B1 (fr) * | 1999-10-15 | 2001-12-14 | Adir | Nouveaux derives polycycliques azaindoliques, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| US6737431B2 (en) * | 2002-03-12 | 2004-05-18 | Bristol-Myers Squibb Company | Benzoxazole derivatives as novel melatonergic agents |
| EP1537113B9 (en) * | 2002-06-21 | 2010-05-26 | Suven Life Sciences Limited | Arylalkyl indoles having serotonin receptor affinity useful as therapeutic agents, process for their preparation and pharmaceutical compositions containing them |
| US6908931B2 (en) * | 2003-04-10 | 2005-06-21 | Bristol-Myers Squibb Company | Tetrahydroisoquinoline derivatives as melatonin MT2 antagonists |
| EP1701718A4 (en) | 2003-12-23 | 2009-06-24 | Abraxis Bioscience Llc | SUBSTITUTED MELATONIN DERIVATIVES, METHOD FOR THE PRODUCTION THEREOF AND METHOD OF ADMINISTRATION |
-
2009
- 2009-07-29 CA CA2731405A patent/CA2731405A1/en not_active Abandoned
- 2009-07-29 WO PCT/EP2009/059829 patent/WO2010012789A1/en not_active Ceased
- 2009-07-29 KR KR1020117002324A patent/KR20110041495A/ko not_active Withdrawn
- 2009-07-29 CN CN2009801300227A patent/CN102112480A/zh active Pending
- 2009-07-29 AU AU2009275918A patent/AU2009275918A1/en not_active Abandoned
- 2009-07-29 UY UY0001032016A patent/UY32016A/es unknown
- 2009-07-29 BR BRPI0916395A patent/BRPI0916395A2/pt not_active IP Right Cessation
- 2009-07-29 JP JP2011520509A patent/JP2011529477A/ja not_active Abandoned
- 2009-07-29 US US13/056,492 patent/US8227501B2/en not_active Expired - Fee Related
- 2009-07-29 PE PE2011000041A patent/PE20110208A1/es not_active Application Discontinuation
- 2009-07-29 AR ARP090102880A patent/AR075262A1/es unknown
- 2009-07-29 TW TW098125512A patent/TW201018695A/zh unknown
- 2009-07-29 MX MX2011001062A patent/MX2011001062A/es active IP Right Grant
- 2009-07-29 EP EP09781255A patent/EP2350088A1/en not_active Withdrawn
- 2009-07-29 RU RU2011107443/04A patent/RU2011107443A/ru not_active Application Discontinuation
-
2011
- 2011-01-28 CL CL2011000184A patent/CL2011000184A1/es unknown
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