JP2010535751A5 - - Google Patents
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- Publication number
- JP2010535751A5 JP2010535751A5 JP2010519520A JP2010519520A JP2010535751A5 JP 2010535751 A5 JP2010535751 A5 JP 2010535751A5 JP 2010519520 A JP2010519520 A JP 2010519520A JP 2010519520 A JP2010519520 A JP 2010519520A JP 2010535751 A5 JP2010535751 A5 JP 2010535751A5
- Authority
- JP
- Japan
- Prior art keywords
- compound
- formula
- compound according
- methyl
- ethyl
- 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
- 150000001875 compounds Chemical class 0.000 claims 28
- 229910052739 hydrogen Inorganic materials 0.000 claims 6
- 239000001257 hydrogen Substances 0.000 claims 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 4
- 150000003839 salts Chemical class 0.000 claims 4
- 239000012453 solvate Substances 0.000 claims 4
- 125000003545 alkoxy group Chemical group 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- ZWLCYOWQGKARQR-UHFFFAOYSA-N 4-(cyclohexylmethyl)-5-[2-[4-(2-methoxyphenyl)piperazin-1-yl]propyl]-2-methyl-1,2,4-triazol-3-one Chemical compound COC1=CC=CC=C1N1CCN(C(C)CC=2N(C(=O)N(C)N=2)CC2CCCCC2)CC1 ZWLCYOWQGKARQR-UHFFFAOYSA-N 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 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 2
- -1 cyclooctyl compound Chemical class 0.000 claims 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- FJRAORURQAFYNK-UHFFFAOYSA-N n-[3-[4-[2-[4-(cyclohexylmethyl)-1-methyl-5-oxo-1,2,4-triazol-3-yl]ethyl]piperazin-1-yl]phenyl]acetamide Chemical compound CC(=O)NC1=CC=CC(N2CCN(CCC=3N(C(=O)N(C)N=3)CC3CCCCC3)CC2)=C1 FJRAORURQAFYNK-UHFFFAOYSA-N 0.000 claims 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 1
- HZWXCIJANPHNHI-UHFFFAOYSA-N 4-(cyclohexylmethyl)-2-ethyl-5-[2-[4-(2-methoxyphenyl)piperazin-1-yl]ethyl]-1,2,4-triazol-3-one Chemical compound C1CCCCC1CN1C(=O)N(CC)N=C1CCN(CC1)CCN1C1=CC=CC=C1OC HZWXCIJANPHNHI-UHFFFAOYSA-N 0.000 claims 1
- RAOZDGXYGZWMRD-UHFFFAOYSA-N 4-(cyclohexylmethyl)-5-[2-[4-(2-methoxyphenyl)piperazin-1-yl]ethyl]-2-methyl-1,2,4-triazol-3-one Chemical compound COC1=CC=CC=C1N1CCN(CCC=2N(C(=O)N(C)N=2)CC2CCCCC2)CC1 RAOZDGXYGZWMRD-UHFFFAOYSA-N 0.000 claims 1
- 208000019901 Anxiety disease Diseases 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- 239000000654 additive Substances 0.000 claims 1
- 230000036506 anxiety Effects 0.000 claims 1
- METKIMKYRPQLGS-UHFFFAOYSA-N atenolol Chemical compound CC(C)NCC(O)COC1=CC=C(CC(N)=O)C=C1 METKIMKYRPQLGS-UHFFFAOYSA-N 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- 238000010511 deprotection reaction Methods 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- 208000035475 disorder Diseases 0.000 claims 1
- 239000002552 dosage form Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens 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
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 238000006798 ring closing metathesis reaction Methods 0.000 claims 1
- 125000004434 sulfur atom Chemical group 0.000 claims 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB0715378.6 | 2007-08-07 | ||
| GB0715378A GB0715378D0 (en) | 2007-08-07 | 2007-08-07 | Novel serotonergic modulators |
| GB0810168A GB0810168D0 (en) | 2008-06-04 | 2008-06-04 | Novel serotonergic modulators |
| GB0810168.5 | 2008-06-04 | ||
| PCT/GB2008/002669 WO2009019472A1 (en) | 2007-08-07 | 2008-08-06 | 1, 2, 4 -triazole derivatives as serotonergic modulators |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2010535751A JP2010535751A (ja) | 2010-11-25 |
| JP2010535751A5 true JP2010535751A5 (enExample) | 2011-09-22 |
| JP5358571B2 JP5358571B2 (ja) | 2013-12-04 |
Family
ID=39767579
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010519520A Expired - Fee Related JP5358571B2 (ja) | 2007-08-07 | 2008-08-06 | セロトニン作動性調節因子としての１，２，４−トリアゾール誘導体 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US8222254B2 (enExample) |
| EP (1) | EP2183227B1 (enExample) |
| JP (1) | JP5358571B2 (enExample) |
| CN (1) | CN101827828B (enExample) |
| CA (1) | CA2694621C (enExample) |
| GB (1) | GB2454290B (enExample) |
| WO (1) | WO2009019472A1 (enExample) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5787237B2 (ja) * | 2010-10-01 | 2015-09-30 | 大正製薬株式会社 | １，２，４−トリアゾロン誘導体 |
| EP2822931B1 (en) | 2012-03-09 | 2017-05-03 | Inception 2, Inc. | Triazolone compounds and uses thereof |
| JP6404230B2 (ja) | 2012-12-20 | 2018-10-10 | インセプション ２、 インコーポレイテッド | トリアゾロン化合物およびその使用 |
| CA2921420A1 (en) | 2013-09-06 | 2015-03-12 | Inception 2, Inc. | Triazolone compounds and uses thereof |
| US12459965B2 (en) | 2017-10-09 | 2025-11-04 | Compass Pathfinder Limited | Preparation of psilocybin, different polymorphic forms, intermediates, formulations and their 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 |
| WO2020212951A1 (en) | 2019-04-17 | 2020-10-22 | Compass Pathfinder Limited | Methods for treating anxiety disorders, headache disorders, and eating disorders with psilocybin |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4166452A (en) | 1976-05-03 | 1979-09-04 | Generales Constantine D J Jr | Apparatus for testing human responses to stimuli |
| US4182763A (en) | 1978-05-22 | 1980-01-08 | Mead Johnson & Company | Buspirone anti-anxiety method |
| US4356108A (en) | 1979-12-20 | 1982-10-26 | The Mead Corporation | Encapsulation process |
| US4265874A (en) | 1980-04-25 | 1981-05-05 | Alza Corporation | Method of delivering drug with aid of effervescent activity generated in environment of use |
| US4487773A (en) * | 1981-03-16 | 1984-12-11 | Mead Johnson & Company | 1,2,4-Triazol-3-one antidepressants |
| US4338317A (en) * | 1981-03-16 | 1982-07-06 | Mead Johnson & Company | Phenoxyethyl-1,2,4,-triazol-3-one antidepressants |
| DE4425144A1 (de) * | 1994-07-15 | 1996-01-18 | Basf Ag | Triazolverbindungen und deren Verwendung |
| AU6517196A (en) * | 1995-07-13 | 1997-02-10 | Knoll Aktiengesellschaft | Piperazine derivatives as therapeutic agents |
| FR2841544B1 (fr) | 2002-06-27 | 2004-08-27 | Heurgue Conseil S A | Dispositif de vidange de silo |
| US7153858B2 (en) | 2003-01-31 | 2006-12-26 | Epix Delaware, Inc. | Arylpiperazinyl compounds |
-
2008
- 2008-08-06 CN CN2008801021328A patent/CN101827828B/zh not_active Expired - Fee Related
- 2008-08-06 GB GB0814351A patent/GB2454290B/en not_active Expired - Fee Related
- 2008-08-06 JP JP2010519520A patent/JP5358571B2/ja not_active Expired - Fee Related
- 2008-08-06 CA CA2694621A patent/CA2694621C/en not_active Expired - Fee Related
- 2008-08-06 WO PCT/GB2008/002669 patent/WO2009019472A1/en not_active Ceased
- 2008-08-06 US US12/670,829 patent/US8222254B2/en not_active Expired - Fee Related
- 2008-08-06 EP EP08776140.9A patent/EP2183227B1/en not_active Not-in-force
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