JP2018522025A5 - - Google Patents
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- Publication number
- JP2018522025A5 JP2018522025A5 JP2018504658A JP2018504658A JP2018522025A5 JP 2018522025 A5 JP2018522025 A5 JP 2018522025A5 JP 2018504658 A JP2018504658 A JP 2018504658A JP 2018504658 A JP2018504658 A JP 2018504658A JP 2018522025 A5 JP2018522025 A5 JP 2018522025A5
- Authority
- JP
- Japan
- Prior art keywords
- compound
- azepine
- alkyl
- naphtho
- cyclopropane
- 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
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- 150000001875 compounds Chemical class 0.000 claims description 234
- 229910052736 halogen Inorganic materials 0.000 claims description 100
- 150000002367 halogens Chemical class 0.000 claims description 86
- 229910052799 carbon Inorganic materials 0.000 claims description 51
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 50
- XYOVOXDWRFGKEX-UHFFFAOYSA-N azepine Chemical compound N1C=CC=CC=C1 XYOVOXDWRFGKEX-UHFFFAOYSA-N 0.000 claims description 48
- 150000003839 salts Chemical class 0.000 claims description 36
- 238000011282 treatment Methods 0.000 claims description 34
- 150000004677 hydrates Chemical class 0.000 claims description 32
- 239000012453 solvate Substances 0.000 claims description 32
- 239000000203 mixture Substances 0.000 claims description 29
- 238000000034 method Methods 0.000 claims description 19
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 16
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 9
- 206010015037 epilepsy Diseases 0.000 claims description 9
- 208000008589 Obesity Diseases 0.000 claims description 6
- 229940079593 drug Drugs 0.000 claims description 6
- 239000003814 drug Substances 0.000 claims description 6
- 235000020824 obesity Nutrition 0.000 claims description 6
- 208000007848 Alcoholism Diseases 0.000 claims description 5
- -1 carbon ring compound Chemical class 0.000 claims description 5
- 206010013663 drug dependence Diseases 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 229910052731 fluorine Inorganic materials 0.000 claims description 5
- 230000037406 food intake Effects 0.000 claims description 5
- 235000012631 food intake Nutrition 0.000 claims description 5
- 230000036186 satiety Effects 0.000 claims description 5
- 235000019627 satiety Nutrition 0.000 claims description 5
- 208000011117 substance-related disease Diseases 0.000 claims description 5
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 5
- 230000037221 weight management Effects 0.000 claims description 5
- FWFYROADMVDKET-MBHSVXNSSA-N (10S)-7-azatetracyclo[8.6.1.05,17.012,16]heptadeca-1,3,5(17)-triene Chemical compound C1=CC=C2CNCC[C@H]3C2=C1C1C(C3)CCC1 FWFYROADMVDKET-MBHSVXNSSA-N 0.000 claims description 4
- HHAADTZQFHIUNG-NSHDSACASA-N (1S)-4,4-dimethyl-11-azatricyclo[7.4.1.05,14]tetradeca-5,7,9(14)-triene Chemical compound CC1(C=2C=CC=C3CNCC[C@@H](C3=2)CC1)C HHAADTZQFHIUNG-NSHDSACASA-N 0.000 claims description 4
- VMYTYRLBTQKCLF-UHFFFAOYSA-N 11-azatricyclo[7.4.1.05,14]tetradeca-5(14),6,8-triene Chemical compound C1NCCC2C=3C1=CC=CC=3CCC2 VMYTYRLBTQKCLF-UHFFFAOYSA-N 0.000 claims description 4
- HHAADTZQFHIUNG-UHFFFAOYSA-N 4,4-dimethyl-11-azatricyclo[7.4.1.05,14]tetradeca-5,7,9(14)-triene Chemical compound CC1(C=2C=CC=C3CNCCC(C3=2)CC1)C HHAADTZQFHIUNG-UHFFFAOYSA-N 0.000 claims description 4
- FMBVGHSNLUXLIL-UHFFFAOYSA-N 4-cyclopropyl-11-azatricyclo[7.4.1.05,14]tetradeca-5,7,9(14)-triene Chemical compound C1(CC1)C1C=2C=CC=C3CNCCC(C3=2)CC1 FMBVGHSNLUXLIL-UHFFFAOYSA-N 0.000 claims description 4
- HIVCEDRLVWVQFE-UHFFFAOYSA-N 6-bromo-11-azatricyclo[7.4.1.05,14]tetradeca-5,7,9(14)-triene Chemical compound BrC1=CC=C2CNCCC3C2=C1CCC3 HIVCEDRLVWVQFE-UHFFFAOYSA-N 0.000 claims description 4
- GBRQYIPFAJQIPF-UHFFFAOYSA-N 6-bromo-4,4-dimethyl-11-azatricyclo[7.4.1.05,14]tetradeca-5,7,9(14)-triene Chemical compound BrC1=CC=C2CNCCC3C2=C1C(CC3)(C)C GBRQYIPFAJQIPF-UHFFFAOYSA-N 0.000 claims description 4
- KDBOSBRTALSDFS-UHFFFAOYSA-N 6-chloro-11-azatricyclo[7.4.1.05,14]tetradeca-5,7,9(14)-triene Chemical compound ClC1=CC=C2CNCCC3C2=C1CCC3 KDBOSBRTALSDFS-UHFFFAOYSA-N 0.000 claims description 4
- AJMXMIIAAMKZRA-UHFFFAOYSA-N 6-cyclopropyl-11-azatricyclo[7.4.1.05,14]tetradeca-5,7,9(14)-triene Chemical compound C1(CC1)C1=CC=C2CNCCC3C2=C1CCC3 AJMXMIIAAMKZRA-UHFFFAOYSA-N 0.000 claims description 4
- AIBWMWKSVYVXPA-UHFFFAOYSA-N 6-fluoro-11-azatricyclo[7.4.1.05,14]tetradeca-5,7,9(14)-triene Chemical compound FC1=CC=C2CNCCC3C2=C1CCC3 AIBWMWKSVYVXPA-UHFFFAOYSA-N 0.000 claims description 4
- UZJZKZGRQPLZTA-UHFFFAOYSA-N 6-methoxy-11-azatricyclo[7.4.1.05,14]tetradeca-5,7,9(14)-triene Chemical compound COC1=CC=C2CNCCC3C2=C1CCC3 UZJZKZGRQPLZTA-UHFFFAOYSA-N 0.000 claims description 4
- FWFYROADMVDKET-UHFFFAOYSA-N 7-azatetracyclo[8.6.1.05,17.012,16]heptadeca-1,3,5(17)-triene Chemical compound C1=CC=C2CNCCC3C2=C1C1C(C3)CCC1 FWFYROADMVDKET-UHFFFAOYSA-N 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 4
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 4
- 239000011737 fluorine Substances 0.000 claims description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- 208000032928 Dyslipidaemia Diseases 0.000 claims description 3
- 206010020772 Hypertension Diseases 0.000 claims description 3
- 208000017170 Lipid metabolism disease Diseases 0.000 claims description 3
- 230000001939 inductive effect Effects 0.000 claims description 3
- 201000002859 sleep apnea Diseases 0.000 claims description 3
- 208000011580 syndromic disease Diseases 0.000 claims description 3
- FWFYROADMVDKET-LXVYMNJGSA-N (10R)-7-azatetracyclo[8.6.1.05,17.012,16]heptadeca-1,3,5(17)-triene Chemical compound C1=CC=C2CNCC[C@@H]3C2=C1C1C(C3)CCC1 FWFYROADMVDKET-LXVYMNJGSA-N 0.000 claims description 2
- HHAADTZQFHIUNG-LLVKDONJSA-N (1R)-4,4-dimethyl-11-azatricyclo[7.4.1.05,14]tetradeca-5,7,9(14)-triene Chemical compound CC1(C=2C=CC=C3CNCC[C@H](C3=2)CC1)C HHAADTZQFHIUNG-LLVKDONJSA-N 0.000 claims description 2
- OIIOPWHTJZYKIL-PMACEKPBSA-N (5S)-5-[[[5-[2-chloro-3-[2-chloro-3-[6-methoxy-5-[[[(2S)-5-oxopyrrolidin-2-yl]methylamino]methyl]pyrazin-2-yl]phenyl]phenyl]-3-methoxypyrazin-2-yl]methylamino]methyl]pyrrolidin-2-one Chemical compound C1(=C(N=C(C2=C(C(C3=CC=CC(=C3Cl)C3=NC(OC)=C(N=C3)CNC[C@H]3NC(=O)CC3)=CC=C2)Cl)C=N1)OC)CNC[C@H]1NC(=O)CC1 OIIOPWHTJZYKIL-PMACEKPBSA-N 0.000 claims description 2
- PAYROHWFGZADBR-UHFFFAOYSA-N 2-[[4-amino-5-(5-iodo-4-methoxy-2-propan-2-ylphenoxy)pyrimidin-2-yl]amino]propane-1,3-diol Chemical compound C1=C(I)C(OC)=CC(C(C)C)=C1OC1=CN=C(NC(CO)CO)N=C1N PAYROHWFGZADBR-UHFFFAOYSA-N 0.000 claims description 2
- WFOVEDJTASPCIR-UHFFFAOYSA-N 3-[(4-methyl-5-pyridin-4-yl-1,2,4-triazol-3-yl)methylamino]-n-[[2-(trifluoromethyl)phenyl]methyl]benzamide Chemical compound N=1N=C(C=2C=CN=CC=2)N(C)C=1CNC(C=1)=CC=CC=1C(=O)NCC1=CC=CC=C1C(F)(F)F WFOVEDJTASPCIR-UHFFFAOYSA-N 0.000 claims description 2
- MNMFOPSOWATZRI-UHFFFAOYSA-N 4,4-dimethyl-3-oxa-11-azatricyclo[7.4.1.05,14]tetradeca-5,7,9(14)-triene Chemical compound CC1(OCC2C3=C(CNCC2)C=CC=C13)C MNMFOPSOWATZRI-UHFFFAOYSA-N 0.000 claims description 2
- GSDQYSSLIKJJOG-UHFFFAOYSA-N 4-chloro-2-(3-chloroanilino)benzoic acid Chemical compound OC(=O)C1=CC=C(Cl)C=C1NC1=CC=CC(Cl)=C1 GSDQYSSLIKJJOG-UHFFFAOYSA-N 0.000 claims description 2
- IRBAWVGZNJIROV-SFHVURJKSA-N 9-(2-cyclopropylethynyl)-2-[[(2s)-1,4-dioxan-2-yl]methoxy]-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound C1=C2C3=CC=C(C#CC4CC4)C=C3CCN2C(=O)N=C1OC[C@@H]1COCCO1 IRBAWVGZNJIROV-SFHVURJKSA-N 0.000 claims description 2
- IYHHRZBKXXKDDY-UHFFFAOYSA-N BI-605906 Chemical compound N=1C=2SC(C(N)=O)=C(N)C=2C(C(F)(F)CC)=CC=1N1CCC(S(C)(=O)=O)CC1 IYHHRZBKXXKDDY-UHFFFAOYSA-N 0.000 claims description 2
- UHNRLQRZRNKOKU-UHFFFAOYSA-N CCN(CC1=NC2=C(N1)C1=CC=C(C=C1N=C2N)C1=NNC=C1)C(C)=O Chemical compound CCN(CC1=NC2=C(N1)C1=CC=C(C=C1N=C2N)C1=NNC=C1)C(C)=O UHNRLQRZRNKOKU-UHFFFAOYSA-N 0.000 claims description 2
- 208000024172 Cardiovascular disease Diseases 0.000 claims description 2
- 241000004297 Draba Species 0.000 claims description 2
- 208000002705 Glucose Intolerance Diseases 0.000 claims description 2
- POFVJRKJJBFPII-UHFFFAOYSA-N N-cyclopentyl-5-[2-[[5-[(4-ethylpiperazin-1-yl)methyl]pyridin-2-yl]amino]-5-fluoropyrimidin-4-yl]-4-methyl-1,3-thiazol-2-amine Chemical compound C1(CCCC1)NC=1SC(=C(N=1)C)C1=NC(=NC=C1F)NC1=NC=C(C=C1)CN1CCN(CC1)CC POFVJRKJJBFPII-UHFFFAOYSA-N 0.000 claims description 2
- 206010033307 Overweight Diseases 0.000 claims description 2
- QBYJBZPUGVGKQQ-SJJAEHHWSA-N aldrin Chemical compound C1[C@H]2C=C[C@@H]1[C@H]1[C@@](C3(Cl)Cl)(Cl)C(Cl)=C(Cl)[C@@]3(Cl)[C@H]12 QBYJBZPUGVGKQQ-SJJAEHHWSA-N 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 201000009104 prediabetes syndrome Diseases 0.000 claims description 2
- KSAVQLQVUXSOCR-UHFFFAOYSA-M sodium lauroyl sarcosinate Chemical compound [Na+].CCCCCCCCCCCC(=O)N(C)CC([O-])=O KSAVQLQVUXSOCR-UHFFFAOYSA-M 0.000 claims description 2
- 238000002560 therapeutic procedure Methods 0.000 claims description 2
- 125000002837 carbocyclic group Chemical group 0.000 claims 1
- 230000003247 decreasing effect Effects 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 description 27
- 125000006512 3,4-dichlorobenzyl group Chemical group [H]C1=C(Cl)C(Cl)=C([H])C(=C1[H])C([H])([H])* 0.000 description 9
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 9
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 9
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 6
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| 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 |
| US12459965B2 (en) | 2017-10-09 | 2025-11-04 | Compass Pathfinder Limited | Preparation of psilocybin, different polymorphic forms, intermediates, formulations and their use |
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| EP3870292A4 (en) | 2018-10-26 | 2022-11-09 | The Research Foundation for The State University of New York | COMBINATION OF SEROTONIN-SPECIFIC RESUPPUT INHIBITOR AND SEROTONIN 1A RECEPTOR PARTIAL AGONIST TO REDUCE L-DOPA-INDUCED DYSKINESIA |
| CN110642721B (zh) * | 2018-12-21 | 2022-09-30 | 安徽贝克生物制药有限公司 | 盐酸司来吉兰的制备方法 |
| CN110668951B (zh) * | 2018-12-21 | 2022-09-30 | 安徽贝克生物制药有限公司 | 一种盐酸司来吉兰的合成工艺 |
| AU2020258086A1 (en) | 2019-04-17 | 2021-11-11 | Compass Pathfinder Limited | Methods of treating neurocognitive disorders, chronic pain and reducing inflammation |
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| US6953787B2 (en) * | 2002-04-12 | 2005-10-11 | Arena Pharmaceuticals, Inc. | 5HT2C receptor modulators |
| TW200307682A (en) * | 2002-04-25 | 2003-12-16 | Wyeth Corp | 1,2,3,4,7,8-Hexahydro-6H-[1,4]diazepino[6,7,1-ij]quinoline derivatives as antipsychotic and antiobesity agents |
| CN1805939B (zh) * | 2003-06-17 | 2010-10-13 | 艾尼纳制药公司 | 用于治疗5ht2c受体相关病症的苯并氮杂卓衍生物 |
| AU2004282101A1 (en) * | 2003-10-08 | 2005-04-28 | Eli Lilly And Company | Compounds and methods for treating dyslipidemia |
| EP2510949A4 (en) * | 2009-12-11 | 2013-11-13 | Astellas Pharma Inc | THERAPEUTICS FOR FIBROMYALGIA |
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| AU2016302755B2 (en) | 2015-07-31 | 2020-09-10 | Arena Pharmaceuticals, Inc. | 5-HT2C receptor agonists and compositions and methods of use |
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