KR102384608B1 - 트랜스-8-클로로-5-메틸-1-[4-(피리딘-2-일옥시)-사이클로헥실]-5,6-다이하이드로-4H-2,3,5,10b-테트라아자-벤조[e]아줄렌 및 그의 결정 형태의 합성 - Google Patents
트랜스-8-클로로-5-메틸-1-[4-(피리딘-2-일옥시)-사이클로헥실]-5,6-다이하이드로-4H-2,3,5,10b-테트라아자-벤조[e]아줄렌 및 그의 결정 형태의 합성 Download PDFInfo
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- KR102384608B1 KR102384608B1 KR1020167017925A KR20167017925A KR102384608B1 KR 102384608 B1 KR102384608 B1 KR 102384608B1 KR 1020167017925 A KR1020167017925 A KR 1020167017925A KR 20167017925 A KR20167017925 A KR 20167017925A KR 102384608 B1 KR102384608 B1 KR 102384608B1
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- 230000015572 biosynthetic process Effects 0.000 title description 40
- 238000003786 synthesis reaction Methods 0.000 title description 34
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- 150000001875 compounds Chemical class 0.000 claims abstract description 293
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- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 76
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 64
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 51
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- 239000002904 solvent Substances 0.000 claims description 29
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 28
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- -1 chloro- Chemical compound 0.000 claims description 16
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- 239000011736 potassium bicarbonate Substances 0.000 claims description 5
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- UKODFQOELJFMII-UHFFFAOYSA-N pentamethyldiethylenetriamine Chemical compound CN(C)CCN(C)CCN(C)C UKODFQOELJFMII-UHFFFAOYSA-N 0.000 claims description 3
- CETVQRFGPOGIQJ-UHFFFAOYSA-N lithium;hexane Chemical compound [Li+].CCCCC[CH2-] CETVQRFGPOGIQJ-UHFFFAOYSA-N 0.000 claims description 2
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- 238000006138 lithiation reaction Methods 0.000 claims 1
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- DIYBTHVWQJYHOY-UHFFFAOYSA-N tert-butyl N-[4-chloro-2-(methylaminomethyl)phenyl]carbamate Chemical compound ClC1=CC(=C(C=C1)NC(OC(C)(C)C)=O)CNC DIYBTHVWQJYHOY-UHFFFAOYSA-N 0.000 description 8
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- AVIOWTWKTMGTCW-UHFFFAOYSA-N 4-pyridin-2-yloxy-N'-(4-pyridin-2-yloxycyclohexanecarbonyl)cyclohexane-1-carbohydrazide Chemical compound N1=C(C=CC=C1)OC1CCC(CC1)C(=O)NNC(=O)C1CCC(CC1)OC1=NC=CC=C1 AVIOWTWKTMGTCW-UHFFFAOYSA-N 0.000 description 3
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Classifications
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- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
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- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
- A61K31/551—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole having two nitrogen atoms, e.g. dilazep
- A61K31/5513—1,4-Benzodiazepines, e.g. diazepam or clozapine
- A61K31/5517—1,4-Benzodiazepines, e.g. diazepam or clozapine condensed with five-membered rings having nitrogen as a ring hetero atom, e.g. imidazobenzodiazepines, triazolam
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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| KR1020217034765A KR102384630B1 (ko) | 2013-12-05 | 2014-12-01 | 트랜스-8-클로로-5-메틸-1-[4-(피리딘-2-일옥시)-사이클로헥실]-5,6-다이하이드로-4H-2,3,5,10b-테트라아자-벤조[e]아줄렌 및 그의 결정 형태의 합성 |
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| KR1020217034765A Division KR102384630B1 (ko) | 2013-12-05 | 2014-12-01 | 트랜스-8-클로로-5-메틸-1-[4-(피리딘-2-일옥시)-사이클로헥실]-5,6-다이하이드로-4H-2,3,5,10b-테트라아자-벤조[e]아줄렌 및 그의 결정 형태의 합성 |
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| CN105793263B (zh) | 2013-12-05 | 2019-08-23 | 豪夫迈·罗氏有限公司 | 一种苯并[e]薁化合物及其晶型的合成 |
| WO2017191117A1 (en) | 2016-05-03 | 2017-11-09 | Bayer Pharma Aktiengesellschaft | V1a receptor antagonists for use in the treatment of renal diseases |
| PL3720424T3 (pl) | 2017-12-08 | 2022-12-27 | F. Hoffmann-La Roche Ag | Preparat farmaceutyczny |
| WO2020139670A1 (en) | 2018-12-27 | 2020-07-02 | Teva Pharmaceuticals International Gmbh | Solid state forms of balovaptan |
| US20240154207A1 (en) | 2021-10-06 | 2024-05-09 | Lg Energy Solution, Ltd. | Battery module |
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| CA1197242A (en) * | 1983-03-02 | 1985-11-26 | Jean A. Gauthier | Pyrimido¬1,2-a|pyrrolo¬2,1-c|¬1, 4|benzodiazepine-3-carboxylic acid derivatives |
| GB0303852D0 (en) | 2003-02-19 | 2003-03-26 | Pfizer Ltd | Triazole compounds useful in therapy |
| ES2277237T3 (es) * | 2003-02-19 | 2007-07-01 | Pfizer Inc. | Compuestos de triazol utiles en terapia. |
| GB0400700D0 (en) | 2004-01-13 | 2004-02-18 | Pfizer Ltd | Compounds useful in therapy |
| JP2008510789A (ja) | 2004-08-25 | 2008-04-10 | ファイザー・インク | トリアゾロベンゾジアゼピン及びバゾプレシンアンタゴニストとしてのそれらの使用 |
| US7601715B2 (en) | 2005-06-22 | 2009-10-13 | Bristol-Myers Squibb Company | Process for preparing triazole substituted azaindoleoxoacetic piperazine derivatives and novel salt forms produced therein |
| PL2358714T3 (pl) * | 2008-11-18 | 2012-12-31 | Hoffmann La Roche | Etery alkilocykloheksylowe dihydrotetraazabenzoazulenu |
| US8492376B2 (en) | 2010-04-21 | 2013-07-23 | Hoffmann-La Roche Inc. | Heteroaryl-cyclohexyl-tetraazabenzo[e]azulenes |
| MX2016001940A (es) | 2013-08-19 | 2016-06-02 | Hoffmann La Roche | Antagonistas de v1a para tratar trastornos del sueño por cambio de fase. |
| CN105793263B (zh) | 2013-12-05 | 2019-08-23 | 豪夫迈·罗氏有限公司 | 一种苯并[e]薁化合物及其晶型的合成 |
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| WO2010060836A1 (en) * | 2008-11-28 | 2010-06-03 | F. Hoffmann-La Roche Ag | Arylcyclohexylethers of dihydrotetraazabenzoazulenes for use as vasopressin via receptor antagonists |
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