CA2931016C - Synthesis of trans-8-chloro-5-methyl-1-[4-(pyridin-2-yloxy)-cyclohexyl]-5,6-dihydro-4h-2,3,5,10b-tetraaza-benzo[e]azulene and crystalline forms thereof - Google Patents
Synthesis of trans-8-chloro-5-methyl-1-[4-(pyridin-2-yloxy)-cyclohexyl]-5,6-dihydro-4h-2,3,5,10b-tetraaza-benzo[e]azulene and crystalline forms thereof Download PDFInfo
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- CA2931016C CA2931016C CA2931016A CA2931016A CA2931016C CA 2931016 C CA2931016 C CA 2931016C CA 2931016 A CA2931016 A CA 2931016A CA 2931016 A CA2931016 A CA 2931016A CA 2931016 C CA2931016 C CA 2931016C
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- 230000015572 biosynthetic process Effects 0.000 title description 12
- 238000003786 synthesis reaction Methods 0.000 title description 6
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- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 55
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 53
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 52
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- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 claims description 10
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 10
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- 239000012458 free base Substances 0.000 claims description 10
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- 229940086066 potassium hydrogencarbonate Drugs 0.000 claims description 4
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 claims description 3
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- CETVQRFGPOGIQJ-UHFFFAOYSA-N lithium;hexane Chemical compound [Li+].CCCCC[CH2-] CETVQRFGPOGIQJ-UHFFFAOYSA-N 0.000 claims description 2
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- 239000003153 chemical reaction reagent Substances 0.000 description 7
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 7
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- 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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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- 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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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D243/00—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms
- C07D243/06—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4
- C07D243/10—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems
- C07D243/14—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/13—Crystalline forms, e.g. polymorphs
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Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA3142754A CA3142754C (en) | 2013-12-05 | 2014-12-01 | Synthesis of trans-8-chloro-5-methyl- 1-[4-(pyridin-2-yloxy)-cyclohexyl]-5,6-dihydro-4h-2,3,5,10b-tetraaza-benzo[e]azulene and crystalline forms thereof |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP13195864.7 | 2013-12-05 | ||
| EP13195864 | 2013-12-05 | ||
| PCT/EP2014/076041 WO2015082370A1 (en) | 2013-12-05 | 2014-12-01 | Synthesis of trans-8-chloro-5-methyl-1 -[4-(pyridin-2-yloxy)-cyclohexyl]-5,6-dihydro-4h-2,3,5,10b-tetraaza-benzo[e]azulene and crytalline forms thereof |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA3142754A Division CA3142754C (en) | 2013-12-05 | 2014-12-01 | Synthesis of trans-8-chloro-5-methyl- 1-[4-(pyridin-2-yloxy)-cyclohexyl]-5,6-dihydro-4h-2,3,5,10b-tetraaza-benzo[e]azulene and crystalline forms thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2931016A1 CA2931016A1 (en) | 2015-06-11 |
| CA2931016C true CA2931016C (en) | 2022-11-01 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2931016A Active CA2931016C (en) | 2013-12-05 | 2014-12-01 | Synthesis of trans-8-chloro-5-methyl-1-[4-(pyridin-2-yloxy)-cyclohexyl]-5,6-dihydro-4h-2,3,5,10b-tetraaza-benzo[e]azulene and crystalline forms thereof |
| CA3142754A Active CA3142754C (en) | 2013-12-05 | 2014-12-01 | Synthesis of trans-8-chloro-5-methyl- 1-[4-(pyridin-2-yloxy)-cyclohexyl]-5,6-dihydro-4h-2,3,5,10b-tetraaza-benzo[e]azulene and crystalline forms thereof |
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| Application Number | Title | Priority Date | Filing Date |
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| CA3142754A Active CA3142754C (en) | 2013-12-05 | 2014-12-01 | Synthesis of trans-8-chloro-5-methyl- 1-[4-(pyridin-2-yloxy)-cyclohexyl]-5,6-dihydro-4h-2,3,5,10b-tetraaza-benzo[e]azulene and crystalline forms thereof |
Country Status (19)
| Country | Link |
|---|---|
| US (3) | US10246460B2 (OSRAM) |
| EP (1) | EP3077396B1 (OSRAM) |
| JP (1) | JP6454707B2 (OSRAM) |
| KR (3) | KR102384629B1 (OSRAM) |
| CN (1) | CN105793263B (OSRAM) |
| AR (1) | AR098592A1 (OSRAM) |
| AU (2) | AU2014359409A1 (OSRAM) |
| CA (2) | CA2931016C (OSRAM) |
| ES (1) | ES2875411T3 (OSRAM) |
| HR (1) | HRP20210966T1 (OSRAM) |
| IL (2) | IL245450A0 (OSRAM) |
| MX (1) | MX372971B (OSRAM) |
| MY (1) | MY175464A (OSRAM) |
| NZ (1) | NZ720340A (OSRAM) |
| PL (1) | PL3077396T3 (OSRAM) |
| SG (1) | SG11201604502SA (OSRAM) |
| SI (1) | SI3077396T1 (OSRAM) |
| WO (1) | WO2015082370A1 (OSRAM) |
| ZA (1) | ZA201603304B (OSRAM) |
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| JP6454707B2 (ja) | 2013-12-05 | 2019-01-16 | エフ．ホフマン−ラ ロシュ アーゲーＦ． Ｈｏｆｆｍａｎｎ−Ｌａ Ｒｏｃｈｅ Ａｋｔｉｅｎｇｅｓｅｌｌｓｃｈａｆｔ | ｔｒａｎｓ−８−クロロ−５−メチル−１−［４−（ピリジン−２−イルオキシ）−シクロヘキシル］−５，６−ジヒドロ−４Ｈ−２，３，５，１０ｂ−テトラアザ−ベンゾ［ｅ］アズレン及びその結晶形態の合成 |
| WO2017191117A1 (en) | 2016-05-03 | 2017-11-09 | Bayer Pharma Aktiengesellschaft | V1a receptor antagonists for use in the treatment of renal diseases |
| IL275144B2 (en) | 2017-12-08 | 2024-12-01 | Hoffmann La Roche | Pharmaceutical formulation |
| WO2020139670A1 (en) | 2018-12-27 | 2020-07-02 | Teva Pharmaceuticals International Gmbh | Solid state forms of balovaptan |
| CN116830362A (zh) | 2021-10-06 | 2023-09-29 | 株式会社 Lg新能源 | 电池模块 |
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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 |
| BRPI0407676A (pt) * | 2003-02-19 | 2006-03-01 | Pfizer | compostos de triazol,uso e processos para fabricação do mesmo |
| GB0400700D0 (en) | 2004-01-13 | 2004-02-18 | Pfizer Ltd | Compounds useful in therapy |
| MX2007002248A (es) | 2004-08-25 | 2008-10-02 | Pfizer | Triazolobenzodiazepinas y su uso como antagonistas de vasopresina. |
| 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 |
| MX2011005119A (es) * | 2008-11-18 | 2011-05-30 | Hoffmann La Roche | Alquilciclohexileteres de dihidrotetraazabenzoazulenos. |
| JP5452608B2 (ja) | 2008-11-28 | 2014-03-26 | エフ．ホフマン−ラ ロシュ アーゲー | バソプレシン介在受容体アンタゴニストとしての使用のためのジヒドロテトラアザベンゾアズレンのアリールシクロヘキシルエーテル |
| US8492376B2 (en) | 2010-04-21 | 2013-07-23 | Hoffmann-La Roche Inc. | Heteroaryl-cyclohexyl-tetraazabenzo[e]azulenes |
| CN105492010B (zh) | 2013-08-19 | 2020-01-03 | 豪夫迈·罗氏有限公司 | 用于治疗相移睡眠障碍的V1a拮抗剂 |
| JP6454707B2 (ja) | 2013-12-05 | 2019-01-16 | エフ．ホフマン−ラ ロシュ アーゲーＦ． Ｈｏｆｆｍａｎｎ−Ｌａ Ｒｏｃｈｅ Ａｋｔｉｅｎｇｅｓｅｌｌｓｃｈａｆｔ | ｔｒａｎｓ−８−クロロ−５−メチル−１−［４−（ピリジン−２−イルオキシ）−シクロヘキシル］−５，６−ジヒドロ−４Ｈ−２，３，５，１０ｂ−テトラアザ−ベンゾ［ｅ］アズレン及びその結晶形態の合成 |
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2014
- 2014-12-01 JP JP2016536746A patent/JP6454707B2/ja active Active
- 2014-12-01 AU AU2014359409A patent/AU2014359409A1/en not_active Abandoned
- 2014-12-01 MX MX2016006558A patent/MX372971B/es active IP Right Grant
- 2014-12-01 HR HRP20210966TT patent/HRP20210966T1/hr unknown
- 2014-12-01 KR KR1020217034768A patent/KR102384629B1/ko active Active
- 2014-12-01 KR KR1020167017925A patent/KR102384608B1/ko active Active
- 2014-12-01 WO PCT/EP2014/076041 patent/WO2015082370A1/en not_active Ceased
- 2014-12-01 KR KR1020217034765A patent/KR102384630B1/ko active Active
- 2014-12-01 EP EP14805290.5A patent/EP3077396B1/en active Active
- 2014-12-01 SI SI201431838T patent/SI3077396T1/sl unknown
- 2014-12-01 PL PL14805290T patent/PL3077396T3/pl unknown
- 2014-12-01 CN CN201480065960.4A patent/CN105793263B/zh active Active
- 2014-12-01 CA CA2931016A patent/CA2931016C/en active Active
- 2014-12-01 MY MYPI2016000870A patent/MY175464A/en unknown
- 2014-12-01 ES ES14805290T patent/ES2875411T3/es active Active
- 2014-12-01 NZ NZ720340A patent/NZ720340A/en unknown
- 2014-12-01 CA CA3142754A patent/CA3142754C/en active Active
- 2014-12-01 SG SG11201604502SA patent/SG11201604502SA/en unknown
- 2014-12-03 AR ARP140104488A patent/AR098592A1/es unknown
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2016
- 2016-05-03 IL IL245450A patent/IL245450A0/en unknown
- 2016-05-16 ZA ZA2016/03304A patent/ZA201603304B/en unknown
- 2016-06-03 US US15/172,542 patent/US10246460B2/en active Active
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- 2019-02-18 IL IL264891A patent/IL264891B/en active IP Right Grant
- 2019-02-20 AU AU2019201183A patent/AU2019201183B2/en active Active
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2021
- 2021-06-03 US US17/337,547 patent/US12459947B2/en active Active
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