JP2014510097A5 - - Google Patents
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- Publication number
- JP2014510097A5 JP2014510097A5 JP2014500512A JP2014500512A JP2014510097A5 JP 2014510097 A5 JP2014510097 A5 JP 2014510097A5 JP 2014500512 A JP2014500512 A JP 2014500512A JP 2014500512 A JP2014500512 A JP 2014500512A JP 2014510097 A5 JP2014510097 A5 JP 2014510097A5
- Authority
- JP
- Japan
- Prior art keywords
- mmol
- ethyl acetate
- mixture
- diastereomers
- flash chromatography
- 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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- XEKOWRVHYACXOJ-UHFFFAOYSA-N acetic acid ethyl ester Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 3
- NUCWDCRUEIUKPN-UHFFFAOYSA-J ethane-1,2-diamine;palladium(2+);phosphonato phosphate Chemical compound [Pd+2].[Pd+2].NCCN.NCCN.[O-]P([O-])(=O)OP([O-])([O-])=O NUCWDCRUEIUKPN-UHFFFAOYSA-J 0.000 description 2
- 238000003818 flash chromatography Methods 0.000 description 2
- 239000008079 hexane Substances 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 2
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 2
- 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 description 1
- 150000005171 halobenzenes Chemical class 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
Description
中間体−４（０．３ｇ、０．９４ミリモル）、メチル３−（３−ブロモフェニル）プロパノエート（０．２８ｇ、０１．１３ミリモル）、およびＣｓ2ＣＯ3（０．４６ｇ、１．４１ミリモル）のトルエン（７ｍＬ）混合物溶液を１５分、窒素パージによって脱気した。続いて、ビス（トリ−ｔｅｒｔ−ブチルホスフィンパラジウム（０）（０．０２４ｇ、０．０４７ミリモル）とトリスジベンジリデンアセトンジパラジウム（０）（０．０２２ｇ、０．０４７ミリモル）を加えた。この反応混合物を１１０℃に加熱し、さらに２０時間、１１０℃で静置した。この反応混合物をＲＴに冷却し、反応の進展をＴＬＣによってモニタリングした。この混合物をエチルアセテートで希釈し、セライトろ過し、真空下で濃縮して粗生成物を得た。１５％のエチルアセテートのヘキサン混合物を用いたフラッシュクロマトグラフィーによって、ジアステレオマーを分離して、実施例−１０ａおよび実施例−１０ｂ（０．０６ｇ、０．０９ｇ、６５％）を得た。ｍ／ｚ：４９６．２
中間体−４と、適宜置換されたハロベンゼンを用いて、実施例−１０ａ、１０ｂに記載されているものと同様の手順に従って、表−２に示されている下記の実施例１１〜３９を調製した。さらに、エチルアセテート／ヘキサン混合物を用いたフラッシュクロマトグラフィーによって、これらのジアステレオマーを分離した。
中間体−４と、適宜置換されたハロベンゼンを用いて、実施例−１０ａ、１０ｂに記載されているものと同様の手順に従って、表−２に示されている下記の実施例１１〜３９を調製した。さらに、エチルアセテート／ヘキサン混合物を用いたフラッシュクロマトグラフィーによって、これらのジアステレオマーを分離した。
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IN367KO2011 | 2011-03-18 | ||
| IN367/KOL/2011 | 2011-03-18 | ||
| PCT/IB2012/051268 WO2012127388A1 (en) | 2011-03-18 | 2012-03-16 | Benzo [b] [1, 4] oxazin derivatives as calcium sensing receptor modulators |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2014510097A JP2014510097A (ja) | 2014-04-24 |
| JP2014510097A5 true JP2014510097A5 (ja) | 2015-04-30 |
| JP6033835B2 JP6033835B2 (ja) | 2016-11-30 |
Family
ID=54192843
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014500512A Expired - Fee Related JP6033835B2 (ja) | 2011-03-18 | 2012-03-16 | カルシウム感知受容体モジュレーターとしてのベンゾ［ｂ］［１，４］オキサジン誘導体 |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US9464063B2 (ja) |
| EP (1) | EP2686306B1 (ja) |
| JP (1) | JP6033835B2 (ja) |
| KR (1) | KR20140051846A (ja) |
| CN (1) | CN103459377B (ja) |
| AP (1) | AP2013007153A0 (ja) |
| AU (1) | AU2012232706B2 (ja) |
| BR (1) | BR112013023914A2 (ja) |
| CA (1) | CA2829466A1 (ja) |
| EA (1) | EA024893B9 (ja) |
| IL (1) | IL228461A0 (ja) |
| MX (1) | MX2013010670A (ja) |
| SG (1) | SG193331A1 (ja) |
| WO (2) | WO2012127388A1 (ja) |
| ZA (1) | ZA201306837B (ja) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR102041154B1 (ko) | 2012-02-24 | 2019-11-07 | 루핀 리미티드 | 칼슘 감지 수용체 조절자로서의 치환 크로만 화합물 |
| WO2013136288A1 (en) | 2012-03-16 | 2013-09-19 | Lupin Limited | Substituted 3,4-dihydro-2h-benzo[b] [1,4]oxazine compounds as calcium sensing receptor modulators |
| AU2013308081A1 (en) | 2012-08-27 | 2015-02-26 | Lupin Atlantis Holdings Sa | Arylalkylamine compounds as calcium sensing receptor modulators |
| TW201602062A (zh) | 2013-08-12 | 2016-01-16 | 魯賓有限公司 | 取代聯苯基化合物作為鈣敏感受體調節劑 |
| US9493396B2 (en) | 2013-08-28 | 2016-11-15 | Lupin Atlantis Holdings Sa | Substituted naphthalene compounds as calcium sensing receptor modulators |
| WO2015059668A1 (en) | 2013-10-25 | 2015-04-30 | Novartis Ag | Ring-fused bicyclic pyridyl derivatives as fgfr4 inhibitors |
| WO2015162538A1 (en) | 2014-04-21 | 2015-10-29 | Lupin Limited | Heterocyclic compounds as calcium sensing receptor modulators for the treatment of hyperparathyroidism, chronic renal failure and chronic kidney disease |
| PL3200786T3 (pl) | 2014-10-03 | 2020-03-31 | Novartis Ag | Zastosowanie pochodnych pirydylowych o skondensowanym układzie bicyklicznym jako inhibitorów fgfr4 |
| CN104464530B (zh) * | 2014-11-18 | 2017-08-25 | 深圳市华星光电技术有限公司 | 曲面型显示装置 |
| US9802917B2 (en) | 2015-03-25 | 2017-10-31 | Novartis Ag | Particles of N-(5-cyano-4-((2-methoxyethyl)amino)pyridin-2-yl)-7-formyl-6-((4-methyl-2-oxopiperazin-1-yl)methyl)-3,4-dihydro-1,8-naphthyridine-1(2H)-carboxamide |
| WO2017007755A1 (en) | 2015-07-06 | 2017-01-12 | Rodin Therapeutics, Inc. | Heterobicyclic n-aminophenyl-amides as inhibitors of histone deacetylase |
| WO2017007756A1 (en) | 2015-07-06 | 2017-01-12 | Rodin Therapeutics, Inc | Hetero-halo inhibitors of histone deacetylase |
| WO2017037616A1 (en) | 2015-08-31 | 2017-03-09 | Lupin Limited | Arylalkylamine compounds as calcium sensing receptor modulators |
| US11072602B2 (en) | 2016-12-06 | 2021-07-27 | Merck Sharp & Dohme Corp. | Antidiabetic heterocyclic compounds |
| ES2909086T3 (es) | 2017-01-11 | 2022-05-05 | Alkermes Inc | Inhibidores bicíclicos de histona desacetilasa |
| HRP20220648T1 (hr) | 2017-08-07 | 2022-09-02 | Alkermes, Inc. | Biciklički inhibitori histonske deacetilaze |
| BR112022012663A2 (pt) | 2019-12-27 | 2022-09-06 | Lupin Ltd | Composição farmacêutica de moduladores de casr e métodos e usos da mesma |
| WO2021144814A1 (en) | 2020-01-17 | 2021-07-22 | Lupin Limited | Methods, processes and intermediates for preparing chroman compounds |
Family Cites Families (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1109880A (zh) | 1994-02-03 | 1995-10-11 | 合成实验室公司 | 3-(2-氨基乙基)-4-[3-(三氟甲基)苯甲酰基]-3，4-二氢-2h-1，4-苯并噁嗪衍生物、制备及其应用 |
| FR2809396B1 (fr) * | 2000-05-24 | 2005-10-14 | Centre Nat Rech Scient | Nouvelles molecules possedant une activite calcimimetique et leur mode de preparation |
| FR2812875B1 (fr) | 2000-08-08 | 2003-12-12 | Centre Nat Rech Scient | Nouvelles diamines possedant une activite modulatrice des casr et leur mode de preparation |
| US6908935B2 (en) * | 2002-05-23 | 2005-06-21 | Amgen Inc. | Calcium receptor modulating agents |
| US7105537B2 (en) | 2003-01-28 | 2006-09-12 | Bristol-Myers Squibb Company | 2-substituted cyclic amines as calcium sensing receptor modulators |
| EP1630157A4 (en) | 2003-05-28 | 2007-05-23 | Japan Tobacco Inc | ANTAGONIST OF CASR |
| CA2608194A1 (en) * | 2005-05-09 | 2006-11-16 | Hydra Biosciences, Inc. | Compounds for modulating trpv3 function |
| US7585886B2 (en) * | 2005-05-19 | 2009-09-08 | Astellas Pharma Inc. | Pyrrolidine derivative or salt thereof |
| WO2008041118A2 (en) | 2006-10-04 | 2008-04-10 | Pfizer Products Inc. | Pyrido[4,3-d]pyrimidin-4(3h)-one derivatives as calcium receptor antagonists |
| MX2009003981A (es) * | 2006-10-26 | 2009-04-27 | Amgen Inc | Agentes moduladores del receptor de calcio. |
| US8153658B2 (en) | 2006-11-16 | 2012-04-10 | Astellas Pharma, Inc. | Piperidine derivative or salt thereof |
| AU2008328362A1 (en) | 2007-11-23 | 2009-05-28 | Leo Pharma A/S | Novel cyclic hydrocarbon compounds for the treatment of diseases |
| CN102239136B (zh) | 2008-10-03 | 2014-09-17 | 味之素株式会社 | CaSR激动剂 |
| US8791147B2 (en) | 2008-10-08 | 2014-07-29 | Amgen Inc. | Calcium receptor modulating agents |
| WO2010090069A1 (ja) * | 2009-02-05 | 2010-08-12 | ヤンマー株式会社 | Ｅｇｒ装置及びこれを備えたエンジン装置 |
| CA2762137A1 (en) | 2009-05-27 | 2010-12-02 | Leo Pharma A/S | Novel calcium sensing receptor modulating compounds and pharmaceutical use thereof |
| WO2010150837A1 (ja) | 2009-06-25 | 2010-12-29 | 第一三共株式会社 | インドリン誘導体 |
-
2012
- 2012-03-16 AP AP2013007153A patent/AP2013007153A0/xx unknown
- 2012-03-16 EP EP12713351.0A patent/EP2686306B1/en active Active
- 2012-03-16 KR KR1020137026964A patent/KR20140051846A/ko not_active Application Discontinuation
- 2012-03-16 CA CA2829466A patent/CA2829466A1/en not_active Abandoned
- 2012-03-16 CN CN201280013968.7A patent/CN103459377B/zh not_active Expired - Fee Related
- 2012-03-16 WO PCT/IB2012/051268 patent/WO2012127388A1/en active Application Filing
- 2012-03-16 SG SG2013067004A patent/SG193331A1/en unknown
- 2012-03-16 EA EA201370205A patent/EA024893B9/ru not_active IP Right Cessation
- 2012-03-16 MX MX2013010670A patent/MX2013010670A/es unknown
- 2012-03-16 JP JP2014500512A patent/JP6033835B2/ja not_active Expired - Fee Related
- 2012-03-16 BR BR112013023914A patent/BR112013023914A2/pt active Search and Examination
- 2012-03-16 US US14/005,944 patent/US9464063B2/en not_active Expired - Fee Related
- 2012-03-16 WO PCT/IB2012/051263 patent/WO2012127385A1/en active Application Filing
- 2012-03-16 AU AU2012232706A patent/AU2012232706B2/en not_active Ceased
-
2013
- 2013-09-11 ZA ZA2013/06837A patent/ZA201306837B/en unknown
- 2013-09-16 IL IL228461A patent/IL228461A0/en unknown
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