JP2018505179A5 - - Google Patents
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- Publication number
- JP2018505179A5 JP2018505179A5 JP2017540562A JP2017540562A JP2018505179A5 JP 2018505179 A5 JP2018505179 A5 JP 2018505179A5 JP 2017540562 A JP2017540562 A JP 2017540562A JP 2017540562 A JP2017540562 A JP 2017540562A JP 2018505179 A5 JP2018505179 A5 JP 2018505179A5
- Authority
- JP
- Japan
- Prior art keywords
- formula
- compound
- reacting
- method comprises
- reaction
- 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 30
- 238000000034 method Methods 0.000 claims 25
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 6
- 238000006243 chemical reaction Methods 0.000 claims 4
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 3
- 239000003638 chemical reducing agent Substances 0.000 claims 3
- 238000002360 preparation method Methods 0.000 claims 3
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 2
- 239000003054 catalyst Substances 0.000 claims 2
- QQVDYSUDFZZPSU-UHFFFAOYSA-M chloromethylidene(dimethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)=CCl QQVDYSUDFZZPSU-UHFFFAOYSA-M 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 2
- PNKUSGQVOMIXLU-UHFFFAOYSA-N Formamidine Chemical compound NC=N PNKUSGQVOMIXLU-UHFFFAOYSA-N 0.000 claims 1
- 229910019213 POCl3 Inorganic materials 0.000 claims 1
- 229910052783 alkali metal Inorganic materials 0.000 claims 1
- 150000001340 alkali metals Chemical class 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 239000003153 chemical reaction reagent Substances 0.000 claims 1
- 230000000694 effects Effects 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims 1
- 150000002500 ions Chemical class 0.000 claims 1
- 238000002955 isolation Methods 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- 238000005580 one pot reaction Methods 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1501593.6 | 2015-01-30 | ||
| GBGB1501593.6A GB201501593D0 (en) | 2015-01-30 | 2015-01-30 | New compounds and processes |
| PCT/GB2016/050204 WO2016120635A1 (en) | 2015-01-30 | 2016-01-29 | Processes for the preparation of compounds, such as 3-arylbutanals, useful in the synthesis of medetomidine |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2018505179A JP2018505179A (ja) | 2018-02-22 |
| JP2018505179A5 true JP2018505179A5 (enExample) | 2019-03-07 |
| JP6702623B2 JP6702623B2 (ja) | 2020-06-03 |
Family
ID=52705534
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017540562A Active JP6702623B2 (ja) | 2015-01-30 | 2016-01-29 | メデトミジンの合成に有用な３−アリールブタナールなどの化合物の調製方法 |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US10053420B2 (enExample) |
| EP (1) | EP3250556B1 (enExample) |
| JP (1) | JP6702623B2 (enExample) |
| KR (1) | KR102458638B1 (enExample) |
| CN (1) | CN107428648B (enExample) |
| DK (1) | DK3250556T3 (enExample) |
| ES (1) | ES2716748T3 (enExample) |
| GB (1) | GB201501593D0 (enExample) |
| HR (1) | HRP20190286T1 (enExample) |
| HU (1) | HUE042626T2 (enExample) |
| PL (1) | PL3250556T3 (enExample) |
| TR (1) | TR201902673T4 (enExample) |
| WO (1) | WO2016120635A1 (enExample) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US12050293B2 (en) | 2018-12-19 | 2024-07-30 | Pgs Geophysical As | Medetomidine compositions having improved anti-fouling characteristics |
| WO2022086416A1 (en) | 2020-10-21 | 2022-04-28 | I-Tech Ab | Antifouling compounds |
| EP4506340A1 (en) | 2022-03-22 | 2025-02-12 | Obshestvo s Ogranichennoj Otvetstvennostju "Vikzdorove Zhivotnyh" | Method for producing medetomidine and its derivatives |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2340812C2 (de) | 1973-08-11 | 1982-05-27 | Basf Ag, 6700 Ludwigshafen | Phenylpropanale sowie ein Verfahren zu deren Herstellung |
| US4416902A (en) | 1982-07-16 | 1983-11-22 | International Flavors & Fragrances Inc. | Flavoring with cyclohexenyl-beta-methyl acrolein derivatives |
| DE19714042A1 (de) * | 1997-04-05 | 1998-10-08 | Henkel Kgaa | Verfahren zur Herstellung aromatischer Aldehyde |
| WO2007111630A1 (en) * | 2005-07-29 | 2007-10-04 | Flexitral, Inc. | Compounds which release an odor on a change in ph |
| CN102458659B (zh) * | 2009-06-03 | 2014-07-09 | 高砂香料工业株式会社 | 不对称氢化催化剂 |
| WO2012069422A1 (en) * | 2010-11-26 | 2012-05-31 | Lonza Ltd | 3-(2,3-dimethylphenyl)-2-butenal and its use as perfume |
| CN103328431B (zh) * | 2011-01-19 | 2015-05-06 | 帝斯曼知识产权资产管理有限公司 | 通过催化碳碳双键加氢制备4-乙酰氧基-2-甲基丁醛的方法 |
| WO2012120070A1 (en) * | 2011-03-10 | 2012-09-13 | Lonza Ltd | Method for preparation of 3-(2,3-dimethylphenyl)-2-butenal |
| WO2013014428A1 (en) * | 2011-07-22 | 2013-01-31 | Cambrex Karlskoga Ab | New processes for preparing 4-substituted imidazoles |
| WO2012172119A2 (en) * | 2012-05-08 | 2012-12-20 | Lonza Ltd | Method for the preparation of medetomidine |
| WO2012172120A2 (en) * | 2012-05-08 | 2012-12-20 | Lonza Ltd | 2-(2,3-dimethylphenyl)-1-propanal and its use as perfume |
| ES2557638T3 (es) * | 2012-05-08 | 2016-01-27 | Lonza Ltd | Método para la preparación de 2-(2,3-dimetilfenil)-1-propanal |
-
2015
- 2015-01-30 GB GBGB1501593.6A patent/GB201501593D0/en not_active Ceased
-
2016
- 2016-01-29 JP JP2017540562A patent/JP6702623B2/ja active Active
- 2016-01-29 ES ES16706396T patent/ES2716748T3/es active Active
- 2016-01-29 KR KR1020177023707A patent/KR102458638B1/ko active Active
- 2016-01-29 WO PCT/GB2016/050204 patent/WO2016120635A1/en not_active Ceased
- 2016-01-29 TR TR2019/02673T patent/TR201902673T4/tr unknown
- 2016-01-29 EP EP16706396.5A patent/EP3250556B1/en active Active
- 2016-01-29 CN CN201680012547.0A patent/CN107428648B/zh active Active
- 2016-01-29 HR HRP20190286TT patent/HRP20190286T1/hr unknown
- 2016-01-29 US US15/547,288 patent/US10053420B2/en active Active
- 2016-01-29 DK DK16706396.5T patent/DK3250556T3/en active
- 2016-01-29 HU HUE16706396A patent/HUE042626T2/hu unknown
- 2016-01-29 PL PL16706396T patent/PL3250556T3/pl unknown
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