JP2013520495A5 - - Google Patents
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- Publication number
- JP2013520495A5 JP2013520495A5 JP2012554971A JP2012554971A JP2013520495A5 JP 2013520495 A5 JP2013520495 A5 JP 2013520495A5 JP 2012554971 A JP2012554971 A JP 2012554971A JP 2012554971 A JP2012554971 A JP 2012554971A JP 2013520495 A5 JP2013520495 A5 JP 2013520495A5
- Authority
- JP
- Japan
- Prior art keywords
- compound
- formula
- organic solvent
- give
- bisphenol
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 claims 20
- 150000001875 compounds Chemical class 0.000 claims 16
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 8
- VVOAZFWZEDHOOU-UHFFFAOYSA-N magnolol Chemical compound OC1=CC=C(CC=C)C=C1C1=CC(CC=C)=CC=C1O VVOAZFWZEDHOOU-UHFFFAOYSA-N 0.000 claims 8
- 239000003960 organic solvent Substances 0.000 claims 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims 4
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims 4
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 claims 4
- 239000012351 deprotecting agent Substances 0.000 claims 4
- 229910052749 magnesium Inorganic materials 0.000 claims 4
- 239000011777 magnesium Substances 0.000 claims 4
- XJUZRXYOEPSWMB-UHFFFAOYSA-N Chloromethyl methyl ether Chemical compound COCCl XJUZRXYOEPSWMB-UHFFFAOYSA-N 0.000 claims 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 3
- 238000006243 chemical reaction Methods 0.000 claims 3
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 claims 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 2
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 2
- 229910052794 bromium Inorganic materials 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 claims 1
- IMHDGJOMLMDPJN-UHFFFAOYSA-N biphenyl-2,2'-diol Chemical compound OC1=CC=CC=C1C1=CC=CC=C1O IMHDGJOMLMDPJN-UHFFFAOYSA-N 0.000 claims 1
- 230000008878 coupling Effects 0.000 claims 1
- 238000010168 coupling process Methods 0.000 claims 1
- 238000005859 coupling reaction Methods 0.000 claims 1
- 150000002009 diols Chemical class 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 150000007530 organic bases Chemical class 0.000 claims 1
- 0 **CC=CCc(cc1)cc(-c2cc(CC=*)ccc2O)c1O Chemical compound **CC=CCc(cc1)cc(-c2cc(CC=*)ccc2O)c1O 0.000 description 1
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PCT/US2010/025378 WO2011106003A1 (en) | 2010-02-25 | 2010-02-25 | Synthesis of magnolol and its analogue compounds |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014150683A Division JP2015007054A (ja) | 2014-07-24 | 2014-07-24 | マグノロールおよびその類似体化合物の合成 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2013520495A JP2013520495A (ja) | 2013-06-06 |
| JP2013520495A5 true JP2013520495A5 (enExample) | 2013-12-19 |
Family
ID=42028117
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2012554971A Pending JP2013520495A (ja) | 2010-02-25 | 2010-02-25 | マグノロールおよびその類似体化合物の合成 |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US8519197B2 (enExample) |
| EP (1) | EP2539310B1 (enExample) |
| JP (1) | JP2013520495A (enExample) |
| CN (1) | CN102884035B (enExample) |
| AR (1) | AR080656A1 (enExample) |
| AU (1) | AU2010346597B2 (enExample) |
| BR (1) | BR112012020603A2 (enExample) |
| CA (1) | CA2789140C (enExample) |
| DK (1) | DK2539310T3 (enExample) |
| ES (1) | ES2507615T3 (enExample) |
| MX (1) | MX2012009817A (enExample) |
| MY (1) | MY162466A (enExample) |
| PH (1) | PH12012501619A1 (enExample) |
| PL (1) | PL2539310T3 (enExample) |
| RU (1) | RU2510938C1 (enExample) |
| SG (1) | SG183120A1 (enExample) |
| TW (1) | TWI438185B (enExample) |
| WO (1) | WO2011106003A1 (enExample) |
| ZA (1) | ZA201206020B (enExample) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2010365812B2 (en) | 2010-12-21 | 2014-12-18 | Colgate-Palmolive Company | Halogenated biphenols as antibacterial agents |
| KR20140112481A (ko) | 2011-12-15 | 2014-09-23 | 콜게이트-파아므올리브캄파니 | 가용화된 마그놀롤 유사체 및 피피쥐-1-피이쥐-9 라우릴 글리콜 에테르를 함유하는 구강 위생 또는 클렌저 조성물 |
| AU2011383311B2 (en) | 2011-12-15 | 2014-08-21 | Colgate-Palmolive Company | Solubilized magnolol analogs |
| US9000231B2 (en) | 2011-12-20 | 2015-04-07 | Colgate-Palmolive Company | Processes for making magnolol and derivatives thereof |
| WO2013095364A1 (en) | 2011-12-20 | 2013-06-27 | Colgate-Palmolive Company | Processes for making magnolol analogs |
| AU2013374909B2 (en) | 2013-01-23 | 2015-10-15 | Colgate-Palmolive Company | Processes for making magnolol derivatives |
| JP2015007054A (ja) * | 2014-07-24 | 2015-01-15 | コルゲート・パーモリブ・カンパニーＣｏｌｇａｔｅ−Ｐａｌｍｏｌｉｖｅ Ｃｏｍｐａｎｙ | マグノロールおよびその類似体化合物の合成 |
| EP3364957B1 (en) * | 2015-10-23 | 2020-12-09 | Colgate-Palmolive Company | Improved synthesis of honokiol |
| CN109053387B (zh) * | 2018-09-19 | 2021-07-09 | 九江学院 | 一种厚朴酚的合成方法 |
| CN113242751B (zh) | 2018-12-18 | 2023-09-19 | 联合利华知识产权控股有限公司 | 抗微生物组合物 |
| CN115581690A (zh) * | 2021-07-05 | 2023-01-10 | 北京红惠新医药科技有限公司 | 厚朴酚或和厚朴酚的芳环氨基取代衍生物在用于制备抗心肌缺血药物中的应用、药物组合物 |
| CN116139115A (zh) * | 2021-11-19 | 2023-05-23 | 北京红惠新医药科技有限公司 | 厚朴酚和/或和厚朴酚芳环氨基取代类衍生物的抗低氧/缺氧损伤用途及药物组合物 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL116942A (en) * | 1991-11-25 | 2000-02-29 | Lilly Co Eli | 2-phenyl-4,5-disubstituted phenol derivatives as chemical intermediates for substituted phenyl phenol leukotriene antagonists |
| US6544409B2 (en) * | 2001-05-16 | 2003-04-08 | Petroleo Brasileiro S.A. - Petrobras | Process for the catalytic oxidation of sulfur, nitrogen and unsaturated compounds from hydrocarbon streams |
| CN1147286C (zh) * | 2001-07-18 | 2004-04-28 | 广州美晨股份有限公司 | 一种中药牙膏 |
| US7347985B2 (en) * | 2002-06-25 | 2008-03-25 | Wm. Wrigley Jr. Company | Breath freshening and oral cleansing product with magnolia bark extract |
| US20060140885A1 (en) | 2004-12-29 | 2006-06-29 | Abdul Gaffar | Method of reducing oral tissue inflammation using magnolia extract |
| WO2008098056A2 (en) * | 2007-02-06 | 2008-08-14 | Epix Pharmaceuticals, Inc. | High relaxivity chelates |
-
2010
- 2010-02-25 PH PH1/2012/501619A patent/PH12012501619A1/en unknown
- 2010-02-25 ES ES10705965.1T patent/ES2507615T3/es active Active
- 2010-02-25 SG SG2012056404A patent/SG183120A1/en unknown
- 2010-02-25 MX MX2012009817A patent/MX2012009817A/es active IP Right Grant
- 2010-02-25 CA CA2789140A patent/CA2789140C/en not_active Expired - Fee Related
- 2010-02-25 EP EP10705965.1A patent/EP2539310B1/en active Active
- 2010-02-25 BR BR112012020603A patent/BR112012020603A2/pt active Search and Examination
- 2010-02-25 CN CN201080064851.2A patent/CN102884035B/zh not_active Expired - Fee Related
- 2010-02-25 MY MYPI2012003487A patent/MY162466A/en unknown
- 2010-02-25 PL PL10705965T patent/PL2539310T3/pl unknown
- 2010-02-25 WO PCT/US2010/025378 patent/WO2011106003A1/en not_active Ceased
- 2010-02-25 DK DK10705965.1T patent/DK2539310T3/da active
- 2010-02-25 AU AU2010346597A patent/AU2010346597B2/en not_active Ceased
- 2010-02-25 RU RU2012140748/04A patent/RU2510938C1/ru not_active IP Right Cessation
- 2010-02-25 US US13/577,627 patent/US8519197B2/en active Active
- 2010-02-25 JP JP2012554971A patent/JP2013520495A/ja active Pending
-
2011
- 2011-02-24 AR ARP110100579A patent/AR080656A1/es unknown
- 2011-02-24 TW TW100106113A patent/TWI438185B/zh not_active IP Right Cessation
-
2012
- 2012-08-10 ZA ZA2012/06020A patent/ZA201206020B/en unknown
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