JP5352477B2 - 2,4−ジヒドロキシフェニル−4−メトキシベンジルケトン類を調製する方法 - Google Patents
2,4−ジヒドロキシフェニル−4−メトキシベンジルケトン類を調製する方法 Download PDFInfo
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- JP5352477B2 JP5352477B2 JP2009550235A JP2009550235A JP5352477B2 JP 5352477 B2 JP5352477 B2 JP 5352477B2 JP 2009550235 A JP2009550235 A JP 2009550235A JP 2009550235 A JP2009550235 A JP 2009550235A JP 5352477 B2 JP5352477 B2 JP 5352477B2
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- alkoxy
- hydrogen
- dihydroxyphenyl
- hydrogen fluoride
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- 238000004519 manufacturing process Methods 0.000 title claims description 5
- GNJTUNGQOITXTK-UHFFFAOYSA-N 1,3-bis(2,4-dihydroxyphenyl)-1,3-bis(4-methoxyphenyl)propan-2-one Chemical class C1=CC(OC)=CC=C1C(C=1C(=CC(O)=CC=1)O)C(=O)C(C=1C(=CC(O)=CC=1)O)C1=CC=C(OC)C=C1 GNJTUNGQOITXTK-UHFFFAOYSA-N 0.000 title 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims description 19
- 229910052801 chlorine Inorganic materials 0.000 claims description 18
- 239000000460 chlorine Substances 0.000 claims description 18
- 229910052731 fluorine Inorganic materials 0.000 claims description 18
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 claims description 18
- 229910000040 hydrogen fluoride Inorganic materials 0.000 claims description 17
- 229910052794 bromium Inorganic materials 0.000 claims description 16
- 239000001257 hydrogen Substances 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 13
- 238000006243 chemical reaction Methods 0.000 claims description 12
- NRPFNQUDKRYCNX-UHFFFAOYSA-N 4-methoxyphenylacetic acid Chemical compound COC1=CC=C(CC(O)=O)C=C1 NRPFNQUDKRYCNX-UHFFFAOYSA-N 0.000 claims description 10
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 10
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 10
- 239000011737 fluorine Substances 0.000 claims description 10
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 9
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 9
- XHBZOAYMBBUURD-UHFFFAOYSA-N 1-(2,4-Dihydroxyphenyl)-2-(4-methoxyphenyl)ethanone Chemical compound C1=CC(OC)=CC=C1CC(=O)C1=CC=C(O)C=C1O XHBZOAYMBBUURD-UHFFFAOYSA-N 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 8
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 7
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 239000003085 diluting agent Substances 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical class OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 claims description 4
- CXJOONIFSVSFAD-UHFFFAOYSA-N 2-(4-methoxyphenyl)acetyl chloride Chemical compound COC1=CC=C(CC(Cl)=O)C=C1 CXJOONIFSVSFAD-UHFFFAOYSA-N 0.000 claims description 3
- 239000002841 Lewis acid Substances 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 150000007517 lewis acids Chemical class 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 6
- GAMYVSCDDLXAQW-AOIWZFSPSA-N Thermopsosid Natural products O(C)c1c(O)ccc(C=2Oc3c(c(O)cc(O[C@H]4[C@H](O)[C@@H](O)[C@H](O)[C@H](CO)O4)c3)C(=O)C=2)c1 GAMYVSCDDLXAQW-AOIWZFSPSA-N 0.000 claims 1
- 229930003944 flavone Natural products 0.000 claims 1
- 150000002212 flavone derivatives Chemical class 0.000 claims 1
- 235000011949 flavones Nutrition 0.000 claims 1
- VHBFFQKBGNRLFZ-UHFFFAOYSA-N vitamin p Natural products O1C2=CC=CC=C2C(=O)C=C1C1=CC=CC=C1 VHBFFQKBGNRLFZ-UHFFFAOYSA-N 0.000 claims 1
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 6
- 150000002431 hydrogen Chemical class 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- -1 for example Natural products 0.000 description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 125000005415 substituted alkoxy group Chemical group 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- OTKCEEWUXHVZQI-UHFFFAOYSA-N 1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(=O)CC1=CC=CC=C1 OTKCEEWUXHVZQI-UHFFFAOYSA-N 0.000 description 2
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 238000005863 Friedel-Crafts acylation reaction Methods 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 229910003902 SiCl 4 Inorganic materials 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- ZZIALNLLNHEQPJ-UHFFFAOYSA-N coumestrol Chemical compound C1=C(O)C=CC2=C1OC(=O)C1=C2OC2=CC(O)=CC=C12 ZZIALNLLNHEQPJ-UHFFFAOYSA-N 0.000 description 2
- ZQSIJRDFPHDXIC-UHFFFAOYSA-N daidzein Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(O)=CC=C2C1=O ZQSIJRDFPHDXIC-UHFFFAOYSA-N 0.000 description 2
- HKQYGTCOTHHOMP-UHFFFAOYSA-N formononetin Chemical compound C1=CC(OC)=CC=C1C1=COC2=CC(O)=CC=C2C1=O HKQYGTCOTHHOMP-UHFFFAOYSA-N 0.000 description 2
- SUSQOBVLVYHIEX-UHFFFAOYSA-N phenylacetonitrile Chemical compound N#CCC1=CC=CC=C1 SUSQOBVLVYHIEX-UHFFFAOYSA-N 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- JAUFWTSSYRTLLB-UHFFFAOYSA-N (2-phenylacetyl) 2-phenylacetate Chemical compound C=1C=CC=CC=1CC(=O)OC(=O)CC1=CC=CC=C1 JAUFWTSSYRTLLB-UHFFFAOYSA-N 0.000 description 1
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- 238000003309 Hoesch reaction Methods 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 229910021617 Indium monochloride Inorganic materials 0.000 description 1
- 229910004013 NO 2 Inorganic materials 0.000 description 1
- 229910018287 SbF 5 Inorganic materials 0.000 description 1
- 235000000126 Styrax benzoin Nutrition 0.000 description 1
- 244000028419 Styrax benzoin Species 0.000 description 1
- 235000008411 Sumatra benzointree Nutrition 0.000 description 1
- ISAKRJDGNUQOIC-UHFFFAOYSA-N Uracil Chemical compound O=C1C=CNC(=O)N1 ISAKRJDGNUQOIC-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 235000007240 daidzein Nutrition 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- RIKPNWPEMPODJD-UHFFFAOYSA-N formononetin Natural products C1=CC(OC)=CC=C1C1=COC2=CC=CC=C2C1=O RIKPNWPEMPODJD-UHFFFAOYSA-N 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- TZBJGXHYKVUXJN-UHFFFAOYSA-N genistein Natural products C1=CC(O)=CC=C1C1=COC2=CC(O)=CC(O)=C2C1=O TZBJGXHYKVUXJN-UHFFFAOYSA-N 0.000 description 1
- 235000006539 genistein Nutrition 0.000 description 1
- 229940045109 genistein Drugs 0.000 description 1
- ZCOLJUOHXJRHDI-CMWLGVBASA-N genistein 7-O-beta-D-glucoside Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=CC(O)=C2C(=O)C(C=3C=CC(O)=CC=3)=COC2=C1 ZCOLJUOHXJRHDI-CMWLGVBASA-N 0.000 description 1
- 235000019382 gum benzoic Nutrition 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- APHGZSBLRQFRCA-UHFFFAOYSA-M indium(1+);chloride Chemical compound [In]Cl APHGZSBLRQFRCA-UHFFFAOYSA-M 0.000 description 1
- 239000002608 ionic liquid Substances 0.000 description 1
- CJWQYWQDLBZGPD-UHFFFAOYSA-N isoflavone Natural products C1=C(OC)C(OC)=CC(OC)=C1C1=COC2=C(C=CC(C)(C)O3)C3=C(OC)C=C2C1=O CJWQYWQDLBZGPD-UHFFFAOYSA-N 0.000 description 1
- 150000002515 isoflavone derivatives Chemical class 0.000 description 1
- 235000008696 isoflavones Nutrition 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 230000000269 nucleophilic effect Effects 0.000 description 1
- 229960003424 phenylacetic acid Drugs 0.000 description 1
- 239000003279 phenylacetic acid Substances 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- KAKQVSNHTBLJCH-UHFFFAOYSA-N trifluoromethanesulfonimidic acid Chemical compound NS(=O)(=O)C(F)(F)F KAKQVSNHTBLJCH-UHFFFAOYSA-N 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
- C07C45/46—Friedel-Crafts reactions
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Pyrane Compounds (AREA)
Description
R1及びR2は、それぞれ、水素、塩素、フッ素、臭素、ヨウ素、CF3、メチル、メトキシ、場合により置換されていてもよいアルコキシ、−OCF3、−C(CH3)3、−CH2(CH3)2、−CH(CH3)2であり;
R3は、水素、Cl、F、Br、場合により置換されていてもよいアルキル、場合により置換されていてもよいアルコキシ、−C(CH3)3であり;及び、
Xは、ヒドロキシル、F、Cl、場合により置換されていてもよいアルコキシ又はBrである。]
で表される2,4−ジヒドロキシフェニル4−メトキシベンジルケトンを高収率及び高純度で合成することが可能であるということが分かった。
1−(2,4−ジヒドロキシフェニル)−2−(4−メトキシフェニル)−エタノンの調製
オートクレーブの中に、−10℃で、4−メトキシフェニル酢酸(83.9g)、レゾルシノール(55g)及びフッ化水素(450g)を最初に入れ、得られた混合物を20℃で12時間撹拌する。次いで、40℃でフッ化水素を留去し、沈澱物を水で洗浄し、乾燥させる。
オートクレーブの中に、−10℃で、4−メトキシフェニルアセチルクロリド(93g)、レゾルシノール(55g)及びフッ化水素(450g)を最初に入れ、得られた混合物を20℃で12時間撹拌する。次いで、40℃でフッ化水素を留去し、沈澱物を水で洗浄し、乾燥させる。
オートクレーブの中に、−10℃で、4−メトキシフェニル酢酸(83.9g)、レゾルシノール(55g)及びフッ化水素(300g)を最初に入れ、得られた混合物を20℃で12時間撹拌する。次いで、40℃でフッ化水素を留去し、沈澱物を水で洗浄し、乾燥させる。
Claims (9)
- 式(I)
R1及びR2は、それぞれ、水素、塩素、フッ素、臭素、ヨウ素、CF3、メチル、アルコキシ、−OCF3、−C(CH3)3、−CH 2 (CH 3 )、−CH(CH3)2であり;及び、
R3は、水素、Cl、F、Br、アルキル、アルコキシ、−C(CH3)3である。]
で表される2,4−ジヒドロキシフェニル4−メトキシベンジルケトンを調製する方法であって、式(II)
R 1 及びR 2 は、上記のとおりであり、
Xは、ヒドロキシル、F、Cl、Br、アルコキシである。]
で表されるフェニル酢酸誘導体をフッ化水素の中、さらなる希釈剤の非存在下で、
式(III)
で表されるフェノールと反応させることによる、前記方法。 - R1及びR2が、それぞれ、水素、塩素、フッ素、臭素、ヨウ素、CF3、メチル、C1−C6−アルコキシ、−OCF3、−C(CH3)3、−CH 2 (CH 3 )、−CH(CH3)2であり;
R3が、水素、Cl、F、Br、C1−C6−アルキル、C1−C6−アルコキシ、−C(CH3)3であり;及び、
Xが、ヒドロキシル、F、C1、Br、C1−C6−アルコキシである;
請求項1に記載の方法。 - R1及びR2が、それぞれ、水素、塩素、フッ素、臭素、ヨウ素、CF3、メチル、C1−C4−アルコキシ、−C(CH3)3、−CH 2 (CH 3 )、−CH(CH3)2であり;
R3が、水素、Cl、F、Br、C1−C6−アルキル、C1−C4−アルコキシ、−C(CH3)3であり;及び、
Xが、ヒドロキシル、F、Cl、C1−C4−アルコキシである;
請求項1に記載の方法。 - 1−(2,4−ジヒドロキシフェニル)−2−(4−メトキシフェニル)エタノンを調製する方法であって、4−メトキシフェニル酢酸又は4−メトキシフェニルアセチルクロリドを、さらなる希釈剤の非存在下で、レゾルシノール及びフッ化水素と反応させることを特徴とする、前記方法。
- フッ化水素と式(III)で表されるフェノールのモル比が50:1〜10:1の範囲内にあることを特徴とする、請求項1に記載の方法。
- 反応温度が10℃〜50℃であることを特徴とする、請求項1に記載の方法。
- 反応をルイス酸の存在下で進行させることを特徴とする、請求項1に記載の方法。
- 1−(2,4−ジヒドロキシフェニル)−2−(4−メトキシフェニル)エタノンを調製する方法であって、4−メトキシフェニル酢酸又は4−メトキシフェニルアセチルクロリドを、さらなる希釈剤の非存在下で、レゾルシノール及びフッ化水素(ここで、フッ化水素とレゾルシノールのモル比は50:1〜10:1の範囲内にある。)と0℃〜40℃の範囲内にある温度で反応させることを特徴とする、前記方法。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP07003860.9 | 2007-02-26 | ||
EP07003860A EP1961727A1 (de) | 2007-02-26 | 2007-02-26 | Verfahren zur Herstellung von 2,4-Dihydroxyphenyl-4-methoxybenzyl-ketonen |
PCT/EP2008/001203 WO2008104297A1 (de) | 2007-02-26 | 2008-02-16 | Verfahren zur herstellung von 2,4-dihydroxyphenyl-4-methoxybenzyl-ketonen |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2010519231A JP2010519231A (ja) | 2010-06-03 |
JP5352477B2 true JP5352477B2 (ja) | 2013-11-27 |
Family
ID=38267561
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2009550235A Expired - Fee Related JP5352477B2 (ja) | 2007-02-26 | 2008-02-16 | 2,4−ジヒドロキシフェニル−4−メトキシベンジルケトン類を調製する方法 |
Country Status (8)
Country | Link |
---|---|
US (1) | US8324431B2 (ja) |
EP (2) | EP1961727A1 (ja) |
JP (1) | JP5352477B2 (ja) |
CN (1) | CN101610989B (ja) |
ES (1) | ES2623432T3 (ja) |
IL (1) | IL199931A (ja) |
TW (1) | TWI410401B (ja) |
WO (1) | WO2008104297A1 (ja) |
Family Cites Families (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2616479C2 (de) * | 1976-04-14 | 1986-12-04 | Brickl, Rolf, Dr., 7951 Warthausen | Substituierte Fluoracylresorcine, Verfahren zu ihrer Herstellung und diese enthaltende Arzneimittel und Kosmetika |
DE2616986A1 (de) * | 1976-04-17 | 1977-10-27 | Bayer Ag | Verfahren zur herstellung von hydroxyketonen |
US4269965A (en) * | 1979-09-17 | 1981-05-26 | E. I. Du Pont De Nemours And Company | Aromatic polyester which forms optically anisotropic melts and filaments thereof |
FR2519975A1 (fr) * | 1982-01-21 | 1983-07-22 | Rhone Poulenc Spec Chim | Procede de preparation de trifluoromethoxy ou trifluoromethylthiophenylcetones |
JPS60188343A (ja) * | 1984-03-07 | 1985-09-25 | Mitsubishi Gas Chem Co Inc | 芳香族ケトンの製造法 |
IT1196264B (it) * | 1984-09-24 | 1988-11-16 | Blaschim Spa | Procedimento per preparare arilalchilchetoni |
ES2029883T3 (es) * | 1987-06-19 | 1992-10-01 | Eli Lilly And Company | Procedimiento para preparar intermedios para antagonistas de leucotrienos. |
AU632117B2 (en) * | 1990-04-18 | 1992-12-17 | Chinoin Gyogyszer Es Vegyeszeti Termekek Gyara | Improved process for the preparation of ketone compounds |
US5981775A (en) * | 1998-09-16 | 1999-11-09 | Board Of Trustees Operating Michigan State University | Process for the preparation of isoflavones |
WO2005054169A1 (en) | 2003-12-08 | 2005-06-16 | Hanbul Cosmetic Co., Ltd. | Preparation method of 2-phenylacetophenone derivatives |
US20060129002A1 (en) * | 2004-12-15 | 2006-06-15 | Honeywell International Inc. | Process for the synthesis of alkylresorcinols |
-
2007
- 2007-02-26 EP EP07003860A patent/EP1961727A1/de not_active Ceased
-
2008
- 2008-02-16 ES ES08715804.4T patent/ES2623432T3/es active Active
- 2008-02-16 JP JP2009550235A patent/JP5352477B2/ja not_active Expired - Fee Related
- 2008-02-16 WO PCT/EP2008/001203 patent/WO2008104297A1/de active Application Filing
- 2008-02-16 US US12/525,023 patent/US8324431B2/en active Active
- 2008-02-16 EP EP08715804.4A patent/EP2114847B1/de not_active Not-in-force
- 2008-02-16 CN CN200880004683.0A patent/CN101610989B/zh not_active Expired - Fee Related
- 2008-02-25 TW TW097106390A patent/TWI410401B/zh not_active IP Right Cessation
-
2009
- 2009-07-16 IL IL199931A patent/IL199931A/en active IP Right Grant
Also Published As
Publication number | Publication date |
---|---|
US8324431B2 (en) | 2012-12-04 |
WO2008104297A1 (de) | 2008-09-04 |
IL199931A (en) | 2012-12-31 |
US20100121082A1 (en) | 2010-05-13 |
EP1961727A1 (de) | 2008-08-27 |
JP2010519231A (ja) | 2010-06-03 |
TW200846313A (en) | 2008-12-01 |
EP2114847B1 (de) | 2017-03-22 |
TWI410401B (zh) | 2013-10-01 |
IL199931A0 (en) | 2010-04-15 |
ES2623432T3 (es) | 2017-07-11 |
CN101610989A (zh) | 2009-12-23 |
EP2114847A1 (de) | 2009-11-11 |
CN101610989B (zh) | 2013-05-15 |
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