JP4437093B2 - 3−[2−(3,4−ジメトキシ−ベンゾイル)−4,5−ジメトキシ−フェニル]−ペンタン−2−オンの製法 - Google Patents
3−[2−(3,4−ジメトキシ−ベンゾイル)−4,5−ジメトキシ−フェニル]−ペンタン−2−オンの製法 Download PDFInfo
- Publication number
- JP4437093B2 JP4437093B2 JP2004559931A JP2004559931A JP4437093B2 JP 4437093 B2 JP4437093 B2 JP 4437093B2 JP 2004559931 A JP2004559931 A JP 2004559931A JP 2004559931 A JP2004559931 A JP 2004559931A JP 4437093 B2 JP4437093 B2 JP 4437093B2
- Authority
- JP
- Japan
- Prior art keywords
- general formula
- dimethoxy
- compound
- process according
- compound represented
- 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.)
- Expired - Fee Related
Links
- ZWUMDFWFKWDFBI-UHFFFAOYSA-N 3-[2-(3,4-dimethoxybenzoyl)-4,5-dimethoxyphenyl]pentan-2-one Chemical compound CCC(C(C)=O)C1=CC(OC)=C(OC)C=C1C(=O)C1=CC=C(OC)C(OC)=C1 ZWUMDFWFKWDFBI-UHFFFAOYSA-N 0.000 title claims description 12
- 238000002360 preparation method Methods 0.000 title claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 57
- 238000000034 method Methods 0.000 claims description 30
- 238000006243 chemical reaction Methods 0.000 claims description 18
- 229910052783 alkali metal Inorganic materials 0.000 claims description 17
- 150000001340 alkali metals Chemical group 0.000 claims description 17
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 claims description 10
- 150000002681 magnesium compounds Chemical class 0.000 claims description 10
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 9
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical group [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 7
- 230000015572 biosynthetic process Effects 0.000 claims description 7
- 229910052749 magnesium Inorganic materials 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 239000011541 reaction mixture Substances 0.000 claims description 6
- 125000002947 alkylene group Chemical group 0.000 claims description 4
- 238000002955 isolation Methods 0.000 claims description 4
- CETVQRFGPOGIQJ-UHFFFAOYSA-N lithium;hexane Chemical compound [Li+].CCCCC[CH2-] CETVQRFGPOGIQJ-UHFFFAOYSA-N 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 150000007522 mineralic acids Chemical class 0.000 claims description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 3
- 230000007062 hydrolysis Effects 0.000 claims description 3
- 238000006460 hydrolysis reaction Methods 0.000 claims description 3
- 229910052744 lithium Inorganic materials 0.000 claims description 3
- 239000002994 raw material Substances 0.000 claims description 3
- 239000005977 Ethylene Substances 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 238000011065 in-situ storage Methods 0.000 claims description 2
- 238000006467 substitution reaction Methods 0.000 claims description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims 1
- 150000002641 lithium Chemical group 0.000 claims 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 17
- -1 3,4-dimethoxy-benzoyl Chemical group 0.000 description 14
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- LNWAOJCHFJZVPU-UHFFFAOYSA-N 3-[2-(3,4-dimethoxybenzoyl)-4,5-dimethoxyphenyl]pentan-2-one;ethene Chemical group C=C.CCC(C(C)=O)C1=CC(OC)=C(OC)C=C1C(=O)C1=CC=C(OC)C(OC)=C1 LNWAOJCHFJZVPU-UHFFFAOYSA-N 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 238000001953 recrystallisation Methods 0.000 description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- RUJBDQSFYCKFAA-UHFFFAOYSA-N Tofisopam Chemical compound N=1N=C(C)C(CC)C2=CC(OC)=C(OC)C=C2C=1C1=CC=C(OC)C(OC)=C1 RUJBDQSFYCKFAA-UHFFFAOYSA-N 0.000 description 4
- WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- DAUAQNGYDSHRET-UHFFFAOYSA-N 3,4-dimethoxybenzoic acid Chemical compound COC1=CC=C(C(O)=O)C=C1OC DAUAQNGYDSHRET-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- GPVDHNVGGIAOQT-UHFFFAOYSA-N Veratric acid Natural products COC1=CC=C(C(O)=O)C(OC)=C1 GPVDHNVGGIAOQT-UHFFFAOYSA-N 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- 150000002642 lithium compounds Chemical class 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 229960002501 tofisopam Drugs 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- WSSLDBVWUSSAGE-UHFFFAOYSA-N 3,4-dimethoxy-n,n-dimethylbenzamide Chemical compound COC1=CC=C(C(=O)N(C)C)C=C1OC WSSLDBVWUSSAGE-UHFFFAOYSA-N 0.000 description 2
- VIOBGCWEHLRBEP-UHFFFAOYSA-N 3,4-dimethoxybenzoyl chloride Chemical compound COC1=CC=C(C(Cl)=O)C=C1OC VIOBGCWEHLRBEP-UHFFFAOYSA-N 0.000 description 2
- BLWGLUGFLOPVHX-UHFFFAOYSA-N 3-(2-bromo-4,5-dimethoxyphenyl)pentan-2-one Chemical compound CCC(C(C)=O)C1=CC(OC)=C(OC)C=C1Br BLWGLUGFLOPVHX-UHFFFAOYSA-N 0.000 description 2
- RUEQJZPDBYLHPF-UHFFFAOYSA-N 3-(2-bromo-4,5-dimethoxyphenyl)pentan-2-one;ethene Chemical group C=C.CCC(C(C)=O)C1=CC(OC)=C(OC)C=C1Br RUEQJZPDBYLHPF-UHFFFAOYSA-N 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 150000001805 chlorine compounds Chemical class 0.000 description 2
- JPBGLQJDCUZXEF-UHFFFAOYSA-N chromenylium Chemical class [O+]1=CC=CC2=CC=CC=C21 JPBGLQJDCUZXEF-UHFFFAOYSA-N 0.000 description 2
- 150000001844 chromium Chemical class 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- BIGQPYZPEWAPBG-UHFFFAOYSA-N methyl 3,4-dimethoxybenzoate Chemical compound COC(=O)C1=CC=C(OC)C(OC)=C1 BIGQPYZPEWAPBG-UHFFFAOYSA-N 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 0 *c(c(*)c1)ccc1C(O*)=O Chemical compound *c(c(*)c1)ccc1C(O*)=O 0.000 description 1
- QSAOUEJSHLKIOA-UHFFFAOYSA-N 1-(2-bromo-4,5-dimethoxyphenyl)pentan-2-one Chemical compound BrC1=C(C=C(C(=C1)OC)OC)CC(CCC)=O QSAOUEJSHLKIOA-UHFFFAOYSA-N 0.000 description 1
- VYRHYSCIJYOTJB-UHFFFAOYSA-N 1-(3,4-dimethoxyphenyl)-4-ethyl-6,7-dimethoxy-3-methyl-3,4-dihydro-1h-isochromene Chemical compound C12=CC(OC)=C(OC)C=C2C(CC)C(C)OC1C1=CC=C(OC)C(OC)=C1 VYRHYSCIJYOTJB-UHFFFAOYSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- 125000006416 CBr Chemical group BrC* 0.000 description 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 1
- 238000003747 Grignard reaction Methods 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- KYOIPUDHYRWSFO-UHFFFAOYSA-N [Br].[Li] Chemical group [Br].[Li] KYOIPUDHYRWSFO-UHFFFAOYSA-N 0.000 description 1
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 1
- REDXJYDRNCIFBQ-UHFFFAOYSA-N aluminium(3+) Chemical compound [Al+3] REDXJYDRNCIFBQ-UHFFFAOYSA-N 0.000 description 1
- 239000002249 anxiolytic agent Substances 0.000 description 1
- 230000000949 anxiolytic effect Effects 0.000 description 1
- 239000011260 aqueous acid Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 235000011089 carbon dioxide Nutrition 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 150000002466 imines Chemical class 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000002183 isoquinolinyl group Chemical class C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- KRKPYFLIYNGWTE-UHFFFAOYSA-N n,o-dimethylhydroxylamine Chemical compound CNOC KRKPYFLIYNGWTE-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Images
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
- C07C45/455—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation with carboxylic acids or their derivatives
-
- 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
- C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
- C07C45/511—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups
- C07C45/515—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups the singly bound functional group being an acetalised, ketalised hemi-acetalised, or hemi-ketalised hydroxyl group
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/29—Saturated compounds containing keto groups bound to rings
- C07C49/35—Saturated compounds containing keto groups bound to rings containing ether groups, groups, groups, or groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU0204342A HU227044B1 (en) | 2002-12-16 | 2002-12-16 | Process for producing 3-[2-(3,4-dimethoxybenzoyl)-4,5-dimethoxyphenyl]-pentan-2-one |
| PCT/HU2002/000178 WO2004054951A1 (en) | 2002-12-16 | 2002-12-31 | Process for the preparation of 3-[2-(3,4-dimethoxy-benzoyl)-4,5-dimethoxy-phenyl]-pentan-2-one |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2006509814A JP2006509814A (ja) | 2006-03-23 |
| JP4437093B2 true JP4437093B2 (ja) | 2010-03-24 |
Family
ID=89981000
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2004559931A Expired - Fee Related JP4437093B2 (ja) | 2002-12-16 | 2002-12-31 | 3−[2−(3,4−ジメトキシ−ベンゾイル)−4,5−ジメトキシ−フェニル]−ペンタン−2−オンの製法 |
Country Status (12)
| Country | Link |
|---|---|
| EP (1) | EP1575890A1 (cs) |
| JP (1) | JP4437093B2 (cs) |
| KR (1) | KR100936306B1 (cs) |
| AU (2) | AU2002361068A1 (cs) |
| BG (1) | BG109230A (cs) |
| CZ (1) | CZ2005388A3 (cs) |
| EA (1) | EA007788B1 (cs) |
| HU (1) | HU227044B1 (cs) |
| PL (1) | PL376530A1 (cs) |
| SK (1) | SK702005A3 (cs) |
| UA (1) | UA78634C2 (cs) |
| WO (2) | WO2004054951A1 (cs) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100714181B1 (ko) * | 2005-07-04 | 2007-05-04 | 주식회사 자동기 | 제설재 살포기용 연료공급장치 |
| CN104098482B (zh) * | 2013-04-12 | 2016-04-20 | 江苏英力科技发展有限公司 | 一种3,4-二甲氧基-n,n-二甲基苯甲酰胺的制备方法 |
| CN104262128B (zh) * | 2014-09-04 | 2016-04-13 | 山东金城医药化工股份有限公司 | 托非索泮中间体的制备方法 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HU194529B (en) * | 1984-07-20 | 1988-02-29 | Gyogyszerkutato Intezet | New process for producing 2-aroyl-phenylacetone-derivatives |
| AU2002348942A1 (en) * | 2001-12-13 | 2003-06-23 | Egis Gyogyszergyar Rt. | Process for the preparation of tofisopam and new intermediates |
-
2002
- 2002-12-16 HU HU0204342A patent/HU227044B1/hu not_active IP Right Cessation
- 2002-12-31 EP EP02791921A patent/EP1575890A1/en not_active Withdrawn
- 2002-12-31 SK SK70-2005A patent/SK702005A3/sk unknown
- 2002-12-31 AU AU2002361068A patent/AU2002361068A1/en not_active Abandoned
- 2002-12-31 PL PL376530A patent/PL376530A1/pl not_active IP Right Cessation
- 2002-12-31 EA EA200500966A patent/EA007788B1/ru not_active IP Right Cessation
- 2002-12-31 WO PCT/HU2002/000178 patent/WO2004054951A1/en active Application Filing
- 2002-12-31 CZ CZ2005388A patent/CZ2005388A3/cs unknown
- 2002-12-31 JP JP2004559931A patent/JP4437093B2/ja not_active Expired - Fee Related
- 2002-12-31 UA UAA200507059A patent/UA78634C2/uk unknown
- 2002-12-31 KR KR1020057011012A patent/KR100936306B1/ko not_active Expired - Fee Related
-
2003
- 2003-12-16 WO PCT/HU2003/000104 patent/WO2004054952A1/en not_active Application Discontinuation
- 2003-12-16 AU AU2003292449A patent/AU2003292449A1/en not_active Abandoned
-
2005
- 2005-07-14 BG BG109230A patent/BG109230A/bg unknown
Also Published As
| Publication number | Publication date |
|---|---|
| HUP0204342A3 (en) | 2004-11-29 |
| HU227044B1 (en) | 2010-05-28 |
| KR100936306B1 (ko) | 2010-01-12 |
| AU2002361068A1 (en) | 2004-07-09 |
| AU2003292449A1 (en) | 2004-07-09 |
| CZ2005388A3 (cs) | 2005-09-14 |
| WO2004054951A1 (en) | 2004-07-01 |
| EA200500966A1 (ru) | 2005-12-29 |
| PL376530A1 (pl) | 2006-01-09 |
| SK702005A3 (sk) | 2005-09-08 |
| BG109230A (bg) | 2006-04-28 |
| EP1575890A1 (en) | 2005-09-21 |
| HU0204342D0 (en) | 2003-02-28 |
| EA007788B1 (ru) | 2007-02-27 |
| HUP0204342A2 (hu) | 2004-07-28 |
| UA78634C2 (en) | 2007-04-10 |
| WO2004054952A1 (en) | 2004-07-01 |
| KR20050085686A (ko) | 2005-08-29 |
| JP2006509814A (ja) | 2006-03-23 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP3411036B2 (ja) | リグナン系化合物の製造方法 | |
| JP4437093B2 (ja) | 3−[2−(3,4−ジメトキシ−ベンゾイル)−4,5−ジメトキシ−フェニル]−ペンタン−2−オンの製法 | |
| JP4892472B2 (ja) | 5−クロロ−2,4−ジヒドロキシピリジンの製造方法 | |
| JP3407082B2 (ja) | アミノメチルピリジン誘導体の製造方法及びその中間体 | |
| JPS6055510B2 (ja) | 4−(p−フルオルベンゾイル)−1−〔3−(p−フルオルベンゾイル)プロピル〕ピペリジンとその酸付加塩の製造方法 | |
| WO1995022533A1 (en) | Process for producing 3-isoxazolecarboxylic acid | |
| JP3097678B2 (ja) | アファノルフィン中間体 | |
| JPS584698B2 (ja) | 2−(3−ベンゾイルフエニル)プロピオン酸の製造方法 | |
| JPH0363247A (ja) | 2―アルキル―3―アルコキシカルボニルメチルシクロペンタノンの製造法 | |
| JP3856241B2 (ja) | 1(2h)−キノリンカルボン酸の新規な誘導体、その合成方法及び抗生剤作用を有する化合物を合成するためのその使用方法 | |
| JP2986003B2 (ja) | 2−アルキル−3−スチリルオキシランカルボン酸エステル及びその製法 | |
| JPS58162585A (ja) | α−アシルラクトン類の製造方法 | |
| JPH07145098A (ja) | アルコキシル基含有化合物 | |
| JPS6241510B2 (cs) | ||
| JP3896557B2 (ja) | 2’−アルキル−3’−メトキシアセトフェノンアセタール誘導体 | |
| JPH0899953A (ja) | 新規ハロケタール化合物 | |
| JPH11302216A (ja) | ジアルコキシ置換インダノン誘導体の製造方法 | |
| JP2003160576A (ja) | 4h−ピラン−4−オンの簡便な製造 | |
| JPH0753704B2 (ja) | フェニルマロン酸モノアニリド誘導体および3―フェニル―2―キノロン誘導体の製造方法 | |
| SK2792004A3 (en) | Process for the preparation of tofisopam and new intermediates | |
| JPH0789891A (ja) | ヒドロキシベンズアルデヒド誘導体の製造方法 | |
| JPS59112975A (ja) | 4−置換イソオキサゾ−ル類の製造法 | |
| JPS62895B2 (cs) | ||
| JPS62896B2 (cs) | ||
| JPS6365671B2 (cs) |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20051227 |
|
| A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20090127 |
|
| A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20090422 |
|
| A602 | Written permission of extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A602 Effective date: 20090430 |
|
| TRDD | Decision of grant or rejection written | ||
| A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20091201 |
|
| A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 |
|
| A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20091228 |
|
| A602 | Written permission of extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A602 Effective date: 20100106 |
|
| A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20100104 |
|
| R150 | Certificate of patent or registration of utility model |
Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20130108 Year of fee payment: 3 |
|
| LAPS | Cancellation because of no payment of annual fees |