ZA200505574B - Method for the production of benzophenones - Google Patents
Method for the production of benzophenones Download PDFInfo
- Publication number
- ZA200505574B ZA200505574B ZA200505574A ZA200505574A ZA200505574B ZA 200505574 B ZA200505574 B ZA 200505574B ZA 200505574 A ZA200505574 A ZA 200505574A ZA 200505574 A ZA200505574 A ZA 200505574A ZA 200505574 B ZA200505574 B ZA 200505574B
- Authority
- ZA
- South Africa
- Prior art keywords
- diluent
- reaction
- ome
- acid chloride
- formula
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 27
- 239000012965 benzophenone Substances 0.000 title claims description 11
- 150000008366 benzophenones Chemical class 0.000 title claims description 8
- 238000004519 manufacturing process Methods 0.000 title claims description 8
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 39
- 239000003085 diluting agent Substances 0.000 claims description 27
- 238000006243 chemical reaction Methods 0.000 claims description 24
- 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 description 21
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 21
- 230000008569 process Effects 0.000 claims description 19
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 16
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 16
- 239000003054 catalyst Substances 0.000 claims description 12
- KCIZTNZGSBSSRM-UHFFFAOYSA-N 3,4,5-Trimethoxytoluene Chemical compound COC1=CC(C)=CC(OC)=C1OC KCIZTNZGSBSSRM-UHFFFAOYSA-N 0.000 claims description 11
- 229910052742 iron Inorganic materials 0.000 claims description 10
- 239000011541 reaction mixture Substances 0.000 claims description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 9
- 238000009835 boiling Methods 0.000 claims description 9
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 7
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 7
- 229910052794 bromium Inorganic materials 0.000 claims description 7
- 239000011261 inert gas Substances 0.000 claims description 7
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
- 238000005727 Friedel-Crafts reaction Methods 0.000 claims description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 6
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 6
- 239000000460 chlorine Substances 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 3
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 2
- 230000015572 biosynthetic process Effects 0.000 claims description 2
- FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 238000002360 preparation method Methods 0.000 description 7
- 238000005863 Friedel-Crafts acylation reaction Methods 0.000 description 5
- 230000031709 bromination Effects 0.000 description 5
- 238000005893 bromination reaction Methods 0.000 description 5
- 238000004821 distillation Methods 0.000 description 5
- YKPFELJFRFLNLJ-UHFFFAOYSA-N 3-bromo-6-methoxy-2-methylbenzoyl chloride Chemical compound COC1=CC=C(Br)C(C)=C1C(Cl)=O YKPFELJFRFLNLJ-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 4
- AMSPWOYQQAWRRM-UHFFFAOYSA-N metrafenone Chemical compound COC1=CC=C(Br)C(C)=C1C(=O)C1=C(C)C=C(OC)C(OC)=C1OC AMSPWOYQQAWRRM-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 230000004048 modification Effects 0.000 description 4
- 238000012986 modification Methods 0.000 description 4
- MICCJGFEXKNBLU-UHFFFAOYSA-N 2-methoxy-6-methylbenzoic acid Chemical compound COC1=CC=CC(C)=C1C(O)=O MICCJGFEXKNBLU-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- PZXLGCIJEFUSLH-UHFFFAOYSA-N 3-bromo-6-methoxy-2-methylbenzoic acid Chemical compound COC1=CC=C(Br)C(C)=C1C(O)=O PZXLGCIJEFUSLH-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 2
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 229910002804 graphite Inorganic materials 0.000 description 2
- 239000010439 graphite Substances 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 238000005580 one pot reaction Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 238000010626 work up procedure Methods 0.000 description 2
- RHEBROAUHQAJJH-UHFFFAOYSA-N (3,6-dichloro-2-methylphenyl)-(2,3,4-trimethoxy-6-methylphenyl)methanone Chemical compound COC1=C(OC)C(OC)=CC(C)=C1C(=O)C1=C(C)C(Cl)=CC=C1Cl RHEBROAUHQAJJH-UHFFFAOYSA-N 0.000 description 1
- ZMZPOOMKGJKAAE-UHFFFAOYSA-N (3-chloro-6-hydroxy-2-methylphenyl)-(2,3,4-trimethoxy-6-methylphenyl)methanone Chemical compound COC1=C(OC)C(OC)=CC(C)=C1C(=O)C1=C(O)C=CC(Cl)=C1C ZMZPOOMKGJKAAE-UHFFFAOYSA-N 0.000 description 1
- XEMRAKSQROQPBR-UHFFFAOYSA-N (trichloromethyl)benzene Chemical compound ClC(Cl)(Cl)C1=CC=CC=C1 XEMRAKSQROQPBR-UHFFFAOYSA-N 0.000 description 1
- GETTZEONDQJALK-UHFFFAOYSA-N (trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC=C1 GETTZEONDQJALK-UHFFFAOYSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- VTLYFUHAOXGGBS-UHFFFAOYSA-N Fe3+ Chemical class [Fe+3] VTLYFUHAOXGGBS-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 238000007171 acid catalysis Methods 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- GKJROTAYDAJLGD-UHFFFAOYSA-N carbonyl dichloride;hydrochloride Chemical compound Cl.ClC(Cl)=O GKJROTAYDAJLGD-UHFFFAOYSA-N 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 239000012320 chlorinating reagent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 230000008570 general process Effects 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 159000000014 iron salts Chemical class 0.000 description 1
- LIKBJVNGSGBSGK-UHFFFAOYSA-N iron(3+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Fe+3].[Fe+3] LIKBJVNGSGBSGK-UHFFFAOYSA-N 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 229910052756 noble gas Inorganic materials 0.000 description 1
- 150000002835 noble gases Chemical class 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
- C07C51/363—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by introduction of halogen; by substitution of halogen atoms by other halogen atoms
-
- 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
-
- 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
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/64—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by introduction of functional groups containing oxygen only in singly bound form
-
- 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
- C07C45/78—Separation; Purification; Stabilisation; Use of additives
- C07C45/81—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/84—Ketones containing a keto group bound to a six-membered aromatic ring containing ether groups, groups, groups, or groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/58—Preparation of carboxylic acid halides
- C07C51/60—Preparation of carboxylic acid halides by conversion of carboxylic acids or their anhydrides or esters, lactones, salts into halides with the same carboxylic acid part
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Crystallography & Structural Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10258669 | 2002-12-13 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200505574B true ZA200505574B (en) | 2006-09-27 |
Family
ID=32518964
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200505574A ZA200505574B (en) | 2002-12-13 | 2005-07-12 | Method for the production of benzophenones |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US7253323B2 (ja) |
| EP (1) | EP1572613B1 (ja) |
| JP (1) | JP4500167B2 (ja) |
| KR (1) | KR20050089035A (ja) |
| CN (1) | CN100339348C (ja) |
| AR (1) | AR042779A1 (ja) |
| AT (1) | ATE336478T1 (ja) |
| AU (1) | AU2003294750B2 (ja) |
| BR (1) | BRPI0316844B1 (ja) |
| CA (1) | CA2508714C (ja) |
| DE (1) | DE50304687D1 (ja) |
| DK (1) | DK1572613T3 (ja) |
| EA (1) | EA008040B1 (ja) |
| ES (1) | ES2271675T3 (ja) |
| IL (1) | IL168500A (ja) |
| MX (1) | MXPA05005239A (ja) |
| PL (1) | PL206020B1 (ja) |
| UA (1) | UA79182C2 (ja) |
| WO (1) | WO2004054953A1 (ja) |
| ZA (1) | ZA200505574B (ja) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8280466B2 (en) * | 2004-03-17 | 2012-10-02 | Telecommunication Systems, Inc. | Four frequency band single GSM antenna |
| JP2010521496A (ja) | 2007-03-14 | 2010-06-24 | ノップ ニューロサイエンシーズ、インク． | キラル精製置換ベンゾチアゾールジアミンの合成 |
| US20110190356A1 (en) | 2008-08-19 | 2011-08-04 | Knopp Neurosciences Inc. | Compositions and Methods of Using (R)- Pramipexole |
| US7772441B1 (en) * | 2009-02-26 | 2010-08-10 | E.I. Du Pont De Nemours And Company | Process for producing 3,4′ dihydroxybenzophenone |
| CN102295546A (zh) * | 2011-06-30 | 2011-12-28 | 浙江工业大学 | 一种制备二苯甲酮类化合物的方法 |
| WO2013096816A1 (en) | 2011-12-22 | 2013-06-27 | Biogen Idec Ma Inc. | Improved synthesis of amine substituted 4,5,6,7-tetrahydrobenzothiazole compounds |
| US9662313B2 (en) | 2013-02-28 | 2017-05-30 | Knopp Biosciences Llc | Compositions and methods for treating amyotrophic lateral sclerosis in responders |
| LT3019167T (lt) | 2013-07-12 | 2021-03-25 | Knopp Biosciences Llc | Eozinofilų ir (arba) bazofilų padidintų kiekių gydymas |
| US9468630B2 (en) | 2013-07-12 | 2016-10-18 | Knopp Biosciences Llc | Compositions and methods for treating conditions related to increased eosinophils |
| EP3038467B1 (en) | 2013-08-13 | 2020-07-29 | Knopp Biosciences LLC | Compositions and methods for treating plasma cell disorders and b-cell prolymphocytic disorders |
| AU2014306597B2 (en) | 2013-08-13 | 2018-05-17 | Knopp Biosciences Llc | Compositions and methods for treating chronic urticaria |
| GB2592668B (en) * | 2020-03-06 | 2024-08-14 | Rotam Agrochem Int Co Ltd | A novel form of metrafenone, a process for its preparation and use of the same |
| CN115701422B (zh) * | 2021-08-02 | 2024-02-09 | 中国科学院昆明植物研究所 | 一种kgp94的制备方法 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH583677A5 (ja) * | 1972-02-03 | 1977-01-14 | Basf Ag | |
| US5476970A (en) * | 1984-02-16 | 1995-12-19 | Velsicol Chemical Corporation | Method for preparing aryl ketones |
| US5210313A (en) * | 1992-01-10 | 1993-05-11 | Maxdem Incorporated | Preparation of 2,5-dichlorobenzophenones |
| US5945567A (en) * | 1997-08-20 | 1999-08-31 | American Cyanamid Company | Fungicidal 2-methoxybenzophenones |
| PT897904E (pt) * | 1997-08-20 | 2002-08-30 | Basf Ag | 2-metoxibenzofenonas fungicidas |
| AU2677201A (en) * | 2000-01-13 | 2001-07-24 | Basf Aktiengesellschaft | A process for the preparation of substituted benzophenones |
| EP1295877A1 (de) * | 2001-09-21 | 2003-03-26 | Basf Aktiengesellschaft | Xanthonderivate, Verfahren zu ihrer Herstellung und ihre Verwendung zur Bekämpfung von Schadpilzen sowie sie enthaltende Mittel |
-
2003
- 2003-01-12 UA UAA200506791A patent/UA79182C2/uk unknown
- 2003-12-01 PL PL377943A patent/PL206020B1/pl not_active IP Right Cessation
- 2003-12-01 EP EP03785691A patent/EP1572613B1/de not_active Expired - Lifetime
- 2003-12-01 AU AU2003294750A patent/AU2003294750B2/en not_active Ceased
- 2003-12-01 AT AT03785691T patent/ATE336478T1/de active
- 2003-12-01 BR BRPI0316844A patent/BRPI0316844B1/pt not_active IP Right Cessation
- 2003-12-01 MX MXPA05005239A patent/MXPA05005239A/es active IP Right Grant
- 2003-12-01 JP JP2004559732A patent/JP4500167B2/ja not_active Expired - Fee Related
- 2003-12-01 DE DE50304687T patent/DE50304687D1/de not_active Expired - Lifetime
- 2003-12-01 KR KR1020057010537A patent/KR20050089035A/ko active IP Right Grant
- 2003-12-01 WO PCT/EP2003/013483 patent/WO2004054953A1/de active IP Right Grant
- 2003-12-01 US US10/535,710 patent/US7253323B2/en not_active Expired - Lifetime
- 2003-12-01 DK DK03785691T patent/DK1572613T3/da active
- 2003-12-01 ES ES03785691T patent/ES2271675T3/es not_active Expired - Lifetime
- 2003-12-01 CN CNB200380105769XA patent/CN100339348C/zh not_active Expired - Lifetime
- 2003-12-01 EA EA200500897A patent/EA008040B1/ru not_active IP Right Cessation
- 2003-12-01 CA CA2508714A patent/CA2508714C/en not_active Expired - Fee Related
- 2003-12-12 AR ARP030104612A patent/AR042779A1/es active IP Right Grant
-
2005
- 2005-05-10 IL IL168500A patent/IL168500A/en active IP Right Grant
- 2005-07-12 ZA ZA200505574A patent/ZA200505574B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AU2003294750B2 (en) | 2010-04-01 |
| ATE336478T1 (de) | 2006-09-15 |
| BR0316844A (pt) | 2005-10-18 |
| CA2508714C (en) | 2011-04-05 |
| CN100339348C (zh) | 2007-09-26 |
| CA2508714A1 (en) | 2004-07-01 |
| DE50304687D1 (de) | 2006-09-28 |
| PL206020B1 (pl) | 2010-06-30 |
| PL377943A1 (pl) | 2006-02-20 |
| BRPI0316844B1 (pt) | 2016-03-08 |
| JP4500167B2 (ja) | 2010-07-14 |
| EP1572613A1 (de) | 2005-09-14 |
| MXPA05005239A (es) | 2005-07-25 |
| JP2006515586A (ja) | 2006-06-01 |
| WO2004054953A1 (de) | 2004-07-01 |
| US7253323B2 (en) | 2007-08-07 |
| US20060009659A1 (en) | 2006-01-12 |
| UA79182C2 (en) | 2007-05-25 |
| CN1726178A (zh) | 2006-01-25 |
| DK1572613T3 (da) | 2006-12-18 |
| ES2271675T3 (es) | 2007-04-16 |
| AU2003294750A1 (en) | 2004-07-09 |
| IL168500A (en) | 2011-03-31 |
| EA008040B1 (ru) | 2007-02-27 |
| EP1572613B1 (de) | 2006-08-16 |
| KR20050089035A (ko) | 2005-09-07 |
| EA200500897A1 (ru) | 2005-12-29 |
| AR042779A1 (es) | 2005-07-06 |
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