ZA200201111B - Process for the preparation of acylated 1,3-dicarbonyl compounds. - Google Patents
Process for the preparation of acylated 1,3-dicarbonyl compounds. Download PDFInfo
- Publication number
- ZA200201111B ZA200201111B ZA200201111A ZA200201111A ZA200201111B ZA 200201111 B ZA200201111 B ZA 200201111B ZA 200201111 A ZA200201111 A ZA 200201111A ZA 200201111 A ZA200201111 A ZA 200201111A ZA 200201111 B ZA200201111 B ZA 200201111B
- Authority
- ZA
- South Africa
- Prior art keywords
- process according
- alkyl
- alkali metal
- acylated
- rearrangement
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 17
- 230000008569 process Effects 0.000 title claims description 17
- -1 enol ester Chemical class 0.000 claims description 26
- 229910052799 carbon Inorganic materials 0.000 claims description 16
- 229910052783 alkali metal Inorganic materials 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 230000008707 rearrangement Effects 0.000 claims description 11
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 125000001188 haloalkyl group Chemical group 0.000 claims description 7
- 239000002585 base Substances 0.000 claims description 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical group [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 claims description 4
- 229910052792 caesium Inorganic materials 0.000 claims description 4
- 230000003197 catalytic effect Effects 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 3
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 3
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 3
- 125000000304 alkynyl group Chemical group 0.000 claims description 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 125000004434 sulfur atom Chemical group 0.000 claims description 3
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 2
- 125000006350 alkyl thio alkyl group Chemical group 0.000 claims description 2
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 239000003444 phase transfer catalyst Substances 0.000 claims description 2
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical group CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims 3
- 125000005843 halogen group Chemical group 0.000 claims 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 2
- 239000002904 solvent Substances 0.000 claims 2
- 125000004122 cyclic group Chemical group 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 125000003944 tolyl group Chemical group 0.000 claims 1
- 239000003054 catalyst Substances 0.000 description 10
- 239000003153 chemical reaction reagent Substances 0.000 description 6
- 150000002367 halogens Chemical group 0.000 description 5
- 125000003118 aryl group Chemical group 0.000 description 4
- OILAIQUEIWYQPH-UHFFFAOYSA-N cyclohexane-1,2-dione Chemical class O=C1CCCCC1=O OILAIQUEIWYQPH-UHFFFAOYSA-N 0.000 description 4
- JGLMVXWAHNTPRF-CMDGGOBGSA-N CCN1N=C(C)C=C1C(=O)NC1=NC2=CC(=CC(OC)=C2N1C\C=C\CN1C(NC(=O)C2=CC(C)=NN2CC)=NC2=CC(=CC(OCCCN3CCOCC3)=C12)C(N)=O)C(N)=O Chemical compound CCN1N=C(C)C=C1C(=O)NC1=NC2=CC(=CC(OC)=C2N1C\C=C\CN1C(NC(=O)C2=CC(C)=NN2CC)=NC2=CC(=CC(OCCCN3CCOCC3)=C12)C(N)=O)C(N)=O JGLMVXWAHNTPRF-CMDGGOBGSA-N 0.000 description 3
- 150000001540 azides Chemical class 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 238000003419 tautomerization reaction Methods 0.000 description 3
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical class CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- 239000003905 agrochemical Substances 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical class Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- HJSLFCCWAKVHIW-UHFFFAOYSA-N cyclohexane-1,3-dione Chemical class O=C1CCCC(=O)C1 HJSLFCCWAKVHIW-UHFFFAOYSA-N 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- LELOWRISYMNNSU-UHFFFAOYSA-N Hydrocyanic acid Natural products N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 150000003927 aminopyridines Chemical class 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 description 1
- AYTVLULEEPNWAX-UHFFFAOYSA-N cesium;azide Chemical compound [Cs+].[N-]=[N+]=[N-] AYTVLULEEPNWAX-UHFFFAOYSA-N 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 230000002363 herbicidal effect Effects 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- GUWHRJQTTVADPB-UHFFFAOYSA-N lithium azide Chemical compound [Li+].[N-]=[N+]=[N-] GUWHRJQTTVADPB-UHFFFAOYSA-N 0.000 description 1
- 125000005394 methallyl group Chemical group 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 1
- 125000006574 non-aromatic ring group Chemical group 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 230000008635 plant growth Effects 0.000 description 1
- TZLVRPLSVNESQC-UHFFFAOYSA-N potassium azide Chemical compound [K+].[N-]=[N+]=[N-] TZLVRPLSVNESQC-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000006462 rearrangement reaction Methods 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000002699 waste material 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
- C07C67/333—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton
- C07C67/343—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
- C07C201/06—Preparation of nitro compounds
- C07C201/12—Preparation of nitro compounds by reactions not involving the formation of nitro groups
-
- 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
- C07C45/54—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 of compounds containing doubly bound oxygen atoms, e.g. esters
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/02—Systems containing only non-condensed rings with a three-membered ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
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)
- Fats And Perfumes (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US37118199A | 1999-08-10 | 1999-08-10 |
Publications (1)
Publication Number | Publication Date |
---|---|
ZA200201111B true ZA200201111B (en) | 2002-11-27 |
Family
ID=23462840
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
ZA200201111A ZA200201111B (en) | 1999-08-10 | 2002-02-08 | Process for the preparation of acylated 1,3-dicarbonyl compounds. |
Country Status (23)
Country | Link |
---|---|
US (1) | US6657074B1 (de) |
EP (1) | EP1202949B1 (de) |
JP (1) | JP4800532B2 (de) |
KR (1) | KR100704519B1 (de) |
CN (1) | CN1185202C (de) |
AR (1) | AR025073A1 (de) |
AT (1) | ATE264829T1 (de) |
AU (1) | AU766368B2 (de) |
BR (1) | BR0013094B1 (de) |
CA (1) | CA2380853C (de) |
DE (1) | DE60010092T2 (de) |
DK (1) | DK1202949T3 (de) |
ES (1) | ES2219389T3 (de) |
HU (1) | HU228357B1 (de) |
IL (2) | IL147830A0 (de) |
MX (1) | MXPA02001248A (de) |
PL (1) | PL198618B1 (de) |
PT (1) | PT1202949E (de) |
RU (1) | RU2248347C2 (de) |
TW (1) | TWI255263B (de) |
UA (1) | UA72537C2 (de) |
WO (1) | WO2001010806A2 (de) |
ZA (1) | ZA200201111B (de) |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2015070392A1 (zh) * | 2013-11-13 | 2015-05-21 | 迈克斯(如东)化工有限公司 | 一种环己烷三酮类化合物的制备方法 |
CN106414414B (zh) * | 2014-06-16 | 2020-07-14 | 组合化学工业株式会社 | 三酮化合物的制造方法 |
US20170327454A1 (en) * | 2016-05-13 | 2017-11-16 | Sirrus, Inc. | High purity 1,1-dicarbonyl substituted-1-alkenes and methods for their preparation |
CN113943235B (zh) * | 2020-07-17 | 2022-06-14 | 沈阳中化农药化工研发有限公司 | 一种制备硝磺草酮除草剂的方法 |
CN117384022A (zh) * | 2022-07-11 | 2024-01-12 | 武汉人福创新药物研发中心有限公司 | 氘代化合物及其用途 |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS52118448A (en) * | 1976-03-29 | 1977-10-04 | Nippon Soda Co Ltd | Synthesis of cyclohexanedione derivatives |
JPS537646A (en) * | 1976-07-08 | 1978-01-24 | Nippon Soda Co Ltd | Synthesis of cyclohexanedione derivatives |
JPS58164543A (ja) * | 1982-03-25 | 1983-09-29 | Ihara Chem Ind Co Ltd | シクロヘキサン誘導体、その製法及びこれを含む植物生長調整剤 |
JPS59196840A (ja) * | 1983-04-22 | 1984-11-08 | Kumiai Chem Ind Co Ltd | シクロヘキサン誘導体および植物生長調節剤 |
GB9501433D0 (en) * | 1995-01-25 | 1995-03-15 | Zeneca Ltd | Chemical process |
-
2000
- 2000-08-08 CN CNB008114390A patent/CN1185202C/zh not_active Expired - Fee Related
- 2000-08-08 KR KR1020027001678A patent/KR100704519B1/ko not_active IP Right Cessation
- 2000-08-08 RU RU2002105506/04A patent/RU2248347C2/ru not_active IP Right Cessation
- 2000-08-08 IL IL14783000A patent/IL147830A0/xx active IP Right Grant
- 2000-08-08 UA UA2002031930A patent/UA72537C2/uk unknown
- 2000-08-08 US US10/049,074 patent/US6657074B1/en not_active Expired - Fee Related
- 2000-08-08 EP EP00960415A patent/EP1202949B1/de not_active Expired - Lifetime
- 2000-08-08 BR BRPI0013094-0A patent/BR0013094B1/pt not_active IP Right Cessation
- 2000-08-08 CA CA002380853A patent/CA2380853C/en not_active Expired - Fee Related
- 2000-08-08 DE DE60010092T patent/DE60010092T2/de not_active Expired - Lifetime
- 2000-08-08 AT AT00960415T patent/ATE264829T1/de active
- 2000-08-08 HU HU0300505A patent/HU228357B1/hu not_active IP Right Cessation
- 2000-08-08 DK DK00960415T patent/DK1202949T3/da active
- 2000-08-08 PL PL353096A patent/PL198618B1/pl not_active IP Right Cessation
- 2000-08-08 JP JP2001515276A patent/JP4800532B2/ja not_active Expired - Fee Related
- 2000-08-08 AR ARP000104085A patent/AR025073A1/es active IP Right Grant
- 2000-08-08 AU AU72734/00A patent/AU766368B2/en not_active Ceased
- 2000-08-08 ES ES00960415T patent/ES2219389T3/es not_active Expired - Lifetime
- 2000-08-08 WO PCT/EP2000/007710 patent/WO2001010806A2/en active IP Right Grant
- 2000-08-08 MX MXPA02001248A patent/MXPA02001248A/es active IP Right Grant
- 2000-08-08 PT PT00960415T patent/PT1202949E/pt unknown
- 2000-08-08 TW TW089115906A patent/TWI255263B/zh not_active IP Right Cessation
-
2002
- 2002-01-24 IL IL147830A patent/IL147830A/en not_active IP Right Cessation
- 2002-02-08 ZA ZA200201111A patent/ZA200201111B/en unknown
Also Published As
Publication number | Publication date |
---|---|
MXPA02001248A (es) | 2002-07-22 |
ATE264829T1 (de) | 2004-05-15 |
TWI255263B (en) | 2006-05-21 |
KR20020019611A (ko) | 2002-03-12 |
AU766368B2 (en) | 2003-10-16 |
PT1202949E (pt) | 2004-08-31 |
EP1202949A2 (de) | 2002-05-08 |
BR0013094B1 (pt) | 2011-10-18 |
DE60010092D1 (de) | 2004-05-27 |
CN1185202C (zh) | 2005-01-19 |
DE60010092T2 (de) | 2004-08-26 |
HU228357B1 (en) | 2013-03-28 |
AR025073A1 (es) | 2002-11-06 |
PL198618B1 (pl) | 2008-07-31 |
HUP0300505A2 (en) | 2003-07-28 |
UA72537C2 (en) | 2005-03-15 |
IL147830A (en) | 2007-09-20 |
CA2380853A1 (en) | 2001-02-15 |
KR100704519B1 (ko) | 2007-04-09 |
IL147830A0 (en) | 2002-08-14 |
CN1368947A (zh) | 2002-09-11 |
WO2001010806A2 (en) | 2001-02-15 |
DK1202949T3 (da) | 2004-07-19 |
ES2219389T3 (es) | 2004-12-01 |
JP2003506421A (ja) | 2003-02-18 |
WO2001010806A3 (en) | 2001-07-05 |
EP1202949B1 (de) | 2004-04-21 |
JP4800532B2 (ja) | 2011-10-26 |
US6657074B1 (en) | 2003-12-02 |
BR0013094A (pt) | 2002-04-30 |
AU7273400A (en) | 2001-03-05 |
RU2248347C2 (ru) | 2005-03-20 |
CA2380853C (en) | 2008-10-07 |
PL353096A1 (en) | 2003-10-20 |
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