ZA200309216B - Process for the preparation 3-aryl-2-hydroxypropionic acid derivative. - Google Patents

Process for the preparation 3-aryl-2-hydroxypropionic acid derivative. Download PDF

Info

Publication number: ZA200309216B
Authority: ZA; South Africa
Prior art keywords: compound; formula; process according; protecting group; group
Prior art date: 2001-06-01

Application number

ZA200309216A

Other languages

English (en)

Inventor

Robert Ehrl

William Mackintosh

Panagiotis Ioannidis

Original Assignee

Astrazeneca Ab

Priority date (The priority date 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 date listed.)

2001-06-01

Filing date

2003-11-26

Publication date

2004-09-16

2001-06-01 Priority claimed from SE0101979A external-priority patent/SE0101979D0/xx

2002-04-02 Priority claimed from SE0201004A external-priority patent/SE0201004D0/xx

2003-11-26 Application filed by Astrazeneca Ab filed Critical Astrazeneca Ab

2004-09-16 Publication of ZA200309216B publication Critical patent/ZA200309216B/en

Links

238000000034 method Methods 0.000 title claims description 40
238000002360 preparation method Methods 0.000 title claims description 14
150000001875 compounds Chemical class 0.000 claims description 35
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 24
239000002253 acid Substances 0.000 claims description 22
125000006239 protecting group Chemical group 0.000 claims description 21
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical group CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 15
239000002585 base Substances 0.000 claims description 13
239000003444 phase transfer catalyst Substances 0.000 claims description 11
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 11
239000002904 solvent Substances 0.000 claims description 8
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 6
230000007062 hydrolysis Effects 0.000 claims description 6
238000006460 hydrolysis reaction Methods 0.000 claims description 6
-1 phenylsulfonyloxy group Chemical group 0.000 claims description 6
229920001223 polyethylene glycol Polymers 0.000 claims description 5
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 4
NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 claims description 4
239000007787 solid Substances 0.000 claims description 4
UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 claims description 3
239000002202 Polyethylene glycol Substances 0.000 claims description 3
150000003983 crown ethers Chemical group 0.000 claims description 3
239000000155 melt Substances 0.000 claims description 3
150000003242 quaternary ammonium salts Chemical class 0.000 claims description 3
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 2
229910052783 alkali metal Inorganic materials 0.000 claims description 2
150000001340 alkali metals Chemical class 0.000 claims description 2
125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims description 2
239000007864 aqueous solution Substances 0.000 claims description 2
BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 claims description 2
150000004649 carbonic acid derivatives Chemical group 0.000 claims description 2
150000004820 halides Chemical class 0.000 claims description 2
150000004679 hydroxides Chemical class 0.000 claims description 2
125000001475 halogen functional group Chemical group 0.000 claims 1
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 30
239000000243 solution Substances 0.000 description 25
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 23
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
238000006243 chemical reaction Methods 0.000 description 19
239000000203 mixture Substances 0.000 description 14
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
235000019439 ethyl acetate Nutrition 0.000 description 11
239000002002 slurry Substances 0.000 description 7
238000003756 stirring Methods 0.000 description 7
BQHDGPXFPFAVOA-UHFFFAOYSA-N 3-(4-methylsulfonyloxyphenyl)propane-1-sulfonic acid Chemical compound CS(=O)(=O)OC1=CC=C(CCCS(O)(=O)=O)C=C1 BQHDGPXFPFAVOA-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
150000002148 esters Chemical class 0.000 description 5
NEJJCKFYYBEQRQ-LBPRGKRZSA-N ethyl (2s)-2-ethoxy-3-(4-hydroxyphenyl)propanoate Chemical compound CCOC(=O)[C@@H](OCC)CC1=CC=C(O)C=C1 NEJJCKFYYBEQRQ-LBPRGKRZSA-N 0.000 description 5
JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 5
208000001072 type 2 diabetes mellitus Diseases 0.000 description 5
XEZNGIUYQVAUSS-UHFFFAOYSA-N 18-crown-6 Chemical compound C1COCCOCCOCCOCCOCCO1 XEZNGIUYQVAUSS-UHFFFAOYSA-N 0.000 description 4
229920002565 Polyethylene Glycol 400 Polymers 0.000 description 4
JMZWKJZJXSKXJL-NRFANRHFSA-N ethyl (2s)-2-ethoxy-3-[4-[2-(4-methylsulfonyloxyphenyl)ethoxy]phenyl]propanoate Chemical compound C1=CC(C[C@H](OCC)C(=O)OCC)=CC=C1OCCC1=CC=C(OS(C)(=O)=O)C=C1 JMZWKJZJXSKXJL-NRFANRHFSA-N 0.000 description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
238000004128 high performance liquid chromatography Methods 0.000 description 4
239000010410 layer Substances 0.000 description 4
239000012071 phase Substances 0.000 description 4
150000003839 salts Chemical class 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
206010022489 Insulin Resistance Diseases 0.000 description 3
208000031773 Insulin resistance syndrome Diseases 0.000 description 3
WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 3
238000001704 evaporation Methods 0.000 description 3
230000008020 evaporation Effects 0.000 description 3
229940011051 isopropyl acetate Drugs 0.000 description 3
GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 3
239000003960 organic solvent Substances 0.000 description 3
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
239000000047 product Substances 0.000 description 3
238000010992 reflux Methods 0.000 description 3
YCCILVSKPBXVIP-UHFFFAOYSA-N 2-(4-hydroxyphenyl)ethanol Chemical compound OCCC1=CC=C(O)C=C1 YCCILVSKPBXVIP-UHFFFAOYSA-N 0.000 description 2
SYBYTAAJFKOIEJ-UHFFFAOYSA-N 3-Methylbutan-2-one Chemical compound CC(C)C(C)=O SYBYTAAJFKOIEJ-UHFFFAOYSA-N 0.000 description 2
201000001320 Atherosclerosis Diseases 0.000 description 2
208000032928 Dyslipidaemia Diseases 0.000 description 2
108010010234 HDL Lipoproteins Proteins 0.000 description 2
102000015779 HDL Lipoproteins Human genes 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical group [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
108010062497 VLDL Lipoproteins Proteins 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
125000000217 alkyl group Chemical group 0.000 description 2
239000000010 aprotic solvent Substances 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
238000001816 cooling Methods 0.000 description 2
DUWWHGPELOTTOE-UHFFFAOYSA-N n-(5-chloro-2,4-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC(OC)=C(NC(=O)CC(C)=O)C=C1Cl DUWWHGPELOTTOE-UHFFFAOYSA-N 0.000 description 2
239000012044 organic layer Substances 0.000 description 2
239000012074 organic phase Substances 0.000 description 2
FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
235000019260 propionic acid Nutrition 0.000 description 2
238000001953 recrystallisation Methods 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
GSUOBIZQBZHTSP-UHFFFAOYSA-N 2-[4-[2-(4-methylsulfonyloxyphenyl)ethoxy]phenyl]propanoic acid Chemical compound CS(=O)(=O)OC1=CC=C(C=C1)CCOC1=CC=C(C=C1)C(C(=O)O)C GSUOBIZQBZHTSP-UHFFFAOYSA-N 0.000 description 1
CXGTZJYQWSUFET-UHFFFAOYSA-N 2-ethoxy-3-[4-[2-(4-methylsulfonyloxyphenyl)ethoxy]phenyl]propanoic acid Chemical compound C1=CC(CC(OCC)C(O)=O)=CC=C1OCCC1=CC=C(OS(C)(=O)=O)C=C1 CXGTZJYQWSUFET-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
206010060378 Hyperinsulinaemia Diseases 0.000 description 1
NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 1
108090001030 Lipoproteins Proteins 0.000 description 1
102000004895 Lipoproteins Human genes 0.000 description 1
239000012359 Methanesulfonyl chloride Substances 0.000 description 1
208000008589 Obesity Diseases 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
208000037849 arterial hypertension Diseases 0.000 description 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
238000009835 boiling Methods 0.000 description 1
125000001246 bromo group Chemical group Br* 0.000 description 1
125000002843 carboxylic acid group Chemical group 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
239000013078 crystal Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000034994 death Effects 0.000 description 1
231100000517 death Toxicity 0.000 description 1
238000010511 deprotection reaction Methods 0.000 description 1
YSSSPARMOAYJTE-UHFFFAOYSA-N dibenzo-18-crown-6 Chemical compound O1CCOCCOC2=CC=CC=C2OCCOCCOC2=CC=CC=C21 YSSSPARMOAYJTE-UHFFFAOYSA-N 0.000 description 1
JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 1
201000010099 disease Diseases 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
238000004821 distillation Methods 0.000 description 1
239000003814 drug Substances 0.000 description 1
230000002526 effect on cardiovascular system Effects 0.000 description 1
230000002255 enzymatic effect Effects 0.000 description 1
125000004185 ester group Chemical group 0.000 description 1
230000020764 fibrinolysis Effects 0.000 description 1
239000012467 final product Substances 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
230000035879 hyperinsulinaemia Effects 0.000 description 1
125000002346 iodo group Chemical group I* 0.000 description 1
239000007788 liquid Substances 0.000 description 1
QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
XKBGEWXEAPTVCK-UHFFFAOYSA-M methyltrioctylammonium chloride Chemical compound [Cl-].CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC XKBGEWXEAPTVCK-UHFFFAOYSA-M 0.000 description 1
208000010125 myocardial infarction Diseases 0.000 description 1
235000020824 obesity Nutrition 0.000 description 1
239000011368 organic material Substances 0.000 description 1
239000002245 particle Substances 0.000 description 1
238000003408 phase transfer catalysis Methods 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011736 potassium bicarbonate Substances 0.000 description 1
229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
235000015497 potassium bicarbonate Nutrition 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
235000011181 potassium carbonates Nutrition 0.000 description 1
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
229940086066 potassium hydrogencarbonate Drugs 0.000 description 1
239000000843 powder Substances 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
108091008012 small dense LDL Proteins 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
235000017550 sodium carbonate Nutrition 0.000 description 1
239000012453 solvate Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000001117 sulphuric acid Substances 0.000 description 1
235000011149 sulphuric acid Nutrition 0.000 description 1
CXGTZJYQWSUFET-IBGZPJMESA-N tesaglitazar Chemical compound C1=CC(C[C@H](OCC)C(O)=O)=CC=C1OCCC1=CC=C(OS(C)(=O)=O)C=C1 CXGTZJYQWSUFET-IBGZPJMESA-N 0.000 description 1
SYZCZDCAEVUSPM-UHFFFAOYSA-M tetrahexylazanium;bromide Chemical compound [Br-].CCCCCC[N+](CCCCCC)(CCCCCC)CCCCCC SYZCZDCAEVUSPM-UHFFFAOYSA-M 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
QBVXKDJEZKEASM-UHFFFAOYSA-M tetraoctylammonium bromide Chemical compound [Br-].CCCCCCCC[N+](CCCCCCCC)(CCCCCCCC)CCCCCCCC QBVXKDJEZKEASM-UHFFFAOYSA-M 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
238000007738 vacuum evaporation Methods 0.000 description 1
230000009278 visceral effect Effects 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/26—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of esters of sulfonic acids
- C07C303/30—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of esters of sulfonic acids by reactions not involving the formation of esterified sulfo groups
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

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)

ZA200309216A 2001-06-01 2003-11-26 Process for the preparation 3-aryl-2-hydroxypropionic acid derivative. ZA200309216B (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
SE0101979A SE0101979D0 (sv)	2001-06-01	2001-06-01	New Process
SE0201004A SE0201004D0 (sv)	2002-04-02	2002-04-02	New process

Publications (1)

Publication Number	Publication Date
ZA200309216B true ZA200309216B (en)	2004-09-16

Family

ID=26655481

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
ZA200309216A ZA200309216B (en)	2001-06-01	2003-11-26	Process for the preparation 3-aryl-2-hydroxypropionic acid derivative.

Country Status (13)

Country	Link
US (1)	US20050014955A1 (es)
EP (1)	EP1404651A1 (es)
JP (1)	JP2004528388A (es)
KR (1)	KR20040004673A (es)
CN (1)	CN1247537C (es)
BR (1)	BR0210125A (es)
CA (1)	CA2448658A1 (es)
IL (1)	IL159063A0 (es)
MX (1)	MXPA03011011A (es)
NO (1)	NO20035273D0 (es)
NZ (1)	NZ529815A (es)
WO (1)	WO2002096865A1 (es)
ZA (1)	ZA200309216B (es)

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
SE9801992D0 (sv) *	1998-06-04	1998-06-04	Astra Ab	New 3-aryl-2-hydroxypropionic acid derivative I
TW574193B (en) *	1999-12-03	2004-02-01	Astrazeneca Ab	Novel phenalkyloxy-phenyl derivatives, pharmaceutical composition containing the same and their uses

2002
- 2002-05-30 NZ NZ529815A patent/NZ529815A/en unknown
- 2002-05-30 IL IL15906302A patent/IL159063A0/xx unknown
- 2002-05-30 BR BR0210125-4A patent/BR0210125A/pt not_active IP Right Cessation
- 2002-05-30 US US10/479,159 patent/US20050014955A1/en not_active Abandoned
- 2002-05-30 KR KR10-2003-7015637A patent/KR20040004673A/ko not_active Application Discontinuation
- 2002-05-30 CA CA002448658A patent/CA2448658A1/en not_active Abandoned
- 2002-05-30 EP EP02736372A patent/EP1404651A1/en not_active Withdrawn
- 2002-05-30 JP JP2003500045A patent/JP2004528388A/ja not_active Withdrawn
- 2002-05-30 MX MXPA03011011A patent/MXPA03011011A/es not_active Application Discontinuation
- 2002-05-30 WO PCT/SE2002/001040 patent/WO2002096865A1/en not_active Application Discontinuation
- 2002-05-30 CN CNB028149653A patent/CN1247537C/zh not_active Expired - Fee Related
2003
- 2003-11-26 ZA ZA200309216A patent/ZA200309216B/en unknown
- 2003-11-27 NO NO20035273A patent/NO20035273D0/no not_active Application Discontinuation

Also Published As

Publication number	Publication date
NO20035273D0 (no)	2003-11-27
WO2002096865A8 (en)	2005-03-17
JP2004528388A (ja)	2004-09-16
KR20040004673A (ko)	2004-01-13
CN1535262A (zh)	2004-10-06
IL159063A0 (en)	2004-05-12
EP1404651A1 (en)	2004-04-07
CA2448658A1 (en)	2002-12-05
NZ529815A (en)	2005-11-25
WO2002096865A1 (en)	2002-12-05
CN1247537C (zh)	2006-03-29
US20050014955A1 (en)	2005-01-20
BR0210125A (pt)	2004-06-08
MXPA03011011A (es)	2004-02-27

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