ZA200601264B - Purification process - Google Patents

Purification process Download PDF

Info

Publication number: ZA200601264B
Authority: ZA; South Africa
Prior art keywords: terbinafine; ppm; distillation; free base; palladium
Prior art date: 2003-08-29

Application number

ZA200601264A

Other languages

English (en)

Inventor

Beutler Ulrich

Penn Gerhard

Original Assignee

Novartis Ag

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.)

2003-08-29

Filing date

2006-02-13

Publication date

2007-06-27

Family has litigation

First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=28686596&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=ZA200601264(B) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.

2006-02-13 Application filed by Novartis Ag filed Critical Novartis Ag

2007-06-27 Publication of ZA200601264B publication Critical patent/ZA200601264B/en

Links

238000000746 purification Methods 0.000 title claims description 8
DOMXUEMWDBAQBQ-WEVVVXLNSA-N terbinafine Chemical compound C1=CC=C2C(CN(C\C=C\C#CC(C)(C)C)C)=CC=CC2=C1 DOMXUEMWDBAQBQ-WEVVVXLNSA-N 0.000 claims description 50
229960002722 terbinafine Drugs 0.000 claims description 49
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 43
238000004821 distillation Methods 0.000 claims description 29
239000010949 copper Substances 0.000 claims description 24
229910052802 copper Inorganic materials 0.000 claims description 23
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 22
239000012458 free base Substances 0.000 claims description 22
229910052763 palladium Inorganic materials 0.000 claims description 21
238000000034 method Methods 0.000 claims description 20
230000008569 process Effects 0.000 claims description 19
239000000047 product Substances 0.000 claims description 13
239000002253 acid Substances 0.000 claims description 12
150000003839 salts Chemical group 0.000 claims description 12
238000000526 short-path distillation Methods 0.000 claims description 9
239000003054 catalyst Substances 0.000 claims description 8
239000012264 purified product Substances 0.000 claims description 8
239000012043 crude product Substances 0.000 claims description 7
238000006243 chemical reaction Methods 0.000 claims description 5
PPWNCLVNXGCGAF-UHFFFAOYSA-N 3,3-dimethylbut-1-yne Chemical compound CC(C)(C)C#C PPWNCLVNXGCGAF-UHFFFAOYSA-N 0.000 claims description 4
239000002585 base Substances 0.000 description 19
239000006227 byproduct Substances 0.000 description 11
239000000203 mixture Substances 0.000 description 10
150000001875 compounds Chemical class 0.000 description 8
238000010438 heat treatment Methods 0.000 description 7
239000000356 contaminant Substances 0.000 description 6
238000004817 gas chromatography Methods 0.000 description 6
235000019483 Peanut oil Nutrition 0.000 description 5
-1 allylamine compound Chemical class 0.000 description 5
238000000354 decomposition reaction Methods 0.000 description 5
239000000312 peanut oil Substances 0.000 description 5
239000000126 substance Substances 0.000 description 5
VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
239000007788 liquid Substances 0.000 description 4
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Substances C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
150000001412 amines Chemical class 0.000 description 3
238000009835 boiling Methods 0.000 description 3
238000001816 cooling Methods 0.000 description 3
238000001704 evaporation Methods 0.000 description 3
230000008020 evaporation Effects 0.000 description 3
239000010408 film Substances 0.000 description 3
238000000338 in vitro Methods 0.000 description 3
YYGNTYWPHWGJRM-UHFFFAOYSA-N (6E,10E,14E,18E)-2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene Chemical compound CC(C)=CCCC(C)=CCCC(C)=CCCC=C(C)CCC=C(C)CCC=C(C)C YYGNTYWPHWGJRM-UHFFFAOYSA-N 0.000 description 2
VCVMWFDNPLLHKP-UHFFFAOYSA-N 2,2,7,7-tetramethylocta-3,5-diyne Chemical compound CC(C)(C)C#CC#CC(C)(C)C VCVMWFDNPLLHKP-UHFFFAOYSA-N 0.000 description 2
241001480043 Arthrodermataceae Species 0.000 description 2
CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-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
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
BHEOSNUKNHRBNM-UHFFFAOYSA-N Tetramethylsqualene Natural products CC(=C)C(C)CCC(=C)C(C)CCC(C)=CCCC=C(C)CCC(C)C(=C)CCC(C)C(C)=C BHEOSNUKNHRBNM-UHFFFAOYSA-N 0.000 description 2
238000004458 analytical method Methods 0.000 description 2
238000000998 batch distillation Methods 0.000 description 2
239000003610 charcoal Substances 0.000 description 2
239000000498 cooling water Substances 0.000 description 2
230000001351 cycling effect Effects 0.000 description 2
230000037304 dermatophytes Effects 0.000 description 2
PRAKJMSDJKAYCZ-UHFFFAOYSA-N dodecahydrosqualene Natural products CC(C)CCCC(C)CCCC(C)CCCCC(C)CCCC(C)CCCC(C)C PRAKJMSDJKAYCZ-UHFFFAOYSA-N 0.000 description 2
230000000694 effects Effects 0.000 description 2
230000008686 ergosterol biosynthesis Effects 0.000 description 2
230000000855 fungicidal effect Effects 0.000 description 2
230000002401 inhibitory effect Effects 0.000 description 2
238000011031 large-scale manufacturing process Methods 0.000 description 2
239000000463 material Substances 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
230000003389 potentiating effect Effects 0.000 description 2
238000010898 silica gel chromatography Methods 0.000 description 2
239000002904 solvent Substances 0.000 description 2
229940031439 squalene Drugs 0.000 description 2
TUHBEKDERLKLEC-UHFFFAOYSA-N squalene Natural products CC(=CCCC(=CCCC(=CCCC=C(/C)CCC=C(/C)CC=C(C)C)C)C)C TUHBEKDERLKLEC-UHFFFAOYSA-N 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
239000010409 thin film Substances 0.000 description 2
238000005292 vacuum distillation Methods 0.000 description 2
QYIMSPSDBYKPPY-BANQPHDMSA-N 2,3-epoxysqualene Chemical compound CC(C)=CCC\C(C)=C\CC\C(C)=C\CC\C=C(/C)CC\C=C(/C)CCC1OC1(C)C QYIMSPSDBYKPPY-BANQPHDMSA-N 0.000 description 1
NQFDBNASDXPZGS-UHFFFAOYSA-N 6,7-dimethyldodeca-1,11-dien-4,8-diyne-6,7-diol Chemical compound C=CCC#CC(O)(C)C(C)(O)C#CCC=C NQFDBNASDXPZGS-UHFFFAOYSA-N 0.000 description 1
241000478345 Afer Species 0.000 description 1
OMUOKNFTKFFOMI-SFECMWDFSA-N C#C\C=C/C#C\C=C/C#C Chemical compound C#C\C=C/C#C\C=C/C#C OMUOKNFTKFFOMI-SFECMWDFSA-N 0.000 description 1
241000222120 Candida <Saccharomycetales> Species 0.000 description 1
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
208000007163 Dermatomycoses Diseases 0.000 description 1
241001480035 Epidermophyton Species 0.000 description 1
206010017533 Fungal infection Diseases 0.000 description 1
241000233866 Fungi Species 0.000 description 1
JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
241001480037 Microsporum Species 0.000 description 1
208000031888 Mycoses Diseases 0.000 description 1
241000223252 Rhodotorula Species 0.000 description 1
240000004808 Saccharomyces cerevisiae Species 0.000 description 1
206010039509 Scab Diseases 0.000 description 1
102000005782 Squalene Monooxygenase Human genes 0.000 description 1
108020003891 Squalene monooxygenase Proteins 0.000 description 1
229920006362 Teflon® Polymers 0.000 description 1
241000223238 Trichophyton Species 0.000 description 1
238000004847 absorption spectroscopy Methods 0.000 description 1
238000009825 accumulation Methods 0.000 description 1
230000009471 action Effects 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
230000000843 anti-fungal effect Effects 0.000 description 1
230000001857 anti-mycotic effect Effects 0.000 description 1
229940121375 antifungal agent Drugs 0.000 description 1
239000002543 antimycotic Substances 0.000 description 1
238000005899 aromatization reaction Methods 0.000 description 1
229940072107 ascorbate Drugs 0.000 description 1
235000010323 ascorbic acid Nutrition 0.000 description 1
239000011668 ascorbic acid Substances 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
125000001246 bromo group Chemical group Br* 0.000 description 1
HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 1
235000011089 carbon dioxide Nutrition 0.000 description 1
230000015556 catabolic process Effects 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
230000010261 cell growth Effects 0.000 description 1
230000008859 change Effects 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
238000004140 cleaning Methods 0.000 description 1
230000003749 cleanliness Effects 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
238000006731 degradation reaction Methods 0.000 description 1
238000009792 diffusion process Methods 0.000 description 1
239000000539 dimer Substances 0.000 description 1
238000003379 elimination reaction Methods 0.000 description 1
238000004880 explosion Methods 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
230000006872 improvement Effects 0.000 description 1
238000009776 industrial production Methods 0.000 description 1
239000003112 inhibitor Substances 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
238000006317 isomerization reaction Methods 0.000 description 1
229940089474 lamisil Drugs 0.000 description 1
229940049920 malate Drugs 0.000 description 1
BJEPYKJPYRNKOW-UHFFFAOYSA-L malate(2-) Chemical compound [O-]C(=O)C(O)CC([O-])=O BJEPYKJPYRNKOW-UHFFFAOYSA-L 0.000 description 1
150000004701 malic acid derivatives Chemical class 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
150000002894 organic compounds Chemical class 0.000 description 1
239000011368 organic material Substances 0.000 description 1
NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
230000001717 pathogenic effect Effects 0.000 description 1
FPCAUUABCRPODB-UHFFFAOYSA-N penta-1,2-dien-4-yne Chemical compound C=C=CC#C FPCAUUABCRPODB-UHFFFAOYSA-N 0.000 description 1
239000003016 pheromone Substances 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
230000002035 prolonged effect Effects 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
238000005096 rolling process Methods 0.000 description 1
238000007789 sealing Methods 0.000 description 1
238000000926 separation method Methods 0.000 description 1
238000001577 simple distillation Methods 0.000 description 1
210000003491 skin Anatomy 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
239000007858 starting material Substances 0.000 description 1
238000003860 storage Methods 0.000 description 1
210000000434 stratum corneum Anatomy 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
238000002560 therapeutic procedure Methods 0.000 description 1
238000001149 thermolysis Methods 0.000 description 1
210000001519 tissue Anatomy 0.000 description 1
230000000699 topical effect Effects 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
230000009466 transformation Effects 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
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/82—Purification; Separation; Stabilisation; Use of additives
- C07C209/84—Purification
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/10—Antimycotics
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/01—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms
- C07C211/26—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring
- C07C211/27—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring having amino groups linked to the six-membered aromatic ring by saturated carbon chains
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/01—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms
- C07C211/26—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring
- C07C211/30—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring the six-membered aromatic ring being part of a condensed ring system formed by two rings

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Life Sciences & Earth Sciences (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Communicable Diseases (AREA)
Pharmacology & Pharmacy (AREA)
Oncology (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

ZA200601264A 2003-08-29 2006-02-13 Purification process ZA200601264B (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GBGB0320312.2A GB0320312D0 (en)	2003-08-29	2003-08-29	Purification process

Publications (1)

Publication Number	Publication Date
ZA200601264B true ZA200601264B (en)	2007-06-27

Family

ID=28686596

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
ZA200601264A ZA200601264B (en)	2003-08-29	2006-02-13	Purification process

Country Status (25)

Country	Link
US (2)	US20060076227A1 (pt)
EP (1)	EP1694631A2 (pt)
JP (1)	JP5208416B2 (pt)
KR (2)	KR101233024B1 (pt)
CN (1)	CN100491334C (pt)
AR (1)	AR045506A1 (pt)
AU (1)	AU2004268051B2 (pt)
BR (1)	BRPI0413896A (pt)
CA (1)	CA2536498C (pt)
EC (1)	ECSP066382A (pt)
GB (1)	GB0320312D0 (pt)
IL (1)	IL173709A (pt)
IS (1)	IS8369A (pt)
MA (1)	MA28030A1 (pt)
MX (1)	MXPA06002348A (pt)
MY (1)	MY149357A (pt)
NO (1)	NO20061404L (pt)
NZ (1)	NZ545445A (pt)
PE (1)	PE20050873A1 (pt)
RU (1)	RU2367649C2 (pt)
SG (1)	SG145782A1 (pt)
TN (1)	TNSN06066A1 (pt)
TW (1)	TWI350829B (pt)
WO (1)	WO2005021483A2 (pt)
ZA (1)	ZA200601264B (pt)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB0503942D0 (en) *	2005-02-25	2005-04-06	Novartis Ag	Purification process
EP1900378A1 (en) *	2006-08-31	2008-03-19	Novartis AG	Pharmaceutical compositions for the treatment of fungal infections
WO2010027468A1 (en)	2008-09-05	2010-03-11	Travanti Pharma Inc.	Iontophoretic drug delivery packaging

Family Cites Families (16)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2862103D1 (en) *	1977-08-19	1982-11-18	Sandoz Ag	Propenyl amines, processes for their production and pharmaceutical compositions containing them
US5132459A (en) *	1979-08-22	1992-07-21	Sandoz Ltd.	Propenylamines, processes for their production, pharmaceutical compositions containing them and their use as pharmaceuticals
DE3069633D1 (en)	1979-08-22	1984-12-20	Sandoz Ag	Propenylamines, processes for their production, pharmaceutical compositions containing them and their use as pharmaceuticals
CS232849B1 (cs) *	1983-05-04	1985-02-14	Ladislav Kalvoda	Způsob přípravy honjugavaných eninů
RU2005717C1 (ru) *	1989-02-17	1994-01-15	Такеда кемикал-индастриз Лтд	Способ получения производных аралкиламинов или их кислотно-аддитивных солей
CH678527A5 (en)	1989-06-22	1991-09-30	Sandoz Ag	Trans(E)-N-(1-naphthyl:methyl)-heptenyl-amine prepn. - by simultaneously converting crude mixt. contg. cis and trans isomers to salt and precipitating trans isomer
JP3116364B2 (ja)	1989-10-02	2000-12-11	萬有製薬株式会社	エンイン誘導体の製造法
NZ280065A (en) *	1995-09-20	1998-04-27	Apotex Inc	Preparation of n-alkyl-n-(1-naphthylmethyl)alk-2-en-4-ynylamine derivatives
US6248363B1 (en) *	1999-11-23	2001-06-19	Lipocine, Inc.	Solid carriers for improved delivery of active ingredients in pharmaceutical compositions
AU6360499A (en)	1999-10-22	2001-04-30	Richter Gedeon Vegyeszeti Gyar Rt.	Process for preparing a substituted allylamine derivative and the salts thereof
GB2357762B (en)	2000-03-13	2002-01-30	Lundbeck & Co As H	Crystalline base of citalopram
ITMI20010421A1 (it) *	2001-03-01	2002-09-02	Ausimont Spa	Membrane porose semipermeabili di fluoropolimeri semicristallini
ITMI20010430A1 (it) *	2001-03-02	2002-09-02	Dinamite Dipharma S P A In For	Metodo per la sintesi di terbinafina
KR100459275B1 (ko) *	2001-12-28	2004-12-03	주식회사유한양행	터비나핀 또는 그의 염산염의 제조방법
ITMI20022534A1 (it) *	2002-11-29	2004-05-30	Dinamite Dipharma S P A	Procedimento per la preparazione di terbinafina mediante l'uso di platino come catalizzatore.
US20060004230A1 (en) *	2004-06-30	2006-01-05	Joseph Kaspi	Process for the preparation of terbinafine and salts thereof

2003
- 2003-08-29 GB GBGB0320312.2A patent/GB0320312D0/en not_active Ceased
2004
- 2004-08-26 AR ARP040103068A patent/AR045506A1/es not_active Application Discontinuation
- 2004-08-27 EP EP04764561A patent/EP1694631A2/en not_active Withdrawn
- 2004-08-27 TW TW093125943A patent/TWI350829B/zh not_active IP Right Cessation
- 2004-08-27 BR BRPI0413896-1A patent/BRPI0413896A/pt not_active IP Right Cessation
- 2004-08-27 SG SG200806418-0A patent/SG145782A1/en unknown
- 2004-08-27 KR KR1020067003979A patent/KR101233024B1/ko not_active Expired - Fee Related
- 2004-08-27 CN CNB2004800249663A patent/CN100491334C/zh not_active Expired - Fee Related
- 2004-08-27 WO PCT/EP2004/009587 patent/WO2005021483A2/en not_active Ceased
- 2004-08-27 AU AU2004268051A patent/AU2004268051B2/en not_active Ceased
- 2004-08-27 MX MXPA06002348A patent/MXPA06002348A/es active IP Right Grant
- 2004-08-27 PE PE2004000823A patent/PE20050873A1/es not_active Application Discontinuation
- 2004-08-27 NZ NZ545445A patent/NZ545445A/en not_active IP Right Cessation
- 2004-08-27 US US10/522,828 patent/US20060076227A1/en not_active Abandoned
- 2004-08-27 MY MYPI20043511A patent/MY149357A/en unknown
- 2004-08-27 JP JP2006524338A patent/JP5208416B2/ja not_active Expired - Fee Related
- 2004-08-27 KR KR1020127012618A patent/KR20120054109A/ko not_active Withdrawn
- 2004-08-27 CA CA2536498A patent/CA2536498C/en not_active Expired - Fee Related
- 2004-08-27 RU RU2006109640/04A patent/RU2367649C2/ru not_active IP Right Cessation
2006
- 2006-02-13 ZA ZA200601264A patent/ZA200601264B/en unknown
- 2006-02-13 IL IL173709A patent/IL173709A/en not_active IP Right Cessation
- 2006-02-17 EC EC2006006382A patent/ECSP066382A/es unknown
- 2006-02-27 TN TNP2006000066A patent/TNSN06066A1/en unknown
- 2006-03-08 MA MA28862A patent/MA28030A1/fr unknown
- 2006-03-23 IS IS8369A patent/IS8369A/is unknown
- 2006-03-28 NO NO20061404A patent/NO20061404L/no not_active Application Discontinuation
2008
- 2008-11-14 US US12/291,863 patent/US7985323B2/en not_active Expired - Fee Related

Also Published As

Publication number	Publication date
WO2005021483A2 (en)	2005-03-10
IL173709A0 (en)	2006-07-05
CA2536498C (en)	2012-10-09
KR101233024B1 (ko)	2013-02-13
WO2005021483A3 (en)	2005-05-12
BRPI0413896A (pt)	2006-10-24
GB0320312D0 (en)	2003-10-01
US20090216047A1 (en)	2009-08-27
RU2006109640A (ru)	2007-10-10
US7985323B2 (en)	2011-07-26
CA2536498A1 (en)	2005-03-10
RU2367649C2 (ru)	2009-09-20
CN1845895A (zh)	2006-10-11
JP5208416B2 (ja)	2013-06-12
CN100491334C (zh)	2009-05-27
US20060076227A1 (en)	2006-04-13
MXPA06002348A (es)	2006-05-22
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EP1694631A2 (en)	2006-08-30
MA28030A1 (fr)	2006-07-03
JP2007504110A (ja)	2007-03-01
TNSN06066A1 (en)	2007-10-03
KR20060119892A (ko)	2006-11-24
AU2004268051B2 (en)	2009-03-05
TWI350829B (en)	2011-10-21
NZ545445A (en)	2010-03-26
NO20061404L (no)	2006-08-25
KR20120054109A (ko)	2012-05-29
ECSP066382A (es)	2006-09-18
IS8369A (is)	2006-03-23
AU2004268051A1 (en)	2005-03-10
TW200523231A (en)	2005-07-16
IL173709A (en)	2012-02-29
MY149357A (en)	2013-08-30
AR045506A1 (es)	2005-11-02
PE20050873A1 (es)	2005-11-21

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