UA77070C2 - Спосіб одержання кислих солей геміфлоксацину - Google Patents

Спосіб одержання кислих солей геміфлоксацину Download PDF

Info

Publication number: UA77070C2
Authority: UA; Ukraine
Prior art keywords: acid; formula; differs; compound; stage
Prior art date: 2002-04-08

Application number

UA20041008144A

Other languages

English (en)

Russian (ru)

Ukrainian (uk)

Inventor

Хун ЧОЙ

Санг-Чул ЧОЙ

До-Хьюн Нам

Бо-Сеунг Чой

Original Assignee

Елджі Лайф Саєнсез Лтд.

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.)

2002-04-08

Filing date

2003-04-04

Publication date

2006-10-16

2003-04-04 Application filed by Елджі Лайф Саєнсез Лтд. filed Critical Елджі Лайф Саєнсез Лтд.

2006-10-16 Publication of UA77070C2 publication Critical patent/UA77070C2/uk

Links

239000002253 acid Substances 0.000 title claims abstract description 21
150000003839 salts Chemical class 0.000 title claims abstract description 18
238000004519 manufacturing process Methods 0.000 title claims abstract description 14
ZRCVYEYHRGVLOC-HYARGMPZSA-N gemifloxacin Chemical class C1C(CN)C(=N/OC)/CN1C(C(=C1)F)=NC2=C1C(=O)C(C(O)=O)=CN2C1CC1 ZRCVYEYHRGVLOC-HYARGMPZSA-N 0.000 title claims abstract description 5
229960003170 gemifloxacin Drugs 0.000 title abstract description 4
238000000034 method Methods 0.000 claims abstract description 39
150000001875 compounds Chemical class 0.000 claims description 48
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 33
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 27
238000006243 chemical reaction Methods 0.000 claims description 20
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 18
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 17
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 14
HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 claims description 12
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 8
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 8
238000005859 coupling reaction Methods 0.000 claims description 8
229940098779 methanesulfonic acid Drugs 0.000 claims description 8
239000003960 organic solvent Substances 0.000 claims description 8
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 6
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 6
239000012046 mixed solvent Substances 0.000 claims description 6
150000007530 organic bases Chemical class 0.000 claims description 6
QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 claims description 6
-1 2-oxybenzaldehyde Chemical compound 0.000 claims description 4
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 claims description 4
238000010511 deprotection reaction Methods 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
150000007524 organic acids Chemical class 0.000 claims description 4
ZRSNZINYAWTAHE-UHFFFAOYSA-N p-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C=C1 ZRSNZINYAWTAHE-UHFFFAOYSA-N 0.000 claims description 4
229920006395 saturated elastomer Polymers 0.000 claims description 4
239000011877 solvent mixture Substances 0.000 claims description 4
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 claims description 4
FPYUJUBAXZAQNL-UHFFFAOYSA-N 2-chlorobenzaldehyde Chemical compound ClC1=CC=CC=C1C=O FPYUJUBAXZAQNL-UHFFFAOYSA-N 0.000 claims description 3
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 claims description 3
125000000217 alkyl group Chemical group 0.000 claims description 3
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 3
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 3
229940071870 hydroiodic acid Drugs 0.000 claims description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 3
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 3
125000003545 alkoxy group Chemical group 0.000 claims description 2
125000003118 aryl group Chemical group 0.000 claims description 2
125000004093 cyano group Chemical group *C#N 0.000 claims description 2
125000000753 cycloalkyl 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
125000004356 hydroxy functional group Chemical group O* 0.000 claims description 2
BTFQKIATRPGRBS-UHFFFAOYSA-N o-tolualdehyde Chemical compound CC1=CC=CC=C1C=O BTFQKIATRPGRBS-UHFFFAOYSA-N 0.000 claims 2
YZBFISOEIGOFAF-UHFFFAOYSA-N (4-methoxyiminopyrrolidin-3-yl)methanamine Chemical class CON=C1CNCC1CN YZBFISOEIGOFAF-UHFFFAOYSA-N 0.000 claims 1
SNLMOXFUCILIPL-UHFFFAOYSA-N 1,8-naphthyridine-2-carboxylic acid Chemical compound C1=CC=NC2=NC(C(=O)O)=CC=C21 SNLMOXFUCILIPL-UHFFFAOYSA-N 0.000 claims 1
239000001431 2-methylbenzaldehyde Substances 0.000 claims 1
125000005843 halogen group Chemical group 0.000 claims 1
125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
239000013067 intermediate product Substances 0.000 claims 1
238000012876 topography Methods 0.000 claims 1
230000008569 process Effects 0.000 abstract description 28
230000008901 benefit Effects 0.000 abstract description 4
230000000845 anti-microbial effect Effects 0.000 abstract description 3
239000003242 anti bacterial agent Substances 0.000 abstract description 2
229940088710 antibiotic agent Drugs 0.000 abstract description 2
230000003389 potentiating effect Effects 0.000 abstract description 2
LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical compound C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 abstract description 2
230000015572 biosynthetic process Effects 0.000 description 18
239000011541 reaction mixture Substances 0.000 description 16
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
239000000047 product Substances 0.000 description 12
239000000203 mixture Substances 0.000 description 11
238000002360 preparation method Methods 0.000 description 8
238000001819 mass spectrum Methods 0.000 description 7
238000001953 recrystallisation Methods 0.000 description 7
238000003756 stirring Methods 0.000 description 7
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
238000003786 synthesis reaction Methods 0.000 description 6
239000012535 impurity Substances 0.000 description 4
PQXMKYVZAQIFBU-UHFFFAOYSA-N methanesulfonic acid;(4-methoxyiminopyrrolidin-3-yl)methanamine Chemical compound CS(O)(=O)=O.CS(O)(=O)=O.CON=C1CNCC1CN PQXMKYVZAQIFBU-UHFFFAOYSA-N 0.000 description 4
239000007787 solid Substances 0.000 description 4
239000002904 solvent Substances 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
239000006227 byproduct Substances 0.000 description 2
239000007810 chemical reaction solvent Substances 0.000 description 2
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 2
VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
SMQUZDBALVYZAC-UHFFFAOYSA-N salicylaldehyde Chemical compound OC1=CC=CC=C1C=O SMQUZDBALVYZAC-UHFFFAOYSA-N 0.000 description 2
239000000126 substance Substances 0.000 description 2
SQAINHDHICKHLX-UHFFFAOYSA-N 1-naphthaldehyde Chemical compound C1=CC=C2C(C=O)=CC=CC2=C1 SQAINHDHICKHLX-UHFFFAOYSA-N 0.000 description 1
MEKOFIRRDATTAG-UHFFFAOYSA-N 2,2,5,8-tetramethyl-3,4-dihydrochromen-6-ol Chemical compound C1CC(C)(C)OC2=C1C(C)=C(O)C=C2C MEKOFIRRDATTAG-UHFFFAOYSA-N 0.000 description 1
XOQQVKDBGLYPGH-UHFFFAOYSA-N 2-oxo-1h-quinoline-3-carboxylic acid Chemical class C1=CC=C2NC(=O)C(C(=O)O)=CC2=C1 XOQQVKDBGLYPGH-UHFFFAOYSA-N 0.000 description 1
WZWIQYMTQZCSKI-UHFFFAOYSA-N 4-cyanobenzaldehyde Chemical compound O=CC1=CC=C(C#N)C=C1 WZWIQYMTQZCSKI-UHFFFAOYSA-N 0.000 description 1
244000298715 Actinidia chinensis Species 0.000 description 1
235000009434 Actinidia chinensis Nutrition 0.000 description 1
235000009436 Actinidia deliciosa Nutrition 0.000 description 1
241000894006 Bacteria Species 0.000 description 1
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
244000068988 Glycine max Species 0.000 description 1
235000010469 Glycine max Nutrition 0.000 description 1
241000581652 Hagenia abyssinica Species 0.000 description 1
241000102542 Kara Species 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
241000282320 Panthera leo Species 0.000 description 1
YASAKCUCGLMORW-UHFFFAOYSA-N Rosiglitazone Chemical compound C=1C=CC=NC=1N(C)CCOC(C=C1)=CC=C1CC1SC(=O)NC1=O YASAKCUCGLMORW-UHFFFAOYSA-N 0.000 description 1
244000172730 Rubus fruticosus Species 0.000 description 1
241001424341 Tara spinosa Species 0.000 description 1
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
239000007985 Tris NaCl EDTA buffer Substances 0.000 description 1
238000010306 acid treatment Methods 0.000 description 1
150000008043 acidic salts Chemical class 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
230000009471 action Effects 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
150000003935 benzaldehydes Chemical class 0.000 description 1
235000021029 blackberry Nutrition 0.000 description 1
MIOPJNTWMNEORI-UHFFFAOYSA-N camphorsulfonic acid Chemical compound C1CC2(CS(O)(=O)=O)C(=O)CC1C2(C)C MIOPJNTWMNEORI-UHFFFAOYSA-N 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
229940079593 drug Drugs 0.000 description 1
239000003814 drug Substances 0.000 description 1
239000012467 final product Substances 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
150000002431 hydrogen Chemical class 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
235000015141 kefir Nutrition 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
YKWNDAOEJQMLGH-UHFFFAOYSA-N phenyl 2,2-diphenylacetate Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)C(=O)OC1=CC=CC=C1 YKWNDAOEJQMLGH-UHFFFAOYSA-N 0.000 description 1
OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical compound OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 description 1
239000000843 powder Substances 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
230000036632 reaction speed Effects 0.000 description 1
230000009467 reduction Effects 0.000 description 1
230000035939 shock Effects 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
QQXLDOJGLXJCSE-KNVOCYPGSA-N tropinone Chemical compound C1C(=O)C[C@H]2CC[C@@H]1N2C QQXLDOJGLXJCSE-KNVOCYPGSA-N 0.000 description 1
JABYJIQOLGWMQW-UHFFFAOYSA-N undec-4-ene Chemical compound CCCCCCC=CCCC JABYJIQOLGWMQW-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Saccharide Compounds (AREA)

UA20041008144A 2002-04-08 2003-04-04 Спосіб одержання кислих солей геміфлоксацину UA77070C2 (uk)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
KR10-2002-0018847A KR100517638B1 (ko)	2002-04-08	2002-04-08	게미플록사신 산염의 새로운 제조방법
PCT/KR2003/000683 WO2003087100A1 (fr)	2002-04-08	2003-04-04	Procede de preparation de sels acides de gemifloxacine

Publications (1)

Publication Number	Publication Date
UA77070C2 true UA77070C2 (uk)	2006-10-16

Family

ID=36241771

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
UA20041008144A UA77070C2 (uk)	2002-04-08	2003-04-04	Спосіб одержання кислих солей геміфлоксацину

Country Status (31)

Country	Link
US (1)	US7361762B2 (fr)
EP (1)	EP1497290B1 (fr)
JP (1)	JP4315815B2 (fr)
KR (1)	KR100517638B1 (fr)
CN (1)	CN1291987C (fr)
AP (1)	AP1786A (fr)
AT (1)	ATE404559T1 (fr)
AU (1)	AU2003219581B2 (fr)
BR (1)	BRPI0309037B8 (fr)
CA (1)	CA2481217C (fr)
CO (1)	CO5611198A2 (fr)
CY (1)	CY1108469T1 (fr)
DE (1)	DE60322872D1 (fr)
DK (1)	DK1497290T3 (fr)
EA (1)	EA007222B1 (fr)
ES (1)	ES2311694T3 (fr)
GE (1)	GEP20074025B (fr)
HR (1)	HRP20040929B1 (fr)
IL (1)	IL164328A (fr)
IS (1)	IS2731B (fr)
MA (1)	MA26408A1 (fr)
MX (1)	MXPA04009777A (fr)
NO (1)	NO330042B1 (fr)
NZ (1)	NZ536174A (fr)
OA (1)	OA12801A (fr)
PL (1)	PL372815A1 (fr)
PT (1)	PT1497290E (fr)
SI (1)	SI1497290T1 (fr)
UA (1)	UA77070C2 (fr)
WO (1)	WO2003087100A1 (fr)
ZA (1)	ZA200408088B (fr)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
KR100892864B1 (ko) *	2001-08-02	2009-04-15	주식회사 엘지생명과학	4-아미노메틸렌-피롤리딘-3-온의 아미노-보호 유도체및/또는 4-아미노메틸렌-피롤리딘-3-알콕시이미노유도체들 및/또는 제미플록사신 또는 그것의 염의 제조를위한 공정
WO2006134431A1 (fr) *	2005-05-03	2006-12-21	Ranbaxy Laboratories Limited	Sel de formiate de la gemifloxacine
EP2159225A1 (fr) *	2005-06-15	2010-03-03	Hetero Drugs Limited	Procédé de gémifloxacine et polymorphes
JP5384119B2 (ja) *	2006-03-07	2014-01-08	ウォックハートリミテッド	ベンゾキノリジン−２−カルボン酸のプロドラッグ
US20100076193A1 (en) *	2006-10-31	2010-03-25	Chandrasekaran Ramasubbu	process for the preparation of gemifloxacin

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UY24504A1 (es)	1996-03-29	1997-09-19	Smithkline Beecham Corp	Dihidrato de eprosartano y un procedimiento para su produccion y formulacion
MA24500A1 (fr) *	1997-03-21	1998-10-01	Lg Life Sciences Ltd	Derive du sel d'acide carboxylique de naphthyridine .
KR100286874B1 (ko) *	1998-03-04	2001-04-16	성재갑	보호된 4-아미노메틸-피롤리딘-3-온의 제조방법
DK1082300T3 (da)	1998-05-29	2003-12-15	Upjohn Co	3-[1'-N-Methylamino)ethyl-N-benzyl]pyrrolidin-monomethansulfonat
GB9820405D0 (en)	1998-09-18	1998-11-11	Smithkline Beecham Plc	Process
PT1223935E (pt)	1999-06-29	2008-04-03	Lg Life Sciences Ltd	Utilização de compostos de gemifloxacina contra bactérias
EP1401440A4 (fr)	1999-09-01	2006-07-05	Lg Life Sciences Ltd	Procedes d'utilisation des composes des fluoroquinolones contre les bacteries
GB9920919D0 (en)	1999-09-03	1999-11-10	Sb Pharmco Inc	Novel compound
GB9920917D0 (en) *	1999-09-03	1999-11-10	Sb Pharmco Inc	Novel process
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2002
- 2002-04-08 KR KR10-2002-0018847A patent/KR100517638B1/ko not_active Expired - Lifetime
2003
- 2003-04-04 HR HRP20040929AA patent/HRP20040929B1/hr not_active IP Right Cessation
- 2003-04-04 NZ NZ536174A patent/NZ536174A/en not_active IP Right Cessation
- 2003-04-04 AT AT03715805T patent/ATE404559T1/de active
- 2003-04-04 JP JP2003584056A patent/JP4315815B2/ja not_active Expired - Fee Related
- 2003-04-04 AU AU2003219581A patent/AU2003219581B2/en not_active Ceased
- 2003-04-04 BR BRPI0309037A patent/BRPI0309037B8/pt not_active IP Right Cessation
- 2003-04-04 AP APAP/P/2004/003148A patent/AP1786A/en active
- 2003-04-04 SI SI200331341T patent/SI1497290T1/sl unknown
- 2003-04-04 WO PCT/KR2003/000683 patent/WO2003087100A1/fr not_active Ceased
- 2003-04-04 GE GEAP8436A patent/GEP20074025B/en unknown
- 2003-04-04 ES ES03715805T patent/ES2311694T3/es not_active Expired - Lifetime
- 2003-04-04 EP EP03715805A patent/EP1497290B1/fr not_active Expired - Lifetime
- 2003-04-04 CN CNB038095483A patent/CN1291987C/zh not_active Expired - Lifetime
- 2003-04-04 MX MXPA04009777A patent/MXPA04009777A/es active IP Right Grant
- 2003-04-04 UA UA20041008144A patent/UA77070C2/uk unknown
- 2003-04-04 OA OA1200400271A patent/OA12801A/en unknown
- 2003-04-04 US US10/510,514 patent/US7361762B2/en not_active Expired - Lifetime
- 2003-04-04 CA CA2481217A patent/CA2481217C/fr not_active Expired - Lifetime
- 2003-04-04 PL PL03372815A patent/PL372815A1/xx not_active Application Discontinuation
- 2003-04-04 EA EA200401328A patent/EA007222B1/ru not_active IP Right Cessation
- 2003-04-04 DK DK03715805T patent/DK1497290T3/da active
- 2003-04-04 DE DE60322872T patent/DE60322872D1/de not_active Expired - Lifetime
- 2003-04-04 PT PT03715805T patent/PT1497290E/pt unknown
2004
- 2004-09-30 IS IS7477A patent/IS2731B/is unknown
- 2004-10-05 CO CO04099283A patent/CO5611198A2/es active IP Right Grant
- 2004-10-07 MA MA27894A patent/MA26408A1/fr unknown
- 2004-10-07 ZA ZA200408088A patent/ZA200408088B/xx unknown
- 2004-10-21 IL IL164328A patent/IL164328A/en unknown
- 2004-10-27 NO NO20044629A patent/NO330042B1/no not_active IP Right Cessation
2008
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Also Published As

Publication number	Publication date
HK1074440A1 (en)	2005-11-11
CY1108469T1 (el)	2014-04-09
IL164328A0 (en)	2005-12-18
EP1497290B1 (fr)	2008-08-13
CO5611198A2 (es)	2006-02-28
MXPA04009777A (es)	2004-12-13
SI1497290T1 (sl)	2008-12-31
KR100517638B1 (ko)	2005-09-28
DE60322872D1 (de)	2008-09-25
MA26408A1 (fr)	2004-12-01
US20050148622A1 (en)	2005-07-07
CN1649868A (zh)	2005-08-03
JP4315815B2 (ja)	2009-08-19
NO20044629L (no)	2004-10-27
AP1786A (en)	2007-10-04
IS7477A (is)	2004-09-30
BRPI0309037B1 (pt)	2018-07-31
ATE404559T1 (de)	2008-08-15
AU2003219581A1 (en)	2003-10-27
ES2311694T3 (es)	2009-02-16
ZA200408088B (en)	2006-05-31
WO2003087100A1 (fr)	2003-10-23
CA2481217C (fr)	2010-06-01
DK1497290T3 (da)	2008-12-15
AP2004003148A0 (en)	2004-12-31
KR20030080292A (ko)	2003-10-17
CN1291987C (zh)	2006-12-27
OA12801A (en)	2006-07-11
EP1497290A4 (fr)	2006-05-10
BRPI0309037B8 (pt)	2021-05-25
PT1497290E (pt)	2008-11-14
PL372815A1 (en)	2005-08-08
AU2003219581B2 (en)	2006-08-24
GEP20074025B (en)	2007-01-25
NO330042B1 (no)	2011-02-07
HRP20040929A2 (en)	2005-02-28
EA007222B1 (ru)	2006-08-25
HRP20040929B1 (hr)	2013-12-06
EA200401328A1 (ru)	2005-06-30
US7361762B2 (en)	2008-04-22
EP1497290A1 (fr)	2005-01-19
IS2731B (is)	2011-04-15
IL164328A (en)	2009-08-03
JP2005529112A (ja)	2005-09-29
BR0309037A (pt)	2005-02-01
NZ536174A (en)	2006-09-29
CA2481217A1 (fr)	2003-10-23

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