US20070155714A1 - Use of oxazolidinone-quinoline hybrid antibiotics for the treatment of anthrax and other infections - Google Patents

Use of oxazolidinone-quinoline hybrid antibiotics for the treatment of anthrax and other infections Download PDF

Info

Publication number: US20070155714A1
Authority: US; United States
Prior art keywords: group; oxo; fluoro; methyl; substituted
Prior art date: 2003-04-30
Legal status (The legal status 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 status listed.): Abandoned

Application number

US10/554,732

Other languages

English (en)

Inventor

Christian Hubschwerlen

Jean-Luc Specklin

Daniel Baeschlin

Hans Locher

Christine Schmitt

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Morphochem GmbH

Original Assignee

Morphochem AG fuer Kombinatorische Chemie

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.)

2003-04-30

Filing date

2004-04-06

Publication date

2007-07-05

2004-04-06 Application filed by Morphochem AG fuer Kombinatorische Chemie filed Critical Morphochem AG fuer Kombinatorische Chemie

2004-04-06 Priority to US10/554,732 priority Critical patent/US20070155714A1/en

2006-09-04 Assigned to MORPHOCHEM AKLIENGESELLSCHAFT FUR KOMBINATORISCHE CHEMIE reassignment MORPHOCHEM AKLIENGESELLSCHAFT FUR KOMBINATORISCHE CHEMIE ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: BAESCHLIN, DANIEL, LOCHER, HANS, HUBSCHWERLEN, CHRISTIAN, SCHMITT, CHRISTINE, SPECKLIN, JEAN-LUC

2007-01-03 Assigned to MORPHOCHEM AKTIENGESELLSCHAFT FUR KOMBINATORISCHE CHEMIE reassignment MORPHOCHEM AKTIENGESELLSCHAFT FUR KOMBINATORISCHE CHEMIE ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: BAESCHLIN, DANIEL, LOCHER, HANS, HUBSCHWERLEN, CHRISTIAN, SCHMITT, CHRISTINE, SPECKLIN, JEAN-LUC

2007-07-05 Publication of US20070155714A1 publication Critical patent/US20070155714A1/en

Status Abandoned legal-status Critical Current

Links

208000015181 infectious disease Diseases 0.000 title claims abstract description 28
241000193738 Bacillus anthracis Species 0.000 title claims abstract description 18
229940088710 antibiotic agent Drugs 0.000 title description 4
239000003242 anti bacterial agent Substances 0.000 title description 3
VRQYUGXGRUGHRB-UHFFFAOYSA-N 1,3-oxazolidin-2-one;quinoline Chemical compound O=C1NCCO1.N1=CC=CC2=CC=CC=C21 VRQYUGXGRUGHRB-UHFFFAOYSA-N 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 70
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238000000034 method Methods 0.000 claims description 79
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-1 and wherein R10 is H Chemical group 0.000 claims description 35
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239000013543 active substance Substances 0.000 description 1
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125000004466 alkoxycarbonylamino group Chemical group 0.000 description 1
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125000003282 alkyl amino group Chemical group 0.000 description 1
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FDDADAAYFIUZLX-UHFFFAOYSA-N benzyl 1-oxa-6-azaspiro[2.5]octane-6-carboxylate Chemical compound C1CC2(OC2)CCN1C(=O)OCC1=CC=CC=C1 FDDADAAYFIUZLX-UHFFFAOYSA-N 0.000 description 1
PZRAJGHBVXPIPV-UHFFFAOYSA-N benzyl 3-methylidenepyrrolidine-1-carboxylate Chemical compound C1C(=C)CCN1C(=O)OCC1=CC=CC=C1 PZRAJGHBVXPIPV-UHFFFAOYSA-N 0.000 description 1
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125000002883 imidazolyl group Chemical group 0.000 description 1
125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 1
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125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
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JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 1
239000008101 lactose Substances 0.000 description 1
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239000006193 liquid solution Substances 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 1
159000000003 magnesium salts Chemical class 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
230000001404 mediated effect Effects 0.000 description 1
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239000002184 metal Substances 0.000 description 1
125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
LSEFCHWGJNHZNT-UHFFFAOYSA-M methyl(triphenyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C)C1=CC=CC=C1 LSEFCHWGJNHZNT-UHFFFAOYSA-M 0.000 description 1
239000013081 microcrystal Substances 0.000 description 1
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239000011707 mineral Substances 0.000 description 1
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BDXCOCKHZBRBQR-ZDUSSCGKSA-N n-[[(5s)-3-[4-(azetidin-3-ylmethoxy)-3-fluorophenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C(C=C1F)=CC=C1OCC1CNC1 BDXCOCKHZBRBQR-ZDUSSCGKSA-N 0.000 description 1
HMHMNBMTWYIFBQ-LBPRGKRZSA-N n-[[(5s)-3-[4-(azetidin-3-yloxy)-3-fluorophenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C(C=C1F)=CC=C1OC1CNC1 HMHMNBMTWYIFBQ-LBPRGKRZSA-N 0.000 description 1
ANPWLBTUUNFQIO-UHFFFAOYSA-N n-bis(phenylmethoxy)phosphanyl-n-propan-2-ylpropan-2-amine Chemical compound C=1C=CC=CC=1COP(N(C(C)C)C(C)C)OCC1=CC=CC=C1 ANPWLBTUUNFQIO-UHFFFAOYSA-N 0.000 description 1
125000001624 naphthyl group Chemical group 0.000 description 1
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FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
239000002245 particle Substances 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
239000002953 phosphate buffered saline Substances 0.000 description 1
239000011505 plaster Substances 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
229940055019 propionibacterium acne Drugs 0.000 description 1
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000003373 pyrazinyl group Chemical group 0.000 description 1
125000003226 pyrazolyl group Chemical group 0.000 description 1
125000002098 pyridazinyl group Chemical group 0.000 description 1
125000000714 pyrimidinyl group Chemical group 0.000 description 1
125000000168 pyrrolyl group Chemical group 0.000 description 1
125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
239000012066 reaction slurry Substances 0.000 description 1
238000010992 reflux Methods 0.000 description 1
208000020029 respiratory tract infectious disease Diseases 0.000 description 1
201000003068 rheumatic fever Diseases 0.000 description 1
229960004889 salicylic acid Drugs 0.000 description 1
239000012047 saturated solution Substances 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
208000013223 septicemia Diseases 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
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235000020183 skimmed milk Nutrition 0.000 description 1
206010040872 skin infection Diseases 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
235000010265 sodium sulphite Nutrition 0.000 description 1
241000894007 species Species 0.000 description 1
239000007921 spray Substances 0.000 description 1
230000006641 stabilisation Effects 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
238000010254 subcutaneous injection Methods 0.000 description 1
239000007929 subcutaneous injection Substances 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
208000024891 symptom Diseases 0.000 description 1
208000011580 syndromic disease Diseases 0.000 description 1
230000009885 systemic effect Effects 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
ULSBMKGFFFMGOI-UHFFFAOYSA-N tert-butyl 1-oxa-6-azaspiro[2.5]octane-6-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC11OC1 ULSBMKGFFFMGOI-UHFFFAOYSA-N 0.000 description 1
PMLBUVZPRKXMOX-UHFFFAOYSA-N tert-butyl 4-oxoazepane-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCCC(=O)CC1 PMLBUVZPRKXMOX-UHFFFAOYSA-N 0.000 description 1
DPKBAXPHAYBPRL-UHFFFAOYSA-M tetrabutylazanium;iodide Chemical compound [I-].CCCC[N+](CCCC)(CCCC)CCCC DPKBAXPHAYBPRL-UHFFFAOYSA-M 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
125000003831 tetrazolyl group Chemical group 0.000 description 1
229940124597 therapeutic agent Drugs 0.000 description 1
125000001113 thiadiazolyl group Chemical group 0.000 description 1
125000000335 thiazolyl group Chemical group 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
206010044008 tonsillitis Diseases 0.000 description 1
230000037317 transdermal delivery Effects 0.000 description 1
IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
201000008827 tuberculosis Diseases 0.000 description 1
231100000397 ulcer Toxicity 0.000 description 1
208000000143 urethritis Diseases 0.000 description 1
208000019206 urinary tract infection Diseases 0.000 description 1
239000000304 virulence factor Substances 0.000 description 1
230000007923 virulence factor Effects 0.000 description 1

Classifications

- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
- A61K31/4709—Non-condensed quinolines and containing further heterocyclic rings
- 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
- 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
- A61P31/04—Antibacterial agents
- 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
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
- A61P31/16—Antivirals for RNA viruses for influenza or rhinoviruses
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00

Definitions

alkenyl and alkinyl refer to an unsaturated straight or branched chain alkyl group (having one, two or more double and/or triple bonds, an alkenyl preferably having one or two double bonds and an alkinyl preferably having one or two triple bonds), containing from two to ten, preferably two to six carbon atoms for example: ethenyl (vinyl), propenyl (allyl), iso-propenyl, n-pentenyl, butenyl, isoprenyl or hexa-2-enyl; ethinyl, propinyl or butinyl groups.
Any alkenyl or alkinyl group as defined herein may be substituted with one, two or more substituents, for example F, Cl, Br, I, NH 2 , OH, SH or NO 2 .
compositions according to the present invention contain at least one compound of Formula (I), (II) or (III) as the active agent and optionally carriers and/or diluents and/or adjuvants.
the pharmaceutical compositions according to the present invention may also contain additional known antibiotics.
infection(s) As used herein, unless otherwise indicated, the terms or phrases “infection(s)”, “bacterial infection(s)”, “protozoal infection(s)”, and “disorders related to bacterial infections or protozoal infections” include the following: pneumonia, otitis media, sinusitus, bronchitis, tonsillitis, and mastoiditis related to infection by Streptococcus pneumoniae, Haemophilus influenzae, Moraxella catarrhalis, Staphylococcus aureus, Enterococcus faecalis, E. faecium, E. casselflavus, S. epidermidis, S.
aureus food poisoning and toxic shock syndrome
Groups A, B, and C streptococci ulcers related to infection by Helicobacter pylori ; systemic febrile syndromes related to infection by Borrelia recurrentis ; Lyme disease related to infection by Borrelia burgdorferi ; conjunctivitis, keratitis, and dacrocystitis related to infection by Chlamydia trachomatis, Neisseria gonorrhoeae, S. aureus, S. pneumoniae, S. pyogenes, H.
Step 4 N-[(5S)- ⁇ 3-(3-fluoro-4-hydroxy-phenyl) ⁇ -2-oxo-oxazolidin-5-ylmethyl]-acetamide
the dimethylformamide was evaporated under reduced pressure and the residue was dissolved in 600 ml of a 9:1 dichloromethane/methanol mixture.
the organic layer was washed with 400 ml water and 400 ml brine.
the organic layer was dried over magnesium sulfate, filtered, and the filtrate diluted with 250 ml ethyl acetate.
the mixture was concentrated under reduced pressure to a final volume of 400 ml.
the slurry was stirred at room temperature over night.
the crystals were filtered and washed successively with 150 ml ethyl acetate and 100 ml pentane. Yield: 31.65 g, 76.7%.
Step 2 7-(4- ⁇ 4-[(5S)-(5-Acetylamino-methyl)-2-oxo-oxazolidin-3-yl]-2-fluoro-phenoxymethyl ⁇ -4-phosphonooxy-piperidin-1-yl)-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid
the catalyst was filtered off using a glass fibre filter paper. The solvents were evaporated under reduced pressure and the residue dissolved in 10 ml methanol. The solution was diluted with 20 ml water while a white solid precipitated. The solid was collected and dried. Yield: 85 mg, 68%. MS: 709.0 (M+H) + , 706.5 (M ⁇ H) ⁇ Method ESI + , ESI ⁇ .
Step 2 Succinic acid 4- ⁇ 4-[(5S)-5-(acetylamino-methyl)-2-oxo-oxazolidin-3-yl]-2-fluoro-phenoxymethyl ⁇ -piperidin-4-yl ester benzyl ester
Step 4 Succinic acid mono-[4- ⁇ 4-[(5S)-5-(acetylamino-methyl)-2-oxo-oxazolidin-3-yl]-2-fluoro-phenoxymethyl ⁇ -1-(6-carboxy-8-cyclopropyl-3-fluoro-5-oxo-5,8-dihydro-[1,8]naphthyridin-2-yl)-piperidin-4-yl]ester

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Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Chemical & Material Sciences (AREA)
Animal Behavior & Ethology (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Public Health (AREA)
Organic Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Communicable Diseases (AREA)
Oncology (AREA)
Epidemiology (AREA)
Virology (AREA)
Pulmonology (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Molecular Biology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)

US10/554,732 2003-04-30 2004-04-06 Use of oxazolidinone-quinoline hybrid antibiotics for the treatment of anthrax and other infections Abandoned US20070155714A1 (en)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
US10/554,732 US20070155714A1 (en)	2003-04-30	2004-04-06	Use of oxazolidinone-quinoline hybrid antibiotics for the treatment of anthrax and other infections

Applications Claiming Priority (4)

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US46694503P	2003-04-30	2003-04-30
US53082203P	2003-12-18	2003-12-18
US10/554,732 US20070155714A1 (en)	2003-04-30	2004-04-06	Use of oxazolidinone-quinoline hybrid antibiotics for the treatment of anthrax and other infections
PCT/EP2004/003650 WO2004096221A1 (en)	2003-04-30	2004-04-06	Use of oxazolidinone-quinoline hybrid antibiotics for the treatment of anthrax and other infections

Related Parent Applications (1)

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PCT/EP2004/003650 A-371-Of-International WO2004096221A1 (en)	2003-04-30	2004-04-06	Use of oxazolidinone-quinoline hybrid antibiotics for the treatment of anthrax and other infections

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US12/987,611 Division US8268812B2 (en)	2003-04-30	2011-01-10	Use of oxazolidinone-quinoline hybrid antibiotics for the treatment of anthrax and other infections

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US10/554,732 Abandoned US20070155714A1 (en)	2003-04-30	2004-04-06	Use of oxazolidinone-quinoline hybrid antibiotics for the treatment of anthrax and other infections
US12/987,611 Expired - Lifetime US8268812B2 (en)	2003-04-30	2011-01-10	Use of oxazolidinone-quinoline hybrid antibiotics for the treatment of anthrax and other infections
US13/596,700 Expired - Fee Related US8513231B2 (en)	2003-04-30	2012-08-28	Use of oxazolidinone-quinoline hybrid antibiotics for the treatment of anthrax and other infections

Family Applications After (2)

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US12/987,611 Expired - Lifetime US8268812B2 (en)	2003-04-30	2011-01-10	Use of oxazolidinone-quinoline hybrid antibiotics for the treatment of anthrax and other infections
US13/596,700 Expired - Fee Related US8513231B2 (en)	2003-04-30	2012-08-28	Use of oxazolidinone-quinoline hybrid antibiotics for the treatment of anthrax and other infections

Country Status (15)

Country	Link
US (3)	US20070155714A1 (de)
EP (1)	EP1620098B1 (de)
JP (2)	JP4805139B2 (de)
KR (1)	KR101101982B1 (de)
AT (1)	ATE397930T1 (de)
AU (2)	AU2004233557B2 (de)
BR (1)	BRPI0409955A (de)
CA (1)	CA2529347C (de)
DE (1)	DE602004014361D1 (de)
ES (1)	ES2308171T3 (de)
IL (1)	IL171546A (de)
MX (1)	MXPA05011654A (de)
NZ (1)	NZ543757A (de)
RU (1)	RU2351335C2 (de)
WO (1)	WO2004096221A1 (de)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US20040132764A1 (en) *	2002-10-23	2004-07-08	Morphochem Aktiengesellschaft Fuer Kombinatorische Chemie	Antibiotics for the treatment of infections in acidic environments
US20050096343A1 (en) *	2001-10-04	2005-05-05	Christian Hubschwerlen	Dual action antibiotics
US20090281088A1 (en) *	2008-03-26	2009-11-12	Global Alliance For Tb Drug Development	Bicyclic nitroimidazole-substituted phenyl oxazolidinones
US20110263571A1 (en) *	2008-10-27	2011-10-27	Mitsubishi Tanabe Pharma Corporation	Novel amide derivative and use thereof as medicine

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* Cited by examiner, † Cited by third party
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JP5536706B2 (ja)	2014-07-02
AU2004233557B2 (en)	2010-02-18
KR101101982B1 (ko)	2012-01-02
BRPI0409955A (pt)	2006-04-25
IL171546A (en)	2014-06-30
AU2004233557A1 (en)	2004-11-11
JP4805139B2 (ja)	2011-11-02
HK1078806A1 (en)	2006-03-24
EP1620098B1 (de)	2008-06-11
MXPA05011654A (es)	2005-12-15
NZ543757A (en)	2009-02-28
US8513231B2 (en)	2013-08-20
EP1620098A1 (de)	2006-02-01
CA2529347C (en)	2011-09-06
US8268812B2 (en)	2012-09-18
US20120135961A1 (en)	2012-05-31
WO2004096221A1 (en)	2004-11-11
RU2005137032A (ru)	2007-06-10
AU2010201659A1 (en)	2010-05-20
ATE397930T1 (de)	2008-07-15
DE602004014361D1 (de)	2008-07-24
JP2006526577A (ja)	2006-11-24
RU2351335C2 (ru)	2009-04-10
KR20060025525A (ko)	2006-03-21
JP2011184441A (ja)	2011-09-22
ES2308171T3 (es)	2008-12-01
CA2529347A1 (en)	2004-11-11
US20120322766A1 (en)	2012-12-20

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