UA77300C2 - 5-thio-?-d-glucopyranoside derivatives and pharmaceutical composition for treating diabetes - Google Patents

5-thio-?-d-glucopyranoside derivatives and pharmaceutical composition for treating diabetes Download PDF

Info

Publication number: UA77300C2
Authority: UA; Ukraine
Prior art keywords: group; alkyl; thio; alkoxy; glucopyranoside
Prior art date: 2002-08-09

Application number

UA20041210074A

Other languages

English (en)

Ukrainian (uk)

Original Assignee

Taisho Pharmaceutical Co Ltd

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.)

2002-08-09

Filing date

2003-08-08

Publication date

2006-11-15

2003-08-08 Application filed by Taisho Pharmaceutical Co Ltd filed Critical Taisho Pharmaceutical Co Ltd

2006-11-15 Publication of UA77300C2 publication Critical patent/UA77300C2/uk

Links

206010012601 diabetes mellitus Diseases 0.000 title claims abstract description 31
239000008194 pharmaceutical composition Substances 0.000 title 1
150000003839 salts Chemical class 0.000 claims abstract description 39
239000003814 drug Substances 0.000 claims abstract description 23
229940079593 drug Drugs 0.000 claims abstract description 11
230000000694 effects Effects 0.000 claims abstract description 9
201000010099 disease Diseases 0.000 claims abstract description 8
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 8
239000004480 active ingredient Substances 0.000 claims abstract description 6
230000003449 preventive effect Effects 0.000 claims abstract description 3
125000000217 alkyl group Chemical group 0.000 claims description 108
125000005843 halogen group Chemical group 0.000 claims description 97
-1 Siv alkyl C 6 oxy Chemical group 0.000 claims description 85
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 73
125000003545 alkoxy group Chemical group 0.000 claims description 67
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 55
238000002360 preparation method Methods 0.000 claims description 51
125000001424 substituent group Chemical group 0.000 claims description 44
125000002252 acyl group Chemical group 0.000 claims description 37
125000003277 amino group Chemical group 0.000 claims description 35
239000003112 inhibitor Substances 0.000 claims description 32
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 30
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 30
239000000556 agonist Substances 0.000 claims description 25
125000003710 aryl alkyl group Chemical group 0.000 claims description 25
NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 claims description 21
125000004423 acyloxy group Chemical group 0.000 claims description 20
125000003118 aryl group Chemical group 0.000 claims description 20
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 18
125000001072 heteroaryl group Chemical group 0.000 claims description 17
125000000592 heterocycloalkyl group Chemical group 0.000 claims description 16
239000011734 sodium Substances 0.000 claims description 16
239000000825 pharmaceutical preparation Substances 0.000 claims description 13
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims description 12
125000004442 acylamino group Chemical group 0.000 claims description 12
125000004414 alkyl thio group Chemical group 0.000 claims description 12
125000001691 aryl alkyl amino group Chemical group 0.000 claims description 12
125000002102 aryl alkyloxo group Chemical group 0.000 claims description 12
125000004104 aryloxy group Chemical group 0.000 claims description 12
239000008103 glucose Substances 0.000 claims description 12
125000001589 carboacyl group Chemical group 0.000 claims description 11
125000004093 cyano group Chemical group *C#N 0.000 claims description 11
125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 11
229940124597 therapeutic agent Drugs 0.000 claims description 11
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 10
229910052799 carbon Inorganic materials 0.000 claims description 10
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229940125396 insulin Drugs 0.000 claims description 10
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125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 9
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229910052739 hydrogen Inorganic materials 0.000 claims description 9
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 9
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125000000542 sulfonic acid group Chemical group 0.000 claims description 8
229940123208 Biguanide Drugs 0.000 claims description 7
239000003316 glycosidase inhibitor Substances 0.000 claims description 7
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 6
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239000003795 chemical substances by application Substances 0.000 claims description 6
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230000001539 anorectic effect Effects 0.000 claims description 5
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 5
206010061428 decreased appetite Diseases 0.000 claims description 5
229940125753 fibrate Drugs 0.000 claims description 5
239000002471 hydroxymethylglutaryl coenzyme A reductase inhibitor Substances 0.000 claims description 5
230000003228 microsomal effect Effects 0.000 claims description 5
239000004059 squalene synthase inhibitor Substances 0.000 claims description 5
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102100030817 Liver carboxylesterase 1 Human genes 0.000 claims description 4
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230000003914 insulin secretion Effects 0.000 claims description 4
UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 claims description 4
XNCOSPRUTUOJCJ-UHFFFAOYSA-N Biguanide Chemical compound NC(N)=NC(N)=N XNCOSPRUTUOJCJ-UHFFFAOYSA-N 0.000 claims description 3
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241000269435 Rana <genus> Species 0.000 claims description 3
239000002404 acyltransferase inhibitor Substances 0.000 claims description 3
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235000013744 Passiflora ligularis Nutrition 0.000 claims 1
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101000870345 Vasconcellea cundinamarcensis Cysteine proteinase 1 Proteins 0.000 claims 1
CMWTZPSULFXXJA-VIFPVBQESA-N naproxen Chemical group C1=C([C@H](C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-VIFPVBQESA-N 0.000 claims 1
238000012876 topography Methods 0.000 claims 1
230000002401 inhibitory effect Effects 0.000 abstract description 8
208000002249 Diabetes Complications Diseases 0.000 abstract description 3
150000004677 hydrates Chemical class 0.000 abstract description 2
206010012655 Diabetic complications Diseases 0.000 abstract 1
108091006269 SLC5A2 Proteins 0.000 abstract 1
102000058081 Sodium-Glucose Transporter 2 Human genes 0.000 abstract 1
150000001875 compounds Chemical class 0.000 description 112
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125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 73
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229910002027 silica gel Inorganic materials 0.000 description 37
238000004440 column chromatography Methods 0.000 description 36
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 36
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OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 27
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239000007864 aqueous solution Substances 0.000 description 21
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HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 20
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FAMRKDQNMBBFBR-UHFFFAOYSA-N ethyl n-ethoxycarbonyliminocarbamate Chemical compound CCOC(=O)N=NC(=O)OCC FAMRKDQNMBBFBR-UHFFFAOYSA-N 0.000 description 11
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150000003626 triacylglycerols Chemical class 0.000 description 1
125000001425 triazolyl group Chemical group 0.000 description 1
SYUVAXDZVWPKSI-UHFFFAOYSA-N tributyl(phenyl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C1=CC=CC=C1 SYUVAXDZVWPKSI-UHFFFAOYSA-N 0.000 description 1
TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-UHFFFAOYSA-N 0.000 description 1
229960001641 troglitazone Drugs 0.000 description 1
GXPHKUHSUJUWKP-UHFFFAOYSA-N troglitazone Chemical compound C1CC=2C(C)=C(O)C(C)=C(C)C=2OC1(C)COC(C=C1)=CC=C1CC1SC(=O)NC1=O GXPHKUHSUJUWKP-UHFFFAOYSA-N 0.000 description 1
GXPHKUHSUJUWKP-NTKDMRAZSA-N troglitazone Natural products C([C@@]1(OC=2C(C)=C(C(=C(C)C=2CC1)O)C)C)OC(C=C1)=CC=C1C[C@H]1SC(=O)NC1=O GXPHKUHSUJUWKP-NTKDMRAZSA-N 0.000 description 1
ZDPHROOEEOARMN-UHFFFAOYSA-N undecanoic acid Chemical class CCCCCCCCCCC(O)=O ZDPHROOEEOARMN-UHFFFAOYSA-N 0.000 description 1
DRTQHJPVMGBUCF-UHFFFAOYSA-N uracil arabinoside Natural products OC1C(O)C(CO)OC1N1C(=O)NC(=O)C=C1 DRTQHJPVMGBUCF-UHFFFAOYSA-N 0.000 description 1
229940045145 uridine Drugs 0.000 description 1
208000019206 urinary tract infection Diseases 0.000 description 1
125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
229940124549 vasodilator Drugs 0.000 description 1
239000003071 vasodilator agent Substances 0.000 description 1
229960001729 voglibose Drugs 0.000 description 1
SXONDGSPUVNZLO-UHFFFAOYSA-N zenarestat Chemical compound O=C1N(CC(=O)O)C2=CC(Cl)=CC=C2C(=O)N1CC1=CC=C(Br)C=C1F SXONDGSPUVNZLO-UHFFFAOYSA-N 0.000 description 1
229950006343 zenarestat Drugs 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc Substances 0.000 description 1

Classifications

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- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/20—Carbocyclic rings
- C07H15/203—Monocyclic carbocyclic rings other than cyclohexane rings; Bicyclic carbocyclic ring systems
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- C07H1/00—Processes for the preparation of sugar derivatives
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- A61P13/00—Drugs for disorders of the urinary system
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- A61P17/00—Drugs for dermatological disorders
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/06—Antigout agents, e.g. antihyperuricemic or uricosuric agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
- A—HUMAN NECESSITIES
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- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
- A—HUMAN NECESSITIES
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- A61P5/48—Drugs for disorders of the endocrine system of the pancreatic hormones
- A61P5/50—Drugs for disorders of the endocrine system of the pancreatic hormones for increasing or potentiating the activity of insulin
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
- A—HUMAN NECESSITIES
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- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/20—Carbocyclic rings

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Health & Medical Sciences (AREA)
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Organic Chemistry (AREA)
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Pharmacology & Pharmacy (AREA)
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Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
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Animal Behavior & Ethology (AREA)
Diabetes (AREA)
Biochemistry (AREA)
Molecular Biology (AREA)
Genetics & Genomics (AREA)
Biotechnology (AREA)
Cardiology (AREA)
Hematology (AREA)
Obesity (AREA)
Heart & Thoracic Surgery (AREA)
Endocrinology (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Urology & Nephrology (AREA)
Vascular Medicine (AREA)
Pain & Pain Management (AREA)
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UA20041210074A 2002-08-09 2003-08-08 5-thio-?-d-glucopyranoside derivatives and pharmaceutical composition for treating diabetes UA77300C2 (en)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
JP2002233015		2002-08-09
JP2003097839		2003-04-01
PCT/JP2003/010159 WO2004014930A1 (ja)	2002-08-09	2003-08-08	選択的なアリール５−チオ−β−Ｄ−アルドヘキソピラノシドの製造法

Publications (1)

Publication Number	Publication Date
UA77300C2 true UA77300C2 (en)	2006-11-15

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UA20041210074A UA77300C2 (en)	2002-08-09	2003-08-08	5-thio-?-d-glucopyranoside derivatives and pharmaceutical composition for treating diabetes

Country Status (18)

Country	Link
US (2)	US7414072B2 (no)
EP (2)	EP1541578A1 (no)
JP (2)	JP3813160B2 (no)
KR (2)	KR20050056194A (no)
CN (2)	CN1312165C (no)
AU (2)	AU2003254903B9 (no)
BR (1)	BR0310006A (no)
CA (2)	CA2493491A1 (no)
HR (1)	HRP20040814A2 (no)
MX (2)	MXPA05000725A (no)
NO (2)	NO20043733L (no)
NZ (1)	NZ535229A (no)
PL (2)	PL372865A1 (no)
RU (1)	RU2322449C2 (no)
TW (2)	TWI274055B (no)
UA (1)	UA77300C2 (no)
WO (2)	WO2004014930A1 (no)
ZA (1)	ZA200407187B (no)

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2003
- 2003-08-08 RU RU2004135914/04A patent/RU2322449C2/ru not_active IP Right Cessation
- 2003-08-08 EP EP03784622A patent/EP1541578A1/en not_active Withdrawn
- 2003-08-08 MX MXPA05000725A patent/MXPA05000725A/es active IP Right Grant
- 2003-08-08 TW TW092121886A patent/TWI274055B/zh not_active IP Right Cessation
- 2003-08-08 WO PCT/JP2003/010159 patent/WO2004014930A1/ja not_active Ceased
- 2003-08-08 KR KR1020057002280A patent/KR20050056194A/ko not_active Ceased
- 2003-08-08 CA CA002493491A patent/CA2493491A1/en not_active Abandoned
- 2003-08-08 UA UA20041210074A patent/UA77300C2/uk unknown
- 2003-08-08 WO PCT/JP2003/010160 patent/WO2004014931A1/ja not_active Ceased
- 2003-08-08 EP EP03784623A patent/EP1528066A4/en not_active Withdrawn
- 2003-08-08 TW TW092121895A patent/TW200409778A/zh unknown
- 2003-08-08 AU AU2003254903A patent/AU2003254903B9/en not_active Ceased
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- 2003-08-08 CA CA002478889A patent/CA2478889A1/en not_active Abandoned
- 2003-08-08 PL PL03372865A patent/PL372865A1/xx not_active Application Discontinuation
- 2003-08-08 CN CNB038056402A patent/CN1312165C/zh not_active Expired - Fee Related
- 2003-08-08 MX MXPA04009265A patent/MXPA04009265A/es active IP Right Grant
- 2003-08-08 PL PL03375298A patent/PL375298A1/xx not_active Application Discontinuation
- 2003-08-08 KR KR1020047014192A patent/KR100588457B1/ko not_active Expired - Fee Related
- 2003-08-08 HR HR20040814A patent/HRP20040814A2/hr not_active Application Discontinuation
- 2003-08-08 BR BR0310006-5A patent/BR0310006A/pt not_active IP Right Cessation
- 2003-08-08 US US10/518,788 patent/US7414072B2/en not_active Expired - Fee Related
- 2003-08-08 JP JP2004527383A patent/JP3813160B2/ja not_active Expired - Fee Related
- 2003-08-08 JP JP2004527382A patent/JPWO2004014930A1/ja not_active Ceased
- 2003-08-08 CN CNB038191423A patent/CN100341885C/zh not_active Expired - Fee Related
- 2003-08-08 US US10/521,809 patent/US7250522B2/en not_active Expired - Fee Related
- 2003-08-08 AU AU2003254904A patent/AU2003254904A1/en not_active Abandoned
2004
- 2004-09-07 NO NO20043733A patent/NO20043733L/no not_active Application Discontinuation
- 2004-09-08 ZA ZA200407187A patent/ZA200407187B/en unknown
2005
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Also Published As

Publication number	Publication date
HRP20040814A2 (en)	2005-06-30
PL372865A1 (en)	2005-08-08
EP1541578A1 (en)	2005-06-15
US7250522B2 (en)	2007-07-31
HK1077582A1 (en)	2006-02-17
KR100588457B1 (ko)	2006-06-12
MXPA04009265A (es)	2005-01-25
HK1079532A1 (en)	2006-04-07
ZA200407187B (en)	2006-02-22
KR20050056194A (ko)	2005-06-14
NO20050650L (no)	2005-03-04
NZ535229A (en)	2006-05-26
AU2003254903A1 (en)	2004-02-25
RU2004135914A (ru)	2005-05-10
NO20043733L (no)	2004-10-20
RU2322449C2 (ru)	2008-04-20
MXPA05000725A (es)	2005-04-08
CN1639180A (zh)	2005-07-13
WO2004014930A1 (ja)	2004-02-19
KR20050018642A (ko)	2005-02-23
BR0310006A (pt)	2005-02-15
US7414072B2 (en)	2008-08-19
TW200406396A (en)	2004-05-01
PL375298A1 (en)	2005-11-28
JPWO2004014930A1 (ja)	2005-12-02
AU2003254904A1 (en)	2004-02-25
EP1528066A1 (en)	2005-05-04
CA2478889A1 (en)	2004-02-19
CA2493491A1 (en)	2004-02-19
AU2003254903B2 (en)	2008-07-31
JP3813160B2 (ja)	2006-08-23
EP1528066A4 (en)	2007-05-02
US20050209309A1 (en)	2005-09-22
CN1312165C (zh)	2007-04-25
TW200409778A (en)	2004-06-16
US20050256317A1 (en)	2005-11-17
CN1675233A (zh)	2005-09-28
JPWO2004014931A1 (ja)	2005-12-02
AU2003254903B9 (en)	2008-08-21
TWI274055B (en)	2007-02-21
CN100341885C (zh)	2007-10-10
WO2004014931A1 (ja)	2004-02-19

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