SK6552003A3 - Condensed purine derivatives as A1 adenosine receptor antagonists and process for the preparation thereof - Google Patents

Condensed purine derivatives as A1 adenosine receptor antagonists and process for the preparation thereof Download PDF

Info

Publication number: SK6552003A3
Authority: SK; Slovakia
Prior art keywords: group; substituted; alkyl; amino; compound
Prior art date: 2000-12-01

Application number

SK655-2003A

Other languages

English (en)

Slovak (sk)

Inventor

Ko-Chung Lin

Chi Vu

Original Assignee

Biogen Inc

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.)

2000-12-01

Filing date

2001-11-30

Publication date

2003-12-02

2001-11-30 Application filed by Biogen Inc filed Critical Biogen Inc

2003-12-02 Publication of SK6552003A3 publication Critical patent/SK6552003A3/sk

Links

238000000034 method Methods 0.000 title claims description 39
238000002360 preparation method Methods 0.000 title claims description 11
230000008569 process Effects 0.000 title claims description 4
101150007969 ADORA1 gene Proteins 0.000 title abstract description 5
239000000296 purinergic P1 receptor antagonist Substances 0.000 title description 13
229940121359 adenosine receptor antagonist Drugs 0.000 title description 9
229940083251 peripheral vasodilators purine derivative Drugs 0.000 title description 2
150000003212 purines Chemical class 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims abstract description 105
238000011282 treatment Methods 0.000 claims abstract description 12
206010007559 Cardiac failure congestive Diseases 0.000 claims abstract description 6
206010019280 Heart failures Diseases 0.000 claims abstract description 6
208000001647 Renal Insufficiency Diseases 0.000 claims abstract description 4
208000006673 asthma Diseases 0.000 claims abstract description 4
201000006370 kidney failure Diseases 0.000 claims abstract description 4
230000008085 renal dysfunction Effects 0.000 claims abstract description 4
206010012601 diabetes mellitus Diseases 0.000 claims abstract description 3
208000037905 systemic hypertension Diseases 0.000 claims abstract description 3
-1 acylaminoalkylamino Chemical group 0.000 claims description 67
125000000217 alkyl group Chemical group 0.000 claims description 53
125000000623 heterocyclic group Chemical group 0.000 claims description 33
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 30
125000003342 alkenyl group Chemical group 0.000 claims description 28
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 27
OIRDTQYFTABQOQ-KQYNXXCUSA-N adenosine Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O OIRDTQYFTABQOQ-KQYNXXCUSA-N 0.000 claims description 26
125000000304 alkynyl group Chemical group 0.000 claims description 26
239000000203 mixture Substances 0.000 claims description 24
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 23
125000001424 substituent group Chemical group 0.000 claims description 23
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 22
239000008194 pharmaceutical composition Substances 0.000 claims description 21
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125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 20
125000003545 alkoxy group Chemical group 0.000 claims description 19
125000003118 aryl group Chemical group 0.000 claims description 18
125000003282 alkyl amino group Chemical group 0.000 claims description 17
150000001414 amino alcohols Chemical class 0.000 claims description 17
125000004663 dialkyl amino group Chemical group 0.000 claims description 17
201000010099 disease Diseases 0.000 claims description 17
239000002253 acid Substances 0.000 claims description 16
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125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 12
125000004656 alkyl sulfonylamino group Chemical group 0.000 claims description 12
150000002367 halogens Chemical class 0.000 claims description 12
SKOLWUPSYHWYAM-UHFFFAOYSA-N carbonodithioic O,S-acid Chemical compound SC(S)=O SKOLWUPSYHWYAM-UHFFFAOYSA-N 0.000 claims description 11
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208000035475 disorder Diseases 0.000 claims description 10
125000003107 substituted aryl group Chemical group 0.000 claims description 10
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BBTNLADSUVOPPN-UHFFFAOYSA-N 5,6-diaminouracil Chemical compound NC=1NC(=O)NC(=O)C=1N BBTNLADSUVOPPN-UHFFFAOYSA-N 0.000 claims description 9
125000002252 acyl group Chemical group 0.000 claims description 8
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125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
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125000004423 acyloxy group Chemical group 0.000 claims description 6
125000003172 aldehyde group Chemical group 0.000 claims description 6
125000006323 alkenyl amino group Chemical group 0.000 claims description 6
125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 6
125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims description 6
125000001691 aryl alkyl amino group Chemical group 0.000 claims description 6
125000004657 aryl sulfonyl amino group Chemical group 0.000 claims description 6
125000005279 aryl sulfonyloxy group Chemical group 0.000 claims description 6
125000004104 aryloxy group Chemical group 0.000 claims description 6
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229940125898 compound 5 Drugs 0.000 claims description 3
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NTNUDYROPUKXNA-UHFFFAOYSA-N methyl 2-(triphenyl-$l^{5}-phosphanylidene)acetate Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=CC(=O)OC)C1=CC=CC=C1 NTNUDYROPUKXNA-UHFFFAOYSA-N 0.000 claims description 3
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ABLZXFCXXLZCGV-UHFFFAOYSA-N phosphonic acid group Chemical group P(O)(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 claims description 3
238000007920 subcutaneous administration Methods 0.000 claims description 3
125000000547 substituted alkyl group Chemical group 0.000 claims description 3
PSMDLYIQGVSZDS-UHFFFAOYSA-N 2-butylhexanedioic acid Chemical compound CCCCC(C(O)=O)CCCC(O)=O PSMDLYIQGVSZDS-UHFFFAOYSA-N 0.000 claims description 2
LXQJPKMORWPZGM-UHFFFAOYSA-N 4-hydroxybicyclo[2.2.2]octane-1-carboxylic acid Chemical compound C1CC2(O)CCC1(C(=O)O)CC2 LXQJPKMORWPZGM-UHFFFAOYSA-N 0.000 claims description 2
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230000009935 nitrosation Effects 0.000 claims description 2
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230000003647 oxidation Effects 0.000 claims description 2
238000007254 oxidation reaction Methods 0.000 claims description 2
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WREHUVWNPSWCPW-UHFFFAOYSA-N 2-(4-hydroxy-1-bicyclo[2.2.2]octanyl)-8-propan-2-yl-4-propyl-7,8-dihydro-1h-imidazo[2,1-f]purin-5-one Chemical compound C1CC(O)(CC2)CCC12C1=NC(N(C(N2CC(N=C22)C(C)C)=O)CCC)=C2N1 WREHUVWNPSWCPW-UHFFFAOYSA-N 0.000 claims 1
WYHPLEBRFOHMGR-UHFFFAOYSA-N 8-ethyl-2-(4-hydroxy-1-bicyclo[2.2.2]octanyl)-4-propyl-8,9-dihydro-7H-imidazo[2,1-f]purin-5-one Chemical compound CCCn1c2nc(nc2c2NC(CC)Cn2c1=O)C12CCC(O)(CC1)CC2 WYHPLEBRFOHMGR-UHFFFAOYSA-N 0.000 claims 1
150000007513 acids Chemical class 0.000 claims 1
XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 claims 1
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 1
239000005557 antagonist Substances 0.000 abstract description 11
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Classifications

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- 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
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A—HUMAN NECESSITIES
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
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- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
- A61K31/52—Purines, e.g. adenine
- 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
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
- A61K31/52—Purines, e.g. adenine
- A61K31/522—Purines, e.g. adenine having oxo groups directly attached to the heterocyclic ring, e.g. hypoxanthine, guanine, acyclovir
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
- 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
- A61P3/08—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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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P31/10—Antimycotics
- A—HUMAN NECESSITIES
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- 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
- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/10—Antioedematous agents; Diuretics
- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/02—Non-specific cardiovascular stimulants, e.g. drugs for syncope, antihypotensives
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains three hetero rings
- C07D487/14—Ortho-condensed systems

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
General Health & Medical Sciences (AREA)
Animal Behavior & Ethology (AREA)
Medicinal Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
General Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Epidemiology (AREA)
Cardiology (AREA)
Heart & Thoracic Surgery (AREA)
Diabetes (AREA)
Hematology (AREA)
Pulmonology (AREA)
Oncology (AREA)
Communicable Diseases (AREA)
Emergency Medicine (AREA)
Endocrinology (AREA)
Obesity (AREA)
Urology & Nephrology (AREA)
Hospice & Palliative Care (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Saccharide Compounds (AREA)

SK655-2003A 2000-12-01 2001-11-30 Condensed purine derivatives as A1 adenosine receptor antagonists and process for the preparation thereof SK6552003A3 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US25065800P	2000-12-01	2000-12-01
PCT/US2001/044991 WO2002044182A1 (en)	2000-12-01	2001-11-30	Condensed purine derivatives as a1 adenosine receptor antagonists

Publications (1)

Publication Number	Publication Date
SK6552003A3 true SK6552003A3 (en)	2003-12-02

Family

ID=22948640

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK655-2003A SK6552003A3 (en)	2000-12-01	2001-11-30	Condensed purine derivatives as A1 adenosine receptor antagonists and process for the preparation thereof

Country Status (32)

Country	Link
US (2)	US6605601B2 (pl)
EP (1)	EP1347981B1 (pl)
JP (2)	JP2004514723A (pl)
KR (1)	KR20040011439A (pl)
CN (1)	CN100497340C (pl)
AR (1)	AR035400A1 (pl)
AT (1)	ATE394402T1 (pl)
AU (2)	AU1997702A (pl)
BG (1)	BG107849A (pl)
BR (1)	BR0115833A (pl)
CA (1)	CA2430508C (pl)
CZ (1)	CZ20031513A3 (pl)
DE (1)	DE60133931D1 (pl)
EA (1)	EA009814B1 (pl)
EE (1)	EE200300260A (pl)
ES (1)	ES2305139T3 (pl)
GE (1)	GEP20094697B (pl)
HU (1)	HUP0400530A3 (pl)
IL (1)	IL156046A0 (pl)
IS (1)	IS6821A (pl)
MX (1)	MXPA03004857A (pl)
MY (1)	MY127120A (pl)
NO (1)	NO20032483L (pl)
NZ (1)	NZ526511A (pl)
PL (1)	PL362642A1 (pl)
SK (1)	SK6552003A3 (pl)
TR (1)	TR200300766T2 (pl)
TW (1)	TWI293301B (pl)
UA (1)	UA75625C2 (pl)
WO (1)	WO2002044182A1 (pl)
YU (1)	YU42903A (pl)
ZA (2)	ZA200304067B (pl)

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ES2238335T3 (es) *	1999-12-24	2005-09-01	Kyowa Hakko Kogyo Co., Ltd.	Derivados de purina condensados.
UA75625C2 (en) *	2000-12-01	2006-05-15	Biogen Inc	Condensed purine derivatives as a1 adenosine receptor antagonists
JP2006518390A (ja) *	2003-02-19	2006-08-10	エンダシア，インコーポレイテッド	Ａ１アデノシンレセプターアンタゴニスト
US20040229901A1 (en) *	2003-02-24	2004-11-18	Lauren Otsuki	Method of treatment of disease using an adenosine A1 receptor antagonist
EP1637532A1 (en) *	2003-04-25	2006-03-22	Kyowa Hakko Kogyo Co., Ltd.	Fused pyrimidine derivative
AU2004233852A1 (en)	2003-04-25	2004-11-11	Novacardia, Inc.	Method of improved diuresis in individuals with impaired renal function
US7247639B2 (en) *	2003-06-06	2007-07-24	Endacea, Inc.	A1 adenosine receptor antagonists
JP2008534445A (ja) *	2005-03-11	2008-08-28	アデリスファーマシューティカルズ，インコーポレイテッド	置換９−アルキルアデニンおよびその使用
WO2007095161A2 (en) *	2006-02-14	2007-08-23	New York University	Methods and compositions for treating disorders associated with increased bone turnover and osteopenia
CA2648281A1 (en) *	2006-04-06	2007-10-18	Novacardia, Inc.	Co-administration of adenosine a1 receptor antagonists and anticonvulsants
RS52062B (sr)	2006-05-19	2012-06-30	Abbott Laboratories	Cns aktivni azabiciklični alkanski derivati koji su supstituisani spojenim bicikloheterociklom
EP2035009A1 (en) *	2006-06-16	2009-03-18	Novacardia, Inc.	Prolonged improvement of renal function comprising infrequent administration of an aa1ra
ATE486874T1 (de)	2006-06-23	2010-11-15	Incyte Corp	Purinonderivate als hm74a-agonisten
AR061625A1 (es)	2006-06-23	2008-09-10	Incyte Corp	Derivados de purinona como agonistas de hm74a
WO2008121882A1 (en) *	2007-03-29	2008-10-09	Novacardia, Inc.	Improved methods of administration of adenosine a1 receptor antagonists
WO2008121893A1 (en) *	2007-03-29	2008-10-09	Novacardia, Inc.	Methods of treating heart failure and renal dysfunction in individuals with an adenosine a1 receptor antagonist
WO2011063268A2 (en) *	2009-11-19	2011-05-26	Biogen Idec Ma Inc	Novel synthetic methods
US20130109645A1 (en)	2010-03-31	2013-05-02	The united States of America,as represented by Secretary,Dept.,of Health and Human Services	Adenosine receptor agonists for the treatment and prevention of vascular or joint capsule calcification disorders
IL275817B2 (en)	2018-01-04	2024-04-01	Impetis Biosciences Ltd	Tricyclic compounds, compositions and medicinal applications thereof

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JPH06102662B2 (ja)	1989-09-01	1994-12-14	協和醗酵工業株式会社	キサンチン誘導体
JP2988711B2 (ja) *	1989-10-20	1999-12-13	協和醗酵工業株式会社	縮合プリン誘導体
CA2254273C (en)	1991-09-23	2003-03-25	Florida State University	Preparation of substituted isoserine esters using metal alkoxides and .beta.-lactams
EP0884318A4 (en) *	1996-10-07	2002-10-23	Kyowa Hakko Kogyo Kk	CONDENSED PURINE DERIVATIVES
AU740770B2 (en)	1997-06-18	2001-11-15	Aderis Pharmaceuticals, Inc.	Compositions and methods for preventing restenosis following revascularization procedures
WO2000001388A1 (en) *	1998-07-02	2000-01-13	Kyowa Hakko Kogyo Co., Ltd.	Remedies for diabetes
ES2238335T3 (es) *	1999-12-24	2005-09-01	Kyowa Hakko Kogyo Co., Ltd.	Derivados de purina condensados.
UA75625C2 (en) *	2000-12-01	2006-05-15	Biogen Inc	Condensed purine derivatives as a1 adenosine receptor antagonists

2001
- 2001-11-30 UA UA2003066041A patent/UA75625C2/uk unknown
- 2001-11-30 EA EA200300629A patent/EA009814B1/ru not_active IP Right Cessation
- 2001-11-30 TR TR2003/00766T patent/TR200300766T2/xx unknown
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- 2001-11-30 US US09/997,740 patent/US6605601B2/en not_active Expired - Fee Related
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- 2001-11-30 KR KR10-2003-7007322A patent/KR20040011439A/ko not_active Abandoned
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2003
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2004
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2009
- 2009-12-07 JP JP2009278047A patent/JP2010053148A/ja not_active Withdrawn

Also Published As

Publication number	Publication date
US7022686B2 (en)	2006-04-04
MXPA03004857A (es)	2003-08-19
AU1997702A (en)	2002-06-11
ES2305139T3 (es)	2008-11-01
HK1059927A1 (en)	2004-07-23
AU2002219977B2 (en)	2008-01-24
CZ20031513A3 (cs)	2003-09-17
JP2004514723A (ja)	2004-05-20
EE200300260A (et)	2003-08-15
CA2430508A1 (en)	2002-06-06
UA75625C2 (en)	2006-05-15
NZ526511A (en)	2005-04-29
MY127120A (en)	2006-11-30
DE60133931D1 (de)	2008-06-19
IL156046A0 (en)	2003-12-23
TWI293301B (en)	2008-02-11
KR20040011439A (ko)	2004-02-05
US20030220358A1 (en)	2003-11-27
US20020111333A1 (en)	2002-08-15
ZA200304067B (en)	2005-05-30
PL362642A1 (pl)	2004-11-02
HUP0400530A3 (en)	2007-05-29
US6605601B2 (en)	2003-08-12
GEP20094697B (en)	2009-06-10
AR035400A1 (es)	2004-05-26
BG107849A (bg)	2004-01-30
ATE394402T1 (de)	2008-05-15
NO20032483L (no)	2003-07-30
BR0115833A (pt)	2003-10-28
IS6821A (is)	2003-05-20
EP1347981A1 (en)	2003-10-01
EA009814B1 (ru)	2008-04-28
HUP0400530A2 (hu)	2004-06-28
NO20032483D0 (no)	2003-06-02
ZA200408755B (en)	2005-07-27
EA200300629A1 (ru)	2003-12-25
JP2010053148A (ja)	2010-03-11
WO2002044182A1 (en)	2002-06-06
CA2430508C (en)	2010-05-18
CN1481387A (zh)	2004-03-10
YU42903A (sh)	2006-05-25
TR200300766T2 (tr)	2004-09-21
EP1347981B1 (en)	2008-05-07
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