SK186599A3 - 2-substituted 4,5-diaryl imidazoles, process for their preparation, pharmaceutical composition containing them and their use - Google Patents

2-substituted 4,5-diaryl imidazoles, process for their preparation, pharmaceutical composition containing them and their use Download PDF

Info

Publication number: SK186599A3
Authority: SK; Slovakia
Prior art keywords: group; carbon atoms; pyridyl; fluorophenyl; imidazole
Prior art date: 1997-06-30

Application number

SK1865-99A

Other languages

English (en)

Slovak (sk)

Inventor

Laszlo Revesz

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.)

1997-06-30

Filing date

1998-06-26

Publication date

2000-06-12

1998-06-26 Application filed by Novartis Ag filed Critical Novartis Ag

2000-06-12 Publication of SK186599A3 publication Critical patent/SK186599A3/sk

Links

238000000034 method Methods 0.000 title claims description 13
238000002360 preparation method Methods 0.000 title claims description 6
239000008194 pharmaceutical composition Substances 0.000 title claims description 4
150000001875 compounds Chemical class 0.000 claims abstract description 65
-1 alkylcycloalkenyl Chemical group 0.000 claims abstract description 57
125000001424 substituent group Chemical group 0.000 claims abstract description 35
150000003839 salts Chemical class 0.000 claims abstract description 21
150000002148 esters Chemical group 0.000 claims abstract description 20
239000002253 acid Substances 0.000 claims abstract description 17
125000002619 bicyclic group Chemical group 0.000 claims abstract description 16
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 14
125000005119 alkyl cycloalkyl group Chemical group 0.000 claims abstract description 13
125000002950 monocyclic group Chemical group 0.000 claims abstract description 12
229910052757 nitrogen Inorganic materials 0.000 claims abstract description 12
125000000392 cycloalkenyl group Chemical group 0.000 claims abstract description 10
125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 9
125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 8
239000003814 drug Substances 0.000 claims abstract description 6
230000002401 inhibitory effect Effects 0.000 claims abstract description 5
125000004665 trialkylsilyl group Chemical group 0.000 claims abstract description 5
125000004391 aryl sulfonyl group Chemical group 0.000 claims abstract description 4
125000005110 aryl thio group Chemical group 0.000 claims abstract description 4
125000004432 carbon atom Chemical group C* 0.000 claims description 64
125000000217 alkyl group Chemical group 0.000 claims description 35
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 21
125000003545 alkoxy group Chemical group 0.000 claims description 19
125000003118 aryl group Chemical group 0.000 claims description 19
125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 15
150000007942 carboxylates Chemical class 0.000 claims description 15
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 12
125000001072 heteroaryl group Chemical group 0.000 claims description 11
229910052736 halogen Inorganic materials 0.000 claims description 10
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 10
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
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IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 7
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239000003018 immunosuppressive agent Substances 0.000 claims description 6
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KLHHFYHTAPSQFN-UHFFFAOYSA-N 2-[[5-(4-fluorophenyl)-4-pyridin-4-ylimidazol-1-yl]methoxy]ethyl-trimethylsilane Chemical compound C[Si](C)(C)CCOCN1C=NC(C=2C=CN=CC=2)=C1C1=CC=C(F)C=C1 KLHHFYHTAPSQFN-UHFFFAOYSA-N 0.000 claims description 5
150000001299 aldehydes Chemical class 0.000 claims description 5
125000000623 heterocyclic group Chemical group 0.000 claims description 5
238000004519 manufacturing process Methods 0.000 claims description 5
125000005936 piperidyl group Chemical group 0.000 claims description 5
125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 claims description 4
125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 4
YXKXKUHMIZHMLM-UHFFFAOYSA-N 2,3,5,6-tetrafluoro-4-[4-(4-fluorophenyl)-5-pyridin-4-yl-1h-imidazol-2-yl]pyridine Chemical compound C1=CC(F)=CC=C1C1=C(C=2C=CN=CC=2)NC(C=2C(=C(F)N=C(F)C=2F)F)=N1 YXKXKUHMIZHMLM-UHFFFAOYSA-N 0.000 claims description 4
RTEHHLKYFIUUEN-UHFFFAOYSA-N 2-[[4-(4-fluorophenyl)-5-pyridin-4-ylimidazol-1-yl]methoxy]ethyl-trimethylsilane Chemical compound C[Si](C)(C)CCOCN1C=NC(C=2C=CC(F)=CC=2)=C1C1=CC=NC=C1 RTEHHLKYFIUUEN-UHFFFAOYSA-N 0.000 claims description 4
BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 claims description 4
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
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XIMIGUBYDJDCKI-UHFFFAOYSA-N diselenium Chemical compound [Se]=[Se] XIMIGUBYDJDCKI-UHFFFAOYSA-N 0.000 claims description 4
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SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 3
125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 2
DKNOJZGVJQZILW-UHFFFAOYSA-N 1-[4-(4-fluorophenyl)-5-pyridin-4-yl-1h-imidazol-2-yl]cyclohexan-1-ol Chemical compound N=1C(C=2C=CC(F)=CC=2)=C(C=2C=CN=CC=2)NC=1C1(O)CCCCC1 DKNOJZGVJQZILW-UHFFFAOYSA-N 0.000 claims description 2
125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims description 2
125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 2
CIWPUIAGXFUHHK-UHFFFAOYSA-N 4-[2-(4-butoxy-1-methylpiperidin-4-yl)-4-(4-fluorophenyl)-1h-imidazol-5-yl]pyridine Chemical compound N=1C(C=2C=CC(F)=CC=2)=C(C=2C=CN=CC=2)NC=1C1(OCCCC)CCN(C)CC1 CIWPUIAGXFUHHK-UHFFFAOYSA-N 0.000 claims description 2
OIENJEGEDXPCRZ-UHFFFAOYSA-N 4-[2-(cyclohexen-1-yl)-4-(4-fluorophenyl)-1h-imidazol-5-yl]pyridine Chemical compound C1=CC(F)=CC=C1C1=C(C=2C=CN=CC=2)NC(C=2CCCCC=2)=N1 OIENJEGEDXPCRZ-UHFFFAOYSA-N 0.000 claims description 2
SIQUUVQVHIMYKO-UHFFFAOYSA-N 4-[4-(4-fluorophenyl)-5-pyridin-4-yl-1h-imidazol-2-yl]-1-methylpiperidin-4-ol Chemical compound C1CN(C)CCC1(O)C1=NC(C=2C=CC(F)=CC=2)=C(C=2C=CN=CC=2)N1 SIQUUVQVHIMYKO-UHFFFAOYSA-N 0.000 claims description 2
125000005865 C2-C10alkynyl group Chemical group 0.000 claims description 2
125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 2
229910005965 SO 2 Inorganic materials 0.000 claims description 2
BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 claims description 2
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QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
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125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 2
239000003085 diluting agent Substances 0.000 claims description 2
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PORWMNRCUJJQNO-UHFFFAOYSA-N tellurium atom Chemical compound [Te] PORWMNRCUJJQNO-UHFFFAOYSA-N 0.000 claims description 2
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239000002884 skin cream Substances 0.000 description 1
239000007787 solid Substances 0.000 description 1
238000003797 solvolysis reaction Methods 0.000 description 1
238000004611 spectroscopical analysis Methods 0.000 description 1
238000012289 standard assay Methods 0.000 description 1
239000010959 steel Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000011550 stock solution Substances 0.000 description 1
150000003460 sulfonic acids Chemical class 0.000 description 1
239000006228 supernatant Substances 0.000 description 1
208000024891 symptom Diseases 0.000 description 1
208000011580 syndromic disease Diseases 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
238000007910 systemic administration Methods 0.000 description 1
201000000596 systemic lupus erythematosus Diseases 0.000 description 1
239000003826 tablet Substances 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
KJAMZCVTJDTESW-UHFFFAOYSA-N tiracizine Chemical compound C1CC2=CC=CC=C2N(C(=O)CN(C)C)C2=CC(NC(=O)OCC)=CC=C21 KJAMZCVTJDTESW-UHFFFAOYSA-N 0.000 description 1
210000001519 tissue Anatomy 0.000 description 1
125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
IHIXIJGXTJIKRB-UHFFFAOYSA-N trisodium vanadate Chemical compound [Na+].[Na+].[Na+].[O-][V]([O-])([O-])=O IHIXIJGXTJIKRB-UHFFFAOYSA-N 0.000 description 1
208000018464 vernal keratoconjunctivitis Diseases 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D451/00—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof
- C07D451/02—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof
- 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
- 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
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
- 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
- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
- A61P19/10—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease for osteoporosis
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
- C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Animal Behavior & Ethology (AREA)
Public Health (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Engineering & Computer Science (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Veterinary Medicine (AREA)
General Health & Medical Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
Immunology (AREA)
Physical Education & Sports Medicine (AREA)
Rheumatology (AREA)
Orthopedic Medicine & Surgery (AREA)
Transplantation (AREA)
Pain & Pain Management (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Steroid Compounds (AREA)

SK1865-99A 1997-06-30 1998-06-26 2-substituted 4,5-diaryl imidazoles, process for their preparation, pharmaceutical composition containing them and their use SK186599A3 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GBGB9713726.9A GB9713726D0 (en)	1997-06-30	1997-06-30	Organic compounds
PCT/EP1998/003930 WO1999001449A1 (fr)	1997-06-30	1998-06-26	4,5-diaryle imidazoles substituees en position 2

Publications (1)

Publication Number	Publication Date
SK186599A3 true SK186599A3 (en)	2000-06-12

Family

ID=10815101

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK1865-99A SK186599A3 (en)	1997-06-30	1998-06-26	2-substituted 4,5-diaryl imidazoles, process for their preparation, pharmaceutical composition containing them and their use

Country Status (28)

Country	Link
US (1)	US6300347B1 (fr)
EP (2)	EP0993456B1 (fr)
JP (1)	JP3704362B2 (fr)
KR (1)	KR20010013215A (fr)
CN (1)	CN1261885A (fr)
AR (1)	AR014886A1 (fr)
AT (1)	ATE275557T1 (fr)
AU (1)	AU744411B2 (fr)
BR (1)	BR9810955A (fr)
CA (1)	CA2291758A1 (fr)
CO (1)	CO4940462A1 (fr)
DE (1)	DE69826127T2 (fr)
ES (1)	ES2226164T3 (fr)
GB (1)	GB9713726D0 (fr)
HU (1)	HUP0003351A3 (fr)
ID (1)	ID23385A (fr)
IL (1)	IL133034A0 (fr)
NO (1)	NO996429D0 (fr)
NZ (1)	NZ501275A (fr)
PE (1)	PE99999A1 (fr)
PL (1)	PL337057A1 (fr)
PT (1)	PT993456E (fr)
RU (1)	RU2214408C2 (fr)
SK (1)	SK186599A3 (fr)
TR (1)	TR199903278T2 (fr)
TW (1)	TW429258B (fr)
WO (1)	WO1999001449A1 (fr)
ZA (1)	ZA985656B (fr)

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1997
- 1997-06-30 GB GBGB9713726.9A patent/GB9713726D0/en active Pending
1998
- 1998-06-11 TW TW087109301A patent/TW429258B/zh active
- 1998-06-25 CO CO98036362A patent/CO4940462A1/es unknown
- 1998-06-26 CA CA002291758A patent/CA2291758A1/fr not_active Abandoned
- 1998-06-26 CN CN98806673A patent/CN1261885A/zh active Pending
- 1998-06-26 EP EP98939541A patent/EP0993456B1/fr not_active Expired - Lifetime
- 1998-06-26 US US09/446,885 patent/US6300347B1/en not_active Expired - Fee Related
- 1998-06-26 JP JP50628899A patent/JP3704362B2/ja not_active Expired - Fee Related
- 1998-06-26 WO PCT/EP1998/003930 patent/WO1999001449A1/fr not_active Application Discontinuation
- 1998-06-26 DE DE69826127T patent/DE69826127T2/de not_active Expired - Fee Related
- 1998-06-26 ID IDW991681A patent/ID23385A/id unknown
- 1998-06-26 EP EP03026996A patent/EP1396491A3/fr not_active Withdrawn
- 1998-06-26 HU HU0003351A patent/HUP0003351A3/hu unknown
- 1998-06-26 TR TR1999/03278T patent/TR199903278T2/xx unknown
- 1998-06-26 ES ES98939541T patent/ES2226164T3/es not_active Expired - Lifetime
- 1998-06-26 RU RU2000101820/04A patent/RU2214408C2/ru not_active IP Right Cessation
- 1998-06-26 PT PT98939541T patent/PT993456E/pt unknown
- 1998-06-26 AU AU88015/98A patent/AU744411B2/en not_active Ceased
- 1998-06-26 SK SK1865-99A patent/SK186599A3/sk unknown
- 1998-06-26 IL IL13303498A patent/IL133034A0/xx unknown
- 1998-06-26 AR ARP980103093A patent/AR014886A1/es unknown
- 1998-06-26 NZ NZ501275A patent/NZ501275A/en unknown
- 1998-06-26 KR KR19997011203A patent/KR20010013215A/ko not_active Application Discontinuation
- 1998-06-26 BR BR9810955-3A patent/BR9810955A/pt not_active IP Right Cessation
- 1998-06-26 PL PL98337057A patent/PL337057A1/xx unknown
- 1998-06-26 PE PE1998000569A patent/PE99999A1/es not_active Application Discontinuation
- 1998-06-26 AT AT98939541T patent/ATE275557T1/de not_active IP Right Cessation
- 1998-06-29 ZA ZA985656A patent/ZA985656B/xx unknown
1999
- 1999-12-23 NO NO996429A patent/NO996429D0/no not_active Application Discontinuation

Also Published As

Publication number	Publication date
EP0993456A1 (fr)	2000-04-19
EP1396491A2 (fr)	2004-03-10
RU2214408C2 (ru)	2003-10-20
US6300347B1 (en)	2001-10-09
PL337057A1 (en)	2000-07-31
HUP0003351A2 (hu)	2001-06-28
DE69826127D1 (de)	2004-10-14
ATE275557T1 (de)	2004-09-15
CN1261885A (zh)	2000-08-02
ES2226164T3 (es)	2005-03-16
ZA985656B (en)	1998-12-30
AU744411B2 (en)	2002-02-21
TR199903278T2 (en)	2000-07-21
WO1999001449A1 (fr)	1999-01-14
JP3704362B2 (ja)	2005-10-12
CA2291758A1 (fr)	1999-01-14
CO4940462A1 (es)	2000-07-24
GB9713726D0 (en)	1997-09-03
PE99999A1 (es)	1999-11-01
NZ501275A (en)	2002-04-26
IL133034A0 (en)	2001-03-19
PT993456E (pt)	2005-01-31
AR014886A1 (es)	2001-04-11
ID23385A (id)	2000-04-20
JP2001506280A (ja)	2001-05-15
AU8801598A (en)	1999-01-25
NO996429L (no)	1999-12-23
KR20010013215A (ko)	2001-02-26
EP1396491A3 (fr)	2004-06-30
HUP0003351A3 (en)	2002-01-28
NO996429D0 (no)	1999-12-23
TW429258B (en)	2001-04-11
DE69826127T2 (de)	2005-09-29
BR9810955A (pt)	2000-09-26
EP0993456B1 (fr)	2004-09-08

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