ZA200200017B - Substituted purine derivatives as inhibitors of cell adhesion. - Google Patents
Substituted purine derivatives as inhibitors of cell adhesion. Download PDFInfo
- Publication number
- ZA200200017B ZA200200017B ZA200200017A ZA200200017A ZA200200017B ZA 200200017 B ZA200200017 B ZA 200200017B ZA 200200017 A ZA200200017 A ZA 200200017A ZA 200200017 A ZA200200017 A ZA 200200017A ZA 200200017 B ZA200200017 B ZA 200200017B
- Authority
- ZA
- South Africa
- Prior art keywords
- alkyl
- aryl
- alkoxy
- cycloalkyl
- heteroaryl
- Prior art date
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- 239000003112 inhibitor Substances 0.000 title claims description 11
- 125000000561 purinyl group Chemical class N1=C(N=C2N=CNC2=C1)* 0.000 title claims description 4
- 230000021164 cell adhesion Effects 0.000 title description 3
- 229940083251 peripheral vasodilators purine derivative Drugs 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims description 54
- -1 nitro, hydroxycarbonyl- Chemical group 0.000 claims description 52
- 125000001424 substituent group Chemical group 0.000 claims description 44
- 229910052757 nitrogen Inorganic materials 0.000 claims description 34
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 33
- 229910052739 hydrogen Inorganic materials 0.000 claims description 26
- 125000003118 aryl group Chemical group 0.000 claims description 25
- 239000001257 hydrogen Substances 0.000 claims description 25
- 229940002612 prodrug Drugs 0.000 claims description 25
- 239000000651 prodrug Substances 0.000 claims description 25
- 125000004432 carbon atom Chemical group C* 0.000 claims description 24
- 125000005842 heteroatom Chemical group 0.000 claims description 24
- 150000003839 salts Chemical class 0.000 claims description 23
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 19
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 19
- 229910052760 oxygen Inorganic materials 0.000 claims description 19
- 239000001301 oxygen Substances 0.000 claims description 19
- 229910052717 sulfur Inorganic materials 0.000 claims description 19
- 239000011593 sulfur Substances 0.000 claims description 19
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 18
- 239000000460 chlorine Substances 0.000 claims description 18
- 229910052801 chlorine Inorganic materials 0.000 claims description 18
- 239000011737 fluorine Substances 0.000 claims description 18
- 229910052731 fluorine Inorganic materials 0.000 claims description 18
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 17
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 17
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 17
- 229910052794 bromium Inorganic materials 0.000 claims description 17
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 16
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- 208000006386 Bone Resorption Diseases 0.000 claims description 14
- 230000024279 bone resorption Effects 0.000 claims description 14
- 239000000203 mixture Substances 0.000 claims description 14
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 13
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 13
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 12
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- 108010048673 Vitronectin Receptors Proteins 0.000 claims description 11
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 11
- 125000001072 heteroaryl group Chemical group 0.000 claims description 10
- 125000000623 heterocyclic group Chemical group 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 10
- 125000004122 cyclic group Chemical group 0.000 claims description 9
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 9
- 230000008569 process Effects 0.000 claims description 8
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- 125000006574 non-aromatic ring group Chemical group 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 238000011321 prophylaxis Methods 0.000 claims description 4
- 239000002464 receptor antagonist Substances 0.000 claims description 4
- 229940044551 receptor antagonist Drugs 0.000 claims description 4
- 238000002560 therapeutic procedure Methods 0.000 claims description 4
- SCNPUDCZXNUNQZ-UHFFFAOYSA-N 4-(furan-2-yl)-1-[(4-methoxyphenyl)methyl]pyrazolo[3,4-d]pyrimidine Chemical group C1=CC(OC)=CC=C1CN1C2=NC=NC(C=3OC=CC=3)=C2C=N1 SCNPUDCZXNUNQZ-UHFFFAOYSA-N 0.000 claims description 3
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- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
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- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 10
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- 125000004448 alkyl carbonyl group Chemical group 0.000 claims 1
- 230000003110 anti-inflammatory effect Effects 0.000 claims 1
- 125000005141 aryl amino sulfonyl group Chemical group 0.000 claims 1
- 125000004657 aryl sulfonyl amino group Chemical group 0.000 claims 1
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- 210000002997 osteoclast Anatomy 0.000 description 14
- 210000004027 cell Anatomy 0.000 description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 11
- 210000000988 bone and bone Anatomy 0.000 description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 7
- 239000005557 antagonist Substances 0.000 description 6
- 125000004429 atom Chemical group 0.000 description 6
- 125000002950 monocyclic group Chemical group 0.000 description 6
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 5
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 5
- IYMAXBFPHPZYIK-BQBZGAKWSA-N Arg-Gly-Asp Chemical compound NC(N)=NCCC[C@H](N)C(=O)NCC(=O)N[C@@H](CC(O)=O)C(O)=O IYMAXBFPHPZYIK-BQBZGAKWSA-N 0.000 description 5
- 125000002252 acyl group Chemical group 0.000 description 5
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- 210000002805 bone matrix Anatomy 0.000 description 5
- 239000002253 acid Substances 0.000 description 4
- ORILYTVJVMAKLC-UHFFFAOYSA-N adamantane Chemical compound C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 description 4
- 230000033115 angiogenesis Effects 0.000 description 4
- 108010072041 arginyl-glycyl-aspartic acid Proteins 0.000 description 4
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 4
- 238000011282 treatment Methods 0.000 description 4
- 125000004417 unsaturated alkyl group Chemical group 0.000 description 4
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 3
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 3
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 201000011510 cancer Diseases 0.000 description 3
- 125000002837 carbocyclic group Chemical group 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 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
- 230000006378 damage Effects 0.000 description 3
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- 230000003993 interaction Effects 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
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- 230000011164 ossification Effects 0.000 description 3
- 125000000547 substituted alkyl group Chemical group 0.000 description 3
- 230000002792 vascular Effects 0.000 description 3
- XLBBKEHLEPNMMF-SSUNCQRMSA-N 129038-42-2 Chemical compound C([C@@H](C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCC(O)=O)C(=O)NCC(=O)N[C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CS)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](C)C(=O)N[C@@H](CCCNC(N)=N)C(=O)NCC(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N[C@@H](CS)C(=O)N[C@@H](CC(N)=O)C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CS)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CS)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC(N)=O)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N[C@@H](CCCCN)C(=O)NCC(=O)N1[C@@H](CCC1)C(=O)N[C@@H](C)C(=O)N[C@@H]([C@@H](C)O)C(O)=O)[C@@H](C)O)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CS)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CS)NC(=O)[C@H](CS)NC(=O)[C@H]1N(CCC1)C(=O)CNC(=O)[C@H](CO)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CS)NC(=O)[C@@H](N)CCC(O)=O)C1=CC=CC=C1 XLBBKEHLEPNMMF-SSUNCQRMSA-N 0.000 description 2
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- 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
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/24—Drugs for disorders of the endocrine system of the sex hormones
-
- 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
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- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Physical Education & Sports Medicine (AREA)
- Rheumatology (AREA)
- Endocrinology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Diabetes (AREA)
- Pain & Pain Management (AREA)
- Neurosurgery (AREA)
- Dermatology (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP99112637A EP1065208A1 (en) | 1999-07-02 | 1999-07-02 | Substituted purine derivatives as inhibitors of cell adhesion |
Publications (1)
Publication Number | Publication Date |
---|---|
ZA200200017B true ZA200200017B (en) | 2003-01-02 |
Family
ID=8238483
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
ZA200200017A ZA200200017B (en) | 1999-07-02 | 2002-01-02 | Substituted purine derivatives as inhibitors of cell adhesion. |
Country Status (30)
Country | Link |
---|---|
US (1) | US6747016B1 (hu) |
EP (2) | EP1065208A1 (hu) |
JP (1) | JP2003503497A (hu) |
KR (1) | KR20020015997A (hu) |
CN (1) | CN1171888C (hu) |
AR (1) | AR034242A1 (hu) |
AT (1) | ATE262528T1 (hu) |
AU (1) | AU774382B2 (hu) |
BG (1) | BG106229A (hu) |
BR (1) | BR0012050A (hu) |
CA (1) | CA2376673A1 (hu) |
CZ (1) | CZ20014553A3 (hu) |
DE (1) | DE60009296T2 (hu) |
EA (1) | EA005372B1 (hu) |
EE (1) | EE200100713A (hu) |
ES (1) | ES2219353T3 (hu) |
HU (1) | HUP0300183A3 (hu) |
IL (1) | IL147245A0 (hu) |
MX (1) | MXPA01013241A (hu) |
MY (1) | MY122631A (hu) |
NO (1) | NO20016403L (hu) |
NZ (1) | NZ516095A (hu) |
PL (1) | PL352281A1 (hu) |
SK (1) | SK18792001A3 (hu) |
TR (1) | TR200103858T2 (hu) |
TW (1) | TWI229080B (hu) |
UA (1) | UA72923C2 (hu) |
WO (1) | WO2001002399A1 (hu) |
YU (1) | YU89701A (hu) |
ZA (1) | ZA200200017B (hu) |
Families Citing this family (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE10042655A1 (de) * | 2000-08-31 | 2002-03-14 | Aventis Pharma Gmbh | Verfahren zur Herstellung von Inhibitoren der Zell-Adhäsion |
FR2847254B1 (fr) | 2002-11-19 | 2005-01-28 | Aventis Pharma Sa | Nouveaux derives antagonistes du recepteur de la vitronectine, leur procede de preparation, leur application comme medicaments et les compositions pharmaceutiques les refermant |
FR2870541B1 (fr) | 2004-05-18 | 2006-07-14 | Proskelia Sas | Derives de pyrimidines antigonistes du recepteur de la vitronectine |
ES2684821T3 (es) | 2005-12-29 | 2018-10-04 | Lexicon Pharmaceuticals, Inc. | Derivados de aminoácidos multicíclicos y métodos de su uso |
CL2007002994A1 (es) * | 2006-10-19 | 2008-02-08 | Wyeth Corp | Compuestos derivados heterociclicos que contienen sulfamoilo, inhibidores de hsp90; composicion farmaceutica; y uso para el tratamiento del cancer, tal como cancer de mama, de colon y prostata, entre otros. |
CN107450106A (zh) * | 2017-09-28 | 2017-12-08 | 北京小米移动软件有限公司 | 饮水安全提示方法、装置及智能水杯 |
WO2021226261A1 (en) | 2020-05-06 | 2021-11-11 | Ajax Therapeutics, Inc. | 6-heteroaryloxy benzimidazoles and azabenzimidazoles as jak2 inhibitors |
AU2022388555A1 (en) | 2021-11-09 | 2024-05-02 | Ajax Therapeutics, Inc. | 6-he tero aryloxy benzimidazoles and azabenzimidazoles as jak2 inhibitors |
Family Cites Families (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5741796A (en) * | 1994-05-27 | 1998-04-21 | Merck & Co., Inc. | Pyridyl and naphthyridyl compounds for inhibiting osteoclast-mediated bone resorption |
EP0934305A4 (en) * | 1996-08-29 | 2001-04-11 | Merck & Co Inc | INTEGRINE ANTAGONISTS |
AU717283B2 (en) * | 1996-10-30 | 2000-03-23 | Merck & Co., Inc. | Integrin antagonists |
DE19653646A1 (de) * | 1996-12-20 | 1998-06-25 | Hoechst Ag | Substituierte Purinderivate, Verfahren zu deren Herstellung, sie enthaltende Mittel und deren Verwendung |
AU729869B2 (en) * | 1997-01-17 | 2001-02-15 | Merck & Co., Inc. | Integrin antagonists |
WO1999037621A1 (en) * | 1998-01-23 | 1999-07-29 | Aventis Pharma Deutschland Gmbh | Novel sulfonamide derivatives as inhibitors of bone resorption and as inhibitors of cell adhesion |
WO1999038621A1 (en) | 1998-01-28 | 1999-08-05 | Danmist Aps | Method of piezoelectrically atomising and pumping fluids and piezoelectric fluid atomising and pumping device |
-
1999
- 1999-07-02 EP EP99112637A patent/EP1065208A1/en not_active Withdrawn
-
2000
- 2000-06-26 AU AU55349/00A patent/AU774382B2/en not_active Ceased
- 2000-06-26 CZ CZ20014553A patent/CZ20014553A3/cs unknown
- 2000-06-26 MX MXPA01013241A patent/MXPA01013241A/es active IP Right Grant
- 2000-06-26 HU HU0300183A patent/HUP0300183A3/hu unknown
- 2000-06-26 US US10/030,290 patent/US6747016B1/en not_active Expired - Fee Related
- 2000-06-26 SK SK1879-2001A patent/SK18792001A3/sk unknown
- 2000-06-26 TR TR2001/03858T patent/TR200103858T2/xx unknown
- 2000-06-26 CN CNB008121001A patent/CN1171888C/zh not_active Expired - Fee Related
- 2000-06-26 NZ NZ516095A patent/NZ516095A/en unknown
- 2000-06-26 JP JP2001507836A patent/JP2003503497A/ja not_active Withdrawn
- 2000-06-26 IL IL14724500A patent/IL147245A0/xx unknown
- 2000-06-26 EP EP00940406A patent/EP1196416B1/en not_active Expired - Lifetime
- 2000-06-26 CA CA002376673A patent/CA2376673A1/en not_active Abandoned
- 2000-06-26 PL PL00352281A patent/PL352281A1/xx not_active Application Discontinuation
- 2000-06-26 EE EEP200100713A patent/EE200100713A/xx unknown
- 2000-06-26 DE DE60009296T patent/DE60009296T2/de not_active Expired - Fee Related
- 2000-06-26 AT AT00940406T patent/ATE262528T1/de not_active IP Right Cessation
- 2000-06-26 EA EA200200121A patent/EA005372B1/ru not_active IP Right Cessation
- 2000-06-26 ES ES00940406T patent/ES2219353T3/es not_active Expired - Lifetime
- 2000-06-26 BR BR0012050-2A patent/BR0012050A/pt not_active IP Right Cessation
- 2000-06-26 UA UA2002020851A patent/UA72923C2/uk unknown
- 2000-06-26 WO PCT/EP2000/005921 patent/WO2001002399A1/en not_active Application Discontinuation
- 2000-06-26 KR KR1020017016962A patent/KR20020015997A/ko not_active Application Discontinuation
- 2000-06-29 AR ARP000103314A patent/AR034242A1/es not_active Application Discontinuation
- 2000-06-29 MY MYPI20002961A patent/MY122631A/en unknown
- 2000-09-01 TW TW089117924A patent/TWI229080B/zh not_active IP Right Cessation
-
2001
- 2001-12-17 BG BG106229A patent/BG106229A/bg unknown
- 2001-12-19 YU YU89701A patent/YU89701A/sh unknown
- 2001-12-28 NO NO20016403A patent/NO20016403L/no not_active Application Discontinuation
-
2002
- 2002-01-02 ZA ZA200200017A patent/ZA200200017B/en unknown
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