SK13862002A3 - Pyrano[2,3-c]imidazo[1,2-a]pyridínové deriváty, farmaceutický prostriedok s ich obsahom a ich použitie - Google Patents
Pyrano[2,3-c]imidazo[1,2-a]pyridínové deriváty, farmaceutický prostriedok s ich obsahom a ich použitie Download PDFInfo
- Publication number
- SK13862002A3 SK13862002A3 SK1386-2002A SK13862002A SK13862002A3 SK 13862002 A3 SK13862002 A3 SK 13862002A3 SK 13862002 A SK13862002 A SK 13862002A SK 13862002 A3 SK13862002 A3 SK 13862002A3
- Authority
- SK
- Slovakia
- Prior art keywords
- imidazo
- hydrogen
- mmol
- salts
- pyrano
- Prior art date
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- 238000011282 treatment Methods 0.000 title claims abstract description 13
- 208000018522 Gastrointestinal disease Diseases 0.000 title claims abstract description 5
- 150000005234 imidazo[1,2-a]pyridines Chemical class 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 69
- 230000002265 prevention Effects 0.000 claims abstract description 5
- -1 hydroxy, methoxy, ethoxy, propoxy, isopropoxy, butoxy, methoxyethoxy Chemical group 0.000 claims description 45
- 150000003839 salts Chemical class 0.000 claims description 40
- 229910052739 hydrogen Inorganic materials 0.000 claims description 31
- 239000001257 hydrogen Substances 0.000 claims description 31
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 24
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 20
- USCXRMHCNWXOPM-UHFFFAOYSA-N 13-oxa-3,6-diazatricyclo[7.4.0.02,6]trideca-1,3,7,9,11-pentaene Chemical class O1C=CC=C2C=CN3CC=NC3=C21 USCXRMHCNWXOPM-UHFFFAOYSA-N 0.000 claims description 12
- 239000003814 drug Substances 0.000 claims description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 2
- 229940124531 pharmaceutical excipient Drugs 0.000 claims description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 80
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 60
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 33
- 239000000203 mixture Substances 0.000 description 30
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 24
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 22
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 20
- 239000007787 solid Substances 0.000 description 19
- 239000000243 solution Substances 0.000 description 18
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 16
- 239000012043 crude product Substances 0.000 description 16
- UTCSSFWDNNEEBH-UHFFFAOYSA-N imidazo[1,2-a]pyridine Chemical compound C1=CC=CC2=NC=CN21 UTCSSFWDNNEEBH-UHFFFAOYSA-N 0.000 description 16
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 15
- 229910052938 sodium sulfate Inorganic materials 0.000 description 15
- 235000011152 sodium sulphate Nutrition 0.000 description 15
- 229920006395 saturated elastomer Polymers 0.000 description 14
- 239000012267 brine Substances 0.000 description 13
- 238000004440 column chromatography Methods 0.000 description 13
- 239000012044 organic layer Substances 0.000 description 13
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 13
- 239000000725 suspension Substances 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 238000000034 method Methods 0.000 description 11
- 235000017557 sodium bicarbonate Nutrition 0.000 description 11
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 11
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 239000002253 acid Substances 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 7
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 6
- 201000010099 disease Diseases 0.000 description 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 6
- 125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 6
- DGMXXYSWFUXSIB-UHFFFAOYSA-N 3H-imidazo[1,2-a]pyridin-7-one Chemical compound O=c1ccn2CC=Nc2c1 DGMXXYSWFUXSIB-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 229960004099 azithromycin Drugs 0.000 description 5
- MQTOSJVFKKJCRP-BICOPXKESA-N azithromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)N(C)C[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 MQTOSJVFKKJCRP-BICOPXKESA-N 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
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- 238000007254 oxidation reaction Methods 0.000 description 5
- 229910052760 oxygen Inorganic materials 0.000 description 5
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- 238000007363 ring formation reaction Methods 0.000 description 5
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- 241000700159 Rattus Species 0.000 description 4
- 239000004480 active ingredient Substances 0.000 description 4
- 230000010933 acylation Effects 0.000 description 4
- 238000005917 acylation reaction Methods 0.000 description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
- 239000003638 chemical reducing agent Substances 0.000 description 4
- 238000004587 chromatography analysis Methods 0.000 description 4
- 230000027119 gastric acid secretion Effects 0.000 description 4
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 238000011321 prophylaxis Methods 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 239000012279 sodium borohydride Substances 0.000 description 4
- 229910000033 sodium borohydride Inorganic materials 0.000 description 4
- 210000002784 stomach Anatomy 0.000 description 4
- DMTADULPJIAIEO-UHFFFAOYSA-N 2,3-dimethyl-6,7-dihydro-5h-imidazo[1,2-a]pyridin-8-one Chemical compound O=C1CCCN2C(C)=C(C)N=C21 DMTADULPJIAIEO-UHFFFAOYSA-N 0.000 description 3
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 3
- 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 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 241000282414 Homo sapiens Species 0.000 description 3
- 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 description 3
- 241001465754 Metazoa Species 0.000 description 3
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- 230000015572 biosynthetic process Effects 0.000 description 3
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- 238000002425 crystallisation Methods 0.000 description 3
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- 150000002009 diols Chemical class 0.000 description 3
- 230000032050 esterification Effects 0.000 description 3
- 238000005886 esterification reaction Methods 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
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- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
- ANRIQLNBZQLTFV-DZUOILHNSA-N pentagastrin Chemical compound C([C@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@@H](NC(=O)[C@H](CC=1[C]2C=CC=CC2=NC=1)NC(=O)CCNC(=O)OC(C)(C)C)CCSC)C(N)=O)C1=CC=CC=C1 ANRIQLNBZQLTFV-DZUOILHNSA-N 0.000 description 3
- 229960000444 pentagastrin Drugs 0.000 description 3
- IUBQJLUDMLPAGT-UHFFFAOYSA-N potassium bis(trimethylsilyl)amide Chemical compound C[Si](C)(C)N([K])[Si](C)(C)C IUBQJLUDMLPAGT-UHFFFAOYSA-N 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
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- UGNWTBMOAKPKBL-UHFFFAOYSA-N tetrachloro-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(Cl)=C(Cl)C1=O UGNWTBMOAKPKBL-UHFFFAOYSA-N 0.000 description 3
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
- 229960000549 4-dimethylaminophenol Drugs 0.000 description 2
- VNHBYKHXBCYPBJ-UHFFFAOYSA-N 5-ethynylimidazo[1,2-a]pyridine Chemical compound C#CC1=CC=CC2=NC=CN12 VNHBYKHXBCYPBJ-UHFFFAOYSA-N 0.000 description 2
- 239000005711 Benzoic acid Substances 0.000 description 2
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- BZGIPVGCJGXQTA-UHFFFAOYSA-N s-[2-(diethylamino)ethyl] n,n-diphenylcarbamothioate Chemical compound C=1C=CC=CC=1N(C(=O)SCCN(CC)CC)C1=CC=CC=C1 BZGIPVGCJGXQTA-UHFFFAOYSA-N 0.000 description 1
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- BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/12—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains three hetero rings
- C07D491/14—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP00106690 | 2000-03-29 | ||
PCT/EP2001/003510 WO2001072755A1 (en) | 2000-03-29 | 2001-03-28 | Pyrano[2,3-c]imidazo[-1,2-a]pyridine derivatives for the treatment of gastrointestinal disorders |
Publications (1)
Publication Number | Publication Date |
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SK13862002A3 true SK13862002A3 (sk) | 2003-03-04 |
Family
ID=8168269
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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SK1386-2002A SK13862002A3 (sk) | 2000-03-29 | 2001-03-28 | Pyrano[2,3-c]imidazo[1,2-a]pyridínové deriváty, farmaceutický prostriedok s ich obsahom a ich použitie |
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US (2) | US20030100578A1 (no) |
EP (1) | EP1286999B1 (no) |
JP (1) | JP2003528877A (no) |
KR (1) | KR20020082494A (no) |
CN (1) | CN1221554C (no) |
AT (1) | ATE381568T1 (no) |
AU (1) | AU784611B2 (no) |
BR (1) | BR0109589A (no) |
CA (1) | CA2404466A1 (no) |
CZ (1) | CZ20023210A3 (no) |
DE (1) | DE60131968T2 (no) |
EA (1) | EA006095B1 (no) |
ES (1) | ES2298233T3 (no) |
HK (1) | HK1053838A1 (no) |
HR (1) | HRP20020855A2 (no) |
HU (1) | HUP0300569A3 (no) |
MX (1) | MXPA02009550A (no) |
NO (1) | NO20024572L (no) |
NZ (1) | NZ520836A (no) |
PL (1) | PL365824A1 (no) |
SK (1) | SK13862002A3 (no) |
WO (1) | WO2001072755A1 (no) |
ZA (1) | ZA200207635B (no) |
Families Citing this family (10)
Publication number | Priority date | Publication date | Assignee | Title |
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CZ20023116A3 (cs) * | 2000-03-29 | 2003-01-15 | Altana Pharma Ag | Alkylované imidazopyridinové sloučeniny |
CA2426616A1 (en) | 2000-10-25 | 2002-05-02 | Altana Pharma Ag | Polysubstituted imidazopyridines as gastric secretion inhibitors |
EP1565465A1 (en) | 2002-11-19 | 2005-08-24 | ALTANA Pharma AG | 8-substituted imidazopyridines |
BRPI0407541A (pt) * | 2003-02-17 | 2006-02-14 | Altana Pharma Ag | combinações e uso de compostos farmaceuticamente ativos selecionados |
AR044129A1 (es) * | 2003-05-06 | 2005-08-24 | Altana Pharma Ag | Compuestos intermedios de imidazopiridina. proceso de preparacion. |
CA2526566A1 (en) * | 2003-05-27 | 2004-12-09 | Altana Pharma Ag | Pharmaceutical combinations of a proton pump inhibitor and a compound which modifies gastrointestinal motility |
WO2005041961A1 (en) | 2003-11-03 | 2005-05-12 | Astrazeneca Ab | Imidazo [1,2-a] pyridine derivatives for the treatment of silent gastro-esophageal reflux |
WO2005058894A1 (en) | 2003-12-19 | 2005-06-30 | Altana Pharma Ag | Intermediates for the preparation of tricyclic dihydropyrano -imidazo -pyridines derivatives |
AR048869A1 (es) * | 2004-04-26 | 2006-06-07 | Altana Pharma Ag | Bencimidazoles triciclicos |
DE102006001335B4 (de) * | 2006-01-09 | 2016-08-04 | Rogers Germany Gmbh | Verwendung eines wärmetransportierenden Mediums |
Family Cites Families (4)
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SE9401197D0 (sv) * | 1994-04-11 | 1994-04-11 | Astra Ab | Active compounds |
EP0984969B1 (en) * | 1997-05-28 | 2008-07-09 | Nycomed GmbH | Fused dihydropyrans |
HUP0001555A3 (en) * | 1997-10-30 | 2001-01-29 | Altana Pharma Ag | Tetrahydro-imidazo-naphthyridine derivatives, pharmaceutical compositions thereof and process for their preparation |
CZ20023116A3 (cs) * | 2000-03-29 | 2003-01-15 | Altana Pharma Ag | Alkylované imidazopyridinové sloučeniny |
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2001
- 2001-03-28 US US10/182,620 patent/US20030100578A1/en not_active Abandoned
- 2001-03-28 HU HU0300569A patent/HUP0300569A3/hu unknown
- 2001-03-28 EA EA200200883A patent/EA006095B1/ru not_active IP Right Cessation
- 2001-03-28 PL PL01365824A patent/PL365824A1/xx unknown
- 2001-03-28 EP EP01929463A patent/EP1286999B1/en not_active Expired - Lifetime
- 2001-03-28 CZ CZ20023210A patent/CZ20023210A3/cs unknown
- 2001-03-28 MX MXPA02009550A patent/MXPA02009550A/es active IP Right Grant
- 2001-03-28 SK SK1386-2002A patent/SK13862002A3/sk unknown
- 2001-03-28 AT AT01929463T patent/ATE381568T1/de not_active IP Right Cessation
- 2001-03-28 KR KR1020027012691A patent/KR20020082494A/ko active IP Right Grant
- 2001-03-28 BR BR0109589-7A patent/BR0109589A/pt not_active Application Discontinuation
- 2001-03-28 CA CA002404466A patent/CA2404466A1/en not_active Abandoned
- 2001-03-28 CN CNB01807166XA patent/CN1221554C/zh not_active Expired - Fee Related
- 2001-03-28 DE DE60131968T patent/DE60131968T2/de not_active Expired - Fee Related
- 2001-03-28 JP JP2001570664A patent/JP2003528877A/ja not_active Withdrawn
- 2001-03-28 NZ NZ520836A patent/NZ520836A/en unknown
- 2001-03-28 AU AU56228/01A patent/AU784611B2/en not_active Ceased
- 2001-03-28 WO PCT/EP2001/003510 patent/WO2001072755A1/en active IP Right Grant
- 2001-03-28 ES ES01929463T patent/ES2298233T3/es not_active Expired - Lifetime
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2002
- 2002-09-23 ZA ZA200207635A patent/ZA200207635B/en unknown
- 2002-09-24 NO NO20024572A patent/NO20024572L/no not_active Application Discontinuation
- 2002-10-28 HR HRP20020855 patent/HRP20020855A2/hr not_active Application Discontinuation
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2003
- 2003-08-27 HK HK03106137A patent/HK1053838A1/xx not_active IP Right Cessation
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2004
- 2004-04-01 US US10/811,496 patent/US6936623B2/en not_active Expired - Fee Related
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NZ520836A (en) | 2005-01-28 |
HK1053838A1 (en) | 2003-11-07 |
CA2404466A1 (en) | 2001-10-04 |
HRP20020855A2 (en) | 2004-12-31 |
AU784611B2 (en) | 2006-05-11 |
ES2298233T3 (es) | 2008-05-16 |
EP1286999B1 (en) | 2007-12-19 |
ATE381568T1 (de) | 2008-01-15 |
DE60131968T2 (de) | 2008-12-11 |
US6936623B2 (en) | 2005-08-30 |
EP1286999A1 (en) | 2003-03-05 |
MXPA02009550A (es) | 2004-05-14 |
JP2003528877A (ja) | 2003-09-30 |
CN1419556A (zh) | 2003-05-21 |
NO20024572D0 (no) | 2002-09-24 |
CZ20023210A3 (cs) | 2003-01-15 |
PL365824A1 (en) | 2005-01-10 |
WO2001072755A1 (en) | 2001-10-04 |
EA200200883A1 (ru) | 2003-04-24 |
HUP0300569A2 (hu) | 2003-07-28 |
BR0109589A (pt) | 2003-02-04 |
CN1221554C (zh) | 2005-10-05 |
US20040180920A1 (en) | 2004-09-16 |
KR20020082494A (ko) | 2002-10-31 |
ZA200207635B (en) | 2003-10-20 |
HUP0300569A3 (en) | 2004-10-28 |
EA006095B1 (ru) | 2005-08-25 |
DE60131968D1 (de) | 2008-01-31 |
NO20024572L (no) | 2002-09-24 |
AU5622801A (en) | 2001-10-08 |
US20030100578A1 (en) | 2003-05-29 |
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