AU777667B2 - Alkoxy substituted benzimidazole compounds, pharmaceutical preparations containing the same, and methods of using the same - Google Patents
Alkoxy substituted benzimidazole compounds, pharmaceutical preparations containing the same, and methods of using the same Download PDFInfo
- Publication number
- AU777667B2 AU777667B2 AU70737/00A AU7073700A AU777667B2 AU 777667 B2 AU777667 B2 AU 777667B2 AU 70737/00 A AU70737/00 A AU 70737/00A AU 7073700 A AU7073700 A AU 7073700A AU 777667 B2 AU777667 B2 AU 777667B2
- Authority
- AU
- Australia
- Prior art keywords
- methoxy
- benzimidazole
- methyl
- dimethyl
- pyridinyl
- Prior art date
- Legal status (The legal status 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 status listed.)
- Ceased
Links
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- 125000003545 alkoxy group Chemical group 0.000 title claims description 39
- 125000003785 benzimidazolyl group Chemical class N1=C(NC2=C1C=CC=C2)* 0.000 title abstract description 7
- 239000000825 pharmaceutical preparation Chemical class 0.000 title description 19
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 39
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- 239000000203 mixture Substances 0.000 claims description 326
- 150000003839 salts Chemical class 0.000 claims description 138
- -1 soivates Chemical class 0.000 claims description 128
- SUBDBMMJDZJVOS-UHFFFAOYSA-N 5-methoxy-2-{[(4-methoxy-3,5-dimethylpyridin-2-yl)methyl]sulfinyl}-1H-benzimidazole Chemical compound N=1C2=CC(OC)=CC=C2NC=1S(=O)CC1=NC=C(C)C(OC)=C1C SUBDBMMJDZJVOS-UHFFFAOYSA-N 0.000 claims description 117
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- 238000009472 formulation Methods 0.000 claims description 56
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 53
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 52
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- 229940071870 hydroiodic acid Drugs 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- UWYVPFMHMJIBHE-OWOJBTEDSA-N hydroxymaleic acid group Chemical group O/C(/C(=O)O)=C/C(=O)O UWYVPFMHMJIBHE-OWOJBTEDSA-N 0.000 description 1
- 229920003063 hydroxymethyl cellulose Polymers 0.000 description 1
- 229940031574 hydroxymethyl cellulose Drugs 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 229920003132 hydroxypropyl methylcellulose phthalate Polymers 0.000 description 1
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- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
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- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- NZHDAMQFAJCLLC-UHFFFAOYSA-N magnesium;tetrahydrate Chemical compound O.O.O.O.[Mg] NZHDAMQFAJCLLC-UHFFFAOYSA-N 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 229960002510 mandelic acid Drugs 0.000 description 1
- 208000008585 mastocytosis Diseases 0.000 description 1
- HEBKCHPVOIAQTA-UHFFFAOYSA-N meso ribitol Natural products OCC(O)C(O)C(O)CO HEBKCHPVOIAQTA-UHFFFAOYSA-N 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 229930182817 methionine Natural products 0.000 description 1
- FYFFGSSZFBZTAH-UHFFFAOYSA-N methylaminomethanetriol Chemical compound CNC(O)(O)O FYFFGSSZFBZTAH-UHFFFAOYSA-N 0.000 description 1
- 125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 239000000041 non-steroidal anti-inflammatory agent Substances 0.000 description 1
- 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 description 1
- 229920001542 oligosaccharide Polymers 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 230000001575 pathological effect Effects 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical class OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 1
- 150000002976 peresters Chemical class 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 150000004965 peroxy acids Chemical class 0.000 description 1
- 229940124531 pharmaceutical excipient Drugs 0.000 description 1
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
- VYMDGNCVAMGZFE-UHFFFAOYSA-N phenylbutazonum Chemical compound O=C1C(CCCC)C(=O)N(C=2C=CC=CC=2)N1C1=CC=CC=C1 VYMDGNCVAMGZFE-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 150000003022 phthalic acids Chemical class 0.000 description 1
- OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical class OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
- 239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 229950008882 polysorbate Drugs 0.000 description 1
- 229940068968 polysorbate 80 Drugs 0.000 description 1
- 229920000053 polysorbate 80 Polymers 0.000 description 1
- 229940100467 polyvinyl acetate phthalate Drugs 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- 229940116317 potato starch Drugs 0.000 description 1
- 238000000634 powder X-ray diffraction Methods 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- OGHBATFHNDZKSO-UHFFFAOYSA-N propan-2-olate Chemical compound CC(C)[O-] OGHBATFHNDZKSO-UHFFFAOYSA-N 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 230000005588 protonation Effects 0.000 description 1
- 239000012629 purifying agent Substances 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000009877 rendering Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 239000011369 resultant mixture Substances 0.000 description 1
- 206010039073 rheumatoid arthritis Diseases 0.000 description 1
- 235000019204 saccharin Nutrition 0.000 description 1
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
- 229940081974 saccharin Drugs 0.000 description 1
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 201000000980 schizophrenia Diseases 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 230000003248 secreting effect Effects 0.000 description 1
- 239000012056 semi-solid material Substances 0.000 description 1
- 238000007873 sieving Methods 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 210000000813 small intestine Anatomy 0.000 description 1
- RPACBEVZENYWOL-XFULWGLBSA-M sodium;(2r)-2-[6-(4-chlorophenoxy)hexyl]oxirane-2-carboxylate Chemical compound [Na+].C=1C=C(Cl)C=CC=1OCCCCCC[C@]1(C(=O)[O-])CO1 RPACBEVZENYWOL-XFULWGLBSA-M 0.000 description 1
- 238000000371 solid-state nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- 238000000935 solvent evaporation Methods 0.000 description 1
- 238000003797 solvolysis reaction Methods 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 230000037351 starvation Effects 0.000 description 1
- 239000012058 sterile packaged powder Substances 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
- 238000012916 structural analysis Methods 0.000 description 1
- 238000009498 subcoating Methods 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 230000002459 sustained effect Effects 0.000 description 1
- 230000009897 systematic effect Effects 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- IXZDIALLLMRYOU-UHFFFAOYSA-N tert-butyl hypochlorite Chemical compound CC(C)(C)OCl IXZDIALLLMRYOU-UHFFFAOYSA-N 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 238000002076 thermal analysis method Methods 0.000 description 1
- 235000010215 titanium dioxide Nutrition 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 230000001131 transforming effect Effects 0.000 description 1
- 229960002622 triacetin Drugs 0.000 description 1
- 229960004799 tryptophan Drugs 0.000 description 1
- 230000036269 ulceration Effects 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 238000005550 wet granulation Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000000811 xylitol Substances 0.000 description 1
- HEBKCHPVOIAQTA-SCDXWVJYSA-N xylitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)CO HEBKCHPVOIAQTA-SCDXWVJYSA-N 0.000 description 1
- 235000010447 xylitol Nutrition 0.000 description 1
- 229960002675 xylitol Drugs 0.000 description 1
Classifications
-
- 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
- C07D401/12—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 linked by a chain containing hetero atoms as chain links
-
- 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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
- A61K47/36—Polysaccharides; Derivatives thereof, e.g. gums, starch, alginate, dextrin, hyaluronic acid, chitosan, inulin, agar or pectin
- A61K47/40—Cyclodextrins; Derivatives thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0019—Injectable compositions; Intramuscular, intravenous, arterial, subcutaneous administration; Compositions to be administered through the skin in an invasive manner
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Organic Chemistry (AREA)
- Dermatology (AREA)
- Inorganic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US15087899P | 1999-08-26 | 1999-08-26 | |
| US60/150878 | 1999-08-26 | ||
| US09/519976 | 2000-03-07 | ||
| US09/519,976 US6262085B1 (en) | 1999-08-26 | 2000-03-07 | Alkoxy substituted Benzimidazole compounds, pharmaceutical preparations containing the same, and methods of using the same |
| PCT/US2000/023363 WO2001014367A1 (en) | 1999-08-26 | 2000-08-25 | Alkoxy substituted benzimidazole compounds, pharmaceutical preparations containing the same, and methods of using the same |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2005200203A Division AU2005200203B2 (en) | 1999-08-26 | 2005-01-17 | Alkoxy substituted benzimidazole compounds, pharmaceutical preparations containing the same, and methods of using the same |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU7073700A AU7073700A (en) | 2001-03-19 |
| AU777667B2 true AU777667B2 (en) | 2004-10-28 |
Family
ID=26848119
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU70737/00A Ceased AU777667B2 (en) | 1999-08-26 | 2000-08-25 | Alkoxy substituted benzimidazole compounds, pharmaceutical preparations containing the same, and methods of using the same |
| AU2005200203A Ceased AU2005200203B2 (en) | 1999-08-26 | 2005-01-17 | Alkoxy substituted benzimidazole compounds, pharmaceutical preparations containing the same, and methods of using the same |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2005200203A Ceased AU2005200203B2 (en) | 1999-08-26 | 2005-01-17 | Alkoxy substituted benzimidazole compounds, pharmaceutical preparations containing the same, and methods of using the same |
Country Status (16)
| Country | Link |
|---|---|
| EP (1) | EP1206466B1 (enExample) |
| JP (1) | JP4312405B2 (enExample) |
| KR (1) | KR100712039B1 (enExample) |
| CN (2) | CN1636564A (enExample) |
| AT (1) | ATE306483T1 (enExample) |
| AU (2) | AU777667B2 (enExample) |
| BR (1) | BR0014145A (enExample) |
| CA (1) | CA2382867A1 (enExample) |
| DE (1) | DE60023154T2 (enExample) |
| HR (1) | HRP20020174A2 (enExample) |
| MX (1) | MXPA02002007A (enExample) |
| NO (1) | NO326849B1 (enExample) |
| RO (1) | RO122491B1 (enExample) |
| RU (1) | RU2263673C2 (enExample) |
| SI (1) | SI20974A (enExample) |
| SK (1) | SK286903B6 (enExample) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2376231A (en) * | 2001-06-06 | 2002-12-11 | Cipla Ltd | Benzimidazole-cyclodextrin inclusion complex |
| WO2006001753A1 (en) | 2004-06-24 | 2006-01-05 | Astrazeneca Ab | New process for the preparation of crystal modifications for use in the preparation of esomeprazole sodium salt |
| ES2246149B1 (es) * | 2004-07-02 | 2007-06-01 | Esteve Quimica, S.A. | Formas solidas de la sal magnesica de s-omeprazol y procedimientos para su preparacion. |
| CN103524491A (zh) * | 2013-10-16 | 2014-01-22 | 江南大学 | 埃索美拉唑镁盐四水合物的三种晶型及其制备方法 |
| EP4117870A4 (en) * | 2020-03-09 | 2024-07-03 | Idexx Laboratories, Inc. | Method for removing interfering components of a liquid sample prior to dispensing same on a chemical reagent test slide |
| CN114558004B (zh) * | 2022-03-29 | 2023-08-11 | 奎马特里克斯有限公司 | Qtx125药物制剂 |
| CN116082247B (zh) * | 2023-01-19 | 2025-08-01 | 浙江工业大学 | 一种苯并咪唑类衍生物及其应用 |
| CN118225938B (zh) * | 2024-04-02 | 2024-08-30 | 江苏海洋大学 | 一种中药复方五神汤的质量检测方法 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5039806A (en) * | 1983-02-11 | 1991-08-13 | Ab Hassle | Novel pharmacologically active compound pyridyl methylsulfinyl benzimidazole |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US895292A (en) * | 1904-07-22 | 1908-08-04 | Marvin A Neeland | Blowing-engine inlet-valve. |
| SE418966B (sv) * | 1974-02-18 | 1981-07-06 | Haessle Ab | Analogiforfarande for framstellning av foreningar med magsyrasekretionsinhiberande verkan |
| SE7804231L (sv) * | 1978-04-14 | 1979-10-15 | Haessle Ab | Magsyrasekretionsmedel |
| SE9301830D0 (sv) * | 1993-05-28 | 1993-05-28 | Ab Astra | New compounds |
-
2000
- 2000-08-25 BR BR0014145-3A patent/BR0014145A/pt not_active Application Discontinuation
- 2000-08-25 CN CNA2004100946486A patent/CN1636564A/zh active Pending
- 2000-08-25 MX MXPA02002007A patent/MXPA02002007A/es active IP Right Grant
- 2000-08-25 KR KR1020027002436A patent/KR100712039B1/ko not_active Expired - Fee Related
- 2000-08-25 JP JP2001518698A patent/JP4312405B2/ja not_active Expired - Fee Related
- 2000-08-25 HR HR20020174A patent/HRP20020174A2/hr not_active Application Discontinuation
- 2000-08-25 AT AT00959404T patent/ATE306483T1/de not_active IP Right Cessation
- 2000-08-25 RU RU2002107421/04A patent/RU2263673C2/ru not_active IP Right Cessation
- 2000-08-25 RO ROA200200206A patent/RO122491B1/ro unknown
- 2000-08-25 EP EP00959404A patent/EP1206466B1/en not_active Expired - Lifetime
- 2000-08-25 SK SK281-2002A patent/SK286903B6/sk not_active IP Right Cessation
- 2000-08-25 CN CNB008149232A patent/CN1183127C/zh not_active Expired - Fee Related
- 2000-08-25 CA CA002382867A patent/CA2382867A1/en not_active Abandoned
- 2000-08-25 DE DE60023154T patent/DE60023154T2/de not_active Expired - Lifetime
- 2000-08-25 SI SI200020039A patent/SI20974A/sl not_active IP Right Cessation
- 2000-08-25 AU AU70737/00A patent/AU777667B2/en not_active Ceased
-
2002
- 2002-02-25 NO NO20020914A patent/NO326849B1/no not_active IP Right Cessation
-
2005
- 2005-01-17 AU AU2005200203A patent/AU2005200203B2/en not_active Ceased
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5039806A (en) * | 1983-02-11 | 1991-08-13 | Ab Hassle | Novel pharmacologically active compound pyridyl methylsulfinyl benzimidazole |
Also Published As
| Publication number | Publication date |
|---|---|
| CN1384831A (zh) | 2002-12-11 |
| CA2382867A1 (en) | 2001-03-01 |
| DE60023154D1 (de) | 2006-02-23 |
| AU2005200203B2 (en) | 2008-01-10 |
| JP2003507475A (ja) | 2003-02-25 |
| CN1183127C (zh) | 2005-01-05 |
| SI20974A (sl) | 2003-02-28 |
| JP4312405B2 (ja) | 2009-08-12 |
| KR20020035861A (ko) | 2002-05-15 |
| RO122491B1 (ro) | 2009-07-30 |
| KR100712039B1 (ko) | 2007-04-27 |
| EP1206466A1 (en) | 2002-05-22 |
| AU7073700A (en) | 2001-03-19 |
| NO326849B1 (no) | 2009-03-02 |
| SK286903B6 (sk) | 2009-07-06 |
| SK2812002A3 (en) | 2002-07-02 |
| HRP20020174A2 (en) | 2005-12-31 |
| EP1206466B1 (en) | 2005-10-12 |
| MXPA02002007A (es) | 2003-08-20 |
| BR0014145A (pt) | 2002-05-14 |
| RU2263673C2 (ru) | 2005-11-10 |
| DE60023154T2 (de) | 2006-06-22 |
| NO20020914D0 (no) | 2002-02-25 |
| ATE306483T1 (de) | 2005-10-15 |
| CN1636564A (zh) | 2005-07-13 |
| NO20020914L (no) | 2002-04-26 |
| AU2005200203A1 (en) | 2005-02-10 |
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