CA2456350A1 - Novel imidazopyridine compounds with therapeutic effect - Google Patents
Novel imidazopyridine compounds with therapeutic effect Download PDFInfo
- Publication number
- CA2456350A1 CA2456350A1 CA002456350A CA2456350A CA2456350A1 CA 2456350 A1 CA2456350 A1 CA 2456350A1 CA 002456350 A CA002456350 A CA 002456350A CA 2456350 A CA2456350 A CA 2456350A CA 2456350 A1 CA2456350 A1 CA 2456350A1
- Authority
- CA
- Canada
- Prior art keywords
- alkyl
- formula
- compound
- het
- hydroxylated
- 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.)
- Abandoned
Links
- 125000004857 imidazopyridinyl group Chemical class N1C(=NC2=C1C=CC=N2)* 0.000 title abstract 2
- 230000001225 therapeutic effect Effects 0.000 title description 2
- 238000011282 treatment Methods 0.000 claims abstract description 15
- 208000017189 Gastrointestinal inflammatory disease Diseases 0.000 claims abstract description 7
- 230000027119 gastric acid secretion Effects 0.000 claims abstract description 7
- 150000001875 compounds Chemical class 0.000 claims description 96
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 50
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 25
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 21
- 229910052757 nitrogen Inorganic materials 0.000 claims description 21
- 150000003839 salts Chemical class 0.000 claims description 20
- 239000002253 acid Substances 0.000 claims description 19
- 229910052760 oxygen Inorganic materials 0.000 claims description 17
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 16
- 238000002360 preparation method Methods 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 15
- -1 nitro, amino Chemical group 0.000 claims description 14
- 229910052736 halogen Inorganic materials 0.000 claims description 13
- 150000002367 halogens Chemical class 0.000 claims description 13
- 125000003118 aryl group Chemical group 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 10
- 229910052799 carbon Inorganic materials 0.000 claims description 10
- 230000008569 process Effects 0.000 claims description 10
- 125000001424 substituent group Chemical group 0.000 claims description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 9
- 239000004480 active ingredient Substances 0.000 claims description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
- 230000005764 inhibitory process Effects 0.000 claims description 8
- 229910052717 sulfur Inorganic materials 0.000 claims description 8
- 239000003814 drug Substances 0.000 claims description 7
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- 238000004519 manufacturing process Methods 0.000 claims description 7
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 7
- 125000004076 pyridyl group Chemical group 0.000 claims description 7
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- 125000002541 furyl group Chemical group 0.000 claims description 6
- 239000012442 inert solvent Substances 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 125000001544 thienyl group Chemical group 0.000 claims description 6
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 claims description 6
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- CLZISMQKJZCZDN-UHFFFAOYSA-N [benzotriazol-1-yloxy(dimethylamino)methylidene]-dimethylazanium Chemical compound C1=CC=C2N(OC(N(C)C)=[N+](C)C)N=NC2=C1 CLZISMQKJZCZDN-UHFFFAOYSA-N 0.000 claims description 4
- 125000001931 aliphatic group Chemical group 0.000 claims description 4
- 239000002585 base Substances 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 230000002401 inhibitory effect Effects 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
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- 125000000623 heterocyclic group Chemical group 0.000 claims description 3
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 3
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- 238000002560 therapeutic procedure Methods 0.000 claims description 3
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- 235000005074 zinc chloride Nutrition 0.000 claims description 3
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 claims description 2
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- 239000002841 Lewis acid Substances 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 2
- 239000003153 chemical reaction reagent Substances 0.000 claims description 2
- 230000008878 coupling Effects 0.000 claims description 2
- 238000010168 coupling process Methods 0.000 claims description 2
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- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- 150000004820 halides Chemical class 0.000 claims description 2
- 150000007517 lewis acids Chemical class 0.000 claims description 2
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 2
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 claims description 2
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 claims 5
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 1
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- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims 1
- 230000003301 hydrolyzing effect Effects 0.000 claims 1
- 229910052708 sodium Inorganic materials 0.000 claims 1
- 239000011734 sodium Substances 0.000 claims 1
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- 230000002265 prevention Effects 0.000 abstract description 3
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- 238000012360 testing method Methods 0.000 description 16
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
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- ZVJHJDDKYZXRJI-UHFFFAOYSA-N pyrroline Natural products C1CC=NC1 ZVJHJDDKYZXRJI-UHFFFAOYSA-N 0.000 description 1
- 229940107700 pyruvic acid Drugs 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 150000007660 quinolones Chemical class 0.000 description 1
- 238000011552 rat model Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000012552 review Methods 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
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 229940045902 sodium stearyl fumarate Drugs 0.000 description 1
- 238000012453 sprague-dawley rat model Methods 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000005846 sugar alcohols Chemical class 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 239000008399 tap water Substances 0.000 description 1
- 235000020679 tap water Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 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
- 229960002180 tetracycline Drugs 0.000 description 1
- 229930101283 tetracycline Natural products 0.000 description 1
- 229940040944 tetracyclines Drugs 0.000 description 1
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 230000036269 ulceration Effects 0.000 description 1
- 235000019871 vegetable fat Nutrition 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- 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
- A61K31/4353—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 ortho- or peri-condensed with heterocyclic ring systems
- A61K31/437—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 ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a five-membered ring having nitrogen as a ring hetero atom, e.g. indolizine, beta-carboline
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Epidemiology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE0102808A SE0102808D0 (sv) | 2001-08-22 | 2001-08-22 | New compounds |
| SE0102808-3 | 2001-08-22 | ||
| PCT/SE2002/001489 WO2003018582A1 (en) | 2001-08-22 | 2002-08-21 | Novel imidazopyridine compounds with therapeutic effect |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2456350A1 true CA2456350A1 (en) | 2003-03-06 |
Family
ID=20285105
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002456350A Abandoned CA2456350A1 (en) | 2001-08-22 | 2002-08-21 | Novel imidazopyridine compounds with therapeutic effect |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US20040220209A1 (enExample) |
| EP (1) | EP1421083A1 (enExample) |
| JP (1) | JP2005501870A (enExample) |
| KR (1) | KR20040036723A (enExample) |
| CN (1) | CN100343252C (enExample) |
| AR (1) | AR035465A1 (enExample) |
| BR (1) | BR0211846A (enExample) |
| CA (1) | CA2456350A1 (enExample) |
| HU (1) | HUP0401350A3 (enExample) |
| IL (1) | IL160143A0 (enExample) |
| IS (1) | IS7159A (enExample) |
| MX (1) | MXPA04001402A (enExample) |
| NO (1) | NO20040760L (enExample) |
| NZ (1) | NZ531110A (enExample) |
| PL (1) | PL367971A1 (enExample) |
| RU (1) | RU2294935C2 (enExample) |
| SE (1) | SE0102808D0 (enExample) |
| WO (1) | WO2003018582A1 (enExample) |
| ZA (1) | ZA200401114B (enExample) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE0301904D0 (sv) | 2003-06-26 | 2003-06-26 | Astrazeneca Ab | Novel imidazopyridine compound II with therapeutic effect |
| EP1682133A1 (en) | 2003-11-03 | 2006-07-26 | AstraZeneca AB | Imidazo 1,2-a pyridine derivatives for the treatment of silent gastro-esophageal reflux |
| US20080033006A1 (en) * | 2004-01-26 | 2008-02-07 | Altana Pharma Ag | 1,2,4-Triazolo[ 1,5-A] Pyridines as Gastric Acid Secretion Inhibitors |
| EA011512B1 (ru) * | 2004-12-17 | 2009-04-28 | Ракуалиа Фарма Инк. | Производные хромана, полезные в качестве антагонистов кислотной помпы |
| GB0513423D0 (en) * | 2005-06-30 | 2005-08-03 | Glaxo Group Ltd | Novel compounds |
| WO2007107827A1 (en) * | 2006-03-17 | 2007-09-27 | Raqualia Pharma Inc. | Chromane derivatives |
| WO2008059373A1 (en) * | 2006-11-17 | 2008-05-22 | Raqualia Pharma Inc. | Imidazo [1, 2-a] pyrazine derivatives and their use as acid pump antagonists |
| KR200449743Y1 (ko) * | 2008-03-11 | 2010-08-05 | 주식회사 보루네오가구 | 파티션용 상부 스크린의 고정구조 |
| FI20086158A0 (fi) | 2008-12-03 | 2008-12-03 | Mikael Dahlstroem | Imidatsopyridiinijohdannaiset |
| EP2452680B1 (en) | 2009-07-09 | 2019-12-18 | RaQualia Pharma Inc. | Acid pump antagonist for the treatment of diseases involved in abnormal gastrointestinal motility |
| MX2012003469A (es) * | 2009-09-24 | 2012-04-19 | Hoffmann La Roche | Derivados de imidazopiridina o imidazopirimidina como inhibidores fosfodiesterasa 10a. |
| FR2962437B1 (fr) | 2010-07-06 | 2012-08-17 | Sanofi Aventis | Derives d'imidazopyridine, leur procede de preparation et leur application en therapeutique |
| KR102120513B1 (ko) * | 2013-01-31 | 2020-06-08 | 네오메드 인스티튜트 | 이미다조피리딘 화합물 및 이의 용도 |
| CN105164126B (zh) * | 2013-04-30 | 2017-05-31 | 豪夫迈·罗氏有限公司 | 吡唑酰胺的Pd‑催化偶联 |
| CN106279151A (zh) * | 2015-06-26 | 2017-01-04 | 江苏太瑞生诺生物医药科技有限公司 | 5-(2-(8-((2,6-二甲基苄基)氨基)-2,3-二甲基咪唑并[1,2-a]吡啶-6-甲酰胺基)乙氧基)-5-氧代戊酸的固体形式及其制备方法 |
| DK3880678T3 (da) | 2018-11-13 | 2025-06-10 | Glaxosmithkline Intellectual Property No 3 Ltd | Krystallinske former af p2x3-modulator methyl(s)-2-((2-(2,6-difluoro-4-(methylcarbamoyl )phenyl)-7-methylimidazo[1,2-a]pyridin-3-yl)methyl)morpholin-4-carboxylat |
| CA3131312A1 (en) | 2019-02-25 | 2020-09-03 | Bellus Health Cough Inc. | Treatment with p2x3 modulators |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ZA81219B (en) * | 1980-01-23 | 1982-01-27 | Schering Corp | Imidazo (1,2-a) pyridines ,process for their preparation and pharmaceutical compositions containing them |
| EP0068378B1 (en) * | 1981-06-26 | 1986-03-05 | Schering Corporation | Novel imidazo(1,2-a)pyridines and pyrazines, processes for their preparation and pharmaceutical compositions containing them |
| US4725601A (en) * | 1985-06-04 | 1988-02-16 | Fujisawa Pharmaceutical Co., Ltd. | Certain imidazo[1,2-a]pyridines useful in the treatment of ulcers |
| EP0228006A1 (en) * | 1985-12-16 | 1987-07-08 | Fujisawa Pharmaceutical Co., Ltd. | Imidazopyridine compounds and processes for preparation thereof |
| IL108520A (en) * | 1993-02-15 | 1997-09-30 | Byk Gulden Lomberg Chem Fab | 2, 3, 8-TRISUBSTITUTED IMIDAZO £1, 2-a| PYRIDINE DERIVATIVES, PROCESSES FOR THE PREPARATION THEREOF AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM |
| UA48122C2 (uk) * | 1993-10-11 | 2002-08-15 | Бік Гульден Ломберг Хеміше Фабрік Гмбх | АЛКОКСІАЛКІЛКАРБАМАТИ ІМІДАЗО[1,2-а]ПІРИДИНІВ, СПОСІБ ЇХ ОДЕРЖАННЯ ТА ЛІКАРСЬКИЙ ЗАСІБ НА ЇХ ОСНОВІ |
| CN1046726C (zh) * | 1994-07-28 | 1999-11-24 | 比克·古尔顿·劳姆贝尔格化学公司 | 咪唑并吡啶－吡咯烷酮、其制法和药用 |
| SE9801526D0 (sv) * | 1998-04-29 | 1998-04-29 | Astra Ab | New compounds |
| SE9802794D0 (sv) * | 1998-08-21 | 1998-08-21 | Astra Ab | New compounds |
-
2001
- 2001-08-22 SE SE0102808A patent/SE0102808D0/xx unknown
-
2002
- 2002-08-09 AR ARP020103019A patent/AR035465A1/es not_active Application Discontinuation
- 2002-08-21 MX MXPA04001402A patent/MXPA04001402A/es unknown
- 2002-08-21 KR KR10-2004-7002466A patent/KR20040036723A/ko not_active Ceased
- 2002-08-21 BR BR0211846-7A patent/BR0211846A/pt not_active IP Right Cessation
- 2002-08-21 HU HU0401350A patent/HUP0401350A3/hu unknown
- 2002-08-21 EP EP02759036A patent/EP1421083A1/en not_active Withdrawn
- 2002-08-21 PL PL02367971A patent/PL367971A1/xx not_active Application Discontinuation
- 2002-08-21 WO PCT/SE2002/001489 patent/WO2003018582A1/en not_active Ceased
- 2002-08-21 CA CA002456350A patent/CA2456350A1/en not_active Abandoned
- 2002-08-21 CN CNB028160177A patent/CN100343252C/zh not_active Expired - Fee Related
- 2002-08-21 RU RU2004103628/04A patent/RU2294935C2/ru not_active IP Right Cessation
- 2002-08-21 NZ NZ531110A patent/NZ531110A/en unknown
- 2002-08-21 IL IL16014302A patent/IL160143A0/xx unknown
- 2002-08-21 JP JP2003523243A patent/JP2005501870A/ja active Pending
- 2002-08-21 US US10/487,149 patent/US20040220209A1/en not_active Abandoned
-
2004
- 2004-02-11 ZA ZA200401114A patent/ZA200401114B/en unknown
- 2004-02-20 IS IS7159A patent/IS7159A/is unknown
- 2004-02-20 NO NO20040760A patent/NO20040760L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| RU2004103628A (ru) | 2005-06-27 |
| US20040220209A1 (en) | 2004-11-04 |
| ZA200401114B (en) | 2005-06-22 |
| RU2294935C2 (ru) | 2007-03-10 |
| PL367971A1 (en) | 2005-03-07 |
| HUP0401350A3 (en) | 2009-03-02 |
| WO2003018582A1 (en) | 2003-03-06 |
| CN100343252C (zh) | 2007-10-17 |
| JP2005501870A (ja) | 2005-01-20 |
| HUP0401350A2 (hu) | 2004-12-28 |
| KR20040036723A (ko) | 2004-04-30 |
| BR0211846A (pt) | 2004-09-08 |
| IS7159A (is) | 2004-02-20 |
| NO20040760L (no) | 2004-02-20 |
| IL160143A0 (en) | 2004-06-20 |
| MXPA04001402A (es) | 2004-05-27 |
| CN1543464A (zh) | 2004-11-03 |
| NZ531110A (en) | 2005-10-28 |
| AR035465A1 (es) | 2004-05-26 |
| SE0102808D0 (sv) | 2001-08-22 |
| EP1421083A1 (en) | 2004-05-26 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Discontinued |