CA2475780A1 - 1-phenyl-2-heteroaryl-substituted benzimidazole derivatives, their use to prepare drugs for treatment of immunological diseases - Google Patents
1-phenyl-2-heteroaryl-substituted benzimidazole derivatives, their use to prepare drugs for treatment of immunological diseases Download PDFInfo
- Publication number
- CA2475780A1 CA2475780A1 CA002475780A CA2475780A CA2475780A1 CA 2475780 A1 CA2475780 A1 CA 2475780A1 CA 002475780 A CA002475780 A CA 002475780A CA 2475780 A CA2475780 A CA 2475780A CA 2475780 A1 CA2475780 A1 CA 2475780A1
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- Prior art keywords
- benzimidazol
- oxy
- alkyl
- methylphenyl
- pyridinyl
- Prior art date
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- 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
-
- 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
-
- 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
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
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- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Immunology (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Pulmonology (AREA)
- Transplantation (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
The invention relates to the novel benzimidazole derivatives of formula (I), to the production and use thereof in the treatment and prophylaxis of diseases that are associated with microglial activation, and of T-cell mediated immunological diseases. The invention also relates to the pharmaceutical preparations that contain the novel benzimidazole derivatives.
Claims (12)
1.) Benzimidazole derivatives of formula I
in which:
R1 denotes a phenyl group, optionally substituted with up to three of the following substituents, independently of each other:
F, CI, Br, J
OH, OR4, OCOR4 SR4, SOR4, SO2R4, R4, NH, NHR4, NR4R4 or two adjacent substituents on R1 together form a -O-CH2-O-, -O-CH2-CH2-O- or -CH2-CH2-CH2- group, R2 denotes a monocyclic or bicyclic 5 - 10-membered heteroaryl group with 1 -
in which:
R1 denotes a phenyl group, optionally substituted with up to three of the following substituents, independently of each other:
F, CI, Br, J
OH, OR4, OCOR4 SR4, SOR4, SO2R4, R4, NH, NHR4, NR4R4 or two adjacent substituents on R1 together form a -O-CH2-O-, -O-CH2-CH2-O- or -CH2-CH2-CH2- group, R2 denotes a monocyclic or bicyclic 5 - 10-membered heteroaryl group with 1 -
2 hetero atoms, chosen from N, S, and O, optionally substituted with up to two of the following substituents, independently of each other:
F, CI, Br, J
OH, OR4, OCOR4, COR4, SR4, SOR4, SO2R4, or two adjacent substituents on R2 together form a ~O-CH2-O-, -O-CH2-CH2-O- or ~CH2-CH2-CH2- group, R3 denotes H, OH or O-C1-6-alkyl, R4 and R4', independently of each other, denote C1-4-perfluoroalkyl or C1-6-alkyl, A denotes a C2-6-alkylene group, optionally substituted with = O, OH, O-C1-3-alkyl, NH2, NH-C1-3-alkyl, N(C1-3-alkyl)2, and N(C1-3-alkyl)(C1-3-alkanoyl), B denotes COOH, CONH2, CONHNH2, CONHR5, CONR5R5', each bonded to a carbon atom of group A, R5 and R5', independently of each other, each denote a group chosen from the group comprising C1-6-alky, C2-6-alkenyl, C2-6-alkynyl, in which a C-atom can be replaced with O, S, SO, SO2, NH, N-C1-3-alkyl or N-C1-3-alkanoyl, also (C0-3-alkanediyl-C3-7-cycloalkyl), in which one ring member in a five-membered cycloalkyl ring can be ring N or ring O and, in a six- or seven-membered cycloalkyl ring, one or two ring members can be ring N
and/or ring O atoms, in which the ring N atoms can optionally be substituted with C1-3-alkyl or C1-3-alkanoyl, as well as (C0-3-alkanediyl-phenyl) and (C0-3-alkanediyl-heteroaryl), in which the heteroaryl group is five- or six-membered and contains one or two heteroatoms, chosen from the group comprising N, S and O, in which all the aforementioned alkyl and cycloalkyl groups can optionally be substituted with up to two groups, chosen from the group comprising CF3, C2F5, OH, O-C1-3-alkyl, NH2, NH-alkyl, NH-C1-3-alkanoyl, N(C1-3-alkyl)2, N(C1-3-alkyl)(C1-3-alkanoyl), COOH, and COO-C1-3-alkyl, and all the aforementioned phenyl and heteroaryl groups can optionally be substituted with up to two groups, chosen from the group comprising F, Cl, Br, CH3, C2H5, OH, OCH3, OC2H5, NO2 N(CH3)2, CF3, C2F5 and SO2NH2, or R5 and R5', together with the N-atom, can form a five- to seven-membered heterocyclic ring that can contain an additional N- or O- or S-atom and can be substituted with C1-4-alkyl (C0-2-alkanediyl-C1-4-alkoxy), C1-4-alkoxycarbonyl, aminocarbonyl or phenyl as well as their optic or geometric isomers or tautomeric forms or pharmaceutically applicable salts, in which the following compounds are ruled out:
6-[[1-phenyl-2-(pyridine-4-yl)-1H-benzimidazol-6-yl]oxy]hexanoic acid, 6-[[1-phenyl-2-(benzothien-2-yl)-1H-benzimidazol-6-yl]oxy]hexanoic acid.
2.) Benzimidazoles according to Claim 1, characterized by the fact that R1 is a phenyl group, optionally substituted with up to two of the following substituents, independently of each other:
F, CI
OH, OR4, OCOR4 SR4, R4 or two adjacent substituents on R1 together form a ~O-CH2-O- or ~CH2-CH2-CH2-group.
F, CI, Br, J
OH, OR4, OCOR4, COR4, SR4, SOR4, SO2R4, or two adjacent substituents on R2 together form a ~O-CH2-O-, -O-CH2-CH2-O- or ~CH2-CH2-CH2- group, R3 denotes H, OH or O-C1-6-alkyl, R4 and R4', independently of each other, denote C1-4-perfluoroalkyl or C1-6-alkyl, A denotes a C2-6-alkylene group, optionally substituted with = O, OH, O-C1-3-alkyl, NH2, NH-C1-3-alkyl, N(C1-3-alkyl)2, and N(C1-3-alkyl)(C1-3-alkanoyl), B denotes COOH, CONH2, CONHNH2, CONHR5, CONR5R5', each bonded to a carbon atom of group A, R5 and R5', independently of each other, each denote a group chosen from the group comprising C1-6-alky, C2-6-alkenyl, C2-6-alkynyl, in which a C-atom can be replaced with O, S, SO, SO2, NH, N-C1-3-alkyl or N-C1-3-alkanoyl, also (C0-3-alkanediyl-C3-7-cycloalkyl), in which one ring member in a five-membered cycloalkyl ring can be ring N or ring O and, in a six- or seven-membered cycloalkyl ring, one or two ring members can be ring N
and/or ring O atoms, in which the ring N atoms can optionally be substituted with C1-3-alkyl or C1-3-alkanoyl, as well as (C0-3-alkanediyl-phenyl) and (C0-3-alkanediyl-heteroaryl), in which the heteroaryl group is five- or six-membered and contains one or two heteroatoms, chosen from the group comprising N, S and O, in which all the aforementioned alkyl and cycloalkyl groups can optionally be substituted with up to two groups, chosen from the group comprising CF3, C2F5, OH, O-C1-3-alkyl, NH2, NH-alkyl, NH-C1-3-alkanoyl, N(C1-3-alkyl)2, N(C1-3-alkyl)(C1-3-alkanoyl), COOH, and COO-C1-3-alkyl, and all the aforementioned phenyl and heteroaryl groups can optionally be substituted with up to two groups, chosen from the group comprising F, Cl, Br, CH3, C2H5, OH, OCH3, OC2H5, NO2 N(CH3)2, CF3, C2F5 and SO2NH2, or R5 and R5', together with the N-atom, can form a five- to seven-membered heterocyclic ring that can contain an additional N- or O- or S-atom and can be substituted with C1-4-alkyl (C0-2-alkanediyl-C1-4-alkoxy), C1-4-alkoxycarbonyl, aminocarbonyl or phenyl as well as their optic or geometric isomers or tautomeric forms or pharmaceutically applicable salts, in which the following compounds are ruled out:
6-[[1-phenyl-2-(pyridine-4-yl)-1H-benzimidazol-6-yl]oxy]hexanoic acid, 6-[[1-phenyl-2-(benzothien-2-yl)-1H-benzimidazol-6-yl]oxy]hexanoic acid.
2.) Benzimidazoles according to Claim 1, characterized by the fact that R1 is a phenyl group, optionally substituted with up to two of the following substituents, independently of each other:
F, CI
OH, OR4, OCOR4 SR4, R4 or two adjacent substituents on R1 together form a ~O-CH2-O- or ~CH2-CH2-CH2-group.
3.) Benzimidazoles according to Claim 1 or 2, in which R2 is a monocyclic 5 - 6-membered heteroaryl group with 1 - 2 hetero atoms, chosen from the group comprising N, S, and O, optionally substituted with up to two of the following substituents, independently of each other:
F, CI, OR4, OCOR4 SR4, SOR4, SO2R4, R4 or two adjacent substituents on R2 form a ~O-CH2-O- or ~CH2-CH2-CH2- group.
F, CI, OR4, OCOR4 SR4, SOR4, SO2R4, R4 or two adjacent substituents on R2 form a ~O-CH2-O- or ~CH2-CH2-CH2- group.
4.) Benzimidazole according to one of the Claims 1-3, characterized by the fact R3 is H.
5.) Benzimidazoles according to one of the Claims 1 to 4, characterized by the fact that R4 and R4,' independently of each other, are C1-2-perfluoroalkyl, C1-4-alkyl.
6.) Benzimidazoles according to one of the Claims 1-5, characterized by the fact that R5 and R5', independently of each other, are C1-6-alky, in which a carbon atom can be replaced with O, S, SO, SO2, C3-5-cycloalkyl-C0-3-alkylene, in which, in a 5-membered cycloalkyl ring, one ring member can bean N or an O, the ring nitrogen is optionally substituted with C1-3-alkyl or C1-3-alkanoyl, C0-2-alkylene (5-6-membered heteroaryl with 1-2 heteroatoms from N, S and O) in which all the aforementioned alkyl and cycloalkyl groups scan be substituted with CF3, OH, NH2, NH-C1-3-alkyl, NH-C1-3-alkanoyl, N(C1-3-alkyl)2, N(C1-3-alkyl)(C1-3-alkanoyl), COOH, CONH2, and all the aforementioned heteroaryl groups can be substituted with one or two substituents from the group consisting of F, Cl, CH3, C2H5, OCH3, OC2H5, CF3, C2F5, or R5 and R5', together with the nitrogen atom, can form a 5-7-membered heterocycle that can contain an additional oxygen, nitrogen or sulfur atom and can be substituted with C1-4-alkyl, C1-5-alkoxy-C0-2-alkyl.
7.) Benzimidazoles according to one of the Claims 1-6, characterized by the fact that A is a straight-chain C3-6-alkylene.
8.) Benzimidazoles according to one of the Claims 1-5, 7, characterized by the fact that B is COOH or CONH2, each bonded to a carbon atom of group A.
9.) 6-[[1-(4-methylphenyl)-2-(3-pyridinyl)-1H-benzimidazol-6-yl]oxy]hexanoic acid 5-[[1-(4-methylphenyl)-2-(3-pyridinyl)-1H-benzimidazol-6-yl]oxy]pentanoic acid 4-[[1-(4-methylphenyl)-2-(3-pyridinyl)-1H-benzimidazol-6-yl]oxy]butyric acid 6-[[1-(4-methylphenyl)-2-(4-pyridinyl)-1H-benzimidazol-6-yl]oxy]hexanoic acid 6-[[1-(4-methylphenyl)-2-(3-thienyl)-1H-benzimidazol-6-yl]oxy]hexanoic acid 5-[[1-(4-methylphenyl)-2-(3-thienyl)-1H-benzimidazol-6-yl]oxy]pentanoic acid 4-[[1-(4-methylphenyl)-2-(3-thienyl)-1H-benzimidazol-6-yl]oxy]butyric acid 5-[[1-phenyl-2-(3-thienyl)-1H-benzimidazol-6-yl]oxy]pentanoic acid 4-[[1-phenyl-2-(3-thienyl)-1H-benzimidazol-6-yl]oxy]butyric acid 6-[[1-phenyl-2-(3-thienyl)-1H-benzimidazol-6-yl]oxy]hexanoic acid 6-[[1-(4-fluorophenyl)-2-(3-thienyl)-1H-benzimidazol-6-yl]oxy]hexanoic acid 5-[[1-(4-fluorophenyl)-2-(3-thienyl)-1H-benzimidazol-6-yl]oxy]pentanoic acid 6-[[1-(4-fluorophenyl)-2-(3-pyridinyl)-1H-benzimidazol-6-yl]oxy]hexanoic acid 5-[[1-(4-fluorophenyl)-2-(3-pyridinyl)-1H-benzimidazol-6-yl]oxy]pentanoic acid 5-[[1-2-(3-pyridinyl)-1H-benzimidazol-6-yl]oxy]pentanoic acid 4-[[1-2-(3-pyridinyl)-1H-benzimidazol-6-yl]oxy]butyric acid 6-[[1-2-(3-pyridinyl)-1H-benzimidazol-6-yl]oxy]hexanoic acid N-(3-methoxypropyl)-6-[[1-(4-methylphenyl)-2-(3-pyridinyl)-1H-benzimidazol-6-yl]oxy]hexanamide 6-[[1-4-methylphenyl)-2-(3-pyridinyl)-1H-benzimidazol-6-yl]oxy]-1-morpholin-1-ylhexan-1-one N-methyl-6-[[1-(4-methylphenyl)-2-(3-pyridinyl)-1H-benzimidazol-6-yl]oxy]hexanamide N,N-dimethyl-6- [[1-(4-methylphenyl)-2-(3-pyridinyl)-1H-benzimidazol-6-yl]oxy]hexanamide 6-[[1-(4-methylphenyl)-2-(3-pyridinyl)-1H-benzimidazol-6-yl]oxy]hexanamide N-cyclopropyl-6-[[1-(4-methylphenyl)-2-(3-thienyl)-1H-benzimidazol-6-yl]oxy]hexanamide N-methyl-6-[[1-(4-methylphenyl)-2-(3-thienyl)-1H-benzimidazol-6-yl]oxy]hexanamide 6-[[1-(4-methylphenyl)-2-1H-benzimidazol-6-yl]oxy]-1-[thiazolidin-3-yl)hexan-1-one N-(2-methoxyethyl)-5-[[1-(4-methylphenyl)-2-(3-pyridinyl)-1H-benzimidazol-6-yl)oxy]pentanamide N,N-dimethyl-5-[[1-(4-methylphenyl)-2-(3-pyridinyl)-1H-benzimidazol-6-yl]oxy]pentanamide 5-[[1-(4-methylphenyl)-2-(3-pyridinyl)-1H-benzimidazol-6-yl]oxy]pentanamide 6-[[1-(4-methylphenyl)-2-(2-thienyl)-1H-benzimidazol-6-yl]oxy]hexanoic acid according to Claim 1.
10.) Use of a compound according to one of the Claims 1-9 for preparation of a drug for treatment or prevention of diseases that are associated with microglia activation.
11.) Use according to Claim 10 for treatment or prevention of inflammatory, allergic, infectious or autoimmune diseases.
12.) Pharmaceutical agents, characterized by the fact that they contain one or more compounds according to one of the Claims 1-9 and one or more vehicles and/or inactive ingredients.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10207844A DE10207844A1 (en) | 2002-02-15 | 2002-02-15 | 1-phenyl-2-heteroaryl-substituted benzimidazole derivatives, their use for the preparation of medicaments and pharmaceutical preparations containing these derivatives |
| DE10207844.0 | 2002-02-15 | ||
| PCT/EP2003/000462 WO2003068766A1 (en) | 2002-02-15 | 2003-01-17 | 1-phenyl-2-heteroaryl-substituted benzimidazole derivatives, the use thereof for producing drugs used in the treatment of immunological diseases |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2475780A1 true CA2475780A1 (en) | 2003-08-21 |
| CA2475780C CA2475780C (en) | 2011-08-02 |
Family
ID=27674913
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2475780A Expired - Fee Related CA2475780C (en) | 2002-02-15 | 2003-01-17 | 1-phenyl-2-heteroaryl-substituted benzimidazole derivatives, their use to prepare drugs for treatment of immunological diseases |
Country Status (30)
| Country | Link |
|---|---|
| EP (1) | EP1474415B1 (en) |
| JP (1) | JP4739675B2 (en) |
| KR (1) | KR101027556B1 (en) |
| CN (1) | CN1317274C (en) |
| AR (1) | AR038492A1 (en) |
| AT (1) | ATE517881T1 (en) |
| AU (1) | AU2003205624B2 (en) |
| BR (1) | BR0307723A (en) |
| CA (1) | CA2475780C (en) |
| CR (1) | CR7442A (en) |
| CY (1) | CY1113230T1 (en) |
| DE (1) | DE10207844A1 (en) |
| DK (1) | DK1474415T3 (en) |
| EC (1) | ECSP045296A (en) |
| ES (1) | ES2369662T3 (en) |
| IL (1) | IL163431A (en) |
| MX (1) | MXPA04007949A (en) |
| NO (1) | NO329667B1 (en) |
| NZ (1) | NZ534660A (en) |
| PE (1) | PE20030941A1 (en) |
| PL (1) | PL216233B1 (en) |
| PT (1) | PT1474415E (en) |
| RS (1) | RS51831B (en) |
| RU (1) | RU2325384C2 (en) |
| SI (1) | SI1474415T1 (en) |
| TW (1) | TWI328583B (en) |
| UA (1) | UA81243C2 (en) |
| UY (1) | UY27661A1 (en) |
| WO (1) | WO2003068766A1 (en) |
| ZA (1) | ZA200407381B (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK1497266T3 (en) | 2002-03-27 | 2008-10-06 | Glaxo Group Ltd | Quinoline derivatives and their use as 5HT6 ligands |
| CN1787817B (en) * | 2003-05-19 | 2011-09-07 | Irm责任有限公司 | Immunosuppressant compounds and compositions |
| WO2014044611A1 (en) | 2012-09-20 | 2014-03-27 | Bayer Pharma Aktiengesellschaft | 1-aryl-2-heteroaryl benzimidazoles for the induction of neuronal regeneration |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4330959A1 (en) * | 1993-09-09 | 1995-03-16 | Schering Ag | New benzimidazole derivatives, processes for their preparation and their pharmaceutical use |
| MXPA02005742A (en) | 2000-01-14 | 2002-09-18 | Schering Ag | 1,2-diaryl benzimidazoles for treating illnesses associated with a microglia activation. |
| US7115645B2 (en) * | 2000-01-14 | 2006-10-03 | Schering Aktiengesellschaft | 1,2 diarylbenzimidazoles and their pharmaceutical use |
| DE10207843A1 (en) * | 2002-02-15 | 2003-09-04 | Schering Ag | Microlia inhibitors for interruption of interleukin 12 and IFN-gamma mediated immune responses |
-
2002
- 2002-02-15 DE DE10207844A patent/DE10207844A1/en not_active Ceased
-
2003
- 2003-01-17 CN CNB038039974A patent/CN1317274C/en not_active Expired - Fee Related
- 2003-01-17 SI SI200332061T patent/SI1474415T1/en unknown
- 2003-01-17 RS YU71404A patent/RS51831B/en unknown
- 2003-01-17 DK DK03702464.3T patent/DK1474415T3/en active
- 2003-01-17 PL PL371269A patent/PL216233B1/en unknown
- 2003-01-17 JP JP2003567893A patent/JP4739675B2/en not_active Expired - Fee Related
- 2003-01-17 WO PCT/EP2003/000462 patent/WO2003068766A1/en active Application Filing
- 2003-01-17 EP EP03702464A patent/EP1474415B1/en not_active Expired - Lifetime
- 2003-01-17 RU RU2004127678/04A patent/RU2325384C2/en not_active IP Right Cessation
- 2003-01-17 KR KR1020047012576A patent/KR101027556B1/en not_active IP Right Cessation
- 2003-01-17 PT PT03702464T patent/PT1474415E/en unknown
- 2003-01-17 ES ES03702464T patent/ES2369662T3/en not_active Expired - Lifetime
- 2003-01-17 AU AU2003205624A patent/AU2003205624B2/en not_active Ceased
- 2003-01-17 NZ NZ534660A patent/NZ534660A/en not_active IP Right Cessation
- 2003-01-17 CA CA2475780A patent/CA2475780C/en not_active Expired - Fee Related
- 2003-01-17 AT AT03702464T patent/ATE517881T1/en active
- 2003-01-17 UA UA20040907405A patent/UA81243C2/en unknown
- 2003-01-17 BR BR0307723-3A patent/BR0307723A/en not_active IP Right Cessation
- 2003-01-17 MX MXPA04007949A patent/MXPA04007949A/en active IP Right Grant
- 2003-01-31 PE PE2003000110A patent/PE20030941A1/en not_active Application Discontinuation
- 2003-02-11 UY UY27661A patent/UY27661A1/en not_active Application Discontinuation
- 2003-02-12 AR ARP030100437A patent/AR038492A1/en not_active Application Discontinuation
- 2003-02-14 TW TW092103073A patent/TWI328583B/en not_active IP Right Cessation
-
2004
- 2004-08-10 IL IL163431A patent/IL163431A/en not_active IP Right Cessation
- 2004-09-01 CR CR7442A patent/CR7442A/en not_active Application Discontinuation
- 2004-09-14 EC EC2004005296A patent/ECSP045296A/en unknown
- 2004-09-14 NO NO20043841A patent/NO329667B1/en not_active IP Right Cessation
- 2004-09-14 ZA ZA2004/07381A patent/ZA200407381B/en unknown
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2011
- 2011-10-26 CY CY20111101016T patent/CY1113230T1/en unknown
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