LV10954B - Benzimidazole derivatives, process for their production and a pharmaceutical composition containing the same - Google Patents
Benzimidazole derivatives, process for their production and a pharmaceutical composition containing the same Download PDFInfo
- Publication number
- LV10954B LV10954B LVP-93-1371A LV931371A LV10954B LV 10954 B LV10954 B LV 10954B LV 931371 A LV931371 A LV 931371A LV 10954 B LV10954 B LV 10954B
- Authority
- LV
- Latvia
- Prior art keywords
- carbon atoms
- alkyl
- compound
- alkoxy
- methoxy
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 39
- 230000008569 process Effects 0.000 title claims description 10
- 238000004519 manufacturing process Methods 0.000 title claims description 8
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 8
- 125000003785 benzimidazolyl group Chemical class N1=C(NC2=C1C=CC=C2)* 0.000 title claims description 4
- 229940058303 antinematodal benzimidazole derivative Drugs 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 216
- 239000003814 drug Substances 0.000 claims abstract description 6
- 239000004480 active ingredient Substances 0.000 claims abstract description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 129
- 125000000217 alkyl group Chemical group 0.000 claims description 93
- 125000003545 alkoxy group Chemical group 0.000 claims description 73
- -1 cationic cation Chemical class 0.000 claims description 55
- 150000003839 salts Chemical class 0.000 claims description 43
- 150000002367 halogens Chemical class 0.000 claims description 40
- 229910052736 halogen Inorganic materials 0.000 claims description 34
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 26
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 26
- 238000002360 preparation method Methods 0.000 claims description 24
- 125000001424 substituent group Chemical group 0.000 claims description 21
- 125000006239 protecting group Chemical group 0.000 claims description 13
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 12
- 125000005843 halogen group Chemical group 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 229910052794 bromium Inorganic materials 0.000 claims description 10
- 239000000460 chlorine Substances 0.000 claims description 10
- 229910052740 iodine Inorganic materials 0.000 claims description 10
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 10
- 241000124008 Mammalia Species 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 9
- 230000027119 gastric acid secretion Effects 0.000 claims description 8
- 125000002071 phenylalkoxy group Chemical group 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 7
- 125000005083 alkoxyalkoxy group Chemical group 0.000 claims description 7
- 125000004414 alkyl thio group Chemical group 0.000 claims description 7
- 150000001768 cations Chemical class 0.000 claims description 7
- 229910052801 chlorine Inorganic materials 0.000 claims description 7
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 7
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 6
- 230000002401 inhibitory effect Effects 0.000 claims description 6
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 6
- 125000004660 phenylalkylthio group Chemical group 0.000 claims description 6
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 5
- 125000001153 fluoro group Chemical group F* 0.000 claims description 5
- 125000004428 fluoroalkoxy group Chemical group 0.000 claims description 5
- 230000003287 optical effect Effects 0.000 claims description 5
- 230000001590 oxidative effect Effects 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 229920006395 saturated elastomer Polymers 0.000 claims description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 4
- 125000001589 carboacyl group Chemical group 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- YKYIFUROKBDHCY-ONEGZZNKSA-N (e)-4-ethoxy-1,1,1-trifluorobut-3-en-2-one Chemical group CCO\C=C\C(=O)C(F)(F)F YKYIFUROKBDHCY-ONEGZZNKSA-N 0.000 claims description 3
- 125000000304 alkynyl group Chemical group 0.000 claims description 3
- 125000005133 alkynyloxy group Chemical group 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 claims description 3
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000001453 quaternary ammonium group Chemical group 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 238000002560 therapeutic procedure Methods 0.000 claims description 2
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 7
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 5
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 4
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 claims 3
- 241000282414 Homo sapiens Species 0.000 claims 3
- 229910052783 alkali metal Inorganic materials 0.000 claims 3
- 210000001035 gastrointestinal tract Anatomy 0.000 claims 2
- 208000027866 inflammatory disease Diseases 0.000 claims 2
- 241000282412 Homo Species 0.000 claims 1
- 150000001340 alkali metals Chemical class 0.000 claims 1
- 150000004703 alkoxides Chemical class 0.000 claims 1
- 229910052751 metal Inorganic materials 0.000 claims 1
- 239000002184 metal Substances 0.000 claims 1
- 150000002829 nitrogen Chemical class 0.000 claims 1
- 239000011593 sulfur Substances 0.000 claims 1
- 239000000203 mixture Substances 0.000 abstract description 53
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 78
- 239000000243 solution Substances 0.000 description 39
- 239000002253 acid Substances 0.000 description 37
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 30
- 229940073584 methylene chloride Drugs 0.000 description 25
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 24
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 20
- 239000002904 solvent Substances 0.000 description 19
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- 125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 description 14
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- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 9
- 159000000000 sodium salts Chemical class 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 8
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 8
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 8
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- 235000000346 sugar Nutrition 0.000 description 8
- 241000282472 Canis lupus familiaris Species 0.000 description 7
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 7
- 239000013543 active substance Substances 0.000 description 7
- 239000004615 ingredient Substances 0.000 description 7
- 150000004702 methyl esters Chemical class 0.000 description 7
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 6
- 238000009472 formulation Methods 0.000 description 6
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 6
- 238000001990 intravenous administration Methods 0.000 description 6
- 239000008101 lactose Substances 0.000 description 6
- 239000012071 phase Substances 0.000 description 6
- 150000003254 radicals Chemical class 0.000 description 6
- 239000011734 sodium Substances 0.000 description 6
- 229940083608 sodium hydroxide Drugs 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 6
- 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
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 5
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- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 4
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- 125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 4
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- 229940086542 triethylamine Drugs 0.000 description 4
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 3
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- 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
- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- 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
- C07D401/14—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 three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D453/00—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids
- C07D453/02—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids containing not further condensed quinuclidine ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6558—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system
- C07F9/65583—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system each of the hetero rings containing nitrogen as ring hetero atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Public Health (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE8604998A SE8604998D0 (sv) | 1986-11-21 | 1986-11-21 | Novel pharmacological compounds |
| SE8605551A SE8605551D0 (sv) | 1986-12-23 | 1986-12-23 | Novel pharmacological compounds |
| SE8704049A SE8704049D0 (sv) | 1987-10-16 | 1987-10-16 | Novel pharmacological compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| LV10954A LV10954A (lv) | 1995-12-20 |
| LV10954B true LV10954B (en) | 1996-08-20 |
Family
ID=27355365
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| LVP-93-1371A LV10954B (en) | 1986-11-21 | 1993-12-23 | Benzimidazole derivatives, process for their production and a pharmaceutical composition containing the same |
Country Status (24)
| Country | Link |
|---|---|
| EP (3) | EP0510719A1 (no) |
| JP (1) | JPH02500744A (no) |
| KR (1) | KR890700125A (no) |
| AT (1) | ATE84032T1 (no) |
| AU (1) | AU612129B2 (no) |
| DE (1) | DE3783356T2 (no) |
| DK (1) | DK365488A (no) |
| EG (1) | EG18379A (no) |
| ES (1) | ES2052603T3 (no) |
| FI (1) | FI892454A (no) |
| GR (1) | GR3007385T3 (no) |
| HU (1) | HU204814B (no) |
| IE (2) | IE940326L (no) |
| IL (1) | IL84504A (no) |
| IS (1) | IS1565B (no) |
| LV (1) | LV10954B (no) |
| MY (1) | MY101784A (no) |
| NO (1) | NO173998C (no) |
| NZ (2) | NZ234564A (no) |
| PL (1) | PL157655B1 (no) |
| PT (1) | PT86186B (no) |
| RU (1) | RU2062778C1 (no) |
| WO (1) | WO1988003921A1 (no) |
| YU (1) | YU47116B (no) |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE8801907D0 (sv) * | 1988-05-20 | 1988-05-20 | Haessle Ab | Novel pharmacological compounds |
| KR920003928B1 (ko) * | 1988-09-20 | 1992-05-18 | 히사미쯔세이야꾸 가부시기가이샤 | 신규의 디벤즈[b,e]옥세핀유도체 |
| SE8804629D0 (sv) * | 1988-12-22 | 1988-12-22 | Ab Haessle | New therapeutically active compounds |
| IE64199B1 (en) * | 1988-12-22 | 1995-07-12 | Haessle Ab | Compound with gastric acid inhibitory effect and process for its preparation |
| US5274099A (en) * | 1989-12-20 | 1993-12-28 | Aktiebolaget Hassle | Therapeutically active fluoro substituted benzimidazoles |
| US4965269A (en) * | 1989-12-20 | 1990-10-23 | Ab Hassle | Therapeutically active chloro substituted benzimidazoles |
| US5049674A (en) * | 1989-12-20 | 1991-09-17 | Aktiebolaget Hassle | Therapeutically active fluoro substituted benzimidazoles |
| SE9002206D0 (sv) | 1990-06-20 | 1990-06-20 | Haessle Ab | New compounds |
| PL166209B1 (pl) * | 1990-06-20 | 1995-04-28 | Astra Ab | Sposób wytwarzania nowych pochodnych benzimidazolu PL |
| EP0481764B1 (en) * | 1990-10-17 | 2000-03-29 | Takeda Chemical Industries, Ltd. | Pyridine derivatives, their production and use |
| SE9103776D0 (sv) * | 1991-12-19 | 1991-12-19 | Astra Ab | New compounds |
| JP2759228B2 (ja) * | 1992-05-21 | 1998-05-28 | 株式会社大塚製薬工場 | ホスホン酸ジエステル誘導体 |
| WO1994026279A1 (en) * | 1993-05-18 | 1994-11-24 | The Upjohn Company | Bisphosphonate esters for treating gastric disorders |
| US6875872B1 (en) | 1993-05-28 | 2005-04-05 | Astrazeneca | Compounds |
| AU6551198A (en) * | 1997-05-30 | 1998-12-30 | Dr. Reddy's Research Foundation | Novel benzimidazole derivatives as antiulcer agents, process for their preparation and pharmaceutical compositions containing them |
| DE69822514T2 (de) * | 1997-12-31 | 2005-03-24 | The University Of Kansas, Lawrence | Wasserlösliche pro-pharmaka von arzneistoffen, die ein tertiäres amin enthalten, und verfahren zu ihrer herstellung |
| US6420384B2 (en) | 1999-12-17 | 2002-07-16 | Ariad Pharmaceuticals, Inc. | Proton pump inhibitors |
| WO2002030920A1 (fr) * | 2000-10-12 | 2002-04-18 | Takeda Chemical Industries, Ltd. | Composes derives de benzimidazole, leur procede de production et leur utilisation |
| WO2003027098A1 (fr) * | 2001-09-25 | 2003-04-03 | Takeda Chemical Industries, Ltd. | Compose de benzymidazole, procede de production et d'utilisation de celui-ci |
| US7893271B2 (en) * | 2005-07-28 | 2011-02-22 | Intervet International B.V. | Benzimidazole carbamates and (thio) carbamates, and the synthesis and use thereof |
| WO2016061190A1 (en) | 2014-10-14 | 2016-04-21 | The Board Of Trustees Of The Leland Stanford Junior University | Method for treating neurodegenerative diseases |
| PT3390367T (pt) | 2015-12-15 | 2020-09-23 | Univ Leland Stanford Junior | Método para prevenir e/ou tratar enfraquecimento cognitivo e neuroinflamação associados ao envelhecimento |
| IL307972A (en) | 2018-08-06 | 2023-12-01 | Univ Leland Stanford Junior | 2-Arylbenzimidazoles as PPARCG1A agonists for the treatment of neurodegenerative diseases |
| MX2022001820A (es) * | 2019-08-20 | 2022-03-17 | Ono Pharmaceutical Co | Sal y forma cristalina de un compuesto que tiene actividad agonista para el receptor 5 de esfingosina-1-fosfato [acido (2s,3r,4e)-2-amino-3-hidroxioctadeca-4-enil-1-fosforico (s1p5). |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE418966B (sv) | 1974-02-18 | 1981-07-06 | Haessle Ab | Analogiforfarande for framstellning av foreningar med magsyrasekretionsinhiberande verkan |
| SE416649B (sv) | 1974-05-16 | 1981-01-26 | Haessle Ab | Forfarande for framstellning av foreningar som paverkar magsyrasekretionen |
| IN148930B (no) | 1977-09-19 | 1981-07-25 | Hoffmann La Roche | |
| SE7804231L (sv) | 1978-04-14 | 1979-10-15 | Haessle Ab | Magsyrasekretionsmedel |
| JPS5836312B2 (ja) * | 1978-08-21 | 1983-08-08 | 日本電信電話株式会社 | 通信用平衡ケ−ブル線路の障害位置測定方式 |
| JPS5687818A (en) * | 1979-12-19 | 1981-07-16 | Ishikawajima Harima Heavy Ind Co Ltd | Reflex type position detector |
| US4359465A (en) * | 1980-07-28 | 1982-11-16 | The Upjohn Company | Methods for treating gastrointestinal inflammation |
| CH644116A5 (de) | 1980-08-21 | 1984-07-13 | Hoffmann La Roche | Imidazolderivate. |
| JPS57137860A (en) * | 1981-02-20 | 1982-08-25 | Sumitomo Electric Ind Ltd | Optical tachometer |
| JPS5999597A (ja) * | 1982-11-30 | 1984-06-08 | 株式会社東芝 | 光学測定装置 |
| SE8300736D0 (sv) * | 1983-02-11 | 1983-02-11 | Haessle Ab | Novel pharmacologically active compounds |
| JPS6020051U (ja) * | 1983-07-19 | 1985-02-12 | 三洋電機株式会社 | カセツト収納装置 |
| AU568441B2 (en) * | 1984-09-24 | 1987-12-24 | Upjohn Company, The | 2-(pyridylalkenesulfinyl) benzimidazole derivatives |
| IL76839A (en) * | 1984-10-31 | 1988-08-31 | Byk Gulden Lomberg Chem Fab | Picoline derivatives,processes for the preparation thereof and pharmaceutical compositions containing the same |
| SE8505112D0 (sv) * | 1985-10-29 | 1985-10-29 | Haessle Ab | Novel pharmacological compounds |
-
1987
- 1987-11-10 NZ NZ234564A patent/NZ234564A/en unknown
- 1987-11-10 NZ NZ222495A patent/NZ222495A/en unknown
- 1987-11-17 IL IL8450487A patent/IL84504A/en not_active IP Right Cessation
- 1987-11-19 IE IE940326A patent/IE940326L/xx unknown
- 1987-11-19 IS IS3284A patent/IS1565B/is unknown
- 1987-11-19 EG EG669/87A patent/EG18379A/xx active
- 1987-11-19 IE IE312587A patent/IE61178B1/en not_active IP Right Cessation
- 1987-11-20 DE DE8787850362T patent/DE3783356T2/de not_active Expired - Fee Related
- 1987-11-20 ES ES87850362T patent/ES2052603T3/es not_active Expired - Lifetime
- 1987-11-20 MY MYPI87003072A patent/MY101784A/en unknown
- 1987-11-20 RU SU874614294A patent/RU2062778C1/ru active
- 1987-11-20 JP JP63500255A patent/JPH02500744A/ja active Pending
- 1987-11-20 YU YU211087A patent/YU47116B/sh unknown
- 1987-11-20 AT AT87850362T patent/ATE84032T1/de not_active IP Right Cessation
- 1987-11-20 HU HU876196A patent/HU204814B/hu not_active IP Right Cessation
- 1987-11-20 EP EP92108817A patent/EP0510719A1/en not_active Withdrawn
- 1987-11-20 EP EP87850362A patent/EP0279149B1/en not_active Expired - Lifetime
- 1987-11-20 EP EP87908006A patent/EP0332647A1/en active Pending
- 1987-11-20 AU AU83302/87A patent/AU612129B2/en not_active Ceased
- 1987-11-20 PT PT86186A patent/PT86186B/pt not_active IP Right Cessation
- 1987-11-20 WO PCT/SE1987/000546 patent/WO1988003921A1/en not_active Application Discontinuation
- 1987-11-21 PL PL1987268927A patent/PL157655B1/pl unknown
-
1988
- 1988-07-01 DK DK365488A patent/DK365488A/da not_active Application Discontinuation
- 1988-07-20 NO NO883229A patent/NO173998C/no unknown
- 1988-07-20 KR KR1019880700859A patent/KR890700125A/ko not_active Application Discontinuation
-
1989
- 1989-05-19 FI FI892454A patent/FI892454A/fi not_active Application Discontinuation
-
1993
- 1993-03-16 GR GR930400598T patent/GR3007385T3/el unknown
- 1993-12-23 LV LVP-93-1371A patent/LV10954B/en unknown
Also Published As
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