FR2488890A1 - Derives tricycliques de l'imidazole, leur preparation et leurs utilisations therapeutiques - Google Patents
Derives tricycliques de l'imidazole, leur preparation et leurs utilisations therapeutiques Download PDFInfo
- Publication number
- FR2488890A1 FR2488890A1 FR8115936A FR8115936A FR2488890A1 FR 2488890 A1 FR2488890 A1 FR 2488890A1 FR 8115936 A FR8115936 A FR 8115936A FR 8115936 A FR8115936 A FR 8115936A FR 2488890 A1 FR2488890 A1 FR 2488890A1
- Authority
- FR
- France
- Prior art keywords
- methyl
- melting
- theory
- pyridyl
- water
- 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.)
- Granted
Links
- RAXXELZNTBOGNW-UHFFFAOYSA-N 1H-imidazole Chemical class C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 title abstract description 40
- 238000002360 preparation method Methods 0.000 title abstract description 18
- 230000001225 therapeutic effect Effects 0.000 title abstract description 5
- -1 2-PYRIDYL Chemical class 0.000 abstract description 65
- 150000001875 compounds Chemical class 0.000 abstract description 53
- 239000002253 acid Substances 0.000 abstract description 35
- 150000007513 acids Chemical class 0.000 abstract description 10
- 230000002496 gastric effect Effects 0.000 abstract description 8
- 230000000694 effects Effects 0.000 abstract description 5
- 230000000767 anti-ulcer Effects 0.000 abstract description 4
- 239000003112 inhibitor Substances 0.000 abstract description 2
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 abstract 1
- 101150065749 Churc1 gene Proteins 0.000 abstract 1
- 102100038239 Protein Churchill Human genes 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 114
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 90
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 85
- 230000008018 melting Effects 0.000 description 81
- 238000002844 melting Methods 0.000 description 81
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 73
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 72
- 239000000203 mixture Substances 0.000 description 70
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 66
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 66
- 239000000243 solution Substances 0.000 description 46
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 44
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 39
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 36
- 229960000583 acetic acid Drugs 0.000 description 35
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 31
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 30
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 29
- 125000006479 2-pyridyl methyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 description 29
- 239000012362 glacial acetic acid Substances 0.000 description 29
- 238000010992 reflux Methods 0.000 description 27
- 150000003839 salts Chemical class 0.000 description 27
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 26
- 229910052739 hydrogen Inorganic materials 0.000 description 25
- 239000001257 hydrogen Substances 0.000 description 25
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 23
- 238000003756 stirring Methods 0.000 description 22
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 21
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 18
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 18
- 125000000217 alkyl group Chemical group 0.000 description 18
- 239000012043 crude product Substances 0.000 description 16
- 239000013078 crystal Substances 0.000 description 16
- 238000000034 method Methods 0.000 description 16
- 239000000047 product Substances 0.000 description 16
- 238000012360 testing method Methods 0.000 description 16
- 238000001704 evaporation Methods 0.000 description 15
- 230000008020 evaporation Effects 0.000 description 15
- 239000011734 sodium Substances 0.000 description 14
- 239000000725 suspension Substances 0.000 description 13
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 12
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- 239000003054 catalyst Substances 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 12
- 230000007935 neutral effect Effects 0.000 description 12
- 229910052938 sodium sulfate Inorganic materials 0.000 description 12
- 235000011152 sodium sulphate Nutrition 0.000 description 12
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 11
- 241001465754 Metazoa Species 0.000 description 10
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 10
- 239000007868 Raney catalyst Substances 0.000 description 9
- 229910000564 Raney nickel Inorganic materials 0.000 description 9
- 238000001953 recrystallisation Methods 0.000 description 9
- JOOFUZFINOTQIW-UHFFFAOYSA-N 5h-[1,3]dioxolo[4,5-f]benzimidazole Chemical compound C1=C2OCOC2=CC2=C1NC=N2 JOOFUZFINOTQIW-UHFFFAOYSA-N 0.000 description 8
- 238000010521 absorption reaction Methods 0.000 description 8
- 239000002585 base Substances 0.000 description 8
- 238000001816 cooling Methods 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- YHMYGUUIMTVXNW-UHFFFAOYSA-N 1,3-dihydrobenzimidazole-2-thione Chemical compound C1=CC=C2NC(S)=NC2=C1 YHMYGUUIMTVXNW-UHFFFAOYSA-N 0.000 description 7
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 7
- 208000025865 Ulcer Diseases 0.000 description 7
- 238000002425 crystallisation Methods 0.000 description 7
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- 230000028327 secretion Effects 0.000 description 7
- 239000007858 starting material Substances 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- 231100000397 ulcer Toxicity 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
- 239000013543 active substance Substances 0.000 description 6
- 230000008025 crystallization Effects 0.000 description 6
- 150000002431 hydrogen Chemical class 0.000 description 6
- 229910017604 nitric acid Inorganic materials 0.000 description 6
- 239000003826 tablet Substances 0.000 description 6
- KBFUPRLHCWUTGK-UHFFFAOYSA-N 1,1,3,3-tetramethylinden-2-one Chemical compound C1=CC=C2C(C)(C)C(=O)C(C)(C)C2=C1 KBFUPRLHCWUTGK-UHFFFAOYSA-N 0.000 description 5
- NJWIMFZLESWFIM-UHFFFAOYSA-N 2-(chloromethyl)pyridine Chemical compound ClCC1=CC=CC=N1 NJWIMFZLESWFIM-UHFFFAOYSA-N 0.000 description 5
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 5
- 229920002261 Corn starch Polymers 0.000 description 5
- 239000007832 Na2SO4 Substances 0.000 description 5
- 229910004298 SiO 2 Inorganic materials 0.000 description 5
- 239000001110 calcium chloride Substances 0.000 description 5
- 229910001628 calcium chloride Inorganic materials 0.000 description 5
- VUWGLJKFJGNHLC-UHFFFAOYSA-N cyclopenta[f]benzimidazole Chemical compound N1=CN=C2C=C3C=CC=C3C=C12 VUWGLJKFJGNHLC-UHFFFAOYSA-N 0.000 description 5
- 239000012074 organic phase Substances 0.000 description 5
- 229910000029 sodium carbonate Inorganic materials 0.000 description 5
- SNHKEQOYVVRBQO-UHFFFAOYSA-N 1,3-benzodioxole-5,6-diamine Chemical compound C1=C(N)C(N)=CC2=C1OCO2 SNHKEQOYVVRBQO-UHFFFAOYSA-N 0.000 description 4
- BVJIXYJOFWYOBL-UHFFFAOYSA-N 2-(5-methyl-1h-imidazol-4-yl)ethanamine;dihydrochloride Chemical compound Cl.Cl.CC=1NC=NC=1CCN BVJIXYJOFWYOBL-UHFFFAOYSA-N 0.000 description 4
- 239000001828 Gelatine Substances 0.000 description 4
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- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 4
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- 125000004429 atom Chemical group 0.000 description 4
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- 229940099112 cornstarch Drugs 0.000 description 4
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
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- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
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- 239000011591 potassium Substances 0.000 description 4
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- JCBJVAJGLKENNC-UHFFFAOYSA-M potassium ethyl xanthate Chemical compound [K+].CCOC([S-])=S JCBJVAJGLKENNC-UHFFFAOYSA-M 0.000 description 4
- 125000003396 thiol group Chemical group [H]S* 0.000 description 4
- 229910052727 yttrium Inorganic materials 0.000 description 4
- OXFSTTJBVAAALW-UHFFFAOYSA-N 1,3-dihydroimidazole-2-thione Chemical compound SC1=NC=CN1 OXFSTTJBVAAALW-UHFFFAOYSA-N 0.000 description 3
- SOMKOFZJHWCRCJ-UHFFFAOYSA-N 3h-benzimidazole-5-thiol Chemical compound SC1=CC=C2NC=NC2=C1 SOMKOFZJHWCRCJ-UHFFFAOYSA-N 0.000 description 3
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- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
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- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 3
- 241000700198 Cavia Species 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
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- OPBQKJZMUAITIZ-UHFFFAOYSA-N 1h-[1,4]dioxino[2,3-f]benzimidazole Chemical compound C1=C2OC=COC2=CC2=C1N=CN2 OPBQKJZMUAITIZ-UHFFFAOYSA-N 0.000 description 2
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring 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
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/06—Compounds containing nitro groups bound to a carbon skeleton having nitro groups bound to carbon atoms of six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/45—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by at least one doubly—bound oxygen atom, not being part of a —CHO group
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/50—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions decreasing the number of carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/04—1,3-Dioxanes; Hydrogenated 1,3-dioxanes
- C07D319/08—1,3-Dioxanes; Hydrogenated 1,3-dioxanes condensed with carbocyclic rings or ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- 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
- C07D491/02—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 two hetero rings
- C07D491/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/08—One of the condensed rings being a six-membered aromatic ring the other ring being five-membered, e.g. indane
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Animal Behavior & Ethology (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH632180A CH644116A5 (de) | 1980-08-21 | 1980-08-21 | Imidazolderivate. |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2488890A1 true FR2488890A1 (fr) | 1982-02-26 |
| FR2488890B1 FR2488890B1 (cg-RX-API-DMAC7.html) | 1985-01-11 |
Family
ID=4307711
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR8115936A Granted FR2488890A1 (fr) | 1980-08-21 | 1981-08-19 | Derives tricycliques de l'imidazole, leur preparation et leurs utilisations therapeutiques |
Country Status (20)
| Country | Link |
|---|---|
| US (3) | US4435406A (cg-RX-API-DMAC7.html) |
| JP (1) | JPS5770886A (cg-RX-API-DMAC7.html) |
| AT (1) | AT376665B (cg-RX-API-DMAC7.html) |
| AU (1) | AU541834B2 (cg-RX-API-DMAC7.html) |
| BE (1) | BE890024A (cg-RX-API-DMAC7.html) |
| CA (1) | CA1134829A (cg-RX-API-DMAC7.html) |
| CH (1) | CH644116A5 (cg-RX-API-DMAC7.html) |
| DE (1) | DE3132613A1 (cg-RX-API-DMAC7.html) |
| DK (1) | DK300981A (cg-RX-API-DMAC7.html) |
| FR (1) | FR2488890A1 (cg-RX-API-DMAC7.html) |
| GB (1) | GB2082580B (cg-RX-API-DMAC7.html) |
| IE (1) | IE51507B1 (cg-RX-API-DMAC7.html) |
| IL (1) | IL63576A (cg-RX-API-DMAC7.html) |
| IT (1) | IT1138156B (cg-RX-API-DMAC7.html) |
| LU (1) | LU83571A1 (cg-RX-API-DMAC7.html) |
| NL (1) | NL8103690A (cg-RX-API-DMAC7.html) |
| NZ (1) | NZ198047A (cg-RX-API-DMAC7.html) |
| PH (1) | PH17937A (cg-RX-API-DMAC7.html) |
| SE (1) | SE452765B (cg-RX-API-DMAC7.html) |
| ZA (1) | ZA815633B (cg-RX-API-DMAC7.html) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2543551A1 (fr) * | 1983-02-11 | 1984-10-05 | Haessle Ab | Benzimidapoles substitues, procede pour leur preparation et compositions pharmaceutiques les contenant, inhibant la secretion d'acide gastrique ou exercant un effet cytoprotecteur du tube digestif |
| EP0292348A1 (fr) * | 1987-04-30 | 1988-11-23 | CENTRE INTERNATIONAL DE RECHERCHES DERMATOLOGIQUES GALDERMA - CIRD GALDERMA Groupement d'Intérêt Economique dit: | Dérivés hétérocycliques polycycliques , leur procédé de préparation et leur utilisation en médecine humaine et vétérinaire |
Families Citing this family (34)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ZA825106B (en) * | 1981-08-13 | 1983-04-27 | Haessle Ab | Novel pharmaceutical compositions |
| DE3216843C2 (de) * | 1982-05-05 | 1986-10-23 | Ludwig Heumann & Co GmbH, 8500 Nürnberg | 3-Thiomethyl-pyridin-Derivate, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel |
| US4686232A (en) * | 1983-02-28 | 1987-08-11 | Sumitomo Chemical Company, Limited | Fungicidal aniline derivatives |
| HU191756B (en) * | 1983-05-03 | 1987-04-28 | Byk Gulden Lomberg Chem Fab | Process for preparing new fluoro-alkoxy-benzimidazole derivatives |
| HU195220B (en) * | 1983-05-03 | 1988-04-28 | Byk Gulden Lomberg Chem Fqb | Process for production of new fluor-alkoxi-benzimidasole-derivatives and medical compositions containig them |
| ZW4585A1 (en) * | 1984-04-19 | 1985-11-20 | Hoffmann La Roche | Imidazole derivatives |
| PL144822B1 (en) * | 1984-05-12 | 1988-07-30 | Boehringer Mannheim Gmbh | Method of obtaining novel pyrolobenzimidazoles |
| IL75400A (en) * | 1984-06-16 | 1988-10-31 | Byk Gulden Lomberg Chem Fab | Dialkoxypyridine methyl(sulfinyl or sulfonyl)benzimidazoles,processes for the preparation thereof and pharmaceutical compositions containing the same |
| 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 |
| GB8526154D0 (en) * | 1985-02-06 | 1985-11-27 | Kotobuki Seiyaku Co Ltd | 2-substituted cyclo-heptoimidazoles |
| DK337086A (da) * | 1985-08-12 | 1987-02-13 | Hoffmann La Roche | Benzimidazolderivater |
| SE8505112D0 (sv) * | 1985-10-29 | 1985-10-29 | Haessle Ab | Novel pharmacological compounds |
| WO1987005296A1 (en) * | 1986-03-07 | 1987-09-11 | Pfizer Inc. | 2-[(2-pyridyl)methylsulfinyl]thienoimidazoles and related compounds as antiulcer agents |
| SE8604566D0 (sv) * | 1986-10-27 | 1986-10-27 | Haessle Ab | Novel compunds |
| NZ234564A (en) | 1986-11-21 | 1991-04-26 | Haessle Ab | 1-substituted benzimidazoles and pharmaceutical compositions |
| SE8604998D0 (sv) | 1986-11-21 | 1986-11-21 | Haessle Ab | Novel pharmacological compounds |
| DE3701277A1 (de) * | 1987-01-17 | 1988-07-28 | Boehringer Mannheim Gmbh | Neue tricyclische benzimidazole, verfahren zu ihrer herstellung und verwendung als arzneimittel |
| US5223515A (en) * | 1988-08-18 | 1993-06-29 | Takeda Chemical Industries, Ltd. | Injectable solution containing a pyridyl methylsulfinylbenzimidazole |
| US5175286A (en) * | 1988-09-20 | 1992-12-29 | Hisamitsu Pharmaceutical Co., Inc. | Dibenz[b,e]oxepin derivatives |
| IE64199B1 (en) * | 1988-12-22 | 1995-07-12 | Haessle Ab | Compound with gastric acid inhibitory effect and process for its preparation |
| SE8804629D0 (sv) | 1988-12-22 | 1988-12-22 | Ab Haessle | New therapeutically active compounds |
| SE8804628D0 (sv) | 1988-12-22 | 1988-12-22 | Ab Haessle | New compounds |
| US5274099A (en) * | 1989-12-20 | 1993-12-28 | Aktiebolaget Hassle | Therapeutically active fluoro substituted benzimidazoles |
| US5049674A (en) * | 1989-12-20 | 1991-09-17 | Aktiebolaget Hassle | Therapeutically active fluoro substituted benzimidazoles |
| US4965269A (en) * | 1989-12-20 | 1990-10-23 | Ab Hassle | Therapeutically active chloro substituted benzimidazoles |
| SE9002206D0 (sv) | 1990-06-20 | 1990-06-20 | Haessle Ab | New compounds |
| DE4027592A1 (de) * | 1990-08-31 | 1992-03-05 | Beiersdorf Ag | Neue pyrrolobenzimidazole, imidazobenzoxazinone und imidazochinolone, verfahren zu ihrer herstellung und ihre verwendung sowie die verbindungen enthaltende zubereitungen |
| US5395952A (en) * | 1991-06-03 | 1995-03-07 | Sumitomo Chemical Company, Limited | Benzimidazole derivatives agricultural and horticultural fungicides containing the same as an active ingredient and intermediate compounds thereof |
| US6207198B1 (en) * | 1995-09-21 | 2001-03-27 | Schwarz Pharma Ag | Composition containing an acid-labile omeprazole and process for its preparation |
| DE19745692A1 (de) * | 1997-07-24 | 1999-01-28 | Bayer Ag | Verfahren zur Herstellung von 2-Chlor-benzimidazol-Derivaten |
| AU753389C (en) * | 1997-12-31 | 2007-08-09 | Pfizer Products Inc. | Aryl fused azapolycyclic compounds |
| CN100349868C (zh) * | 2002-07-17 | 2007-11-21 | 京都药品工业株式会社 | 二氢吲哚化合物和其医药用途 |
| US20060024362A1 (en) | 2004-07-29 | 2006-02-02 | Pawan Seth | Composition comprising a benzimidazole and process for its manufacture |
| CN102140099A (zh) * | 2010-02-02 | 2011-08-03 | 山东轩竹医药科技有限公司 | 新的吡啶衍生物 |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2331340A1 (fr) * | 1974-05-16 | 1977-06-10 | Haessle Ab | Nouveaux derives du benzimidazole, procede pour leur obtention et compositions pharmaceutiques les contenant |
| EP0001279A1 (de) * | 1977-09-19 | 1979-04-04 | F. HOFFMANN-LA ROCHE & CO. Aktiengesellschaft | Imidazolderivate deren Herstellung und diese enthaltende Präparate |
| EP0005129B1 (en) * | 1978-04-14 | 1981-04-29 | Aktiebolaget Hässle | Substituted pyridylsulfinylbenzimidazoles having gastric acid secretion properties, pharmaceutical preparations containing same, and intermediates for their preparation |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE5129C1 (cg-RX-API-DMAC7.html) | 1894-05-19 | |||
| SE418966B (sv) * | 1974-02-18 | 1981-07-06 | Haessle Ab | Analogiforfarande for framstellning av foreningar med magsyrasekretionsinhiberande verkan |
-
1980
- 1980-08-21 CH CH632180A patent/CH644116A5/de not_active IP Right Cessation
-
1981
- 1981-07-07 DK DK300981A patent/DK300981A/da not_active Application Discontinuation
- 1981-08-05 NL NL8103690A patent/NL8103690A/xx not_active Application Discontinuation
- 1981-08-05 PH PH26015A patent/PH17937A/en unknown
- 1981-08-05 US US06/290,032 patent/US4435406A/en not_active Expired - Fee Related
- 1981-08-14 NZ NZ198047A patent/NZ198047A/en unknown
- 1981-08-14 ZA ZA815633A patent/ZA815633B/xx unknown
- 1981-08-14 AU AU74089/81A patent/AU541834B2/en not_active Ceased
- 1981-08-14 IL IL63576A patent/IL63576A/xx unknown
- 1981-08-18 DE DE19813132613 patent/DE3132613A1/de not_active Withdrawn
- 1981-08-18 IT IT23556/81A patent/IT1138156B/it active
- 1981-08-19 FR FR8115936A patent/FR2488890A1/fr active Granted
- 1981-08-19 CA CA000384169A patent/CA1134829A/en not_active Expired
- 1981-08-20 GB GB8125486A patent/GB2082580B/en not_active Expired
- 1981-08-20 AT AT0364381A patent/AT376665B/de not_active IP Right Cessation
- 1981-08-20 BE BE0/205721A patent/BE890024A/fr not_active IP Right Cessation
- 1981-08-20 LU LU83571A patent/LU83571A1/de unknown
- 1981-08-20 SE SE8104941A patent/SE452765B/sv not_active IP Right Cessation
- 1981-08-20 IE IE1912/81A patent/IE51507B1/en unknown
- 1981-08-20 JP JP56129475A patent/JPS5770886A/ja active Pending
-
1983
- 1983-12-12 US US06/560,698 patent/US4554280A/en not_active Expired - Fee Related
- 1983-12-12 US US06/560,699 patent/US4599347A/en not_active Expired - Fee Related
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2331340A1 (fr) * | 1974-05-16 | 1977-06-10 | Haessle Ab | Nouveaux derives du benzimidazole, procede pour leur obtention et compositions pharmaceutiques les contenant |
| EP0001279A1 (de) * | 1977-09-19 | 1979-04-04 | F. HOFFMANN-LA ROCHE & CO. Aktiengesellschaft | Imidazolderivate deren Herstellung und diese enthaltende Präparate |
| EP0005129B1 (en) * | 1978-04-14 | 1981-04-29 | Aktiebolaget Hässle | Substituted pyridylsulfinylbenzimidazoles having gastric acid secretion properties, pharmaceutical preparations containing same, and intermediates for their preparation |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2543551A1 (fr) * | 1983-02-11 | 1984-10-05 | Haessle Ab | Benzimidapoles substitues, procede pour leur preparation et compositions pharmaceutiques les contenant, inhibant la secretion d'acide gastrique ou exercant un effet cytoprotecteur du tube digestif |
| EP0292348A1 (fr) * | 1987-04-30 | 1988-11-23 | CENTRE INTERNATIONAL DE RECHERCHES DERMATOLOGIQUES GALDERMA - CIRD GALDERMA Groupement d'Intérêt Economique dit: | Dérivés hétérocycliques polycycliques , leur procédé de préparation et leur utilisation en médecine humaine et vétérinaire |
Also Published As
| Publication number | Publication date |
|---|---|
| SE8104941L (sv) | 1982-02-22 |
| NZ198047A (en) | 1985-05-31 |
| FR2488890B1 (cg-RX-API-DMAC7.html) | 1985-01-11 |
| ATA364381A (de) | 1984-05-15 |
| AU7408981A (en) | 1982-02-25 |
| IE51507B1 (en) | 1987-01-07 |
| BE890024A (fr) | 1982-02-22 |
| NL8103690A (nl) | 1982-03-16 |
| GB2082580B (en) | 1984-03-07 |
| IL63576A0 (en) | 1981-11-30 |
| US4435406A (en) | 1984-03-06 |
| PH17937A (en) | 1985-02-05 |
| LU83571A1 (de) | 1983-06-08 |
| DE3132613A1 (de) | 1982-06-24 |
| US4554280A (en) | 1985-11-19 |
| SE452765B (sv) | 1987-12-14 |
| ZA815633B (en) | 1982-08-25 |
| IE811912L (en) | 1982-02-21 |
| IL63576A (en) | 1985-10-31 |
| IT8123556A0 (it) | 1981-08-18 |
| CA1134829A (en) | 1982-11-02 |
| CH644116A5 (de) | 1984-07-13 |
| AT376665B (de) | 1984-12-27 |
| IT1138156B (it) | 1986-09-17 |
| AU541834B2 (en) | 1985-01-24 |
| DK300981A (da) | 1982-02-22 |
| US4599347A (en) | 1986-07-08 |
| GB2082580A (en) | 1982-03-10 |
| JPS5770886A (en) | 1982-05-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| ST | Notification of lapse |